NP-MRD: Showing NP-Card for methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate (NP0221017)

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Record Information

Version

2.0

Created at

2022-09-05 22:29:15 UTC

Updated at

2022-09-05 22:29:15 UTC

NP-MRD ID

NP0221017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate

Description

SCHEMBL13752042 belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate is found in Salinispora tropica. Based on a literature review very few articles have been published on SCHEMBL13752042.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200292D          

 23 24  0  0  1  0            999 V2000
    0.2044    0.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564   -0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634   -0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8183    0.5954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -0.8023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6674   -0.1892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4125    0.5954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744   -0.3607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0264    0.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334    0.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0883   -0.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5363   -1.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7293   -1.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4480   -1.2872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -2.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180   -2.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5279   -2.0718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0128   -2.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333   -2.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3182   -3.3205    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7828   -1.2872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3413   -0.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.4503    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
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  6  7  1  1  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0221017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(N=C(O)[C@H](CCCl)[C@]1(C)O)[C@@H](O)[C@H]1CCCC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H24ClNO5/c1-15(22)11(8-9-17)13(20)18-16(15,14(21)23-2)12(19)10-6-4-3-5-7-10/h4,6,10-12,19,22H,3,5,7-9H2,1-2H3,(H,18,20)/t10-,11+,12+,15+,16+/m1/s1

> <INCHI_KEY>
JVJAKTQDSOUGCF-BFPXCNAZSA-N

> <FORMULA>
C16H24ClNO5

> <MOLECULAR_WEIGHT>
345.82

> <EXACT_MASS>
345.1343006

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.43966657342525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R,3S,4R)-4-(2-chloroethyl)-2-[(S)-[(1S)-cyclohex-2-en-1-yl](hydroxy)methyl]-3,5-dihydroxy-3-methyl-3,4-dihydro-2H-pyrrole-2-carboxylate

> <JCHEM_LOGP>
1.5408617856666678

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.432471927371658

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.751423731009192

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3489662907909659

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
86.1683

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R,3S,4R)-4-(2-chloroethyl)-2-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4H-pyrrole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.381   0.471   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.412  -0.673   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.918  -0.353   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.394   1.111   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.949  -1.498   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.979  -0.353   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.503   1.111   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.486  -0.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.516   0.471   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.022   0.151   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.498  -1.314   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.468  -2.458   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.961  -2.138   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.703  -2.403   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.179  -3.867   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.274  -5.113   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.719  -3.867   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.624  -5.113   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.155  -4.952   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       8.061  -6.198   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       5.195  -2.403   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.237  -1.269   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.704  -2.707   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14   21                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    5   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17    5   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄ClNO₅

Average Mass

345.8200 Da

Monoisotopic Mass

345.13430 Da

IUPAC Name

methyl (2R,3S,4R)-4-(2-chloroethyl)-2-[(S)-[(1S)-cyclohex-2-en-1-yl](hydroxy)methyl]-3,5-dihydroxy-3-methyl-3,4-dihydro-2H-pyrrole-2-carboxylate

Traditional Name

methyl (2R,3S,4R)-4-(2-chloroethyl)-2-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4H-pyrrole-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(N=C(O)[C@H](CCCl)[C@]1(C)O)[C@@H](O)[C@H]1CCCC=C1

InChI Identifier

InChI=1S/C16H24ClNO5/c1-15(22)11(8-9-17)13(20)18-16(15,14(21)23-2)12(19)10-6-4-3-5-7-10/h4,6,10-12,19,22H,3,5,7-9H2,1-2H3,(H,18,20)/t10-,11+,12+,15+,16+/m1/s1

InChI Key

JVJAKTQDSOUGCF-BFPXCNAZSA-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
Salinispora tropica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Hydroxy acid
Fatty acyl
Pyrrolidone
2-pyrrolidone
Methyl ester
Pyrrolidine
Tertiary alcohol
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Alcohol
Organohalogen compound
Organochloride
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Alkyl halide
Alkyl chloride
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	1.54	ChemAxon
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	86.17 m³·mol⁻¹	ChemAxon
Polarizability	35.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

9511860

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11336915

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate (NP0221017)

MOL for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

3D MOL for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

3D SDF for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

3D-SDF for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

PDB for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

3D PDB for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

SMILES for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

INCHI for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

Structure for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)

3D Structure for NP0221017 (methyl (2r,3s,4r)-4-(2-chloroethyl)-2-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-3,5-dihydroxy-3-methyl-4h-pyrrole-2-carboxylate)