(3E,4S,5R)-3-[(3R,4E,8Z)-3,10-dihydroxy-4,8-dimethyldeca-4,8-dienylidene]-4-hydroxy-5-(2-methylprop-1-enyl)oxolan-2-one

Details

• Internal ID: 6c54d716-4a53-4a10-820b-c2357da8c2d8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (3E,4S,5R)-3-[(3R,4E,8Z)-3,10-dihydroxy-4,8-dimethyldeca-4,8-dienylidene]-4-hydroxy-5-(2-methylprop-1-enyl)oxolan-2-one
• SMILES (Canonical): CC(=CC1C(C(=CCC(C(=CCCC(=CCO)C)C)O)C(=O)O1)O)C
• SMILES (Isomeric): CC(=C[C@@H]1[C@H](/C(=C\C[C@H](/C(=C/CC/C(=C\CO)/C)/C)O)/C(=O)O1)O)C
• InChI: InChI=1S/C20H30O5/c1-13(2)12-18-19(23)16(20(24)25-18)8-9-17(22)15(4)7-5-6-14(3)10-11-21/h7-8,10,12,17-19,21-23H,5-6,9,11H2,1-4H3/b14-10-,15-7+,16-8+/t17-,18-,19+/m1/s1
• InChI Key: XTDIHRJVDHZHKP-KCDKUVQKSA-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: 2.80
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9436	94.36%
Caco-2	-	0.6080	60.80%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7609	76.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.7812	78.12%
OCT2 inhibitior	-	0.5042	50.42%
BSEP inhibitior	+	0.6483	64.83%
P-glycoprotein inhibitior	-	0.6707	67.07%
P-glycoprotein substrate	-	0.7936	79.36%
CYP3A4 substrate	+	0.5738	57.38%
CYP2C9 substrate	-	0.8096	80.96%
CYP2D6 substrate	-	0.8734	87.34%
CYP3A4 inhibition	-	0.6846	68.46%
CYP2C9 inhibition	-	0.8541	85.41%
CYP2C19 inhibition	-	0.7832	78.32%
CYP2D6 inhibition	-	0.9071	90.71%
CYP1A2 inhibition	-	0.7286	72.86%
CYP2C8 inhibition	-	0.8449	84.49%
CYP inhibitory promiscuity	-	0.9175	91.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9328	93.28%
Carcinogenicity (trinary)	Non-required	0.6435	64.35%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8292	82.92%
Skin irritation	-	0.5126	51.26%
Skin corrosion	-	0.9562	95.62%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5165	51.65%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8671	86.71%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.5386	53.86%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5623	56.23%
Acute Oral Toxicity (c)	III	0.5938	59.38%
Estrogen receptor binding	+	0.6636	66.36%
Androgen receptor binding	-	0.5971	59.71%
Thyroid receptor binding	+	0.5702	57.02%
Glucocorticoid receptor binding	+	0.7602	76.02%
Aromatase binding	+	0.6023	60.23%
PPAR gamma	+	0.6343	63.43%
Honey bee toxicity	-	0.7983	79.83%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9151	91.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.36%	83.82%
CHEMBL2581	P07339	Cathepsin D	93.27%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.15%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.50%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	85.94%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.39%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.65%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.16%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.14%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.58%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.97%	85.14%

Plants that contains it

• Perymenium hintonii

Cross-Links

• PubChem: 163190409
• LOTUS: LTS0218322
• wikiData: Q105341470