NP-MRD: Showing NP-Card for (3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol (NP0245574)

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Record Information

Version

2.0

Created at

2022-09-07 06:42:14 UTC

Updated at

2022-09-07 06:42:14 UTC

NP-MRD ID

NP0245574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol

Description

Dehydrovariecolorin L belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on Dehydrovariecolorin L.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208422D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072208422D          

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M  END
> <DATABASE_ID>
NP0245574

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1N=C(O)\C(=C\C2=C(NC3=CC=C(CC=C(C)C)C(CC=C(C)C)=C23)C(C)(C)C=C)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H37N3O2/c1-9-29(7,8)26-22(16-24-28(34)30-19(6)27(33)32-24)25-21(14-11-18(4)5)20(12-10-17(2)3)13-15-23(25)31-26/h9-11,13,15-16,19,31H,1,12,14H2,2-8H3,(H,30,34)(H,32,33)/b24-16-/t19-/m0/s1

> <INCHI_KEY>
QSQTZUHCCQQTGU-UZXDDYOISA-N

> <FORMULA>
C29H37N3O2

> <MOLECULAR_WEIGHT>
459.634

> <EXACT_MASS>
459.288577443

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.072789536636726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z,6S)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-6-methyl-3,6-dihydropyrazine-2,5-diol

> <JCHEM_LOGP>
6.618755835010609

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.804604724823315

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.382036940655989

> <JCHEM_PKA_STRONGEST_BASIC>
3.3552672317550707

> <JCHEM_POLAR_SURFACE_AREA>
80.97

> <JCHEM_REFRACTIVITY>
144.58629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,6S)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-6-methyl-6H-pyrazine-2,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.320   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.592  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.227  -7.837   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       4.187  -4.838   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       5.217  -5.982   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.723  -5.662   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.741  -7.447   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.772  -8.591   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.235  -7.767   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17    8   24                                                  
CONECT   24   23    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₇N₃O₂

Average Mass

459.6340 Da

Monoisotopic Mass

459.28858 Da

IUPAC Name

(3Z,6S)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-6-methyl-3,6-dihydropyrazine-2,5-diol

Traditional Name

(3Z,6S)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-6-methyl-6H-pyrazine-2,5-diol

CAS Registry Number

Not Available

SMILES

C[C@@H]1N=C(O)\C(=C\C2=C(NC3=CC=C(CC=C(C)C)C(CC=C(C)C)=C23)C(C)(C)C=C)N=C1O

InChI Identifier

InChI=1S/C29H37N3O2/c1-9-29(7,8)26-22(16-24-28(34)30-19(6)27(33)32-24)25-21(14-11-18(4)5)20(12-10-17(2)3)13-15-23(25)31-26/h9-11,13,15-16,19,31H,1,12,14H2,2-8H3,(H,30,34)(H,32,33)/b24-16-/t19-/m0/s1

InChI Key

QSQTZUHCCQQTGU-UZXDDYOISA-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Alpha-amino acid or derivatives
Indole
Indole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
1,4-diazinane
Piperazine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Lactam
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	6.62	ChemAxon
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	3.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	80.97 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	144.59 m³·mol⁻¹	ChemAxon
Polarizability	54.07 Å³	ChemAxon
Number of Rings	3	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

C00048686

Chemspider ID

27023832

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25147188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol (NP0245574)

MOL for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

3D MOL for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

3D SDF for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

3D-SDF for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

PDB for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

3D PDB for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

SMILES for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

INCHI for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

Structure for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)

3D Structure for NP0245574 ((3z,6s)-3-{[4,5-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-6-methyl-6h-pyrazine-2,5-diol)