1,-(4-((3R,4R)-3-((3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yloxy)-4-formyl-4-hydroxy-5-methyltetrahydrofuran-2-yloxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine

ID: ALA4087771

PubChem CID: 137643646

Max Phase: Preclinical

Molecular Formula: C21H39N7O12

Molecular Weight: 581.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@H]1C(O[C@H]2C(OC3C(O)C(O)C(NC(=N)N)C(O)C3NC(=N)N)OC(C)[C@]2(O)C=O)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5?,6-,7?,8?,9-,10-,11?,12?,13-,14?,15?,16+,17?,18?,21-/m1/s1

Standard InChI Key:  UCSJYZPVAKXKNQ-WPFINQCMSA-N

Molfile:  

     RDKit          2D

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  2 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087771

   ---

Molecule Features

Natural Product: Yes

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: 581.58

Molecular Weight (Monoisotopic): 581.2657

AlogP: -7.74

#Rotatable Bonds: 9

Polar Surface Area: 331.43

Molecular Species: BASE

HBA: 15

HBD: 14

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 16

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 10.88

CX Basic pKa: 11.48

CX LogP: -7.49

CX LogD: -12.13

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.07

Np Likeness Score: 1.69

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature