NP-MRD: Showing NP-Card for bruceolline j (NP0244073)

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Record Information

Version

2.0

Created at

2022-09-07 04:46:21 UTC

Updated at

2022-09-07 04:46:22 UTC

NP-MRD ID

NP0244073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bruceolline j

Description

Bruceolline J 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. Bruceolline J is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. bruceolline j is found in Brucea mollis. bruceolline j was first documented in 2013 (PMID: 24109417). Based on a literature review a small amount of articles have been published on bruceolline J (PMID: 30496663) (PMID: 23937106).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.2895   -1.7359   -0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672   -0.5654   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060   -0.5295    1.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950   -0.5624   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010   -1.3754    0.0442 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075   -0.6135    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2580   -0.9509    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608    0.0793    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.4096    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4352    1.7318    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    0.7032    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183    0.7476   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615    1.6314   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1335    2.8039    0.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0896    0.7352   -0.7548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3685    1.1810   -0.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9435   -2.6825   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736   -1.6303   -1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3830   -1.6381   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    0.5400    1.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650   -0.8264    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6492   -1.1032    2.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7934   -2.4320    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768   -1.9757    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163   -0.1702    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    2.2026    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021    2.7700   -0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8664    0.6160   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4917    1.6398    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4  2  1  0
 11  6  1  0
 11 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
 15 28  1  6
 16 29  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END


  Mrv1652309072206462D          

 16 18  0  0  1  0            999 V2000
    2.0394    0.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693   -0.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1591   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942   -0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4519   -0.0860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322   -0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962   -0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568   -1.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -1.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230   -2.6863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299   -1.3898    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9505   -1.6601    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0244073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H](O)C(=O)C2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C13H13NO2/c1-13(2)11-9(10(15)12(13)16)7-5-3-4-6-8(7)14-11/h3-6,12,14,16H,1-2H3/t12-/m0/s1

> <INCHI_KEY>
QLFDLIVQYIHVGJ-LBPRGKRZSA-N

> <FORMULA>
C13H13NO2

> <MOLECULAR_WEIGHT>
215.252

> <EXACT_MASS>
215.094628663

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.149267451530548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-hydroxy-3,3-dimethyl-1H,2H,3H,4H-cyclopenta[b]indol-1-one

> <JCHEM_LOGP>
1.7272268756666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.165666506221626

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.2635646321107

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7885926466081488

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
61.051600000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3,3-dimethyl-2H,4H-cyclopenta[b]indol-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.807   0.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.676  -1.121   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.164  -0.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.216  -1.090   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.444  -0.161   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.707  -1.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.207  -0.691   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.260  -1.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.813  -3.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.313  -3.639   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.260  -2.515   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.720  -2.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.493  -3.475   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.523  -5.014   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.229  -2.594   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.774  -3.099   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   15                                             
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₃NO₂

Average Mass

215.2520 Da

Monoisotopic Mass

215.09463 Da

IUPAC Name

(2R)-2-hydroxy-3,3-dimethyl-1H,2H,3H,4H-cyclopenta[b]indol-1-one

Traditional Name

(2R)-2-hydroxy-3,3-dimethyl-2H,4H-cyclopenta[b]indol-1-one

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H](O)C(=O)C2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C13H13NO2/c1-13(2)11-9(10(15)12(13)16)7-5-3-4-6-8(7)14-11/h3-6,12,14,16H,1-2H3/t12-/m0/s1

InChI Key

QLFDLIVQYIHVGJ-LBPRGKRZSA-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
Brucea mollis	LOTUS Database	35616633

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 ketone
Aryl alkyl ketone
Benzenoid
Pyrrole
Vinylogous amide
Heteroaromatic compound
Secondary alcohol
Ketone
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:68921 )
organic heterotricyclic compound (CHEBI:68921 )
secondary alcohol (CHEBI:68921 )
indole alkaloid (CHEBI:68921 )

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	1.73	ChemAxon
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	61.05 m³·mol⁻¹	ChemAxon
Polarizability	23.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28532613

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56833858

PDB ID

Not Available

ChEBI ID

68921

Good Scents ID

Not Available

References

General References

Samat N, Ng MF, Lee HM, Ling SK, Tan PJ, Patel V: Canthin-6-one Isolated from Bruceajavanica Root Blocks Cancer Cells in the G2/M phase and Synergizes with Cisplatin. Nat Prod Commun. 2017 May;12(5):771-778. [PubMed:30496663 ]
Lopchuk JM, Gribble GW, Millikan SP, Jasinski JP: Bruceolline J: 2-hy-droxy-3,3-dimethyl-2,3-di-hydro-cyclo-penta-[b]indol-1(4H)-one. Acta Crystallogr Sect E Struct Rep Online. 2013 Jul 31;69(Pt 8):o1351-2. doi: 10.1107/S1600536813020527. eCollection 2013. [PubMed:24109417 ]
Lopchuk JM, Green IL, Badenock JC, Gribble GW: A short, protecting group-free total synthesis of bruceollines D, E, and J. Org Lett. 2013 Sep 6;15(17):4485-7. doi: 10.1021/ol402042f. Epub 2013 Aug 12. [PubMed:23937106 ]
LOTUS database [Link]

Showing NP-Card for bruceolline j (NP0244073)

MOL for NP0244073 (bruceolline j)

3D MOL for NP0244073 (bruceolline j)

3D SDF for NP0244073 (bruceolline j)

3D-SDF for NP0244073 (bruceolline j)

PDB for NP0244073 (bruceolline j)

3D PDB for NP0244073 (bruceolline j)

SMILES for NP0244073 (bruceolline j)

INCHI for NP0244073 (bruceolline j)

Structure for NP0244073 (bruceolline j)

3D Structure for NP0244073 (bruceolline j)