NP-MRD: Showing NP-Card for (3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate (NP0190731)

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Record Information

Version

2.0

Created at

2022-09-04 07:27:28 UTC

Updated at

2022-09-04 07:27:28 UTC

NP-MRD ID

NP0190731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate

Description

(3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate is found in Thapsia garganica.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209272D          

 35 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652309042209272D          

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 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  1  0  0  0
 35 32  1  6  0  0  0
  7 35  1  0  0  0  0
 28 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190731

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1C[C@](C)(OC(C)=O)[C@H]2[C@H](OC(=O)[C@H](C)CC)C=C(C)[C@H]2[C@@H]2OC(=O)[C@@](C)(O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O9/c1-8-10-18(28)32-17-12-25(6,35-15(5)27)20-16(33-23(29)13(3)9-2)11-14(4)19(20)22-21(17)26(7,31)24(30)34-22/h11,13,16-17,19-22,31H,8-10,12H2,1-7H3/t13-,16-,17+,19-,20+,21-,22+,25+,26+/m1/s1

> <INCHI_KEY>
DPGCVTONCGVDNK-RPNNJQEHSA-N

> <FORMULA>
C26H38O9

> <MOLECULAR_WEIGHT>
494.581

> <EXACT_MASS>
494.251582804

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.109014000552726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,6S,6aR,7R,9aS,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-7-yl (2R)-2-methylbutanoate

> <JCHEM_LOGP>
2.737259654

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.206578297460874

> <JCHEM_PKA_STRONGEST_BASIC>
-4.020642652690612

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000002

> <JCHEM_REFRACTIVITY>
123.8439

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,6S,6aR,7R,9aS,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-7-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0     -13.692  10.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.548   9.784   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.083  10.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.939   9.230   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -10.259   7.723   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -8.474   9.706   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.330   8.675   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.905   9.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.559   8.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.128   9.987   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.022   8.417   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.174   9.702   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.863  11.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.637   9.610   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.307   6.990   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.338   5.846   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.568   4.512   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.194   3.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.061   4.832   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.900   6.364   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.567   7.134   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.233   6.364   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.233   4.824   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.101   7.134   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.101   8.674   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.434   6.364   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.768   7.134   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.875   5.938   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.799   4.705   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.256   5.203   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -10.515   4.317   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -9.233   6.743   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.767   6.605   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -9.531   8.254   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -7.761   7.197   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   20                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   16   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32    7   28                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₉

Average Mass

494.5810 Da

Monoisotopic Mass

494.25158 Da

IUPAC Name

(3S,3aR,4S,6S,6aR,7R,9aS,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-7-yl (2R)-2-methylbutanoate

Traditional Name

(3S,3aR,4S,6S,6aR,7R,9aS,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-7-yl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1C[C@](C)(OC(C)=O)[C@H]2[C@H](OC(=O)[C@H](C)CC)C=C(C)[C@H]2[C@@H]2OC(=O)[C@@](C)(O)[C@H]12

InChI Identifier

InChI=1S/C26H38O9/c1-8-10-18(28)32-17-12-25(6,35-15(5)27)20-16(33-23(29)13(3)9-2)11-14(4)19(20)22-21(17)26(7,31)24(30)34-22/h11,13,16-17,19-22,31H,8-10,12H2,1-7H3/t13-,16-,17+,19-,20+,21-,22+,25+,26+/m1/s1

InChI Key

DPGCVTONCGVDNK-RPNNJQEHSA-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
Thapsia garganica	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	2.74	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	123.84 m³·mol⁻¹	ChemAxon
Polarizability	53.11 Å³	ChemAxon
Number of Rings	3	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate (NP0190731)

MOL for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

3D MOL for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

3D SDF for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

3D-SDF for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

PDB for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

3D PDB for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

SMILES for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

INCHI for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

Structure for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)

3D Structure for NP0190731 ((3s,3ar,4s,6s,6ar,7r,9as,9bs)-6-(acetyloxy)-4-(butanoyloxy)-3-hydroxy-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-7-yl (2r)-2-methylbutanoate)