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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:51:20 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036689

Secondary Accession Numbers

HMDB36689

Metabolite Identification

Common Name

Millefin

Description

Millefin belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on Millefin.

Structure

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

HMDB0036689
     RDKit          3D
Millefin
 51 52  0  0  0  0  0  0  0  0999 V2000
    6.3028    0.7843    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    0.8297   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6360    1.5382   -1.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9587    0.0523   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    0.0152   -0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -1.4025   -0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907   -2.0043    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -2.0856    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6601   -2.7208    1.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271   -1.5850   -0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.4709   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0503   -0.8306   -0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0453   -0.9682    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251   -1.3559   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941   -0.7693    1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4150    0.7742   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    1.1711   -1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832    1.0872    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    0.5607    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    0.5204    2.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0290    2.5448   -1.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547    3.0786   -1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806    4.2895   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810    1.9974   -0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338    2.1026   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7526    1.8086   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9394    0.0082   -0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514    0.6240    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5768    0.7046   -1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -1.9844   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7607   -1.4763   -1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -2.4043    1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -3.6665    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717   -3.0012    2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739   -2.0337    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409   -2.4404   -1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320   -1.2428   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -0.3128    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1882   -0.6449    0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -1.3171   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6607   -2.4021    0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102    0.6082   -2.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5929    0.6171   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    1.4899    1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -0.3254    2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    0.3263    2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772    1.4844    2.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    2.0410    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979    3.1313   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1252    1.9190    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396    1.3361   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 19  5  1  0
 24 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  END


  Mrv0541 02241218502D          

 25 26  0  0  0  0            999 V2000
   -1.4259    1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0014    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0014    1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7157   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7157    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369   -0.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416   -0.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116   -0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -1.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448    0.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443    1.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585    1.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5730    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585    0.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    1.2173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  2  0  0  0  0
  3 16  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 19  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036689

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)\C=C(C)\C(C\C=C(C)\CC2OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-10-6-7-15(23-13(4)20)11(2)9-17-18(12(3)19(22)25-17)16(8-10)24-14(5)21/h6,9,12,15-18H,7-8H2,1-5H3/b10-6+,11-9+

> <INCHI_KEY>
OHMAVTDVTQMMMR-BBYAVRKXSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.4061

> <EXACT_MASS>
350.172938564

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.844566798680525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(acetyloxy)-3,6,10-trimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.9807898959999999

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.55868800426366

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
91.5322

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(acetyloxy)-3,6,10-trimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036689
     RDKit          3D
Millefin
 51 52  0  0  0  0  0  0  0  0999 V2000
    6.3028    0.7843    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    0.8297   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6360    1.5382   -1.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9587    0.0523   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    0.0152   -0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -1.4025   -0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907   -2.0043    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -2.0856    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6601   -2.7208    1.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271   -1.5850   -0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.4709   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0503   -0.8306   -0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0453   -0.9682    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251   -1.3559   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941   -0.7693    1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4150    0.7742   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    1.1711   -1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832    1.0872    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    0.5607    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    0.5204    2.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0290    2.5448   -1.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547    3.0786   -1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806    4.2895   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810    1.9974   -0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338    2.1026   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7526    1.8086   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9394    0.0082   -0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514    0.6240    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5768    0.7046   -1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -1.9844   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7607   -1.4763   -1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -2.4043    1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -3.6665    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717   -3.0012    2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739   -2.0337    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409   -2.4404   -1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320   -1.2428   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -0.3128    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1882   -0.6449    0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -1.3171   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6607   -2.4021    0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102    0.6082   -2.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5929    0.6171   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    1.4899    1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -0.3254    2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    0.3263    2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772    1.4844    2.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    2.0410    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979    3.1313   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1252    1.9190    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396    1.3361   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 19  5  1  0
 24 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.662   2.272   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.662   0.731   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.328  -0.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.003   0.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.003   2.272   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.328   3.040   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.336  -0.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.731   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   2.272   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.336   3.040   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.654  -1.543   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.180  -1.704   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.802  -0.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.092   1.183   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.998  -0.040   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.328  -1.581   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.951  -3.040   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.310   0.011   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.003   3.040   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.336   2.270   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.670   3.040   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.336   0.728   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.334   0.731   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.670  -0.040   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.334   2.272   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    7                                                       
CONECT    5    6   10   14                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   19                                                  
CONECT   10    5    9                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    8   12   18                                                  
CONECT   14    5                                                            
CONECT   15    2   23                                                       
CONECT   16    3                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    9   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0036689
HETATM    1  C1  UNL     1       6.303   0.784   0.026  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.943   0.830  -0.570  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.636   1.538  -1.563  1.00  0.00           O  
HETATM    4  O2  UNL     1       3.959   0.052  -0.004  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.624   0.015  -0.487  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.198  -1.403  -0.854  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.391  -2.004   0.239  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.064  -2.086   0.251  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.660  -2.721   1.417  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.827  -1.585  -0.829  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.714  -0.471  -0.278  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.050  -0.831  -0.571  1.00  0.00           O  
HETATM   13  C10 UNL     1      -4.045  -0.968   0.351  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.425  -1.356  -0.094  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.794  -0.769   1.554  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.415   0.774  -1.076  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.033   1.171  -1.033  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.583   1.087   0.343  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.766   0.561   0.599  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.239   0.520   2.033  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.029   2.545  -1.378  1.00  0.00           O  
HETATM   22  C17 UNL     1      -1.255   3.079  -1.087  1.00  0.00           C  
HETATM   23  O6  UNL     1      -1.581   4.289  -1.306  1.00  0.00           O  
HETATM   24  C18 UNL     1      -2.081   1.997  -0.493  1.00  0.00           C  
HETATM   25  C19 UNL     1      -3.534   2.103  -0.865  1.00  0.00           C  
HETATM   26  H1  UNL     1       6.753   1.809  -0.098  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.939   0.008  -0.431  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.251   0.624   1.125  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.577   0.705  -1.354  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.165  -1.984  -0.911  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.761  -1.476  -1.848  1.00  0.00           H  
HETATM   32  H7  UNL     1       1.975  -2.404   1.094  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.125  -3.667   1.057  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.072  -3.001   2.215  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.374  -2.034   1.879  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.441  -2.440  -1.219  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.232  -1.243  -1.686  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.570  -0.313   0.799  1.00  0.00           H  
HETATM   39  H14 UNL     1      -6.188  -0.645   0.285  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.479  -1.317  -1.200  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.661  -2.402   0.192  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.710   0.608  -2.109  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.593   0.617  -1.781  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.049   1.490   1.154  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.711  -0.325   2.498  1.00  0.00           H  
HETATM   46  H21 UNL     1       3.323   0.326   2.014  1.00  0.00           H  
HETATM   47  H22 UNL     1       2.077   1.484   2.526  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.935   2.041   0.603  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.798   3.131  -1.173  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.125   1.919   0.078  1.00  0.00           H  
HETATM   51  H26 UNL     1      -3.840   1.336  -1.606  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   19   29
CONECT    6    7   30   31
CONECT    7    8    8   32
CONECT    8    9   10
CONECT    9   33   34   35
CONECT   10   11   36   37
CONECT   11   12   16   38
CONECT   12   13
CONECT   13   14   15   15
CONECT   14   39   40   41
CONECT   16   17   24   42
CONECT   17   18   21   43
CONECT   18   19   19   44
CONECT   19   20
CONECT   20   45   46   47
CONECT   21   22
CONECT   22   23   23   24
CONECT   24   25   48
CONECT   25   49   50   51
END

HMDB0036689
     RDKit          3D
Millefin
 51 52  0  0  0  0  0  0  0  0999 V2000
    6.3028    0.7843    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    0.8297   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6360    1.5382   -1.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9587    0.0523   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    0.0152   -0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -1.4025   -0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907   -2.0043    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -2.0856    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6601   -2.7208    1.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271   -1.5850   -0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.4709   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0503   -0.8306   -0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0453   -0.9682    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251   -1.3559   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941   -0.7693    1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4150    0.7742   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    1.1711   -1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832    1.0872    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657    0.5607    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    0.5204    2.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0290    2.5448   -1.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547    3.0786   -1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806    4.2895   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810    1.9974   -0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338    2.1026   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7526    1.8086   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9394    0.0082   -0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514    0.6240    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5768    0.7046   -1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -1.9844   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7607   -1.4763   -1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -2.4043    1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -3.6665    1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717   -3.0012    2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739   -2.0337    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409   -2.4404   -1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320   -1.2428   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -0.3128    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1882   -0.6449    0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -1.3171   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6607   -2.4021    0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102    0.6082   -2.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5929    0.6171   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    1.4899    1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -0.3254    2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    0.3263    2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772    1.4844    2.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    2.0410    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979    3.1313   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1252    1.9190    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396    1.3361   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 19  5  1  0
 24 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-(Acetyloxy)-3,6,10-trimethyl-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl acetic acid	HMDB

Chemical Formula

C₁₉H₂₆O₆

Average Molecular Weight

350.4061

Monoisotopic Molecular Weight

350.172938564

IUPAC Name

4-(acetyloxy)-3,6,10-trimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

Traditional Name

4-(acetyloxy)-3,6,10-trimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

CAS Registry Number

39262-27-6

SMILES

CC1C2C(OC1=O)\C=C(C)\C(C\C=C(C)\CC2OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C19H26O6/c1-10-6-7-15(23-13(4)20)11(2)9-17-18(12(3)19(22)25-17)16(8-10)24-14(5)21/h6,9,12,15-18H,7-8H2,1-5H3/b10-6+,11-9+

InChI Key

OHMAVTDVTQMMMR-BBYAVRKXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036689)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036689)

Source

Endogenous

Endogenous (HMDB: HMDB0036689)

Plant

Plant (HMDB: HMDB0036689)

Animal

Animal (HMDB: HMDB0036689)

Exogenous

Food

Food (HMDB: HMDB0036689)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036689)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036689)

Cellular process

Cell signaling (HMDB: HMDB0036689)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036689)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036689)

Nutrient

Nutrient (HMDB: HMDB0036689)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036689)

Emulsifier (HMDB: HMDB0036689)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	209 - 210 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15.68 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	0.065 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.98	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.53 m³·mol⁻¹	ChemAxon
Polarizability	36.84 Å³	ChemAxon
Number of Rings	2	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]+	182.665	31661259
DarkChem	[M-H]-	179.314	31661259
DeepCCS	[M+H]+	183.007	30932474
DeepCCS	[M-H]-	180.649	30932474
DeepCCS	[M-2H]-	214.858	30932474
DeepCCS	[M+Na]+	190.085	30932474
AllCCS	[M+H]+	185.6	32859911
AllCCS	[M+H-H2O]+	182.7	32859911
AllCCS	[M+NH4]+	188.2	32859911
AllCCS	[M+Na]+	189.0	32859911
AllCCS	[M-H]-	187.5	32859911
AllCCS	[M+Na-2H]-	187.9	32859911
AllCCS	[M+HCOO]-	188.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Millefin	CC1C2C(OC1=O)\C=C(C)\C(C\C=C(C)\CC2OC(C)=O)OC(C)=O	3372.6	Standard polar	33892256
Millefin	CC1C2C(OC1=O)\C=C(C)\C(C\C=C(C)\CC2OC(C)=O)OC(C)=O	2348.0	Standard non polar	33892256
Millefin	CC1C2C(OC1=O)\C=C(C)\C(C\C=C(C)\CC2OC(C)=O)OC(C)=O	2416.0	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 - Millefin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9071000000-2d81073fd33e45c69675	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Millefin 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 - Millefin 10V, Positive-QTOF	splash10-0zfu-0059000000-684eb1cd405f0501e6be	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 20V, Positive-QTOF	splash10-05no-2092000000-49f1f30107d2a5ba10f3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 40V, Positive-QTOF	splash10-0gb9-9460000000-04e5d862d86a411b5b91	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 10V, Negative-QTOF	splash10-0a4j-0029000000-2499d7c09ef73fa8e6c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 20V, Negative-QTOF	splash10-0a4i-3079000000-cabc338d263d13f77f31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 40V, Negative-QTOF	splash10-0k9l-9281000000-365b36d23147562fc721	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 10V, Positive-QTOF	splash10-000x-0090000000-b5c1a9e6e991867cc16e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 20V, Positive-QTOF	splash10-003s-0090000000-8160e6e7436496f70a92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 40V, Positive-QTOF	splash10-004i-1090000000-0fbd709be7add85fcaa1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 10V, Negative-QTOF	splash10-0002-0096000000-5c79319a6e925ab232ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 20V, Negative-QTOF	splash10-0a4l-9031000000-630d1c8ba3621eff899b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Millefin 40V, Negative-QTOF	splash10-0a4l-9000000000-560c36bc1aba47465cbb	2021-09-22	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

FDB015619

KNApSAcK ID

C00011756

Chemspider ID

4478045

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319830

PDB ID

Not Available

ChEBI ID

175476

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856471

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 Millefin (HMDB0036689)

MOL for HMDB0036689 (Millefin)

3D MOL for HMDB0036689 (Millefin)

3D SDF for HMDB0036689 (Millefin)

3D-SDF for HMDB0036689 (Millefin)

PDB for HMDB0036689 (Millefin)

3D PDB for HMDB0036689 (Millefin)

SMILES for HMDB0036689 (Millefin)

INCHI for HMDB0036689 (Millefin)

Structure for HMDB0036689 (Millefin)

3D Structure for HMDB0036689 (Millefin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra