(1R,5R,6S,10S,11S,14S)-11-hydroxy-3,14-dimethyl-9-methylidene-6-prop-1-en-2-yl-13-oxatetracyclo[9.4.0.01,14.05,10]pentadec-3-ene-2,12-dione

Details

• Internal ID: 7980aea0-ddef-4c8a-b2c1-9fa5f79f0a84
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1R,5R,6S,10S,11S,14S)-11-hydroxy-3,14-dimethyl-9-methylidene-6-prop-1-en-2-yl-13-oxatetracyclo[9.4.0.01,14.05,10]pentadec-3-ene-2,12-dione
• SMILES (Canonical): CC1=CC2C(CCC(=C)C2C3(C(=O)OC4(C3(C4)C1=O)C)O)C(=C)C
• SMILES (Isomeric): CC1=C[C@@H]2[C@H](CCC(=C)[C@H]2[C@]3(C(=O)O[C@@]4([C@]3(C4)C1=O)C)O)C(=C)C
• InChI: InChI=1S/C20H24O4/c1-10(2)13-7-6-11(3)15-14(13)8-12(4)16(21)19-9-18(19,5)24-17(22)20(15,19)23/h8,13-15,23H,1,3,6-7,9H2,2,4-5H3/t13-,14-,15-,18+,19+,20-/m1/s1
• InChI Key: VGBQQGAEMBZMIP-TYWUSVEKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9686	96.86%
Caco-2	-	0.5177	51.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6721	67.21%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8883	88.83%
OATP1B3 inhibitior	+	0.8768	87.68%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7124	71.24%
BSEP inhibitior	-	0.7574	75.74%
P-glycoprotein inhibitior	-	0.8076	80.76%
P-glycoprotein substrate	-	0.7456	74.56%
CYP3A4 substrate	+	0.6356	63.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8885	88.85%
CYP3A4 inhibition	-	0.5723	57.23%
CYP2C9 inhibition	-	0.8251	82.51%
CYP2C19 inhibition	-	0.8093	80.93%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.5517	55.17%
CYP2C8 inhibition	-	0.6278	62.78%
CYP inhibitory promiscuity	-	0.9229	92.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5547	55.47%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8502	85.02%
Skin irritation	+	0.5251	52.51%
Skin corrosion	-	0.8079	80.79%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5987	59.87%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.7336	73.36%
skin sensitisation	-	0.7705	77.05%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7370	73.70%
Acute Oral Toxicity (c)	III	0.4007	40.07%
Estrogen receptor binding	+	0.6193	61.93%
Androgen receptor binding	+	0.7509	75.09%
Thyroid receptor binding	+	0.5880	58.80%
Glucocorticoid receptor binding	+	0.7316	73.16%
Aromatase binding	-	0.6573	65.73%
PPAR gamma	-	0.5401	54.01%
Honey bee toxicity	-	0.8876	88.76%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9754	97.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.06%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.92%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.45%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.23%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.52%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.22%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.54%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.78%	99.23%
CHEMBL1871	P10275	Androgen Receptor	82.62%	96.43%
CHEMBL4530	P00488	Coagulation factor XIII	81.22%	96.00%

Plants that contains it

• Joannesia princeps

Cross-Links

• PubChem: 101700057
• LOTUS: LTS0001557
• wikiData: Q105285703