NP-MRD: Showing NP-Card for (1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione (NP0200144)

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Record Information

Version

2.0

Created at

2022-09-04 18:55:20 UTC

Updated at

2022-09-04 18:55:20 UTC

NP-MRD ID

NP0200144

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1S,3'R,3'aS,5R,7'R,7'aS)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3',3'a,4',6',7',7'a-octahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione is found in Hypericum geminiflorum. Based on a literature review very few articles have been published on (1S,3'R,3'aS,5R,7'R,7'aS)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3',3'a,4',6',7',7'a-octahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220552D          

 33 35  0  0  1  0            999 V2000
    4.1172    4.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309042220552D          

 33 35  0  0  1  0            999 V2000
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 17 18  2  0  0  0  0
 19 17  1  6  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 22 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 28 31  1  0  0  0  0
 19 31  1  0  0  0  0
 19 32  1  0  0  0  0
  7 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0200144

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)C1=C(O)[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/C27H40O6/c1-8-16(4)20(28)19-21(29)24(5,11-9-15(2)3)23(31)27(22(19)30)13-18-17(26(7,33)14-27)10-12-25(18,6)32/h9,16-18,29,32-33H,8,10-14H2,1-7H3/t16?,17-,18-,24+,25+,26+,27+/m0/s1

> <INCHI_KEY>
KSRRLFUYYFYAAH-YOSVQTMISA-N

> <FORMULA>
C27H40O6

> <MOLECULAR_WEIGHT>
460.611

> <EXACT_MASS>
460.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.22166196056933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
4.534478456

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.453434137014842

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.576664251820148

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8976801883025267

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
129.06479999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3'R,3'aS,5R,7'R,7'aS)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-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                                 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       7.686   9.164   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.134   7.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.082   6.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.582   6.914   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.530   5.093   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.030   4.744   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.479   3.968   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.927   2.494   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.427   2.146   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.875   1.370   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.166   0.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.272  -0.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.197  -1.278   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.593  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.518  -3.926   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.064  -2.881   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.375   1.718   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.323   0.593   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.927   3.191   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.875   2.066   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.375   2.415   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.927   3.888   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.613   3.917   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.116   2.461   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.112   1.533   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.669   0.206   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.843   0.177   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.978   5.013   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.688   5.853   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.582   6.430   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.479   4.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.979   4.316   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.530   5.789   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   32                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   31   32                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   19                                                       
CONECT   32   19    7   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₆

Average Mass

460.6110 Da

Monoisotopic Mass

460.28249 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)C1=C(O)[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/C27H40O6/c1-8-16(4)20(28)19-21(29)24(5,11-9-15(2)3)23(31)27(22(19)30)13-18-17(26(7,33)14-27)10-12-25(18,6)32/h9,16-18,29,32-33H,8,10-14H2,1-7H3/t16?,17-,18-,24+,25+,26+,27+/m0/s1

InChI Key

KSRRLFUYYFYAAH-YOSVQTMISA-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 geminiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Polyol
Enol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

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

23330044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione (NP0200144)

MOL for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D MOL for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D SDF for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D-SDF for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

PDB for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D PDB for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

SMILES for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

INCHI for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

Structure for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D Structure for NP0200144 ((1s,3'r,3'as,5r,7'r,7'as)-3',4,7'-trihydroxy-3',5,7'-trimethyl-5-(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)