NP-MRD: Showing NP-Card for methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate (NP0307463)

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Record Information

Version

2.0

Created at

2022-09-11 00:36:12 UTC

Updated at

2022-09-11 00:36:13 UTC

NP-MRD ID

NP0307463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate

Description

Methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-c]pyran-3-yl}acetate belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Based on a literature review very few articles have been published on methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-c]pyran-3-yl}acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112202362D          

 36 39  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
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 29 30  1  0  0  0  0
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  8 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  6 36  1  0  0  0  0
M  END

     RDKit          3D

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   -3.3230    0.1696   -1.3273 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112202362D          

 36 39  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  6 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1CC2(O)C(=O)C3=CC=C(C4CC(C(O)C(C)O4)N(C)C)C(O)=C3C(=O)C2(O)C(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO10/c1-11-20(28)16(26(3)4)9-17(35-11)14-6-7-15-19(21(14)29)23(31)25(33)12(2)36-13(8-18(27)34-5)10-24(25,32)22(15)30/h6-7,11-13,16-17,20,28-29,32-33H,8-10H2,1-5H3

> <INCHI_KEY>
GAVNVFNXYZXONL-UHFFFAOYSA-N

> <FORMULA>
C25H33NO10

> <MOLECULAR_WEIGHT>
507.536

> <EXACT_MASS>
507.210446267

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.72340778933452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-c]pyran-3-yl}acetate

> <JCHEM_LOGP>
-0.6053566558928691

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.804601166648796

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.27080402329907

> <JCHEM_PKA_STRONGEST_BASIC>
7.977633881976839

> <JCHEM_POLAR_SURFACE_AREA>
163.06

> <JCHEM_REFRACTIVITY>
125.4862

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl {8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1H,3H,4H-naphtho[2,3-c]pyran-3-yl}acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      16.004  -4.620   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   32                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   16                                                       
CONECT   27   15   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   12   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    8   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    6                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4ah,5H,10H,10ah-naphtho[2,3-c]pyran-3-yl}acetic acid	Generator

Chemical Formula

C₂₅H₃₃NO₁₀

Average Mass

507.5360 Da

Monoisotopic Mass

507.21045 Da

IUPAC Name

methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-c]pyran-3-yl}acetate

Traditional Name

methyl {8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1H,3H,4H-naphtho[2,3-c]pyran-3-yl}acetate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1CC2(O)C(=O)C3=CC=C(C4CC(C(O)C(C)O4)N(C)C)C(O)=C3C(=O)C2(O)C(C)O1

InChI Identifier

InChI=1S/C25H33NO10/c1-11-20(28)16(26(3)4)9-17(35-11)14-6-7-15-19(21(14)29)23(31)25(33)12(2)36-13(8-18(27)34-5)10-24(25,32)22(15)30/h6-7,11-13,16-17,20,28-29,32-33H,8-10H2,1-5H3

InChI Key

GAVNVFNXYZXONL-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Pyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Methyl ester
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	-0.61	ChemAxon
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	7.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	163.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.49 m³·mol⁻¹	ChemAxon
Polarizability	52.72 Å³	ChemAxon
Number of Rings	4	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

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

162815596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate (NP0307463)

MOL for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

3D MOL for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

3D SDF for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

3D-SDF for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

PDB for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

3D PDB for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

SMILES for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

INCHI for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

Structure for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)

3D Structure for NP0307463 (methyl 2-{8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4a,9,10a-trihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl}acetate)