5,8-dihydroxy-6-isopentyl-2,2,4-trimethylanthra[9,1-de][1,3]oxazin-7(2H)-one

ID: ALA2152650

PubChem CID: 136236397

Max Phase: Preclinical

Molecular Formula: C23H25NO4

Molecular Weight: 379.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(O)c(CCC(C)C)c2c3c1OC(C)(C)N=C3c1cccc(O)c1C2=O

Standard InChI:  InChI=1S/C23H25NO4/c1-11(2)9-10-14-17-18-19(13-7-6-8-15(25)16(13)21(17)27)24-23(4,5)28-22(18)12(3)20(14)26/h6-8,11,25-26H,9-10H2,1-5H3

Standard InChI Key:  WMURTDFNFBXFFU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.0109   -0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276   -1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -0.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5894   -2.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883   -3.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031   -4.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -2.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -3.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -4.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -3.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1645   -3.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8801   -3.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -2.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341   -4.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050   -4.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1691   -4.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5830   -2.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5976   -3.9868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219   -1.5276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7231   -2.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4314   -2.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427   -2.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1415   -1.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8854   -5.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8899   -6.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6067   -6.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1781   -6.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
 13 14  1  0
 14 23  2  0
  7  4  1  0
 10 15  2  0
  2  1  1  0
  6 16  1  0
  4  5  2  0
 12 17  1  0
  8  9  1  0
 14 18  1  0
  3  2  1  0
 13 19  1  0
 20 21  2  0
  9 10  1  0
 10 11  1  0
 21  8  1  0
  5  6  1  0
 22 11  2  0
 20  2  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
  6  9  2  0
 17 25  1  0
 11 12  1  0
 25 26  1  0
 26 27  1  0
 12 13  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2152650

   ---

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: 379.46

Molecular Weight (Monoisotopic): 379.1784

AlogP: 4.51

#Rotatable Bonds: 3

Polar Surface Area: 79.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.40

CX Basic pKa: 0.21

CX LogP: 6.10

CX LogD: 6.06

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: 1.72

References

1. Hu Y, Martinez ED, MacMillan JB..  (2012)  Anthraquinones from a marine-derived Streptomyces spinoverrucosus.,  75  (10): [PMID:23057874] [10.1021/np3004326]

Source

Source(1):

• Scientific Literature