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Showing NP-Card for 7-Hydroxycoumarin (NP0331763)

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Record Information
Version1.0
Created at2023-08-11 16:01:12 UTC
Updated at2024-05-13 01:17:35 UTC
NP-MRD IDNP0331763
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-Hydroxycoumarin
DescriptionUmbelliferone, also known as 7-hydroxycoumarin or hydrangin, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Umbelliferone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Umbelliferone is found, on average, in the highest concentration within anises and beers. Umbelliferone has also been detected, but not quantified in, several different foods, such as common buckwheats, sweet oranges, red beetroots, kohlrabis, and wild celeries. This could make umbelliferone a potential biomarker for the consumption of these foods. It was first documented in 2013 (PMID: 23224618). A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0331763 (7-Hydroxycoumarin)


  Mrv1652311132100522D          

 12 13  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
    4.2868   -0.0000    0.0000 O   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  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
M  END
Download

3D MOL for NP0331763 (7-Hydroxycoumarin)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -3.5567    1.7318    0.2418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    0.9796    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449   -0.3633    0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303   -1.1788    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3866   -0.6287    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7594   -1.3953    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -0.8634   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389    0.4901   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3872    1.0523   -0.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927    1.2570   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2551    0.7257   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3376    1.4745   -0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7077   -0.7917    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -2.2433    0.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -2.4646    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -1.4926   -0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9755    1.3885    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0866    2.3224   -0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2 12  1  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
 11  5  1  0
 10 18  1  0
  9 17  1  0
  7 16  1  0
  6 15  1  0
  4 14  1  0
  3 13  1  0
M  END
Download

3D SDF for NP0331763 (7-Hydroxycoumarin)


  Mrv1652311132100522D          

 12 13  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
    4.2868   -0.0000    0.0000 O   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  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H

> <INCHI_KEY>
ORHBXUUXSCNDEV-UHFFFAOYSA-N

> <FORMULA>
C9H6O3

> <MOLECULAR_WEIGHT>
162.144

> <EXACT_MASS>
162.031694053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.369727808099249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.4797942936666666

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8357602201831815

> <JCHEM_PKA_STRONGEST_BASIC>
-6.940639034952481

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.5295

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
umbelliferone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0331763 (7-Hydroxycoumarin)

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PDB for NP0331763 (7-Hydroxycoumarin)
HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         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  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0331763 (7-Hydroxycoumarin)
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SMILES for NP0331763 (7-Hydroxycoumarin)
OC1=CC2=C(C=C1)C=CC(=O)O2
Download
INCHI for NP0331763 (7-Hydroxycoumarin)
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
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View in JSmol
Synonyms
ValueSource
7-Hydroxy-2H-1-benzopyran-2-oneChEBI
7-HydroxycoumarinChEBI
beta-UmbelliferoneChEBI
HydranginChEBI
SkimmetinChEBI
b-UmbelliferoneGenerator
Β-umbelliferoneGenerator
7-Hydroxy-2H-chromen-2-oneHMDB
7-Hydroxy-coumarinHMDB
7-Hydroxycoumarin sulfateHMDB
7-Hydroxycoumarin sulphateHMDB
7-Hydroxycoumarin, 14C-labeledHMDB
7-OxycoumarinHMDB
beta -UmbelliferoneHMDB
HydrangineHMDB
SkimmetineHMDB
UmbelliferonHMDB
Umbelliferone (hydrangin, skimmetin)HMDB
Chemical FormulaC9H6O3
Average Mass162.1440 Da
Monoisotopic Mass162.03169 Da
IUPAC Name7-hydroxy-2H-chromen-2-one
Traditional Nameumbelliferone
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(C=C1)C=CC(=O)O2
InChI Identifier
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChI KeyORHBXUUXSCNDEV-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D_DEPT NMR13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D_DEPT NMR13C NMR Spectrum (1D, 101 MHz, C2D6OS, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, C2D6OS, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D_DEPT NMR13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)blanco-carcache.1@buckeyemail.osu,eduNot AvailableNot Available2024-05-12View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-11View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-11View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
ovoidea
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassHydroxycoumarins  
Direct Parent7-hydroxycoumarins  
Alternative Parents
Substituents
  • 7-hydroxycoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.85ALOGPS
logP1.48ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.84ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.53 m³·mol⁻¹ChemAxon
Polarizability15.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029865  
DrugBank IDNot Available
Phenol Explorer Compound ID641  
FoodDB IDFDB001094  
KNApSAcK IDC00002503  
Chemspider ID4444774  
KEGG Compound IDC09315  
BioCyc IDCPD-8186  
BiGG IDNot Available
Wikipedia LinkUmbelliferone  
METLIN IDNot Available
PubChem Compound5281426  
PDB ID07L  
ChEBI ID27510  
Good Scents IDNot Available
References
General References
  1. Gok E: Investigation of binding properties of umbelliferone (7hydroxycoumarin) to lysozyme. J Fluoresc. 2013 Mar;23(2):333-8. doi: 10.1007/s10895-012-1151-0. Epub 2012 Dec 8. [PubMed:23224618  ] 
  1. Blanco Carcache PJ, Anaya Eugenio GD, Ninh TN, Moore CE, Rivera-Chavez J, Ren Y, Soejarto DD, Kinghorn AD: Cytotoxic constituents of Glycosmis ovoidea collected in Vietnam. Fitoterapia. 2022 Oct;162:105265. doi: 10.1016/j.fitote.2022.105265. Epub 2022  Aug 10. [PubMed:35963484  ]