NP-MRD: Showing NP-Card for epi-beta-santalene (NP0045003)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-10 18:52:34 UTC

Updated at

2022-03-10 22:20:38 UTC

NP-MRD ID

NP0045003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epi-beta-santalene

Description

Epi-beta-Santalene, also known as epi-santalene, belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Technically Epi-beta-santalene is a carbobicyclic compound that is bicyclo[2.2.1]Heptane in which the hydrogens at position 3 are substituted by a methylidene group, while the 2-exo- and 2-endo- hydrogens are subsitituted by 2-methylpent-2-en-5-yl and methyl groups, respectively (the 1S,2R,4R enantiomer). Epi-beta-Santalene is a hydrophobic, neutral molecule that is insoluble in water. Epi-beta-Santalene is one of many terpenes that are found in cannabis plants (PMID: 6991645 ). It is also found in the essential oil of sandalwood which is a tropical tree (PMID: 24324844 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.3883    2.3683    0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    1.1997    0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1787    0.6941    0.1769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1992   -0.4582    1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5268   -1.5627    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -0.8886   -0.9550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2611    0.0046   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9894    0.1743   -0.6417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5701    0.7941   -1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753   -0.4101    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2887    0.5112    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3431   -0.3454    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688   -0.4611    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9414    0.2803   -0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -1.3069    1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002    3.0153    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4050    2.7949    0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080    1.4625    0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6798   -0.2587    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -0.7460    1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7419   -2.0028    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855   -2.3373   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -1.5358   -1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0978    0.7104   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1805   -0.5890   -1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    0.0838   -2.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1704    1.6956   -2.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4840    1.0855   -1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104   -1.2494   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -0.9012    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    1.0265   -0.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310    1.1627    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756   -0.8741    2.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2561   -0.0061   -1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    1.3695   -0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704    0.0183   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7395   -2.2832    0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5402   -0.7647    1.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378   -1.4702    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 13 12  2  3
 12 11  1  0
 11 10  1  0
  8 10  1  1
  8  9  1  0
  8  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  7  1  0
  3  2  1  0
  2  1  2  3
  2  8  1  0
  7  6  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 12 33  1  0
 11 31  1  0
 11 32  1  0
 10 29  1  0
 10 30  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  6 23  1  6
  5 21  1  0
  5 22  1  0
  4 19  1  0
  4 20  1  0
  3 18  1  1
  7 24  1  0
  7 25  1  0
  1 16  1  0
  1 17  1  0
M  END


  Mrv1652303192001303D          

 15 16  0  0  0  0            999 V2000
    3.4735    1.1372    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9502   -1.3250    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1645   -0.9523    1.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769    1.9245    0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    0.3728   -1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926   -0.6313   -0.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -1.5563   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587   -0.3134   -1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    0.3821   -1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1149    0.3549    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1345   -0.2998   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037   -0.4711    0.9576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4134   -1.0210    0.8916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3796    0.8144   -0.4166 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8782    0.5827   -0.0377 C   0  0  1  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  2  0  0  0  0
 15  4  1  1  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 11  2  3  0  0  0
  7  8  1  0  0  0  0
 13  7  1  6  0  0  0
 14  8  1  6  0  0  0
  9 15  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045003

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14+,15-/m1/s1

> <INCHI_KEY>
PGBNIHXXFQBCPU-QLFBSQMISA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.123279103120158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
4.519309391666669

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.45239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane

> <JCHEM_VEBER_RULE>
1

$$$$

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       3.474   1.137   0.157  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.950  -1.325   0.684  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.165  -0.952   1.855  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.477   1.925   0.585  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.276   0.373  -1.466  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.093  -0.631  -0.777  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.692  -1.556  -0.460  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.859  -0.313  -1.329  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.168   0.382  -1.292  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.115   0.355   0.822  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.135  -0.300  -0.005  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.004  -0.471   0.958  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.413  -1.021   0.892  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.380   0.814  -0.417  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.878   0.583  -0.038  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5    6    9                                                       
CONECT    6    5   11                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9    5   15                                                       
CONECT   10   13   14                                                       
CONECT   11    1    2    6                                                  
CONECT   12    3   13   15                                                  
CONECT   13    7   10   12                                                  
CONECT   14    8   10   15                                                  
CONECT   15    4    9   12   14                                             
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
Epi-b-santalene	Generator
Epi-β-santalene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1S,2S,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane

Traditional Name

(1S,2S,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@]1(C)[C@H]2CC[C@H](C2)C1=C

InChI Identifier

InChI=1S/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14+,15-/m1/s1

InChI Key

PGBNIHXXFQBCPU-QLFBSQMISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia xerophytica	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Eryngium foetidum	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Osyris tenuifolia	Plant	KNApSAcK
Petasites albus	Plant	KNApSAcK
Petasites hybridus	Plant	KNApSAcK
Santalum album	Plant	KNApSAcK
Santalum spicatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.56	ALOGPS
logP	4.52	ChemAxon
logS	-4.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.45 m³·mol⁻¹	ChemAxon
Polarizability	26.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11106484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Diaz-Chavez ML, Moniodis J, Madilao LL, Jancsik S, Keeling CI, Barbour EL, Ghisalberti EL, Plummer JA, Jones CG, Bohlmann J: Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol. PLoS One. 2013 Sep 18;8(9):e75053. doi: 10.1371/journal.pone.0075053. eCollection 2013. [PubMed:24324844 ]

Showing NP-Card for epi-beta-santalene (NP0045003)

MOL for NP0045003 (epi-beta-santalene)

3D MOL for NP0045003 (epi-beta-santalene)

3D SDF for NP0045003 (epi-beta-santalene)

3D-SDF for NP0045003 (epi-beta-santalene)

PDB for NP0045003 (epi-beta-santalene)

3D PDB for NP0045003 (epi-beta-santalene)

SMILES for NP0045003 (epi-beta-santalene)

INCHI for NP0045003 (epi-beta-santalene)

Structure for NP0045003 (epi-beta-santalene)

3D Structure for NP0045003 (epi-beta-santalene)