Palmarumycin B6; 6-Chloro-5-hydroxy-2,3-dihydro-4H-spiro[naphthalene-1,2'-naphtho[1,8-de][1,3]dioxin]-4-one

ID: ALA4217179

PubChem CID: 145974718

Max Phase: Preclinical

Molecular Formula: C20H13ClO4

Molecular Weight: 352.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCC2(Oc3cccc4cccc(c34)O2)c2ccc(Cl)c(O)c21

Standard InChI:  InChI=1S/C20H13ClO4/c21-13-8-7-12-18(19(13)23)14(22)9-10-20(12)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-8,23H,9-10H2

Standard InChI Key:  RTMDACDGYGBZCM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    5.6004  -14.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3146  -13.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3100  -12.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930  -12.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3102  -17.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0282  -16.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0254  -15.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937  -16.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646  -15.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663  -16.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8812  -17.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817  -15.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5921  -15.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3043  -15.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3121  -14.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832  -14.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817  -13.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822  -12.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691  -12.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550  -12.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586  -13.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723  -14.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1686  -11.6520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5869  -11.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379  -12.4800    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 17  1  0
  2  3  1  0
  3  4  1  0
  4 18  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
 15  1  1  0
  1 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 19 23  1  0
  4 24  2  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4217179

   ---

Molecule Features

Natural Product: No

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: 352.77

Molecular Weight (Monoisotopic): 352.0502

AlogP: 4.80

#Rotatable Bonds: ┄

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.01

CX Basic pKa: ┄

CX LogP: 5.27

CX LogD: 4.74

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: 1.14

References

1. Liu X, Wang W, Zhao Y, Lai D, Zhou L, Liu Z, Wang M..  (2018)  Total Synthesis and Structure Revision of Palmarumycin B6.,  81  (8): [PMID:30102534] [10.1021/acs.jnatprod.8b00258]

Source

Source(1):

• Scientific Literature