NP-MRD: Showing NP-Card for Anisomycin (NP0137185)

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Record Information

Version

2.0

Created at

2022-05-30 16:44:21 UTC

Updated at

2022-05-30 16:44:21 UTC

NP-MRD ID

NP0137185

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Anisomycin

Description

4-Hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anisomycin is found in Streptomyces hygrospinosus and Streptomyces werraensis. 4-Hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    6.2038   -0.4043   -0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2513   -0.6761   -1.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -0.7597   -1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9243   -1.0255   -2.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5861   -1.1078   -1.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -0.9214   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221   -0.9977    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9064    0.3517   -0.0499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1468    1.2328    0.8577 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838    2.4163    0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582    1.8182    1.0552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7656    1.8712    2.3851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    0.3730    0.5843 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3272    0.1434   -0.2684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3028   -0.7885   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3892   -0.9086   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2782   -1.5308    0.8813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.6582    0.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5030   -0.5746    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897    0.5177    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1928   -1.2354    0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2093   -0.2891   -0.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526   -1.1713   -3.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.3224   -2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151   -1.7206   -0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2582   -1.3347    1.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471    0.8062   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2503    0.7971    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    3.1078    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685    2.8764   -0.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    2.4029    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3283    2.6805    2.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -0.3100    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603   -0.9350   -2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0149   -1.8083   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0910   -0.0447   -1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9038   -0.5049    1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2552   -0.3656    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 13  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 13 33  1  1
 16 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
M  END


  Mrv1533004151520052D          

 19 20  0  0  0  0            999 V2000
    2.2501    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597    3.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598    3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314    4.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160    4.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    4.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.0027    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137185

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2NCC(O)C2OC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3

> <INCHI_KEY>
YKJYKKNCCRKFSL-UHFFFAOYSA-N

> <FORMULA>
C14H19NO4

> <MOLECULAR_WEIGHT>
265.309

> <EXACT_MASS>
265.131408096

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.142231963576013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.7312822379999993

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.766854111930687

> <JCHEM_PKA_STRONGEST_BASIC>
9.220643194596146

> <JCHEM_POLAR_SURFACE_AREA>
67.78999999999999

> <JCHEM_REFRACTIVITY>
69.3019

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anisomycin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       4.200  12.745   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.200  11.205   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.867  10.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.867   8.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.533   8.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.199   8.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.134   8.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.134   6.585   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.111   5.680   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.364   4.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.904   4.215   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.810   2.969   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.380   5.680   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.845   6.156   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.165   7.662   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.630   8.138   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.021   8.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.199  10.435   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.533  11.205   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    6   19                                                       
CONECT   19   18    3                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetic acid	Generator
Anisomycin	MeSH

Chemical Formula

C₁₄H₁₉NO₄

Average Mass

265.3090 Da

Monoisotopic Mass

265.13141 Da

IUPAC Name

4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate

Traditional Name

anisomycin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC2NCC(O)C2OC(C)=O)C=C1

InChI Identifier

InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3

InChI Key

YKJYKKNCCRKFSL-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
Streptomyces hygrospinosus	LOTUS Database	35616633
Streptomyces werraensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Pyrrolidine
Amino acid or derivatives
1,2-aminoalcohol
Carboxylic acid ester
Secondary alcohol
Azacycle
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Secondary amine
Organopnictogen compound
Alcohol
Carbonyl group
Organic oxide
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	0.97	ALOGPS
logP	0.73	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.3 m³·mol⁻¹	ChemAxon
Polarizability	28.14 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

2199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Anisomycin (NP0137185)

MOL for NP0137185 (Anisomycin)

3D MOL for NP0137185 (Anisomycin)

3D SDF for NP0137185 (Anisomycin)

3D-SDF for NP0137185 (Anisomycin)

PDB for NP0137185 (Anisomycin)

3D PDB for NP0137185 (Anisomycin)

SMILES for NP0137185 (Anisomycin)

INCHI for NP0137185 (Anisomycin)

Structure for NP0137185 (Anisomycin)

3D Structure for NP0137185 (Anisomycin)