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Showing NP-Card for Hericenone A (NP0048366)

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Record Information
Version2.0
Created at2022-03-17 20:55:21 UTC
Updated at2022-03-17 20:55:21 UTC
NP-MRD IDNP0048366
Secondary Accession NumbersNone
Natural Product Identification
Common NameHericenone A
DescriptionHericenone A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Hericenone A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Hericenone A has been detected, but not quantified in, mushrooms. Hericenone A is found in Hericium erinaceum . This could make hericenone a a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048366 (Hericenone A)


  Mrv0541 05061308462D          

 24 25  0  0  0  0            999 V2000
    3.3523   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
 18 16  2  0  0  0  0
 19 15  1  0  0  0  0
 20 13  2  0  0  0  0
 21 18  1  0  0  0  0
 22 19  2  0  0  0  0
 23  4  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
Download

3D MOL for NP0048366 (Hericenone A)

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3D SDF for NP0048366 (Hericenone A)

  Mrv0541 05061308462D          

 24 25  0  0  0  0            999 V2000
    3.3523   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
 18 16  2  0  0  0  0
 19 15  1  0  0  0  0
 20 13  2  0  0  0  0
 21 18  1  0  0  0  0
 22 19  2  0  0  0  0
 23  4  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O5/c1-11(2)7-13(20)8-12(3)5-6-14-17(23-4)9-15-16(18(14)21)10-24-19(15)22/h5,7,9,21H,6,8,10H2,1-4H3/b12-5+

> <INCHI_KEY>
IDSCVDJWBRGNKG-LFYBBSHMSA-N

> <FORMULA>
C19H22O5

> <MOLECULAR_WEIGHT>
330.375

> <EXACT_MASS>
330.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.89210281439617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.6355221893333334

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.368428725274441

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.004235309674947

> <JCHEM_PKA_STRONGEST_BASIC>
-4.307900945664196

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
93.74549999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-3H-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048366 (Hericenone A)
Download
PDB for NP0048366 (Hericenone A)
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       6.258 -11.313   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   23                                                            
CONECT    5    6   12                                                       
CONECT    6    5   14                                                       
CONECT    7   11   13                                                       
CONECT    8   12   13                                                       
CONECT    9   15   17                                                       
CONECT   10   16   24                                                       
CONECT   11    1    2    7                                                  
CONECT   12    3    5    8                                                  
CONECT   13    7    8   20                                                  
CONECT   14    6   17   18                                                  
CONECT   15    9   16   19                                                  
CONECT   16   10   15   18                                                  
CONECT   17    9   14   23                                                  
CONECT   18   14   16   21                                                  
CONECT   19   15   22   24                                                  
CONECT   20   13                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23    4   17                                                       
CONECT   24   10   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

Download
3D PDB for NP0048366 (Hericenone A)
Download
SMILES for NP0048366 (Hericenone A)
COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1
Download
INCHI for NP0048366 (Hericenone A)
InChI=1S/C19H22O5/c1-11(2)7-13(20)8-12(3)5-6-14-17(23-4)9-15-16(18(14)21)10-24-19(15)22/h5,7,9,21H,6,8,10H2,1-4H3/b12-5+
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View in JSmol
Synonyms
ValueSource
Hericenone aMeSH
Chemical FormulaC19H22O5
Average Mass330.3750 Da
Monoisotopic Mass330.14672 Da
IUPAC Name5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-1,3-dihydro-2-benzofuran-1-one
Traditional Name5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-3H-2-benzofuran-1-one
CAS Registry Number126654-52-2
SMILES
COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1
InChI Identifier
InChI=1S/C19H22O5/c1-11(2)7-13(20)8-12(3)5-6-14-17(23-4)9-15-16(18(14)21)10-24-19(15)22/h5,7,9,21H,6,8,10H2,1-4H3/b12-5+
InChI KeyIDSCVDJWBRGNKG-LFYBBSHMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Hericium erinaceusFungi
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene lactones  
Alternative Parents
Substituents
  • Terpene lactone
    • 

  • Monoterpenoid
    • 

  • Isobenzofuranone
    • 

  • Aromatic monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Phthalide
    • 

  • Isocoumaran
    • 

  • Anisole
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Enone
    • 

  • Acryloyl-group
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.74ALOGPS
logP3.64ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity93.75 m³·mol⁻¹ChemAxon
Polarizability34.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035879  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014660  
KNApSAcK IDC00023975  
Chemspider ID9957159  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11782478  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References