Shornephine A

ID: ALA4205964

PubChem CID: 10194855

Max Phase: Preclinical

Molecular Formula: C25H26N2O5

Molecular Weight: 434.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)[C@]12Nc3c(O)cccc3[C@@]1(O)C[C@H]1C(=O)O[C@@H](Cc3ccccc3)C(=O)N12

Standard InChI:  InChI=1S/C25H26N2O5/c1-4-23(2,3)25-24(31,16-11-8-12-18(28)20(16)26-25)14-17-22(30)32-19(21(29)27(17)25)13-15-9-6-5-7-10-15/h4-12,17,19,26,28,31H,1,13-14H2,2-3H3/t17-,19-,24-,25+/m0/s1

Standard InChI Key:  VMKCIRAJEVFSFR-LQTXRJQHSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   22.4821  -10.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7747  -11.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3602  -11.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8607   -9.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8596  -10.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.5727   -9.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2880   -9.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2929  -10.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0803  -11.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0725   -9.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5640  -10.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5524   -9.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3404   -9.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3453  -10.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0584  -10.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7713  -10.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7666   -9.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0488   -8.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3329   -8.4249    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0429   -8.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2094  -11.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4877  -10.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2002  -10.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5755  -12.0067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6539   -8.9582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1896  -11.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4009  -12.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9142  -10.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6263  -10.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6231   -9.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9018   -8.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1926   -9.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11  8  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 13 11  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 20  1  6
 19 21  2  0
 16 22  2  0
 17 23  1  1
 23 24  1  0
  6 25  1  0
 11 26  1  6
 12  2  1  6
  2 27  1  0
 27 28  2  0
 24 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4205964

   Shornephine A

Molecule Features

Natural Product: Yes

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: 434.49

Molecular Weight (Monoisotopic): 434.1842

AlogP: 2.68

#Rotatable Bonds: 4

Polar Surface Area: 99.10

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.98

CX Basic pKa: 1.30

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: 1.65

References

1. Aparicio-Cuevas MA, Rivero-Cruz I, Sánchez-Castellanos M, Menéndez D, Raja HA, Joseph-Nathan P, González MDC, Figueroa M..  (2017)  Dioxomorpholines and Derivatives from a Marine-Facultative Aspergillus Species.,  80  (8): [PMID:28796494] [10.1021/acs.jnatprod.7b00331]

Source

Source(1):

• Scientific Literature