Zerumin A

Details

• Internal ID: a6cfe57f-47d7-4034-ba78-9e75ffe2e904
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-formylpent-3-enoic acid
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2CC=C(CC(=O)O)C=O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CCC(=C)[C@@H]2C/C=C(/CC(=O)O)\C=O)(C)C
• InChI: InChI=1S/C20H30O3/c1-14-6-9-17-19(2,3)10-5-11-20(17,4)16(14)8-7-15(13-21)12-18(22)23/h7,13,16-17H,1,5-6,8-12H2,2-4H3,(H,22,23)/b15-7-/t16-,17-,20+/m0/s1
• InChI Key: ZAWWSYIDZKWRAI-DTFKRFDDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.78
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• CHEMBL2332435
• (Z)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-formylpent-3-enoic acid
• 176050-48-9
• BDBM50429856
• AKOS040735558

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.5754	57.54%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6404	64.04%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8344	83.44%
OATP1B3 inhibitior	+	0.8388	83.88%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6406	64.06%
P-glycoprotein inhibitior	-	0.6900	69.00%
P-glycoprotein substrate	-	0.8275	82.75%
CYP3A4 substrate	+	0.6192	61.92%
CYP2C9 substrate	-	0.7859	78.59%
CYP2D6 substrate	-	0.9118	91.18%
CYP3A4 inhibition	-	0.6213	62.13%
CYP2C9 inhibition	-	0.8779	87.79%
CYP2C19 inhibition	-	0.8716	87.16%
CYP2D6 inhibition	-	0.9438	94.38%
CYP1A2 inhibition	-	0.9106	91.06%
CYP2C8 inhibition	-	0.6105	61.05%
CYP inhibitory promiscuity	-	0.9110	91.10%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6950	69.50%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8233	82.33%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7736	77.36%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5976	59.76%
skin sensitisation	+	0.6983	69.83%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6836	68.36%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6039	60.39%
Acute Oral Toxicity (c)	III	0.7921	79.21%
Estrogen receptor binding	+	0.5800	58.00%
Androgen receptor binding	+	0.5342	53.42%
Thyroid receptor binding	+	0.5801	58.01%
Glucocorticoid receptor binding	+	0.6296	62.96%
Aromatase binding	-	0.5063	50.63%
PPAR gamma	+	0.7550	75.50%
Honey bee toxicity	-	0.9323	93.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	10400 nM	IC50	PMID: 23387824
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	7400 nM	IC50	PMID: 23387824

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.82%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.15%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	87.96%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.79%	97.25%
CHEMBL2581	P07339	Cathepsin D	87.18%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.76%	94.45%
CHEMBL5028	O14672	ADAM10	86.42%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	84.66%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.93%	95.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.80%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.77%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.87%	94.33%

Plants that contains it

• Acacia linarioides
• Alpinia calcarata
• Alpinia zerumbet
• Anadenanthera colubrina
• Aquilegia viridiflora
• Astragalus kabadianus
• Brombya platynema
• Cerbera odollam
• Cichorium endivia
• Clinopodium gracile
• Coelogyne prolifera
• Curcuma heyneana
• Daphne arisanensis
• Denhamia disperma
• Guadua angustifolia
• Hedychium coronarium
• Jaborosa leucotricha
• Kiggelaria africana
• Lippia abyssinica
• Lupinus luteus
• Morinda morindoides
• Perymenium jelskii
• Phenax angustifolius
• Potentilla candicans
• Prunus mahaleb
• Rhamnus cathartica
• Rhamnus formosana
• Senecio ruwenzoriensis
• Senna didymobotrya
• Spiraea formosana
• Strychnos elaeocarpa
• Strychnos wallichiana
• Tinadendron noumeanum
• Trichilia havanensis
• Tripterospermum lanceolatum
• Vachellia leucophloea
• Veronica liwanensis
• Viburnum betulifolium
• Zingiber ottensii

Cross-Links

• PubChem: 11723433
• NPASS: NPC75485
• ChEMBL: CHEMBL2332435
• LOTUS: LTS0238581
• wikiData: Q104399475