(1S,2S,5R,9S,10R)-5-ethenyl-2,9,10-trihydroxy-5,11,11-trimethyl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadec-6-en-8-one

Details

• Internal ID: 05ce9da4-86af-4a6a-b4c0-750b215a4c53
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: (1S,2S,5R,9S,10R)-5-ethenyl-2,9,10-trihydroxy-5,11,11-trimethyl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadec-6-en-8-one
• SMILES (Canonical): CC1(CCCC23C1(C(C(=O)C4=CC(CCC42O)(C)C=C)(OC3)O)O)C
• SMILES (Isomeric): C[C@@]1(CC[C@]2(C(=C1)C(=O)[C@@]3([C@@]4([C@@]2(CCCC4(C)C)CO3)O)O)O)C=C
• InChI: InChI=1S/C20H28O5/c1-5-16(4)9-10-18(22)13(11-16)14(21)19(23)20(24)15(2,3)7-6-8-17(18,20)12-25-19/h5,11,22-24H,1,6-10,12H2,2-4H3/t16-,17-,18+,19+,20+/m0/s1
• InChI Key: KPUJVADRTZEHMX-CENDIDJXSA-N
• Popularity: 1 reference 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): 87.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9663	96.63%
Caco-2	+	0.5827	58.27%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7760	77.60%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.8931	89.31%
OATP1B3 inhibitior	+	0.9068	90.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6792	67.92%
BSEP inhibitior	+	0.5757	57.57%
P-glycoprotein inhibitior	-	0.8408	84.08%
P-glycoprotein substrate	-	0.7822	78.22%
CYP3A4 substrate	+	0.5993	59.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8487	84.87%
CYP3A4 inhibition	-	0.8492	84.92%
CYP2C9 inhibition	-	0.7025	70.25%
CYP2C19 inhibition	-	0.8160	81.60%
CYP2D6 inhibition	-	0.9303	93.03%
CYP1A2 inhibition	-	0.7994	79.94%
CYP2C8 inhibition	-	0.7972	79.72%
CYP inhibitory promiscuity	-	0.9419	94.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5589	55.89%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8723	87.23%
Skin irritation	+	0.5436	54.36%
Skin corrosion	-	0.9274	92.74%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4078	40.78%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6212	62.12%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6834	68.34%
Acute Oral Toxicity (c)	III	0.6084	60.84%
Estrogen receptor binding	+	0.7108	71.08%
Androgen receptor binding	+	0.7294	72.94%
Thyroid receptor binding	+	0.6159	61.59%
Glucocorticoid receptor binding	+	0.5427	54.27%
Aromatase binding	+	0.7180	71.80%
PPAR gamma	-	0.4897	48.97%
Honey bee toxicity	-	0.7996	79.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9949	99.49%

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	97.19%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.18%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.38%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.91%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.20%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	85.98%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.07%	96.09%
CHEMBL4208	P20618	Proteasome component C5	84.29%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.34%	100.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.09%	94.42%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.20%	89.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101434881
• LOTUS: LTS0199412
• wikiData: Q105144386