D-Amethopterin

Details

• Internal ID: 80213a10-7884-4460-ad2e-9dd2ee251c7d
• Taxonomy: Organoheterocyclic compounds > Pteridines and derivatives > Pterins and derivatives > Folic acids and derivatives > Folic acids
• IUPAC Name: (2R)-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-/m1/s1
• InChI Key: FBOZXECLQNJBKD-CYBMUJFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂N₈O₅
• Molecular Weight: 454.40 g/mol
• Exact Mass: 454.17131583 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): 0.27
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• D-Methotrexate
• 51865-79-3
• (R)-Methotrexate
• Methotrexate, (R)-
• R-methotrexate
• (-)Amethopterin
• CHEMBL156
• (2R)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
• TCMDC-125488
• W12798130R
• D(-)-AMETHOPTERIN
• NSC 117356
• Methotrexate, d-
• (2~{r})-2-[[4-[[2,4-Bis(Azanyl)pteridin-6-Yl]methyl-Methyl-Amino]phenyl]carbonylamino]pentanedioic Acid
• 331717-43-2
• EINECS 257-482-2
• NSC117356
• CAS-59-05-2
• UNII-W12798130R
• Lopac-A-6770
• Lopac-A-9898
• D-(-)-N-(2,4-Diamino-6-pteridinyl(dimethylamino)benzoyl)glutamic acid
• N-(4-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-D-glutamic acid
• Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, D-
• Lopac0_000095
• SCHEMBL171251
• d(-)-Amethopterin hydrate,98
• CAS-59-05-2-Batch2
• R-METHOTREXATE [USP-RS]
• DTXSID201317276
• BDBM50420238
• AKOS015895149
• CCG-204190
• D-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
• D-glutamic acid, N-(4-(((2,4-diamino-6-pteridyl)methyl)methylamino)benzoyl)-
• NCGC00015079-01
• NCGC00015079-02
• NCGC00016264-01
• NCGC00016264-02
• METHOTREXATE IMPURITY F [EP IMPURITY]
• A 9898
• A828817
• Q27292170
• (2R)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid
• D-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl][methyl]amino]benzoyl]-
• (2R)-2-((4-(((2,4-DIAMINOPTERIDIN-6-YL)METHYL)METHYLAMINO)BENZOYL)AMINO)PENTANEDIOIC ACID
• (2R)-2-[[[4-[(2,4-diamino-6-pteridinyl)methyl-methylamino]phenyl]-oxomethyl]amino]pentanedioic acid
• (2R)-2-[[4-[[2,4-bis(azanyl)pteridin-6-yl]methyl-methyl-amino]phenyl]carbonylamino]pentanedioic acid
• 6UV

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6037	60.37%
Caco-2	-	0.8662	86.62%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.4349	43.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8317	83.17%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	+	0.6132	61.32%
CYP3A4 substrate	+	0.6130	61.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8393	83.93%
CYP3A4 inhibition	-	0.8333	83.33%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8005	80.05%
CYP inhibitory promiscuity	-	0.9739	97.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6979	69.79%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9749	97.49%
Skin irritation	-	0.7792	77.92%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3920	39.20%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.8819	88.19%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.5145	51.45%
Acute Oral Toxicity (c)	II	0.7310	73.10%
Estrogen receptor binding	-	0.6478	64.78%
Androgen receptor binding	-	0.5352	53.52%
Thyroid receptor binding	+	0.8275	82.75%
Glucocorticoid receptor binding	-	0.8662	86.62%
Aromatase binding	+	0.6479	64.79%
PPAR gamma	+	0.7066	70.66%
Honey bee toxicity	-	0.8615	86.15%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.7653	76.53%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	100 nM; 158.5 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL202	P00374	Dihydrofolate reductase	0.00034 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	5 nM; 4.5 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	354.8 nM; 501.2 nM; 89.1 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1952	P04818	Thymidylate synthase	600 nM	Ki	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	199.5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.79%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.63%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	97.55%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	97.03%	93.10%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.90%	89.34%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.59%	95.17%
CHEMBL2581	P07339	Cathepsin D	92.18%	98.95%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	90.73%	95.48%
CHEMBL1255126	O15151	Protein Mdm4	90.25%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.96%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	89.17%	94.73%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	88.41%	100.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.17%	81.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.04%	87.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.53%	90.71%
CHEMBL1781	P11387	DNA topoisomerase I	84.97%	97.00%
CHEMBL1907	P15144	Aminopeptidase N	84.89%	93.31%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.24%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.20%	86.33%
CHEMBL1892	Q04609	Glutamate carboxypeptidase II	81.95%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.36%	96.90%
CHEMBL3232685	O00257	E3 SUMO-protein ligase CBX4	80.70%	93.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 72440
• LOTUS: LTS0148365
• wikiData: Q27292170