NP-MRD: Showing NP-Card for Obliquin (NP0080775)

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Record Information

Version

2.0

Created at

2022-04-29 01:46:17 UTC

Updated at

2022-04-29 01:46:17 UTC

NP-MRD ID

NP0080775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Obliquin

Description

OBLIQUIN belongs to the class of organic compounds known as p-dioxolo[2,3-g]coumarins. These are organic aromatic compounds that contain a p-dioxole ring that is linearly fused to the benzene ring of a coumarin. Obliquin is found in Actinobole uliginosum, Ageratum fastigiatum, Cedrelopsis grevei, Cedrelopsis microfoliata, Cneorum tricoccon, Filago congesta, Helichrysum dasyanthum, Ifloga spicata, leontopodium alpinum, Ozothamnus stirlingii, Plecostachys serpyllifolia, Polycalymma stuartii and Ptaeroxylon obliquum . Obliquin was first documented in 2002 (PMID: 12350164). Based on a literature review very few articles have been published on OBLIQUIN (PMID: 14630167).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.4970   -1.0272    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4110   -0.1559   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6068    0.5579   -0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    0.1157   -0.6708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7967    1.5743   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336    1.8086    0.3005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.9936    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748    1.3933    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398    0.5096    0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680    0.9333    0.4924 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1093    0.1387    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2348    0.6549    0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9352   -1.2099    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -1.7318    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032   -0.8297    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2911   -1.2446   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304   -0.3640    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798   -0.7305   -0.1355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -1.5805    1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4592   -1.2164    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3412    1.4567   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2505    0.9332    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2474   -0.0690   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309   -0.1567   -1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431    2.1275    0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    2.0333   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512    2.4639    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8007   -1.8848    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655   -2.7713   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0975   -2.3055   -0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
 18  4  1  0
  9 15  1  0
  8  7  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  1 19  1  0
  1 20  1  0
  4 24  1  6
  5 25  1  0
  5 26  1  0
 16 30  1  0
 14 29  1  0
 13 28  1  0
  8 27  1  0
M  END


  Mrv1652304292203462D          

 18 20  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   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    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
   -1.4289    0.8250    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  2  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1COC2=C(O1)C=C1C=CC(=O)OC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4/c1-8(2)13-7-16-11-6-10-9(5-12(11)17-13)3-4-14(15)18-10/h3-6,13H,1,7H2,2H3/t13-/m1/s1

> <INCHI_KEY>
DUECABXXAMFFBH-CYBMUJFWSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.59035350126053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(prop-1-en-2-yl)-2H,3H,7H-[1,4]dioxino[2,3-g]chromen-7-one

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.330870305666666

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6397392232439705

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
65.6209

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(prop-1-en-2-yl)-2H,3H-[1,4]dioxino[2,3-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₂O₄

Average Mass

244.2460 Da

Monoisotopic Mass

244.07356 Da

IUPAC Name

(2S)-2-(prop-1-en-2-yl)-2H,3H,7H-[1,4]dioxino[2,3-g]chromen-7-one

Traditional Name

(2S)-2-(prop-1-en-2-yl)-2H,3H-[1,4]dioxino[2,3-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1COC2=C(O1)C=C1C=CC(=O)OC1=C2

InChI Identifier

InChI=1S/C14H12O4/c1-8(2)13-7-16-11-6-10-9(5-12(11)17-13)3-4-14(15)18-10/h3-6,13H,1,7H2,2H3/t13-/m1/s1

InChI Key

DUECABXXAMFFBH-CYBMUJFWSA-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
Actinobole uliginosum	LOTUS Database	35616633
Ageratum fastigiatum	LOTUS Database	35616633
Cedrelopsis grevei	LOTUS Database	35616633
Cedrelopsis microfoliata	Plant	KNApSAcK
Cneorum tricoccon	LOTUS Database	35616633
Filago congesta	LOTUS Database	35616633
Helichrysum dasyanthum	LOTUS Database	35616633
Ifloga spicata	LOTUS Database	35616633
Leontopodium alpinum	-	KNApSAcK
Ozothamnus stirlingii	LOTUS Database	35616633
Plecostachys serpyllifolia	LOTUS Database	35616633
Polycalymma stuartii	LOTUS Database	35616633
Ptaeroxylon obliquum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-dioxolo[2,3-g]coumarins. These are organic aromatic compounds that contain a p-dioxole ring that is linearly fused to the benzene ring of a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

p-Dioxolo[2,3-g]coumarins

Direct Parent

p-Dioxolo[2,3-g]coumarins

Alternative Parents

Substituents

P-dioxolo[2,3-g]coumarin
Benzo-1,4-dioxane
Benzodioxane
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Para-dioxin
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	2.58	ALOGPS
logP	2.33	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.62 m³·mol⁻¹	ChemAxon
Polarizability	24.59 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

C00037569

Chemspider ID

5140747

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6708593

PDB ID

Not Available

ChEBI ID

113544

Good Scents ID

Not Available

References

General References

Koorbanally NA, Randrianarivelojosia M, Mulholland DA, Quarles van Ufford L, van den Berg AJ: Bioactive constituents of Cedrelopsis microfoliata. J Nat Prod. 2002 Sep;65(9):1349-52. doi: 10.1021/np0200562. [PubMed:12350164 ]
Um BH, Lobstein A, Weniger B, Spiegel C, Yice F, Rakotoarison O, Andriantsitohaina R, Anton R: New coumarins from Cedrelopsis grevei. Fitoterapia. 2003 Dec;74(7-8):638-42. doi: 10.1016/s0367-326x(03)00181-3. [PubMed:14630167 ]

Showing NP-Card for Obliquin (NP0080775)

MOL for NP0080775 (Obliquin)

3D MOL for NP0080775 (Obliquin)

3D SDF for NP0080775 (Obliquin)

3D-SDF for NP0080775 (Obliquin)

PDB for NP0080775 (Obliquin)

3D PDB for NP0080775 (Obliquin)

SMILES for NP0080775 (Obliquin)

INCHI for NP0080775 (Obliquin)

Structure for NP0080775 (Obliquin)

3D Structure for NP0080775 (Obliquin)