Oroidin

Details

• Internal ID: 74d5fb72-9fdd-4e0f-86c2-0d1d632af3bf
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Carboxylic acid derivatives > Carboxylic acid amides > 2-heteroaryl carboxamides
• IUPAC Name: N-[(E)-3-(2-amino-1H-imidazol-5-yl)prop-2-enyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
• SMILES (Canonical): C1=C(NC(=C1Br)Br)C(=O)NCC=CC2=CN=C(N2)N
• SMILES (Isomeric): C1=C(NC(=C1Br)Br)C(=O)NC/C=C/C2=CN=C(N2)N
• InChI: InChI=1S/C11H11Br2N5O/c12-7-4-8(18-9(7)13)10(19)15-3-1-2-6-5-16-11(14)17-6/h1-2,4-5,18H,3H2,(H,15,19)(H3,14,16,17)/b2-1+
• InChI Key: QKJAXHBFQSBDAR-OWOJBTEDSA-N
• Popularity: 60 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₁Br₂N₅O
• Molecular Weight: 389.05 g/mol
• Exact Mass: 388.93099 g/mol
• Topological Polar Surface Area (TPSA): 99.60 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 3
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• Oroidine
• 34649-22-4
• UNII-PF75E92XKM
• PF75E92XKM
• CHEMBL397591
• CHEBI:70037
• N-[(E)-3-(2-amino-1H-imidazol-5-yl)prop-2-enyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
• oroidin base
• OROIDIN [MI]
• D08BMM
• C11H11Br2N5O
• MLS001250229
• SCHEMBL12597862
• DTXSID001020635
• C11-H11-Br2-N5-O
• BDBM50220547
• SMR001216083
• Q15425298
• 1H-Pyrrole-2-carboxamide, N-[(2E)-3-(2-amino-1H-imidazol-5-yl)-2-propenyl]-4,5-dibromo-
• 4,5-Dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-1H-imidazol-4-yl)-allyl]-amide
• 4,5-Dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-3H-imidazol-4-yl)-allyl]-amide
• N-(3-(2-Amino-1H-imidazole-5-yl)allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide
• N-[(E)-3-(2-amino-1H-imidazol-5-yl)allyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
• 1H-PYRROLE-2-CARBOXAMIDE, N-((2E)-3-(2-AMINO-1H-IMIDAZOL-4-YL)-2-PROPENYL)-4,5-DIBROMO-
• 1H-Pyrrole-2-carboxamide, N-(3-(2-amino-1H-imidazol-4-yl)-2-propenyl)-4,5-dibromo-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9753	97.53%
Caco-2	-	0.6328	63.28%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4007	40.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9280	92.80%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	0.9409	94.09%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6006	60.06%
P-glycoprotein inhibitior	-	0.9360	93.60%
P-glycoprotein substrate	-	0.6199	61.99%
CYP3A4 substrate	-	0.5172	51.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.8759	87.59%
CYP2C9 inhibition	-	0.7685	76.85%
CYP2C19 inhibition	-	0.7295	72.95%
CYP2D6 inhibition	-	0.8519	85.19%
CYP1A2 inhibition	+	0.6471	64.71%
CYP2C8 inhibition	-	0.7336	73.36%
CYP inhibitory promiscuity	-	0.7000	70.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8222	82.22%
Carcinogenicity (trinary)	Non-required	0.4500	45.00%
Eye corrosion	-	0.9792	97.92%
Eye irritation	-	0.9193	91.93%
Skin irritation	-	0.7750	77.50%
Skin corrosion	-	0.9295	92.95%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6857	68.57%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8644	86.44%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7740	77.40%
Acute Oral Toxicity (c)	III	0.5121	51.21%
Estrogen receptor binding	+	0.6886	68.86%
Androgen receptor binding	-	0.6784	67.84%
Thyroid receptor binding	+	0.7043	70.43%
Glucocorticoid receptor binding	+	0.7941	79.41%
Aromatase binding	+	0.8224	82.24%
PPAR gamma	+	0.6593	65.93%
Honey bee toxicity	-	0.8166	81.66%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.3652	36.52%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3587	Q02750	Dual specificity mitogen-activated protein kinase kinase 1	2500 nM	IC50	PMID: 11784156

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.31%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.96%	89.34%
CHEMBL221	P23219	Cyclooxygenase-1	91.36%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.31%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.47%	99.17%
CHEMBL4208	P20618	Proteasome component C5	88.95%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.92%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	87.05%	94.73%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.42%	81.11%
CHEMBL2535	P11166	Glucose transporter	85.84%	98.75%
CHEMBL1829	O15379	Histone deacetylase 3	85.14%	95.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	83.49%	92.29%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.01%	91.07%
CHEMBL4040	P28482	MAP kinase ERK2	82.65%	83.82%
CHEMBL1952	P04818	Thymidylate synthase	80.86%	93.53%
CHEMBL230	P35354	Cyclooxygenase-2	80.68%	89.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.16%	95.56%

Plants that contains it

• Artemisia vestita
• Leiboldia serrata
• Marah fabacea
• Monochaetum vulcanicum

Cross-Links

• PubChem: 6312649
• NPASS: NPC206148
• ChEMBL: CHEMBL397591
• LOTUS: LTS0199062
• wikiData: Q15425298