2-((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-(((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-((1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yloxy)tetrahydro-2H-pyran-4-ylcarbamoyloxy)methyl)-2-nitrophenoxy)tetrahydro-2H-pyran-2-yl)acetic acid

ID: ALA2058275

PubChem CID: 70694727

Max Phase: Preclinical

Molecular Formula: C42H44N2O22

Molecular Weight: 928.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](NC(=O)OCc2ccc(O[C@@H]3O[C@H](CC(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c([N+](=O)[O-])c2)[C@H](O)[C@H](C)O1

Standard InChI:  InChI=1S/C42H44N2O22/c1-15-32(49)19(43-41(57)62-14-16-6-7-21(20(8-16)44(59)60)65-40-39(56)38(55)35(52)23(66-40)10-26(47)48)9-27(63-15)64-24-12-42(58,25(46)13-45)11-18-29(24)37(54)31-30(34(18)51)33(50)17-4-3-5-22(61-2)28(17)36(31)53/h3-8,15,19,23-24,27,32,35,38-40,45,49,51-52,54-56,58H,9-14H2,1-2H3,(H,43,57)(H,47,48)/t15-,19-,23+,24-,27-,32+,35+,38-,39+,40+,42-/m0/s1

Standard InChI Key:  MSFSWIQEZQEUBC-OSRGRKTGSA-N

Molfile:  

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M  CHG  2  49   1  51  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2058275

   2-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]carbamoyloxymethyl]-2-nitrophenoxy]oxan-2-yl]acetic 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: 928.81

Molecular Weight (Monoisotopic): 928.2386

AlogP: -0.46

#Rotatable Bonds: 13

Polar Surface Area: 377.97

Molecular Species: ACID

HBA: 21

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 24

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.25

CX Basic pKa: ┄

CX LogP: 1.44

CX LogD: -2.09

Aromatic Rings: 3

Heavy Atoms: 66

QED Weighted: 0.05

Np Likeness Score: 1.19

References

1. Legigan T, Clarhaut J, Renoux B, Tranoy-Opalinski I, Monvoisin A, Berjeaud JM, Guilhot F, Papot S..  (2012)  Synthesis and antitumor efficacy of a β-glucuronidase-responsive albumin-binding prodrug of doxorubicin.,  55  (9): [PMID:22515366] [10.1021/jm300348r]

Source

Source(1):

• Scientific Literature