Nodulisporic acid D1 methyl ester

ID: ALA445248

PubChem CID: 11250520

Max Phase: Preclinical

Molecular Formula: C39H51NO5

Molecular Weight: 613.84

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Nodulisporic Acid D1 Methyl Ester | CHEMBL445248|Nodulisporic acid D1 methyl ester

Canonical SMILES:  COC(=O)/C(C)=C/[C@@H]1C[C@@]2(C)[C@@H]3CC[C@H]4Cc5c([nH]c6cc7c(cc56)C5=CC(C)(C)OC(C)(C)[C@H]5C7)[C@]4(C)[C@@]3(C)CC[C@]2(O)O1

Standard InChI:  InChI=1S/C39H51NO5/c1-21(33(41)43-9)14-24-19-37(7)31-11-10-23-17-27-26-18-25-22(15-29-28(25)20-34(2,3)45-35(29,4)5)16-30(26)40-32(27)38(23,8)36(31,6)12-13-39(37,42)44-24/h14,16,18,20,23-24,29,31,40,42H,10-13,15,17,19H2,1-9H3/b21-14+/t23-,24+,29-,31+,36-,37-,38+,39-/m0/s1

Standard InChI Key:  IEBHNEDRQAMFNT-XJLPSLHVSA-N

Molfile:  

     RDKit          2D

 48 55  0  0  0  0  0  0  0  0999 V2000
    8.8491   -3.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3763   -4.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7298   -4.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6752   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0255   -4.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5574   -4.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0585   -5.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8152   -4.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8382   -5.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5605   -5.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5126   -3.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2356   -4.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2616   -5.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0558   -5.4017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4135   -5.5504    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9740   -5.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6539   -5.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9176   -2.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0654   -3.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0150   -4.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5185   -4.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4837   -3.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2761   -3.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2920   -4.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6957   -3.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9724   -3.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2665   -2.7854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2837   -5.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7157   -4.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0161   -4.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0286   -5.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7425   -6.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0089   -3.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7084   -5.2390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4250   -3.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4351   -4.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4467   -5.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2268   -5.8610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6974   -5.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2080   -4.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4404   -6.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5260   -5.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9506   -5.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7792   -5.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5466   -6.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2054   -6.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1848   -5.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0340   -6.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  2  0
 11  8  1  0
 12 13  1  0
 13 14  1  0
 14 21  1  0
 20 12  1  0
  6 15  1  1
  3 16  1  0
  3 17  1  0
  1 18  1  0
  1 19  1  0
 20 21  2  0
 21 24  1  0
 23 22  1  0
 22 20  1  0
 23 24  1  0
 23 26  1  0
 24 30  1  0
 29 25  1  0
 25 26  1  0
 23 27  1  1
 24 28  1  6
 29 30  1  0
 29 36  1  0
 30 31  1  0
 31 32  1  0
 32 37  1  0
 30 33  1  1
 29 34  1  6
 36 35  1  1
 36 37  1  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 36  1  0
  5  4  2  0
 37 41  1  6
  5  6  1  0
 39 42  1  1
  6  7  1  0
 42 43  2  0
  7  9  1  0
 43 44  1  0
  8  5  1  0
 43 45  1  0
  8  9  2  0
  9 10  1  0
 44 46  1  0
 44 47  2  0
 10 13  2  0
 46 48  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA445248

   NODULISPORIC ACID D1 METHYL ESTER

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: 613.84

Molecular Weight (Monoisotopic): 613.3767

AlogP: 7.55

#Rotatable Bonds: 2

Polar Surface Area: 80.78

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.66

CX Basic pKa: ┄

CX LogP: 7.37

CX LogD: 7.37

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.27

Np Likeness Score: 2.88

References

1. Singh SB, Ondeyka JG, Jayasuriya H, Zink DL, Ha SN, Dahl-Roshak A, Greene J, Kim JA, Smith MM, Shoop W, Tkacz JS..  (2004)  Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships.,  67  (9): [PMID:15387649] [10.1021/np0498455]

Source

Source(1):

• Scientific Literature