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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:17:38 UTC

Update Date

2021-09-26 23:12:37 UTC

HMDB ID

HMDB0256728

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Praeruptorin B

Description

8,8-dimethyl-10-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-9-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. Based on a literature review very few articles have been published on 8,8-dimethyl-10-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-9-yl 2-methylbut-2-enoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Praeruptorin b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Praeruptorin B 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


  Mrv1533004171502492D          

 31 33  0  0  0  0            999 V2000
    3.6829   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 13 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
  8 31  1  0  0  0  0
 21 31  1  0  0  0  0
M  END

HMDB0256728
     RDKit          3D
Praeruptorin B
 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.2839    2.7728    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    1.8476    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551    1.3458   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    1.7064   -2.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195    0.4308   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -0.0462   -2.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    0.0494    0.1110 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -0.8260    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0324   -2.0382    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -2.4898    1.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -3.6291    2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418   -4.3545    2.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -3.8910    1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5943   -4.5814    1.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -4.1075    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410   -2.9628   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149   -2.5445   -1.0666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0998   -2.3519   -0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593   -2.7511    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -1.8123    1.9361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6069   -1.0008    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7902   -0.1284    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9408   -1.9000   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245   -0.0810    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101    0.9739   -0.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    2.2880    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    2.4562    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916    3.4231   -0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458    4.7828   -0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5840    3.2956   -1.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6389    1.9334   -2.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3246    3.4496   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2184    2.1490    0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    3.3655    1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.5942    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3211    2.8121   -2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5899    1.6144   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1422    1.1906   -2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -1.1105   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -3.9830    3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6544   -5.2388    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -5.4765    1.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4656   -4.6473    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5727   -0.7896    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1920    0.2990    0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162    0.7126    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812   -1.9668   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894   -2.9367    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780   -1.5137   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393    0.3357    1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    5.1125    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803    5.4917   -0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312    4.8539    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718    4.1420   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    2.0021   -3.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    1.4501   -2.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659    1.2785   -1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  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
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28 30  2  3
 30 31  1  0
 24  8  1  0
 19  9  1  0
 19 13  2  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 29 51  1  0
 29 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 31 56  1  0
 31 57  1  0
M  END


  Mrv1533004171502492D          

 31 33  0  0  0  0            999 V2000
    3.6829   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 13 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
  8 31  1  0  0  0  0
 21 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256728

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=C(C)C(=O)OC1C(OC(=O)C(C)=CC)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3

> <INCHI_KEY>
PNTWXEIQXBRCPS-UHFFFAOYSA-N

> <FORMULA>
C24H26O7

> <MOLECULAR_WEIGHT>
426.465

> <EXACT_MASS>
426.167853177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.786852345205496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12,12-dimethyl-14-[(2-methylbut-2-enoyl)oxy]-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-13-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
5.239271929333334

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.898852514525875

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000001

> <JCHEM_REFRACTIVITY>
115.20799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,12-dimethyl-14-[(2-methylbut-2-enoyl)oxy]-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-13-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256728
     RDKit          3D
Praeruptorin B
 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.2839    2.7728    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    1.8476    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551    1.3458   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    1.7064   -2.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195    0.4308   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -0.0462   -2.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    0.0494    0.1110 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -0.8260    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0324   -2.0382    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -2.4898    1.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -3.6291    2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418   -4.3545    2.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -3.8910    1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5943   -4.5814    1.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -4.1075    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410   -2.9628   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149   -2.5445   -1.0666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0998   -2.3519   -0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593   -2.7511    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -1.8123    1.9361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6069   -1.0008    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7902   -0.1284    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9408   -1.9000   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245   -0.0810    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101    0.9739   -0.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    2.2880    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    2.4562    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916    3.4231   -0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458    4.7828   -0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5840    3.2956   -1.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6389    1.9334   -2.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3246    3.4496   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2184    2.1490    0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    3.3655    1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.5942    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3211    2.8121   -2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5899    1.6144   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1422    1.1906   -2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -1.1105   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -3.9830    3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6544   -5.2388    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -5.4765    1.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4656   -4.6473    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5727   -0.7896    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1920    0.2990    0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162    0.7126    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812   -1.9668   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894   -2.9367    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780   -1.5137   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393    0.3357    1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    5.1125    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803    5.4917   -0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312    4.8539    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718    4.1420   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    2.0021   -3.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    1.4501   -2.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659    1.2785   -1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  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
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28 30  2  3
 30 31  1  0
 24  8  1  0
 19  9  1  0
 19 13  2  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 29 51  1  0
 29 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 31 56  1  0
 31 57  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.875  -9.542   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.105  -8.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.875  -6.875   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415  -6.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.105  -5.541   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.565  -5.541   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.485  -5.541   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.055  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.615  -2.530   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.615  -0.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.565  -0.206   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.185  -2.874   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17    9   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24   31                                                  
CONECT   31   30    8   21                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0256728
HETATM    1  C1  UNL     1      -4.284   2.773   0.367  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.126   1.848   0.286  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.755   1.346  -0.875  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.497   1.706  -2.108  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.619   0.431  -0.996  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.268  -0.046  -2.105  1.00  0.00           O  
HETATM    7  O2  UNL     1      -0.880   0.049   0.111  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.222  -0.826   0.062  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.032  -2.038   0.882  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.986  -2.490   1.764  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.726  -3.629   2.489  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.442  -4.355   2.386  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.408  -3.891   1.487  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.594  -4.581   1.348  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.550  -4.108   0.447  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.241  -2.963  -0.255  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.115  -2.545  -1.067  1.00  0.00           O  
HETATM   18  O4  UNL     1      -2.100  -2.352  -0.079  1.00  0.00           O  
HETATM   19  C15 UNL     1      -1.159  -2.751   0.756  1.00  0.00           C  
HETATM   20  O5  UNL     1       2.211  -1.812   1.936  1.00  0.00           O  
HETATM   21  C16 UNL     1       2.607  -1.001   0.845  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.790  -0.128   1.196  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.941  -1.900  -0.300  1.00  0.00           C  
HETATM   24  C19 UNL     1       1.424  -0.081   0.557  1.00  0.00           C  
HETATM   25  O6  UNL     1       1.810   0.974  -0.287  1.00  0.00           O  
HETATM   26  C20 UNL     1       1.808   2.288   0.143  1.00  0.00           C  
HETATM   27  O7  UNL     1       1.431   2.456   1.354  1.00  0.00           O  
HETATM   28  C21 UNL     1       2.192   3.423  -0.669  1.00  0.00           C  
HETATM   29  C22 UNL     1       2.146   4.783  -0.090  1.00  0.00           C  
HETATM   30  C23 UNL     1       2.584   3.296  -1.915  1.00  0.00           C  
HETATM   31  C24 UNL     1       2.639   1.933  -2.523  1.00  0.00           C  
HETATM   32  H1  UNL     1      -4.325   3.450  -0.519  1.00  0.00           H  
HETATM   33  H2  UNL     1      -5.218   2.149   0.313  1.00  0.00           H  
HETATM   34  H3  UNL     1      -4.274   3.366   1.301  1.00  0.00           H  
HETATM   35  H4  UNL     1      -2.596   1.594   1.188  1.00  0.00           H  
HETATM   36  H5  UNL     1      -3.321   2.812  -2.254  1.00  0.00           H  
HETATM   37  H6  UNL     1      -4.590   1.614  -1.930  1.00  0.00           H  
HETATM   38  H7  UNL     1      -3.142   1.191  -2.996  1.00  0.00           H  
HETATM   39  H8  UNL     1       0.333  -1.110  -1.025  1.00  0.00           H  
HETATM   40  H9  UNL     1       1.494  -3.983   3.193  1.00  0.00           H  
HETATM   41  H10 UNL     1      -0.654  -5.239   2.943  1.00  0.00           H  
HETATM   42  H11 UNL     1      -2.781  -5.476   1.927  1.00  0.00           H  
HETATM   43  H12 UNL     1      -4.466  -4.647   0.344  1.00  0.00           H  
HETATM   44  H13 UNL     1       4.573  -0.790   1.614  1.00  0.00           H  
HETATM   45  H14 UNL     1       4.192   0.299   0.255  1.00  0.00           H  
HETATM   46  H15 UNL     1       3.516   0.713   1.852  1.00  0.00           H  
HETATM   47  H16 UNL     1       2.181  -1.967  -1.084  1.00  0.00           H  
HETATM   48  H17 UNL     1       3.189  -2.937   0.026  1.00  0.00           H  
HETATM   49  H18 UNL     1       3.878  -1.514  -0.792  1.00  0.00           H  
HETATM   50  H19 UNL     1       1.139   0.336   1.568  1.00  0.00           H  
HETATM   51  H20 UNL     1       3.130   5.112   0.304  1.00  0.00           H  
HETATM   52  H21 UNL     1       1.880   5.492  -0.899  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.431   4.854   0.764  1.00  0.00           H  
HETATM   54  H23 UNL     1       2.872   4.142  -2.526  1.00  0.00           H  
HETATM   55  H24 UNL     1       3.045   2.002  -3.575  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.636   1.450  -2.560  1.00  0.00           H  
HETATM   57  H26 UNL     1       3.366   1.278  -1.993  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3   35
CONECT    3    4    5
CONECT    4   36   37   38
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   24   39
CONECT    9   10   10   19
CONECT   10   11   20
CONECT   11   12   12   40
CONECT   12   13   41
CONECT   13   14   19   19
CONECT   14   15   15   42
CONECT   15   16   43
CONECT   16   17   17   18
CONECT   18   19
CONECT   20   21
CONECT   21   22   23   24
CONECT   22   44   45   46
CONECT   23   47   48   49
CONECT   24   25   50
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   29   30   30
CONECT   29   51   52   53
CONECT   30   31   54
CONECT   31   55   56   57
END

HMDB0256728
     RDKit          3D
Praeruptorin B
 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.2839    2.7728    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    1.8476    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551    1.3458   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    1.7064   -2.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195    0.4308   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -0.0462   -2.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    0.0494    0.1110 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -0.8260    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0324   -2.0382    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -2.4898    1.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -3.6291    2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418   -4.3545    2.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -3.8910    1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5943   -4.5814    1.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -4.1075    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410   -2.9628   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149   -2.5445   -1.0666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0998   -2.3519   -0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593   -2.7511    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106   -1.8123    1.9361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6069   -1.0008    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7902   -0.1284    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9408   -1.9000   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245   -0.0810    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101    0.9739   -0.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    2.2880    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    2.4562    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916    3.4231   -0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458    4.7828   -0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5840    3.2956   -1.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6389    1.9334   -2.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3246    3.4496   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2184    2.1490    0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    3.3655    1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.5942    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3211    2.8121   -2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5899    1.6144   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1422    1.1906   -2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -1.1105   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -3.9830    3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6544   -5.2388    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -5.4765    1.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4656   -4.6473    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5727   -0.7896    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1920    0.2990    0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162    0.7126    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812   -1.9668   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894   -2.9367    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780   -1.5137   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393    0.3357    1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    5.1125    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803    5.4917   -0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312    4.8539    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718    4.1420   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    2.0021   -3.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    1.4501   -2.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659    1.2785   -1.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  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
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28 30  2  3
 30 31  1  0
 24  8  1  0
 19  9  1  0
 19 13  2  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 29 51  1  0
 29 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 31 56  1  0
 31 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8,8-Dimethyl-10-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,8H,9H,10H-pyrano[2,3-H]chromen-9-yl 2-methylbut-2-enoic acid	Generator
Anomalin	MeSH
Anomalin, (Z,Z)-isomer	MeSH
Anomalin, (9S-(9alpha(Z),10alpha(Z)))-isomer	MeSH
Anomalin, (9alpha(e),10alpha(e))	MeSH

Chemical Formula

C₂₄H₂₆O₇

Average Molecular Weight

426.465

Monoisotopic Molecular Weight

426.167853177

IUPAC Name

12,12-dimethyl-14-[(2-methylbut-2-enoyl)oxy]-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-13-yl 2-methylbut-2-enoate

Traditional Name

12,12-dimethyl-14-[(2-methylbut-2-enoyl)oxy]-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-13-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1C(OC(=O)C(C)=CC)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12

InChI Identifier

InChI=1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3

InChI Key

PNTWXEIQXBRCPS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Fatty acid ester
Pyranone
Dicarboxylic acid or derivatives
Pyran
Fatty acyl
Benzenoid
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	4.87	ALOGPS
logP	5.24	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.21 m³·mol⁻¹	ChemAxon
Polarizability	43.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	231.381	30932474
DeepCCS	[M+Na]+	206.609	30932474

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.	8.71 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6383 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.31 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3142.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	336.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	634.2 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	687.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1245.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	646.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1623.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	230.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	233.1 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Praeruptorin B	CC=C(C)C(=O)OC1C(OC(=O)C(C)=CC)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12	4600.9	Standard polar	33892256
Praeruptorin B	CC=C(C)C(=O)OC1C(OC(=O)C(C)=CC)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12	3211.1	Standard non polar	33892256
Praeruptorin B	CC=C(C)C(=O)OC1C(OC(=O)C(C)=CC)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12	3086.0	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 - Praeruptorin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-057i-9024100000-657b7e50acf6959c5773	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Praeruptorin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

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

143336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163334

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 Praeruptorin B (HMDB0256728)

MOL for HMDB0256728 (Praeruptorin B)

3D MOL for HMDB0256728 (Praeruptorin B)

3D SDF for HMDB0256728 (Praeruptorin B)

3D-SDF for HMDB0256728 (Praeruptorin B)

PDB for HMDB0256728 (Praeruptorin B)

3D PDB for HMDB0256728 (Praeruptorin B)

SMILES for HMDB0256728 (Praeruptorin B)

INCHI for HMDB0256728 (Praeruptorin B)

Structure for HMDB0256728 (Praeruptorin B)

3D Structure for HMDB0256728 (Praeruptorin B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra