(4R,4aS,5R,7aS)-5-hydroxy-4,7-bis(hydroxymethyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one

Details

• Internal ID: 3940f566-42db-4bd0-b241-f50b193056e0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4R,4aS,5R,7aS)-5-hydroxy-4,7-bis(hydroxymethyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one
• SMILES (Canonical): C1C2C(C(C=C2CO)O)C(C(=O)O1)CO
• SMILES (Isomeric): C1[C@H]2[C@H]([C@H](C=C2CO)O)[C@@H](C(=O)O1)CO
• InChI: InChI=1S/C10H14O5/c11-2-5-1-8(13)9-6(3-12)10(14)15-4-7(5)9/h1,6-9,11-13H,2-4H2/t6-,7+,8-,9+/m0/s1
• InChI Key: VVELVVLHDHICNB-UYXSQOIJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.21 g/mol
• Exact Mass: 214.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.32
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9083	90.83%
Caco-2	-	0.8106	81.06%
Blood Brain Barrier	-	0.5322	53.22%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6744	67.44%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9110	91.10%
OATP1B3 inhibitior	+	0.9674	96.74%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9600	96.00%
P-glycoprotein inhibitior	-	0.9821	98.21%
P-glycoprotein substrate	-	0.9243	92.43%
CYP3A4 substrate	-	0.5997	59.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.8515	85.15%
CYP2C9 inhibition	-	0.8758	87.58%
CYP2C19 inhibition	-	0.7490	74.90%
CYP2D6 inhibition	-	0.8933	89.33%
CYP1A2 inhibition	-	0.7271	72.71%
CYP2C8 inhibition	-	0.9539	95.39%
CYP inhibitory promiscuity	-	0.7399	73.99%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.6824	68.24%
Eye corrosion	-	0.9572	95.72%
Eye irritation	-	0.6630	66.30%
Skin irritation	-	0.6818	68.18%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7814	78.14%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5584	55.84%
skin sensitisation	-	0.8358	83.58%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6144	61.44%
Acute Oral Toxicity (c)	III	0.3331	33.31%
Estrogen receptor binding	-	0.8072	80.72%
Androgen receptor binding	-	0.4838	48.38%
Thyroid receptor binding	-	0.8270	82.70%
Glucocorticoid receptor binding	-	0.6654	66.54%
Aromatase binding	-	0.8723	87.23%
PPAR gamma	-	0.7581	75.81%
Honey bee toxicity	-	0.8571	85.71%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8661	86.61%

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	95.06%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	94.27%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.12%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.84%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.50%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.28%	96.61%
CHEMBL2581	P07339	Cathepsin D	83.75%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.63%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.42%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.28%	97.25%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 11492213
• NPASS: NPC176627
• LOTUS: LTS0050763
• wikiData: Q105297618