NAV

(2R)-3-{[{[(2S)-2,3-DIHYDROXYPROPYL]OXY}(HYDROXY)PHOSPHORYL]OXY}-2-[(9E)-HEXADEC-9-ENOYLOXY]PROPYL (9E)-OCTADEC-9-ENOATE

Identification

Generic Name
(2R)-3-{[{[(2S)-2,3-DIHYDROXYPROPYL]OXY}(HYDROXY)PHOSPHORYL]OXY}-2-[(9E)-HEXADEC-9-ENOYLOXY]PROPYL (9E)-OCTADEC-9-ENOATE
DrugBank Accession Number
DB04683
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 746.9913
Monoisotopic: 746.509785132
Chemical Formula
C40H75O10P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USteroidogenic factor 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphoglycerols
Direct Parent
Phosphatidylglycerols
Alternative Parents
Fatty acid esters / Dialkyl phosphates / Dicarboxylic acids and derivatives / Secondary alcohols / Carboxylic acid esters / 1,2-diols / Primary alcohols / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1,2-diacylglycerophosphoglycerol / 1,2-diol / Alcohol / Aliphatic acyclic compound / Alkyl phosphate / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl phosphate / Dicarboxylic acid or derivatives
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QGIXWNRQEFVVRM-CTDKCSBDSA-N
InChI
InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h14,16-18,37-38,41-42H,3-13,15,19-36H2,1-2H3,(H,45,46)/b16-14-,18-17-/t37-,38-/m1/s1
IUPAC Name
[(2R)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](CO[P@](O)(=O)OC[C@H](O)CO)OC(=O)CCCCCCC\C=C/CCCCCC

References

General References
Not Available
PubChem Compound
5288113
PubChem Substance
46507864
ChemSpider
4450344
ZINC
ZINC000053683609
PDBe Ligand
DR9
PDB Entries
1ymt / 7kc4 / 7z0s

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000105 mg/mLALOGPS
logP8.02ALOGPS
logP11.1Chemaxon
logS-6.8ALOGPS
pKa (Strongest Acidic)1.89Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area148.82 Å2Chemaxon
Rotatable Bond Count40Chemaxon
Refractivity206.74 m3·mol-1Chemaxon
Polarizability89.88 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5761
Blood Brain Barrier+0.8748
Caco-2 permeable-0.6215
P-glycoprotein substrateSubstrate0.5557
P-glycoprotein inhibitor INon-inhibitor0.7535
P-glycoprotein inhibitor IINon-inhibitor0.8996
Renal organic cation transporterNon-inhibitor0.954
CYP450 2C9 substrateNon-substrate0.889
CYP450 2D6 substrateNon-substrate0.8292
CYP450 3A4 substrateNon-substrate0.5805
CYP450 1A2 substrateNon-inhibitor0.8116
CYP450 2C9 inhibitorNon-inhibitor0.8471
CYP450 2D6 inhibitorNon-inhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.8047
CYP450 3A4 inhibitorNon-inhibitor0.6986
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9696
Ames testNon AMES toxic0.8494
CarcinogenicityNon-carcinogens0.6453
BiodegradationNot ready biodegradable0.5169
Rat acute toxicity2.0274 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8742
hERG inhibition (predictor II)Non-inhibitor0.6753
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2816092800-16180c702d61b7243f85
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0000000900-7c06aaf0724190df4fc0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-9361442300-8d133c4bb59a356ccc6e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2100094000-fc00e92ae1d53e438a5b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0596-5773900000-b538c731e14be6d6ee42
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9581611000-eddcb74f198201969eac
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-286.50015
predicted
DeepCCS 1.0 (2019)
[M+H]+288.32504
predicted
DeepCCS 1.0 (2019)
[M+Na]+293.93094
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Steroidogenic factor 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Transcriptional activator. Seems to be essential for sexual differentiation and formation of the primary steroidogenic tissues. Binds to the Ad4 site found in the promoter region of steroidogenic P...
Gene Name
NR5A1
Uniprot ID
Q13285
Uniprot Name
Steroidogenic factor 1
Molecular Weight
51635.47 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52