5-[2-(3-Hydroxy-phenyl)-vinyl]-benzene-1,3-diol

ID: ALA99852

Cas Number: 150258-84-7

PubChem CID: 10059651

Max Phase: Preclinical

Molecular Formula: C14H12O3

Molecular Weight: 228.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (E)-3,3',5'-Trihydroxystilbene | Trans-3,3',5-Trihydroxystilbene | 150258-84-7|CHEMBL99852|1,3-Benzenediol, 5-[(1E)-2-(3-hydroxyphenyl)ethenyl]-|(E)-5-(3-Hydroxystyryl)benzene-1,3-diol|3,5,3'-trihydroxystilbene|5-[(E)-2-(3-hydroxyphenyl)ethenyl]benzene-1,3-diol|SCHEMBL4742460|SCHEMBL4742462|Trans-3,3',5-Trihydroxystilbene|3,3',5-trihydroxy-trans-stilbene|(E)-3,3',5'-Trihydroxystilbene|BDBM50045922|AKOS040762881|5-[2-(3-Hydroxy-phenyl)-vinyl]-benzene-1,3-diol

Canonical SMILES:  Oc1cccc(/C=C/c2cc(O)cc(O)c2)c1

Standard InChI:  InChI=1S/C14H12O3/c15-12-3-1-2-10(6-12)4-5-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b5-4+

Standard InChI Key:  QUGCFFKLKWANMQ-SNAWJCMRSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    5.6167   -5.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -6.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -5.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -6.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -6.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0875   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -4.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -7.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4875   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1042   -7.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -7.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5125   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  6  1  0
  5  7  1  0
  6  8  2  0
  7  3  2  0
  8  3  1  0
  9  2  1  0
 10  9  1  0
 11 10  2  0
 12  5  1  0
 13  6  1  0
 14 11  1  0
 15 16  1  0
 16  9  2  0
 17 15  2  0
  4  5  2  0
 11 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA99852

   1,3-Benzenediol, 5-[(1E)-2-(3-hydroxyphenyl)ethenyl]-

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: 228.25

Molecular Weight (Monoisotopic): 228.0786

AlogP: 2.97

#Rotatable Bonds: 2

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.47

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.37

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.69

Np Likeness Score: 0.68

References

1. Thakkar K, Geahlen RL, Cushman M..  (1993)  Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogues of piceatannol.,  36  (20): [PMID:8411012] [10.1021/jm00072a015]

2. Albert S, Horbach R, Deising HB, Siewert B, Csuk R..  (2011)  Synthesis and antimicrobial activity of (E) stilbene derivatives.,  19  (17): [PMID:21803587] [10.1016/j.bmc.2011.07.015]

3. Wang G, Guo X, Chen H, Lin T, Xu Y, Chen Q, Liu J, Zeng J, Zhang XK, Yao X..  (2012)  A resveratrol analog, phoyunbene B, induces G2/M cell cycle arrest and apoptosis in HepG2 liver cancer cells.,  22  (5): [PMID:22326393] [10.1016/j.bmcl.2011.12.095]

4. Uzura S, Sekine-Suzuki E, Nakanishi I, Sonoda M, Tanimori S..  (2016)  A facile and rapid access to resveratrol derivatives and their radioprotective activity.,  26  (16): [PMID:27426305] [10.1016/j.bmcl.2016.07.018]

5. Nakao S, Mabuchi M, Wang S, Kogure Y, Shimizu T, Noguchi K, Tanaka A, Dai Y..  (2017)  Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor.,  27  (14): [PMID:28576617] [10.1016/j.bmcl.2017.05.025]

Source

Source(1):

• Scientific Literature