Gelsedine

ID: ALA4866349

PubChem CID: 164624141

Max Phase: Preclinical

Molecular Formula: C19H24N2O3

Molecular Weight: 328.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@H]1N[C@H]2C[C@@]3(C(=O)N(OC)c4ccccc43)[C@@H]3C[C@@H]1[C@@H]2CO3

Standard InChI:  InChI=1S/C19H24N2O3/c1-3-14-11-8-17-19(9-15(20-14)12(11)10-24-17)13-6-4-5-7-16(13)21(23-2)18(19)22/h4-7,11-12,14-15,17,20H,3,8-10H2,1-2H3/t11-,12+,14-,15+,17+,19+/m1/s1

Standard InChI Key:  LDBVYQSHIPCQPT-AICUKFAOSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    4.5043  -10.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204  -10.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7534  -11.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688  -11.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8459  -10.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -9.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6796  -10.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9160  -11.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2261  -11.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2261  -12.6522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4778  -13.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6930  -11.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0869   -9.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6640   -9.1325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2489   -8.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8321   -9.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6571   -9.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2402   -9.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4950  -10.5806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8321  -10.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5017  -10.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0199  -10.8442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0641   -9.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5061  -10.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -9.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0695   -8.4094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2382   -8.4060    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2620   -9.8399    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
  5  6  2  0
  6  1  1  0
  7  5  1  6
  8  7  1  0
  9  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
  8 12  2  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  0
 21 20  1  0
  7 21  1  0
 16 20  1  0
 20 22  1  6
 18 23  1  1
 23 24  1  0
 17 25  1  0
 13 25  1  0
 17 26  1  1
 16 27  1  6
 13 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4866349

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 328.41

Molecular Weight (Monoisotopic): 328.1787

AlogP: 2.01

#Rotatable Bonds: 2

Polar Surface Area: 50.80

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.29

CX LogP: 1.73

CX LogD: -1.43

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.90

Np Likeness Score: 2.51

References

1. Otogo N'Nang E, Le Pogam P, Ndong Mba T, Sima Obiang C, Mouray E, Grellier P, Kumulungui B, Champy P, Beniddir MA..  (2021)  Targeted Isolation of Hemitheion from Mostuea brunonis, a Proposed Biosynthetic Intermediate of Theionbrunonines.,  84  (4.0): [PMID:33825474] [10.1021/acs.jnatprod.1c00143]

Source

Source(1):

• Scientific Literature