Hemiphloin

Details

• Internal ID: 31061d73-601e-4fd7-824c-0aec42560524
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C1=O)C(=C(C(=C2)O)C3C(C(C(C(O3)CO)O)O)O)O)C4=CC=C(C=C4)O
• SMILES (Isomeric): C1[C@H](OC2=C(C1=O)C(=C(C(=C2)O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C4=CC=C(C=C4)O
• InChI: InChI=1S/C21H22O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-4,6,12,14,17,19-23,25-29H,5,7H2/t12-,14+,17+,19-,20+,21-/m0/s1
• InChI Key: QKPKGDDHOGIEOO-JVVVWQBKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.40 g/mol
• Exact Mass: 434.12129689 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.02
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• Hemiphloin
• 3682-03-9
• (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydrochromen-4-one
• 71963-94-5
• Compound TBBP06469
• MEGxp0_001171
• SCHEMBL7170759
• ACon1_001147
• DTXSID50958027
• CHEBI:189521
• AKOS040740421
• NCGC00169631-01
• Naringenin-6-C-glucoside, >=95% (LC/MS-ELSD)
• BRD-K06034297-001-01-8
• (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydrochromen-4-one
• 1,5-Anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]hexitol
• 4H-1-Benzopyran-4-one, 6-beta-D-glucopyranosyl-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-
• NCGC00169631-03!(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydrochromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6665	66.65%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5728	57.28%
OATP2B1 inhibitior	-	0.5656	56.56%
OATP1B1 inhibitior	+	0.8299	82.99%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7089	70.89%
P-glycoprotein inhibitior	-	0.7006	70.06%
P-glycoprotein substrate	-	0.8587	85.87%
CYP3A4 substrate	+	0.5644	56.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7947	79.47%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.4448	44.48%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7252	72.52%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8400	84.00%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5701	57.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.4914	49.14%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6122	61.22%
Acute Oral Toxicity (c)	IV	0.3746	37.46%
Estrogen receptor binding	+	0.6955	69.55%
Androgen receptor binding	+	0.6154	61.54%
Thyroid receptor binding	+	0.5479	54.79%
Glucocorticoid receptor binding	+	0.6032	60.32%
Aromatase binding	+	0.6152	61.52%
PPAR gamma	+	0.7699	76.99%
Honey bee toxicity	-	0.8142	81.42%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.6921	69.21%

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	99.51%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.97%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.13%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.20%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.98%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.07%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.63%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.52%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.83%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	86.71%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	84.21%	94.73%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.11%	85.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.89%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.10%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.67%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.24%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.50%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.77%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.08%	99.17%

Plants that contains it

• Acacia retinodes
• Ageratina areolaris
• Amsinckia tessellata
• Aspalathus linearis
• Aucuba chinensis
• Blechnum minus
• Brickellia vernicosa
• Cedronella canariensis
• Citrus × aurantium
• Crocus minimus
• Cunonia macrophylla
• Curculigo pilosa
• Cynometra lujae
• Entada rheedei
• Gleditsia caspica
• Haplophyllum ramosissimum
• Helichrysum mixtum
• Jacaratia spinosa
• Lysiana subfalcata
• Macaranga peltata
• Osteospermum muricatum
• Peperomia vulcanica
• Persicaria vivipara
• Physalis peruviana
• Platycarya strobilacea
• Premna tomentosa
• Psephellus huber-morathii
• Sagittaria sagittifolia
• Saussurea amara
• Sideritis euboea
• Sisyrinchium californicum
• Sorbus tianschanica
• Stephania elegans
• Swertia swertopsis
• Taxus brevifolia
• Tsuga chinensis
• Ulmus wallichiana
• Utricularia australis
• Virgilia divaricata

Cross-Links

• PubChem: 160711
• NPASS: NPC38684
• LOTUS: LTS0210908
• wikiData: Q82938531