NP-MRD: Showing NP-Card for Isocryptaustoline (NP0333597)

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Record Information

Version

2.0

Created at

2024-07-11 18:56:45 UTC

Updated at

2025-06-11 02:39:02 UTC

NP-MRD ID

NP0333597

Natural Product DOI

https://doi.org/10.57994/3076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isocryptaustoline

Description

Based on a literature review very few articles have been published on Isocryptaustoline.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03252321312D          

 26 29  0  0  1  0            999 V2000
   -0.4663   -4.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -2.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2746   -3.8532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4562   -1.8312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2799   -1.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509   -2.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    1.9287   -4.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  0  0  0  0
 11 25  1  0  0  0  0
 25  4  1  0  0  0  0
 25 26  1  6  0  0  0
M  CHG  1  25   1
M  END


  Mrv2104 03252321312D          

 26 29  0  0  1  0            999 V2000
   -0.4663   -4.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -2.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2746   -3.8532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4562   -1.8312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2799   -1.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509   -2.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    1.9287   -4.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  0  0  0  0
 11 25  1  0  0  0  0
 25  4  1  0  0  0  0
 25 26  1  6  0  0  0
M  CHG  1  25   1
M  END
> <DATABASE_ID>
NP0333597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC3=C(C=C(O)C(OC)=C3)[N@+]1(C)CCC1=CC(OC)=C(OC)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO4/c1-21-6-5-12-8-19(24-3)20(25-4)10-14(12)16(21)7-13-9-18(23-2)17(22)11-15(13)21/h8-11,16H,5-7H2,1-4H3/p+1/t16-,21-/m0/s1

> <INCHI_KEY>
ZUFLALMKKZDCDU-KKSFZXQISA-O

> <FORMULA>
C20H24NO4

> <MOLECULAR_WEIGHT>
342.414

> <EXACT_MASS>
342.169984677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.310420452268474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7R,12aS)-9-hydroxy-2,3,10-trimethoxy-7-methyl-5H,6H,7H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

> <JCHEM_LOGP>
-0.8796118794717452

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.787361814914057

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.240903571385767

> <JCHEM_PKA_STRONGEST_BASIC>
-4.418709273296609

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
107.95179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(7R,12aS)-9-hydroxy-2,3,10-trimethoxy-7-methyl-5H,6H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAR-23         0                                  
HETATM    1  O   UNK     0      -0.870  -7.658   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.425  -6.826   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.794  -7.531   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.090  -6.699   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.016  -5.161   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.648  -4.455   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.352  -5.287   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.017  -4.582   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.312  -5.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.457  -4.616   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.420  -5.817   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       6.113  -7.193   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       6.958  -5.905   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.803  -4.618   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.340  -4.706   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.185  -3.418   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.722  -3.506   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.033  -6.081   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.570  -6.169   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.415  -4.882   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.188  -7.369   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.650  -7.281   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.805  -8.568   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.268  -8.480   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       4.575  -7.105   0.000  0.00  0.00           N+1
HETATM   26  C   UNK     0       3.600  -8.297   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   13   25                                             
CONECT   12   11                                                            
CONECT   13   11   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   13   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   11    4   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄NO₄

Average Mass

342.4140 Da

Monoisotopic Mass

342.16998 Da

IUPAC Name

(7R,12aS)-9-hydroxy-2,3,10-trimethoxy-7-methyl-5H,6H,7H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

Traditional Name

(7R,12aS)-9-hydroxy-2,3,10-trimethoxy-7-methyl-5H,6H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC3=C(C=C(O)C(OC)=C3)[N@+]1(C)CCC1=CC(OC)=C(OC)C=C21

InChI Identifier

InChI=1S/C20H23NO4/c1-21-6-5-12-8-19(24-3)20(25-4)10-14(12)16(21)7-13-9-18(23-2)17(22)11-15(13)21/h8-11,16H,5-7H2,1-4H3/p+1/t16-,21-/m0/s1

InChI Key

ZUFLALMKKZDCDU-KKSFZXQISA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
HSQCTOCSY NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	pierre.le-pogam-alluard@universite-paris-saclay.fr	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cryptocarya oubatchensis		Not Available

Chemical Taxonomy

Classification

Not classified

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	-0.88	ChemAxon
pKa (Strongest Acidic)	9.24	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.95 m³·mol⁻¹	ChemAxon
Polarizability	38.31 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Isocryptaustoline (NP0333597)

MOL for NP0333597 (Isocryptaustoline)

3D MOL for NP0333597 (Isocryptaustoline)

3D SDF for NP0333597 (Isocryptaustoline)

3D-SDF for NP0333597 (Isocryptaustoline)

PDB for NP0333597 (Isocryptaustoline)

3D PDB for NP0333597 (Isocryptaustoline)

SMILES for NP0333597 (Isocryptaustoline)

INCHI for NP0333597 (Isocryptaustoline)

Structure for NP0333597 (Isocryptaustoline)

3D Structure for NP0333597 (Isocryptaustoline)