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molecular formula C19H16O4 B565621 (R)-Warfarin CAS No. 5543-58-8

(R)-Warfarin

Cat. No. B565621
M. Wt: 308.3 g/mol
InChI Key: PJVWKTKQMONHTI-OAHLLOKOSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04734282

Procedure details

Control, blank, and experimental reaction mixtures were made for each experiment. Control and blank reaction mixtures were made up with vitamin K and without vitamin K, respectively. Experimental reaction mixtures contained both vitamin K and a vitamin K antagonist. The control reaction mixture contained 3.00 ml of microsomal suspension, 0.81 ml of buffer II, 1.20 ml of an ATP-generating system (final concentrations: 1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl; added 0.5 min prior to reaction initiation), and at the time of reaction initiation 0.030 ml of vitamin K1 (final concentration 20 μg/ml) diluted in 0.85% sodium chloride solution. This vitamin K concentration is associated with maximal in vitro incorporation of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776). The blank reaction mixture consisted of the same components except that vitamin K was replaced by an equal volume of isotonic saline. The experimental reaction mixtures were made up in the same way as the control reaction mixtures with the exceptions that: (1) a volume of buffer II was replaced by a volume of buffer II containing an inhibitor of vitamin K-dependent carboxylation, and (2) all individual volumes were two-thirds of those in the control reaction mixtures. The sodium salts of TCP, phenindione, and warfarin were formed in aqueous sodium hydroxide solution (J. Am. Chem. Soc. 83, 2676-2679) and were freely soluble in buffer II at all concentrations used in these studies. Chloro-K1 was formulated as an oil-in-water emulsion with Tween 80 (5% v/v final concentration), while chloro-K3 was formulated as a suspension in Tween 80 (5% v/v final concentration) (Molecular Pharmacology 10, 373-380).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0.03 mL
Type
reactant
Reaction Step Two
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Eight
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eleven
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Twelve
[Compound]
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Reaction Step Thirteen
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Fourteen
Name
Quantity
1.2 mL
Type
reactant
Reaction Step Fifteen

Identifiers

REACTION_CXSMILES
P([O:13][CH2:14][C@H:15]1[O:19][C@@H:18](N2C3N=CN=C(N)C=3N=C2)[C@H:17](O)[C@@H:16]1[OH:31])(OP(OP(O)(O)=O)(O)=O)(=O)O.[CH3:32][C:33]1[C:43](=O)[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:35](=[O:36])[C:34]=1[CH2:45]/[CH:46]=[C:47](/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\[CH3:48].[OH-:65].[Na+]>[Cl-].[Na+]>[CH:32]1[CH:40]=[CH:41][C:42]([CH:37]2[C:35](=[O:36])[C:34]3[CH:45]=[CH:46][CH:47]=[CH:48][C:39]=3[C:38]2=[O:65])=[CH:43][CH:33]=1.[CH3:46][C:45]([CH2:34][CH:35]([C:15]1[C:14](=[O:13])[O:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:17]=2[C:16]=1[OH:31])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:65] |f:2.3,4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Step Two
Name
Quantity
0.03 mL
Type
reactant
Smiles
CC1=C(C(=O)C=2C=CC=CC2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
Step Three
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Six
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Seven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eight
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
[Cl-].[Na+]
Step Nine
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Ten
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eleven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Twelve
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Thirteen
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Smiles
Step Fourteen
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Fifteen
Name
Quantity
1.2 mL
Type
reactant
Smiles
P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC12)O)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
Control, blank, and experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
Control and blank reaction mixtures
CUSTOM
Type
CUSTOM
Details
Experimental reaction
CUSTOM
Type
CUSTOM
Details
The control reaction mixture
CONCENTRATION
Type
CONCENTRATION
Details
concentrations
DISSOLUTION
Type
DISSOLUTION
Details
1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl
ADDITION
Type
ADDITION
Details
added 0.5 min
Duration
0.5 min
CUSTOM
Type
CUSTOM
Details
to reaction initiation), and
CONCENTRATION
Type
CONCENTRATION
Details
This vitamin K concentration
ADDITION
Type
ADDITION
Details
of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776)
CUSTOM
Type
CUSTOM
Details
The blank reaction mixture
CUSTOM
Type
CUSTOM
Details
The experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
were made up in the same way as the control reaction mixtures with the exceptions that
CUSTOM
Type
CUSTOM
Details
in the control reaction mixtures

Outcomes

Product
Name
Type
product
Smiles
Name
Type
product
Smiles
C=1C=CC(=CC1)C2C(=O)C=3C=CC=CC3C2=O
Name
Type
product
Smiles
CC(=O)CC(C=1C=CC=CC1)C2=C(C=3C=CC=CC3OC2=O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04734282

Procedure details

Control, blank, and experimental reaction mixtures were made for each experiment. Control and blank reaction mixtures were made up with vitamin K and without vitamin K, respectively. Experimental reaction mixtures contained both vitamin K and a vitamin K antagonist. The control reaction mixture contained 3.00 ml of microsomal suspension, 0.81 ml of buffer II, 1.20 ml of an ATP-generating system (final concentrations: 1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl; added 0.5 min prior to reaction initiation), and at the time of reaction initiation 0.030 ml of vitamin K1 (final concentration 20 μg/ml) diluted in 0.85% sodium chloride solution. This vitamin K concentration is associated with maximal in vitro incorporation of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776). The blank reaction mixture consisted of the same components except that vitamin K was replaced by an equal volume of isotonic saline. The experimental reaction mixtures were made up in the same way as the control reaction mixtures with the exceptions that: (1) a volume of buffer II was replaced by a volume of buffer II containing an inhibitor of vitamin K-dependent carboxylation, and (2) all individual volumes were two-thirds of those in the control reaction mixtures. The sodium salts of TCP, phenindione, and warfarin were formed in aqueous sodium hydroxide solution (J. Am. Chem. Soc. 83, 2676-2679) and were freely soluble in buffer II at all concentrations used in these studies. Chloro-K1 was formulated as an oil-in-water emulsion with Tween 80 (5% v/v final concentration), while chloro-K3 was formulated as a suspension in Tween 80 (5% v/v final concentration) (Molecular Pharmacology 10, 373-380).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0.03 mL
Type
reactant
Reaction Step Two
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Eight
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eleven
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Twelve
[Compound]
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Reaction Step Thirteen
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Fourteen
Name
Quantity
1.2 mL
Type
reactant
Reaction Step Fifteen

Identifiers

REACTION_CXSMILES
P([O:13][CH2:14][C@H:15]1[O:19][C@@H:18](N2C3N=CN=C(N)C=3N=C2)[C@H:17](O)[C@@H:16]1[OH:31])(OP(OP(O)(O)=O)(O)=O)(=O)O.[CH3:32][C:33]1[C:43](=O)[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:35](=[O:36])[C:34]=1[CH2:45]/[CH:46]=[C:47](/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\[CH3:48].[OH-:65].[Na+]>[Cl-].[Na+]>[CH:32]1[CH:40]=[CH:41][C:42]([CH:37]2[C:35](=[O:36])[C:34]3[CH:45]=[CH:46][CH:47]=[CH:48][C:39]=3[C:38]2=[O:65])=[CH:43][CH:33]=1.[CH3:46][C:45]([CH2:34][CH:35]([C:15]1[C:14](=[O:13])[O:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:17]=2[C:16]=1[OH:31])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:65] |f:2.3,4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Step Two
Name
Quantity
0.03 mL
Type
reactant
Smiles
CC1=C(C(=O)C=2C=CC=CC2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
Step Three
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Six
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Seven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eight
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
[Cl-].[Na+]
Step Nine
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Ten
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eleven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Twelve
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Thirteen
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Smiles
Step Fourteen
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Fifteen
Name
Quantity
1.2 mL
Type
reactant
Smiles
P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC12)O)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
Control, blank, and experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
Control and blank reaction mixtures
CUSTOM
Type
CUSTOM
Details
Experimental reaction
CUSTOM
Type
CUSTOM
Details
The control reaction mixture
CONCENTRATION
Type
CONCENTRATION
Details
concentrations
DISSOLUTION
Type
DISSOLUTION
Details
1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl
ADDITION
Type
ADDITION
Details
added 0.5 min
Duration
0.5 min
CUSTOM
Type
CUSTOM
Details
to reaction initiation), and
CONCENTRATION
Type
CONCENTRATION
Details
This vitamin K concentration
ADDITION
Type
ADDITION
Details
of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776)
CUSTOM
Type
CUSTOM
Details
The blank reaction mixture
CUSTOM
Type
CUSTOM
Details
The experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
were made up in the same way as the control reaction mixtures with the exceptions that
CUSTOM
Type
CUSTOM
Details
in the control reaction mixtures

Outcomes

Product
Name
Type
product
Smiles
Name
Type
product
Smiles
C=1C=CC(=CC1)C2C(=O)C=3C=CC=CC3C2=O
Name
Type
product
Smiles
CC(=O)CC(C=1C=CC=CC1)C2=C(C=3C=CC=CC3OC2=O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04734282

Procedure details

Control, blank, and experimental reaction mixtures were made for each experiment. Control and blank reaction mixtures were made up with vitamin K and without vitamin K, respectively. Experimental reaction mixtures contained both vitamin K and a vitamin K antagonist. The control reaction mixture contained 3.00 ml of microsomal suspension, 0.81 ml of buffer II, 1.20 ml of an ATP-generating system (final concentrations: 1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl; added 0.5 min prior to reaction initiation), and at the time of reaction initiation 0.030 ml of vitamin K1 (final concentration 20 μg/ml) diluted in 0.85% sodium chloride solution. This vitamin K concentration is associated with maximal in vitro incorporation of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776). The blank reaction mixture consisted of the same components except that vitamin K was replaced by an equal volume of isotonic saline. The experimental reaction mixtures were made up in the same way as the control reaction mixtures with the exceptions that: (1) a volume of buffer II was replaced by a volume of buffer II containing an inhibitor of vitamin K-dependent carboxylation, and (2) all individual volumes were two-thirds of those in the control reaction mixtures. The sodium salts of TCP, phenindione, and warfarin were formed in aqueous sodium hydroxide solution (J. Am. Chem. Soc. 83, 2676-2679) and were freely soluble in buffer II at all concentrations used in these studies. Chloro-K1 was formulated as an oil-in-water emulsion with Tween 80 (5% v/v final concentration), while chloro-K3 was formulated as a suspension in Tween 80 (5% v/v final concentration) (Molecular Pharmacology 10, 373-380).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0.03 mL
Type
reactant
Reaction Step Two
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Eight
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eleven
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Twelve
[Compound]
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Reaction Step Thirteen
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Fourteen
Name
Quantity
1.2 mL
Type
reactant
Reaction Step Fifteen

Identifiers

REACTION_CXSMILES
P([O:13][CH2:14][C@H:15]1[O:19][C@@H:18](N2C3N=CN=C(N)C=3N=C2)[C@H:17](O)[C@@H:16]1[OH:31])(OP(OP(O)(O)=O)(O)=O)(=O)O.[CH3:32][C:33]1[C:43](=O)[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:35](=[O:36])[C:34]=1[CH2:45]/[CH:46]=[C:47](/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\[CH3:48].[OH-:65].[Na+]>[Cl-].[Na+]>[CH:32]1[CH:40]=[CH:41][C:42]([CH:37]2[C:35](=[O:36])[C:34]3[CH:45]=[CH:46][CH:47]=[CH:48][C:39]=3[C:38]2=[O:65])=[CH:43][CH:33]=1.[CH3:46][C:45]([CH2:34][CH:35]([C:15]1[C:14](=[O:13])[O:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:17]=2[C:16]=1[OH:31])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:65] |f:2.3,4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Step Two
Name
Quantity
0.03 mL
Type
reactant
Smiles
CC1=C(C(=O)C=2C=CC=CC2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
Step Three
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Six
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Seven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eight
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
[Cl-].[Na+]
Step Nine
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Ten
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eleven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Twelve
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Thirteen
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Smiles
Step Fourteen
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Fifteen
Name
Quantity
1.2 mL
Type
reactant
Smiles
P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC12)O)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
Control, blank, and experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
Control and blank reaction mixtures
CUSTOM
Type
CUSTOM
Details
Experimental reaction
CUSTOM
Type
CUSTOM
Details
The control reaction mixture
CONCENTRATION
Type
CONCENTRATION
Details
concentrations
DISSOLUTION
Type
DISSOLUTION
Details
1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl
ADDITION
Type
ADDITION
Details
added 0.5 min
Duration
0.5 min
CUSTOM
Type
CUSTOM
Details
to reaction initiation), and
CONCENTRATION
Type
CONCENTRATION
Details
This vitamin K concentration
ADDITION
Type
ADDITION
Details
of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776)
CUSTOM
Type
CUSTOM
Details
The blank reaction mixture
CUSTOM
Type
CUSTOM
Details
The experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
were made up in the same way as the control reaction mixtures with the exceptions that
CUSTOM
Type
CUSTOM
Details
in the control reaction mixtures

Outcomes

Product
Name
Type
product
Smiles
Name
Type
product
Smiles
C=1C=CC(=CC1)C2C(=O)C=3C=CC=CC3C2=O
Name
Type
product
Smiles
CC(=O)CC(C=1C=CC=CC1)C2=C(C=3C=CC=CC3OC2=O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04734282

Procedure details

Control, blank, and experimental reaction mixtures were made for each experiment. Control and blank reaction mixtures were made up with vitamin K and without vitamin K, respectively. Experimental reaction mixtures contained both vitamin K and a vitamin K antagonist. The control reaction mixture contained 3.00 ml of microsomal suspension, 0.81 ml of buffer II, 1.20 ml of an ATP-generating system (final concentrations: 1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl; added 0.5 min prior to reaction initiation), and at the time of reaction initiation 0.030 ml of vitamin K1 (final concentration 20 μg/ml) diluted in 0.85% sodium chloride solution. This vitamin K concentration is associated with maximal in vitro incorporation of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776). The blank reaction mixture consisted of the same components except that vitamin K was replaced by an equal volume of isotonic saline. The experimental reaction mixtures were made up in the same way as the control reaction mixtures with the exceptions that: (1) a volume of buffer II was replaced by a volume of buffer II containing an inhibitor of vitamin K-dependent carboxylation, and (2) all individual volumes were two-thirds of those in the control reaction mixtures. The sodium salts of TCP, phenindione, and warfarin were formed in aqueous sodium hydroxide solution (J. Am. Chem. Soc. 83, 2676-2679) and were freely soluble in buffer II at all concentrations used in these studies. Chloro-K1 was formulated as an oil-in-water emulsion with Tween 80 (5% v/v final concentration), while chloro-K3 was formulated as a suspension in Tween 80 (5% v/v final concentration) (Molecular Pharmacology 10, 373-380).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0.03 mL
Type
reactant
Reaction Step Two
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Eight
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eleven
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Twelve
[Compound]
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Reaction Step Thirteen
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Fourteen
Name
Quantity
1.2 mL
Type
reactant
Reaction Step Fifteen

Identifiers

REACTION_CXSMILES
P([O:13][CH2:14][C@H:15]1[O:19][C@@H:18](N2C3N=CN=C(N)C=3N=C2)[C@H:17](O)[C@@H:16]1[OH:31])(OP(OP(O)(O)=O)(O)=O)(=O)O.[CH3:32][C:33]1[C:43](=O)[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:35](=[O:36])[C:34]=1[CH2:45]/[CH:46]=[C:47](/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\[CH3:48].[OH-:65].[Na+]>[Cl-].[Na+]>[CH:32]1[CH:40]=[CH:41][C:42]([CH:37]2[C:35](=[O:36])[C:34]3[CH:45]=[CH:46][CH:47]=[CH:48][C:39]=3[C:38]2=[O:65])=[CH:43][CH:33]=1.[CH3:46][C:45]([CH2:34][CH:35]([C:15]1[C:14](=[O:13])[O:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:17]=2[C:16]=1[OH:31])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:65] |f:2.3,4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Step Two
Name
Quantity
0.03 mL
Type
reactant
Smiles
CC1=C(C(=O)C=2C=CC=CC2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
Step Three
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Six
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Seven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eight
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
[Cl-].[Na+]
Step Nine
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Ten
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eleven
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Twelve
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Thirteen
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Smiles
Step Fourteen
Name
II
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Fifteen
Name
Quantity
1.2 mL
Type
reactant
Smiles
P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC12)O)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
Control, blank, and experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
Control and blank reaction mixtures
CUSTOM
Type
CUSTOM
Details
Experimental reaction
CUSTOM
Type
CUSTOM
Details
The control reaction mixture
CONCENTRATION
Type
CONCENTRATION
Details
concentrations
DISSOLUTION
Type
DISSOLUTION
Details
1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl
ADDITION
Type
ADDITION
Details
added 0.5 min
Duration
0.5 min
CUSTOM
Type
CUSTOM
Details
to reaction initiation), and
CONCENTRATION
Type
CONCENTRATION
Details
This vitamin K concentration
ADDITION
Type
ADDITION
Details
of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776)
CUSTOM
Type
CUSTOM
Details
The blank reaction mixture
CUSTOM
Type
CUSTOM
Details
The experimental reaction mixtures
CUSTOM
Type
CUSTOM
Details
were made up in the same way as the control reaction mixtures with the exceptions that
CUSTOM
Type
CUSTOM
Details
in the control reaction mixtures

Outcomes

Product
Name
Type
product
Smiles
Name
Type
product
Smiles
C=1C=CC(=CC1)C2C(=O)C=3C=CC=CC3C2=O
Name
Type
product
Smiles
CC(=O)CC(C=1C=CC=CC1)C2=C(C=3C=CC=CC3OC2=O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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