methyl (13S,15S,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraen-17-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

Details

• Internal ID: 551b7444-5e3e-477e-ad5e-83d3eed51256
• Taxonomy: Alkaloids and derivatives > Plumeran-type alkaloids
• IUPAC Name: methyl (13S,15S,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraen-17-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate
• SMILES (Canonical): CCC12CN3CCC4=C(C(CC(C3)C1O2)(C5CC67C8N5CC=CC8(C(C(C6N(C9=C7C=CC(=C9)OC)C)(C(=O)OC)O)OC(=O)C)CC)C(=O)OC)NC1=CC=CC=C41
• SMILES (Isomeric): CC[C@]12CN3CCC4=C([C@](C[C@@H](C3)[C@H]1O2)(C5C[C@@]67[C@H]8N5CC=C[C@]8([C@H]([C@@]([C@@H]6N(C9=C7C=CC(=C9)OC)C)(C(=O)OC)O)OC(=O)C)CC)C(=O)OC)NC1=CC=CC=C41
• InChI: InChI=1S/C46H56N4O9/c1-8-42-18-12-19-50-34(23-44(37(42)50)31-16-15-28(55-5)21-33(31)48(4)38(44)46(54,41(53)57-7)39(42)58-26(3)51)45(40(52)56-6)22-27-24-49(25-43(9-2)36(27)59-43)20-17-30-29-13-10-11-14-32(29)47-35(30)45/h10-16,18,21,27,34,36-39,47,54H,8-9,17,19-20,22-25H2,1-7H3/t27-,34?,36+,37-,38+,39+,42+,43-,44+,45-,46-/m0/s1
• InChI Key: OHDAOWKAOQAEGR-CZUAIMPLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₆N₄O₉
• Molecular Weight: 809.00 g/mol
• Exact Mass: 808.40472938 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.03
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8673	86.73%
Caco-2	-	0.7828	78.28%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5109	51.09%
OATP2B1 inhibitior	-	0.6210	62.10%
OATP1B1 inhibitior	+	0.8084	80.84%
OATP1B3 inhibitior	+	0.9062	90.62%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8288	82.88%
P-glycoprotein substrate	+	0.8905	89.05%
CYP3A4 substrate	+	0.7658	76.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7860	78.60%
CYP3A4 inhibition	-	0.6385	63.85%
CYP2C9 inhibition	-	0.8055	80.55%
CYP2C19 inhibition	-	0.8007	80.07%
CYP2D6 inhibition	-	0.8833	88.33%
CYP1A2 inhibition	-	0.8767	87.67%
CYP2C8 inhibition	+	0.7049	70.49%
CYP inhibitory promiscuity	-	0.7834	78.34%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5410	54.10%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9216	92.16%
Skin irritation	-	0.7920	79.20%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7607	76.07%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.6474	64.74%
skin sensitisation	-	0.8639	86.39%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7377	73.77%
Acute Oral Toxicity (c)	III	0.6051	60.51%
Estrogen receptor binding	+	0.8411	84.11%
Androgen receptor binding	+	0.7932	79.32%
Thyroid receptor binding	+	0.6981	69.81%
Glucocorticoid receptor binding	+	0.8346	83.46%
Aromatase binding	+	0.5568	55.68%
PPAR gamma	+	0.8035	80.35%
Honey bee toxicity	-	0.6970	69.70%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9751	97.51%

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	99.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.37%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.26%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.21%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.46%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.24%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.40%	95.56%
CHEMBL2535	P11166	Glucose transporter	94.19%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.10%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.05%	94.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.51%	94.08%
CHEMBL255	P29275	Adenosine A2b receptor	91.48%	98.59%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.89%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.50%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.30%	96.77%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.30%	93.99%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	89.17%	97.50%
CHEMBL205	P00918	Carbonic anhydrase II	88.08%	98.44%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.77%	95.17%
CHEMBL233	P35372	Mu opioid receptor	86.86%	97.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.68%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.30%	97.09%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	86.11%	92.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.25%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	85.23%	95.12%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.54%	93.65%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.22%	93.00%
CHEMBL240	Q12809	HERG	83.73%	89.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.24%	99.17%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.20%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.18%	97.14%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.08%	90.95%
CHEMBL5028	O14672	ADAM10	81.84%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.58%	91.19%
CHEMBL256	P0DMS8	Adenosine A3 receptor	81.55%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.94%	99.23%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.85%	98.33%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 6325522
• NPASS: NPC142656