ANPDB

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Angustifolioside B

Family: Plantae - Oleaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Secoiridoid Diglucoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2ccc(cc2)CCOC(=O)C[C@H]2/C(=C\C)/[C@@H](OC=C2C(=O)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C31H42O17/c1-3-16-17(18(28(41)42-2)13-44-29(16)48-31-27(40)25(38)23(36)20(12-33)47-31)10-21(34)43-9-8-14-4-6-15(7-5-14)45-30-26(39)24(37)22(35)19(11-32)46-30/h3-7,13,17,19-20,22-27,29-33,35-40H,8-12H2,1-2H3/b16-3+/t17-,19+,20+,22+,23+,24-,25-,26+,27+,29-,30+,31-/m0/s1
InChIKey	AZIMXRPUOIPIKL-DTYPFZMBSA-N
Formula	C₃₁H₄₂O₁₇
HBA	17
HBD	8
MW	686.66
Rotatable Bonds	12
TPSA	260.59
LogP	-2.87
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	48
Formal Charge	0
Fraction CSP3	0.61
Exact Mass	686.24
Number of Lipinski Rule Violations	3

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

Showing of synonyms

Calis I, Hosny M, et al. (1993). Secoiridoids from Fraxinus angustifolia. Phytochemistry,1993,33(6),1453-1456. [View]
Hosny M, Ca̧liş I, et al. (1991). Secoiridoids from Fraxinus angustifolia. Planta Medica,1991,2-A81. [View]

Pubchem: 101637167

Zinc: ZINC000255197534

Nmrshiftdb2: 60023924

No compound-protein relationship available.

SMILES: O1CCCCC1OC2OC=CC(C2=C)CC(=O)OCCc3ccc(cc3)OC4CCCCO4

Level: 3

Mol. Weight: 686.66 g/mol

SMILES: c1ccccc1CCOC(=O)CC(C2=C)C=COC2OC3CCCCO3

Level: 2

Mol. Weight: 686.66 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)OCCc2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 686.66 g/mol

SMILES: C1OC=CC(C1=C)CC(=O)OCCc2ccccc2

Level: 1

Mol. Weight: 686.66 g/mol

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 686.66 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 686.66 g/mol

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 686.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 686.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 686.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.39
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.830
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 79.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.800
Plasma Protein Binding: 72.84
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: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.180
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.200
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.800
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.230
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: -145902.310
Rat (Acute): 2.840
Rat (Chronic Oral): 5.160
Fathead Minnow: 198.800
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 10612.890
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 0.300
Log(P): -1.78
Log S: -2.13
Log(Vapor Pressure): -348.89
Melting Point: 200.14
pKa Acid: 3.28
pKa Basic: 2.64

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.9034
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.9034
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8890
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8890
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8411
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8411
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8368
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8368
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7887
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7887
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7775
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7775
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7707
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7707
Raucaffricine-O-beta-D-glucosidase	Q9SPP9	RG1_RAUSE	Rauvolfia serpentina	4	0.7449
Raucaffricine-O-beta-D-glucosidase	Q9SPP9	RG1_RAUSE	Rauvolfia serpentina	4	0.7449
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7379
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7379
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7368
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7368
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7366
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7366
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7341
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7341
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7309
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7309
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7304
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7304
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7260
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7260
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7233
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7233
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7197
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7197
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7178
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7178
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7154
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7154
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7101
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7101

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