NP-MRD: Showing NP-Card for meso-Hannokinol (NP0140156)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-06-29 20:48:35 UTC

Updated at

2022-06-29 20:48:36 UTC

NP-MRD ID

NP0140156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

meso-Hannokinol

Description

Meso-Hannokinol belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. meso-Hannokinol is found in Curcuma kwangsiensis. meso-Hannokinol was first documented in 2008 (PMID: 18523923). Based on a literature review very few articles have been published on meso-Hannokinol (PMID: 24915829).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 48  0  0  0  0  0  0  0  0999 V2000
    6.6097    0.6760   -1.8520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6029    0.6553   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3940    1.2690   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3462    1.2724   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221    0.6420    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4933    0.5619    2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6756   -0.6951    1.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -0.7214    0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0556    0.3577    0.6503 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -1.9829    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321   -1.9690   -0.8968 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4465   -1.8166   -1.9155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862   -0.9180   -1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.1330    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7258   -0.1218   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8210   -0.3984   -0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8679    0.4937   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8506    1.6960   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9057    2.6157   -0.3635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468    1.9509    0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6906    1.0661    0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431    0.0232    1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579    0.0274    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4937    0.2204   -1.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161    1.7770   -2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259    1.7753   -0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749    1.4094    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337    0.7020    3.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9559   -0.6747    2.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808   -1.6104    2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398   -0.5320   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3640    1.1925    0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5409   -2.1101    1.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8585   -2.8835    0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582   -2.9950   -1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -1.0240   -2.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0692   -1.0971   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2181    0.1056   -1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806   -2.1341   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972   -1.1320    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8594   -1.3491   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7124    0.2448   -1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9014    3.3453   -1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    2.8897    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263    1.2668    1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8757   -0.4776    2.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6983   -0.4605    0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 23  1  0
 23 22  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 22  5  1  0
 21 15  1  0
  9 32  1  0
  8 31  1  6
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
  4 26  1  0
  3 25  1  0
  1 24  1  0
 23 47  1  0
 22 46  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  6
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END


  Mrv1652306292222482D          

 23 24  0  0  1  0            999 V2000
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 11 21  1  6  0  0  0
  9 22  1  6  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140156

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H](CCC1=CC=C(O)C=C1)C[C@H](O)CCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-4,7-10,18-23H,5-6,11-13H2/t18-,19+

> <INCHI_KEY>
GZVIQGVWSNEONZ-KDURUIRLSA-N

> <FORMULA>
C19H24O4

> <MOLECULAR_WEIGHT>
316.397

> <EXACT_MASS>
316.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.94416419116175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5S)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
3.279090129666666

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.597052655077775

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.9950043606834

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7258572950245847

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
90.6584

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5S)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667 -10.780   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000 -10.780   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -8.002  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21   11                                                            
CONECT   22    9                                                            
CONECT   23    3                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₄

Average Mass

316.3970 Da

Monoisotopic Mass

316.16746 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@@H](CCC1=CC=C(O)C=C1)C[C@H](O)CCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C19H24O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-4,7-10,18-23H,5-6,11-13H2/t18-,19+

InChI Key

GZVIQGVWSNEONZ-KDURUIRLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Curcuma kwangsiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Bis-desmethoxycurcumin
Fatty alcohol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26621127

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25763835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee KY, Kim SH, Sung SH, Kim YC: Inhibitory constituents of lipopolysaccharide-induced nitric oxide production in BV2 microglia isolated from Amomum tsao-ko. Planta Med. 2008 Jun;74(8):867-9. doi: 10.1055/s-2008-1074552. Epub 2008 Jun 3. [PubMed:18523923 ]
Zhang TT, Lu CL, Jiang JG: Bioactivity evaluation of ingredients identified from the fruits of Amomum tsaoko Crevost et Lemaire, a Chinese spice. Food Funct. 2014 Aug;5(8):1747-54. doi: 10.1039/c4fo00169a. [PubMed:24915829 ]

Showing NP-Card for meso-Hannokinol (NP0140156)

MOL for NP0140156 (meso-Hannokinol)

3D MOL for NP0140156 (meso-Hannokinol)

3D SDF for NP0140156 (meso-Hannokinol)

3D-SDF for NP0140156 (meso-Hannokinol)

PDB for NP0140156 (meso-Hannokinol)

3D PDB for NP0140156 (meso-Hannokinol)

SMILES for NP0140156 (meso-Hannokinol)

INCHI for NP0140156 (meso-Hannokinol)

Structure for NP0140156 (meso-Hannokinol)

3D Structure for NP0140156 (meso-Hannokinol)