Deoxyvasicinone

Details

• Internal ID: 3488a19a-78d0-4bb9-8fad-8fd1d6a25e8e
• Taxonomy: Organoheterocyclic compounds > Diazanaphthalenes > Benzodiazines > Quinazolines
• IUPAC Name: 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
• SMILES (Canonical): C1CC2=NC3=CC=CC=C3C(=O)N2C1
• SMILES (Isomeric): C1CC2=NC3=CC=CC=C3C(=O)N2C1
• InChI: InChI=1S/C11H10N2O/c14-11-8-4-1-2-5-9(8)12-10-6-3-7-13(10)11/h1-2,4-5H,3,6-7H2
• InChI Key: VARHXCYGZKSOOO-UHFFFAOYSA-N
• Popularity: 65 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.21 g/mol
• Exact Mass: 186.079312947 g/mol
• Topological Polar Surface Area (TPSA): 32.70 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.34
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 530-53-0
• 2,3-Trimethylene-4-quinazolone
• 2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
• 2,3-Dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
• Pegenone
• 1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-one
• CHEBI:4435
• CHEMBL456881
• Pyrrolo[2,1-b]quinazolin-9(1H)-one, 2,3-dihydro-
• NSC 159478
• 3H-Quinazolin-4-one, 2,3-trimethyleno
• 9-Oxodeoxypeganine; Deoxyvasicinone; NSC 159478
• Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-
• Desoxyvasicinon
• cid_68261
• MLS000088451
• SCHEMBL864139
• Pyrrolo[2,1-b]quinazolin-9(1H)-one,2,3-dihydro-
• DTXSID90201049
• VARHXCYGZKSOOO-UHFFFAOYSA-N
• HMS2507B03
• HY-N3735
• BBL028460
• BDBM50244216
• MFCD00247051
• NSC159478
• STL373117
• AKOS002210198
• NSC-159478
• SMR000024071
• VS-08779
• CS-0024129
• EN300-205076
• A870835
• SR-01000434191
• SR-01000434191-1
• Q27106382
• 1,2,3,10-tetrahydro-pyrrolo[2,1-b]quinazolin-9-one
• Z275210418
• B2703-143596
• InChI=1/C11H10N2O/c14-11-8-4-1-2-5-9(8)12-10-6-3-7-13(10)11/h1-2,4-5H,3,6-7H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.9064	90.64%
Blood Brain Barrier	+	0.9038	90.38%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8334	83.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9661	96.61%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	+	0.6612	66.12%
BSEP inhibitior	-	0.9122	91.22%
P-glycoprotein inhibitior	-	0.9792	97.92%
P-glycoprotein substrate	-	0.9464	94.64%
CYP3A4 substrate	-	0.5611	56.11%
CYP2C9 substrate	-	0.6157	61.57%
CYP2D6 substrate	-	0.8477	84.77%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9010	90.10%
CYP2D6 inhibition	-	0.9127	91.27%
CYP1A2 inhibition	+	0.9734	97.34%
CYP2C8 inhibition	-	0.9077	90.77%
CYP inhibitory promiscuity	+	0.7012	70.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6365	63.65%
Eye corrosion	-	0.9825	98.25%
Eye irritation	+	0.6771	67.71%
Skin irritation	-	0.8221	82.21%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	+	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6359	63.59%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.9097	90.97%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.4855	48.55%
Acute Oral Toxicity (c)	II	0.6795	67.95%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.7888	78.88%
Thyroid receptor binding	+	0.5222	52.22%
Glucocorticoid receptor binding	-	0.7274	72.74%
Aromatase binding	+	0.5280	52.80%
PPAR gamma	+	0.7562	75.62%
Honey bee toxicity	-	0.9400	94.00%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.6044	60.44%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	3162.3 nM	Potency	via CMAUP
CHEMBL1914	P06276	Butyrylcholinesterase	25100 nM	IC50	PMID: 18524585
CHEMBL3356	P05177	Cytochrome P450 1A2	6309.57 nM	AC50	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	28183.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	8912.5 nM	Potency	via CMAUP
CHEMBL1741200	Q2TB90	Putative hexokinase HKDC1	4320 nM	IC50	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	39810.7 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	3981.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.04%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.88%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.01%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.60%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.99%	86.33%
CHEMBL5805	Q9NR97	Toll-like receptor 8	88.36%	96.25%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.60%	92.67%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	84.77%	96.47%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.81%	91.11%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.43%	96.67%
CHEMBL1781	P11387	DNA topoisomerase I	82.32%	97.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.20%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.03%	94.00%

Plants that contains it

• Arundo donax
• Dioscorea althaeoides
• Dioscorea futschauensis
• Dioscorea gracillima
• Dioscorea nipponica
• Dioscorea panthaica
• Dioscorea septemloba
• Galega officinalis
• Isatis tinctoria
• Justicia adhatoda
• Nitraria schoberi
• Peganum harmala
• Peganum nigellastrum
• Persicaria tinctoria

Cross-Links

• PubChem: 68261
• NPASS: NPC207428
• ChEMBL: CHEMBL456881
• LOTUS: LTS0239836
• wikiData: Q27106382