NP-MRD: Showing NP-Card for 2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione (NP0290080)

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Record Information

Version

2.0

Created at

2022-09-09 20:35:43 UTC

Updated at

2022-09-09 20:35:43 UTC

NP-MRD ID

NP0290080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione

Description

2-Hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,5,6,7,8,9-hexahydro-3H-1,4-benzodiazepine-5,9-dione belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review very few articles have been published on 2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,5,6,7,8,9-hexahydro-3H-1,4-benzodiazepine-5,9-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092222352D          

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 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 12 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  6 35  2  0  0  0  0
 11 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290080

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1CCC(=O)C2=C1C(=O)NC(CC1=CNC3=C(CC=C(C)C)C(O)=CC=C13)C(O)=N2

> <INCHI_IDENTIFIER>
InChI=1S/C28H33N3O4/c1-15(2)5-7-17-8-11-23(33)26-24(17)28(35)30-21(27(34)31-26)13-18-14-29-25-19(18)10-12-22(32)20(25)9-6-16(3)4/h5-6,10,12,14,17,21,29,32H,7-9,11,13H2,1-4H3,(H,30,35)(H,31,34)

> <INCHI_KEY>
NGQHQXSBYFBPOA-UHFFFAOYSA-N

> <FORMULA>
C28H33N3O4

> <MOLECULAR_WEIGHT>
475.589

> <EXACT_MASS>
475.247106555

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.81444805381382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,5,6,7,8,9-hexahydro-3H-1,4-benzodiazepine-5,9-dione

> <JCHEM_LOGP>
4.772765224333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.841676723953668

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355553255319651

> <JCHEM_PKA_STRONGEST_BASIC>
0.28119614758148115

> <JCHEM_POLAR_SURFACE_AREA>
114.78

> <JCHEM_REFRACTIVITY>
139.26339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3H-1,4-benzodiazepine-5,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.344   1.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.678   0.990   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.011   1.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.678  -0.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.344  -1.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.344  -2.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.678  -3.630   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.011  -2.860   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.678  -5.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.344  -5.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.010  -5.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.546  -5.646   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.070  -7.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.563  -7.431   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.198  -8.927   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.199  -9.574   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.222 -11.114   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.576  -8.885   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.896  -7.379   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -1.918  -6.189   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -0.379  -6.213   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.310  -4.835   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.361  -6.903   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.681  -5.397   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.506  -7.934   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.185  -9.440   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.721  -9.916   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.401 -11.422   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.936 -11.898   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.616 -13.404   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.151 -13.880   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.760 -14.435   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.641  -4.400   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.546  -3.154   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       4.010  -3.630   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                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   27                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   12   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃N₃O₄

Average Mass

475.5890 Da

Monoisotopic Mass

475.24711 Da

IUPAC Name

2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,5,6,7,8,9-hexahydro-3H-1,4-benzodiazepine-5,9-dione

Traditional Name

2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3H-1,4-benzodiazepine-5,9-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1CCC(=O)C2=C1C(=O)NC(CC1=CNC3=C(CC=C(C)C)C(O)=CC=C13)C(O)=N2

InChI Identifier

InChI=1S/C28H33N3O4/c1-15(2)5-7-17-8-11-23(33)26-24(17)28(35)30-21(27(34)31-26)13-18-14-29-25-19(18)10-12-22(32)20(25)9-6-16(3)4/h5-6,10,12,14,17,21,29,32H,7-9,11,13H2,1-4H3,(H,30,35)(H,31,34)

InChI Key

NGQHQXSBYFBPOA-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 aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Aromatic monoterpenoid
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
Para-diazepine
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Substituted pyrrole
Benzenoid
Vinylogous amide
Pyrrole
Heteroaromatic compound
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
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	4.77	ChemAxon
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	0.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	114.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.26 m³·mol⁻¹	ChemAxon
Polarizability	52.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162868784

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione (NP0290080)

MOL for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

3D MOL for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

3D SDF for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

3D-SDF for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

PDB for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

3D PDB for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

SMILES for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

INCHI for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

Structure for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)

3D Structure for NP0290080 (2-hydroxy-3-{[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-6-(3-methylbut-2-en-1-yl)-4,6,7,8-tetrahydro-3h-1,4-benzodiazepine-5,9-dione)