NP-MRD: Showing NP-Card for Adouetine X (NP0051087)

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Record Information

Version

2.0

Created at

2022-04-27 22:31:17 UTC

Updated at

2022-04-27 22:31:17 UTC

NP-MRD ID

NP0051087

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Adouetine X

Description

Adouetine X belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Adouetine X is found in Ceanothus americanus , Melochia chamaedrys, Waltheria americana and Zizyphus jujuba var.inermis . Adouetine X was first documented in 2007 (PMID: 17169385). Based on a literature review very few articles have been published on Adouetine X (PMID: 19231884).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200312D          

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  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  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
 27 29  1  0  0  0  0
 25 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 12 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C)[C@@H](OC2=CC=C(C=C2)\C=C/NC1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44N4O4/c1-9-19(6)23-27(34)29-15-14-20-10-12-21(13-11-20)36-25(18(4)5)24(28(35)30-23)31-26(33)22(32(7)8)16-17(2)3/h10-15,17-19,22-25H,9,16H2,1-8H3,(H,29,34)(H,30,35)(H,31,33)/b15-14-/t19-,22-,23-,24-,25-/m0/s1

> <INCHI_KEY>
OMVRKRVDDRUXPW-RJJCKBEYSA-N

> <FORMULA>
C28H44N4O4

> <MOLECULAR_WEIGHT>
500.684

> <EXACT_MASS>
500.336255913

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.5175527959577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-N-[(3S,4S,7S,10Z)-7-[(2S)-butan-2-yl]-5,8-dioxo-3-(propan-2-yl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-2-(dimethylamino)-4-methylpentanamide

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.8926659659999983

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.553159525402389

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.380822786268542

> <JCHEM_PKA_STRONGEST_BASIC>
7.801097097949061

> <JCHEM_POLAR_SURFACE_AREA>
99.77

> <JCHEM_REFRACTIVITY>
141.7712

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-N-[(3S,4S,7S,10Z)-7-[(2S)-butan-2-yl]-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-2-(dimethylamino)-4-methylpentanamide

> <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       0.160  -4.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.417  -4.422   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.178  -3.075   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.514  -1.655   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.021  -1.715   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.821  -3.026   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.480  -0.037   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.780   1.405   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.640   2.177   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.259   2.120   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.686   3.599   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.640   1.317   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.501   0.021   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.722  -1.516   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.257  -1.638   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.261  -3.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.195  -4.155   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.743  -4.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.085  -5.412   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.440  -6.811   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.618  -5.271   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       5.594  -3.772   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.928  -3.002   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.928  -1.462   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.262  -3.772   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.595  -3.002   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.929  -3.772   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.263  -3.002   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.929  -5.312   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       8.262  -5.312   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       9.595  -6.082   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.928  -6.082   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.696   2.438   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.195   2.084   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.251   3.205   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.254   3.913   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17    1                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   12   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄N₄O₄

Average Mass

500.6840 Da

Monoisotopic Mass

500.33626 Da

IUPAC Name

(2S)-N-[(3S,4S,7S,10Z)-7-[(2S)-butan-2-yl]-5,8-dioxo-3-(propan-2-yl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-2-(dimethylamino)-4-methylpentanamide

Traditional Name

(2S)-N-[(3S,4S,7S,10Z)-7-[(2S)-butan-2-yl]-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-2-(dimethylamino)-4-methylpentanamide

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C)[C@@H](OC2=CC=C(C=C2)\C=C/NC1=O)C(C)C

InChI Identifier

InChI=1S/C28H44N4O4/c1-9-19(6)23-27(34)29-15-14-20-10-12-21(13-11-20)36-25(18(4)5)24(28(35)30-23)31-26(33)22(32(7)8)16-17(2)3/h10-15,17-19,22-25H,9,16H2,1-8H3,(H,29,34)(H,30,35)(H,31,33)/b15-14-/t19-,22-,23-,24-,25-/m0/s1

InChI Key

OMVRKRVDDRUXPW-RJJCKBEYSA-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
Ceanothus americanus	Plant	KNApSAcK
Melochia chamaedrys	Plant	KNApSAcK
Waltheria americana	Plant	KNApSAcK
Zizyphus jujuba var.inermis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Leucine or derivatives
N-acyl-alpha amino acid or derivatives
Macrolactam
Alpha-amino acid amide
Alpha-amino acid or derivatives
Alkyl aryl ether
N-acyl-amine
Fatty amide
Fatty acyl
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Lactam
Carboxamide group
Amino acid or derivatives
Oxacycle
Ether
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic peptide (CHEBI:2492 )

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	3.42	ALOGPS
logP	3.89	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	11.38	ChemAxon
pKa (Strongest Basic)	7.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.77 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	141.77 m³·mol⁻¹	ChemAxon
Polarizability	55.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

C00001988

Chemspider ID

4444898

KEGG Compound ID

C09993

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281577

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1841251

References

General References

Trevisan G, Maldaner G, Velloso NA, Sant'Anna Gda S, Ilha V, Velho Gewehr Cde C, Rubin MA, Morel AF, Ferreira J: Antinociceptive effects of 14-membered cyclopeptide alkaloids. J Nat Prod. 2009 Apr;72(4):608-12. doi: 10.1021/np800377y. [PubMed:19231884 ]
Dias GC, Gressler V, Hoenzel SC, Silva UF, Dalcol II, Morel AF: Constituents of the roots of Melochia chamaedrys. Phytochemistry. 2007 Mar;68(5):668-72. doi: 10.1016/j.phytochem.2006.11.004. Epub 2006 Dec 13. [PubMed:17169385 ]

Showing NP-Card for Adouetine X (NP0051087)

MOL for NP0051087 (Adouetine X)

3D MOL for NP0051087 (Adouetine X)

3D SDF for NP0051087 (Adouetine X)

3D-SDF for NP0051087 (Adouetine X)

PDB for NP0051087 (Adouetine X)

3D PDB for NP0051087 (Adouetine X)

SMILES for NP0051087 (Adouetine X)

INCHI for NP0051087 (Adouetine X)

Structure for NP0051087 (Adouetine X)

3D Structure for NP0051087 (Adouetine X)