Tetrahydrogambogic Acid

Details

• Internal ID: 33d2cd18-3ddc-401b-a6a7-0b9a3622001d
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (Z)-4-[12,18-dihydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14-oxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid
• SMILES (Canonical): CC(=CCCC1(C=CC2=C(C3=C(C(=C2O1)CC=C(C)C)OC45C(C3=O)CC6CC4C(OC5(C6O)CC=C(C)C(=O)O)(C)C)O)C)C
• SMILES (Isomeric): CC(=CCCC1(C=CC2=C(C3=C(C(=C2O1)CC=C(C)C)OC45C(C3=O)CC6CC4C(OC5(C6O)C/C=C(/C)\C(=O)O)(C)C)O)C)C
• InChI: InChI=1S/C38H48O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,23,26-27,33,39,41H,9,12,15,17-19H2,1-8H3,(H,42,43)/b22-13-
• InChI Key: CXFIQFGADOTDPF-XKZIYDEJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₈O₈
• Molecular Weight: 632.80 g/mol
• Exact Mass: 632.33491849 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 7.20
• Atomic LogP (AlogP): 7.11
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• Spectrum5_000028
• BSPBio_002718
• SPECTRUM201540
• CHEMBL1605700
• CHEBI:183958
• CCG-38451
• NCGC00095544-01
• NCGC00095544-02
• SR-05000002769
• SR-05000002769-1
• (Z)-4-[12,18-dihydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14-oxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9755	97.55%
Caco-2	-	0.8021	80.21%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7701	77.01%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	-	0.7739	77.39%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9920	99.20%
P-glycoprotein inhibitior	+	0.8076	80.76%
P-glycoprotein substrate	+	0.6472	64.72%
CYP3A4 substrate	+	0.7010	70.10%
CYP2C9 substrate	-	0.8119	81.19%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.5184	51.84%
CYP2C19 inhibition	-	0.6123	61.23%
CYP2D6 inhibition	-	0.9014	90.14%
CYP1A2 inhibition	+	0.5438	54.38%
CYP2C8 inhibition	+	0.6743	67.43%
CYP inhibitory promiscuity	-	0.7416	74.16%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5100	51.00%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9032	90.32%
Skin irritation	-	0.6203	62.03%
Skin corrosion	-	0.8994	89.94%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4311	43.11%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7916	79.16%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9094	90.94%
Acute Oral Toxicity (c)	I	0.4970	49.70%
Estrogen receptor binding	+	0.8427	84.27%
Androgen receptor binding	+	0.7673	76.73%
Thyroid receptor binding	+	0.6331	63.31%
Glucocorticoid receptor binding	+	0.8406	84.06%
Aromatase binding	+	0.7582	75.82%
PPAR gamma	+	0.7480	74.80%
Honey bee toxicity	-	0.7796	77.96%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	29906.8 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	12589.3 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	35481.3 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.55%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.69%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.01%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.31%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.66%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.64%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.01%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.60%	85.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.29%	95.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.98%	99.23%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.54%	89.34%
CHEMBL1951	P21397	Monoamine oxidase A	87.25%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.79%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.12%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.73%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.82%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.46%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.46%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.03%	95.89%

Plants that contains it

• Garcinia hanburyi

Cross-Links

• PubChem: 9917275
• NPASS: NPC102810
• ChEMBL: CHEMBL1605700