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GI-3

Family: Plantae - Oleaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Tetracyclic Diterpenoid

Canonical Smiles	OC[C@H]1OC(O[C@H]2OC=C(C(/C/2=C/C)CC(=O)OC[C@H]2OC(OCCc3ccc(cc3)OC(=O)CC3/C(=C\C)/[C@@H](OC=C3C(=O)OC)OC3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C48H64O27/c1-5-22-24(26(42(62)64-3)17-68-44(22)74-47-40(60)36(56)33(53)28(15-49)71-47)13-31(51)67-19-30-35(55)38(58)39(59)46(73-30)66-12-11-20-7-9-21(10-8-20)70-32(52)14-25-23(6-2)45(69-18-27(25)43(63)65-4)75-48-41(61)37(57)34(54)29(16-50)72-48/h5-10,17-18,24-25,28-30,33-41,44-50,53-61H,11-16,19H2,1-4H3/b22-5-,23-6+/t24?,25?,28-,29-,30-,33-,34-,35-,36+,37+,38+,39-,40-,41-,44-,45+,46?,47?,48?/m1/s1
InChIKey	SMSRUMQQXKEQCV-RAHBEWDKSA-N
Formula	C₄₈H₆₄O₂₇
HBA	27
HBD	11
MW	1073.01
Rotatable Bonds	19
TPSA	401.57
LogP	-4.13
Number Rings	6
Number Aromatic Rings	1
Heavy Atom Count	75
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	1072.36
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fraxinus excelsior	Oleaceae	Plantae	38873
2	Fraxinus excelsior	Oleaceae	Plantae	38873
3	Fraxinus angustifolia	Oleaceae	Plantae	166594

Showing of synonyms

Ibarra A, Bai N, et al. (2011). Fraxinus excelsior seed extract FraxiPureTM limits weight gains and hyperglycemia in high-fat diet-induced obese mice. Phytomedicine,2011,18(6),479-485. [View]
Bai N, He K, et al. (2010). Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and PPARalpha activation activity. Journal of Natural Products,2010,73(1),2-6. [View] [PubMed]
García-Villalba R, Tomás-Barberán FA, et al. (2015). Targeted and untargeted metabolomics to explore the bioavailability of the secoiridoids from a seed/fruit extract (Fraxinus angustifolia Vahl) in human healthy volunteers: a preliminary study. Molecules,2015,20(12),22202-22219. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OC2OC=CC(C2=C)CC(=O)OCC3CCCC(O3)OCCc4ccc(cc4)OC(=O)CC(C5=C)C=COC5OC6CCCCO6

Level: 5

Mol. Weight: 1073.01 g/mol

SMILES: O1CCCCC1OC2OC=CC(C2=C)CC(=O)OCC3CCCC(O3)OCCc4ccc(cc4)OC(=O)CC(C5=C)C=COC5

Level: 4

Mol. Weight: 1073.01 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)OCC2CCCC(O2)OCCc3ccc(cc3)OC(=O)CC(C4=C)C=COC4OC5CCCCO5

Level: 4

Mol. Weight: 1073.01 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)OCC2CCCC(O2)OCCc3ccc(cc3)OC(=O)CC(C4=C)C=COC4

Level: 3

Mol. Weight: 1073.01 g/mol

SMILES: O1CCCCC1OC2OC=CC(C2=C)CC(=O)OCC3CCCC(O3)OCCc4ccccc4

Level: 3

Mol. Weight: 1073.01 g/mol

SMILES: O1CCCCC1OC2OC=CC(C2=C)CC(=O)Oc(cc3)ccc3CCOC4CCCCO4

Level: 3

Mol. Weight: 1073.01 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)OCC2CCCC(O2)OCCc3ccccc3

Level: 2

Mol. Weight: 1073.01 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)Oc(cc2)ccc2CCOC3CCCCO3

Level: 2

Mol. Weight: 1073.01 g/mol

SMILES: O1CCCCC1COC(=O)CC(C2=C)C=COC2OC3CCCCO3

Level: 2

Mol. Weight: 1073.01 g/mol

SMILES: c1ccccc1OC(=O)CC(C2=C)C=COC2OC3CCCCO3

Level: 2

Mol. Weight: 1073.01 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 1073.01 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)Oc2ccccc2

Level: 1

Mol. Weight: 1073.01 g/mol

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 1073.01 g/mol

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 1073.01 g/mol

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 1073.01 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1073.01 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1073.01 g/mol

Adipocyte differentiation-inhibitory

Antidiabetic

Antiobesity property

Absorption

Caco-2 (logPapp): -6.36
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 258165.14
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 33740028.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.58
Plasma Protein Binding: 36.83
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.08
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -784712.9
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.17
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -61236527367.39
Rat (Acute): 3.12
Rat (Chronic Oral): 133.63
Fathead Minnow: 77298035.99
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 6887404123.5
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -3819.68
Log(P): -2.51
Log S: -2.41
Log(Vapor Pressure): -226798665.3
Melting Point: 194.15
pKa Acid: -1652491.9
pKa Basic: -13285.34

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7689
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7689
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7044
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7044

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