NP-MRD: Showing NP-Card for beta-Santalol (NP0048580)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:43 UTC

Updated at

2022-03-17 20:58:43 UTC

NP-MRD ID

NP0048580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Santalol

Description

Beta-Santalol, also known as b-santalenol or fema 3006, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, beta-santalol is considered to be an isoprenoid lipid molecule. Beta-Santalol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Beta-Santalol is a woody tasting compound. Outside of the human body, beta-Santalol has been detected, but not quantified in, gingers. beta-Santalol is found in Atalantia buxifolia, Citrus latifolia, Clausena lansium , Santalum album , Santalum spicatum and Xylopia sericea . This could make beta-santalol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02241219552D          

 16 17  0  0  0  0            999 V2000
   -2.8286   -0.4419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5430   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5430   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -2.0920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1141   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141   -0.8545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3996   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6852   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7438   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7438   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4582   -2.0920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -1.2388    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  6  0  0  0
  5 15  2  0  0  0  0
  1 16  1  1  0  0  0
  4 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0048580

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)12(2)13-6-7-14(15)9-13/h5,13-14,16H,2,4,6-10H2,1,3H3/b11-5-/t13-,14+,15+/m1/s1

> <INCHI_KEY>
OJYKYCDSGQGTRJ-GQYWAMEOSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.21036724476403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl]pent-2-en-1-ol

> <ALOGPS_LOGP>
4.42

> <JCHEM_LOGP>
3.238538235000001

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.644023469944937

> <JCHEM_PKA_STRONGEST_BASIC>
-2.079704134246084

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.2271

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-santalol

> <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      -5.280  -0.825   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.614  -1.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.614  -3.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.280  -3.905   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.946  -3.135   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.946  -1.595   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.613  -0.825   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.279  -1.595   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.055  -0.825   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.388  -1.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.722  -0.825   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.388  -3.135   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.722  -3.905   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.946  -0.055   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.613  -3.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.881  -2.312   0.000  0.00  0.00           C+0
CONECT    1    2    6   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    1    7   14                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    6                                                            
CONECT   15    5                                                            
CONECT   16    1    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(1S-(1alpha,2alpha(Z),4alpha))-2-Methyl-5-(2-methyl-3-methylenebicyclo(2.2.1)hept-2-yl)-2-penten-1-ol	ChEBI
2-Methyl-5-(2-methyl-3-methylene-2-norbornyl)-2-penten-1-ol	ChEBI
beta-Santalenol	ChEBI
(1S-(1a,2a(Z),4a))-2-Methyl-5-(2-methyl-3-methylenebicyclo(2.2.1)hept-2-yl)-2-penten-1-ol	Generator
(1S-(1Α,2α(Z),4α))-2-methyl-5-(2-methyl-3-methylenebicyclo(2.2.1)hept-2-yl)-2-penten-1-ol	Generator
b-Santalenol	Generator
Β-santalenol	Generator
b-Santalol	Generator
Β-santalol	Generator
(-)-(Z)-beta-Santalol	HMDB
(-)-beta-Santalol	HMDB
(Z)-beta-Santalol	HMDB
beta-(Z)-Santalol	HMDB
cis-b-Santalol	HMDB
cis-beta-Santalol	HMDB
FEMA 3006	HMDB

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3505 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(2Z)-2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl]pent-2-en-1-ol

Traditional Name

β-santalol

CAS Registry Number

77-42-9

SMILES

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

InChI Identifier

InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)12(2)13-6-7-14(15)9-13/h5,13-14,16H,2,4,6-10H2,1,3H3/b11-5-/t13-,14+,15+/m1/s1

InChI Key

OJYKYCDSGQGTRJ-GQYWAMEOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Atalantia buxifolia	LOTUS Database	35616633
Citrus latifolia	LOTUS Database	35616633
Clausena lansium	Plant	KNApSAcK
Santalum album	Plant	KNApSAcK
Santalum spicatum	Plant	KNApSAcK
Xylopia sericea	Plant	KNApSAcK
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

penten-1-ols (CHEBI:10441 )
norbornane monoterpenoid (CHEBI:10441 )
Campherenane and santalane sesquiterpenoids (LMPR0103800003 )

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	4.42	ALOGPS
logP	3.24	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.23 m³·mol⁻¹	ChemAxon
Polarizability	27.21 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