Robustic acid

Details

• Internal ID: 67e26efc-3d03-4b8c-a9a9-936775a47d79
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Hydroxyisoflavonoids
• IUPAC Name: 6-hydroxy-5-methoxy-7-(4-methoxyphenyl)-2,2-dimethylpyrano[3,2-g]chromen-8-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C3C(=C2OC)C(=C(C(=O)O3)C4=CC=C(C=C4)OC)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C3C(=C2OC)C(=C(C(=O)O3)C4=CC=C(C=C4)OC)O)C
• InChI: InChI=1S/C22H20O6/c1-22(2)10-9-14-15(28-22)11-16-18(20(14)26-4)19(23)17(21(24)27-16)12-5-7-13(25-3)8-6-12/h5-11,23H,1-4H3
• InChI Key: MBZKDBQDALOSRP-UHFFFAOYSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₆
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.12598835 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.37
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 5307-59-5
• 2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 4-hydroxy-5-methoxy-3-(4-methoxyphenyl)-8,8-dimethyl-
• 2H,8H-Benzo(1,2-b:5,4-b')dipyran-2-one, 4-hydroxy-5-methoxy-3-(4-methoxyphenyl)-8,8-dimethyl-
• Spectrum_000556
• SpecPlus_000613
• Spectrum2_001165
• Spectrum3_001802
• Spectrum4_001592
• Spectrum5_000304
• BSPBio_003383
• KBioGR_002204
• KBioSS_001036
• SPECTRUM240673
• DivK1c_006709
• SCHEMBL572212
• SPBio_001149
• CHEMBL400777
• SCHEMBL15941305
• CHEBI:92953
• KBio1_001653
• KBio2_001036
• KBio2_003604
• KBio2_006172
• KBio3_002886
• DTXSID30201149
• MBZKDBQDALOSRP-UHFFFAOYSA-N
• CCG-39045
• LMPK12160025
• AKOS040753805
• NCGC00095552-01
• NCGC00095552-02
• 2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 4-hydroxy-5-methoxy-3-(p-methoxyphenyl)-8,8-dimethyl-
• SR-05000002632
• SR-05000002632-1
• BRD-K54411430-001-02-5
• Q27164688
• 4-Hydroxy-5-methoxy-3-(4-methoxyphenyl)-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one #
• 6-hydroxy-5-methoxy-7-(4-methoxyphenyl)-2,2-dimethyl-8-pyrano[3,2-g][1]benzopyranone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	+	0.8576	85.76%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8040	80.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8838	88.38%
P-glycoprotein inhibitior	+	0.8858	88.58%
P-glycoprotein substrate	-	0.8102	81.02%
CYP3A4 substrate	+	0.6309	63.09%
CYP2C9 substrate	-	0.5650	56.50%
CYP2D6 substrate	-	0.8655	86.55%
CYP3A4 inhibition	+	0.5398	53.98%
CYP2C9 inhibition	-	0.6007	60.07%
CYP2C19 inhibition	+	0.6030	60.30%
CYP2D6 inhibition	-	0.8800	88.00%
CYP1A2 inhibition	-	0.8511	85.11%
CYP2C8 inhibition	+	0.7491	74.91%
CYP inhibitory promiscuity	+	0.5226	52.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Danger	0.6331	63.31%
Eye corrosion	-	0.9881	98.81%
Eye irritation	+	0.6315	63.15%
Skin irritation	-	0.7765	77.65%
Skin corrosion	-	0.9734	97.34%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3727	37.27%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9039	90.39%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7679	76.79%
Acute Oral Toxicity (c)	III	0.4427	44.27%
Estrogen receptor binding	+	0.9487	94.87%
Androgen receptor binding	+	0.8447	84.47%
Thyroid receptor binding	+	0.7814	78.14%
Glucocorticoid receptor binding	+	0.8428	84.28%
Aromatase binding	+	0.6694	66.94%
PPAR gamma	+	0.8769	87.69%
Honey bee toxicity	-	0.8615	86.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9843	98.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	0.0631 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.61%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.82%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.28%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.27%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.96%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.69%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.64%	98.95%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	93.27%	80.96%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.69%	89.00%
CHEMBL1907	P15144	Aminopeptidase N	91.69%	93.31%
CHEMBL4208	P20618	Proteasome component C5	90.89%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.74%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.37%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.26%	94.73%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.94%	96.67%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	83.59%	93.24%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.53%	93.99%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.89%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.54%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.29%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.21%	86.92%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.07%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.95%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%
CHEMBL2535	P11166	Glucose transporter	80.22%	98.75%

Plants that contains it

• Deguelia hatschbachii
• Deguelia scandens
• Erythrina variegata
• Millettia thonningii

Cross-Links

• PubChem: 54677407
• LOTUS: LTS0166354
• wikiData: Q27164688