NP-MRD: Showing NP-Card for 2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid (NP0157000)

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Record Information

Version

2.0

Created at

2022-09-02 14:17:44 UTC

Updated at

2022-09-02 14:17:44 UTC

NP-MRD ID

NP0157000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid

Description

Antibiotic X 14885A belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Based on a literature review very few articles have been published on Antibiotic X 14885A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216172D          

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     RDKit          3D

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 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
 23 35  1  0  0  0  0
 21 36  1  0  0  0  0
 12 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1OC2(CC[C@@H](C)[C@@H](CC3=NC4=C(C(O)=O)C(O)=CC=C4O3)O2)CC[C@H]1C)C(=O)C1=CC=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32N2O7/c1-14-8-10-27(11-9-15(2)25(36-27)16(3)24(31)17-5-4-12-28-17)35-20(14)13-21-29-23-19(34-21)7-6-18(30)22(23)26(32)33/h4-7,12,14-16,20,25,28,30H,8-11,13H2,1-3H3,(H,32,33)/t14-,15-,16?,20-,25?,27?/m1/s1

> <INCHI_KEY>
DXLFHVNETQTLLA-QBYXERAJSA-N

> <FORMULA>
C27H32N2O7

> <MOLECULAR_WEIGHT>
496.56

> <EXACT_MASS>
496.220951378

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.864113463723136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2R,3R,9R)-3,9-dimethyl-8-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
5.127964182

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.921495786649269

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1708334543731347

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1211765158840511

> <JCHEM_POLAR_SURFACE_AREA>
134.88000000000002

> <JCHEM_REFRACTIVITY>
130.04269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2R,3R,9R)-3,9-dimethyl-8-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.796  -1.187   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.256  -1.187   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.486  -2.521   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.946  -2.521   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.256  -3.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.629  -5.261   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.774  -6.292   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.107  -5.522   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.787  -4.015   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.486   0.147   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.256   1.480   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.486   2.814   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.946   2.814   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.176   1.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.946   0.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.176  -1.187   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.026   2.814   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.796   4.148   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.026   5.481   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.796   6.815   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.486   5.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.716   6.815   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.176   6.815   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.730   8.061   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       2.194   7.585   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.528   8.355   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.528   9.895   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.194  10.665   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.862  10.665   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.862   7.585   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.195   8.355   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.862   6.045   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.528   5.275   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.194   6.045   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.730   5.569   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.716   4.148   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    2   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17   36                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   36                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   25   35                                                  
CONECT   35   34   23                                                       
CONECT   36   21   12                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂N₂O₇

Average Mass

496.5600 Da

Monoisotopic Mass

496.22095 Da

IUPAC Name

2-{[(2R,3R,9R)-3,9-dimethyl-8-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid

Traditional Name

2-{[(2R,3R,9R)-3,9-dimethyl-8-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C1OC2(CC[C@@H](C)[C@@H](CC3=NC4=C(C(O)=O)C(O)=CC=C4O3)O2)CC[C@H]1C)C(=O)C1=CC=CN1

InChI Identifier

InChI=1S/C27H32N2O7/c1-14-8-10-27(11-9-15(2)25(36-27)16(3)24(31)17-5-4-12-28-17)35-20(14)13-21-29-23-19(34-21)7-6-18(30)22(23)26(32)33/h4-7,12,14-16,20,25,28,30H,8-11,13H2,1-3H3,(H,32,33)/t14-,15-,16?,20-,25?,27?/m1/s1

InChI Key

DXLFHVNETQTLLA-QBYXERAJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acid and derivatives

Alternative Parents

Substituents

Salicylic acid or derivatives
Benzoxazole
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Ketal
Oxane
Substituted pyrrole
Azole
Oxazole
Pyrrole
Heteroaromatic compound
Vinylogous acid
Ketone
Oxacycle
Azacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aldehyde
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.05	ALOGPS
logP	5.13	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-0.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	134.88 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.04 m³·mol⁻¹	ChemAxon
Polarizability	52.86 Å³	ChemAxon
Number of Rings	5	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

C00018527

Chemspider ID

2328784

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3068837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid (NP0157000)

MOL for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

3D MOL for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

3D SDF for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

3D-SDF for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

PDB for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

3D PDB for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

SMILES for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

INCHI for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

Structure for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)

3D Structure for NP0157000 (2-{[(2r,3r,9r)-3,9-dimethyl-8-[1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-5-hydroxy-1,3-benzoxazole-4-carboxylic acid)