Carnosifloside I

Details

• Internal ID: 0e818694-2891-46a9-bff2-2f8fbef3d0eb
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (3S,8S,9R,10R,13R,14S,17R)-3-hydroxy-4,4,9,13,14-pentamethyl-17-[(E,2R)-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC(CCC=C(C)COC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)C3CCC4(C3(CC(=O)C5(C4CC=C6C5CCC(C6(C)C)O)C)C)C
• SMILES (Isomeric): C[C@H](CC/C=C(\C)/CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)[C@H]3CC[C@@]4([C@@]3(CC(=O)[C@@]5([C@H]4CC=C6[C@H]5CC[C@@H](C6(C)C)O)C)C)C
• InChI: InChI=1S/C42H68O13/c1-21(19-52-37-36(51)34(49)32(47)27(55-37)20-53-38-35(50)33(48)31(46)26(18-43)54-38)9-8-10-22(2)23-15-16-40(5)28-13-11-24-25(12-14-29(44)39(24,3)4)42(28,7)30(45)17-41(23,40)6/h9,11,22-23,25-29,31-38,43-44,46-51H,8,10,12-20H2,1-7H3/b21-9+/t22-,23-,25-,26-,27-,28+,29+,31-,32-,33+,34+,35-,36-,37-,38-,40+,41-,42+/m1/s1
• InChI Key: FHOKVOIILRHONR-NOLKYRRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₈O₁₃
• Molecular Weight: 781.00 g/mol
• Exact Mass: 780.46599222 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• 109985-90-2
• C08790
• (3S,8S,9R,10R,13R,14S,17R)-3-hydroxy-4,4,9,13,14-pentamethyl-17-[(E,2R)-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• CHEBI:3425
• DTXSID50474616
• Q27106071
• (3S,8S,9R,10R,13R,14S,17R)-17-[(E,1R)-1,5-dimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-hex-4-enyl]-3-hydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8258	82.58%
Caco-2	-	0.8775	87.75%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8432	84.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8310	83.10%
OATP1B3 inhibitior	-	0.3515	35.15%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.8563	85.63%
P-glycoprotein inhibitior	+	0.7510	75.10%
P-glycoprotein substrate	+	0.5109	51.09%
CYP3A4 substrate	+	0.7218	72.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.9446	94.46%
CYP2C9 inhibition	-	0.8769	87.69%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9147	91.47%
CYP2C8 inhibition	+	0.5795	57.95%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9145	91.45%
Skin irritation	-	0.5396	53.96%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.7837	78.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7866	78.66%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6504	65.04%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6273	62.73%
Acute Oral Toxicity (c)	III	0.6642	66.42%
Estrogen receptor binding	+	0.7889	78.89%
Androgen receptor binding	+	0.7496	74.96%
Thyroid receptor binding	-	0.5637	56.37%
Glucocorticoid receptor binding	+	0.7236	72.36%
Aromatase binding	+	0.6821	68.21%
PPAR gamma	+	0.7372	73.72%
Honey bee toxicity	-	0.7322	73.22%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9477	94.77%

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	98.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.71%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	96.55%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.43%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.10%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.58%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.63%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.32%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.91%	93.56%
CHEMBL4581	P52732	Kinesin-like protein 1	85.41%	93.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.66%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.22%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.82%	93.00%
CHEMBL3401	O75469	Pregnane X receptor	83.71%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	83.59%	97.79%
CHEMBL5255	O00206	Toll-like receptor 4	82.87%	92.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.09%	90.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.01%	93.04%
CHEMBL1907	P15144	Aminopeptidase N	80.44%	93.31%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.20%	96.61%

Plants that contains it

• Aconitum carmichaelii
• Hemsleya carnosiflora
• Hemsleya panacis-scandens

Cross-Links

• PubChem: 11953915
• NPASS: NPC141718
• LOTUS: LTS0053264
• wikiData: Q27106071