NP-MRD: Showing NP-Card for 9-hydroxyellipticine (NP0213895)

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Record Information

Version

1.0

Created at

2022-09-05 13:01:32 UTC

Updated at

2022-09-05 13:01:32 UTC

NP-MRD ID

NP0213895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxyellipticine

Description

9-Hydroxyellipticine, also known as 9-OH-e or 9HE, belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. 9-Hydroxyellipticine is a very strong basic compound (based on its pKa). 9-hydroxyellipticine is found in Ochrosia elliptica. It was first documented in 1981 (PMID: 7049365). A organic heterotetracyclic compound that is ellipticine in which the hydrogen at position 9 has been replaced by a hydroxy group (PMID: 10737712) (PMID: 11724337) (PMID: 12083739) (PMID: 12570841).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -2.1606    2.6025   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    1.2421   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051    0.1461   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7648    0.3760   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5820   -0.7345   -0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0504   -1.9668    0.0308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183   -2.1922    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502   -1.1407    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -1.3214    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -2.6649    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172   -0.1823    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2168    1.0937   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689    1.9872   -0.0312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356    1.3238   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.8001   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2991    0.9595    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445   -0.4003    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1691   -1.2325    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582   -0.9024    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6899   -0.0476    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963    2.8353    0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    3.3211   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775    2.7304   -0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1362    1.3856   -0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6495   -0.5425   -0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377   -3.1987    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -2.7251    1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -3.5086    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7444   -2.8456   -0.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373    3.0186   -0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3771    2.8844   -0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3003    1.3669    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5627   -1.5047    0.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6646   -1.9624    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 20  2  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 12  2  1  0
 15 14  1  0
  8  3  1  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 19 34  1  0
 18 33  1  0
 16 32  1  0
 15 31  1  0
M  END


  Mrv1533004241501462D          

 20 23  0  0  0  0            999 V2000
    3.4623    2.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    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
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 11 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0213895

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2O/c1-9-14-8-18-6-5-12(14)10(2)17-16(9)13-7-11(20)3-4-15(13)19-17/h3-8,19-20H,1-2H3

> <INCHI_KEY>
QZTWUDDGLIDXSE-UHFFFAOYSA-N

> <FORMULA>
C17H14N2O

> <MOLECULAR_WEIGHT>
262.312

> <EXACT_MASS>
262.110613079

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.25439673863042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,11-dimethyl-6H-pyrido[4,3-b]carbazol-9-ol

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
3.5859674759999995

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.65257535819223

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.670075952787439

> <JCHEM_PKA_STRONGEST_BASIC>
5.917735634768203

> <JCHEM_POLAR_SURFACE_AREA>
48.910000000000004

> <JCHEM_REFRACTIVITY>
79.82880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxyellipticine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.463   4.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.159   2.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.627  -0.248   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.552  -0.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.249  -1.724   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.397   0.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.449  -1.742   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.225   2.026   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.358   3.069   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
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   20                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    2   11                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
5,11-Dimethyl-6H-pyrido[4,3-b]carbazol-9-ol	ChEBI
9-Hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole	ChEBI
9-OH-e	ChEBI
9HE	ChEBI
9-Hydroxyellipticine, radical ion (1+)	MeSH
9-Hydroxyellipticine monohydrochloride	MeSH

Chemical Formula

C₁₇H₁₄N₂O

Average Mass

262.3120 Da

Monoisotopic Mass

262.11061 Da

IUPAC Name

5,11-dimethyl-6H-pyrido[4,3-b]carbazol-9-ol

Traditional Name

9-hydroxyellipticine

CAS Registry Number

Not Available

SMILES

CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=C(O)C=C1

InChI Identifier

InChI=1S/C17H14N2O/c1-9-14-8-18-6-5-12(14)10(2)17-16(9)13-7-11(20)3-4-15(13)19-17/h3-8,19-20H,1-2H3

InChI Key

QZTWUDDGLIDXSE-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, 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

Species Name	Source	Reference
Ochrosia elliptica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Isoquinoline
Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
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	4.08	ALOGPS
logP	3.59	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	5.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.83 m³·mol⁻¹	ChemAxon
Polarizability	29.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

91643

PDB ID

Not Available

ChEBI ID

88297

Good Scents ID

Not Available

References

General References

Mizumoto K, Sato N, Kusumoto M, Niiyama H, Maehara N, Nishio S, Li Z, Ogawa T, Tanaka M: Diverse effects of 9-hydroxyellipticine on the chemosensitivity of human pancreatic cancer cells harboring p53 mutations. Cancer Lett. 2000 Feb 28;149(1-2):85-94. doi: 10.1016/s0304-3835(99)00345-6. [PubMed:10737712 ]
Sugikawa E, Tsunoda S, Nakanishi N, Ohashi M: 9-Hydroxyellipticine alters the conformation and DNA binding characteristics of mutated p53 protein. Anticancer Res. 2001 Jul-Aug;21(4A):2671-5. [PubMed:11724337 ]
Saeki K, Obi I, Ogiku N, Shigekawa M, Imagawa T, Matsumoto T: Cardioprotective effects of 9-hydroxyellipticine on ischemia and reperfusion in isolated rat heart. Jpn J Pharmacol. 2002 May;89(1):21-8. doi: 10.1254/jjp.89.21. [PubMed:12083739 ]
Harding MM, Grummitt AR: 9-hydroxyellipticine and derivatives as chemotherapy agents. Mini Rev Med Chem. 2003 Mar;3(2):67-76. doi: 10.2174/1389557033405377. [PubMed:12570841 ]
Paoletti C, Auclair C, Lesca P, Tocanne JF, Malvy C, Pinto M: Ellipticine, 9-hydroxyellipticine, and 9-hydroxyellipiticinum: some biochemical properties of possible pharmacologic significance. Cancer Treat Rep. 1981;65 Suppl 3:107-18. [PubMed:7049365 ]
LOTUS database [Link]

Showing NP-Card for 9-hydroxyellipticine (NP0213895)

MOL for NP0213895 (9-hydroxyellipticine)

3D MOL for NP0213895 (9-hydroxyellipticine)

3D SDF for NP0213895 (9-hydroxyellipticine)

3D-SDF for NP0213895 (9-hydroxyellipticine)

PDB for NP0213895 (9-hydroxyellipticine)

3D PDB for NP0213895 (9-hydroxyellipticine)

SMILES for NP0213895 (9-hydroxyellipticine)

INCHI for NP0213895 (9-hydroxyellipticine)

Structure for NP0213895 (9-hydroxyellipticine)

3D Structure for NP0213895 (9-hydroxyellipticine)