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Amphipaniculoside D

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[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O)O)O)C
InChI	InChI=1S/C53H86O21/c1-22(2)10-9-11-23(3)32-26(69-45-40(63)36(59)28(20-55)70-45)18-50(7)29-12-13-30-51(8,48(66)74-44-41(64)37(60)33(56)24(4)67-44)31(14-15-52(30)21-53(29,52)17-16-49(32,50)6)72-47-43(39(62)34(57)25(5)68-47)73-46-42(65)38(61)35(58)27(19-54)71-46/h10,23-47,54-65H,9,11-21H2,1-8H3/t23-,24?,25?,26-,27?,28-,29?,30?,31+,32+,33+,34+,35-,36+,37+,38?,39+,40?,41?,42+,43?,44+,45-,46+,47+,49-,50+,51+,52-,53+/m1/s1
InChIKey	DTVJERQJXPAODQ-QBGDHTETSA-N
Formula	C₅₃H₈₆O₂₁
HBA	21
HBD	12
MW	1059.25
Rotatable Bonds	14
TPSA	333.67
LogP	-0.37
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	74
Formal Charge	0
Fraction CSP3	0.94
Exact Mass	1058.57
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: 162867142

Nmrshiftdb2: 70078202

No compound-protein relationship available.

SMILES: O1CCCCC1OC2C(OCCC2)OC(CC3)C(C(=O)OC4CCCCO4)C(C3(C567)C5)CCC6C8C(CC7)CC(C8)OC9CCCO9

Level: 4

Mol. Weight: 1059.25 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)C(C(=O)OC6CCCCO6)C(CC4)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1059.25 g/mol

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

Level: 3

Mol. Weight: 1059.25 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC(CC3)CC(C3(C456)C4)CCC5C7C(CC6)CC(C7)OC8CCCO8

Level: 3

Mol. Weight: 1059.25 g/mol

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

Level: 2

Mol. Weight: 1059.25 g/mol

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

Level: 2

Mol. Weight: 1059.25 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 1059.25 g/mol

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

Level: 2

Mol. Weight: 1059.25 g/mol

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

Level: 1

Mol. Weight: 1059.25 g/mol

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

Level: 1

Mol. Weight: 1059.25 g/mol

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

Level: 1

Mol. Weight: 1059.25 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1059.25 g/mol

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

Level: 0

Mol. Weight: 1059.25 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1059.25 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 1059.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.36
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 198741.250
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 25974006.6

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.680
Plasma Protein Binding: 80.32
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: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 1.450
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -604091.350
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.210
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.050
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: -47141566522.370
Rat (Acute): 4.130
Rat (Chronic Oral): 102.150
Fathead Minnow: 59506174.490
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 5302115085.310
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -2934.150
Log(P): 2.29
Log S: -3.9
Log(Vapor Pressure): -174595781.71
Melting Point: 272.98
pKa Acid: -1272109.76
pKa Basic: -10218.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7309
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7309
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7288
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7288
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7013
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7013

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