(1R,18S,19R,20S)-18-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-19-ethenyl-6-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,15-pentaen-14-one

Details

• Internal ID: 9f08ffab-32e4-42e7-bfa0-351475f3b001
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: (1R,18S,19R,20S)-18-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-19-ethenyl-6-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,15-pentaen-14-one
• SMILES (Canonical): C=CC1C2CC3C4=C(CCN3C(=O)C2=COC1OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C7=C(N4)C=C(C=C7)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2C[C@@H]3C4=C(CCN3C(=O)C2=CO[C@H]1O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C7=C(N4)C=C(C=C7)O
• InChI: InChI=1S/C32H40N2O14/c1-2-13-16-8-19-22-15(14-4-3-12(37)7-18(14)33-22)5-6-34(19)29(43)17(16)11-44-30(13)48-32-28(26(41)24(39)21(10-36)46-32)47-31-27(42)25(40)23(38)20(9-35)45-31/h2-4,7,11,13,16,19-21,23-28,30-33,35-42H,1,5-6,8-10H2/t13-,16+,19-,20-,21-,23-,24-,25+,26+,27-,28-,30+,31+,32+/m1/s1
• InChI Key: SJIFBOXHPPOQJW-ZOJHWHDTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀N₂O₁₄
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.24795395 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.00
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8317	83.17%
Caco-2	-	0.8853	88.53%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.6207	62.07%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.8111	81.11%
OATP1B3 inhibitior	+	0.9274	92.74%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8823	88.23%
P-glycoprotein inhibitior	+	0.5891	58.91%
P-glycoprotein substrate	+	0.5769	57.69%
CYP3A4 substrate	+	0.7095	70.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8525	85.25%
CYP3A4 inhibition	-	0.7764	77.64%
CYP2C9 inhibition	-	0.8181	81.81%
CYP2C19 inhibition	-	0.8541	85.41%
CYP2D6 inhibition	-	0.8323	83.23%
CYP1A2 inhibition	-	0.6171	61.71%
CYP2C8 inhibition	+	0.6991	69.91%
CYP inhibitory promiscuity	-	0.6100	61.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5676	56.76%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.9286	92.86%
Skin irritation	-	0.7577	75.77%
Skin corrosion	-	0.9325	93.25%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8613	86.13%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.6602	66.02%
skin sensitisation	-	0.8601	86.01%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8501	85.01%
Acute Oral Toxicity (c)	III	0.5983	59.83%
Estrogen receptor binding	+	0.8176	81.76%
Androgen receptor binding	+	0.7331	73.31%
Thyroid receptor binding	-	0.4908	49.08%
Glucocorticoid receptor binding	-	0.4778	47.78%
Aromatase binding	+	0.5584	55.84%
PPAR gamma	+	0.7180	71.80%
Honey bee toxicity	-	0.6976	69.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9121	91.21%

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	99.30%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.26%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.77%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.54%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.68%	93.40%
CHEMBL2581	P07339	Cathepsin D	95.67%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.33%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.17%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.98%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.30%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.04%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.50%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.01%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.54%	95.83%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.52%	96.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.61%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.44%	85.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.41%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.33%	90.00%
CHEMBL1902	P62942	FK506-binding protein 1A	83.23%	97.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.78%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	82.72%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.61%	90.71%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.76%	83.57%
CHEMBL4530	P00488	Coagulation factor XIII	81.62%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.34%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.70%	97.36%

Plants that contains it

• Uncaria rhynchophylla

Cross-Links

• PubChem: 44255119
• LOTUS: LTS0243770
• wikiData: Q105254314