(1S,2R,7R,9S,11R)-13-hydroxy-15-[(1S)-1-[(1S,2R,4S,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-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: 3becfa74-28bf-4c7b-bcdc-15ca3495ca04
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: (1S,2R,7R,9S,11R)-13-hydroxy-15-[(1S)-1-[(1S,2R,4S,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-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): CC(C1CC2(C(O2)(C(O1)O)C)C)C3=CC4=C(C5CC6C7(O6)CC=CC(=O)C7(C5CC4)C)C(=C3)O
• SMILES (Isomeric): C[C@H]([C@@H]1C[C@]2([C@](O2)([C@@H](O1)O)C)C)C3=CC4=C([C@@H]5C[C@H]6[C@@]7(O6)CC=CC(=O)[C@@]7([C@H]5CC4)C)C(=C3)O
• InChI: InChI=1S/C28H34O6/c1-14(20-13-25(2)27(4,34-25)24(31)32-20)16-10-15-7-8-18-17(23(15)19(29)11-16)12-22-28(33-22)9-5-6-21(30)26(18,28)3/h5-6,10-11,14,17-18,20,22,24,29,31H,7-9,12-13H2,1-4H3/t14-,17+,18-,20-,22-,24+,25-,26-,27+,28-/m0/s1
• InChI Key: ARFKQZFIEWFLNC-CDZVSYRDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₆
• Molecular Weight: 466.60 g/mol
• Exact Mass: 466.23553880 g/mol
• Topological Polar Surface Area (TPSA): 91.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.87
• H-Bond Acceptor: 6
• 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	+	0.9406	94.06%
Caco-2	-	0.6608	66.08%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6873	68.73%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8433	84.33%
OATP1B3 inhibitior	+	0.9072	90.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9179	91.79%
P-glycoprotein inhibitior	+	0.7064	70.64%
P-glycoprotein substrate	+	0.6180	61.80%
CYP3A4 substrate	+	0.6980	69.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8578	85.78%
CYP3A4 inhibition	-	0.9240	92.40%
CYP2C9 inhibition	-	0.9052	90.52%
CYP2C19 inhibition	-	0.8117	81.17%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	+	0.6010	60.10%
CYP2C8 inhibition	+	0.6649	66.49%
CYP inhibitory promiscuity	-	0.9364	93.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5888	58.88%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9527	95.27%
Skin irritation	-	0.6238	62.38%
Skin corrosion	-	0.9242	92.42%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5089	50.89%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6208	62.08%
skin sensitisation	-	0.8220	82.20%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7561	75.61%
Acute Oral Toxicity (c)	III	0.4126	41.26%
Estrogen receptor binding	+	0.7829	78.29%
Androgen receptor binding	+	0.7642	76.42%
Thyroid receptor binding	+	0.6578	65.78%
Glucocorticoid receptor binding	+	0.8053	80.53%
Aromatase binding	+	0.7122	71.22%
PPAR gamma	+	0.5896	58.96%
Honey bee toxicity	-	0.7465	74.65%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9922	99.22%

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	99.50%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.73%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.89%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.36%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.76%	97.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	93.52%	85.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.37%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.60%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.25%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.92%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.13%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.50%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	89.45%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.26%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	88.93%	91.49%
CHEMBL4208	P20618	Proteasome component C5	88.72%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.51%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.22%	99.23%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.79%	91.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.78%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.32%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	85.27%	91.19%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.22%	99.15%
CHEMBL220	P22303	Acetylcholinesterase	84.89%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.77%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.73%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.29%	92.94%
CHEMBL259	P32245	Melanocortin receptor 4	82.67%	95.38%
CHEMBL237	P41145	Kappa opioid receptor	82.51%	98.10%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.21%	80.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.02%	92.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.00%	96.61%

Plants that contains it

• Salpichroa origanifolia

Cross-Links

• PubChem: 162847215
• LOTUS: LTS0261814
• wikiData: Q104917277