NP-MRD: Showing NP-Card for Dihydroxystearic acid (NP0046331)

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Record Information

Version

2.0

Created at

2022-03-17 19:56:19 UTC

Updated at

2022-03-17 19:56:20 UTC

NP-MRD ID

NP0046331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydroxystearic acid

Description

Dihydroxystearic acid, also known as dihydroxystearate, 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. Dihydroxystearic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533007131513332D          

 22 21  0  0  0  0            999 V2000
    6.7105   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7296   -5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5546   -3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCC(O)(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(21,22)17(19)20/h21-22H,2-16H2,1H3,(H,19,20)

> <INCHI_KEY>
SXNBVULTHKFMNO-UHFFFAOYSA-N

> <FORMULA>
C18H36O4

> <MOLECULAR_WEIGHT>
316.482

> <EXACT_MASS>
316.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.15117672639202

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dihydroxyoctadecanoic acid

> <ALOGPS_LOGP>
5.64

> <JCHEM_LOGP>
6.0084578969999995

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.13443804110639

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.562775198532868

> <JCHEM_PKA_STRONGEST_BASIC>
-5.040931589657114

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
89.43059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-dihydroxyoctadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      12.526  -8.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.860  -8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.194  -8.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.527  -8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.861  -8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.195  -8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.528  -8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.862  -8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.196  -8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.529  -8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.863  -8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.197  -8.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.530  -8.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.864  -8.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.198  -8.772   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.532  -8.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.199  -9.542   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.865  -8.772   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      36.533  -8.772   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      35.199 -11.082   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      33.095 -10.106   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      34.635  -7.438   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                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   18                                                       
CONECT   17   18   19   20                                                  
CONECT   18   16   17   21   22                                             
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
Dihydroxystearate	Generator

Chemical Formula

C₁₈H₃₆O₄

Average Mass

316.4820 Da

Monoisotopic Mass

316.26136 Da

IUPAC Name

2,2-dihydroxyoctadecanoic acid

Traditional Name

2,2-dihydroxyoctadecanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCC(O)(O)C(O)=O

InChI Identifier

InChI=1S/C18H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(21,22)17(19)20/h21-22H,2-16H2,1H3,(H,19,20)

InChI Key

SXNBVULTHKFMNO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Hydroxy acid
Alpha-hydroxy acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carbonyl hydrate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	5.64	ALOGPS
logP	6.01	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.56	ChemAxon
pKa (Strongest Basic)	-5	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	89.43 m³·mol⁻¹	ChemAxon
Polarizability	40.15 Å³	ChemAxon
Number of Rings	0	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

FDB004024

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20391236

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dihydroxystearic acid (NP0046331)

MOL for NP0046331 (Dihydroxystearic acid)

3D MOL for NP0046331 (Dihydroxystearic acid)

3D SDF for NP0046331 (Dihydroxystearic acid)

3D-SDF for NP0046331 (Dihydroxystearic acid)

PDB for NP0046331 (Dihydroxystearic acid)

3D PDB for NP0046331 (Dihydroxystearic acid)

SMILES for NP0046331 (Dihydroxystearic acid)

INCHI for NP0046331 (Dihydroxystearic acid)

Structure for NP0046331 (Dihydroxystearic acid)

3D Structure for NP0046331 (Dihydroxystearic acid)