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133073-73-1 molecular structure
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(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid hydrate

ChemBase ID: 130867
Molecular Formular: C20H24N8O6
Molecular Mass: 472.45456
Monoisotopic Mass: 472.18188053
SMILES and InChIs

SMILES:
CN(Cc1cnc2c(n1)c(nc(n2)N)N)c1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O.O
Canonical SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C.O
InChI:
InChI=1S/C20H22N8O5.H2O/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);1H2/t13-;/m0./s1
InChIKey:
FPJYMUQSRFJSEW-ZOWNYOTGSA-N

Cite this record

CBID:130867 http://www.chembase.cn/molecule-130867.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid hydrate
IUPAC Traditional name
hydrate methotrexate
Synonyms
4-Amino-10-methylfolic acid hydrate
L-4-Amino-N10-methylpteroylglutamic acid hydrate
L-Amethopterin hydrate
Antifolan hydrate
MTX hydrate
Methotrexate hydrate
Methylaminopterin hydrate
L-Amethopterin hydrate
Methotrexate hydrate
Methotrexate
L-氨甲喋呤 水合物
甲氨蝶呤 水合物
对-[(2,4-二氨基喋啶-6)-N-甲基甲氨基]苯甲酰谷氨酸 水合物
L-氨甲喋呤 水合物
MTX 水合物
氟安定 水合物
氨甲叶酸 水合物
氨甲喋呤 水合物
甲氨蝶呤 水合物
甲氨蝶呤
CAS Number
133073-73-1
EC Number
200-413-8
MDL Number
MFCD00150847
PubChem SID
24897252
24278233
24897373
162225145
24853414
PubChem CID
165528

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 165528 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.2608879  H Acceptors 12 
H Donor LogD (pH = 5.5) -3.640823 
LogD (pH = 7.4) -6.5636883  Log P -0.23654379 
Molar Refractivity 119.2108 cm3 Polarizability 43.521362 Å3
Polar Surface Area 210.54 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
H2O: insoluble expand Show data source
Apperance
powder expand Show data source
yellow powder expand Show data source
Optical Rotation
[α]25/D +17°, c = 1 in 0.05 M Na2CO3 expand Show data source
RTECS
MA1225000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
1544 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
46-61-25-36/38 expand Show data source
61-25-36/38 expand Show data source
Safety Statements
53-26-36/37-45 expand Show data source
53-26-36-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H315-H319-H340-H360 expand Show data source
H301-H315-H319-H360 expand Show data source
GHS Precautionary statements
P201-P301 + P310-P305 + P351 + P338-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 1544 6.1/PG 3 expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... DHFRP1(573971), FPGS(2356), SLC19A1(6573), TYMS(7298)mouse ... Dhfr(13361)rat ... Dhfr(24312) expand Show data source
Purity
≥98% (HPLC) expand Show data source
85% expand Show data source
98% expand Show data source
Suitability
meets EP, USP testing specifications expand Show data source
meets USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for insect cell culture expand Show data source
Empirical Formula (Hill Notation)
C20H22N8O5 · xH2O expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - A6770 external link
Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.
Sigma Aldrich - M8407 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Recommended for use in cell culture and molecular biology applications at 0.01-300 μM in nucleoside-free cell culture medium to select for DHFR expression.
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.
Biochem/physiol Actions
Methotrexate used to inhibit dihyrofolate reductase and select for DHFR overexpresssion.
Sigma Aldrich - M4010 external link
Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.
Sigma Aldrich - 223948 external link
Packaging
100 mg in glass bottle
Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3
Sigma Aldrich - 06564 external link
Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.
Sigma Aldrich - M9929 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Methotrexate is an allosteric inhibititor of dihydrofolate reductase (DHFR), the enzyme that catalyzes the conversion of dihydrofolate to tetrahydrofolate. Since tetrahydrolfolate is required for purine and pyrimidine synthesis, methotrexate treatment results in the inhibition of DNA and RNA synthesis.
Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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