NP-MRD: Showing NP-Card for Cryptowolinol (NP0333596)

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Record Information

Version

2.0

Created at

2024-07-11 18:54:09 UTC

Updated at

2025-06-11 02:39:01 UTC

NP-MRD ID

NP0333596

Natural Product DOI

https://doi.org/10.57994/3075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cryptowolinol

Description

Cryptowolinol belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Cryptowolinol was first documented in 2024 (PMID: 38567800). Based on a literature review very few articles have been published on Cryptowolinol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03252321282D          

 26 30  0  0  1  0            999 V2000
   -3.2552   -1.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -2.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0704   -2.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086   -3.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1697   -4.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8856   -3.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244   -2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3986   -2.7553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9067   -3.4053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6795   -4.1984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -3.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6529   -2.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3524   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810   -2.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099   -3.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3642   -2.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8561   -1.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -3.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -2.0139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -2.0713    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    1.3900   -1.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250   -1.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -1.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -1.8992    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 11 19  1  0  0  0  0
  8 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 12  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 25  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
M  CHG  1  21   1
M  END


  Mrv2104 03252321282D          

 26 30  0  0  1  0            999 V2000
   -3.2552   -1.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -2.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0704   -2.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086   -3.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1697   -4.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8856   -3.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244   -2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3986   -2.7553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9067   -3.4053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6795   -4.1984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -3.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6529   -2.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3524   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810   -2.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099   -3.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3642   -2.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8561   -1.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -3.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -2.0139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -2.0713    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    1.3900   -1.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250   -1.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -1.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -1.8992    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 11 19  1  0  0  0  0
  8 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 12  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 25  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
NP0333596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@H](O)C3=C(C=C4OCOC4=C3)[N@+]1(C)CCC1=CC(OC)=C(O)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO5/c1-20-4-3-10-5-15(23-2)14(21)6-11(10)18(20)19(22)12-7-16-17(8-13(12)20)25-9-24-16/h5-8,18-19,22H,3-4,9H2,1-2H3/p+1/t18-,19-,20+/m1/s1

> <INCHI_KEY>
DNOKYJRHGJVFFF-AQNXPRMDSA-O

> <FORMULA>
C19H20NO5

> <MOLECULAR_WEIGHT>
342.37

> <EXACT_MASS>
342.133599168

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.013021771112996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,11R,12R)-11,15-dihydroxy-16-methoxy-1-methyl-5,7-dioxa-1-azapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaen-1-ium

> <JCHEM_LOGP>
-1.8600320274717448

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.956984517817999

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.8104159962092

> <JCHEM_PKA_STRONGEST_BASIC>
-4.143168891697744

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
101.9998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,11R,12R)-11,15-dihydroxy-16-methoxy-1-methyl-5,7-dioxa-1-azapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaen-1-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  C   UNK     0      -6.076  -3.331   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.401  -4.715   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.865  -4.822   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.189  -6.206   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.050  -7.483   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.653  -6.313   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.792  -5.036   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.744  -5.143   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.692  -6.357   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.268  -7.837   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.139  -5.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.085  -4.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.391  -3.474   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.751  -4.197   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.805  -5.736   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.286  -6.160   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.147  -4.883   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.198  -3.670   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.499  -6.552   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       0.069  -3.759   0.000  0.00  0.00           H+0
HETATM   21  N   UNK     0       1.605  -3.866   0.000  0.00  0.00           N+1
HETATM   22  C   UNK     0       2.595  -2.686   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.930  -2.482   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.607  -2.375   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.468  -3.652   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.004  -3.545   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9   20   21                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   15   11                                                       
CONECT   20    8                                                            
CONECT   21    8   12   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25    7   24   26                                                  
CONECT   26   25    3                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀NO₅

Average Mass

342.3700 Da

Monoisotopic Mass

342.13360 Da

IUPAC Name

(1R,11R,12R)-11,15-dihydroxy-16-methoxy-1-methyl-5,7-dioxa-1-azapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaen-1-ium

Traditional Name

(1R,11R,12R)-11,15-dihydroxy-16-methoxy-1-methyl-5,7-dioxa-1-azapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaen-1-ium

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@H](O)C3=C(C=C4OCOC4=C3)[N@+]1(C)CCC1=CC(OC)=C(O)C=C21

InChI Identifier

InChI=1S/C19H19NO5/c1-20-4-3-10-5-15(23-2)14(21)6-11(10)18(20)19(22)12-7-16-17(8-13(12)20)25-9-24-16/h5-8,18-19,22H,3-4,9H2,1-2H3/p+1/t18-,19-,20+/m1/s1

InChI Key

DNOKYJRHGJVFFF-AQNXPRMDSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	[email protected]	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	[email protected]	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
HSQCTOCSY NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	UMR CNRS 8076	Le Pogam	2024-07-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	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

Description

This compound 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
Indole or derivatives
Benzodioxole
Anisole
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Alkyl aryl ether
Benzenoid
Piperidine
Quaternary ammonium salt
Pyrroline
Meta-dioxolane
Secondary alcohol
Oxacycle
Azacycle
Ether
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Organic cation
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	-1.9	ChemAxon
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	102 m³·mol⁻¹	ChemAxon
Polarizability	36.01 Å³	ChemAxon
Number of Rings	5	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

Miyakoshi T, Kronenberg D, Tamaki S, Lombardi R, Baudoin O: Studies towards the Enantioselective Synthesis of Cryptowolinol via Pd(0)-Catalyzed C(sp(3))-H Arylation/Parallel Kinetic Resolution. Org Lett. 2024 Apr 19;26(15):2923-2927. doi: 10.1021/acs.orglett.4c00386. Epub 2024 Apr 3. [PubMed:38567800 ]

Showing NP-Card for Cryptowolinol (NP0333596)

MOL for NP0333596 (Cryptowolinol)

3D MOL for NP0333596 (Cryptowolinol)

3D SDF for NP0333596 (Cryptowolinol)

3D-SDF for NP0333596 (Cryptowolinol)

PDB for NP0333596 (Cryptowolinol)

3D PDB for NP0333596 (Cryptowolinol)

SMILES for NP0333596 (Cryptowolinol)

INCHI for NP0333596 (Cryptowolinol)

Structure for NP0333596 (Cryptowolinol)

3D Structure for NP0333596 (Cryptowolinol)