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Showing NP-Card for Clovamide (NP0337998)

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Record Information
Version2.0
Created at2024-09-11 13:23:24 UTC
Updated at2024-09-11 13:23:25 UTC
NP-MRD IDNP0337998
Secondary Accession NumbersNone
Natural Product Identification
Common NameClovamide
DescriptionClovamide belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Clovamide was first documented in 2020 (PMID: 32953564). Based on a literature review a significant number of articles have been published on Clovamide (PMID: 33039740) (PMID: 38740144) (PMID: 38611422) (PMID: 37344361) (PMID: 36990292) (PMID: 34868112).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0337998 (Clovamide)


  Mrv2104 05262315552D          

 26 27  0  0  0  0            999 V2000
    4.1950    2.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457    2.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592    0.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457    0.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    0.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1950    0.3432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950   -0.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321   -0.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -0.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6099   -0.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1524   -0.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728    2.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9153    0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    0.3432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047   -1.6396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4576   -1.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -2.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -1.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950   -1.7919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 25  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 18  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
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
Download

3D MOL for NP0337998 (Clovamide)

Download
3D SDF for NP0337998 (Clovamide)

  Mrv2104 05262315552D          

 26 27  0  0  0  0            999 V2000
    4.1950    2.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457    2.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592    0.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457    0.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    0.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1950    0.3432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950   -0.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321   -0.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -0.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6099   -0.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1524   -0.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728    2.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9153    0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    0.3432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047   -1.6396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4576   -1.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -2.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -1.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950   -1.7919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 25  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 18  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
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337998

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(CC1=CC=C(O)C(O)=C1)NC(=O)\C=C/C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-

> <INCHI_KEY>
GPZFXSWMDFBRGS-UTCJRWHENA-N

> <FORMULA>
C18H17NO7

> <MOLECULAR_WEIGHT>
359.334

> <EXACT_MASS>
359.100501891

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.68630004635767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)-2-[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enamido]propanoic acid

> <JCHEM_LOGP>
2.041632343666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.951570641837908

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2217271494250985

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6932307838590303

> <JCHEM_POLAR_SURFACE_AREA>
147.32

> <JCHEM_REFRACTIVITY>
92.89989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4-dihydroxyphenyl)-2-[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0337998 (Clovamide)
Download
PDB for NP0337998 (Clovamide)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0       7.831   3.772   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.549   2.918   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.125   3.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.844   2.918   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.844   1.495   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.125   0.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.549   1.495   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.831   0.641   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -7.831  -0.214   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.407  -1.068   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.125  -0.214   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.844  -0.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.420  -0.214   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.138  -1.068   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.284  -0.214   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.563   3.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.138   2.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.709   1.352   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.274   0.641   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.569  -3.061   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.854  -2.633   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.850  -3.772   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.844  -2.491   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.125  -3.345   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.549  -2.491   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -7.831  -3.345   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   18                                                       
CONECT   16    4   17                                                       
CONECT   17   16   18                                                       
CONECT   18   15   17   19                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   14   20   22                                                  
CONECT   22   21                                                            
CONECT   23   12   24                                                       
CONECT   24   23   25                                                       
CONECT   25   10   24   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

Download
3D PDB for NP0337998 (Clovamide)
Download
SMILES for NP0337998 (Clovamide)
OC(=O)C(CC1=CC=C(O)C(O)=C1)NC(=O)\C=C/C1=CC=C(O)C(O)=C1
Download
INCHI for NP0337998 (Clovamide)
InChI=1/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H17NO7
Average Mass359.3340 Da
Monoisotopic Mass359.10050 Da
IUPAC Name3-(3,4-dihydroxyphenyl)-2-[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enamido]propanoic acid
Traditional Name3-(3,4-dihydroxyphenyl)-2-[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enamido]propanoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(CC1=CC=C(O)C(O)=C1)NC(=O)\C=C/C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-
InChI KeyGPZFXSWMDFBRGS-UTCJRWHENA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentTyrosine and derivatives  
Alternative Parents
Substituents
  • Tyrosine or derivatives
    • 

  • Phenylalanine or derivatives
    • 

  • N-acyl-alpha-amino acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • Cinnamic acid amide
    • 

  • Cinnamic acid or derivatives
    • 

  • Hydroxycinnamic acid or derivatives
    • 

  • 3-phenylpropanoic-acid
    • 

  • Amphetamine or derivatives
    • 

  • Styrene
    • 

  • Catechol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic 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
logP2.04ChemAxon
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)-0.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area147.32 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity92.9 m³·mol⁻¹ChemAxon
Polarizability34.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClovamide  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ye N, Belli S, Caruso F, Roy G, Rossi M: Antioxidant studies by hydrodynamic voltammetry and DFT, quantitative analyses by HPLC-DAD of clovamide, a natural phenolic compound found in Theobroma Cacao L. beans. Food Chem. 2021 Mar 30;341(Pt 2):128260. doi: 10.1016/j.foodchem.2020.128260.  Epub 2020 Oct 1. [PubMed:33039740  ] 
  2. Abouelela ME, Orabi MAA, Abdelhamid RA, Abdelkader MS, Madkor HR, Darwish FMM, Hatano T, Elsadek BEM: Ethyl acetate extract of Ceiba pentandra (L.) Gaertn. reduces methotrexate-induced renal damage in rats via antioxidant, anti-inflammatory, and antiapoptotic actions. J Tradit Complement Med. 2019 Aug 28;10(5):478-486. doi:  10.1016/j.jtcme.2019.08.006. eCollection 2020 Sep. [PubMed:32953564  ] 
  3. Xu F, Takiguchi Y, Makabe K, Konno H: Synthesis and evaluation of catecholamine derivatives as amyloid-beta aggregation inhibitors. Bioorg Med Chem Lett. 2024 Jul 15;107:129788. doi: 10.1016/j.bmcl.2024.129788.  Epub 2024 May 11. [PubMed:38740144  ] 
  4. Kolodziejczyk-Czepas J: Clovamide and Its Derivatives-Bioactive Components of Theobroma cacao and Other Plants in the Context of Human Health. Foods. 2024 Apr 6;13(7):1118. doi: 10.3390/foods13071118. [PubMed:38611422  ] 
  5. Thi Thu Ha T, Thi Cuc N, Tai BH, Trung KH, Dang Khanh T, Van Kiem P: Pelliolatifolias A-D, Four Undescribed Compounds from Pellionia latifolia Boerl. and Their Nitric Oxide Production Inhibitory Activity. Chem Biodivers. 2023 Aug;20(8):e202300731. doi: 10.1002/cbdv.202300731. Epub 2023  Jul 6. [PubMed:37344361  ] 
  6. Akissi ZLE, Magid AA, Kouassi-Yao AP, Ouattara N, Koffi JK, Voutquenne-Nazabadioko L: New diterpenoids and phenolic amides from Icacina mannii Oliv. Fitoterapia. 2023 Jun;167:105487. doi: 10.1016/j.fitote.2023.105487. Epub 2023  Mar 27. [PubMed:36990292  ] 
  7. Sullivan ML, Knollenberg BJ: Red Clover HDT, a BAHD Hydroxycinnamoyl-Coenzyme A:L-3,4-Dihydroxyphenylalanine (L-DOPA) Hydroxycinnamoyl Transferase That Synthesizes Clovamide and Other N-Hydroxycinnamoyl-Aromatic Amino Acid Amides. Front Plant Sci. 2021 Nov 9;12:727461. doi: 10.3389/fpls.2021.727461. eCollection  2021. [PubMed:34868112  ] 
  8. Knollenberg BJ, Li GX, Lambert JD, Maximova SN, Guiltinan MJ: Clovamide, a Hydroxycinnamic Acid Amide, Is a Resistance Factor Against Phytophthora spp. in Theobroma cacao. Front Plant Sci. 2020 Dec 23;11:617520. doi: 10.3389/fpls.2020.617520.  eCollection 2020. [PubMed:33424909  ] 
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