NP-MRD: Showing NP-Card for Seselin (NP0047911)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:57 UTC

Updated at

2022-03-17 20:47:57 UTC

NP-MRD ID

NP0047911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Seselin

Description

Seselin, also known as amyrolin, 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. Seselin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Seselin has been detected, but not quantified in, several different foods, such as fennels, lemons, herbs and spices, sweet oranges, and anises. Seselin is found in Amyris pinnata, Foeniculum vulgare , Angelica gigas, Apium leptophyllum , Carum roxburghianum, Citropsis articulata, Citrus aurantium , Citrus japonica, Citrus junos , Citrus paradisi, Citrus sinensis, Citrus spp., Citrus sulcata, Citrus tachibana, Poncirus trifoliata , Dinosperma stipitatum, Ficus erecta, Flindersia australis, Flindersia bennettiana, Flindersia pimenteliana, Haplophyllum acutifolium, Haplophyllum cappadocicum, Haplophyllum dshungaricum, Haplophyllum dubium, Haplophyllum thesioides, Hortia superba, Melicope semecarpifolia, Myrtopsis macrocarpa, Nematolepis phebalioides, Phellodendron amurense, Phellodendron amurense var.wilsonii , Pleiospermium alatum, Plumbago zeylanica , Rhadinothamnus anceps, Rhadinothamnus rudis, Seseli elatum, Seseli indicum and Swinglea glutinosa. This could make seselin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

Seselin
  Mrv1572001071617272D          

 17 19  0  0  0  0            999 V2000
   14.8500   -9.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6962   -9.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1400   -9.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2937   -9.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9950  -10.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5512  -10.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9950  -10.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500   -8.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2937   -8.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5512  -10.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2937  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5925   -8.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6962  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4387  -10.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4387  -10.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2312   -8.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1900   -9.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  5  1  0  0  0  0
  2 14  1  0  0  0  0
  3 14  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  9  1  0  0  0  0
  5  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  8 12  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  2  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c1-14(2)8-7-10-11(17-14)5-3-9-4-6-12(15)16-13(9)10/h3-8H,1-2H3

> <INCHI_KEY>
QUVCQYQEIOLHFZ-UHFFFAOYSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.247

> <EXACT_MASS>
228.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.91271836708977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,8-dimethyl-2H,8H-pyrano[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.6839830173333334

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.90678503664917

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
65.94200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,8-dimethylpyrano[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Seselin                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      27.720 -18.172   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      33.033 -18.172   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.728 -18.172   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      30.415 -18.172   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.724 -18.942   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.029 -18.942   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.724 -20.482   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.720 -16.632   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.415 -16.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.029 -20.482   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.415 -21.252   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.106 -15.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.033 -21.252   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.419 -18.942   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.419 -20.482   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.565 -15.477   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.488 -17.479   0.000  0.00  0.00           C+0
CONECT    1    6    8                                                       
CONECT    2    5   14                                                       
CONECT    3   14                                                            
CONECT    4    5    6    9                                                  
CONECT    5    2    4    7                                                  
CONECT    6    1    4   10                                                  
CONECT    7    5   11   13                                                  
CONECT    8    1   12   16   17                                             
CONECT    9    4   12                                                       
CONECT   10    6   11                                                       
CONECT   11    7   10                                                       
CONECT   12    8    9                                                       
CONECT   13    7   15                                                       
CONECT   14    2    3   15                                                  
CONECT   15   13   14                                                       
CONECT   16    8                                                            
CONECT   17    8                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
3',4'-Di-O-(-)-camphanoyl-(+)-cis-khellactone	HMDB
8,8-Dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-2-one	HMDB
8,8-Dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one	HMDB
8,8-Dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 9ci	HMDB
8,8-Dimethyl-2H,8H-pyrano[2,3-F]chromen-2-one	HMDB
Amyrolin	HMDB
Pyranocoumarin deriv.	HMDB
Seseline	HMDB

Chemical Formula

C₁₄H₁₂O₃

Average Mass

228.2470 Da

Monoisotopic Mass

228.07864 Da

IUPAC Name

8,8-dimethyl-2H,8H-pyrano[2,3-h]chromen-2-one

Traditional Name

8,8-dimethylpyrano[2,3-h]chromen-2-one

CAS Registry Number

523-59-1

SMILES

CC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C=C2

InChI Identifier

InChI=1S/C14H12O3/c1-14(2)8-7-10-11(17-14)5-3-9-4-6-12(15)16-13(9)10/h3-8H,1-2H3

InChI Key

QUVCQYQEIOLHFZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amyris pinnata	LOTUS Database	35616633
Anethum foeniculum	Plant	KNApSAcK
Angelica gigas	LOTUS Database	35616633
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium leptophyllum	Plant	KNApSAcK
Carum roxburghianum	Plant	KNApSAcK
Citropsis articulata	LOTUS Database	35616633
Citrus aurantium	Plant	KNApSAcK
Citrus japonica	LOTUS Database	35616633
Citrus junos	Plant	KNApSAcK
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus paradisi	LOTUS Database	35616633
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus sinensis	LOTUS Database	35616633
Citrus spp.	Plant	KNApSAcK
Citrus sulcata	LOTUS Database	35616633
Citrus tachibana	Plant	KNApSAcK
Citrus trifoliata	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dinosperma stipitatum	LOTUS Database	35616633
Ficus erecta	LOTUS Database	35616633
Flindersia australis	LOTUS Database	35616633
Flindersia bennettiana	Plant	KNApSAcK
Flindersia pimenteliana	Plant	KNApSAcK
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Haplophyllum acutifolium	LOTUS Database	35616633
Haplophyllum cappadocicum	LOTUS Database	35616633
Haplophyllum dshungaricum	LOTUS Database	35616633
Haplophyllum dubium	Plant	KNApSAcK
Haplophyllum thesioides	LOTUS Database	35616633
Hortia superba	LOTUS Database	35616633
Melicope semecarpifolia	LOTUS Database	35616633
Myrtopsis macrocarpa	Plant	KNApSAcK
Nematolepis phebalioides	LOTUS Database	35616633
Phellodendron amurense	LOTUS Database	35616633
Phellodendron amurense var.wilsonii	Plant	KNApSAcK
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pleiospermium alatum	LOTUS Database	35616633
Plumbago zeylanica	Plant	KNApSAcK
Rhadinothamnus anceps	LOTUS Database	35616633
Rhadinothamnus rudis	LOTUS Database	35616633
Seseli elatum	LOTUS Database	35616633
Seseli indicum	Plant	KNApSAcK
Swinglea glutinosa	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
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:69040 )
coumarins (C09312 )

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	ALOGPS
logP	2.68	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.94 m³·mol⁻¹	ChemAxon
Polarizability	23.91 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

HMDB0034257

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68229

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Seselin (NP0047911)

MOL for NP0047911 (Seselin)

3D MOL for NP0047911 (Seselin)

3D SDF for NP0047911 (Seselin)

3D-SDF for NP0047911 (Seselin)

PDB for NP0047911 (Seselin)

3D PDB for NP0047911 (Seselin)

SMILES for NP0047911 (Seselin)

INCHI for NP0047911 (Seselin)

Structure for NP0047911 (Seselin)

3D Structure for NP0047911 (Seselin)