Mussaenosidic acid

Details

• Internal ID: b5af8a59-50f3-4ec8-bc68-66dca9a63f28
• 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-(hydroxymethyl)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)CO)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)CO)O)O)O)O
• InChI: InChI=1S/C16H24O10/c1-16(23)3-2-6-7(13(21)22)5-24-14(9(6)16)26-15-12(20)11(19)10(18)8(4-17)25-15/h5-6,8-12,14-15,17-20,23H,2-4H2,1H3,(H,21,22)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1
• InChI Key: VLCHQFXSBHIBRV-NJPMDSMTSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.36 g/mol
• Exact Mass: 376.13694696 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.10
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 82451-22-7
• (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• MEGxp0_000766
• SCHEMBL2636258
• CHEMBL3426657
• CHEBI:167726
• DTXSID701345616
• AKOS040734297
• NCGC00347506-02

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7659	76.59%
Caco-2	-	0.8657	86.57%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7195	71.95%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	-	0.3229	32.29%
OATP1B3 inhibitior	+	0.9184	91.84%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7879	78.79%
BSEP inhibitior	-	0.9339	93.39%
P-glycoprotein inhibitior	-	0.8961	89.61%
P-glycoprotein substrate	-	0.9076	90.76%
CYP3A4 substrate	+	0.6090	60.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8863	88.63%
CYP3A4 inhibition	-	0.9341	93.41%
CYP2C9 inhibition	-	0.8851	88.51%
CYP2C19 inhibition	-	0.9071	90.71%
CYP2D6 inhibition	-	0.9191	91.91%
CYP1A2 inhibition	-	0.8644	86.44%
CYP2C8 inhibition	-	0.6473	64.73%
CYP inhibitory promiscuity	-	0.8847	88.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6368	63.68%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9714	97.14%
Skin irritation	-	0.5643	56.43%
Skin corrosion	-	0.9285	92.85%
Ames mutagenesis	-	0.6640	66.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.6077	60.77%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8690	86.90%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5573	55.73%
Acute Oral Toxicity (c)	III	0.4596	45.96%
Estrogen receptor binding	+	0.6141	61.41%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5214	52.14%
Glucocorticoid receptor binding	+	0.5395	53.95%
Aromatase binding	+	0.5706	57.06%
PPAR gamma	+	0.5649	56.49%
Honey bee toxicity	-	0.8929	89.29%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7550	75.50%
Fish aquatic toxicity	+	0.7290	72.90%

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	97.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.70%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.24%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.34%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	85.30%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.57%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.52%	97.25%
CHEMBL4208	P20618	Proteasome component C5	83.20%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.01%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.80%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.45%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.33%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.27%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.45%	94.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.16%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.02%	96.61%

Plants that contains it

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

Cross-Links

• PubChem: 21633105
• NPASS: NPC217922
• LOTUS: LTS0016590
• wikiData: Q105288278