Zaragozic Acid A

Details

• Internal ID: ce4a328f-402a-4ba9-8b67-02fdbc406e8f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
• InChI: InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1
• InChI Key: DFKDOZMCHOGOBR-NCSQYGPNSA-N
• Popularity: 115 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₁₄
• Molecular Weight: 690.70 g/mol
• Exact Mass: 690.28875614 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 17

Synonyms

• squalestatin 1
• 142561-96-4
• Squalestatin
• squalestatin s1
• CHEMBL280978
• CHEBI:75170
• 1117HVX02L
• (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
• 1S-((4S-acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(E)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3S,4S,5R-tricarboxylic acid
• Squalestatin A
• L-erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-c-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-((2E,4S,6S)-4,6-dimethyl-2-octenoate), (7S)-
• L-694599
• ZaragozicacidA
• UNII-1117HVX02L
• 3vjc
• 3vje
• (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetoxy-5-methyl-3-methylene-6-phenyl-hexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
• L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S)-
• ZGA
• SQUALESTATIN I
• SQUALASTATIN S1
• 144541-82-2
• SCHEMBL408941
• ZARAGOZIC ACID A [MI]
• GTPL3057
• DTXSID701018091
• BDBM50051873
• LMPK00000001
• GR 105155X
• GR-105155X
• L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-(4,6-dimethyl-2-octenoate), (5(2E,4S,6S),7S)-
• HY-116290
• CS-0064870
• J-007666
• L 694599
• Q8066579
• (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,7-dihydroxy-6-((S)-6-methyl-4-methyl-oct-2-enoyloxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
• (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
• (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
• (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-methyl-3-methylidene-6-phenylhexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid (non-preferred name)
• 138682-84-5
• 7-[3,5-dimethyl-(E)-1-heptenylcarbonyloxy]-2,6-dihydroxy-5-[3-(2-methyl-1-methylcarbonyloxy-3-phenylpropyl)-3-butenyl]-4,8-dioxabicyclo[3.2.1]octane-1,2,3-tricarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8336	83.36%
Caco-2	-	0.8598	85.98%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6786	67.86%
OATP2B1 inhibitior	-	0.7157	71.57%
OATP1B1 inhibitior	+	0.8213	82.13%
OATP1B3 inhibitior	-	0.3817	38.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7627	76.27%
P-glycoprotein inhibitior	+	0.7517	75.17%
P-glycoprotein substrate	+	0.6861	68.61%
CYP3A4 substrate	+	0.6866	68.66%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8937	89.37%
CYP3A4 inhibition	+	0.5230	52.30%
CYP2C9 inhibition	-	0.6716	67.16%
CYP2C19 inhibition	-	0.6520	65.20%
CYP2D6 inhibition	-	0.9120	91.20%
CYP1A2 inhibition	-	0.7573	75.73%
CYP2C8 inhibition	+	0.8087	80.87%
CYP inhibitory promiscuity	-	0.7929	79.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9141	91.41%
Skin irritation	-	0.5788	57.88%
Skin corrosion	-	0.9083	90.83%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4748	47.48%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5801	58.01%
skin sensitisation	-	0.8356	83.56%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8129	81.29%
Acute Oral Toxicity (c)	III	0.3258	32.58%
Estrogen receptor binding	+	0.8124	81.24%
Androgen receptor binding	+	0.7414	74.14%
Thyroid receptor binding	+	0.6008	60.08%
Glucocorticoid receptor binding	+	0.7780	77.80%
Aromatase binding	+	0.6405	64.05%
PPAR gamma	+	0.7116	71.16%
Honey bee toxicity	-	0.6800	68.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5445	54.45%
Fish aquatic toxicity	+	0.9957	99.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.59%	90.17%
CHEMBL2581	P07339	Cathepsin D	98.88%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.70%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	93.11%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.17%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.89%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.43%	94.62%
CHEMBL1951	P21397	Monoamine oxidase A	86.01%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.29%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.20%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.84%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.42%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.60%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.66%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.54%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.27%	96.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6438355
• LOTUS: LTS0042680
• wikiData: Q8066579