(+)-Longifolene

Details

• Internal ID: afbd4084-8c80-433f-a89d-b277c8a0497d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.02,9]undecane
• SMILES (Canonical): CC1(CCCC2(C3C1C(C2=C)CC3)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]3[C@H]1CC[C@@H]3C2=C)(C)C
• InChI: InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1
• InChI Key: PDSNLYSELAIEBU-GUIRCDHDSA-N
• Popularity: 461 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: 5.10
• Atomic LogP (AlogP): 4.42
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 475-20-7
• Junipene
• Kuromatsuene
• Kuromatsuen
• Longifolen
• Junipen
• LONGIFOLENE
• (+)-Longifolen
• (1S,3aR,4S,8aS)-4,8,8-trimethyl-9-methylenedecahydro-1,4-methanoazulene
• 3YXH7YY8WM
• .alpha.-Longifolene
• DTXSID9047045
• CHEBI:49282
• LONGIFOLENE [MI]
• EINECS 207-491-2
• NSC 150808
• DTXCID7027045
• (1S,3aR,4S,8aS)-(+)-decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
• (1S,3aR,4S,8aS)-4,8,8-trimethyl-9-methylidenedecahydro-1,4-methanoazulene
• 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, (1S,3aR,4S,8aS)-
• NSC-150808
• 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-
• 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, (1S-(1alpha,3abeta,4alpha,8abeta))
• 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, (1S-(1alpha,3abeta,4alpha,8abeta))-
• (1S-(1.ALPHA.,3A.BETA.,4.ALPHA.,8A.BETA.))DECAHYDRO-4,8,8-TRIMETHYL-9-METHYLENE-1,4-METHANOAZULENE
• 1,4-Methanoazulene, decahydro-9-methylene-4,8,8-trimethyl-, (1S-(1-alpha,3a-beta,4-alpha,8a-beta))-
• CHEBI:6530
• (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo(5.4.0.02,9)undecane
• (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.02,9]undecane
• 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, (1S,3aR,4S,8aS)-(+)-
• 1,4-METHANOAZULENE, DECAHYDRO-4,8,8-TRIMETHYL-9-METHYLENE-, (1S-(1.ALPHA.,3A.BETA.,4.ALPHA.,8A.BETA.))-
• ALPHA-LONGIFOLENE
• RefChem:800034
• LONGIFOLENE [INCI]
• 3,3,7-trimethyl-8-methylidenetricyclo(5.4.0.02,9)undecane
• 3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.02,9]undecane
• (1S-(1ALPHA,3ABETA,4ALPHA,8ABETA))DECAHYDRO-4,8,8-TRIMETHYL-9-METHYLENE-1,4-METHANOAZULENE
• 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, (1S-(1alpha,3abeta,4alpha,8abeta))-(9CI)
• d-Longifolene
• Longifolene (>75%)
• MFCD23380551
• [1S-(1alpha,3abeta,4alpha,8abeta)]-Decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
• UNII-3YXH7YY8WM
• (1S-(1alpha,3Abeta,4alpha,8abeta))-decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
• LONGIFORENE
• (+)-Longifolene (Standard)
• CHEMBL519092
• orb1685423
• SCHEMBL3693901
• HY-N6662R
• PDSNLYSELAIEBU-GUIRCDHDSA-N
• HY-N6662
• Tox21_302307
• MSK014167
• s5614
• AKOS030242126
• CCG-266608
• FL40142
• LMPR0103500017
• NCGC00256076-01
• AS-56611
• CAS-475-20-7
• SY410283
• CS-0083201
• Q6673936
• (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylene-tricyclo[5.4.0.02,9]undecane

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.7297	72.97%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.7752	77.52%
OATP2B1 inhibitior	-	0.8448	84.48%
OATP1B1 inhibitior	+	0.8707	87.07%
OATP1B3 inhibitior	+	0.8296	82.96%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8896	88.96%
P-glycoprotein inhibitior	-	0.9267	92.67%
P-glycoprotein substrate	-	0.9392	93.92%
CYP3A4 substrate	+	0.5362	53.62%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.7441	74.41%
CYP3A4 inhibition	-	0.8639	86.39%
CYP2C9 inhibition	-	0.7857	78.57%
CYP2C19 inhibition	-	0.7457	74.57%
CYP2D6 inhibition	-	0.9386	93.86%
CYP1A2 inhibition	-	0.7484	74.84%
CYP2C8 inhibition	-	0.6354	63.54%
CYP inhibitory promiscuity	-	0.6722	67.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.4950	49.50%
Eye corrosion	-	0.9480	94.80%
Eye irritation	+	0.9708	97.08%
Skin irritation	+	0.5266	52.66%
Skin corrosion	-	0.9769	97.69%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5492	54.92%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6517	65.17%
skin sensitisation	+	0.8187	81.87%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.4655	46.55%
Acute Oral Toxicity (c)	III	0.7957	79.57%
Estrogen receptor binding	-	0.8790	87.90%
Androgen receptor binding	+	0.5904	59.04%
Thyroid receptor binding	-	0.8098	80.98%
Glucocorticoid receptor binding	-	0.6194	61.94%
Aromatase binding	-	0.7369	73.69%
PPAR gamma	-	0.8146	81.46%
Honey bee toxicity	-	0.8612	86.12%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.9200	92.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.78%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.84%	91.11%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	89.81%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.00%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.57%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.50%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.10%	100.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.15%	99.18%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.06%	92.94%
CHEMBL238	Q01959	Dopamine transporter	83.97%	95.88%
CHEMBL233	P35372	Mu opioid receptor	83.63%	97.93%
CHEMBL237	P41145	Kappa opioid receptor	82.57%	98.10%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.53%	95.50%

Plants that contains it

• Abies magnifica
• Acacia simplicifolia
• Acorus calamus
• Acorus gramineus
• Ammodendron karelinii
• Anacyclus pyrethrum
• Aquilaria malaccensis
• Aquilaria sinensis
• Aster tataricus
• Bellardia trixago
• Bowdichia virgilioides
• Brachylaena perrieri
• Buglossoides arvensis
• Cedrela fissilis
• Centaurea zuccariniana
• Cinnamomum philippinense
• Cousinia canescens
• Crinum jagus
• Crocus sativus
• Cuscuta australis
• Cyperus rotundus
• Daucus carota
• Diplotropis ferruginea
• Elettaria cardamomum
• Eucalyptus viminalis
• Euphrasia regelii
• Firmiana simplex
• Halocarpus biformis
• Herbertus dicranus
• Hortonia angustifolia
• Illicium verum
• Julbernardia globiflora
• Laggera crispata
• Larix gmelinii var. gmelinii
• Manoao colensoi
• Medicosma fareana
• Mentha longifolia subsp. longifolia
• Mikania grazielae
• Miliusa balansae
• Mimusops laurifolia
• Mosla chinensis
• Myrrhis odorata
• Nauclea parva
• Othonna macrophylla
• Pentachondra pumila
• Phagnalon rupestre
• Phlomoides ostrowskiana
• Phlox paniculata
• Picea abies
• Piliostigma thonningii
• Pimpinella peregrina
• Pinus brutia var. pityusa
• Pinus monticola
• Pinus palustris
• Pinus ponderosa
• Piper betle
• Prumnopitys andina
• Salix petiolaris
• Salvia lanigera
• Salvia pisidica
• Scutellaria baicalensis
• Senna alexandrina
• Solanum crinitum
• Symplocos glauca
• Teucrium scorodonia
• Tinospora hainanensis
• Titanotrichum oldhamii
• Tubocapsicum anomalum
• Uncaria longiflora
• Ursinia speciosa
• Uvaria littoralis
• Veronica anagallis
• Waitzia acuminata
• Wrightia tinctoria

Cross-Links

• PubChem: 1796220
• NPASS: NPC229403
• LOTUS: LTS0248662
• wikiData: Q6673936