NP-MRD: Showing NP-Card for (3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol (NP0046159)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:49:26 UTC

Updated at

2022-03-17 19:49:26 UTC

NP-MRD ID

NP0046159

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol

Description

(3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol has been detected, but not quantified in, herbs and spices and turmerics. (3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol is found in Calea jamaicensis and Greenmaniella resinosa. This could make (3S,4S,6R,7S)-1,10-bisaboladiene-3,4-diol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305552D          

 17 17  0  0  0  0            999 V2000
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15  4  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046159

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C)C1CC(O)C(C)(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-11(2)6-5-7-12(3)13-8-9-15(4,17)14(16)10-13/h6,8-9,12-14,16-17H,5,7,10H2,1-4H3

> <INCHI_KEY>
YRFJMOGROZTYPC-UHFFFAOYSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.3657

> <EXACT_MASS>
238.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.884776862292654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-(6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
2.9586734603333316

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.919243882117662

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.496607911198122

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2645266583532138

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
73.7386

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-(6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   12                                                       
CONECT    8    9   13                                                       
CONECT    9    8   15                                                       
CONECT   10   13   14                                                       
CONECT   11    1    2    6                                                  
CONECT   12    3    7   13                                                  
CONECT   13    8   10   12                                                  
CONECT   14   10   15   16                                                  
CONECT   15    4    9   14   17                                             
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
1-Methyl-2,6-diphenyl-4-piperidinone O-benzyloxime	HMDB
[1S-[1alpha,2beta,5beta(R*)]]-5-(1,5-dimethyl-4-hexenyl)-2-methyl-3-cyclohexene-1,2-diol	HMDB

Chemical Formula

C₁₅H₂₆O₂

Average Mass

238.3657 Da

Monoisotopic Mass

238.19328 Da

IUPAC Name

2-methyl-5-(6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol

Traditional Name

2-methyl-5-(6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol

CAS Registry Number

129673-87-6

SMILES

CC(CCC=C(C)C)C1CC(O)C(C)(O)C=C1

InChI Identifier

InChI=1S/C15H26O2/c1-11(2)6-5-7-12(3)13-8-9-15(4,17)14(16)10-13/h6,8-9,12-14,16-17H,5,7,10H2,1-4H3

InChI Key

YRFJMOGROZTYPC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Calea jamaicensis	LOTUS Database	35616633
Curcuma longa	FooDB	KNAPSACK
Greenmaniella resinosa	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

Bisabolane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	3.38	ALOGPS
logP	2.96	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.74 m³·mol⁻¹	ChemAxon
Polarizability	28.88 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031383

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003450

KNApSAcK ID

C00011598

Chemspider ID

24022800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14633005

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol (NP0046159)

MOL for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

3D MOL for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

3D SDF for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

3D-SDF for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

PDB for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

3D PDB for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

SMILES for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

INCHI for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

Structure for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)

3D Structure for NP0046159 ((3S,4S,6R,7S)-1,10-Bisaboladiene-3,4-diol)