NP-MRD: Showing NP-Card for (2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid (NP0147693)

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Record Information

Version

2.0

Created at

2022-09-02 03:20:41 UTC

Updated at

2022-09-02 03:20:41 UTC

NP-MRD ID

NP0147693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid

Description

Aspergillamide C belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Based on a literature review very few articles have been published on Aspergillamide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205202D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022205202D          

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 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 36  1  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H](N=C(C)O)C(=O)N(C)[C@@H](CC1=CC=C(O)C=C1)C(O)=N\C=C/C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C28H34N4O4/c1-5-18(2)26(31-19(3)33)28(36)32(4)25(16-20-10-12-22(34)13-11-20)27(35)29-15-14-21-17-30-24-9-7-6-8-23(21)24/h6-15,17-18,25-26,30,34H,5,16H2,1-4H3,(H,29,35)(H,31,33)/b15-14-/t18-,25-,26-/m0/s1

> <INCHI_KEY>
NZRQIPUGMHEHIL-AQFPYVEVSA-N

> <FORMULA>
C28H34N4O4

> <MOLECULAR_WEIGHT>
490.604

> <EXACT_MASS>
490.258005591

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.15004820047905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S,3S)-2-[(1-hydroxyethylidene)amino]-N,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-N-[(Z)-2-(1H-indol-3-yl)ethenyl]propanimidic acid

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
3.5761801735430137

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.250445464998659

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3441888013477716

> <JCHEM_PKA_STRONGEST_BASIC>
5.629649603722625

> <JCHEM_POLAR_SURFACE_AREA>
121.51000000000002

> <JCHEM_REFRACTIVITY>
140.64120000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S,3S)-2-[(1-hydroxyethylidene)amino]-N,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-N-[(Z)-2-(1H-indol-3-yl)ethenyl]propanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.215  -9.736   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.549 -10.506   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.883  -9.736   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.883  -8.196   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.217 -10.506   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      13.217 -12.046   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      11.883 -12.816   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.883 -14.356   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.549 -12.046   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.550  -9.736   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.550  -8.196   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      15.884 -10.506   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      15.884 -12.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.218  -9.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.551 -10.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.551 -12.046   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.885 -12.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.885 -14.356   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.551 -15.126   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.551 -16.666   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.218 -14.356   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.218 -12.816   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.218  -8.196   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.884  -7.426   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0      18.551  -7.426   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      19.885  -8.196   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.219  -7.426   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.219  -5.886   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.973  -4.981   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      20.449  -3.516   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      21.989  -3.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      23.019  -2.372   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.525  -2.692   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      25.001  -4.157   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.971  -5.301   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.464  -4.981   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16                                                       
CONECT   23   14   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   28   31                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄N₄O₄

Average Mass

490.6040 Da

Monoisotopic Mass

490.25801 Da

IUPAC Name

(2S)-2-[(2S,3S)-2-[(1-hydroxyethylidene)amino]-N,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-N-[(Z)-2-(1H-indol-3-yl)ethenyl]propanimidic acid

Traditional Name

(2S)-2-[(2S,3S)-2-[(1-hydroxyethylidene)amino]-N,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-N-[(Z)-2-(1H-indol-3-yl)ethenyl]propanimidic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H](N=C(C)O)C(=O)N(C)[C@@H](CC1=CC=C(O)C=C1)C(O)=N\C=C/C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C28H34N4O4/c1-5-18(2)26(31-19(3)33)28(36)32(4)25(16-20-10-12-22(34)13-11-20)27(35)29-15-14-21-17-30-24-9-7-6-8-23(21)24/h6-15,17-18,25-26,30,34H,5,16H2,1-4H3,(H,29,35)(H,31,33)/b15-14-/t18-,25-,26-/m0/s1

InChI Key

NZRQIPUGMHEHIL-AQFPYVEVSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Tyrosine or derivatives
Phenylalanine or derivatives
Isoleucine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Amphetamine or derivatives
Alpha-amino acid or derivatives
Indole or derivatives
Indole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Substituted pyrrole
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Heteroaromatic compound
Acetamide
Tertiary carboxylic acid amide
Pyrrole
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.23	ALOGPS
logP	3.58	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.34	ChemAxon
pKa (Strongest Basic)	5.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.51 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	140.64 m³·mol⁻¹	ChemAxon
Polarizability	53.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146683613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid (NP0147693)

MOL for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

3D MOL for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

3D SDF for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

3D-SDF for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

PDB for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

3D PDB for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

SMILES for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

INCHI for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

Structure for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)

3D Structure for NP0147693 ((2s)-2-[(2s,3s)-2-[(1-hydroxyethylidene)amino]-n,3-dimethylpentanamido]-3-(4-hydroxyphenyl)-n-[(1z)-2-(1h-indol-3-yl)ethenyl]propanimidic acid)