Gynocardin

Details

• Internal ID: bcd9624e-fd23-46d0-8667-24831f5067a1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: 4,5-dihydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
• SMILES (Canonical): C1=CC(C(C1O)O)(C#N)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): C1=CC(C(C1O)O)(C#N)OC2C(C(C(C(O2)CO)O)O)O
• InChI: InChI=1S/C12H17NO8/c13-4-12(2-1-5(15)10(12)19)21-11-9(18)8(17)7(16)6(3-14)20-11/h1-2,5-11,14-19H,3H2
• InChI Key: HASDUOHKNMHNJA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₇NO₈
• Molecular Weight: 303.26 g/mol
• Exact Mass: 303.09541650 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.64
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• KCS-5CA
• 14332-17-3
• NSC370274
• NSC-140698
• NSC-370274
• 1-(hexopyranosyloxy)-4,5-dihydroxycyclopent-2-ene-1-carbonitrile
• DTXSID30931818
• NSC140698
• 1-(b-D-Glucopyranosyloxy)-4,5-dihydroxy-2-cyclopentene-1-carbonitrile, 8CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8985	89.85%
Caco-2	-	0.9284	92.84%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6834	68.34%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9131	91.31%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9688	96.88%
P-glycoprotein inhibitior	-	0.9190	91.90%
P-glycoprotein substrate	-	0.9708	97.08%
CYP3A4 substrate	-	0.5117	51.17%
CYP2C9 substrate	-	0.8050	80.50%
CYP2D6 substrate	-	0.8334	83.34%
CYP3A4 inhibition	-	0.8820	88.20%
CYP2C9 inhibition	-	0.8732	87.32%
CYP2C19 inhibition	-	0.8454	84.54%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	-	0.8614	86.14%
CYP2C8 inhibition	-	0.7598	75.98%
CYP inhibitory promiscuity	-	0.7893	78.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6662	66.62%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9909	99.09%
Skin irritation	-	0.8256	82.56%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3755	37.55%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.7800	78.00%
skin sensitisation	-	0.8521	85.21%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7327	73.27%
Acute Oral Toxicity (c)	III	0.5454	54.54%
Estrogen receptor binding	-	0.7937	79.37%
Androgen receptor binding	-	0.6537	65.37%
Thyroid receptor binding	+	0.5419	54.19%
Glucocorticoid receptor binding	-	0.4763	47.63%
Aromatase binding	-	0.5172	51.72%
PPAR gamma	+	0.5525	55.25%
Honey bee toxicity	-	0.7446	74.46%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7250	72.50%
Fish aquatic toxicity	-	0.9013	90.13%

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	97.20%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.06%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.54%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.14%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.88%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.44%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.09%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.26%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.40%	89.00%

Plants that contains it

• Ceratiosicyos laevis
• Kiggelaria africana
• Passiflora incarnata
• Rawsonia lucida
• Ryparosa kurrangii

Cross-Links

• PubChem: 122812
• LOTUS: LTS0227273
• wikiData: Q105025023