NP-MRD: Showing NP-Card for 12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid (NP0050306)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:12 UTC

Updated at

2022-04-27 20:52:12 UTC

NP-MRD ID

NP0050306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid

Description

(9S,10E)-9-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-10-enoic acid 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. 12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid is found in Lyngbya majuscula. Based on a literature review very few articles have been published on (9S,10E)-9-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-10-enoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222522D          

 22 22  0  0  1  0            999 V2000
    2.7770    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4914    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7783    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4927    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4927    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1914    1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    2.2539    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  2  0  0  0  0
  9 11  1  0  0  0  0
  1 12  1  6  0  0  0
  1 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C[C@@H]1O[C@H]1\C=C\[C@@H](O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O4/c1-2-3-7-11-16-17(22-16)14-13-15(19)10-8-5-4-6-9-12-18(20)21/h3,7,13-17,19H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-,14-13+/t15-,16-,17-/m0/s1

> <INCHI_KEY>
MGYJEJUWQRJNBN-SZTSADAQSA-N

> <FORMULA>
C18H30O4

> <MOLECULAR_WEIGHT>
310.434

> <EXACT_MASS>
310.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.15918726407703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10E)-9-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-10-enoic acid

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
4.047054625666666

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.889239887963747

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745183845104

> <JCHEM_PKA_STRONGEST_BASIC>
-2.847246473022021

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
89.4012

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10E)-9-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-10-enoic 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       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.517   2.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.851   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.185   2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.518   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.852   2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.186   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.519   2.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.853   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      17.187   2.874   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.853   0.564   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.184   0.564   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.850   2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.516   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.183   2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.357   2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.025   2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.358   0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.025  -0.206   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.413   4.207   0.000  0.00  0.00           O+0
CONECT    1    2   12   13                                                  
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                                                            
CONECT   12    1                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   16   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(9S,10E)-9-Hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-10-enoate	Generator

Chemical Formula

C₁₈H₃₀O₄

Average Mass

310.4340 Da

Monoisotopic Mass

310.21441 Da

IUPAC Name

(9S,10E)-9-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-10-enoic acid

Traditional Name

(9S,10E)-9-hydroxy-11-[(2S,3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl]undec-10-enoic acid

CAS Registry Number

Not Available

SMILES

CC\C=C/C[C@@H]1O[C@H]1\C=C\[C@@H](O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O4/c1-2-3-7-11-16-17(22-16)14-13-15(19)10-8-5-4-6-9-12-18(20)21/h3,7,13-17,19H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-,14-13+/t15-,16-,17-/m0/s1

InChI Key

MGYJEJUWQRJNBN-SZTSADAQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lyngbya majuscula	-	KNApSAcK

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

Molecular Framework

Aliphatic heteromonocyclic 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	4.58	ALOGPS
logP	4.05	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-2.8	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	13	ChemAxon
Refractivity	89.4 m³·mol⁻¹	ChemAxon
Polarizability	37.16 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

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

162845303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid (NP0050306)

MOL for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

3D MOL for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

3D SDF for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

3D-SDF for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

PDB for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

3D PDB for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

SMILES for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

INCHI for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

Structure for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)

3D Structure for NP0050306 (12S,13S-Epoxy-9S-hydroxy-10E,15Z-octadecadienoic acid)