NP-MRD: Showing NP-Card for Americine (NP0051090)

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Record Information

Version

2.0

Created at

2022-04-27 22:31:28 UTC

Updated at

2022-04-27 22:31:28 UTC

NP-MRD ID

NP0051090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Americine

Description

Americine 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. Americine is found in Ceanothus americans L. and Ceanothus americanus . Based on a literature review very few articles have been published on Americine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200312D          

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M  END

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M  END


  Mrv1652304282200312D          

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    5.2613   -0.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0459   -0.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0459    0.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7604    0.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4748    0.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4748   -0.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7604   -0.9200    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  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
  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
 26 28  1  0  0  0  0
 25 29  1  1  0  0  0
 29 30  1  0  0  0  0
 12 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 35 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H](C(C)C)C(=O)N[C@H]1[C@@H](OC2=CC=C(C=C2)\C=C/NC(=O)[C@H](CC2=CNC3=CC=CC=C23)NC1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H39N5O4/c1-18(2)26(32-5)30(38)36-27-28(19(3)4)40-22-12-10-20(11-13-22)14-15-33-29(37)25(35-31(27)39)16-21-17-34-24-9-7-6-8-23(21)24/h6-15,17-19,25-28,32,34H,16H2,1-5H3,(H,33,37)(H,35,39)(H,36,38)/b15-14-/t25-,26-,27-,28-/m0/s1

> <INCHI_KEY>
SBDJWBSJRCPRDV-DAEFBSHISA-N

> <FORMULA>
C31H39N5O4

> <MOLECULAR_WEIGHT>
545.684

> <EXACT_MASS>
545.300204756

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.49445324849723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.566027568000001

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.475462583445225

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.28560739101041

> <JCHEM_PKA_STRONGEST_BASIC>
8.899908875635521

> <JCHEM_POLAR_SURFACE_AREA>
124.35

> <JCHEM_REFRACTIVITY>
153.90739999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-N-[(3S,4S,7S,10Z)-7-(1H-indol-3-ylmethyl)-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-3-methyl-2-(methylamino)butanamide

> <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       1.115   2.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.308   4.194   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.064   5.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.622   5.714   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.368   4.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.664   3.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.022   6.525   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.618   6.677   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.015   5.864   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.808   4.451   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.294   4.854   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.839   2.853   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       7.179   1.445   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.980   0.458   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.673  -0.917   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.470   0.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.932   0.392   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.643   1.308   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.319  -1.021   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.790  -1.197   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.237  -2.258   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.505  -1.460   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       5.856  -2.199   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.890  -3.739   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.172  -1.400   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.522  -2.139   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.057  -2.266   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.557  -3.679   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       7.137   0.140   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       8.453   0.940   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.345   2.533   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.821   1.069   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.916  -0.177   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       9.821  -1.423   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      11.286  -0.947   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.286   0.593   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.619   1.363   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.953   0.593   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.953  -0.947   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.619  -1.717   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   31                                                  
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   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30                                                       
CONECT   30   29                                                            
CONECT   31   12   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   32   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₉N₅O₄

Average Mass

545.6840 Da

Monoisotopic Mass

545.30020 Da

IUPAC Name

(2S)-N-[(3S,4S,7S,10Z)-7-[(1H-indol-3-yl)methyl]-5,8-dioxo-3-(propan-2-yl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-3-methyl-2-(methylamino)butanamide

Traditional Name

(2S)-N-[(3S,4S,7S,10Z)-7-(1H-indol-3-ylmethyl)-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-3-methyl-2-(methylamino)butanamide

CAS Registry Number

Not Available

SMILES

CN[C@@H](C(C)C)C(=O)N[C@H]1[C@@H](OC2=CC=C(C=C2)\C=C/NC(=O)[C@H](CC2=CNC3=CC=CC=C23)NC1=O)C(C)C

InChI Identifier

InChI=1S/C31H39N5O4/c1-18(2)26(32-5)30(38)36-27-28(19(3)4)40-22-12-10-20(11-13-22)14-15-33-29(37)25(35-31(27)39)16-21-17-34-24-9-7-6-8-23(21)24/h6-15,17-19,25-28,32,34H,16H2,1-5H3,(H,33,37)(H,35,39)(H,36,38)/b15-14-/t25-,26-,27-,28-/m0/s1

InChI Key

SBDJWBSJRCPRDV-DAEFBSHISA-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 americans L.	Plant	KNApSAcK
Ceanothus americanus	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
Valine or derivatives
Macrolactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Alkyl aryl ether
Fatty amide
N-acyl-amine
Fatty acyl
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Ether
Oxacycle
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic peptide (CHEBI:2632 )

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	2.9	ALOGPS
logP	3.57	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	11.29	ChemAxon
pKa (Strongest Basic)	8.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	124.35 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	153.91 m³·mol⁻¹	ChemAxon
Polarizability	59.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00001991

Chemspider ID

4444901

KEGG Compound ID

C09996

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1842881

References

General References

Not Available

Showing NP-Card for Americine (NP0051090)

MOL for NP0051090 (Americine)

3D MOL for NP0051090 (Americine)

3D SDF for NP0051090 (Americine)

3D-SDF for NP0051090 (Americine)

PDB for NP0051090 (Americine)

3D PDB for NP0051090 (Americine)

SMILES for NP0051090 (Americine)

INCHI for NP0051090 (Americine)

Structure for NP0051090 (Americine)

3D Structure for NP0051090 (Americine)