Gamabufotalin

Details

• Internal ID: 249ad0c9-53e0-4c5a-8f98-ed8ac7c4667f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: 5-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
• SMILES (Canonical): CC12CCC(CC1CCC3C2C(CC4(C3(CCC4C5=COC(=O)C=C5)O)C)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2[C@@H](C[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O)O
• InChI: InChI=1S/C24H34O5/c1-22-9-7-16(25)11-15(22)4-5-18-21(22)19(26)12-23(2)17(8-10-24(18,23)28)14-3-6-20(27)29-13-14/h3,6,13,15-19,21,25-26,28H,4-5,7-12H2,1-2H3/t15-,16+,17-,18-,19-,21-,22+,23-,24+/m1/s1
• InChI Key: FMTLOAVOGWSPEF-KJRPADTMSA-N
• Popularity: 69 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₅
• Molecular Weight: 402.50 g/mol
• Exact Mass: 402.24062418 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 465-11-2
• Gamabufagin
• Gamabufogenin
• Gammabufotalin
• 5-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
• UNII-5HH3KM165O
• 5HH3KM165O
• CHEBI:80826
• NSC 90384
• NSC-90384
• Gamabufalin
• 3-beta,11-alpha,14-Trihydroxy-5-beta-bufa-20,22-dienolide
• GAMABUFOTALIN [MI]
• 5beta-Bufa-20,22-dienolide, 3beta,11alpha,14-trihydroxy-
• SCHEMBL866038
• 5-beta-BUFA-20,22-DIENOLIDE, 3-beta,11-alpha,14-TRIHYDROXY-
• CHEMBL465318
• Bufa-20,22-dienolide, 3,11,14-trihydroxy-, (3-beta,5-beta,11-alpha)-
• DTXSID40878664
• HY-N0883
• NSC90384
• MFCD01740822
• AKOS030526148
• CS-3701
• NCGC00485918-01
• AC-34676
• AS-77298
• C16962
• A827057
• Q-100490
• Q27149869
• 5.beta.-Bufa-20, 3.beta.,11.alpha.,14-trihydroxy-
• Bufa-20, 3,11,14-trihydroxy-, (3.beta.,5.beta.,11.alpha.)-
• (3-beta,5-beta,11-alpha)-3,11,14-Trihydroxybufa-20,22-dienolide
• (3.BETA.,5.BETA.,11.ALPHA.)-3,11,14-TRIHYDROXYBUFA-20,22-DIENOLIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	-	0.6773	67.73%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8181	81.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8622	86.22%
OATP1B3 inhibitior	+	0.9006	90.06%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8108	81.08%
BSEP inhibitior	+	0.7094	70.94%
P-glycoprotein inhibitior	-	0.7881	78.81%
P-glycoprotein substrate	-	0.7512	75.12%
CYP3A4 substrate	+	0.7197	71.97%
CYP2C9 substrate	-	0.7957	79.57%
CYP2D6 substrate	-	0.8281	82.81%
CYP3A4 inhibition	-	0.5796	57.96%
CYP2C9 inhibition	-	0.9318	93.18%
CYP2C19 inhibition	-	0.9263	92.63%
CYP2D6 inhibition	-	0.9495	94.95%
CYP1A2 inhibition	-	0.6989	69.89%
CYP2C8 inhibition	-	0.6313	63.13%
CYP inhibitory promiscuity	-	0.9365	93.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5815	58.15%
Eye corrosion	-	0.9951	99.51%
Eye irritation	-	0.9653	96.53%
Skin irritation	-	0.5486	54.86%
Skin corrosion	-	0.9189	91.89%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6649	66.49%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5949	59.49%
skin sensitisation	-	0.9066	90.66%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6279	62.79%
Acute Oral Toxicity (c)	III	0.3936	39.36%
Estrogen receptor binding	+	0.8748	87.48%
Androgen receptor binding	+	0.7744	77.44%
Thyroid receptor binding	+	0.5615	56.15%
Glucocorticoid receptor binding	+	0.7188	71.88%
Aromatase binding	+	0.7421	74.21%
PPAR gamma	+	0.6111	61.11%
Honey bee toxicity	-	0.8107	81.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	96.30%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.03%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.12%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.87%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.22%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.18%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.81%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.77%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	86.76%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.53%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.53%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.08%	93.04%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.05%	96.77%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.44%	96.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.25%	99.23%

Plants that contains it

• Aruncus dioicus
• Buxus sempervirens
• Dysoxylum lenticellatum
• Hesperocyparis macrocarpa
• Isocoma veneta
• Kochia trichophylla
• Leuzea carthamoides
• Nelumbo nucifera
• Petchia madagascariensis
• Piper kadsura
• Potentilla multifida
• Psephellus trinervius
• Saururus cernuus
• Seriphidium oranense
• Strychnos fendleri
• Vicia villosa
• Vitex megapotamica

Cross-Links

• PubChem: 259803
• NPASS: NPC295843
• LOTUS: LTS0148150
• wikiData: Q27149869