NP-MRD: Showing NP-Card for 7S,8S-Dihydroxylinoleic acid (NP0050311)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:23 UTC

Updated at

2022-04-27 20:52:23 UTC

NP-MRD ID

NP0050311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7S,8S-Dihydroxylinoleic acid

Description

7(S),8(S)-DiHODE, also known as (7S,8S)-dihode, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 7(S),8(S)-dihode is considered to be an octadecanoid. 7S,8S-Dihydroxylinoleic acid is found in Gaeumannomyces graminis. 7S,8S-Dihydroxylinoleic acid was first documented in 1994 (PMID: 8117115). Based on a literature review a small amount of articles have been published on 7(S),8(S)-DiHODE.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222522D          

 22 21  0  0  1  0            999 V2000
    0.8546    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    7.5059    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
 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  2  0  0  0  0
 16 18  1  0  0  0  0
 10 19  1  6  0  0  0
  9 20  1  6  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/[C@H](O)[C@@H](O)CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-10-13-16(19)17(20)14-11-9-12-15-18(21)22/h6-7,10,13,16-17,19-20H,2-5,8-9,11-12,14-15H2,1H3,(H,21,22)/b7-6-,13-10-/t16-,17-/m0/s1

> <INCHI_KEY>
NMONGVDUESEHOK-MPOZZNMKSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.45

> <EXACT_MASS>
312.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.657404051746326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoic acid

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
4.116162120333333

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.669296017554668

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.533043285667047

> <JCHEM_PKA_STRONGEST_BASIC>
-3.169709514402756

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
91.3958

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7S,8S)-DiHODE

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       1.595  11.701   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.929  10.931   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.929   9.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.595   8.621   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.595   7.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.929   6.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.596   6.311   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.595  13.241   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.262  14.011   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
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   20                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   10                                                            
CONECT   20    9                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
(7S,8S)-DiHODE	ChEBI
(7S,8S)-Dihydroxylinoleic acid	ChEBI
(9Z,12Z)-(7S,8S)-Dihydroxyoctadeca-9,12-dienoate	ChEBI
(9Z,12Z)-(7S,8S)-Dihydroxyoctadeca-9,12-dienoic acid	ChEBI
(7S,8S,9Z,12Z)-7,8-Dihydroxyoctadeca-9,12-dienoate	Kegg
(7S,8S)-Dihydroxylinoleate	Generator
(7S,8S,9Z,12Z)-7,8-Dihydroxyoctadeca-9,12-dienoic acid	Generator
7,8-Dihydroxylinoleic acid	MeSH

Chemical Formula

C₁₈H₃₂O₄

Average Mass

312.4500 Da

Monoisotopic Mass

312.23006 Da

IUPAC Name

(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoic acid

Traditional Name

(7S,8S)-DiHODE

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/[C@H](O)[C@@H](O)CCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-10-13-16(19)17(20)14-11-9-12-15-18(21)22/h6-7,10,13,16-17,19-20H,2-5,8-9,11-12,14-15H2,1H3,(H,21,22)/b7-6-,13-10-/t16-,17-/m0/s1

InChI Key

NMONGVDUESEHOK-MPOZZNMKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gaeumannomyces graminis	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dihydroxy monocarboxylic acid (CHEBI:15658 )
octadecanoid (CHEBI:15658 )
Hydroxy fatty acids (C07354 )
Other Octadecanoids (LMFA02000224 )

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	5.05	ALOGPS
logP	4.12	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-3.2	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	14	ChemAxon
Refractivity	91.4 m³·mol⁻¹	ChemAxon
Polarizability	36.66 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

Not Available

KNApSAcK ID

C00000399

Chemspider ID

4573945

KEGG Compound ID

C07354

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5460412

PDB ID

Not Available

ChEBI ID

15658

Good Scents ID

Not Available

References

General References

Hamberg M, Zhang LY, Brodowsky ID, Oliw EH: Sequential oxygenation of linoleic acid in the fungus Gaeumannomyces graminis: stereochemistry of dioxygenase and hydroperoxide isomerase reactions. Arch Biochem Biophys. 1994 Feb 15;309(1):77-80. doi: 10.1006/abbi.1994.1087. [PubMed:8117115 ]

Showing NP-Card for 7S,8S-Dihydroxylinoleic acid (NP0050311)

MOL for NP0050311 (7S,8S-Dihydroxylinoleic acid)

3D MOL for NP0050311 (7S,8S-Dihydroxylinoleic acid)

3D SDF for NP0050311 (7S,8S-Dihydroxylinoleic acid)

3D-SDF for NP0050311 (7S,8S-Dihydroxylinoleic acid)

PDB for NP0050311 (7S,8S-Dihydroxylinoleic acid)

3D PDB for NP0050311 (7S,8S-Dihydroxylinoleic acid)

SMILES for NP0050311 (7S,8S-Dihydroxylinoleic acid)

INCHI for NP0050311 (7S,8S-Dihydroxylinoleic acid)

Structure for NP0050311 (7S,8S-Dihydroxylinoleic acid)

3D Structure for NP0050311 (7S,8S-Dihydroxylinoleic acid)