NP-MRD: Showing NP-Card for 3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol (NP0257004)

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Record Information

Version

2.0

Created at

2022-09-07 22:00:30 UTC

Updated at

2022-09-07 22:00:31 UTC

NP-MRD ID

NP0257004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol

Description

4-(2-Chloroethyl)-2-[(cyclohex-2-en-1-yl)(hydroxy)methyl]-3-methyl-2H-pyrrol-5-ol belongs to the class of organic compounds known as cyclic carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group), where the carboximidic acid group is part of a cycle. 3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol is found in Salinispora tropica. Based on a literature review very few articles have been published on 4-(2-chloroethyl)-2-[(cyclohex-2-en-1-yl)(hydroxy)methyl]-3-methyl-2H-pyrrol-5-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    1.9015   -2.3276    0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739   -1.0500   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814   -0.2128   -0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0590   -0.3880   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.7537    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    0.8858    1.8570 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.9143   -1.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.9787   -1.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6426    0.7274   -1.2467 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -0.4950   -0.5713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5516   -0.3846    0.6207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6580   -1.7126    1.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9323   -0.0014    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8387    0.0497    1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174    0.2634    1.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4506    0.4159   -0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5527    1.3207   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364    1.3023   -0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.7967    0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -3.0906    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108   -2.1871    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5440   -0.4020   -1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2544   -1.3154   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5979    1.7155   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7577    0.5434    0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605    2.0399   -2.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1794   -1.2038   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395    0.2989    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058   -2.2134    0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4011   -0.8067   -0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728   -0.0756    2.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804    0.3238    1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277    0.7052   -0.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3943   -0.6183   -0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    2.3676   -1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4341    0.9824   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124    2.0888    0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040    1.6047   -1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 10  2  1  0
 14 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  6
 11 28  1  1
 12 29  1  0
 13 30  1  6
 18 37  1  0
 18 38  1  0
 17 35  1  0
 17 36  1  0
 16 33  1  0
 16 34  1  0
 15 32  1  0
 14 31  1  0
M  END


  Mrv1652309082200002D          

 18 19  0  0  0  0            999 V2000
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -1.8262    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -2.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  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
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(CCCl)C(O)=NC1C(O)C1CCCC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20ClNO2/c1-9-11(7-8-15)14(18)16-12(9)13(17)10-5-3-2-4-6-10/h3,5,10,12-13,17H,2,4,6-8H2,1H3,(H,16,18)

> <INCHI_KEY>
IZKIYDNYHNTWOM-UHFFFAOYSA-N

> <FORMULA>
C14H20ClNO2

> <MOLECULAR_WEIGHT>
269.77

> <EXACT_MASS>
269.1182566

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.513505677187613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-chloroethyl)-2-[(cyclohex-2-en-1-yl)(hydroxy)methyl]-3-methyl-2H-pyrrol-5-ol

> <JCHEM_LOGP>
2.576913183333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.2086197659089

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.886332852367643

> <JCHEM_PKA_STRONGEST_BASIC>
2.865011933342989

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
74.433

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5H-pyrrol-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.512  -2.854   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.657  -3.885   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       9.121  -3.409   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.477  -6.041   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.032  -4.795   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.053  -3.885   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.916  -0.317   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀ClNO₂

Average Mass

269.7700 Da

Monoisotopic Mass

269.11826 Da

IUPAC Name

4-(2-chloroethyl)-2-[(cyclohex-2-en-1-yl)(hydroxy)methyl]-3-methyl-2H-pyrrol-5-ol

Traditional Name

3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5H-pyrrol-2-ol

CAS Registry Number

Not Available

SMILES

CC1=C(CCCl)C(O)=NC1C(O)C1CCCC=C1

InChI Identifier

InChI=1S/C14H20ClNO2/c1-9-11(7-8-15)14(18)16-12(9)13(17)10-5-3-2-4-6-10/h3,5,10,12-13,17H,2,4,6-8H2,1H3,(H,16,18)

InChI Key

IZKIYDNYHNTWOM-UHFFFAOYSA-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 cyclic carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group), where the carboximidic acid group is part of a cycle.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Cyclic carboximidic acids

Alternative Parents

Substituents

Cyclic carboximidic acid
Secondary alcohol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl chloride
Alkyl halide
Hydrocarbon derivative
Organopnictogen compound
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	2.58	ChemAxon
pKa (Strongest Acidic)	5.89	ChemAxon
pKa (Strongest Basic)	2.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.43 m³·mol⁻¹	ChemAxon
Polarizability	29.51 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

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

72952373

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol (NP0257004)

MOL for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

3D MOL for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

3D SDF for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

3D-SDF for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

PDB for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

3D PDB for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

SMILES for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

INCHI for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

Structure for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)

3D Structure for NP0257004 (3-(2-chloroethyl)-5-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-methyl-5h-pyrrol-2-ol)