Rubratoxin acid B

Details

• Internal ID: 130e754e-e2d0-4b0d-b531-b4ea15ed169d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: (4S,5S,6Z,9S)-9-[(1R,2R)-1,2-dihydroxyhexyl]-4-hydroxy-5-[(1S)-1-hydroxyheptyl]-1,3-dioxo-5,8,9,10-tetrahydro-4H-cyclonona[c]furan-6,7-dicarboxylic acid
• SMILES (Canonical): CCCCCCC(C1C(C2=C(CC(CC(=C1C(=O)O)C(=O)O)C(C(CCCC)O)O)C(=O)OC2=O)O)O
• SMILES (Isomeric): CCCCCC[C@@H]([C@H]/1[C@@H](C2=C(C[C@H](C/C(=C1/C(=O)O)/C(=O)O)[C@H]([C@@H](CCCC)O)O)C(=O)OC2=O)O)O
• InChI: InChI=1S/C26H38O11/c1-3-5-7-8-10-16(27)20-18(24(33)34)14(23(31)32)11-13(21(29)17(28)9-6-4-2)12-15-19(22(20)30)26(36)37-25(15)35/h13,16-17,20-22,27-30H,3-12H2,1-2H3,(H,31,32)(H,33,34)/b18-14-/t13-,16-,17+,20+,21+,22+/m0/s1
• InChI Key: VDOFXRXPIGETKV-ZHYFBHNKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₁₁
• Molecular Weight: 526.60 g/mol
• Exact Mass: 526.24141202 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.46
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 13

Synonyms

• (4S,5S,6Z,9S)-9-((1R,2R)-1,2-dihydroxyhexyl)-4-hydroxy-5-((1S)-1-hydroxyheptyl)-1,3-dioxo-5,8,9,10-tetrahydro-4H-cyclonona(c)furan-6,7-dicarboxylic acid
• (4S,5S,6Z,9S)-9-[(1R,2R)-1,2-dihydroxyhexyl]-4-hydroxy-5-[(1S)-1-hydroxyheptyl]-1,3-dioxo-5,8,9,10-tetrahydro-4H-cyclonona[c]furan-6,7-dicarboxylic acid
• (4S,5S,9S)-9-((1R,2R)-1,2-Dihydroxyhexyl)-4-hydroxy-5-((1S)-1-hydroxyheptyl)-1,3-dioxo-1H,3H,4H,5H,8H,9H,10H-cyclonona(c)furan-6,7-dicarboxylate
• (4S,5S,9S)-9-[(1R,2R)-1,2-Dihydroxyhexyl]-4-hydroxy-5-[(1S)-1-hydroxyheptyl]-1,3-dioxo-1H,3H,4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylate
• RefChem:180232
• CHEMBL4561475
• CHEBI:225781
• (4S,5S,6Z,9S)-9-[(1R,2R)-1,2-dihydroxyhexyl]-4-hydroxy-5-[(1S)-1-hydroxyheptyl]-1,3-dioxo-5,8,9,10-tetrahydro-4H-cyclonona[c]uran-6,7-dicarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9447	94.47%
Caco-2	-	0.8037	80.37%
Blood Brain Barrier	+	0.5105	51.05%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7203	72.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8645	86.45%
P-glycoprotein inhibitior	-	0.5958	59.58%
P-glycoprotein substrate	+	0.5715	57.15%
CYP3A4 substrate	+	0.6034	60.34%
CYP2C9 substrate	-	0.5898	58.98%
CYP2D6 substrate	-	0.8860	88.60%
CYP3A4 inhibition	+	0.6827	68.27%
CYP2C9 inhibition	-	0.7725	77.25%
CYP2C19 inhibition	-	0.5853	58.53%
CYP2D6 inhibition	-	0.9064	90.64%
CYP1A2 inhibition	-	0.6143	61.43%
CYP2C8 inhibition	+	0.4579	45.79%
CYP inhibitory promiscuity	-	0.9291	92.91%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6011	60.11%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.7943	79.43%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5909	59.09%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8616	86.16%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.4921	49.21%
Acute Oral Toxicity (c)	II	0.5320	53.20%
Estrogen receptor binding	+	0.7047	70.47%
Androgen receptor binding	+	0.6428	64.28%
Thyroid receptor binding	-	0.6221	62.21%
Glucocorticoid receptor binding	+	0.6230	62.30%
Aromatase binding	-	0.5615	56.15%
PPAR gamma	+	0.5702	57.02%
Honey bee toxicity	-	0.9281	92.81%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5466	54.66%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.25%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.09%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.63%	90.17%
CHEMBL299	P17252	Protein kinase C alpha	94.33%	98.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.97%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.69%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.10%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.34%	96.38%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.23%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.92%	90.71%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	87.23%	92.08%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.87%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.75%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.30%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.42%	93.00%
CHEMBL1907	P15144	Aminopeptidase N	84.28%	93.31%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.75%	92.86%
CHEMBL240	Q12809	HERG	83.19%	89.76%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.05%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	82.83%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.62%	97.25%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.16%	97.29%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	81.12%	91.81%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.43%	97.09%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.26%	85.94%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 145721303
• LOTUS: LTS0094945
• wikiData: Q105284292