NP-MRD: Showing NP-Card for 12S-HHT (NP0339033)

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Record Information

Version

2.0

Created at

2024-09-11 19:21:44 UTC

Updated at

2024-09-11 19:21:44 UTC

NP-MRD ID

NP0339033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12S-HHT

Description

12S-HHT, also known as 12-hhtre, 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. Thus, 12S-HHT is considered to be an eicosanoid lipid molecule. 12S-HHT is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 20 19  0  0  1  0            999 V2000
    8.0403  -15.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4528  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2778  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6903  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5153  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9278  -13.3391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5153  -12.6247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7528  -13.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1653  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9903  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4028  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2278  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6403  -15.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4653  -15.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8778  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7028  -14.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1153  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9403  -14.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3528  -14.7681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3528  -13.3391    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  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339033

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1

> <INCHI_KEY>
KUKJHGXXZWHSBG-WBGSEQOASA-N

> <FORMULA>
C17H28O3

> <MOLECULAR_WEIGHT>
280.4024

> <EXACT_MASS>
280.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.14970120106609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8E,10E,12S)-12-hydroxyheptadeca-5,8,10-trienoic acid

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
4.384575405666666

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677863984817

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.889630655845193

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759706509493094

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.5499

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-HHTrE

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      15.009 -28.901   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.779 -27.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.319 -27.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.089 -26.233   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.629 -26.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.399 -24.900   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.629 -23.566   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      21.939 -24.900   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.709 -26.233   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.249 -26.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.019 -27.567   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.559 -27.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.329 -28.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.869 -28.901   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.639 -27.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.179 -27.567   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.949 -26.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.489 -26.233   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      34.259 -27.567   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      34.259 -24.900   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6    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   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
12-HHTrE	ChEBI
12S-Hydroxy-5Z,8E,10E-heptadecatrienoic acid	ChEBI
(12S,5Z,8E,10E)-12-Hydroxy-5,8,10-heptadecatrienoic acid	Kegg
12S-Hydroxy-5Z,8E,10E-heptadecatrienoate	Generator
(12S,5Z,8E,10E)-12-Hydroxy-5,8,10-heptadecatrienoate	Generator
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoate	HMDB
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid	HMDB
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid anion	HMDB
12-Hydroxyheptadecatrienoate	HMDB
12-Hydroxyheptadecatrienoic acid	HMDB
HHT	HMDB
Hydroxyheptadecatrienate	HMDB
Hydroxyheptadecatrienoate	HMDB
Hydroxyheptadecatrienoic acid	HMDB
Hydroxyheptadecatrienoic acid anion	HMDB
12-L-Hydroxy-5,8,10-heptadecatrienoic acid	HMDB
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-isomer	HMDB
12-HHT	HMDB
12-Hydroxy-5,8,10-heptadecatrienoic acid	HMDB
12-Hydroxy-5,8,10-heptadecatrienoic acid, (e,Z,Z)-isomer	HMDB
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(e,Z,Z)-isomer	HMDB
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(Z,e,e)-isomer	HMDB
12S-HHT	ChEBI

Chemical Formula

C₁₇H₂₈O₃

Average Mass

280.4024 Da

Monoisotopic Mass

280.20384 Da

IUPAC Name

(5Z,8E,10E,12S)-12-hydroxyheptadeca-5,8,10-trienoic acid

Traditional Name

12-HHTrE

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1

InChI Key

KUKJHGXXZWHSBG-WBGSEQOASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Unsaturated fatty acid
Secondary alcohol
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

12-HHTrE (CHEBI:63977 )
Hydroxy/hydroperoxyeicosatrienoic acids (LMFA03050002 )

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	4.99	ALOGPS
logP	4.38	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	86.55 m³·mol⁻¹	ChemAxon
Polarizability	34.15 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

HMDB0012535

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029115

KNApSAcK ID

Not Available

Chemspider ID

4446265

KEGG Compound ID

C20388

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283141

PDB ID

Not Available

ChEBI ID

63977

Good Scents ID

Not Available

References

General References

Showing NP-Card for 12S-HHT (NP0339033)

MOL for NP0339033 (12S-HHT)

3D MOL for NP0339033 (12S-HHT)

3D SDF for NP0339033 (12S-HHT)

3D-SDF for NP0339033 (12S-HHT)

PDB for NP0339033 (12S-HHT)

3D PDB for NP0339033 (12S-HHT)

SMILES for NP0339033 (12S-HHT)

INCHI for NP0339033 (12S-HHT)

Structure for NP0339033 (12S-HHT)

3D Structure for NP0339033 (12S-HHT)