alpha-Lupulic acid

Details

• Internal ID: f39dcc5c-2a09-41c3-91ee-c5e1c7810d05
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Acyloins
• IUPAC Name: (6S)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• SMILES (Isomeric): CC(C)CC(=O)C1=C(C(=C([C@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• InChI: InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m0/s1
• InChI Key: VMSLCPKYRPDHLN-NRFANRHFSA-N
• Popularity: 64 references 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): 94.80 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.25
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• .alpha.-Bitter acid
• .alpha.-Lupulic acid
• NSC56351
• UNII-KHB4767H3K
• CCRIS 7249
• KHB4767H3K
• EINECS 247-725-0
• NSC 56351
• NSC-56351
• n-humulone
• 3,5,6beta-Trihydroxy-2-isovaleryl-4,6alpha-bis(3-methyl-2-butenyl)-2,4-cyclohexadienon
• 2',3'-Dihydro-3'beta,4',6'-trihydroxy-3'alpha,5'-bis(3-methyl-2-butenyl)-2'-oxoisovalerophenon
• Humolon
• 1,4,6-Trihydroxy-1,3-bis(2-isopentenyl)-5-isovaleryl-3,5-cyclohexadien-2-on
• (-)-humulone
• HUMULON [MI]
• CHEMBL463491
• SCHEMBL6125218
• DTXSID601019084
• DTXSID901019083
• (6R)-3,5,6-Trihydroxy-4,6-bis(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
• AKOS015896738
• Q28362389
• (6R)-3,5,6-TRIHYDROXY-4,6-BIS(3-METHYL-2-BUTENYL)-2-(3-METHYL-1-OXOBUTYL)-2,4-CYCLOHEXADIEN-1-ONE
• (6R)-3,5,6-Trihydroxy-4-(3-methylbutanoyl)-2,6-bis(3-methyl-2-buten-1-yl)-2,4-cyclohexadien-1-one
• (6R)-3,5,6-trihydroxy-4-(3-methylbutanoyl)-2,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• (6S)-3,5,6-Trihydroxy-4,6-bis(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
• 1263285-59-1
• 176022-26-7
• 2-Cyclohexadien-1-one, 3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-, 6(R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9470	94.70%
Caco-2	+	0.5177	51.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7691	76.91%
OATP2B1 inhibitior	-	0.5705	57.05%
OATP1B1 inhibitior	+	0.8852	88.52%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8448	84.48%
P-glycoprotein inhibitior	-	0.8623	86.23%
P-glycoprotein substrate	-	0.7157	71.57%
CYP3A4 substrate	+	0.5061	50.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.8410	84.10%
CYP2C9 inhibition	-	0.8449	84.49%
CYP2C19 inhibition	-	0.7358	73.58%
CYP2D6 inhibition	-	0.9062	90.62%
CYP1A2 inhibition	-	0.9235	92.35%
CYP2C8 inhibition	-	0.9067	90.67%
CYP inhibitory promiscuity	-	0.9491	94.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6776	67.76%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.5769	57.69%
Skin irritation	-	0.6171	61.71%
Skin corrosion	-	0.9183	91.83%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6798	67.98%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	+	0.7054	70.54%
skin sensitisation	-	0.5401	54.01%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7742	77.42%
Acute Oral Toxicity (c)	II	0.3666	36.66%
Estrogen receptor binding	+	0.6003	60.03%
Androgen receptor binding	+	0.5259	52.59%
Thyroid receptor binding	-	0.5495	54.95%
Glucocorticoid receptor binding	+	0.7939	79.39%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.7915	79.15%
Honey bee toxicity	-	0.8574	85.74%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9721	97.21%

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	95.61%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.24%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.57%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	90.33%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.43%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.95%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.36%	85.14%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.20%	83.10%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.84%	91.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.75%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	80.74%	94.73%

Plants that contains it

• Alkanna cappadocica
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Crambe tatarica
• Diospyros eriantha
• Fritillaria monantha
• Hoffmannia strigillosa
• Humulus lupulus
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Pteris semipinnata
• Salvia hispanica
• Scorzonera pseudodivaricata
• Stenocereus griseus
• Syncarpia hillii

Cross-Links

• PubChem: 72625
• NPASS: NPC287154
• LOTUS: LTS0086907
• wikiData: Q28362389