NP-MRD: Showing NP-Card for (10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0294762)

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Record Information

Version

2.0

Created at

2022-09-10 03:27:25 UTC

Updated at

2022-09-10 03:27:26 UTC

NP-MRD ID

NP0294762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Teleocidin A2 belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. (10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol is found in Kitasatospora mediocidica. (10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol was first documented in 2016 (PMID: 28116092). Based on a literature review very few articles have been published on Teleocidin A2 (PMID: 29195005).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102205272D          

 32 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102205272D          

 32 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0294762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1N(C)C2=C3C(C[C@@H](CO)N=C1O)=CNC3=C(C=C2)[C@@](C)(CCC=C(C)C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27+/m0/s1

> <INCHI_KEY>
KISDGNGREAJPQR-QOAWAWRESA-N

> <FORMULA>
C27H39N3O2

> <MOLECULAR_WEIGHT>
437.628

> <EXACT_MASS>
437.304227508

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.33012999855294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S,13S)-5-[(3S)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

> <JCHEM_LOGP>
5.718160800069639

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.081800095121668

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.149220750010379

> <JCHEM_PKA_STRONGEST_BASIC>
5.203897585381636

> <JCHEM_POLAR_SURFACE_AREA>
71.85

> <JCHEM_REFRACTIVITY>
134.77349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10S,13S)-5-[(3S)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.503   0.732   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.379  -0.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.274  -1.926   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.926  -3.321   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.121  -2.578   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.384  -1.697   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.779  -2.349   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.041  -1.468   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.436  -2.120   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.909   0.067   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.669  -1.273   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.801   0.261   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.196   0.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.244   0.035   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.326  -1.502   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.378  -2.627   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.633  -3.975   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.121  -3.683   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.931  -2.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.907  -2.813   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.197  -1.973   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.428  -2.898   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.845  -2.294   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       8.646  -0.499   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       8.042   0.917   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.167   1.969   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.669   1.615   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.855   3.144   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.624   4.069   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.272   3.747   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       5.169   1.267   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       4.329   2.557   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11   15                                                  
CONECT   20   16   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   14   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉N₃O₂

Average Mass

437.6280 Da

Monoisotopic Mass

437.30423 Da

IUPAC Name

(10S,13S)-5-[(3S)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

Traditional Name

(10S,13S)-5-[(3S)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N(C)C2=C3C(C[C@@H](CO)N=C1O)=CNC3=C(C=C2)[C@@](C)(CCC=C(C)C)C=C

InChI Identifier

InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27+/m0/s1

InChI Key

KISDGNGREAJPQR-QOAWAWRESA-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
Kitasatospora mediocidica	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
Heteroaromatic compound
Pyrrole
Carboxamide group
Lactam
Tertiary amine
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Primary alcohol
Amine
Alcohol
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	5.72	ChemAxon
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	71.85 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.77 m³·mol⁻¹	ChemAxon
Polarizability	51.33 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

10472343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13749857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stein J, Stahn S, Neudorfl JM, Sperlich J, Schmalz HG, Teusch N: Synthetic Indolactam V Analogues as Inhibitors of PAR2-Induced Calcium Mobilization in Triple-Negative Breast Cancer Cells. ChemMedChem. 2018 Jan 22;13(2):147-154. doi: 10.1002/cmdc.201700640. Epub 2018 Jan 4. [PubMed:29195005 ]
Stahn S, Thelen L, Albrecht IM, Bitzer J, Henkel T, Teusch NE: Teleocidin A2 inhibits human proteinase-activated receptor 2 signaling in tumor cells. Pharmacol Res Perspect. 2016 Jun 10;4(4):e00230. doi: 10.1002/prp2.230. eCollection 2016 Aug. [PubMed:28116092 ]
LOTUS database [Link]

Showing NP-Card for (10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0294762)

MOL for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D MOL for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D SDF for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D-SDF for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

PDB for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D PDB for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

SMILES for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

INCHI for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

Structure for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D Structure for NP0294762 ((10s,13s)-5-[(3s)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)