arvenin III

Details

• Internal ID: 12c7fd97-4e4d-4d58-90aa-13302d129ff1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• SMILES (Canonical): CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2CC(C1=O)OC5C(C(C(C(O5)CO)O)O)O)C)C)C(C)(C(=O)C=CC(C)(C)O)O)O)C)C
• SMILES (Isomeric): C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)[C@](C)(C(=O)/C=C/C(C)(C)O)O)O
• InChI: InChI=1S/C36H54O12/c1-31(2,45)12-11-23(39)36(8,46)28-19(38)14-33(5)22-10-9-17-18(35(22,7)24(40)15-34(28,33)6)13-20(29(44)32(17,3)4)47-30-27(43)26(42)25(41)21(16-37)48-30/h9,11-12,18-22,25-28,30,37-38,41-43,45-46H,10,13-16H2,1-8H3/b12-11+/t18-,19-,20+,21-,22+,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1
• InChI Key: GOWXUGYRPHOTEQ-QYNXQQORSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₂
• Molecular Weight: 678.80 g/mol
• Exact Mass: 678.36152715 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 65597-45-7
• 19-Norlanosta-5,23-diene-3,11,22-trione, 2-(beta-D-glucopyranosyloxy)-16,20,25-trihydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)-
• CHEMBL538201
• MEGxp0_000823
• DTXSID201107003
• AKOS040734579
• NCGC00385061-01
• (2beta,9beta,10alpha,16alpha,23E)-2-(beta-D-Glucopyranosyloxy)-16,20,25-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione
• NCGC00385061-01_C36H54O12_Estr-5-ene-3,11-dione, 17-[(1R,3E)-1,5-dihydroxy-1,5-dimethyl-2-oxo-3-hexen-1-yl]-2-(beta-D-glucopyranosyloxy)-16-hydroxy-4,4,9,14-tetramethyl-, (2beta,9beta,10alpha,16alpha,17beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9049	90.49%
Caco-2	-	0.8559	85.59%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8255	82.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8214	82.14%
OATP1B3 inhibitior	+	0.8709	87.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6457	64.57%
P-glycoprotein inhibitior	+	0.7341	73.41%
P-glycoprotein substrate	-	0.5635	56.35%
CYP3A4 substrate	+	0.7181	71.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.7781	77.81%
CYP2C9 inhibition	-	0.8433	84.33%
CYP2C19 inhibition	-	0.9144	91.44%
CYP2D6 inhibition	-	0.9454	94.54%
CYP1A2 inhibition	-	0.8551	85.51%
CYP2C8 inhibition	+	0.6445	64.45%
CYP inhibitory promiscuity	-	0.9191	91.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6753	67.53%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9164	91.64%
Skin irritation	-	0.5459	54.59%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6918	69.18%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.6092	60.92%
skin sensitisation	-	0.8945	89.45%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4887	48.87%
Acute Oral Toxicity (c)	III	0.6142	61.42%
Estrogen receptor binding	+	0.7217	72.17%
Androgen receptor binding	+	0.7549	75.49%
Thyroid receptor binding	-	0.4949	49.49%
Glucocorticoid receptor binding	+	0.7662	76.62%
Aromatase binding	+	0.7194	71.94%
PPAR gamma	+	0.6776	67.76%
Honey bee toxicity	-	0.6695	66.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9826	98.26%

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	99.04%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.51%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.08%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.00%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.01%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.80%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.25%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.09%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.18%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.64%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.61%	86.33%
CHEMBL4208	P20618	Proteasome component C5	86.12%	90.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	85.46%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.69%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.87%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.72%	91.07%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.69%	96.61%
CHEMBL5255	O00206	Toll-like receptor 4	81.89%	92.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.81%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.42%	86.92%

Plants that contains it

• Begonia heracleifolia
• Bryonia cretica
• Cucumis melo
• Helicteres angustifolia
• Luffa operculata
• Lysimachia arvensis

Cross-Links

• PubChem: 21579640
• NPASS: NPC58571
• LOTUS: LTS0114643
• wikiData: Q104393318