NP-MRD: Showing NP-Card for (3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid (NP0156432)

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Record Information

Version

2.0

Created at

2022-09-02 13:38:24 UTC

Updated at

2022-09-02 13:38:25 UTC

NP-MRD ID

NP0156432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid

Description

(3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid is found in Mahurea palustris.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215382D          

 38 39  0  0  1  0            999 V2000
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  9 36  1  0  0  0  0
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 36 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022215382D          

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    0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -5.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -4.6629    0.0000 C   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 30 36  1  0  0  0  0
  9 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H](CC(O)=O)C1=C2OC(O)=C(C(=O)[C@H](C)CC)C(=O)[C@@]2(CC=C(C)C)C[C@H](CC=C(C)C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O6/c1-10-12-22(17-24(33)34)26-29-32(16-15-20(5)6,18-23(31(26,8)9)14-13-19(3)4)28(36)25(30(37)38-29)27(35)21(7)11-2/h13,15,21-23,37H,10-12,14,16-18H2,1-9H3,(H,33,34)/t21-,22+,23+,32-/m1/s1

> <INCHI_KEY>
YCKXZLNJJBVOJD-BVFDLDEOSA-N

> <FORMULA>
C32H48O6

> <MOLECULAR_WEIGHT>
528.73

> <EXACT_MASS>
528.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
59.657788016644034

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-[(4aS,6S)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2R)-2-methylbutanoyl]-4-oxo-4a,5,6,7-tetrahydro-4H-chromen-8-yl]hexanoic acid

> <ALOGPS_LOGP>
5.68

> <JCHEM_LOGP>
8.185844416333335

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.265151162418401

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3930728921504723

> <JCHEM_PKA_STRONGEST_BASIC>
-5.479436918854639

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
163.60400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-[(4aS,6S)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2R)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid

> <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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.873  -9.956   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.150  -8.704   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   36                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   14   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   10   24   29                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30    9   37   38                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₈O₆

Average Mass

528.7300 Da

Monoisotopic Mass

528.34509 Da

IUPAC Name

(3S)-3-[(4aS,6S)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2R)-2-methylbutanoyl]-4-oxo-4a,5,6,7-tetrahydro-4H-chromen-8-yl]hexanoic acid

Traditional Name

(3S)-3-[(4aS,6S)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2R)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid

CAS Registry Number

Not Available

SMILES

CCC[C@@H](CC(O)=O)C1=C2OC(O)=C(C(=O)[C@H](C)CC)C(=O)[C@@]2(CC=C(C)C)C[C@H](CC=C(C)C)C1(C)C

InChI Identifier

InChI=1S/C32H48O6/c1-10-12-22(17-24(33)34)26-29-32(16-15-20(5)6,18-23(31(26,8)9)14-13-19(3)4)28(36)25(30(37)38-29)27(35)21(7)11-2/h13,15,21-23,37H,10-12,14,16-18H2,1-9H3,(H,33,34)/t21-,22+,23+,32-/m1/s1

InChI Key

YCKXZLNJJBVOJD-BVFDLDEOSA-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
Mahurea palustris	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	5.68	ALOGPS
logP	8.19	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	2.39	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	163.6 m³·mol⁻¹	ChemAxon
Polarizability	59.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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 (3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid (NP0156432)

MOL for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D MOL for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D SDF for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D-SDF for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

PDB for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D PDB for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

SMILES for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

INCHI for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

Structure for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)

3D Structure for NP0156432 ((3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid)