Machaerogenin

Details

• Internal ID: d060c89f-7ff8-4960-b34b-5c253d164ee0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,4S,5R,10S,13R,18S,20S,21S)-10-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-22-oxahexacyclo[19.2.1.01,18.04,17.05,14.08,13]tetracos-16-en-23-one
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1O)C)CC=C4C3(CCC56C4CC(C(C5)OC6=O)(C)CO)C)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C(C1CC[C@@]3(C2CC=C4[C@]3(CC[C@]56[C@H]4C[C@@]([C@H](C5)OC6=O)(C)CO)C)C)(C)C)O
• InChI: InChI=1S/C30H46O4/c1-25(2)20-9-12-29(6)21(27(20,4)11-10-22(25)32)8-7-18-19-15-26(3,17-31)23-16-30(19,24(33)34-23)14-13-28(18,29)5/h7,19-23,31-32H,8-17H2,1-6H3/t19-,20?,21?,22-,23-,26-,27-,28+,29+,30+/m0/s1
• InChI Key: CHTCCKSXBYVSBJ-IQQHCVDNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₄
• Molecular Weight: 470.70 g/mol
• Exact Mass: 470.33960994 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.66
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• MLS000563519
• SMR000470880
• CHEMBL1710708
• BDBM80033
• cid_23641104
• HMS2269C16

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	-	0.5706	57.06%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7969	79.69%
OATP2B1 inhibitior	-	0.7130	71.30%
OATP1B1 inhibitior	+	0.8716	87.16%
OATP1B3 inhibitior	+	0.9395	93.95%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5141	51.41%
BSEP inhibitior	+	0.8691	86.91%
P-glycoprotein inhibitior	-	0.7422	74.22%
P-glycoprotein substrate	-	0.8356	83.56%
CYP3A4 substrate	+	0.6880	68.80%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8004	80.04%
CYP3A4 inhibition	-	0.6485	64.85%
CYP2C9 inhibition	-	0.7694	76.94%
CYP2C19 inhibition	-	0.8879	88.79%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	-	0.8168	81.68%
CYP2C8 inhibition	-	0.6263	62.63%
CYP inhibitory promiscuity	-	0.8466	84.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4931	49.31%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9370	93.70%
Skin irritation	+	0.5497	54.97%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5250	52.50%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8665	86.65%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6259	62.59%
Acute Oral Toxicity (c)	III	0.6100	61.00%
Estrogen receptor binding	+	0.8012	80.12%
Androgen receptor binding	+	0.7058	70.58%
Thyroid receptor binding	+	0.5860	58.60%
Glucocorticoid receptor binding	+	0.8588	85.88%
Aromatase binding	+	0.7249	72.49%
PPAR gamma	+	0.5738	57.38%
Honey bee toxicity	-	0.8353	83.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	92.71%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.42%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.65%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.19%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.68%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.32%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.39%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.00%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.44%	98.95%

Plants that contains it

• Stenocereus stellatus

Cross-Links

• PubChem: 23641104
• LOTUS: LTS0055532
• wikiData: Q104402810