(4S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1,3,4,4a,5,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 4aaabf16-d6c4-4ec6-8349-8f4b5eb070de
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (4S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1,3,4,4a,5,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C1C2C(C(CO1)C(=O)O)C(C=C2CO)O
• SMILES (Isomeric): C1[C@H]2[C@@H]([C@@H](CO1)C(=O)O)[C@H](C=C2CO)O
• InChI: InChI=1S/C10H14O5/c11-2-5-1-8(12)9-6(5)3-15-4-7(9)10(13)14/h1,6-9,11-12H,2-4H2,(H,13,14)/t6-,7-,8+,9+/m1/s1
• InChI Key: DIIADJQOLFWUFJ-HXFLIBJXSA-N
• Popularity: 0 references 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: -1.90
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• (4S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1,3,4,4a,5,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• DTXSID70780165

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9343	93.43%
Caco-2	-	0.8164	81.64%
Blood Brain Barrier	-	0.5822	58.22%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6299	62.99%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.9053	90.53%
OATP1B3 inhibitior	+	0.9613	96.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9729	97.29%
P-glycoprotein inhibitior	-	0.9828	98.28%
P-glycoprotein substrate	-	0.9289	92.89%
CYP3A4 substrate	-	0.6175	61.75%
CYP2C9 substrate	+	0.5818	58.18%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.8580	85.80%
CYP2C9 inhibition	-	0.8732	87.32%
CYP2C19 inhibition	-	0.7413	74.13%
CYP2D6 inhibition	-	0.8857	88.57%
CYP1A2 inhibition	-	0.7355	73.55%
CYP2C8 inhibition	-	0.8974	89.74%
CYP inhibitory promiscuity	-	0.8788	87.88%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7008	70.08%
Eye corrosion	-	0.9492	94.92%
Eye irritation	-	0.5418	54.18%
Skin irritation	-	0.7380	73.80%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8524	85.24%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5550	55.50%
skin sensitisation	-	0.8358	83.58%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5902	59.02%
Acute Oral Toxicity (c)	III	0.4149	41.49%
Estrogen receptor binding	-	0.7832	78.32%
Androgen receptor binding	+	0.5293	52.93%
Thyroid receptor binding	-	0.8236	82.36%
Glucocorticoid receptor binding	-	0.6535	65.35%
Aromatase binding	-	0.8900	89.00%
PPAR gamma	-	0.7299	72.99%
Honey bee toxicity	-	0.9258	92.58%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.7586	75.86%

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	92.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.48%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.98%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.26%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.86%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	80.56%	83.82%

Plants that contains it

• Galium macedonicum

Cross-Links

• PubChem: 71355980
• LOTUS: LTS0119754
• wikiData: Q82743159