NP-MRD: Showing NP-Card for CBDP (NP0139208)

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Record Information

Version

1.0

Created at

2022-06-29 19:44:01 UTC

Updated at

2022-06-29 19:44:01 UTC

NP-MRD ID

NP0139208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CBDP

Description

4H-1,3,2-Benzodioxaphosphorin, 2-(2-methylphenoxy)-, 2-oxide, also known as 0-tosylsaligenin phosphate or 2-(2-cresyl)-4H-1-3-2-benzodioxaphosphorin-2-oxide, belongs to the class of organic compounds known as aryl phosphotriesters. These are aryl phosphates in which the phosphate is esterified at exactly three positions. It was first documented in 1984 (PMID: 6724216). Based on a literature review a small amount of articles have been published on 4H-1,3,2-Benzodioxaphosphorin, 2-(2-methylphenoxy)-, 2-oxide (PMID: 31557052) (PMID: 1446009) (PMID: 3590185).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.3536   -2.0085    1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3978   -0.8391    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5388   -0.1003    0.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5751    0.9686   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730    1.3293   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101    0.5952   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.4778    0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1364   -1.2019    0.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -1.0626   -0.3645 P   0  0  1  0  0  5  0  0  0  0  0  0
    0.7691   -2.4084   -1.0072 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    0.0939   -1.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4189    1.1409   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210    0.7290   -0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9061    1.3140   -1.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1415    0.9499   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966   -0.0185    0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0336   -0.6000    0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718   -0.2366    0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5893   -0.7932    0.8444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275   -2.5329    1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801   -1.7225    2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863   -2.7296    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4133   -0.4195    1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4971    1.5182   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160    2.1830   -1.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4544    0.9250   -1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626    1.8938   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323    1.6764   -0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8354    2.0831   -1.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0391    1.4324   -0.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1645   -0.3100    0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0570   -1.3718    1.6741 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  9  8  1  1
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  7  2  1  0
 19  9  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END


  Mrv1652306292221442D          

 19 21  0  0  0  0            999 V2000
   -1.7229   -0.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320    1.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501    0.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139208

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=CC=C1OP1(=O)OCC2=CC=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H13O4P/c1-11-6-2-4-8-13(11)17-19(15)16-10-12-7-3-5-9-14(12)18-19/h2-9H,10H2,1H3

> <INCHI_KEY>
LKQSEFCGKYFESN-UHFFFAOYSA-N

> <FORMULA>
C14H13O4P

> <MOLECULAR_WEIGHT>
276.228

> <EXACT_MASS>
276.055145897

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.64350474953615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-methylphenoxy)-2,4-dihydro-1,3,2lambda5-benzodioxaphosphinin-2-one

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.694343933333333

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.293988824159142

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
71.24980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-methylphenoxy)-4H-1,3,2lambda5-benzodioxaphosphinin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -3.216  -1.508   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.226  -0.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.753   1.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.763   2.299   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.246   2.031   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.280   0.584   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.710  -0.595   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.183  -2.043   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       1.334  -2.310   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       0.807  -3.757   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   19                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
0-Tosylsaligenin phosphate	HMDB
2-(2-Cresyl)-4H-1-3-2-benzodioxaphosphorin-2-oxide	HMDB
2-(O-Cresyl)-4H-1-3-2-benzodioxaphosphorin-2-oxide	HMDB
2-TSLPH	HMDB
2-Tolylsaligenin phosphate	HMDB
2-Tosylsaligenin phosphate	HMDB
SCOTP	HMDB
Cresylsaligenin phosphate	HMDB
O-TSP	HMDB
Saligenin cyclic-3-tolylphosphate	HMDB

Chemical Formula

C₁₄H₁₃O₄P

Average Mass

276.2280 Da

Monoisotopic Mass

276.05515 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC=CC=C1OP1(=O)OCC2=CC=CC=C2O1

InChI Identifier

InChI=1S/C14H13O4P/c1-11-6-2-4-8-13(11)17-19(15)16-10-12-7-3-5-9-14(12)18-19/h2-9H,10H2,1H3

InChI Key

LKQSEFCGKYFESN-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl phosphotriesters. These are aryl phosphates in which the phosphate is esterified at exactly three positions.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Aryl phosphotriesters

Alternative Parents

Substituents

Aryl phosphotriester
Phenoxy compound
Toluene
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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

External Links

HMDB ID

HMDB0249713

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104993

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]
Wu SY, Casida JE: Neuropathy target esterase inhibitors: 2-alkyl-, 2-alkoxy-, and 2-(aryloxy)-4H-1,3,2-benzodioxaphosphorin 2-oxides. Chem Res Toxicol. 1992 Sep-Oct;5(5):680-4. doi: 10.1021/tx00029a014. [PubMed:1446009 ]
Clement JG, Benschop HP, DeJong LP, Wolthuis OL: Stereoisomers of soman (pinacolyl methylphosphonofluoridate): inhibition of serum carboxylic ester hydrolase and potentiation of their toxicity by CBDP (2-(2-methylphenoxy)-4H-1,3,2-benzodioxaphosphorin-2-oxide) in mice. Toxicol Appl Pharmacol. 1987 Jun 15;89(1):141-3. doi: 10.1016/0041-008x(87)90184-0. [PubMed:3590185 ]
Clement JG: Role of aliesterase in organophosphate poisoning. Fundam Appl Toxicol. 1984 Apr;4(2 Pt 2):S96-105. doi: 10.1016/0272-0590(84)90141-6. [PubMed:6724216 ]

Showing NP-Card for CBDP (NP0139208)

MOL for NP0139208 (CBDP)

3D MOL for NP0139208 (CBDP)

3D SDF for NP0139208 (CBDP)

3D-SDF for NP0139208 (CBDP)

PDB for NP0139208 (CBDP)

3D PDB for NP0139208 (CBDP)

SMILES for NP0139208 (CBDP)

INCHI for NP0139208 (CBDP)

Structure for NP0139208 (CBDP)

3D Structure for NP0139208 (CBDP)