MiMeDB: Showing metabocard for LysoPA(15:0cycw5/0:0) (MMDBc0056519)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-07-07 21:51:50 UTC

Update Date

2023-12-14 16:53:42 UTC

Metabolite ID

MMDBc0056519

Metabolite Identification

Common Name

LysoPA(15:0cycw5/0:0)

Description

LysoPA(15:0cycw5/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. LysoPA(15:0cycw5/0:0) in particular, consists of one chain of cis-9,10-Methylenetetradecanoic acid. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid and is extremely important biologically, influencing many biochemical processes.

Structure

MOL SDF PDB SMILES InChI

LPA(15:0cycw5/0:0)
  Mrv1652308091922422D          

 26 26  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -3.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

LPA(15:0cycw5/0:0)
  Mrv1652308091922422D          

 26 26  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -3.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056519

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCC1CC1CCCCCCCC(=O)OCC(O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H35O7P/c1-2-3-9-15-12-16(15)10-7-5-4-6-8-11-18(20)24-13-17(19)14-25-26(21,22)23/h15-17,19H,2-14H2,1H3,(H2,21,22,23)

> <INCHI_KEY>
MMKGPHVKZFVYHL-UHFFFAOYSA-N

> <FORMULA>
C18H35O7P

> <MOLECULAR_WEIGHT>
394.445

> <EXACT_MASS>
394.212040465

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.759556920395696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-hydroxypropoxy)phosphonic acid

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
3.735080143333334

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
98.47239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-AUG-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LPA(15:0cycw5/0:0)                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-AUG-19         0                                  
HETATM    1  O   UNK     0      17.163  -8.364   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.687  -6.808   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.718  -9.888   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.243  -8.332   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      18.703  -8.348   0.000  0.00  0.00           P+0
HETATM    6  C   UNK     0      15.645  -7.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.319  -8.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.977  -7.537   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.652  -8.321   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.336  -9.833   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.310  -7.566   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.310  -6.126   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.977  -8.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.644  -7.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.311  -8.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.978  -7.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.645  -8.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.312  -7.566   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.979  -8.337   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.354  -7.566   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.687  -8.337   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.020  -7.566   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.353  -8.337   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.686  -7.566   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.019  -8.337   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.352  -7.566   0.000  0.00  0.00           C+0
CONECT    1    6    5                                                       
CONECT    2    5                                                            
CONECT    3    5                                                            
CONECT    4    5                                                            
CONECT    5    1    2    3    4                                             
CONECT    6    1    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   11                                                       
CONECT   10    7                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   20   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

Synonyms

Value	Source
(3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-hydroxypropoxy)phosphonate	Generator

Molecular Formula

C₁₈H₃₅O₇P

Average Mass

394.445

Monoisotopic Mass

394.212040465

IUPAC Name

(3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-hydroxypropoxy)phosphonic acid

Traditional Name

3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCC1CC1CCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C18H35O7P/c1-2-3-9-15-12-16(15)10-7-5-4-6-8-11-18(20)24-13-17(19)14-25-26(21,22)23/h15-17,19H,2-14H2,1H3,(H2,21,22,23)

InChI Key

MMKGPHVKZFVYHL-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.004 g/L	ALOGPS
logP	3.32	ALOGPS
logP	3.74	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	98.47 m³·mol⁻¹	ChemAxon
Polarizability	43.76 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for LysoPA(15:0cycw5/0:0) (MMDBc0056519)

MOL for #<Metabolite:0x00007feca29e93a0>

3D MOL for #<Metabolite:0x00007feca29e93a0>

3D SDF for #<Metabolite:0x00007feca29e93a0>

3D-SDF for #<Metabolite:0x00007feca29e93a0>

PDB for #<Metabolite:0x00007feca29e93a0>

3D PDB for #<Metabolite:0x00007feca29e93a0>

SMILES for #<Metabolite:0x00007feca29e93a0>

INCHI for #<Metabolite:0x00007feca29e93a0>

Structure for #<Metabolite:0x00007feca29e93a0>

3D Structure for #<Metabolite:0x00007feca29e93a0>