Phenyl-carbamic acid 1-[4-(4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-ethyl ester hydrochloride

ID: ALA2093887

PubChem CID: 70682910

Max Phase: Preclinical

Molecular Formula: C33H35ClN2O10

Molecular Weight: 618.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1OC(O[C@H]2C[C@](O)([C@@H](C)OC(=O)Nc3ccccc3)Cc3c(O)c4c(c(O)c32)C(=O)c2ccccc2C4=O)C[C@H](N)[C@@H]1O.Cl

Standard InChI:  InChI=1S/C33H34N2O10.ClH/c1-15-27(36)21(34)12-23(43-15)45-22-14-33(42,16(2)44-32(41)35-17-8-4-3-5-9-17)13-20-24(22)31(40)26-25(30(20)39)28(37)18-10-6-7-11-19(18)29(26)38;/h3-11,15-16,21-23,27,36,39-40,42H,12-14,34H2,1-2H3,(H,35,41);1H/t15-,16+,21-,22-,23?,27+,33-;/m0./s1

Standard InChI Key:  UKSRABFVDYBQPH-BTNHKROMSA-N

Molfile:  

     RDKit          2D

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    8.0934    3.0236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5272   -3.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0979    3.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409   -0.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8271    0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8271   -0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8217    5.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3928    5.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103    5.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
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  7 14  1  0
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 15 19  1  0
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 13 23  1  6
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  4 27  2  0
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M  END

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: 618.64

Molecular Weight (Monoisotopic): 618.2213

AlogP: 3.07

#Rotatable Bonds: 5

Polar Surface Area: 197.87

Molecular Species: BASE

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.03

CX Basic pKa: 9.32

CX LogP: 3.48

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 45

QED Weighted: 0.18

Np Likeness Score: 0.99

References

1. Adams N, Blake C, Broadhurst MJ, Bushnell DJ, Hassall CH, Hartmann HR, Keech E, Stratton AR, Thomas GJ..  (1990)  Synthesis and antitumor activity of 9-[(carbamoyloxy)alkyl]anthracyclines: a novel class of anthracycline derivatives.,  33  (9): [PMID:2391682] [10.1021/jm00171a011]

Source

Source(1):

• Scientific Literature