NP-MRD: Showing NP-Card for (2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid (NP0250260)

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Record Information

Version

2.0

Created at

2022-09-07 13:02:37 UTC

Updated at

2022-09-07 13:02:38 UTC

NP-MRD ID

NP0250260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid

Description

(2S)-2-{[(2E)-5-[(1S,5S,6S,7S,9S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]Tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. (2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid is found in Streptomyces platensis. Based on a literature review very few articles have been published on (2S)-2-{[(2E)-5-[(1S,5S,6S,7S,9S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]Tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215022D          

 33 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072215022D          

 33 36  0  0  1  0            999 V2000
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 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/CC[C@@]1(C)[C@H]2[C@@H]3CC4C[C@]2(C[C@]4(C)O3)C=CC1=O)C(O)=N[C@@H](CCC(O)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34N2O6/c1-14(21(30)27-16(22(31)32)6-7-19(26)29)5-4-9-23(2)18(28)8-10-25-12-15-11-17(20(23)25)33-24(15,3)13-25/h5,8,10,15-17,20H,4,6-7,9,11-13H2,1-3H3,(H2,26,29)(H,27,30)(H,31,32)/b14-5+/t15?,16-,17-,20+,23+,24-,25-/m0/s1

> <INCHI_KEY>
LSLTZMQPHAAWAW-TVJMVYBOSA-N

> <FORMULA>
C25H34N2O6

> <MOLECULAR_WEIGHT>
458.555

> <EXACT_MASS>
458.241686823

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.76715486690033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2E)-5-[(1S,5S,6S,7S,9S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_LOGP>
0.5852474267005665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.8142536172942365

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.4140765132732094

> <JCHEM_PKA_STRONGEST_BASIC>
12.942937704895508

> <JCHEM_POLAR_SURFACE_AREA>
140.27

> <JCHEM_REFRACTIVITY>
133.3359

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2E)-5-[(1S,5S,6S,7S,9S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.085  -0.969   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.361  -2.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.822  -2.380   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.007  -1.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.532  -1.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.347   0.182   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.449  -0.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.135   0.709   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.341  -0.248   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.311   2.271   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.026   3.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.583   2.717   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.515   4.055   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.032   3.478   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.736   1.769   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.146   0.345   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.747   0.578   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.815   2.199   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.306   2.586   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.144   2.682   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.677   1.058   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.175  -3.635   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.451  -4.994   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      -5.714  -3.583   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -6.529  -4.890   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.068  -4.838   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.883  -6.145   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -10.422  -6.093   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0     -11.236  -7.400   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0     -11.146  -4.734   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.804  -6.249   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.265  -6.301   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.619  -7.556   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   21                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20   21                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   12                                                       
CONECT   21   16   12    6                                                  
CONECT   22    2   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(2E)-5-[(1S,5S,6S,7S,9S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1,.0,]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoate	Generator

Chemical Formula

C₂₅H₃₄N₂O₆

Average Mass

458.5550 Da

Monoisotopic Mass

458.24169 Da

IUPAC Name

(2S)-2-{[(2E)-5-[(1S,5S,6S,7S,9S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

Traditional Name

(2S)-2-{[(2E)-5-[(1S,5S,6S,7S,9S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

CAS Registry Number

Not Available

SMILES

C\C(=C/CC[C@@]1(C)[C@H]2[C@@H]3CC4C[C@]2(C[C@]4(C)O3)C=CC1=O)C(O)=N[C@@H](CCC(O)=N)C(O)=O

InChI Identifier

InChI=1S/C25H34N2O6/c1-14(21(30)27-16(22(31)32)6-7-19(26)29)5-4-9-23(2)18(28)8-10-25-12-15-11-17(20(23)25)33-24(15,3)13-25/h5,8,10,15-17,20H,4,6-7,9,11-13H2,1-3H3,(H2,26,29)(H,27,30)(H,31,32)/b14-5+/t15?,16-,17-,20+,23+,24-,25-/m0/s1

InChI Key

LSLTZMQPHAAWAW-TVJMVYBOSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces platensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid 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

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cyclohexenone
Oxepane
Heterocyclic fatty acid
Branched fatty acid
Fatty acyl
Oxane
Tetrahydrofuran
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.59	ChemAxon
pKa (Strongest Acidic)	-0.41	ChemAxon
pKa (Strongest Basic)	12.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.27 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.34 m³·mol⁻¹	ChemAxon
Polarizability	53.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

139586191

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid (NP0250260)

MOL for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D MOL for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D SDF for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D-SDF for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

PDB for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D PDB for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

SMILES for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

INCHI for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

Structure for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D Structure for NP0250260 ((2s)-2-{[(2e)-5-[(1s,5s,6s,7s,9s)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1⁷,¹⁰.0¹,⁶]tridec-2-en-5-yl]-1-hydroxy-2-methylpent-2-en-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)