Surfactin A

Details

• Internal ID: 2dc592a9-c0c0-41c1-992f-140dc4f59282
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: 3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-12-propan-2-yl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl]propanoic acid
• InChI: InChI=1S/C51H89N7O13/c1-28(2)18-16-14-13-15-17-19-34-26-41(59)52-35(20-21-42(60)61)45(64)53-36(22-29(3)4)46(65)55-38(24-31(7)8)49(68)58-44(33(11)12)50(69)56-39(27-43(62)63)48(67)54-37(23-30(5)6)47(66)57-40(25-32(9)10)51(70)71-34/h28-40,44H,13-27H2,1-12H3,(H,52,59)(H,53,64)(H,54,67)(H,55,65)(H,56,69)(H,57,66)(H,58,68)(H,60,61)(H,62,63)/t34-,35+,36+,37-,38-,39+,40+,44+/m1/s1
• InChI Key: PBEDWPIWZYHNPL-RHKAOURMSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₈₉N₇O₁₃
• Molecular Weight: 1008.30 g/mol
• Exact Mass: 1007.65183592 g/mol
• Topological Polar Surface Area (TPSA): 305.00 Ų
• XlogP: 7.70
• Atomic LogP (AlogP): 4.26
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 22

Synonyms

• CHEBI:71976
• 3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-3,6,15,18-tetraisobutyl-12-isopropyl-25-(8-methylnonyl)-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-21-yl]propanoic acid
• 3-((3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-3,6,15,18-tetraisobutyl-12-isopropyl-25-(8-methylnonyl)-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-21-yl)propanoic acid
• RefChem:186820
• 3-((3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-12-propan-2-yl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl)propanoic acid
• Surfactin A1
• E5UL4K2TAR
• SCHEMBL29382215
• Q27139838
• 1419881-43-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5924	59.24%
Caco-2	-	0.8590	85.90%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6768	67.68%
OATP2B1 inhibitior	-	0.7193	71.93%
OATP1B1 inhibitior	+	0.8744	87.44%
OATP1B3 inhibitior	+	0.8746	87.46%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7890	78.90%
BSEP inhibitior	+	0.8181	81.81%
P-glycoprotein inhibitior	+	0.7386	73.86%
P-glycoprotein substrate	+	0.8085	80.85%
CYP3A4 substrate	+	0.6320	63.20%
CYP2C9 substrate	+	0.6276	62.76%
CYP2D6 substrate	-	0.8892	88.92%
CYP3A4 inhibition	-	0.7473	74.73%
CYP2C9 inhibition	-	0.9410	94.10%
CYP2C19 inhibition	-	0.9381	93.81%
CYP2D6 inhibition	-	0.9416	94.16%
CYP1A2 inhibition	-	0.9491	94.91%
CYP2C8 inhibition	-	0.6775	67.75%
CYP inhibitory promiscuity	-	0.9847	98.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6658	66.58%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8986	89.86%
Skin irritation	-	0.7776	77.76%
Skin corrosion	-	0.9367	93.67%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4194	41.94%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8813	88.13%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6780	67.80%
Acute Oral Toxicity (c)	III	0.6639	66.39%
Estrogen receptor binding	+	0.8127	81.27%
Androgen receptor binding	+	0.6454	64.54%
Thyroid receptor binding	+	0.5155	51.55%
Glucocorticoid receptor binding	+	0.6347	63.47%
Aromatase binding	+	0.6755	67.55%
PPAR gamma	+	0.7051	70.51%
Honey bee toxicity	-	0.8832	88.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	-	0.3853	38.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.14%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	97.56%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.52%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	96.05%	90.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.57%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	94.66%	96.47%
CHEMBL1937	Q92769	Histone deacetylase 2	92.76%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.60%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.68%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.06%	94.45%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	90.85%	95.00%
CHEMBL2996	Q05655	Protein kinase C delta	88.82%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.38%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.02%	93.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.28%	82.38%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.96%	88.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.59%	97.09%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	85.88%	92.32%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.84%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.21%	90.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.80%	95.50%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	84.57%	96.11%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.26%	85.31%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.57%	96.90%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.56%	99.23%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	82.82%	97.64%
CHEMBL340	P08684	Cytochrome P450 3A4	82.76%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.60%	93.00%
CHEMBL299	P17252	Protein kinase C alpha	81.98%	98.03%
CHEMBL236	P41143	Delta opioid receptor	81.04%	99.35%
CHEMBL3524	P56524	Histone deacetylase 4	80.20%	92.97%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 70789014
• LOTUS: LTS0246445
• wikiData: Q27139838