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Showing NP-Card for Dehydrocurdione (NP0048236)

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Record Information
Version2.0
Created at2022-03-17 20:53:16 UTC
Updated at2022-03-17 20:53:17 UTC
NP-MRD IDNP0048236
Secondary Accession NumbersNone
Natural Product Identification
Common NameDehydrocurdione
DescriptionDehydrocurdione belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Dehydrocurdione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dehydrocurdione has been detected, but not quantified in, turmerics. Dehydrocurdione is found in Curcuma aeruginosa, Curcuma aromatica, Curcuma heyneana and Curcuma zedoaria . This could make dehydrocurdione a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048236 (Dehydrocurdione)


  Mrv0541 05061308252D          

 17 17  0  0  0  0            999 V2000
    0.0418   -0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -1.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234    1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6363    1.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2400    0.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2216   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0326    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381    0.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308   -1.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3376    1.1509    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
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
M  END
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3D MOL for NP0048236 (Dehydrocurdione)

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3D SDF for NP0048236 (Dehydrocurdione)

  Mrv0541 05061308252D          

 17 17  0  0  0  0            999 V2000
    0.0418   -0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271    2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -1.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234    1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6363    1.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2400    0.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2216   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0326    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381    0.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308   -1.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3376    1.1509    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
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC\C=C(C)/CC(=O)C(CC1=O)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10(2)13-9-14(16)12(4)7-5-6-11(3)8-15(13)17/h6,12H,5,7-9H2,1-4H3/b11-6-

> <INCHI_KEY>
ZYPUZCWWTYIGFV-WDZFZDKYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.918422214315758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6Z)-6,10-dimethyl-3-(propan-2-ylidene)cyclodec-6-ene-1,4-dione

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
3.592981008333333

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.48921638821996

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.186411407355573

> <JCHEM_PKA_STRONGEST_BASIC>
-5.043670798483267

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
71.59929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6Z)-6,10-dimethyl-3-(propan-2-ylidene)cyclodec-6-ene-1,4-dione

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048236 (Dehydrocurdione)
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PDB for NP0048236 (Dehydrocurdione)
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       0.078  -1.366   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.662   1.197   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.037   5.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.257  -2.647   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.407   0.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.777   2.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.517  -0.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.188   3.119   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.558  -0.939   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.448   0.129   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   3.546   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.147  -1.579   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.928   0.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -2.006   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.818   1.624   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.297  -3.501   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.630   2.148   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   12                                                       
CONECT    8   11   15                                                       
CONECT    9   13   14                                                       
CONECT   10    1    2   13                                                  
CONECT   11    3    6    8                                                  
CONECT   12    4    7   14                                                  
CONECT   13    9   10   15                                                  
CONECT   14    9   12   16                                                  
CONECT   15    8   13   17                                                  
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

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3D PDB for NP0048236 (Dehydrocurdione)
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SMILES for NP0048236 (Dehydrocurdione)
CC1CC\C=C(C)/CC(=O)C(CC1=O)=C(C)C
Download
INCHI for NP0048236 (Dehydrocurdione)
InChI=1S/C15H22O2/c1-10(2)13-9-14(16)12(4)7-5-6-11(3)8-15(13)17/h6,12H,5,7-9H2,1-4H3/b11-6-
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View in JSmol
Synonyms
ValueSource
1(10),7(11)-Germacradiene-5,8-dioneHMDB
DehydrocurdioneMeSH
Chemical FormulaC15H22O2
Average Mass234.3340 Da
Monoisotopic Mass234.16198 Da
IUPAC Name(6Z)-6,10-dimethyl-3-(propan-2-ylidene)cyclodec-6-ene-1,4-dione
Traditional Name(6Z)-6,10-dimethyl-3-(propan-2-ylidene)cyclodec-6-ene-1,4-dione
CAS Registry Number38230-32-9
SMILES
CC1CC\C=C(C)/CC(=O)C(CC1=O)=C(C)C
InChI Identifier
InChI=1S/C15H22O2/c1-10(2)13-9-14(16)12(4)7-5-6-11(3)8-15(13)17/h6,12H,5,7-9H2,1-4H3/b11-6-
InChI KeyZYPUZCWWTYIGFV-WDZFZDKYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Curcuma aeruginosaLOTUS Database
Curcuma aromaticaLOTUS Database
Curcuma heyneanaLOTUS Database
Curcuma longaFooDB
Curcuma zedoariaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentGermacrane sesquiterpenoids  
Alternative Parents
Substituents
  • Germacrane sesquiterpenoid
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP3.33ALOGPS
logP3.59ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.6 m³·mol⁻¹ChemAxon
Polarizability26.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035407  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014082  
KNApSAcK IDC00011732  
Chemspider IDNot Available
KEGG Compound IDC16949  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14191392  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References