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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 04:02:15 UTC

Update Date

2021-09-26 23:00:28 UTC

HMDB ID

HMDB0249526

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one

Description

4-hydroxy-3,4,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-one belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review very few articles have been published on 4-hydroxy-3,4,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (4r,5s)-4-hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4h)-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one 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

HMDB0249526
     RDKit          3D
(4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)...
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.7913   -1.0176   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    0.2645   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316    1.4973   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    2.3723   -0.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102    1.8053   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    0.4912   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -0.4190    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0195   -1.1682    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -1.4552   -0.8351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.0874    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    1.3583   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999    1.9741   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154    1.1154    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -0.2605    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -0.8865    0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127   -2.0941   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525    2.3027   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766    3.5194   -0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839   -0.9373   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1099   -1.2505    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3120   -1.8862   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    1.6820   -0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833   -0.4866    2.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -1.8644    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1686   -1.8348    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8694   -1.0208   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    2.0942   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2694    2.9699    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455    1.4630    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8811    1.1132    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9388   -0.9200    0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520   -0.1049   -0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136   -1.1902    1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384   -2.8834   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222   -2.5995   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -1.8306   -1.5595 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
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  2  0
  6  2  1  0
 15 10  1  0
 17  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

  Mrv1533004171515392D          

 18 20  0  0  0  0            999 V2000
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    0.0660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  2  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249526

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2=C1C(C)(O)C1=C(OC=C1C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-5-4-6-10-11(8)15(3,17)12-9(2)7-18-14(12)13(10)16/h7-8,17H,4-6H2,1-3H3

> <INCHI_KEY>
VNNQNPHIASWXBS-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.96278921391029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,4,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-one

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.409631537333333

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.107663816139219

> <JCHEM_PKA_STRONGEST_BASIC>
-2.941493052679379

> <JCHEM_POLAR_SURFACE_AREA>
50.440000000000005

> <JCHEM_REFRACTIVITY>
69.43929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epicacalone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249526
     RDKit          3D
(4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)...
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.7913   -1.0176   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    0.2645   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316    1.4973   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    2.3723   -0.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102    1.8053   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    0.4912   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -0.4190    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0195   -1.1682    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -1.4552   -0.8351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.0874    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    1.3583   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999    1.9741   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154    1.1154    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -0.2605    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -0.8865    0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127   -2.0941   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525    2.3027   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766    3.5194   -0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839   -0.9373   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1099   -1.2505    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3120   -1.8862   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    1.6820   -0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833   -0.4866    2.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -1.8644    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1686   -1.8348    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8694   -1.0208   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    2.0942   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2694    2.9699    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455    1.4630    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8811    1.1132    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9388   -0.9200    0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520   -0.1049   -0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136   -1.1902    1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384   -2.8834   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222   -2.5995   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -1.8306   -1.5595 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
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  2  0
  6  2  1  0
 15 10  1  0
 17  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.914   0.123   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.934   0.123   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    6   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0249526
HETATM    1  C1  UNL     1       3.791  -1.018  -0.212  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.136   0.265  -0.399  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.632   1.497  -0.742  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.686   2.372  -0.804  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.510   1.805  -0.515  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.743   0.491  -0.253  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.688  -0.419   0.149  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.020  -1.168   1.433  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.692  -1.455  -0.835  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.682   0.087   0.136  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.923   1.358  -0.101  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.300   1.974  -0.049  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.215   1.115   0.791  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.132  -0.260   0.160  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.796  -0.887   0.389  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.713  -2.094  -0.484  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.152   2.303  -0.445  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.077   3.519  -0.677  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.784  -0.937  -0.762  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.110  -1.250   0.827  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.312  -1.886  -0.697  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.687   1.682  -0.931  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.283  -0.487   2.252  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.839  -1.864   1.168  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.169  -1.835   1.673  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.869  -1.021  -1.702  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.717   2.094  -1.062  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.269   2.970   0.418  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.246   1.463   0.674  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.881   1.113   1.843  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.939  -0.920   0.475  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.252  -0.105  -0.941  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.714  -1.190   1.448  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.038  -2.883  -0.100  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.722  -2.600  -0.564  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.489  -1.831  -1.559  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    6
CONECT    3    4   22
CONECT    4    5
CONECT    5    6    6   17
CONECT    6    7
CONECT    7    8    9   10
CONECT    8   23   24   25
CONECT    9   26
CONECT   10   11   11   15
CONECT   11   12   17
CONECT   12   13   27   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   33
CONECT   16   34   35   36
CONECT   17   18   18
END

HMDB0249526
     RDKit          3D
(4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)...
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.7913   -1.0176   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    0.2645   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316    1.4973   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    2.3723   -0.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102    1.8053   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    0.4912   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -0.4190    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0195   -1.1682    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -1.4552   -0.8351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.0874    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228    1.3583   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999    1.9741   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154    1.1154    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -0.2605    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -0.8865    0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127   -2.0941   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525    2.3027   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766    3.5194   -0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839   -0.9373   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1099   -1.2505    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3120   -1.8862   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    1.6820   -0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833   -0.4866    2.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -1.8644    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1686   -1.8348    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8694   -1.0208   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    2.0942   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2694    2.9699    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455    1.4630    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8811    1.1132    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9388   -0.9200    0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520   -0.1049   -0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136   -1.1902    1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384   -2.8834   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222   -2.5995   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -1.8306   -1.5595 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
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  2  0
  6  2  1  0
 15 10  1  0
 17  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 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

4-hydroxy-3,4,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-one

Traditional Name

epicacalone

CAS Registry Number

Not Available

SMILES

CC1CCCC2=C1C(C)(O)C1=C(OC=C1C)C2=O

InChI Identifier

InChI=1S/C15H18O3/c1-8-5-4-6-10-11(8)15(3,17)12-9(2)7-18-14(12)13(10)16/h7-8,17H,4-6H2,1-3H3

InChI Key

VNNQNPHIASWXBS-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Aryl ketone
Heteroaromatic compound
Tertiary alcohol
Furan
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.27	ALOGPS
logP	2.41	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.44 m³·mol⁻¹	ChemAxon
Polarizability	26.96 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]+	165.103	30932474
DeepCCS	[M-H]-	162.745	30932474
DeepCCS	[M-2H]-	195.63	30932474
DeepCCS	[M+Na]+	171.196	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one	CC1CCCC2=C1C(C)(O)C1=C(OC=C1C)C2=O	3126.7	Standard polar	33892256
(4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one	CC1CCCC2=C1C(C)(O)C1=C(OC=C1C)C2=O	1874.2	Standard non polar	33892256
(4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one	CC1CCCC2=C1C(C)(O)C1=C(OC=C1C)C2=O	2103.5	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 - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0mc0-7590000000-aac74c44b8d3b2f9e7d3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one 10V, Positive-QTOF	splash10-0002-0090000000-c64eaa7887ba0c9c032e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one 20V, Positive-QTOF	splash10-002b-1290000000-dd8751b5f12cf2035c53	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one 40V, Positive-QTOF	splash10-000w-9530000000-43e22f54bf41f9200922	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one 10V, Negative-QTOF	splash10-0002-0090000000-851e47b490f6973ef9e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one 20V, Negative-QTOF	splash10-0002-0190000000-6729cfbde597e7fed024	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one 40V, Negative-QTOF	splash10-0006-9270000000-f67888b49af5bf849618	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

58817801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73817341

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 (4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one (HMDB0249526)

MOL for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

3D MOL for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

3D SDF for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

3D-SDF for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

PDB for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

3D PDB for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

SMILES for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

INCHI for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

Structure for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

3D Structure for HMDB0249526 ((4R,5S)-4-Hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-9(4H)-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra