NP-MRD: Showing NP-Card for (-)-Tubastrindole H (NP0082118)

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Record Information

Version

2.0

Created at

2022-04-29 03:10:30 UTC

Updated at

2022-04-29 03:10:30 UTC

NP-MRD ID

NP0082118

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Tubastrindole H

Description

(2'R,3'S,4R)-2'-(1H-indol-3-yl)-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,2'',5,5''-tetrone belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. (-)-Tubastrindole H is found in Tubastraea aurea. Based on a literature review very few articles have been published on (2'R,3'S,4R)-2'-(1H-indol-3-yl)-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,2'',5,5''-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205102D          

 38 44  0  0  1  0            999 V2000
    2.3165   -0.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0298   -1.1724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6960   -1.6591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4389   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292205102D          

 38 44  0  0  1  0            999 V2000
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  4 28  1  0  0  0  0
 28 29  2  0  0  0  0
 27 30  1  0  0  0  0
 24 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  1 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 32 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0082118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)N(C)[C@]2(CC3=C(NC4=CC=CC=C34)[C@@]3([C@@H]2C2=CNC4=CC=CC=C24)N(C)C(=O)N(C)C3=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26N6O4/c1-31-23(35)27(33(3)25(31)37)13-17-15-9-6-8-12-20(15)30-22(17)28(24(36)32(2)26(38)34(28)4)21(27)18-14-29-19-11-7-5-10-16(18)19/h5-12,14,21,29-30H,13H2,1-4H3/t21-,27+,28-/m1/s1

> <INCHI_KEY>
MHAYPWZWSGPJAV-AOLGGSBGSA-N

> <FORMULA>
C28H26N6O4

> <MOLECULAR_WEIGHT>
510.554

> <EXACT_MASS>
510.201553341

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.66010284498665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2'R,3'S,4R)-2'-(1H-indol-3-yl)-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,2'',5,5''-tetrone

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
1.9535408263333343

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.227379374865176

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.556916981545434

> <JCHEM_PKA_STRONGEST_BASIC>
-7.531084679357784

> <JCHEM_POLAR_SURFACE_AREA>
112.82

> <JCHEM_REFRACTIVITY>
138.4795

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2'R,3'S,4R)-2'-(1H-indol-3-yl)-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,2'',5,5''-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.324  -1.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.328   0.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.664   0.892   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.996   0.118   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.991  -1.422   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.656  -2.188   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.899  -3.097   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.419  -4.560   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.825  -6.161   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       4.879  -4.556   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.407  -3.090   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.912  -3.361   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.996  -5.913   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.340  -3.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.153  -2.332   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.732  -1.573   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.759  -2.720   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       9.985  -4.052   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       8.480  -3.728   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.266  -2.404   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.746  -0.941   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.719   0.207   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.211  -0.110   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       7.161   1.649   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       8.668   1.965   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.205   3.523   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0       9.434   0.630   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       8.401  -0.512   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.863  -1.739   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.141   1.206   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.637   3.184   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.865   0.605   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.956  -0.639   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.858  -1.887   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       0.425  -0.473   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.197   0.935   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.711   2.179   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.242   2.013   0.000  0.00  0.00           C+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24   28                                             
CONECT    5    4    6   15                                                  
CONECT    6    5    1    7   11                                             
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    7                                                            
CONECT   15    5   16   19                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
CONECT   24    4   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27    4   29                                                  
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31   24                                                            
CONECT   32    2   33   38                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33    1                                                       
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   32                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₆N₆O₄

Average Mass

510.5540 Da

Monoisotopic Mass

510.20155 Da

IUPAC Name

(2'R,3'S,4R)-2'-(1H-indol-3-yl)-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,2'',5,5''-tetrone

Traditional Name

(2'R,3'S,4R)-2'-(1H-indol-3-yl)-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,2'',5,5''-tetrone

CAS Registry Number

Not Available

SMILES

CN1C(=O)N(C)[C@]2(CC3=C(NC4=CC=CC=C34)[C@@]3([C@@H]2C2=CNC4=CC=CC=C24)N(C)C(=O)N(C)C3=O)C1=O

InChI Identifier

InChI=1S/C28H26N6O4/c1-31-23(35)27(33(3)25(31)37)13-17-15-9-6-8-12-20(15)30-22(17)28(24(36)32(2)26(38)34(28)4)21(27)18-14-29-19-11-7-5-10-16(18)19/h5-12,14,21,29-30H,13H2,1-4H3/t21-,27+,28-/m1/s1

InChI Key

MHAYPWZWSGPJAV-AOLGGSBGSA-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
Tubastraea aurea	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Hydantoin
3-alkylindole
Alpha-amino acid or derivatives
Indole
Ureide
N-acyl urea
Benzenoid
Substituted pyrrole
Imidazolidinone
Heteroaromatic compound
Pyrrole
Imidazolidine
Dicarboximide
Urea
Carbonic acid derivative
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	3.59	ALOGPS
logP	1.95	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	15.56	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	138.48 m³·mol⁻¹	ChemAxon
Polarizability	52.66 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

74180173

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134860243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Tubastrindole H (NP0082118)

MOL for NP0082118 ((-)-Tubastrindole H)

3D MOL for NP0082118 ((-)-Tubastrindole H)

3D SDF for NP0082118 ((-)-Tubastrindole H)

3D-SDF for NP0082118 ((-)-Tubastrindole H)

PDB for NP0082118 ((-)-Tubastrindole H)

3D PDB for NP0082118 ((-)-Tubastrindole H)

SMILES for NP0082118 ((-)-Tubastrindole H)

INCHI for NP0082118 ((-)-Tubastrindole H)

Structure for NP0082118 ((-)-Tubastrindole H)

3D Structure for NP0082118 ((-)-Tubastrindole H)