(3R,5R)-1,7-Bis(4-hydroxyphenyl)-3,5-heptanediol

Details

• Internal ID: 84893138-fa26-4e4d-bb00-8b9bf0474458
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: (3R,5R)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol
• SMILES (Canonical): C1=CC(=CC=C1CCC(CC(CCC2=CC=C(C=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CC[C@H](C[C@@H](CCC2=CC=C(C=C2)O)O)O)O
• InChI: InChI=1S/C19H24O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-4,7-10,18-23H,5-6,11-13H2/t18-,19-/m1/s1
• InChI Key: GZVIQGVWSNEONZ-RTBURBONSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₄
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.16745924 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• 408324-76-5
• (3R,5R)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol
• (+)-Hannokinol
• CHEMBL474475
• BDBM246502
• AKOS032949020
• (3R,5R)-3,5-dihydroxy-1,7-bis(4-hydroxyphenyl)-3,5-heptanediol (22)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9182	91.82%
Caco-2	-	0.5428	54.28%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8656	86.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9073	90.73%
OATP1B3 inhibitior	+	0.9316	93.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5292	52.92%
P-glycoprotein inhibitior	-	0.7199	71.99%
P-glycoprotein substrate	-	0.6581	65.81%
CYP3A4 substrate	-	0.6662	66.62%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	+	0.4565	45.65%
CYP3A4 inhibition	+	0.6442	64.42%
CYP2C9 inhibition	-	0.6908	69.08%
CYP2C19 inhibition	-	0.5348	53.48%
CYP2D6 inhibition	-	0.8526	85.26%
CYP1A2 inhibition	-	0.6522	65.22%
CYP2C8 inhibition	-	0.8433	84.33%
CYP inhibitory promiscuity	-	0.6325	63.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8411	84.11%
Carcinogenicity (trinary)	Non-required	0.6588	65.88%
Eye corrosion	-	0.9827	98.27%
Eye irritation	+	0.5607	56.07%
Skin irritation	-	0.6412	64.12%
Skin corrosion	-	0.8712	87.12%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4019	40.19%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7627	76.27%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7796	77.96%
Acute Oral Toxicity (c)	III	0.7823	78.23%
Estrogen receptor binding	+	0.8969	89.69%
Androgen receptor binding	+	0.8288	82.88%
Thyroid receptor binding	+	0.6399	63.99%
Glucocorticoid receptor binding	+	0.5558	55.58%
Aromatase binding	+	0.5199	51.99%
PPAR gamma	+	0.7676	76.76%
Honey bee toxicity	-	0.8347	83.47%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9147	91.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	94.92%	98.35%
CHEMBL2581	P07339	Cathepsin D	94.85%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.18%	96.09%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	88.40%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.79%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.02%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.37%	85.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.19%	94.45%

Plants that contains it

• Alnus japonica
• Curcuma comosa
• Curcuma kwangsiensis
• Dioscorea oppositifolia
• Lanxangia tsaoko
• Tacca chantrieri

Cross-Links

• PubChem: 11034432
• NPASS: NPC91461
• LOTUS: LTS0220098
• wikiData: Q105024654