Maytanprine

Details

• Internal ID: 42170de1-3905-481b-a486-8bb5910c16e9
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: [(1S,2R,3S,5S,6S,16E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl(propanoyl)amino]propanoate
• SMILES (Canonical): CCC(=O)N(C)C(C)C(=O)OC1CC(=O)N(C2=C(C(=CC(=C2)CC(=CC=CC(C3(CC(C(C4C1(O4)C)C)OC(=O)N3)O)OC)C)OC)Cl)C
• SMILES (Isomeric): CCC(=O)N(C)[C@@H](C)C(=O)O[C@H]1CC(=O)N(C2=C(C(=CC(=C2)C/C(=C/C=C[C@H]([C@]3(C[C@@H]([C@H]([C@H]4[C@]1(O4)C)C)OC(=O)N3)O)OC)/C)OC)Cl)C
• InChI: InChI=1S/C35H48ClN3O10/c1-10-28(40)38(6)21(4)32(42)48-27-17-29(41)39(7)23-15-22(16-24(45-8)30(23)36)14-19(2)12-11-13-26(46-9)35(44)18-25(47-33(43)37-35)20(3)31-34(27,5)49-31/h11-13,15-16,20-21,25-27,31,44H,10,14,17-18H2,1-9H3,(H,37,43)/b13-11?,19-12+/t20-,21+,25+,26-,27+,31+,34+,35+/m1/s1
• InChI Key: BVXGVRDMHBYRCQ-FFVBGLEHSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₈ClN₃O₁₀
• Molecular Weight: 706.20 g/mol
• Exact Mass: 705.3028224 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• Maytansine, N(2')-deacetyl-N(2')-(1-oxopropyl)-
• C35H48ClN3O10
• C35-H48-Cl-N3-O10
• NSC165013
• 38997-09-0
• NSC-165013

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9410	94.10%
Caco-2	-	0.8095	80.95%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Lysosomes	0.5262	52.62%
OATP2B1 inhibitior	+	0.5750	57.50%
OATP1B1 inhibitior	+	0.8312	83.12%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9925	99.25%
P-glycoprotein inhibitior	+	0.8204	82.04%
P-glycoprotein substrate	+	0.7903	79.03%
CYP3A4 substrate	+	0.7466	74.66%
CYP2C9 substrate	-	0.7923	79.23%
CYP2D6 substrate	-	0.8516	85.16%
CYP3A4 inhibition	-	0.8751	87.51%
CYP2C9 inhibition	-	0.8529	85.29%
CYP2C19 inhibition	-	0.8416	84.16%
CYP2D6 inhibition	-	0.8961	89.61%
CYP1A2 inhibition	-	0.8695	86.95%
CYP2C8 inhibition	+	0.6671	66.71%
CYP inhibitory promiscuity	-	0.7304	73.04%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7319	73.19%
Carcinogenicity (trinary)	Non-required	0.4295	42.95%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.9266	92.66%
Skin irritation	-	0.7653	76.53%
Skin corrosion	-	0.9188	91.88%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3609	36.09%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8376	83.76%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7936	79.36%
Acute Oral Toxicity (c)	III	0.5684	56.84%
Estrogen receptor binding	+	0.8160	81.60%
Androgen receptor binding	+	0.7647	76.47%
Thyroid receptor binding	+	0.6402	64.02%
Glucocorticoid receptor binding	+	0.8031	80.31%
Aromatase binding	+	0.6914	69.14%
PPAR gamma	+	0.7957	79.57%
Honey bee toxicity	-	0.5895	58.95%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9846	98.46%

Targets

Proven Targets:

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	99.63%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.72%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.75%	97.25%
CHEMBL261	P00915	Carbonic anhydrase I	95.45%	96.76%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.62%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.45%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.09%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.70%	94.00%
CHEMBL2581	P07339	Cathepsin D	91.34%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.90%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	88.90%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.71%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.68%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.58%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	87.87%	94.75%
CHEMBL220	P22303	Acetylcholinesterase	87.76%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	87.69%	90.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.10%	96.90%
CHEMBL4208	P20618	Proteasome component C5	86.94%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.53%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.43%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.35%	97.09%
CHEMBL5314	Q06418	Tyrosine-protein kinase receptor TYRO3	86.00%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.68%	91.19%
CHEMBL1914	P06276	Butyrylcholinesterase	83.51%	95.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.51%	98.75%
CHEMBL2535	P11166	Glucose transporter	82.72%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.51%	89.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.44%	96.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.57%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.51%	99.17%

Plants that contains it

• Gymnosporia acuminata
• Gymnosporia serrata

Cross-Links

• PubChem: 54610538
• NPASS: NPC161920