NP-MRD: Showing NP-Card for Borreverine (NP0050839)

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Record Information

Version

2.0

Created at

2022-04-27 22:14:41 UTC

Updated at

2022-04-27 22:14:41 UTC

NP-MRD ID

NP0050839

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Borreverine

Description

3'-Epi-Borreverine belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Borreverine is found in Flindersia fournieri and Borreria verticillata . Based on a literature review very few articles have been published on 3'-epi-Borreverine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200142D          

 36 42  0  0  1  0            999 V2000
    5.2674    3.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9437    4.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    4.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6293    3.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9531    2.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7721    2.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310    1.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    1.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    2.0693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1111    0.6887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7155    0.1272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2440    0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7 33  1  0  0  0  0
 33 34  1  0  0  0  0
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 35 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282200142D          

 36 42  0  0  1  0            999 V2000
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 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  6  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 22 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 31  1  0  0  0  0
 29 32  1  0  0  0  0
  7 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050839

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCCC1=C(NC2=CC=CC=C12)[C@@H]1[C@@H]2[C@@H](C=C(C)CC2(C)C)[C@]23NC4=CC=CC=C4[C@]12CCN3C

> <INCHI_IDENTIFIER>
InChI=1S/C32H40N4/c1-20-18-24-27(30(2,3)19-20)28(29-22(14-16-33-4)21-10-6-8-12-25(21)34-29)31-15-17-36(5)32(24,31)35-26-13-9-7-11-23(26)31/h6-13,18,24,27-28,33-35H,14-17,19H2,1-5H3/t24-,27+,28+,31-,32-/m1/s1

> <INCHI_KEY>
PHMBUGRSZKDHNS-POFWMSJRSA-N

> <FORMULA>
C32H40N4

> <MOLECULAR_WEIGHT>
480.7

> <EXACT_MASS>
480.325297304

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.355698851588116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl(2-{2-[(1S,9R,10R,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.0^{1,9}.0^{2,7}.0^{10,15}]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl}ethyl)amine

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
5.389988191333334

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.765646326554137

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.604358087201007

> <JCHEM_PKA_STRONGEST_BASIC>
10.293909895379697

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
151.61929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl(2-{2-[(1S,9R,10R,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.0^{1,9}.0^{2,7}.0^{10,15}]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl}ethyl)amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.832   6.306   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.228   7.723   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.699   7.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.775   6.676   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.379   5.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.908   5.075   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.205   3.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.859   2.814   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.731   3.863   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.674   1.286   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.802   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.789   0.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.492   1.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.949   0.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.245  -0.945   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.085  -1.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.263  -2.001   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       8.918  -2.750   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       8.154  -1.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.625  -0.975   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.329   0.537   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.872   1.035   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.711   0.023   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.008  -1.488   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.465  -1.987   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.847  -2.501   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.900   2.230   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.319   2.509   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       9.282  -2.208   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      10.628  -1.459   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.331   0.052   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.097  -3.737   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.601   2.915   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.861   3.801   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      13.258   3.153   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      14.518   4.038   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   33                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11   21                                                  
CONECT   11   10   12   19   31                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   11   20   29                                             
CONECT   20   19   21   25                                                  
CONECT   21   20   10   22                                                  
CONECT   22   21   23   27   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24                                                            
CONECT   27   22                                                            
CONECT   28   22                                                            
CONECT   29   19   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   11                                                       
CONECT   32   29                                                            
CONECT   33    7   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₀N₄

Average Mass

480.7000 Da

Monoisotopic Mass

480.32530 Da

IUPAC Name

methyl(2-{2-[(1S,9R,10R,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.0^{1,9}.0^{2,7}.0^{10,15}]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl}ethyl)amine

Traditional Name

methyl(2-{2-[(1S,9R,10R,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.0^{1,9}.0^{2,7}.0^{10,15}]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl}ethyl)amine

CAS Registry Number

Not Available

SMILES

CNCCC1=C(NC2=CC=CC=C12)[C@@H]1[C@@H]2[C@@H](C=C(C)CC2(C)C)[C@]23NC4=CC=CC=C4[C@]12CCN3C

InChI Identifier

InChI=1S/C32H40N4/c1-20-18-24-27(30(2,3)19-20)28(29-22(14-16-33-4)21-10-6-8-12-25(21)34-29)31-15-17-36(5)32(24,31)35-26-13-9-7-11-23(26)31/h6-13,18,24,27-28,33-35H,14-17,19H2,1-5H3/t24-,27+,28+,31-,32-/m1/s1

InChI Key

PHMBUGRSZKDHNS-POFWMSJRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Flindersia fournieri	Plant	KNApSAcK
Hedyotis verticillata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Tryptamine
2,3-cyclopentanoindoline
3-alkylindole
Indole
Dihydroindole
Aralkylamine
Substituted pyrrole
N-alkylpyrrolidine
Benzenoid
Heteroaromatic compound
Pyrrolidine
Pyrrole
Secondary amine
Azacycle
Secondary aliphatic amine
Amine
Organonitrogen compound
Hydrocarbon derivative
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	5.57	ALOGPS
logP	5.39	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	151.62 m³·mol⁻¹	ChemAxon
Polarizability	56.36 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

102127847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Borreverine (NP0050839)

MOL for NP0050839 (Borreverine)

3D MOL for NP0050839 (Borreverine)

3D SDF for NP0050839 (Borreverine)

3D-SDF for NP0050839 (Borreverine)

PDB for NP0050839 (Borreverine)

3D PDB for NP0050839 (Borreverine)

SMILES for NP0050839 (Borreverine)

INCHI for NP0050839 (Borreverine)

Structure for NP0050839 (Borreverine)

3D Structure for NP0050839 (Borreverine)