NP-MRD: Showing NP-Card for Butin (NP0045580)

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Record Information

Version

2.0

Created at

2022-03-17 19:32:12 UTC

Updated at

2022-03-17 19:32:12 UTC

NP-MRD ID

NP0045580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Butin

Description

Butin is found in Acacia baileyana, Acacia binervata, Acacia buxifolia, Acacia calamifolia, Acacia cardiophylla, Acacia chrysotricha, Acacia clunies-rossiae, Acacia constablei, Acacia dealbata, Acacia deanei, Acacia decora, Acacia falciformis, Acacia filicifolia, Acacia irrorata, Acacia kettlewelliae, Acacia lanigera, Acacia leucoclada, Acacia mearnsii , Acacia mollifolia, Acacia neriifolia, Acacia oshanesii, Acacia parramattensis, Acacia peuce, Acacia pycnantha, Acacia rubida, Acacia silvestris, Acacia terminalis, Acacia trachyphloia, Acacia vestita, Brucea javanica, Butea frondosa , Dalbergia odorifera , Dipteryx lacunifera, Dipteryx odorata , Gliricidia sepium , Hydnophytum formicarum, Machaerium villosum, Mangifera spp., Peltogyne paniculata, Peltogyne venosa, Robinia pseudoacacia, Spatholobus suberectus Dunn , Taxus fuana, Taxus yunnanensis and Umtiza listerana. Butin was first documented in 1986 (PMID: 3821138).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303082006222D          

 20 22  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   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
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
  9 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C(=O)C[C@H](OC2=C1)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-6,14,16-17,19H,7H2/t14-/m0/s1

> <INCHI_KEY>
MJBPUQUGJNAPAZ-AWEZNQCLSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.47523892330289

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.185108050333333

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.228785081185164

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.781562217766302

> <JCHEM_PKA_STRONGEST_BASIC>
-4.939956994421496

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.28980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11    2                                                       
CONECT   13    9   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(-)-Butin	ChEBI
7,3',4'-Trihydroxyflavanone	ChEBI

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2528 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

butin

CAS Registry Number

492-14-8

SMILES

OC1=CC=C2C(=O)C[C@H](OC2=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-6,14,16-17,19H,7H2/t14-/m0/s1

InChI Key

MJBPUQUGJNAPAZ-AWEZNQCLSA-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
Acacia baileyana	Plant	KNApSAcK
Acacia binervata	Plant	KNApSAcK
Acacia buxifolia	Plant	KNApSAcK
Acacia calamifolia	Plant	KNApSAcK
Acacia cardiophylla	Plant	KNApSAcK
Acacia chrysotricha	Plant	KNApSAcK
Acacia clunies-rossiae	Plant	KNApSAcK
Acacia constablei	Plant	KNApSAcK
Acacia dealbata	Plant	KNApSAcK
Acacia deanei	Plant	KNApSAcK
Acacia decora	Plant	KNApSAcK
Acacia falciformis	Plant	KNApSAcK
Acacia filicifolia	Plant	KNApSAcK
Acacia irrorata	Plant	KNApSAcK
Acacia kettlewelliae	Plant	KNApSAcK
Acacia lanigera	Plant	KNApSAcK
Acacia leucoclada	Plant	KNApSAcK
Acacia mearnsii	Plant	KNApSAcK
Acacia mollifolia	Plant	KNApSAcK
Acacia neriifolia	Plant	KNApSAcK
Acacia oshanesii	Plant	KNApSAcK
Acacia parramattensis	Plant	KNApSAcK
Acacia peuce	Plant	KNApSAcK
Acacia pycnantha	Plant	KNApSAcK
Acacia rubida	Plant	KNApSAcK
Acacia silvestris	Plant	KNApSAcK
Acacia terminalis	Plant	KNApSAcK
Acacia trachyphloia	Plant	KNApSAcK
Acacia vestita	Plant	KNApSAcK
Brucea javanica	LOTUS Database	35616633
Butea monosperma	Plant	KNApSAcK
Dalbergia odorifera	Plant	KNApSAcK
Dipteryx lacunifera	LOTUS Database	35616633
Dipteryx odorata	Plant	KNApSAcK
Gliricidia sepium	Plant	KNApSAcK
Hydnophytum formicarum	LOTUS Database	35616633
Machaerium villosum	Plant	KNApSAcK
Mangifera indica	FooDB	KNAPSACK
Mangifera spp.	Plant	KNApSAcK
Peltogyne paniculata	Plant	KNApSAcK
Peltogyne venosa	Plant	KNApSAcK
Robinia pseudoacacia	LOTUS Database	35616633
Spatholobus suberectus	Plant	KNApSAcK
Taxus fuana	Plant	KNApSAcK
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Umtiza listerana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Catechol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavanone (CHEBI:27725 )
flavanones (C09614 )
Flavanones (LMPK12140075 )

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	2.55	ALOGPS
logP	2.19	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.29 m³·mol⁻¹	ChemAxon
Polarizability	26.48 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

FDB001471

KNApSAcK ID

C00000945

Chemspider ID

Not Available

KEGG Compound ID

C09614

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butin_(molecule)

METLIN ID

Not Available

PubChem Compound

92775

PDB ID

Not Available

ChEBI ID

27725

Good Scents ID

Not Available

References

General References

Zhang R, Chae S, Kang KA, Piao MJ, Ko DO, Wang ZH, Park DB, Park JW, You HJ, Hyun JW: Protective effect of butin against hydrogen peroxide-induced apoptosis by scavenging reactive oxygen species and activating antioxidant enzymes. Mol Cell Biochem. 2008 Nov;318(1-2):33-42. doi: 10.1007/s11010-008-9854-x. Epub 2008 Jul 2. [PubMed:18594949 ]
Kang KA, Lee JH, Chae S, Zhang R, Piao MJ, Kim HS, You HJ, Hyun JW: Butin decreases oxidative stress-induced 8-hydroxy-2'-deoxyguanosine levels via activation of oxoguanine glycosylase 1. Chem Biol Interact. 2009 Oct 30;181(3):338-42. doi: 10.1016/j.cbi.2009.07.011. Epub 2009 Jul 22. [PubMed:19631197 ]
Zhang R, Kang KA, Piao MJ, Chang WY, Maeng YH, Chae S, Lee IK, Kim BJ, Hyun JW: Butin reduces oxidative stress-induced mitochondrial dysfunction via scavenging of reactive oxygen species. Food Chem Toxicol. 2010 Mar;48(3):922-7. doi: 10.1016/j.fct.2010.01.001. Epub 2010 Jan 12. [PubMed:20060874 ]
Zhang R, Lee IK, Piao MJ, Kim KC, Kim AD, Kim HS, Chae S, Kim HS, Hyun JW: Butin (7,3',4'-trihydroxydihydroflavone) reduces oxidative stress-induced cell death via inhibition of the mitochondria-dependent apoptotic pathway. Int J Mol Sci. 2011;12(6):3871-87. doi: 10.3390/ijms12063871. Epub 2011 Jun 10. [PubMed:21747713 ]
Zhang R, Chae S, Lee JH, Hyun JW: The cytoprotective effect of butin against oxidative stress is mediated by the up-regulation of manganese superoxide dismutase expression through a PI3K/Akt/Nrf2-dependent pathway. J Cell Biochem. 2012 Jun;113(6):1987-97. doi: 10.1002/jcb.24068. [PubMed:22253095 ]
Cho N, Choi JH, Yang H, Jeong EJ, Lee KY, Kim YC, Sung SH: Neuroprotective and anti-inflammatory effects of flavonoids isolated from Rhus verniciflua in neuronal HT22 and microglial BV2 cell lines. Food Chem Toxicol. 2012 Jun;50(6):1940-5. doi: 10.1016/j.fct.2012.03.052. Epub 2012 Mar 20. [PubMed:22465834 ]
Kang SY, Kang JY, Oh MJ: Antiviral activities of flavonoids isolated from the bark of Rhus verniciflua stokes against fish pathogenic viruses In Vitro. J Microbiol. 2012 Apr;50(2):293-300. doi: 10.1007/s12275-012-2068-7. Epub 2012 Apr 27. [PubMed:22538659 ]
Bhargava SK: Estrogenic and postcoital anticonceptive activity in rats of butin isolated from Butea monosperma seed. J Ethnopharmacol. 1986 Oct;18(1):95-101. doi: 10.1016/0378-8741(86)90046-2. [PubMed:3821138 ]

Showing NP-Card for Butin (NP0045580)

MOL for NP0045580 (Butin)

3D MOL for NP0045580 (Butin)

3D SDF for NP0045580 (Butin)

3D-SDF for NP0045580 (Butin)

PDB for NP0045580 (Butin)

3D PDB for NP0045580 (Butin)

SMILES for NP0045580 (Butin)

INCHI for NP0045580 (Butin)

Structure for NP0045580 (Butin)

3D Structure for NP0045580 (Butin)