(4aS,5R,6S,7S,7aS)-5,6,7a-trihydroxy-7-methyl-4a,5,6,7-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 0181a4d7-f9e8-4fe3-adc2-3712e1cc5de0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (4aS,5R,6S,7S,7aS)-5,6,7a-trihydroxy-7-methyl-4a,5,6,7-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1C(C(C2C1(COC=C2C(=O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@@H]([C@H]2[C@@]1(COC=C2C(=O)O)O)O)O
• InChI: InChI=1S/C10H14O6/c1-4-7(11)8(12)6-5(9(13)14)2-16-3-10(4,6)15/h2,4,6-8,11-12,15H,3H2,1H3,(H,13,14)/t4-,6-,7-,8+,10-/m0/s1
• InChI Key: ZCPRKXVRISCLMR-HZHVFOLNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₆
• Molecular Weight: 230.21 g/mol
• Exact Mass: 230.07903816 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.30
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8660	86.60%
Caco-2	-	0.7905	79.05%
Blood Brain Barrier	-	0.5072	50.72%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6069	60.69%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9744	97.44%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9582	95.82%
P-glycoprotein inhibitior	-	0.9563	95.63%
P-glycoprotein substrate	-	0.8918	89.18%
CYP3A4 substrate	-	0.5868	58.68%
CYP2C9 substrate	-	0.6101	61.01%
CYP2D6 substrate	-	0.8858	88.58%
CYP3A4 inhibition	-	0.9679	96.79%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.8636	86.36%
CYP2D6 inhibition	-	0.8695	86.95%
CYP1A2 inhibition	-	0.7266	72.66%
CYP2C8 inhibition	-	0.9327	93.27%
CYP inhibitory promiscuity	-	0.9467	94.67%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6097	60.97%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.8548	85.48%
Skin irritation	-	0.5822	58.22%
Skin corrosion	-	0.8964	89.64%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8677	86.77%
Micronuclear	-	0.5941	59.41%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8217	82.17%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6104	61.04%
Acute Oral Toxicity (c)	III	0.3810	38.10%
Estrogen receptor binding	-	0.5442	54.42%
Androgen receptor binding	-	0.6454	64.54%
Thyroid receptor binding	-	0.6617	66.17%
Glucocorticoid receptor binding	-	0.6457	64.57%
Aromatase binding	-	0.7910	79.10%
PPAR gamma	-	0.6900	69.00%
Honey bee toxicity	-	0.8898	88.98%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4107	41.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.26%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.29%	89.00%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 101855969
• LOTUS: LTS0039855
• wikiData: Q105371356