Leucocianidol

Details

• Internal ID: e24a3387-efa4-49c8-bc14-4c3fd970ca98
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,5,7-tetrol
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(C3=C(C=C(C=C3O2)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1[C@@H]2[C@H]([C@H](C3=C(C=C(C=C3O2)O)O)O)O)O)O
• InChI: InChI=1S/C15H14O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,13-21H/t13-,14-,15+/m0/s1
• InChI Key: SBZWTSHAFILOTE-SOUVJXGZSA-N
• Popularity: 30 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.27 g/mol
• Exact Mass: 306.07395278 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 1

Synonyms

• Leucocyanidol
• Leukocyanidine
• Leucoanthocyanidol
• Catechin-4beta-ol
• Leucocyanidin
• (2R,3S,4S)-leucocyanidin
• 3,4-Cyanidiol
• 2,3-trans-3,4-cis-Leucocyanidin
• 93527-39-0
• Procyanidol
• Resivit
• CHEBI:11412
• (2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,5,7-tetrol
• Leucocianidol (INN)
• Leucocianidol [INN]
• 3,3',4,4',5,7-Flavanhexol
• Leucocyanidin [MI]
• 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
• Leucocianidol [MART.]
• Leucocianidol [WHO-DD]
• 480-17-1
• Flavan (TN)
• CHEMBL124022
• SCHEMBL1649595
• DTXSID70331530
• 2H-1-Benzopyran-3,4,5,7-tetrol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)-
• 2,3-trans,3,4-cis-Leucocyanidin
• LMPK12020203
• C05906
• D08112
• F82290
• Q8085718
• 2r-(3,4-dihydroxyphenyl)chromane-3t,4t,5,7-tetrol
• (2R)-2alpha-(3,4-Dihydroxyphenyl)chroman-3beta,4beta,5,7-tetrol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8661	86.61%
Caco-2	-	0.9607	96.07%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4950	49.50%
OATP2B1 inhibitior	-	0.6930	69.30%
OATP1B1 inhibitior	+	0.9550	95.50%
OATP1B3 inhibitior	+	0.9699	96.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9311	93.11%
P-glycoprotein inhibitior	-	0.9281	92.81%
P-glycoprotein substrate	-	0.9742	97.42%
CYP3A4 substrate	-	0.5624	56.24%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	+	0.3999	39.99%
CYP3A4 inhibition	-	0.5171	51.71%
CYP2C9 inhibition	-	0.5147	51.47%
CYP2C19 inhibition	-	0.8415	84.15%
CYP2D6 inhibition	-	0.9060	90.60%
CYP1A2 inhibition	+	0.8329	83.29%
CYP2C8 inhibition	+	0.5136	51.36%
CYP inhibitory promiscuity	+	0.6713	67.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6194	61.94%
Eye corrosion	-	0.9880	98.80%
Eye irritation	+	0.9404	94.04%
Skin irritation	+	0.5520	55.20%
Skin corrosion	-	0.9055	90.55%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5266	52.66%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.7386	73.86%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6913	69.13%
Acute Oral Toxicity (c)	II	0.6350	63.50%
Estrogen receptor binding	-	0.7011	70.11%
Androgen receptor binding	+	0.5484	54.84%
Thyroid receptor binding	+	0.7481	74.81%
Glucocorticoid receptor binding	+	0.6105	61.05%
Aromatase binding	+	0.6687	66.87%
PPAR gamma	+	0.6826	68.26%
Honey bee toxicity	-	0.8294	82.94%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.8833	88.33%

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	98.39%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.02%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	96.44%	83.82%
CHEMBL3194	P02766	Transthyretin	91.53%	90.71%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.22%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.85%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.66%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.45%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.31%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	82.77%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.74%	97.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.57%	96.12%

Plants that contains it

• Actiniopteris radiata
• Aglaia laxiflora
• Arabidopsis thaliana
• Artemisia carvifolia
• Callicarpa maingayi
• Cassia javanica
• Cephalaria uralensis
• Crotalaria aegyptiaca
• Dicoma capensis
• Digitalis isabelliana
• Ericameria parryi
• Euphorbia turczaninowii
• Geranium sylvaticum
• Gossypium hirsutum
• Haplophyllum ferganicum
• Musa × paradisiaca
• Scopolia carniolica
• Sonchus ortunoi
• Styrax ferrugineus
• Terminalia arjuna
• Vincetoxicum hirundinaria

Cross-Links

• PubChem: 440833
• NPASS: NPC194454
• LOTUS: LTS0174045
• wikiData: Q8085718