Pochonin N

ID: ALA1684401

PubChem CID: 53320828

Max Phase: Preclinical

Molecular Formula: C18H21ClO7

Molecular Weight: 384.81

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pochonin N | CHEMBL1684401

Canonical SMILES:  C[C@@H]1C[C@@H](O)/C=C\[C@H](O)CCC(=O)Cc2c(Cl)c(O)cc(O)c2C(=O)O1

Standard InChI:  InChI=1S/C18H21ClO7/c1-9-6-11(21)4-2-10(20)3-5-12(22)7-13-16(18(25)26-9)14(23)8-15(24)17(13)19/h2,4,8-11,20-21,23-24H,3,5-7H2,1H3/b4-2-/t9-,10+,11+/m1/s1

Standard InChI Key:  UGYZEXDMXHEULY-SLTYSDCVSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.7845    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729   -1.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0747    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577    0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3586   -0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3563    0.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    1.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    1.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3537    1.2494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7879    0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4973   -0.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983    0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3588   -1.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682   -2.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0957   -2.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8154   -2.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766    2.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -0.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3401   -2.4845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -2.0564    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4960    0.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    1.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -1.2329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  7  1  0
  6 14  1  0
  7 10  1  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
 11 13  1  0
 18 12  1  0
 12 13  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7 19  2  0
  9 20  1  6
 18 21  1  1
 15 22  2  0
  3 23  1  0
 11 24  1  6
  4 25  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1684401

   POCHONIN N

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: 384.81

Molecular Weight (Monoisotopic): 384.0976

AlogP: 1.87

#Rotatable Bonds: ┄

Polar Surface Area: 124.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.02

CX Basic pKa: ┄

CX LogP: 2.36

CX LogD: 1.84

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: 2.06

References

1. Yang SX, Gao JM, Zhang Q, Laatsch H..  (2011)  Toxic polyketides produced by Fusarium sp., an endophytic fungus isolated from Melia azedarach.,  21  (6): [PMID:21353539] [10.1016/j.bmcl.2010.12.043]

2. Mejia EJ, Loveridge ST, Stepan G, Tsai A, Jones GS, Barnes T, White KN, Drašković M, Tenney K, Tsiang M, Geleziunas R, Cihlar T, Pagratis N, Tian Y, Yu H, Crews P..  (2014)  Study of marine natural products including resorcyclic acid lactones from Humicola fuscoatra that reactivate latent HIV-1 expression in an in vitro model of central memory CD4+ T cells.,  77  (3): [PMID:24495105] [10.1021/np400889x]

Source

Source(1):

• Scientific Literature