[(1R,5aS,6R,9R,9aS,9bS)-1-hydroxy-6,9a-dimethyl-6-(4-methylpent-3-enyl)-1,3,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-9-yl] acetate

Details

• Internal ID: a03a276f-6236-47a8-9ecc-5b7eaea604ed
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(1R,5aS,6R,9R,9aS,9bS)-1-hydroxy-6,9a-dimethyl-6-(4-methylpent-3-enyl)-1,3,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-9-yl] acetate
• SMILES (Canonical): CC(=CCCC1(CCC(C2(C1CC=C3C2C(OC3)O)C)OC(=O)C)C)C
• SMILES (Isomeric): CC(=CCC[C@@]1(CC[C@H]([C@]2([C@H]1CC=C3[C@@H]2[C@@H](OC3)O)C)OC(=O)C)C)C
• InChI: InChI=1S/C22H34O4/c1-14(2)7-6-11-21(4)12-10-18(26-15(3)23)22(5)17(21)9-8-16-13-25-20(24)19(16)22/h7-8,17-20,24H,6,9-13H2,1-5H3/t17-,18+,19+,20+,21+,22+/m0/s1
• InChI Key: KGMGBBURGHXQKU-SNMGDHFUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.50 g/mol
• Exact Mass: 362.24570956 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.38
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	+	0.7852	78.52%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8748	87.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8069	80.69%
OATP1B3 inhibitior	+	0.8362	83.62%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.6768	67.68%
P-glycoprotein inhibitior	-	0.4727	47.27%
P-glycoprotein substrate	-	0.7624	76.24%
CYP3A4 substrate	+	0.6655	66.55%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8685	86.85%
CYP3A4 inhibition	-	0.5983	59.83%
CYP2C9 inhibition	-	0.6061	60.61%
CYP2C19 inhibition	-	0.7727	77.27%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.6769	67.69%
CYP2C8 inhibition	+	0.4770	47.70%
CYP inhibitory promiscuity	-	0.6478	64.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6190	61.90%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9462	94.62%
Skin irritation	-	0.5308	53.08%
Skin corrosion	-	0.9529	95.29%
Ames mutagenesis	-	0.5623	56.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.6908	69.08%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5757	57.57%
skin sensitisation	-	0.8431	84.31%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7048	70.48%
Estrogen receptor binding	+	0.8064	80.64%
Androgen receptor binding	+	0.5552	55.52%
Thyroid receptor binding	+	0.6561	65.61%
Glucocorticoid receptor binding	+	0.7138	71.38%
Aromatase binding	+	0.5322	53.22%
PPAR gamma	+	0.6285	62.85%
Honey bee toxicity	-	0.7897	78.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9962	99.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.18%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.94%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.99%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.60%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.89%	98.95%
CHEMBL5028	O14672	ADAM10	84.92%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	84.16%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.33%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.66%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.91%	92.94%

Plants that contains it

• Fossombronia wondraczekii

Cross-Links

• PubChem: 101740645
• LOTUS: LTS0164701
• wikiData: Q105140841