NP-MRD: Showing NP-Card for Ipriflavone (NP0332246)

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Record Information

Version

2.0

Created at

2023-12-21 00:00:49 UTC

Updated at

2024-09-03 04:18:33 UTC

NP-MRD ID

NP0332246

Natural Product DOI

https://doi.org/10.57994/1432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ipriflavone

Description

Ipriflavone, also known as osten or FL-113, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Ipriflavone has been described as a phytoestrogen. Ipriflavone is an extremely weak basic (essentially neutral) compound (based on its pKa). The drug prevents bone loss via mechanisms that are distinct from those of estrogens. A double-blind study reveals that ipriflavone might be effective on reducing tinnitus on otosclerosis sufferers. A clinical trial reported in 2001 that it was not effective in prevention or treatment of osteoporosis. Ipriflavone (INN, JAN; brand name Yambolap) is a synthetic isoflavone which may be used to inhibit bone resorption, maintain bone density and to prevent osteoporosis in postmenopausal women. However, this is incorrect, as the drug does not bind to or activate the estrogen receptor and shows no estrogenic effects in postmenopausal women. It is not used to treat osteoporosis. Ipriflavone was first documented in 2001 (PMID: 11255425). It slows down the action of the osteoclasts (bone-eroding cells), possibly allowing the osteoblasts (bone-building cells) to build up bone mass (PMID: 23265084) (PMID: 17297162) (PMID: 21594876) (PMID: 24084576).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306502D          

 21 23  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  9  1  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 11  1  0  0  0  0
 20 17  1  0  0  0  0
 21 12  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O3/c1-12(2)21-14-8-9-15-17(10-14)20-11-16(18(15)19)13-6-4-3-5-7-13/h3-12H,1-2H3

> <INCHI_KEY>
SFBODOKJTYAUCM-UHFFFAOYSA-N

> <FORMULA>
C18H16O3

> <MOLECULAR_WEIGHT>
280.3178

> <EXACT_MASS>
280.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.91218383930779

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-7-(propan-2-yloxy)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
3.953280068333334

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.749152773155711

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
81.3708

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
osten

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   13                                                       
CONECT    7    5   13                                                       
CONECT    8    9   14                                                       
CONECT    9    8   15                                                       
CONECT   10   14   17                                                       
CONECT   11   16   20                                                       
CONECT   12    1    2   21                                                  
CONECT   13    6    7   16                                                  
CONECT   14    8   10   21                                                  
CONECT   15    9   17   18                                                  
CONECT   16   11   13   18                                                  
CONECT   17   10   15   20                                                  
CONECT   18   15   16   19                                                  
CONECT   19   18                                                            
CONECT   20   11   17                                                       
CONECT   21   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
7-(1-Methylethoxy)-3-phenyl-4H-1-benzopyran-4-one	ChEBI
7-Isopropoxyisoflavone	ChEBI
FL-113	ChEBI
Ipriflavona	ChEBI
Ipriflavonum	ChEBI
Iprosten	ChEBI
Osten	ChEBI
Yambolap	ChEBI
(Ipriflavone)	HMDB
3-Phenyl-7-(propan-2-yloxy)-4H-chromen-4-one	HMDB
7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one	HMDB
FL113	HMDB
Ipriflavone, inn	HMDB
Osteochin	HMDB
Osteofix	HMDB
Osteoquine	HMDB
Quinogin	HMDB

Chemical Formula

C₁₈H₁₆O₃

Average Mass

280.3178 Da

Monoisotopic Mass

280.10994 Da

IUPAC Name

3-phenyl-7-(propan-2-yloxy)-4H-chromen-4-one

Traditional Name

osten

CAS Registry Number

Not Available

SMILES

CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H16O3/c1-12(2)21-14-8-9-15-17(10-14)20-11-16(18(15)19)13-6-4-3-5-7-13/h3-12H,1-2H3

InChI Key

SFBODOKJTYAUCM-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Chromone
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:31719 )
isoflavones (CHEBI:31719 )

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	4.39	ALOGPS
logP	3.95	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.37 m³·mol⁻¹	ChemAxon
Polarizability	30.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032987

DrugBank ID

DB13618

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010976

KNApSAcK ID

Not Available

Chemspider ID

3616

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ipriflavone

METLIN ID

Not Available

PubChem Compound

3747

PDB ID

Not Available

ChEBI ID

31719

Good Scents ID

Not Available

References

General References

Bae M, Woo M, Kusuma IW, Arung ET, Yang CH, Kim YU: Inhibitory effects of isoflavonoids on rat prostate testosterone 5alpha-reductase. J Acupunct Meridian Stud. 2012 Dec;5(6):319-22. doi: 10.1016/j.jams.2012.07.022. Epub 2012 Aug 9. [PubMed:23265084 ]
Alexandersen P, Toussaint A, Christiansen C, Devogelaer JP, Roux C, Fechtenbaum J, Gennari C, Reginster JY: Ipriflavone in the treatment of postmenopausal osteoporosis: a randomized controlled trial. JAMA. 2001 Mar 21;285(11):1482-8. doi: 10.1001/jama.285.11.1482. [PubMed:11255425 ]
Yao J, Zhang J, Hou JF: Effects of ipriflavone on caged layer bone metabolism in vitro and in vivo. Poult Sci. 2007 Mar;86(3):503-7. doi: 10.1093/ps/86.3.503. [PubMed:17297162 ]
Yun C, Ding L, Leng Y, Zhu H, Wen A, Yang L: Determination of ipriflavone in human plasma by LC-MS and its application in a pharmacokinetic study. Biomed Chromatogr. 2012 Jan;26(1):123-8. doi: 10.1002/bmc.1641. Epub 2011 May 19. [PubMed:21594876 ]
Xiao Z, Huang C, Wu J, Sun L, Hao W, Leung LK, Huang J: The neuroprotective effects of ipriflavone against H (2)O (2) and amyloid beta induced toxicity in human neuroblastoma SH-SY5Y cells. Eur J Pharmacol. 2013 Dec 5;721(1-3):286-93. doi: 10.1016/j.ejphar.2013.09.023. Epub 2013 Sep 29. [PubMed:24084576 ]

Showing NP-Card for Ipriflavone (NP0332246)

MOL for NP0332246 (Ipriflavone)

3D MOL for NP0332246 (Ipriflavone)

3D SDF for NP0332246 (Ipriflavone)

3D-SDF for NP0332246 (Ipriflavone)

PDB for NP0332246 (Ipriflavone)

3D PDB for NP0332246 (Ipriflavone)

SMILES for NP0332246 (Ipriflavone)

INCHI for NP0332246 (Ipriflavone)

Structure for NP0332246 (Ipriflavone)

3D Structure for NP0332246 (Ipriflavone)