[(2S)-3-hydroxy-2-[(E)-octadec-9-enoyl]oxypropyl] (E)-octadec-9-enoate

Details

• Internal ID: 198a37d3-3234-4b54-b1d6-a961788d71c5
• Taxonomy: Lipids and lipid-like molecules > Glycerolipids > Diradylglycerols > Diacylglycerols > 1,2-diacylglycerols
• IUPAC Name: [(2S)-3-hydroxy-2-[(E)-octadec-9-enoyl]oxypropyl] (E)-octadec-9-enoate
• SMILES (Canonical): CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCCCCCCCC
• SMILES (Isomeric): CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC/C=C/CCCCCCCC
• InChI: InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17+,20-18+/t37-/m0/s1
• InChI Key: AFSHUZFNMVJNKX-BIJVAZSDSA-N
• Popularity: 272 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₇₂O₅
• Molecular Weight: 621.00 g/mol
• Exact Mass: 620.53797539 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 14.30
• Atomic LogP (AlogP): 11.51
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 34

Synonyms

• [(2S)-3-hydroxy-2-[(E)-octadec-9-enoyl]oxypropyl] (E)-octadec-9-enoate
• (?)-1,2-Dielaidin
• BDBM50087240
• AKOS037647393
• AS-73508
• Bis(9-octadecenoic acid)(S)-3-hydroxypropane-1,2-diyl ester
• (2S)-1-hydroxy-3-(octadec-9-enoyloxy)propan-2-yl octadec-9-enoate
• (E)-Octadec-9-enoic acid (S)-1-hydroxymethyl-2-((E)-octadec-9-enoyloxy)-ethyl ester
• Octadec-9-enoic acid 1-hydroxymethyl-2-octadec-9-enoyloxy-ethyl ester(DIOLEIN)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9538	95.38%
Caco-2	-	0.7547	75.47%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7837	78.37%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.7841	78.41%
OATP1B3 inhibitior	+	0.9322	93.22%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6216	62.16%
P-glycoprotein inhibitior	+	0.6761	67.61%
P-glycoprotein substrate	-	0.8668	86.68%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.6878	68.78%
CYP2C9 inhibition	-	0.8855	88.55%
CYP2C19 inhibition	-	0.8587	85.87%
CYP2D6 inhibition	-	0.9144	91.44%
CYP1A2 inhibition	-	0.8081	80.81%
CYP2C8 inhibition	-	0.8282	82.82%
CYP inhibitory promiscuity	-	0.9154	91.54%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7423	74.23%
Carcinogenicity (trinary)	Non-required	0.6711	67.11%
Eye corrosion	-	0.9049	90.49%
Eye irritation	-	0.7152	71.52%
Skin irritation	-	0.7718	77.18%
Skin corrosion	-	0.9766	97.66%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4564	45.64%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.9227	92.27%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	-	0.9667	96.67%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.6237	62.37%
Acute Oral Toxicity (c)	IV	0.4570	45.70%
Estrogen receptor binding	+	0.7135	71.35%
Androgen receptor binding	-	0.8045	80.45%
Thyroid receptor binding	-	0.5791	57.91%
Glucocorticoid receptor binding	-	0.5676	56.76%
Aromatase binding	-	0.6767	67.67%
PPAR gamma	+	0.5552	55.52%
Honey bee toxicity	-	0.9489	94.89%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	+	0.7858	78.58%
Fish aquatic toxicity	+	0.9389	93.89%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL299	P17252	Protein kinase C alpha	87.2 nM	Ki	PMID: 10762046

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.81%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	95.33%	97.29%
CHEMBL2581	P07339	Cathepsin D	94.44%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.38%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	93.25%	89.63%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	92.77%	85.94%
CHEMBL299	P17252	Protein kinase C alpha	92.40%	98.03%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.48%	92.08%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.75%	92.86%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.66%	96.95%
CHEMBL5255	O00206	Toll-like receptor 4	88.36%	92.50%
CHEMBL1781	P11387	DNA topoisomerase I	85.45%	97.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	85.31%	91.81%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.95%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.78%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.25%	91.19%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.07%	95.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.90%	100.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.41%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.21%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.94%	94.33%

Plants that contains it

• Aconitum burnatii
• Alseodaphne paludosa
• Annona impressivenia
• Bersama yangambiensis
• Caloncoba echinata
• Castanopsis sclerophylla
• Conocephalum japonicum
• Cordylanthus kingii
• Croton cascarilloides
• Disynaphia halimifolia
• Eragrostis viscosa
• Forsteronia refracta
• Fridericia chica
• Grewia mollis
• Gymnocarpium robertianum
• Heliotropium floridum
• Heterotheca grandiflora
• Hovenia acerba
• Juglans nigra
• Kaempferia marginata
• Kaunia saltensis
• Mangifera indica
• Nauclea officinalis
• Ruta pinnata
• Salvia dorrii
• Sophora flavescens var. flavescens
• Stevia polycephala
• Teucrium cubense
• Thymus piperella
• Trichilia rubescens
• Uraria picta

Cross-Links

• PubChem: 6505653
• NPASS: NPC141481
• ChEMBL: CHEMBL57517