Kukoamine A

Details

• Internal ID: 9f686eac-f8e1-4cea-8457-bd7cf0b40d0a
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 3-(3,4-dihydroxyphenyl)-N-[3-[4-[3-[3-(3,4-dihydroxyphenyl)propanoylamino]propylamino]butylamino]propyl]propanamide
• SMILES (Canonical): C1=CC(=C(C=C1CCC(=O)NCCCNCCCCNCCCNC(=O)CCC2=CC(=C(C=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CCC(=O)NCCCNCCCCNCCCNC(=O)CCC2=CC(=C(C=C2)O)O)O)O
• InChI: InChI=1S/C28H42N4O6/c33-23-9-5-21(19-25(23)35)7-11-27(37)31-17-3-15-29-13-1-2-14-30-16-4-18-32-28(38)12-8-22-6-10-24(34)26(36)20-22/h5-6,9-10,19-20,29-30,33-36H,1-4,7-8,11-18H2,(H,31,37)(H,32,38)
• InChI Key: IOLDDENZPBFBHV-UHFFFAOYSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂N₄O₆
• Molecular Weight: 530.70 g/mol
• Exact Mass: 530.31043507 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 8
• H-Bond Donor: 8
• Rotatable Bonds: 19

Synonyms

• 75288-96-9
• 3-(3,4-dihydroxyphenyl)-N-[3-[4-[3-[3-(3,4-dihydroxyphenyl)propanoylamino]propylamino]butylamino]propyl]propanamide
• 9YM64FBW2R
• DTXSID401318256
• 3-(3,4-dihydroxyphenyl)-N-(3-(4-(3-(3-(3,4-dihydroxyphenyl)propanoylamino)propylamino)butylamino)propyl)propanamide
• N(1),N(12)-bis(dihydrocaffeoyl)spermine
• RefChem:924273
• DTXCID701748042
• MFCD29904538
• CHEMBL79129
• CHEBI:81220
• N1,N12-Bis(dihydrocaffeoyl) spermine
• N1,N2-bis(dihydrocaffeoyl)spermine
• A1BDT
• Kukoamine A (Standard)
• orb1297612
• SCHEMBL16547596
• SCHEMBL29372410
• SCHEMBL30255643
• HY-N2392R
• 1,14-Bis(dihydrocaffeoyl)spermine
• HY-N2392
• BDBM50240622
• MSK158321
• AKOS032945995
• ZINC-13513540
• FK74515
• AC-34134
• DA-54700
• MS-29818
• CS-0022594
• C17615
• Q27155166
• Benzenepropanamide, N,N'-[1,4-butanediylbis(imino-3,1-propanediyl)]bis[3,4-dihydroxy-
• N,N'-[1,4-butanediylbis(imino-3,1-propanediyl)]bis[3,4-dihydroxybenzenepropanamide]
• 3-(3,4-Bis(oxidanyl)phenyl)-N-(3-(4-(3-(3-(3,4-bis(oxidanyl)phenyl)propanoylamino)propylamino)butylamino)propyl)propanamide
• 3-(3,4-Dihydroxy-phenyl)-N-[3-(4-{3-[3-(3,4-dihydroxy-phenyl)-propionylamino]-propylamino}-butylamino)-propyl]-propionamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6289	62.89%
Caco-2	-	0.8712	87.12%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6528	65.28%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9347	93.47%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5537	55.37%
P-glycoprotein inhibitior	+	0.7030	70.30%
P-glycoprotein substrate	+	0.5492	54.92%
CYP3A4 substrate	-	0.5485	54.85%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	+	0.3571	35.71%
CYP3A4 inhibition	-	0.5732	57.32%
CYP2C9 inhibition	-	0.8998	89.98%
CYP2C19 inhibition	-	0.8657	86.57%
CYP2D6 inhibition	-	0.8274	82.74%
CYP1A2 inhibition	-	0.8246	82.46%
CYP2C8 inhibition	-	0.6677	66.77%
CYP inhibitory promiscuity	-	0.9547	95.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.7434	74.34%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.8918	89.18%
Skin irritation	-	0.7569	75.69%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8912	89.12%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8181	81.81%
Acute Oral Toxicity (c)	III	0.6893	68.93%
Estrogen receptor binding	+	0.7059	70.59%
Androgen receptor binding	+	0.7657	76.57%
Thyroid receptor binding	+	0.5761	57.61%
Glucocorticoid receptor binding	-	0.4703	47.03%
Aromatase binding	+	0.6410	64.10%
PPAR gamma	+	0.7029	70.29%
Honey bee toxicity	-	0.9033	90.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7483	74.83%

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	99.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.08%	98.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	95.85%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.53%	99.17%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	90.46%	89.33%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	89.85%	96.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.32%	96.09%
CHEMBL4208	P20618	Proteasome component C5	88.10%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.68%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.19%	90.71%
CHEMBL2535	P11166	Glucose transporter	86.11%	98.75%
CHEMBL3902	P09211	Glutathione S-transferase Pi	85.84%	93.81%
CHEMBL3401	O75469	Pregnane X receptor	83.77%	94.73%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.43%	85.31%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	81.83%	98.11%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.45%	100.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.11%	96.37%
CHEMBL4578	Q14680	Maternal embryonic leucine zipper kinase	81.07%	81.58%

Plants that contains it

• Lycium chinense

Cross-Links

• PubChem: 5318865
• NPASS: NPC271808
• ChEMBL: CHEMBL79129