(1S,4aR,5S,8aR)-1,4a-dimethyl-5-[[(2R)-3-methyl-1,1-dioxo-2,5-dihydrothiophen-2-yl]methyl]-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 7909cc95-095e-4f47-8c4e-0f7928d0e0f9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aR,5S,8aR)-1,4a-dimethyl-5-[[(2R)-3-methyl-1,1-dioxo-2,5-dihydrothiophen-2-yl]methyl]-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCS(=O)(=O)C1CC2C(=C)CCC3C2(CCCC3(C)C(=O)O)C
• SMILES (Isomeric): CC1=CCS(=O)(=O)[C@@H]1C[C@H]2C(=C)CC[C@@H]3[C@@]2(CCC[C@]3(C)C(=O)O)C
• InChI: InChI=1S/C20H30O4S/c1-13-6-7-17-19(3,9-5-10-20(17,4)18(21)22)15(13)12-16-14(2)8-11-25(16,23)24/h8,15-17H,1,5-7,9-12H2,2-4H3,(H,21,22)/t15-,16+,17+,19+,20-/m0/s1
• InChI Key: DZRBOYRYIIIJJU-PNDFQMOFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄S
• Molecular Weight: 366.50 g/mol
• Exact Mass: 366.18648061 g/mol
• Topological Polar Surface Area (TPSA): 79.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.98
• 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	+	0.9749	97.49%
Caco-2	+	0.5387	53.87%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4998	49.98%
OATP2B1 inhibitior	-	0.8680	86.80%
OATP1B1 inhibitior	+	0.8143	81.43%
OATP1B3 inhibitior	+	0.9185	91.85%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.6854	68.54%
P-glycoprotein inhibitior	-	0.6685	66.85%
P-glycoprotein substrate	-	0.7404	74.04%
CYP3A4 substrate	+	0.6581	65.81%
CYP2C9 substrate	-	0.6031	60.31%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	+	0.5489	54.89%
CYP2C9 inhibition	-	0.7549	75.49%
CYP2C19 inhibition	-	0.6857	68.57%
CYP2D6 inhibition	-	0.8749	87.49%
CYP1A2 inhibition	-	0.7197	71.97%
CYP2C8 inhibition	-	0.6362	63.62%
CYP inhibitory promiscuity	-	0.8982	89.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6300	63.00%
Carcinogenicity (trinary)	Non-required	0.6698	66.98%
Eye corrosion	-	0.9739	97.39%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.7295	72.95%
Skin corrosion	-	0.8965	89.65%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4816	48.16%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.6091	60.91%
skin sensitisation	-	0.8248	82.48%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6655	66.55%
Acute Oral Toxicity (c)	III	0.6189	61.89%
Estrogen receptor binding	+	0.6535	65.35%
Androgen receptor binding	+	0.6130	61.30%
Thyroid receptor binding	+	0.6457	64.57%
Glucocorticoid receptor binding	+	0.8001	80.01%
Aromatase binding	+	0.5310	53.10%
PPAR gamma	-	0.6118	61.18%
Honey bee toxicity	-	0.8967	89.67%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	95.65%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.53%	96.09%
CHEMBL2581	P07339	Cathepsin D	84.20%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.94%	91.11%
CHEMBL5028	O14672	ADAM10	82.09%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.26%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.52%	100.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.33%	97.50%

Plants that contains it

• Fritillaria anhuiensis

Cross-Links

• PubChem: 71551593
• LOTUS: LTS0235796
• wikiData: Q104991952