Cannabis Compound Database: Showing Compound Card for (+)-Sativene (CDB000484)

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Record Information

Version

1.0

Created at

2020-03-19 00:39:27 UTC

Updated at

2020-11-18 16:35:12 UTC

CannabisDB ID

CDB000484

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

(+)-Sativene

Description

Sativene belongs to the class of organic compounds known as sesquiterpenoids. A sesquiterpene that is octahydro-1H-1,4-methanoindene bearing methyl, isopropyl and methylene substituents at positions 4, 7 and 8 respectively (the 1R,3aS,4R,7R,7aR-isomer). 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-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). 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. Sativene is possibly neutral and it is one of the terpenes that are known to occur in cannabis plants (PMID: 25454145 ). It was also identified in the essential oil from Kyllinga erecta Schumach (navua sedge) (DOI: 10.1021/jf00026a027), Croton sonderianus (marmeleiro preto) (PMID: 15979097 ), Stachys aleurites (Lamb's Ear) (0.2% relative to total oil constituents) (DOI: 10.1016/j.bse.2004.05.013), and the essential oil from fruits of Schinus terebinthifolia Raddi (Brazilian pepper tree) (0.93% relative to total oil constituents) (PMID: 21729280 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(+)-Sativene	ChEBI
(1R,3AS,4R,7R,7ar)-7-isopropyl-4-methyl-8-methyleneoctahydro-1H-1,4-methanoindene	ChEBI

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.36

Monoisotopic Molecular Weight

204.1878

IUPAC Name

(1S,2R,3R,6R,8R)-6-methyl-7-methylidene-3-(propan-2-yl)tricyclo[4.4.0.0^{2,8}]decane

Traditional Name

(1S,2R,3R,6R,8R)-3-isopropyl-6-methyl-7-methylidenetricyclo[4.4.0.0^{2,8}]decane

CAS Registry Number

3650-28-0

SMILES

CC(C)[C@H]1CC[C@]2(C)[C@H]3CC[C@H]([C@@H]13)C2=C

InChI Identifier

InChI=1S/C15H24/c1-9(2)11-7-8-15(4)10(3)12-5-6-13(15)14(11)12/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13+,14-,15+/m1/s1

InChI Key

VOBBUADSYROGAT-FQKPHLNHSA-N

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

Oplopane sesquiterpenoid
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:64800 )
sesquiterpene (CHEBI:64800 )

Ontology

Not Available

Physical Properties

State

Solid

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	4.12	ALOGPS
logP	4.15	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	1	ChemAxon
Refractivity	64.7 m³·mol⁻¹	ChemAxon
Polarizability	25.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

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

CPD-8804

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11830550

PDB ID

Not Available

ChEBI ID

64800

References

General References

Marchini M, Charvoz C, Dujourdy L, Baldovini N, Filippi JJ: Multidimensional analysis of cannabis volatile constituents: identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L. J Chromatogr A. 2014 Nov 28;1370:200-15. doi: 10.1016/j.chroma.2014.10.045. Epub 2014 Oct 23. [PubMed:25454145 ]
Santos FA, Jeferson FA, Santos CC, Silveira ER, Rao VS: Antinociceptive effect of leaf essential oil from Croton sonderianus in mice. Life Sci. 2005 Oct 21;77(23):2953-63. doi: 10.1016/j.lfs.2005.05.032. [PubMed:15979097 ]
Kweka EJ, Nyindo M, Mosha F, Silva AG: Insecticidal activity of the essential oil from fruits and seeds of Schinus terebinthifolia Raddi against African malaria vectors. Parasit Vectors. 2011 Jul 5;4:129. doi: 10.1186/1756-3305-4-129. [PubMed:21729280 ]
Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]

Showing Compound Card for (+)-Sativene (CDB000484)

Structure for CDB000484 ((+)-Sativene)