NP-MRD: Showing NP-Card for 8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate (NP0279638)

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Record Information

Version

2.0

Created at

2022-09-09 05:06:09 UTC

Updated at

2022-09-09 05:06:09 UTC

NP-MRD ID

NP0279638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate

Description

(+)-Anomalin, also known as praeruptorin b or anomalin, belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. 8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate is found in Peucedanum japonicum. 8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate was first documented in 2016 (PMID: 26849943). Based on a literature review a small amount of articles have been published on (+)-Anomalin (PMID: 35544308) (PMID: 32377290) (PMID: 31154290) (PMID: 36017263).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207062D          

 31 33  0  0  0  0            999 V2000
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092207062D          

 31 33  0  0  0  0            999 V2000
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0279638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)OC1C(OC(=O)C(\C)=C/C)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7-,14-8-

> <INCHI_KEY>
PNTWXEIQXBRCPS-PVRNWPCDSA-N

> <FORMULA>
C24H26O7

> <MOLECULAR_WEIGHT>
426.465

> <EXACT_MASS>
426.167853177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.3855871708702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12,12-dimethyl-14-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
5.239271929333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.898852514525875

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000002

> <JCHEM_REFRACTIVITY>
115.208

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
12,12-dimethyl-14-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184   7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.724   4.771   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.804   2.104   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.344   4.771   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    9   13                                                  
CONECT   20   10   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21    8   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Anomalin, (9S-(9alpha(Z),10alpha(Z)))-isomer	MeSH
Anomalin, (9alpha(e),10alpha(e))	MeSH
Praeruptorin b	MeSH
Anomalin	MeSH
Anomalin, (Z,Z)-isomer	MeSH

Chemical Formula

C₂₄H₂₆O₇

Average Mass

426.4650 Da

Monoisotopic Mass

426.16785 Da

IUPAC Name

12,12-dimethyl-14-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl (2Z)-2-methylbut-2-enoate

Traditional Name

12,12-dimethyl-14-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)OC1C(OC(=O)C(\C)=C/C)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12

InChI Identifier

InChI=1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7-,14-8-

InChI Key

PNTWXEIQXBRCPS-PVRNWPCDSA-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
Peucedanum japonicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Fatty acid ester
Pyranone
Dicarboxylic acid or derivatives
Pyran
Fatty acyl
Benzenoid
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	5.24	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.21 m³·mol⁻¹	ChemAxon
Polarizability	44.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

4953058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6450453

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Onder A, Trendafilova A: A Review on Anomalin: A Natural Bioactive Pyranocoumarin from the Past to the Future. Chem Biodivers. 2022 Sep;19(9):e202200167. doi: 10.1002/cbdv.202200167. Epub 2022 Aug 31. [PubMed:35544308 ]
Hassanein EHM, Sayed AM, Hussein OE, Mahmoud AM: Coumarins as Modulators of the Keap1/Nrf2/ARE Signaling Pathway. Oxid Med Cell Longev. 2020 Apr 22;2020:1675957. doi: 10.1155/2020/1675957. eCollection 2020. [PubMed:32377290 ]
Khan A, Khan S, Ali H, Shah KU, Ali H, Shehzad O, Onder A, Kim YS: Anomalin attenuates LPS-induced acute lungs injury through inhibition of AP-1 signaling. Int Immunopharmacol. 2019 Aug;73:451-460. doi: 10.1016/j.intimp.2019.05.032. Epub 2019 May 31. [PubMed:31154290 ]
Khan S, Choi RJ, Lee J, Kim YS: Attenuation of neuropathic pain and neuroinflammatory responses by a pyranocoumarin derivative, anomalin in animal and cellular models. Eur J Pharmacol. 2016 Mar 5;774:95-104. doi: 10.1016/j.ejphar.2016.02.008. Epub 2016 Feb 2. [PubMed:26849943 ]
Liu Z, Sun Q, Liu X, Song Z, Song F, Lu C, Zhang Y, Song X, Yang Y, Li Y: Network pharmacology analysis and experimental verification reveal the mechanism of the traditional Chinese medicine YU-Pingfeng San alleviating allergic rhinitis inflammatory responses. Front Plant Sci. 2022 Aug 9;13:934130. doi: 10.3389/fpls.2022.934130. eCollection 2022. [PubMed:36017263 ]
LOTUS database [Link]

Showing NP-Card for 8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate (NP0279638)

MOL for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

PDB for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

Structure for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0279638 (8,8-dimethyl-10-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl (2z)-2-methylbut-2-enoate)