Rifamycin S

Details

• Internal ID: 1d331ccd-0633-4acb-bfdc-dd65417dede8
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate
• InChI: InChI=1S/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
• InChI Key: BTVYFIMKUHNOBZ-ODRIEIDWSA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₅NO₁₂
• Molecular Weight: 695.80 g/mol
• Exact Mass: 695.29417587 g/mol
• Topological Polar Surface Area (TPSA): 195.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 13553-79-2
• Rifomycin S
• Rifampicin S
• NCI 144-130
• Rifamycin, 1,4-dideoxy-1,4-dihydro-1,4-dioxo-
• PI53N820JV
• CHEBI:34948
• 1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin
• Rafamycin S
• EINECS 236-938-4
• NSC 144130
• BRN 0604802
• UNII-PI53N820JV
• rifamycin-S
• NSC144130
• NSC-144130
• RIFAMYCIN S [MI]
• SCHEMBL415695
• CHEMBL236921
• BTVYFIMKUHNOBZ-ODRIEIDWSA-N
• RIFAMYCIN S [EP IMPURITY]
• DTXSID301043935
• MFCD06198807
• s4425
• 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,6,9,11(2H)-tetrone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate
• RIFAXIMIN IMPURITY E [EP IMPURITY]
• RIFAMYCIN SODIUM IMPURITY B [EP IMPURITY]
• Q27116328
• ((2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-5,17,19-TRIHYDROXY-23-METHOXY-2,4,12,16,18,20,22-HEPTAMETHYL-1,6,9,11-TETRAOXO-1,2-DIHYDRO-2,7-(EPOXYPENTADECA(1,11,13)TRIENAZANO)NAPHTHO(2,1-B)FURAN-21-YL ACETATE
• [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9503	95.03%
Caco-2	-	0.8418	84.18%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Plasma membrane	0.5008	50.08%
OATP2B1 inhibitior	+	0.5112	51.12%
OATP1B1 inhibitior	+	0.7461	74.61%
OATP1B3 inhibitior	+	0.9296	92.96%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9806	98.06%
P-glycoprotein inhibitior	-	0.5273	52.73%
P-glycoprotein substrate	+	0.7730	77.30%
CYP3A4 substrate	+	0.6922	69.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8946	89.46%
CYP3A4 inhibition	-	0.6870	68.70%
CYP2C9 inhibition	-	0.7845	78.45%
CYP2C19 inhibition	-	0.8325	83.25%
CYP2D6 inhibition	-	0.8802	88.02%
CYP1A2 inhibition	-	0.7959	79.59%
CYP2C8 inhibition	+	0.6966	69.66%
CYP inhibitory promiscuity	+	0.6167	61.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Danger	0.5157	51.57%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.7991	79.91%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3980	39.80%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.8496	84.96%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6708	67.08%
Acute Oral Toxicity (c)	III	0.5789	57.89%
Estrogen receptor binding	+	0.8150	81.50%
Androgen receptor binding	+	0.7966	79.66%
Thyroid receptor binding	+	0.5422	54.22%
Glucocorticoid receptor binding	+	0.8041	80.41%
Aromatase binding	+	0.6172	61.72%
PPAR gamma	+	0.7889	78.89%
Honey bee toxicity	-	0.6970	69.70%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8903	89.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.50%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.79%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.23%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.48%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	93.34%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.02%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.33%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.65%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.46%	94.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.48%	96.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.16%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.08%	97.28%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.92%	93.03%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.82%	96.67%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.57%	97.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.27%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.14%	91.07%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.10%	93.40%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6436726
• LOTUS: LTS0256211
• wikiData: Q27116328