Kurchessine

Details

• Internal ID: 098fdfc6-7442-47d3-9892-55066d748c5e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Azasteroids and derivatives
• IUPAC Name: (3S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine
• SMILES (Canonical): CC(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)N(C)C)C)C)N(C)C
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)N(C)C)C)C)N(C)C
• InChI: InChI=1S/C25H44N2/c1-17(26(4)5)21-10-11-22-20-9-8-18-16-19(27(6)7)12-14-24(18,2)23(20)13-15-25(21,22)3/h8,17,19-23H,9-16H2,1-7H3/t17-,19-,20-,21+,22-,23-,24-,25+/m0/s1
• InChI Key: YTNIUPZRMQLHNV-XSIUSZODSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₄N₂
• Molecular Weight: 372.60 g/mol
• Exact Mass: 372.350449412 g/mol
• Topological Polar Surface Area (TPSA): 6.50 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.45
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Irehdiamine I
• Sarcodinine
• Kurchessine [MI]
• 6869-45-0
• UNII-618227L15H
• CHEBI:6145
• CHEMBL344384
• 618227L15H
• (3beta,20S)-N,N,N,N-Tetramethylpregn-5-ene-3,20-diamine
• Pregn-5-ene-3,20-diamine, N3,N3,N20,N20-tetramethyl-, (3beta,20S)-
• Pregn-5-ene-3.beta.,20.alpha.-diamine, N,N,N',N'-tetramethyl-
• Pregn-5-ene-3,20-diamine, N,N,N',N'-tetramethyl-, (3.beta.,20S)-
• (3S,8S,9S,10R,13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-N,N,10,13-tetramethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-amine
• (3S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine
• Kurchessin
• C10813
• SCHEMBL2230965
• DTXSID30332028
• YTNIUPZRMQLHNV-XSIUSZODSA-N
• BDBM50421628
• 3.beta.,20.alpha.-Bis(dimethylamino)pregn-5-ene
• Q27107104
• (3.BETA.,20S)-N,N,N,N-TETRAMETHYLPREGN-5-ENE-3,20-DIAMINE
• PREGN-5-ENE-3,20-DIAMINE, N3,N3,N20,N20-TETRAMETHYL-, (3.BETA.,20S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9792	97.92%
Caco-2	+	0.6557	65.57%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.3562	35.62%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.9477	94.77%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.6235	62.35%
P-glycoprotein inhibitior	-	0.5981	59.81%
P-glycoprotein substrate	+	0.5182	51.82%
CYP3A4 substrate	+	0.7072	70.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5718	57.18%
CYP3A4 inhibition	-	0.7716	77.16%
CYP2C9 inhibition	-	0.7857	78.57%
CYP2C19 inhibition	-	0.7959	79.59%
CYP2D6 inhibition	-	0.8808	88.08%
CYP1A2 inhibition	-	0.7848	78.48%
CYP2C8 inhibition	-	0.7019	70.19%
CYP inhibitory promiscuity	+	0.5499	54.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5471	54.71%
Eye corrosion	-	0.9620	96.20%
Eye irritation	-	0.9675	96.75%
Skin irritation	-	0.6599	65.99%
Skin corrosion	-	0.6175	61.75%
Ames mutagenesis	-	0.7544	75.44%
Human Ether-a-go-go-Related Gene inhibition	-	0.4855	48.55%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.8035	80.35%
skin sensitisation	-	0.6810	68.10%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7743	77.43%
Acute Oral Toxicity (c)	III	0.5975	59.75%
Estrogen receptor binding	+	0.8886	88.86%
Androgen receptor binding	+	0.7354	73.54%
Thyroid receptor binding	-	0.5195	51.95%
Glucocorticoid receptor binding	+	0.7375	73.75%
Aromatase binding	+	0.5228	52.28%
PPAR gamma	-	0.5107	51.07%
Honey bee toxicity	-	0.7586	75.86%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	39810.72 nM	IC50	PMID: 14643329

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.93%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.61%	97.25%
CHEMBL1871	P10275	Androgen Receptor	91.92%	96.43%
CHEMBL2581	P07339	Cathepsin D	91.73%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.92%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.80%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.13%	97.14%
CHEMBL237	P41145	Kappa opioid receptor	84.93%	98.10%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.36%	90.71%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.06%	85.30%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.67%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.61%	85.31%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.31%	93.99%
CHEMBL221	P23219	Cyclooxygenase-1	83.22%	90.17%
CHEMBL1914	P06276	Butyrylcholinesterase	81.98%	95.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.76%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.61%	93.56%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	80.54%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.17%	95.56%

Plants that contains it

• Alpinia formosana
• Anisocycla grandidieri
• Asparagus setaceus
• Bambusa tulda
• Bidens parviflora
• Croton flavens
• Elsholtzia stauntonii
• Flindersia australis
• Haemanthus coccineus
• Heliotropium angiospermum
• Holarrhena pubescens
• Mentha suaveolens
• Pinus bungeana
• Piper hostmannianum
• Protea compacta
• Sarcococca saligna
• Typhonium flagelliforme

Cross-Links

• PubChem: 442979
• NPASS: NPC21773
• ChEMBL: CHEMBL344384
• LOTUS: LTS0139615
• wikiData: Q27107104