NP-MRD: Showing NP-Card for Homomorphin C (NP0333325)

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Record Information

Version

2.0

Created at

2024-05-30 14:46:28 UTC

Updated at

2024-11-01 00:37:25 UTC

NP-MRD ID

NP0333325

Natural Product DOI

https://doi.org/10.57994/2683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Homomorphin C

Description

Homomorphin C belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on Homomorphin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02112317222D          

 33 35  0  0  1  0            999 V2000
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -2.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0892   -2.0515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6288   -2.9346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857    0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11  6  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 21  1  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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  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
 29 31  1  0  0  0  0
 26 32  2  0  0  0  0
 14 32  1  0  0  0  0
 22 32  1  0  0  0  0
  9 33  2  0  0  0  0
M  END


  Mrv2104 02112317222D          

 33 35  0  0  1  0            999 V2000
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -2.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0892   -2.0515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6288   -2.9346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857    0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11  6  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 21  1  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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  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
 29 31  1  0  0  0  0
 26 32  2  0  0  0  0
 14 32  1  0  0  0  0
 22 32  1  0  0  0  0
  9 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC2=C(NC3=CC=CC(CC=C(C)C)=C23)C(C)(C)C=C)NC(=O)[C@@]([H])(NC1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H35N3O2/c1-8-26(6,7)23-18(14-20-24(30)29-22(16(4)5)25(31)28-20)21-17(13-12-15(2)3)10-9-11-19(21)27-23/h8-12,16,20,22,27H,1,13-14H2,2-7H3,(H,28,31)(H,29,30)/t20-,22-/m0/s1

> <INCHI_KEY>
LSBWFIAGGXZTFQ-UNMCSNQZSA-N

> <FORMULA>
C26H35N3O2

> <MOLECULAR_WEIGHT>
421.585

> <EXACT_MASS>
421.272927379

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.703338638075344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-3-{[4-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-(propan-2-yl)piperazine-2,5-dione

> <JCHEM_LOGP>
4.903750659666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.388431977045924

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.27367835727094

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9089709989535635

> <JCHEM_POLAR_SURFACE_AREA>
73.99000000000001

> <JCHEM_REFRACTIVITY>
126.7272

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-3-isopropyl-6-{[4-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}piperazine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-FEB-23         0                                  
HETATM    1  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.376  -5.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.406  -4.150   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.839  -6.118   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0      -3.900  -3.829   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      -2.393  -3.509   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.887  -3.189   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       1.174  -5.478   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.320  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.320   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.653   1.007   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.424  -2.365   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8    9                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9    4   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19                                                            
CONECT   21   15   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26   14   22                                                  
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₅N₃O₂

Average Mass

421.5850 Da

Monoisotopic Mass

421.27293 Da

IUPAC Name

(3S,6S)-3-{[4-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-(propan-2-yl)piperazine-2,5-dione

Traditional Name

(3S,6S)-3-isopropyl-6-{[4-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}piperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC2=C(NC3=CC=CC(CC=C(C)C)=C23)C(C)(C)C=C)NC(=O)[C@@]([H])(NC1=O)C(C)C

InChI Identifier

InChI=1S/C26H35N3O2/c1-8-26(6,7)23-18(14-20-24(30)29-22(16(4)5)25(31)28-20)21-17(13-12-15(2)3)10-9-11-19(21)27-23/h8-12,16,20,22,27H,1,13-14H2,2-7H3,(H,28,31)(H,29,30)/t20-,22-/m0/s1

InChI Key

LSBWFIAGGXZTFQ-UNMCSNQZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCL3, experimental)	shuyilin@usc.edu	University of Southern California	Shu-Yi Lin	2024-05-30	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCL3, experimental)	shuyilin@usc.edu	University of Southern California	Shu-Yi Lin	2024-05-30	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCL3, experimental)	shuyilin@usc.edu	University of Southern California	Shu-Yi Lin	2024-05-30	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCL3, experimental)	shuyilin@usc.edu	University of Southern California	Shu-Yi Lin	2024-05-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCL3, experimental)	shuyilin@usc.edu	University of Southern California	Shu-Yi Lin	2024-05-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCL3, experimental)	shuyilin@usc.edu	University of Southern California	Shu-Yi Lin	2024-05-30	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.065587839, CDCl₃, simulated)	shuyilin@usc.edu	University of Southern California	Shu-Yi Lin	2024-05-30	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
homomorphus		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Valine or derivatives
N-acyl-alpha amino acid or derivatives
Triptan
Alpha-amino acid amide
Indole or derivatives
Indole
2,5-dioxopiperazine
Dioxopiperazine
Fatty acyl
Benzenoid
Piperazine
N-acyl-amine
Fatty amide
1,4-diazinane
Heteroaromatic compound
Pyrroline
Pyrrole
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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	4.9	ChemAxon
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.73 m³·mol⁻¹	ChemAxon
Polarizability	47.7 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Homomorphin C (NP0333325)

MOL for NP0333325 (Homomorphin C)

3D MOL for NP0333325 (Homomorphin C)

3D SDF for NP0333325 (Homomorphin C)

3D-SDF for NP0333325 (Homomorphin C)

PDB for NP0333325 (Homomorphin C)

3D PDB for NP0333325 (Homomorphin C)

SMILES for NP0333325 (Homomorphin C)

INCHI for NP0333325 (Homomorphin C)

Structure for NP0333325 (Homomorphin C)

3D Structure for NP0333325 (Homomorphin C)