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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:14:59 UTC

Update Date

2022-03-07 02:54:27 UTC

HMDB ID

HMDB0035293

Secondary Accession Numbers

HMDB35293

Metabolite Identification

Common Name

Norambreinolide

Description

Norambreinolide belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Norambreinolide is an ambergris, dry, and labdanum tasting compound. Norambreinolide has been detected, but not quantified in, herbs and spices. This could make norambreinolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Norambreinolide.

Structure

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

HMDB0035293
     RDKit          3D
Norambreinolide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.5939   -1.8355    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.4381   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8229    0.0662   -1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    0.3596    1.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196    1.7136    0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3470    1.8343    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862    0.7086   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0234    1.2208   -1.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -0.5498   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -1.4817    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313   -1.8870    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890   -0.6858    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201   -0.5861    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3984   -0.9657   -0.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7557    0.1352   -1.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9264    0.4921   -1.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    0.8474   -1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6474    0.5891   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -1.8055   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -2.6102   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.0364    1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.1297   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996   -0.4945   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2865   -0.1481   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.2186    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3791    0.4351    1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    2.2344    2.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4357    2.2978    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437    1.9575    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2552    2.8332   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8008    1.9841   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    0.3832   -2.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380    1.7995   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -1.1152   -1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.9342    1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.3986    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020   -2.6924    0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878   -2.2327   -0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    0.4096    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758   -1.3931    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088   -0.6274    1.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    1.9172   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0573    0.3951   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    1.3931    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  9  2  1  0
 18 12  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
M  END


  Mrv0541 05061308212D          

 18 20  0  0  0  0            999 V2000
    5.5018    1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672    1.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312   -0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565    1.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 15  8  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  4  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035293

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3

> <INCHI_KEY>
IMKJGXCIJJXALX-UHFFFAOYSA-N

> <FORMULA>
C16H26O2

> <MOLECULAR_WEIGHT>
250.3764

> <EXACT_MASS>
250.193280076

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
29.231292315177278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan-2-one

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.6016039386666656

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.054801000656158

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
71.1553

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sclareolide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035293
     RDKit          3D
Norambreinolide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.5939   -1.8355    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.4381   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8229    0.0662   -1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    0.3596    1.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196    1.7136    0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3470    1.8343    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862    0.7086   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0234    1.2208   -1.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -0.5498   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -1.4817    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313   -1.8870    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890   -0.6858    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201   -0.5861    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3984   -0.9657   -0.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7557    0.1352   -1.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9264    0.4921   -1.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    0.8474   -1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6474    0.5891   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -1.8055   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -2.6102   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.0364    1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.1297   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996   -0.4945   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2865   -0.1481   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.2186    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3791    0.4351    1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    2.2344    2.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4357    2.2978    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437    1.9575    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2552    2.8332   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8008    1.9841   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    0.3832   -2.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380    1.7995   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -1.1152   -1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.9342    1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.3986    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020   -2.6924    0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878   -2.2327   -0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    0.4096    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758   -1.3931    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088   -0.6274    1.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    1.9172   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0573    0.3951   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    1.3931    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  9  2  1  0
 18 12  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.270   2.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.525   3.635   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.845  -0.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.279   3.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.923  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.490   3.388   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.651   0.818   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.384  -0.587   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.950   3.340   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.039  -0.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.301   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.034   0.674   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.614   0.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.840   2.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.573   0.722   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.222   1.983   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.305  -0.731   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.727   1.616   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5    7    8                                                       
CONECT    6    9   11                                                       
CONECT    7    5   14                                                       
CONECT    8    5   15                                                       
CONECT    9    6   16                                                       
CONECT   10   12   13                                                       
CONECT   11    6   14   15                                                  
CONECT   12   10   15   16                                                  
CONECT   13   10   17   18                                                  
CONECT   14    1    2    7   11                                             
CONECT   15    3    8   11   12                                             
CONECT   16    4    9   12   18                                             
CONECT   17   13                                                            
CONECT   18   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0035293
HETATM    1  C1  UNL     1      -2.594  -1.836   0.239  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.044  -0.438  -0.088  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.823   0.066  -1.260  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.278   0.360   1.172  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.720   1.714   1.000  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.347   1.834   0.505  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.186   0.709  -0.345  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.023   1.221  -1.796  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.585  -0.550  -0.283  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.042  -1.482   0.804  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.331  -1.887   0.248  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.189  -0.686   0.376  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.620  -0.586   1.846  1.00  0.00           C  
HETATM   14  O1  UNL     1       3.398  -0.966  -0.351  1.00  0.00           O  
HETATM   15  C14 UNL     1       3.756   0.135  -1.077  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.926   0.492  -1.429  1.00  0.00           O  
HETATM   17  C15 UNL     1       2.481   0.847  -1.378  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.647   0.589  -0.117  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.697  -1.805  -0.005  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.164  -2.610  -0.388  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.563  -2.036   1.330  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.138   1.130  -1.169  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.800  -0.495  -1.362  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.286  -0.148  -2.208  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.866  -0.219   2.016  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.379   0.435   1.308  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.817   2.234   2.001  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.436   2.298   0.347  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.344   1.958   1.393  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.255   2.833  -0.013  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.801   1.984  -2.027  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.033   0.383  -2.512  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.938   1.799  -1.838  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.410  -1.115  -1.246  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.147  -0.934   1.736  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.606  -2.399   0.906  1.00  0.00           H  
HETATM   37  H19 UNL     1       1.702  -2.692   0.904  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.188  -2.233  -0.794  1.00  0.00           H  
HETATM   39  H21 UNL     1       2.303   0.410   2.265  1.00  0.00           H  
HETATM   40  H22 UNL     1       2.176  -1.393   2.459  1.00  0.00           H  
HETATM   41  H23 UNL     1       3.709  -0.627   1.972  1.00  0.00           H  
HETATM   42  H24 UNL     1       2.755   1.917  -1.470  1.00  0.00           H  
HETATM   43  H25 UNL     1       2.057   0.395  -2.267  1.00  0.00           H  
HETATM   44  H26 UNL     1       2.015   1.393   0.595  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    9
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8    9   18
CONECT    8   31   32   33
CONECT    9   10   34
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   14   18
CONECT   13   39   40   41
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   42   43
CONECT   18   44
END

HMDB0035293
     RDKit          3D
Norambreinolide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.5939   -1.8355    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.4381   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8229    0.0662   -1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    0.3596    1.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196    1.7136    0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3470    1.8343    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862    0.7086   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0234    1.2208   -1.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -0.5498   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -1.4817    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313   -1.8870    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890   -0.6858    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201   -0.5861    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3984   -0.9657   -0.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7557    0.1352   -1.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9264    0.4921   -1.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    0.8474   -1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6474    0.5891   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -1.8055   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -2.6102   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.0364    1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.1297   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7996   -0.4945   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2865   -0.1481   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.2186    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3791    0.4351    1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    2.2344    2.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4357    2.2978    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437    1.9575    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2552    2.8332   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8008    1.9841   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    0.3832   -2.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380    1.7995   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -1.1152   -1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.9342    1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.3986    0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020   -2.6924    0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878   -2.2327   -0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    0.4096    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758   -1.3931    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088   -0.6274    1.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547    1.9172   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0573    0.3951   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    1.3931    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  9  2  1  0
 18 12  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Norambreinolide	HMDB
12-Norambreinolide	HMDB
3a,6,6,9a-Tetramethyl-decahydro-naphtho[2,1-b]furan-2-one	HMDB
3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]Furan-2(1H)-one	HMDB
Decahydrotetramethylnaphthofuranone	HMDB
FEMA 3794	HMDB
Norambreinolid	HMDB
Norambreinolide dorm	HMDB
Sclareolide	HMDB

Chemical Formula

C₁₆H₂₆O₂

Average Molecular Weight

250.3764

Monoisotopic Molecular Weight

250.193280076

IUPAC Name

3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan-2-one

Traditional Name

sclareolide

CAS Registry Number

564-20-5

SMILES

CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2

InChI Identifier

InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3

InChI Key

IMKJGXCIJJXALX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0035293)
Cell membrane (HMDB: HMDB0035293)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035293)

Source

Exogenous

Exogenous (HMDB: HMDB0035293)

Food

Food (HMDB: HMDB0035293)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0035293)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0035293)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035293)

Biological role

Nutrient (HMDB: HMDB0035293)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	122 - 125 °C	Not Available
Boiling Point	320.00 to 321.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	11.99 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.151 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0028 g/L	ALOGPS
logP	4.29	ALOGPS
logP	3.6	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.16 m³·mol⁻¹	ChemAxon
Polarizability	29.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.221	31661259
DarkChem	[M-H]-	155.096	31661259
DeepCCS	[M-2H]-	194.134	30932474
DeepCCS	[M+Na]+	169.816	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	157.0	32859911
AllCCS	[M+NH4]+	163.7	32859911
AllCCS	[M+Na]+	164.7	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	168.6	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.86 minutes	32390414
Predicted by Siyang on May 30, 2022	19.1779 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2670.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	606.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	228.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	484.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	858.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	935.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1525.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	498.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1630.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	620.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	520.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	588.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norambreinolide	CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2	2681.3	Standard polar	33892256
Norambreinolide	CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2	1915.6	Standard non polar	33892256
Norambreinolide	CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2	2083.9	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 - Norambreinolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kg9-1970000000-9bb3c07c120cdf287074	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norambreinolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norambreinolide 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 - Norambreinolide 10V, Positive-QTOF	splash10-0udi-0190000000-79e30f095ad019575c6a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 20V, Positive-QTOF	splash10-0udi-2590000000-79b3ccd278824dce9431	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 40V, Positive-QTOF	splash10-052p-9630000000-2432ca12bbc5b792f12d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 10V, Negative-QTOF	splash10-0002-0090000000-902bb4c0ff306165a7b0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 20V, Negative-QTOF	splash10-052b-0090000000-1f61b09bb60147aa9497	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 40V, Negative-QTOF	splash10-0udu-9870000000-ad9c2baccef8d25f02b1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 10V, Positive-QTOF	splash10-0udi-0190000000-3e08cef9800d1bd5a628	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 20V, Positive-QTOF	splash10-001i-9550000000-79718e042312d242ffdf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 40V, Positive-QTOF	splash10-00di-7900000000-e9f09b26ee0205d61d70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 10V, Negative-QTOF	splash10-0002-0090000000-075bfc89a13828361707	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 20V, Negative-QTOF	splash10-0002-0090000000-480f6ea2fb15cfc9441f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norambreinolide 40V, Negative-QTOF	splash10-0002-2090000000-7c02cfeca67577f56b64	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013958

KNApSAcK ID

C00048497

Chemspider ID

55077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sclareolide

METLIN ID

Not Available

PubChem Compound

61129

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1038441

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Norambreinolide (HMDB0035293)

MOL for HMDB0035293 (Norambreinolide)

3D MOL for HMDB0035293 (Norambreinolide)

3D SDF for HMDB0035293 (Norambreinolide)

3D-SDF for HMDB0035293 (Norambreinolide)

PDB for HMDB0035293 (Norambreinolide)

3D PDB for HMDB0035293 (Norambreinolide)

SMILES for HMDB0035293 (Norambreinolide)

INCHI for HMDB0035293 (Norambreinolide)

Structure for HMDB0035293 (Norambreinolide)

3D Structure for HMDB0035293 (Norambreinolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra