Moracin O

ID: ALA205924

PubChem CID: 14539883

Max Phase: Preclinical

Molecular Formula: C19H18O5

Molecular Weight: 326.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+/-)-Moracin O | Moracin O | Moracin O|CHEMBL205924|(-)-Moracin O|5-[6-(2-hydroxypropan-2-yl)-5,6-dihydrofuro[3,2-f][1]benzofuran-2-yl]benzene-1,3-diol|(+/-)-Moracin O|CHEBI:175160|5-[(6R)-6-(2-hydroxypropan-2-yl)-5,6-dihydrofuro[3,2-f][1]benzofuran-2-yl]benzene-1,3-diol|YEA70297|BDBM50179013|FT-0775368|B0005-477256|5-[2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydrofuro[3,2-f]benzofuran-6-yl]benzene-1,3-diol|5-[6-(2-hydroxypropan-2-yl)-5,6-dihydrouro[3,2-][1]benzouran-2-yl]benzene-1,3-diol|5-[11-(2-hyShow More⌵

Canonical SMILES:  CC(C)(O)C1Cc2cc3cc(-c4cc(O)cc(O)c4)oc3cc2O1

Standard InChI:  InChI=1S/C19H18O5/c1-19(2,22)18-7-11-3-10-6-15(23-16(10)9-17(11)24-18)12-4-13(20)8-14(21)5-12/h3-6,8-9,18,20-22H,7H2,1-2H3

Standard InChI Key:  HMTMYIWMPJSCAZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    1.7426  -16.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042  -17.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884  -17.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149  -17.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557  -17.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649  -16.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031  -15.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044  -18.5149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798  -16.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081  -16.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844  -16.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7768  -17.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0020  -17.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5022  -16.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850  -17.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793  -17.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952  -17.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2050  -16.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961  -16.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4741  -17.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2990  -17.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1240  -17.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2938  -17.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3041  -16.2318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  1  0
 13  9  2  0
  9 10  1  0
 15 12  2  0
  1  2  2  0
 11 14  2  0
 14 18  1  0
 15 17  1  0
  6  7  1  0
 17 18  2  0
  3  4  2  0
  4  8  1  0
  2  9  1  0
  4  5  1  0
 16 17  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  2  3  1  0
 20 21  1  0
  5  6  2  0
 21 22  1  0
  6  1  1  0
 21 23  1  0
 10 11  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA205924

   MORACIN O

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: 326.35

Molecular Weight (Monoisotopic): 326.1154

AlogP: 3.59

#Rotatable Bonds: 2

Polar Surface Area: 83.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.82

CX Basic pKa: ┄

CX LogP: 3.04

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 1.87

References

1. Cui L, Na M, Oh H, Bae EY, Jeong DG, Ryu SE, Kim S, Kim BY, Oh WK, Ahn JS..  (2006)  Protein tyrosine phosphatase 1B inhibitors from Morus root bark.,  16  (5): [PMID:16356713] [10.1016/j.bmcl.2005.11.071]

2. Dat NT, Jin X, Lee K, Hong YS, Kim YH, Lee JJ..  (2009)  Hypoxia-inducible factor-1 inhibitory benzofurans and chalcone-derived diels-alder adducts from Morus species.,  72  (1): [PMID:19072214] [10.1021/np800491u]

3. Xia Y, Jin Y, Kaur N, Choi Y, Lee K..  (2011)  HIF-1α inhibitors: synthesis and biological evaluation of novel moracin O and P analogues.,  46  (6): [PMID:21481991] [10.1016/j.ejmech.2011.03.022]

4. Heger V, Benesova B, Viskupicova J, Majekova M, Zoofishan Z, Hunyadi A, Horakova L..  (2020)  Phenolic Compounds from Morus nigra Regulate Viability and Apoptosis of Pancreatic β-Cells Possibly via SERCA Activity.,  11  (5): [PMID:32435418] [10.1021/acsmedchemlett.0c00047]

Source

Source(1):

• Scientific Literature