(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]-4-hydroxybutanal

Details

• Internal ID: 92d8ee82-4eab-4e97-b03e-e306391bc434
• 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]-4-hydroxybutanal
• SMILES (Canonical): CC1(CCCC2(C1CCC3(C2CC(=C(CCO)C=O)O3)C)C)C
• SMILES (Isomeric): C[C@@]12CCCC([C@H]1CC[C@]3([C@H]2C/C(=C(\CCO)/C=O)/O3)C)(C)C
• InChI: InChI=1S/C20H32O3/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/h13,16-17,21H,5-12H2,1-4H3/b15-14-/t16-,17+,19-,20+/m1/s1
• InChI Key: KLSZLVNNDDPPMI-CKOITNQJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.8218	82.18%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5423	54.23%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.8181	81.81%
OATP1B3 inhibitior	+	0.9553	95.53%
MATE1 inhibitior	-	0.6812	68.12%
OCT2 inhibitior	-	0.5317	53.17%
BSEP inhibitior	+	0.6406	64.06%
P-glycoprotein inhibitior	-	0.5952	59.52%
P-glycoprotein substrate	-	0.8802	88.02%
CYP3A4 substrate	+	0.5722	57.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.7574	75.74%
CYP2C9 inhibition	-	0.6838	68.38%
CYP2C19 inhibition	-	0.7483	74.83%
CYP2D6 inhibition	-	0.9027	90.27%
CYP1A2 inhibition	-	0.8045	80.45%
CYP2C8 inhibition	-	0.6368	63.68%
CYP inhibitory promiscuity	-	0.7534	75.34%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5783	57.83%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.9524	95.24%
Skin irritation	-	0.7042	70.42%
Skin corrosion	-	0.9532	95.32%
Ames mutagenesis	-	0.7870	78.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3701	37.01%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6942	69.42%
skin sensitisation	-	0.6371	63.71%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5126	51.26%
Acute Oral Toxicity (c)	III	0.6776	67.76%
Estrogen receptor binding	+	0.8414	84.14%
Androgen receptor binding	-	0.5084	50.84%
Thyroid receptor binding	+	0.6641	66.41%
Glucocorticoid receptor binding	+	0.8307	83.07%
Aromatase binding	+	0.6287	62.87%
PPAR gamma	+	0.6667	66.67%
Honey bee toxicity	-	0.9387	93.87%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9298	92.98%

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	96.75%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.65%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.78%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.40%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.20%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.69%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.43%	95.50%
CHEMBL2581	P07339	Cathepsin D	86.34%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.55%	94.45%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	84.35%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.02%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	82.25%	94.73%

Plants that contains it

• Silphium perfoliatum

Cross-Links

• PubChem: 163104738
• LOTUS: LTS0105963
• wikiData: Q105142802