cis-Isohumulone

Details

• Internal ID: 6169ffa4-bd96-42c8-b0d5-6689a0f2a96d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: (4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
• SMILES (Canonical): CC(C)CC(=O)C1=C(C(C(C1=O)CC=C(C)C)(C(=O)CC=C(C)C)O)O
• SMILES (Isomeric): CC(C)CC(=O)C1=C([C@]([C@@H](C1=O)CC=C(C)C)(C(=O)CC=C(C)C)O)O
• InChI: InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3/t15-,21+/m1/s1
• InChI Key: QARXXMMQVDCYGZ-VFNWGFHPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.50 g/mol
• Exact Mass: 362.20932405 g/mol
• Topological Polar Surface Area (TPSA): 91.70 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• Isohumulone B
• Isohumulone A1
• Isohumulone, cis-(+)-
• (+)-cis-Isohumulone
• 1534-03-8
• UNII-V3K20018SL
• V3K20018SL
• (4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
• 2-Cyclopenten-1-one, 3,4-dihydroxy-2-isovaleryl-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-, stereoisomer
• 2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-penten-1-yl)-, (4R,5S)-
• 2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-, (4R,5S)-
• 2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-, (4R-cis)-
• (+)-cis isohumulone
• cis-(+)-isohumulone
• SCHEMBL820691
• QARXXMMQVDCYGZ-VFNWGFHPSA-N
• Q27291492
• 2-Cyclopenten-1-one, 3,4-dihydroxy-2-isovaleryl-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-, ()-, stereoisomer

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9647	96.47%
Caco-2	+	0.5113	51.13%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7843	78.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8898	88.98%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5752	57.52%
P-glycoprotein inhibitior	-	0.7264	72.64%
P-glycoprotein substrate	-	0.6717	67.17%
CYP3A4 substrate	+	0.5532	55.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.9186	91.86%
CYP2C9 inhibition	-	0.8322	83.22%
CYP2C19 inhibition	-	0.7575	75.75%
CYP2D6 inhibition	-	0.9127	91.27%
CYP1A2 inhibition	-	0.8623	86.23%
CYP2C8 inhibition	-	0.8959	89.59%
CYP inhibitory promiscuity	-	0.9397	93.97%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9023	90.23%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9770	97.70%
Eye irritation	-	0.7959	79.59%
Skin irritation	-	0.5970	59.70%
Skin corrosion	-	0.8993	89.93%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7700	77.00%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.5712	57.12%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.7336	73.36%
Acute Oral Toxicity (c)	II	0.4128	41.28%
Estrogen receptor binding	+	0.5494	54.94%
Androgen receptor binding	+	0.5437	54.37%
Thyroid receptor binding	-	0.5291	52.91%
Glucocorticoid receptor binding	+	0.6876	68.76%
Aromatase binding	+	0.5915	59.15%
PPAR gamma	+	0.8725	87.25%
Honey bee toxicity	-	0.8293	82.93%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9754	97.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.84%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.89%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.31%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	90.36%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.04%	89.34%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.09%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.81%	96.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.58%	96.47%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.12%	91.24%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 21594782
• NPASS: NPC229225