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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:20:59 UTC

Update Date

2021-09-26 23:06:53 UTC

HMDB ID

HMDB0253585

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Irofulven

Description

rac-Irofulven belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Based on a literature review very few articles have been published on rac-Irofulven. This compound has been identified in human blood as reported by (PMID: 31557052 ). Irofulven is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Irofulven 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

HMDB0253585
     RDKit          3D
Irofulven
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.9283    1.7961   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201    1.3665   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181    0.0809   -0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927   -1.0801   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751   -1.9706    0.7241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    0.1464   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -0.7681   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -2.2012   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.5202    0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -1.6046    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107   -1.4512   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808    0.8865    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1438    1.2748    1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8857    1.1342   -1.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058    1.8805    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438    3.0955    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2956    1.5670   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    2.2709   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594    1.1518   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    2.8474   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    1.7333    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595   -0.6816   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -1.5685   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -2.8906    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3765   -2.6192    0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584   -2.3892   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382   -2.8222   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3943   -1.4144    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -2.5011    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120   -2.0770   -1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.0033   -0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797    0.6202    2.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074    1.2449    0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9794    2.3120    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666    0.8084   -1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4308    3.3459   -0.0726 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
  4  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18  2  1  0
 17  6  1  0
 11  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
M  END


  Mrv1652309112114212D          

 18 20  0  0  0  0            999 V2000
   -0.1184   -0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6781   -0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202    0.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113   -0.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086   -0.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3908   -0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753   -0.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1872   -1.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -1.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -1.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633   -2.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7962   -1.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722   -1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641   -1.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0237    0.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    0.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444    1.2029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
  5 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253585

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(CO)C2=C(C)C3(CC3)C(C)(O)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3

> <INCHI_KEY>
NICJCIQSJJKZAH-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.33482426480085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-6',7'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
0.6721893616666668

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.412013440466907

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.765375591027716

> <JCHEM_PKA_STRONGEST_BASIC>
-1.743769308953517

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
70.9055

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-indene]-7'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253585
     RDKit          3D
Irofulven
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.9283    1.7961   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201    1.3665   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181    0.0809   -0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927   -1.0801   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751   -1.9706    0.7241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    0.1464   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -0.7681   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -2.2012   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.5202    0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -1.6046    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107   -1.4512   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808    0.8865    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1438    1.2748    1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8857    1.1342   -1.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058    1.8805    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438    3.0955    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2956    1.5670   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    2.2709   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594    1.1518   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    2.8474   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    1.7333    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595   -0.6816   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -1.5685   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -2.8906    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3765   -2.6192    0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584   -2.3892   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382   -2.8222   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3943   -1.4144    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -2.5011    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120   -2.0770   -1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.0033   -0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797    0.6202    2.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074    1.2449    0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9794    2.3120    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666    0.8084   -1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4308    3.3459   -0.0726 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
  4  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18  2  1  0
 17  6  1  0
 11  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.221  -0.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.266  -0.961   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.464   0.006   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.754  -0.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.243  -0.440   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.329  -1.531   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.421  -0.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.816  -1.933   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.928  -3.018   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.440  -3.414   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.038  -4.900   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.353  -2.323   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.815  -2.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.400  -3.471   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.375  -4.492   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.644   1.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.387   1.544   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.016   2.245   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6    8                                                       
CONECT    8    7    6                                                       
CONECT    9    6   10   14   15                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12    2                                                       
CONECT   14    9                                                            
CONECT   15    9                                                            
CONECT   16    5                                                            
CONECT   17    3   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0253585
HETATM    1  C1  UNL     1       3.928   1.796  -0.348  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.520   1.367  -0.225  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.118   0.081  -0.220  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.993  -1.080  -0.332  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.975  -1.971   0.724  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.642   0.146  -0.080  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.295  -0.768  -0.025  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.158  -2.201  -0.116  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.757  -0.520   0.123  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.514  -1.605   0.780  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.711  -1.451  -0.660  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.181   0.886   0.109  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.144   1.275   1.213  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.886   1.134  -1.098  1.00  0.00           O  
HETATM   15  C13 UNL     1      -1.106   1.880   0.128  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.444   3.096   0.278  1.00  0.00           O  
HETATM   17  C14 UNL     1       0.296   1.567  -0.012  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.412   2.271  -0.098  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.459   1.152  -1.086  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.010   2.847  -0.657  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.386   1.733   0.669  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.060  -0.682  -0.285  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.009  -1.569  -1.345  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.040  -2.891   0.311  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.376  -2.619   0.870  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.858  -2.389  -0.920  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.738  -2.822  -0.459  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.394  -1.414   1.426  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.960  -2.501   1.125  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.312  -2.077  -1.450  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.698  -1.003  -0.991  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.080   0.620   2.093  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.207   1.245   0.869  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.979   2.312   1.575  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.267   0.808  -1.813  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.431   3.346  -0.073  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4    6
CONECT    4    5   22   23
CONECT    5   24
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   25   26   27
CONECT    9   10   11   12
CONECT   10   11   28   29
CONECT   11   30   31
CONECT   12   13   14   15
CONECT   13   32   33   34
CONECT   14   35
CONECT   15   16   16   17
CONECT   17   18   18
CONECT   18   36
END

HMDB0253585
     RDKit          3D
Irofulven
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.9283    1.7961   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201    1.3665   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181    0.0809   -0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927   -1.0801   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751   -1.9706    0.7241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    0.1464   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -0.7681   -0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -2.2012   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.5202    0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -1.6046    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107   -1.4512   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808    0.8865    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1438    1.2748    1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8857    1.1342   -1.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058    1.8805    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438    3.0955    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2956    1.5670   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    2.2709   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594    1.1518   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    2.8474   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    1.7333    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595   -0.6816   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -1.5685   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -2.8906    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3765   -2.6192    0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584   -2.3892   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382   -2.8222   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3943   -1.4144    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -2.5011    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120   -2.0770   -1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.0033   -0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797    0.6202    2.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074    1.2449    0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9794    2.3120    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666    0.8084   -1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4308    3.3459   -0.0726 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
  4  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18  2  1  0
 17  6  1  0
 11  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.306

Monoisotopic Molecular Weight

246.12559444

IUPAC Name

6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-6',7'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one

Traditional Name

6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-indene]-7'-one

CAS Registry Number

Not Available

SMILES

CC1=C(CO)C2=C(C)C3(CC3)C(C)(O)C(=O)C2=C1

InChI Identifier

InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3

InChI Key

NICJCIQSJJKZAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Acyloin
Tertiary alcohol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	1.19	ALOGPS
logP	0.67	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.77	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.91 m³·mol⁻¹	ChemAxon
Polarizability	27.33 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]+	170.153	30932474
DeepCCS	[M-H]-	167.795	30932474
DeepCCS	[M-2H]-	200.681	30932474
DeepCCS	[M+Na]+	176.246	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.5	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	162.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Irofulven	CC1=C(CO)C2=C(C)C3(CC3)C(C)(O)C(=O)C2=C1	3408.7	Standard polar	33892256
Irofulven	CC1=C(CO)C2=C(C)C3(CC3)C(C)(O)C(=O)C2=C1	2103.2	Standard non polar	33892256
Irofulven	CC1=C(CO)C2=C(C)C3(CC3)C(C)(O)C(=O)C2=C1	2071.9	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 - Irofulven GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fai-2980000000-20a3405402d86b4239ff	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irofulven GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irofulven GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irofulven GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irofulven GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irofulven GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irofulven GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irofulven GC-MS (TBDMS_2_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 - Irofulven 10V, Positive-QTOF	splash10-004j-0090000000-ad77c046cdc2a20f2610	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irofulven 20V, Positive-QTOF	splash10-004j-1290000000-b1912b88259991685297	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irofulven 40V, Positive-QTOF	splash10-0002-3390000000-1024e76404ae81be5ea0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irofulven 10V, Negative-QTOF	splash10-0002-0490000000-7037811bc8337fc6a5fc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irofulven 20V, Negative-QTOF	splash10-0f6t-0390000000-946427c3899f153c2bd9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irofulven 40V, Negative-QTOF	splash10-00kb-0980000000-c44c35638cc5562d636f	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

3069907

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3844471

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 Irofulven (HMDB0253585)

MOL for HMDB0253585 (Irofulven)

3D MOL for HMDB0253585 (Irofulven)

3D SDF for HMDB0253585 (Irofulven)

3D-SDF for HMDB0253585 (Irofulven)

PDB for HMDB0253585 (Irofulven)

3D PDB for HMDB0253585 (Irofulven)

SMILES for HMDB0253585 (Irofulven)

INCHI for HMDB0253585 (Irofulven)

Structure for HMDB0253585 (Irofulven)

3D Structure for HMDB0253585 (Irofulven)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra