Guaiazulene

Details

• Internal ID: add6b24c-69ec-4c54-a902-34d6d102c2d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: 1,4-dimethyl-7-propan-2-ylazulene
• InChI: InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
• InChI Key: FWKQNCXZGNBPFD-UHFFFAOYSA-N
• Popularity: 409 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈
• Molecular Weight: 198.30 g/mol
• Exact Mass: 198.140850574 g/mol
• Topological Polar Surface Area (TPSA): 0.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.53
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 489-84-9
• 1,4-Dimethyl-7-isopropylazulene
• Vetivazulen
• 7-Isopropyl-1,4-dimethylazulene
• Azulon
• Kessazulen
• Purazulen
• Silazulon
• Uroazulen
• Azunol
• S-Guaiazulene
• guaiazulen
• Guajazulene
• 1,4-dimethyl-7-propan-2-ylazulene
• 3,8-Dimethyl-5-(2-propyl)azulene
• Vaumigan
• Azulene, 1,4-dimethyl-7-(1-methylethyl)-
• 1,4-Dimethyl-7-(1-methylethyl)azulene
• 1,4-dimethyl-7-(propan-2-yl)azulene
• 2OZ1K9JKQC
• NSC-4714
• CHEBI:5550
• DTXSID7045996
• DTXCID5025996
• RefChem:144607
• 207-701-2
• Eucazulen
• Guiazulene
• Cuteazul
• Gurjunazulen
• Azulen-beris
• Azulol
• hepatoprotectant
• NSC 4714
• Azulene, 7-isopropyl-1,4-dimethyl-
• AZ-8 beris
• Azunol (TN)
• 7-isopropyl-1,4-dimethyl-azulene
• AZULENE, 1,4-DIMETHYL-7-ISOPROPYL-
• MFCD00003811
• 1,4-Dimethyl-7-isopropyl-Azulene
• 1,4-Dimethyl-7-isopropylazulene (JAN)
• NCGC00095836-02
• Eucazulene
• CAS-489-84-9
• 1,4-DIMETHYL-7-ISOPROPYLAZULENE [JAN]
• 7-isopropyl- 1,4-dimethylazulene
• EINECS 207-701-2
• UNII-2OZ1K9JKQC
• BRN 1365001
• Guajazulen
• Kessazulene
• 1,3,5,7,9-Guaiapentaene
• Guaiazulene, 99%
• Azulene,4-dimethyl-
• Guaiazulene (Standard)
• Spectrum_001198
• GUAIAZULENE [MI]
• Spectrum2_001089
• Spectrum3_001537
• Spectrum4_000762
• Spectrum5_001090
• GUAIAZULENE [MART.]
• SCHEMBL26982
• BSPBio_002954
• GUAIAZULENE [WHO-DD]
• KBioGR_001144
• KBioSS_001678
• 4-05-00-01751 (Beilstein Handbook Reference)
• MLS002207286
• DivK1c_001006
• SPECTRUM1502249
• SPBio_001138
• AZ-8
• orb1304476
• 1,4-Dimethyl-7-isopropylazulen
• CHEMBL1408759
• SCHEMBL29639620
• HMS503I13
• HY-N6951R
• KBio1_001006
• KBio2_001678
• KBio2_004246
• KBio2_006814
• KBio3_002454
• Azulene,4-dimethyl-7-isopropyl-
• NSC4714
• NINDS_001006
• 1, 4-Dimethyl-7-isopropylazulene
• HMS5082D13
• HY-N6951
• Tox21_111526
• BBL027440
• CCG-40099
• s3995
• STK801958
• 1,4-dimethyl-7-(methylethyl)azulene
• AKOS001082716
• Tox21_111526_1
• DB13329
• FG34015
• LMPR0103410006
• SDCCGMLS-0066686.P001
• WLN: L57J B1 F1 IY1&1
• IDI1_001006
• Azulene,4-dimethyl-7-(1-methylethyl)-
• NCGC00095836-01
• NCGC00095836-03
• NCGC00095836-05
• NCGC00178373-01
• 1,4-dimethyl-7-(1-methylethyl)-azulene
• AS-13972
• SMR001306801
• ST098714
• DB-051592
• 1,4-Dimethyl-7-isopropylazulene;Guaiazulene
• Azulene, 7-isopropyl-1,4-dimethyl- (8CI)
• CS-0021588
• G0228
• NS00008692
• 7-isopropyl-1,4-dimethyl-azulene;Guaiazulene
• EN300-16623
• 1,4-Dimethyl-7-(1-methyl)-azulene (azulon)
• 1,4-Dimethyl-7-(1-methylethyl)azulene, 9CI
• A10803
• C09675
• D01037
• Z-1019
• A827639
• SR-05000002441
• GUAIAZULENE (CONSTITUENT OF CHAMOMILE) [DSC]
• Q3026266
• SR-05000002441-1
• BRD-K36719159-001-04-9
• Z56347227
• InChI=1/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.8760	87.60%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.8714	87.14%
Subcellular localzation	Lysosomes	0.7827	78.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9554	95.54%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5147	51.47%
P-glycoprotein inhibitior	-	0.9446	94.46%
P-glycoprotein substrate	-	0.8663	86.63%
CYP3A4 substrate	-	0.7434	74.34%
CYP2C9 substrate	-	0.7802	78.02%
CYP2D6 substrate	+	0.3462	34.62%
CYP3A4 inhibition	-	0.9298	92.98%
CYP2C9 inhibition	-	0.9051	90.51%
CYP2C19 inhibition	-	0.8945	89.45%
CYP2D6 inhibition	-	0.8698	86.98%
CYP1A2 inhibition	-	0.6173	61.73%
CYP2C8 inhibition	-	0.9694	96.94%
CYP inhibitory promiscuity	-	0.8212	82.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6200	62.00%
Carcinogenicity (trinary)	Warning	0.4146	41.46%
Eye corrosion	+	0.6733	67.33%
Eye irritation	+	0.9373	93.73%
Skin irritation	+	0.7366	73.66%
Skin corrosion	-	0.9481	94.81%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6516	65.16%
Micronuclear	-	0.8875	88.75%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	+	0.6918	69.18%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6923	69.23%
Acute Oral Toxicity (c)	III	0.7976	79.76%
Estrogen receptor binding	-	0.5961	59.61%
Androgen receptor binding	-	0.6312	63.12%
Thyroid receptor binding	-	0.5540	55.40%
Glucocorticoid receptor binding	-	0.7169	71.69%
Aromatase binding	-	0.6534	65.34%
PPAR gamma	-	0.8546	85.46%
Honey bee toxicity	-	0.9395	93.95%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9266	92.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.53%	98.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	93.13%	90.24%
CHEMBL260	Q16539	MAP kinase p38 alpha	92.81%	97.78%
CHEMBL1907	P15144	Aminopeptidase N	91.99%	93.31%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	88.30%	93.65%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.91%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.65%	94.73%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.48%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.34%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.55%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.13%	93.40%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.53%	99.15%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.49%	93.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.10%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.03%	91.11%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	82.58%	97.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.47%	90.71%
CHEMBL2337	P48067	Glycine transporter 1	81.57%	95.45%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	81.09%	95.70%
CHEMBL2039	P27338	Monoamine oxidase B	80.51%	92.51%

Plants that contains it

• Abrus melanospermus subsp. melanospermus
• Aquilaria malaccensis
• Artemisia thuscula
• Casearia corymbulosa
• Castanopsis eyrei
• Cedrela odorata
• Cinnamomum parthenoxylon
• Croton jacobinensis
• Ephedra sinica
• Eucalyptus decorticans
• Euryops rupestris
• Halocarpus kirkii
• Holarrhena pubescens
• Hymenophyllum nephrophyllum
• Hypericum carinatum
• Illicium difengpi
• Isodon loxothyrsus
• Juniperus excelsa
• Litchi chinensis
• Litsea verticillata
• Mastigophora diclados
• Micromeria juliana
• Mikania cordifolia
• Panax ginseng
• Persicaria mitis
• Santolina corsica
• Valeriana officinalis

Cross-Links

• PubChem: 3515
• NPASS: NPC297358
• ChEMBL: CHEMBL1408759
• LOTUS: LTS0214586
• wikiData: Q3026266