Decarine

Details

• Internal ID: 38d710a0-5e94-4f0e-9955-774b18af6e5c
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Phenanthridines and derivatives
• IUPAC Name: 1-methoxy-[1,3]benzodioxolo[5,6-c]phenanthridin-2-ol
• SMILES (Canonical): COC1=C(C=CC2=C3C=CC4=CC5=C(C=C4C3=NC=C21)OCO5)O
• SMILES (Isomeric): COC1=C(C=CC2=C3C=CC4=CC5=C(C=C4C3=NC=C21)OCO5)O
• InChI: InChI=1S/C19H13NO4/c1-22-19-14-8-20-18-12(11(14)4-5-15(19)21)3-2-10-6-16-17(7-13(10)18)24-9-23-16/h2-8,21H,9H2,1H3
• InChI Key: GJJFWGQGJJGJEO-UHFFFAOYSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₃NO₄
• Molecular Weight: 319.30 g/mol
• Exact Mass: 319.08445790 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.98
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 54354-62-0
• Rutaceline
• Zanthoxyline
• 1-methoxy-[1,3]benzodioxolo[5,6-c]phenanthridin-2-ol
• [1,3]Benzodioxolo[5,6-c]phenanthridin-2-ol, 1-methoxy-
• CHEBI:65727
• 1-methoxy-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-2-ol
• 1-Methoxy[1,3]benzodioxolo[5,6-c]phenanthridin-2-ol; Decarine; Rutaceline; Zanthoxylin
• (1,3)Benzodioxolo(5,6-c)phenanthridin-2-ol, 1-methoxy-
• CHEMBL458702
• SCHEMBL3855119
• DTXSID90202738
• AKOS028108611
• Q27134211
• 1-methoxy-[1,3]benzodioxolo[6,5-c]phenanthridin-2-ol
• B0005-190022

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9812	98.12%
Caco-2	+	0.6609	66.09%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6773	67.73%
OATP2B1 inhibitior	-	0.8678	86.78%
OATP1B1 inhibitior	+	0.9531	95.31%
OATP1B3 inhibitior	+	0.9662	96.62%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6353	63.53%
P-glycoprotein inhibitior	-	0.7562	75.62%
P-glycoprotein substrate	-	0.8497	84.97%
CYP3A4 substrate	-	0.5133	51.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7137	71.37%
CYP3A4 inhibition	+	0.8552	85.52%
CYP2C9 inhibition	-	0.5152	51.52%
CYP2C19 inhibition	+	0.7587	75.87%
CYP2D6 inhibition	+	0.8214	82.14%
CYP1A2 inhibition	+	0.9018	90.18%
CYP2C8 inhibition	+	0.6131	61.31%
CYP inhibitory promiscuity	+	0.8323	83.23%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4096	40.96%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.6154	61.54%
Skin irritation	-	0.7835	78.35%
Skin corrosion	-	0.9637	96.37%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6964	69.64%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.6877	68.77%
skin sensitisation	-	0.8225	82.25%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4637	46.37%
Acute Oral Toxicity (c)	III	0.7061	70.61%
Estrogen receptor binding	+	0.9350	93.50%
Androgen receptor binding	+	0.6945	69.45%
Thyroid receptor binding	+	0.7869	78.69%
Glucocorticoid receptor binding	+	0.9274	92.74%
Aromatase binding	+	0.7860	78.60%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.9320	93.20%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.76%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.00%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.81%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.96%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.11%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.65%	96.77%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	92.14%	85.30%
CHEMBL2535	P11166	Glucose transporter	91.73%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.16%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.72%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.33%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	87.24%	83.82%
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	86.53%	95.39%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.13%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.47%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	83.96%	94.73%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	82.47%	93.24%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.30%	80.96%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.74%	85.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.40%	89.00%

Plants that contains it

• Aframomum daniellii
• Alchornea cordifolia
• Aralia bipinnata
• Atalantia wightii
• Balanophora japonica
• Corydalis persica
• Corynanthe pachyceras
• Cota tinctoria
• Cynoglossum amabile
• Glycosmis pseudoracemosa
• Iphiona grantioides
• Juniperus horizontalis
• Lathyrus tingitanus
• Plectranthus caninus
• Rauvolfia salicifolia
• Strychnos spinosa
• Tetradium glabrifolium
• Turraeanthus africanus
• Zanthoxylum ailanthoides
• Zanthoxylum armatum
• Zanthoxylum beecheyanum
• Zanthoxylum integrifoliolum
• Zanthoxylum leprieurii
• Zanthoxylum madagascariense
• Zanthoxylum nitidum
• Zanthoxylum rhoifolium
• Zanthoxylum simulans
• Zanthoxylum spinosum
• Zanthoxylum syncarpum
• Zanthoxylum tetraspermum
• Zanthoxylum thomense
• Zanthoxylum viride

Cross-Links

• PubChem: 179640
• NPASS: NPC118121
• ChEMBL: CHEMBL458702
• LOTUS: LTS0167145
• wikiData: Q27134211