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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:29:55 UTC

Update Date

2022-03-07 02:55:40 UTC

HMDB ID

HMDB0038219

Secondary Accession Numbers

HMDB38219

Metabolite Identification

Common Name

Rosmadial

Description

Rosmadial belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Rosmadial is found, on average, in the highest concentration within rosemaries (Rosmarinus officinalis). Rosmadial has also been detected, but not quantified in, several different foods, such as herbs and spices, pepper (spice), star anises (Illicium verum), cumins (Cuminum cyminum), and sweet bays (Laurus nobilis). This could make rosmadial a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Rosmadial.

Structure

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

HMDB0038219
     RDKit          3D
Rosmadial
 49 51  0  0  0  0  0  0  0  0999 V2000
    4.9234    0.1386   -1.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478    0.5694   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -0.2110    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    0.3510    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311   -0.3455   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790   -0.5846   -0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662   -1.3531   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -1.7594   -2.6734 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3376   -0.1207    0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0814    0.5697    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    0.8051    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793    1.5163    2.1554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    0.9449    2.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    0.5013    2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183    0.6243    3.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833   -0.1357    0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5860   -1.5107    1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -1.9458    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4200   -1.0933   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    0.3674   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    0.6470    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    1.1460   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9081    0.7998    0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673    1.1890   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    1.1233   -2.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2731    0.7008   -2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    0.4265   -1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329   -0.9597   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611    1.6363   -0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094   -0.5483    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0638    0.4462    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -1.1124    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -0.7176   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -1.6188   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1448    1.7401    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -1.7801    2.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7591   -2.2165    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -2.1354    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -2.9781    0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -1.3063   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378   -1.2768   -0.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2428    0.7532    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -0.1938    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8931    1.5732    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0437    1.2078   -1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    2.1741   -1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8562    0.5964   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342    1.7958    0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.5602   -1.0609 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 11  4  1  0
 23 16  1  0
 16  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  7 34  1  0
 12 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
M  END


  Mrv0541 05061310182D          

 25 27  0  0  0  0            999 V2000
    6.8985   -1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6597    0.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9317   -1.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4234   -2.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -0.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718   -0.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995   -0.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -0.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -2.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -0.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5590   -0.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4342   -1.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583   -1.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652   -1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    1.0048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -3.0706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7978   -2.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7755   -3.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -2.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19  6  1  0  0  0  0
 19 14  1  0  0  0  0
 20  7  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21  9  2  0  0  0  0
 22 10  2  0  0  0  0
 23 16  1  0  0  0  0
 24 18  2  0  0  0  0
 25 17  1  0  0  0  0
 25 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038219

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-11(2)13-8-12(9-21)15-17(16(13)23)25-18(24)20(15)7-5-6-19(3,4)14(20)10-22/h8-11,14,23H,5-7H2,1-4H3

> <INCHI_KEY>
JBWRHBJFAVSAMJ-UHFFFAOYSA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.4016

> <EXACT_MASS>
344.162373878

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.725717977925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3',3'-dimethyl-2-oxo-6-(propan-2-yl)-2H-spiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
4.365722117666666

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.223501409945946

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.500204506862795

> <JCHEM_PKA_STRONGEST_BASIC>
-5.571579231100668

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
94.02449999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-6-isopropyl-3',3'-dimethyl-2-oxospiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038219
     RDKit          3D
Rosmadial
 49 51  0  0  0  0  0  0  0  0999 V2000
    4.9234    0.1386   -1.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478    0.5694   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -0.2110    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    0.3510    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311   -0.3455   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790   -0.5846   -0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662   -1.3531   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -1.7594   -2.6734 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3376   -0.1207    0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0814    0.5697    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    0.8051    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793    1.5163    2.1554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    0.9449    2.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    0.5013    2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183    0.6243    3.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833   -0.1357    0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5860   -1.5107    1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -1.9458    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4200   -1.0933   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    0.3674   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    0.6470    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    1.1460   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9081    0.7998    0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673    1.1890   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    1.1233   -2.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2731    0.7008   -2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    0.4265   -1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329   -0.9597   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611    1.6363   -0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094   -0.5483    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0638    0.4462    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -1.1124    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -0.7176   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -1.6188   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1448    1.7401    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -1.7801    2.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7591   -2.2165    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -2.1354    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -2.9781    0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -1.3063   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378   -1.2768   -0.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2428    0.7532    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -0.1938    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8931    1.5732    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0437    1.2078   -1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    2.1741   -1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8562    0.5964   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342    1.7958    0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.5602   -1.0609 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 11  4  1  0
 23 16  1  0
 16  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  7 34  1  0
 12 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  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      12.877  -2.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.431   0.018   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.739  -2.324   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.657  -4.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.672  -0.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.307  -1.116   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.972  -1.227   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.395  -0.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.894   0.432   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.480  -5.018   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.895  -1.426   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.876  -0.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.377  -1.683   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.544  -3.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.340  -2.198   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.841  -3.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.322  -3.384   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.006  -4.302   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.243  -2.654   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.908  -2.765   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.431   1.876   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.115  -5.732   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.823  -4.313   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.181  -5.603   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.497  -4.685   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    6    7                                                       
CONECT    6    5   19                                                       
CONECT    7    5   20                                                       
CONECT    8   12   13                                                       
CONECT    9   12   21                                                       
CONECT   10   14   22                                                       
CONECT   11    1    2   13                                                  
CONECT   12    8    9   15                                                  
CONECT   13    8   11   16                                                  
CONECT   14   10   19   20                                                  
CONECT   15   12   17   20                                                  
CONECT   16   13   17   23                                                  
CONECT   17   15   16   25                                                  
CONECT   18   20   24   25                                                  
CONECT   19    3    4    6   14                                             
CONECT   20    7   14   15   18                                             
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   16                                                            
CONECT   24   18                                                            
CONECT   25   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0038219
HETATM    1  C1  UNL     1       4.923   0.139  -1.567  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.548   0.569  -0.163  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.314  -0.211   0.871  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.091   0.351   0.088  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.331  -0.346  -0.822  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.979  -0.585  -0.633  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.266  -1.353  -1.607  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.820  -1.759  -2.673  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.338  -0.121   0.497  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.081   0.570   1.412  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.450   0.805   1.207  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.179   1.516   2.155  1.00  0.00           O  
HETATM   13  O3  UNL     1       0.290   0.945   2.490  1.00  0.00           O  
HETATM   14  C11 UNL     1      -0.968   0.501   2.298  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.918   0.624   3.166  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.083  -0.136   0.962  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.586  -1.511   1.155  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.829  -1.946   0.508  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.420  -1.093  -0.544  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.272   0.367  -0.200  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.194   0.647   1.014  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.922   1.146  -1.321  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.908   0.800   0.131  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.167   1.189  -1.090  1.00  0.00           C  
HETATM   25  O5  UNL     1      -1.648   1.123  -2.197  1.00  0.00           O  
HETATM   26  H1  UNL     1       4.273   0.701  -2.258  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.985   0.426  -1.720  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.833  -0.960  -1.646  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.761   1.636  -0.034  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.609  -0.548   1.647  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.064   0.446   1.341  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.810  -1.112   0.409  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.789  -0.718  -1.705  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.759  -1.619  -1.482  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.145   1.740   2.103  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.655  -1.780   2.257  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.759  -2.216   0.830  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.633  -2.135   1.285  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.717  -2.978   0.052  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.115  -1.306  -1.586  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.538  -1.277  -0.558  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.243   0.753   0.663  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.071  -0.194   1.714  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.893   1.573   1.536  1.00  0.00           H  
HETATM   45  H20 UNL     1      -5.044   1.208  -1.153  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.511   2.174  -1.401  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.856   0.596  -2.294  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.034   1.796   0.682  1.00  0.00           H  
HETATM   49  H24 UNL     1      -0.137   1.560  -1.061  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   29
CONECT    3   30   31   32
CONECT    4    5    5   11
CONECT    5    6   33
CONECT    6    7    9    9
CONECT    7    8    8   34
CONECT    9   10   16
CONECT   10   11   11   13
CONECT   11   12
CONECT   12   35
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   23
CONECT   17   18   36   37
CONECT   18   19   38   39
CONECT   19   20   40   41
CONECT   20   21   22   23
CONECT   21   42   43   44
CONECT   22   45   46   47
CONECT   23   24   48
CONECT   24   25   25   49
END

HMDB0038219
     RDKit          3D
Rosmadial
 49 51  0  0  0  0  0  0  0  0999 V2000
    4.9234    0.1386   -1.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478    0.5694   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -0.2110    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    0.3510    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311   -0.3455   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790   -0.5846   -0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662   -1.3531   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -1.7594   -2.6734 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3376   -0.1207    0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0814    0.5697    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    0.8051    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793    1.5163    2.1554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    0.9449    2.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    0.5013    2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183    0.6243    3.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833   -0.1357    0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5860   -1.5107    1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -1.9458    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4200   -1.0933   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    0.3674   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    0.6470    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    1.1460   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9081    0.7998    0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673    1.1890   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    1.1233   -2.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2731    0.7008   -2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    0.4265   -1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329   -0.9597   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611    1.6363   -0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094   -0.5483    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0638    0.4462    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -1.1124    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -0.7176   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -1.6188   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1448    1.7401    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -1.7801    2.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7591   -2.2165    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -2.1354    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -2.9781    0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -1.3063   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378   -1.2768   -0.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2428    0.7532    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -0.1938    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8931    1.5732    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0437    1.2078   -1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    2.1741   -1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8562    0.5964   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342    1.7958    0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.5602   -1.0609 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 11  4  1  0
 23 16  1  0
 16  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  7 34  1  0
 12 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Rosmadial	HMDB

Chemical Formula

C₂₀H₂₄O₅

Average Molecular Weight

344.4016

Monoisotopic Molecular Weight

344.162373878

IUPAC Name

7-hydroxy-3',3'-dimethyl-2-oxo-6-(propan-2-yl)-2H-spiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde

Traditional Name

7-hydroxy-6-isopropyl-3',3'-dimethyl-2-oxospiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde

CAS Registry Number

85514-31-4

SMILES

CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2

InChI Identifier

InChI=1S/C20H24O5/c1-11(2)13-8-12(9-21)15-17(16(13)23)25-18(24)20(15)7-5-6-19(3,4)14(20)10-22/h8-11,14,23H,5-7H2,1-4H3

InChI Key

JBWRHBJFAVSAMJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Coumaran
Aryl-aldehyde
Benzenoid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038219)

Cellular substructure

Extracellular (HMDB: HMDB0038219)
Membrane (HMDB: HMDB0038219)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038219)

Source

Endogenous

Endogenous (HMDB: HMDB0038219)

Plant

Plant (HMDB: HMDB0038219)

Exogenous

Food

Food (HMDB: HMDB0038219)

Herb and spice

Spice

Herb

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0038219)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	225 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	47.08 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.76	ALOGPS
logP	4.37	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.02 m³·mol⁻¹	ChemAxon
Polarizability	36.73 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
DarkChem	[M+H]+	181.122	31661259
DarkChem	[M-H]-	179.331	31661259
DeepCCS	[M+H]+	189.312	30932474
DeepCCS	[M-H]-	186.954	30932474
DeepCCS	[M-2H]-	221.079	30932474
DeepCCS	[M+Na]+	196.306	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	177.1	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	188.5	32859911
AllCCS	[M+Na-2H]-	188.6	32859911
AllCCS	[M+HCOO]-	189.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rosmadial	CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2	3628.2	Standard polar	33892256
Rosmadial	CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2	2517.8	Standard non polar	33892256
Rosmadial	CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2	2603.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rosmadial,1TMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C)OC(=O)C21CCCC(C)(C)C1C=O	2732.0	Semi standard non polar	33892256
Rosmadial,1TMS,isomer #2	CC(C)C1=CC(C=O)=C2C(=C1O)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C	2682.5	Semi standard non polar	33892256
Rosmadial,2TMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C	2674.9	Semi standard non polar	33892256
Rosmadial,2TMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C	2721.5	Standard non polar	33892256
Rosmadial,1TBDMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C21CCCC(C)(C)C1C=O	2955.7	Semi standard non polar	33892256
Rosmadial,1TBDMS,isomer #2	CC(C)C1=CC(C=O)=C2C(=C1O)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C	2898.2	Semi standard non polar	33892256
Rosmadial,2TBDMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C	3059.6	Semi standard non polar	33892256
Rosmadial,2TBDMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C	3135.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmadial GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-0309000000-f623455987c2374d4235	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmadial GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-2319800000-5ad28cbc5884f92494d2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmadial GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmadial 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 - Rosmadial 10V, Negative-QTOF	splash10-0006-0019000000-95758903e99ee99ca15a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 20V, Negative-QTOF	splash10-0006-0339000000-c956fea811809f0b7052	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 40V, Negative-QTOF	splash10-03du-2932000000-ca31d768dd21e98e053b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 10V, Negative-QTOF	splash10-0006-0009000000-d8ca376d8bc744bbe377	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 20V, Negative-QTOF	splash10-00kr-0079000000-a062efcc8c2bfa4cdca3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 40V, Negative-QTOF	splash10-000f-1192000000-0b134d3261fd43b8271a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 10V, Positive-QTOF	splash10-0002-0209000000-968194b31f34fbdf2e7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 20V, Positive-QTOF	splash10-0hi2-3239000000-57a02ee126ff42746a02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 40V, Positive-QTOF	splash10-00o0-9802000000-557fab0dce37174b9809	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 10V, Positive-QTOF	splash10-002b-0009000000-f24d35e11655ca15cf1c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 20V, Positive-QTOF	splash10-00kb-1049000000-433bc20527bf55bf702e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmadial 40V, Positive-QTOF	splash10-05r1-6692000000-b44b4b653ee7412f3799	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72996596

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1082821

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 Rosmadial (HMDB0038219)

MOL for HMDB0038219 (Rosmadial)

3D MOL for HMDB0038219 (Rosmadial)

3D SDF for HMDB0038219 (Rosmadial)

3D-SDF for HMDB0038219 (Rosmadial)

PDB for HMDB0038219 (Rosmadial)

3D PDB for HMDB0038219 (Rosmadial)

SMILES for HMDB0038219 (Rosmadial)

INCHI for HMDB0038219 (Rosmadial)

Structure for HMDB0038219 (Rosmadial)

3D Structure for HMDB0038219 (Rosmadial)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra