NP-MRD: Showing NP-Card for (2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one (NP0217893)

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Record Information

Version

2.0

Created at

2022-09-05 18:23:06 UTC

Updated at

2022-09-05 18:23:06 UTC

NP-MRD ID

NP0217893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Description

1-[(3R)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. (2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one is found in Humulus lupulus. 1-[(3R)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303281714303D          

 27 29  0  0  0  0            999 V2000
    7.1572  -30.8235    7.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1423  -31.6327    7.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8426  -32.0311    7.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5578  -31.6203    7.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5727  -30.8112    7.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8724  -30.4127    7.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2582  -32.0188    7.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433  -32.8279    8.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9734  -31.6080    7.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6738  -32.0065    8.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3889  -31.5958    8.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2879  -30.4005    7.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3028  -29.5913    7.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8278  -32.8402    7.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4568  -30.4250    7.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0893  -31.9942    8.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8045  -31.5835    8.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8194  -30.7743    8.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1190  -30.3759    8.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4038  -30.7866    7.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5346  -30.3636    8.1974 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4271  -32.0433    7.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7268  -31.6449    7.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7268  -30.8199    7.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5740  -29.9439    6.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9555  -30.8591    8.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2075  -31.8546    7.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
  1  2  2  0  0  0  0
  4  7  1  0  0  0  0
  3  4  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  1 15  1  0  0  0  0
  9 10  2  0  0  0  0
 11 16  2  0  0  0  0
  2  3  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 17 18  2  0  0  0  0
  5  6  2  0  0  0  0
 18 19  1  0  0  0  0
  5 12  1  0  0  0  0
 19 20  2  0  0  0  0
 20 11  1  0  0  0  0
  6  1  1  0  0  0  0
 18 21  1  0  0  0  0
  2 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 15  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 22  1  0  0  0  0
 23 27  1  0  0  0  0
M  END


  Mrv1652303281714303D          

 27 29  0  0  0  0            999 V2000
    7.1572  -30.8235    7.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1423  -31.6327    7.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8426  -32.0311    7.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5578  -31.6203    7.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5727  -30.8112    7.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8724  -30.4127    7.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2582  -32.0188    7.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433  -32.8279    8.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9734  -31.6080    7.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6738  -32.0065    8.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3889  -31.5958    8.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2879  -30.4005    7.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3028  -29.5913    7.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8278  -32.8402    7.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4568  -30.4250    7.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0893  -31.9942    8.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8045  -31.5835    8.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8194  -30.7743    8.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1190  -30.3759    8.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4038  -30.7866    7.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5346  -30.3636    8.1974 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4271  -32.0433    7.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7268  -31.6449    7.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7268  -30.8199    7.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5740  -29.9439    6.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9555  -30.8591    8.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2075  -31.8546    7.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
  1  2  2  0  0  0  0
  4  7  1  0  0  0  0
  3  4  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  1 15  1  0  0  0  0
  9 10  2  0  0  0  0
 11 16  2  0  0  0  0
  2  3  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 17 18  2  0  0  0  0
  5  6  2  0  0  0  0
 18 19  1  0  0  0  0
  5 12  1  0  0  0  0
 19 20  2  0  0  0  0
 20 11  1  0  0  0  0
  6  1  1  0  0  0  0
 18 21  1  0  0  0  0
  2 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 15  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 22  1  0  0  0  0
 23 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C[C@@H](O)C(C)(C)O2)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+/t18-/m1/s1

> <INCHI_KEY>
GUQGMEWOCKDLDE-AHKGRUIUSA-N

> <FORMULA>
C21H22O6

> <MOLECULAR_WEIGHT>
370.401

> <EXACT_MASS>
370.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.5705737949713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-[(3R)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
3.7245573916666666

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.043975345178815

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.341817914200762

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3326512486799613

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
102.09430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-[(3R)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAR-17         0                                  
HETATM    1  C   UNK     0       7.157 -30.823   7.405  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.142 -31.633   7.565  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.843 -32.031   7.742  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.558 -31.620   7.759  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.573 -30.811   7.599  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.872 -30.413   7.422  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.258 -32.019   7.936  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.243 -32.828   8.095  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.973 -31.608   7.952  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.674 -32.007   8.129  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.389 -31.596   8.146  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.288 -30.401   7.616  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.303 -29.591   7.456  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.828 -32.840   7.901  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.457 -30.425   7.228  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.089 -31.994   8.323  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.805 -31.584   8.340  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.819 -30.774   8.180  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.119 -30.376   8.004  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.404 -30.787   7.987  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.535 -30.364   8.197  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.427 -32.043   7.548  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.727 -31.645   7.371  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.727 -30.820   7.371  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.574 -29.944   6.738  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.955 -30.859   8.141  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.207 -31.855   7.977  0.00  0.00           O+0
CONECT    1    2   15    6                                                  
CONECT    2    1    3   22                                                  
CONECT    3    4   14    2                                                  
CONECT    4    7    3    5                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   16   10   20                                                  
CONECT   12   13    5                                                       
CONECT   13   12                                                            
CONECT   14    3                                                            
CONECT   15    1   24                                                       
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   11                                                       
CONECT   21   18                                                            
CONECT   22    2   23                                                       
CONECT   23   24   22   27                                                  
CONECT   24   23   15   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₆

Average Mass

370.4010 Da

Monoisotopic Mass

370.14164 Da

IUPAC Name

(2E)-1-[(3R)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1-[(3R)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C[C@@H](O)C(C)(C)O2)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+/t18-/m1/s1

InChI Key

GUQGMEWOCKDLDE-AHKGRUIUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Hydroxycinnamic acid or derivatives
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Anisole
Styrene
Aryl ketone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Organic oxide
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	3.21	ALOGPS
logP	3.72	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.34	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.09 m³·mol⁻¹	ChemAxon
Polarizability	39.57 Å³	ChemAxon
Number of Rings	3	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one (NP0217893)

MOL for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D MOL for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D SDF for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D-SDF for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

PDB for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D PDB for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

SMILES for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

INCHI for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

Structure for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D Structure for NP0217893 ((2e)-1-[(3r)-3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one)