Rhodexin A

Details

• Internal ID: 3e7d9b20-0597-4cc5-976c-9addeaf43c7c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-11,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3C(CC5(C4(CCC5C6=CC(=O)OC6)O)C)O)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3[C@@H](C[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)O)O
• InChI: InChI=1S/C29H44O9/c1-14-23(32)24(33)25(34)26(37-14)38-17-6-8-27(2)16(11-17)4-5-19-22(27)20(30)12-28(3)18(7-9-29(19,28)35)15-10-21(31)36-13-15/h10,14,16-20,22-26,30,32-35H,4-9,11-13H2,1-3H3/t14-,16+,17-,18+,19+,20+,22+,23-,24+,25+,26-,27-,28+,29-/m0/s1
• InChI Key: HFMLTKBZNAPPNY-CEKKCSHUSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₉
• Molecular Weight: 536.70 g/mol
• Exact Mass: 536.29853298 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 545-49-3
• Sarmentogenin 3-O-alpha-L-rhamnoside
• Sarmentogenin, 3-(6-deoxy-alpha-L-mannopyranoside)
• 4-((3S,5R,8R,9S,10S,11R,13R,14S,17R)-11,14-dihydroxy-10,13-dimethyl-3-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• Sarmentogenin-L-rhamnosid
• Sarmentogenin-L-rhamnosid [German]
• 3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-11,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• Sarmentogenin, 3-(6-deoxy-.alpha.-L-mannopyranoside)
• DTXSID301318334
• LMST01120010
• AKOS040753755
• 5-beta-Card-20(22)-enolide, 3-beta-((6-deoxy-alpha-L-mannopyranosyl)oxy)-11-alpha,14-dihydroxy-
• C08877
• Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy]-11,14-dihydroxy-, (3beta,5beta,11alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9219	92.19%
Caco-2	-	0.8434	84.34%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8297	82.97%
OATP2B1 inhibitior	-	0.6164	61.64%
OATP1B1 inhibitior	+	0.9486	94.86%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6275	62.75%
P-glycoprotein inhibitior	-	0.5290	52.90%
P-glycoprotein substrate	+	0.6292	62.92%
CYP3A4 substrate	+	0.7116	71.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.9279	92.79%
CYP2C9 inhibition	-	0.9196	91.96%
CYP2C19 inhibition	-	0.9385	93.85%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.9261	92.61%
CYP2C8 inhibition	-	0.7415	74.15%
CYP inhibitory promiscuity	-	0.9279	92.79%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5632	56.32%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9401	94.01%
Skin irritation	+	0.5359	53.59%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8097	80.97%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.8018	80.18%
skin sensitisation	-	0.9042	90.42%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7351	73.51%
Acute Oral Toxicity (c)	I	0.7867	78.67%
Estrogen receptor binding	+	0.7877	78.77%
Androgen receptor binding	+	0.8216	82.16%
Thyroid receptor binding	-	0.6128	61.28%
Glucocorticoid receptor binding	+	0.6480	64.80%
Aromatase binding	+	0.6937	69.37%
PPAR gamma	+	0.5293	52.93%
Honey bee toxicity	-	0.6838	68.38%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9750	97.50%

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	98.59%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.10%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.73%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.19%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.06%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.59%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.37%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.39%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.30%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.75%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.28%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.79%	82.69%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.64%	91.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.58%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.28%	89.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.41%	81.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.67%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.02%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.60%	95.89%

Plants that contains it

• Convallaria keiskei
• Dipcadi glaucum
• Ornithogalum arcuatum
• Ornithogalum nutans
• Rohdea japonica
• Speirantha gardenii

Cross-Links

• PubChem: 441868
• LOTUS: LTS0258449
• wikiData: Q76100211