Showing Compound Card for PA(16:0/16:0) (CDB000806)

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Record Information
Version1.0
Created at2020-03-30 17:44:01 UTC
Updated at2020-12-07 19:07:47 UTC
CannabisDB IDCDB000806
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePA(16:0/16:0)
DescriptionPA(16:0/16:0)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(16:0/16:0), in particular, consists of two hexadecanoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC35H69O8P
Average Molecular Weight648.9
Monoisotopic Molecular Weight648.473
IUPAC Name[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid
Traditional Namedipalmitoyl
CAS Registry Number7091-44-3
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1
InChI KeyPORPENFLTBBHSG-MGBGTMOVSA-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 Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.66ALOGPS
logP11.88ChemAxon
logS-6.7ALOGPS
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 Count36ChemAxon
Refractivity178.57 m³·mol⁻¹ChemAxon
Polarizability80.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPA(16:0/16:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-9236341000-d0296e5b3dd53599a39dSpectrum
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Probable phospholipid-transporting ATPase IGATP11CQ8NB49 details
Probable phospholipid-transporting ATPase IHATP11A13q34P98196 details
Probable phospholipid-transporting ATPase VAATP10A15q11.2O60312 details
Probable phospholipid-transporting ATPase ICATP8B118q21-q22|18q21.31O43520 details
Probable phospholipid-transporting ATPase IIAATP9A20q13.2O75110 details
Probable phospholipid-transporting ATPase VDATP10D4p12Q9P241 details
Probable phospholipid-transporting ATPase IBATP8A213q12Q9NTI2 details
Probable phospholipid-transporting ATPase IAATP8A14p13Q9Y2Q0 details
Probable phospholipid-transporting ATPase IMATP8B415q21.2Q8TF62 details
Probable phospholipid-transporting ATPase IFATP11B3q27Q9Y2G3 details
Probable phospholipid-transporting ATPase IKATP8B319p13.3O60423 details
Probable phospholipid-transporting ATPase VBATP10B5q34O94823 details
Probable phospholipid-transporting ATPase IDATP8B21q21.3P98198 details
Metal Bindings
Receptors
Protein NameGene NameLocusUniprot IDDetails
Phospholipase D2PLD217p13.1O14939 details
Diacylglycerol kinase thetaDGKQ4p16.3P52824 details
Diacylglycerol kinase gammaDGKG3q27.2-q27.3P49619 details
Diacylglycerol kinase alphaDGKA12q13.3P23743 details
Diacylglycerol kinase deltaDGKD2q37.1Q16760 details
Lipid phosphate phosphohydrolase 1PPAP2A5q11O14494 details
Diacylglycerol kinase betaDGKB7p21.2Q9Y6T7 details
Diacylglycerol kinase iotaDGKI7q32.3-q33O75912 details
Lipid phosphate phosphohydrolase 3PPAP2B1p32.2O14495 details
Diacylglycerol kinase zetaDGKZ11p11.2Q13574 details
Phosphatidylinositol-glycan-specific phospholipase DGPLD16p22.1P80108 details
Diacylglycerol kinase etaDGKH13q14.11Q86XP1 details
Diacylglycerol kinase kappaDGKKQ5KSL6 details
Acylglycerol kinase, mitochondrialAGK7q34Q53H12 details
Diacylglycerol kinase, epsilon 64kDaDGKE17q22A1L4Q0 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Lipid phosphate phosphohydrolase 3PPAP2B1p32.2O14495 details
Concentrations Data
Not Available
HMDB IDHMDB0000674
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022175
KNApSAcK IDNot Available
Chemspider ID393518
KEGG Compound IDC00416
BioCyc IDCPD0-1422
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5644
PubChem Compound446066
PDB IDNot Available
ChEBI ID73246
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 109 proteins in total.

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Enzymes

Enzyme Details
1. Phospholipase D2
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
Enzyme Details
2. Diacylglycerol kinase theta
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
Enzyme Details
3. Diacylglycerol kinase gamma
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
Enzyme Details
4. Lipid phosphate phosphohydrolase 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 PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
Enzyme Details
5. Diacylglycerol kinase alpha
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
Enzyme Details
6. Diacylglycerol kinase delta
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
Enzyme Details
7. Lipid phosphate phosphohydrolase 1
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
Enzyme Details
8. Diacylglycerol kinase beta
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
Enzyme Details
9. Diacylglycerol kinase iota
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
Enzyme Details
10. Lipid phosphate phosphohydrolase 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 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

Transporters

Enzyme Details
1. Probable phospholipid-transporting ATPase IG
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11C
Uniprot ID:
Q8NB49
Molecular weight:
129476.0
Enzyme Details
2. Probable phospholipid-transporting ATPase IH
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11A
Uniprot ID:
P98196
Molecular weight:
129754.6
Enzyme Details
3. Probable phospholipid-transporting ATPase VA
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10A
Uniprot ID:
O60312
Molecular weight:
167686.6
Enzyme Details
4. Probable phospholipid-transporting ATPase IC
General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids in the canicular membrane. May have a role in transport of bile acids into the canaliculus, uptake of bile acids from intestinal contents into intestinal mucosa or both
Gene Name:
ATP8B1
Uniprot ID:
O43520
Molecular weight:
143694.1
Enzyme Details
5. Probable phospholipid-transporting ATPase IIA
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP9A
Uniprot ID:
O75110
Molecular weight:
118581.5
Enzyme Details
6. Probable phospholipid-transporting ATPase VD
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10D
Uniprot ID:
Q9P241
Molecular weight:
160272.3
Enzyme Details
7. Probable phospholipid-transporting ATPase IB
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP8A2
Uniprot ID:
Q9NTI2
Molecular weight:
129240.4
Enzyme Details
8. Probable phospholipid-transporting ATPase IA
General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:
ATP8A1
Uniprot ID:
Q9Y2Q0
Molecular weight:
131368.2
Enzyme Details
9. Probable phospholipid-transporting ATPase IM
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP8B4
Uniprot ID:
Q8TF62
Molecular weight:
135867.0
Enzyme Details
10. Probable phospholipid-transporting ATPase IF
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11B
Uniprot ID:
Q9Y2G3
Molecular weight:
134188.6

Only showing the first 10 proteins. There are 109 proteins in total.

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