Seric Acid C; (2S,3S)-2-(4-hydroxyphenyl)-4-[(E)-1-(4-hydroxyphenyl)methylidene]-5-oxotetrahydro-3-furancarboxylic acid

ID: ALA4535786

PubChem CID: 155547889

Max Phase: Preclinical

Molecular Formula: C18H14O6

Molecular Weight: 326.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1O[C@H](c2ccc(O)cc2)[C@@H](C(=O)O)/C1=C\c1ccc(O)cc1

Standard InChI:  InChI=1S/C18H14O6/c19-12-5-1-10(2-6-12)9-14-15(17(21)22)16(24-18(14)23)11-3-7-13(20)8-4-11/h1-9,15-16,19-20H,(H,21,22)/b14-9+/t15-,16+/m0/s1

Standard InChI Key:  VCGDDWQSRJLRHG-IYSULOHHSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   21.8072   -4.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6244   -4.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8788   -3.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2158   -3.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5571   -3.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7279   -4.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7268   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4348   -5.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1445   -4.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1417   -3.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4331   -3.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0188   -5.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8478   -3.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3260   -5.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5134   -5.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6575   -6.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1040   -5.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7686   -6.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2474   -6.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0611   -6.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3937   -6.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9128   -5.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5416   -7.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2146   -2.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  7 12  1  0
 10 13  1  0
 13  5  2  0
  1 14  1  1
 14 15  2  0
 14 16  1  0
  2 17  1  6
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
  4 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4535786

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 326.30

Molecular Weight (Monoisotopic): 326.0790

AlogP: 2.48

#Rotatable Bonds: 3

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.67

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: -0.33

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: 0.98

References

1. Murata T, Katagiri T, Ishikawa Y, Abe M, Takahashi E, Iwahana R, Sakamoto Y, Sasaki K..  (2019)  Inhibitory Effects of Phenylpropanoid Derivatives from Oenanthe javanica on Antigen-Stimulated Degranulation in RBL-2H3 Cells.,  82  (6): [PMID:31125231] [10.1021/acs.jnatprod.8b01054]

Source

Source(1):

• Scientific Literature