(1R,2S,3S,5R,10R)-5-ethenyl-3-hydroxy-2,5,11,11-tetramethyl-15-oxatetracyclo[8.4.1.01,10.02,7]pentadec-13-en-12-one

Details

• Internal ID: 8346e065-b0ae-4b01-8df1-130e90babf5f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,2S,3S,5R,10R)-5-ethenyl-3-hydroxy-2,5,11,11-tetramethyl-15-oxatetracyclo[8.4.1.01,10.02,7]pentadec-13-en-12-one
• SMILES (Canonical): CC1(C(=O)C=CC23C1(O2)CCC4C3(C(CC(C4)(C)C=C)O)C)C
• SMILES (Isomeric): C[C@@]1(C[C@@H]([C@@]2(C(C1)CC[C@@]34[C@@]2(O3)C=CC(=O)C4(C)C)C)O)C=C
• InChI: InChI=1S/C20H28O3/c1-6-17(4)11-13-7-9-19-16(2,3)14(21)8-10-20(19,23-19)18(13,5)15(22)12-17/h6,8,10,13,15,22H,1,7,9,11-12H2,2-5H3/t13?,15-,17+,18-,19+,20+/m0/s1
• InChI Key: VNIPYFUGQSQYAQ-SNZBZHPLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 3
• 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	+	0.9917	99.17%
Caco-2	+	0.7723	77.23%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5222	52.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8831	88.31%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7231	72.31%
P-glycoprotein inhibitior	-	0.8095	80.95%
P-glycoprotein substrate	-	0.8058	80.58%
CYP3A4 substrate	+	0.6313	63.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.6223	62.23%
CYP2C9 inhibition	-	0.6756	67.56%
CYP2C19 inhibition	-	0.6378	63.78%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.5967	59.67%
CYP2C8 inhibition	-	0.7678	76.78%
CYP inhibitory promiscuity	-	0.9521	95.21%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6492	64.92%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9294	92.94%
Skin irritation	+	0.4907	49.07%
Skin corrosion	-	0.9152	91.52%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8375	83.75%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5443	54.43%
skin sensitisation	-	0.6399	63.99%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6561	65.61%
Acute Oral Toxicity (c)	III	0.5722	57.22%
Estrogen receptor binding	+	0.7153	71.53%
Androgen receptor binding	+	0.6211	62.11%
Thyroid receptor binding	+	0.7691	76.91%
Glucocorticoid receptor binding	+	0.6857	68.57%
Aromatase binding	+	0.8080	80.80%
PPAR gamma	-	0.5183	51.83%
Honey bee toxicity	-	0.8786	87.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9845	98.45%

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	96.36%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.66%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.62%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.44%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.60%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.12%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.59%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.49%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	82.50%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.47%	86.33%

Plants that contains it

• Vellozia candida

Cross-Links

• PubChem: 163085461
• LOTUS: LTS0017842
• wikiData: Q105289652