2-Amino-4-{3-[5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-2-phosphonooxy-Hydroxyphosphinoylamino-phosphonic acid-propylsulfanyl}-butyric acid

ID: ALA3706403

PubChem CID: 14015345

Max Phase: Preclinical

Molecular Formula: C16H28N7O14P3S

Molecular Weight: 667.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CC(CSCC[C@H](N)C(=O)O)OP(=O)(O)OP(=O)(O)NP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H28N7O14P3S/c17-8(16(26)27)1-2-41-4-7(36-40(33,34)37-39(31,32)22-38(28,29)30)3-9-11(24)12(25)15(35-9)23-6-21-10-13(18)19-5-20-14(10)23/h5-9,11-12,15,24-25H,1-4,17H2,(H,26,27)(H,33,34)(H2,18,19,20)(H4,22,28,29,30,31,32)/t7?,8-,9+,11+,12+,15+/m0/s1

Standard InChI Key:  RNHQQJAVJKCFTI-JGCREQEZSA-N

Molfile:  

     RDKit          2D

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 15 35  1  1
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M  END

Alternative Forms

1. Parent:

   

   ALA3706403

   (2S)-2-amino-4-[3-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-2-[hydroxy-[hydroxy-(phosphonoamino)phosphoryl]oxyphosphoryl]oxypropyl]sulfanylbutanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 667.42

Molecular Weight (Monoisotopic): 667.0628

AlogP: -1.76

#Rotatable Bonds: 15

Polar Surface Area: 345.25

Molecular Species: ZWITTERION

HBA: 16

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.33

CX Basic pKa: 9.50

CX LogP: -7.95

CX LogD: -15.08

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.07

Np Likeness Score: 1.00

References

1. Kappler F, Vrudhula VM, Hampton A..  (1988)  Toward the synthesis of isozyme-specific enzyme inhibitors. Potent inhibitors of rat methionine adenosyltransferases. Effect of one-atom elongation of the ribose-P alpha bridge in two covalent adducts of L-methionine and beta,gamma-imido-ATP.,  31  (2): [PMID:3257524] [10.1021/jm00397a020]

Source

Source(1):

• Scientific Literature