NP-MRD: Showing NP-Card for (-)-Virenamide A (NP0077351)

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Record Information

Version

2.0

Created at

2022-04-28 22:30:46 UTC

Updated at

2022-04-28 22:30:46 UTC

NP-MRD ID

NP0077351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Virenamide A

Description

(2S)-2-{[(2S)-2-[bis(3-methylbut-2-en-1-yl)amino]-1-hydroxy-3-phenylpropylidene]amino}-3-methyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]butanimidic acid 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. (-)-Virenamide A is found in Diplosoma virens. Based on a literature review very few articles have been published on (2S)-2-{[(2S)-2-[bis(3-methylbut-2-en-1-yl)amino]-1-hydroxy-3-phenylpropylidene]amino}-3-methyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]butanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200302D          

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M  END

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M  END


  Mrv1652304292200302D          

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    9.7153   -3.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5079   -3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7061   -4.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1116   -5.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3190   -4.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7245   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9226   -6.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7153   -6.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9134   -7.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3097   -5.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1484   -6.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1392   -7.8795    0.0000 C   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  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  9 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
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077351

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(CC=C(C)C)CC=C(C)C)C(=O)N[C@@H](C(C)C)C1=NC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C31H46N4O2S/c1-21(2)14-17-35(18-15-22(3)4)26(20-25-12-10-9-11-13-25)29(36)33-27(23(5)6)30(37)34-28(24(7)8)31-32-16-19-38-31/h9-16,19,23-24,26-28H,17-18,20H2,1-8H3,(H,33,36)(H,34,37)/t26-,27-,28-/m0/s1

> <INCHI_KEY>
VXPIPADKEDUIDI-KCHLEUMXSA-N

> <FORMULA>
C31H46N4O2S

> <MOLECULAR_WEIGHT>
538.8

> <EXACT_MASS>
538.334147911

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
61.83719467310997

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-[bis(3-methylbut-2-en-1-yl)amino]-3-phenylpropanamido]-3-methyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]butanamide

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
6.296137052666663

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.324503013464824

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.262593621756398

> <JCHEM_PKA_STRONGEST_BASIC>
6.7509161908462

> <JCHEM_POLAR_SURFACE_AREA>
74.33000000000001

> <JCHEM_REFRACTIVITY>
159.07140000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.73e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-[bis(3-methylbut-2-en-1-yl)amino]-3-phenylpropanamido]-3-methyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]butanamide

> <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      12.957 -13.213   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.066 -12.146   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.696 -10.651   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      14.806  -9.583   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      14.436  -8.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.957  -7.661   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.587  -6.166   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.847  -8.729   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.367  -8.302   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.997  -6.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.518  -6.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.107  -5.739   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.258  -9.369   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.628 -10.864   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       7.778  -8.942   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.038 -11.505   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.929 -12.573   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.518 -11.932   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.189  -9.583   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.974 -10.529   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.698  -9.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.126  -8.186   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0       4.665  -8.135   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0      15.546  -7.020   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.025  -7.447   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.135  -6.379   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.615  -6.807   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.985  -8.302   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.875  -9.369   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.395  -8.942   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.286 -10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.656 -11.505   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.135 -11.932   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.505 -13.427   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.245 -10.864   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.477 -12.786   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.327 -14.708   0.000  0.00  0.00           C+0
CONECT    1    2   37   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6   25                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   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   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20                                                       
CONECT   25    5   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32    4   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(2S)-2-[bis(3-methylbut-2-en-1-yl)amino]-1-hydroxy-3-phenylpropylidene]amino}-3-methyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]butanimidate	Generator

Chemical Formula

C₃₁H₄₆N₄O₂S

Average Mass

538.8000 Da

Monoisotopic Mass

538.33415 Da

IUPAC Name

(2S)-2-[(2S)-2-[bis(3-methylbut-2-en-1-yl)amino]-3-phenylpropanamido]-3-methyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]butanamide

Traditional Name

(2S)-2-[(2S)-2-[bis(3-methylbut-2-en-1-yl)amino]-3-phenylpropanamido]-3-methyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]butanamide

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(CC=C(C)C)CC=C(C)C)C(=O)N[C@@H](C(C)C)C1=NC=CS1

InChI Identifier

InChI=1S/C31H46N4O2S/c1-21(2)14-17-35(18-15-22(3)4)26(20-25-12-10-9-11-13-25)29(36)33-27(23(5)6)30(37)34-28(24(7)8)31-32-16-19-38-31/h9-16,19,23-24,26-28H,17-18,20H2,1-8H3,(H,33,36)(H,34,37)/t26-,27-,28-/m0/s1

InChI Key

VXPIPADKEDUIDI-KCHLEUMXSA-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
Diplosoma virens	Plant	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
Phenylalanine or derivatives
Valine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Aralkylamine
N-acyl-amine
Fatty amide
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Heteroaromatic compound
Azole
Thiazole
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	5.19	ALOGPS
logP	6.3	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.33 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	159.07 m³·mol⁻¹	ChemAxon
Polarizability	61.84 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

8160326

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9984736

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Virenamide A (NP0077351)

MOL for NP0077351 ((-)-Virenamide A)

3D MOL for NP0077351 ((-)-Virenamide A)

3D SDF for NP0077351 ((-)-Virenamide A)

3D-SDF for NP0077351 ((-)-Virenamide A)

PDB for NP0077351 ((-)-Virenamide A)

3D PDB for NP0077351 ((-)-Virenamide A)

SMILES for NP0077351 ((-)-Virenamide A)

INCHI for NP0077351 ((-)-Virenamide A)

Structure for NP0077351 ((-)-Virenamide A)

3D Structure for NP0077351 ((-)-Virenamide A)