cis-Isohumulone

Details

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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

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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

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

2D Structure

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2D Structure of cis-Isohumulone

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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

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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.
Humulus lupulus

Cross-Links

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PubChem 21594782
NPASS NPC229225