NP-MRD: Showing NP-Card for (3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol (NP0329100)

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Record Information

Version

2.0

Created at

2022-09-12 13:09:46 UTC

Updated at

2022-09-12 13:09:47 UTC

NP-MRD ID

NP0329100

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol

Description

Horsfiline belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. (3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol was first documented in 2014 (PMID: 25155110). Based on a literature review a small amount of articles have been published on Horsfiline (PMID: 35479130) (PMID: 35517527) (PMID: 29048900) (PMID: 24410404).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.9876    1.2312   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5936    1.4024   -0.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625    0.4387   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770   -0.7132    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -1.6766    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0591   -1.5043    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -0.3659    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006    0.5934   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9305   -0.5058    0.2905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6114   -0.4688   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.2159   -0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9978    0.4930    0.5813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6796    1.7677    0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205    0.6385    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1558   -1.7979    0.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4181   -2.3800    1.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0196   -2.3354    1.1619 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4548    2.0625   -1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    1.2643    0.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2614    0.2852   -1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703   -0.8455    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8442   -2.5690    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246    1.4884   -0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    0.4055   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4913   -1.4207   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    0.3073   -1.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934   -1.2277   -0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    1.6795   -0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005    2.5841    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1594    2.0463    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    1.5844    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5607    0.5071    2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5095   -2.7530    2.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 17  1  0
 17 15  2  0
 15 16  1  0
  9 15  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9  7  1  0
  7  8  2  0
  8  3  1  0
  7  6  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
 16 33  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
  8 23  1  0
M  END


  Mrv1652309122215092D          

 17 19  0  0  1  0            999 V2000
    6.3410    2.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238    2.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2132    1.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197    1.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4091    0.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0853    1.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3960    1.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095    0.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5336    0.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898    1.8911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    2.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824    1.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3365    0.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -0.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1291   -0.2161    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  9  7  1  6  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
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329100

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2N=C(O)[C@]3(CCN(C)C3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O2/c1-15-6-5-13(8-15)10-7-9(17-2)3-4-11(10)14-12(13)16/h3-4,7H,5-6,8H2,1-2H3,(H,14,16)/t13-/m0/s1

> <INCHI_KEY>
RVOLLKGLJIUGLG-ZDUSSCGKSA-N

> <FORMULA>
C13H16N2O2

> <MOLECULAR_WEIGHT>
232.283

> <EXACT_MASS>
232.121177763

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.912854824479638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidine]-2-ol

> <JCHEM_LOGP>
-1.0333869464523036

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.533762848653286

> <JCHEM_PKA_STRONGEST_BASIC>
9.093628746525072

> <JCHEM_POLAR_SURFACE_AREA>
45.06

> <JCHEM_REFRACTIVITY>
67.64860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
horsfiline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      11.837   5.363   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.311   5.151   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.731   3.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.677   2.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.097   1.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.571   0.871   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.626   2.087   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.206   3.514   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.178   1.563   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.729   1.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.784   2.255   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.648   3.530   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.124   4.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.127   3.102   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.228   0.024   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.013  -0.921   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       7.708  -0.403   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   14   15                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9                                                       
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
(+)-Horsfiline	MeSH
(-)-Horsfiline	MeSH
(R)-Horsfiline	MeSH

Chemical Formula

C₁₃H₁₆N₂O₂

Average Mass

232.2830 Da

Monoisotopic Mass

232.12118 Da

IUPAC Name

(3R)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidine]-2-ol

Traditional Name

horsfiline

CAS Registry Number

Not Available

SMILES

COC1=CC=C2N=C(O)[C@]3(CCN(C)C3)C2=C1

InChI Identifier

InChI=1S/C13H16N2O2/c1-15-6-5-13(8-15)10-7-9(17-2)3-4-11(10)14-12(13)16/h3-4,7H,5-6,8H2,1-2H3,(H,14,16)/t13-/m0/s1

InChI Key

RVOLLKGLJIUGLG-ZDUSSCGKSA-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 indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Ether
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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
logP	-1	ChemAxon
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.65 m³·mol⁻¹	ChemAxon
Polarizability	24.91 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026829

Chemspider ID

9217785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Horsfiline

METLIN ID

Not Available

PubChem Compound

11042617

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sathish M, Sakla AP, Nachtigall FM, Santos LS, Shankaraiah N: TCCA-mediated oxidative rearrangement of tetrahydro-beta-carbolines: facile access to spirooxindoles and the total synthesis of (+/-)-coerulescine and (+/-)-horsfiline. RSC Adv. 2021 May 5;11(27):16537-16546. doi: 10.1039/d1ra02381k. eCollection 2021 Apr 30. [PubMed:35479130 ]
Sathish M, Nachtigall FM, Santos LS: Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-beta-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement. RSC Adv. 2020 Oct 21;10(63):38672-38677. doi: 10.1039/d0ra07705d. eCollection 2020 Oct 15. [PubMed:35517527 ]
Buev EM, Moshkin VS, Sosnovskikh VY: Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids. J Org Chem. 2017 Dec 1;82(23):12827-12833. doi: 10.1021/acs.joc.7b02193. Epub 2017 Nov 1. [PubMed:29048900 ]
Mukaiyama T, Ogata K, Sato I, Hayashi Y: Asymmetric organocatalyzed Michael addition of nitromethane to a 2-oxoindoline-3-ylidene acetaldehyde and the three one-pot sequential synthesis of (-)-horsfiline and (-)-coerulescine. Chemistry. 2014 Oct 13;20(42):13583-8. doi: 10.1002/chem.201403932. Epub 2014 Aug 25. [PubMed:25155110 ]
Lv J, Zhang-Negrerie D, Deng J, Du Y, Zhao K: Metal-free synthesis of 2-oxindoles via PhI(OAc)2-mediated oxidative C-C bond formation. J Org Chem. 2014 Feb 7;79(3):1111-9. doi: 10.1021/jo4025539. [PubMed:24410404 ]
LOTUS database [Link]

Showing NP-Card for (3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol (NP0329100)

MOL for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

3D MOL for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

3D SDF for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

3D-SDF for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

PDB for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

3D PDB for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

SMILES for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

INCHI for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

Structure for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)

3D Structure for NP0329100 ((3r)-5-methoxy-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol)