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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:57:08 UTC

Update Date

2022-03-07 02:55:03 UTC

HMDB ID

HMDB0036777

Secondary Accession Numbers

HMDB36777

Metabolite Identification

Common Name

Diosbulbin B

Description

Diosbulbin B belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Diosbulbin B has been detected, but not quantified in, root vegetables. This could make diosbulbin b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Diosbulbin B.

Structure

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

  Mrv0541 02241219542D          

 25 30  0  0  0  0            999 V2000
   -3.2010   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7271   -0.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7271   -1.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0666    1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293    0.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4617   -0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574    1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849    0.3948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    1.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010    1.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3553   -0.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0391    0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926   -0.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    0.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926    0.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1180    0.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2764    1.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299    1.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201    1.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

HMDB0036777
     RDKit          3D
Diosbulbin B
 45 50  0  0  0  0  0  0  0  0999 V2000
    0.1715   -2.2595    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.8589    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -0.8289   -0.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -0.8537   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976   -0.2093   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658    1.1306   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895    1.2708   -1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239    0.0612   -1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447   -0.8483   -1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383   -0.3772    1.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    0.0892    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522    1.5105    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510    1.7114    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    1.0525    2.1240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199    0.1558    2.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2449   -0.4445    3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    1.0227   -0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525    1.3886   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634    0.6101    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -0.7766    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -1.2737    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.4401   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9310   -0.4631   -1.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.8467   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    1.4651   -2.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -2.2823    1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -2.5504    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.9613   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    0.0496   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -1.7467   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226   -1.9632    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.9834   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    2.2169   -1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964   -1.9195   -1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    2.1515    1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.6902   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192    2.7635    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    1.4878   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643    2.4594   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    1.0080    0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    0.6355    1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794   -1.4882    0.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160   -1.1427    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1957   -2.3332    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2809   -0.7394   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 11  2  1  0
 22 17  1  0
 22  2  1  0
  9  5  2  0
 15 11  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
M  END

  Mrv0541 02241219542D          

 25 30  0  0  0  0            999 V2000
   -3.2010   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7271   -0.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7271   -1.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0666    1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293    0.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4617   -0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574    1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849    0.3948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    1.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010    1.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3553   -0.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0391    0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926   -0.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    0.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926    0.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1180    0.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2764    1.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299    1.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201    1.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036777

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC(OC11CC(OC1=O)C1C3CC(CC21)OC3=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O6/c1-18-6-13(9-2-3-22-8-9)25-19(18)7-14(24-17(19)21)15-11-4-10(5-12(15)18)23-16(11)20/h2-3,8,10-15H,4-7H2,1H3

> <INCHI_KEY>
QEANLIISUSNNDX-UHFFFAOYSA-N

> <FORMULA>
C19H20O6

> <MOLECULAR_WEIGHT>
344.3585

> <EXACT_MASS>
344.125988372

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.003923355151485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(furan-3-yl)-5-methyl-2,9,14-trioxapentacyclo[11.2.1.1⁸,¹¹.0¹,⁵.0⁶,¹²]heptadecane-10,15-dione

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.6067359776666663

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1561745720997254

> <JCHEM_POLAR_SURFACE_AREA>
74.97

> <JCHEM_REFRACTIVITY>
83.0563

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(furan-3-yl)-5-methyl-2,9,14-trioxapentacyclo[11.2.1.1⁸,¹¹.0¹,⁵.0⁶,¹²]heptadecane-10,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036777
     RDKit          3D
Diosbulbin B
 45 50  0  0  0  0  0  0  0  0999 V2000
    0.1715   -2.2595    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.8589    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -0.8289   -0.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -0.8537   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976   -0.2093   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658    1.1306   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895    1.2708   -1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239    0.0612   -1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447   -0.8483   -1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383   -0.3772    1.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    0.0892    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522    1.5105    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510    1.7114    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    1.0525    2.1240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199    0.1558    2.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2449   -0.4445    3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    1.0227   -0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525    1.3886   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634    0.6101    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -0.7766    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -1.2737    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.4401   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9310   -0.4631   -1.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.8467   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    1.4651   -2.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -2.2823    1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -2.5504    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.9613   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    0.0496   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -1.7467   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226   -1.9632    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.9834   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    2.2169   -1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964   -1.9195   -1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    2.1515    1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.6902   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192    2.7635    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    1.4878   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643    2.4594   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    1.0080    0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    0.6355    1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794   -1.4882    0.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160   -1.1427    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1957   -2.3332    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2809   -0.7394   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 11  2  1  0
 22 17  1  0
 22  2  1  0
  9  5  2  0
 15 11  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  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      -5.975  -2.507   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.091  -1.327   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.614  -1.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.614  -3.246   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.091  -3.688   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.991   2.065   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.548   0.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.729  -0.590   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.204   0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.467   1.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.467   2.507   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.385   0.737   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.089   2.213   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.975   3.393   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.663  -1.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.073   0.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.106  -1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.434  -0.885   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.434   0.590   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.106   1.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.220   1.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.811   3.098   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.516   3.688   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.549   2.655   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.024   3.098   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4                                                       
CONECT    6    7   11   22                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10   13                                                  
CONECT   12    9   13                                                       
CONECT   13   11   12   14                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16    7   15   17   20                                             
CONECT   17   16   18                                                       
CONECT   18    3   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   16   19   21   24                                             
CONECT   21   20   22                                                       
CONECT   22    6   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   20   23   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

COMPND    HMDB0036777
HETATM    1  C1  UNL     1       0.171  -2.259   0.725  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.108  -0.859   0.148  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.191  -0.829  -0.934  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.419  -0.854  -0.021  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.598  -0.209  -0.624  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.866   1.131  -0.681  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.090   1.271  -1.345  1.00  0.00           C  
HETATM    8  O1  UNL     1       5.524   0.061  -1.666  1.00  0.00           O  
HETATM    9  C8  UNL     1       4.645  -0.848  -1.244  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.038  -0.377   1.202  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.775   0.089   1.121  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.652   1.511   0.649  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.851   1.711   0.901  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.015   1.052   2.124  1.00  0.00           O  
HETATM   15  C12 UNL     1       0.020   0.156   2.383  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.245  -0.444   3.441  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.510   1.023  -0.268  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.952   1.389  -0.297  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.763   0.610   0.745  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.683  -0.777   0.103  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.276  -1.274   0.355  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.221  -0.440  -0.338  1.00  0.00           C  
HETATM   23  O5  UNL     1      -3.931  -0.463  -1.253  1.00  0.00           O  
HETATM   24  C19 UNL     1      -3.582   0.847  -1.524  1.00  0.00           C  
HETATM   25  O6  UNL     1      -3.758   1.465  -2.590  1.00  0.00           O  
HETATM   26  H1  UNL     1       1.079  -2.282   1.401  1.00  0.00           H  
HETATM   27  H2  UNL     1      -0.683  -2.550   1.328  1.00  0.00           H  
HETATM   28  H3  UNL     1       0.407  -2.961  -0.100  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.144   0.050  -1.569  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.150  -1.747  -1.549  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.623  -1.963   0.152  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.313   1.983  -0.317  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.572   2.217  -1.546  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.796  -1.920  -1.400  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.170   2.152   1.387  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.931   1.690  -0.382  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.119   2.764   0.894  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.047   1.488  -1.190  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.064   2.459  -0.167  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.790   1.008   0.720  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.306   0.635   1.734  1.00  0.00           H  
HETATM   42  H17 UNL     1      -4.379  -1.488   0.537  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.116  -1.143   1.450  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.196  -2.333   0.018  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.281  -0.739  -1.428  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   11   22
CONECT    3    4   29   30
CONECT    4    5   10   31
CONECT    5    6    9    9
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9
CONECT    9   34
CONECT   10   11
CONECT   11   12   15
CONECT   12   13   35   36
CONECT   13   14   17   37
CONECT   14   15
CONECT   15   16   16
CONECT   17   18   22   38
CONECT   18   19   24   39
CONECT   19   20   40   41
CONECT   20   21   23   42
CONECT   21   22   43   44
CONECT   22   45
CONECT   23   24
CONECT   24   25   25
END

HMDB0036777
     RDKit          3D
Diosbulbin B
 45 50  0  0  0  0  0  0  0  0999 V2000
    0.1715   -2.2595    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.8589    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -0.8289   -0.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -0.8537   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976   -0.2093   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658    1.1306   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895    1.2708   -1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239    0.0612   -1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447   -0.8483   -1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383   -0.3772    1.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    0.0892    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522    1.5105    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510    1.7114    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    1.0525    2.1240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199    0.1558    2.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2449   -0.4445    3.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097    1.0227   -0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525    1.3886   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634    0.6101    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -0.7766    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -1.2737    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.4401   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9310   -0.4631   -1.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.8467   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    1.4651   -2.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -2.2823    1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -2.5504    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.9613   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    0.0496   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -1.7467   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226   -1.9632    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.9834   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    2.2169   -1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964   -1.9195   -1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    2.1515    1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.6902   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192    2.7635    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    1.4878   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643    2.4594   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    1.0080    0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    0.6355    1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794   -1.4882    0.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160   -1.1427    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1957   -2.3332    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2809   -0.7394   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 11  2  1  0
 22 17  1  0
 22  2  1  0
  9  5  2  0
 15 11  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8b,12A:15,16-diepoxy-19-nor-13(16),14-clerodadiene-17,6b:18,2a-diolide	HMDB
Diosbulbin b	MeSH

Chemical Formula

C₁₉H₂₀O₆

Average Molecular Weight

344.3585

Monoisotopic Molecular Weight

344.125988372

IUPAC Name

3-(furan-3-yl)-5-methyl-2,9,14-trioxapentacyclo[11.2.1.1⁸,¹¹.0¹,⁵.0⁶,¹²]heptadecane-10,15-dione

Traditional Name

3-(furan-3-yl)-5-methyl-2,9,14-trioxapentacyclo[11.2.1.1⁸,¹¹.0¹,⁵.0⁶,¹²]heptadecane-10,15-dione

CAS Registry Number

20086-06-0

SMILES

CC12CC(OC11CC(OC1=O)C1C3CC(CC21)OC3=O)C1=COC=C1

InChI Identifier

InChI=1S/C19H20O6/c1-18-6-13(9-2-3-22-8-9)25-19(18)7-14(24-17(19)21)15-11-4-10(5-12(15)18)23-16(11)20/h2-3,8,10-15H,4-7H2,1H3

InChI Key

QEANLIISUSNNDX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Heteroaromatic compound
Furan
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036777)

Source

Endogenous

Endogenous (HMDB: HMDB0036777)

Plant

Plant (HMDB: HMDB0036777)

Exogenous

Food

Food (HMDB: HMDB0036777)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0036777)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036777)

Role

Biological role

Energy source (HMDB: HMDB0036777)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036777)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285 °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	0.21 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.61	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.06 m³·mol⁻¹	ChemAxon
Polarizability	34 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.101	31661259
DarkChem	[M-H]-	172.78	31661259
DeepCCS	[M-2H]-	213.192	30932474
DeepCCS	[M+Na]+	188.512	30932474
AllCCS	[M+H]+	182.1	32859911
AllCCS	[M+H-H2O]+	179.1	32859911
AllCCS	[M+NH4]+	184.8	32859911
AllCCS	[M+Na]+	185.6	32859911
AllCCS	[M-H]-	186.7	32859911
AllCCS	[M+Na-2H]-	186.2	32859911
AllCCS	[M+HCOO]-	185.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diosbulbin B	CC12CC(OC11CC(OC1=O)C1C3CC(CC21)OC3=O)C1=COC=C1	3896.6	Standard polar	33892256
Diosbulbin B	CC12CC(OC11CC(OC1=O)C1C3CC(CC21)OC3=O)C1=COC=C1	2577.9	Standard non polar	33892256
Diosbulbin B	CC12CC(OC11CC(OC1=O)C1C3CC(CC21)OC3=O)C1=COC=C1	3045.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diosbulbin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-9275000000-2ef4280e82f903237ba5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diosbulbin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diosbulbin B 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 - Diosbulbin B 10V, Positive-QTOF	splash10-0002-0039000000-a6572b8a79f2176ce9f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 20V, Positive-QTOF	splash10-0fdk-1395000000-1f676a5457ebef2fc9fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 40V, Positive-QTOF	splash10-00dj-8921000000-a6ae5cbdb602fd749d46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 10V, Negative-QTOF	splash10-0007-0059000000-b90a5764839968f560fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 20V, Negative-QTOF	splash10-014m-5089000000-32a45f1eaa1c12b859c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 40V, Negative-QTOF	splash10-014i-2290000000-c1477989aed404305441	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 10V, Positive-QTOF	splash10-0002-0009000000-76730524e176cf7619b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 20V, Positive-QTOF	splash10-0002-0059000000-5e3cd9a0855916ba5486	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 40V, Positive-QTOF	splash10-000t-4292000000-d28ccbac0adf55777beb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 10V, Negative-QTOF	splash10-0006-0009000000-48250ff27042a4c0a8fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 20V, Negative-QTOF	splash10-00kf-0019000000-5b8c40239e60b0777cdf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosbulbin B 40V, Negative-QTOF	splash10-00kb-9174000000-30066b55c0bb525a25df	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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

FDB015719

KNApSAcK ID

Not Available

Chemspider ID

21136500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15559043

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1857131

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 Diosbulbin B (HMDB0036777)

MOL for HMDB0036777 (Diosbulbin B)

3D MOL for HMDB0036777 (Diosbulbin B)

3D SDF for HMDB0036777 (Diosbulbin B)

3D-SDF for HMDB0036777 (Diosbulbin B)

PDB for HMDB0036777 (Diosbulbin B)

3D PDB for HMDB0036777 (Diosbulbin B)

SMILES for HMDB0036777 (Diosbulbin B)

INCHI for HMDB0036777 (Diosbulbin B)

Structure for HMDB0036777 (Diosbulbin B)

3D Structure for HMDB0036777 (Diosbulbin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra