NP-MRD: Showing NP-Card for Psychotrimine (NP0068650)

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Record Information

Version

2.0

Created at

2022-04-28 13:54:22 UTC

Updated at

2022-04-28 13:54:22 UTC

NP-MRD ID

NP0068650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Psychotrimine

Description

1,2,3,3A,8,8aalpha-Hexahydro-1-methyl-3aalpha,7-bis[3-[2-(methylamino)ethyl]-1H-indole-1-yl]pyrrolo[2,3-b]indole 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. Psychotrimine is found in Psychotria rostrata . Based on a literature review very few articles have been published on 1,2,3,3a,8,8aalpha-Hexahydro-1-methyl-3aalpha,7-bis[3-[2-(methylamino)ethyl]-1H-indole-1-yl]pyrrolo[2,3-b]indole.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215542D          

 39 45  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282215542D          

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    0.6144    2.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8443    3.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374    3.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2176    4.7233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345    5.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693    0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9243    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -0.4065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -1.2315    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  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
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 24 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 23 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 22 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 21 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068650

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCCC1=CN(C2=CC=CC=C12)C1=CC=CC2=C1N[C@H]1N(C)CC[C@@]21N1C=C(CCNC)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C33H38N6/c1-34-18-15-23-21-38(28-12-6-4-9-25(23)28)30-14-8-11-27-31(30)36-32-33(27,17-20-37(32)3)39-22-24(16-19-35-2)26-10-5-7-13-29(26)39/h4-14,21-22,32,34-36H,15-20H2,1-3H3/t32-,33+/m0/s1

> <INCHI_KEY>
MCOLFDIAHITOQJ-JHOUSYSJSA-N

> <FORMULA>
C33H38N6

> <MOLECULAR_WEIGHT>
518.709

> <EXACT_MASS>
518.315795248

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
61.47071085524766

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{1-[(3aR,8aS)-1-methyl-3a-{3-[2-(methylamino)ethyl]-1H-indol-1-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1H-indol-3-yl}ethyl)(methyl)amine

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
5.212319924666664

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.184269088062143

> <JCHEM_PKA_STRONGEST_BASIC>
10.58565464786686

> <JCHEM_POLAR_SURFACE_AREA>
49.190000000000005

> <JCHEM_REFRACTIVITY>
172.17759999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{1-[(3aR,8aS)-1-methyl-3a-{3-[2-(methylamino)ethyl]indol-1-yl}-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]indol-3-yl}ethyl)(methyl)amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.033  -0.684   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.568  -0.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.424  -1.238   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.744  -2.745   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.209  -3.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.353  -2.190   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.568   1.332   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -5.033   1.808   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.938   0.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.478   0.562   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.248  -0.771   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -9.788  -0.771   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0     -10.558  -2.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.323   2.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.484   3.769   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.238   4.674   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.169   4.048   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.330   2.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.916   1.611   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -0.440   0.146   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.100   0.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.576   1.611   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.052   3.076   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.517   3.552   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.517   5.092   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.850   5.862   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.184   5.092   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.184   3.552   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.850   2.782   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.052   5.567   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.147   4.322   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.576   7.032   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.070   7.352   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -0.406   8.817   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       0.624   9.961   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.116   1.611   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.592   0.146   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       2.346  -0.759   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       2.346  -2.299   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8    1   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    7   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   38                                                  
CONECT   22   21   18   23   36                                             
CONECT   23   22   24   31                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   25   31   32                                                  
CONECT   31   30   23                                                       
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   22   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   21   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₈N₆

Average Mass

518.7090 Da

Monoisotopic Mass

518.31580 Da

IUPAC Name

(2-{1-[(3aR,8aS)-1-methyl-3a-{3-[2-(methylamino)ethyl]-1H-indol-1-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1H-indol-3-yl}ethyl)(methyl)amine

Traditional Name

(2-{1-[(3aR,8aS)-1-methyl-3a-{3-[2-(methylamino)ethyl]indol-1-yl}-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]indol-3-yl}ethyl)(methyl)amine

CAS Registry Number

Not Available

SMILES

CNCCC1=CN(C2=CC=CC=C12)C1=CC=CC2=C1N[C@H]1N(C)CC[C@@]21N1C=C(CCNC)C2=CC=CC=C12

InChI Identifier

InChI=1S/C33H38N6/c1-34-18-15-23-21-38(28-12-6-4-9-25(23)28)30-14-8-11-27-31(30)36-32-33(27,17-20-37(32)3)39-22-24(16-19-35-2)26-10-5-7-13-29(26)39/h4-14,21-22,32,34-36H,15-20H2,1-3H3/t32-,33+/m0/s1

InChI Key

MCOLFDIAHITOQJ-JHOUSYSJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Psychotria rostrata	Plant	KNApSAcK

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
Tryptamine
N-alkylindole
3-alkylindole
Indole
Dihydroindole
Aralkylamine
Substituted pyrrole
N-alkylpyrrolidine
Benzenoid
Heteroaromatic compound
Pyrrolidine
Pyrrole
Secondary amine
Azacycle
Secondary aliphatic amine
Amine
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen 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	4.51	ALOGPS
logP	5.21	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.18	ChemAxon
pKa (Strongest Basic)	10.59	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	49.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	172.18 m³·mol⁻¹	ChemAxon
Polarizability	61.47 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

10184282

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12147974

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Psychotrimine (NP0068650)

MOL for NP0068650 (Psychotrimine)

3D MOL for NP0068650 (Psychotrimine)

3D SDF for NP0068650 (Psychotrimine)

3D-SDF for NP0068650 (Psychotrimine)

PDB for NP0068650 (Psychotrimine)

3D PDB for NP0068650 (Psychotrimine)

SMILES for NP0068650 (Psychotrimine)

INCHI for NP0068650 (Psychotrimine)

Structure for NP0068650 (Psychotrimine)

3D Structure for NP0068650 (Psychotrimine)