(1S,3S)-1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

Details

• Internal ID: 5a9570d8-ebdf-404a-bbbb-cad69ce16467
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (1S,3S)-1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• SMILES (Canonical): COC(=O)C1=COC(C(C1CC2C3=C(CC(N2)C(=O)O)C4=CC=CC=C4N3)C=C)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C3=C(C[C@H](N2)C(=O)O)C4=CC=CC=C4N3)C=C)O[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O
• InChI: InChI=1S/C28H34N2O11/c1-3-12-14(8-18-21-15(9-19(29-18)25(35)36)13-6-4-5-7-17(13)30-21)16(26(37)38-2)11-39-27(12)41-28-24(34)23(33)22(32)20(10-31)40-28/h3-7,11-12,14,18-20,22-24,27-34H,1,8-10H2,2H3,(H,35,36)/t12-,14+,18+,19+,20+,22+,23-,24+,27+,28-/m1/s1
• InChI Key: LHKZIVMTXZLOTP-AZAOCEFRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄N₂O₁₁
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.21625990 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8170	81.70%
Caco-2	-	0.8888	88.88%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Nucleus	0.5108	51.08%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.7768	77.68%
OATP1B3 inhibitior	+	0.9436	94.36%
MATE1 inhibitior	-	0.9420	94.20%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8447	84.47%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5866	58.66%
CYP3A4 substrate	+	0.7150	71.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8422	84.22%
CYP3A4 inhibition	-	0.9029	90.29%
CYP2C9 inhibition	-	0.7560	75.60%
CYP2C19 inhibition	-	0.8235	82.35%
CYP2D6 inhibition	-	0.8044	80.44%
CYP1A2 inhibition	-	0.7398	73.98%
CYP2C8 inhibition	+	0.7306	73.06%
CYP inhibitory promiscuity	-	0.7535	75.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6472	64.72%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9473	94.73%
Skin irritation	-	0.7843	78.43%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8190	81.90%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6966	69.66%
skin sensitisation	-	0.8327	83.27%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.5666	56.66%
Acute Oral Toxicity (c)	III	0.6014	60.14%
Estrogen receptor binding	+	0.7961	79.61%
Androgen receptor binding	+	0.6823	68.23%
Thyroid receptor binding	+	0.5152	51.52%
Glucocorticoid receptor binding	+	0.5870	58.70%
Aromatase binding	-	0.5136	51.36%
PPAR gamma	+	0.6767	67.67%
Honey bee toxicity	-	0.7119	71.19%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.7012	70.12%

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	98.23%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.02%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.30%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	91.62%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.10%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.84%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.67%	89.00%
CHEMBL5028	O14672	ADAM10	88.46%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	87.78%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.77%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.20%	95.83%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.05%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.24%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.48%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.14%	95.89%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	81.98%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	81.57%	94.73%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.29%	94.08%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.45%	92.62%

Plants that contains it

• Psychotria bahiensis
• Simira rubescens
• Stenostomum acreanum

Cross-Links

• PubChem: 163194024
• LOTUS: LTS0079556
• wikiData: Q105151823