(4aS,12bR)-4a,8-dihydroxy-3-methyl-4,4a,5,6-tetrahydrotetraphene-1,7,12(12bH)-trione

ID: ALA4853561

Cas Number: 114687-52-4

PubChem CID: 130757

Max Phase: Preclinical

Molecular Formula: C19H16O5

Molecular Weight: 324.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)[C@@H]2C3=C(CC[C@]2(O)C1)C(=O)c1c(O)cccc1C3=O

Standard InChI:  InChI=1S/C19H16O5/c1-9-7-13(21)16-15-11(5-6-19(16,24)8-9)17(22)14-10(18(15)23)3-2-4-12(14)20/h2-4,7,16,20,24H,5-6,8H2,1H3/t16-,19+/m1/s1

Standard InChI Key:  URTQKYFPDHWPGU-APWZRJJASA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   28.1674   -8.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1662   -9.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8806  -10.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8788   -8.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5937   -8.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5945   -9.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3093  -10.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3036   -8.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0190   -8.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0227   -9.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7413  -10.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4568   -9.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7300   -8.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4478   -8.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1579   -8.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1513   -7.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4288   -7.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7217   -7.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0031   -7.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8612   -7.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1572   -9.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7249   -9.3021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.3115  -10.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2993   -7.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8825  -10.9704    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
  6  7  1  0
  7 10  1  0
  9  8  1  0
  8  5  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 14  1  0
 13  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 13  1  0
 18 19  2  0
 16 20  1  0
 14 21  1  6
 13 22  1  6
  7 23  2  0
  8 24  2  0
  3 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4853561

   cis-(+)-4a,5,6,12b-Tetrahydro-4a,8-dihydroxy-3-methylbenz(a)anthracene-1,7,12(4H)-trione

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: 324.33

Molecular Weight (Monoisotopic): 324.0998

AlogP: 2.13

#Rotatable Bonds: ┄

Polar Surface Area: 91.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.25

CX Basic pKa: ┄

CX LogP: 2.22

CX LogD: 2.16

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: 1.81

References

1. Saepua S, Kornsakulkarn J, Choowong W, Suriyachadkun C, Boonlarppradab C, Thongpanchang C..  (2021)  Antimicrobial and Cytotoxic Angucyclic Quinones from Actinomadura miaoliensis.,  84  (11.0): [PMID:34748348] [10.1021/acs.jnatprod.1c00232]

Source

Source(1):

• Scientific Literature