NP-MRD: Showing NP-Card for Haplosinine (NP0083550)

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Record Information

Version

2.0

Created at

2022-04-29 04:33:36 UTC

Updated at

2022-04-29 04:33:36 UTC

NP-MRD ID

NP0083550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haplosinine

Description

(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R,5S,6S)-2-({4,8-dimethoxyfuro[2,3-b]quinolin-7-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Haplosinine is found in Haplophyllum acutifolium and Haplophyllum perforatum. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-{[(2S,3R,4R,5S,6S)-2-({4,8-dimethoxyfuro[2,3-b]quinolin-7-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206332D          

 39 43  0  0  1  0            999 V2000
    9.7825   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.2115    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4970    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2115    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7825    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0681    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6391    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  2 11  1  0  0  0  0
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 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292206332D          

 39 43  0  0  1  0            999 V2000
    9.7825   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  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
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 30 34  2  0  0  0  0
 26 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 27 37  2  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=NC2=C(OC)C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO13/c1-9-15(28)22(39-24-18(31)17(30)16(29)13(8-27)38-24)19(32)25(36-9)37-12-5-4-10-14(21(12)34-3)26-23-11(6-7-35-23)20(10)33-2/h4-7,9,13,15-19,22,24-25,27-32H,8H2,1-3H3/t9-,13+,15-,16+,17-,18+,19+,22+,24-,25-/m0/s1

> <INCHI_KEY>
UKJOUZLGIHETHT-QGKIOJNKSA-N

> <FORMULA>
C25H31NO13

> <MOLECULAR_WEIGHT>
553.517

> <EXACT_MASS>
553.179540062

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
54.533946160610505

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R,5S,6S)-2-({4,8-dimethoxyfuro[2,3-b]quinolin-7-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.9534156983333326

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.465960517215155

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.941246354049971

> <JCHEM_PKA_STRONGEST_BASIC>
1.6437229356224208

> <JCHEM_POLAR_SURFACE_AREA>
202.78999999999996

> <JCHEM_REFRACTIVITY>
126.69429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R,5S,6S)-2-({4,8-dimethoxyfuro[2,3-b]quinolin-7-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      18.261  -0.237   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.261   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.594   2.073   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.928   1.303   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      19.594   3.613   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      20.928   4.383   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      18.261   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.261   5.923   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      16.927   6.693   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.927   3.613   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      16.927   2.073   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.593   1.303   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.593   4.383   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.592   3.613   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.926   1.303   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.926  -0.237   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.591  -0.237   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.925  -1.007   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   21                                                       
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   18   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28   37                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   30   26   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   27   23   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₁NO₁₃

Average Mass

553.5170 Da

Monoisotopic Mass

553.17954 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R,5S,6S)-2-({4,8-dimethoxyfuro[2,3-b]quinolin-7-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R,5S,6S)-2-({4,8-dimethoxyfuro[2,3-b]quinolin-7-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=C2C=COC2=NC2=C(OC)C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)=CC=C12

InChI Identifier

InChI=1S/C25H31NO13/c1-9-15(28)22(39-24-18(31)17(30)16(29)13(8-27)38-24)19(32)25(36-9)37-12-5-4-10-14(21(12)34-3)26-23-11(6-7-35-23)20(10)33-2/h4-7,9,13,15-19,22,24-25,27-32H,8H2,1-3H3/t9-,13+,15-,16+,17-,18+,19+,22+,24-,25-/m0/s1

InChI Key

UKJOUZLGIHETHT-QGKIOJNKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Haplophyllum acutifolium	LOTUS Database	35616633
Haplophyllum perforatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Furanoquinoline
Disaccharide
O-glycosyl compound
Quinoline
Furopyridine
Anisole
Alkyl aryl ether
Benzenoid
Pyridine
Oxane
Heteroaromatic compound
Furan
Secondary alcohol
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Hydrocarbon derivative
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	0.17	ALOGPS
logP	-0.95	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	1.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	202.79 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.69 m³·mol⁻¹	ChemAxon
Polarizability	54.53 Å³	ChemAxon
Number of Rings	5	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

C00052307

Chemspider ID

10254898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13918930

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Haplosinine (NP0083550)

MOL for NP0083550 (Haplosinine)

3D MOL for NP0083550 (Haplosinine)

3D SDF for NP0083550 (Haplosinine)

3D-SDF for NP0083550 (Haplosinine)

PDB for NP0083550 (Haplosinine)

3D PDB for NP0083550 (Haplosinine)

SMILES for NP0083550 (Haplosinine)

INCHI for NP0083550 (Haplosinine)

Structure for NP0083550 (Haplosinine)

3D Structure for NP0083550 (Haplosinine)