artobiloxanthone

ID: ALA1099162

PubChem CID: 46887866

Max Phase: Preclinical

Molecular Formula: C25H22O7

Molecular Weight: 434.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Artobiloxanthone | artobiloxanthone|CHEMBL1099162|CHEBI:172673|DTXSID001316834|BDBM50317859|(16R)-11,18,19,21-tetrahydroxy-7,7-dimethyl-16-prop-1-en-2-yl-2,8-dioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one

Canonical SMILES:  C=C(C)[C@H]1Cc2c(oc3c4c(cc(O)c3c2=O)OC(C)(C)C=C4)-c2c(O)cc(O)c(O)c21

Standard InChI:  InChI=1S/C25H22O7/c1-10(2)12-7-13-21(29)20-15(27)9-17-11(5-6-25(3,4)32-17)23(20)31-24(13)19-14(26)8-16(28)22(30)18(12)19/h5-6,8-9,12,26-28,30H,1,7H2,2-4H3/t12-/m1/s1

Standard InChI Key:  ZIYAGIMFLYOZDS-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   15.4432  -14.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1581  -15.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8716  -13.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8750  -14.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5903  -15.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5835  -13.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3033  -13.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3085  -14.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0224  -15.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7358  -14.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0120  -13.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7250  -13.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4363  -13.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4359  -12.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7181  -12.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0098  -12.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1510  -13.9128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1493  -12.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2937  -12.2711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4536  -15.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4605  -15.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1647  -14.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5931  -15.9880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4444  -13.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1515  -13.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1477  -12.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4385  -12.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7314  -12.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7335  -13.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0125  -13.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1417  -12.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1586  -15.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  8  1  0
 14 15  1  0
  7  6  1  0
 15 16  2  0
 16 11  1  0
  7  8  2  0
 13 17  1  0
  3 25  2  0
 14 18  1  0
  3  4  1  0
 16 19  1  0
 24  1  2  0
 10 20  1  1
 20 21  1  0
  7 11  1  0
 20 22  2  0
  8  9  1  0
  5 23  2  0
 24 25  1  0
  9 10  1  0
 10 12  1  0
  1  2  1  0
  2  4  2  0
 11 12  2  0
  3  6  1  0
 24 29  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 12 13  1  0
 28 30  1  0
  4  5  1  0
 28 31  1  0
 13 14  2  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099162

   ARTOBILOXANTHONE

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: 434.44

Molecular Weight (Monoisotopic): 434.1366

AlogP: 4.68

#Rotatable Bonds: 1

Polar Surface Area: 120.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.51

CX Basic pKa: ┄

CX LogP: 4.42

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: 2.92

References

1. Ren Y, Kardono LB, Riswan S, Chai H, Farnsworth NR, Soejarto DD, Carcache de Blanco EJ, Kinghorn AD..  (2010)  Cytotoxic and NF-kappaB inhibitory constituents of Artocarpus rigida.,  73  (5): [PMID:20384315] [10.1021/np1002065]

2. Toume K, Habu T, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M..  (2015)  Prenylated flavonoids and resveratrol derivatives isolated from Artocarpus communis with the ability to overcome TRAIL resistance.,  78  (1): [PMID:25537111] [10.1021/np500734t]

Source

Source(1):

• Scientific Literature