NP-MRD: Showing NP-Card for 2,3,9,10-Tetrahydroxyberberine (NP0138397)

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Record Information

Version

1.0

Created at

2022-05-31 17:57:43 UTC

Updated at

2022-05-31 17:57:43 UTC

NP-MRD ID

NP0138397

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3,9,10-Tetrahydroxyberberine

Description

2,3,9,10-Tetrahydroxyberberine 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. Based on a literature review very few articles have been published on 2,3,9,10-Tetrahydroxyberberine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    5.8312    0.0066   -0.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529    0.0432   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172   -1.0935    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -1.1008    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952    0.0260   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066    1.1580   -0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    1.1488   -0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    2.2604   -1.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414   -0.0498   -0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5018    1.0668   -0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8916    1.0204   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017    2.1647   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662    2.1194   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746    0.9807    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9619    0.9434    0.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -0.1688    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5143   -1.2779    0.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4836   -0.1315    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389   -1.2348    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.1451    0.4204 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.3563   -2.3254    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141   -2.3312    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042    0.8272   -0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3956   -1.9819    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8252    2.0611   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587    3.0735   -1.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334    1.9732   -0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    3.0093   -0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5552    2.9921   -0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5496    1.7271   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0856   -2.1245    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1518   -2.1546    0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777   -3.1541    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0933   -2.5988    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.5813    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -3.1478   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 14  1  0
 18 11  1  0
 20  9  1  0
  4  5  1  0
 15 30  1  0
 13 29  1  0
 12 28  1  0
 10 27  1  0
  6 25  1  0
  8 26  1  0
  1 23  1  0
  3 24  1  0
 22 35  1  0
 22 36  1  0
 21 33  1  0
 21 34  1  0
 19 32  1  0
 17 31  1  0
M  CHG  1  20   1
M  END


  Mrv1652305312219572D          

 22 25  0  0  0  0            999 V2000
   -1.6203   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -3.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009   -2.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -4.3914    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.0802   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -4.8591    0.0000 O   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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 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
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  CHG  1  18   1
M  END
> <DATABASE_ID>
NP0138397

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C=C3C4=CC(O)=C(O)C=C4CC[N+]3=CC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO4/c19-14-2-1-9-5-13-11-7-16(21)15(20)6-10(11)3-4-18(13)8-12(9)17(14)22/h1-2,5-8H,3-4H2,(H3,19,20,21,22)/p+1

> <INCHI_KEY>
DAHMYCXNJSCLGA-UHFFFAOYSA-O

> <FORMULA>
C17H14NO4

> <MOLECULAR_WEIGHT>
296.301

> <EXACT_MASS>
296.091734355

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.13825053441009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,10,11-tetrahydroxy-7,8-dihydro-6lambda5-azatetraphen-6-ylium

> <JCHEM_LOGP>
-1.8054645088050787

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.786670958841778

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7703189756578395

> <JCHEM_PKA_STRONGEST_BASIC>
-6.30702236485642

> <JCHEM_POLAR_SURFACE_AREA>
84.8

> <JCHEM_REFRACTIVITY>
82.75359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,4,10,11-tetrahydroxy-7,8-dihydro-6lambda5-azatetraphen-6-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  O   UNK     0      -3.024  -6.742   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.512  -6.451   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.008  -4.996   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.504  -4.705   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.512  -5.869   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.024  -5.578   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.033  -6.742   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.545  -6.451   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.049  -4.996   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.561  -4.705   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.065  -3.250   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.569  -5.869   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.082  -5.578   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.065  -7.324   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.553  -7.615   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.049  -9.070   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.537  -9.361   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.529  -8.197   0.000  0.00  0.00           N+1
HETATM   19  C   UNK     0       2.016  -8.488   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.008  -7.324   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.504  -7.615   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.008  -9.070   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    5   21                                                  
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄NO₄

Average Mass

296.3010 Da

Monoisotopic Mass

296.09173 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

162854-37-7

SMILES

OC1=CC=C2C=C3C4=CC(O)=C(O)C=C4CC[N+]3=CC2=C1O

InChI Identifier

InChI=1S/C17H13NO4/c19-14-2-1-9-5-13-11-7-16(21)15(20)6-10(11)3-4-18(13)8-12(9)17(14)22/h1-2,5-8H,3-4H2,(H3,19,20,21,22)/p+1

InChI Key

DAHMYCXNJSCLGA-UHFFFAOYSA-O

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 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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Pyridinium
Benzenoid
Heteroaromatic compound
Polyol
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Organonitrogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:31070 )

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

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

391871

KEGG Compound ID

C12331

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,3,9,10-Tetrahydroxyberberine (NP0138397)

MOL for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

3D MOL for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

3D SDF for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

3D-SDF for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

PDB for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

3D PDB for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

SMILES for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

INCHI for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

Structure for NP0138397 (2,3,9,10-Tetrahydroxyberberine)

3D Structure for NP0138397 (2,3,9,10-Tetrahydroxyberberine)