NP-MRD: Showing NP-Card for Sterculic acid (NP0046335)

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Record Information

Version

2.0

Created at

2022-03-17 19:56:23 UTC

Updated at

2022-03-17 19:56:23 UTC

NP-MRD ID

NP0046335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sterculic acid

Description

Sterculic acid, also known as 9,10-MT 9C-18:1 Or sterculia-saeure, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Sterculic acid is found in Abelmoschus esculentus, Abutilon ramosum, Acacia chundra , Amaranthus paniculatus, Apis cerana, Azima tetracantha, Brunfelsia americana, Caesalpinia coriaria , Cassia fistula , Cassia renigera, Cordia sinensis, Crotalaria retusa, Delonix regia, Plectranthus mollis, Eriolaena hookeriana, Firmiana simplex , Gossypium hirsutum , Hibiscus syriacus , Indigofera glabra, Juglans regia, Malva sylvestris, Pithecellobium dulce, Sterculia foetida , Sterculia pallens, Sterculia tragacantha, Syzygium cumini, Trichodesma zeylanicum and Turnera ulmifolia. Sterculic acid was first documented in 1974 (PMID: 4469675). Sterculic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223322D          

 21 21  0  0  0  0            999 V2000
    6.4819   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7673   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0553   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1981   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580    0.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9114   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6260   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0540   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7687   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4819   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7685    0.6184    0.0000 O   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
  2 21  2  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC1=C(CCCCCCCC(O)=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21)

> <INCHI_KEY>
PQRKPYLNZGDCFH-UHFFFAOYSA-N

> <FORMULA>
C19H34O2

> <MOLECULAR_WEIGHT>
294.4721

> <EXACT_MASS>
294.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.415062883589364

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-(2-octylcycloprop-1-en-1-yl)octanoic acid

> <ALOGPS_LOGP>
6.37

> <JCHEM_LOGP>
6.362226426666666

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.754162576920003

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.56299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sterculic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0      12.100  -1.154   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.766  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.437  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.103  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.769  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.437  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.103  -1.154   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.769  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.435  -1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.104  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.668   0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.438  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.769  -1.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.103  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.435  -1.154   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.769  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.100  -1.154   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.434  -0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.768  -1.154   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.100  -0.385   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.768   1.154   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   10   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-Octyl-1-cyclopropene-1-octanoic acid	ChEBI
8-(2-Octyl-cycloprop-1-enyl)-octansaeure	ChEBI
9,10-Methylene-9-octadecenoic acid	ChEBI
9,10-MT 9C-18:1	ChEBI
Omega-(2-N-octylcycloprop-1-enyl)octanoic acid	ChEBI
Sterculia-saeure	ChEBI
Sterculinic acid	ChEBI
Sterculinsaeure	ChEBI
2-Octyl-1-cyclopropene-1-octanoate	Generator
9,10-Methylene-9-octadecenoate	Generator
Omega-(2-N-octylcycloprop-1-enyl)octanoate	Generator
Sterculinate	Generator
Sterculate	Generator

Chemical Formula

C₁₉H₃₄O₂

Average Mass

294.4721 Da

Monoisotopic Mass

294.25588 Da

IUPAC Name

8-(2-octylcycloprop-1-en-1-yl)octanoic acid

Traditional Name

sterculic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCC1=C(CCCCCCCC(O)=O)C1

InChI Identifier

InChI=1S/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21)

InChI Key

PQRKPYLNZGDCFH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	LOTUS Database	35616633
Abutilon ramosum	LOTUS Database	35616633
Acacia chundra	Plant	KNApSAcK
Amaranthus paniculatus	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Azima tetracantha	LOTUS Database	35616633
Brunfelsia americana	LOTUS Database	35616633
Caesalpinia coriaria	Plant	KNApSAcK
Cassia fistula	Plant	KNApSAcK
Cassia renigera	Plant	KNApSAcK
Cordia sinensis	LOTUS Database	35616633
Crotalaria retusa	LOTUS Database	35616633
Delonix regia	LOTUS Database	35616633
Equilabium molle	LOTUS Database	35616633
Eriolaena hookeriana	LOTUS Database	35616633
Firmiana simplex	Plant	KNApSAcK
Gossypium hirsutum	Plant	KNApSAcK
Hibiscus sabbariffa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hibiscus syriacus	Plant	KNApSAcK
Indigofera glabra	Plant	KNApSAcK
Juglans regia	LOTUS Database	35616633
Malva sylvestris	LOTUS Database	35616633
Pithecellobium dulce	LOTUS Database	35616633
Sterculia foetida	Plant	KNApSAcK
Sterculia pallens	Plant	KNApSAcK
Sterculia tragacantha	LOTUS Database	35616633
Syzygium cumini	LOTUS Database	35616633
Trichodesma zeylanicum	LOTUS Database	35616633
Turnera ulmifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:9261 )
monounsaturated fatty acid (CHEBI:9261 )
cyclopropenyl fatty acid (CHEBI:9261 )
Carbocyclic fatty acids (C08366 )
Fatty acids (C08366 )
Carbocyclic fatty acids (LMFA01140018 )

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	6.37	ALOGPS
logP	6.36	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	89.56 m³·mol⁻¹	ChemAxon
Polarizability	38.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

FDB004049

KNApSAcK ID

C00001239

Chemspider ID

Not Available

KEGG Compound ID

C08366

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sterculic acid

METLIN ID

Not Available

PubChem Compound

12921

PDB ID

Not Available

ChEBI ID

9261

Good Scents ID

Not Available

References

General References

Scarpelli DG: Mitogenic activity of sterculic acid, a cyclopropenoid fatty acid. Science. 1974 Sep 13;185(4155):958-60. doi: 10.1126/science.185.4155.958. [PubMed:4469675 ]

Showing NP-Card for Sterculic acid (NP0046335)

MOL for NP0046335 (Sterculic acid)

3D MOL for NP0046335 (Sterculic acid)

3D SDF for NP0046335 (Sterculic acid)

3D-SDF for NP0046335 (Sterculic acid)

PDB for NP0046335 (Sterculic acid)

3D PDB for NP0046335 (Sterculic acid)

SMILES for NP0046335 (Sterculic acid)

INCHI for NP0046335 (Sterculic acid)

Structure for NP0046335 (Sterculic acid)

3D Structure for NP0046335 (Sterculic acid)