Isoolivil

Details

• Internal ID: c2886bde-12c5-4945-b3d7-3253e57e6283
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans > 9,9p-dihydroxyaryltetralin lignans
• IUPAC Name: (2S,3S,4S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol
• SMILES (Canonical): COC1=C(C=C2C(C(C(CC2=C1)(CO)O)CO)C3=CC(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1=C(C=C2[C@@H]([C@H]([C@@](CC2=C1)(CO)O)CO)C3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C20H24O7/c1-26-17-5-11(3-4-15(17)23)19-13-7-16(24)18(27-2)6-12(13)8-20(25,10-22)14(19)9-21/h3-7,14,19,21-25H,8-10H2,1-2H3/t14-,19+,20-/m1/s1
• InChI Key: KCIQZCNOUZCRGH-VOBQZIQPSA-N
• Popularity: 7 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): 120.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.13
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• Isoolivil
• 3064-05-9
• rel-Isoolivil
• (+)-Cycloolivil
• (2S,3S,4S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol
• CHEMBL516536
• 163381-96-2
• 2,3-Naphthalenedimethanol, 1,2,3,4-tetrahydro-3,7-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-, (1S,2S,3S)-
• MEGxp0_001281
• SCHEMBL2902615
• Cycloolivil, analytical standard
• ACon1_001444
• CHEBI:167779
• DTXSID101347745
• HY-N3670
• BDBM50250506
• AKOS032949006
• Cycloolivil, >=95% (LC/MS-ELSD)
• CS-0024029
• BRD-K14461684-001-01-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9271	92.71%
Caco-2	+	0.5262	52.62%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6963	69.63%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9600	96.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6107	61.07%
P-glycoprotein inhibitior	-	0.6912	69.12%
P-glycoprotein substrate	-	0.6937	69.37%
CYP3A4 substrate	+	0.5862	58.62%
CYP2C9 substrate	-	0.5774	57.74%
CYP2D6 substrate	+	0.3843	38.43%
CYP3A4 inhibition	-	0.8017	80.17%
CYP2C9 inhibition	-	0.8825	88.25%
CYP2C19 inhibition	-	0.7100	71.00%
CYP2D6 inhibition	-	0.9141	91.41%
CYP1A2 inhibition	+	0.6736	67.36%
CYP2C8 inhibition	+	0.6388	63.88%
CYP inhibitory promiscuity	-	0.8395	83.95%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6096	60.96%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.7879	78.79%
Skin irritation	-	0.7986	79.86%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8067	80.67%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.8400	84.00%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6524	65.24%
Acute Oral Toxicity (c)	III	0.6784	67.84%
Estrogen receptor binding	+	0.8455	84.55%
Androgen receptor binding	+	0.5942	59.42%
Thyroid receptor binding	+	0.7776	77.76%
Glucocorticoid receptor binding	+	0.7569	75.69%
Aromatase binding	+	0.6481	64.81%
PPAR gamma	+	0.5898	58.98%
Honey bee toxicity	-	0.9067	90.67%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8792	87.92%

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	99.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.62%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.79%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.34%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.70%	95.89%
CHEMBL4208	P20618	Proteasome component C5	89.53%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.20%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.14%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.22%	92.94%
CHEMBL2581	P07339	Cathepsin D	87.98%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.71%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.48%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.73%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.30%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.50%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.84%	94.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.84%	89.62%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.61%	90.24%
CHEMBL3438	Q05513	Protein kinase C zeta	81.50%	88.48%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.20%	93.99%

Plants that contains it

• Acer carpinifolium
• Cerbera manghas
• Chamaecytisus austriacus
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium brevicornu
• Epimedium diphyllum
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense
• Eucommia ulmoides
• Fraxinus chinensis subsp. rhynchophylla
• Galium rubioides
• Gmelina asiatica
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hypericum revolutum
• Leuzea centauroides
• Litsea salicifolia
• Mesembryanthemum expansum
• Nestegis cunninghamii
• Olea europaea
• Osmorhiza aristata
• Psychotria serpens
• Pycnandra acuminata
• Sambucus williamsii
• Stereospermum acuminatissimum
• Stereospermum cylindricum
• Stereospermum kunthianum
• Stipa robusta
• Strychnos guianensis
• Succisa pratensis
• Tabebuia ochracea

Cross-Links

• PubChem: 5316262
• NPASS: NPC311256
• LOTUS: LTS0112294
• wikiData: Q104396243