NP-MRD: Showing NP-Card for Lupulone F (NP0078590)

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Record Information

Version

1.0

Created at

2022-04-28 23:38:31 UTC

Updated at

2022-04-28 23:38:31 UTC

NP-MRD ID

NP0078590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lupulone F

Description

1-[(2S)-5-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Lupulone F is found in Humulus lupulus L. . It was first documented in 2022 (PMID: 35501128). Based on a literature review a significant number of articles have been published on 1-[(2S)-5-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one (PMID: 35501127) (PMID: 35501126) (PMID: 35501125) (PMID: 35501124).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -3.9004    1.9671   -0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5146    0.4514   -0.1798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0223   -0.0450    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0547    0.3208   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4607    1.4751   -0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358   -0.8430   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7557   -2.1132   -0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529   -2.4457   -0.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8280   -3.1878   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5091   -2.9561   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0184   -1.6819   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -0.6301   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9514    0.6102   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621    0.1729   -0.6081 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3210    0.7272    0.4275 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3406    2.2412    0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030    0.1754    0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.3551    1.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290   -1.2138   -0.5124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9739    2.0133    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3194    2.4216    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7584    2.4335   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454    0.0753   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199    0.7577    1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0509   -0.4018    1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3581   -0.8368    1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956   -2.0797   -0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2398   -4.1769   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897   -3.8003   -0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8732    1.0279    0.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725    1.3863   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6932    0.5402   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    2.6160    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460    2.5332   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2271    2.6066    0.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3235    0.1762    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6390   -0.8806   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109    0.7385   -0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877   -0.5298    1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6 12  2  0
 12 13  1  0
 13 14  1  0
 14 19  1  0
 19 11  1  0
 11 10  2  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  1
  7  6  1  0
 11 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  3 26  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
 10 29  1  0
  9 28  1  0
  8 27  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
M  END


  Mrv1652304292201382D          

 19 20  0  0  1  0            999 V2000
    3.3523    1.9354    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
    2.6378    0.6979    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
    1.9233    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   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
    0.6538    1.5229    0.0000 C   0  0  2  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
   -0.1712    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1=C2C[C@H](OC2=CC=C1O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8(2)14(17)13-9-7-12(15(3,4)18)19-11(9)6-5-10(13)16/h5-6,8,12,16,18H,7H2,1-4H3/t12-/m0/s1

> <INCHI_KEY>
MIUCKEYAKGZFDI-LBPRGKRZSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.808314389882117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S)-5-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
3.0698841299999997

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.296465618041903

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.578289969382862

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106391463014921

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
72.4354

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2S)-5-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.590   6.693   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.860   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.320   4.383   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.320   1.303   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    4                                                       
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

1-[(2S)-5-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one

Traditional Name

1-[(2S)-5-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1=C2C[C@H](OC2=CC=C1O)C(C)(C)O

InChI Identifier

InChI=1S/C15H20O4/c1-8(2)14(17)13-9-7-12(15(3,4)18)19-11(9)6-5-10(13)16/h5-6,8,12,16,18H,7H2,1-4H3/t12-/m0/s1

InChI Key

MIUCKEYAKGZFDI-LBPRGKRZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Tertiary alcohol
Ketone
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.28	ALOGPS
logP	3.07	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.44 m³·mol⁻¹	ChemAxon
Polarizability	28.81 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163105037

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Booke F, Fauser D, Reims N, Bethge M: Unemployment due to the SARS-CoV-2-pandemic among people with and without severe disabilities: a difference-in-differences analysis. Occup Environ Med. 2022 May 2. pii: oemed-2021-108125. doi: 10.1136/oemed-2021-108125. [PubMed:35501128 ]
Ritonja JA, Aronson KJ, Leung M, Flaten L, Topouza DG, Duan QL, Durocher F, Tranmer JE, Bhatti P: Investigating the relationship between melatonin patterns and methylation in circadian genes among day shift and night shift workers. Occup Environ Med. 2022 May 2. pii: oemed-2021-108111. doi: 10.1136/oemed-2021-108111. [PubMed:35501127 ]
Kelly-Reif K, Bertke SJ, Samet J, Sood A, Schubauer-Berigan MK: Health burdens of uranium miners will extend beyond the radiation exposure compensation act deadline. Occup Environ Med. 2022 May 2. pii: oemed-2022-108311. doi: 10.1136/oemed-2022-108311. [PubMed:35501126 ]
Guseva Canu I, Gaillen-Guedy A, Antilla A, Charles S, Fraize-Frontier S, Luce D, McElvenny DM, Merletti F, Michel C, Pukkala E, Schubauer-Berigan MK, Straif K, Wild P, Richardson DB: Lung cancer mortality in the European cohort of titanium dioxide workers: a reanalysis of the exposure-response relationship. Occup Environ Med. 2022 May 2. pii: oemed-2021-108030. doi: 10.1136/oemed-2021-108030. [PubMed:35501125 ]
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Showing NP-Card for Lupulone F (NP0078590)

MOL for NP0078590 (Lupulone F)

3D MOL for NP0078590 (Lupulone F)

3D SDF for NP0078590 (Lupulone F)

3D-SDF for NP0078590 (Lupulone F)

PDB for NP0078590 (Lupulone F)

3D PDB for NP0078590 (Lupulone F)

SMILES for NP0078590 (Lupulone F)

INCHI for NP0078590 (Lupulone F)

Structure for NP0078590 (Lupulone F)

3D Structure for NP0078590 (Lupulone F)