methyl N-[(1R,4Z,8S,13E)-1-hydroxy-8-[(2S,3R,4R,5R,6R)-4-hydroxy-5-(6-hydroxy-9H-pyrido[3,4-b]indole-1-carbonyl)-3-[(2S,4S,5S)-4-methoxy-5-(propan-2-ylamino)oxan-2-yl]oxy-6-methyl-5-methylsulfanyloxan-2-yl]oxy-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-10-bicyclo[7.3.1]trideca-4,9-dien-2,6-diynyl]carbamate

Details

• Internal ID: d12f13e9-9ca3-452f-92d7-3ea5ca5ad478
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: methyl N-[(1R,4Z,8S,13E)-1-hydroxy-8-[(2S,3R,4R,5R,6R)-4-hydroxy-5-(6-hydroxy-9H-pyrido[3,4-b]indole-1-carbonyl)-3-[(2S,4S,5S)-4-methoxy-5-(propan-2-ylamino)oxan-2-yl]oxy-6-methyl-5-methylsulfanyloxan-2-yl]oxy-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-10-bicyclo[7.3.1]trideca-4,9-dien-2,6-diynyl]carbamate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C#CC=CC#CC3(CC(=O)C(=C2C3=CCSSSC)NC(=O)OC)O)OC4CC(C(CO4)NC(C)C)OC)O)(C(=O)C5=NC=CC6=C5NC7=C6C=C(C=C7)O)SC
• SMILES (Isomeric): C[C@@H]1[C@]([C@@H]([C@H]([C@H](O1)O[C@H]2C#C/C=C\C#C[C@@]\3(CC(=O)C(=C2/C3=C\CSSSC)NC(=O)OC)O)O[C@H]4C[C@@H]([C@H](CO4)NC(C)C)OC)O)(C(=O)C5=NC=CC6=C5NC7=C6C=C(C=C7)O)SC
• InChI: InChI=1S/C46H52N4O12S4/c1-24(2)48-31-23-59-35(21-34(31)57-4)62-40-42(54)46(63-6,41(53)39-37-27(15-18-47-39)28-20-26(51)13-14-30(28)49-37)25(3)60-43(40)61-33-12-10-8-9-11-17-45(56)22-32(52)38(50-44(55)58-5)36(33)29(45)16-19-65-66-64-7/h8-9,13-16,18,20,24-25,31,33-35,40,42-43,48-49,51,54,56H,19,21-23H2,1-7H3,(H,50,55)/b9-8-,29-16+/t25-,31+,33+,34+,35+,40-,42-,43-,45+,46-/m1/s1
• InChI Key: FVNYJZKDBPDHIP-XBORIWGASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₂N₄O₁₂S₄
• Molecular Weight: 981.20 g/mol
• Exact Mass: 980.24645780 g/mol
• Topological Polar Surface Area (TPSA): 321.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 5.19
• H-Bond Acceptor: 18
• H-Bond Donor: 6
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9112	91.12%
Caco-2	-	0.8604	86.04%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.4543	45.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8037	80.37%
OATP1B3 inhibitior	+	0.9337	93.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9681	96.81%
P-glycoprotein inhibitior	+	0.7573	75.73%
P-glycoprotein substrate	+	0.8528	85.28%
CYP3A4 substrate	+	0.7594	75.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8504	85.04%
CYP3A4 inhibition	+	0.7802	78.02%
CYP2C9 inhibition	-	0.6860	68.60%
CYP2C19 inhibition	-	0.6203	62.03%
CYP2D6 inhibition	-	0.8487	84.87%
CYP1A2 inhibition	-	0.6672	66.72%
CYP2C8 inhibition	+	0.8427	84.27%
CYP inhibitory promiscuity	+	0.5982	59.82%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.4835	48.35%
Eye corrosion	-	0.9789	97.89%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.7547	75.47%
Skin corrosion	-	0.9140	91.40%
Ames mutagenesis	-	0.5154	51.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6813	68.13%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8287	82.87%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5816	58.16%
Acute Oral Toxicity (c)	III	0.5458	54.58%
Estrogen receptor binding	+	0.8279	82.79%
Androgen receptor binding	+	0.7733	77.33%
Thyroid receptor binding	+	0.6248	62.48%
Glucocorticoid receptor binding	+	0.7406	74.06%
Aromatase binding	+	0.6716	67.16%
PPAR gamma	+	0.7853	78.53%
Honey bee toxicity	-	0.5978	59.78%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9969	99.69%

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%
CHEMBL4040	P28482	MAP kinase ERK2	99.45%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.30%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.04%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.95%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.98%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.54%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.73%	89.00%
CHEMBL4208	P20618	Proteasome component C5	94.48%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.25%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.13%	99.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.89%	93.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.49%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.86%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.31%	95.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.10%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.57%	95.56%
CHEMBL2243	O00519	Anandamide amidohydrolase	90.21%	97.53%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.94%	91.07%
CHEMBL1914	P06276	Butyrylcholinesterase	89.27%	95.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.82%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.84%	99.15%
CHEMBL255	P29275	Adenosine A2b receptor	87.40%	98.59%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	87.37%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.77%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.83%	91.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.66%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.14%	95.89%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.27%	92.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.09%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	83.06%	91.19%
CHEMBL2535	P11166	Glucose transporter	82.95%	98.75%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	82.02%	83.10%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	81.61%	93.24%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.92%	93.56%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	80.70%	92.29%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.54%	91.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163186453
• LOTUS: LTS0244708
• wikiData: Q105002607