NP-MRD: Showing NP-Card for (2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol (NP0272802)

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Record Information

Version

2.0

Created at

2022-09-08 19:35:32 UTC

Updated at

2022-09-08 19:35:32 UTC

NP-MRD ID

NP0272802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol

Description

CHEMBL182980 belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. (2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol is found in Dracaena angustifolia. CHEMBL182980 is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05031423522D          

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M  END

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  Mrv0541 05031423522D          

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 32 14  1  0  0  0  0
 32 24  1  0  0  0  0
 33 25  1  0  0  0  0
 33 27  1  0  0  0  0
 34 26  1  0  0  0  0
 34 28  1  0  0  0  0
 18 35  1  6  0  0  0
 19 36  1  1  0  0  0
 27 37  1  6  0  0  0
 28 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0272802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C)CN(CCOC2=CC=C(C=C2)[C@]2([H])OC3=C(S[C@]2([H])C2=CC=C(O)C=C2)C=C(O)C=C3)C[C@]1([H])C

> <INCHI_IDENTIFIER>
InChI=1S/C28H31NO4S/c1-18-16-29(17-19(18)2)13-14-32-24-10-5-20(6-11-24)27-28(21-3-7-22(30)8-4-21)34-26-15-23(31)9-12-25(26)33-27/h3-12,15,18-19,27-28,30-31H,13-14,16-17H2,1-2H3/t18-,19-,27-,28+/m0/s1

> <INCHI_KEY>
COJFASLRENZFLP-UXHLOXSISA-N

> <FORMULA>
C28H31NO4S

> <MOLECULAR_WEIGHT>
477.615

> <EXACT_MASS>
477.197379175

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
52.6063777223999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-2-(4-{2-[(3R,4R)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol

> <ALOGPS_LOGP>
5.94

> <JCHEM_LOGP>
5.1365561474977675

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.20535430901184

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.151058406278823

> <JCHEM_PKA_STRONGEST_BASIC>
9.663413300954517

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
136.9804

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-(4-{2-[(3R,4R)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   35  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    7   21                                                       
CONECT    4    8   21                                                       
CONECT    5   10   20                                                       
CONECT    6   11   20                                                       
CONECT    7    3   22                                                       
CONECT    8    4   22                                                       
CONECT    9   12   23                                                       
CONECT   10    5   24                                                       
CONECT   11    6   24                                                       
CONECT   12    9   25                                                       
CONECT   13   14   29                                                       
CONECT   14   13   32                                                       
CONECT   15   23   26                                                       
CONECT   16   18   29                                                       
CONECT   17   19   29                                                       
CONECT   18    1   16   19   35                                             
CONECT   19    2   17   18   36                                             
CONECT   20    5    6   27                                                  
CONECT   21    3    4   28                                                  
CONECT   22    7    8   30                                                  
CONECT   23    9   15   31                                                  
CONECT   24   10   11   32                                                  
CONECT   25   12   26   33                                                  
CONECT   26   15   25   34                                                  
CONECT   27   20   28   33   37                                             
CONECT   28   21   27   34   38                                             
CONECT   29   13   16   17                                                  
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32   14   24                                                       
CONECT   33   25   27                                                       
CONECT   34   26   28                                                       
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   27                                                            
CONECT   38   28                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₁NO₄S

Average Mass

477.6150 Da

Monoisotopic Mass

477.19738 Da

IUPAC Name

(2S,3R)-2-(4-{2-[(3R,4R)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol

Traditional Name

(2S,3R)-2-(4-{2-[(3R,4R)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol

CAS Registry Number

Not Available

SMILES

[H][C@]1(C)CN(CCOC2=CC=C(C=C2)[C@]2([H])OC3=C(S[C@]2([H])C2=CC=C(O)C=C2)C=C(O)C=C3)C[C@]1([H])C

InChI Identifier

InChI=1S/C28H31NO4S/c1-18-16-29(17-19(18)2)13-14-32-24-10-5-20(6-11-24)27-28(21-3-7-22(30)8-4-21)34-26-15-23(31)9-12-25(26)33-27/h3-12,15,18-19,27-28,30-31H,13-14,16-17H2,1-2H3/t18-,19-,27-,28+/m0/s1

InChI Key

COJFASLRENZFLP-UXHLOXSISA-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
Dracaena angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Phenoxy compound
Aryl thioether
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkylarylthioether
Monocyclic benzene moiety
1,4-benzooxathiin
1,4-oxathiin
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Thioether
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organopnictogen 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	5.94	ALOGPS
logP	5.14	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.98 m³·mol⁻¹	ChemAxon
Polarizability	52.61 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

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

449205

PDB ID

AIH

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol (NP0272802)

MOL for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

3D MOL for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

3D SDF for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

3D-SDF for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

PDB for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

3D PDB for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

SMILES for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

INCHI for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

Structure for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)

3D Structure for NP0272802 ((2s,3r)-2-(4-{2-[(3r,4r)-3,4-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-3-(4-hydroxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol)