Olivil

Details

• Internal ID: badfd9b7-32ea-4bce-98f7-c3262f095e72
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,9-epoxylignans
• IUPAC Name: (3S,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2(COC(C2CO)C3=CC(=C(C=C3)O)OC)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@]2(CO[C@@H]([C@H]2CO)C3=CC(=C(C=C3)O)OC)O)O
• InChI: InChI=1S/C20H24O7/c1-25-17-7-12(3-5-15(17)22)9-20(24)11-27-19(14(20)10-21)13-4-6-16(23)18(8-13)26-2/h3-8,14,19,21-24H,9-11H2,1-2H3/t14-,19-,20-/m1/s1
• InChI Key: BVHIKUCXNBQDEM-JSNMRZPZSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.15220310 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.77
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• (-)-Olivil
• 2955-23-9
• Olivil [MI]
• (-)-Olivile
• UNII-P22CU5PR9T
• P22CU5PR9T
• (3S,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol
• 3-Furanmethanol, tetrahydro-4-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2S,3R,4S)-
• (-)-Olivile; Vladinol C
• (-)-Olivir
• SCHEMBL2979176
• AKOS032962306
• Q27286020
• (3S,4R,5S)-5-(4-hydroxy-3-methoxy-phenyl)-3-[(4-hydroxy-3-methoxy-phenyl)methyl]-4-(hydroxymethyl)tetrahydrofuran-3-ol
• [2S-(2-alpha,3-beta,4-alpha)]-Tetrahydro-4-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-furanmethanol
• 3-Furanmethanol, 2-(4-hydroxy-3-methoxyphenyl)tetrahydro-4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (2S,3R,4S)-
• 3-Furanmethanol, tetrahydro-4-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, [2S-(2.alpha.,3.beta.,4.alpha.)]-
• 3-Furanmethanol, tetrahydro-4-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-vanillyl-, stereoisomer

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8737	87.37%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7825	78.25%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5668	56.68%
P-glycoprotein inhibitior	+	0.5935	59.35%
P-glycoprotein substrate	-	0.7385	73.85%
CYP3A4 substrate	+	0.5741	57.41%
CYP2C9 substrate	-	0.7924	79.24%
CYP2D6 substrate	-	0.6715	67.15%
CYP3A4 inhibition	-	0.7101	71.01%
CYP2C9 inhibition	-	0.7071	70.71%
CYP2C19 inhibition	-	0.6443	64.43%
CYP2D6 inhibition	-	0.9041	90.41%
CYP1A2 inhibition	-	0.7460	74.60%
CYP2C8 inhibition	+	0.6924	69.24%
CYP inhibitory promiscuity	+	0.5930	59.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5868	58.68%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8735	87.35%
Skin irritation	-	0.8278	82.78%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7717	77.17%
Micronuclear	-	0.5126	51.26%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8388	83.88%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7320	73.20%
Acute Oral Toxicity (c)	III	0.6285	62.85%
Estrogen receptor binding	+	0.8652	86.52%
Androgen receptor binding	+	0.6451	64.51%
Thyroid receptor binding	+	0.6947	69.47%
Glucocorticoid receptor binding	+	0.6291	62.91%
Aromatase binding	+	0.5977	59.77%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8923	89.23%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8594	85.94%

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	99.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.84%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.00%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.92%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.62%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.88%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.52%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.12%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.75%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.58%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.37%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.02%	99.17%
CHEMBL2535	P11166	Glucose transporter	83.46%	98.75%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.10%	97.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.63%	92.94%

Plants that contains it

• Acer carpinifolium
• Cerbera manghas
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium sagittatum
• Eucommia ulmoides
• Fraxinus mandshurica
• Galium rubioides
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hypericum revolutum
• Jasminum officinale
• Leuzea centauroides
• Litsea salicifolia
• Mesembryanthemum expansum
• Olea europaea
• Osmorhiza aristata
• Premna corymbosa
• Psychotria serpens
• Pycnandra acuminata
• Rosa multiflora
• Stereospermum cylindricum
• Stereospermum kunthianum
• Stipa robusta
• Strophanthus gratus
• Succisa pratensis
• Viburnum foetidum

Cross-Links

• PubChem: 5273570
• NPASS: NPC93953
• LOTUS: LTS0178537
• wikiData: Q27286020