(1S,4aR,5S,8aR)-5-[2-[(2S)-2-hydroxy-5-oxo-2H-furan-4-yl]ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 9afeae06-33a2-4f14-ab63-e72d9dccbf05
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1S,4aR,5S,8aR)-5-[2-[(2S)-2-hydroxy-5-oxo-2H-furan-4-yl]ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC(=C)C2CCC3=CC(OC3=O)O)(C)C(=O)O
• SMILES (Isomeric): C[C@]12CCC[C@]([C@@H]1CCC(=C)[C@@H]2CCC3=C[C@H](OC3=O)O)(C)C(=O)O
• InChI: InChI=1S/C20H28O5/c1-12-5-8-15-19(2,9-4-10-20(15,3)18(23)24)14(12)7-6-13-11-16(21)25-17(13)22/h11,14-16,21H,1,4-10H2,2-3H3,(H,23,24)/t14-,15+,16-,19+,20-/m0/s1
• InChI Key: CKMAUJLOUQNVRZ-RQQUZUBOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9777	97.77%
Caco-2	+	0.5874	58.74%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7040	70.40%
OATP2B1 inhibitior	-	0.8648	86.48%
OATP1B1 inhibitior	+	0.7905	79.05%
OATP1B3 inhibitior	+	0.8215	82.15%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5874	58.74%
BSEP inhibitior	-	0.7498	74.98%
P-glycoprotein inhibitior	-	0.7194	71.94%
P-glycoprotein substrate	-	0.8090	80.90%
CYP3A4 substrate	+	0.6586	65.86%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.9000	90.00%
CYP3A4 inhibition	-	0.6452	64.52%
CYP2C9 inhibition	-	0.8412	84.12%
CYP2C19 inhibition	-	0.8787	87.87%
CYP2D6 inhibition	-	0.9343	93.43%
CYP1A2 inhibition	-	0.6323	63.23%
CYP2C8 inhibition	-	0.6994	69.94%
CYP inhibitory promiscuity	-	0.8564	85.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5640	56.40%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.8599	85.99%
Skin irritation	+	0.5206	52.06%
Skin corrosion	-	0.9061	90.61%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4174	41.74%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6692	66.92%
skin sensitisation	-	0.7044	70.44%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.3579	35.79%
Estrogen receptor binding	+	0.7717	77.17%
Androgen receptor binding	+	0.6038	60.38%
Thyroid receptor binding	+	0.6994	69.94%
Glucocorticoid receptor binding	+	0.7958	79.58%
Aromatase binding	+	0.7118	71.18%
PPAR gamma	+	0.5946	59.46%
Honey bee toxicity	-	0.8274	82.74%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	96.78%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.83%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.69%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	89.21%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.48%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.23%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	85.65%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.79%	86.33%

Plants that contains it

• Calocedrus formosana
• Pinus armandii
• Platycladus orientalis

Cross-Links

• PubChem: 38361819
• LOTUS: LTS0138463
• wikiData: Q104962520