Prenylagaramide A

Details

• Internal ID: 4f9d08fd-9807-4385-b6d1-c31ecce43e8a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: 3-[(3S,6S,9S,12S,18S,24S,27S)-3-(2-amino-2-oxoethyl)-6,9-dibenzyl-18-[(1R)-1-hydroxyethyl]-24-[[4-(3-methylbut-2-enoxy)phenyl]methyl]-2,5,8,11,14,17,20,23,26-nonaoxo-1,4,7,10,13,16,19,22,25-nonazabicyclo[25.3.0]triacontan-12-yl]propanoic acid
• SMILES (Canonical): CC(C1C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NCC(=O)N1)CC3=CC=C(C=C3)OCC=C(C)C)CC(=O)N)CC4=CC=CC=C4)CC5=CC=CC=C5)CCC(=O)O)O
• SMILES (Isomeric): C[C@H]([C@H]1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)NCC(=O)N1)CC3=CC=C(C=C3)OCC=C(C)C)CC(=O)N)CC4=CC=CC=C4)CC5=CC=CC=C5)CCC(=O)O)O
• InChI: InChI=1S/C54H68N10O14/c1-31(2)22-24-78-36-18-16-35(17-19-36)27-38-48(71)56-30-45(68)63-47(32(3)65)53(76)57-29-44(67)58-37(20-21-46(69)70)49(72)59-39(25-33-11-6-4-7-12-33)50(73)60-40(26-34-13-8-5-9-14-34)51(74)62-41(28-43(55)66)54(77)64-23-10-15-42(64)52(75)61-38/h4-9,11-14,16-19,22,32,37-42,47,65H,10,15,20-21,23-30H2,1-3H3,(H2,55,66)(H,56,71)(H,57,76)(H,58,67)(H,59,72)(H,60,73)(H,61,75)(H,62,74)(H,63,68)(H,69,70)/t32-,37+,38+,39+,40+,41+,42+,47+/m1/s1
• InChI Key: LXDPLRBOMKUKGF-DEOTVAGQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₆₈N₁₀O₁₄
• Molecular Weight: 1081.20 g/mol
• Exact Mass: 1080.49164688 g/mol
• Topological Polar Surface Area (TPSA): 363.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): -1.67
• H-Bond Acceptor: 13
• H-Bond Donor: 11
• Rotatable Bonds: 15

Synonyms

• CHEMBL507696
• DTXSID801046134

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8811	88.11%
Caco-2	-	0.8685	86.85%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6492	64.92%
OATP2B1 inhibitior	-	0.7149	71.49%
OATP1B1 inhibitior	+	0.8738	87.38%
OATP1B3 inhibitior	+	0.9281	92.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9349	93.49%
P-glycoprotein inhibitior	+	0.7493	74.93%
P-glycoprotein substrate	+	0.8270	82.70%
CYP3A4 substrate	+	0.7108	71.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7975	79.75%
CYP3A4 inhibition	-	0.9253	92.53%
CYP2C9 inhibition	-	0.8966	89.66%
CYP2C19 inhibition	-	0.8561	85.61%
CYP2D6 inhibition	-	0.8953	89.53%
CYP1A2 inhibition	-	0.8998	89.98%
CYP2C8 inhibition	+	0.6885	68.85%
CYP inhibitory promiscuity	-	0.8702	87.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5516	55.16%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9008	90.08%
Skin irritation	-	0.7702	77.02%
Skin corrosion	-	0.9308	93.08%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6468	64.68%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.5715	57.15%
skin sensitisation	-	0.8778	87.78%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7065	70.65%
Acute Oral Toxicity (c)	III	0.5934	59.34%
Estrogen receptor binding	+	0.8072	80.72%
Androgen receptor binding	+	0.7004	70.04%
Thyroid receptor binding	+	0.5723	57.23%
Glucocorticoid receptor binding	+	0.5549	55.49%
Aromatase binding	+	0.6386	63.86%
PPAR gamma	+	0.7614	76.14%
Honey bee toxicity	-	0.7629	76.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9547	95.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.84%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.40%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.64%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.15%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.52%	94.45%
CHEMBL4071	P08311	Cathepsin G	96.94%	94.64%
CHEMBL221	P23219	Cyclooxygenase-1	96.94%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	96.91%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	96.49%	93.00%
CHEMBL1801	P00747	Plasminogen	96.30%	92.44%
CHEMBL4447	Q9Y337	Kallikrein 5	96.09%	87.50%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	95.36%	97.64%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	94.62%	82.38%
CHEMBL4208	P20618	Proteasome component C5	94.32%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.89%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.44%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.49%	97.09%
CHEMBL3524	P56524	Histone deacetylase 4	89.22%	92.97%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.01%	90.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.33%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.12%	95.50%
CHEMBL4040	P28482	MAP kinase ERK2	87.69%	83.82%
CHEMBL5203	P33316	dUTP pyrophosphatase	85.41%	99.18%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	84.90%	98.00%
CHEMBL1902	P62942	FK506-binding protein 1A	83.76%	97.05%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.57%	97.14%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.03%	92.67%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.62%	97.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.02%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.62%	99.15%
CHEMBL255	P29275	Adenosine A2b receptor	80.90%	98.59%
CHEMBL2443	P49862	Kallikrein 7	80.75%	94.00%

Plants that contains it

• Elsholtzia bodinieri
• Ipomoea purpurea

Cross-Links

• PubChem: 10748669
• NPASS: NPC241164
• LOTUS: LTS0009339
• wikiData: Q77422255