MiMeDB: Showing metabocard for Octadecanoyl-phosphate (n-C18:1) (MMDBc0031628)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:42:00 UTC

Update Date

2022-08-31 18:22:38 UTC

Metabolite ID

MMDBc0031628

Metabolite Identification

Common Name

Octadecanoyl-phosphate (n-C18:1)

Description

Caprylic acid belongs to the class of Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain. (inferred from compound structure)Caprylic acid is invovled in Biosynthesis of alkaloids derived from terpenoid and polyketide, Biosynthesis of plant secondary metabolites, and Fatty acid biosynthesis. (KEGG)Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. It is found naturally in the milk of various mammals, and it is a minor constituent of coconut oil and palm kernel oil. It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste. Two other acids are named after goats: caproic (C6) and capric (C10). Along with caprylic acid these total 15% in goat milk fat. (WikiPedia)

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10101207462D          

 24 23  0  0  0  0            999 V2000
   -4.9500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    2.8579    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
   -1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000    1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.7750    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.7750    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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  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  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
M  CHG  2  22  -1  23  -1
M  END
> <DATABASE_ID>
MMDBc0031628

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)OP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H35O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)23-24(20,21)22/h9-10H,2-8,11-17H2,1H3,(H2,20,21,22)/p-2/b10-9-

> <INCHI_KEY>
VHHMNNRGNQWMKU-KTKRTIGZSA-L

> <FORMULA>
C18H33O5P

> <MOLECULAR_WEIGHT>
360.4254

> <EXACT_MASS>
360.206560678

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.02517730429497

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(9Z)-octadec-9-enoyloxy]phosphonate

> <ALOGPS_LOGP>
6.07

> <JCHEM_LOGP>
6.129933305333334

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.269641390864118

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2343681146728933

> <JCHEM_PKA_STRONGEST_BASIC>
-7.424671212634207

> <JCHEM_POLAR_SURFACE_AREA>
89.49000000000001

> <JCHEM_REFRACTIVITY>
96.31849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z)-octadec-9-enoyloxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0      -9.240   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.700   8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.930   6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.390   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.620   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.310   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.540   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850   6.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.240   5.335   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.240   2.667   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      10.780   2.667   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      12.320   2.667   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      10.780   1.127   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0      10.780   4.207   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    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   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Value	Source
Octadecanoyl-phosphoric acid (N-C18:1)	Generator
[(9Z)-Octadec-9-enoyloxy]phosphonic acid	Generator

Molecular Formula

C₁₈H₃₃O₅P

Average Mass

360.4254

Monoisotopic Mass

360.206560678

IUPAC Name

[(9Z)-octadec-9-enoyloxy]phosphonate

Traditional Name

(9Z)-octadec-9-enoyloxyphosphonate

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)OP([O-])([O-])=O

InChI Identifier

InChI=1S/C18H35O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)23-24(20,21)22/h9-10H,2-8,11-17H2,1H3,(H2,20,21,22)/p-2/b10-9-

InChI Key

VHHMNNRGNQWMKU-KTKRTIGZSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Acyl monophosphates

Alternative Parents

Substituents

Acyl monophosphate
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	6.07	ALOGPS
logP	6.13	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.49 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	96.32 m³·mol⁻¹	ChemAxon
Polarizability	41.03 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ik9-0009000000-2361557116c422dd00d6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-4139000000-1795c42a0a7754845d94	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9410000000-530d4b2e72fd8b625fc0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-3b954eee98387c233d8d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1029000000-2899c44aaa96fd4487a1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-298a95de0af3ec70d62c	2015-09-15	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

20981657

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for Octadecanoyl-phosphate (n-C18:1) (MMDBc0031628)

MOL for #<Metabolite:0x00007fed151f38d0>

3D MOL for #<Metabolite:0x00007fed151f38d0>

3D SDF for #<Metabolite:0x00007fed151f38d0>

3D-SDF for #<Metabolite:0x00007fed151f38d0>

PDB for #<Metabolite:0x00007fed151f38d0>

3D PDB for #<Metabolite:0x00007fed151f38d0>

SMILES for #<Metabolite:0x00007fed151f38d0>

INCHI for #<Metabolite:0x00007fed151f38d0>

Structure for #<Metabolite:0x00007fed151f38d0>

3D Structure for #<Metabolite:0x00007fed151f38d0>