5-Deoxyleucopelargonidin

Details

• Internal ID: 67f7b469-4b23-47ee-8658-7fc581b94f88
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Leucoanthocyanidins
• IUPAC Name: (2R,3S,4S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,7-triol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(C3=C(O2)C=C(C=C3)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H]([C@H](C3=C(O2)C=C(C=C3)O)O)O)O
• InChI: InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-14(19)13(18)11-6-5-10(17)7-12(11)20-15/h1-7,13-19H/t13-,14-,15+/m0/s1
• InChI Key: NTLUSUFJOUMRLA-SOUVJXGZSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.63
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 3,4,4',7-Tetrahydroxyflavan
• 38412-82-7
• (2R,3S,4S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,7-triol
• CHEBI:80488
• DTXSID701344151
• Q27149539
• 113725-62-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9373	93.73%
Caco-2	-	0.8928	89.28%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6922	69.22%
OATP2B1 inhibitior	-	0.5863	58.63%
OATP1B1 inhibitior	+	0.7952	79.52%
OATP1B3 inhibitior	+	0.9930	99.30%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8713	87.13%
P-glycoprotein inhibitior	-	0.8927	89.27%
P-glycoprotein substrate	-	0.9127	91.27%
CYP3A4 substrate	-	0.5545	55.45%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.4488	44.88%
CYP3A4 inhibition	-	0.8362	83.62%
CYP2C9 inhibition	+	0.8918	89.18%
CYP2C19 inhibition	-	0.5999	59.99%
CYP2D6 inhibition	-	0.9008	90.08%
CYP1A2 inhibition	+	0.8639	86.39%
CYP2C8 inhibition	+	0.5163	51.63%
CYP inhibitory promiscuity	+	0.5761	57.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5357	53.57%
Eye corrosion	-	0.9871	98.71%
Eye irritation	+	0.9563	95.63%
Skin irritation	+	0.5803	58.03%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6869	68.69%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.7059	70.59%
skin sensitisation	-	0.7870	78.70%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6986	69.86%
Acute Oral Toxicity (c)	II	0.6941	69.41%
Estrogen receptor binding	-	0.6351	63.51%
Androgen receptor binding	-	0.5187	51.87%
Thyroid receptor binding	+	0.7375	73.75%
Glucocorticoid receptor binding	+	0.5934	59.34%
Aromatase binding	+	0.6570	65.70%
PPAR gamma	+	0.7072	70.72%
Honey bee toxicity	-	0.8651	86.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9072	90.72%

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	96.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.47%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.18%	97.09%
CHEMBL2535	P11166	Glucose transporter	85.30%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.14%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.49%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	83.65%	96.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.51%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.42%	95.89%
CHEMBL242	Q92731	Estrogen receptor beta	81.50%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.94%	86.33%

Plants that contains it

• Acacia cultriformis
• Guibourtia coleosperma
• Vachellia luederitzii

Cross-Links

• PubChem: 13886897
• LOTUS: LTS0255922
• wikiData: Q27149539