NP-MRD: Showing NP-Card for 4-methylumbelliferyl sulfate (NP0302986)

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Record Information

Version

2.0

Created at

2022-09-10 16:55:32 UTC

Updated at

2022-09-10 16:55:32 UTC

NP-MRD ID

NP0302986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methylumbelliferyl sulfate

Description

4-Methylumbelliferone sulfate, also known as 7-sulfooxy-4-methylcoumarin or hymecromone 7-sulfate, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 4-methylumbelliferyl sulfate is found in Apis cerana. 4-methylumbelliferyl sulfate was first documented in 1986 (PMID: 3713703). 4-Methylumbelliferone sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 3619646) (PMID: 8355186).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310081917512D          

 17 18  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    4.2868    0.8250    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
    3.5724    1.2375    0.0000 C   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
    2.8579    0.8250    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11 10  2  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  7  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)OC2=C1C=CC(OS(O)(=O)=O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O6S/c1-6-4-10(11)15-9-5-7(2-3-8(6)9)16-17(12,13)14/h2-5H,1H3,(H,12,13,14)

> <INCHI_KEY>
FUYLLJCBCKRIAL-UHFFFAOYSA-N

> <FORMULA>
C10H8O6S

> <MOLECULAR_WEIGHT>
256.23

> <EXACT_MASS>
256.004159152

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.734811404066637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4-methyl-2-oxo-2H-chromen-7-yl)oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
1.3038755523333332

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.3172372512717567

> <JCHEM_PKA_STRONGEST_BASIC>
-6.950925780746796

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
57.803300000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylumbelliferyl sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-19         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
CONECT    1    6                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    6   10                                                       
CONECT    5    7    9                                                       
CONECT    6    1    4    8                                                  
CONECT    7    2    5   16                                                  
CONECT    8    3    6    9                                                  
CONECT    9    5    8   15                                                  
CONECT   10    4   11   15                                                  
CONECT   11   10                                                            
CONECT   12   17                                                            
CONECT   13   17                                                            
CONECT   14   17                                                            
CONECT   15    9   10                                                       
CONECT   16    7   17                                                       
CONECT   17   12   13   14   16                                             
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
(4-Methyl-2-oxidanylidene-chromen-7-yl) hydrogen sulfate	ChEBI
(4-Methyl-2-oxochromen-7-yl) hydrogen sulfate	ChEBI
4-Methyl-2-oxo-2H-1-benzopyran-7-yl hydrogen sulfate	ChEBI
4-Methyl-7-(sulfooxy)-2H-1-benzopyran-2-one	ChEBI
4-Methylumbelliferyl sulfate	ChEBI
7-Sulfooxy-4-methylcoumarin	ChEBI
Hymecromone 7-sulfate	ChEBI
(4-Methyl-2-oxidanylidene-chromen-7-yl) hydrogen sulfuric acid	Generator
(4-Methyl-2-oxidanylidene-chromen-7-yl) hydrogen sulphate	Generator
(4-Methyl-2-oxidanylidene-chromen-7-yl) hydrogen sulphuric acid	Generator
(4-Methyl-2-oxochromen-7-yl) hydrogen sulfuric acid	Generator
(4-Methyl-2-oxochromen-7-yl) hydrogen sulphate	Generator
(4-Methyl-2-oxochromen-7-yl) hydrogen sulphuric acid	Generator
4-Methyl-2-oxo-2H-1-benzopyran-7-yl hydrogen sulfuric acid	Generator
4-Methyl-2-oxo-2H-1-benzopyran-7-yl hydrogen sulphate	Generator
4-Methyl-2-oxo-2H-1-benzopyran-7-yl hydrogen sulphuric acid	Generator
4-Methyl-7-(sulphooxy)-2H-1-benzopyran-2-one	Generator
4-Methylumbelliferyl sulfuric acid	Generator
4-Methylumbelliferyl sulphate	Generator
4-Methylumbelliferyl sulphuric acid	Generator
7-Sulphooxy-4-methylcoumarin	Generator
Hymecromone 7-sulfuric acid	Generator
Hymecromone 7-sulphate	Generator
Hymecromone 7-sulphuric acid	Generator
4-Methylumbelliferone sulfuric acid	Generator
4-Methylumbelliferone sulphate	Generator
4-Methylumbelliferone sulphuric acid	Generator
4-Methylumbelliferyl sulfate, potassium salt	MeSH
4-Methylumbelliferone sulfate	MeSH
Hymecromone sulfate	MeSH

Chemical Formula

C₁₀H₈O₆S

Average Mass

256.2300 Da

Monoisotopic Mass

256.00416 Da

IUPAC Name

(4-methyl-2-oxo-2H-chromen-7-yl)oxidanesulfonic acid

Traditional Name

4-methylumbelliferyl sulfate

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)OC2=C1C=CC(OS(O)(=O)=O)=C2

InChI Identifier

InChI=1S/C10H8O6S/c1-6-4-10(11)15-9-5-7(2-3-8(6)9)16-17(12,13)14/h2-5H,1H3,(H,12,13,14)

InChI Key

FUYLLJCBCKRIAL-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
Arylsulfate
1-benzopyran
Pyranone
Pyran
Sulfuric acid monoester
Sulfate-ester
Benzenoid
Sulfuric acid ester
Organic sulfuric acid or derivatives
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

heterocyclyl sulfate (CHEBI:1905 )

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	-0.23	ALOGPS
logP	1.3	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.8 m³·mol⁻¹	ChemAxon
Polarizability	22.73 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

HMDB0240465

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093644

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11585

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

1905

Good Scents ID

Not Available

References

General References

Anundi I, Kauffman FC, el-Mouelhi M, Thurman RG: Hydrolysis of 4-methylumbelliferyl sulfate in periportal and pericentral areas of the liver lobule. Arch Toxicol. 1987;60(1-3):69-72. doi: 10.1007/BF00296950. [PubMed:3619646 ]
Anundi IM, Kauffman FC, el-Mouelhi M, Thurman RG: Hydrolysis of organic sulfates in periportal and pericentral regions of the liver lobule: studies with 4-methylumbelliferyl sulfate in the perfused rat liver. Mol Pharmacol. 1986 Jun;29(6):599-605. [PubMed:3713703 ]
Chiba M, Pang KS: Effect of protein binding on 4-methylumbelliferyl sulfate desulfation kinetics in perfused rat liver. J Pharmacol Exp Ther. 1993 Aug;266(2):492-9. [PubMed:8355186 ]
LOTUS database [Link]

Showing NP-Card for 4-methylumbelliferyl sulfate (NP0302986)

MOL for NP0302986 (4-methylumbelliferyl sulfate)

3D MOL for NP0302986 (4-methylumbelliferyl sulfate)

3D SDF for NP0302986 (4-methylumbelliferyl sulfate)

3D-SDF for NP0302986 (4-methylumbelliferyl sulfate)

PDB for NP0302986 (4-methylumbelliferyl sulfate)

3D PDB for NP0302986 (4-methylumbelliferyl sulfate)

SMILES for NP0302986 (4-methylumbelliferyl sulfate)

INCHI for NP0302986 (4-methylumbelliferyl sulfate)

Structure for NP0302986 (4-methylumbelliferyl sulfate)

3D Structure for NP0302986 (4-methylumbelliferyl sulfate)