Palmarumycin C5

ID: ALA4095349

PubChem CID: 101671804

Max Phase: Preclinical

Molecular Formula: C21H16O5

Molecular Weight: 348.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1CCC2(Oc3cccc4cccc(c34)O2)C2=C1C(=O)C=CC2=O

Standard InChI:  InChI=1S/C21H16O5/c1-24-15-10-11-21(20-14(23)9-8-13(22)19(15)20)25-16-6-2-4-12-5-3-7-17(26-21)18(12)16/h2-9,15H,10-11H2,1H3/t15-/m0/s1

Standard InChI Key:  LHCSRRCODDHFNE-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   25.6099  -11.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6028   -9.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8870  -10.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8915  -10.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3189  -14.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0405  -13.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0362  -13.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6039  -13.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1754  -13.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1779  -13.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8906  -14.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8914  -12.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6015  -13.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3142  -12.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3218  -11.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8938  -11.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3187  -10.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3256  -10.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0363  -11.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0266   -9.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0221   -8.9026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7441  -10.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7477  -10.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0425  -12.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6003   -8.9111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8846   -8.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0
  1  4  1  0
 17  2  1  0
  2  3  1  0
  3  4  1  0
  8  5  1  0
  5  6  2  0
  6  7  1  0
  7 14  2  0
  8 13  1  0
 12  9  1  0
  9 10  2  0
 10 11  1  0
 11  8  2  0
 12 13  2  0
 12 16  1  0
 13 14  1  0
 14 15  1  0
  1 15  1  0
  1 16  1  0
 17 18  2  0
 17 20  1  0
 18 19  1  0
 19 23  1  0
 22 20  1  0
 20 21  2  0
 23 22  2  0
 19 24  2  0
  2 25  1  6
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095349

   (5'S)-5'-methoxyspiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-3,8'-6,7-dihydro-5H-naphthalene]-1',4'-dione

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: 348.35

Molecular Weight (Monoisotopic): 348.0998

AlogP: 3.12

#Rotatable Bonds: 1

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: 1.59

References

1. Siridechakorn I, Yue Z, Mittraphab Y, Lei X, Pudhom K..  (2017)  Identification of spirobisnaphthalene derivatives with anti-tumor activities from the endophytic fungus Rhytidhysteron rufulum AS21B.,  25  (11): [PMID:28274675] [10.1016/j.bmc.2017.02.054]

Source

Source(1):

• Scientific Literature