NP-MRD: Showing NP-Card for angelitriol (NP0307499)

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Record Information

Version

2.0

Created at

2022-09-11 00:39:40 UTC

Updated at

2022-09-11 00:39:40 UTC

NP-MRD ID

NP0307499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

angelitriol

Description

Angelitriol 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). Angelitriol 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. angelitriol is found in Angelica pubescens and Citrus paradisi. angelitriol was first documented in 1995 (PMID: 17238102). Based on a literature review very few articles have been published on angelitriol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    1.7208    3.8228   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944    2.6814   -0.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4563    1.4384   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    1.0094   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277   -0.2861    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961   -0.6851    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6089   -1.8939    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8082   -2.2142    0.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268   -2.7879    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2916   -2.4051    0.9094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994   -1.1268    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7051   -0.6863    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    0.5626   -0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9724    1.1094   -0.1075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9337    2.3503   -0.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121    0.4837   -0.4420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2155    1.4511    0.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -0.7858   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145   -2.0265   -0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0335   -1.0313    1.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1532   -0.6896   -0.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9630    4.4410   -1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0830    4.5162   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540    3.6700   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890    1.6404   -0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -3.7665    1.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -3.1312    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855   -1.3921    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1131    1.6392    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138    2.6293   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4364    0.6111   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9353    1.5001    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -2.6434   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8550   -1.7180   -1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270   -2.7167   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564   -0.9972    2.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4975   -2.0263    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8336   -0.3160    1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804   -0.2305   -1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
  4  3  1  0
  5 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 12 28  1  0
 10 27  1  0
  9 26  1  0
  4 25  1  0
 14 29  1  1
 15 30  1  0
 16 31  1  6
 17 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
M  END


  Mrv1652309112202392D          

 21 22  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  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 O   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
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    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   -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 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  3 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C2C=CC(=O)OC2=C1)[C@@H](O)[C@H](O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O6/c1-15(2,19)14(18)13(17)9-6-8-4-5-12(16)21-10(8)7-11(9)20-3/h4-7,13-14,17-19H,1-3H3/t13-,14+/m1/s1

> <INCHI_KEY>
PCSZTTAMZGNQNB-KGLIPLIRSA-N

> <FORMULA>
C15H18O6

> <MOLECULAR_WEIGHT>
294.303

> <EXACT_MASS>
294.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.76591285877553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.29482039133333304

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.059194356336338

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.708771316231942

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1306521187266068

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
75.8097

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-6-[(1R,2S)-1,2,3-trihydroxy-3-methylbutyl]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -2.310   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -4.620   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  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.437  -1.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.897  -4.414   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₆

Average Mass

294.3030 Da

Monoisotopic Mass

294.11034 Da

IUPAC Name

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

Traditional Name

7-methoxy-6-[(1R,2S)-1,2,3-trihydroxy-3-methylbutyl]chromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(C=C2C=CC(=O)OC2=C1)[C@@H](O)[C@H](O)C(C)(C)O

InChI Identifier

InChI=1S/C15H18O6/c1-15(2,19)14(18)13(17)9-6-8-4-5-12(16)21-10(8)7-11(9)20-3/h4-7,13-14,17-19H,1-3H3/t13-,14+/m1/s1

InChI Key

PCSZTTAMZGNQNB-KGLIPLIRSA-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
Citrus paradisi	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
1,2-diol
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
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	0.29	ChemAxon
pKa (Strongest Acidic)	12.71	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.81 m³·mol⁻¹	ChemAxon
Polarizability	29.77 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

8192891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10017318

PDB ID

Not Available

ChEBI ID

132402

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 angelitriol (NP0307499)

MOL for NP0307499 (angelitriol)

3D MOL for NP0307499 (angelitriol)

3D SDF for NP0307499 (angelitriol)

3D-SDF for NP0307499 (angelitriol)

PDB for NP0307499 (angelitriol)

3D PDB for NP0307499 (angelitriol)

SMILES for NP0307499 (angelitriol)

INCHI for NP0307499 (angelitriol)

Structure for NP0307499 (angelitriol)

3D Structure for NP0307499 (angelitriol)