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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:02 UTC

Update Date

2022-03-07 02:52:15 UTC

HMDB ID

HMDB0029682

Secondary Accession Numbers

HMDB29682

Metabolite Identification

Common Name

Cyclovariegatin

Description

Cyclovariegatin belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Cyclovariegatin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyclovariegatin has been detected, but not quantified in, mushrooms. This could make cyclovariegatin a potential biomarker for the consumption of these foods. The variants cyclovariegatin-pentaacetate, cyclovariegatin-2,3',8-triacetate, and cyclovariegatin-2-acetate have also been described. It has been isolated from the browned skin of Suillus grevillei var. badius, and becomes the pigment thelephoric acid. It is derived from atromentin. It is distinguishable by its UV-Vis spectra with maxima at 257, 296, and 430 nm. Cyclovariegatin is a pigment. Its chemical name is 1,4-Dihydro-2,7,8-trihydroxy-3-(3,4-dihydroxyphenyl)-l,4-dioxodibenzofuran.

Structure

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


  Mrv0541 02241218452D          

 26 29  0  0  0  0            999 V2000
    1.1959   -0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -2.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -2.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -0.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784   -0.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416    0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8659    0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309    1.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5259    2.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6810    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1861    1.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309   -1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209   -0.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -3.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460   -2.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    3.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883    1.4022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    3.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  2  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  2 20  2  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  2  0  0  0  0
  7 23  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 25  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 24  1  0  0  0  0
 17 18  2  0  0  0  0
 17 26  1  0  0  0  0
 18 19  1  0  0  0  0
M  END

HMDB0029682
     RDKit          3D
Cyclovariegatin
 36 39  0  0  0  0  0  0  0  0999 V2000
    1.0744    1.5649    1.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    0.7413    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -0.1955   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -0.1383    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3540   -0.1193    1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7168   -0.0342    1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5465    0.0380    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9051    0.1239    0.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9621    0.0202   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7737    0.0910   -2.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -0.0667   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -1.0805   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261   -1.9406   -1.5455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -1.1510   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171   -1.9970   -1.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -0.2230   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9592    0.7082    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    1.4271    1.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    1.0403    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520    1.4541    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4776    0.8620    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7551    1.3181    1.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2727   -0.1608   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3463   -0.8066   -0.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -0.6282   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -0.0078    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -0.1687    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.0289    2.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4196    0.1378    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460    0.0840   -2.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616   -0.0764   -2.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -1.9269   -2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4523    2.2690    1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5988    0.8890    0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3094   -0.5780   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8817   -1.4406   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
  3 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 17  2  1  0
 26 19  1  0
 11  4  1  0
 26 16  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 20 33  1  0
 22 34  1  0
 24 35  1  0
 25 36  1  0
M  END


  Mrv0541 02241218452D          

 26 29  0  0  0  0            999 V2000
    1.1959   -0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -2.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -2.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -0.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784   -0.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416    0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8659    0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309    1.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5259    2.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6810    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1861    1.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309   -1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209   -0.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -3.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460   -2.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    3.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883    1.4022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    3.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  2  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  2 20  2  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  2  0  0  0  0
  7 23  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 25  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 24  1  0  0  0  0
 17 18  2  0  0  0  0
 17 26  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029682

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1O)C1=C(O)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H10O8/c19-8-2-1-6(3-9(8)20)13-15(23)16(24)14-7-4-10(21)11(22)5-12(7)26-18(14)17(13)25/h1-5,19-23H

> <INCHI_KEY>
YXRBIRYXOSYHBV-UHFFFAOYSA-N

> <FORMULA>
C18H10O8

> <MOLECULAR_WEIGHT>
354.2672

> <EXACT_MASS>
354.037567296

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
34.022610014488606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(3,4-dihydroxyphenyl)-4,11,12-trihydroxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),4,10,12-pentaene-3,6-dione

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.5086113023333334

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.14058383476065

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.266706795920388

> <JCHEM_PKA_STRONGEST_BASIC>
-4.503254559011112

> <JCHEM_POLAR_SURFACE_AREA>
148.43

> <JCHEM_REFRACTIVITY>
89.24489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3,4-dihydroxyphenyl)-4,11,12-trihydroxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),4,10,12-pentaene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029682
     RDKit          3D
Cyclovariegatin
 36 39  0  0  0  0  0  0  0  0999 V2000
    1.0744    1.5649    1.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    0.7413    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -0.1955   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -0.1383    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3540   -0.1193    1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7168   -0.0342    1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5465    0.0380    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9051    0.1239    0.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9621    0.0202   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7737    0.0910   -2.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -0.0667   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -1.0805   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261   -1.9406   -1.5455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -1.1510   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171   -1.9970   -1.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -0.2230   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9592    0.7082    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    1.4271    1.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    1.0403    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520    1.4541    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4776    0.8620    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7551    1.3181    1.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2727   -0.1608   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3463   -0.8066   -0.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -0.6282   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -0.0078    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -0.1687    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.0289    2.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4196    0.1378    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460    0.0840   -2.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616   -0.0764   -2.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -1.9269   -2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4523    2.2690    1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5988    0.8890    0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3094   -0.5780   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8817   -1.4406   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
  3 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 17  2  1  0
 26 19  1  0
 11  4  1  0
 26 16  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 20 33  1  0
 22 34  1  0
 24 35  1  0
 25 36  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       2.232  -0.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.308  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.230  -1.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.308  -2.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.308  -4.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.695  -4.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.926  -4.004   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.926  -2.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.695  -1.693   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.386  -0.153   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.846   0.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.078   1.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.616   1.077   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.540   2.309   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.924   3.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.848   4.927   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.388   4.773   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.005   3.387   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.081   2.155   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.924  -3.079   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.772  -0.615   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.695  -6.314   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.313  -4.773   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.232   6.314   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.538   2.617   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.313   6.006   0.000  0.00  0.00           O+0
CONECT    1    2   13   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    3   10   12                                                  
CONECT   12   11   13   25                                                  
CONECT   13    1   12   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   14   18                                                       
CONECT   20    2                                                            
CONECT   21    1                                                            
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24   16                                                            
CONECT   25   12                                                            
CONECT   26   17                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0029682
HETATM    1  O1  UNL     1       1.074   1.565   1.496  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.496   0.741   0.764  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.304  -0.196  -0.033  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.753  -0.138   0.011  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.354  -0.119   1.279  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.717  -0.034   1.455  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.547   0.038   0.356  1.00  0.00           C  
HETATM    8  O2  UNL     1       6.905   0.124   0.444  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.962   0.020  -0.910  1.00  0.00           C  
HETATM   10  O3  UNL     1       5.774   0.091  -2.030  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.587  -0.067  -1.066  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.720  -1.080  -0.819  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.526  -1.941  -1.546  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.753  -1.151  -0.917  1.00  0.00           C  
HETATM   15  O5  UNL     1      -1.317  -1.997  -1.667  1.00  0.00           O  
HETATM   16  C11 UNL     1      -1.549  -0.223  -0.127  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.959   0.708   0.700  1.00  0.00           C  
HETATM   18  O6  UNL     1      -1.883   1.427   1.303  1.00  0.00           O  
HETATM   19  C13 UNL     1      -3.075   1.040   0.934  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.352   1.454   1.261  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.478   0.862   0.714  1.00  0.00           C  
HETATM   22  O7  UNL     1      -6.755   1.318   1.080  1.00  0.00           O  
HETATM   23  C16 UNL     1      -5.273  -0.161  -0.172  1.00  0.00           C  
HETATM   24  O8  UNL     1      -6.346  -0.807  -0.764  1.00  0.00           O  
HETATM   25  C17 UNL     1      -4.010  -0.628  -0.547  1.00  0.00           C  
HETATM   26  C18 UNL     1      -2.923  -0.008   0.024  1.00  0.00           C  
HETATM   27  H1  UNL     1       2.723  -0.169   2.156  1.00  0.00           H  
HETATM   28  H2  UNL     1       5.123  -0.029   2.467  1.00  0.00           H  
HETATM   29  H3  UNL     1       7.420   0.138   1.317  1.00  0.00           H  
HETATM   30  H4  UNL     1       5.346   0.084  -2.947  1.00  0.00           H  
HETATM   31  H5  UNL     1       3.162  -0.076  -2.054  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.423  -1.927  -2.549  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.452   2.269   1.970  1.00  0.00           H  
HETATM   34  H8  UNL     1      -7.599   0.889   0.747  1.00  0.00           H  
HETATM   35  H9  UNL     1      -7.309  -0.578  -0.592  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.882  -1.441  -1.248  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4   12   12
CONECT    4    5    5   11
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8    9
CONECT    8   29
CONECT    9   10   11   11
CONECT   10   30
CONECT   11   31
CONECT   12   13   14
CONECT   13   32
CONECT   14   15   15   16
CONECT   16   17   17   26
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   26
CONECT   20   21   33
CONECT   21   22   23   23
CONECT   22   34
CONECT   23   24   25
CONECT   24   35
CONECT   25   26   26   36
END

HMDB0029682
     RDKit          3D
Cyclovariegatin
 36 39  0  0  0  0  0  0  0  0999 V2000
    1.0744    1.5649    1.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    0.7413    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -0.1955   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -0.1383    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3540   -0.1193    1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7168   -0.0342    1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5465    0.0380    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9051    0.1239    0.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9621    0.0202   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7737    0.0910   -2.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -0.0667   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -1.0805   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261   -1.9406   -1.5455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -1.1510   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3171   -1.9970   -1.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -0.2230   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9592    0.7082    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    1.4271    1.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    1.0403    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520    1.4541    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4776    0.8620    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7551    1.3181    1.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2727   -0.1608   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3463   -0.8066   -0.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -0.6282   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -0.0078    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -0.1687    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.0289    2.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4196    0.1378    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460    0.0840   -2.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616   -0.0764   -2.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -1.9269   -2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4523    2.2690    1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5988    0.8890    0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3094   -0.5780   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8817   -1.4406   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
  3 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 17  2  1  0
 26 19  1  0
 11  4  1  0
 26 16  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 20 33  1  0
 22 34  1  0
 24 35  1  0
 25 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₀O₈

Average Molecular Weight

354.2672

Monoisotopic Molecular Weight

354.037567296

IUPAC Name

5-(3,4-dihydroxyphenyl)-4,11,12-trihydroxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),4,10,12-pentaene-3,6-dione

Traditional Name

5-(3,4-dihydroxyphenyl)-4,11,12-trihydroxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),4,10,12-pentaene-3,6-dione

CAS Registry Number

55692-59-6

SMILES

OC1=CC=C(C=C1O)C1=C(O)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O

InChI Identifier

InChI=1S/C18H10O8/c19-8-2-1-6(3-9(8)20)13-15(23)16(24)14-7-4-10(21)11(22)5-12(7)26-18(14)17(13)25/h1-5,19-23H

InChI Key

YXRBIRYXOSYHBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Vinylogous acid
Ketone
Enol
Polyol
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029682)
Cytoplasm (HMDB: HMDB0029682)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029682)

Source

Endogenous

Endogenous (HMDB: HMDB0029682)

Plant

Plant (HMDB: HMDB0029682)

Exogenous

Food

Food (HMDB: HMDB0029682)

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	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
Water Solubility	0.37 g/L	ALOGPS
logP	2.17	ALOGPS
logP	1.51	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	148.43 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.24 m³·mol⁻¹	ChemAxon
Polarizability	34.02 Å³	ChemAxon
Number of Rings	4	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+H]+	183.073	30932474
DeepCCS	[M-H]-	180.715	30932474
DeepCCS	[M-2H]-	214.596	30932474
DeepCCS	[M+Na]+	189.825	30932474
AllCCS	[M+H]+	181.5	32859911
AllCCS	[M+H-H2O]+	178.2	32859911
AllCCS	[M+NH4]+	184.5	32859911
AllCCS	[M+Na]+	185.4	32859911
AllCCS	[M-H]-	179.3	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	177.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclovariegatin	OC1=CC=C(C=C1O)C1=C(O)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O	4704.8	Standard polar	33892256
Cyclovariegatin	OC1=CC=C(C=C1O)C1=C(O)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O	3130.9	Standard non polar	33892256
Cyclovariegatin	OC1=CC=C(C=C1O)C1=C(O)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O	3516.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclovariegatin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O)C=C34)C2=O)C=C1O	3571.7	Semi standard non polar	33892256
Cyclovariegatin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O)C=C34)C2=O)=CC=C1O	3602.5	Semi standard non polar	33892256
Cyclovariegatin,1TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	3542.7	Semi standard non polar	33892256
Cyclovariegatin,1TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C(O)=C(C2=CC=C(O)C(O)=C2)C1=O	3549.5	Semi standard non polar	33892256
Cyclovariegatin,1TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C(C2=CC=C(O)C(O)=C2)=C(O)C1=O	3538.1	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #1	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	3459.7	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #10	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C1=C(O2)C(=O)C(C2=CC=C(O)C(O)=C2)=C(O)C1=O	3481.3	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C)=C(O)C=C34)C2=O)C=C1O	3633.1	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O[Si](C)(C)C)C=C34)C2=O)C=C1O	3650.6	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O)C=C34)C2=O)C=C1O[Si](C)(C)C	3496.9	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #5	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	3456.3	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #6	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C)=C(O)C=C34)C2=O)=CC=C1O	3643.8	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #7	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O[Si](C)(C)C)C=C34)C2=O)=CC=C1O	3661.6	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #8	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C)C=C1O2	3422.9	Semi standard non polar	33892256
Cyclovariegatin,2TMS,isomer #9	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O)C=C1O2	3441.5	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #1	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	3408.7	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #10	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O2	3424.4	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #2	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C)C=C1O2	3563.6	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O)C=C1O2	3591.8	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C34)C2=O)C=C1O	3553.6	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=C(O)C1=O	3535.7	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #6	C[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C(O)=C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1=O	3556.0	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #7	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C)C=C1O2	3545.3	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #8	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O)C=C1O2	3573.8	Semi standard non polar	33892256
Cyclovariegatin,3TMS,isomer #9	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C34)C2=O)=CC=C1O	3535.2	Semi standard non polar	33892256
Cyclovariegatin,4TMS,isomer #1	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C)C=C1O2	3527.3	Semi standard non polar	33892256
Cyclovariegatin,4TMS,isomer #2	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O)C=C1O2	3547.6	Semi standard non polar	33892256
Cyclovariegatin,4TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O2	3538.5	Semi standard non polar	33892256
Cyclovariegatin,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C34)C2=O)C=C1O[Si](C)(C)C	3506.8	Semi standard non polar	33892256
Cyclovariegatin,4TMS,isomer #5	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O2	3526.7	Semi standard non polar	33892256
Cyclovariegatin,5TMS,isomer #1	C[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O2	3530.8	Semi standard non polar	33892256
Cyclovariegatin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O)C=C34)C2=O)C=C1O	3871.7	Semi standard non polar	33892256
Cyclovariegatin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O)C=C34)C2=O)=CC=C1O	3877.3	Semi standard non polar	33892256
Cyclovariegatin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	3828.8	Semi standard non polar	33892256
Cyclovariegatin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C(O)=C(C2=CC=C(O)C(O)=C2)C1=O	3856.4	Semi standard non polar	33892256
Cyclovariegatin,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C(C2=CC=C(O)C(O)=C2)=C(O)C1=O	3843.1	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	4017.1	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1=C(O2)C(=O)C(C2=CC=C(O)C(O)=C2)=C(O)C1=O	3978.8	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C34)C2=O)C=C1O	4150.1	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C34)C2=O)C=C1O	4168.5	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O)C=C34)C2=O)C=C1O[Si](C)(C)C(C)(C)C	3986.7	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	4013.6	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C34)C2=O)=CC=C1O	4148.7	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C34)C2=O)=CC=C1O	4173.8	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C1O2	3996.2	Semi standard non polar	33892256
Cyclovariegatin,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C1O2	4016.3	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O2	4161.6	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O2	4181.8	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C1O2	4368.4	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C1O2	4394.7	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C34)C2=O)C=C1O	4313.0	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=C(O)C1=O	4287.3	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C(O)=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C1=O	4308.5	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C1O2	4330.3	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C1O2	4360.7	Semi standard non polar	33892256
Cyclovariegatin,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C34)C2=O)=CC=C1O	4297.4	Semi standard non polar	33892256
Cyclovariegatin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C1O2	4425.8	Semi standard non polar	33892256
Cyclovariegatin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C1O2	4452.2	Semi standard non polar	33892256
Cyclovariegatin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O2	4479.6	Semi standard non polar	33892256
Cyclovariegatin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(OC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C34)C2=O)C=C1O[Si](C)(C)C(C)(C)C	4448.9	Semi standard non polar	33892256
Cyclovariegatin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O2	4468.0	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 - Cyclovariegatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-0629000000-801b40e0538769e6610d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclovariegatin GC-MS (4 TMS) - 70eV, Positive	splash10-00di-3360097000-3bfa109993d4ea6c9e74	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclovariegatin 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 - Cyclovariegatin 10V, Positive-QTOF	splash10-0a4i-0109000000-948ead8898fd1f361948	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 20V, Positive-QTOF	splash10-0a6r-0629000000-7248704a89c6d1847cea	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 40V, Positive-QTOF	splash10-05fs-4931000000-cfbbca3ec16bd1573fdf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 10V, Negative-QTOF	splash10-0udi-0009000000-111ccf8ce5276512a14d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 20V, Negative-QTOF	splash10-0udj-0459000000-e8732a333f5a40c00ca4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 40V, Negative-QTOF	splash10-0kbb-1942000000-de111c34e61aa29f9a00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 10V, Negative-QTOF	splash10-0udi-0009000000-8538792e1bf5205df48f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 20V, Negative-QTOF	splash10-0udi-0009000000-cabb4506a03518164144	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 40V, Negative-QTOF	splash10-0002-0392000000-ff2ce7d772e02e731f86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 10V, Positive-QTOF	splash10-0a4i-0009000000-7d26137e096af06cdeab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 20V, Positive-QTOF	splash10-0a4i-0009000000-2d8c7bad1f8f55823972	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclovariegatin 40V, Positive-QTOF	splash10-004i-0984000000-624318bfe8ab7c76873a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB000868

KNApSAcK ID

Not Available

Chemspider ID

30776786

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclovariegatin

METLIN ID

Not Available

PubChem Compound

137185900

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cyclovariegatin (HMDB0029682)

MOL for HMDB0029682 (Cyclovariegatin)

3D MOL for HMDB0029682 (Cyclovariegatin)

3D SDF for HMDB0029682 (Cyclovariegatin)

3D-SDF for HMDB0029682 (Cyclovariegatin)

PDB for HMDB0029682 (Cyclovariegatin)

3D PDB for HMDB0029682 (Cyclovariegatin)

SMILES for HMDB0029682 (Cyclovariegatin)

INCHI for HMDB0029682 (Cyclovariegatin)

Structure for HMDB0029682 (Cyclovariegatin)

3D Structure for HMDB0029682 (Cyclovariegatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra