NP-MRD: Showing NP-Card for (3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol (NP0286114)

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Record Information

Version

2.0

Created at

2022-09-09 14:33:22 UTC

Updated at

2022-09-09 14:33:23 UTC

NP-MRD ID

NP0286114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol

Description

CHEMBL251233 belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. Based on a literature review very few articles have been published on CHEMBL251233.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216332D          

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     RDKit          3D

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  Mrv1652309092216332D          

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   -3.5724    3.7125    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
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1994    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  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
 18 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 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
 14 27  2  0  0  0  0
 21 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 13 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  2  0  0  0  0
  3 35  1  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 11 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286114

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(O)=C3CO[C@@H](C)[C@@H](O)C3=C(C2=C1)C1=C2C=C3[C@H](O)[C@H](C)OCC3=C(O)C2=C(OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H32O10/c1-12-28(33)15-8-17-23(20(32)9-22(39-5)25(17)30(35)18(15)10-40-12)26-16-6-14(37-3)7-21(38-4)24(16)31(36)19-11-41-13(2)29(34)27(19)26/h6-9,12-13,28-29,32-36H,10-11H2,1-5H3/t12-,13-,28+,29+/m0/s1

> <INCHI_KEY>
SCANZLMQCZBPCM-SAAODOGCSA-N

> <FORMULA>
C31H32O10

> <MOLECULAR_WEIGHT>
564.587

> <EXACT_MASS>
564.19954723

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.944337641574414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S)-6-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4,7,10-triol

> <JCHEM_LOGP>
3.04220317

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.385116207160069

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.826713328035463

> <JCHEM_PKA_STRONGEST_BASIC>
-3.498767723783611

> <JCHEM_POLAR_SURFACE_AREA>
147.29999999999998

> <JCHEM_REFRACTIVITY>
150.4329

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-6-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4,7,10-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -0.000   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  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -0.000   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  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+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   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.574   2.604   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.239   3.556   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   34                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   41                                                  
CONECT   12   11   13   36                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   33                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   14   21                                                  
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   24                                                       
CONECT   34   13    8   35                                                  
CONECT   35   34    3                                                       
CONECT   36   12   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   11                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₂O₁₀

Average Mass

564.5870 Da

Monoisotopic Mass

564.19955 Da

IUPAC Name

(3S,4S)-6-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4,7,10-triol

Traditional Name

(3S,4S)-6-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4,7,10-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(O)=C3CO[C@@H](C)[C@@H](O)C3=C(C2=C1)C1=C2C=C3[C@H](O)[C@H](C)OCC3=C(O)C2=C(OC)C=C1O

InChI Identifier

InChI=1S/C31H32O10/c1-12-28(33)15-8-17-23(20(32)9-22(39-5)25(17)30(35)18(15)10-40-12)26-16-6-14(37-3)7-21(38-4)24(16)31(36)19-11-41-13(2)29(34)27(19)26/h6-9,12-13,28-29,32-36H,10-11H2,1-5H3/t12-,13-,28+,29+/m0/s1

InChI Key

SCANZLMQCZBPCM-SAAODOGCSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Arylnaphthalene lignans

Sub Class

Not Available

Direct Parent

Arylnaphthalene lignans

Alternative Parents

Substituents

Arylnaphthalene lignan skeleton
Naphthopyran
2-naphthol
1-naphthol
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Pyran
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen 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	3.04	ChemAxon
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	147.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	150.43 m³·mol⁻¹	ChemAxon
Polarizability	58.94 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

23310875

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23657293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol (NP0286114)

MOL for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

3D MOL for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

3D SDF for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

3D-SDF for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

PDB for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

3D PDB for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

SMILES for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

INCHI for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

Structure for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)

3D Structure for NP0286114 ((3s,4s)-6-[(3s,4s)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-5-yl]-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4,7,10-triol)