delta-23-Nodulisporic acid C4

ID: ALA449872

PubChem CID: 11377261

Max Phase: Preclinical

Molecular Formula: C43H57NO4

Molecular Weight: 651.93

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Delta-23-Nodulisporic Acid C4 | CHEMBL449872|delta-23-Nodulisporic acid C4

Canonical SMILES:  CC(C)=CCc1c2c(cc3c4c([nH]c13)[C@@]1(C)[C@@H](CC[C@H]3[C@](C)(CC/C=C(\C)C(=O)O)[C@@H](O)CC[C@@]31C)C4)C1=CC(C)(C)OC(C)(C)C1=C2

Standard InChI:  InChI=1S/C43H57NO4/c1-24(2)13-15-27-29-22-33-32(23-39(4,5)48-40(33,6)7)28(29)21-30-31-20-26-14-16-34-41(8,18-11-12-25(3)38(46)47)35(45)17-19-42(34,9)43(26,10)37(31)44-36(27)30/h12-13,21-23,26,34-35,44-45H,11,14-20H2,1-10H3,(H,46,47)/b25-12+/t26-,34-,35-,41-,42-,43+/m0/s1

Standard InChI Key:  HDJXFKXAERMFQW-QFIVBDMGSA-N

Molfile:  

     RDKit          2D

 50 56  0  0  0  0  0  0  0  0999 V2000
   -4.3096    2.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812    1.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4286    0.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4850    2.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1354    1.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6025    0.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025    0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    1.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3244    0.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6035    0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515    1.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9298    1.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040    0.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1113    0.2982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1827    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5043    0.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916    2.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520    1.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    0.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158    2.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065    2.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1223    1.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5233    2.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8014    2.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970    2.9092    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140    0.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432    1.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449    0.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574    0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5699   -0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378    1.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    0.4606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510    1.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611    0.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2727    0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -0.3212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    0.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4376    0.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0601    0.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8429    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8996   -0.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4677    0.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0058    1.4136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804   -0.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616   -1.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661   -2.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5342   -2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 20  1  0
 19 12  1  0
  3 15  1  0
  3 16  1  0
  1 17  1  0
  1 18  1  0
 19 20  2  0
 20 23  1  0
 22 21  1  0
 21 19  1  0
 22 23  1  0
 22 25  1  0
 23 29  1  0
 28 24  1  0
 24 25  1  0
 22 26  1  1
 23 27  1  6
 28 29  1  0
 28 35  1  0
 29 30  1  0
 30 31  1  0
 31 36  1  0
 29 32  1  1
 28 33  1  6
 35 34  1  1
 35 36  1  0
  1  2  1  0
  1  4  1  0
 37 35  1  0
  2  3  1  0
 36 38  1  1
  3  6  1  0
 37 39  1  0
  5  4  2  0
 39 40  1  0
  5  6  1  0
 40 41  2  0
  6  7  2  0
 41 42  1  0
  7  9  1  0
 41 43  1  0
  8  5  1  0
  8  9  2  0
 42 44  1  0
 42 45  2  0
  9 10  1  0
 10 46  1  0
 10 13  2  0
 46 47  1  0
 12 11  2  0
 47 48  2  0
 11  8  1  0
 48 49  1  0
 12 13  1  0
 48 50  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA449872

   delta-23-Nodulisporic acid C4

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: 651.93

Molecular Weight (Monoisotopic): 651.4288

AlogP: 9.86

#Rotatable Bonds: 6

Polar Surface Area: 82.55

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.58

CX Basic pKa: ┄

CX LogP: 8.97

CX LogD: 6.22

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.21

Np Likeness Score: 3.00

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