Saccatoside

Details

• Internal ID: bb0506be-dfc7-4bbb-ae3d-38f024d1b3a8
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[[(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]oxy]-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C=CC6=CC=C(C=C6)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC(=O)/C=C/C6=CC=C(C=C6)O)O)O
• InChI: InChI=1S/C30H38O16/c1-12-19(35)22(38)25(43-17(34)7-4-13-2-5-14(33)6-3-13)29(41-12)44-24-15-8-9-40-27(18(15)30(11-32)26(24)46-30)45-28-23(39)21(37)20(36)16(10-31)42-28/h2-9,12,15-16,18-29,31-33,35-39H,10-11H2,1H3/b7-4+/t12-,15+,16+,18+,19-,20+,21-,22+,23+,24-,25+,26-,27-,28-,29-,30+/m0/s1
• InChI Key: XIPQZLUSSJDAIC-UYESFEPRSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₆
• Molecular Weight: 654.60 g/mol
• Exact Mass: 654.21598512 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.77
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• 85819-35-8
• MEGxp0_000464
• ACon1_001532
• DTXSID401345786
• AKOS040734225
• NCGC00180408-01
• NCGC00180408-03
• BRD-K51601450-001-01-1
• Catalpol 6-O-[2-O-(4-hydroxycinnamoyl)-L-rhamnopyranoside]
• [(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[[(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]oxy]-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• NCGC00180408-03_C30H38O16_(1aS,1bS,2S,5aR,6S,6aS)-6-({6-Deoxy-2-O-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-alpha-L-mannopyranosyl}oxy)-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-2-yl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5971	59.71%
Caco-2	-	0.8913	89.13%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6535	65.35%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.8040	80.40%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5743	57.43%
P-glycoprotein inhibitior	-	0.4943	49.43%
P-glycoprotein substrate	+	0.5188	51.88%
CYP3A4 substrate	+	0.6958	69.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	-	0.9353	93.53%
CYP2C9 inhibition	-	0.8943	89.43%
CYP2C19 inhibition	-	0.8021	80.21%
CYP2D6 inhibition	-	0.9053	90.53%
CYP1A2 inhibition	-	0.8736	87.36%
CYP2C8 inhibition	+	0.7036	70.36%
CYP inhibitory promiscuity	-	0.7103	71.03%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5310	53.10%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9213	92.13%
Skin irritation	-	0.7718	77.18%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3733	37.33%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.7944	79.44%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7803	78.03%
Acute Oral Toxicity (c)	III	0.4935	49.35%
Estrogen receptor binding	+	0.7312	73.12%
Androgen receptor binding	+	0.5323	53.23%
Thyroid receptor binding	+	0.5317	53.17%
Glucocorticoid receptor binding	+	0.6067	60.67%
Aromatase binding	-	0.4859	48.59%
PPAR gamma	+	0.6717	67.17%
Honey bee toxicity	-	0.6939	69.39%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.7612	76.12%

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	99.18%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.94%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.60%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.43%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.80%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	92.16%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.96%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.22%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	89.10%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.78%	89.67%
CHEMBL2581	P07339	Cathepsin D	87.26%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.58%	99.17%
CHEMBL4208	P20618	Proteasome component C5	85.38%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.68%	97.09%
CHEMBL3194	P02766	Transthyretin	82.30%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.20%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.73%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	81.39%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.39%	95.89%

Plants that contains it

• Dimorphotheca fruticosa
• Glinus oppositifolius
• Gmelina philippensis
• Hypericum reflexum
• Markhamia stipulata
• Nicotiana alata
• Premna corymbosa
• Premna microphylla
• Senecio sandersonii
• Sideritis soluta
• Sideritis trojana
• Sidneya tenuifolia
• Verbascum macrurum
• Verbascum phlomoides
• Verbascum pyroliforme subsp. dudleyanum
• Verbascum saccatum
• Verbascum salviifolium
• Verbascum thapsus
• Vinca minor

Cross-Links

• PubChem: 15736668
• NPASS: NPC53556
• LOTUS: LTS0178252
• wikiData: Q104396407