Anhydroleucovorin

Details

• Internal ID: d5531eda-8c8e-4125-a2b2-ba825b3d109b
• Taxonomy: Organoheterocyclic compounds > Pteridines and derivatives > Pterins and derivatives > Tetrahydrofolic acids and derivatives > Tetrahydrofolic acids
• IUPAC Name: (2S)-2-[[4-[(6aR)-3-amino-1-oxo-5,6,6a,7-tetrahydro-2H-imidazo[1,5-f]pteridin-10-ium-8-yl]benzoyl]amino]-5-hydroxy-5-oxopentanoate
• InChI: InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1
• InChI Key: MEANFMOQMXYMCT-OLZOCXBDSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁N₇O₆
• Molecular Weight: 455.40 g/mol
• Exact Mass: 455.15533142 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.95
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• methenyl-THF
• Anhydroleucovorin A
• 5,10-methenyl-THF
• CH-THF
• methenyl-tetrahydrofolate
• Methenyltetrahydrofolic acid
• n5-n10-CH-THF
• n5-n10-methenyltetrahydrofolate
• 5,10-methenyltetrahydrofolate
• 5,10-Methenyltetrahydropteroylglutamate
• anhydro-leucovorin
• anhydro-leucovorin a
• Leucovorin, anhydro-
• methenyltetrahydrofolate
• Leucovorin A, anhydro-
• MEANFMOQMXYMCT-OLZOCXBDSA-N
• PD133487
• HY-153039
• CS-0647785
• (6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-1H,4H,5H,6H,6aH,7H,8H-2,4,5,8,10000000$l^{5}-imidazo[1,5-f]pteridin-10-ylium
• (S)-2-(4-((R)-3-Amino-1-oxo-1,4,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8-ium-8-yl)benzamido)-4-carboxybutanoate
• 1H-Imidazo[1,5-f]pteridin-10-ium, 3-amino-8-[p-[(1,3-dicarboxypropyl)carbamoyl]phenyl]-2,5,6,6a,7,8-hexahydro-1-oxo-, hydroxide, inner salt (8CI)
• 3-Amino-8-[p-[(1,3-dicarboxypropyl)carbamoyl]phenyl]-1,2,5,6,6a,7-hexahydro-1-oxo-8H-imidazo[1,5-f]pteridin-10-ium hydroxide, inner salt (7CI)
• 3-Amino-8-[p-[(L-1,3-dicarboxypropyl)carbamoyl]phenyl]-1,2,5,6,6a,7-hexahydro-1-oxo-8H-imidazo[1,5-f]pteridin-10-ium hydroxide, inner salt (6CI)
• Imidazo[1,5-f]pteridinium, 3-amino-8-[4-[[(1,3-dicarboxypropyl)amino]carbonyl]phenyl]-1,2,5,6,6a,7-hexahydro-1-oxo-, inner salt, [R-(R*,S*)]-
• Imidazo[1,5-f]pteridinium, 3-amino-8-[4-[[[(1S)-1,3-dicarboxypropyl]amino]carbonyl]phenyl]-1,2,5,6,6a,7-hexahydro-1-oxo-, inner salt, (6aR)- (9CI)
• L-glutamic acid, N-[4-[(6aR)-3-amino-1,4,5,6,6a,7-hexahydro-1-oxoimidazo[1,5-f]pteridinium-8-yl]benzoyl]-, inner salt

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8190	81.90%
Caco-2	-	0.8948	89.48%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Nucleus	0.4601	46.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9182	91.82%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.9209	92.09%
OCT2 inhibitior	-	0.7423	74.23%
BSEP inhibitior	-	0.8000	80.00%
P-glycoprotein inhibitior	-	0.5861	58.61%
P-glycoprotein substrate	+	0.6947	69.47%
CYP3A4 substrate	+	0.6061	60.61%
CYP2C9 substrate	-	0.7941	79.41%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	-	0.9203	92.03%
CYP2C9 inhibition	-	0.9078	90.78%
CYP2C19 inhibition	-	0.9052	90.52%
CYP2D6 inhibition	-	0.8526	85.26%
CYP1A2 inhibition	-	0.8005	80.05%
CYP2C8 inhibition	-	0.5980	59.80%
CYP inhibitory promiscuity	-	0.9623	96.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6048	60.48%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.9741	97.41%
Skin irritation	-	0.7694	76.94%
Skin corrosion	-	0.9353	93.53%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5618	56.18%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8561	85.61%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8705	87.05%
Acute Oral Toxicity (c)	III	0.6221	62.21%
Estrogen receptor binding	+	0.6451	64.51%
Androgen receptor binding	+	0.6106	61.06%
Thyroid receptor binding	+	0.6146	61.46%
Glucocorticoid receptor binding	-	0.4725	47.25%
Aromatase binding	+	0.6847	68.47%
PPAR gamma	+	0.5977	59.77%
Honey bee toxicity	-	0.8807	88.07%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.6528	65.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.03%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.26%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.53%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.39%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.24%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.40%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.80%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.90%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.44%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.44%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.05%	96.90%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.87%	96.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.68%	95.56%
CHEMBL1781	P11387	DNA topoisomerase I	83.75%	97.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.59%	93.10%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	82.66%	95.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.33%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.86%	93.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.45%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.09%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 135450599
• LOTUS: LTS0033985
• wikiData: Q2823228