NP-MRD: Showing NP-Card for Aurantiamide (NP0077886)

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Record Information

Version

2.0

Created at

2022-04-28 23:01:57 UTC

Updated at

2024-09-03 04:16:59 UTC

NP-MRD ID

NP0077886

Natural Product DOI

https://doi.org/10.57994/0879

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aurantiamide

Description

Aurantiamide belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Aurantiamide is found in Curcuma aromatica, Hybanthus enneasperma, Murraya paniculata, Piper wallichii and Xylocarpus granatum . Aurantiamide was first documented in 2021 (PMID: 34301301). Based on a literature review a small amount of articles have been published on Aurantiamide (PMID: 34472261) (PMID: 34581048) (PMID: 34159261) (PMID: 33995019).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201012D          

 30 32  0  0  1  0            999 V2000
    5.8453   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555   -1.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1955   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9255   -2.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154   -3.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -2.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -2.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -2.0171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4149   -2.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -1.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -0.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -1.7052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7946   -2.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -3.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -2.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -3.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -4.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -4.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -3.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -1.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4444   -2.0171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6358   -0.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0957    0.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    0.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3052   -1.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
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   -3.9325   -1.7103    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8344   -2.4804   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8464   -3.1729    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9284   -3.0691    1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  1  0
  2  1  2  0
  2 25  1  0
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 29 30  2  0
 24 19  1  0
 11  6  1  0
 30 25  1  0
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 15 41  1  1
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M  END


  Mrv1652304292201012D          

 30 32  0  0  1  0            999 V2000
    5.8453   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555   -1.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1955   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8748   -1.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -0.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -1.7052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7946   -2.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  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
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  7  8  1  0  0  0  0
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 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077886

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26N2O3/c28-18-22(16-19-10-4-1-5-11-19)26-25(30)23(17-20-12-6-2-7-13-20)27-24(29)21-14-8-3-9-15-21/h1-15,22-23,28H,16-18H2,(H,26,30)(H,27,29)/t22-,23-/m0/s1

> <INCHI_KEY>
KSVKECXWDNCRTM-GOTSBHOMSA-N

> <FORMULA>
C25H26N2O3

> <MOLECULAR_WEIGHT>
402.494

> <EXACT_MASS>
402.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.82743255227365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-3-phenyl-2-(phenylformamido)propanamide

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.550168926666667

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.841395768086407

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.899505409466514

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2995814354992423

> <JCHEM_POLAR_SURFACE_AREA>
78.43

> <JCHEM_REFRACTIVITY>
117.27960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-3-phenyl-2-(phenylformamido)propanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      10.911  -3.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.424  -2.892   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.432  -4.056   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.928  -5.511   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.415  -5.802   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.407  -4.638   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.895  -4.929   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.887  -3.765   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.375  -4.056   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.366  -2.892   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.870  -1.437   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.854  -3.183   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.350  -4.638   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.358  -5.802   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.870  -5.511   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.879  -6.675   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.375  -8.131   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.862  -8.422   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.854  -7.258   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.846  -2.019   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.830  -3.765   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.326  -1.146   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.187  -1.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.195  -0.273   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.691   1.182   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.179   1.473   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.830   0.309   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.391  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.903  -2.019   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   12   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29    8   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆N₂O₃

Average Mass

402.4940 Da

Monoisotopic Mass

402.19434 Da

IUPAC Name

(2S)-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-3-phenyl-2-(phenylformamido)propanamide

Traditional Name

(2S)-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-3-phenyl-2-(phenylformamido)propanamide

CAS Registry Number

Not Available

SMILES

OC[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C25H26N2O3/c28-18-22(16-19-10-4-1-5-11-19)26-25(30)23(17-20-12-6-2-7-13-20)27-24(29)21-14-8-3-9-15-21/h1-15,22-23,28H,16-18H2,(H,26,30)(H,27,29)/t22-,23-/m0/s1

InChI Key

KSVKECXWDNCRTM-GOTSBHOMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	hxkuang@hljucm.net	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Curcuma aromatica	LOTUS Database	35616633
Datura metel		Not Available
Hybanthus enneasperma	-	KNApSAcK
Murraya paniculata	LOTUS Database	35616633
Piper wallichii	LOTUS Database	35616633
Xylocarpus granatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Hippuric acid or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Amphetamine or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Fatty amide
Secondary carboxylic acid amide
Carboxamide group
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Primary 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
logP	2.72	ALOGPS
logP	3.55	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.28 m³·mol⁻¹	ChemAxon
Polarizability	43.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00020778

Chemspider ID

161599

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185904

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Deng Y, Ding T, Deng L, Hao X, Mu S: Active constituents of Zanthoxylum nitidium from Yunnan Province against leukaemia cells in vitro. BMC Chem. 2021 Jul 23;15(1):44. doi: 10.1186/s13065-021-00771-0. [PubMed:34301301 ]
Chai LS, Liu GS, Zhu YX, Wang SY, Yang CS, Li Y: [Chemical constituents of Physalis minima]. Zhongguo Zhong Yao Za Zhi. 2021 Aug;46(15):3865-3872. doi: 10.19540/j.cnki.cjcmm.20210525.202. [PubMed:34472261 ]
Guo JM, Yu XM, Jiang B, Su QT, Cao WQ, Liu YP, Fu YH: [Chemical constituents from Clausena excavata and their inhibitory activities against proliferation of synoviocytes]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(17):4438-4445. doi: 10.19540/j.cnki.cjcmm.20210429.203. [PubMed:34581048 ]
Ndifor AR, Stanislaus NN, Fru CG, Talontsi F, Tabopda TK, Menkem EZ, Tchaleu NB, Owusu YS: Two new sphingolipids from the stem bark of Synsepalum msolo (Sapotaceae). Biochem Biophys Rep. 2021 Jun 11;27:101014. doi: 10.1016/j.bbrep.2021.101014. eCollection 2021 Sep. [PubMed:34159261 ]
Ye X, Wu J, Zhang D, Lan Z, Yang S, Zhu J, Yang M, Gong Q, Zhong L: How Aconiti Radix Cocta can Treat Gouty Arthritis Based on Systematic Pharmacology and UPLC-QTOF-MS/MS. Front Pharmacol. 2021 Apr 30;12:618844. doi: 10.3389/fphar.2021.618844. eCollection 2021. [PubMed:33995019 ]
DOI: 10.1002/cbdv.202300693
DOI: 10.1016/j.phytol.2022.04.008
PII: s1874390022000866

Showing NP-Card for Aurantiamide (NP0077886)

MOL for NP0077886 (Aurantiamide)

3D MOL for NP0077886 (Aurantiamide)

3D SDF for NP0077886 (Aurantiamide)

3D-SDF for NP0077886 (Aurantiamide)

PDB for NP0077886 (Aurantiamide)

3D PDB for NP0077886 (Aurantiamide)

SMILES for NP0077886 (Aurantiamide)

INCHI for NP0077886 (Aurantiamide)

Structure for NP0077886 (Aurantiamide)

3D Structure for NP0077886 (Aurantiamide)