4a,5-Dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene

Details

• Internal ID: 745ef2d0-ede5-4704-bfdf-2571c8f688b4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: 4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
• SMILES (Canonical): CC1CCC=C2C1(CC(CC2)C(=C)C)C
• SMILES (Isomeric): CC1CCC=C2C1(CC(CC2)C(=C)C)C
• InChI: InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3
• InChI Key: QEBNYNLSCGVZOH-UHFFFAOYSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35 g/mol
• Exact Mass: 204.187800766 g/mol
• Topological Polar Surface Area (TPSA): 0.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.73
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
• Valencene (natural)
• Oxo-Tremorine
• NSC-148969
• Valencene 85
• 4.alpha.,9-octalin
• 4.beta.H,11-diene
• 4.beta.H,5.alpha.-Eremophila-1(10),11-diene
• 3-Isopropenyl-4a,5-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene #
• DTXSID60859879
• (3R,4aS,5R)-4a,5-Dimethyl-3-isopropenyl-1,2,3,4,4a,5,6,7-octahydronaphthalene
• QEBNYNLSCGVZOH-UHFFFAOYSA-N
• Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, [1R-(1.alpha.,7.beta.,8a.alpha.)]-
• Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, [1S-(1.alpha.,7.alpha.,8a.alpha.)]-
• NSC148969
• AKOS015955612
• VS-08621
• CS-0331354
• FT-0772964
• 4beta H,5alpha -Eremophila-1(10),11-diene
• Naphthalene,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, [1R-(1.alpha.,7.beta.,8a.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.9131	91.31%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Lysosomes	0.7353	73.53%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9407	94.07%
OATP1B3 inhibitior	+	0.8581	85.81%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7672	76.72%
P-glycoprotein inhibitior	-	0.9390	93.90%
P-glycoprotein substrate	-	0.8368	83.68%
CYP3A4 substrate	-	0.5102	51.02%
CYP2C9 substrate	-	0.7731	77.31%
CYP2D6 substrate	-	0.7252	72.52%
CYP3A4 inhibition	-	0.7864	78.64%
CYP2C9 inhibition	-	0.6915	69.15%
CYP2C19 inhibition	-	0.5906	59.06%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.7810	78.10%
CYP2C8 inhibition	-	0.7208	72.08%
CYP inhibitory promiscuity	-	0.5706	57.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.4601	46.01%
Eye corrosion	-	0.9524	95.24%
Eye irritation	-	0.5129	51.29%
Skin irritation	-	0.6639	66.39%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4703	47.03%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	+	0.7720	77.20%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.6272	62.72%
Acute Oral Toxicity (c)	III	0.7804	78.04%
Estrogen receptor binding	-	0.8816	88.16%
Androgen receptor binding	-	0.7740	77.40%
Thyroid receptor binding	-	0.8320	83.20%
Glucocorticoid receptor binding	-	0.5424	54.24%
Aromatase binding	+	0.7488	74.88%
PPAR gamma	-	0.8261	82.61%
Honey bee toxicity	-	0.9124	91.24%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	94.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.59%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	92.57%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.53%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.97%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	88.79%	83.82%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.07%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.04%	97.09%
CHEMBL1871	P10275	Androgen Receptor	84.02%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.47%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.78%	90.00%
CHEMBL2581	P07339	Cathepsin D	81.34%	98.95%

Plants that contains it

• Alpinia chinensis
• Bupleurum gibraltaricum
• Callicarpa americana
• Cinnamomum parthenoxylon
• Citrus × aurantium
• Croton eluteria
• Cryptocarya agathophylla
• Cynara cardunculus
• Cyperus rotundus
• Daniellia oliveri
• Dumortiera hirsuta
• Garcinia mangostana
• Grindelia hirsutula
• Helichrysum bracteiferum
• Helichrysum odoratissimum
• Hypericum hyssopifolium
• Hyptis suaveolens
• Juniperus comitana
• Lepechinia floribunda
• Ligularia cyathiceps
• Ligularia franchetiana
• Ligularia kanaitzensis
• Ligularia lamarum
• Ligularia subspicata
• Ligularia vellerea
• Ligularia virgaurea
• Lippia multiflora
• Marsupella emarginata
• Oenanthe aquatica
• Parthenium confertum
• Persea americana
• Persicaria minor
• Petasites hybridus subsp. hybridus
• Porella acutifolia
• Tanacetum annuum
• Thymus nummularius
• Valeriana jatamansi
• Virola surinamensis
• Xylopia sericea

Cross-Links

• PubChem: 288227
• LOTUS: LTS0031707
• wikiData: Q105219112