NP-MRD: Showing NP-Card for Hepoxilin B3 (NP0050322)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:48 UTC

Updated at

2022-04-27 20:52:48 UTC

NP-MRD ID

NP0050322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hepoxilin B3

Description

(10R)-hydroxy-(11S,12S)-epoxyicosa-(5Z,8Z,14Z)-trienoic acid belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain. Hepoxilin B3 is found in Murrayella periclados. Based on a literature review very few articles have been published on (10R)-hydroxy-(11S,12S)-epoxyicosa-(5Z,8Z,14Z)-trienoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222522D          

 24 24  0  0  1  0            999 V2000
   -4.9204    0.3316    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2059    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3493    2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0638    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7783    2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4927    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2072    2.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4927    4.0441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204   -0.4934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5079   -1.2079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7934   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329   -1.2079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349    0.7441    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  2  0  0  0  0
 10 12  1  0  0  0  0
 13  1  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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  1  0  0  0  0
 21 22  1  0  0  0  0
 14 23  1  0  0  0  0
 13 23  1  0  0  0  0
  1 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C[C@@H]1O[C@H]1[C@H](O)\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/b7-6-,12-9-,14-11-/t17-,18+,20+/m1/s1

> <INCHI_KEY>
DWNBPRRXEVJMPO-OANGEUSWSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.237090762851096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,10R)-10-hydroxy-10-[(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
4.730177758999999

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.747890205027268

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840400463

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3464728245471864

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
99.5658

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z,10R)-10-hydroxy-10-[(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

> <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      -9.185   0.619   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.851   1.389   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.851   2.929   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.185   3.699   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.185   5.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.518   6.009   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.852   5.239   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.186   6.009   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -14.519   5.239   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -15.853   6.009   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -17.187   5.239   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0     -15.853   7.549   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -9.185  -0.921   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.415  -2.255   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.081  -3.025   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.081  -4.565   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.747  -5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.080  -5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.413  -5.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.921  -4.565   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.955  -2.255   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0     -10.518   1.389   0.000  0.00  0.00           O+0
CONECT    1    2   13   24                                                  
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   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14   23                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   14   13                                                       
CONECT   24    1                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
(10R)-Hydroxy-(11S,12S)-epoxyeicosa-(5Z,8Z,14Z)-trienoic acid	ChEBI
(10R)-Hydroxy-(11S,12S)-epoxyeicosa-(5Z,8Z,14Z)-trienoate	Generator
(10R)-Hydroxy-(11S,12S)-epoxyicosa-(5Z,8Z,14Z)-trienoate	Generator

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

(5Z,8Z,10R)-10-hydroxy-10-[(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

Traditional Name

(5Z,8Z,10R)-10-hydroxy-10-[(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C[C@@H]1O[C@H]1[C@H](O)\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/b7-6-,12-9-,14-11-/t17-,18+,20+/m1/s1

InChI Key

DWNBPRRXEVJMPO-OANGEUSWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Murrayella periclados	-	KNApSAcK
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hepoxilins

Alternative Parents

Substituents

Hepoxilin
Medium-chain hydroxy acid
Medium-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:75696 )
epoxy fatty acid (CHEBI:75696 )
trienoic fatty acid (CHEBI:75696 )
hydroxy fatty acid (CHEBI:75696 )

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	5.11	ALOGPS
logP	4.73	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	39.24 Å³	ChemAxon
Number of Rings	1	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

Not Available

Chemspider ID

9242835

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11067683

PDB ID

Not Available

ChEBI ID

75696

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hepoxilin B3 (NP0050322)

MOL for NP0050322 (Hepoxilin B3)

3D MOL for NP0050322 (Hepoxilin B3)

3D SDF for NP0050322 (Hepoxilin B3)

3D-SDF for NP0050322 (Hepoxilin B3)

PDB for NP0050322 (Hepoxilin B3)

3D PDB for NP0050322 (Hepoxilin B3)

SMILES for NP0050322 (Hepoxilin B3)

INCHI for NP0050322 (Hepoxilin B3)

Structure for NP0050322 (Hepoxilin B3)

3D Structure for NP0050322 (Hepoxilin B3)