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Showing NP-Card for (±)-3-Carene (NP0137550)

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Record Information
Version2.0
Created at2022-05-30 16:55:55 UTC
Updated at2022-05-30 16:55:55 UTC
NP-MRD IDNP0137550
Secondary Accession NumbersNone
Natural Product Identification
Common Name(±)-3-Carene
Description(+)-Car-3-ene, also known as isodiprene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (±)-3-Carene is found in Artemisia annua, Artemisia vulgaris, Callitropsis nootkatensis, Cedrus libani, Centaurea benedicta, Citrus maxima, Coespeletia timotensis, Juniperus communis, Kippistia suaedifolia, Larix sibirica, Lavandula angustifolia, Molopospermum peloponnesiacum, Mosla chinensis, Myrtus communis, Picea abies, Pinus jeffreyi, Pinus sylvestris, Pistacia atlantica, Sideritis tragoriganum, Vaccinium macrocarpon and Zieria aspalathoides. (±)-3-Carene was first documented in 1993 (PMID: 8373196). Thus, (+)-car-3-ene is considered to be an isoprenoid lipid molecule (+)-car-3-ene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 22183881) (PMID: 22277889).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0137550 ((±)-3-Carene)


  Mrv1652309272007472D          

 10 11  0  0  0  0            999 V2000
 9998.3223 9999.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8650 9999.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.344810000.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7176 9999.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.291710000.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.577210000.3928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.5772 9999.5677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.2917 9999.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0062 9999.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.006210000.3928    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
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9  4  1  0  0  0  0
  6  2  1  6  0  0  0
  7  2  1  6  0  0  0
M  END
Download

3D MOL for NP0137550 ((±)-3-Carene)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.3530   -0.3365    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -0.3725    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -0.6347   -1.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563   -0.6615   -1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4921    0.5453   -0.9267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1657    0.8036    0.4965 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8350   -0.1257    1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5346    0.3956    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5874    1.4872    0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -0.9721    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293    0.1369   -0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4278    0.2167    1.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311   -1.3643    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605   -0.8205   -1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0140   -0.6544   -2.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792   -1.6200   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550    1.4226   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    1.8847    0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111   -1.0818    1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255    0.3409    1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    2.4855   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716    1.5606    1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809    1.2444   -0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7077   -0.8999    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175   -1.7390    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -1.2408   -0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  7  2  1  0
  8  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  6
  6 18  1  6
  7 19  1  0
  7 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for NP0137550 ((±)-3-Carene)


  Mrv1652309272007472D          

 10 11  0  0  0  0            999 V2000
 9998.3223 9999.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8650 9999.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.344810000.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7176 9999.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.291710000.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.577210000.3928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.5772 9999.5677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.2917 9999.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0062 9999.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.006210000.3928    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
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9  4  1  0  0  0  0
  6  2  1  6  0  0  0
  7  2  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@@H]2[C@H](C1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m1/s1

> <INCHI_KEY>
BQOFWKZOCNGFEC-BDAKNGLRSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.280605059297645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
2.801661446333333

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
44.722300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-delta(3)-carene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0137550 ((±)-3-Carene)

Download
PDB for NP0137550 ((±)-3-Carene)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8663.5358665.478   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.5488666.638   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8663.5778667.839   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.8738665.088   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8667.2118668.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.8778667.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8665.8778665.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.2118665.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.5458665.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.5458667.400   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6    7                                             
CONECT    3    2                                                            
CONECT    4    9                                                            
CONECT    5    6   10                                                       
CONECT    6    5    7    2                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    4                                                  
CONECT   10    5    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

Download
3D PDB for NP0137550 ((±)-3-Carene)
Download
SMILES for NP0137550 ((±)-3-Carene)
CC1=CC[C@@H]2[C@H](C1)C2(C)C
Download
INCHI for NP0137550 ((±)-3-Carene)
InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(+)-3-CareneChEBI
(+)-alpha-CareneChEBI
(+)-Delta(3)-CareneChEBI
(1S)-(+)-3-CareneChEBI
(1S)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-eneChEBI
(1S,6R)-(+)-3-CareneChEBI
(S)-(+)-3-CareneChEBI
IsodipreneChEBI
(1S,6R)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-eneKegg
(+)-a-CareneGenerator
(+)-Α-careneGenerator
(+)-Δ(3)-careneGenerator
3-CareneMeSH
3-Carene, (S)-(cis)-isomerMeSH
3-Carene, (R)-isomerMeSH
(+)-Car-3-eneKEGG
(+)-Carene-3PhytoBank
(+)-delta3-CarenePhytoBank
(+)-Δ3-CarenePhytoBank
(1S)-3-CarenePhytoBank
(1S,6R)-3-CarenePhytoBank
3,7,7-Trimethylbicyclo[4.1.0]hept-3-enePhytoBank
(±)-3-CarenePhytoBank
(±)-delta3-CarenePhytoBank
(±)-Δ3-CarenePhytoBank
delta3-CarenePhytoBank
Δ3-CarenePhytoBank
delta-3-CarenePhytoBank
δ-3-CarenePhytoBank
Chemical FormulaC10H16
Average Mass136.2380 Da
Monoisotopic Mass136.12520 Da
IUPAC Name(1S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene
Traditional Name(+)-delta(3)-carene
CAS Registry NumberNot Available
SMILES
CC1=CC[C@@H]2[C@H](C1)C2(C)C
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m1/s1
InChI KeyBQOFWKZOCNGFEC-BDAKNGLRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia annuaLOTUS Database
Artemisia vulgarisLOTUS Database
Callitropsis nootkatensisLOTUS Database
Cedrus libaniLOTUS Database
Centaurea benedictaLOTUS Database
Citrus maximaLOTUS Database
Espeletia timotensisLOTUS Database
Juniperus communisLOTUS Database
Kippistia suaedifoliaLOTUS Database
Larix sibiricaLOTUS Database
Lavandula angustifoliaLOTUS Database
Molopospermum peloponnesiacumLOTUS Database
Mosla chinensisLOTUS Database
Myrtus communisLOTUS Database
Picea abiesLOTUS Database
Pinus jeffreyiLOTUS Database
Pinus sylvestrisLOTUS Database
Pistacia atlanticaLOTUS Database
Sideritis tragoriganumLOTUS Database
Vaccinium macrocarponLOTUS Database
Zieria aspalathoidesLOTUS Database
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
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.64ALOGPS
logP2.8ChemAxon
logS-3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.72 m³·mol⁻¹ChemAxon
Polarizability17.28 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 IDC00011044  
Chemspider IDNot Available
KEGG Compound IDC11382  
BioCyc IDCPD-8756  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443156  
PDB IDNot Available
ChEBI ID7  
Good Scents IDNot Available
References
General References
  1. Dvorakova M, Valterova I, Saman D, Vanek T: Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture. Molecules. 2011 Dec 19;16(12):10541-55. doi: 10.3390/molecules161210541. [PubMed:22183881  ] 
  2. Miyazawa M, Koutari S: Quantitative evaluation of (+)-Delta(3)-carene metabolites from living larvae of Spodoptera litura by headspace solid-phase microextraction. J Oleo Sci. 2012;61(2):65-8. doi: 10.5650/jos.61.65. [PubMed:22277889  ] 
  3. Savage TJ, Croteau R: Biosynthesis of monoterpenes: regio- and stereochemistry of (+)-3-carene biosynthesis. Arch Biochem Biophys. 1993 Sep;305(2):581-7. doi: 10.1006/abbi.1993.1464. [PubMed:8373196  ]