NP-MRD: Showing NP-Card for 1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate (NP0293536)

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Record Information

Version

2.0

Created at

2022-09-10 01:35:38 UTC

Updated at

2022-09-10 01:35:38 UTC

NP-MRD ID

NP0293536

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate

Description

1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl acetate 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. 1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate is found in Fusarium incarnatum. Based on a literature review very few articles have been published on 1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.1319   -2.1371   -0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8729   -1.3230   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0269   -1.5431   -1.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6043   -0.3212    0.3274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436    0.4594    0.2762 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5211    1.4556    1.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    2.5678    0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861    2.7096   -0.4810 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    1.3453   -0.9157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0214    1.2449   -1.3427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496    0.1570   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210   -0.4012   -0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2909   -1.4616   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4821   -1.9833    0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2481   -1.4055    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -0.3216    0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653   -2.1973    0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -1.6837   -1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -3.1667   -0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860    1.8208    1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493    1.0175    2.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798    3.4741    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133    2.1225    0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    3.1498   -0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0620    1.0734   -1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    1.8761   -2.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757    0.0053   -1.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2590   -1.9246   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7936   -2.8324    1.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771   -1.7767    1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9  5  1  0
 16 11  1  0
 16  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  6
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END


  Mrv1652309102203352D          

 16 18  0  0  0  0            999 V2000
    2.3419    2.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224    1.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    1.3956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379   -0.1470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131   -0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554   -0.6613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.5999    0.0000 C   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  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  5 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC12CCNC1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O2/c1-8(15)16-12-6-7-13-11(12)14-10-5-3-2-4-9(10)12/h2-5,11,13-14H,6-7H2,1H3

> <INCHI_KEY>
DOQFLEAHYAUFGW-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O2

> <MOLECULAR_WEIGHT>
218.256

> <EXACT_MASS>
218.105527699

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.32797525766627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.7817198776666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.754227675389362

> <JCHEM_PKA_STRONGEST_BASIC>
7.211101952038057

> <JCHEM_POLAR_SURFACE_AREA>
50.36

> <JCHEM_REFRACTIVITY>
60.16840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.371   5.225   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.876   3.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.389   3.479   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.868   2.605   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.373   1.150   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.601   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.864   1.199   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.417  -0.274   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.878  -0.305   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.650  -1.234   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.387  -0.354   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.887  -0.704   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.166   0.420   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.281   1.894   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.781   2.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.833   1.120   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9   16                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11    5                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
1H,2H,3H,3AH,8H,8ah-pyrrolo[2,3-b]indol-3a-yl acetic acid	Generator

Chemical Formula

C₁₂H₁₄N₂O₂

Average Mass

218.2560 Da

Monoisotopic Mass

218.10553 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC12CCNC1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C12H14N2O2/c1-8(15)16-12-6-7-13-11(12)14-10-5-3-2-4-9(10)12/h2-5,11,13-14H,6-7H2,1H3

InChI Key

DOQFLEAHYAUFGW-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
Fusarium incarnatum	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
Pyrrole
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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

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

74384401

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate (NP0293536)

MOL for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

3D MOL for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

3D SDF for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

3D-SDF for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

PDB for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

3D PDB for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

SMILES for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

INCHI for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

Structure for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)

3D Structure for NP0293536 (1h,2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl acetate)