(3S,4aS,8R,8aS)-8-[2-(furan-3-yl)-2-oxoethyl]-3-hydroxy-4,4,8a-trimethyl-7-methylidene-1,3,4a,5,6,8-hexahydronaphthalen-2-one

Details

• Internal ID: 7f027a98-2aa8-4033-a9ce-dbaea1f41afd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (3S,4aS,8R,8aS)-8-[2-(furan-3-yl)-2-oxoethyl]-3-hydroxy-4,4,8a-trimethyl-7-methylidene-1,3,4a,5,6,8-hexahydronaphthalen-2-one
• SMILES (Canonical): CC1(C2CCC(=C)C(C2(CC(=O)C1O)C)CC(=O)C3=COC=C3)C
• SMILES (Isomeric): C[C@@]12CC(=O)[C@H](C([C@H]1CCC(=C)[C@H]2CC(=O)C3=COC=C3)(C)C)O
• InChI: InChI=1S/C20H26O4/c1-12-5-6-17-19(2,3)18(23)16(22)10-20(17,4)14(12)9-15(21)13-7-8-24-11-13/h7-8,11,14,17-18,23H,1,5-6,9-10H2,2-4H3/t14-,17-,18-,20+/m1/s1
• InChI Key: DZWVYGYFOOXIST-ZESCBINXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 67.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.80
• H-Bond Acceptor: 4
• 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	+	0.9924	99.24%
Caco-2	+	0.6514	65.14%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7453	74.53%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.7425	74.25%
OATP1B3 inhibitior	-	0.4114	41.14%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5032	50.32%
BSEP inhibitior	-	0.6224	62.24%
P-glycoprotein inhibitior	-	0.7140	71.40%
P-glycoprotein substrate	-	0.7539	75.39%
CYP3A4 substrate	+	0.6451	64.51%
CYP2C9 substrate	-	0.8005	80.05%
CYP2D6 substrate	-	0.7982	79.82%
CYP3A4 inhibition	+	0.6038	60.38%
CYP2C9 inhibition	-	0.6781	67.81%
CYP2C19 inhibition	-	0.5974	59.74%
CYP2D6 inhibition	-	0.9309	93.09%
CYP1A2 inhibition	-	0.5425	54.25%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.7418	74.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6096	60.96%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9169	91.69%
Skin irritation	+	0.4933	49.33%
Skin corrosion	-	0.9173	91.73%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7692	76.92%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5717	57.17%
skin sensitisation	-	0.7798	77.98%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5141	51.41%
Acute Oral Toxicity (c)	III	0.5133	51.33%
Estrogen receptor binding	+	0.5548	55.48%
Androgen receptor binding	+	0.5610	56.10%
Thyroid receptor binding	+	0.5458	54.58%
Glucocorticoid receptor binding	+	0.6124	61.24%
Aromatase binding	+	0.6199	61.99%
PPAR gamma	-	0.5831	58.31%
Honey bee toxicity	-	0.8772	87.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.10%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.65%	90.17%
CHEMBL4040	P28482	MAP kinase ERK2	91.53%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.22%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.72%	97.25%
CHEMBL2581	P07339	Cathepsin D	87.39%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.90%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.98%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.59%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.98%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.43%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.98%	95.89%

Plants that contains it

• Planaltoa lychnophoroides

Cross-Links

• PubChem: 163026281
• LOTUS: LTS0200494
• wikiData: Q104992077