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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:12:40 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036147

Secondary Accession Numbers

HMDB36147

Metabolite Identification

Common Name

Furanojaponin

Description

Furanojaponin belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on Furanojaponin.

Structure

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

HMDB0036147
     RDKit          3D
Furanojaponin
 51 53  0  0  0  0  0  0  0  0999 V2000
    7.0204    1.2249    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5525    1.3056    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.4451    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5486   -0.6319   -0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994    0.5935    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169    1.5192    1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -0.2640   -0.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.1662   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.0515   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442    0.3205   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    1.8460   -1.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -0.3634   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990   -1.4660   -1.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    0.6402   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -0.1653    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -0.0062    0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7921    1.0774    0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724   -1.0293    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -1.7536    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -1.2750    1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -1.8016    1.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -0.8552    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -1.3882    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4161    2.2561    1.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2722    0.7131    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4739    0.6607    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089    2.1023    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254   -1.3195   -0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1935   -0.2374   -0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975   -1.2043    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9040    0.7261    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991   -0.8581   -2.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006    0.8854   -2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652    0.0528   -2.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.2529   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099    2.2348   -2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    2.1583   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349   -1.7880   -2.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389   -2.3480   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3722   -1.1147   -1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031    1.3883    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307    1.0670   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580    0.8747    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5644    1.9865    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5086    1.3192   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2695   -1.1839    2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -2.8524    0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -1.7688    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718    0.0498    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8568   -1.7446    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -2.1663   -0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  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  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23  8  1  0
 22 12  1  0
 20 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
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 14 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

  Mrv0541 05061308542D          

 23 25  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  1  0  0  0  0
 13 11  2  0  0  0  0
 14  4  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 18 17  2  0  0  0  0
 19 12  1  0  0  0  0
 20  5  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 19  2  0  0  0  0
 22 11  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036147

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(/C)C(=O)OC1CC(C)C2(C)CC3=C(CC2C1)OC=C3C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-6-12(2)19(21)23-16-7-14(4)20(5)10-17-13(3)11-22-18(17)9-15(20)8-16/h6,11,14-16H,7-10H2,1-5H3/b12-6+

> <INCHI_KEY>
DDJITDJHDCLHOK-WUXMJOGZSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
37.64041688758531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-7-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
5.255995139333333

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4769170809076488

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
92.14629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-7-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036147
     RDKit          3D
Furanojaponin
 51 53  0  0  0  0  0  0  0  0999 V2000
    7.0204    1.2249    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5525    1.3056    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.4451    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5486   -0.6319   -0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994    0.5935    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169    1.5192    1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -0.2640   -0.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.1662   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.0515   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442    0.3205   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    1.8460   -1.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -0.3634   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990   -1.4660   -1.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    0.6402   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -0.1653    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -0.0062    0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7921    1.0774    0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724   -1.0293    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -1.7536    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -1.2750    1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -1.8016    1.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -0.8552    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -1.3882    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4161    2.2561    1.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2722    0.7131    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4739    0.6607    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089    2.1023    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254   -1.3195   -0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1935   -0.2374   -0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975   -1.2043    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9040    0.7261    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991   -0.8581   -2.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006    0.8854   -2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652    0.0528   -2.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.2529   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099    2.2348   -2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    2.1583   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349   -1.7880   -2.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389   -2.3480   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3722   -1.1147   -1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031    1.3883    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307    1.0670   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580    0.8747    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5644    1.9865    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5086    1.3192   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2695   -1.1839    2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -2.8524    0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -1.7688    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718    0.0498    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8568   -1.7446    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -2.1663   -0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  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  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23  8  1  0
 22 12  1  0
 20 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  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      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5   20                                                            
CONECT    6    1   12                                                       
CONECT    7   14   16                                                       
CONECT    8   15   16                                                       
CONECT    9   15   18                                                       
CONECT   10   17   20                                                       
CONECT   11   13   22                                                       
CONECT   12    2    6   19                                                  
CONECT   13    3   11   17                                                  
CONECT   14    4    7   20                                                  
CONECT   15    8    9   20                                                  
CONECT   16    7    8   23                                                  
CONECT   17   10   13   18                                                  
CONECT   18    9   17   22                                                  
CONECT   19   12   21   23                                                  
CONECT   20    5   10   14   15                                             
CONECT   21   19                                                            
CONECT   22   11   18                                                       
CONECT   23   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0036147
HETATM    1  C1  UNL     1       7.020   1.225   1.417  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.552   1.306   1.312  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.851   0.445   0.602  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.549  -0.632  -0.109  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.399   0.593   0.549  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.817   1.519   1.162  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.589  -0.264  -0.171  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.215  -0.166  -0.252  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.716   0.052  -1.656  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.744   0.321  -1.720  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.925   1.846  -1.677  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.603  -0.363  -0.740  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.399  -1.466  -1.442  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.669   0.640  -0.261  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.588  -0.165   0.609  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.929  -0.006   0.895  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.792   1.077   0.356  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.272  -1.029   1.753  1.00  0.00           C  
HETATM   19  O3  UNL     1      -4.207  -1.754   1.966  1.00  0.00           O  
HETATM   20  C17 UNL     1      -3.175  -1.275   1.303  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.786  -1.802   1.273  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.939  -0.855   0.501  1.00  0.00           C  
HETATM   23  C20 UNL     1       0.468  -1.388   0.250  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.416   2.256   1.496  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.272   0.713   2.370  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.474   0.661   0.599  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.009   2.102   1.834  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.825  -1.320  -0.597  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.194  -0.237  -0.936  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.198  -1.204   0.611  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.904   0.726   0.367  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.999  -0.858  -2.240  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.301   0.885  -2.098  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.065   0.053  -2.772  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.723   2.253  -0.690  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.110   2.235  -2.356  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.868   2.158  -2.144  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.835  -1.788  -2.362  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.539  -2.348  -0.825  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.372  -1.115  -1.790  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.203   1.388   0.415  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.231   1.067  -1.089  1.00  0.00           H  
HETATM   43  H20 UNL     1      -6.858   0.875   0.485  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.564   1.986   0.986  1.00  0.00           H  
HETATM   45  H22 UNL     1      -5.509   1.319  -0.689  1.00  0.00           H  
HETATM   46  H23 UNL     1      -6.269  -1.184   2.166  1.00  0.00           H  
HETATM   47  H24 UNL     1      -1.720  -2.852   0.973  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.431  -1.769   2.344  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.772   0.050   1.159  1.00  0.00           H  
HETATM   50  H27 UNL     1       0.857  -1.745   1.222  1.00  0.00           H  
HETATM   51  H28 UNL     1       0.472  -2.166  -0.530  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   27
CONECT    3    4    5
CONECT    4   28   29   30
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   23   31
CONECT    9   10   32   33
CONECT   10   11   12   34
CONECT   11   35   36   37
CONECT   12   13   14   22
CONECT   13   38   39   40
CONECT   14   15   41   42
CONECT   15   16   20   20
CONECT   16   17   18   18
CONECT   17   43   44   45
CONECT   18   19   46
CONECT   19   20
CONECT   20   21
CONECT   21   22   47   48
CONECT   22   23   49
CONECT   23   50   51
END

HMDB0036147
     RDKit          3D
Furanojaponin
 51 53  0  0  0  0  0  0  0  0999 V2000
    7.0204    1.2249    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5525    1.3056    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.4451    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5486   -0.6319   -0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994    0.5935    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169    1.5192    1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -0.2640   -0.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.1662   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.0515   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442    0.3205   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    1.8460   -1.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -0.3634   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990   -1.4660   -1.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    0.6402   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -0.1653    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -0.0062    0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7921    1.0774    0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724   -1.0293    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -1.7536    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -1.2750    1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -1.8016    1.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -0.8552    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4680   -1.3882    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4161    2.2561    1.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2722    0.7131    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4739    0.6607    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089    2.1023    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254   -1.3195   -0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1935   -0.2374   -0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975   -1.2043    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9040    0.7261    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991   -0.8581   -2.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006    0.8854   -2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652    0.0528   -2.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.2529   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099    2.2348   -2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    2.1583   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349   -1.7880   -2.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389   -2.3480   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3722   -1.1147   -1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031    1.3883    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307    1.0670   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580    0.8747    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5644    1.9865    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5086    1.3192   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2695   -1.1839    2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -2.8524    0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -1.7688    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718    0.0498    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8568   -1.7446    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -2.1663   -0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  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  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23  8  1  0
 22 12  1  0
 20 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4a,5-Trimethyl-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-7-yl (2E)-2-methylbut-2-enoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-7-yl (2E)-2-methylbut-2-enoate

Traditional Name

3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-7-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

34335-98-3

SMILES

C\C=C(/C)C(=O)OC1CC(C)C2(C)CC3=C(CC2C1)OC=C3C

InChI Identifier

InChI=1S/C20H28O3/c1-6-12(2)19(21)23-16-7-14(4)20(5)10-17-13(3)11-22-18(17)9-15(20)8-16/h6,11,14-16H,7-10H2,1-5H3/b12-6+

InChI Key

DDJITDJHDCLHOK-WUXMJOGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Fatty acid ester
Fatty acyl
Furan
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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: HMDB0036147)

Source

Endogenous

Endogenous (HMDB: HMDB0036147)

Plant

Plant (HMDB: HMDB0036147)

Animal

Animal (HMDB: HMDB0036147)

Exogenous

Food

Food (HMDB: HMDB0036147)

Vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0036147)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036147)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036147)

Lipid metabolism pathway (HMDB: HMDB0036147)

Cellular process

Cell signaling (HMDB: HMDB0036147)

Biochemical process

Lipid transport (HMDB: HMDB0036147)

Role

Biological role

Energy source (HMDB: HMDB0036147)

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	0.025 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0065 g/L	ALOGPS
logP	5.02	ALOGPS
logP	5.26	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.15 m³·mol⁻¹	ChemAxon
Polarizability	37.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.495	31661259
DarkChem	[M-H]-	173.182	31661259
DeepCCS	[M+H]+	177.945	30932474
DeepCCS	[M-H]-	175.587	30932474
DeepCCS	[M-2H]-	209.687	30932474
DeepCCS	[M+Na]+	184.972	30932474
AllCCS	[M+H]+	179.8	32859911
AllCCS	[M+H-H2O]+	176.8	32859911
AllCCS	[M+NH4]+	182.5	32859911
AllCCS	[M+Na]+	183.3	32859911
AllCCS	[M-H]-	186.3	32859911
AllCCS	[M+Na-2H]-	186.4	32859911
AllCCS	[M+HCOO]-	186.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Furanojaponin	C\C=C(/C)C(=O)OC1CC(C)C2(C)CC3=C(CC2C1)OC=C3C	3103.2	Standard polar	33892256
Furanojaponin	C\C=C(/C)C(=O)OC1CC(C)C2(C)CC3=C(CC2C1)OC=C3C	2237.9	Standard non polar	33892256
Furanojaponin	C\C=C(/C)C(=O)OC1CC(C)C2(C)CC3=C(CC2C1)OC=C3C	2358.0	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 - Furanojaponin GC-MS (Non-derivatized) - 70eV, Positive	splash10-053i-4911000000-1e6c57e1825ab304a4b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furanojaponin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furanojaponin 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 - Furanojaponin 10V, Positive-QTOF	splash10-014i-4159000000-64d49d3ff0bc594942cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 20V, Positive-QTOF	splash10-067i-9351000000-9b961376b72ede30801f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 40V, Positive-QTOF	splash10-0f89-9200000000-4f6fe44eefc351f2fbb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 10V, Negative-QTOF	splash10-014i-1029000000-24ba7215de5ef8968ad9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 20V, Negative-QTOF	splash10-0159-9087000000-b0ea859edd98a719908c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 40V, Negative-QTOF	splash10-0zgj-8390000000-f132c3a6942bd8aa6b7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 10V, Positive-QTOF	splash10-00kr-0091000000-45751ff543da86e979a2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 20V, Positive-QTOF	splash10-02t9-2490000000-19afb4a241fb41157cc3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 40V, Positive-QTOF	splash10-0cdj-4940000000-b076d060fc260bf4b69a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 10V, Negative-QTOF	splash10-001j-8092000000-f009227d523375e0c67f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 20V, Negative-QTOF	splash10-0002-9000000000-86a2ef610e54952992c9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furanojaponin 40V, Negative-QTOF	splash10-0gb9-5090000000-5722a034bcb9587c1ed6	2021-09-25	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

FDB014998

KNApSAcK ID

C00017364

Chemspider ID

35014103

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751918

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853751

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Furanojaponin (HMDB0036147)

MOL for HMDB0036147 (Furanojaponin)

3D MOL for HMDB0036147 (Furanojaponin)

3D SDF for HMDB0036147 (Furanojaponin)

3D-SDF for HMDB0036147 (Furanojaponin)

PDB for HMDB0036147 (Furanojaponin)

3D PDB for HMDB0036147 (Furanojaponin)

SMILES for HMDB0036147 (Furanojaponin)

INCHI for HMDB0036147 (Furanojaponin)

Structure for HMDB0036147 (Furanojaponin)

3D Structure for HMDB0036147 (Furanojaponin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra