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Showing metabocard for Coumarin (HMDB0001218)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:32 UTC
HMDB IDHMDB0001218
Secondary Accession Numbers
  • HMDB01218
Metabolite Identification
Common NameCoumarin
DescriptionCoumarin belongs to the class of chemicals known as chromenones. Specifically it is a chromenone having the keto group located at the 2-position. A chromenone is a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain forming a second six-membered heterocycle that shares two carbons with the benzene ring. Coumarin is also described as a benzopyrone and is considered as a lactone. Coumarin is a colorless crystalline solid with a bitter taste and sweet odor resembling the scent of vanilla or the scent of newly-mowed or recently cut hay. It is a chemical poison found in many plants where it may serve as a chemical defense against predators. Coumarin occurs naturally in many plants and foods such as the tonka bean, woodruff, bison grass, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, tobacco, wine, and other foodstuffs. Coumarin concentrations in these plants, spices, and foods range from <1 mg/kg in celery, to 7000 mg/kg in cinnamon, and up to 87,000 mg/kg in cassia. An estimate of human exposure to coumarin from the diet has been calculated to be 0.02 mg/kg/day. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5% To 6.4% In fine fragrances to <0.01% In detergents. An estimate for systemic exposure of humans from the use of fragranced cosmetic products is 0.04 mg/kg BW/day, assuming complete dermal penetration. The use of coumarin as a food additive was banned by the FDA in 1954 based on reports of hepatotoxicity in rats. It has clinical value as the precursor for several anticoagulants, notably warfarin. Coumarins, as a class, are comprised of numerous naturally occurring benzo-alpha-pyrone compounds with important and diverse physiological activities. Due to its potential hepatotoxic effects in humans, the European Commission restricted coumarin from naturals as a direct food additive to 2 mg/kg food/day, with exceptions granting higher levels for alcoholic beverages, caramel, chewing gum, and certain 'traditional foods'. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. Exposure ranges from 11 mg/day for consumption of natural food ingredients to 7 g/day following clinical administration. Although adverse effects in humans following coumarin exposure are rare, and only associated with clinical doses, recent evidence indicates coumarin causes liver tumors in rats and mice and Clara cell toxicity and lung tumors in mice. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity/carcinogenicity and its human relevance. These investigations have revealed significant species differences in coumarin metabolism and toxicity such that the mechanism of coumarin induced effects in rodents, and the relevance of these findings for the safety assessment of coumarin exposure in humans are now better understood. In October 2004, the European Food Safety Authority (EFSA, 2004) reviewed coumarin to establish a tolerable daily intake (TDI) in foods. EFSA issued an opinion indicating that coumarin is not genotoxic, and that a threshold approach to safety assessment was most appropriate. EFSA recommended a TDI of 0 to 0.1 Mg/kg BW/day. Including dietary contributions, the total human exposure is estimated to be 0.06 Mg/kg/day. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. Unlike coumadin and other coumarin derivatives, coumarin has no anti-coagulant activity. However, at low doses (typically 7 to 10 mg/day), coumarin has been used as a 'venotonic' to promote vein health and small venule blood flow. Additionally, coumarin has been used clinically in the treatment of high-protein lymphedema arising from various etiologies. (PMID: 16203076 ).
Structure
Data?1676999732
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001218 (Coumarin)

Coumarin
  Mrv1652309042000192D          

 11 12  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0001218 (Coumarin)

HMDB0001218
     RDKit          3D
Coumarin
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.2947   -1.7915    0.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110   -1.0135    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    0.3496    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    1.1487    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    0.5421   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    1.3085   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2577    0.7316   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980   -0.6414   -0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551   -1.4055   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114   -0.8323    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0973   -1.5416    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4781    0.8141    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4469    2.2083    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9047    2.3933   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734    1.3371   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.1126   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -2.4950   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  2  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0001218 (Coumarin)

Coumarin
  Mrv1652309042000192D          

 11 12  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001218

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1OC2=CC=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H

> <INCHI_KEY>
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N

> <FORMULA>
C9H6O2

> <MOLECULAR_WEIGHT>
146.145

> <EXACT_MASS>
146.036779433

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.362215597078222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2H-chromen-2-one

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.783359615333333

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.940141845991088

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
41.54860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coumarin

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001218 (Coumarin)

HMDB0001218
     RDKit          3D
Coumarin
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.2947   -1.7915    0.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110   -1.0135    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    0.3496    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    1.1487    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    0.5421   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    1.3085   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2577    0.7316   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980   -0.6414   -0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551   -1.4055   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114   -0.8323    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0973   -1.5416    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4781    0.8141    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4469    2.2083    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9047    2.3933   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734    1.3371   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.1126   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -2.4950   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  2  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0001218 (Coumarin)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Coumarin                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0001218 (Coumarin)

COMPND    HMDB0001218
HETATM    1  O1  UNL     1      -3.295  -1.791   0.329  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.311  -1.014   0.225  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.508   0.350   0.206  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.392   1.149   0.089  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.133   0.542  -0.003  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.007   1.309  -0.121  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.258   0.732  -0.213  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.398  -0.641  -0.188  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.255  -1.405  -0.070  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.011  -0.832   0.023  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.097  -1.542   0.135  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.478   0.814   0.276  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.447   2.208   0.066  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.905   2.393  -0.140  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.173   1.337  -0.307  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.377  -1.113  -0.260  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.298  -2.495  -0.045  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   12
CONECT    4    5   13
CONECT    5    6    6   10
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   11
END
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SMILES for HMDB0001218 (Coumarin)

O=C1OC2=CC=CC=C2C=C1
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INCHI for HMDB0001218 (Coumarin)

InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,2-BenzopyroneChEBI
2-Propenoic acid, 3-(2-hydroxyphenyl)-, D-lactoneChEBI
2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactoneChEBI
2H-1-Benzopyran-2-oneChEBI
2H-Benzo[b]pyran-2-oneChEBI
5,6-Benzo-2-pyroneChEBI
Benzo-a-pyroneChEBI
Benzo-alpha-pyroneChEBI
cis-O-Coumarinic acid lactoneChEBI
CoumarineChEBI
Coumarinic anhydrideChEBI
CumarinChEBI
O-Hydroxycinnamic acid delta-lactoneChEBI
O-Hydroxycinnamic acid lactoneChEBI
RattexChEBI
Tonka bean camphorChEBI
Venalot monoKegg
2-Propenoate, 3-(2-hydroxyphenyl)-, D-lactoneGenerator
2-Propenoate, 3-(2-hydroxyphenyl)-, delta-lactoneGenerator
2-Propenoate, 3-(2-hydroxyphenyl)-, δ-lactoneGenerator
2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactoneGenerator
Benzo-α-pyroneGenerator
cis-O-Coumarinate lactoneGenerator
O-Hydroxycinnamate delta-lactoneGenerator
O-Hydroxycinnamate δ-lactoneGenerator
O-Hydroxycinnamic acid δ-lactoneGenerator
O-Hydroxycinnamate lactoneGenerator
5,6-Benzo-alpha-pyroneMeSH
1, 2-BenzopyroneHMDB
2-oxo-1,2-BenzopyranHMDB
2-oxo-2H-1-BenzopyranHMDB
2H-Chromen-2-oneHMDB
2H-Chromen-2-one (acd/name 4.0)HMDB
KumarinHMDB
O-Hydroxycinnamic lactoneHMDB
O-Hydroxyzimtsaure-lactonHMDB
{2h-benzo[b]pyran-2-one}HMDB
Chemical FormulaC9H6O2
Average Molecular Weight146.145
Monoisotopic Molecular Weight146.036779433
IUPAC Name2H-chromen-2-one
Traditional Namecoumarin
CAS Registry Number91-64-5
SMILES
O=C1OC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
InChI KeyZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point71 °CNot Available
Boiling Point297.00 to 301.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.9 mg/mLNot Available
LogP2.23Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available122.248http://allccs.zhulab.cn/database/detail?ID=AllCCS00001384
Predicted Molecular Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP1.72ALOGPS
logP1.78ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.55 m³·mol⁻¹ChemAxon
Polarizability14.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.14831661259
DarkChem[M-H]-127.03531661259
AllCCS[M+H]+127.9532859911
AllCCS[M-H]-126.17932859911
DeepCCS[M+H]+130.79330932474
DeepCCS[M-H]-127.9330932474
DeepCCS[M-2H]-164.48630932474
DeepCCS[M+Na]+139.87330932474
AllCCS[M+H]+127.932859911
AllCCS[M+H-H2O]+123.132859911
AllCCS[M+NH4]+132.532859911
AllCCS[M+Na]+133.832859911
AllCCS[M-H]-126.232859911
AllCCS[M+Na-2H]-126.932859911
AllCCS[M+HCOO]-127.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.52 minutes32390414
Predicted by Siyang on May 30, 202213.1524 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.95 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1794.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid508.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid186.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid323.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid211.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid468.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid504.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)165.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1066.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid389.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1228.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid347.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid338.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate479.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA378.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water61.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CoumarinO=C1OC2=CC=CC=C2C=C12312.9Standard polar33892256
CoumarinO=C1OC2=CC=CC=C2C=C11370.1Standard non polar33892256
CoumarinO=C1OC2=CC=CC=C2C=C11475.2Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04665
Phenol Explorer Compound ID635
FooDB IDFDB011938
KNApSAcK IDC00002460
Chemspider ID13848793
KEGG Compound IDC05851
BioCyc IDCOUMARIN
BiGG ID46647
Wikipedia LinkCoumarin
METLIN ID3525
PubChem Compound323
PDB IDNot Available
ChEBI ID28794
Food Biomarker OntologyNot Available
VMH IDCOUMARIN
MarkerDB IDNot Available
Good Scents IDrw1003832
References
Synthesis ReferenceHuang, Zhong-jing. Synthesis of coumarin under microwave irradiation. Guangxi Huagong (2001), 30(3), 1-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Felter SP, Vassallo JD, Carlton BD, Daston GP: A safety assessment of coumarin taking into account species-specificity of toxicokinetics. Food Chem Toxicol. 2006 Apr;44(4):462-75. Epub 2005 Oct 3. [PubMed:16203076 ]

Enzymes

Enzyme Details
1. Cytochrome P450 2A13
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity.
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Molecular weight:
56687.095
Enzyme Details
2. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005