Fusidic Acid

Details

• Internal ID: 8a7daaf5-7a3e-4f46-933a-26cc86cd4eb6
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid esters
• IUPAC Name: (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
• InChI: InChI=1S/C31H48O6/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1
• InChI Key: IECPWNUMDGFDKC-MZJAQBGESA-N
• Popularity: 4,753 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₈O₆
• Molecular Weight: 516.70 g/mol
• Exact Mass: 516.34508925 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.67
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 6990-06-3
• Ramycin
• Fucidic acid
• Fucidin acid
• Fucithalmic
• Taksta
• Acide fusidique
• Acido fusidico
• Acidum fusidicum
• Anhydrous Fusidic Acid
• (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
• NSC-56192
• SQ-16603
• 59XE10C19C
• DTXSID0023086
• CHEBI:29013
• 29-Nordammara-17(20),24-dien-21-oic acid, 16-(acetyloxy)-3,11-dihydroxy-, (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17Z)-
• Fucidin caviject
• Acid, Fusidic
• Fusidate, Silver
• (2Z)-2-((3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta(a)phenanthren-17-ylidene)-6-methylhept-5-enoic acid
• RefChem:5848
• DTXCID103086
• D06AX01
• J01XC01
• S01AA13
• 230-256-0
• Fusidine
• FUCIDIN
• Fucidate
• Flucidin
• CEM-102
• SQ 16,603
• MFCD00865135
• (-)-Fusidic acid
• (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid
• Fusidic acid (Standard)
• SQ 16603
• MLS001332649
• SMR000857101
• (2E)-2-[(3R,4S,5S,8S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
• (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-hept-5-enoic acid
• Fusidinic Acid
• (-)-16beta-acetoxy-3alpha,11alpha-dihydroxyfusida-17(20)Z,24-diene-21-oic acid
• (Z)-2-((3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyldodecahydro-1H-cyclopenta[a]phenanthren-17(2H,10H,14H)-ylidene)-6-methylhept-5-enoic acid
• 3alpha,11alpha,16beta-Trihydroxy-29-nor-8alpha,9beta,13alpha,14beta-dammara-17(20),24-dien-21-oic acid 16-acetate
• Fusidic acid (USAN/INN)
• fusidic-acid
• C31H48O6
• 1qca
• Fusidic acid CRS
• Fusidate (Standard)
• C.A.S. 62,602
• Prestwick2_000390
• FUSIDIC ACID [MI]
• FUSIDIC ACID [INN]
• FUSIDIC ACID [USAN]
• SCHEMBL25646
• MLS001332650
• MLS002207094
• UNII-59XE10C19C
• Acide fusidique [INN-French]
• Acido fusidico [INN-Spanish]
• Acidum fusidicum [INN-Latin]
• FUSIDIC ACID [WHO-DD]
• CEM102
• CHEMBL374975
• orb1309560
• orb3025513
• Fusidic acid [USAN:INN:BAN]
• BDBM58924
• cid_3000226
• GTPL10815
• HY-B1350R
• GLXC-06549
• HMS2235B11
• FUSIDIC ACID [EP IMPURITY]
• EX-A3797
• FUSIDIC ACID [EP MONOGRAPH]
• HY-B1350
• NSC56192
• EINECS 230-256-0
• EBC-27263
• MSK157136
• NSC 56192
• s3971
• 16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid
• AKOS005146257
• AF23629
• CCG-269829
• DB02703
• DS-3261
• LMPR0106040001
• Fusidic acid for peak identification CRS
• NCGC00485232-01
• (2Z)-2-[(17Z)-16beta-acetoxy-3alpha,11alpha-dihydroxy-4alpha,8alpha,10,14beta-tetramethyl-5alpha,9beta,13alpha-gonan-17-ylidene]-6-methylhept-5-enoic acid
• (2Z)-2-[(3alpha,4alpha,5alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17Z)-16-(acetyloxy)-3,11-dihydroxy-4,8,10,14-tetramethylgonan-17-ylidene]-6-methylhept-5-enoic acid
• 2-[(1Z,2S,3aS,3bS,5aS,6S,7R,9aS,9bS,10R,11aR)-2-(acetyloxy)-7,10-dihydroxy-3a,3b,6,9a-tetramethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid
• SY056012
• C.A.S. 62,602; Diethanolamine fusidate
• CS-0013095
• F1007
• NS00007426
• C06694
• D04281
• EN300-22411576
• F794556
• Q259930
• Fusidic acid, European Pharmacopoeia (EP) Reference Standard
• Fusidic acid for peak identification, European Pharmacopoeia (EP) Reference Standard
• (17Z)-16beta-(Acetyloxy)-3alpha,11alpha-dihydroxy-4alpha,8,14-trimethyl-5alpha,8alpha,9beta,13alpha,14beta-18-norcholesta-17,24-dien-21-oic acid
• (2Z)-2-[(3beta,4beta,5alpha,8alpha,9beta,11beta,13alpha,16beta,17Z)-16-(acetyloxy)-3,11-dihydroxy-4,8,10,14-tetramethylgonan-17-ylidene]-6-methylhept-5-enoic acid
• (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-5-heptenoic acid
• (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-4,8,10,14-tetramethyl-3,11-bis(oxidanyl)-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-hept-5-enoic acid
• (3|A,4|A,8|A,9|A,11|A,13|A,14|A,16|A,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid
• (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,147beta,167beta,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid
• 29-Nor-8.alpha.,13.alpha.,14.beta.-dammara-17(20),24-dien-21-oic acid, 3.alpha.,11.alpha.,16.beta.-trihydroxy-, 16-acetate, (Z)-
• 29-Nor-8alpha,9beta,13alpha,14beta-dammara-17(20),24-dien-21-oic acid, 3alpha,11alpha,16beta-trihydroxy-, 16-acetate, (Z)-
• 29-Nordammara-17(20), 16-(acetyloxy)-3,11-dihydroxy-, (3.alpha.,4.alpha.,8.alpha.,9.beta.,11.alpha.,13.alpha.,14.beta.,16.beta.,17Z)-
• 29-NORDAMMARA-17(20),24-DIEN-21-OIC ACID, 16-(ACETYLOXY)-3,11-DIHYDROXY-, (3.ALPHA.,4.ALPHA.,8.ALPHA.,9.BETA.,11.ALPHA.,13.ALPHA.,14.BETA.,16.BETA.,17Z)
• 29-Nordammara-17(20),24-dien-21-oic acid, 16-(acetyloxy)-3,11-dihydroxy-, (3a,4a,8a,9b,11a,13a,14b,16b,17Z)-
• 3.alpha.,16.beta.-Trihydroxy-29-nor-8.alpha.,9.beta.,13.alpha.,14.beta.-dammara-17(20),24-dien-21-oic acid 16-acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	-	0.6911	69.11%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8700	87.00%
OATP2B1 inhibitior	-	0.7130	71.30%
OATP1B1 inhibitior	-	0.7739	77.39%
OATP1B3 inhibitior	-	0.4292	42.92%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7032	70.32%
BSEP inhibitior	+	0.9724	97.24%
P-glycoprotein inhibitior	+	0.8964	89.64%
P-glycoprotein substrate	-	0.5701	57.01%
CYP3A4 substrate	+	0.7114	71.14%
CYP2C9 substrate	-	0.7828	78.28%
CYP2D6 substrate	-	0.9079	90.79%
CYP3A4 inhibition	-	0.7600	76.00%
CYP2C9 inhibition	-	0.8834	88.34%
CYP2C19 inhibition	-	0.9347	93.47%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.9337	93.37%
CYP2C8 inhibition	+	0.4818	48.18%
CYP inhibitory promiscuity	-	0.8190	81.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7047	70.47%
Eye corrosion	-	0.9958	99.58%
Eye irritation	-	0.9212	92.12%
Skin irritation	+	0.6627	66.27%
Skin corrosion	-	0.9642	96.42%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4078	40.78%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.9166	91.66%
skin sensitisation	-	0.6636	66.36%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8529	85.29%
Acute Oral Toxicity (c)	III	0.4932	49.32%
Estrogen receptor binding	+	0.6995	69.95%
Androgen receptor binding	+	0.7688	76.88%
Thyroid receptor binding	+	0.5204	52.04%
Glucocorticoid receptor binding	+	0.7545	75.45%
Aromatase binding	+	0.7566	75.66%
PPAR gamma	+	0.6504	65.04%
Honey bee toxicity	-	0.6228	62.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.51%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.22%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.21%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.28%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.81%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.84%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.07%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.97%	82.69%
CHEMBL2581	P07339	Cathepsin D	86.94%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.61%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.15%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.39%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.74%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.67%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	81.92%	97.05%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.89%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.36%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.13%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 3000226
• LOTUS: LTS0182146
• wikiData: Q259930