Maitansine

Details

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Internal ID de5f4a1e-8a7c-4eb8-9607-67b5a7bed5ad
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-[acetyl(methyl)amino]propanoate
SMILES (Canonical) CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)C)C)C)OC)(NC(=O)O2)O
SMILES (Isomeric) C[C@@H]1[C@@H]2C[C@]([C@@H](C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)\C)OC)(NC(=O)O2)O
InChI InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10?,18-11+/t19-,20+,25+,26-,27+,30+,33+,34+/m1/s1
InChI Key WKPWGQKGSOKKOO-WLNOZUDTSA-N
Popularity 823 references in papers

Physical and Chemical Properties

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Molecular Formula C34H46ClN3O10
Molecular Weight 692.20 g/mol
Exact Mass 691.2871724 g/mol
Topological Polar Surface Area (TPSA) 157.00 Ų
XlogP 2.00
Atomic LogP (AlogP) 3.53
H-Bond Acceptor 10
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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Maytansin
MAYTANSINE
Maysanine
Maytansine (USAN
MLS002703019
C34-H46-Cl-N3-O10
NSC153858
35846-53-8
Alanine, 6-ester with 11-chloro-6,21-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1(10,24).0(3,5)]hexacosa-10,12,14[26],16,18-pentaene-8,23-dione
L-Alanine, 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 ester, [1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*)]-

2D Structure

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2D Structure of Maitansine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9277 92.77%
Caco-2 - 0.8056 80.56%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Lysosomes 0.5455 54.55%
OATP2B1 inhibitior + 0.5794 57.94%
OATP1B1 inhibitior + 0.8337 83.37%
OATP1B3 inhibitior + 0.9353 93.53%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior + 0.9906 99.06%
P-glycoprotein inhibitior + 0.8271 82.71%
P-glycoprotein substrate + 0.7828 78.28%
CYP3A4 substrate + 0.7464 74.64%
CYP2C9 substrate - 0.7923 79.23%
CYP2D6 substrate - 0.8516 85.16%
CYP3A4 inhibition - 0.9409 94.09%
CYP2C9 inhibition - 0.8944 89.44%
CYP2C19 inhibition - 0.8924 89.24%
CYP2D6 inhibition - 0.9150 91.50%
CYP1A2 inhibition - 0.9000 90.00%
CYP2C8 inhibition + 0.6202 62.02%
CYP inhibitory promiscuity - 0.8138 81.38%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.7319 73.19%
Carcinogenicity (trinary) Danger 0.4453 44.53%
Eye corrosion - 0.9816 98.16%
Eye irritation - 0.9285 92.85%
Skin irritation - 0.7656 76.56%
Skin corrosion - 0.9191 91.91%
Ames mutagenesis + 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7158 71.58%
Micronuclear + 0.8200 82.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.8402 84.02%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.7544 75.44%
Acute Oral Toxicity (c) III 0.5724 57.24%
Estrogen receptor binding + 0.8174 81.74%
Androgen receptor binding + 0.7580 75.80%
Thyroid receptor binding + 0.6555 65.55%
Glucocorticoid receptor binding + 0.8134 81.34%
Aromatase binding + 0.6969 69.69%
PPAR gamma + 0.8093 80.93%
Honey bee toxicity - 0.5796 57.96%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9806 98.06%

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 99.33% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.52% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.81% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.46% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.92% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.95% 91.11%
CHEMBL261 P00915 Carbonic anhydrase I 92.94% 96.76%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 91.21% 97.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.94% 97.25%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.53% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 90.04% 91.19%
CHEMBL1914 P06276 Butyrylcholinesterase 89.88% 95.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.85% 94.00%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 89.04% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 88.56% 94.75%
CHEMBL4208 P20618 Proteasome component C5 88.29% 90.00%
CHEMBL2581 P07339 Cathepsin D 87.86% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 87.31% 94.73%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 85.55% 96.90%
CHEMBL217 P14416 Dopamine D2 receptor 85.46% 95.62%
CHEMBL5314 Q06418 Tyrosine-protein kinase receptor TYRO3 85.10% 96.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.22% 95.89%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.68% 96.77%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 83.07% 91.03%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.71% 89.50%
CHEMBL2535 P11166 Glucose transporter 81.95% 98.75%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 81.74% 98.75%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 81.58% 85.11%

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.
Gymnosporia acuminata
Gymnosporia serrata

Cross-Links

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PubChem 54604312
NPASS NPC258572