Garcimangosone A

Details

• Internal ID: 348bf871-5254-4eae-bae0-5e374eea7ce5
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 11,22-dihydroxy-7,7,18,18-tetramethyl-15-(3-methylbut-2-enyl)-2,6,17-trioxapentacyclo[12.8.0.03,12.05,10.016,21]docosa-1(14),3,5(10),8,11,15,19,21-octaen-13-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1C(=O)C4=C(C5=C(C=C4O3)OC(C=C5)(C)C)O)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1C(=O)C4=C(C5=C(C=C4O3)OC(C=C5)(C)C)O)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C28H28O6/c1-14(2)7-8-16-20-24(31)21-19(13-18-15(22(21)29)9-11-27(3,4)33-18)32-26(20)23(30)17-10-12-28(5,6)34-25(16)17/h7,9-13,29-30H,8H2,1-6H3
• InChI Key: SSITWAPGVBPANU-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₈O₆
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.18858861 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 6.23
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 11,22-dihydroxy-7,7,18,18-tetramethyl-15-(3-methylbut-2-enyl)-2,6,17-trioxapentacyclo[12.8.0.03,12.05,10.016,21]docosa-1(14),3,5(10),8,11,15,19,21-octaen-13-one
• SCHEMBL17056910
• CHEBI:185604
• 5,12-dihydroxy-2,2,9,9-tetramethyl-14-(3-methylbut-2-en-1-yl)-9,13-dihydro-2H-1,6,8-trioxapentacen-13-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	-	0.5805	58.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7159	71.59%
OATP2B1 inhibitior	-	0.7128	71.28%
OATP1B1 inhibitior	+	0.8547	85.47%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9341	93.41%
P-glycoprotein inhibitior	+	0.8432	84.32%
P-glycoprotein substrate	-	0.5676	56.76%
CYP3A4 substrate	+	0.6075	60.75%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	-	0.8677	86.77%
CYP2C9 inhibition	+	0.7303	73.03%
CYP2C19 inhibition	+	0.7855	78.55%
CYP2D6 inhibition	-	0.7304	73.04%
CYP1A2 inhibition	-	0.5591	55.91%
CYP2C8 inhibition	+	0.5392	53.92%
CYP inhibitory promiscuity	+	0.7538	75.38%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6419	64.19%
Eye corrosion	-	0.9903	99.03%
Eye irritation	+	0.5271	52.71%
Skin irritation	-	0.6959	69.59%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.6199	61.99%
skin sensitisation	-	0.6213	62.13%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8281	82.81%
Acute Oral Toxicity (c)	III	0.7431	74.31%
Estrogen receptor binding	+	0.8614	86.14%
Androgen receptor binding	+	0.7155	71.55%
Thyroid receptor binding	+	0.6523	65.23%
Glucocorticoid receptor binding	+	0.8344	83.44%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.8290	82.90%
Honey bee toxicity	-	0.7817	78.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9822	98.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.59%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	97.21%	89.34%
CHEMBL2581	P07339	Cathepsin D	94.54%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.65%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.22%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.67%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL4208	P20618	Proteasome component C5	86.11%	90.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.12%	85.30%
CHEMBL1951	P21397	Monoamine oxidase A	84.77%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.26%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.25%	90.71%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	84.17%	80.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.38%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.55%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.45%	99.23%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.88%	95.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.48%	94.42%

Plants that contains it

• Aster bellidiastrum
• Caragana halodendron
• Davallia divaricata
• Dolomiaea souliei
• Eucalyptus camaldulensis
• Garcinia mangostana
• Ligularia vellerea
• Lonicera hypoleuca
• Nicotiana sylvestris
• Serpocaulon triseriale

Cross-Links

• PubChem: 10874207
• NPASS: NPC221202
• LOTUS: LTS0117541
• wikiData: Q105259703