6'-O-p-Hydroxybenzoylmussaenosidic acid

Details

• Internal ID: f3d12168-9113-494c-8036-9e76b386d887
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(4-hydroxybenzoyl)oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)COC(=O)C4=CC=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C4=CC=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C23H28O12/c1-23(31)7-6-12-13(19(28)29)8-33-21(15(12)23)35-22-18(27)17(26)16(25)14(34-22)9-32-20(30)10-2-4-11(24)5-3-10/h2-5,8,12,14-18,21-22,24-27,31H,6-7,9H2,1H3,(H,28,29)/t12-,14-,15-,16-,17+,18-,21+,22+,23+/m1/s1
• InChI Key: IUXOFSAPFXGQID-KLZCBZFCSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₂
• Molecular Weight: 496.50 g/mol
• Exact Mass: 496.15807632 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.52
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• ACon1_000891
• AKOS040734169
• 6'-O-p-Hydroxybenzoylmussaenosidic acid
• NCGC00169258-01
• NCGC00169258-03
• BRD-K32375164-001-01-3
• 6'-(p-Hydroxybenzoyl)mussaenosidic acid, >=95% (LC/MS-ELSD)
• (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(4-hydroxybenzoyl)oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8525	85.25%
Caco-2	-	0.8747	87.47%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7597	75.97%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.7120	71.20%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7867	78.67%
BSEP inhibitior	-	0.7209	72.09%
P-glycoprotein inhibitior	-	0.6339	63.39%
P-glycoprotein substrate	-	0.7291	72.91%
CYP3A4 substrate	+	0.6630	66.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8806	88.06%
CYP3A4 inhibition	-	0.8787	87.87%
CYP2C9 inhibition	-	0.7952	79.52%
CYP2C19 inhibition	-	0.8243	82.43%
CYP2D6 inhibition	-	0.8937	89.37%
CYP1A2 inhibition	-	0.7746	77.46%
CYP2C8 inhibition	+	0.7991	79.91%
CYP inhibitory promiscuity	-	0.8366	83.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5555	55.55%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9169	91.69%
Skin irritation	-	0.6166	61.66%
Skin corrosion	-	0.9218	92.18%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4814	48.14%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7726	77.26%
skin sensitisation	-	0.8583	85.83%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6552	65.52%
Acute Oral Toxicity (c)	I	0.5007	50.07%
Estrogen receptor binding	+	0.7616	76.16%
Androgen receptor binding	+	0.6454	64.54%
Thyroid receptor binding	+	0.5297	52.97%
Glucocorticoid receptor binding	+	0.7137	71.37%
Aromatase binding	+	0.5707	57.07%
PPAR gamma	+	0.6667	66.67%
Honey bee toxicity	-	0.8840	88.40%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6550	65.50%
Fish aquatic toxicity	+	0.9633	96.33%

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	96.33%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.98%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.11%	97.09%
CHEMBL4208	P20618	Proteasome component C5	91.79%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.29%	91.11%
CHEMBL5255	O00206	Toll-like receptor 4	89.16%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.42%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	85.49%	85.31%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.06%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.85%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.58%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.36%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.06%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.95%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.27%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.77%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.44%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	80.10%	95.93%

Plants that contains it

• Abies alba
• Alkanna hirsutissima
• Amsinckia menziesii
• Buddleja davidii
• Calea megacephala
• Cordyline indivisa
• Corydalis cornuta
• Delphinium campylocentrum
• Disepalum plagioneurum
• Eremophila serrulata
• Grindelia hirsutula
• Hakea salicifolia
• Haloxylon salicornicum
• Jasminum grandiflorum
• Leucanthemum maximum
• Melaleuca uncinata
• Mentha arvensis
• Persea indica
• Phegopteris microstegia
• Picris asplenioides subsp. asplenioides
• Piper aequale
• Primula hirsuta
• Putranjiva roxburghii
• Rhododendron ferrugineum
• Rodgersia podophylla
• Salvia nubicola
• Scapania nemorea
• Senecio scandens
• Vallaris solanacea
• Viscum coloratum
• Vitex agnus-castus
• Vitex negundo
• Vitex trifolia

Cross-Links

• PubChem: 23955877
• NPASS: NPC269888
• LOTUS: LTS0030191
• wikiData: Q105120904