NP-MRD: Showing NP-Card for 9,10,13-TriHOME (NP0049963)

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Record Information

Version

2.0

Created at

2022-03-17 21:20:57 UTC

Updated at

2022-03-17 21:20:57 UTC

NP-MRD ID

NP0049963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,10,13-TriHOME

Description

9,10,13-TriHOME 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, 9,10,13-trihome is considered to be an octadecanoid lipid molecule. 9,10,13-TriHOME is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 9,10,13-TriHOME has been detected, but not quantified in, garden onions. This could make 9,10,13-trihome a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208042D          

 23 22  0  0  1  0            999 V2000
    4.1099  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8244  -14.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2532  -14.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9677  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6820  -14.9671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3964  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1109  -14.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8253  -15.3797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5397  -14.9671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2541  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9685  -14.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6829  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3974  -14.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8262  -14.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5406  -15.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2550  -14.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9695  -15.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2550  -14.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6820  -14.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5397  -14.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8253  -16.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
  6 21  1  6  0  0  0
 10 22  1  1  0  0  0
  9 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0049963

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O5/c1-2-3-7-10-15(19)13-14-17(21)16(20)11-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17+/m0/s1

> <INCHI_KEY>
NTVFQBIHLSPEGQ-SYMVGPSASA-N

> <FORMULA>
C18H34O5

> <MOLECULAR_WEIGHT>
330.4596

> <EXACT_MASS>
330.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.10363721885078

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
3.24727271

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.636226193576103

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615325350751434

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8471920611950203

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
91.79469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid

> <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       7.672 -28.709   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.005 -27.939   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.339 -28.709   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.673 -27.939   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.006 -28.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.340 -27.939   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.673 -28.709   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.007 -27.939   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.341 -28.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.674 -27.939   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.008 -28.709   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.341 -27.939   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.675 -28.709   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.008 -27.939   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.342 -28.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.676 -27.939   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.009 -28.709   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.343 -27.939   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      31.676 -28.709   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      30.343 -26.399   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.340 -26.399   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      19.674 -26.399   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      18.341 -30.249   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   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   22                                                  
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                                                            
CONECT   21    6                                                            
CONECT   22   10                                                            
CONECT   23    9                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
(9S,10R,11E,13S)-9,10,13-Trihydroxyoctadec-11-enoate	HMDB
9,10,13-Trihydroxyoctadec-11-enoic acid	HMDB
(11E)-9,10,13-Trihydroxyoctadec-11-enoate	HMDB
(11E)-9,10,13-Trihydroxyoctadec-11-enoic acid	HMDB
(e)-9,10,13-Trihydroxy-11-octadecenoate	HMDB
(e)-9,10,13-Trihydroxy-11-octadecenoic acid	HMDB
9,10,13-Trihydroxy-11-octadecenoate	HMDB
9,10,13-Trihydroxy-11-octadecenoic acid	HMDB
9,10,13-Trihydroxyoctadec-11-enoate	HMDB

Chemical Formula

C₁₈H₃₄O₅

Average Mass

330.4596 Da

Monoisotopic Mass

330.24062 Da

IUPAC Name

(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid

Traditional Name

(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid

CAS Registry Number

29907-57-1

SMILES

CCCCC[C@H](O)\C=C\[C@@H](O)[C@@H](O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O5/c1-2-3-7-10-15(19)13-14-17(21)16(20)11-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17+/m0/s1

InChI Key

NTVFQBIHLSPEGQ-SYMVGPSASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Polyol
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

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	3.76	ALOGPS
logP	3.25	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.79 m³·mol⁻¹	ChemAxon
Polarizability	39.1 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

HMDB0004710

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023419

KNApSAcK ID

Not Available

Chemspider ID

30776564

KEGG Compound ID

C14835

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14968868

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 9,10,13-TriHOME (NP0049963)

MOL for NP0049963 (9,10,13-TriHOME)

3D MOL for NP0049963 (9,10,13-TriHOME)

3D SDF for NP0049963 (9,10,13-TriHOME)

3D-SDF for NP0049963 (9,10,13-TriHOME)

PDB for NP0049963 (9,10,13-TriHOME)

3D PDB for NP0049963 (9,10,13-TriHOME)

SMILES for NP0049963 (9,10,13-TriHOME)

INCHI for NP0049963 (9,10,13-TriHOME)

Structure for NP0049963 (9,10,13-TriHOME)

3D Structure for NP0049963 (9,10,13-TriHOME)