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Showing NP-Card for Humulol (NP0337888)

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Record Information
Version2.0
Created at2024-09-11 12:53:50 UTC
Updated at2024-09-11 12:53:51 UTC
NP-MRD IDNP0337888
Secondary Accession NumbersNone
Natural Product Identification
Common NameHumulol
DescriptionHumulol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Humulol was first documented in 2021 (PMID: 34263932). Based on a literature review very few articles have been published on Humulol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337888 (Humulol)


  Mrv2104 05262315262D          

 16 16  0  0  0  0            999 V2000
   -3.6830   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975   -4.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686   -4.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541   -6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -4.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6830   -6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3340   -6.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090   -6.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -7.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8836   -7.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1120   -6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541   -3.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686   -3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  9  2  0  0  0  0
  1  4  1  0  0  0  0
  5  4  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
 11  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
M  END
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3D MOL for NP0337888 (Humulol)

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3D SDF for NP0337888 (Humulol)

  Mrv2104 05262315262D          

 16 16  0  0  0  0            999 V2000
   -3.6830   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975   -4.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686   -4.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541   -6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -4.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6830   -6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3340   -6.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090   -6.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -7.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8836   -7.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1120   -6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541   -3.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686   -3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  9  2  0  0  0  0
  1  4  1  0  0  0  0
  5  4  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
 11  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CC(C)(C)\C=C\CC(C)(O)CCC1

> <INCHI_IDENTIFIER>
InChI=1/C15H26O/c1-13-7-5-10-15(4,16)11-6-9-14(2,3)12-8-13/h6,8-9,16H,5,7,10-12H2,1-4H3/b9-6+,13-8+

> <INCHI_KEY>
ZLMAVMBYWKVCLV-IMWXLZLDNA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.582733834300548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,7E)-1,5,5,8-tetramethylcycloundeca-3,7-dien-1-ol

> <JCHEM_LOGP>
3.8906976309999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.29646369594343

> <JCHEM_PKA_STRONGEST_BASIC>
-0.919526779394344

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
72.45760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,7E)-1,5,5,8-tetramethylcycloundeca-3,7-dien-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0337888 (Humulol)
Download
PDB for NP0337888 (Humulol)
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      -6.875  -8.195   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.209  -8.965   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.209 -10.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.541  -8.965   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.208  -8.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.208 -11.275   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.874 -10.505   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.874  -8.965   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.875 -11.275   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.223 -12.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.683 -12.740   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.778 -13.985   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.383 -14.112   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.542 -11.275   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.208  -6.655   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.541  -7.425   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    3                                                       
CONECT    3    2    9   14                                                  
CONECT    4    1    5                                                       
CONECT    5    4    8   15   16                                             
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    7    5                                                       
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3                                                            
CONECT   15    5                                                            
CONECT   16    5                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Download
3D PDB for NP0337888 (Humulol)
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SMILES for NP0337888 (Humulol)
C\C1=C/CC(C)(C)\C=C\CC(C)(O)CCC1
Download
INCHI for NP0337888 (Humulol)
InChI=1/C15H26O/c1-13-7-5-10-15(4,16)11-6-9-14(2,3)12-8-13/h6,8-9,16H,5,7,10-12H2,1-4H3/b9-6+,13-8+
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H26O
Average Mass222.3720 Da
Monoisotopic Mass222.19837 Da
IUPAC Name(3E,7E)-1,5,5,8-tetramethylcycloundeca-3,7-dien-1-ol
Traditional Name(3E,7E)-1,5,5,8-tetramethylcycloundeca-3,7-dien-1-ol
CAS Registry NumberNot Available
SMILES
C\C1=C/CC(C)(C)\C=C\CC(C)(O)CCC1
InChI Identifier
InChI=1/C15H26O/c1-13-7-5-10-15(4,16)11-6-9-14(2,3)12-8-13/h6,8-9,16H,5,7,10-12H2,1-4H3/b9-6+,13-8+
InChI KeyZLMAVMBYWKVCLV-IMWXLZLDNA-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Humulane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Tertiary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP3.89ChemAxon
pKa (Strongest Acidic)19.3ChemAxon
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.46 m³·mol⁻¹ChemAxon
Polarizability27.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00061038  
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. Janzen D, Slavik B, Zehe M, Sotriffer C, Loos HM, Buettner A, Villmann C: Sesquiterpenes and sesquiterpenoids harbor modulatory allosteric potential and affect inhibitory GABA(A) receptor function in vitro. J Neurochem. 2021 Oct;159(1):101-115. doi: 10.1111/jnc.15469. Epub 2021 Jul 31. [PubMed:34263932  ]