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Amphipaniculoside C

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Triterpenoid Glycoside

Canonical Smiles	OC[C@H]1O[C@H](C([C@H]1O)O)O[C@@H]1C[C@@]2([C@]([C@H]1[C@@H](CCC=C(C)C)C)(C)CC[C@@]13C2CCC2[C@]3(C1)CC[C@@H]([C@@]2(C)C(=O)O[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O)O[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O)C
InChI	InChI=1S/C47H76O16/c1-21(2)10-9-11-22(3)30-25(60-41-36(54)33(51)26(19-48)61-41)18-44(7)27-12-13-28-45(8,42(57)63-40-38(56)35(53)32(50)24(5)59-40)29(62-39-37(55)34(52)31(49)23(4)58-39)14-15-46(28)20-47(27,46)17-16-43(30,44)6/h10,22-41,48-56H,9,11-20H2,1-8H3/t22-,23?,24?,25-,26-,27?,28?,29+,30+,31+,32+,33+,34+,35+,36?,37?,38?,39+,40+,41-,43-,44+,45+,46-,47+/m1/s1
InChIKey	ITKGAUOSWSGWTN-FYVCSJOKSA-N
Formula	C₄₇H₇₆O₁₆
HBA	16
HBD	9
MW	897.11
Rotatable Bonds	11
TPSA	254.52
LogP	1.81
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	63
Formal Charge	0
Fraction CSP3	0.94
Exact Mass	896.51
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Amphilophium paniculatum	Bignoniaceae	Plantae	353927

Showing of synonyms

Samy MN, Khalil HE, et al. (2015). Amphipaniculosides A-D, triterpenoid glycosides, and amphipaniculoside E, an aliphatic alcohol glycoside from the leaves of Amphilophium paniculatum. Phytochemistry,2015,115,261-268. [View] [PubMed]

Pubchem: 162817417

Nmrshiftdb2: 70078206

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C(C(CC2)OC3CCCCO3)C(C2(C456)C4)CCC5C7C(CC6)CC(C7)OC8CCCO8

Level: 3

Mol. Weight: 897.11 g/mol

SMILES: O1CCCCC1OC(=O)C(C(CC2)OC3CCCCO3)C(C2(C456)C4)CCC5C7C(CC6)CCC7

Level: 2

Mol. Weight: 897.11 g/mol

SMILES: O1CCCCC1OC(=O)C(CCC2)C(C2(C345)C3)CCC4C6C(CC5)CC(C6)OC7CCCO7

Level: 2

Mol. Weight: 897.11 g/mol

SMILES: O1CCCCC1OC(CC2)CC(C2(C345)C3)CCC4C6C(CC5)CC(C6)OC7CCCO7

Level: 2

Mol. Weight: 897.11 g/mol

SMILES: O1CCCCC1OC(=O)C(CCC2)C(C2(C345)C3)CCC4C6C(CC5)CCC6

Level: 1

Mol. Weight: 897.11 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC6CCCCO6

Level: 1

Mol. Weight: 897.11 g/mol

SMILES: C1CCCC(C1(C234)C2)CCC3C5C(CC4)CC(C5)OC6CCCO6

Level: 1

Mol. Weight: 897.11 g/mol

SMILES: C1CCCC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 897.11 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 897.11 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 897.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.1
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 975.070
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 128188.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 96.81
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: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 2.250
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -2978.670
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.340
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.440
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: -232657622.730
Rat (Acute): 4.050
Rat (Chronic Oral): 4.800
Fathead Minnow: 293687.700
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 26164148.320
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 0.490
Log(P): 3.83
Log S: -4.5
Log(Vapor Pressure): -861428.2
Melting Point: 273.22
pKa Acid: -6193.67
pKa Basic: -18.84

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	4	0.8524
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	4	0.8524
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7505
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7505
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7363
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7363
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7122
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7122

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