Aureobasidin A

Details

• Internal ID: 2b85ccb5-baa6-4ad0-815f-db988f288d31
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3S,6S,9S,12R,15S,18S,21S,24S,27S)-3,6-dibenzyl-12,24-bis[(2R)-butan-2-yl]-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo[25.3.0]triacontane-2,5,8,11,14,17,20,23,26-nonone
• SMILES (Canonical): CCC(C)C1C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)N2CCCC2C(=O)N1)CC3=CC=CC=C3)C)CC4=CC=CC=C4)C(C)C)C)C(C)CC)C(C)(C)O)C)CC(C)C)C(C)C)C
• SMILES (Isomeric): CC[C@@H](C)[C@H]1C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N2CCC[C@H]2C(=O)N1)CC3=CC=CC=C3)C)CC4=CC=CC=C4)C(C)C)C)[C@H](C)CC)C(C)(C)O)C)CC(C)C)C(C)C)C
• InChI: InChI=1S/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46+,47+,48+,49-,50-/m1/s1
• InChI Key: RLMLFADXHJLPSQ-QKCBWMAHSA-N
• Popularity: 465 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₀H₉₂N₈O₁₁
• Molecular Weight: 1101.40 g/mol
• Exact Mass: 1100.68855578 g/mol
• Topological Polar Surface Area (TPSA): 235.00 Ų
• XlogP: 8.50
• Atomic LogP (AlogP): 4.37
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 13

Synonyms

• 127785-64-2
• Basifungin
• VV0USO6I6U
• LY295337
• LY-295337
• NK 204
• R106-1
• DTXSID201017531
• NK-204
• (3S,6S,9S,12R,15S,18S,21S,24S,27S)-3,6-dibenzyl-12,24-bis[(2R)-butan-2-yl]-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo[25.3.0]triacontane-2,5,8,11,14,17,20,23,26-nonone
• R106 1
• Basifungina
• Basifungine
• R-106-1
• basifunginum
• (3S,6S,9S,12R,15S,18S,21S,24S,27S)-3,6-dibenzyl-12,24-bis((2R)-butan-2-yl)-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo(25.3.0)triacontane-2,5,8,11,14,17,20,23,26-nonone
• RefChem:561099
• DTXCID701475720
• DTXCID901475819
• (3S,6S,9S,12S,15S,18S,21S,24R,27S)-3,6-dibenzyl-12,24-bis((2R)-butan-2-yl)-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo(25.3.0)triacontane-2,5,8,11,14,17,20,23,26-nonone
• cyclo-(D-Hmp(1)-L-MeVal(2)-L-Phe(3)-L-MePhe(4)-L-Pro(5)-L-aIle+ ++(6)-L-MeVal(7)-L-Leu(8)-L-betaHOMeVal(9))
• (3R,6S,9S,12S,15S,21S,24S,29aS)-21,24-dibenzyl-15-((2R)-butan-2-yl)-9-isobutyl-6,12,18-triisopropyl-5,11,23-trimethyl-3-((2R)-3-methylbutan-2-yl)octadecahydro-1H,15H-pyrrolo(1,2-m)(1,4,7,10,13,16,19,22,25)oxaoctaazacycloheptacosine-1,4,7,10,13,16,19,22,25-nonone
• Antibiotic R106I
• CHEBI:61739
• DTXSID801017634
• CHEMBL1793802
• Basifungin [USAN:INN]
• UNII-VV0USO6I6U
• Basifungin; AbA
• Ly 295337
• BASIFUNGIN [INN]
• Basifungin (USAN/INN)
• BASIFUNGIN [USAN]
• Aureobasidin A pound notAbA
• Aureobasidin A(Basifungin)?
• SCHEMBL301215
• orb1298229
• HY-P1975
• BDBM50408926
• EX-A13442
• EBC-616463
• (3S,6S,9S,12S,15R,18S,21S,24S,29aS)-21,24-dibenzyl-3,15-bis[(2R)-butan-2-yl]-12-(2-hydroxypropan-2-yl)-5,11,17,23-tetramethyl-9-(2-methylpropyl)-6,18-bis(propan-2-yl)-octacosahydropyrrolo[1,2-m]1-oxa-4,7,10,13,16,19,22,25-octaazacycloheptacosane-1,4,7,10,13,16,19,22,25-nonone
• DA-50942
• MS-31962
• N-((2R,3R)-2-Hydroxy-3-methylvaleryl)-N-methyl-L-valyl-L-phenylalanyl-N-methyl-L-phenylalanyl-L-prolyl-L-alloisoleucyl-N-methyl-L-valyl-L-leucyl-3-hydroxy-N-methyl-L-valine alpha1-lactone
• CS-0104069
• NS00011675
• D03057
• Q27292033
• (3S,6S,9S,12S,15R,18S,21S,24S,29aS)-21,24-Dibenzyl-3,15-di[(2R)-butan-2-yl]-12-(2-hydroxypropan-2-yl)-5,11,17,23-tetramethyl-9-(2-methylpropyl)-6,18-di(propan-2-yl)octadecahydro-1H,15H-pyrrolo[1,2-m][1,4,7,10,13,16,19,22,25]oxaoctaazacycloheptacosine-1,4,7,10,13,16,19,22,25-nonone
• N-((2R,3R)-2-HYDROXY-3-METHYLVALERYL)-N-METHYL-L-VALYL-L-PHENYLALANYL-N-METHYL-L-PHENYLALANYL-L-PROLYL-L-ALLOISOLEUCYL-N-METHYL-L-VALYL-L-LEUCYL-3-HYDROXY-N-METHYL-L-VALINE .ALPHA.(SUB 1)-LACTONE
• Valine, 3-hydroxy-N-(N-(N-(N-(1-(N-(N-(N-(2-hydroxy-3-methyl-1-oxopentyl)-N-methylvalyl)phenylalanyl)-N-methylphenylalanyl)prolyl)alloisoleucyl)-N-methylvalyl)leucyl)-N-methyl-, alpha-1-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7460	74.60%
Caco-2	-	0.8653	86.53%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4523	45.23%
OATP2B1 inhibitior	-	0.7134	71.34%
OATP1B1 inhibitior	+	0.8303	83.03%
OATP1B3 inhibitior	+	0.9136	91.36%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9315	93.15%
P-glycoprotein inhibitior	+	0.7581	75.81%
P-glycoprotein substrate	+	0.8527	85.27%
CYP3A4 substrate	+	0.7033	70.33%
CYP2C9 substrate	-	0.6108	61.08%
CYP2D6 substrate	-	0.8243	82.43%
CYP3A4 inhibition	+	0.5159	51.59%
CYP2C9 inhibition	-	0.6869	68.69%
CYP2C19 inhibition	-	0.7383	73.83%
CYP2D6 inhibition	-	0.8677	86.77%
CYP1A2 inhibition	-	0.9399	93.99%
CYP2C8 inhibition	+	0.6632	66.32%
CYP inhibitory promiscuity	-	0.9254	92.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6312	63.12%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9034	90.34%
Skin irritation	-	0.7844	78.44%
Skin corrosion	-	0.9217	92.17%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6473	64.73%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7539	75.39%
Acute Oral Toxicity (c)	III	0.6738	67.38%
Estrogen receptor binding	+	0.7878	78.78%
Androgen receptor binding	+	0.7457	74.57%
Thyroid receptor binding	+	0.6341	63.41%
Glucocorticoid receptor binding	+	0.7239	72.39%
Aromatase binding	+	0.5774	57.74%
PPAR gamma	+	0.8074	80.74%
Honey bee toxicity	-	0.7502	75.02%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9803	98.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.87%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.15%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.12%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.69%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.81%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	93.73%	82.38%
CHEMBL333	P08253	Matrix metalloproteinase-2	93.71%	96.31%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	93.43%	97.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.72%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	90.07%	90.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.06%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.67%	93.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.85%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	88.77%	97.05%
CHEMBL3524	P56524	Histone deacetylase 4	87.90%	92.97%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.18%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.71%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.63%	99.23%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.84%	90.08%
CHEMBL3401	O75469	Pregnane X receptor	84.28%	94.73%
CHEMBL4616	Q92847	Ghrelin receptor	83.78%	92.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.50%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.73%	93.56%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.69%	95.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.27%	98.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.96%	97.09%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.87%	99.18%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9919816
• LOTUS: LTS0110479
• wikiData: Q27292033