NP-MRD: Showing NP-Card for 8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione (NP0316390)

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Record Information

Version

2.0

Created at

2022-09-11 15:33:28 UTC

Updated at

2022-09-11 15:33:28 UTC

NP-MRD ID

NP0316390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

Description

8-Hydroxy-4-(hydroxymethyl)-9-(1H-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-10,12,14-triene-3,6-dione 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. Based on a literature review very few articles have been published on 8-hydroxy-4-(hydroxymethyl)-9-(1H-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-10,12,14-triene-3,6-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217332D          

 35 40  0  0  0  0            999 V2000
    1.9902   -0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -0.5255    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0675   -1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656   -0.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6717   -1.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8270   -0.2591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2958   -1.6089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1144   -1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162   -0.9420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112217332D          

 35 40  0  0  0  0            999 V2000
    1.9902   -0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0316390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC12C(O)C3(C(NC4=CC=CC=C34)N1C(=O)C(CO)(SC)N(C)C2=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H26N4O4S2/c1-28-22(33)25(35-3)19(31)24(16-12-26-17-10-6-4-8-14(16)17)15-9-5-7-11-18(15)27-20(24)29(25)21(32)23(28,13-30)34-2/h4-12,19-20,26-27,30-31H,13H2,1-3H3

> <INCHI_KEY>
ZOGJUGRLERZFOU-UHFFFAOYSA-N

> <FORMULA>
C25H26N4O4S2

> <MOLECULAR_WEIGHT>
510.63

> <EXACT_MASS>
510.139547681

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
51.86728422835803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-hydroxy-4-(hydroxymethyl)-9-(1H-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

> <JCHEM_LOGP>
2.9805281106666683

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.216320811639665

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.078848892746795

> <JCHEM_PKA_STRONGEST_BASIC>
1.6264856592360988

> <JCHEM_POLAR_SURFACE_AREA>
108.89999999999999

> <JCHEM_REFRACTIVITY>
148.17560000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-4-(hydroxymethyl)-9-(1H-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.715  -0.433   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       5.154  -0.981   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       5.399  -2.501   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.859  -2.479   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.109  -1.134   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.854  -1.996   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.144  -0.484   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       8.019  -3.003   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.547  -2.812   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      10.670  -1.758   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      12.019  -2.501   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.474  -1.996   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.639  -3.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.349  -4.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.894  -5.021   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.729  -4.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.201  -4.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.393  -5.734   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.270  -6.787   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       9.924  -8.181   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      11.452  -7.989   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.617  -8.996   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.072  -8.491   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.362  -6.979   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.197  -5.971   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.742  -6.477   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.078  -5.259   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.335  -6.608   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.729  -4.516   0.000  0.00  0.00           C+0
HETATM   30  S   UNK     0       7.599  -6.050   0.000  0.00  0.00           S+0
HETATM   31  C   UNK     0       8.104  -7.505   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.274  -5.021   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.984  -6.534   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       5.109  -4.014   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       3.655  -4.519   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6   34                                             
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   29                                                  
CONECT    9    8   10   17                                                  
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   17                                                  
CONECT   17   16    9   18   27                                             
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   21                                                  
CONECT   27   17   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    8   30   32                                             
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxy-4-(hydroxymethyl)-9-(1H-indol-3-yl)-5-methyl-4,7-bis(methylsulphanyl)-2,5,16-triazatetracyclo[7.7.0.0,.0,]hexadeca-10,12,14-triene-3,6-dione	Generator

Chemical Formula

C₂₅H₂₆N₄O₄S₂

Average Mass

510.6300 Da

Monoisotopic Mass

510.13955 Da

IUPAC Name

8-hydroxy-4-(hydroxymethyl)-9-(1H-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

Traditional Name

8-hydroxy-4-(hydroxymethyl)-9-(1H-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

CAS Registry Number

Not Available

SMILES

CSC12C(O)C3(C(NC4=CC=CC=C34)N1C(=O)C(CO)(SC)N(C)C2=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C25H26N4O4S2/c1-28-22(33)25(35-3)19(31)24(16-12-26-17-10-6-4-8-14(16)17)15-9-5-7-11-18(15)27-20(24)29(25)21(32)23(28,13-30)34-2/h4-12,19-20,26-27,30-31H,13H2,1-3H3

InChI Key

ZOGJUGRLERZFOU-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

Not Available

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
Alpha-amino acid or derivatives
3-alkylindole
Indole
Dihydroindole
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
Secondary aliphatic/aromatic amine
N-methylpiperazine
N-alkylpiperazine
Benzenoid
1,4-diazinane
Piperazine
Substituted pyrrole
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrole
Pyrrolidine
Carboxamide group
Amino acid or derivatives
Lactam
Secondary alcohol
Sulfenyl compound
Hemithioaminal
Thioether
Carboxylic acid derivative
Dialkylthioether
Secondary amine
Azacycle
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Amine
Primary alcohol
Alcohol
Hydrocarbon derivative
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	2.98	ChemAxon
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	1.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	148.18 m³·mol⁻¹	ChemAxon
Polarizability	51.87 Å³	ChemAxon
Number of Rings	6	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

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

72822391

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione (NP0316390)

MOL for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

3D MOL for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

3D SDF for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

3D-SDF for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

PDB for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

3D PDB for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

SMILES for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

INCHI for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

Structure for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)

3D Structure for NP0316390 (8-hydroxy-4-(hydroxymethyl)-9-(1h-indol-3-yl)-5-methyl-4,7-bis(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione)