NP-MRD: Showing NP-Card for 1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol (NP0309797)

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Record Information

Version

2.0

Created at

2022-09-11 04:38:38 UTC

Updated at

2022-09-11 04:38:38 UTC

NP-MRD ID

NP0309797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol

Description

Alline belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Alline is a very strong basic compound (based on its pKa). Outside of the human body, Alline has been detected, but not quantified in, onion-family vegetables. 1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol is found in Allium anisopodium, Allium ramosum and Allium sativum. This could make alline a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.7167    1.6765   -0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2408    0.5959    0.2028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918   -0.7066   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1339   -1.3295   -0.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217   -0.7030    0.5275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5366   -1.3074    1.7530 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -0.5435    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -1.3082    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4901   -0.9258   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080    0.2606   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4814    1.0228   -0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175    0.6429   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795    1.2631   -0.6285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449    0.7170    0.4840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8097    1.4538   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0322    2.5537   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    2.0360   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1352   -0.7212   -1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9915   -1.3484    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1551   -2.4245   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -0.9319   -1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440   -1.9978    1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1246   -2.2344    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -1.5330    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714    0.5963   -1.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5666    1.9684   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    1.9322   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6091    1.2959    1.3829 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  5  1  0
  5  6  1  1
  5 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
 14  2  1  0
  7 12  1  0
  7  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
 14 28  1  1
 13 27  1  0
 11 26  1  0
 10 25  1  0
  9 24  1  0
  8 23  1  0
M  END


  Mrv0541 05061305192D          

 14 16  0  0  0  0            999 V2000
    0.3153    3.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1008    2.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    2.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973    1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762    3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    1.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739    2.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    2.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727    3.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    3.7260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    3.2118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788    1.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2(O)C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O/c1-13-7-6-11(14)8-4-2-3-5-9(8)12-10(11)13/h2-5,10,12,14H,6-7H2,1H3

> <INCHI_KEY>
CBQYNPHHHJTCJS-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O

> <MOLECULAR_WEIGHT>
190.2417

> <EXACT_MASS>
190.11061308

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.59861205629609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-ol

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
0.7236424046666671

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.689232761533868

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.075291792481

> <JCHEM_PKA_STRONGEST_BASIC>
6.382744350774536

> <JCHEM_POLAR_SURFACE_AREA>
35.5

> <JCHEM_REFRACTIVITY>
56.311600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.589   7.223   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.655   3.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.102   5.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.155   3.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.049   6.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.335   3.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.071   4.522   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.102   4.601   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.549   6.075   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.058   6.026   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.563   4.571   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.286   6.955   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       1.518   5.995   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       4.067   3.116   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8    4    9   11                                                  
CONECT    9    5    8   12                                                  
CONECT   10   11   12   13                                                  
CONECT   11    6    8   10   14                                             
CONECT   12    9   10                                                       
CONECT   13    1    7   10                                                  
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Value	Source
2,3,8,8a-Tetrahydro-1-methylpyrrolo[2,3-b]indol-3a(1H)-ol, 9ci	HMDB

Chemical Formula

C₁₁H₁₄N₂O

Average Mass

190.2417 Da

Monoisotopic Mass

190.11061 Da

IUPAC Name

1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-ol

Traditional Name

1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-ol

CAS Registry Number

Not Available

SMILES

CN1CCC2(O)C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C11H14N2O/c1-13-7-6-11(14)8-4-2-3-5-9(8)12-10(11)13/h2-5,10,12,14H,6-7H2,1H3

InChI Key

CBQYNPHHHJTCJS-UHFFFAOYSA-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
Allium anisopodium	LOTUS Database	35616633
Allium odorum	LOTUS Database	35616633
Allium sativum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Indole
Dihydroindole
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Tertiary alcohol
Azacycle
Secondary amine
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
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	1.08	ALOGPS
logP	0.72	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	6.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	35.5 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.31 m³·mol⁻¹	ChemAxon
Polarizability	20.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030533

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002406

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

73124019

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol (NP0309797)

MOL for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

3D MOL for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

3D SDF for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

3D-SDF for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

PDB for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

3D PDB for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

SMILES for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

INCHI for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

Structure for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)

3D Structure for NP0309797 (1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-ol)