NP-MRD: Showing NP-Card for Borrecapine (NP0331607)

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Record Information

Version

2.0

Created at

2023-04-26 20:03:26 UTC

Updated at

2024-09-03 04:16:14 UTC

NP-MRD ID

NP0331607

Natural Product DOI

https://doi.org/10.57994/0588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Borrecapine

Description

Borrecapine belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Borrecapine was first documented in 2023 (PMID: 37247764). Based on a literature review very few articles have been published on Borrecapine (PMID: 39149871).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304262322032D          

 23 25  0  0  1  0            999 V2000
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2587   -3.0752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -2.9890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6313   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3763   -4.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693   -4.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9284   -4.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508   -2.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -1.7695    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8639   -1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -1.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018   -0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 13 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@H]1C[C@@](C)(C=C)[C@@H](N1)C(=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O/c1-5-20(4)11-14(10-13(2)3)22-19(20)18(23)16-12-21-17-9-7-6-8-15(16)17/h5-10,12,14,19,21-22H,1,11H2,2-4H3/t14-,19-,20+/m0/s1

> <INCHI_KEY>
ZSWYXBSEVUNDFU-PNHOKKKMSA-N

> <FORMULA>
C20H24N2O

> <MOLECULAR_WEIGHT>
308.425

> <EXACT_MASS>
308.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.67328953432076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2R,3S,5R)-3-ethenyl-3-methyl-5-(2-methylprop-1-en-1-yl)pyrrolidine-2-carbonyl]-1H-indole

> <JCHEM_LOGP>
4.060427147666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.752813846476705

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.145797129776238

> <JCHEM_PKA_STRONGEST_BASIC>
8.56221248526241

> <JCHEM_POLAR_SURFACE_AREA>
44.89

> <JCHEM_REFRACTIVITY>
95.27110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2R,3S,5R)-3-ethenyl-3-methyl-5-(2-methylprop-1-en-1-yl)pyrrolidine-2-carbonyl]-1H-indole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-23         0                                  
HETATM    1  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.483  -5.740   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.015  -5.579   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.045  -6.724   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.569  -8.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.063  -8.509   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.600  -9.333   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.335  -4.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.001  -3.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.613  -1.890   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.109  -2.048   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.750  -0.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924  -2.843   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
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10    3   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    2   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   15                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N₂O

Average Mass

308.4250 Da

Monoisotopic Mass

308.18886 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@H]1C[C@@](C)(C=C)[C@@H](N1)C(=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H24N2O/c1-5-20(4)11-14(10-13(2)3)22-19(20)18(23)16-12-21-17-9-7-6-8-15(16)17/h5-10,12,14,19,21-22H,1,11H2,2-4H3/t14-,19-,20+/m0/s1

InChI Key

ZSWYXBSEVUNDFU-PNHOKKKMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	Not Available	Not Available	2023-04-26	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Aryl alkyl ketone
Aryl ketone
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Vinylogous amide
Pyrrolidine
Pyrrole
Alpha-aminoketone
Ketone
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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

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

Lavernhe R, Wang Q, Zhu J: [4+1] Heteroannulation to Form 1-Pyrrolines through Alder-Ene Reaction of in situ Generated Ynimines: Development and Application in Total Synthesis of Borrecapine. Angew Chem Int Ed Engl. 2024 Aug 16:e202414612. doi: 10.1002/anie.202414612. [PubMed:39149871 ]
Beniddir MA, Jagora A, Szwarc S, Hafidi W, Gallard JF, Retailleau P, Buevich AV, Le Pogam P: Unifying the configuration of historical alkaloids from Borreria capitata through an extensive spectroscopic reinvestigation. Phytochemistry. 2023 Aug;212:113741. doi: 10.1016/j.phytochem.2023.113741. Epub 2023 May 27. [PubMed:37247764 ]

Showing NP-Card for Borrecapine (NP0331607)

MOL for NP0331607 (Borrecapine)

3D MOL for NP0331607 (Borrecapine)

3D SDF for NP0331607 (Borrecapine)

3D-SDF for NP0331607 (Borrecapine)

PDB for NP0331607 (Borrecapine)

3D PDB for NP0331607 (Borrecapine)

SMILES for NP0331607 (Borrecapine)

INCHI for NP0331607 (Borrecapine)

Structure for NP0331607 (Borrecapine)

3D Structure for NP0331607 (Borrecapine)