(1S,2R,7R,9S,11R)-15-[(1S)-1-[(2R,5R,6S)-5,6-dihydroxy-4,5-dimethyl-2,6-dihydropyran-2-yl]ethyl]-2-methyl-8-oxapentacyclo[9.8.0.02,7.07,9.012,17]nonadeca-4,12(17),13,15-tetraen-3-one

Details

• Internal ID: 9b07e5da-702e-4b47-893b-dd879fcf0170
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: (1S,2R,7R,9S,11R)-15-[(1S)-1-[(2R,5R,6S)-5,6-dihydroxy-4,5-dimethyl-2,6-dihydropyran-2-yl]ethyl]-2-methyl-8-oxapentacyclo[9.8.0.02,7.07,9.012,17]nonadeca-4,12(17),13,15-tetraen-3-one
• SMILES (Canonical): CC1=CC(OC(C1(C)O)O)C(C)C2=CC3=C(C=C2)C4CC5C6(O5)CC=CC(=O)C6(C4CC3)C
• SMILES (Isomeric): CC1=C[C@@H](O[C@@H]([C@]1(C)O)O)[C@@H](C)C2=CC3=C(C=C2)[C@@H]4C[C@H]5[C@@]6(O5)CC=CC(=O)[C@@]6([C@H]4CC3)C
• InChI: InChI=1S/C28H34O5/c1-15-12-22(32-25(30)27(15,4)31)16(2)17-7-9-19-18(13-17)8-10-21-20(19)14-24-28(33-24)11-5-6-23(29)26(21,28)3/h5-7,9,12-13,16,20-22,24-25,30-31H,8,10-11,14H2,1-4H3/t16-,20-,21-,22+,24-,25-,26-,27+,28-/m0/s1
• InChI Key: HGWVJOKYHSMESK-LZSBBJQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₅
• Molecular Weight: 450.60 g/mol
• Exact Mass: 450.24062418 g/mol
• Topological Polar Surface Area (TPSA): 79.30 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.93
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9427	94.27%
Caco-2	-	0.7078	70.78%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7304	73.04%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8675	86.75%
OATP1B3 inhibitior	+	0.9629	96.29%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8441	84.41%
P-glycoprotein inhibitior	+	0.6947	69.47%
P-glycoprotein substrate	+	0.6895	68.95%
CYP3A4 substrate	+	0.7043	70.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8694	86.94%
CYP3A4 inhibition	-	0.9247	92.47%
CYP2C9 inhibition	-	0.8968	89.68%
CYP2C19 inhibition	-	0.7973	79.73%
CYP2D6 inhibition	-	0.9233	92.33%
CYP1A2 inhibition	-	0.5849	58.49%
CYP2C8 inhibition	+	0.6236	62.36%
CYP inhibitory promiscuity	-	0.9547	95.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6256	62.56%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9688	96.88%
Skin irritation	-	0.6205	62.05%
Skin corrosion	-	0.9297	92.97%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6791	67.91%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6711	67.11%
skin sensitisation	-	0.7357	73.57%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7834	78.34%
Acute Oral Toxicity (c)	III	0.4207	42.07%
Estrogen receptor binding	+	0.8186	81.86%
Androgen receptor binding	+	0.7572	75.72%
Thyroid receptor binding	+	0.7062	70.62%
Glucocorticoid receptor binding	+	0.7884	78.84%
Aromatase binding	+	0.7058	70.58%
PPAR gamma	+	0.6085	60.85%
Honey bee toxicity	-	0.7309	73.09%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9840	98.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.06%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.39%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.60%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.09%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.94%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.99%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.68%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.65%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.36%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.38%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.74%	93.56%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	85.74%	95.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.55%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.38%	91.19%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.06%	85.11%
CHEMBL4208	P20618	Proteasome component C5	84.96%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.95%	99.23%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	84.21%	97.23%
CHEMBL4444	P04070	Vitamin K-dependent protein C	83.73%	93.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.57%	93.03%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	83.45%	90.24%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.67%	97.25%
CHEMBL4302	P08183	P-glycoprotein 1	82.58%	92.98%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.52%	97.14%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	81.91%	92.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.04%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	80.70%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.59%	96.21%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.39%	93.04%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.32%	93.40%

Plants that contains it

• Salpichroa origanifolia

Cross-Links

• PubChem: 21604160
• LOTUS: LTS0054119
• wikiData: Q105028018