Hexadecanoic acid, (1S,1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-1,3-bis(hydroxymethyl)-1,6,8-trimethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester

Details

• Internal ID: acc274f5-dbbc-4388-a4df-38f8ff12f392
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids > Phorbol esters
• IUPAC Name: [(1S,2S,6R,10S,11R,12S,13S,14R,15R)-13-acetyloxy-1,6-dihydroxy-8,12-bis(hydroxymethyl)-4,12,15-trimethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] hexadecanoate
• InChI: InChI=1S/C38H60O9/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-31(42)46-34-26(3)37(45)29(32-35(5,24-40)38(32,34)47-27(4)41)21-28(23-39)22-36(44)30(37)20-25(2)33(36)43/h20-21,26,29-30,32,34,39-40,44-45H,6-19,22-24H2,1-5H3/t26-,29+,30-,32-,34-,35-,36-,37-,38-/m1/s1
• InChI Key: DYHBGVHTKOPQDM-SGPTVBMASA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₀O₉
• Molecular Weight: 660.90 g/mol
• Exact Mass: 660.42373349 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 5.51
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 18

Synonyms

• 53202-98-5
• 16-hydroxyphorbol 13-decanoate 12-palmitate
• 12-O-Palmitoyl-16-hydroxyphorbol 13-acetate
• 12-O-Palmitoyl-16-hydroxyphorbol-13-acetate
• 12-O-Hexadecanoyl-16-hydroxyphorbol-13-acetate
• NSC338250
• (1S,1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-1,3-bis(hydroxymethyl)-1,6,8-trimethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl hexadecanoate
• [(1S,2S,6R,10S,11R,12S,13S,14R,15R)-13-acetyloxy-1,6-dihydroxy-8,12-bis(hydroxymethyl)-4,12,15-trimethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] hexadecanoate
• PHORBOL-13-ACETATE, 12-O-PALMITOYL-16-HYDROXY
• CHEBI:744
• CHEMBL4296990
• DTXSID301098259
• NSC-338250
• C09153
• Q27105348
• Hexadecanoic acid, (1S,1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-1,3-bis(hydroxymethyl)-1,6,8-trimethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester
• Hexadecanoic acid,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-1,3-bis(hydroxymethyl)-1,6,8-trimethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, (1S-(1.alpha.,1a.alpha.,1b.beta.,4a.beta.,7a.alpha.,7b.alpha.,8.alpha.,9.beta.,9a.alpha.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9664	96.64%
Caco-2	-	0.8199	81.99%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8239	82.39%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.6119	61.19%
BSEP inhibitior	+	0.8783	87.83%
P-glycoprotein inhibitior	+	0.7476	74.76%
P-glycoprotein substrate	+	0.6466	64.66%
CYP3A4 substrate	+	0.6923	69.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9180	91.80%
CYP3A4 inhibition	-	0.7683	76.83%
CYP2C9 inhibition	+	0.6560	65.60%
CYP2C19 inhibition	-	0.8660	86.60%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.9039	90.39%
CYP2C8 inhibition	+	0.6445	64.45%
CYP inhibitory promiscuity	-	0.8805	88.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6912	69.12%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9041	90.41%
Skin irritation	+	0.4897	48.97%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3614	36.14%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5158	51.58%
skin sensitisation	-	0.9137	91.37%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5880	58.80%
Acute Oral Toxicity (c)	III	0.4829	48.29%
Estrogen receptor binding	+	0.7444	74.44%
Androgen receptor binding	+	0.7347	73.47%
Thyroid receptor binding	-	0.5992	59.92%
Glucocorticoid receptor binding	+	0.6417	64.17%
Aromatase binding	+	0.6364	63.64%
PPAR gamma	+	0.5847	58.47%
Honey bee toxicity	-	0.8184	81.84%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.7476	74.76%
Fish aquatic toxicity	+	0.9813	98.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2996	Q05655	Protein kinase C delta	99.14%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	98.82%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.01%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.84%	97.25%
CHEMBL3045	P05771	Protein kinase C beta	95.39%	97.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.12%	91.11%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.50%	91.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.07%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.80%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.74%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.38%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	86.30%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.91%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.88%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.82%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.64%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.56%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.25%	96.95%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.37%	91.81%
CHEMBL340	P08684	Cytochrome P450 3A4	81.52%	91.19%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.26%	85.94%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	80.85%	97.50%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.08%	97.29%

Plants that contains it

• Croton flavens
• Vernicia fordii

Cross-Links

• PubChem: 334044
• LOTUS: LTS0104951
• wikiData: Q27105348