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Showing NP-Card for delta4-carene (NP0044984)

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Record Information
Version2.0
Created at2022-03-10 18:52:15 UTC
Updated at2022-03-10 22:20:20 UTC
NP-MRD IDNP0044984
Secondary Accession NumbersNone
Natural Product Identification
Common Namedelta4-carene
DescriptionDelta-4-Carene or (+)-4-Carene, or simply 4-Carene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Delta4-Carene is also classified as a cycloalkene (with molecular formula of C10H16) although it is biochemically a monoterpenoid as it synthesized via multiple isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are several isomers of Carene, including Delta-2-Carene, Delta-3-Carene and Delta-4-Carene. Delta-4-Carene is a hydrophobic, neutral molecule that is insoluble in water. Delta-4-Carene has been detected, but not quantified in rosemary, black currants and as a volatile component in tomatoes (PMID: 24096821 ). It exhibits larvicidal activities and appears to be active against the third stage larvae of mosquitoes that carry malaria, Dengue and filariasis (PMID: 27151483 ). It is one of many terpenes that are found in cannabis plants (PMID: 6991645 ). Delta-4-Carene is one of more than 140 terpenes in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. Savita.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0044984 (delta4-carene)


  Mrv1652303192001293D          

 10 11  0  0  0  0            999 V2000
    3.1103    0.7114    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4341   -0.6890   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030    0.7703    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6699   -1.2242   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364   -1.7404   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    1.1008    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351    0.0863    0.5572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6108   -0.8584    0.1942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3216    0.4258   -0.6681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6166   -0.0712   -0.3907 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for NP0044984 (delta4-carene)

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3D SDF for NP0044984 (delta4-carene)

  Mrv1652303192001293D          

 10 11  0  0  0  0            999 V2000
    3.1103    0.7114    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4341   -0.6890   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030    0.7703    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6699   -1.2242   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364   -1.7404   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    1.1008    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351    0.0863    0.5572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6108   -0.8584    0.1942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3216    0.4258   -0.6681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6166   -0.0712   -0.3907 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044984

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H]2[C@H](C=C1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4-5,7-9H,6H2,1-3H3/t7-,8+,9+/m1/s1

> <INCHI_KEY>
LGNSZMLHOYDATP-VGMNWLOBSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.311434026197762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
2.845319271

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
44.98890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0044984 (delta4-carene)
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PDB for NP0044984 (delta4-carene)
HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0       3.110   0.711   0.441  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.434  -0.689  -1.521  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.503   0.770   0.525  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.670  -1.224  -0.139  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.436  -1.740  -0.339  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.712   1.101   0.111  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.735   0.086   0.557  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.611  -0.858   0.194  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.322   0.426  -0.668  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.617  -0.071  -0.391  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    7    9                                                       
CONECT    7    1    4    6                                                  
CONECT    8    5    9   10                                                  
CONECT    9    6    8   10                                                  
CONECT   10    2    3    8    9                                             
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0044984 (delta4-carene)
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SMILES for NP0044984 (delta4-carene)
C[C@H]1C[C@H]2[C@H](C=C1)C2(C)C
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INCHI for NP0044984 (delta4-carene)
InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4-5,7-9H,6H2,1-3H3/t7-,8+,9+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16
Average Mass136.2380 Da
Monoisotopic Mass136.12520 Da
IUPAC Name(1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene
Traditional Name(1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene
CAS Registry NumberNot Available
SMILES
C[C@H]1C[C@H]2[C@H](C=C1)C2(C)C
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4-5,7-9H,6H2,1-3H3/t7-,8+,9+/m1/s1
InChI KeyLGNSZMLHOYDATP-VGMNWLOBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaNULL
      Not Available
Salvia rosmarinusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Carane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.46ALOGPS
logP2.85ChemAxon
logS-4.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.99 m³·mol⁻¹ChemAxon
Polarizability17.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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 Compound90473900  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References