NP-MRD: Showing NP-Card for (+)-Hemiasterlin C (NP0068744)

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Record Information

Version

1.0

Created at

2022-04-28 14:00:28 UTC

Updated at

2022-04-28 14:00:29 UTC

NP-MRD ID

NP0068744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Hemiasterlin C

Description

21-Desmethylhemiasterlin 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. (+)-Hemiasterlin C is found in Hemiasterella minor. Based on a literature review very few articles have been published on 21-Desmethylhemiasterlin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216002D          

 37 38  0  0  1  0            999 V2000
   -1.6113    5.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7868    5.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3508    4.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395    3.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    3.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    4.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    2.8422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097    2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 36  1  0  0  0  0
  7 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282216002D          

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  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 22 33  1  0  0  0  0
 12 34  1  1  0  0  0
 34 35  1  0  0  0  0
 10 36  1  0  0  0  0
  7 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@H](C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@H](\C=C(/C)C(O)=O)C(C)C)C(C)(C)C1=CN(C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C29H44N4O4/c1-17(2)23(15-19(5)28(36)37)33(10)27(35)24(18(3)4)31-26(34)25(30-8)29(6,7)21-16-32(9)22-14-12-11-13-20(21)22/h11-18,23-25,30H,1-10H3,(H,31,34)(H,36,37)/b19-15+/t23-,24+,25-/m1/s1

> <INCHI_KEY>
XLMQHOWHUACFMZ-OMZRSGGISA-N

> <FORMULA>
C29H44N4O4

> <MOLECULAR_WEIGHT>
512.695

> <EXACT_MASS>
512.336255913

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.73040611508262

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4S)-4-[(2S)-N,3-dimethyl-2-[(2S)-3-methyl-3-(1-methyl-1H-indol-3-yl)-2-(methylamino)butanamido]butanamido]-2,5-dimethylhex-2-enoic acid

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
1.951445545429242

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.888496319527594

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.363407030331158

> <JCHEM_PKA_STRONGEST_BASIC>
8.549406920793475

> <JCHEM_POLAR_SURFACE_AREA>
103.67

> <JCHEM_REFRACTIVITY>
146.9022

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4S)-4-[(2S)-N,3-dimethyl-2-[(2S)-3-methyl-2-(methylamino)-3-(1-methylindol-3-yl)butanamido]butanamido]-2,5-dimethylhex-2-enoic acid

> <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      -3.008   9.451   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.469   9.502   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.655   8.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.380   6.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.919   6.785   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.733   8.092   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.347   5.305   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.071   4.442   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.856   5.388   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.623   4.961   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.196   3.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.103   4.534   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.213   5.601   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.843   7.096   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       4.692   5.174   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.802   6.242   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.432   7.737   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.542   8.805   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.952   8.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.282   5.815   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.651   4.320   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       8.391   6.883   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       9.871   6.456   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.980   7.524   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.460   7.096   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.570   8.164   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.049   7.737   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      13.200   9.659   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.830   5.601   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.241   4.961   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.720   4.534   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.131   3.893   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.021   8.378   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.473   3.039   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       3.952   2.612   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.051   6.440   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.795   4.781   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   37                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12   36                                             
CONECT   11   10                                                            
CONECT   12   10   13   34                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   33                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   23   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   22                                                            
CONECT   34   12   35                                                       
CONECT   35   34                                                            
CONECT   36   10                                                            
CONECT   37    7                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₄N₄O₄

Average Mass

512.6950 Da

Monoisotopic Mass

512.33626 Da

IUPAC Name

(2E,4S)-4-[(2S)-N,3-dimethyl-2-[(2S)-3-methyl-3-(1-methyl-1H-indol-3-yl)-2-(methylamino)butanamido]butanamido]-2,5-dimethylhex-2-enoic acid

Traditional Name

(2E,4S)-4-[(2S)-N,3-dimethyl-2-[(2S)-3-methyl-2-(methylamino)-3-(1-methylindol-3-yl)butanamido]butanamido]-2,5-dimethylhex-2-enoic acid

CAS Registry Number

Not Available

SMILES

CN[C@H](C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@H](\C=C(/C)C(O)=O)C(C)C)C(C)(C)C1=CN(C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C29H44N4O4/c1-17(2)23(15-19(5)28(36)37)33(10)27(35)24(18(3)4)31-26(34)25(30-8)29(6,7)21-16-32(9)22-14-12-11-13-20(21)22/h11-18,23-25,30H,1-10H3,(H,31,34)(H,36,37)/b19-15+/t23-,24+,25-/m1/s1

InChI Key

XLMQHOWHUACFMZ-OMZRSGGISA-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
Hemiasterella minor	-	KNApSAcK

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
Valine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Triptan
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
N-alkylindole
3-alkylindole
Indole or derivatives
Indole
Medium-chain fatty acid
Heterocyclic fatty acid
Amino fatty acid
Methyl-branched fatty acid
Branched fatty acid
Aralkylamine
Fatty acyl
Unsaturated fatty acid
N-methylpyrrole
Substituted pyrrole
N-acyl-amine
Fatty acid
Fatty amide
Benzenoid
Tertiary carboxylic acid amide
Pyrrole
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Azacycle
Organoheterocyclic compound
Secondary amine
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
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	3.56	ALOGPS
logP	1.95	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	8.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.67 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	146.9 m³·mol⁻¹	ChemAxon
Polarizability	57.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

4580950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5470574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Hemiasterlin C (NP0068744)

MOL for NP0068744 ((+)-Hemiasterlin C)

3D MOL for NP0068744 ((+)-Hemiasterlin C)

3D SDF for NP0068744 ((+)-Hemiasterlin C)

3D-SDF for NP0068744 ((+)-Hemiasterlin C)

PDB for NP0068744 ((+)-Hemiasterlin C)

3D PDB for NP0068744 ((+)-Hemiasterlin C)

SMILES for NP0068744 ((+)-Hemiasterlin C)

INCHI for NP0068744 ((+)-Hemiasterlin C)

Structure for NP0068744 ((+)-Hemiasterlin C)

3D Structure for NP0068744 ((+)-Hemiasterlin C)