NP-MRD: Showing NP-Card for Clivojuline (NP0066750)

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Record Information

Version

2.0

Created at

2022-04-28 10:59:35 UTC

Updated at

2022-04-28 10:59:35 UTC

NP-MRD ID

NP0066750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Clivojuline

Description

2-[(5S,7S,7aS)-5-(acetyloxy)-1-methyl-2,3,5,6,7,7a-hexahydro-1H-indol-7-yl]benzoic acid belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Clivojuline is found in Clivia miniata and Clivia miniata Regel . Based on a literature review very few articles have been published on 2-[(5S,7S,7aS)-5-(acetyloxy)-1-methyl-2,3,5,6,7,7a-hexahydro-1H-indol-7-yl]benzoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    4.9690   -2.8775   -0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -2.0951   -0.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381   -2.1053   -2.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1056   -1.3232    0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9672   -0.5465   -0.1154 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1537    0.8866    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975    1.6412    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1863    3.0913    0.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296    3.4838    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320    2.2681    0.2421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0194    2.1291   -1.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359    1.1884    0.8889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3859   -0.1306    0.3451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5559   -0.9122    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542   -2.1982   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4193   -3.0064   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7047   -2.5904   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9436   -1.3472   -0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -0.5327    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013    0.6829    0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9642    1.4889    0.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    0.9675    2.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -0.9811    0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7741   -2.1117   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202   -3.4811    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2807   -3.5258   -1.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6323   -0.6520   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375    1.3080   -0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290    3.6211    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248    3.2636    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6798    3.9133    1.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    4.2214   -0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7017    1.3617   -1.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284    2.0069   -1.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192    3.1132   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2484    1.2942    1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804    0.0420   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3776   -2.6028   -0.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2664   -3.9942   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871   -3.1668   -0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9396   -0.9587    0.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877    1.8199    2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -2.0360    0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -0.6176    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5 23  1  0
 23 13  1  0
 13 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 12 10  1  0
 19 14  1  0
 12  7  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
  9 31  1  0
  9 32  1  0
  8 29  1  0
  8 30  1  0
  6 28  1  0
  5 27  1  6
 23 43  1  0
 23 44  1  0
 13 37  1  6
 12 36  1  1
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 22 42  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652304282212592D          

 23 25  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    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
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   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  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  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
  5 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 16 19  1  0  0  0  0
  2 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2=C[C@H](C[C@H]([C@H]12)C1=CC=CC=C1C(O)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO4/c1-11(20)23-13-9-12-7-8-19(2)17(12)16(10-13)14-5-3-4-6-15(14)18(21)22/h3-6,9,13,16-17H,7-8,10H2,1-2H3,(H,21,22)/t13-,16+,17-/m1/s1

> <INCHI_KEY>
GSIMSPGRWYRESN-XOKHGSTOSA-N

> <FORMULA>
C18H21NO4

> <MOLECULAR_WEIGHT>
315.369

> <EXACT_MASS>
315.14705816

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.22331326968394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(5S,7S,7aS)-5-(acetyloxy)-1-methyl-2,3,5,6,7,7a-hexahydro-1H-indol-7-yl]benzoic acid

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
-0.8095010520946315

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4536326824828922

> <JCHEM_PKA_STRONGEST_BASIC>
8.74840117381967

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
87.00510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(5S,7S,7aS)-5-(acetyloxy)-1-methyl-2,3,5,6,7,7a-hexahydroindol-7-yl]benzoic acid

> <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       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   8.233   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.925   6.693   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.925  -1.007   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17    4                                                       
CONECT   19   16                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
2-[(5S,7S,7AS)-5-(acetyloxy)-1-methyl-2,3,5,6,7,7a-hexahydro-1H-indol-7-yl]benzoate	Generator

Chemical Formula

C₁₈H₂₁NO₄

Average Mass

315.3690 Da

Monoisotopic Mass

315.14706 Da

IUPAC Name

2-[(5S,7S,7aS)-5-(acetyloxy)-1-methyl-2,3,5,6,7,7a-hexahydro-1H-indol-7-yl]benzoic acid

Traditional Name

2-[(5S,7S,7aS)-5-(acetyloxy)-1-methyl-2,3,5,6,7,7a-hexahydroindol-7-yl]benzoic acid

CAS Registry Number

Not Available

SMILES

CN1CCC2=C[C@H](C[C@H]([C@H]12)C1=CC=CC=C1C(O)=O)OC(C)=O

InChI Identifier

InChI=1S/C18H21NO4/c1-11(20)23-13-9-12-7-8-19(2)17(12)16(10-13)14-5-3-4-6-15(14)18(21)22/h3-6,9,13,16-17H,7-8,10H2,1-2H3,(H,21,22)/t13-,16+,17-/m1/s1

InChI Key

GSIMSPGRWYRESN-XOKHGSTOSA-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
Clivia miniata	LOTUS Database	35616633
Clivia miniata Regel	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up 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

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Benzoic acid or derivatives
Benzoic acid
Indole or derivatives
Benzoyl
Aralkylamine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Amino acid
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Azacycle
Carboxylic acid
Carboxylic acid derivative
Amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
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	1.89	ALOGPS
logP	-0.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	8.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.01 m³·mol⁻¹	ChemAxon
Polarizability	33.22 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

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

163002390

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Clivojuline (NP0066750)

MOL for NP0066750 (Clivojuline)

3D MOL for NP0066750 (Clivojuline)

3D SDF for NP0066750 (Clivojuline)

3D-SDF for NP0066750 (Clivojuline)

PDB for NP0066750 (Clivojuline)

3D PDB for NP0066750 (Clivojuline)

SMILES for NP0066750 (Clivojuline)

INCHI for NP0066750 (Clivojuline)

Structure for NP0066750 (Clivojuline)

3D Structure for NP0066750 (Clivojuline)