Niazicin A

Details

• Internal ID: 56694d7f-6185-4be7-9fe5-34e395835e5d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[4-[(methoxycarbothioylamino)methyl]phenoxy]-2-methyloxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC=C(C=C2)CNC(=S)OC)O)O)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)CNC(=S)OC)O)O)OC(=O)C
• InChI: InChI=1S/C17H23NO7S/c1-9-15(24-10(2)19)13(20)14(21)16(23-9)25-12-6-4-11(5-7-12)8-18-17(26)22-3/h4-7,9,13-16,20-21H,8H2,1-3H3,(H,18,26)/t9-,13-,14+,15-,16-/m0/s1
• InChI Key: HMXLIRAHSHWREJ-QOYUQHOESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃NO₇S
• Molecular Weight: 385.40 g/mol
• Exact Mass: 385.11952325 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.48
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• Niazicin B
• S5WKZ900CX
• 159768-74-8
• (2S,3R,4S,5R,6S)-4,5-Dihydroxy-6-(4-(((methoxymethanethioyl)amino)methyl)phenoxy)-2-methyloxan-3-yl acetate
• Carbamothioic acid, N-((4-((4-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy)phenyl)methyl)-, O-methyl ester
• [(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[4-[(methoxycarbothioylamino)methyl]phenoxy]-2-methyloxan-3-yl] acetate
• CARBAMOTHIOIC ACID, N-((4-((4-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)PHENYL)METHYL)-, O-METHYL ESTER
• ((2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(4-((methoxycarbothioylamino)methyl)phenoxy)-2-methyloxan-3-yl) acetate
• RefChem:165638
• UNII-S5WKZ900CX
• Niazicin
• CHEMBL1223971
• CHEBI:179523
• DTXSID601318452

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5916	59.16%
Caco-2	-	0.6089	60.89%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5797	57.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9050	90.50%
OATP1B3 inhibitior	+	0.9275	92.75%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7947	79.47%
P-glycoprotein inhibitior	-	0.6855	68.55%
P-glycoprotein substrate	-	0.7037	70.37%
CYP3A4 substrate	+	0.6184	61.84%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.8772	87.72%
CYP3A4 inhibition	-	0.5350	53.50%
CYP2C9 inhibition	-	0.7556	75.56%
CYP2C19 inhibition	-	0.6144	61.44%
CYP2D6 inhibition	-	0.8169	81.69%
CYP1A2 inhibition	-	0.7395	73.95%
CYP2C8 inhibition	-	0.7716	77.16%
CYP inhibitory promiscuity	-	0.5283	52.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.6182	61.82%
Eye corrosion	-	0.9851	98.51%
Eye irritation	-	0.9860	98.60%
Skin irritation	-	0.7856	78.56%
Skin corrosion	-	0.9444	94.44%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4584	45.84%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6447	64.47%
skin sensitisation	-	0.8564	85.64%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7805	78.05%
Acute Oral Toxicity (c)	III	0.5172	51.72%
Estrogen receptor binding	-	0.4873	48.73%
Androgen receptor binding	-	0.6307	63.07%
Thyroid receptor binding	+	0.6252	62.52%
Glucocorticoid receptor binding	-	0.5503	55.03%
Aromatase binding	-	0.5889	58.89%
PPAR gamma	-	0.6268	62.68%
Honey bee toxicity	-	0.6396	63.96%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.7261	72.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.09%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.98%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.12%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	90.30%	94.73%
CHEMBL4208	P20618	Proteasome component C5	89.74%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.84%	99.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.95%	81.11%
CHEMBL221	P23219	Cyclooxygenase-1	83.99%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.94%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.67%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.42%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.86%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.71%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.57%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.24%	95.89%

Plants that contains it

• Calamus draco
• Excoecaria acerifolia
• Garrya laurifolia
• Goupia glabra
• Laggera alata
• Medinilla magnifica
• Mesua ferrea
• Moringa oleifera
• Onobrychis bobrovii
• Papaver persicum
• Petteria ramentacea
• Senecio cathcartensis
• Sequoia sempervirens
• Syncarpha gnaphaloides

Cross-Links

• PubChem: 10068657
• NPASS: NPC97282
• LOTUS: LTS0078356
• wikiData: Q76415060