NP-MRD: Showing NP-Card for Pangelin (NP0139974)

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Record Information

Version

2.0

Created at

2022-06-29 20:19:11 UTC

Updated at

2022-06-29 20:19:11 UTC

NP-MRD ID

NP0139974

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pangelin

Description

Pangelin belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Pangelin is found in Angelica dahurica, Angelica japonica and Ducrosia anethifolia. Pangelin was first documented in 2003 (PMID: 14648403). Based on a literature review very few articles have been published on Pangelin (PMID: 15646793).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4263   -0.8492    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604   -0.0880    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5474    1.3408   -0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0041   -0.6854    0.1770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3762   -0.4975   -1.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2061    0.0293    1.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -0.3858    1.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1369   -0.4156    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3755   -1.5399   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -2.7903   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773   -3.5186   -1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455   -2.7681   -1.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412   -1.5831   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -0.4923   -1.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313    0.6318   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8229    1.6729   -0.6601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596    2.7926    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4403    3.7632   -0.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    2.9032    0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    1.8306    1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9653    0.6789    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3515   -1.8844    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4249   -0.4364    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6051    1.5951   -0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2313    1.4307   -1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087    2.0365    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.7626    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4248    0.4793   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7412   -0.1585    2.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    1.1164    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836   -3.1268    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3008   -4.5250   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018   -0.5447   -1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336    3.8273    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9686    1.9238    1.8269 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8 21  2  0
 21 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  9  8  1  0
 15 21  1  0
 12 13  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  1 22  1  0
  1 23  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  0
  6 30  1  0
 20 35  1  0
 19 34  1  0
 14 33  1  0
 10 31  1  0
 11 32  1  0
M  END


  Mrv1652306292222192D          

 21 23  0  0  1  0            999 V2000
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -4.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -5.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719   -5.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   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
  7  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 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
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
  4 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0139974

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H](O)COC1=C2C=CC(=O)OC2=CC2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-9(2)12(17)8-20-16-10-3-4-15(18)21-14(10)7-13-11(16)5-6-19-13/h3-7,12,17H,1,8H2,2H3/t12-/m0/s1

> <INCHI_KEY>
BVMOMQJYQYBMKL-LBPRGKRZSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.87761069853196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.1290879033333323

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.839075846782379

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8322390835293763

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
76.26010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]oxy}furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.523  -8.730   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.149 -10.137   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.681  -9.976   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H](O)COC1=C2C=CC(=O)OC2=CC2=C1C=CO2

InChI Identifier

InChI=1S/C16H14O5/c1-9(2)12(17)8-20-16-10-3-4-15(18)21-14(10)7-13-11(16)5-6-19-13/h3-7,12,17H,1,8H2,2H3/t12-/m0/s1

InChI Key

BVMOMQJYQYBMKL-LBPRGKRZSA-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
Angelica dahurica	LOTUS Database	35616633
Angelica japonica	LOTUS Database	35616633
Ducrosia anethifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Benzofuran
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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

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

26648040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44144315

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thanh PN, Jin W, Song G, Bae K, Kang SS: Cytotoxic coumarins from the root of Angelica dahurica. Arch Pharm Res. 2004 Dec;27(12):1211-5. doi: 10.1007/BF02975883. [PubMed:15646793 ]
Stavri M, Mathew KT, Bucar F, Gibbons S: Pangelin, an antimycobacterial coumarin from Ducrosia anethifolia. Planta Med. 2003 Oct;69(10):956-9. doi: 10.1055/s-2003-45109. [PubMed:14648403 ]

Showing NP-Card for Pangelin (NP0139974)

MOL for NP0139974 (Pangelin)

3D MOL for NP0139974 (Pangelin)

3D SDF for NP0139974 (Pangelin)

3D-SDF for NP0139974 (Pangelin)

PDB for NP0139974 (Pangelin)

3D PDB for NP0139974 (Pangelin)

SMILES for NP0139974 (Pangelin)

INCHI for NP0139974 (Pangelin)

Structure for NP0139974 (Pangelin)

3D Structure for NP0139974 (Pangelin)