NP-MRD: Showing NP-Card for (3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate (NP0217848)

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Record Information

Version

2.0

Created at

2022-09-05 18:19:32 UTC

Updated at

2022-09-05 18:19:32 UTC

NP-MRD ID

NP0217848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate

Description

(3S,4R)-9-[(S)-[(2S)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-4-yl acetate belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. (3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate is found in Aspergillus rugulosus. Based on a literature review very few articles have been published on (3S,4R)-9-[(S)-[(2S)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052220192D          

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M  END

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M  END


  Mrv1652309052220192D          

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 25 27  2  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  2  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0217848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]([C@@H]1OC1(C)C)C1=C2OC3=CC(C)=C4OC[C@@H]([C@@H](OC(C)=O)C4=C3C(=O)C2=C(O)C=C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O8/c1-12(2)16-11-33-23-13(3)10-18-20(21(23)25(16)34-14(4)29)22(31)19-17(30)9-8-15(24(19)35-18)26(32-7)27-28(5,6)36-27/h8-10,16,25-27,30H,1,11H2,2-7H3/t16-,25-,26+,27+/m1/s1

> <INCHI_KEY>
SFYPAIOIHIQQBW-PCSAQGNASA-N

> <FORMULA>
C28H30O8

> <MOLECULAR_WEIGHT>
494.54

> <EXACT_MASS>
494.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.742513924304724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R)-9-[(S)-[(2S)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-4-yl acetate

> <JCHEM_LOGP>
4.621030158333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.347981631201696

> <JCHEM_PKA_STRONGEST_BASIC>
-3.510206581714605

> <JCHEM_POLAR_SURFACE_AREA>
103.82000000000002

> <JCHEM_REFRACTIVITY>
131.21810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-9-[(S)-[(2S)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  -7.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.660  -6.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.148  -7.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.660  -2.686   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   0.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.709  -1.522   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.734  -0.940   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.246  -0.649   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.750   0.807   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.726   0.224   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.270   0.729   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.435   1.737   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.013   3.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.682   2.640   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.197  -5.887   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.685  -6.178   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.181  -7.633   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.189  -8.798   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.128  -8.758   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   13   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   11   31                                                  
CONECT   31   30    7   32                                                  
CONECT   32   31    4   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3S,4R)-9-[(S)-[(2S)-3,3-Dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-4-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₀O₈

Average Mass

494.5400 Da

Monoisotopic Mass

494.19407 Da

IUPAC Name

(3S,4R)-9-[(S)-[(2S)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-4-yl acetate

Traditional Name

(3S,4R)-9-[(S)-[(2S)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-4-yl acetate

CAS Registry Number

Not Available

SMILES

CO[C@H]([C@@H]1OC1(C)C)C1=C2OC3=CC(C)=C4OC[C@@H]([C@@H](OC(C)=O)C4=C3C(=O)C2=C(O)C=C1)C(C)=C

InChI Identifier

InChI=1S/C28H30O8/c1-12(2)16-11-33-23-13(3)10-18-20(21(23)25(16)34-14(4)29)22(31)19-17(30)9-8-15(24(19)35-18)26(32-7)27-28(5,6)36-27/h8-10,16,25-27,30H,1,11H2,2-7H3/t16-,25-,26+,27+/m1/s1

InChI Key

SFYPAIOIHIQQBW-PCSAQGNASA-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
Aspergillus rugulosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Chromone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen 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	4.62	ChemAxon
pKa (Strongest Acidic)	8.35	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.22 m³·mol⁻¹	ChemAxon
Polarizability	52.74 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162986725

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate (NP0217848)

MOL for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

3D MOL for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

3D SDF for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

3D-SDF for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

PDB for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

3D PDB for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

SMILES for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

INCHI for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

Structure for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)

3D Structure for NP0217848 ((3s,4r)-9-[(s)-[(2s)-3,3-dimethyloxiran-2-yl](methoxy)methyl]-6-hydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-4-yl acetate)