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Showing NP-Card for Oxyhumulinic acid (NP0336814)

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Record Information
Version2.0
Created at2024-09-11 07:55:57 UTC
Updated at2024-09-11 07:55:58 UTC
NP-MRD IDNP0336814
Secondary Accession NumbersNone
Natural Product Identification
Common NameOxyhumulinic acid
DescriptionOxyhumulinic acid is also known as oxyhumulinate. Oxyhumulinic acid was first documented in 2014 (PMID: 25354357). Based on a literature review very few articles have been published on Oxyhumulinic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336814 (Oxyhumulinic acid)


  Mrv2104 05262310282D          

 20 20  0  0  0  0            999 V2000
    1.1619    3.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    3.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
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3D MOL for NP0336814 (Oxyhumulinic acid)

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3D SDF for NP0336814 (Oxyhumulinic acid)

  Mrv2104 05262310282D          

 20 20  0  0  0  0            999 V2000
    1.1619    3.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    3.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C1=C(O)C(O)C(O)(CC=C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1/C15H22O5/c1-8(2)5-6-15(20)13(18)11(12(17)14(15)19)10(16)7-9(3)4/h5,9,14,17,19-20H,6-7H2,1-4H3

> <INCHI_KEY>
QSHUUGSBRMSXKV-UHFFFAOYNA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.096121236171285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclopent-2-en-1-one

> <JCHEM_LOGP>
1.655397568

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.293299339369243

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1065248641388763

> <JCHEM_PKA_STRONGEST_BASIC>
-3.885378803690752

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
76.5715

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336814 (Oxyhumulinic acid)
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PDB for NP0336814 (Oxyhumulinic acid)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       2.169   7.298   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.151   5.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.268  -5.595   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.426  -4.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.614   4.689   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.645   5.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.029   3.224   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    9                                                            
CONECT    5    6    8                                                       
CONECT    6    5   15                                                       
CONECT    7    9   10                                                       
CONECT    8    1    2    5                                                  
CONECT    9    3    4    7                                                  
CONECT   10    7   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   14   17                                                  
CONECT   13   11   15   18                                                  
CONECT   14   12   15   19                                                  
CONECT   15    6   13   14   20                                             
CONECT   16   10                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

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3D PDB for NP0336814 (Oxyhumulinic acid)
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SMILES for NP0336814 (Oxyhumulinic acid)
CC(C)CC(=O)C1=C(O)C(O)C(O)(CC=C(C)C)C1=O
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INCHI for NP0336814 (Oxyhumulinic acid)
InChI=1/C15H22O5/c1-8(2)5-6-15(20)13(18)11(12(17)14(15)19)10(16)7-9(3)4/h5,9,14,17,19-20H,6-7H2,1-4H3
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Synonyms
ValueSource
OxyhumulinateGenerator
Chemical FormulaC15H22O5
Average Mass282.3360 Da
Monoisotopic Mass282.14672 Da
IUPAC Name3,4,5-trihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclopent-2-en-1-one
Traditional Name3,4,5-trihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclopent-2-en-1-one
CAS Registry NumberNot Available
SMILES
CC(C)CC(=O)C1=C(O)C(O)C(O)(CC=C(C)C)C1=O
InChI Identifier
InChI=1/C15H22O5/c1-8(2)5-6-15(20)13(18)11(12(17)14(15)19)10(16)7-9(3)4/h5,9,14,17,19-20H,6-7H2,1-4H3
InChI KeyQSHUUGSBRMSXKV-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAcyloins  
Alternative Parents
Substituents
  • Acyloin
    • 

  • Vinylogous acid
    • 

  • Tertiary alcohol
    • 

  • Cyclic ketone
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • 1,2-diol
    • 

  • Polyol
    • 

  • Enol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP1.66ChemAxon
pKa (Strongest Acidic)1.11ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.57 m³·mol⁻¹ChemAxon
Polarizability30.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Taniguchi Y, Taniguchi H, Yamada M, Matsukura Y, Koizumi H, Furihata K, Shindo K: Analysis of the components of hard resin in hops (Humulus lupulus L.) and structural elucidation of their transformation products formed during the brewing process. J Agric Food Chem. 2014 Nov 26;62(47):11602-12. doi: 10.1021/jf504394h. Epub 2014  Nov 12. [PubMed:25354357  ]