Dicentrinone

Details

• Internal ID: e24a567a-653b-49eb-b5b3-20f92bcd8a76
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 16,17-dimethoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C3=C4C(=CC5=C3OCO5)C=CN=C4C2=O)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C3=C4C(=CC5=C3OCO5)C=CN=C4C2=O)OC
• InChI: InChI=1S/C19H13NO5/c1-22-12-6-10-11(7-13(12)23-2)18(21)17-15-9(3-4-20-17)5-14-19(16(10)15)25-8-24-14/h3-7H,8H2,1-2H3
• InChI Key: NEQVOBXBOFZEMR-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₃NO₅
• Molecular Weight: 335.30 g/mol
• Exact Mass: 335.07937252 g/mol
• Topological Polar Surface Area (TPSA): 66.90 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Oxodicentrine
• 16408-78-9
• K6CE5RM6EI
• NSC 617671
• NSC-617671
• 8H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-one, 10,11-dimethoxy-
• 8H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-8-one, 10,11-dimethoxy-
• NSC617671
• UNII-K6CE5RM6EI
• CHEMBL463284
• SCHEMBL6685214
• DTXSID20167705
• 10,11-dimethoxy-8H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinolin-8-one
• 10,11-DIMETHOXY-8H-BENZO(G)-1,3-BENZODIOXOLO(6,5,4-DE)QUINOLIN-8-ONE
• NORAPORPHIN-7-ONE, 4,5,6,6A-TETRADEHYDRO-9,10-DIMETHOXY-1,2-(METHYLENEDIOXY)-
• 16,17-dimethoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one
• InChI=1/C19H13NO5/c1-22-12-6-10-11(7-13(12)23-2)18(21)17-15-9(3-4-20-17)5-14-19(16(10)15)25-8-24-14/h3-7H,8H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9872	98.72%
Caco-2	+	0.8766	87.66%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6170	61.70%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9443	94.43%
OATP1B3 inhibitior	+	0.9520	95.20%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7126	71.26%
P-glycoprotein inhibitior	-	0.5293	52.93%
P-glycoprotein substrate	-	0.8039	80.39%
CYP3A4 substrate	+	0.5627	56.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7812	78.12%
CYP3A4 inhibition	+	0.9390	93.90%
CYP2C9 inhibition	+	0.5574	55.74%
CYP2C19 inhibition	+	0.8585	85.85%
CYP2D6 inhibition	-	0.5112	51.12%
CYP1A2 inhibition	+	0.9356	93.56%
CYP2C8 inhibition	+	0.5114	51.14%
CYP inhibitory promiscuity	+	0.9451	94.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5466	54.66%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.5357	53.57%
Skin irritation	-	0.7973	79.73%
Skin corrosion	-	0.9640	96.40%
Ames mutagenesis	+	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4532	45.32%
Micronuclear	+	0.7174	71.74%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.8131	81.31%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6717	67.17%
Acute Oral Toxicity (c)	III	0.6735	67.35%
Estrogen receptor binding	+	0.8812	88.12%
Androgen receptor binding	-	0.5433	54.33%
Thyroid receptor binding	+	0.7580	75.80%
Glucocorticoid receptor binding	+	0.9206	92.06%
Aromatase binding	+	0.7222	72.22%
PPAR gamma	+	0.8302	83.02%
Honey bee toxicity	-	0.7957	79.57%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.6612	66.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.09%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.96%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.31%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	93.95%	95.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.09%	89.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	93.03%	82.67%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	92.43%	96.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.09%	96.09%
CHEMBL5014	O43353	Serine/threonine-protein kinase RIPK2	89.37%	86.79%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	89.32%	96.09%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	89.11%	96.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.81%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.48%	93.10%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.35%	99.23%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	87.28%	92.38%
CHEMBL2581	P07339	Cathepsin D	85.73%	98.95%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.30%	94.03%
CHEMBL2535	P11166	Glucose transporter	85.29%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.17%	91.11%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.03%	94.42%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.54%	92.62%
CHEMBL1937	Q92769	Histone deacetylase 2	84.46%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	82.72%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.31%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.84%	100.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.14%	80.96%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.77%	85.14%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	80.67%	96.69%

Plants that contains it

• Alstonia angustiloba
• Amphiachyris dracunculoides
• Annona cherimola
• Avena fatua
• Baccharis grandicapitulata
• Beesia calthifolia
• Boschniakia rossica
• Botrychium ternatum
• Bursera kerberi
• Clerodendrum trichotomum
• Clinacanthus nutans
• Crotalaria stolzii
• Curcuma aeruginosa
• Dasymaschalon dasymaschalum
• Delphinium giraldii
• Duguetia furfuracea
• Eucalyptus albens
• Euonymus fortunei
• Euploca racemosa
• Hedysarum gmelinii
• Helenium integrifolium
• Helichrysum fulvum
• Illigera luzonensis
• Illigera pentaphylla
• Juniperus scopulorum
• Lasianthaea podocephala
• Lindera megaphylla
• Lupinus cosentinii
• Magnolia arcabucoana
• Magnolia coco
• Melampodium leucanthum
• Mitrephora maingayi
• Myrica pensylvanica
• Neopallasia pectinata
• Ocotea leucoxylon
• Ocotea macropoda
• Papaver pseudocanescens
• Pellacalyx axillaris
• Peperomia filiformis
• Phlomis crinita
• Piper sylvaticum
• Psidium acutangulum
• Pyrolirion flavum
• Renealmia alpinia
• Rhododendron mucronulatum
• Seseli libanotis
• Sideritis dasygnaphala
• Sinomenium acutum
• Stellaria media
• Stephania abyssinica
• Stephania dinklagei
• Stephania tetrandra
• Stephania zippeliana
• Tephroseris kirilowii
• Tephroseris palustris
• Xylopia championii

Cross-Links

• PubChem: 177744
• NPASS: NPC189903
• LOTUS: LTS0151114
• wikiData: Q83037134