NP-MRD: Showing NP-Card for (1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione (NP0156595)

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Record Information

Version

2.0

Created at

2022-09-02 13:49:21 UTC

Updated at

2022-09-02 13:49:21 UTC

NP-MRD ID

NP0156595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione

Description

(1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione is found in Hypericum ascyron.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215492D          

 37 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022215492D          

 37 39  0  0  1  0            999 V2000
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    2.4269    3.1015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707    2.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342    2.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378    2.5416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7940    3.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574    4.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1172    4.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1610    3.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    1.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5145    1.1497    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
  2  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  1  0  0  0
 17 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 23 26  1  0  0  0  0
 14 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 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
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 29 36  2  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)[C@@]2(C[C@@H]3[C@H](CC[C@]3(C)O)[C@@](C)(O)C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O6/c1-18(2)9-13-30(14-10-19(3)4)25(33)24(23(32)15-20(5)6)26(34)31(27(30)35)16-22-21(29(8,37)17-31)11-12-28(22,7)36/h9-10,20-22,33,36-37H,11-17H2,1-8H3/t21-,22+,28-,29-,31+/m0/s1

> <INCHI_KEY>
LGRNQCJSSZYILA-UWXFRRLOSA-N

> <FORMULA>
C31H46O6

> <MOLECULAR_WEIGHT>
514.703

> <EXACT_MASS>
514.329439201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
58.859837110877926

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3'S,3'aR,7'S,7'aS)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3',3'a,4',6',7',7'a-octahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
5.493656884000001

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.453433880347877

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5491916570739144

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8976801898180913

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
148.2405

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3'S,3'aR,7'S,7'aS)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.064  -2.881   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.139  -1.650   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.611  -1.835   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.743  -0.233   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.272  -0.047   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.875   1.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.166   0.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.539   1.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.829   0.386   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.747  -1.152   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.202   1.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.375   1.718   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.323   0.593   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.927   3.191   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.875   2.066   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.375   2.415   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.927   3.888   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.613   3.917   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.116   2.461   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.112   1.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.669   0.206   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.843   0.177   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.978   5.013   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.688   5.853   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.582   6.430   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.479   4.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.979   4.316   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.530   5.789   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.479   3.968   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.530   5.093   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.030   4.744   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.082   6.566   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.134   7.691   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.686   9.164   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.634   7.342   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.927   2.494   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.427   2.146   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   36                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   26   27                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   14                                                       
CONECT   27   14   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   36                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   29    6   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₆O₆

Average Mass

514.7030 Da

Monoisotopic Mass

514.32944 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)[C@@]2(C[C@@H]3[C@H](CC[C@]3(C)O)[C@@](C)(O)C2)C1=O

InChI Identifier

InChI=1S/C31H46O6/c1-18(2)9-13-30(14-10-19(3)4)25(33)24(23(32)15-20(5)6)26(34)31(27(30)35)16-22-21(29(8,37)17-31)11-12-28(22,7)36/h9-10,20-22,33,36-37H,11-17H2,1-8H3/t21-,22+,28-,29-,31+/m0/s1

InChI Key

LGRNQCJSSZYILA-UWXFRRLOSA-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
Hypericum ascyron	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	3.59	ALOGPS
logS	-5	ALOGPS

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione (NP0156595)

MOL for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D MOL for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D SDF for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D-SDF for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

PDB for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D PDB for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

SMILES for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

INCHI for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

Structure for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D Structure for NP0156595 ((1s,3's,3'ar,7's,7'as)-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)