NP-MRD: Showing NP-Card for 5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0256276)

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Record Information

Version

2.0

Created at

2022-09-07 21:02:12 UTC

Updated at

2022-09-07 21:02:13 UTC

NP-MRD ID

NP0256276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol

Description

5-(3,7-Dimethylocta-1,6-dien-3-yl)-13-(methoxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]Pentadeca-1,4,6,8(15),11-pentaen-11-ol belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. 5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol is found in Streptomyces blastmyceticus. 5-(3,7-Dimethylocta-1,6-dien-3-yl)-13-(methoxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]Pentadeca-1,4,6,8(15),11-pentaen-11-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241518032D          

 33 35  0  0  0  0            999 V2000
    6.4491   -0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7896    0.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0306   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3711    0.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4617   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5501    0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    0.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5524    2.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241518032D          

 33 35  0  0  0  0            999 V2000
    6.4491   -0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 22  1  0  0  0  0
 13 23  2  0  0  0  0
  6 23  1  0  0  0  0
  9 23  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0256276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC1CC2=CNC3=C(C=CC(N(C)C(C(C)C)C(=O)N1)=C23)C(C)(CCC=C(C)C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H41N3O2/c1-9-28(6,14-10-11-18(2)3)22-12-13-23-24-20(16-29-25(22)24)15-21(17-33-8)30-27(32)26(19(4)5)31(23)7/h9,11-13,16,19,21,26,29H,1,10,14-15,17H2,2-8H3,(H,30,32)

> <INCHI_KEY>
XEIXQLUJVVEPSF-UHFFFAOYSA-N

> <FORMULA>
C28H41N3O2

> <MOLECULAR_WEIGHT>
451.655

> <EXACT_MASS>
451.319877572

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.086318294498696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(methoxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15)-tetraen-11-one

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
5.929059184000001

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.097792263738505

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.157456293058186

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6827044468366469

> <JCHEM_POLAR_SURFACE_AREA>
57.36

> <JCHEM_REFRACTIVITY>
139.003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15)-tetraen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      12.038  -0.387   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.807   0.538   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.390  -0.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.159   0.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.869   0.019   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.340   0.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.595  -1.143   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.083  -0.851   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.893   0.677   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.631   1.559   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.763   3.093   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.158   3.746   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.206   2.868   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.131   4.099   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.291   5.389   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.631   4.447   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.817   5.976   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.234   6.579   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.586   6.901   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.004   3.750   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.129   4.801   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       8.608   2.333   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       4.288   1.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.236   0.906   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.417   2.301   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.159   0.254   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.422   1.135   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.816   0.483   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.079   1.365   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.474   0.712   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.947   2.899   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.889  -0.489   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.007  -1.751   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    4                                                       
CONECT   23   13    6    9                                                  
CONECT   24   10   25   26   32                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   24   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₁N₃O₂

Average Mass

451.6550 Da

Monoisotopic Mass

451.31988 Da

IUPAC Name

5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(methoxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15)-tetraen-11-one

Traditional Name

5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15)-tetraen-11-one

CAS Registry Number

Not Available

SMILES

COCC1CC2=CNC3=C(C=CC(N(C)C(C(C)C)C(=O)N1)=C23)C(C)(CCC=C(C)C)C=C

InChI Identifier

InChI=1S/C28H41N3O2/c1-9-28(6,14-10-11-18(2)3)22-12-13-23-24-20(16-29-25(22)24)15-21(17-33-8)30-27(32)26(19(4)5)31(23)7/h9,11-13,16,19,21,26,29H,1,10,14-15,17H2,2-8H3,(H,30,32)

InChI Key

XEIXQLUJVVEPSF-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

Species Name	Source	Reference
Streptomyces blastmyceticus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide 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 amides

Alternative Parents

Substituents

Alpha-amino acid amide
Aromatic monoterpenoid
Monoterpenoid
3-alkylindole
Indole
Indole or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Dialkyl ether
Ether
Amine
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen 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	5.33	ALOGPS
logP	5.93	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	-0.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139 m³·mol⁻¹	ChemAxon
Polarizability	53.09 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0256276)

MOL for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D MOL for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D SDF for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D-SDF for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

PDB for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D PDB for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

SMILES for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

INCHI for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

Structure for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D Structure for NP0256276 (5-(3,7-dimethylocta-1,6-dien-3-yl)-10-isopropyl-13-(methoxymethyl)-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)