NP-MRD: Showing NP-Card for 4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0255651)

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Record Information

Version

2.0

Created at

2022-09-07 20:12:56 UTC

Updated at

2022-09-07 20:12:57 UTC

NP-MRD ID

NP0255651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

4,5-Dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-5,8-dihydro-2H-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Xanthium strumarium. 4,5-Dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-5,8-dihydro-2H-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261501442D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261501442D          

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  2  4  1  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  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
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  4  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(COC2OC(CO)C(O)C(O)C2OC(=O)C=CC2=CC=C(O)C(O)=C2)=CC(=O)C2=C1SCC(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C26H29NO11S/c1-26(2)13(8-16(31)20-24(26)39-11-18(32)27-20)10-36-25-23(22(35)21(34)17(9-28)37-25)38-19(33)6-4-12-3-5-14(29)15(30)7-12/h3-8,17,21-23,25,28-30,34-35H,9-11H2,1-2H3,(H,27,32)

> <INCHI_KEY>
FDTNSLCBUZJFSU-UHFFFAOYSA-N

> <FORMULA>
C26H29NO11S

> <MOLECULAR_WEIGHT>
563.57

> <EXACT_MASS>
563.146131932

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.29948525872062

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(8,8-dimethyl-3,5-dioxo-3,4,5,8-tetrahydro-2H-1,4-benzothiazin-7-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
-0.027898191333332323

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.730946900519132

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207461977936514

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98108419941208

> <JCHEM_POLAR_SURFACE_AREA>
192.07999999999998

> <JCHEM_REFRACTIVITY>
140.78470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(8,8-dimethyl-3,5-dioxo-2,4-dihydro-1,4-benzothiazin-7-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.990   1.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0       2.667  -0.000   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8                                                       
CONECT   15    4   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-5,8-dihydro-2H-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₆H₂₉NO₁₁S

Average Mass

563.5700 Da

Monoisotopic Mass

563.14613 Da

IUPAC Name

2-[(8,8-dimethyl-3,5-dioxo-3,4,5,8-tetrahydro-2H-1,4-benzothiazin-7-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

2-[(8,8-dimethyl-3,5-dioxo-2,4-dihydro-1,4-benzothiazin-7-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1(C)C(COC2OC(CO)C(O)C(O)C2OC(=O)C=CC2=CC=C(O)C(O)=C2)=CC(=O)C2=C1SCC(=O)N2

InChI Identifier

InChI=1S/C26H29NO11S/c1-26(2)13(8-16(31)20-24(26)39-11-18(32)27-20)10-36-25-23(22(35)21(34)17(9-28)37-25)38-19(33)6-4-12-3-5-14(29)15(30)7-12/h3-8,17,21-23,25,28-30,34-35H,9-11H2,1-2H3,(H,27,32)

InChI Key

FDTNSLCBUZJFSU-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
Xanthium strumarium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Benzothiazine
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Para-thiazine
Monocyclic benzene moiety
Monosaccharide
Oxane
Vinylogous thioester
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Thioenolether
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Ketone
Lactam
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic nitrogen 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
logP	1.52	ALOGPS
logP	-0.028	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.08 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	140.78 m³·mol⁻¹	ChemAxon
Polarizability	56.3 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0255651)

MOL for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0255651 (4,5-dihydroxy-2-[(3-hydroxy-8,8-dimethyl-5-oxo-2h-1,4-benzothiazin-7-yl)methoxy]-6-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)