Deoxygambogenin

Details

• Internal ID: de8bbb5d-2a16-4f6a-8add-f2cf721a41c5
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: (1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dienyl]-6,8-dihydroxy-17,17-dimethyl-5,15-bis(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=CC4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C)CC=C(C)C)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C(=C2C(=C1O)C(=O)C3=C[C@@H]4C[C@@H]5[C@@]3(O2)[C@](C4=O)(OC5(C)C)CC=C(C)C)CC=C(C)C)O)/C)C
• InChI: InChI=1S/C38H48O6/c1-21(2)11-10-12-24(7)14-16-26-31(39)27(15-13-22(3)4)34-30(32(26)40)33(41)28-19-25-20-29-36(8,9)44-37(35(25)42,18-17-23(5)6)38(28,29)43-34/h11,13-14,17,19,25,29,39-40H,10,12,15-16,18,20H2,1-9H3/b24-14+/t25-,29+,37+,38-/m1/s1
• InChI Key: BYSLEZZCJZXNQG-FZHSXGHWSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₈O₆
• Molecular Weight: 600.80 g/mol
• Exact Mass: 600.34508925 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 9.20
• Atomic LogP (AlogP): 8.20
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• Desoxygambogenin
• 173614-93-2
• (1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dienyl]-6,8-dihydroxy-17,17-dimethyl-5,15-bis(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione
• (-)-Desoxygambogenin
• CHEMBL4528043
• DTXSID501315081

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	-	0.7608	76.08%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7796	77.96%
OATP2B1 inhibitior	-	0.7141	71.41%
OATP1B1 inhibitior	+	0.7465	74.65%
OATP1B3 inhibitior	-	0.2132	21.32%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6064	60.64%
BSEP inhibitior	+	0.9970	99.70%
P-glycoprotein inhibitior	+	0.8366	83.66%
P-glycoprotein substrate	-	0.5142	51.42%
CYP3A4 substrate	+	0.6837	68.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8338	83.38%
CYP3A4 inhibition	-	0.7104	71.04%
CYP2C9 inhibition	-	0.6081	60.81%
CYP2C19 inhibition	-	0.7690	76.90%
CYP2D6 inhibition	-	0.8998	89.98%
CYP1A2 inhibition	-	0.5093	50.93%
CYP2C8 inhibition	+	0.6646	66.46%
CYP inhibitory promiscuity	-	0.6794	67.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5796	57.96%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8835	88.35%
Skin irritation	-	0.6524	65.24%
Skin corrosion	-	0.9164	91.64%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4411	44.11%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7073	70.73%
skin sensitisation	-	0.8050	80.50%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6716	67.16%
Acute Oral Toxicity (c)	III	0.3657	36.57%
Estrogen receptor binding	+	0.8091	80.91%
Androgen receptor binding	+	0.7606	76.06%
Thyroid receptor binding	+	0.6575	65.75%
Glucocorticoid receptor binding	+	0.8380	83.80%
Aromatase binding	+	0.7935	79.35%
PPAR gamma	+	0.7185	71.85%
Honey bee toxicity	-	0.6550	65.50%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9960	99.60%

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	99.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.03%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.49%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	92.11%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.19%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.90%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.42%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.99%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.24%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.02%	85.14%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	80.80%	92.68%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.55%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.43%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.25%	95.89%

Plants that contains it

• Callitriche stagnalis
• Croton discolor
• Eclipta prostrata
• Fragaria chiloensis
• Garcinia hanburyi
• Hemionitis glauca
• Millettia extensa
• Rhizomnium pseudopunctatum
• Ruscus hypoglossum
• Salix babylonica
• Scrophularia glabrata
• Toxicodendron radicans
• Vernonanthura discolor
• Wrightia coccinea

Cross-Links

• PubChem: 10817397
• NPASS: NPC30617
• LOTUS: LTS0017110
• wikiData: Q104400278