NP-MRD: Showing NP-Card for Capsidiol (NP0048411)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:56:03 UTC

Updated at

2022-03-17 20:56:03 UTC

NP-MRD ID

NP0048411

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Capsidiol

Description

Capsidiol belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Capsidiol is found in Capsicum annuam, Capsicum frutescens , Laurencia dendroidea, Nicotiana attenuate, Nicotiana clevelandii, Nicotiana debneyi, Nicotiana sylvestris, Nicotiana tabacum and Nicotiana tomentosiformis. Capsidiol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920282D          

 17 18  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048411

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)CC(O)C2=CCC(CC12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3

> <INCHI_KEY>
BXXSHQYDJWZXPB-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.97713950165548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
1.9069395216666671

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.109427768957616

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.349248791835812

> <JCHEM_PKA_STRONGEST_BASIC>
-2.870269296051214

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
70.51679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,5,6,7-hexahydro-1H-naphthalene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   15                                                            
CONECT    5    6   11                                                       
CONECT    6    5   12                                                       
CONECT    7   13   14                                                       
CONECT    8   11   15                                                       
CONECT    9    1    2   11                                                  
CONECT   10    3   13   15                                                  
CONECT   11    5    8    9                                                  
CONECT   12    6   14   15                                                  
CONECT   13    7   10   16                                                  
CONECT   14    7   12   17                                                  
CONECT   15    4    8   10   12                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3499 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol

Traditional Name

4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,5,6,7-hexahydro-1H-naphthalene-1,3-diol

CAS Registry Number

37208-05-2

SMILES

CC1C(O)CC(O)C2=CCC(CC12C)C(C)=C

InChI Identifier

InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3

InChI Key

BXXSHQYDJWZXPB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Capsicum annuam	Plant	KNApSAcK
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum frutescens L.	Plant	KNApSAcK
Laurencia dendroidea	-	KNApSAcK
Nicotiana attenuate	Plant	KNApSAcK
Nicotiana clevelandii	LOTUS Database	35616633
Nicotiana debneyi	LOTUS Database	35616633
Nicotiana sylvestris	Plant	KNApSAcK
Nicotiana tabacum	Plant	KNApSAcK
Nicotiana tomentosiformis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a sesquiterpenoid (CPD-4661 )

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	2.7	ALOGPS
logP	1.91	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-2.9	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	1	ChemAxon
Refractivity	70.52 m³·mol⁻¹	ChemAxon
Polarizability	27.98 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014812

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Capsidiol

METLIN ID

Not Available

PubChem Compound

494902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Capsidiol (NP0048411)

MOL for NP0048411 (Capsidiol)

3D MOL for NP0048411 (Capsidiol)

3D SDF for NP0048411 (Capsidiol)

3D-SDF for NP0048411 (Capsidiol)

PDB for NP0048411 (Capsidiol)

3D PDB for NP0048411 (Capsidiol)

SMILES for NP0048411 (Capsidiol)

INCHI for NP0048411 (Capsidiol)

Structure for NP0048411 (Capsidiol)

3D Structure for NP0048411 (Capsidiol)