NP-MRD: Showing NP-Card for Dehydrocheilanthifoline (NP0351737)

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Record Information

Version

2.0

Created at

2025-11-05 02:49:15 UTC

Updated at

2025-11-06 01:00:59 UTC

NP-MRD ID

NP0351737

Natural Product DOI

https://doi.org/10.57994/4807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydrocheilanthifoline

Description

ZINC5526682 belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. ZINC5526682 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151517082D          

 24 28  0  0  0  0            999 V2000
    1.5210   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739   -1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -0.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238   -1.3167    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.4487   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6969   -1.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -2.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   -3.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8937   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -3.5038    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  8 20  2  0  0  0  0
 20 21  1  0  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0351737

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)C1=[N+](CC2)C=C2C3=C(OCO3)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H15NO4/c1-22-18-7-12-4-5-20-9-14-11(2-3-17-19(14)24-10-23-17)6-15(20)13(12)8-16(18)21/h2-3,6-9H,4-5,10H2,1H3/p+1

> <INCHI_KEY>
BNXZOIDSAUKXGW-UHFFFAOYSA-O

> <FORMULA>
C19H16NO4

> <MOLECULAR_WEIGHT>
322.339

> <EXACT_MASS>
322.107384419

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.881924916205584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-hydroxy-17-methoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

> <ALOGPS_LOGP>
-0.39

> <JCHEM_LOGP>
-1.4292063418050789

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.55027298303078

> <JCHEM_PKA_STRONGEST_BASIC>
-4.533068963751586

> <JCHEM_POLAR_SURFACE_AREA>
51.8

> <JCHEM_REFRACTIVITY>
89.04100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-17-methoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       2.839  -5.242   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.589  -3.897   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.129  -3.873   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.878  -2.528   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.418  -2.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.168  -1.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.707  -1.136   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      10.498  -2.458   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      12.037  -2.435   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.828  -3.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.368  -3.733   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.380  -2.573   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.797  -3.178   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.659  -4.712   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.158  -5.055   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.408  -6.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.868  -6.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.078  -5.102   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.538  -5.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748  -3.803   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.208  -3.827   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.459  -5.172   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.919  -5.195   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.169  -6.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    8   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₆NO₄

Average Mass

322.3390 Da

Monoisotopic Mass

322.10738 Da

IUPAC Name

16-hydroxy-17-methoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

Traditional Name

16-hydroxy-17-methoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)C1=[N+](CC2)C=C2C3=C(OCO3)C=CC2=C1

InChI Identifier

InChI=1S/C19H15NO4/c1-22-18-7-12-4-5-20-9-14-11(2-3-17-19(14)24-10-23-17)6-15(20)13(12)8-16(18)21/h2-3,6-9H,4-5,10H2,1H3/p+1

InChI Key

BNXZOIDSAUKXGW-UHFFFAOYSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3CN, experimental)	bouchalerik@gmail.com	Institute of Organic Chemistry and Biochemistry of the CAS	Erik Bouchal	2025-11-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	bouchalerik@gmail.com	Institute of Organic Chemistry and Biochemistry of the CAS	Erik Bouchal	2025-11-05	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	bouchalerik@gmail.com	Institute of Organic Chemistry and Biochemistry of the CAS	Erik Bouchal	2025-11-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	bouchalerik@gmail.com	Institute of Organic Chemistry and Biochemistry of the CAS	Erik Bouchal	2025-11-05	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	bouchalerik@gmail.com	Institute of Organic Chemistry and Biochemistry of the CAS	Erik Bouchal	2025-11-05	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	bouchalerik@gmail.com	Institute of Organic Chemistry and Biochemistry of the CAS	Erik Bouchal	2025-11-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3CN, experimental)	bouchalerik@gmail.com	Institute of Organic Chemistry and Biochemistry of the CAS	Erik Bouchal	2025-11-05	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Macleaya cordata		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Isoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Pyridinium
Benzenoid
Heteroaromatic compound
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
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	-0.39	ALOGPS
logP	-1.4	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.04 m³·mol⁻¹	ChemAxon
Polarizability	34.88 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

45490416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Dehydrocheilanthifoline (NP0351737)

MOL for NP0351737 (Dehydrocheilanthifoline)

3D MOL for NP0351737 (Dehydrocheilanthifoline)

3D SDF for NP0351737 (Dehydrocheilanthifoline)

3D-SDF for NP0351737 (Dehydrocheilanthifoline)

PDB for NP0351737 (Dehydrocheilanthifoline)

3D PDB for NP0351737 (Dehydrocheilanthifoline)

SMILES for NP0351737 (Dehydrocheilanthifoline)

INCHI for NP0351737 (Dehydrocheilanthifoline)

Structure for NP0351737 (Dehydrocheilanthifoline)

3D Structure for NP0351737 (Dehydrocheilanthifoline)