NP-MRD: Showing NP-Card for vitexdoin A (NP0034751)

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Record Information

Version

2.0

Created at

2021-06-20 18:23:25 UTC

Updated at

2021-06-30 00:05:20 UTC

NP-MRD ID

NP0034751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

vitexdoin A

Provided By

JEOL Database JEOL Logo

Description

VITEXDOIN A belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. vitexdoin A is found in Vitex negundo. vitexdoin A was first documented in 2009 (PMID: 19715321). Based on a literature review very few articles have been published on VITEXDOIN A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120233D          

 43 45  0  0  0  0            999 V2000
   -2.9443    1.1750   -1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906    0.1254   -1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997   -0.9373   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -1.0628    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.2163    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795   -2.3824    1.7049 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5428   -2.0158    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -2.8887   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -2.5321   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -3.3390   -1.9220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -1.3201   -0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975   -0.9761   -1.4893 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -0.4427    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.7858    1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7265    0.1533    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -0.2467    3.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    0.7386    4.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    0.4326    4.8991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -1.6492    3.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0252   -2.4783    4.1448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0606   -1.9347    5.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -3.2333    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -3.1116    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356   -1.9711   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -1.8773   -1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0320    0.8116   -1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928    1.9271   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.6590   -0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5433   -0.2732    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5779   -3.4585    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -3.8271   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -4.1296   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -1.7331   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286    0.4974    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    1.1624    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122    1.7568    3.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -1.5874    3.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -2.5740    3.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -3.4895    4.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326   -1.3329    5.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -4.1302    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -3.8970    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125   -1.0093   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 16 17  1  0  0  0  0
  8  7  1  0  0  0  0
 17 36  1  0  0  0  0
 11  9  1  0  0  0  0
 17 18  2  0  0  0  0
 14 13  1  0  0  0  0
 19 20  1  0  0  0  0
 13 11  2  0  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
  5 22  1  0  0  0  0
  7  6  1  0  0  0  0
 22 23  2  0  0  0  0
  6 19  1  0  0  0  0
 23 24  1  0  0  0  0
 19 16  1  0  0  0  0
 24  3  2  0  0  0  0
 16 15  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 14  7  2  0  0  0  0
 24 25  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
 20 21  1  0  0  0  0
  8 31  1  0  0  0  0
 13 34  1  0  0  0  0
  6 30  1  1  0  0  0
 19 37  1  1  0  0  0
 15 35  1  0  0  0  0
 12 33  1  0  0  0  0
 10 32  1  0  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 22 41  1  0  0  0  0
 23 42  1  0  0  0  0
  4 29  1  0  0  0  0
 25 43  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 21 40  1  0  0  0  0
M  END

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.9443    1.1750   -1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906    0.1254   -1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997   -0.9373   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -1.0628    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.2163    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795   -2.3824    1.7049 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5428   -2.0158    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -2.8887   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -2.5321   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -3.3390   -1.9220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -1.3201   -0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975   -0.9761   -1.4893 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -0.4427    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.7858    1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7265    0.1533    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -0.2467    3.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    0.7386    4.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    0.4326    4.8991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -1.6492    3.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0252   -2.4783    4.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606   -1.9347    5.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -3.2333    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -3.1116    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356   -1.9711   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -1.8773   -1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0320    0.8116   -1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928    1.9271   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.6590   -0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5433   -0.2732    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5779   -3.4585    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -3.8271   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -4.1296   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -1.7331   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286    0.4974    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    1.1624    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122    1.7568    3.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -1.5874    3.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -2.5740    3.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -3.4895    4.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326   -1.3329    5.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -4.1302    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -3.8970    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125   -1.0093   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0
 16 17  1  0
  8  7  1  0
 17 36  1  0
 11  9  1  0
 17 18  2  0
 14 13  1  0
 19 20  1  0
 13 11  2  0
  6  5  1  0
 14 15  1  0
  5 22  1  0
  7  6  1  0
 22 23  2  0
  6 19  1  0
 23 24  1  0
 19 16  1  0
 24  3  2  0
 16 15  2  0
  3  4  1  0
  4  5  2  0
 14  7  2  0
 24 25  1  0
 11 12  1  0
  3  2  1  0
  2  1  1  0
  9 10  1  0
 20 21  1  0
  8 31  1  0
 13 34  1  0
  6 30  1  1
 19 37  1  1
 15 35  1  0
 12 33  1  0
 10 32  1  0
 20 38  1  0
 20 39  1  0
 22 41  1  0
 23 42  1  0
  4 29  1  0
 25 43  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 21 40  1  0
M  END


  Mrv1652306202120233D          

 43 45  0  0  0  0            999 V2000
   -2.9443    1.1750   -1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906    0.1254   -1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997   -0.9373   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -1.0628    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.2163    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795   -2.3824    1.7049 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5428   -2.0158    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -2.8887   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -2.5321   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -3.3390   -1.9220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -1.3201   -0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975   -0.9761   -1.4893 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -0.4427    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.7858    1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7265    0.1533    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -0.2467    3.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    0.7386    4.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    0.4326    4.8991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -1.6492    3.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0252   -2.4783    4.1448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0606   -1.9347    5.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -3.2333    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -3.1116    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356   -1.9711   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -1.8773   -1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0320    0.8116   -1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928    1.9271   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.6590   -0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5433   -0.2732    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5779   -3.4585    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -3.8271   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -4.1296   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -1.7331   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286    0.4974    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    1.1624    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122    1.7568    3.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -1.5874    3.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -2.5740    3.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -3.4895    4.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326   -1.3329    5.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -4.1302    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -3.8970    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125   -1.0093   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 16 17  1  0  0  0  0
  8  7  1  0  0  0  0
 17 36  1  0  0  0  0
 11  9  1  0  0  0  0
 17 18  2  0  0  0  0
 14 13  1  0  0  0  0
 19 20  1  0  0  0  0
 13 11  2  0  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
  5 22  1  0  0  0  0
  7  6  1  0  0  0  0
 22 23  2  0  0  0  0
  6 19  1  0  0  0  0
 23 24  1  0  0  0  0
 19 16  1  0  0  0  0
 24  3  2  0  0  0  0
 16 15  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 14  7  2  0  0  0  0
 24 25  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
 20 21  1  0  0  0  0
  8 31  1  0  0  0  0
 13 34  1  0  0  0  0
  6 30  1  1  0  0  0
 19 37  1  1  0  0  0
 15 35  1  0  0  0  0
 12 33  1  0  0  0  0
 10 32  1  0  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 22 41  1  0  0  0  0
 23 42  1  0  0  0  0
  4 29  1  0  0  0  0
 25 43  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 21 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1O[H])[C@]([H])(C1=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C1[H])[C@]([H])(C(C([H])=O)=C2[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O6/c1-25-18-6-10(2-3-15(18)22)19-13-7-17(24)16(23)5-11(13)4-12(8-20)14(19)9-21/h2-8,14,19,21-24H,9H2,1H3/t14-,19-/m0/s1

> <INCHI_KEY>
PNRPRUVCFFHMMC-LIRRHRJNSA-N

> <FORMULA>
C19H18O6

> <MOLECULAR_WEIGHT>
342.347

> <EXACT_MASS>
342.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.67700832160614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S)-6,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-3,4-dihydronaphthalene-2-carbaldehyde

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
1.7034660316666665

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.078235721819542

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.96610325200467

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6341967486864917

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
93.1804

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitexdoin A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.9443    1.1750   -1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906    0.1254   -1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997   -0.9373   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -1.0628    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.2163    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795   -2.3824    1.7049 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5428   -2.0158    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -2.8887   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -2.5321   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -3.3390   -1.9220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -1.3201   -0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975   -0.9761   -1.4893 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -0.4427    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.7858    1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7265    0.1533    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -0.2467    3.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    0.7386    4.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    0.4326    4.8991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -1.6492    3.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0252   -2.4783    4.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606   -1.9347    5.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -3.2333    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -3.1116    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356   -1.9711   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -1.8773   -1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0320    0.8116   -1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928    1.9271   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.6590   -0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5433   -0.2732    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5779   -3.4585    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -3.8271   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -4.1296   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -1.7331   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286    0.4974    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    1.1624    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122    1.7568    3.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -1.5874    3.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -2.5740    3.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -3.4895    4.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326   -1.3329    5.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -4.1302    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -3.8970    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125   -1.0093   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0
 16 17  1  0
  8  7  1  0
 17 36  1  0
 11  9  1  0
 17 18  2  0
 14 13  1  0
 19 20  1  0
 13 11  2  0
  6  5  1  0
 14 15  1  0
  5 22  1  0
  7  6  1  0
 22 23  2  0
  6 19  1  0
 23 24  1  0
 19 16  1  0
 24  3  2  0
 16 15  2  0
  3  4  1  0
  4  5  2  0
 14  7  2  0
 24 25  1  0
 11 12  1  0
  3  2  1  0
  2  1  1  0
  9 10  1  0
 20 21  1  0
  8 31  1  0
 13 34  1  0
  6 30  1  1
 19 37  1  1
 15 35  1  0
 12 33  1  0
 10 32  1  0
 20 38  1  0
 20 39  1  0
 22 41  1  0
 23 42  1  0
  4 29  1  0
 25 43  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.944   1.175  -1.433  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.891   0.125  -1.265  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.500  -0.937  -0.492  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.284  -1.063   0.184  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.997  -2.216   0.942  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.680  -2.382   1.705  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.543  -2.016   0.868  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.987  -2.889  -0.143  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.078  -2.532  -0.924  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.549  -3.339  -1.922  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.728  -1.320  -0.713  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.797  -0.976  -1.489  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.301  -0.443   0.274  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.205  -0.786   1.073  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.727   0.153   2.092  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.164  -0.247   3.012  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.628   0.739   4.019  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.426   0.433   4.899  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.730  -1.649   3.081  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.025  -2.478   4.145  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.061  -1.935   5.459  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.966  -3.233   1.023  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.183  -3.112   0.354  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.436  -1.971  -0.394  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.637  -1.877  -1.042  0.00  0.00           O+0
HETATM   26  H   UNK     0      -2.032   0.812  -1.917  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.393   1.927  -2.089  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.720   1.659  -0.476  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.543  -0.273   0.129  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.578  -3.458   1.912  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.466  -3.827  -0.312  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.984  -4.130  -1.968  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.914  -1.733  -2.098  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.829   0.497   0.408  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.128   1.162   2.073  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.212   1.757   3.937  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.778  -1.587   3.408  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.088  -2.574   3.895  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.393  -3.490   4.195  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.833  -1.333   5.511  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.783  -4.130   1.611  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.930  -3.897   0.417  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.612  -1.009  -1.490  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3   24    4    2                                                  
CONECT    4    3    5   29                                                  
CONECT    5    6   22    4                                                  
CONECT    6    5    7   19   30                                             
CONECT    7    8    6   14                                                  
CONECT    8    9    7   31                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   32                                                       
CONECT   11    9   13   12                                                  
CONECT   12   11   33                                                       
CONECT   13   14   11   34                                                  
CONECT   14   13   15    7                                                  
CONECT   15   14   16   35                                                  
CONECT   16   17   19   15                                                  
CONECT   17   16   36   18                                                  
CONECT   18   17                                                            
CONECT   19   20    6   16   37                                             
CONECT   20   19   21   38   39                                             
CONECT   21   20   40                                                       
CONECT   22    5   23   41                                                  
CONECT   23   22   24   42                                                  
CONECT   24   23    3   25                                                  
CONECT   25   24   43                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    6                                                            
CONECT   31    8                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   23                                                            
CONECT   43   25                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
   -2.9443    1.1750   -1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906    0.1254   -1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997   -0.9373   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -1.0628    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.2163    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795   -2.3824    1.7049 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5428   -2.0158    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -2.8887   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0783   -2.5321   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -3.3390   -1.9220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -1.3201   -0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975   -0.9761   -1.4893 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -0.4427    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.7858    1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7265    0.1533    2.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -0.2467    3.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    0.7386    4.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    0.4326    4.8991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -1.6492    3.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0252   -2.4783    4.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606   -1.9347    5.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659   -3.2333    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -3.1116    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4356   -1.9711   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -1.8773   -1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0320    0.8116   -1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928    1.9271   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.6590   -0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5433   -0.2732    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5779   -3.4585    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -3.8271   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -4.1296   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136   -1.7331   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286    0.4974    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    1.1624    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122    1.7568    3.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -1.5874    3.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -2.5740    3.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -3.4895    4.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326   -1.3329    5.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -4.1302    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -3.8970    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125   -1.0093   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0
 16 17  1  0
  8  7  1  0
 17 36  1  0
 11  9  1  0
 17 18  2  0
 14 13  1  0
 19 20  1  0
 13 11  2  0
  6  5  1  0
 14 15  1  0
  5 22  1  0
  7  6  1  0
 22 23  2  0
  6 19  1  0
 23 24  1  0
 19 16  1  0
 24  3  2  0
 16 15  2  0
  3  4  1  0
  4  5  2  0
 14  7  2  0
 24 25  1  0
 11 12  1  0
  3  2  1  0
  2  1  1  0
  9 10  1  0
 20 21  1  0
  8 31  1  0
 13 34  1  0
  6 30  1  1
 19 37  1  1
 15 35  1  0
 12 33  1  0
 10 32  1  0
 20 38  1  0
 20 39  1  0
 22 41  1  0
 23 42  1  0
  4 29  1  0
 25 43  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 21 40  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈O₆

Average Mass

342.3470 Da

Monoisotopic Mass

342.11034 Da

IUPAC Name

(3R,4S)-6,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-3,4-dihydronaphthalene-2-carbaldehyde

Traditional Name

vitexdoin A

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1O[H])[C@]([H])(C1=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C1[H])[C@]([H])(C(C([H])=O)=C2[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C19H18O6/c1-25-18-6-10(2-3-15(18)22)19-13-7-17(24)16(23)5-11(13)4-12(8-20)14(19)9-21/h2-8,14,19,21-24H,9H2,1H3/t14-,19-/m0/s1

InChI Key

PNRPRUVCFFHMMC-LIRRHRJNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vitex negundo	JEOL database	Zheng, C. -J., et al, J. Nat. Prod. 72, 1627 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
2-naphthol
Cinnamaldehyde
Naphthalene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Alcohol
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.23	ALOGPS
logP	1.7	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.18 m³·mol⁻¹	ChemAxon
Polarizability	34.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24657214

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44478946

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zheng CJ, Huang BK, Han T, Zhang QY, Zhang H, Rahman K, Qin LP: Nitric oxide scavenging lignans from Vitex negundo seeds. J Nat Prod. 2009 Sep;72(9):1627-30. doi: 10.1021/np900320e. [PubMed:19715321 ]
Zheng, C. -J., et al. (2009). Zheng, C. -J., et al, J. Nat. Prod. 72, 1627 (2009). J. Nat. Prod..

Showing NP-Card for vitexdoin A (NP0034751)

MOL for NP0034751 (vitexdoin A)

3D MOL for NP0034751 (vitexdoin A)

3D SDF for NP0034751 (vitexdoin A)

3D-SDF for NP0034751 (vitexdoin A)

PDB for NP0034751 (vitexdoin A)

3D PDB for NP0034751 (vitexdoin A)

SMILES for NP0034751 (vitexdoin A)

INCHI for NP0034751 (vitexdoin A)

Structure for NP0034751 (vitexdoin A)

3D Structure for NP0034751 (vitexdoin A)