Ascosteroside

Details

• Internal ID: 3aca5425-6768-44c5-aa38-aa78b3555a2f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (3S,5R,10S,13R,14S,15R,17R)-3-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-15-hydroxy-10,13-dimethyl-4-methylidene-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid
• SMILES (Canonical): CC(C)C(=C)CCC(C)C1CC(C2(C1(CCC3=C2CCC4C3(CCC(C4=C)OC5C(C(C(C(O5)CO)OC)O)O)C)C)C(=O)O)O
• SMILES (Isomeric): C[C@H](CCC(=C)C(C)C)[C@H]1C[C@H]([C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4=C)O[C@H]5[C@H]([C@@H]([C@H]([C@@H](O5)CO)OC)O)O)C)C)C(=O)O)O
• InChI: InChI=1S/C37H58O9/c1-19(2)20(3)9-10-21(4)26-17-29(39)37(34(42)43)25-12-11-23-22(5)27(14-15-35(23,6)24(25)13-16-36(26,37)7)45-33-31(41)30(40)32(44-8)28(18-38)46-33/h19,21,23,26-33,38-41H,3,5,9-18H2,1-2,4,6-8H3,(H,42,43)/t21-,23+,26-,27+,28+,29-,30+,31+,32+,33-,35+,36-,37-/m1/s1
• InChI Key: VWTJLWBUAZAHKW-VFKIOILVSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₈O₉
• Molecular Weight: 646.80 g/mol
• Exact Mass: 646.40808342 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.77
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

• (3S,5R,10S,13R,14S,15R,17R)-3-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-15-hydroxy-10,13-dimethyl-4-methylidene-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid
• (3S,5R,10S,13R,14S,15R,17R)-3-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxy-tetrahydropyran-2-yl]oxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-15-hydroxy-10,13-dimethyl-4-methylene-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8532	85.32%
Caco-2	-	0.8469	84.69%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7681	76.81%
OATP2B1 inhibitior	-	0.7212	72.12%
OATP1B1 inhibitior	+	0.8196	81.96%
OATP1B3 inhibitior	+	0.8404	84.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7542	75.42%
BSEP inhibitior	+	0.6119	61.19%
P-glycoprotein inhibitior	+	0.7122	71.22%
P-glycoprotein substrate	+	0.5530	55.30%
CYP3A4 substrate	+	0.7136	71.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.7791	77.91%
CYP2C9 inhibition	-	0.8206	82.06%
CYP2C19 inhibition	-	0.8506	85.06%
CYP2D6 inhibition	-	0.9240	92.40%
CYP1A2 inhibition	-	0.7766	77.66%
CYP2C8 inhibition	+	0.6410	64.10%
CYP inhibitory promiscuity	-	0.9166	91.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6762	67.62%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9185	91.85%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6907	69.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.3759	37.59%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7001	70.01%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7282	72.82%
Acute Oral Toxicity (c)	III	0.5990	59.90%
Estrogen receptor binding	+	0.7861	78.61%
Androgen receptor binding	+	0.7386	73.86%
Thyroid receptor binding	-	0.5613	56.13%
Glucocorticoid receptor binding	+	0.6039	60.39%
Aromatase binding	+	0.6779	67.79%
PPAR gamma	+	0.6482	64.82%
Honey bee toxicity	-	0.6629	66.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7355	73.55%
Fish aquatic toxicity	+	0.9600	96.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.88%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.45%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.07%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.84%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	94.15%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.86%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.64%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.58%	94.45%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	88.54%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.49%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.87%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.82%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.42%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.78%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.51%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.50%	89.05%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.88%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.60%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.39%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.66%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.57%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	82.23%	91.19%
CHEMBL5028	O14672	ADAM10	81.47%	97.50%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	81.08%	92.50%
CHEMBL1907	P15144	Aminopeptidase N	80.92%	93.31%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.64%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.26%	93.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 483859
• LOTUS: LTS0185399
• wikiData: Q105298275