Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl ester

ID: ALA394931

Cas Number: 52762-28-4

PubChem CID: 44349539

Max Phase: Preclinical

Molecular Formula: C28H38N2O9

Molecular Weight: 546.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1/C=C\C=C(/C)C(=O)NC2=CC(=O)C(O)=C(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@@H]1OC(N)=O)C2=O

Standard InChI:  InChI=1S/C28H38N2O9/c1-14-10-18-24(33)19(13-20(31)25(18)34)30-27(35)15(2)8-7-9-21(37-5)26(39-28(29)36)17(4)12-16(3)23(32)22(11-14)38-6/h7-9,12-14,16,21-23,26,32,34H,10-11H2,1-6H3,(H2,29,36)(H,30,35)/b9-7-,15-8+,17-12+/t14-,16+,21+,22+,23-,26+/m1/s1

Standard InChI Key:  KKZJVQQMUCBLHR-LVBRMASUSA-N

Molfile:  

     RDKit          2D

 39 40  0  0  1  0  0  0  0  0999 V2000
    3.7000   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5496   -0.3727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4122   -2.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1187   -2.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1218   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667    0.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9785   -0.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2718    0.8603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9734   -1.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6956    0.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8369    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8475    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372    1.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4164    0.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1464    2.1022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1163   -3.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8296   -4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5452   -3.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3752   -3.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5476   -2.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6852   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6801   -2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9630   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3867   -2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7020   -4.5922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971   -2.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5214   -4.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8483   -5.4454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0141   -4.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -2.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6097   -1.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4007   -4.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9832   -2.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7055    1.2914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0
  6 20  1  0
  8 10  2  0
 20 21  1  0
  2 15  1  0
 21 22  2  0
  9 11  2  0
 22 23  1  0
  4  5  1  0
 22 24  1  0
  9 12  1  0
 11 25  1  0
 13 14  1  0
 25 26  2  0
  5  6  1  0
 26 27  1  0
 27 23  1  0
  4  3  1  0
 27 28  1  1
 14  7  2  0
 23 29  1  1
  5 30  1  1
  2  8  1  0
 29 31  1  0
  1 13  1  0
 31 32  1  0
 13 18  2  0
 31 33  2  0
 14 15  1  0
  6 34  1  6
 15 16  2  0
 28 35  1  0
 16 17  1  0
 20 36  1  6
 17 18  1  0
  3 37  1  6
  8  9  1  0
 30 38  1  0
 17 19  2  0
 18 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA394931

   17-O-Demethylgeldanamycin

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: 546.62

Molecular Weight (Monoisotopic): 546.2577

AlogP: 2.32

#Rotatable Bonds: 3

Polar Surface Area: 174.48

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 5.89

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: 0.52

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.31

Np Likeness Score: 2.62

References

1. Schnur RC, Corman ML, Gallaschun RJ, Cooper BA, Dee MF, Doty JL, Muzzi ML, Moyer JD, DiOrio CI, Barbacci EG..  (1995)  Inhibition of the oncogene product p185erbB-2 in vitro and in vivo by geldanamycin and dihydrogeldanamycin derivatives.,  38  (19): [PMID:7562911] [10.1021/jm00019a010]

2. Tadtong S, Meksuriyen D, Tanasupawat S, Isobe M, Suwanborirux K..  (2007)  Geldanamycin derivatives and neuroprotective effect on cultured P19-derived neurons.,  17  (10): [PMID:17442565] [10.1016/j.bmcl.2006.12.041]

3. 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]

4. Xie Y, Guo L, Huang J, Huang X, Cong Z, Liu Q, Wang Q, Pang X, Xiang S, Zhou X, Liu Y, Wang J, Wang J..  (2021)  Cyclopentenone-Containing Tetrahydroquinoline and Geldanamycin Alkaloids from Streptomyces malaysiensis as Potential Anti-Androgens against Prostate Cancer Cells.,  84  (7.0): [PMID:34225450] [10.1021/acs.jnatprod.1c00297]

5. Choi JW, Lee Y, Kim J, Kwon H, Deyrup ST, Lee JW, Lee D, Kang HS, Joo H, Shim SH..  (2023)  Discovery of Bioactive Metabolites by Acidic Stress to a Geldanamycin Producer, Streptomyces samsunensis.,  86  (4): [PMID:37042709] [10.1021/acs.jnatprod.2c01151]

Source

Source(1):

• Scientific Literature