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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015487

Secondary Accession Numbers

HMDB15487

Metabolite Identification

Common Name

Acenocoumarol

Description

Acenocoumarol, also known as mini-sintrom or acenokumarin, belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton. Acenocoumarol is a drug which is used for the treatment and prevention of thromboembolic diseases. more specifically, it is indicated for the prevention of cerebral embolism, deep vein thrombosis, pulmonary embolism, thromboembolism in infarction and transient ischemic attacks. it is used for the treatment of deep vein thrombosis and myocardial infarction. A hydroxycoumarin that is warfarin in which the hydrogen at position 4 of the phenyl substituent is replaced by a nitro group. Acenocoumarol is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, acenocoumarol is involved in acenocoumarol action pathway. Acenocoumarol is a potentially toxic compound.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

 
  Mrv0541 04191212182D          

 26 28  0  0  0  0            999 V2000
    9.4462   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4462   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1607  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8752   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8752   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1607   -8.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5897  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3041   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3041   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5897   -8.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0186  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7331   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7331   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0186   -8.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4475  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1620   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1620   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4475   -8.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5897  -11.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0186  -11.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7453  -11.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4561  -11.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7451  -12.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8899   -8.7371    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   16.6013   -9.1477    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   15.8896   -7.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  2  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 13 18  2  0  0  0  0
  7 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  CHG  2  24   1  25  -1
M  END

HMDB0243714
     RDKit          3D
(S)-Acenocoumarol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.4938    4.6307    0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2263    3.2832   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991    3.1810   -1.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025    2.1767    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    0.8443   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -0.1658    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7033   -0.5114    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139   -1.4294    1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449   -2.0254    1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -2.9675    1.6182 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2991   -3.5046    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4280   -3.2905    2.9467 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5619   -1.6860   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -0.7638   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    0.4276   -0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846   -0.4889   -1.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -0.9905   -2.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045   -0.8785   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0987   -1.7870   -1.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -2.1873   -1.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1373   -1.6896   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087   -0.7939    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2038   -0.3628    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426    0.4905    0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    0.9031    0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    1.7476    1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    5.4400   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512    4.8198    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    4.7501    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838    2.1389    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    2.4903   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9854    0.9087   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791   -0.0652    2.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -1.7057    2.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2960   -2.1488   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6963   -0.5204   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498   -0.7838   -2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5241   -2.1667   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -2.8947   -2.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1560   -2.0201   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0759   -0.4043    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 14  6  1  0
 25 15  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  CHG  2  10   1  12  -1
M  END

 
  Mrv0541 04191212182D          

 26 28  0  0  0  0            999 V2000
    9.4462   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4462   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1607  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8752   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8752   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1607   -8.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5897  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3041   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3041   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5897   -8.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0186  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7331   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7331   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0186   -8.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4475  -10.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1620   -9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1620   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4475   -8.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5897  -11.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0186  -11.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7453  -11.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4561  -11.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7451  -12.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8899   -8.7371    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   16.6013   -9.1477    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   15.8896   -7.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  2  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 13 18  2  0  0  0  0
  7 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  CHG  2  24   1  25  -1
M  END
> <DATABASE_ID>
HMDB0015487

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3

> <INCHI_KEY>
VABCILAOYCMVPS-UHFFFAOYSA-N

> <FORMULA>
C19H15NO6

> <MOLECULAR_WEIGHT>
353.3255

> <EXACT_MASS>
353.089937217

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
34.34892877125328

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.6846915516666665

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.284281499738075

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.793037768490707

> <JCHEM_PKA_STRONGEST_BASIC>
-6.825925280097388

> <JCHEM_POLAR_SURFACE_AREA>
109.41999999999999

> <JCHEM_REFRACTIVITY>
94.18479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acenocumarolo

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243714
     RDKit          3D
(S)-Acenocoumarol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.4938    4.6307    0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2263    3.2832   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991    3.1810   -1.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025    2.1767    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    0.8443   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -0.1658    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7033   -0.5114    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139   -1.4294    1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449   -2.0254    1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -2.9675    1.6182 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2991   -3.5046    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4280   -3.2905    2.9467 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5619   -1.6860   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -0.7638   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    0.4276   -0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846   -0.4889   -1.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -0.9905   -2.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045   -0.8785   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0987   -1.7870   -1.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -2.1873   -1.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1373   -1.6896   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087   -0.7939    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2038   -0.3628    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426    0.4905    0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    0.9031    0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    1.7476    1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    5.4400   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512    4.8198    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    4.7501    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838    2.1389    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    2.4903   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9854    0.9087   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791   -0.0652    2.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -1.7057    2.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2960   -2.1488   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6963   -0.5204   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498   -0.7838   -2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5241   -2.1667   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -2.8947   -2.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1560   -2.0201   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0759   -0.4043    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 14  6  1  0
 25 15  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  CHG  2  10   1  12  -1
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      17.633 -17.094   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.633 -18.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.967 -19.404   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.300 -18.634   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.300 -17.094   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.967 -16.324   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.634 -19.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.968 -18.634   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.968 -17.094   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      21.634 -16.324   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.301 -19.404   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.635 -18.634   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.635 -17.094   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      24.301 -16.324   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      26.969 -19.404   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.302 -18.634   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.302 -17.094   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.969 -16.324   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      21.634 -20.944   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      24.301 -20.944   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.658 -21.727   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.985 -20.962   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.658 -23.254   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      29.661 -16.309   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0      30.989 -17.076   0.000  0.00  0.00           O-1
HETATM   26  O   UNK     0      29.661 -14.784   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   19                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    5                                                       
CONECT   11    8   12   20                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   18                                                       
CONECT   14    9                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   13                                                       
CONECT   19    7                                                            
CONECT   20   11   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0015487
HETATM    1  C1  UNL     1       0.435  -4.315   0.248  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.324  -2.971  -0.371  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.553  -2.789  -1.197  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.277  -1.930   0.043  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.958  -0.666  -0.727  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.873   0.442  -0.371  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.310   1.338  -1.362  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.154   2.351  -1.039  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.622   2.556   0.244  1.00  0.00           C  
HETATM   10  N1  UNL     1       4.508   3.629   0.536  1.00  0.00           N1+
HETATM   11  O2  UNL     1       4.936   3.812   1.689  1.00  0.00           O  
HETATM   12  O3  UNL     1       4.879   4.458  -0.490  1.00  0.00           O1-
HETATM   13  C9  UNL     1       3.194   1.675   1.222  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.338   0.645   0.907  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.462  -0.317  -0.708  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.237  -0.179   0.440  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.644  -0.389   1.643  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.574   0.161   0.348  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.384   0.310   1.440  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.711   0.650   1.303  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.296   0.860   0.060  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.494   0.714  -1.036  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.160   0.371  -0.891  1.00  0.00           C  
HETATM   24  O5  UNL     1      -2.412   0.236  -1.944  1.00  0.00           O  
HETATM   25  C19 UNL     1      -1.145  -0.085  -1.911  1.00  0.00           C  
HETATM   26  O6  UNL     1      -0.546  -0.180  -3.020  1.00  0.00           O  
HETATM   27  H1  UNL     1       1.243  -4.884  -0.293  1.00  0.00           H  
HETATM   28  H2  UNL     1      -0.479  -4.923   0.117  1.00  0.00           H  
HETATM   29  H3  UNL     1       0.781  -4.265   1.300  1.00  0.00           H  
HETATM   30  H4  UNL     1       1.337  -1.801   1.130  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.293  -2.255  -0.291  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.217  -0.923  -1.799  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.944   1.184  -2.379  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.479   3.037  -1.838  1.00  0.00           H  
HETATM   35  H9  UNL     1       3.572   1.853   2.218  1.00  0.00           H  
HETATM   36  H10 UNL     1       2.052  -0.000   1.721  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.067  -0.328   2.549  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.988   0.161   2.432  1.00  0.00           H  
HETATM   39  H13 UNL     1      -5.358   0.769   2.167  1.00  0.00           H  
HETATM   40  H14 UNL     1      -6.324   1.124  -0.062  1.00  0.00           H  
HETATM   41  H15 UNL     1      -4.891   0.864  -2.028  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3    4
CONECT    4    5   30   31
CONECT    5    6   15   32
CONECT    6    7    7   14
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   10   13
CONECT   10   11   11   12
CONECT   13   14   14   35
CONECT   14   36
CONECT   15   16   16   25
CONECT   16   17   18
CONECT   17   37
CONECT   18   19   19   23
CONECT   19   20   38
CONECT   20   21   21   39
CONECT   21   22   40
CONECT   22   23   23   41
CONECT   23   24
CONECT   24   25
CONECT   25   26   26
END

HMDB0243714
     RDKit          3D
(S)-Acenocoumarol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.4938    4.6307    0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2263    3.2832   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991    3.1810   -1.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025    2.1767    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    0.8443   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -0.1658    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7033   -0.5114    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139   -1.4294    1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449   -2.0254    1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -2.9675    1.6182 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2991   -3.5046    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4280   -3.2905    2.9467 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5619   -1.6860   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -0.7638   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    0.4276   -0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846   -0.4889   -1.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -0.9905   -2.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045   -0.8785   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0987   -1.7870   -1.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -2.1873   -1.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1373   -1.6896   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087   -0.7939    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2038   -0.3628    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426    0.4905    0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    0.9031    0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    1.7476    1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    5.4400   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512    4.8198    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    4.7501    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838    2.1389    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    2.4903   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9854    0.9087   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791   -0.0652    2.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -1.7057    2.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2960   -2.1488   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6963   -0.5204   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498   -0.7838   -2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5241   -2.1667   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -2.8947   -2.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1560   -2.0201   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0759   -0.4043    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 14  6  1  0
 25 15  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  CHG  2  10   1  12  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(alpha-(4'-Nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin	ChEBI
3-(alpha-(p-Nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin	ChEBI
3-(alpha-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin	ChEBI
3-(alpha-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarin	ChEBI
3-(alpha-p-Nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin	ChEBI
4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-one	ChEBI
4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one	ChEBI
Acenocoumarin	ChEBI
Acenocoumarolum	ChEBI
Acenocumarol	ChEBI
Acenocumarolo	ChEBI
Acenokumarin	ChEBI
Nicoumalone	ChEBI
Nicumalon	ChEBI
Nitrophenylacetylethyl-4-hydroxycoumarine	ChEBI
Nitrovarfarian	ChEBI
Nitrowarfarin	ChEBI
Mini-sintrom	Kegg
3-(a-(4'-Nitrophenyl)-b-acetylethyl)-4-hydroxycoumarin	Generator
3-(Α-(4'-nitrophenyl)-β-acetylethyl)-4-hydroxycoumarin	Generator
3-(a-(p-Nitrophenol)-b-acetylethyl)-4-hydroxycoumarin	Generator
3-(Α-(p-nitrophenol)-β-acetylethyl)-4-hydroxycoumarin	Generator
3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin	Generator
3-(Α-acetonyl-4-nitrobenzyl)-4-hydroxycoumarin	Generator
3-(a-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarin	Generator
3-(Α-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin	Generator
3-(a-p-Nitrophenyl-b-acetylethyl)-4-hydroxycoumarin	Generator
3-(Α-p-nitrophenyl-β-acetylethyl)-4-hydroxycoumarin	Generator
Ciba-geigy brand OF acenocoumarol	HMDB
Mini sintrom	HMDB
Novartis brand OF acenocoumarol	HMDB
Sinkumar	HMDB
Syncoumar	HMDB
Synthrom	HMDB
Acenocoumarol alliance brand	HMDB
Acenocoumarol novartis brand	HMDB
Alliance brand OF acenocoumarol	HMDB
Ciba geigy brand OF acenocoumarol	HMDB
MiniSintrom	HMDB
Syncumar	HMDB
Acenocoumarol ciba-geigy brand	HMDB
Sinthrome	HMDB
Sintrom	HMDB

Chemical Formula

C₁₉H₁₅NO₆

Average Molecular Weight

353.3255

Monoisotopic Molecular Weight

353.089937217

IUPAC Name

4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one

Traditional Name

acenocumarolo

CAS Registry Number

152-72-7

SMILES

CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O

InChI Identifier

InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3

InChI Key

VABCILAOYCMVPS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
Benzopyran
1-benzopyran
Nitrobenzene
Nitroaromatic compound
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
C-nitro compound
Organic nitro compound
Oxacycle
Organic oxoazanium
Organoheterocyclic compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-nitro compound (CHEBI:53766 )
methyl ketone (CHEBI:53766 )
hydroxycoumarin (CHEBI:53766 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015487)
Membrane (HMDB: HMDB0015487)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Acenocoumarol Action Pathway (PathBank: SMP0000269)

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticoagulant (HMDB: HMDB0015487)

EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor (HMDB: HMDB0015487)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	197 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.011 g/L	Not Available
LogP	1.98	SANGSTER (1994)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.68	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	5.79	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.18 m³·mol⁻¹	ChemAxon
Polarizability	34.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.905	31661259
DarkChem	[M-H]-	183.06	31661259
DeepCCS	[M+H]+	182.779	30932474
DeepCCS	[M-H]-	180.421	30932474
DeepCCS	[M-2H]-	214.625	30932474
DeepCCS	[M+Na]+	189.855	30932474
AllCCS	[M+H]+	181.7	32859911
AllCCS	[M+H-H2O]+	178.5	32859911
AllCCS	[M+NH4]+	184.7	32859911
AllCCS	[M+Na]+	185.5	32859911
AllCCS	[M-H]-	182.2	32859911
AllCCS	[M+Na-2H]-	181.6	32859911
AllCCS	[M+HCOO]-	181.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acenocoumarol	CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O	4278.3	Standard polar	33892256
Acenocoumarol	CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O	1704.5	Standard non polar	33892256
Acenocoumarol	CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O	3199.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acenocoumarol,1TMS,isomer #1	CC(=O)CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O	3213.3	Semi standard non polar	33892256
Acenocoumarol,1TMS,isomer #2	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3315.9	Semi standard non polar	33892256
Acenocoumarol,1TMS,isomer #3	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3236.5	Semi standard non polar	33892256
Acenocoumarol,2TMS,isomer #1	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3311.8	Semi standard non polar	33892256
Acenocoumarol,2TMS,isomer #1	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3046.6	Standard non polar	33892256
Acenocoumarol,2TMS,isomer #1	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3728.1	Standard polar	33892256
Acenocoumarol,2TMS,isomer #2	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3230.0	Semi standard non polar	33892256
Acenocoumarol,2TMS,isomer #2	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2921.6	Standard non polar	33892256
Acenocoumarol,2TMS,isomer #2	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3729.3	Standard polar	33892256
Acenocoumarol,1TBDMS,isomer #1	CC(=O)CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O	3491.6	Semi standard non polar	33892256
Acenocoumarol,1TBDMS,isomer #2	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3611.0	Semi standard non polar	33892256
Acenocoumarol,1TBDMS,isomer #3	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3540.1	Semi standard non polar	33892256
Acenocoumarol,2TBDMS,isomer #1	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3829.8	Semi standard non polar	33892256
Acenocoumarol,2TBDMS,isomer #1	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3498.9	Standard non polar	33892256
Acenocoumarol,2TBDMS,isomer #1	CC(=CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3827.7	Standard polar	33892256
Acenocoumarol,2TBDMS,isomer #2	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3740.5	Semi standard non polar	33892256
Acenocoumarol,2TBDMS,isomer #2	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3342.6	Standard non polar	33892256
Acenocoumarol,2TBDMS,isomer #2	C=C(CC(C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3835.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-4394000000-cee5104d5911648240f0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (1 TMS) - 70eV, Positive	splash10-0h90-9486300000-ff32bbb6638456fac0ab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acenocoumarol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acenocoumarol 10V, Positive-QTOF	splash10-0udi-0009000000-a9c658b6227fbe717786	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acenocoumarol 20V, Positive-QTOF	splash10-0a4r-0009000000-b7023b451fda1f0da396	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acenocoumarol 40V, Positive-QTOF	splash10-000i-3509000000-10dd28ff6a33134ff631	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acenocoumarol 10V, Negative-QTOF	splash10-0udi-1009000000-bb35e9834abd3581b7c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acenocoumarol 20V, Negative-QTOF	splash10-0udi-2009000000-0b9b626833d64db8299c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acenocoumarol 40V, Negative-QTOF	splash10-0a4i-9104000000-feadec6c8ab265c3c1b3	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Acenocoumarol Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01418	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01418	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01418

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10443441

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acenocoumarol

METLIN ID

Not Available

PubChem Compound

54676537

PDB ID

Not Available

ChEBI ID

53766

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ufer M: Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46. [PubMed:16372822 ]
Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. [PubMed:16611310 ]
Girard P, Nony P, Erhardtsen E, Delair S, Ffrench P, Dechavanne M, Boissel JP: Population pharmacokinetics of recombinant factor VIIa in volunteers anticoagulated with acenocoumarol. Thromb Haemost. 1998 Jul;80(1):109-13. [PubMed:9684795 ]
Cesar JM, Garcia-Avello A, Navarro JL, Herraez MV: Aging and oral anticoagulant therapy using acenocoumarol. Blood Coagul Fibrinolysis. 2004 Oct;15(8):673-6. [PubMed:15613922 ]
Lengyel M: [Warfarin or acenocoumarol is better in the anticoagulant treatment of chronic atrial fibrillation?]. Orv Hetil. 2004 Dec 26;145(52):2619-21. [PubMed:15724697 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Ufer M: Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46. [PubMed:16372822 ]
Morales-Molina JA, Arrebola MA, Robles PA, Mangana JC: Possible interaction between topical terbinafine and acenocoumarol. Ann Pharmacother. 2009 Nov;43(11):1911-2. doi: 10.1345/aph.1M299. Epub 2009 Oct 20. [PubMed:19843835 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Stehle S, Kirchheiner J, Lazar A, Fuhr U: Pharmacogenetics of oral anticoagulants: a basis for dose individualization. Clin Pharmacokinet. 2008;47(9):565-94. [PubMed:18698879 ]
Bodin L, Verstuyft C, Tregouet DA, Robert A, Dubert L, Funck-Brentano C, Jaillon P, Beaune P, Laurent-Puig P, Becquemont L, Loriot MA: Cytochrome P450 2C9 (CYP2C9) and vitamin K epoxide reductase (VKORC1) genotypes as determinants of acenocoumarol sensitivity. Blood. 2005 Jul 1;106(1):135-40. Epub 2005 Mar 24. [PubMed:15790782 ]
Gonzalez-Conejero R, Corral J, Roldan V, Ferrer F, Sanchez-Serrano I, Sanchez-Blanco JJ, Marin F, Vicente V: The genetic interaction between VKORC1 c1173t and calumenin a29809g modulates the anticoagulant response of acenocoumarol. J Thromb Haemost. 2007 Aug;5(8):1701-6. Epub 2007 May 21. [PubMed:17596133 ]
Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. [PubMed:16611310 ]
Rettie AE, Farin FM, Beri NG, Srinouanprachanh SL, Rieder MJ, Thijssen HH: A case study of acenocoumarol sensitivity and genotype-phenotype discordancy explained by combinations of polymorphisms in VKORC1 and CYP2C9. Br J Clin Pharmacol. 2006 Nov;62(5):617-20. Epub 2006 Jul 21. [PubMed:16869821 ]
Schalekamp T, Brasse BP, Roijers JF, Chahid Y, van Geest-Daalderop JH, de Vries-Goldschmeding H, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and acenocoumarol anticoagulation status: interaction between both genotypes affects overanticoagulation. Clin Pharmacol Ther. 2006 Jul;80(1):13-22. [PubMed:16815313 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

5. Vitamin K epoxide reductase complex subunit 1

General function:: Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:: Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:: VKORC1
Uniprot ID:: Q9BQB6
Molecular weight:: 18234.3

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Bodin L, Verstuyft C, Tregouet DA, Robert A, Dubert L, Funck-Brentano C, Jaillon P, Beaune P, Laurent-Puig P, Becquemont L, Loriot MA: Cytochrome P450 2C9 (CYP2C9) and vitamin K epoxide reductase (VKORC1) genotypes as determinants of acenocoumarol sensitivity. Blood. 2005 Jul 1;106(1):135-40. Epub 2005 Mar 24. [PubMed:15790782 ]
Gonzalez-Conejero R, Corral J, Roldan V, Ferrer F, Sanchez-Serrano I, Sanchez-Blanco JJ, Marin F, Vicente V: The genetic interaction between VKORC1 c1173t and calumenin a29809g modulates the anticoagulant response of acenocoumarol. J Thromb Haemost. 2007 Aug;5(8):1701-6. Epub 2007 May 21. [PubMed:17596133 ]
Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. [PubMed:16611310 ]
Rettie AE, Farin FM, Beri NG, Srinouanprachanh SL, Rieder MJ, Thijssen HH: A case study of acenocoumarol sensitivity and genotype-phenotype discordancy explained by combinations of polymorphisms in VKORC1 and CYP2C9. Br J Clin Pharmacol. 2006 Nov;62(5):617-20. Epub 2006 Jul 21. [PubMed:16869821 ]
Schalekamp T, Brasse BP, Roijers JF, Chahid Y, van Geest-Daalderop JH, de Vries-Goldschmeding H, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and acenocoumarol anticoagulation status: interaction between both genotypes affects overanticoagulation. Clin Pharmacol Ther. 2006 Jul;80(1):13-22. [PubMed:16815313 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Acenocoumarol (HMDB0015487)

MOL for HMDB0015487 (Acenocoumarol)

3D MOL for HMDB0015487 (Acenocoumarol)

3D SDF for HMDB0015487 (Acenocoumarol)

3D-SDF for HMDB0015487 (Acenocoumarol)

PDB for HMDB0015487 (Acenocoumarol)

3D PDB for HMDB0015487 (Acenocoumarol)

SMILES for HMDB0015487 (Acenocoumarol)

INCHI for HMDB0015487 (Acenocoumarol)

Structure for HMDB0015487 (Acenocoumarol)

3D Structure for HMDB0015487 (Acenocoumarol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References