NP-MRD: Showing NP-Card for (3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol (NP0216117)

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Record Information

Version

2.0

Created at

2022-09-05 15:57:28 UTC

Updated at

2022-09-05 15:57:28 UTC

NP-MRD ID

NP0216117

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol

Description

Laccarin belongs to the class of organic compounds known as pyrrolopyridines. Pyrrolopyridines are compounds containing a pyrrolopyridine moiety, which consists of a pyrrole ring fused to a pyridine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center. (3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol is found in Laccaria vinaceoavellanea and Lactarius subplinthogalus. (3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol was first documented in 2004 (PMID: 14984090). Based on a literature review a small amount of articles have been published on Laccarin (PMID: 20237659) (PMID: 34373435) (PMID: 17392964).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    2.9826   -1.5235    0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -0.1628    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479    0.6909   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5784    0.2865   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    1.5910   -0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    2.6534   -1.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044    1.6083   -1.0708 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331    0.3613   -0.7801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3792   -0.5063   -0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -1.6689    0.1367 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212   -2.0326    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.9541    0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    0.3982    0.3294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7753    1.4835    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2905   -2.2757    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -1.4786    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0062   -1.8428    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    1.4544    0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152    3.6053   -1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1539   -0.1077   -1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5751   -2.9374    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869   -2.3459   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -1.1508    1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690   -0.9532   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873    0.6182    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1170    1.4333   -0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5919    1.3124    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855    2.4436    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  5  4  1  0
  4  2  2  0
  2  1  1  0
  2  3  1  0
  8 13  1  0
  4  9  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 13 25  1  1
 12 23  1  0
 12 24  1  0
 11 21  1  0
 11 22  1  0
  8 20  1  6
  6 19  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
M  END


  Mrv1652309052217572D          

 14 15  0  0  0  0            999 V2000
    0.1536    1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216117

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCN=C2C1N=C(O)\C2=C(\C)O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O2/c1-5-3-4-11-9-7(6(2)13)10(14)12-8(5)9/h5,8,13H,3-4H2,1-2H3,(H,12,14)/b7-6-

> <INCHI_KEY>
VJFIILVPPZGOTO-SREVYHEPSA-N

> <FORMULA>
C10H14N2O2

> <MOLECULAR_WEIGHT>
194.234

> <EXACT_MASS>
194.105527699

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.728799372622117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-3-(1-hydroxyethylidene)-7-methyl-3H,5H,6H,7H,7aH-pyrrolo[3,2-b]pyridin-2-ol

> <JCHEM_LOGP>
0.5323230790340537

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.4582507722484

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3925395355722605

> <JCHEM_PKA_STRONGEST_BASIC>
5.408779260934625

> <JCHEM_POLAR_SURFACE_AREA>
65.18

> <JCHEM_REFRACTIVITY>
54.10680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-(1-hydroxyethylidene)-7-methyl-5H,6H,7H,7aH-pyrrolo[3,2-b]pyridin-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.287   2.552   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.250   1.728   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄N₂O₂

Average Mass

194.2340 Da

Monoisotopic Mass

194.10553 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1CCN=C2C1N=C(O)\C2=C(\C)O

InChI Identifier

InChI=1S/C10H14N2O2/c1-5-3-4-11-9-7(6(2)13)10(14)12-8(5)9/h5,8,13H,3-4H2,1-2H3,(H,12,14)/b7-6-

InChI Key

VJFIILVPPZGOTO-SREVYHEPSA-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
Laccaria vinaceoavellanea	LOTUS Database	35616633
Lactarius subplinthogalus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolopyridines. Pyrrolopyridines are compounds containing a pyrrolopyridine moiety, which consists of a pyrrole ring fused to a pyridine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyridines

Sub Class

Not Available

Direct Parent

Pyrrolopyridines

Alternative Parents

Substituents

Pyrrolopyridine
Tetrahydropyridine
2-pyrrolidone
Pyrrolidone
Pyridine
Vinylogous acid
Pyrrolidine
Secondary carboxylic acid amide
Lactam
Ketimine
Carboxamide group
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Enol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.53	ChemAxon
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	5.41	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.18 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.11 m³·mol⁻¹	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136927122

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Y, Yang SP, Wu Y, Yue JM: Alkaloids from the fungus Lactarius subplinthogalus. Nat Prod Res. 2004 Apr;18(2):159-62. doi: 10.1080/14786410310001608073. [PubMed:14984090 ]
Bower JF, Rujirawanich J, Gallagher T: N-heterocycle construction via cyclic sulfamidates. Applications in synthesis. Org Biomol Chem. 2010 Apr 7;8(7):1505-19. doi: 10.1039/b921842d. Epub 2010 Jan 28. [PubMed:20237659 ]
Ren J, Li P, Yan D, Li M, Qi J, Wang M, Zhong G, Wu M: Interplay between the Gut Microbiome and Metabolism in Ulcerative Colitis Mice Treated with the Dietary Ingredient Phloretin. J Microbiol Biotechnol. 2021 Oct 28;31(10):1409-1419. doi: 10.4014/jmb.2104.04038. [PubMed:34373435 ]
Bower JF, Riis-Johannessen T, Szeto P, Whitehead AJ, Gallagher T: Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin. Chem Commun (Camb). 2007 Feb 21;(7):728-30. doi: 10.1039/b617260a. Epub 2007 Jan 18. [PubMed:17392964 ]
LOTUS database [Link]

Showing NP-Card for (3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol (NP0216117)

MOL for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

3D MOL for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

3D SDF for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

3D-SDF for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

PDB for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

3D PDB for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

SMILES for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

INCHI for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

Structure for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)

3D Structure for NP0216117 ((3z)-3-(1-hydroxyethylidene)-7-methyl-5h,6h,7h,7ah-pyrrolo[3,2-b]pyridin-2-ol)