NP-MRD: Showing NP-Card for 9,10-Dihydroxystearic acid (NP0046328)

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Record Information

Version

2.0

Created at

2022-03-17 19:56:16 UTC

Updated at

2022-03-17 19:56:16 UTC

NP-MRD ID

NP0046328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,10-Dihydroxystearic acid

Description

9,10-Dihydroxystearic acid, also known as 9,10-dhsa or 9,10-dioh 18:0, 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. 9,10-Dihydroxystearic acid is found in Apis cerana, Fusarium oxysporum, Ricinus communis and Trypanosoma brucei. 9,10-Dihydroxystearic acid was first documented in 2004 (PMID: 15005144). 9,10-Dihydroxystearic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161506232D          

 22 21  0  0  0  0            999 V2000
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    4.8908    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
  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC(O)C(O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)

> <INCHI_KEY>
VACHUYIREGFMSP-UHFFFAOYSA-N

> <FORMULA>
C18H36O4

> <MOLECULAR_WEIGHT>
316.482

> <EXACT_MASS>
316.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.78884256408016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,10-dihydroxyoctadecanoic acid

> <ALOGPS_LOGP>
5.27

> <JCHEM_LOGP>
4.684097973666667

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.909717016038154

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615325350944831

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1440192571762076

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
89.3166

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,10-dihydroxystearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      27.816  12.979   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      29.149   9.129   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.150  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      41.153  11.439   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      39.819   9.129   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
9,10-DHSA	ChEBI
9,10-Dihydroxystearinsaeure	ChEBI
9,10-DiOH 18:0	ChEBI
9,10-DiOH C18:0	ChEBI
DHSA	ChEBI
Dioxystearinsaeure	ChEBI
9,10-Dihydroxystearate	Generator
9,10-Dihydroxystearic acid, ammonium salt	MeSH
9,10-Dihydroxystearic acid, magnesium salt	MeSH
9,10-Dihydroxystearic acid, monocalcium salt	MeSH
9,10-Dihydroxystearic acid, sodium salt	MeSH
9,10-Dihydroxystearic acid, (r,s)-isomer	MeSH
9,10-Dihydroxystearic acid, potassium salt	MeSH
9,10-Dihydroxystearic acid, (r,r)-isomer	MeSH
9,10-Dihydroxystearic acid, dicalcium salt	MeSH
9,10-Dihydroxystearic acid, lithium salt	MeSH

Chemical Formula

C₁₈H₃₆O₄

Average Mass

316.4820 Da

Monoisotopic Mass

316.26136 Da

IUPAC Name

9,10-dihydroxyoctadecanoic acid

Traditional Name

9,10-dihydroxystearic acid

CAS Registry Number

120-87-6

SMILES

CCCCCCCCC(O)C(O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)

InChI Key

VACHUYIREGFMSP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fusarium oxysporum	Fungi	KNApSAcK
Ricinus communis	Plant	KNApSAcK
Trypanosoma brucei	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
Hydroxy fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dihydroxy monocarboxylic acid (CHEBI:28724 )
hydroxy fatty acid (CHEBI:28724 )
Other Octadecanoids (LMFA02000142 )

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	5.27	ALOGPS
logP	4.68	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	89.32 m³·mol⁻¹	ChemAxon
Polarizability	39.79 Å³	ChemAxon
Number of Rings	0	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

FDB004012

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19622

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

89377

PDB ID

Not Available

ChEBI ID

28724

Good Scents ID

Not Available

References

General References

Awang R, Basri M, Ahmad S, Salleh AB: Lipase-catalyzed esterification of palm-based 9,10-dihydroxystearic acid and 1-octanol in hexane--a kinetic study. Biotechnol Lett. 2004 Jan;26(1):11-4. doi: 10.1023/b:bile.0000009452.73477.26. [PubMed:15005144 ]

Showing NP-Card for 9,10-Dihydroxystearic acid (NP0046328)

MOL for NP0046328 (9,10-Dihydroxystearic acid)

3D MOL for NP0046328 (9,10-Dihydroxystearic acid)

3D SDF for NP0046328 (9,10-Dihydroxystearic acid)

3D-SDF for NP0046328 (9,10-Dihydroxystearic acid)

PDB for NP0046328 (9,10-Dihydroxystearic acid)

3D PDB for NP0046328 (9,10-Dihydroxystearic acid)

SMILES for NP0046328 (9,10-Dihydroxystearic acid)

INCHI for NP0046328 (9,10-Dihydroxystearic acid)

Structure for NP0046328 (9,10-Dihydroxystearic acid)

3D Structure for NP0046328 (9,10-Dihydroxystearic acid)