NP-MRD: Showing NP-Card for thunberginol f (NP0212175)

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Record Information

Version

2.0

Created at

2022-09-05 10:45:25 UTC

Updated at

2022-09-05 10:45:25 UTC

NP-MRD ID

NP0212175

Secondary Accession Numbers

None

Natural Product Identification

Common Name

thunberginol f

Description

Thunberginol F belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position. Thunberginol F is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. thunberginol f is found in Hydrangea macrophylla and Hydrangea serrata. thunberginol f was first documented in 2011 (PMID: 21650157). Based on a literature review very few articles have been published on thunberginol F (PMID: 30828074).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.6949   -2.2696    2.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320   -1.3639    1.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -0.8944    0.9057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112    0.1155   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917    0.7620   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6980    0.4365   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5755    1.5241   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9279    1.3088   -0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3988    0.0269   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7779   -0.2213   -0.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212   -1.0395   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591   -2.3174   -0.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718   -0.8311   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689    0.2882   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8846    1.1464   -0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481    1.0862   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8196    0.1964    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0062   -0.6572    1.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5735   -1.5480    1.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6403   -0.6149    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632    1.5283   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2251    2.5192   -0.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6396    2.1484   -0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3899    0.5806   -0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0347   -2.4784    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4876   -1.6559   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085    1.8299   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441    1.7790   -1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8948    0.2248    0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5671   -1.6096    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  2  0
 20  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  4 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 14 20  1  0
 13  6  1  0
 19 30  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv1652309052212452D          

 20 22  0  0  0  0            999 V2000
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    1.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   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  2  2  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212175

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2C(=O)O\C(=C/C3=CC=C(O)C(O)=C3)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-10-5-4-8(6-12(10)18)7-13-9-2-1-3-11(17)14(9)15(19)20-13/h1-7,16-18H/b13-7-

> <INCHI_KEY>
CFXQRFYFWXTZOJ-QPEQYQDCSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.24

> <EXACT_MASS>
270.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.70835979894794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-3-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-1,3-dihydro-2-benzofuran-1-one

> <JCHEM_LOGP>
3.0905989056666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.058530378711065

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.423807675198347

> <JCHEM_PKA_STRONGEST_BASIC>
-4.818082415412854

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
73.1118

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
thunberginol F

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.887   0.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.393   0.904   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.869   2.368   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.376   2.688   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.839   3.513   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.315   4.977   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6                                                       
CONECT   14    4   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14    2                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(Z)-3-((3,4-Dihydroxyphenyl)methylene)-7-hydroxy-isobenzofuran-1(3H)-one	ChEBI

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2400 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

(3Z)-3-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-1,3-dihydro-2-benzofuran-1-one

Traditional Name

thunberginol F

CAS Registry Number

Not Available

SMILES

OC1=C2C(=O)O\C(=C/C3=CC=C(O)C(O)=C3)C2=CC=C1

InChI Identifier

InChI=1S/C15H10O5/c16-10-5-4-8(6-12(10)18)7-13-9-2-1-3-11(17)14(9)15(19)20-13/h1-7,16-18H/b13-7-

InChI Key

CFXQRFYFWXTZOJ-QPEQYQDCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Hydrangea macrophylla	LOTUS Database	35616633
Hydrangea serrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Isobenzofuranones

Direct Parent

Isobenzofuranones

Alternative Parents

Substituents

Isobenzofuranone
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Enol ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechols (CHEBI:68139 )
gamma-lactone (CHEBI:68139 )
isobenzofuranone (CHEBI:68139 )

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	3.09	ChemAxon
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.11 m³·mol⁻¹	ChemAxon
Polarizability	26.71 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

4943896

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thunberginol F

METLIN ID

Not Available

PubChem Compound

6439493

PDB ID

Not Available

ChEBI ID

68139

Good Scents ID

rw1590161

References

General References

Bader A, De Tommasi N, Cotugno R, Braca A: Phenolic compounds from the roots of Jordanian viper's grass, Scorzonera judaica. J Nat Prod. 2011 Jun 24;74(6):1421-6. doi: 10.1021/np200143s. Epub 2011 Jun 8. [PubMed:21650157 ]
Shin JS, Han HS, Lee SB, Myung DB, Lee K, Lee SH, Kim HJ, Lee KT: Chemical Constituents from Leaves of Hydrangea serrata and Their Anti-photoaging Effects on UVB-Irradiated Human Fibroblasts. Biol Pharm Bull. 2019;42(3):424-431. doi: 10.1248/bpb.b18-00742. [PubMed:30828074 ]
LOTUS database [Link]

Showing NP-Card for thunberginol f (NP0212175)

MOL for NP0212175 (thunberginol f)

3D MOL for NP0212175 (thunberginol f)

3D SDF for NP0212175 (thunberginol f)

3D-SDF for NP0212175 (thunberginol f)

PDB for NP0212175 (thunberginol f)

3D PDB for NP0212175 (thunberginol f)

SMILES for NP0212175 (thunberginol f)

INCHI for NP0212175 (thunberginol f)

Structure for NP0212175 (thunberginol f)

3D Structure for NP0212175 (thunberginol f)