[(1R,2S,4S,5R,8R,9S,10R,13R,15R)-15-acetyloxy-10-hydroxy-5-methoxycarbonyl-5,9-dimethyl-14-methylidene-2-propanoyloxy-8-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 3a5ec714-f5b5-4f5f-ad82-3429e2cb957e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: [(1R,2S,4S,5R,8R,9S,10R,13R,15R)-15-acetyloxy-10-hydroxy-5-methoxycarbonyl-5,9-dimethyl-14-methylidene-2-propanoyloxy-8-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CCC(=O)OC1CC2C(CCC(C2(C3(C14CC(CC3)C(=C)C4OC(=O)C)O)C)OC(=O)C5(C(O5)C)C)(C)C(=O)OC
• SMILES (Isomeric): CCC(=O)O[C@H]1C[C@@H]2[C@](CC[C@H]([C@]2([C@]3([C@]14C[C@@H](CC3)C(=C)[C@H]4OC(=O)C)O)C)OC(=O)[C@@]5([C@H](O5)C)C)(C)C(=O)OC
• InChI: InChI=1S/C31H44O10/c1-9-23(33)39-22-14-20-27(5,25(34)37-8)12-11-21(40-26(35)29(7)17(3)41-29)28(20,6)31(36)13-10-19-15-30(22,31)24(16(19)2)38-18(4)32/h17,19-22,24,36H,2,9-15H2,1,3-8H3/t17-,19-,20-,21-,22+,24-,27-,28+,29+,30-,31-/m1/s1
• InChI Key: ALHHAXMXDXKBQY-PICDMUPMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₁₀
• Molecular Weight: 576.70 g/mol
• Exact Mass: 576.29344760 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9862	98.62%
Caco-2	-	0.7628	76.28%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5897	58.97%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.8454	84.54%
OATP1B3 inhibitior	+	0.9089	90.89%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9274	92.74%
P-glycoprotein inhibitior	+	0.7277	72.77%
P-glycoprotein substrate	+	0.6543	65.43%
CYP3A4 substrate	+	0.7235	72.35%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8602	86.02%
CYP3A4 inhibition	+	0.7208	72.08%
CYP2C9 inhibition	-	0.5896	58.96%
CYP2C19 inhibition	-	0.6075	60.75%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.7172	71.72%
CYP2C8 inhibition	+	0.5347	53.47%
CYP inhibitory promiscuity	-	0.8813	88.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6726	67.26%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8762	87.62%
Skin irritation	+	0.5083	50.83%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6731	67.31%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.5077	50.77%
skin sensitisation	-	0.8445	84.45%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7408	74.08%
Acute Oral Toxicity (c)	III	0.3055	30.55%
Estrogen receptor binding	+	0.7626	76.26%
Androgen receptor binding	+	0.7402	74.02%
Thyroid receptor binding	+	0.5463	54.63%
Glucocorticoid receptor binding	+	0.7471	74.71%
Aromatase binding	+	0.7397	73.97%
PPAR gamma	+	0.6998	69.98%
Honey bee toxicity	-	0.7025	70.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	97.89%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.23%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.86%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.41%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.01%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.49%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	90.36%	89.50%
CHEMBL2996	Q05655	Protein kinase C delta	88.99%	97.79%
CHEMBL3837	P07711	Cathepsin L	88.83%	96.61%
CHEMBL259	P32245	Melanocortin receptor 4	88.51%	95.38%
CHEMBL4072	P07858	Cathepsin B	87.59%	93.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.01%	97.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.57%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.29%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.19%	96.38%
CHEMBL340	P08684	Cytochrome P450 3A4	84.35%	91.19%
CHEMBL2581	P07339	Cathepsin D	84.08%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.45%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.29%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.13%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.11%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.00%	82.69%
CHEMBL5028	O14672	ADAM10	81.77%	97.50%
CHEMBL233	P35372	Mu opioid receptor	81.65%	97.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.60%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.44%	94.00%
CHEMBL1871	P10275	Androgen Receptor	81.13%	96.43%

Plants that contains it

• Nidorella welwitschii
• Platycarphella carlinoides

Cross-Links

• PubChem: 162944535
• LOTUS: LTS0166812
• wikiData: Q104917954