NP-MRD: Showing NP-Card for 11-Hydroxycryptolepine (NP0083233)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 04:16:38 UTC

Updated at

2022-04-29 04:16:38 UTC

NP-MRD ID

NP0083233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Hydroxycryptolepine

Description

5-Methyl-5H-indolo[3,2-b]quinolin-11-ol belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline. 11-Hydroxycryptolepine is found in Cryptolepis sanguinolenta . 5-Methyl-5H-indolo[3,2-b]quinolin-11-ol is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -0.1201   -2.0360    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4759   -0.7689    0.3201 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    0.0525    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356   -0.0496    0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -1.0229    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442   -0.8332    0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    0.3668    0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908    1.3273   -0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    1.1472   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334    1.9441   -0.7945 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509    1.3600   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676    1.6817   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796    2.9090   -1.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0702    0.7997   -0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3970    1.1258   -0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130    0.2716   -0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485   -0.9540    0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8099   -1.2876    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -0.4461    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -2.6414    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750   -1.9329    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0172   -2.6305    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4427   -1.9508    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -1.5612    0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7020    0.5029    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1953    2.2564   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6614    3.5639   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6148    2.0979   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4286    0.5690   -0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9608   -1.6101    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6760   -2.2507    0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 11  3  1  0
 19 14  1  0
  9  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv1533004171509342D          

 19 22  0  0  0  0            999 V2000
    2.8119    1.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    0.9396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997   -0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623   -1.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -0.8190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.3944    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
  2 19  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C3C=CC=CC3=NC2=C(O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O/c1-18-13-9-5-3-7-11(13)16(19)14-15(18)10-6-2-4-8-12(10)17-14/h2-9,19H,1H3

> <INCHI_KEY>
GOTUAZGWJVYHRE-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O

> <MOLECULAR_WEIGHT>
248.285

> <EXACT_MASS>
248.094963014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.32834513412286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-5H-indolo[3,2-b]quinolin-11-ol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
3.554501414333333

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.02580229434264

> <JCHEM_PKA_STRONGEST_BASIC>
2.948885503548573

> <JCHEM_POLAR_SURFACE_AREA>
38.05

> <JCHEM_REFRACTIVITY>
73.8991

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methylindolo[3,2-b]quinolin-11-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       5.249   3.264   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.552   1.754   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.012   1.262   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.167   2.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.627   1.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.930   0.278   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.774  -0.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.315  -0.248   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.159  -1.266   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.463  -2.775   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.700  -0.774   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.358  -1.529   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.225  -0.486   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.692  -0.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.200   0.626   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.442   2.026   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.976   2.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.867   0.914   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.397   0.736   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    2   11                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂N₂O

Average Mass

248.2850 Da

Monoisotopic Mass

248.09496 Da

IUPAC Name

5-methyl-5H-indolo[3,2-b]quinolin-11-ol

Traditional Name

5-methylindolo[3,2-b]quinolin-11-ol

CAS Registry Number

Not Available

SMILES

CN1C2=C3C=CC=CC3=NC2=C(O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C16H12N2O/c1-18-13-9-5-3-7-11(13)16(19)14-15(18)10-6-2-4-8-12(10)17-14/h2-9,19H,1H3

InChI Key

GOTUAZGWJVYHRE-UHFFFAOYSA-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
Cryptolepis sanguinolenta	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Indoloquinolines

Direct Parent

Indoloquinolines

Alternative Parents

Substituents

Indoloquinoline
Indole or derivatives
Indole
Hydroxypyridine
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	2.17	ALOGPS
logP	3.55	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	2.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.05 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.9 m³·mol⁻¹	ChemAxon
Polarizability	27.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

Showing NP-Card for 11-Hydroxycryptolepine (NP0083233)

MOL for NP0083233 (11-Hydroxycryptolepine)

3D MOL for NP0083233 (11-Hydroxycryptolepine)

3D SDF for NP0083233 (11-Hydroxycryptolepine)

3D-SDF for NP0083233 (11-Hydroxycryptolepine)

PDB for NP0083233 (11-Hydroxycryptolepine)

3D PDB for NP0083233 (11-Hydroxycryptolepine)

SMILES for NP0083233 (11-Hydroxycryptolepine)

INCHI for NP0083233 (11-Hydroxycryptolepine)

Structure for NP0083233 (11-Hydroxycryptolepine)

3D Structure for NP0083233 (11-Hydroxycryptolepine)