Compound Summary
Compound Information
methotrexate
Compound Name: | methotrexate |
Compound CID: | 126941 |
Synonyms: | methotrexate 59-05-2 Rheumatrex Amethopterin Abitrexate More... |
Iupac Name: | (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid |
InChI: | InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1 |
InChIKey: | FBOZXECLQNJBKD-ZDUSSCGKSA-N |
Canonical Smiles: | CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O |
Isomeric Smiles: | CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O |
Molecular Weight: | 454.4 |
Molecular Formula: | C20H22N8O5 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
methotrexate
Molecular Weight: | 454.4 |
Molecular Formula: | C20H22N8O5 |
Hydrogen Bond Donor Count: | 5 |
Hydrogen Bond Acceptor Count: | 12 |
Rotatable Bond Count: | 9 |
Heavy Atom Count: | 33 |
Complexity: | 704 |
Synonyms
methotrexate
| methotrexate | methotrexate |
|---|---|
methotrexate |
59-05-2 |
Rheumatrex |
Amethopterin |
Abitrexate |
Trexall |
Metatrexan |
Hdmtx |
Methylaminopterinum |
(S)-2-(4-(((2,4-Diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioic acid |
MTX |
4-Amino-10-methylfolic acid |
Methylaminopterin |
Methotrexatum |
Metotrexato |
Maxtrex |
Rasuvo |
Mexate-Aq |
N-Bismethylpteroylglutamic acid |
NSC-740 |
NCI-C04671 |
Methotrexate Lpf |
133073-73-1 |
CL-14377 |
UNII-YL5FZ2Y5U1 |
Amethopterine |
Farmitrexat |
EMT 25,299 |
L-Amethopterin |
Methotrexat-Ebewe |
TCMDC-125858 |
(2S)-2-4-(2,4-diaminopteridin-6-yl)methyl-methylaminobenzoylaminopentanedioic acid |
Abitrexate (Methotrexate) |
R 9985 |
YL5FZ2Y5U1 |
Methotextrate |
Methotrexat |
CL 14377 |
CHEMBL34259 |
NSC740 |
CHEBI:44185 |
N-4-(2,4-diamino-6-pteridinyl)methylmethylaminobenzoyl-L-glutamic acid |
N-(4-{(2,4-diaminopteridin-6-yl)methyl(methyl)amino}phenyl)carbonyl-L-glutamic acid |
CL14377 |
NCGC00025060-04 |
NSC 740 |
C20H22N8O5 |
4-amino-N(10)-methylpteroylglutamic acid |
A-Methopterin |
DSSTox_CID_822 |
A-Methpterin |
Amethopterin L- |
Folex-Pfs |
MFCD00150847 |
(2S)-2-(4-{(2,4-diaminopteridin-6-yl)methyl(methyl)amino}phenyl)formamidopentanedioic acid |
DSSTox_RID_75810 |
Methotrexate, L- |
DSSTox_GSID_20822 |
R-methotrexate |
X 133 |
Metotressato DCIT |
Fauldexato |
Medsatrexate |
Methoblastin |
Metotressato |
Brimexate |
Emthexat |
Emthexate |
Lantarel |
Lumexon |
Metrotex |
Novatrex |
Otrexup |
Tremetex |
Trexeron |
Trixilem |
Metex |
Texate |
MLS001401431 |
Methotrexatum INN-Latin |
Metotrexato INN-Spanish |
3Hmethotrexate |
SMR000112001 |
3H-methotrexate |
CCRIS 1109 |
4-Aminomethylpteroylglutamic acid |
HSDB 3123 |
L-(+)-N-(p-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)glutamic acid |
N-(p-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-(+)-glutamic acid |
SR-01000075682 |
SMR000449324 |
EINECS 200-413-8 |
Metolate |
Nordimet |
Xatmep |
AI3-25299 |
Antifolan hydrate |
Intradose-MTX |
MTX hydrate |
4-Amino-N(sup 10)-methylpteroylglutamic acid |
1dhi |
1dhj |
2drc |
4ocx |
(2S)-2-4-(2,4-diaminopteridin-6-yl)methyl-methyl-aminobenzoylaminopentanedioic acid |
CAS-59-05-2 |
Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, L- |
Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-L-glutamova |
MPI-2505 |
Prestwick_322 |
Otrexup (TN) |
Xatmep (TN) |
folic acid antagonist |
An-PDN |
Kyselina 4-amino-N(sup 10)-methylpteroylglutamova Czech |
Methylaminopterin; MTX |
DL-Amethopterin hydrate |
Methotrexate USAN:USP:INN:BAN:JAN |
Spectrum_001836 |
Tocris-1230 |
4kn0 |
WR-19039 |
Methylaminopterin hydrate |
Prestwick0_000135 |
Prestwick1_000135 |
Prestwick2_000135 |
Spectrum2_001077 |
Spectrum3_000497 |
Spectrum4_000616 |
Spectrum5_000958 |
Methotrexate - Abitrexate |
N-(p-(((2,4-Diamino-6-pteridyl)methyl)methylamino)benzoyl)glutamic acid |
L(+)-Amethopterin hydrate |
N-(4-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutamicacid |
NCIMech_000767 |
SCHEMBL3711 |
Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-L-glutamova Czech |
BIDD:PXR0175 |
Lopac0_000020 |
KBioGR_001172 |
KBioSS_002341 |
Kyselina 4-amino-N(sup 10)-methylpteroylglutamova |
MLS000049968 |
MLS002154208 |
DivK1c_000114 |
SPBio_001094 |
SPBio_002149 |
AMY235 |
cid_126941 |
cid_165528 |
GTPL4674 |
GTPL4815 |
DTXSID4020822 |
SCHEMBL12421860 |
SCHEMBL23111732 |
BDBM18050 |
BDBM66082 |
HMS500F16 |
KBio1_000114 |
KBio2_002338 |
KBio2_004906 |
KBio2_007474 |
KBio3_001493 |
Methotrexate (JP17/USP/INN) |
AOB5585 |
g301 |
NINDS_000114 |
Bio1_000486 |
Bio1_000975 |
Bio1_001464 |
HMS1568K12 |
HMS2095K12 |
HMS2233O18 |
HMS3260C21 |
HMS3414L09 |
HMS3678L07 |
HMS3712K12 |
ACT03341 |
ADX-2191 |
APC-2002 |
BCP13701 |
MPI-5004 |
ZINC1529323 |
Tox21_110944 |
Tox21_300269 |
Tox21_500020 |
4-Amino-10-methylfolic acid hydrate |
CCG-35800 |
EMT-25299 |
MFCD00064370 |
s1210 |
STL535338 |
(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamic acid |
AKOS016340329 |
Tox21_110944_1 |
ACN-050905 |
CS-1732 |
DB00563 |
KS-5093 |
LP00020 |
MCULE-6523054194 |
SDCCGSBI-0050009.P003 |
WR19039 |
IDI1_000114 |
N-(4-{(2,4-diaminopteridin-6-yl)methyl(methyl)amino}benzoyl)-L-glutamic acid |
SMP2_000020 |
(methyl)amino)benzamido)pentanedioic acid |
NCGC00025060-01 |
NCGC00025060-02 |
NCGC00025060-03 |
NCGC00025060-05 |
NCGC00025060-06 |
NCGC00025060-07 |
NCGC00025060-08 |
NCGC00025060-09 |
NCGC00025060-10 |
NCGC00025060-11 |
NCGC00025060-12 |
NCGC00025060-13 |
NCGC00025060-15 |
NCGC00025060-16 |
NCGC00254216-01 |
NCGC00260705-01 |
HY-14519 |
EU-0100020 |
G-301 |
SW198601-3 |
Methotrexate 1.0 mg/ml in Dimethyl Sulfoxide |
1771-EP0930075A1 |
1771-EP2269989A1 |
1771-EP2269994A1 |
1771-EP2270001A1 |
1771-EP2270008A1 |
1771-EP2270018A1 |
1771-EP2270505A1 |
1771-EP2272825A2 |
1771-EP2272827A1 |
1771-EP2272832A1 |
1771-EP2275413A1 |
1771-EP2275420A1 |
1771-EP2277565A2 |
1771-EP2277566A2 |
1771-EP2277567A1 |
1771-EP2277568A2 |
1771-EP2277569A2 |
1771-EP2277570A2 |
1771-EP2277865A1 |
1771-EP2277876A1 |
1771-EP2280012A2 |
1771-EP2281563A1 |
1771-EP2281815A1 |
1771-EP2287156A1 |
1771-EP2289892A1 |
1771-EP2289894A2 |
1771-EP2292233A2 |
1771-EP2292280A1 |
1771-EP2292595A1 |
1771-EP2292614A1 |
1771-EP2292615A1 |
1771-EP2292617A1 |
1771-EP2295055A2 |
1771-EP2295416A2 |
1771-EP2295426A1 |
1771-EP2295427A1 |
1771-EP2298743A1 |
1771-EP2298748A2 |
1771-EP2298764A1 |
1771-EP2298765A1 |
1771-EP2298768A1 |
1771-EP2298772A1 |
1771-EP2298778A1 |
1771-EP2298780A1 |
1771-EP2301928A1 |
1771-EP2301933A1 |
1771-EP2305243A1 |
1771-EP2305640A2 |
1771-EP2305642A2 |
1771-EP2305660A1 |
1771-EP2305668A1 |
1771-EP2305671A1 |
1771-EP2305679A1 |
1771-EP2305689A1 |
1771-EP2308833A2 |
1771-EP2308839A1 |
1771-EP2308855A1 |
1771-EP2308861A1 |
1771-EP2311453A1 |
1771-EP2311807A1 |
1771-EP2311808A1 |
1771-EP2311825A1 |
1771-EP2311827A1 |
1771-EP2311829A1 |
1771-EP2311840A1 |
1771-EP2311842A2 |
1771-EP2311850A1 |
1771-EP2314590A1 |
1771-EP2316459A1 |
1771-EP2316832A1 |
1771-EP2316833A1 |
1771-EP2316834A1 |
1771-EP2371811A2 |
1771-EP2374454A1 |
5947-EP0930075A1 |
5947-EP2269994A1 |
5947-EP2289892A1 |
73M731 |
A10021 |
C01937 |
D00142 |
J10045 |
R-9985 |
DL-4-Amino-N10-methylpteroylglutamic acid hydrate |
Q422232 |
SR-01000597411 |
W-60383 |
(S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl) |
Q-201366 |
SR-01000075682-1 |
SR-01000075682-2 |
SR-01000075682-6 |
SR-01000597411-1 |
W-105347 |
2,2-(9,10-anthracenediylidene)-bis-propanedinitrile |
BRD-K59456551-001-09-3 |
BRD-K59456551-001-11-9 |
WLN: T66 BN DN GN JNJ CZ EZ H1N1&R DVMYVQ2VQ |
Z1541638527 |
N,N,N,N-ETHYLENEDIAMINETETRA(METHYLENEPHOSPHONICACID) |
UNII-99ITO15X8S component FBOZXECLQNJBKD-ZDUSSCGKSA-N |
Methotrexate, European Pharmacopoeia (EP) Reference Standard |
Methotrexate, United States Pharmacopeia (USP) Reference Standard |
Glutamic acid,4-diamino-6-pteridinyl)methyl methylaminobenzoyl-, L-(+)- |
L-Glutamic acid,4-diamino-6-pteridinyl)methyl- methylaminobenzoyl- |
(S)-2-(4-(((2,4-Diaminopteridin-6-yl)methyl)-(methyl)amino)benzamido)pentanedioic acid |
L-Glutamic acid,N-4-(2,4-diamino-6-pteridinyl)methylmethylaminobenzoyl-,hydrate(9ci) |
Methotrexate for peak identification, European Pharmacopoeia (EP) Reference Standard |
Methotrexate for system suitability, European Pharmacopoeia (EP) Reference Standard |
Methotrexate, Pharmaceutical Secondary Standard; Certified Reference Material |
N-4-(2,4-Diamino-6-pteridinyl)methyl methylaminobenzoyl-L-glutamic acid |
(2S)-2-4-(2,4-diamino-6-pteridinyl)methyl-methylaminophenyl-oxomethylaminopentanedioic acid;hydrate |
(2S)-2-4-(2,4-diaminopteridin-6-yl)methyl-methyl-aminobenzoylaminoglutaric acid;hydrate |
(2S)-2-4-2,4-bis(azanyl)pteridin-6-ylmethyl-methyl-aminophenylcarbonylaminopentanedioic acid;hydrate |
102613-64-9 |
70359-39-6 |
L-Glutamic acid,N-4-(2,4-diamino-6-pteridinyl)methylmethylaminobenzoyl-, hydrate (9CI) |
Methotrexate, PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production, meets EP, USP testing specifications |
Experimental Data
methotrexate
| Species | Dosage | Unit | CG Lifespan(AVG/MED days) | TG Lifespan(AVG/MED days) | Lifespan Change(AVG/MED%) | CG Lifespan(MAX days) | TG Lifespan(MAX days) | Lifespan Change(MAX%) | Significant | Strain | Gender | PubMed | Active Label |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Caenorhabditis elegans | 33 | umol/L | -6 | NS | N2 | 24134630 | Inactive |
Experimental Data Visualization
methotrexate
Statistics Data
methotrexate
| Species | Lifespan Change(AVG/MED%) | Lifespan Change(MAX%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | -6 | 1 | 1 |
Statistics Data Visualization
methotrexate
