Specioside

Details

• Internal ID: 484f8d0f-e726-424e-a7cd-2ebb36f1f325
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=COC(C2C1C(C3C2(O3)CO)OC(=O)C=CC4=CC=C(C=C4)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1=CO[C@H]([C@H]2[C@@H]1[C@@H]([C@H]3[C@@]2(O3)CO)OC(=O)/C=C/C4=CC=C(C=C4)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C24H28O12/c25-9-14-17(29)18(30)19(31)23(33-14)35-22-16-13(7-8-32-22)20(21-24(16,10-26)36-21)34-15(28)6-3-11-1-4-12(27)5-2-11/h1-8,13-14,16-23,25-27,29-31H,9-10H2/b6-3+/t13-,14-,16-,17-,18+,19-,20+,21+,22+,23+,24-/m1/s1
• InChI Key: SKNVKBJSSSJNCI-UIBFFPKISA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₂
• Molecular Weight: 508.50 g/mol
• Exact Mass: 508.15807632 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.62
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 72514-90-0
• CHEMBL2332355
• [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• [(1aS)-1a,1balpha,2,5aalpha,6,6abeta-Hexahydro-1abeta-hydroxymethyl-6alpha-[[(E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]oxireno[4,5]cyclopenta[1,2-c]pyran-2alpha-yl]beta-D-glucopyranoside
• 6-O-(p-Coumaroyl)catalpol
• (-)-Specioside;6-O-(E)-p-Coumaroylcatalpol
• CHEBI:181647
• DTXSID801318410
• HY-N1206
• BDBM50429455
• AKOS040762362
• FS-8992
• NCGC00347822-02
• beta-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-1a-(hydroxymethyl)-6-(((2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl
• CS-0016593
• NCGC00347822-02_C24H28O12_2-Propenoic acid, 3-(4-hydroxyphenyl)-, (1aS,1bS,2S,5aR,6S,6aS)-2-(beta-D-glucopyranosyloxy)-1a,1b,2,5a,6,6a-hexahydro-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-6-yl ester, (2E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5631	56.31%
Caco-2	-	0.9196	91.96%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6002	60.02%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.8143	81.43%
OATP1B3 inhibitior	+	0.9565	95.65%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5639	56.39%
P-glycoprotein inhibitior	-	0.6542	65.42%
P-glycoprotein substrate	-	0.6706	67.06%
CYP3A4 substrate	+	0.6680	66.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8675	86.75%
CYP3A4 inhibition	-	0.9111	91.11%
CYP2C9 inhibition	-	0.8998	89.98%
CYP2C19 inhibition	-	0.7733	77.33%
CYP2D6 inhibition	-	0.8787	87.87%
CYP1A2 inhibition	-	0.8773	87.73%
CYP2C8 inhibition	+	0.6776	67.76%
CYP inhibitory promiscuity	-	0.7594	75.94%
UGT catelyzed	-	0.7638	76.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5420	54.20%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9452	94.52%
Skin irritation	-	0.7661	76.61%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4161	41.61%
Micronuclear	-	0.5267	52.67%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.7853	78.53%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6281	62.81%
Acute Oral Toxicity (c)	III	0.4388	43.88%
Estrogen receptor binding	+	0.7023	70.23%
Androgen receptor binding	+	0.5297	52.97%
Thyroid receptor binding	+	0.5715	57.15%
Glucocorticoid receptor binding	-	0.4858	48.58%
Aromatase binding	+	0.6046	60.46%
PPAR gamma	+	0.7604	76.04%
Honey bee toxicity	-	0.7160	71.60%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7544	75.44%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	26 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.21%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.61%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.28%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.70%	89.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.58%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	90.96%	94.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.45%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.78%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.73%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.88%	94.45%
CHEMBL3194	P02766	Transthyretin	86.79%	90.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.75%	94.62%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	86.68%	94.97%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.36%	94.08%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.22%	83.57%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.99%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	83.73%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.10%	86.92%
CHEMBL4208	P20618	Proteasome component C5	81.11%	90.00%

Plants that contains it

• Ailanthus integrifolia
• Catalpa bignonioides
• Catalpa ovata
• Catalpa speciosa
• Kigelia africana subsp. africana
• Penstemon ambiguus
• Stereospermum acuminatissimum
• Tabebuia rosea
• Verbascum phlomoides

Cross-Links

• PubChem: 11948661
• LOTUS: LTS0205399
• wikiData: Q104397139