NP-MRD: Showing NP-Card for methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate (NP0317523)

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Record Information

Version

2.0

Created at

2022-09-11 17:27:59 UTC

Updated at

2022-09-11 17:27:59 UTC

NP-MRD ID

NP0317523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate

Description

4-HYDROXY-2,8-DIMETHYL-1-OXO-6-(4,5,6-TRIMETHOXY-1H-INDOLE-2-CARBONYL)-1,2,3,6,7,8-HEXAHYDRO-3,6-DIAZA-AS-INDACENE-2-CARBOXYLIC ACID METHYL ESTER, also known as 4-hydroxy-2,8-dimethyl-1-oxo-6-(4,5,6-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2-carboxylate methyl ester, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. 4-HYDROXY-2,8-DIMETHYL-1-OXO-6-(4,5,6-TRIMETHOXY-1H-INDOLE-2-CARBONYL)-1,2,3,6,7,8-HEXAHYDRO-3,6-DIAZA-AS-INDACENE-2-CARBOXYLIC ACID METHYL ESTER is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041403042D          

 38 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05041403042D          

 38 42  0  0  1  0            999 V2000
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 29 10  1  0  0  0  0
 29 14  1  0  0  0  0
 29 24  1  0  0  0  0
 30 15  1  0  0  0  0
 31 23  2  0  0  0  0
 32 24  2  0  0  0  0
 33 25  2  0  0  0  0
 34  3  1  0  0  0  0
 34 16  1  0  0  0  0
 35  4  1  0  0  0  0
 35 21  1  0  0  0  0
 36  5  1  0  0  0  0
 36 22  1  0  0  0  0
 37  6  1  0  0  0  0
 37 25  1  0  0  0  0
 11 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0317523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C)CN(C(=O)C2=CC3=CC(OC)=C(OC)C(OC)=C3N2)C2=CC(O)=C3N[C@@](C)(C(=O)OC)C(=O)C3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H27N3O8/c1-11-10-29(14-9-15(30)20-18(17(11)14)23(31)26(2,28-20)25(33)37-6)24(32)13-7-12-8-16(34-3)21(35-4)22(36-5)19(12)27-13/h7-9,11,27-28,30H,10H2,1-6H3/t11-,26-/m1/s1

> <INCHI_KEY>
WQAYQZWERWNDPV-RPHGYIDUSA-N

> <FORMULA>
C26H27N3O8

> <MOLECULAR_WEIGHT>
509.5079

> <EXACT_MASS>
509.179814855

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
53.962448319654165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R,8S)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1H,2H,3H,6H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.530974663

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.24079072437388

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.152948721170361

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1211492305316293

> <JCHEM_POLAR_SURFACE_AREA>
139.42

> <JCHEM_REFRACTIVITY>
134.32309999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R,8S)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   26                                                            
CONECT    3   34                                                            
CONECT    4   35                                                            
CONECT    5   36                                                            
CONECT    6   37                                                            
CONECT    7   12   13                                                       
CONECT    8   12   16                                                       
CONECT    9   14   15                                                       
CONECT   10   11   29                                                       
CONECT   11    1   10   17   38                                             
CONECT   12    7    8   19                                                  
CONECT   13    7   24   27                                                  
CONECT   14    9   17   29                                                  
CONECT   15    9   20   30                                                  
CONECT   16    8   21   34                                                  
CONECT   17   11   14   18                                                  
CONECT   18   17   20   23                                                  
CONECT   19   12   22   27                                                  
CONECT   20   15   18   28                                                  
CONECT   21   16   22   35                                                  
CONECT   22   19   21   36                                                  
CONECT   23   18   26   31                                                  
CONECT   24   13   29   32                                                  
CONECT   25   26   33   37                                                  
CONECT   26    2   23   25   28                                             
CONECT   27   13   19                                                       
CONECT   28   20   26                                                       
CONECT   29   10   14   24                                                  
CONECT   30   15                                                            
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   25                                                            
CONECT   34    3   16                                                       
CONECT   35    4   21                                                       
CONECT   36    5   22                                                       
CONECT   37    6   25                                                       
CONECT   38   11                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
4-HYDROXY-2,8-dimethyl-1-oxo-6-(4,5,6-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2-carboxylate methyl ester	Generator
Methyl (2R,8S)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1H,2H,3H,6H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylic acid	Generator

Chemical Formula

C₂₆H₂₇N₃O₈

Average Mass

509.5079 Da

Monoisotopic Mass

509.17981 Da

IUPAC Name

methyl (2R,8S)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1H,2H,3H,6H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

Traditional Name

methyl (2R,8S)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)CN(C(=O)C2=CC3=CC(OC)=C(OC)C(OC)=C3N2)C2=CC(O)=C3N[C@@](C)(C(=O)OC)C(=O)C3=C12

InChI Identifier

InChI=1S/C26H27N3O8/c1-11-10-29(14-9-15(30)20-18(17(11)14)23(31)26(2,28-20)25(33)37-6)24(32)13-7-12-8-16(34-3)21(35-4)22(36-5)19(12)27-13/h7-9,11,27-28,30H,10H2,1-6H3/t11-,26-/m1/s1

InChI Key

WQAYQZWERWNDPV-RPHGYIDUSA-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 alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Indolecarboxamide derivative
Indolecarboxylic acid
Indolecarboxylic acid derivative
Pyrroloindole
Indole
Indole or derivatives
Dihydroindole
2-heteroaryl carboxamide
Anisole
Phenol ether
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aryl ketone
Aryl alkyl ketone
Secondary aliphatic/aromatic amine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Vinylogous amide
Methyl ester
Tertiary carboxylic acid amide
Heteroaromatic compound
Pyrrole
Ketone
Carboxamide group
Carboxylic acid ester
Monocarboxylic acid or derivatives
Secondary amine
Organoheterocyclic compound
Azacycle
Ether
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
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	3.41	ALOGPS
logP	2.53	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.32 m³·mol⁻¹	ChemAxon
Polarizability	53.96 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

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

5288126

PDB ID

DUO

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate (NP0317523)

MOL for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

3D MOL for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

3D SDF for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

3D-SDF for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

PDB for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

3D PDB for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

SMILES for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

INCHI for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

Structure for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)

3D Structure for NP0317523 (methyl (2r,8s)-4-hydroxy-2,8-dimethyl-1-oxo-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-3h,7h,8h-pyrrolo[3,2-e]indole-2-carboxylate)