Gardoside

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	3011f50f-338b-4b1c-a40e-3668821e0915
Taxonomy	Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name	(1S,4aS,6S,7aS)-6-hydroxy-7-methylidene-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical)	C=C1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
SMILES (Isomeric)	C=C1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChI	InChI=1S/C16H22O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4,6,8-13,15-21H,1-3H2,(H,22,23)/t6-,8+,9-,10-,11-,12+,13-,15+,16+/m1/s1
InChI Key	JSKCJJNYSGWZDU-RQJSCMEKSA-N
Popularity	1 reference in papers

Physical and Chemical Properties

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Molecular Formula	C₁₆H₂₂O₁₀
Molecular Weight	374.34 g/mol
Exact Mass	374.12129689 g/mol
Topological Polar Surface Area (TPSA)	166.00 Å²
XlogP	-2.50
Atomic LogP (AlogP)	-2.32
H-Bond Acceptor	9
H-Bond Donor	6
Rotatable Bonds	4

Synonyms

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54835-76-6

(1S,4aS,6S,7aS)-6-hydroxy-7-methylidene-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

CHEMBL3622810

CHEBI:80827

HY-N8046

CS-0139030

C16963

E87199

Q27149870

(1S,4AS,6S,7aS)-1-(|A-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylenecyclopenta[c]pyran-4-carboxylic acid

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5803	58.03%
Caco-2	-	0.8995	89.95%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5877	58.77%
OATP2B1 inhibitior	-	0.7177	71.77%
OATP1B1 inhibitior	+	0.7258	72.58%
OATP1B3 inhibitior	+	0.9516	95.16%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9806	98.06%
P-glycoprotein inhibitior	-	0.8888	88.88%
P-glycoprotein substrate	-	0.9059	90.59%
CYP3A4 substrate	+	0.5330	53.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8723	87.23%
CYP3A4 inhibition	-	0.8439	84.39%
CYP2C9 inhibition	-	0.9240	92.40%
CYP2C19 inhibition	-	0.8599	85.99%
CYP2D6 inhibition	-	0.8838	88.38%
CYP1A2 inhibition	-	0.8890	88.90%
CYP2C8 inhibition	-	0.7345	73.45%
CYP inhibitory promiscuity	-	0.8568	85.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7487	74.87%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.8846	88.46%
Skin irritation	-	0.7650	76.50%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6078	60.78%
Micronuclear	-	0.6841	68.41%
Hepatotoxicity	-	0.8214	82.14%
skin sensitisation	-	0.8465	84.65%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6278	62.78%
Acute Oral Toxicity (c)	III	0.4029	40.29%
Estrogen receptor binding	+	0.5579	55.79%
Androgen receptor binding	+	0.5400	54.00%
Thyroid receptor binding	+	0.6152	61.52%
Glucocorticoid receptor binding	-	0.5787	57.87%
Aromatase binding	+	0.6959	69.59%
PPAR gamma	+	0.5318	53.18%
Honey bee toxicity	-	0.7940	79.40%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.6594	65.94%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	94.88%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.90%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.17%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.91%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.48%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.92%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.66%	95.71%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Physostegia virginiana

Plantago alpina

Plantago ovata

Platycodon grandiflorus