Oxychelerythrine

Details

• Internal ID: b5bb8339-7f78-406c-b240-396eed4e3a5f
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Phenanthridines and derivatives
• IUPAC Name: 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-13-one
• SMILES (Canonical): CN1C2=C(C=CC3=CC4=C(C=C32)OCO4)C5=C(C1=O)C(=C(C=C5)OC)OC
• SMILES (Isomeric): CN1C2=C(C=CC3=CC4=C(C=C32)OCO4)C5=C(C1=O)C(=C(C=C5)OC)OC
• InChI: InChI=1S/C21H17NO5/c1-22-19-13(5-4-11-8-16-17(9-14(11)19)27-10-26-16)12-6-7-15(24-2)20(25-3)18(12)21(22)23/h4-9H,10H2,1-3H3
• InChI Key: IHTXRYTWDARUKX-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₇NO₅
• Molecular Weight: 363.40 g/mol
• Exact Mass: 363.11067264 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 28342-33-8
• 6-Oxochelerythrine
• Dihydrooxochelerythrine
• CCRIS 3805
• BRN 0345198
• 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-13-one
• Chelerythrine, 12,13-dihydro-13-oxo-
• (1,3)Benzodioxolo(5,6-c)phenanthridin-13(12H)-one, 1,2-dimethoxy-12-methyl-
• 4-27-00-06655 (Beilstein Handbook Reference)
• (1,3)Benzodioxolo(5,6-c)phenanthridin-13(12H)-one, 1,2-dimethoxy-12-methyl- (9CI)
• Oxycheleritrine
• SCHEMBL10633372
• CHEBI:31141
• DTXSID70182584
• AKOS032948933
• LS-52943
• Q27114173
• 7,8-dimethoxy-2,3-methylenedioxy-5-methylbenzo [c]phenanthridin-6(5h)-one
• 1,2-Dimethoxy-12-methyl-(1,3)benzodioxolo(5,6-c)phenanthridin-13(12H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9187	91.87%
Caco-2	+	0.9387	93.87%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.3695	36.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9559	95.59%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9348	93.48%
BSEP inhibitior	+	0.7948	79.48%
P-glycoprotein inhibitior	+	0.7945	79.45%
P-glycoprotein substrate	-	0.7485	74.85%
CYP3A4 substrate	+	0.5320	53.20%
CYP2C9 substrate	-	0.7985	79.85%
CYP2D6 substrate	-	0.8493	84.93%
CYP3A4 inhibition	+	0.5994	59.94%
CYP2C9 inhibition	-	0.8147	81.47%
CYP2C19 inhibition	+	0.7330	73.30%
CYP2D6 inhibition	-	0.7993	79.93%
CYP1A2 inhibition	+	0.7320	73.20%
CYP2C8 inhibition	-	0.7428	74.28%
CYP inhibitory promiscuity	+	0.7506	75.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4485	44.85%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8774	87.74%
Skin irritation	-	0.8380	83.80%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4475	44.75%
Micronuclear	+	0.7774	77.74%
Hepatotoxicity	+	0.7775	77.75%
skin sensitisation	-	0.8803	88.03%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7106	71.06%
Acute Oral Toxicity (c)	III	0.6461	64.61%
Estrogen receptor binding	+	0.9193	91.93%
Androgen receptor binding	+	0.7553	75.53%
Thyroid receptor binding	+	0.7149	71.49%
Glucocorticoid receptor binding	+	0.9251	92.51%
Aromatase binding	-	0.5941	59.41%
PPAR gamma	+	0.7542	75.42%
Honey bee toxicity	-	0.8041	80.41%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.7205	72.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.91%	96.77%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.59%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.42%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.24%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.57%	92.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.41%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.83%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.56%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.27%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.21%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.20%	89.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	88.55%	92.38%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.18%	94.42%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.45%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.08%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	84.51%	94.75%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.75%	80.78%
CHEMBL2535	P11166	Glucose transporter	82.21%	98.75%
CHEMBL240	Q12809	HERG	82.08%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.10%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.53%	99.23%

Plants that contains it

• Acronychia pedunculata
• Aframomum daniellii
• Agave deserti
• Aglaia silvestris
• Alchornea cordifolia
• Asclepias subulata
• Atalantia wightii
• Balanophora japonica
• Celastrus monospermus
• Conium maculatum
• Corydalis persica
• Corynanthe pachyceras
• Cota tinctoria
• Cynoglossum amabile
• Eutrochium purpureum
• Glycosmis pseudoracemosa
• Hibiscus tilliaceus
• Hortonia floribunda
• Hosta sieboldiana
• Inula salsoloides
• Iphiona grantioides
• Jacobaea cannabifolia
• Juniperus horizontalis
• Lathyrus tingitanus
• Lepidaploa lilacina
• Morinda coreia
• Passiflora morifolia
• Plectranthus caninus
• Rauvolfia salicifolia
• Solanum spirale
• Sophora leachiana
• Strychnos spinosa
• Tetradium glabrifolium
• Toddalia asiatica
• Zanthoxylum bungeanum
• Zanthoxylum nitidum
• Zanthoxylum simulans
• Zanthoxylum spinosum

Cross-Links

• PubChem: 147279
• NPASS: NPC205689
• LOTUS: LTS0124369
• wikiData: Q27114173