NP-MRD: Showing NP-Card for β-santalene (NP0272843)

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Record Information

Version

2.0

Created at

2022-09-08 19:39:00 UTC

Updated at

2022-09-08 19:39:00 UTC

NP-MRD ID

NP0272843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-santalene

Description

(-)-Beta-santalene, also known as β-santalene or alpha-santalene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. β-santalene is found in Artemisia xerophytica, Asarum macranthum, Atalantia buxifolia, Cinnamomum camphora, Citrus latifolia, Daphne genkwa, Dysoxylum spectabile, Erigeron canadensis, Gackstroemia magellanica, Gossypium hirsutum, Hamamelis virginiana, Gymnomitrion alpinum, Ophrys arachnitiformis, Osyris quadripartita, Piper aduncum, Rhaponticum carthamoides, Santalum album, Santalum spicatum and Smallanthus uvedalia. β-santalene was first documented in 2019 (PMID: 30922222). Based on a literature review a small amount of articles have been published on (-)-beta-santalene (PMID: 35933050) (PMID: 33121934) (PMID: 31930246).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.0257   -1.6209   -1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700   -0.8628   -0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0430   -1.4030   -0.1961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1751   -1.3775   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1935    0.1290   -1.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3926    0.7990   -0.4439 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5820   -0.2480    0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255    0.6056   -0.7612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5110    1.3653   -1.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354    1.0167    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4216    0.6893    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274    1.1113    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0723    0.2216    1.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697    0.6789    2.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -1.2151    1.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -2.7055   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8214   -1.2665   -2.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9185   -2.3279    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -1.9721   -2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1060   -1.6536   -0.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    0.4864   -1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    0.2396   -2.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6977    1.7912   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812   -0.4261    0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841   -0.0704    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556    1.7245   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751    2.2634   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    0.7734   -2.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250    2.1261    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    0.5400    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7181    1.2905   -0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5601   -0.3819   -0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560    2.1375    1.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9212    1.0765    2.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1122   -0.2110    3.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3779    1.4054    3.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017   -1.7782    1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -1.3026    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -1.6481    1.3886 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  1
  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

  Mrv1652309082221392D          

 15 16  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5082    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4372    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0363    1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4236    2.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481    2.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    3.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  3  7  1  6  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272843

> <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-ILXRZTDVSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.375092661939973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.519309391666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.4524

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
β-santalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.949   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.816   2.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.262   2.953   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.801   3.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.524   4.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.063   4.421   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.708   5.673   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    3                                                       
CONECT    8    6    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
(1S-exo)-2-Methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane	ChEBI
beta-Santalene	ChEBI
b-Santalene	Generator
Β-santalene	Generator
(-)-b-Santalene	Generator
(-)-Β-santalene	Generator
alpha-Santalene	MeSH

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

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

Traditional Name

β-santalene

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-ILXRZTDVSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Asarum macranthum	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Cinnamomum camphora	LOTUS Database	35616633
Citrus latifolia	LOTUS Database	35616633
Daphne genkwa	LOTUS Database	35616633
Dysoxylum spectabile	LOTUS Database	35616633
Erigeron canadensis	LOTUS Database	35616633
Gackstroemia magellanica	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Marsupella alpina	LOTUS Database	35616633
Ophrys x arachnitiformis	LOTUS Database	35616633
Osyris quadripartita	LOTUS Database	35616633
Piper aduncum	LOTUS Database	35616633
Rhaponticum carthamoides	LOTUS Database	35616633
Santalum album	LOTUS Database	35616633
Santalum spicatum	LOTUS Database	35616633
Smallanthus uvedalia	LOTUS Database	35616633

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

bridged compound (CHEBI:10440 )
carbobicyclic compound (CHEBI:10440 )
sesquiterpene (CHEBI:10440 )
polycyclic olefin (CHEBI:10440 )

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	4.52	ChemAxon
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	26.38 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

C00003181

Chemspider ID

9064282

KEGG Compound ID

Not Available

BioCyc ID

CPD-11378

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10889018

PDB ID

Not Available

ChEBI ID

10440

Good Scents ID

rw1103631

References

General References

Chen X, Zhang Y, Yan H, Niu M, Xiong Y, Zhang X, Li Y, Teixeira da Silva JA, Ma G: Cloning and functional analysis of 1-deoxy-D-xylulose-5-phosphate synthase (DXS) in Santalum album L. Gene. 2022 Aug 3:146762. doi: 10.1016/j.gene.2022.146762. [PubMed:35933050 ]
Di Girolamo A, Durairaj J, van Houwelingen A, Verstappen F, Bosch D, Cankar K, Bouwmeester H, de Ridder D, van Dijk ADJ, Beekwilder J: The santalene synthase from Cinnamomum camphora: Reconstruction of a sesquiterpene synthase from a monoterpene synthase. Arch Biochem Biophys. 2020 Nov 30;695:108647. doi: 10.1016/j.abb.2020.108647. Epub 2020 Oct 26. [PubMed:33121934 ]
Najera C, Foubelo F, Sansano JM, Yus M: Stereodivergent routes in organic synthesis: carbohydrates, amino acids, alkaloids and terpenes. Org Biomol Chem. 2020 Feb 19;18(7):1232-1278. doi: 10.1039/c9ob02419k. [PubMed:31930246 ]
Zhang X, Niu M, Teixeira da Silva JA, Zhang Y, Yuan Y, Jia Y, Xiao Y, Li Y, Fang L, Zeng S, Ma G: Identification and functional characterization of three new terpene synthase genes involved in chemical defense and abiotic stresses in Santalum album. BMC Plant Biol. 2019 Mar 28;19(1):115. doi: 10.1186/s12870-019-1720-3. [PubMed:30922222 ]
LOTUS database [Link]

Showing NP-Card for β-santalene (NP0272843)

MOL for NP0272843 (β-santalene)

3D MOL for NP0272843 (β-santalene)

3D SDF for NP0272843 (β-santalene)

3D-SDF for NP0272843 (β-santalene)

PDB for NP0272843 (β-santalene)

3D PDB for NP0272843 (β-santalene)

SMILES for NP0272843 (β-santalene)

INCHI for NP0272843 (β-santalene)

Structure for NP0272843 (β-santalene)

3D Structure for NP0272843 (β-santalene)