[1',1'':1,4'-terphenyl]-2',3',5'-triol 2'-O-beta-glucuronide

ID: ALA3120853

PubChem CID: 24123416

Max Phase: Preclinical

Molecular Formula: C24H22O9

Molecular Weight: 454.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1O[C@@H](Oc2c(-c3ccccc3)cc(O)c(-c3ccccc3)c2O)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C24H22O9/c25-15-11-14(12-7-3-1-4-8-12)21(17(26)16(15)13-9-5-2-6-10-13)32-24-20(29)18(27)19(28)22(33-24)23(30)31/h1-11,18-20,22,24-29H,(H,30,31)/t18-,19-,20+,22-,24+/m0/s1

Standard InChI Key:  QQDLPJHEFJKVHT-MJRVOHGCSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   21.5547   -4.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7276   -4.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3345   -5.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7674   -5.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5975   -5.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9868   -4.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8114   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5098   -5.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2440   -5.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0677   -5.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4591   -4.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0206   -4.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1982   -4.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0833   -4.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2594   -4.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8657   -5.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3019   -5.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1244   -5.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2962   -3.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9472   -3.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0320   -6.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6896   -2.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5183   -2.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9116   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4838   -1.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6581   -1.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2602   -2.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4355   -2.1821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2290   -0.7311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8798   -0.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7364   -2.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1651   -2.8074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1324   -1.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  3  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  7  1  0
  8 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  8  1  0
  2 19  1  0
  1 20  1  0
  5 21  1  0
 22 19  1  1
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 26 29  1  1
 25 30  1  6
 24 31  1  1
 31 32  2  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3120853

   Echoside C

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: 454.43

Molecular Weight (Monoisotopic): 454.1264

AlogP: 1.70

#Rotatable Bonds: 5

Polar Surface Area: 156.91

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.33

CX Basic pKa: ┄

CX LogP: 2.41

CX LogD: -1.02

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: 1.41

References

1. Deng J, Lu C, Li S, Hao H, Li Z, Zhu J, Li Y, Shen Y..  (2014)  p-Terphenyl O-β-glucuronides, DNA topoisomerase inhibitors from Streptomyces sp. LZ35ΔgdmAI.,  24  (5): [PMID:24507923] [10.1016/j.bmcl.2014.01.037]

Source

Source(1):

• Scientific Literature