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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:07:19 UTC

Update Date

2022-09-22 18:35:00 UTC

HMDB ID

HMDB0341111

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid

Description

(2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on (2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092221452D          

 25 24  0  0  0  0            999 V2000
   -0.1914   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  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
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.1105    0.0000 O   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
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.1270    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341111

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCC(C)C(C)O)=C(\C)C(O)C\C([H])=C(/C)\C(\[H])=C(/[H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O4/c1-12(9-11-17(20)21)8-10-16(19)14(3)7-5-6-13(2)15(4)18/h7-9,11,13,15-16,18-19H,5-6,10H2,1-4H3,(H,20,21)/b11-9+,12-8+,14-7+

> <INCHI_KEY>
RCKDDMWGRIYLCN-WRHFRISWSA-N

> <FORMULA>
C17H28O4

> <MOLECULAR_WEIGHT>
296.407

> <EXACT_MASS>
296.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.99931436930425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid

> <JCHEM_LOGP>
2.797637669666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.248542946240303

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.792511616220976

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0597067373077431

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
87.50569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0      -0.357  -0.206   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   3.644   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.025   1.334   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.025  -0.206   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.692   1.334   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -5.692  -0.206   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      -7.026   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.026   3.644   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.359   1.334   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -8.359  -0.206   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      -9.693   2.104   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      -9.693   3.644   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0     -11.027   1.334   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -11.027  -0.206   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -12.360   2.104   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,4E,8E)-7,13-Dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoate	Generator

Chemical Formula

C₁₇H₂₈O₄

Average Molecular Weight

296.407

Monoisotopic Molecular Weight

296.198759382

IUPAC Name

(2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid

Traditional Name

(2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCC(C)C(C)O)=C(\C)C(O)C\C([H])=C(/C)\C(\[H])=C(/[H])C(O)=O

InChI Identifier

InChI=1S/C17H28O4/c1-12(9-11-17(20)21)8-10-16(19)14(3)7-5-6-13(2)15(4)18/h7-9,11,13,15-16,18-19H,5-6,10H2,1-4H3,(H,20,21)/b11-9+,12-8+,14-7+

InChI Key

RCKDDMWGRIYLCN-WRHFRISWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Long-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.8	ChemAxon
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-1.1	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	9	ChemAxon
Refractivity	87.51 m³·mol⁻¹	ChemAxon
Polarizability	35 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

Predicted Chromatographic Properties

Predicted Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

22912724

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23786291

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for (2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid (HMDB0341111)

MOL for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

3D MOL for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

3D SDF for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

3D-SDF for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

PDB for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

3D PDB for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

SMILES for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

INCHI for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

Structure for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

3D Structure for HMDB0341111 ((2E,4E,8E)-7,13-dihydroxy-4,8,12-trimethyltetradeca-2,4,8-trienoic acid)

Predicted Retention Times

Predicted Kovats Retention Indices