Officimalonic acid C

Details

• Internal ID: 74288a5a-7af0-4e5a-ba48-dd00d597bfea
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 3-[(1R,2R,3'S,4'S,5S,8R,10R,14R,17R,18R,20S)-2-hydroxy-3',4',5,9,9,14,18-heptamethyl-5',12-dioxospiro[21-oxapentacyclo[12.8.0.01,17.04,13.05,10]docos-4(13)-ene-20,2'-oxolane]-8-yl]oxy-3-oxopropanoic acid
• SMILES (Canonical): CC1CC2(C(C(C(=O)O2)C)C)OCC34C1CCC3(C5=C(CC4O)C6(CCC(C(C6CC5=O)(C)C)OC(=O)CC(=O)O)C)C
• SMILES (Isomeric): C[C@@H]1C[C@]2([C@H]([C@@H](C(=O)O2)C)C)OC[C@@]34[C@@H]1CC[C@]3(C5=C(C[C@H]4O)[C@]6(CC[C@H](C([C@@H]6CC5=O)(C)C)OC(=O)CC(=O)O)C)C
• InChI: InChI=1S/C34H48O9/c1-17-15-34(19(3)18(2)29(40)43-34)41-16-33-20(17)8-11-32(33,7)28-21(12-24(33)36)31(6)10-9-25(42-27(39)14-26(37)38)30(4,5)23(31)13-22(28)35/h17-20,23-25,36H,8-16H2,1-7H3,(H,37,38)/t17-,18+,19+,20-,23+,24-,25-,31-,32+,33+,34+/m1/s1
• InChI Key: JVTKEEUUSBPFFJ-NGPOTDMGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₈O₉
• Molecular Weight: 600.70 g/mol
• Exact Mass: 600.32983310 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.83
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 3-[(1R,2R,3'S,4'S,5S,8R,10R,14R,17R,18R,20S)-2-hydroxy-3',4',5,9,9,14,18-heptamethyl-5',12-dioxospiro[21-oxapentacyclo[12.8.0.01,17.04,13.05,10]docos-4(13)-ene-20,2'-oxolane]-8-yl]oxy-3-oxopropanoic acid
• Officimalonate C
• 3-((1'r,2S,2'r,3S,4S,5's,8'r,10'r,14'r,17'r,18'r)-2'-Hydroxy-3,4,5',9',9',14',18'-heptamethyl-5,12'-dioxo-21'-oxaspiro(oxolane-2,20'-pentacyclo(12.8.0.0,.0,.0,)docosan)-4'(13')-en-8'-yloxy)-3-oxopropanoate
• 3-((1R,2R,3'S,4'S,5S,8R,10R,14R,17R,18R,20S)-2-hydroxy-3',4',5,9,9,14,18-heptamethyl-5',12-dioxospiro(21-oxapentacyclo(12.8.0.01,17.04,13.05,10)docos-4(13)-ene-20,2'-oxolane)-8-yl)oxy-3-oxopropanoic acid
• 3-[(1'r,2S,2'r,3S,4S,5's,8'r,10'r,14'r,17'r,18'r)-2'-Hydroxy-3,4,5',9',9',14',18'-heptamethyl-5,12'-dioxo-21'-oxaspiro[oxolane-2,20'-pentacyclo[12.8.0.0,.0,.0,]docosan]-4'(13')-en-8'-yloxy]-3-oxopropanoate
• RefChem:167963
• CHEBI:210070

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	-	0.8030	80.30%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8713	87.13%
OATP2B1 inhibitior	-	0.5727	57.27%
OATP1B1 inhibitior	+	0.7883	78.83%
OATP1B3 inhibitior	+	0.9271	92.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6146	61.46%
BSEP inhibitior	+	0.8102	81.02%
P-glycoprotein inhibitior	+	0.7549	75.49%
P-glycoprotein substrate	+	0.6107	61.07%
CYP3A4 substrate	+	0.7290	72.90%
CYP2C9 substrate	-	0.8149	81.49%
CYP2D6 substrate	-	0.8941	89.41%
CYP3A4 inhibition	-	0.6612	66.12%
CYP2C9 inhibition	-	0.5869	58.69%
CYP2C19 inhibition	-	0.9088	90.88%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.8236	82.36%
CYP2C8 inhibition	+	0.6604	66.04%
CYP inhibitory promiscuity	-	0.8529	85.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4320	43.20%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9177	91.77%
Skin irritation	+	0.5428	54.28%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4740	47.40%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6448	64.48%
skin sensitisation	-	0.8790	87.90%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5675	56.75%
Acute Oral Toxicity (c)	III	0.4279	42.79%
Estrogen receptor binding	+	0.6992	69.92%
Androgen receptor binding	+	0.7614	76.14%
Thyroid receptor binding	+	0.5295	52.95%
Glucocorticoid receptor binding	+	0.8206	82.06%
Aromatase binding	+	0.7907	79.07%
PPAR gamma	+	0.6907	69.07%
Honey bee toxicity	-	0.6595	65.95%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5450	54.50%
Fish aquatic toxicity	+	0.9953	99.53%

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	98.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.93%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.52%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.05%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	94.38%	89.05%
CHEMBL340	P08684	Cytochrome P450 3A4	88.57%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.70%	96.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.09%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.98%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.47%	93.00%
CHEMBL5028	O14672	ADAM10	85.39%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.28%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.53%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.98%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.93%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	81.48%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.40%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.37%	92.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.81%	95.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.53%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.00%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139588240
• LOTUS: LTS0174152
• wikiData: Q105135944