Formyl-leurosine

Details

• Internal ID: 6546fc9f-2b80-49ac-bc39-823c0522968f
• Taxonomy: Alkaloids and derivatives > Vinca alkaloids
• IUPAC Name: methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-8-formyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-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)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC1=CC=CC=C41
• SMILES (Isomeric): CC[C@]12CN3CCC4=C([C@](C[C@H](C3)[C@H]1O2)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC1=CC=CC=C41
• InChI: InChI=1S/C46H54N4O10/c1-7-42-15-11-17-49-19-16-44(37(42)49)30-20-31(34(56-4)21-33(30)50(25-51)38(44)46(55,41(54)58-6)39(42)59-26(3)52)45(40(53)57-5)22-27-23-48(24-43(8-2)36(27)60-43)18-14-29-28-12-9-10-13-32(28)47-35(29)45/h9-13,15,20-21,25,27,36-39,47,55H,7-8,14,16-19,22-24H2,1-6H3/t27-,36-,37+,38-,39-,42-,43+,44-,45+,46+/m1/s1
• InChI Key: GLDSBTCHEGZWCV-HLTPFJCJSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₄N₄O₁₀
• Molecular Weight: 822.90 g/mol
• Exact Mass: 822.38399393 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.53
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• Formylleurosine
• 54022-49-0
• 22-Oxoleurosine
• f-Leu
• methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-8-formyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-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
• N-Formyl Leurosine (Vincristine Impurity G)
• SCHEMBL2034392
• DTXSID60968854
• GLDSBTCHEGZWCV-HLTPFJCJSA-N
• NSC269419
• AKOS030242406
• 22-Oxo-O~3'~,3'-cyclovincaleukoblastine
• (3'a,4'a)-4'-Deoxy-3',4'-epoxy-22-oxovincaleukoblastine
• Vincaleukoblastine,4'-epoxy-22-oxo-, (3'.alpha.,4'.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8751	87.51%
Caco-2	-	0.7322	73.22%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5165	51.65%
OATP2B1 inhibitior	-	0.7988	79.88%
OATP1B1 inhibitior	+	0.8321	83.21%
OATP1B3 inhibitior	+	0.9126	91.26%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8235	82.35%
P-glycoprotein substrate	+	0.9200	92.00%
CYP3A4 substrate	+	0.7789	77.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8002	80.02%
CYP3A4 inhibition	-	0.5627	56.27%
CYP2C9 inhibition	-	0.7881	78.81%
CYP2C19 inhibition	-	0.7779	77.79%
CYP2D6 inhibition	-	0.8745	87.45%
CYP1A2 inhibition	-	0.8882	88.82%
CYP2C8 inhibition	+	0.5310	53.10%
CYP inhibitory promiscuity	-	0.7815	78.15%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5567	55.67%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9343	93.43%
Skin irritation	-	0.7888	78.88%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7390	73.90%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.7176	71.76%
skin sensitisation	-	0.8715	87.15%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6076	60.76%
Acute Oral Toxicity (c)	III	0.5964	59.64%
Estrogen receptor binding	+	0.8715	87.15%
Androgen receptor binding	+	0.8104	81.04%
Thyroid receptor binding	+	0.7745	77.45%
Glucocorticoid receptor binding	+	0.8657	86.57%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8347	83.47%
Honey bee toxicity	-	0.6865	68.65%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5853	58.53%
Fish aquatic toxicity	+	0.9764	97.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.70%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.67%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.99%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	93.58%	95.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.33%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	92.11%	92.98%
CHEMBL2535	P11166	Glucose transporter	91.82%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.57%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.32%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.18%	97.14%
CHEMBL205	P00918	Carbonic anhydrase II	89.79%	98.44%
CHEMBL5028	O14672	ADAM10	88.67%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.49%	94.00%
CHEMBL2581	P07339	Cathepsin D	87.97%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.59%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.03%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.93%	89.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.92%	94.08%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.45%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.98%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.21%	99.23%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.79%	96.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.55%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.32%	96.77%

Plants that contains it

• Catharanthus roseus
• Taiwania cryptomerioides

Cross-Links

• PubChem: 320745
• LOTUS: LTS0161628
• wikiData: Q105114156