(2Z)-2-[(3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-ylidene]butane-1,4-diol

Details

• Internal ID: f2915083-e8f2-4bb1-ab07-498630c42c79
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (2Z)-2-[(3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-ylidene]butane-1,4-diol
• SMILES (Canonical): CC1(CCCC2(C1CCC3(C2CC(=C(CCO)CO)O3)C)C)C
• SMILES (Isomeric): C[C@@]12CCCC([C@H]1CC[C@]3([C@H]2C/C(=C(\CCO)/CO)/O3)C)(C)C
• InChI: InChI=1S/C20H34O3/c1-18(2)8-5-9-19(3)16(18)6-10-20(4)17(19)12-15(23-20)14(13-22)7-11-21/h16-17,21-22H,5-13H2,1-4H3/b15-14-/t16-,17+,19-,20+/m1/s1
• InChI Key: QHXLKPAAORFEPJ-CKOITNQJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9894	98.94%
Caco-2	+	0.8076	80.76%
Blood Brain Barrier	+	0.6385	63.85%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4638	46.38%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8540	85.40%
OATP1B3 inhibitior	+	0.9562	95.62%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.6358	63.58%
BSEP inhibitior	-	0.4815	48.15%
P-glycoprotein inhibitior	-	0.7616	76.16%
P-glycoprotein substrate	-	0.8599	85.99%
CYP3A4 substrate	+	0.5762	57.62%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.7208	72.08%
CYP3A4 inhibition	-	0.7445	74.45%
CYP2C9 inhibition	-	0.7663	76.63%
CYP2C19 inhibition	-	0.7450	74.50%
CYP2D6 inhibition	-	0.8882	88.82%
CYP1A2 inhibition	-	0.8647	86.47%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.6695	66.95%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5497	54.97%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.8173	81.73%
Skin irritation	-	0.7847	78.47%
Skin corrosion	-	0.9567	95.67%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.6476	64.76%
skin sensitisation	-	0.7119	71.19%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5755	57.55%
Acute Oral Toxicity (c)	III	0.6010	60.10%
Estrogen receptor binding	+	0.8110	81.10%
Androgen receptor binding	+	0.5232	52.32%
Thyroid receptor binding	+	0.6481	64.81%
Glucocorticoid receptor binding	+	0.7813	78.13%
Aromatase binding	+	0.7028	70.28%
PPAR gamma	+	0.5656	56.56%
Honey bee toxicity	-	0.9364	93.64%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9174	91.74%

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	96.91%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.49%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.57%	82.69%
CHEMBL237	P41145	Kappa opioid receptor	85.17%	98.10%
CHEMBL2581	P07339	Cathepsin D	84.95%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.20%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.59%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.97%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.83%	95.50%

Plants that contains it

• Silphium perfoliatum

Cross-Links

• PubChem: 163105656
• LOTUS: LTS0159301
• wikiData: Q105221194