Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:43:22 UTC

Update Date

2022-03-07 02:52:59 UTC

HMDB ID

HMDB0031452

Secondary Accession Numbers

HMDB31452

Metabolite Identification

Common Name

Lignans

Description

Lignans, also known as neolignans, belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Lignans has been detected, but not quantified in, several different foods, such as wheats (Triticum), ryes (Secale cereale), quinoas (Chenopodium quinoa), hard wheats (Triticum durum), and soy beans (Glycine max). This could make lignans a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Lignans.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241221352D          

 30 34  0  0  1  0            999 V2000
    1.9233   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  6  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 13 26  1  1  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 20 30  1  1  0  0  0
M  END

HMDB0031452
     RDKit          3D
Lignans
 52 56  0  0  0  0  0  0  0  0999 V2000
    2.1999   -3.0471    2.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0084   -2.2638    1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -1.4267    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534   -1.3069    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419   -0.4824   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -0.3404   -0.8748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4489    0.7304   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    1.7105    0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    2.7263    1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    2.7031    1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4490    1.7222    0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    0.7281    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6907   -0.3274   -0.5689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4961   -0.8914    0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9352   -1.3479   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687   -2.7310   -1.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3185   -3.5275   -1.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -2.7707   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0433   -3.1306   -1.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968   -1.5698   -0.6261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0745    3.8011    2.0921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    4.6661    2.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    3.8436    1.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    0.2509   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9091    0.1629   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636    0.8649   -1.8751 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    1.7579   -2.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.6806   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208   -0.7961    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3096    0.0805    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5559   -2.3500    3.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -3.7111    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -3.5927    3.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4447   -1.8801    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209   -0.0624   -1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968    1.7708    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    1.7110    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636    0.2117   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -0.7355    1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -1.0637   -2.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466   -3.0003   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1846   -2.9007   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335   -1.7516    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379    5.0326    3.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    5.4805    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    0.9061   -2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373    2.3748   -2.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746    1.1663   -3.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4231    2.3784   -3.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    1.0576    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2003   -0.3723    1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493    0.2219    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  6
  8 36  1  0
 11 37  1  0
 13 38  1  6
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 20 43  1  1
 22 44  1  0
 22 45  1  0
 24 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
M  END


  Mrv0541 02241221352D          

 30 34  0  0  1  0            999 V2000
    1.9233   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  6  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 13 26  1  1  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 20 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0031452

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13?,18-,19-,20+/m1/s1

> <INCHI_KEY>
YJGVMLPVUAXIQN-BCVBHCCTSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.4053

> <EXACT_MASS>
414.13146768

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
41.66443263959232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11S,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.6227982693333332

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.015751296514601

> <JCHEM_PKA_STRONGEST_BASIC>
-3.229310382904514

> <JCHEM_POLAR_SURFACE_AREA>
92.68

> <JCHEM_REFRACTIVITY>
103.90499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epipodophyllotoxins

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031452
     RDKit          3D
Lignans
 52 56  0  0  0  0  0  0  0  0999 V2000
    2.1999   -3.0471    2.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0084   -2.2638    1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -1.4267    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534   -1.3069    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419   -0.4824   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -0.3404   -0.8748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4489    0.7304   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    1.7105    0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    2.7263    1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    2.7031    1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4490    1.7222    0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    0.7281    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6907   -0.3274   -0.5689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4961   -0.8914    0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9352   -1.3479   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687   -2.7310   -1.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3185   -3.5275   -1.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -2.7707   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0433   -3.1306   -1.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968   -1.5698   -0.6261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0745    3.8011    2.0921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    4.6661    2.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    3.8436    1.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    0.2509   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9091    0.1629   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636    0.8649   -1.8751 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    1.7579   -2.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.6806   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208   -0.7961    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3096    0.0805    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5559   -2.3500    3.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -3.7111    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -3.5927    3.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4447   -1.8801    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209   -0.0624   -1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968    1.7708    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    1.7110    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636    0.2117   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -0.7355    1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -1.0637   -2.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466   -3.0003   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1846   -2.9007   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335   -1.7516    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379    5.0326    3.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    5.4805    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    0.9061   -2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373    2.3748   -2.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746    1.1663   -3.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4231    2.3784   -3.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    1.0576    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2003   -0.3723    1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493    0.2219    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  6
  8 36  1  0
 11 37  1  0
 13 38  1  6
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 20 43  1  1
 22 44  1  0
 22 45  1  0
 24 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.590 -11.313   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.590  -9.773   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.924 -12.083   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   26                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18                                                            
CONECT   20   15   21   30                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   13   21                                                  
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23                                                       
CONECT   30   20                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

COMPND    HMDB0031452
HETATM    1  C1  UNL     1       2.200  -3.047   2.444  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.008  -2.264   1.617  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.517  -1.427   0.625  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.153  -1.307   0.380  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.642  -0.482  -0.599  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.793  -0.340  -0.875  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.449   0.730  -0.101  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.681   1.711   0.467  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.293   2.726   1.200  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.665   2.703   1.326  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.449   1.722   0.759  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.808   0.728   0.037  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.691  -0.327  -0.569  1.00  0.00           C  
HETATM   14  O2  UNL     1      -4.496  -0.891   0.412  1.00  0.00           O  
HETATM   15  C13 UNL     1      -2.935  -1.348  -1.327  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.469  -2.731  -1.298  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.318  -3.528  -1.528  1.00  0.00           O  
HETATM   18  C15 UNL     1      -1.160  -2.771  -1.353  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.043  -3.131  -1.767  1.00  0.00           O  
HETATM   20  C16 UNL     1      -1.597  -1.570  -0.626  1.00  0.00           C  
HETATM   21  O5  UNL     1      -3.074   3.801   2.092  1.00  0.00           O  
HETATM   22  C17 UNL     1      -1.964   4.666   2.227  1.00  0.00           C  
HETATM   23  O6  UNL     1      -0.855   3.844   1.893  1.00  0.00           O  
HETATM   24  C18 UNL     1       1.560   0.251  -1.360  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.909   0.163  -1.152  1.00  0.00           C  
HETATM   26  O7  UNL     1       3.864   0.865  -1.875  1.00  0.00           O  
HETATM   27  C20 UNL     1       3.526   1.758  -2.918  1.00  0.00           C  
HETATM   28  C21 UNL     1       3.358  -0.681  -0.157  1.00  0.00           C  
HETATM   29  O8  UNL     1       4.721  -0.796   0.083  1.00  0.00           O  
HETATM   30  C22 UNL     1       5.310   0.081   1.019  1.00  0.00           C  
HETATM   31  H1  UNL     1       1.556  -2.350   3.031  1.00  0.00           H  
HETATM   32  H2  UNL     1       1.524  -3.711   1.883  1.00  0.00           H  
HETATM   33  H3  UNL     1       2.820  -3.593   3.183  1.00  0.00           H  
HETATM   34  H4  UNL     1       0.445  -1.880   0.976  1.00  0.00           H  
HETATM   35  H5  UNL     1      -0.921  -0.062  -1.962  1.00  0.00           H  
HETATM   36  H6  UNL     1       0.397   1.771   0.396  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.524   1.711   0.862  1.00  0.00           H  
HETATM   38  H8  UNL     1      -4.364   0.212  -1.269  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.151  -0.735   1.325  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.737  -1.064  -2.374  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.947  -3.000  -0.327  1.00  0.00           H  
HETATM   42  H12 UNL     1      -4.185  -2.901  -2.127  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.733  -1.752   0.451  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.938   5.033   3.257  1.00  0.00           H  
HETATM   45  H15 UNL     1      -2.103   5.481   1.492  1.00  0.00           H  
HETATM   46  H16 UNL     1       1.190   0.906  -2.135  1.00  0.00           H  
HETATM   47  H17 UNL     1       2.637   2.375  -2.679  1.00  0.00           H  
HETATM   48  H18 UNL     1       3.275   1.166  -3.844  1.00  0.00           H  
HETATM   49  H19 UNL     1       4.423   2.378  -3.154  1.00  0.00           H  
HETATM   50  H20 UNL     1       5.558   1.058   0.600  1.00  0.00           H  
HETATM   51  H21 UNL     1       6.200  -0.372   1.506  1.00  0.00           H  
HETATM   52  H22 UNL     1       4.549   0.222   1.831  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3
CONECT    3    4    4   28
CONECT    4    5   34
CONECT    5    6   24   24
CONECT    6    7   20   35
CONECT    7    8    8   12
CONECT    8    9   36
CONECT    9   10   10   23
CONECT   10   11   21
CONECT   11   12   12   37
CONECT   12   13
CONECT   13   14   15   38
CONECT   14   39
CONECT   15   16   20   40
CONECT   16   17   41   42
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   43
CONECT   21   22
CONECT   22   23   44   45
CONECT   24   25   46
CONECT   25   26   28   28
CONECT   26   27
CONECT   27   47   48   49
CONECT   28   29
CONECT   29   30
CONECT   30   50   51   52
END

HMDB0031452
     RDKit          3D
Lignans
 52 56  0  0  0  0  0  0  0  0999 V2000
    2.1999   -3.0471    2.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0084   -2.2638    1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -1.4267    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534   -1.3069    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419   -0.4824   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -0.3404   -0.8748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4489    0.7304   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    1.7105    0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    2.7263    1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    2.7031    1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4490    1.7222    0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    0.7281    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6907   -0.3274   -0.5689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4961   -0.8914    0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9352   -1.3479   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687   -2.7310   -1.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3185   -3.5275   -1.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -2.7707   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0433   -3.1306   -1.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968   -1.5698   -0.6261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0745    3.8011    2.0921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    4.6661    2.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    3.8436    1.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    0.2509   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9091    0.1629   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636    0.8649   -1.8751 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    1.7579   -2.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.6806   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208   -0.7961    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3096    0.0805    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5559   -2.3500    3.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -3.7111    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -3.5927    3.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4447   -1.8801    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209   -0.0624   -1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968    1.7708    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    1.7110    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636    0.2117   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -0.7355    1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -1.0637   -2.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466   -3.0003   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1846   -2.9007   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335   -1.7516    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379    5.0326    3.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    5.4805    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    0.9061   -2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373    2.3748   -2.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746    1.1663   -3.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4231    2.3784   -3.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    1.0576    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2003   -0.3723    1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493    0.2219    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  6
  8 36  1  0
 11 37  1  0
 13 38  1  6
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 20 43  1  1
 22 44  1  0
 22 45  1  0
 24 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Neolignans	MeSH
Lignan	MeSH
Neolignan	MeSH
Picropodophyllotoxin	HMDB
Podophyllotoxin	HMDB
Lignans	MeSH

Chemical Formula

C₂₂H₂₂O₈

Average Molecular Weight

414.4053

Monoisotopic Molecular Weight

414.13146768

IUPAC Name

(10R,11S,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

Traditional Name

epipodophyllotoxins

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13?,18-,19-,20+/m1/s1

InChI Key

YJGVMLPVUAXIQN-BCVBHCCTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Podophyllotoxins

Direct Parent

Podophyllotoxins

Alternative Parents

Substituents

Podophyllotoxin
1-aryltetralin lignan
Linear furanonaphthodioxole
Naphthofuran
Tetralin
Benzodioxole
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Lignans (C10871 )

Ontology

Not Available

Urine (PMID: 10744130)

Cellular substructure

Extracellular (HMDB: HMDB0031452)
Cytoplasm (HMDB: HMDB0031452)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031452)

Source

Exogenous

Exogenous (HMDB: HMDB0031452)

Food

Food (HMDB: HMDB0031452)

Cereal and cereal product

Cereal

Cereal product

Cereals and cereal products (FooDB: FOOD00858)

Soy

Soy bean (FooDB: FOOD00085)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Herb

Amaranth (FooDB: FOOD00288)
Teff (FooDB: FOOD00489)

Other seed

Quinoa (FooDB: FOOD00441)

Vegetable

Tuber

Arrowroot (FooDB: FOOD00290)

Endogenous

Endogenous (HMDB: HMDB0031452)

Plant

Plant (HMDB: HMDB0031452)

Process

Not Available

Role

Biological role

Industrial application

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.1 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.62	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.02	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.9 m³·mol⁻¹	ChemAxon
Polarizability	41.66 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	197.769	31661259
DarkChem	[M-H]-	193.363	31661259
DeepCCS	[M-2H]-	225.704	30932474
DeepCCS	[M+Na]+	201.129	30932474
AllCCS	[M+H]+	196.0	32859911
AllCCS	[M+H-H2O]+	193.3	32859911
AllCCS	[M+NH4]+	198.4	32859911
AllCCS	[M+Na]+	199.1	32859911
AllCCS	[M-H]-	199.4	32859911
AllCCS	[M+Na-2H]-	199.4	32859911
AllCCS	[M+HCOO]-	199.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.49 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6845 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.49 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2154.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	214.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	79.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	435.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	615.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	176.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	982.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	437.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1397.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	310.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	229.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	82.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lignans	COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12	5169.2	Standard polar	33892256
Lignans	COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12	3345.7	Standard non polar	33892256
Lignans	COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12	3477.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lignans,1TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C)C3COC(=O)[C@H]32)OCO4)=CC(OC)=C1OC	3326.9	Semi standard non polar	33892256
Lignans,1TBDMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C(C)(C)C)C3COC(=O)[C@H]32)OCO4)=CC(OC)=C1OC	3564.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lignans GC-MS (Non-derivatized) - 70eV, Positive	splash10-005j-0109000000-14f78dbe46f8312a8fb5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lignans GC-MS (1 TMS) - 70eV, Positive	splash10-0kmi-1003900000-d43e5f990afbda30580d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lignans GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lignans GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 10V, Positive-QTOF	splash10-00kb-0009500000-4616d49ee91153709c32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 20V, Positive-QTOF	splash10-014j-0029100000-07a109dcecbceb611534	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 40V, Positive-QTOF	splash10-0gc0-0029000000-866502321774872dbd1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 10V, Negative-QTOF	splash10-03di-0003900000-0a5bb4d2c68362569d3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 20V, Negative-QTOF	splash10-02ta-0009200000-dc7b8f1ae65bdd58832d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 40V, Negative-QTOF	splash10-014j-1039000000-d11a736e9337d8575e1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 10V, Positive-QTOF	splash10-014i-0020900000-1608d78c8539edf24423	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 20V, Positive-QTOF	splash10-014i-0043900000-e81bc57018acf33199a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 40V, Positive-QTOF	splash10-02vi-0039000000-552005d9b6b201ff3563	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 10V, Negative-QTOF	splash10-03di-0100900000-ec8194ed366395157a1b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 20V, Negative-QTOF	splash10-00lr-0009100000-bcb75b5aa88155a81414	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lignans 40V, Negative-QTOF	splash10-004i-2019100000-98fbf20ab2f57af37164	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.246 +/- 0.269 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.161 +/- 0.135 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	1.373 +/- 2.313 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17353586	details
Urine	Detected and Quantified	0.331 +/- 0.419 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lignan

METLIN ID

Not Available

PubChem Compound

443013

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lima LM, Perazzo FF, Tavares Carvalho JC, Bastos JK: Anti-inflammatory and analgesic activities of the ethanolic extracts from Zanthoxylum riedelianum (Rutaceae) leaves and stem bark. J Pharm Pharmacol. 2007 Aug;59(8):1151-8. [PubMed:17725859 ]
Valimaa AL, Honkalampi-Hamalainen U, Pietarinen S, Willfor S, Holmbom B, von Wright A: Antimicrobial and cytotoxic knotwood extracts and related pure compounds and their effects on food-associated microorganisms. Int J Food Microbiol. 2007 Apr 10;115(2):235-43. Epub 2006 Dec 22. [PubMed:17188387 ]
Ma CJ, Sung SH, Kim YC: New neuroprotective dibenzylbutane lignans isolated from Machilus thunbergii. Nat Prod Res. 2010 Apr;24(6):562-8. doi: 10.1080/14786410902823279. [PubMed:20397106 ]
Kassuya CA, Leite DF, de Melo LV, Rehder VL, Calixto JB: Anti-inflammatory properties of extracts, fractions and lignans isolated from Phyllanthus amarus. Planta Med. 2005 Aug;71(8):721-6. [PubMed:16142635 ]
(). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .

Showing metabocard for Lignans (HMDB0031452)

MOL for HMDB0031452 (Lignans)

3D MOL for HMDB0031452 (Lignans)

3D SDF for HMDB0031452 (Lignans)

3D-SDF for HMDB0031452 (Lignans)

PDB for HMDB0031452 (Lignans)

3D PDB for HMDB0031452 (Lignans)

SMILES for HMDB0031452 (Lignans)

INCHI for HMDB0031452 (Lignans)

Structure for HMDB0031452 (Lignans)

3D Structure for HMDB0031452 (Lignans)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra