Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-09 04:03:36 UTC
Update Date2022-11-30 19:26:07 UTC
HMDB IDHMDB0115247
Secondary Accession NumbersNone
Metabolite Identification
Common NamePA(22:0/18:1(11Z))
DescriptionPA(22:0/18:1(11Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(22:0/18:1(11Z)), in particular, consists of one chain of behenic acid at the C-1 position and one chain of cis-vaccenic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
Structure
Data?1563873576
Synonyms
ValueSource
1-behenoyl-2-cis-vaccenoyl-sn-glycero-3-phosphate SMPDB, HMDB
1-behenoyl-2-cis-vaccenoyl-sn-phosphatidic acid SMPDB, HMDB
PA(22:0/18:1) SMPDB, HMDB
PA(22:0/18:1n7) SMPDB, HMDB
PA(22:0/18:1w7) SMPDB, HMDB
PA(40:1) SMPDB, HMDB
Phosphatidic acid(22:0/18:1(11Z)) SMPDB, HMDB
Phosphatidic acid(22:0/18:1) SMPDB, HMDB
Phosphatidic acid(22:0/18:1n7) SMPDB, HMDB
Phosphatidic acid(22:0/18:1w7) SMPDB, HMDB
Phosphatidic acid(40:1) SMPDB, HMDB
Phosphatidate(22:0/18:1(11Z)) SMPDB, HMDB
Phosphatidate(22:0/18:1) SMPDB, HMDB
Phosphatidate(22:0/18:1n7) SMPDB, HMDB
Phosphatidate(22:0/18:1w7) SMPDB, HMDB
Phosphatidate(40:1)SMPDB, HMDB
PA(22:0/18:1(11Z))SMPDB
[(2R)-3-(Docosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonateGenerator, HMDB
Chemical FormulaC43H83O8P
Average Molecular Weight759.103
Monoisotopic Molecular Weight758.582556631
IUPAC Name[(2R)-3-(docosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-(docosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C43H83O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-42(44)49-39-41(40-50-52(46,47)48)51-43(45)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h14,16,41H,3-13,15,17-40H2,1-2H3,(H2,46,47,48)/b16-14-/t41-/m1/s1
InChI KeyQQWDHWISBPGDTI-MITQYPHISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP9.8ALOGPS
logP15.07ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity216.5 m³·mol⁻¹ChemAxon
Polarizability96.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+291.15531661259
DarkChem[M-H]-277.63431661259
DeepCCS[M+H]+280.30930932474
DeepCCS[M-H]-277.04930932474
DeepCCS[M-2H]-311.30430932474
DeepCCS[M+Na]+287.80730932474
AllCCS[M+H]+292.332859911
AllCCS[M+H-H2O]+292.232859911
AllCCS[M+NH4]+292.432859911
AllCCS[M+Na]+292.432859911
AllCCS[M-H]-278.832859911
AllCCS[M+Na-2H]-284.532859911
AllCCS[M+HCOO]-290.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PA(22:0/18:1(11Z))[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC4755.3Standard polar33892256
PA(22:0/18:1(11Z))[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC4628.5Standard non polar33892256
PA(22:0/18:1(11Z))[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC5417.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PA(22:0/18:1(11Z)),1TMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C5369.5Semi standard non polar33892256
PA(22:0/18:1(11Z)),1TMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C4734.6Standard non polar33892256
PA(22:0/18:1(11Z)),1TMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C6191.2Standard polar33892256
PA(22:0/18:1(11Z)),1TBDMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C5619.0Semi standard non polar33892256
PA(22:0/18:1(11Z)),1TBDMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C4826.9Standard non polar33892256
PA(22:0/18:1(11Z)),1TBDMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C6161.1Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 10V, Positive-QTOFsplash10-06di-2187903700-adb8ed4168fb96cb50a52019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 20V, Positive-QTOFsplash10-01ba-3298403200-4986857a24ec326f6dbc2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 40V, Positive-QTOFsplash10-007k-1198014100-b09401d3bae497d6df002019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 10V, Negative-QTOFsplash10-05ci-4049400300-bfc999be7e9e71accddb2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 20V, Negative-QTOFsplash10-004i-9014000000-469a648d6a6f3edff9192019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 40V, Negative-QTOFsplash10-004i-9000000000-b9f6c7a56f6ef97f11332019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 10V, Positive-QTOFsplash10-052f-0000000900-540cfac6970230e32fac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 20V, Positive-QTOFsplash10-0bt9-0000005900-17a866e7ada6cfea56232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 40V, Positive-QTOFsplash10-0400-0000906200-ae0b162e4a5fc7f03a872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 10V, Negative-QTOFsplash10-0a4i-0000000900-942ad965209c5d0744ca2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 20V, Negative-QTOFsplash10-05s0-0033900400-ebd90348663747a421492021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 40V, Negative-QTOFsplash10-0019-1169600100-577663326f1203c448132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 10V, Positive-QTOFsplash10-001i-0000000900-c739ae06c037ae9254ce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 20V, Positive-QTOFsplash10-001i-0000009900-eaeda140a740dcc44fcd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(22:0/18:1(11Z)) 40V, Positive-QTOFsplash10-001m-0000922400-73d14e990b0180a0c7482021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131822057
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 61 proteins in total.

Enzymes

General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485
General function:
Involved in diacylglycerol kinase activity
Specific function:
Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:
DGKQ
Uniprot ID:
P52824
Molecular weight:
101154.0
General function:
Involved in diacylglycerol kinase activity
Specific function:
Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:
DGKG
Uniprot ID:
P49619
Molecular weight:
89095.3
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
General function:
Involved in diacylglycerol kinase activity
Specific function:
Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:
DGKA
Uniprot ID:
P23743
Molecular weight:
82629.5
General function:
Involved in diacylglycerol kinase activity
Specific function:
Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:
DGKD
Uniprot ID:
Q16760
Molecular weight:
134524.2
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
General function:
Involved in diacylglycerol kinase activity
Specific function:
Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:
DGKB
Uniprot ID:
Q9Y6T7
Molecular weight:
90594.7
General function:
Involved in diacylglycerol kinase activity
Specific function:
ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:
DGKI
Uniprot ID:
O75912
Molecular weight:
116996.2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61

Only showing the first 10 proteins. There are 61 proteins in total.