NP-MRD: Showing NP-Card for Oleracein E (NP0044059)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:43 UTC

Updated at

2021-11-26 17:44:58 UTC

NP-MRD ID

NP0044059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oleracein E

Description

(+)-Oleracein E belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Oleracein E is found in Trollius chinensis. It was first documented in 2005 (PMID: 16203019). Based on a literature review a significant number of articles have been published on (+)-Oleracein E (PMID: 34662767) (PMID: 33895604) (PMID: 32691626) (PMID: 32387233).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -4.0622   -1.2139    0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1077   -0.4344    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138    1.0218    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489    1.2540   -0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940    0.4712    0.5132 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3960    0.2961    0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    1.3553    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049    1.2925   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    2.3840    0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1012    0.1272   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    0.0584   -0.9478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -0.9510   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204   -0.8553   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -2.0003   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9659   -2.0274    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -0.7990    0.5107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159    1.5436    1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0364    1.2829   -0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5971    2.3294   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8450    0.7720   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260    0.9053    1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930    2.2850    0.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617    3.2369    0.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8307   -0.7830   -1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -1.8893   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6075   -1.7519   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5385   -2.9587   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317   -2.8993    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069   -2.0519    1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2 16  1  0
 16  5  1  0
  5  6  1  0
  6 13  2  0
 13 14  1  0
 14 15  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
 15 16  1  0
  6  7  1  0
  5 21  1  1
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 12 25  1  0
 11 24  1  0
  9 23  1  0
  7 22  1  0
  4 19  1  0
  4 20  1  0
  3 17  1  0
  3 18  1  0
M  END


  Mrv1652311132100472D          

 17 19  0  0  1  0            999 V2000
    4.2295   -0.5732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047    1.2069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  5 14  2  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
  4 17  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC(=O)N1CCC1=CC(O)=C(O)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO3/c14-10-5-7-3-4-13-9(1-2-12(13)16)8(7)6-11(10)15/h5-6,9,14-15H,1-4H2/t9-/m1/s1

> <INCHI_KEY>
LJIDRFNRDLYHNC-SECBINFHSA-N

> <FORMULA>
C12H13NO3

> <MOLECULAR_WEIGHT>
219.24

> <EXACT_MASS>
219.089543283

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.555741127882545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10bR)-8,9-dihydroxy-1H,2H,3H,5H,6H,10bH-pyrrolo[2,1-a]isoquinolin-3-one

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.8610648176666669

> <ALOGPS_LOGS>
-1.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.631162810125101

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.19046668990712

> <JCHEM_PKA_STRONGEST_BASIC>
-1.576397323579585

> <JCHEM_POLAR_SURFACE_AREA>
60.77000000000001

> <JCHEM_REFRACTIVITY>
58.708800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10bR)-8,9-dihydroxy-1H,2H,5H,6H,10bH-pyrrolo[2,1-a]isoquinolin-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0       7.895  -1.070   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.223  -0.443   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.745   0.674   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       3.742   2.253   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   15   17                                             
CONECT    5    4    6   14                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5                                                       
CONECT   15    4   16                                                       
CONECT   16   15    2                                                       
CONECT   17    4                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₃NO₃

Average Mass

219.2400 Da

Monoisotopic Mass

219.08954 Da

IUPAC Name

(10bR)-8,9-dihydroxy-1H,2H,3H,5H,6H,10bH-pyrrolo[2,1-a]isoquinolin-3-one

Traditional Name

(10bR)-8,9-dihydroxy-1H,2H,5H,6H,10bH-pyrrolo[2,1-a]isoquinolin-3-one

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC(=O)N1CCC1=CC(O)=C(O)C=C21

InChI Identifier

InChI=1S/C12H13NO3/c14-10-5-7-3-4-13-9(1-2-12(13)16)8(7)6-11(10)15/h5-6,9,14-15H,1-4H2/t9-/m1/s1

InChI Key

LJIDRFNRDLYHNC-SECBINFHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trollius chinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyrrolidone
Benzenoid
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Carboxylic acid derivative
Azacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
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	0.66	ALOGPS
logP	0.86	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	58.71 m³·mol⁻¹	ChemAxon
Polarizability	22.56 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

30825689

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54597686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiang L, Xing D, Wang W, Wang R, Ding Y, Du L: Alkaloids from Portulaca oleracea L. Phytochemistry. 2005 Nov;66(21):2595-601. doi: 10.1016/j.phytochem.2005.08.011. Epub 2005 Oct 3. [PubMed:16203019 ]
Rai R, Kumar S, Singh KB, Khanka S, Singh Y, Arya KR, Kanojiya S, Maurya R, Singh D: Extract and fraction of Musa paradisiaca flower have osteogenic effect and prevent ovariectomy induced osteopenia. Phytomedicine. 2021 Dec;93:153750. doi: 10.1016/j.phymed.2021.153750. Epub 2021 Sep 14. [PubMed:34662767 ]
Afridi S, Adnan M, Hameed MW, Khalil AW, Iqbal Z, Hoessli DC, Shahid M, Khan SU, Iqbal J, Zhang X, Wu Z: Small organic molecules accelerate the expansion of regulatory T cells. Bioorg Chem. 2021 Jun;111:104908. doi: 10.1016/j.bioorg.2021.104908. Epub 2021 Apr 20. [PubMed:33895604 ]
Gu Y, Leng A, Zhang W, Ying X, Stien D: A novel alkaloid from Portulaca oleracea L. and its anti-inflammatory activity. Nat Prod Res. 2020 Jul 21:1-6. doi: 10.1080/14786419.2020.1795855. [PubMed:32691626 ]
Zhao F, Bai R, Li J, Feng X, Jiao S, Wuken S, Ge F, Zhang Q, Zhou X, Tu P, Chai X: Meconopsis horridula Hook. f. & Thomson extract and its alkaloid oleracein E exert cardioprotective effects against acute myocardial ischaemic injury in mice. J Ethnopharmacol. 2020 Aug 10;258:112893. doi: 10.1016/j.jep.2020.112893. Epub 2020 May 5. [PubMed:32387233 ]

Showing NP-Card for Oleracein E (NP0044059)

MOL for NP0044059 (Oleracein E)

3D MOL for NP0044059 (Oleracein E)

3D SDF for NP0044059 (Oleracein E)

3D-SDF for NP0044059 (Oleracein E)

PDB for NP0044059 (Oleracein E)

3D PDB for NP0044059 (Oleracein E)

SMILES for NP0044059 (Oleracein E)

INCHI for NP0044059 (Oleracein E)

Structure for NP0044059 (Oleracein E)

3D Structure for NP0044059 (Oleracein E)