NP-MRD: Showing NP-Card for alpha-Santalene (NP0048087)

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Record Information

Version

2.0

Created at

2022-03-17 20:50:52 UTC

Updated at

2022-03-17 20:50:52 UTC

NP-MRD ID

NP0048087

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Santalene

Description

Alpha-Santalene, also known as α-santalene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Alpha-Santalene is possibly neutral. Alpha-Santalene is a woody tasting compound. Outside of the human body, alpha-santalene is found, on average, in the highest concentration in star anises. Alpha-santalene has also been detected, but not quantified in, several different foods, such as allspices, giant butterburs, pepper (spice), and sweet basils. alpha-Santalene is found in Achyrospermum africanum, Aframomum angustifolium, Alpinia galanga, Aristolochia debilis, Artemisia xerophytica, Atalantia buxifolia, Ayapana amygdalina, Basella alba, Cinnamomum camphora , Citrus latifolia, Clausena lansium , Commiphora guidottii, Cryptomeria japonica, Cymbopogon schoenanthus, Daphne genkwa, Daucus carota, Echinops grijsii, Gossypium hirsutum, Illicium tsangii, Lavandin abrialis, Lavandula angustifolia , Osyris quadripartita, Osyris tenuifolia, Petasites albus , Petasites hybridus , Plexaurella grisea, Pseudowintera colorata, Santalum album , Santalum spicatum, Schisandra chinensis , Severinia buxifolia , Smallanthus uvedalia, Umbellularia californica, Valeriana jatamansi, Xylopia rubescens and Zingiber officinale . This could make alpha-santalene a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218592D          

 15 17  0  0  0  0            999 V2000
   -1.0665    0.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2961    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -0.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7113   -0.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744   -1.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708    0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968    0.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817    0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968    1.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2447   -0.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5411    0.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708    0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  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
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC1(C)C2CC3C(C2)C13C

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

> <INCHI_KEY>
KWFJIXPIFLVMPM-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.38698963616168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,7-dimethyl-7-(4-methylpent-3-en-1-yl)tricyclo[2.2.1.0²,⁶]heptane

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
4.101158186333333

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
65.6944

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,7-dimethyl-7-(4-methylpent-3-en-1-yl)tricyclo[2.2.1.0²,⁶]heptane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.991   1.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.553   1.272   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.111  -0.055   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.659  -0.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.328  -1.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.209  -0.719   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.872  -2.047   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.425   0.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.541   0.276   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.766   1.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.659   1.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.541   2.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.323  -1.161   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.877   0.276   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.425   0.498   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6   11                                             
CONECT    5    4                                                            
CONECT    6    4    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    6    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    4   10   12                                                  
CONECT   12    8   11                                                       
CONECT   13   14                                                            
CONECT   14    1   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
a-Santalene	Generator
Α-santalene	Generator
(-)-alpha -Santalene	HMDB
alpha -Santalene	HMDB
Hexaphenyl-cyclotrisiloxane	HMDB
Santalen	HMDB
Santalene	HMDB
beta-Santalene	MeSH
alpha-Santalene	MeSH

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

1,7-dimethyl-7-(4-methylpent-3-en-1-yl)tricyclo[2.2.1.0²,⁶]heptane

Traditional Name

1,7-dimethyl-7-(4-methylpent-3-en-1-yl)tricyclo[2.2.1.0²,⁶]heptane

CAS Registry Number

512-61-8

SMILES

CC(C)=CCCC1(C)C2CC3C(C2)C13C

InChI Identifier

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

InChI Key

KWFJIXPIFLVMPM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achyrospermum africanum	LOTUS Database	35616633
Aframomum angustifolium	LOTUS Database	35616633
Alpinia galanga	LOTUS Database	35616633
Apium graveolens var. dulce	FooDB	Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Apium graveolens var. rapaceum	FooDB	Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Aristolochia debilis	LOTUS Database	35616633
Artemisia xerophytica	LOTUS Database	35616633
Atalantia buxifolia	Plant	KNApSAcK
Ayapana amygdalina	LOTUS Database	35616633
Basella alba	LOTUS Database	35616633
Cinnamomum camphora	Plant	KNApSAcK
Citrus latifolia	LOTUS Database	35616633
Clausena lansium	Plant	KNApSAcK
Commiphora guidottii	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cymbopogon schoenanthus	LOTUS Database	35616633
Daphne genkwa	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Daucus carota ssp. sativus	FooDB	12926889
Echinops grijsii	Plant	KNApSAcK
Gossypium hirsutum	LOTUS Database	35616633
Illicium tsangii	LOTUS Database	35616633
Illicium verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lavandin abrialis	-	KNApSAcK
Lavandula angustifolia	Plant	KNApSAcK
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Osyris quadripartita	LOTUS Database	35616633
Osyris tenuifolia	Plant	KNApSAcK
Petasites albus	Plant	KNApSAcK
Petasites hybridus	Plant	KNApSAcK
Petasites japonicus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pimenta dioica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Plexaurella grisea	LOTUS Database	35616633
Pseudowintera colorata	LOTUS Database	35616633
Santalum album	Plant	KNApSAcK
Santalum spicatum	Plant	KNApSAcK
Schisandra chinensis	Plant	KNApSAcK
Severinia buxifolia	Plant	KNApSAcK
Smallanthus uvedalia	LOTUS Database	35616633
Umbellularia californica	LOTUS Database	35616633
Valeriana jatamansi	LOTUS Database	35616633
Xylopia rubescens	Plant	KNApSAcK
Zingiber officinale	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

Santalane 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

a sesquiterpenoid (CPD-11377 )

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	4.96	ALOGPS
logP	4.1	ChemAxon
logS	-5.2	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	65.69 m³·mol⁻¹	ChemAxon
Polarizability	26.39 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

External Links

HMDB ID

HMDB0034939

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013531

KNApSAcK ID

C00021850

Chemspider ID

84980

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94164

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for alpha-Santalene (NP0048087)

MOL for NP0048087 (alpha-Santalene)

3D MOL for NP0048087 (alpha-Santalene)

3D SDF for NP0048087 (alpha-Santalene)

3D-SDF for NP0048087 (alpha-Santalene)

PDB for NP0048087 (alpha-Santalene)

3D PDB for NP0048087 (alpha-Santalene)

SMILES for NP0048087 (alpha-Santalene)

INCHI for NP0048087 (alpha-Santalene)

Structure for NP0048087 (alpha-Santalene)

3D Structure for NP0048087 (alpha-Santalene)