Cleomiscosin C

Details

• Internal ID: 7d815935-ac89-4ac5-ac49-cec6305ad38c
• Taxonomy: Lignans, neolignans and related compounds > Coumarinolignans
• IUPAC Name: (2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C(OC3=C4C(=CC(=C3O2)OC)C=CC(=O)O4)CO
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H](OC3=C4C(=CC(=C3O2)OC)C=CC(=O)O4)CO
• InChI: InChI=1S/C21H20O9/c1-25-12-7-11(8-13(26-2)17(12)24)18-15(9-22)28-21-19-10(4-5-16(23)29-19)6-14(27-3)20(21)30-18/h4-8,15,18,22,24H,9H2,1-3H3/t15-,18-/m1/s1
• InChI Key: GZXPCBAETDEQAX-CRAIPNDOSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₉
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.11073221 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 84575-10-0
• Aquillochin
• (2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• CleomiscosinC
• CHEMBL465491
• SCHEMBL4545353
• AKOS032948612

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9099	90.99%
Caco-2	-	0.5479	54.79%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7924	79.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8062	80.62%
OATP1B3 inhibitior	-	0.4172	41.72%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8351	83.51%
P-glycoprotein inhibitior	+	0.8133	81.33%
P-glycoprotein substrate	-	0.8029	80.29%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8212	82.12%
CYP2D6 substrate	-	0.8135	81.35%
CYP3A4 inhibition	-	0.9029	90.29%
CYP2C9 inhibition	-	0.7504	75.04%
CYP2C19 inhibition	-	0.8518	85.18%
CYP2D6 inhibition	-	0.9343	93.43%
CYP1A2 inhibition	-	0.9270	92.70%
CYP2C8 inhibition	-	0.5729	57.29%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6663	66.63%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8221	82.21%
Skin irritation	-	0.8543	85.43%
Skin corrosion	-	0.9774	97.74%
Ames mutagenesis	-	0.6914	69.14%
Human Ether-a-go-go-Related Gene inhibition	-	0.7257	72.57%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9235	92.35%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7562	75.62%
Acute Oral Toxicity (c)	III	0.6358	63.58%
Estrogen receptor binding	+	0.8963	89.63%
Androgen receptor binding	+	0.7369	73.69%
Thyroid receptor binding	+	0.5473	54.73%
Glucocorticoid receptor binding	+	0.8567	85.67%
Aromatase binding	-	0.5178	51.78%
PPAR gamma	+	0.7000	70.00%
Honey bee toxicity	-	0.8384	83.84%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7363	73.63%

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	98.78%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.09%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.26%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.13%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.47%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.78%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.83%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.36%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.86%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.47%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.20%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.69%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.44%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.42%	97.09%

Plants that contains it

• Acer maximowiczianum
• Aesculus turbinata
• Aloe microstigma subsp. microstigma
• Androsace septentrionalis
• Aquilaria malaccensis
• Artemisia minor
• Astragalus thracicus
• Bulbophyllum crabro
• Calocephalus knappii
• Cleome viscosa
• Coptis japonica
• Dioscorea gracillima
• Dodonaea viscosa
• Echium rubrum
• Entada africana
• Entada polystachya
• Epimedium wushanense
• Euphorbia bupleuroides
• Euphorbia fortissima
• Fumaria indica
• Hibiscus syriacus
• Hibiscus taiwanensis
• Iberis sempervirens
• Neocussonia longipedicellata
• Parthenocissus tricuspidata
• Plectranthus verticillatus
• Pontederia crassipes
• Pseuduvaria trimera
• Pteris spinescens
• Rhododendron collettianum
• Roemeria carica
• Schumanniophyton magnificum
• Theobroma speciosum
• Vitex limonifolia
• Xanthium strumarium

Cross-Links

• PubChem: 11464176
• NPASS: NPC205727
• LOTUS: LTS0200101
• wikiData: Q104400804