NP-MRD: Showing NP-Card for 4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one (NP0216832)

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Record Information

Version

2.0

Created at

2022-09-05 16:57:23 UTC

Updated at

2022-09-05 16:57:24 UTC

NP-MRD ID

NP0216832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Lupulone C belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one is found in Humulus lupulus. Based on a literature review very few articles have been published on Lupulone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218572D          

 31 32  0  0  0  0            999 V2000
    5.7897    1.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2594    0.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5416    0.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042    3.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863    4.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1988    4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560    4.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    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
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 29 30  2  0  0  0  0
  6 30  1  0  0  0  0
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M  END

     RDKit          3D

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    2.5167    2.4632   -2.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9399    1.9679   -2.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4012   -1.2581    3.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309052218572D          

 31 32  0  0  0  0            999 V2000
    5.7897    1.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2594    0.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6378   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0216832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C1=C2OC(CC2=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O)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/h9-10,17,20,28,30H,11-14H2,1-8H3

> <INCHI_KEY>
LFIUJFSCSONDPE-UHFFFAOYSA-N

> <FORMULA>
C26H38O5

> <MOLECULAR_WEIGHT>
430.585

> <EXACT_MASS>
430.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.198131272106885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.610158848333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.336164325823042

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.205589164214875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106449509759524

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
127.44359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-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      10.807   2.811   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.818   1.631   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.344   0.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.301   1.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.774   3.345   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.784   5.060   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.794   6.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.321   7.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.838   7.954   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.331   8.866   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.590  -1.007   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -2.547   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591  -3.317   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924  -3.317   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.860   2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.320   4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.320   1.303   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.924   5.923   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   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   23   29                                                       
CONECT   29   28   21   30                                                  
CONECT   30   29    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

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C1=C2OC(CC2=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O)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/h9-10,17,20,28,30H,11-14H2,1-8H3

InChI Key

LFIUJFSCSONDPE-UHFFFAOYSA-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

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Oxolane
Tertiary alcohol
Vinylogous ester
Ketone
Cyclic ketone
Enol
Oxacycle
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aldehyde
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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
logP	4.61	ChemAxon
pKa (Strongest Acidic)	7.21	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	49.2 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042710

Chemspider ID

9387648

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11212586

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one (NP0216832)

MOL for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D MOL for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D SDF for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D-SDF for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

PDB for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D PDB for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

SMILES for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

INCHI for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

Structure for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D Structure for NP0216832 (4-hydroxy-2-(2-hydroxypropan-2-yl)-5,5-bis(3-methylbut-2-en-1-yl)-7-(3-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)