(4R,5S)-4-hydroxy-5-[(1S,2R,3R)-1,2,3-trihydroxy-3-phenylpropyl]oxolan-2-one

Details

• Internal ID: c05e98e4-b91a-4ae5-b818-b784a0839ae9
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (4R,5S)-4-hydroxy-5-[(1S,2R,3R)-1,2,3-trihydroxy-3-phenylpropyl]oxolan-2-one
• SMILES (Canonical): C1C(C(OC1=O)C(C(C(C2=CC=CC=C2)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC1=O)[C@H]([C@@H]([C@@H](C2=CC=CC=C2)O)O)O)O
• InChI: InChI=1S/C13H16O6/c14-8-6-9(15)19-13(8)12(18)11(17)10(16)7-4-2-1-3-5-7/h1-5,8,10-14,16-18H,6H2/t8-,10-,11-,12+,13+/m1/s1
• InChI Key: ITWCBKGNWXDVFP-XTAFZBPGSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₆
• Molecular Weight: 268.26 g/mol
• Exact Mass: 268.09468823 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.88
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• (+)-Cardiobutanolide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5826	58.26%
Caco-2	-	0.8033	80.33%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6288	62.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9451	94.51%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9753	97.53%
P-glycoprotein inhibitior	-	0.9224	92.24%
P-glycoprotein substrate	-	0.9153	91.53%
CYP3A4 substrate	-	0.5886	58.86%
CYP2C9 substrate	-	0.6009	60.09%
CYP2D6 substrate	-	0.8014	80.14%
CYP3A4 inhibition	-	0.8813	88.13%
CYP2C9 inhibition	-	0.9588	95.88%
CYP2C19 inhibition	-	0.9408	94.08%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.9143	91.43%
CYP2C8 inhibition	-	0.9581	95.81%
CYP inhibitory promiscuity	-	0.9350	93.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6145	61.45%
Eye corrosion	-	0.9705	97.05%
Eye irritation	-	0.8832	88.32%
Skin irritation	-	0.5332	53.32%
Skin corrosion	-	0.8874	88.74%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7915	79.15%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	+	0.6350	63.50%
skin sensitisation	-	0.7884	78.84%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.5337	53.37%
Acute Oral Toxicity (c)	III	0.5051	50.51%
Estrogen receptor binding	-	0.6775	67.75%
Androgen receptor binding	-	0.6530	65.30%
Thyroid receptor binding	-	0.7211	72.11%
Glucocorticoid receptor binding	-	0.5812	58.12%
Aromatase binding	-	0.8334	83.34%
PPAR gamma	-	0.5370	53.70%
Honey bee toxicity	-	0.8404	84.04%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.4863	48.63%

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	94.90%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.53%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.42%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.79%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	83.73%	90.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.65%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.52%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.18%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.33%	94.08%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.15%	96.61%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.13%	93.56%

Plants that contains it

• Aucklandia costus
• Goniothalamus cardiopetalus

Cross-Links

• PubChem: 639643
• NPASS: NPC138549
• LOTUS: LTS0250145
• wikiData: Q105120332