NP-MRD: Showing NP-Card for Malvalic acid (NP0046333)

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Record Information

Version

2.0

Created at

2022-03-17 19:56:21 UTC

Updated at

2022-03-17 19:56:21 UTC

NP-MRD ID

NP0046333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Malvalic acid

Description

Malvalic acid, also known as malvalsaeure, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Malvalic acid is found in Abelmoschus esculentus, Abutilon ramosum, Acacia chundra , Amaranthus paniculatus, Azima tetracantha, Brunfelsia americana, Caesalpinia coriaria , Cassia fistula , Cassia renigera, Cordia sinensis, Crotalaria pallida, Crotalaria retusa, Delonix regia, Plectranthus mollis, Eriolaena hookeriana, Gnetum edule, Gnetum scandens, Gossypium barbadense, Gossypium hirsutum, Hibiscus syriacus , Indigofera glabra, Jasminum auriculatum , Malva sylvestris, Pithecellobium dulce, Sterculia pallens, Sterculia tragacantha, Syzygium cumini, Trichodesma zeylanicum, Turnera ulmifolia and Urena lobata. Malvalic acid was first documented in 1957 (PMID: 13430715). Malvalic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 5512548).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223332D          

 20 20  0  0  0  0            999 V2000
   -1.6449    0.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    1.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    2.1264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2809    1.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0832    1.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844    0.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030    0.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2006    0.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207    0.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623   -2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5647   -2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0461   -1.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054   -0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3670   -0.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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>
NP0046333

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O2/c1-2-3-4-5-6-9-12-16-15-17(16)13-10-7-8-11-14-18(19)20/h2-15H2,1H3,(H,19,20)

> <INCHI_KEY>
HPSSZFFAYWBIPY-UHFFFAOYSA-N

> <FORMULA>
C18H32O2

> <MOLECULAR_WEIGHT>
280.4455

> <EXACT_MASS>
280.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.606303850845855

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(2-octylcycloprop-1-en-1-yl)heptanoic acid

> <ALOGPS_LOGP>
6.00

> <JCHEM_LOGP>
5.917657761666668

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7541625768608435

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.96199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
malvalic 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      -3.070   1.721   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.921   3.369   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.418   3.969   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.872   4.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.373   4.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.524   3.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.022   3.219   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.771   1.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.872   0.523   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.374   0.373   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.972   1.122   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.972  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.722  -1.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.972  -3.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.674  -3.070   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.423  -4.418   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.921  -4.418   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.819  -3.220   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.370  -1.722   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.418  -0.524   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-Octyl-1-cyclopropene-1-heptanoic acid	ChEBI
8,9-Methylen-8-heptadecensaeure	ChEBI
8,9-Methylene-8Z-heptadecenoic acid	ChEBI
Malvalsaeure	ChEBI
2-Octyl-1-cyclopropene-1-heptanoate	Generator
8,9-Methylene-8Z-heptadecenoate	Generator
Malvalate	Generator

Chemical Formula

C₁₈H₃₂O₂

Average Mass

280.4455 Da

Monoisotopic Mass

280.24023 Da

IUPAC Name

7-(2-octylcycloprop-1-en-1-yl)heptanoic acid

Traditional Name

malvalic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCC1=C(CCCCCCC(O)=O)C1

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-9-12-16-15-17(16)13-10-7-8-11-14-18(19)20/h2-15H2,1H3,(H,19,20)

InChI Key

HPSSZFFAYWBIPY-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
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 pallida	LOTUS Database	35616633
Crotalaria retusa	LOTUS Database	35616633
Delonix regia	LOTUS Database	35616633
Equilabium molle	LOTUS Database	35616633
Eriolaena hookeriana	LOTUS Database	35616633
Gnetum edule	LOTUS Database	35616633
Gnetum scandens	Plant	KNApSAcK
Gossypium barbadense	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hibiscus syriacus	Plant	KNApSAcK
Indigofera glabra	Plant	KNApSAcK
Jasminum auriculatum	Plant	KNApSAcK
Malva sylvestris	LOTUS Database	35616633
Pithecellobium dulce	LOTUS Database	35616633
Sterculia pallens	Plant	KNApSAcK
Sterculia tragacantha	LOTUS Database	35616633
Syzygium cumini	LOTUS Database	35616633
Trichodesma zeylanicum	LOTUS Database	35616633
Turnera ulmifolia	LOTUS Database	35616633
Urena lobata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-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:6673 )
monounsaturated fatty acid (CHEBI:6673 )
cyclopropenyl fatty acid (CHEBI:6673 )
Carbocyclic fatty acids (C08321 )
Fatty acids (C08321 )
Carbocyclic fatty acids (LMFA01140002 )

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	ALOGPS
logP	5.92	ChemAxon
logS	-4.9	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	14	ChemAxon
Refractivity	84.96 m³·mol⁻¹	ChemAxon
Polarizability	36.61 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

FDB004042

KNApSAcK ID

C00001227

Chemspider ID

Not Available

KEGG Compound ID

C08321

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Malvalic acid

METLIN ID

Not Available

PubChem Compound

10416

PDB ID

Not Available

ChEBI ID

6673

Good Scents ID

Not Available

References

General References

MACFARLANE JJ, SHENSTONE FS, VICKERY JR: Malvalic acid and its structure. Nature. 1957 Apr 20;179(4564):830-1. doi: 10.1038/179830a0. [PubMed:13430715 ]
Roomi MW, Hopkins CY: Some reactions of sterculic and malvalic acids. A new source of malvalic acid. Can J Biochem. 1970 Jul;48(7):759-62. doi: 10.1139/o70-119. [PubMed:5512548 ]

Showing NP-Card for Malvalic acid (NP0046333)

MOL for NP0046333 (Malvalic acid)

3D MOL for NP0046333 (Malvalic acid)

3D SDF for NP0046333 (Malvalic acid)

3D-SDF for NP0046333 (Malvalic acid)

PDB for NP0046333 (Malvalic acid)

3D PDB for NP0046333 (Malvalic acid)

SMILES for NP0046333 (Malvalic acid)

INCHI for NP0046333 (Malvalic acid)

Structure for NP0046333 (Malvalic acid)

3D Structure for NP0046333 (Malvalic acid)