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Showing NP-Card for Rosmadial (NP0049058)

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Record Information
Version2.0
Created at2022-03-17 21:06:27 UTC
Updated at2022-03-17 21:06:27 UTC
NP-MRD IDNP0049058
Secondary Accession NumbersNone
Natural Product Identification
Common NameRosmadial
DescriptionRosmadial 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Rosmadial is found, on average, in the highest concentration within rosemaries. Rosmadial has also been detected, but not quantified in, several different foods, such as gingers, star anises, herbs and spices, sweet bay, and pepper (spice). Rosmadial is found in Laurus nobilis, Salvia africana, Salvia africana-lutea , Salvia columbariae, Salvia mellifera and Salvia przewalskii . This could make rosmadial a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049058 (Rosmadial)


  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
Download

3D MOL for NP0049058 (Rosmadial)

Download
3D SDF for NP0049058 (Rosmadial)

  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>
NP0049058

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

Download
3D-SDF for NP0049058 (Rosmadial)
Download
PDB for NP0049058 (Rosmadial)
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

Download
3D PDB for NP0049058 (Rosmadial)
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SMILES for NP0049058 (Rosmadial)
CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2
Download
INCHI for NP0049058 (Rosmadial)
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
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View in JSmol
Synonyms
ValueSource
(-)-RosmadialHMDB
Chemical FormulaC20H24O5
Average Mass344.4016 Da
Monoisotopic Mass344.16237 Da
IUPAC Name7-hydroxy-3',3'-dimethyl-2-oxo-6-(propan-2-yl)-2H-spiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde
Traditional Name7-hydroxy-6-isopropyl-3',3'-dimethyl-2-oxospiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde
CAS Registry Number85514-31-4
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 KeyJBWRHBJFAVSAMJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carum carviFooDB
Cinnamomum verumFooDB
Cuminum cyminumFooDB
Illicium verumFooDB
Laurus nobilisLOTUS Database
Laurus nobilis L.FooDB
Myristica fragransFooDB
Piper nigrum L.FooDB
Salvia africanaLOTUS Database
Salvia africana-luteaPlant
Salvia columbariaeLOTUS Database
Salvia melliferaLOTUS Database
Salvia officinalisFooDB
Salvia przewalskiiPlant
Salvia rosmarinusFooDB
Syzygium aromaticumFooDB
Zingiber officinaleFooDB
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassNot Available
Direct ParentBenzofurans  
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.76ALOGPS
logP4.37ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability36.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038219  
DrugBank IDNot Available
Phenol Explorer Compound ID670  
FoodDB IDFDB017461  
KNApSAcK IDC00031190  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72996596  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available