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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:41:24 UTC

Update Date

2021-09-26 22:55:53 UTC

HMDB ID

HMDB0246672

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Description

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 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). Based on a literature review very few articles have been published on 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. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv0541 04121513282D          

 30 34  0  0  0  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
    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   -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
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  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  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
    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
    6.2803   -1.2680    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   -2.6029    0.0000 O   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
  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  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 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  0  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 22 30  1  0  0  0  0
M  END

HMDB0246672
     RDKit          3D
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6...
 52 56  0  0  0  0  0  0  0  0999 V2000
    2.7459    1.9475    2.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382    1.9082    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285    1.1617    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935    0.3947    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9233   -0.3326   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -1.1288    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -0.3981   -0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    0.7492   -0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445    1.4156   -1.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9993    0.9175   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015   -0.2318    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6984   -0.8936    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7393   -2.1251    1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1289   -1.8729    2.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4334   -2.8356    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -3.6583    2.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -3.6588    2.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7616   -2.5088    1.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644   -2.2135    1.8041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703   -1.7334    1.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0155    1.7914   -0.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5716    2.5123   -2.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781    2.5805   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4912   -0.2968   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.4610   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.5053   -2.9114 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -0.1851   -4.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1753    1.1750   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232    1.9295   -0.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2560    3.2673   -1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5315    2.4095    3.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    2.4776    3.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820    0.9277    3.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640    0.3830    1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785   -1.9745   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344    1.1335   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127   -0.6161    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -2.8276    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8703   -2.4538    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.3931    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -4.7156    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -3.2115    3.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -0.9636    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7889    1.9081   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286    3.5199   -2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0932   -0.8442   -2.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    0.3548   -4.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728   -1.2148   -3.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -0.3248   -4.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852    3.7687   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2629    3.7077   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    3.3061   -2.3934 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  0
  8 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 20 43  1  0
 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 04121513282D          

 30 34  0  0  0  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
    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   -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
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  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  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
    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
    6.2803   -1.2680    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   -2.6029    0.0000 O   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
  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  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 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  0  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 22 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246672

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(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

> <INCHI_KEY>
YJGVMLPVUAXIQN-UHFFFAOYSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.6697944198208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
picropodophyllin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246672
     RDKit          3D
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6...
 52 56  0  0  0  0  0  0  0  0999 V2000
    2.7459    1.9475    2.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382    1.9082    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285    1.1617    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935    0.3947    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9233   -0.3326   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -1.1288    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -0.3981   -0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    0.7492   -0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445    1.4156   -1.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9993    0.9175   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015   -0.2318    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6984   -0.8936    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7393   -2.1251    1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1289   -1.8729    2.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4334   -2.8356    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -3.6583    2.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -3.6588    2.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7616   -2.5088    1.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644   -2.2135    1.8041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703   -1.7334    1.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0155    1.7914   -0.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5716    2.5123   -2.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781    2.5805   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4912   -0.2968   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.4610   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.5053   -2.9114 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -0.1851   -4.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1753    1.1750   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232    1.9295   -0.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2560    3.2673   -1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5315    2.4095    3.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    2.4776    3.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820    0.9277    3.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640    0.3830    1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785   -1.9745   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344    1.1335   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127   -0.6161    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -2.8276    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8703   -2.4538    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.3931    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -4.7156    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -3.2115    3.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -0.9636    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7889    1.9081   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286    3.5199   -2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0932   -0.8442   -2.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    0.3548   -4.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728   -1.2148   -3.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -0.3248   -4.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852    3.7687   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2629    3.7077   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    3.3061   -2.3934 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  0
  8 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 20 43  1  0
 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                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         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  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.591 -12.083   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  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.628  -3.613   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      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   30                                                  
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   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   13   22                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

COMPND    HMDB0251859
HETATM    1  C1  UNL     1       2.029  -0.273  -3.627  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.934   0.134  -2.629  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.510   0.020  -1.289  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.241  -0.480  -1.028  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.827  -0.591   0.274  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.512  -1.109   0.640  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.533  -0.051   0.694  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.217   1.189   1.252  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.135   2.202   1.333  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.414   2.009   0.852  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.725   0.793   0.304  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.793  -0.218   0.229  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.223  -1.496  -0.390  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.432  -2.460   0.613  1.00  0.00           O  
HETATM   15  C13 UNL     1      -2.010  -1.950  -1.170  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.140  -3.292  -1.821  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.759  -3.690  -1.889  1.00  0.00           O  
HETATM   18  C15 UNL     1      -0.026  -3.056  -0.882  1.00  0.00           C  
HETATM   19  O4  UNL     1       1.220  -3.216  -0.798  1.00  0.00           O  
HETATM   20  C16 UNL     1      -0.986  -2.287  -0.095  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.173   3.175   1.039  1.00  0.00           O  
HETATM   22  C17 UNL     1      -3.233   4.191   1.322  1.00  0.00           C  
HETATM   23  O6  UNL     1      -2.102   3.513   1.827  1.00  0.00           O  
HETATM   24  C18 UNL     1       1.671  -0.208   1.299  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.927   0.287   1.040  1.00  0.00           C  
HETATM   26  O7  UNL     1       3.778   0.675   2.104  1.00  0.00           O  
HETATM   27  C20 UNL     1       3.307   0.543   3.452  1.00  0.00           C  
HETATM   28  C21 UNL     1       3.337   0.397  -0.260  1.00  0.00           C  
HETATM   29  O8  UNL     1       4.613   0.900  -0.514  1.00  0.00           O  
HETATM   30  C22 UNL     1       4.767   2.302  -0.686  1.00  0.00           C  
HETATM   31  H1  UNL     1       1.113   0.345  -3.506  1.00  0.00           H  
HETATM   32  H2  UNL     1       2.471  -0.177  -4.636  1.00  0.00           H  
HETATM   33  H3  UNL     1       1.756  -1.359  -3.510  1.00  0.00           H  
HETATM   34  H4  UNL     1       0.606  -0.770  -1.855  1.00  0.00           H  
HETATM   35  H5  UNL     1      -0.412  -1.445   1.734  1.00  0.00           H  
HETATM   36  H6  UNL     1      -0.227   1.369   1.636  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.726   0.635  -0.075  1.00  0.00           H  
HETATM   38  H8  UNL     1      -4.130  -1.414  -0.985  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.403  -2.544   0.835  1.00  0.00           H  
HETATM   40  H10 UNL     1      -1.704  -1.172  -1.863  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.664  -3.973  -1.109  1.00  0.00           H  
HETATM   42  H12 UNL     1      -2.620  -3.289  -2.799  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.538  -3.003   0.601  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.965   4.673   0.359  1.00  0.00           H  
HETATM   45  H15 UNL     1      -3.586   4.909   2.083  1.00  0.00           H  
HETATM   46  H16 UNL     1       1.362  -0.289   2.328  1.00  0.00           H  
HETATM   47  H17 UNL     1       3.988   1.014   4.164  1.00  0.00           H  
HETATM   48  H18 UNL     1       2.304   1.026   3.569  1.00  0.00           H  
HETATM   49  H19 UNL     1       3.237  -0.534   3.707  1.00  0.00           H  
HETATM   50  H20 UNL     1       5.255   2.770   0.210  1.00  0.00           H  
HETATM   51  H21 UNL     1       5.349   2.464  -1.599  1.00  0.00           H  
HETATM   52  H22 UNL     1       3.785   2.808  -0.794  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

HMDB0246672
     RDKit          3D
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6...
 52 56  0  0  0  0  0  0  0  0999 V2000
    2.7459    1.9475    2.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382    1.9082    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285    1.1617    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935    0.3947    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9233   -0.3326   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -1.1288    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -0.3981   -0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    0.7492   -0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445    1.4156   -1.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9993    0.9175   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015   -0.2318    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6984   -0.8936    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7393   -2.1251    1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1289   -1.8729    2.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4334   -2.8356    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -3.6583    2.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -3.6588    2.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7616   -2.5088    1.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644   -2.2135    1.8041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703   -1.7334    1.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0155    1.7914   -0.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5716    2.5123   -2.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781    2.5805   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4912   -0.2968   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.4610   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.5053   -2.9114 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -0.1851   -4.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1753    1.1750   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232    1.9295   -0.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2560    3.2673   -1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5315    2.4095    3.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    2.4776    3.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820    0.9277    3.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640    0.3830    1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785   -1.9745   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344    1.1335   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127   -0.6161    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -2.8276    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8703   -2.4538    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.3931    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -4.7156    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -3.2115    3.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -0.9636    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7889    1.9081   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286    3.5199   -2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0932   -0.8442   -2.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    0.3548   -4.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728   -1.2148   -3.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -0.3248   -4.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852    3.7687   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2629    3.7077   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    3.3061   -2.3934 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  0
  8 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 20 43  1  0
 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
Ardern brand OF podophyllotoxin	MeSH, HMDB
CPH86	MeSH, HMDB
Canderm brand OF podophyllotoxin	MeSH, HMDB
Condyline	MeSH, HMDB
Condylox	MeSH, HMDB
Epipodophyllotoxin	MeSH, HMDB
Fides ecopharma brand OF podophyllotoxin	MeSH, HMDB
Hamilton brand OF podophyllotoxin	MeSH, HMDB
Newport brand OF podophyllotoxin	MeSH, HMDB
Oclassen brand OF podophyllotoxin	MeSH, HMDB
Paddock brand OF podophyllotoxin	MeSH, HMDB
Paladin brand OF podophyllotoxin	MeSH, HMDB
PODOCON-25	MeSH, HMDB
Podofilm	MeSH, HMDB
Podofilox	MeSH, HMDB
Podophyllotoxin	MeSH, HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomer	MeSH, HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomer	MeSH, HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomer	MeSH, HMDB
Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomer	MeSH, HMDB
Stiefel brand OF podophyllotoxin	MeSH, HMDB
Wartec	MeSH, HMDB
Warticon	MeSH, HMDB
Wolff brand OF podophyllotoxin	MeSH, HMDB
Yamanouchi brand OF podophyllotoxin	MeSH, HMDB

Chemical Formula

C₂₂H₂₂O₈

Average Molecular Weight

414.41

Monoisotopic Molecular Weight

414.131467668

IUPAC Name

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

picropodophyllin

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(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

InChI Key

YJGVMLPVUAXIQN-UHFFFAOYSA-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

a lignan (CPD-8959 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256538)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	41.67 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
DeepCCS	[M-2H]-	222.421	30932474
DeepCCS	[M+Na]+	197.649	30932474
AllCCS	[M+H]+	195.4	32859911
AllCCS	[M+H-H2O]+	192.9	32859911
AllCCS	[M+NH4]+	197.6	32859911
AllCCS	[M+Na]+	198.3	32859911
AllCCS	[M-H]-	194.5	32859911
AllCCS	[M+Na-2H]-	194.3	32859911
AllCCS	[M+HCOO]-	194.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC	3398.9	Semi standard non polar	33892256
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC	3372.3	Standard non polar	33892256
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC	4780.2	Standard polar	33892256
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TBDMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C(C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC	3646.9	Semi standard non polar	33892256
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TBDMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C(C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC	3613.5	Standard non polar	33892256
5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TBDMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C(C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC	4854.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4699

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one (HMDB0246672)

MOL for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

3D MOL for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

3D SDF for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

3D-SDF for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

PDB for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

3D PDB for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

SMILES for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

INCHI for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

Structure for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

3D Structure for HMDB0246672 (5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized