Rabdosiin

Details

• Internal ID: 917e7332-d006-4444-95b4-1b08e79945a9
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (2R)-2-[(1R,2S)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C2C(C3=CC(=C(C=C3C=C2C(=O)OC(CC4=CC(=C(C=C4)O)O)C(=O)O)O)O)C5=CC(=C(C=C5)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)[C@H]2[C@@H](C3=CC(=C(C=C3C=C2C(=O)O[C@H](CC4=CC(=C(C=C4)O)O)C(=O)O)O)O)C5=CC(=C(C=C5)O)O)O)O
• InChI: InChI=1S/C36H30O16/c37-21-4-1-15(7-24(21)40)9-29(33(45)46)51-35(49)20-11-18-13-27(43)28(44)14-19(18)31(17-3-6-23(39)26(42)12-17)32(20)36(50)52-30(34(47)48)10-16-2-5-22(38)25(41)8-16/h1-8,11-14,29-32,37-44H,9-10H2,(H,45,46)(H,47,48)/t29-,30-,31-,32-/m1/s1
• InChI Key: VKWZFIDWHLCPHJ-SEVDZJIVSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₀O₁₆
• Molecular Weight: 718.60 g/mol
• Exact Mass: 718.15338487 g/mol
• Topological Polar Surface Area (TPSA): 289.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• 119152-54-4
• (-)-Rabdosiin
• 2,3-Naphthalenedicarboxylic acid, 1-(3,4-dihydroxyphenyl)-1,2-dihydro-6,7-dihydroxy-, bis((1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl) ester,(1R,2S)-
• 2,3-Naphthalenedicarboxylic acid, 1-(3,4-dihydroxyphenyl)-1,2-dihydro-6,7-dihydroxy-, bis[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl] ester,(1R,2S)-
• CHEMBL355103
• HY-N6880A
• DTXSID90152325
• (2R)-2-[(1R,2S)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
• CS-0616166
• (2R)-3-(3,4-dihydroxyphenyl)-2-[(1R,2S)-1-(3,4-dihydroxyphenyl)-3-[(1R)-1-[(3,4-dihydroxyphenyl)methyl]-2-hydroxy-2-oxo-ethoxy]carbonyl-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-propanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9629	96.29%
Caco-2	-	0.9074	90.74%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8069	80.69%
OATP2B1 inhibitior	-	0.5647	56.47%
OATP1B1 inhibitior	+	0.8915	89.15%
OATP1B3 inhibitior	+	0.9279	92.79%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8419	84.19%
P-glycoprotein inhibitior	+	0.7408	74.08%
P-glycoprotein substrate	-	0.7132	71.32%
CYP3A4 substrate	+	0.5902	59.02%
CYP2C9 substrate	-	0.5984	59.84%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.8993	89.93%
CYP2C9 inhibition	+	0.6172	61.72%
CYP2C19 inhibition	-	0.8165	81.65%
CYP2D6 inhibition	-	0.8863	88.63%
CYP1A2 inhibition	-	0.5120	51.20%
CYP2C8 inhibition	+	0.7056	70.56%
CYP inhibitory promiscuity	-	0.6275	62.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8997	89.97%
Carcinogenicity (trinary)	Non-required	0.5372	53.72%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8776	87.76%
Skin irritation	-	0.7084	70.84%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8193	81.93%
Micronuclear	+	0.7618	76.18%
Hepatotoxicity	-	0.6698	66.98%
skin sensitisation	-	0.6355	63.55%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8141	81.41%
Acute Oral Toxicity (c)	III	0.4486	44.86%
Estrogen receptor binding	+	0.8034	80.34%
Androgen receptor binding	+	0.7868	78.68%
Thyroid receptor binding	+	0.5157	51.57%
Glucocorticoid receptor binding	+	0.5628	56.28%
Aromatase binding	-	0.6322	63.22%
PPAR gamma	+	0.6864	68.64%
Honey bee toxicity	-	0.6558	65.58%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.66%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.16%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.86%	95.17%
CHEMBL1951	P21397	Monoamine oxidase A	96.46%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.23%	99.15%
CHEMBL2581	P07339	Cathepsin D	93.40%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	90.81%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.40%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.59%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.55%	86.92%
CHEMBL221	P23219	Cyclooxygenase-1	85.48%	90.17%
CHEMBL3194	P02766	Transthyretin	84.75%	90.71%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.86%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.63%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.02%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.08%	94.62%

Plants that contains it

• Arnebia euchroma
• Eucalyptus coccifera
• Isodon japonicus
• Rhizomnium magnifolium
• Salvia yunnanensis

Cross-Links

• PubChem: 471121
• NPASS: NPC266084
• LOTUS: LTS0238572
• wikiData: Q83018945