Pitipeptolide A

Details

• Internal ID: 096de7dc-58ab-483d-91fd-014f2131e1a2
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3S,6S,9S,13S,19S,22S)-6-benzyl-3,19-bis[(2S)-butan-2-yl]-7,12,12-trimethyl-13-pent-4-ynyl-9-propan-2-yl-4,14-dioxa-1,7,10,17,20-pentazabicyclo[20.3.0]pentacosane-2,5,8,11,15,18,21-heptone
• InChI: InChI=1S/C44H65N5O9/c1-11-14-16-23-33-44(8,9)43(56)47-35(27(4)5)40(53)48(10)32(25-30-20-17-15-18-21-30)42(55)58-37(29(7)13-3)41(54)49-24-19-22-31(49)38(51)46-36(28(6)12-2)39(52)45-26-34(50)57-33/h1,15,17-18,20-21,27-29,31-33,35-37H,12-14,16,19,22-26H2,2-10H3,(H,45,52)(H,46,51)(H,47,56)/t28-,29-,31-,32-,33-,35-,36-,37-/m0/s1
• InChI Key: MGUMDFGKOQUYTD-XXMTWPQQSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₅N₅O₉
• Molecular Weight: 808.00 g/mol
• Exact Mass: 807.47822867 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 3.55
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

• DTXSID101046652
• (3S,6S,9S,13S,19S,22S)-6-benzyl-3,19-bis((2S)-butan-2-yl)-7,12,12-trimethyl-13-pent-4-ynyl-9-propan-2-yl-4,14-dioxa-1,7,10,17,20-pentazabicyclo(20.3.0)pentacosane-2,5,8,11,15,18,21-heptone
• (3S,6S,9S,13S,19S,22S)-6-benzyl-3,19-bis[(2S)-butan-2-yl]-7,12,12-trimethyl-13-pent-4-ynyl-9-propan-2-yl-4,14-dioxa-1,7,10,17,20-pentazabicyclo[20.3.0]pentacosane-2,5,8,11,15,18,21-heptone
• RefChem:174602
• DTXCID901528474
• 334706-26-2
• CHEMBL505780
• SCHEMBL16431797
• CHEBI:211644
• (3S,6S,9S,13S,19S,22S)-6-benzyl-9-isopropyl-7,12,12-trimethyl-3,19-bis[(1S)-1-methylpropyl]-13-pent-4-ynyl-4,14-dioxa-1,7,10,17,20-pentazabicyclo[20.3.0]pentacosane-2,5,8,11,15,18,21-heptone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4869	48.69%
Caco-2	-	0.8450	84.50%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.6132	61.32%
OATP2B1 inhibitior	-	0.7104	71.04%
OATP1B1 inhibitior	+	0.8107	81.07%
OATP1B3 inhibitior	+	0.9232	92.32%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9654	96.54%
P-glycoprotein inhibitior	+	0.7930	79.30%
P-glycoprotein substrate	+	0.8504	85.04%
CYP3A4 substrate	+	0.7206	72.06%
CYP2C9 substrate	-	0.6250	62.50%
CYP2D6 substrate	-	0.8312	83.12%
CYP3A4 inhibition	-	0.5916	59.16%
CYP2C9 inhibition	-	0.7901	79.01%
CYP2C19 inhibition	-	0.7553	75.53%
CYP2D6 inhibition	-	0.8975	89.75%
CYP1A2 inhibition	-	0.8909	89.09%
CYP2C8 inhibition	+	0.7128	71.28%
CYP inhibitory promiscuity	-	0.9431	94.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5890	58.90%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9160	91.60%
Skin irritation	-	0.7797	77.97%
Skin corrosion	-	0.9100	91.00%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6539	65.39%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.7069	70.69%
skin sensitisation	-	0.8744	87.44%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6674	66.74%
Acute Oral Toxicity (c)	III	0.6493	64.93%
Estrogen receptor binding	+	0.8316	83.16%
Androgen receptor binding	+	0.6787	67.87%
Thyroid receptor binding	+	0.6031	60.31%
Glucocorticoid receptor binding	+	0.7102	71.02%
Aromatase binding	+	0.6273	62.73%
PPAR gamma	+	0.7966	79.66%
Honey bee toxicity	-	0.7145	71.45%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9034	90.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.72%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	98.74%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL333	P08253	Matrix metalloproteinase-2	96.79%	96.31%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	96.67%	82.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.99%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.96%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	93.80%	93.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.04%	90.08%
CHEMBL1902	P62942	FK506-binding protein 1A	92.04%	97.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.96%	91.11%
CHEMBL3524	P56524	Histone deacetylase 4	91.36%	92.97%
CHEMBL5203	P33316	dUTP pyrophosphatase	90.81%	99.18%
CHEMBL3837	P07711	Cathepsin L	89.90%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.76%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.73%	86.33%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	89.71%	97.64%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.32%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.68%	94.45%
CHEMBL4588	P22894	Matrix metalloproteinase 8	85.17%	94.66%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.88%	99.23%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.78%	92.67%
CHEMBL1978	P11511	Cytochrome P450 19A1	83.99%	91.76%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.44%	88.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.84%	90.24%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	81.73%	96.42%
CHEMBL4208	P20618	Proteasome component C5	80.96%	90.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.95%	85.94%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.62%	98.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.27%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.09%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11803484
• LOTUS: LTS0118153
• wikiData: Q105163583