Compound page

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C20H22O6
APtclcactv08042323242D 0   0.00000     0.00000
 
 48 50  0  0  1  0  0  0  0  0999 V2000
    5.1350    0.5000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2690    1.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8950    0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950    2.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6613    3.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2033    0.7838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000    0.6900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6719   -3.8100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    3.8100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8010    0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8010    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6651    0.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369    1.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -3.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030    3.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6651    2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -2.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    0.1900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690    0.3800    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350    3.1200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8878   -0.1546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8878    3.1546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321   -0.6900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -0.6900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044    0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015    0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924    2.6077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909    1.9174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -2.3100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2813    3.5265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6589    4.1441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0413    3.5218    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830   -3.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -4.1200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0230   -3.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 25  1  0  0  0  0
 10 25  1  0  0  0  0
 17 21  1  0  0  0  0
 19 26  1  0  0  0  0
 11 26  1  0  0  0  0
  8 22  1  0  0  0  0
 20 23  1  0  0  0  0
  9 24  1  0  0  0  0
  1 28  1  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  6  0  0  0
 28 29  1  0  0  0  0
  3 28  2  0  0  0  0
 29 30  1  0  0  0  0
  4 29  2  0  0  0  0
  2 27  1  0  0  0  0
  2  8  1  1  0  0  0
  5 16  1  0  0  0  0
  6 16  2  0  0  0  0
 27 30  2  0  0  0  0
  9 27  1  0  0  0  0
  3 17  1  0  0  0  0
  4 18  1  0  0  0  0
 17 18  2  0  0  0  0
  5 19  2  0  0  0  0
  6  7  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  2  0  0  0  0
 12 21  1  0  0  0  0
 13 22  1  0  0  0  0
 14 23  1  0  0  0  0
 15 24  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  0  0  0  0
 30 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
  7 42  1  0  0  0  0
 10 43  1  0  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
 11 46  1  0  0  0  0
 11 47  1  0  0  0  0
 11 48  1  0  0  0  0
M  END
$$$$

MOL SMILES InChIKey

Compound Description

A lignan that consists of 7,8-dihydronaphthalen-2-ol substituted by a 4-hydroxy-3-methoxyphenyl group at position 8, hydroxymethyl groups at positions 6 and 7 and a methoxy group at position 3 (the 7R,8S stereoisomer). Isolated from Vitex negundo, it exhibits inhibitory activity against lipoxygenase.

Identification

IUPAC Names

(7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-7,8-dihydronaphthalen-2-ol

Molecular Formula

C20H22O6

Mass

358.38510

Monoisotopic Mass

358.14164

Charge

InChI

InChI=1S/C20H22O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-8,15,20-24H,9-10H2,1-2H3/t15-,20-/m0/s1

InChIKey

AKOLXLNVZGAYAV-YWZLYKJASA-N

SMILES

[H][C@]1([C@@H](CO)C(CO)=Cc2cc(OC)c(O)cc12)c1ccc(O)c(OC)c1

Species

vitex negundo

NCBI:txid361442 15520511

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Europe PubMed Central results

Enzyme inhibiting lignans from Vitex negundo.

Author: Azhar-Ul-Haq, Malik A, Anis I, Khan SB, Ahmed E, Ahmed Z, Nawaz SA, Choudhary MI.

Abstract: Two new lignans trivially named negundins A (1) and B (2), were isolated along with (+)-diasyringaresinol (3), (+)-lyoniresinol (4), vitrofolal E (5) and vitrofolal F (6), reported for the first time from this species. The structures of the new compounds were established through spectral studies. Compound 2 showed potent inhibitory activity against lipoxygenase enzyme, while 5 showed moderate activity against butyryl-cholinesterase.

DOI: 10.1248/cpb.52.1269

Connect to another EMBL location

MTBLC66613: negundin B

Identification

Species

Europe PubMed Central results

Enzyme inhibiting lignans from Vitex negundo.

Author: Azhar-Ul-Haq, Malik A, Anis I, Khan SB, Ahmed E, Ahmed Z, Nawaz SA, Choudhary MI.