NP-MRD: Showing NP-Card for Fraxinellone (NP0058534)

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Record Information

Version

2.0

Created at

2022-04-28 03:53:09 UTC

Updated at

2022-04-28 03:53:09 UTC

NP-MRD ID

NP0058534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fraxinellone

Description

Fraxinellone belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. Fraxinellone is found in Dictamnus albus L. , Dictamnus angustifolius, Dictamnus dasycarpus , Dictamnus radicis Cortex, Dictamus albus , Fagaropsis glabra, Melia azedarach and Raulinoa echinata. Fraxinellone was first documented in 2021 (PMID: 34717966). Based on a literature review a small amount of articles have been published on Fraxinellone (PMID: 34519225) (PMID: 34463097) (PMID: 33953684) (PMID: 33845055).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.3102    1.7482   -0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937    0.6450   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413    0.9594    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034    2.2066    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    3.3098    0.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551    1.9291   -0.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211    0.6098   -0.6176 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4537    0.0032   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3286    0.0314    0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4368   -0.7010    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2198   -1.1342   -1.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656   -0.7546   -1.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0443   -0.0745    0.1993 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4963   -0.1605    1.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.3601   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7604   -1.6971    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7808   -0.7499   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537    2.4448    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    2.2904   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.3545   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8222    0.6540   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000    0.5236    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3160   -0.8827    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480   -0.9806   -2.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8972    0.8268    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542   -0.4619    2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2929   -0.9063    1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2533   -2.2190   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5828   -1.3319   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0411   -2.7616    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804   -1.5078    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -0.9977   -1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7609   -0.8549    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8 12  2  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  7 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 13  3  1  0
  9  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  6
 12 24  1  0
 10 23  1  0
  9 22  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
M  END


  Mrv1652304282205532D          

 17 19  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    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
    1.4289    0.8250    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5546   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -2.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8242   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8242   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -0.8205    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  2 17  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0058534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C(=O)O[C@@H](C3=COC=C3)[C@]2(C)CCC1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3/t12-,14+/m0/s1

> <INCHI_KEY>
XYYAFLHHHZVPRN-GXTWGEPZSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.279

> <EXACT_MASS>
232.109944375

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.632656353048823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR)-3-(furan-3-yl)-3a,7-dimethyl-1,3,3a,4,5,6-hexahydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.1124907010000005

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8889030412881707

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
63.106200000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fraxinellone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.941   3.481   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.370   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.941  -1.941   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.035  -3.186   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.941  -4.432   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.405  -3.956   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.405  -2.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.161  -1.532   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11   17                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    3    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₃

Average Mass

232.2790 Da

Monoisotopic Mass

232.10994 Da

IUPAC Name

(3R,3aR)-3-(furan-3-yl)-3a,7-dimethyl-1,3,3a,4,5,6-hexahydro-2-benzofuran-1-one

Traditional Name

fraxinellone

CAS Registry Number

Not Available

SMILES

CC1=C2C(=O)O[C@@H](C3=COC=C3)[C@]2(C)CCC1

InChI Identifier

InChI=1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3/t12-,14+/m0/s1

InChI Key

XYYAFLHHHZVPRN-GXTWGEPZSA-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
Dictamnus albus	Plant	KNApSAcK
Dictamnus angustifolius	Plant	KNApSAcK
Dictamnus dasycarpus	Plant	KNApSAcK
Dictamnus radicis Cortex	Plant	KNApSAcK
Dictamus albus	-	KNApSAcK
Fagaropsis glabra	LOTUS Database	35616633
Melia azedarach	Plant	KNApSAcK
Raulinoa echinata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isobenzofurans

Sub Class

Not Available

Direct Parent

Isobenzofurans

Alternative Parents

Substituents

Isobenzofuran
Gamma butyrolactone
Furan
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	3.19	ALOGPS
logP	3.11	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	63.11 m³·mol⁻¹	ChemAxon
Polarizability	24.63 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011939

Chemspider ID

110550

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lu T, Peng S, Wang J, Yang S, Xu X, Li H, Shen H, Li X, Cui G, Chen G: Fraxinellone ameliorates intracerebral hemorrhage-induced secondary brain injury by regulating Kruppel-like transcription factor 2 expression in rats. Brain Res Bull. 2021 Dec;177:340-351. doi: 10.1016/j.brainresbull.2021.10.018. Epub 2021 Oct 28. [PubMed:34717966 ]
Li J, Feng T, Yang W, Xu Y, Wang S, Cai H, Liu Z, Qiang H, Zhang J: Rational formulation engineering of fraxinellone utilizing 6-O-alpha-D-maltosyl-beta-cyclodextrin for enhanced oral bioavailability and hepatic fibrosis therapy. Drug Deliv. 2021 Dec;28(1):1890-1902. doi: 10.1080/10717544.2021.1976310. [PubMed:34519225 ]
Bui D, Yin T, Duan S, Wei B, Yang P, Wong SJ, You M, Singh R, Hu M: Pharmacokinetic Characterization and Bioavailability Barrier for the Key Active Components of Botanical Drug Antitumor B (ATB) in Mice for Chemoprevention of Oral Cancer. J Nat Prod. 2021 Sep 24;84(9):2486-2495. doi: 10.1021/acs.jnatprod.1c00501. Epub 2021 Aug 31. [PubMed:34463097 ]
He B, Zhang W, He J: Fraxinellone Has Anticancer Activity by Inducing Osteosarcoma Cell Apoptosis via Promoting Excessive Autophagy Flux. Front Pharmacol. 2021 Apr 19;12:653212. doi: 10.3389/fphar.2021.653212. eCollection 2021. [PubMed:33953684 ]
Zheng B, Yuan M, Wang S, Tan Y, Xu Y, Ye J, Gao Y, Sun X, Wang T, Kong L, Wu X, Xu Q: Fraxinellone alleviates kidney fibrosis by inhibiting CUG-binding protein 1-mediated fibroblast activation. Toxicol Appl Pharmacol. 2021 Jun 1;420:115530. doi: 10.1016/j.taap.2021.115530. Epub 2021 Apr 13. [PubMed:33845055 ]

Showing NP-Card for Fraxinellone (NP0058534)

MOL for NP0058534 (Fraxinellone)

3D MOL for NP0058534 (Fraxinellone)

3D SDF for NP0058534 (Fraxinellone)

3D-SDF for NP0058534 (Fraxinellone)

PDB for NP0058534 (Fraxinellone)

3D PDB for NP0058534 (Fraxinellone)

SMILES for NP0058534 (Fraxinellone)

INCHI for NP0058534 (Fraxinellone)

Structure for NP0058534 (Fraxinellone)

3D Structure for NP0058534 (Fraxinellone)