[(1S,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-diacetyloxy-9-butoxy-5-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-10-yl] acetate

Details

• Internal ID: b7f4e341-101e-4bbf-a4c7-7eb4d097b396
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: [(1S,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-diacetyloxy-9-butoxy-5-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-10-yl] acetate
• SMILES (Canonical): CCCCOC1C(C(C2CC(C=C3C2(C1OC(=O)C)C(OC3OC(=O)C)OC(=O)C)O)(C)CC=C(C)C=C)C
• SMILES (Isomeric): CCCCO[C@@H]1[C@H]([C@@]([C@@H]2C[C@H](C=C3[C@@]2([C@H]1OC(=O)C)[C@@H](O[C@@H]3OC(=O)C)OC(=O)C)O)(C)C/C=C(\C)/C=C)C
• InChI: InChI=1S/C30H44O9/c1-9-11-14-35-25-18(4)29(8,13-12-17(3)10-2)24-16-22(34)15-23-27(37-20(6)32)39-28(38-21(7)33)30(23,24)26(25)36-19(5)31/h10,12,15,18,22,24-28,34H,2,9,11,13-14,16H2,1,3-8H3/b17-12+/t18-,22+,24+,25-,26+,27+,28-,29-,30-/m1/s1
• InChI Key: RGZYRGOVDQQYTL-LBVJXXHISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄O₉
• Molecular Weight: 548.70 g/mol
• Exact Mass: 548.29853298 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.38
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	-	0.7087	70.87%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6960	69.60%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.8205	82.05%
OATP1B3 inhibitior	+	0.9557	95.57%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9533	95.33%
P-glycoprotein inhibitior	+	0.8217	82.17%
P-glycoprotein substrate	+	0.5269	52.69%
CYP3A4 substrate	+	0.7049	70.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	+	0.6450	64.50%
CYP2C9 inhibition	-	0.7436	74.36%
CYP2C19 inhibition	-	0.8685	86.85%
CYP2D6 inhibition	-	0.9217	92.17%
CYP1A2 inhibition	-	0.8074	80.74%
CYP2C8 inhibition	+	0.6322	63.22%
CYP inhibitory promiscuity	-	0.8174	81.74%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4892	48.92%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.8993	89.93%
Skin irritation	+	0.7106	71.06%
Skin corrosion	-	0.9157	91.57%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7472	74.72%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8761	87.61%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6370	63.70%
Acute Oral Toxicity (c)	III	0.7531	75.31%
Estrogen receptor binding	+	0.8254	82.54%
Androgen receptor binding	+	0.6659	66.59%
Thyroid receptor binding	-	0.5082	50.82%
Glucocorticoid receptor binding	+	0.8055	80.55%
Aromatase binding	+	0.6977	69.77%
PPAR gamma	+	0.7428	74.28%
Honey bee toxicity	-	0.7329	73.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.84%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.30%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.65%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.12%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.69%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.59%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.08%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	90.43%	97.79%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.03%	94.80%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.62%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	87.40%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	85.90%	91.19%
CHEMBL3891	P07384	Calpain 1	84.52%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.14%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.45%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.15%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.04%	95.56%
CHEMBL4530	P00488	Coagulation factor XIII	81.70%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.10%	92.94%
CHEMBL299	P17252	Protein kinase C alpha	80.96%	98.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.14%	100.00%

Plants that contains it

• Casearia sylvestris

Cross-Links

• PubChem: 101602075
• LOTUS: LTS0112466
• wikiData: Q105236204