4-{(1S,2S)-1-Hydroxy-2-[2-methoxy-4-((E)-propenyl)-phenoxy]-propyl}-2-methoxy-phenol

ID: ALA185692

PubChem CID: 904797

Max Phase: Preclinical

Molecular Formula: C20H24O5

Molecular Weight: 344.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Machilin D | CHEMBL185692|(1S,2S)-1-(4-Hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(1-propenyl)phenoxy]-1-propanol|4-[(1S,2S)-1-hydroxy-2-[2-methoxy-4-[(E)-prop-1-enyl]phenoxy]propyl]-2-methoxyphenol

Canonical SMILES:  C/C=C/c1ccc(O[C@@H](C)[C@@H](O)c2ccc(O)c(OC)c2)c(OC)c1

Standard InChI:  InChI=1S/C20H24O5/c1-5-6-14-7-10-17(19(11-14)24-4)25-13(2)20(22)15-8-9-16(21)18(12-15)23-3/h5-13,20-22H,1-4H3/b6-5+/t13-,20+/m0/s1

Standard InChI Key:  WCFYXOLUODJLKB-QONXFYDISA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    5.5736    0.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5724   -0.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2872   -0.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0037   -0.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0008    0.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2854    0.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2870   -1.7319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576   -0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435   -0.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830    1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9962    1.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9937    2.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0014   -2.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0012   -2.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7160   -1.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2866   -3.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7156   -3.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8605   -3.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8599   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5793   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904   -4.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464   -2.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470   -2.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458   -4.6192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  7 13  1  0
  1  2  2  0
 13 14  1  0
  3  7  1  0
 13 15  1  1
  3  4  2  0
 14 16  1  0
  2  8  1  0
 14 17  1  1
 16 18  2  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  6 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 22 16  1  0
 10 11  2  0
 19 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA185692

   MACHILIN D

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: 344.41

Molecular Weight (Monoisotopic): 344.1624

AlogP: 3.94

#Rotatable Bonds: 7

Polar Surface Area: 68.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: 1.02

References

1. Lee WS, Baek YI, Kim JR, Cho KH, Sok DE, Jeong TS..  (2004)  Antioxidant activities of a new lignan and a neolignan from Saururus chinensis.,  14  (22): [PMID:15482936] [10.1016/j.bmcl.2004.08.054]

2. Ahn BT, Lee S, Lee SB, Lee ES, Kim JG, Bok SH, Jeong TS..  (2001)  Low-density lipoprotein-antioxidant constituents of Saururus chinensis.,  64  (12): [PMID:11754613] [10.1021/np0006061]

3. Jin Q, Lee JW, Kim JG, Lee D, Hong JT, Kim Y, Lee MK, Hwang BY..  (2019)  Lignans from Saururus chinensis with Inhibitory Effects on Nitric Oxide Production.,  82  (11): [PMID:31642320] [10.1021/acs.jnatprod.9b00520]

Source

Source(1):

• Scientific Literature