NP-MRD: Showing NP-Card for (1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione (NP0250950)

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Record Information

Version

2.0

Created at

2022-09-07 13:58:09 UTC

Updated at

2022-09-07 13:58:09 UTC

NP-MRD ID

NP0250950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215582D          

 34 36  0  0  1  0            999 V2000
    3.7940    3.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072215582D          

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 23 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  6  0  0  0
 29 32  1  0  0  0  0
 20 32  1  0  0  0  0
 20 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0250950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1(CC=C(C)C)C(O)=C(C(C)=O)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/C28H40O6/c1-16(2)8-12-27(13-9-17(3)4)22(30)21(18(5)29)23(31)28(24(27)32)14-20-19(26(7,34)15-28)10-11-25(20,6)33/h8-9,19-20,30,33-34H,10-15H2,1-7H3/t19-,20+,25-,26-,28-/m1/s1

> <INCHI_KEY>
BMTORNFHNMDAAJ-TZGUHJPRSA-N

> <FORMULA>
C28H40O6

> <MOLECULAR_WEIGHT>
472.622

> <EXACT_MASS>
472.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.56180514493825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
4.061533275666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.453433735561898

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5046299207386955

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8976801898155387

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
134.464

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.082   6.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.530   5.093   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.030   4.744   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.479   3.968   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.927   2.494   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.427   2.146   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.875   1.370   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.166   0.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.083  -1.009   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.710  -1.706   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.627  -3.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.420  -0.866   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.272  -0.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.743  -0.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.139  -1.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.611  -1.835   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.064  -2.881   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.375   1.718   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.323   0.593   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.927   3.191   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.875   2.066   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.375   2.415   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.927   3.888   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.613   3.917   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.116   2.461   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.112   1.533   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.669   0.206   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.843   0.177   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.978   5.013   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.688   5.853   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.582   6.430   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.479   4.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.979   4.316   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.530   5.789   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13   18                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    7   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   32   33                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   20                                                       
CONECT   33   20    4   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₆

Average Mass

472.6220 Da

Monoisotopic Mass

472.28249 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1(CC=C(C)C)C(O)=C(C(C)=O)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/C28H40O6/c1-16(2)8-12-27(13-9-17(3)4)22(30)21(18(5)29)23(31)28(24(27)32)14-20-19(26(7,34)15-28)10-11-25(20,6)33/h8-9,19-20,30,33-34H,10-15H2,1-7H3/t19-,20+,25-,26-,28-/m1/s1

InChI Key

BMTORNFHNMDAAJ-TZGUHJPRSA-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
Harrisonia perforata	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	4.06	ChemAxon
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.46 m³·mol⁻¹	ChemAxon
Polarizability	52.56 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	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione (NP0250950)

MOL for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D MOL for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D SDF for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D-SDF for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

PDB for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D PDB for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

SMILES for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

INCHI for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

Structure for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)

3D Structure for NP0250950 ((1s,3'r,3'as,7'r,7'ar)-3-acetyl-3',4,7'-trihydroxy-3',7'-dimethyl-5,5-bis(3-methylbut-2-en-1-yl)-1',2',3'a,4',6',7'a-hexahydrospiro[cyclohexane-1,5'-inden]-3-ene-2,6-dione)