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Showing NP-Card for Osthenol (NP0047865)

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Record Information
Version2.0
Created at2022-03-17 20:47:13 UTC
Updated at2022-03-17 20:47:14 UTC
NP-MRD IDNP0047865
Secondary Accession NumbersNone
Natural Product Identification
Common NameOsthenol
DescriptionOsthenol 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. Osthenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Osthenol has been detected, but not quantified in, several different foods, such as angelica, fennels, green vegetables, and wild celeries. This could make osthenol a potential biomarker for the consumption of these foods. Osthenol is found in Angelica dahurica, Angelica pubescens, Citrus medica, Citrus paradisi, Citrus sulcata, Feroniella lucida, Hansenia weberbaueriana, Haplophyllum patavinum, Heracleum candicans, Heracleum candicans WALL. , Juniperus chinensis, Limonia acidissima, Melicope semecarpifolia, Notopterygium incisum , Ostericum grosseserratum, Phellodendron amurense, Phellodendron amurense var.wilsonii , Prangos ferulacea, Prangos uloptera and Zanthoxylum beecheyanum. Osthenol was first documented in 2008 (PMID: 18386483). A hydroxycoumarin that is umbelliferone in which the hydrogen at position 8 has been replaced by a prenyl group (PMID: 24354545) (PMID: 26552172) (PMID: 20931624) (PMID: 26918393).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047865 (Osthenol)


  Mrv0541 05061307362D          

 17 18  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  2  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
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3D MOL for NP0047865 (Osthenol)

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3D SDF for NP0047865 (Osthenol)

  Mrv0541 05061307362D          

 17 18  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  2  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3

> <INCHI_KEY>
RAKJVIPCCGXHHS-UHFFFAOYSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.2592

> <EXACT_MASS>
230.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.633239155375353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
3.2083612930000003

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.642400845567916

> <JCHEM_PKA_STRONGEST_BASIC>
-6.941572258614706

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.7723

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-8-(3-methylbut-2-en-1-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047865 (Osthenol)
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PDB for NP0047865 (Osthenol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    6    9                                                       
CONECT    4    7   10                                                       
CONECT    5    8   10                                                       
CONECT    6    3   11                                                       
CONECT    7    4   12                                                       
CONECT    8    5   13                                                       
CONECT    9    1    2    3                                                  
CONECT   10    4    5   14                                                  
CONECT   11    6   12   14                                                  
CONECT   12    7   11   15                                                  
CONECT   13    8   16   17                                                  
CONECT   14   10   11   17                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

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3D PDB for NP0047865 (Osthenol)
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SMILES for NP0047865 (Osthenol)
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2
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INCHI for NP0047865 (Osthenol)
InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3
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View in JSmol
Synonyms
ValueSource
7-Hydroxy-8-(3-methyl-but-2-enyl)coumarinChEBI
7-Hydroxy-8-prenylcoumarinChEBI
8-(3-Methylbut-2-en-1-yl)umbelliferoneChEBI
8-PrenylumbelliferoneChEBI
7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-oneHMDB
7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ciHMDB
Chemical FormulaC14H14O3
Average Mass230.2592 Da
Monoisotopic Mass230.09429 Da
IUPAC Name7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
Traditional Name7-hydroxy-8-(3-methylbut-2-en-1-yl)chromen-2-one
CAS Registry Number484-14-0
SMILES
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2
InChI Identifier
InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3
InChI KeyRAKJVIPCCGXHHS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica dahuricaLOTUS Database
Angelica keiskeiFooDB
Angelica pubescensLOTUS Database
Apium graveolensFooDB
Citrus medicaLOTUS Database
Citrus paradisiLOTUS Database
Citrus sulcataLOTUS Database
Feroniella lucidaLOTUS Database
Foeniculum vulgareFooDB
Hansenia weberbauerianaLOTUS Database
Haplophyllum patavinumPlant
Heracleum candicansLOTUS Database
Heracleum candicans WALL.Plant
Juniperus chinensisLOTUS Database
Limonia acidissimaLOTUS Database
Melicope semecarpifoliaPlant
Notopterygium incisumPlant
Ostericum grosseserratumLOTUS Database
Phellodendron amurenseLOTUS Database
Phellodendron amurense var.wilsoniiPlant
Prangos ferulaceaLOTUS Database
Prangos ulopteraLOTUS Database
Zanthoxylum beecheyanumLOTUS Database
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
logP3.24ALOGPS
logP3.21ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.64ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.77 m³·mol⁻¹ChemAxon
Polarizability24.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034130  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012404  
KNApSAcK IDC00030900  
Chemspider ID4478430  
KEGG Compound IDC18080  
BioCyc IDCPD-9838  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320318  
PDB IDNot Available
ChEBI ID81485  
Good Scents IDNot Available
References
General References
  1. Karamat F, Olry A, Munakata R, Koeduka T, Sugiyama A, Paris C, Hehn A, Bourgaud F, Yazaki K: A coumarin-specific prenyltransferase catalyzes the crucial biosynthetic reaction for furanocoumarin formation in parsley. Plant J. 2014 Feb;77(4):627-38. doi: 10.1111/tpj.12409. Epub 2014 Jan 24. [PubMed:24354545  ] 
  2. Deng GG, Yang XW, Zhang YB, Xu W, Wei W, Chen TL: [Chemical constituents from lipophilic parts in roots of Angelica dahurica var. formosana cv. Chuanbaizhi]. Zhongguo Zhong Yao Za Zhi. 2015 Jun;40(11):2148-56. [PubMed:26552172  ] 
  3. Montagner C, de Souza SM, Groposoa C, Delle Monache F, Smania EF, Smania A Jr: Antifungal activity of coumarins. Z Naturforsch C J Biosci. 2008 Jan-Feb;63(1-2):21-8. doi: 10.1515/znc-2008-1-205. [PubMed:18386483  ] 
  4. Xie Y, Zhao W, Zhou T, Fan G, Wu Y: An efficient strategy based on MAE, HPLC-DAD-ESI-MS/MS and 2D-prep-HPLC-DAD for the rapid extraction, separation, identification and purification of five active coumarin components from Radix Angelicae Dahuricae. Phytochem Anal. 2010 Sep-Oct;21(5):473-82. doi: 10.1002/pca.1222. [PubMed:20931624  ] 
  5. Munakata R, Olry A, Karamat F, Courdavault V, Sugiyama A, Date Y, Krieger C, Silie P, Foureau E, Papon N, Grosjean J, Yazaki K, Bourgaud F, Hehn A: Molecular evolution of parsnip (Pastinaca sativa) membrane-bound prenyltransferases for linear and/or angular furanocoumarin biosynthesis. New Phytol. 2016 Jul;211(1):332-44. doi: 10.1111/nph.13899. Epub 2016 Feb 25. [PubMed:26918393  ]