NP-MRD: Showing NP-Card for 2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one (NP0173876)

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Record Information

Version

2.0

Created at

2022-09-03 11:04:07 UTC

Updated at

2022-09-03 11:04:07 UTC

NP-MRD ID

NP0173876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one

Description

2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one is found in Dryopteris fragrans.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032213042D          

 33 35  0  0  1  0            999 V2000
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  6 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032213042D          

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 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 14 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0173876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)C1=C(O)C(C)(C)C(O)=C(CCC2=CC[C@H]3C(C)(C)CCC[C@]3(C)[C@H]2CO)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O5/c1-7-9-20(30)22-23(31)18(24(32)27(4,5)25(22)33)12-10-17-11-13-21-26(2,3)14-8-15-28(21,6)19(17)16-29/h11,19,21,29,32-33H,7-10,12-16H2,1-6H3/t19-,21-,28+/m0/s1

> <INCHI_KEY>
FBMMMZXEBGFGTG-BDHWGLMFSA-N

> <FORMULA>
C28H42O5

> <MOLECULAR_WEIGHT>
458.639

> <EXACT_MASS>
458.303224452

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.24201274623334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{2-[(1S,4aS,8aS)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
5.086720143

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.1769904438751535

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.710609094477829

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2275827579573981

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
134.0512

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{2-[(1S,4aS,8aS)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.518  -5.657   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.528  -3.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000  -7.700   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   32                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   20   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   17   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   14    6   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

C₂₈H₄₂O₅

Average Mass

458.6390 Da

Monoisotopic Mass

458.30322 Da

IUPAC Name

2-{2-[(1S,4aS,8aS)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one

Traditional Name

2-{2-[(1S,4aS,8aS)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one

CAS Registry Number

Not Available

SMILES

CCCC(=O)C1=C(O)C(C)(C)C(O)=C(CCC2=CC[C@H]3C(C)(C)CCC[C@]3(C)[C@H]2CO)C1=O

InChI Identifier

InChI=1S/C28H42O5/c1-7-9-20(30)22-23(31)18(24(32)27(4,5)25(22)33)12-10-17-11-13-21-26(2,3)14-8-15-28(21,6)19(17)16-29/h11,19,21,29,32-33H,7-10,12-16H2,1-6H3/t19-,21-,28+/m0/s1

InChI Key

FBMMMZXEBGFGTG-BDHWGLMFSA-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
Dryopteris fragrans	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	5.15	ALOGPS
logP	5.09	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.05 m³·mol⁻¹	ChemAxon
Polarizability	53.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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 2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one (NP0173876)

MOL for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

3D MOL for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

3D SDF for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

3D-SDF for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

PDB for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

3D PDB for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

SMILES for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

INCHI for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

Structure for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)

3D Structure for NP0173876 (2-{2-[(1s,4as,8as)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethyl}-6-butanoyl-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one)