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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:25:46 UTC

Update Date

2021-09-26 23:05:09 UTC

HMDB ID

HMDB0252515

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fumagillol

Description

5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. 5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Fumagillol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fumagillol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252515
     RDKit          3D
Fumagillol
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.6831   -2.4450    1.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625   -1.8671    0.5305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.4989    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5765    0.1476    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935   -0.5816    1.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552    0.2719   -0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3920    0.9708   -1.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    1.3632   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569    2.4695   -1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325    2.4970   -0.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4252    0.0718   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    0.2786   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    1.1806    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    0.4231   -1.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -0.7881   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860   -1.1140    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1781   -0.0472    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191   -0.2199   -0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097    0.8755    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -1.4864   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -3.5419    1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2681   -2.0912    2.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -2.0748    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.1928    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    1.1745    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -0.3000    2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1454    0.9217   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.6996   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    0.2103   -2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8797    1.8319   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    3.1392   -2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    2.6159   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.5771   -1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.5956    1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    2.0811    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7061    1.6056    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -1.6168   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -1.4786    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -2.0313   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    0.8887    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    1.8209    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1784    0.6284    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8575    1.0505   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2425   -1.6084   -1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -1.4763   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6709   -2.3769   -0.0030 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 11  3  1  0
 15 12  1  0
 10  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

  Mrv1533004251511502D          

 20 22  0  0  0  0            999 V2000
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465    2.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608    1.5593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0825    2.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997    3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0121    3.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943    4.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    4.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7640    4.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252515

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C(O)CCC2(CO2)C1C1(C)OC1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O4/c1-10(2)5-6-12-15(3,20-12)14-13(18-4)11(17)7-8-16(14)9-19-16/h5,11-14,17H,6-9H2,1-4H3

> <INCHI_KEY>
CEVCTNCUIVEQOY-UHFFFAOYSA-N

> <FORMULA>
C16H26O4

> <MOLECULAR_WEIGHT>
282.38

> <EXACT_MASS>
282.183109317

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
31.809676511788496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.6101178576666666

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.176889355046487

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1588285961026665

> <JCHEM_POLAR_SURFACE_AREA>
54.52

> <JCHEM_REFRACTIVITY>
76.30420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252515
     RDKit          3D
Fumagillol
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.6831   -2.4450    1.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625   -1.8671    0.5305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.4989    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5765    0.1476    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935   -0.5816    1.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552    0.2719   -0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3920    0.9708   -1.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    1.3632   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569    2.4695   -1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325    2.4970   -0.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4252    0.0718   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    0.2786   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    1.1806    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    0.4231   -1.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -0.7881   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860   -1.1140    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1781   -0.0472    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191   -0.2199   -0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097    0.8755    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -1.4864   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -3.5419    1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2681   -2.0912    2.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -2.0748    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.1928    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    1.1745    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -0.3000    2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1454    0.9217   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.6996   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    0.2103   -2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8797    1.8319   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    3.1392   -2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    2.6159   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.5771   -1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.5956    1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    2.0811    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7061    1.6056    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -1.6168   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -1.4786    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -2.0313   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    0.8887    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    1.8209    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1784    0.6284    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8575    1.0505   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2425   -1.6084   -1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -1.4763   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6709   -2.3769   -0.0030 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 11  3  1  0
 15 12  1  0
 10  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.954   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.513   4.427   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.113   2.911   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.154   4.427   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.373   5.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.889   6.142   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.416   7.589   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.933   7.856   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.426   8.769   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8   10                                                       
CONECT   10    9    8                                                       
CONECT   11    8    3   12                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   12   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0252515
HETATM    1  C1  UNL     1      -1.683  -2.445   1.646  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.263  -1.867   0.530  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.195  -0.499   0.498  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.577   0.148   0.632  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.394  -0.582   1.464  1.00  0.00           O  
HETATM    6  C4  UNL     1      -4.255   0.272  -0.712  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.392   0.971  -1.737  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.067   1.363  -1.075  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.357   2.470  -1.627  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.032   2.497  -0.306  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.425   0.072  -0.640  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.035   0.279  -0.220  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.263   1.181   0.957  1.00  0.00           C  
HETATM   14  O4  UNL     1       0.961   0.423  -1.253  1.00  0.00           O  
HETATM   15  C11 UNL     1       0.984  -0.788  -0.547  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.186  -1.114   0.269  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.178  -0.047   0.417  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.419  -0.220  -0.009  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.410   0.876   0.151  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.831  -1.486  -0.641  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.749  -3.542   1.651  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.268  -2.091   2.526  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.638  -2.075   1.830  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.657  -0.193   1.438  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.494   1.175   1.046  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.175  -0.300   2.408  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.145   0.922  -0.555  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.656  -0.700  -1.081  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.126   0.210  -2.517  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.880   1.832  -2.208  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.831   3.139  -2.349  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.257   2.616  -1.529  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.426  -0.577  -1.545  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.756   0.596   1.784  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.864   2.081   0.733  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.706   1.606   1.361  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.574  -1.617  -1.202  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.806  -1.479   1.268  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.664  -2.031  -0.174  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.916   0.889   0.873  1.00  0.00           H  
HETATM   41  H21 UNL     1       4.943   1.821   0.486  1.00  0.00           H  
HETATM   42  H22 UNL     1       6.178   0.628   0.924  1.00  0.00           H  
HETATM   43  H23 UNL     1       5.857   1.050  -0.849  1.00  0.00           H  
HETATM   44  H24 UNL     1       4.242  -1.608  -1.568  1.00  0.00           H  
HETATM   45  H25 UNL     1       5.908  -1.476  -0.896  1.00  0.00           H  
HETATM   46  H26 UNL     1       4.671  -2.377  -0.003  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4   11   24
CONECT    4    5    6   25
CONECT    5   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   10   11
CONECT    9   10   31   32
CONECT   11   12   33
CONECT   12   13   14   15
CONECT   13   34   35   36
CONECT   14   15
CONECT   15   16   37
CONECT   16   17   38   39
CONECT   17   18   18   40
CONECT   18   19   20
CONECT   19   41   42   43
CONECT   20   44   45   46
END

HMDB0252515
     RDKit          3D
Fumagillol
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.6831   -2.4450    1.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625   -1.8671    0.5305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.4989    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5765    0.1476    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935   -0.5816    1.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552    0.2719   -0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3920    0.9708   -1.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    1.3632   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569    2.4695   -1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325    2.4970   -0.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4252    0.0718   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    0.2786   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    1.1806    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    0.4231   -1.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -0.7881   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860   -1.1140    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1781   -0.0472    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191   -0.2199   -0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097    0.8755    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -1.4864   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -3.5419    1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2681   -2.0912    2.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -2.0748    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.1928    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    1.1745    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -0.3000    2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1454    0.9217   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.6996   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    0.2103   -2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8797    1.8319   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    3.1392   -2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    2.6159   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.5771   -1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.5956    1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    2.0811    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7061    1.6056    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -1.6168   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -1.4786    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -2.0313   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    0.8887    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    1.8209    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1784    0.6284    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8575    1.0505   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2425   -1.6084   -1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -1.4763   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6709   -2.3769   -0.0030 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 11  3  1  0
 15 12  1  0
 10  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₆O₄

Average Molecular Weight

282.38

Monoisotopic Molecular Weight

282.183109317

IUPAC Name

5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol

Traditional Name

5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol

CAS Registry Number

Not Available

SMILES

COC1C(O)CCC2(CO2)C1C1(C)OC1CC=C(C)C

InChI Identifier

InChI=1S/C16H26O4/c1-10(2)5-6-12-15(3,20-12)14-13(18-4)11(17)7-8-16(14)9-19-16/h5,11-14,17H,6-9H2,1-4H3

InChI Key

CEVCTNCUIVEQOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.67	ALOGPS
logP	1.61	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.3 m³·mol⁻¹	ChemAxon
Polarizability	31.81 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	169.325	30932474
DeepCCS	[M-H]-	166.967	30932474
DeepCCS	[M-2H]-	199.853	30932474
DeepCCS	[M+Na]+	175.418	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	176.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fumagillol	COC1C(O)CCC2(CO2)C1C1(C)OC1CC=C(C)C	2899.1	Standard polar	33892256
Fumagillol	COC1C(O)CCC2(CO2)C1C1(C)OC1CC=C(C)C	1901.6	Standard non polar	33892256
Fumagillol	COC1C(O)CCC2(CO2)C1C1(C)OC1CC=C(C)C	2101.2	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 - Fumagillol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kur-9460000000-7599b23d1932a18bcb1d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumagillol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumagillol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumagillol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Fumagillol 10V, Positive-QTOF	splash10-001i-0090000000-80cb4a1822fd8bab460c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumagillol 20V, Positive-QTOF	splash10-001i-4690000000-b39ffa875e6266a80593	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumagillol 40V, Positive-QTOF	splash10-00lu-9320000000-e1779bc519bd48b77070	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumagillol 10V, Negative-QTOF	splash10-001i-0090000000-31dbe78e84d5eeb6827d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumagillol 20V, Negative-QTOF	splash10-003s-0690000000-7c8eff798bcf229cf548	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumagillol 40V, Negative-QTOF	splash10-0006-1900000000-dcabdddda97967235db2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

219089

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Fumagillol (HMDB0252515)

MOL for HMDB0252515 (Fumagillol)

3D MOL for HMDB0252515 (Fumagillol)

3D SDF for HMDB0252515 (Fumagillol)

3D-SDF for HMDB0252515 (Fumagillol)

PDB for HMDB0252515 (Fumagillol)

3D PDB for HMDB0252515 (Fumagillol)

SMILES for HMDB0252515 (Fumagillol)

INCHI for HMDB0252515 (Fumagillol)

Structure for HMDB0252515 (Fumagillol)

3D Structure for HMDB0252515 (Fumagillol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra