carbamic acid (4E,10E)-(8S,9S,12S,13R,14S,16R)-13,19,20-trihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl ester

ID: ALA401784

PubChem CID: 44446533

Max Phase: Preclinical

Molecular Formula: C28H42N2O8

Molecular Weight: 534.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1C[C@H](C)Cc2cc(cc(O)c2O)NC(=O)/C(C)=C/CC[C@H](OC)[C@@H](OC(N)=O)/C(C)=C/[C@H](C)[C@H]1O

Standard InChI:  InChI=1S/C28H42N2O8/c1-15-10-19-13-20(14-21(31)25(19)33)30-27(34)16(2)8-7-9-22(36-5)26(38-28(29)35)18(4)12-17(3)24(32)23(11-15)37-6/h8,12-15,17,22-24,26,31-33H,7,9-11H2,1-6H3,(H2,29,35)(H,30,34)/b16-8+,18-12+/t15-,17+,22+,23+,24-,26+/m1/s1

Standard InChI Key:  LQCLDVBADKXMJS-WCTXHBHRSA-N

Molfile:  

     RDKit          2D

 38 39  0  0  1  0  0  0  0  0999 V2000
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    6.6737  -14.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9632  -13.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710  -12.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2448  -13.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6893  -12.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2604  -12.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5421  -12.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2682  -11.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577  -11.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655  -10.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800   -9.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800   -9.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9944  -10.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7135   -9.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7135   -9.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9944   -8.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4274  -10.2768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1424   -9.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8563  -10.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1436   -9.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8552  -11.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5714   -9.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5691  -11.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5680  -12.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8529  -12.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1390  -12.3403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4746  -13.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393  -11.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8315  -12.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9235  -14.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7474  -14.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1224  -13.5225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1963  -14.9495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4240  -12.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1402  -11.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933   -7.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5646   -8.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  1 35  1  0
 19 20  1  0
  9 10  1  0
 19 21  2  0
  3  5  1  6
 20 22  2  0
 10 11  1  0
 20 23  1  0
 12 13  1  0
 22 24  1  0
 24 25  1  0
  4  6  1  6
 25 26  1  0
  2  3  1  0
 26 27  1  1
  4  7  1  0
 26 28  1  0
 13 11  1  0
  1 28  1  0
  1  2  2  0
 10 29  1  6
  7  8  1  1
  8 30  1  0
 12 17  2  0
 28 31  1  1
 13 14  2  0
 31 32  1  0
 14 15  1  0
 32 33  2  0
 15 16  2  0
 32 34  1  0
 16 17  1  0
  3  4  1  0
 27 36  1  0
 15 18  1  0
 17 37  1  0
  7  9  1  0
 12 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA401784

   [(4E,8S,9S,10E,12S,13R,14S,16R)-13,19,20-trihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(22),4,10,18,20-pentaen-9-yl] carbamate

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: 534.65

Molecular Weight (Monoisotopic): 534.2941

AlogP: 3.78

#Rotatable Bonds: 3

Polar Surface Area: 160.57

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.30

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.79

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: 1.99

References

1. Onodera H, Kaneko M, Takahashi Y, Uochi Y, Funahashi J, Nakashima T, Soga S, Suzuki M, Ikeda S, Yamashita Y, Rahayu ES, Kanda Y, Ichimura M..  (2008)  Conformational significance of EH21A1-A4, phenolic derivatives of geldanamycin, for Hsp90 inhibitory activity.,  18  (5): [PMID:18243703] [10.1016/j.bmcl.2008.01.072]

2. Nong XH, Tu ZC, Qi SH..  (2020)  Ansamycin derivatives from the marine-derived Streptomyces sp. SCSGAA 0027 and their cytotoxic and antiviral activities.,  30  (11): [PMID:32273216] [10.1016/j.bmcl.2020.127168]

Source

Source(1):

• Scientific Literature