2,4,6-Decatrienoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-

Details

• Internal ID: b214e679-bd5b-4c56-a89c-0923b639821d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids > Phorbol esters
• IUPAC Name: [(1S,2S,6R,10S,11R,13S,14R,15R)-13-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] (2E,4E,6E)-deca-2,4,6-trienoate
• InChI: InChI=1S/C32H42O8/c1-7-8-9-10-11-12-13-14-25(35)39-28-20(3)31(38)23(26-29(5,6)32(26,28)40-21(4)34)16-22(18-33)17-30(37)24(31)15-19(2)27(30)36/h9-16,20,23-24,26,28,33,37-38H,7-8,17-18H2,1-6H3/b10-9+,12-11+,14-13+/t20-,23+,24-,26-,28-,30-,31-,32-/m1/s1
• InChI Key: UUDRJPRIBMGADE-YNOQIDMFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₈
• Molecular Weight: 554.70 g/mol
• Exact Mass: 554.28796829 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.52
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• NSC-336793
• 2,4,6-Decatrienoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
• 41568-95-0
• 2,4,6-Decatrienoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, [1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha)]-
• F2Y2AD9QJM
• CHEMBL446957
• 13-O-Acetyl-12-O-deca-2,4,6-trienoylphorbol
• (1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0{2,6}.0{11,13}]pentadeca-3,8-dien-14-yl (2E,4E,6E)-deca-2,4,6-trienoate
• 2,4,6-Decatrienoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, [1aR-[1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta(2E,4E,6E),9aalpha]]-
• 38937-42-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9670	96.70%
Caco-2	-	0.7977	79.77%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7048	70.48%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8176	81.76%
OATP1B3 inhibitior	+	0.9233	92.33%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7526	75.26%
BSEP inhibitior	+	0.9350	93.50%
P-glycoprotein inhibitior	+	0.7933	79.33%
P-glycoprotein substrate	+	0.6286	62.86%
CYP3A4 substrate	+	0.6891	68.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9209	92.09%
CYP3A4 inhibition	-	0.7730	77.30%
CYP2C9 inhibition	+	0.7518	75.18%
CYP2C19 inhibition	-	0.8842	88.42%
CYP2D6 inhibition	-	0.9142	91.42%
CYP1A2 inhibition	-	0.8742	87.42%
CYP2C8 inhibition	+	0.6712	67.12%
CYP inhibitory promiscuity	-	0.7494	74.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6494	64.94%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9149	91.49%
Skin irritation	-	0.6062	60.62%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7931	79.31%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5723	57.23%
skin sensitisation	-	0.8177	81.77%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7436	74.36%
Acute Oral Toxicity (c)	III	0.5825	58.25%
Estrogen receptor binding	+	0.7378	73.78%
Androgen receptor binding	+	0.7240	72.40%
Thyroid receptor binding	+	0.6429	64.29%
Glucocorticoid receptor binding	+	0.7598	75.98%
Aromatase binding	+	0.6826	68.26%
PPAR gamma	+	0.6393	63.93%
Honey bee toxicity	-	0.7767	77.67%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9137	91.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.76%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.75%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.43%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	94.42%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.74%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.99%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	90.76%	98.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.41%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.50%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.48%	89.34%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.86%	93.00%
CHEMBL4208	P20618	Proteasome component C5	83.65%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.27%	94.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.98%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.84%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.62%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.86%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.70%	94.80%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.25%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.06%	91.07%

Plants that contains it

• Aquilaria malaccensis

Cross-Links

• PubChem: 6450291
• LOTUS: LTS0109826
• wikiData: Q105279253