NP-MRD: Showing NP-Card for (1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate (NP0328118)

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Record Information

Version

2.0

Created at

2022-09-12 11:17:53 UTC

Updated at

2022-09-12 11:17:53 UTC

NP-MRD ID

NP0328118

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate

Description

Not Available

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213172D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122213172D          

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    0.9343   -0.4517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7134   -0.7230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355   -1.1088    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5731   -1.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -1.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355   -2.7588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -2.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789   -1.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042   -0.3985    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4263   -0.4675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2225   -0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3516    0.3541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776   -1.2140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5997   -1.2830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -0.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8927   -0.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193    0.1409    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  1  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 15  1  1  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  6  0  0  0
 32 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0328118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1[C@H](OC(C)=O)[C@](C)(O)[C@H]2[C@@H]3C\C(C)=C/C[C@H](O)[C@](C)(OC(=O)CCC)[C@@H](O3)[C@H]2[C@@H]1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O9/c1-9-11-21(33)38-26-23(16(3)4)24-25(29(7,35)28(26)36-18(6)31)19-15-17(5)13-14-20(32)30(8,27(24)37-19)39-22(34)12-10-2/h13,16,19-20,23-28,32,35H,9-12,14-15H2,1-8H3/b17-13-/t19-,20-,23-,24-,25-,26+,27-,28-,29+,30-/m0/s1

> <INCHI_KEY>
ZPYLRKSSMZANRZ-WFASTBGXSA-N

> <FORMULA>
C30H48O9

> <MOLECULAR_WEIGHT>
552.705

> <EXACT_MASS>
552.329833126

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.662012053647494

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,4R,5S,6R,7R,8S,10E,13S,14S)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-6,10,14-trimethyl-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadec-10-en-4-yl butanoate

> <JCHEM_LOGP>
3.4972728146666645

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.04591045448434

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.41955798315066

> <JCHEM_PKA_STRONGEST_BASIC>
-3.307968805689703

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
143.4051

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,4R,5S,6R,7R,8S,10E,13S,14S)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadec-10-en-4-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.342  -7.969   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.687  -6.575   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.152  -6.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.496  -5.053   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.375  -3.788   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -4.962  -4.924   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.306  -3.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.771  -3.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.892  -4.666   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.358  -4.538   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.548  -6.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.116  -2.008   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.661  -2.515   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.226  -1.147   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.962   0.796   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.031   2.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.557   2.468   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.525   4.007   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.897   1.961   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.776   0.697   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.744  -0.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.198  -1.350   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.813  -2.070   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.070  -3.588   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.147  -2.840   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.147  -4.380   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.813  -5.150   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.480  -5.150   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.814  -4.380   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.814  -2.840   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.995  -0.744   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.529  -0.873   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.015  -0.469   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.390   0.661   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.185  -2.266   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.719  -2.395   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -7.598  -1.130   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.133  -1.259   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.943   0.263   0.000  0.00  0.00           O+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   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   31                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   13   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   15   12   32                                                  
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32    7   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₉

Average Mass

552.7050 Da

Monoisotopic Mass

552.32983 Da

IUPAC Name

(1S,2S,3S,4R,5S,6R,7R,8S,10E,13S,14S)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-6,10,14-trimethyl-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadec-10-en-4-yl butanoate

Traditional Name

(1S,2S,3S,4R,5S,6R,7R,8S,10E,13S,14S)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadec-10-en-4-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1[C@H](OC(C)=O)[C@](C)(O)[C@H]2[C@@H]3C\C(C)=C/C[C@H](O)[C@](C)(OC(=O)CCC)[C@@H](O3)[C@H]2[C@@H]1C(C)C

InChI Identifier

InChI=1S/C30H48O9/c1-9-11-21(33)38-26-23(16(3)4)24-25(29(7,35)28(26)36-18(6)31)19-15-17(5)13-14-20(32)30(8,27(24)37-19)39-22(34)12-10-2/h13,16,19-20,23-28,32,35H,9-12,14-15H2,1-8H3/b17-13-/t19-,20-,23-,24-,25-,26+,27-,28-,29+,30-/m0/s1

InChI Key

ZPYLRKSSMZANRZ-WFASTBGXSA-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

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	3.5	ChemAxon
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	143.41 m³·mol⁻¹	ChemAxon
Polarizability	59.66 Å³	ChemAxon
Number of Rings	3	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate (NP0328118)

MOL for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

3D MOL for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

3D SDF for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

3D-SDF for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

PDB for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

3D PDB for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

SMILES for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

INCHI for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

Structure for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)

3D Structure for NP0328118 ((1s,2s,3s,4r,5s,6r,7r,8s,10e,13s,14s)-5-(acetyloxy)-14-(butanoyloxy)-6,13-dihydroxy-3-isopropyl-6,10,14-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadec-10-en-4-yl butanoate)