Gedunin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	9fed9e24-3a31-4cce-90be-eb4bf399b061
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name	[(1S,2R,4S,7S,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadec-13-en-19-yl] acetate
SMILES (Canonical)	CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C45C(O4)C(=O)OC(C5(CC3)C)C6=COC=C6)C)C)(C)C
SMILES (Isomeric)	CC(=O)O[C@@H]1C[C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1([C@]45[C@H](O4)C(=O)O[C@H]([C@@]5(CC3)C)C6=COC=C6)C)C
InChI	InChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
InChI Key	YJXDGWUNRYLINJ-BHAPSIHVSA-N
Popularity	73 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₈H₃₄O₇
Molecular Weight	482.60 g/mol
Exact Mass	482.23045342 g/mol
Topological Polar Surface Area (TPSA)	95.30 Å²
XlogP	4.20
Atomic LogP (AlogP)	4.56
H-Bond Acceptor	7
H-Bond Donor	0
Rotatable Bonds	2

Synonyms

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Gedunine

2753-30-2

(-)-gedunin

NSC 113497

CHEBI:65954

(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(Furan-3-yl)-4b,7,7,10a,12a-pentamethyl-3,8-dioxo-1,3,3a,4b,5,6,6a,7,8,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]oxireno[2,3-d]isochromen-5-yl acetate

(4aR,6R,6aS,6bR,7aS,10R,10aS,12aR,12bR)-10-(3-furyl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydrooxireno[c]phenanthro[1,2-d]pyran-6-yl acetate

Oxireno(c)phenanthro(1,2-d)pyran-3,8(3aH,4bH)-dione, 5-(acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyl-,(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-

VH4BN8F5Z5

C28H34O7

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9839	98.39%
Caco-2	-	0.6162	61.62%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7303	73.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4656	46.56%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8982	89.82%
P-glycoprotein inhibitior	+	0.8201	82.01%
P-glycoprotein substrate	-	0.5404	54.04%
CYP3A4 substrate	+	0.7058	70.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.8310	83.10%
CYP2C19 inhibition	-	0.7598	75.98%
CYP2D6 inhibition	-	0.9256	92.56%
CYP1A2 inhibition	-	0.8083	80.83%
CYP2C8 inhibition	+	0.6305	63.05%
CYP inhibitory promiscuity	-	0.8411	84.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5008	50.08%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8693	86.93%
Skin irritation	-	0.6925	69.25%
Skin corrosion	-	0.8594	85.94%
Ames mutagenesis	-	0.6719	67.19%
Human Ether-a-go-go-Related Gene inhibition	+	0.8499	84.99%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.7954	79.54%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6056	60.56%
Acute Oral Toxicity (c)	III	0.3657	36.57%
Estrogen receptor binding	+	0.8871	88.71%
Androgen receptor binding	+	0.7550	75.50%
Thyroid receptor binding	+	0.7521	75.21%
Glucocorticoid receptor binding	+	0.8436	84.36%
Aromatase binding	+	0.7722	77.22%
PPAR gamma	+	0.7214	72.14%
Honey bee toxicity	-	0.8238	82.38%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	11220.2 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	12589.3 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	28183.8 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	10000 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	97.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.13%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.69%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.83%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.20%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.76%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.63%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.92%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.76%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.53%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.53%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.59%	91.19%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.57%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.09%	99.23%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.93%	94.23%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Azadirachta indica

Cedrela odorata

Cedrela salvadorensis

Entandrophragma angolense