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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:26 UTC

Update Date

2022-03-07 02:52:39 UTC

HMDB ID

HMDB0030688

Secondary Accession Numbers

HMDB30688

Metabolite Identification

Common Name

Cyclomulberrin

Description

Cyclomulberrin belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Thus, cyclomulberrin is considered to be a flavonoid. Cyclomulberrin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Cyclomulberrin.

Structure

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


  Mrv0541 05061305262D          

 31 34  0  0  0  0            999 V2000
    5.5583   -1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    4.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    5.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    4.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    4.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    3.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  2  0  0  0  0
 14  6  1  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 11  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20  9  1  0  0  0  0
 21 18  2  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 15  2  0  0  0  0
 24 21  1  0  0  0  0
 25 16  1  0  0  0  0
 25 22  2  0  0  0  0
 26 14  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 23  2  0  0  0  0
 30 19  1  0  0  0  0
 30 20  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  1  0  0  0  0
M  END

HMDB0030688
     RDKit          3D
Cyclomulberrin
 55 58  0  0  0  0  0  0  0  0999 V2000
   -5.1749   -1.7250    1.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7734   -0.5754    0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8681    0.3381    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345   -0.4042    0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346    0.6679   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    0.1950   -1.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.3440   -2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1877   -0.4798   -2.6546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668   -0.7864   -3.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046   -0.6712   -3.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269   -1.1097   -4.4428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -0.1219   -2.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -0.0113   -2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -0.4038   -3.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    0.5568   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    0.9781   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    0.8483   -0.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.3162   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.5610    1.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    2.0106    2.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910    2.5703    3.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547    2.6767    3.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    3.2538    4.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4880    2.2386    2.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    1.6614    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    1.2178    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512    0.6738   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -0.6868   -1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9938   -1.6593   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762   -1.5469    1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5706   -2.9754   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4522   -2.5514    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3428   -1.3864    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -2.1023    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4494   -0.0613   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5790    0.3828    1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    1.3697    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7963   -1.1414    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715    1.3182   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    1.4113    0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8644   -0.1979   -1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -1.2091   -4.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749   -1.5128   -5.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    1.8904    2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931    2.8995    4.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    4.2569    4.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    2.3401    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7071    1.3673   -1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2337   -0.8798   -2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -2.5546    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -1.1890    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862   -0.8839    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6589   -2.8437   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460   -3.7765   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1115   -3.2096   -1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 18  6  1  0
 25 19  1  0
 18 12  2  0
 27 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 27 48  1  0
 28 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
 31 53  1  0
 31 54  1  0
 31 55  1  0
M  END


  Mrv0541 05061305262D          

 31 34  0  0  0  0            999 V2000
    5.5583   -1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    4.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    5.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    4.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    4.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    3.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  2  0  0  0  0
 14  6  1  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 11  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20  9  1  0  0  0  0
 21 18  2  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 15  2  0  0  0  0
 24 21  1  0  0  0  0
 25 16  1  0  0  0  0
 25 22  2  0  0  0  0
 26 14  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 23  2  0  0  0  0
 30 19  1  0  0  0  0
 30 20  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030688

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O6/c1-12(2)5-7-15-17(27)11-18(28)21-23(29)22-20(9-13(3)4)30-19-10-14(26)6-8-16(19)25(22)31-24(15)21/h5-6,8-11,20,26-28H,7H2,1-4H3

> <INCHI_KEY>
SYFDWXWLRGHYAJ-UHFFFAOYSA-N

> <FORMULA>
C25H24O6

> <MOLECULAR_WEIGHT>
420.4545

> <EXACT_MASS>
420.1572885

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
45.48489850960898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,8-trihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
5.331954428333335

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.598989655612732

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.389473914093079

> <JCHEM_PKA_STRONGEST_BASIC>
-4.822474122671532

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
120.27879999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclomulberrin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030688
     RDKit          3D
Cyclomulberrin
 55 58  0  0  0  0  0  0  0  0999 V2000
   -5.1749   -1.7250    1.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7734   -0.5754    0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8681    0.3381    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345   -0.4042    0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346    0.6679   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    0.1950   -1.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.3440   -2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1877   -0.4798   -2.6546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668   -0.7864   -3.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046   -0.6712   -3.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269   -1.1097   -4.4428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -0.1219   -2.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -0.0113   -2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -0.4038   -3.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    0.5568   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    0.9781   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    0.8483   -0.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.3162   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.5610    1.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    2.0106    2.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910    2.5703    3.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547    2.6767    3.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    3.2538    4.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4880    2.2386    2.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    1.6614    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    1.2178    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512    0.6738   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -0.6868   -1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9938   -1.6593   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762   -1.5469    1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5706   -2.9754   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4522   -2.5514    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3428   -1.3864    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -2.1023    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4494   -0.0613   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5790    0.3828    1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    1.3697    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7963   -1.1414    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715    1.3182   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    1.4113    0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8644   -0.1979   -1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -1.2091   -4.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749   -1.5128   -5.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    1.8904    2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931    2.8995    4.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    4.2569    4.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    2.3401    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7071    1.3673   -1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2337   -0.8798   -2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -2.5546    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -1.1890    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862   -0.8839    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6589   -2.8437   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460   -3.7765   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1115   -3.2096   -1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 18  6  1  0
 25 19  1  0
 18 12  2  0
 27 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 27 48  1  0
 28 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
 31 53  1  0
 31 54  1  0
 31 55  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.375  -2.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.855  -1.868   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.839   8.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.855  10.356   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.871  -0.121   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.831   1.625   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.384   0.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.343   1.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.359   7.737   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.327   4.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.904   3.371   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.367  -1.577   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.351   8.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.822   2.789   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.888   1.625   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.847   3.371   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.400   1.916   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.896   4.535   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.839   4.535   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.855   6.281   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.384   4.244   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.863   5.117   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.375   5.408   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.880   2.789   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.359   3.662   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.310   2.498   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      14.408   0.752   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      13.400   5.990   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.880   6.863   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.343   5.990   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.367   2.498   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    7   12                                                       
CONECT    6    8   14                                                       
CONECT    7    5   15                                                       
CONECT    8    6   16                                                       
CONECT    9   13   20                                                       
CONECT   10   14   19                                                       
CONECT   11   17   18                                                       
CONECT   12    1    2    5                                                  
CONECT   13    3    4    9                                                  
CONECT   14    6   10   26                                                  
CONECT   15    7   17   24                                                  
CONECT   16    8   19   25                                                  
CONECT   17   11   15   27                                                  
CONECT   18   11   21   28                                                  
CONECT   19   10   16   30                                                  
CONECT   20    9   22   30                                                  
CONECT   21   18   23   24                                                  
CONECT   22   20   23   25                                                  
CONECT   23   21   22   29                                                  
CONECT   24   15   21   31                                                  
CONECT   25   16   22   31                                                  
CONECT   26   14                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   23                                                            
CONECT   30   19   20                                                       
CONECT   31   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0030688
HETATM    1  C1  UNL     1      -5.175  -1.725   1.885  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.773  -0.575   0.990  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.868   0.338   0.610  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.534  -0.404   0.615  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.035   0.668  -0.250  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.204   0.195  -1.392  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.799  -0.344  -2.495  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.188  -0.480  -2.655  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.967  -0.786  -3.530  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.605  -0.671  -3.416  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.227  -1.110  -4.443  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.008  -0.122  -2.292  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.363  -0.011  -2.190  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.118  -0.404  -3.110  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.874   0.557  -1.017  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.017   0.978  -0.023  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.286   0.848  -0.175  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.817   0.316  -1.269  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.611   1.561   1.179  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.763   2.011   2.199  1.00  0.00           C  
HETATM   21  C17 UNL     1       1.291   2.570   3.328  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.655   2.677   3.429  1.00  0.00           C  
HETATM   23  O5  UNL     1       3.190   3.254   4.593  1.00  0.00           O  
HETATM   24  C19 UNL     1       3.488   2.239   2.435  1.00  0.00           C  
HETATM   25  C20 UNL     1       2.965   1.661   1.269  1.00  0.00           C  
HETATM   26  O6  UNL     1       3.781   1.218   0.270  1.00  0.00           O  
HETATM   27  C21 UNL     1       3.351   0.674  -0.939  1.00  0.00           C  
HETATM   28  C22 UNL     1       3.896  -0.687  -1.221  1.00  0.00           C  
HETATM   29  C23 UNL     1       3.994  -1.659  -0.339  1.00  0.00           C  
HETATM   30  C24 UNL     1       3.576  -1.547   1.072  1.00  0.00           C  
HETATM   31  C25 UNL     1       4.571  -2.975  -0.789  1.00  0.00           C  
HETATM   32  H1  UNL     1      -4.452  -2.551   1.815  1.00  0.00           H  
HETATM   33  H2  UNL     1      -5.343  -1.386   2.915  1.00  0.00           H  
HETATM   34  H3  UNL     1      -6.132  -2.102   1.473  1.00  0.00           H  
HETATM   35  H4  UNL     1      -6.449  -0.061  -0.247  1.00  0.00           H  
HETATM   36  H5  UNL     1      -6.579   0.383   1.499  1.00  0.00           H  
HETATM   37  H6  UNL     1      -5.558   1.370   0.376  1.00  0.00           H  
HETATM   38  H7  UNL     1      -2.796  -1.141   0.990  1.00  0.00           H  
HETATM   39  H8  UNL     1      -3.871   1.318  -0.646  1.00  0.00           H  
HETATM   40  H9  UNL     1      -2.409   1.411   0.323  1.00  0.00           H  
HETATM   41  H10 UNL     1      -4.864  -0.198  -1.999  1.00  0.00           H  
HETATM   42  H11 UNL     1      -2.455  -1.209  -4.392  1.00  0.00           H  
HETATM   43  H12 UNL     1      -0.175  -1.513  -5.268  1.00  0.00           H  
HETATM   44  H13 UNL     1      -0.318   1.890   2.045  1.00  0.00           H  
HETATM   45  H14 UNL     1       0.593   2.900   4.084  1.00  0.00           H  
HETATM   46  H15 UNL     1       3.339   4.257   4.605  1.00  0.00           H  
HETATM   47  H16 UNL     1       4.561   2.340   2.553  1.00  0.00           H  
HETATM   48  H17 UNL     1       3.707   1.367  -1.741  1.00  0.00           H  
HETATM   49  H18 UNL     1       4.234  -0.880  -2.238  1.00  0.00           H  
HETATM   50  H19 UNL     1       3.568  -2.555   1.535  1.00  0.00           H  
HETATM   51  H20 UNL     1       2.525  -1.189   1.145  1.00  0.00           H  
HETATM   52  H21 UNL     1       4.286  -0.884   1.630  1.00  0.00           H  
HETATM   53  H22 UNL     1       5.659  -2.844  -0.965  1.00  0.00           H  
HETATM   54  H23 UNL     1       4.346  -3.777  -0.054  1.00  0.00           H  
HETATM   55  H24 UNL     1       4.112  -3.210  -1.766  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4    4
CONECT    3   35   36   37
CONECT    4    5   38
CONECT    5    6   39   40
CONECT    6    7    7   18
CONECT    7    8    9
CONECT    8   41
CONECT    9   10   10   42
CONECT   10   11   12
CONECT   11   43
CONECT   12   13   18   18
CONECT   13   14   14   15
CONECT   15   16   16   27
CONECT   16   17   19
CONECT   17   18
CONECT   19   20   20   25
CONECT   20   21   44
CONECT   21   22   22   45
CONECT   22   23   24
CONECT   23   46
CONECT   24   25   25   47
CONECT   25   26
CONECT   26   27
CONECT   27   28   48
CONECT   28   29   29   49
CONECT   29   30   31
CONECT   30   50   51   52
CONECT   31   53   54   55
END

HMDB0030688
     RDKit          3D
Cyclomulberrin
 55 58  0  0  0  0  0  0  0  0999 V2000
   -5.1749   -1.7250    1.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7734   -0.5754    0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8681    0.3381    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345   -0.4042    0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346    0.6679   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    0.1950   -1.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.3440   -2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1877   -0.4798   -2.6546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668   -0.7864   -3.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046   -0.6712   -3.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269   -1.1097   -4.4428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -0.1219   -2.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -0.0113   -2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -0.4038   -3.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    0.5568   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    0.9781   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    0.8483   -0.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.3162   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.5610    1.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    2.0106    2.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910    2.5703    3.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547    2.6767    3.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    3.2538    4.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4880    2.2386    2.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    1.6614    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    1.2178    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512    0.6738   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -0.6868   -1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9938   -1.6593   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762   -1.5469    1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5706   -2.9754   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4522   -2.5514    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3428   -1.3864    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -2.1023    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4494   -0.0613   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5790    0.3828    1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    1.3697    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7963   -1.1414    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715    1.3182   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    1.4113    0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8644   -0.1979   -1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -1.2091   -4.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749   -1.5128   -5.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    1.8904    2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931    2.8995    4.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    4.2569    4.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    2.3401    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7071    1.3673   -1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2337   -0.8798   -2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -2.5546    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -1.1890    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862   -0.8839    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6589   -2.8437   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460   -3.7765   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1115   -3.2096   -1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 18  6  1  0
 25 19  1  0
 18 12  2  0
 27 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 27 48  1  0
 28 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
 31 53  1  0
 31 54  1  0
 31 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,8,10-Trihydroxy-11-(3-methyl-2-butenyl)-6-(2-methyl-1-propenyl)-6H,7H-[1]benzopyrano[4,3-b][1]benzopyran-7-one, 9ci	HMDB

Chemical Formula

C₂₅H₂₄O₆

Average Molecular Weight

420.4545

Monoisotopic Molecular Weight

420.1572885

IUPAC Name

1,3,8-trihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-11,12-dihydro-5,10-dioxatetraphen-12-one

Traditional Name

cyclomulberrin

CAS Registry Number

19275-51-5

SMILES

CC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O

InChI Identifier

InChI=1S/C25H24O6/c1-12(2)5-7-15-17(27)11-18(28)21-23(29)22-20(9-13(3)4)30-19-10-14(26)6-8-16(19)25(22)31-24(15)21/h5-6,8-11,20,26-28H,7H2,1-4H3

InChI Key

SYFDWXWLRGHYAJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Polyol
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110932 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030688)
Cell membrane (HMDB: HMDB0030688)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030688)

Source

Endogenous

Endogenous (HMDB: HMDB0030688)

Plant

Plant (HMDB: HMDB0030688)

Exogenous

Food

Food (HMDB: HMDB0030688)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030688)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	245 - 246 °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	0.0077 g/L	ALOGPS
logP	4.47	ALOGPS
logP	5.33	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	120.28 m³·mol⁻¹	ChemAxon
Polarizability	45.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	202.078	30932474
DeepCCS	[M-H]-	199.682	30932474
DeepCCS	[M-2H]-	232.837	30932474
DeepCCS	[M+Na]+	208.129	30932474
AllCCS	[M+H]+	202.4	32859911
AllCCS	[M+H-H2O]+	199.7	32859911
AllCCS	[M+NH4]+	204.8	32859911
AllCCS	[M+Na]+	205.5	32859911
AllCCS	[M-H]-	197.0	32859911
AllCCS	[M+Na-2H]-	196.5	32859911
AllCCS	[M+HCOO]-	196.2	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.	9.47 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9569 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.13 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3291.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	314.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	209.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	740.4 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	757.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1295.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	709.6 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	1587.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	486.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	197.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	240.4 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclomulberrin	CC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O	5549.4	Standard polar	33892256
Cyclomulberrin	CC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O	3707.3	Standard non polar	33892256
Cyclomulberrin	CC(C)=CCC1=C2OC3=C(C(OC4=C3C=CC(O)=C4)C=C(C)C)C(=O)C2=C(O)C=C1O	3792.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclomulberrin,1TMS,isomer #1	CC(C)=CCC1=C(O)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C21	3695.6	Semi standard non polar	33892256
Cyclomulberrin,1TMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C21	3666.3	Semi standard non polar	33892256
Cyclomulberrin,1TMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C21	3666.2	Semi standard non polar	33892256
Cyclomulberrin,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C21	3595.2	Semi standard non polar	33892256
Cyclomulberrin,2TMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C21	3612.7	Semi standard non polar	33892256
Cyclomulberrin,2TMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C21	3552.1	Semi standard non polar	33892256
Cyclomulberrin,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=CC=C21	3553.9	Semi standard non polar	33892256
Cyclomulberrin,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3929.6	Semi standard non polar	33892256
Cyclomulberrin,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C21	3897.7	Semi standard non polar	33892256
Cyclomulberrin,1TBDMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C21	3891.0	Semi standard non polar	33892256
Cyclomulberrin,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	4028.5	Semi standard non polar	33892256
Cyclomulberrin,2TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	4060.4	Semi standard non polar	33892256
Cyclomulberrin,2TBDMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=CC=C21	3986.9	Semi standard non polar	33892256
Cyclomulberrin,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	4142.1	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 - Cyclomulberrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6u-3449500000-b0c4f508485b909ccc20	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclomulberrin GC-MS (3 TMS) - 70eV, Positive	splash10-00di-2000049000-7bc0dfe9b13feece76ff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclomulberrin 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 - Cyclomulberrin 10V, Positive-QTOF	splash10-00di-1003900000-a8a0b37cb5840caad0e4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Positive-QTOF	splash10-014i-3149300000-e243ed99e4d684dc3c97	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Positive-QTOF	splash10-014i-9110100000-503470b143240bb8e9a7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 10V, Negative-QTOF	splash10-014i-0000900000-006a3fbd24235bcbecdc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Negative-QTOF	splash10-014i-0106900000-8d01ab175ce87619c15f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Negative-QTOF	splash10-0pdi-3915100000-bf6aaab044167770d183	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 10V, Negative-QTOF	splash10-014i-0000900000-e89f00937a4f746a0b2c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Negative-QTOF	splash10-014i-0000900000-e89f00937a4f746a0b2c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Negative-QTOF	splash10-014l-0190200000-a1118abed2e9f1ffe42a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 10V, Positive-QTOF	splash10-00di-0000900000-2c722d7f3ff1673a173f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 20V, Positive-QTOF	splash10-00di-0000900000-2c722d7f3ff1673a173f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclomulberrin 40V, Positive-QTOF	splash10-00di-0091500000-3ae896b8f74c53ff643a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002607

KNApSAcK ID

C00004061

Chemspider ID

9917576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11742872

PDB ID

Not Available

ChEBI ID

132869

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Cyclomulberrin → 6-{[1,8-dihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-12-oxo-11,12-dihydro-5,10-dioxatetraphen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Cyclomulberrin → 6-{[3,8-dihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-12-oxo-11,12-dihydro-5,10-dioxatetraphen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Cyclomulberrin → 6-{[1,3-dihydroxy-4-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-12-oxo-11,12-dihydro-5,10-dioxatetraphen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Cyclomulberrin (HMDB0030688)

MOL for HMDB0030688 (Cyclomulberrin)

3D MOL for HMDB0030688 (Cyclomulberrin)

3D SDF for HMDB0030688 (Cyclomulberrin)

3D-SDF for HMDB0030688 (Cyclomulberrin)

PDB for HMDB0030688 (Cyclomulberrin)

3D PDB for HMDB0030688 (Cyclomulberrin)

SMILES for HMDB0030688 (Cyclomulberrin)

INCHI for HMDB0030688 (Cyclomulberrin)

Structure for HMDB0030688 (Cyclomulberrin)

3D Structure for HMDB0030688 (Cyclomulberrin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions