(S)-2-{4-[(2-Amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid

ID: ALA1679

Chembl Id: CHEMBL1679

Max Phase: Approved

First Approval: 1952

Molecular Formula: C20H23N7O7

Molecular Weight: 473.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Leucovorin

Synonyms from Alternative Forms(30): Calcium folinate | Folinic acid | Folinic acid calcium salt pentahydrate | Anhydrous calcium folinate | Calcii folinas | Calcium folinate pentahydrate | Citrovorum factor | Folaren | Foliben | Folinate-sf calcium | Lederfolat | Lederfolin | Leucosar | Leucovorin calcium | Leucovorin calcium pentahydrate | Rescufolin | Rescuvolin | Tonofolin | NSC-3590 | Calc folinate | Folacal | Fusilev | Leucovorin calcium preservative free | Wellcovorin | Folic acid related compound a | Sodium folinate | Disodium folinate | Folinic acid disodium | Leucovorin sodium | Oncofolic

Canonical SMILES:  Nc1nc(=O)c2c([nH]1)NCC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)N2C=O

Standard InChI:  InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m0/s1

Standard InChI Key:  VVIAGPKUTFNRDU-ABLWVSNPSA-N

Alternative Forms

1. Parent:

   

   ALA1679

   LEUCOVORIN

2. Alternative Forms:

   

   ALA1679

   Folinic acid calcium salt hydrate
3. 

   ALA1679

   Folinic acid, calcium salt pentahydrate
4. 

   ALA1679

   SODIUM FOLINATE

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 473.45

Molecular Weight (Monoisotopic): 473.1659

AlogP: -0.73

#Rotatable Bonds: 10

Polar Surface Area: 219.84

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.55

CX Basic pKa: 4.67

CX LogP: -3.76

CX LogD: -8.79

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: 0.20

References

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22. Unpublished dataset, 

23. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

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Source

Source(6):

• Scientific Literature
• Clinical Candidates
• DrugMatrix
• TP-search Transporter Database
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6