NP-MRD: Showing NP-Card for 4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate (NP0165740)

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Record Information

Version

2.0

Created at

2022-09-03 00:57:27 UTC

Updated at

2022-09-03 00:57:27 UTC

NP-MRD ID

NP0165740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate

Description

Batzelladine C belongs to the class of organic compounds known as hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.E. Containing less than the maximum number of double bonds.). It was first documented in 2004 (PMID: 15070310). Based on a literature review a small amount of articles have been published on Batzelladine C (PMID: 33911315) (PMID: 26404724) (PMID: 19907792) (PMID: 18928319).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202572D          

 35 37  0  0  1  0            999 V2000
   -8.4341    3.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6387    2.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540    3.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2409    2.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4563    2.7449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032202572D          

 35 37  0  0  1  0            999 V2000
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   -1.1726    2.0172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    2.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432    2.1928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8871    3.2547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  8 34  1  0  0  0  0
 33 35  1  0  0  0  0
 13 35  1  0  0  0  0
 10 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC[C@H]1CC2CCC3=C([C@@H](CCCCC)NC(=N1)N23)C(=O)OCCCCNC(N)=N

> <INCHI_IDENTIFIER>
InChI=1S/C27H48N6O2/c1-3-5-7-8-10-13-20-19-21-15-16-23-24(25(34)35-18-12-11-17-30-26(28)29)22(14-9-6-4-2)32-27(31-20)33(21)23/h20-22H,3-19H2,1-2H3,(H,31,32)(H4,28,29,30)/t20-,21?,22+/m0/s1

> <INCHI_KEY>
JHUNDPSWNACCLC-JAFNVKOHSA-N

> <FORMULA>
C27H48N6O2

> <MOLECULAR_WEIGHT>
488.721

> <EXACT_MASS>
488.38387481

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.36811092528511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-carbamimidamidobutyl (6R,10S)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0^{4,12}]dodeca-4,8-diene-5-carboxylate

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.698271245333333

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
11.997275347409133

> <JCHEM_POLAR_SURFACE_AREA>
115.83

> <JCHEM_REFRACTIVITY>
152.878

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-carbamimidamidobutyl (6R,10S)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0^{4,12}]dodeca-4,8-diene-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0     -15.744   6.312   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.279   6.787   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.135   5.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.670   6.233   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.525   5.202   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.061   5.678   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.916   4.648   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.452   5.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.132   6.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.667   7.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.041   8.513   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.509   8.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.189   6.845   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.855   6.075   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.479   6.845   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.479   8.385   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.812   6.075   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.146   6.845   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.480   6.075   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.813   6.845   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.147   6.075   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       8.481   6.845   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       9.814   6.075   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      11.148   6.845   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       9.814   4.535   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -0.855   4.535   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.479   3.765   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.812   4.535   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.146   3.765   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.480   4.535   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.813   3.765   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -2.189   3.765   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -3.843   4.569   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -5.307   4.093   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      -3.523   6.075   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   35                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   14   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   26   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33    8                                                       
CONECT   35   33   13   10                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₈N₆O₂

Average Mass

488.7210 Da

Monoisotopic Mass

488.38387 Da

IUPAC Name

4-carbamimidamidobutyl (6R,10S)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0^{4,12}]dodeca-4,8-diene-5-carboxylate

Traditional Name

4-carbamimidamidobutyl (6R,10S)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0^{4,12}]dodeca-4,8-diene-5-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCCC[C@H]1CC2CCC3=C([C@@H](CCCCC)NC(=N1)N23)C(=O)OCCCCNC(N)=N

InChI Identifier

InChI=1S/C27H48N6O2/c1-3-5-7-8-10-13-20-19-21-15-16-23-24(25(34)35-18-12-11-17-30-26(28)29)22(14-9-6-4-2)32-27(31-20)33(21)23/h20-22H,3-19H2,1-2H3,(H,31,32)(H4,28,29,30)/t20-,21?,22+/m0/s1

InChI Key

JHUNDPSWNACCLC-JAFNVKOHSA-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 hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.E. Containing less than the maximum number of double bonds.).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Hydropyrimidines

Alternative Parents

Substituents

1,2,3,4-tetrahydropyrimidine
1,4,5,6-tetrahydropyrimidine
Hydropyrimidine
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Guanidine
Carboxylic acid ester
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Monocarboxylic acid or derivatives
Enamine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.51	ALOGPS
logP	4.7	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	12	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.83 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	152.88 m³·mol⁻¹	ChemAxon
Polarizability	60.37 Å³	ChemAxon
Number of Rings	3	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

C00028137

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

124081059

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Economou C, Romaire JP, Scott TZ, Parr BT, Herzon SB: A convergent approach to batzelladine alkaloids. Total syntheses of (+)-batzelladine E, (-)-dehydrobatzelladine C, and (+)-batzelladine K. Tetrahedron. 2018 Jun;74(26):3188-3197. doi: 10.1016/j.tet.2018.04.050. Epub 2018 Apr 18. [PubMed:33911315 ]
Ahmed N, Brahmbhatt KG, Khan SI, Jacob M, Tekwani BL, Sabde S, Mitra D, Singh IP, Khan IA, Bhutani KK: Synthesis and biological evaluation of tricyclic guanidine analogues of batzelladine K for antimalarial, antileishmanial, antibacterial, antifungal and anti-HIV activities. Chem Biol Drug Des. 2012 Jun 15. doi: 10.1111/j.1747-0285.2012.01427.x. [PubMed:26404724 ]
Butters M, Davies CD, Elliott MC, Hill-Cousins J, Kariuki BM, Ooi LL, Wood JL, Wordingham SV: Synthesis and stereochemical determination of batzelladine C methyl ester. Org Biomol Chem. 2009 Dec 7;7(23):5001-9. doi: 10.1039/b914744f. Epub 2009 Oct 13. [PubMed:19907792 ]
Yu M, Pochapsky SS, Snider BB: Synthesis of 7-epineoptilocaulin, mirabilin B, and isoptilocaulin. A unified biosynthetic proposal for the ptilocaulin and batzelladine alkaloids. Synthesis and structure revision of netamines E and G. J Org Chem. 2008 Nov 21;73(22):9065-74. doi: 10.1021/jo801956w. Epub 2008 Oct 18. [PubMed:18928319 ]
Collins SK, McDonald AI, Overman LE, Rhee YH: Enantioselective total synthesis of (-)-dehydrobatzelladine C. [structure: see text]. Org Lett. 2004 Apr 15;6(8):1253-5. doi: 10.1021/ol0498141. [PubMed:15070310 ]
LOTUS database [Link]

Showing NP-Card for 4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate (NP0165740)

MOL for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

3D MOL for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

3D SDF for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

3D-SDF for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

PDB for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

3D PDB for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

SMILES for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

INCHI for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

Structure for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)

3D Structure for NP0165740 (4-carbamimidamidobutyl (6r,10s)-10-heptyl-6-pentyl-7,9,12-triazatricyclo[6.3.1.0⁴,¹²]dodeca-4,8-diene-5-carboxylate)