NP-MRD: Showing NP-Card for Multifidol (NP0051549)

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Record Information

Version

2.0

Created at

2022-04-27 22:52:23 UTC

Updated at

2022-04-27 22:52:23 UTC

NP-MRD ID

NP0051549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Multifidol

Description

Multifidol belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Multifidol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Multifidol is found in Helichrysum zeyheri, Jatropha multifida and Phyllanthus emblica. Multifidol was first documented in 2005 (PMID: 16252923). Based on a literature review a small amount of articles have been published on multifidol (PMID: 34227310) (PMID: 29287473) (PMID: 25793563) (PMID: 19002080).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.1150    1.5707   -1.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.1330   -1.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8533   -0.0347    0.1548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9971    0.5048    0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5764    0.4778    0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6783    1.5976    1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.0953    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9849   -1.2788   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -2.0832   -0.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -1.7609   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522   -1.0176    0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488   -1.5005    0.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052    0.1915    0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288    0.6410    1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6126    1.8593    1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106    1.5718   -2.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826    1.9463   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    2.2267   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -0.3052   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9405   -0.3716   -1.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522   -1.1434    0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661   -0.1780    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6708    0.4618    2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641    1.5351    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -2.9668   -0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4530   -2.7243   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070   -2.3885   -0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9588    0.7433    1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3878    2.3883    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  6
  4 22  1  0
  4 23  1  0
  4 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
M  END


  Mrv1652304282200522D          

 15 15  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  1  0  0  0
  5 13  1  0  0  0  0
  3 14  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)C1=C(O)C=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O4/c1-3-6(2)11(15)10-8(13)4-7(12)5-9(10)14/h4-6,12-14H,3H2,1-2H3/t6-/m0/s1

> <INCHI_KEY>
ASABIRFQGVWRDC-LURJTMIESA-N

> <FORMULA>
C11H14O4

> <MOLECULAR_WEIGHT>
210.229

> <EXACT_MASS>
210.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.609836636295345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
3.60828816

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.668404160193782

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.961962708052002

> <JCHEM_PKA_STRONGEST_BASIC>
-4.609883233333284

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
56.20589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    5                                                            
CONECT   14    3                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(S)-(+)-(2-Methylbutyryl)phloroglucinol	ChEBI
(S)-2-Methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one	ChEBI
2-Methylbutanoyl phloroglucinol	ChEBI

Chemical Formula

C₁₁H₁₄O₄

Average Mass

210.2290 Da

Monoisotopic Mass

210.08921 Da

IUPAC Name

(2S)-2-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one

Traditional Name

(2S)-2-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)C1=C(O)C=C(O)C=C1O

InChI Identifier

InChI=1S/C11H14O4/c1-3-6(2)11(15)10-8(13)4-7(12)5-9(10)14/h4-6,12-14H,3H2,1-2H3/t6-/m0/s1

InChI Key

ASABIRFQGVWRDC-LURJTMIESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Helichrysum zeyheri	LOTUS Database	35616633
Jatropha multifida	Plant	KNApSAcK
Phyllanthus emblica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acylphloroglucinol derivative
Butyrophenone
Benzenetriol
Phloroglucinol derivative
Phenylpropane
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Polyol
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenetriol (CHEBI:7020 )
butanone (CHEBI:7020 )

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
logP	2.33	ALOGPS
logP	3.61	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.21 m³·mol⁻¹	ChemAxon
Polarizability	21.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002703

Chemspider ID

29368599

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14412553

PDB ID

Not Available

ChEBI ID

7020

Good Scents ID

Not Available

References

General References

Shen S, Yang Y, Wang J, Chen X, Liu T, Zhuo Q: [Analysis of differences between unifloral honeys from different botanical origins based on non-targeted metabolomics by ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry]. Se Pu. 2021 Mar;39(3):291-300. doi: 10.3724/SP.J.1123.2020.06029. [PubMed:34227310 ]
Spreng S, Hofmann T: Activity-Guided Identification of in Vitro Antioxidants in Beer. J Agric Food Chem. 2018 Jan 24;66(3):720-731. doi: 10.1021/acs.jafc.7b05674. Epub 2018 Jan 16. [PubMed:29287473 ]
Dresel M, Dunkel A, Hofmann T: Sensomics analysis of key bitter compounds in the hard resin of hops (Humulus lupulus L.) and their contribution to the bitter profile of Pilsner-type beer. J Agric Food Chem. 2015 Apr 8;63(13):3402-18. doi: 10.1021/acs.jafc.5b00239. Epub 2015 Mar 27. [PubMed:25793563 ]
Wang XW, Mao Y, Wang NL, Yao XS: A new phloroglucinol diglycoside derivative from Hypericum japonicum Thunb. Molecules. 2008 Nov 7;13(11):2796-803. doi: 10.3390/molecules13112796. [PubMed:19002080 ]
Bohr G, Gerhauser C, Knauft J, Zapp J, Becker H: Anti-inflammatory acylphloroglucinol derivatives from Hops (Humulus lupulus). J Nat Prod. 2005 Oct;68(10):1545-8. doi: 10.1021/np050164z. [PubMed:16252923 ]

Showing NP-Card for Multifidol (NP0051549)

MOL for NP0051549 (Multifidol)

3D MOL for NP0051549 (Multifidol)

3D SDF for NP0051549 (Multifidol)

3D-SDF for NP0051549 (Multifidol)

PDB for NP0051549 (Multifidol)

3D PDB for NP0051549 (Multifidol)

SMILES for NP0051549 (Multifidol)

INCHI for NP0051549 (Multifidol)

Structure for NP0051549 (Multifidol)

3D Structure for NP0051549 (Multifidol)