NP-MRD: Showing NP-Card for angelol-j (NP0286518)

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Record Information

Version

2.0

Created at

2022-09-09 15:07:42 UTC

Updated at

2022-09-09 15:07:42 UTC

NP-MRD ID

NP0286518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

angelol-j

Description

Angelol-J belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Angelol-J 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. angelol-j is found in Angelica pubescens. angelol-j was first documented in 1995 (PMID: 17238102). Based on a literature review very few articles have been published on angelol-J.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
   -1.1769    2.1147    3.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.7441    2.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    0.9282    1.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707   -0.1726    0.2893 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7016   -0.2975   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3148    0.8164   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049    0.8040   -0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088    1.9225   -1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110    1.8812   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4010    0.7648   -0.9528 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    0.7084   -1.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856   -0.2825   -0.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658   -0.2701   -0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8245   -1.4132    0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444   -1.4102    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280   -2.4638    0.7787 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2314   -3.6877    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4170    0.1825   -1.0371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2547   -1.1309   -1.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8643    0.4448   -1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390   -0.4292   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826    0.1137   -2.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1814    1.7469   -0.7191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179    2.8092    2.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075    1.9022    4.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1413    2.5427    2.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2212    0.3289    2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.0983    2.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1313   -1.1068    0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132    1.7025   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    2.7805   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    2.7685   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3933   -2.2599    0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -4.2406    1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323   -3.6357    1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3872   -4.2890    0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841    0.8179   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6093   -1.7683   -1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.1226    0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138   -1.4173    0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775   -0.5757   -0.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -0.1325   -3.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9612    0.9002   -2.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9645   -0.8588   -2.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1822    1.8966   -0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  4  5  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  7 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  1
 18 37  1  6
 19 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 14 33  1  0
  9 32  1  0
  8 31  1  0
  6 30  1  0
M  END


  Mrv1652309092217072D          

 23 24  0  0  1  0            999 V2000
   -2.1434   -0.4125    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
   -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  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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   -1.6500    0.0000 C   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
    0.0000   -1.6500    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
    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
    1.1270    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  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
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCO[C@@H]([C@@H](O)C(C)(C)O)C1=C(OC)C=C2OC(=O)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O6/c1-5-22-15(16(19)17(2,3)20)11-8-10-6-7-14(18)23-12(10)9-13(11)21-4/h6-9,15-16,19-20H,5H2,1-4H3/t15-,16-/m1/s1

> <INCHI_KEY>
SPEUNNBYNAGBGC-HZPDHXFCSA-N

> <FORMULA>
C17H22O6

> <MOLECULAR_WEIGHT>
322.357

> <EXACT_MASS>
322.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.37002915996072

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1R,2R)-1-ethoxy-2,3-dihydroxy-3-methylbutyl]-7-methoxy-2H-chromen-2-one

> <JCHEM_LOGP>
1.294754849666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.080292035890473

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.912648384949783

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1308702035482954

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
85.3095

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1R,2R)-1-ethoxy-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one

> <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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104   0.976   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564   3.644   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    5   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    4   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
Angelol J	ChEBI

Chemical Formula

C₁₇H₂₂O₆

Average Mass

322.3570 Da

Monoisotopic Mass

322.14164 Da

IUPAC Name

6-[(1R,2R)-1-ethoxy-2,3-dihydroxy-3-methylbutyl]-7-methoxy-2H-chromen-2-one

Traditional Name

6-[(1R,2R)-1-ethoxy-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one

CAS Registry Number

Not Available

SMILES

CCO[C@@H]([C@@H](O)C(C)(C)O)C1=C(OC)C=C2OC(=O)C=CC2=C1

InChI Identifier

InChI=1S/C17H22O6/c1-5-22-15(16(19)17(2,3)20)11-8-10-6-7-14(18)23-12(10)9-13(11)21-4/h6-9,15-16,19-20H,5H2,1-4H3/t15-,16-/m1/s1

InChI Key

SPEUNNBYNAGBGC-HZPDHXFCSA-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 pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Phenol ether
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Secondary alcohol
Lactone
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	1.29	ChemAxon
pKa (Strongest Acidic)	12.91	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.31 m³·mol⁻¹	ChemAxon
Polarizability	33.37 Å³	ChemAxon
Number of Rings	2	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

8263009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10087472

PDB ID

Not Available

ChEBI ID

132768

Good Scents ID

Not Available

References

General References

Liu JH, Xu SX, Yao XS, Kobayashi H: Two new 6-alkylcoumarins from Angelica pubescens f. biserrata. Planta Med. 1995 Oct;61(5):482-4. doi: 10.1055/s-2006-958145. [PubMed:17238102 ]
LOTUS database [Link]

Showing NP-Card for angelol-j (NP0286518)

MOL for NP0286518 (angelol-j)

3D MOL for NP0286518 (angelol-j)

3D SDF for NP0286518 (angelol-j)

3D-SDF for NP0286518 (angelol-j)

PDB for NP0286518 (angelol-j)

3D PDB for NP0286518 (angelol-j)

SMILES for NP0286518 (angelol-j)

INCHI for NP0286518 (angelol-j)

Structure for NP0286518 (angelol-j)

3D Structure for NP0286518 (angelol-j)