NP-MRD: Showing NP-Card for mono-n-butylphthalate (NP0155174)

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Record Information

Version

2.0

Created at

2022-09-02 12:11:08 UTC

Updated at

2022-09-02 12:11:08 UTC

NP-MRD ID

NP0155174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

mono-n-butylphthalate

Description

Monobutylphthalate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Monobutylphthalate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Monobutylphthalate has been detected, but not quantified in, cereals and cereal products. This could make monobutylphthalate a potential biomarker for the consumption of these foods. . DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. DBP was permanently banned in children's toys, Monobutylphthalate inhibits steroidogenesis by downregulating steroidogenic acute regulatory protein expression. Monobutylphthalate is a potentially toxic compound. It is a suspected endocrine disruptor. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. DBP is also used as an ectoparasiticide. mono-n-butylphthalate is found in Glycyrrhiza glabra, Nelumbo nucifera and Oecophylla smaragdina. mono-n-butylphthalate was first documented in 2000 (PMID: 11049818). Monobutylphthalate (MBP), is an active metabolite of di-n-butyl phthalate (DBP).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    4.7939   -0.9460    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8983   -0.2652   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4487   -0.2154    0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    0.4689   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2989    0.6104   -0.4178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124   -0.3606   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0521   -1.5406   -0.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.3314    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068   -1.5441    0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0437   -1.6232    0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7362   -0.4390    0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1340    0.7779    0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7606    0.8158    0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090    2.1408    0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865    3.1634    0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    2.4137   -0.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8407   -0.6934    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6251   -0.4705    1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6699   -2.0368    0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -0.7610   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949    0.7618   -0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.4178    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -1.1997    0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8653   -0.0150   -1.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790    1.5085   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1247   -2.4431    0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5526   -2.5794    0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8117   -0.5132    0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7096    1.7066    0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721    3.1920   -0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
M  END


  Mrv1652303102016512D          

 16 16  0  0  0  0            999 V2000
   13.3579  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3579  -12.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6433  -11.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6433  -12.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9289  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9289  -12.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6433  -10.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3578   -9.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9288   -9.8056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2144  -11.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2144  -10.2181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5000  -11.4556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7855  -11.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0710  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3565  -11.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6420  -11.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)C1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-2-3-8-16-12(15)10-7-5-4-6-9(10)11(13)14/h4-7H,2-3,8H2,1H3,(H,13,14)

> <INCHI_KEY>
YZBOVSFWWNVKRJ-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.481124312343454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(butoxycarbonyl)benzoic acid

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.9582047026666665

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.08472720984912

> <JCHEM_PKA_STRONGEST_BASIC>
-6.956425236846911

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
59.21310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
monobutyl phthalate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      24.935 -21.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.935 -22.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.601 -20.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.601 -23.694   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.267 -21.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.267 -22.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.601 -19.074   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.935 -18.304   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      22.267 -18.304   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      20.934 -20.614   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      20.934 -19.074   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      19.600 -21.384   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      18.266 -20.614   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.933 -21.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.599 -20.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.265 -21.384   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    7                                                  
CONECT    4    2    6                                                       
CONECT    5    3    6   10                                                  
CONECT    6    4    5                                                       
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
Monobutylphthalic acid	Generator
-N-Butyl-phthalate	HMDB
2-(Butoxycarbonyl)benzoate	HMDB
2-(Butoxycarbonyl)benzoic acid	HMDB
Butyl hydrogen phthalate	HMDB
mono-N-Butyl phthalate	HMDB
MONOBUTYL phthalATE	HMDB
Phthalic acid monobutyl ester	HMDB
Phthalic acid, monobutyl ester	HMDB
Monobutyl phthalate, copper (2+) salt	HMDB
Monobutyl phthalate, potassium salt	HMDB
Monobutyl phthalate, manganese (2+) salt	HMDB
Monobutyl phthalate, sodium salt	HMDB
Monobutyl phthalate, cobalt (2+) salt	HMDB

Chemical Formula

C₁₂H₁₄O₄

Average Mass

222.2372 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

2-(butoxycarbonyl)benzoic acid

Traditional Name

monobutyl phthalate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)C1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C12H14O4/c1-2-3-8-16-12(15)10-7-5-4-6-9(10)11(13)14/h4-7H,2-3,8H2,1H3,(H,13,14)

InChI Key

YZBOVSFWWNVKRJ-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
Glycyrrhiza glabra	LOTUS Database	35616633
Nelumbo nucifera	LOTUS Database	35616633
Oecophylla smaragdina	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoic acid
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.48	ALOGPS
logP	2.96	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	59.21 m³·mol⁻¹	ChemAxon
Polarizability	23.48 Å³	ChemAxon
Number of Rings	1	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

HMDB0013247

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012951

KNApSAcK ID

Not Available

Chemspider ID

8257

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8575

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Blount BC, Silva MJ, Caudill SP, Needham LL, Pirkle JL, Sampson EJ, Lucier GW, Jackson RJ, Brock JW: Levels of seven urinary phthalate metabolites in a human reference population. Environ Health Perspect. 2000 Oct;108(10):979-82. doi: 10.1289/ehp.00108979. [PubMed:11049818 ]
LOTUS database [Link]

Showing NP-Card for mono-n-butylphthalate (NP0155174)

MOL for NP0155174 (mono-n-butylphthalate)

3D MOL for NP0155174 (mono-n-butylphthalate)

3D SDF for NP0155174 (mono-n-butylphthalate)

3D-SDF for NP0155174 (mono-n-butylphthalate)

PDB for NP0155174 (mono-n-butylphthalate)

3D PDB for NP0155174 (mono-n-butylphthalate)

SMILES for NP0155174 (mono-n-butylphthalate)

INCHI for NP0155174 (mono-n-butylphthalate)

Structure for NP0155174 (mono-n-butylphthalate)

3D Structure for NP0155174 (mono-n-butylphthalate)