(1S,12S,18S,19R,20S)-19-ethenyl-18-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid

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Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	7b077be7-6629-46ff-aa24-b8c7c478376c
Taxonomy	Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
IUPAC Name	(1S,12S,18S,19R,20S)-19-ethenyl-18-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid
SMILES (Canonical)	C=CC1C2CC3C4=C(CC(N3CC2=COC1OC5C(C(C(C(O5)CO)O)O)O)C(=O)O)C6=CC=CC=C6N4
SMILES (Isomeric)	C=C[C@@H]1[C@@H]2C[C@H]3C4=C(C[C@H](N3CC2=CO[C@H]1O[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O)C(=O)O)C6=CC=CC=C6N4
InChI	InChI=1S/C27H32N2O9/c1-2-13-15-7-18-21-16(14-5-3-4-6-17(14)28-21)8-19(25(34)35)29(18)9-12(15)11-36-26(13)38-27-24(33)23(32)22(31)20(10-30)37-27/h2-6,11,13,15,18-20,22-24,26-28,30-33H,1,7-10H2,(H,34,35)/t13-,15-,18+,19+,20+,22+,23-,24+,26+,27-/m1/s1
InChI Key	YWKCKNNZOGDZTJ-BJJMRNPYSA-N
Popularity	0 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₇H₃₂N₂O₉
Molecular Weight	528.50 g/mol
Exact Mass	528.21078060 g/mol
Topological Polar Surface Area (TPSA)	165.00 Å²
XlogP	-2.00
Atomic LogP (AlogP)	0.40
H-Bond Acceptor	9
H-Bond Donor	6
Rotatable Bonds	5

Synonyms

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There are no found synonyms.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7591	75.91%
Caco-2	-	0.8465	84.65%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5113	51.13%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8011	80.11%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9228	92.28%
P-glycoprotein inhibitior	-	0.4499	44.99%
P-glycoprotein substrate	-	0.5564	55.64%
CYP3A4 substrate	+	0.7063	70.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8068	80.68%
CYP3A4 inhibition	-	0.9567	95.67%
CYP2C9 inhibition	-	0.8156	81.56%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.8530	85.30%
CYP1A2 inhibition	-	0.6422	64.22%
CYP2C8 inhibition	+	0.7530	75.30%
CYP inhibitory promiscuity	-	0.7155	71.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5788	57.88%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9599	95.99%
Skin irritation	-	0.7624	76.24%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8623	86.23%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5591	55.91%
skin sensitisation	-	0.8449	84.49%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5676	56.76%
Acute Oral Toxicity (c)	III	0.5594	55.94%
Estrogen receptor binding	+	0.7698	76.98%
Androgen receptor binding	+	0.6809	68.09%
Thyroid receptor binding	+	0.5142	51.42%
Glucocorticoid receptor binding	-	0.4869	48.69%
Aromatase binding	-	0.5126	51.26%
PPAR gamma	+	0.6605	66.05%
Honey bee toxicity	-	0.7524	75.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9074	90.74%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.87%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.18%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.42%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.11%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.00%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.48%	94.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.16%	95.83%
CHEMBL220	P22303	Acetylcholinesterase	83.86%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	83.35%	91.49%
CHEMBL5028	O14672	ADAM10	82.77%	97.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.14%	94.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.09%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.93%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.26%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.46%	86.92%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.38%	85.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.