NP-MRD: Showing NP-Card for (2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one (NP0208591)

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Record Information

Version

2.0

Created at

2022-09-05 05:39:01 UTC

Updated at

2022-09-05 05:39:01 UTC

NP-MRD ID

NP0208591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one

Description

(2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one is found in Humulus lupulus.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207392D          

 31 32  0  0  1  0            999 V2000
    2.9166   -1.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738   -1.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825    1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1647    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9772    2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075    1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2593    2.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 17 22  1  0  0  0  0
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 27 29  1  0  0  0  0
 23 30  2  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 69 70  0  0  0  0  0  0  0  0999 V2000
    2.5614    0.3395   -4.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    0.4442   -2.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0312   -3.4657    0.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9615   -2.1969   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6844   -3.5043   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309052207392D          

 31 32  0  0  1  0            999 V2000
    2.9166   -1.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0208591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C2=C1O[C@H](C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O5/c1-15(2)9-11-26(12-10-16(3)4)23(28)18-14-20(25(7,8)30)31-22(18)21(24(26)29)19(27)13-17(5)6/h9-10,17,20,29-30H,11-14H2,1-8H3/t20-/m1/s1

> <INCHI_KEY>
HWYZDQMASKCQDN-HXUWFJFHSA-N

> <FORMULA>
C26H38O5

> <MOLECULAR_WEIGHT>
430.585

> <EXACT_MASS>
430.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.00318659201035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3,4,5-tetrahydro-1-benzofuran-4-one

> <JCHEM_LOGP>
4.610158848333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.321863971692448

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.494773050605566

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1064761643670264

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
127.44359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.444  -2.269   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.928  -2.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.938  -3.181   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.401  -0.554   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.391   0.626   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.381   2.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.907   3.787   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.424   4.055   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.414   2.875   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.951   5.502   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.253   2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.713   4.383   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.713   1.303   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.864   6.693   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.137   9.003   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.530   9.003   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.198   4.383   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   30                                             
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   22                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   17   14                                                       
CONECT   23   15   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23    6   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₅

Average Mass

430.5850 Da

Monoisotopic Mass

430.27192 Da

IUPAC Name

(2R)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3,4,5-tetrahydro-1-benzofuran-4-one

Traditional Name

(2R)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C2=C1O[C@H](C2)C(C)(C)O

InChI Identifier

InChI=1S/C26H38O5/c1-15(2)9-11-26(12-10-16(3)4)23(28)18-14-20(25(7,8)30)31-22(18)21(24(26)29)19(27)13-17(5)6/h9-10,17,20,29-30H,11-14H2,1-8H3/t20-/m1/s1

InChI Key

HWYZDQMASKCQDN-HXUWFJFHSA-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
Humulus lupulus	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	4.61	ChemAxon
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.44 m³·mol⁻¹	ChemAxon
Polarizability	49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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 (2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one (NP0208591)

MOL for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D MOL for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D SDF for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D-SDF for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

PDB for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D PDB for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

SMILES for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

INCHI for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

Structure for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D Structure for NP0208591 ((2r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-4-one)