(4S)-3-[(E)-2-[(4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-4-hydroxyoxolan-2-one

Details

• Internal ID: 40c6ca92-3f0e-43ee-92e9-14d5906c72a1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (4S)-3-[(E)-2-[(4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-4-hydroxyoxolan-2-one
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2C=CC3C(COC3=O)O)(C)CO)O
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)C2/C=C/C3[C@@H](COC3=O)O)(C)CO)O
• InChI: InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5-6,13-17,21-23H,1,4,7-11H2,2-3H3/b6-5+/t13?,14?,15-,16+,17-,19+,20+/m1/s1
• InChI Key: CKZDDLBOPCFVJG-BUUDKCCUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.20932405 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• AC-1862

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9401	94.01%
Caco-2	-	0.5387	53.87%
Blood Brain Barrier	+	0.6777	67.77%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7024	70.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8947	89.47%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.5338	53.38%
BSEP inhibitior	+	0.6692	66.92%
P-glycoprotein inhibitior	-	0.8043	80.43%
P-glycoprotein substrate	-	0.7394	73.94%
CYP3A4 substrate	+	0.6714	67.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9326	93.26%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.7763	77.63%
CYP inhibitory promiscuity	-	0.8964	89.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5856	58.56%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9681	96.81%
Skin irritation	+	0.5319	53.19%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6564	65.64%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	-	0.9081	90.81%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6525	65.25%
Acute Oral Toxicity (c)	III	0.5328	53.28%
Estrogen receptor binding	+	0.7195	71.95%
Androgen receptor binding	+	0.5334	53.34%
Thyroid receptor binding	+	0.6696	66.96%
Glucocorticoid receptor binding	+	0.7785	77.85%
Aromatase binding	+	0.6085	60.85%
PPAR gamma	-	0.5246	52.46%
Honey bee toxicity	-	0.8272	82.72%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9803	98.03%

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	96.14%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.84%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.86%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.61%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.76%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	84.23%	95.93%
CHEMBL1977	P11473	Vitamin D receptor	83.38%	99.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.43%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.35%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.08%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	80.69%	83.82%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 45358107
• NPASS: NPC251599