Amphipaniculoside B - Compound Card

Amphipaniculoside B

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Amphipaniculoside B

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid Glycoside
Canonical Smiles OCC1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@](C3C3=CCC4[C@@]([C@@]3(CC2)C)(C)CCC2[C@]4(C)C[C@H]([C@@H]([C@@]2(C)CO)O)O)(C)O)C)[C@H](C([C@@H]1O)O)O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C42H68O16/c1-19-9-12-42(36(53)58-35-31(29(50)27(48)23(17-44)56-35)57-34-30(51)28(49)26(47)22(16-43)55-34)14-13-39(4)20(32(42)41(19,6)54)7-8-25-37(2)15-21(46)33(52)38(3,18-45)24(37)10-11-40(25,39)5/h7,19,21-35,43-52,54H,8-18H2,1-6H3/t19-,21-,22?,23?,24?,25?,26-,27-,28?,29?,30+,31+,32?,33+,34+,35+,37+,38+,39-,40-,41-,42+/m1/s1
InChIKey RSNOJNCMDSVLCU-JPROIMBPSA-N
Formula C42H68O16
HBA 16
HBD 11
MW 828.99
Rotatable Bonds 7
TPSA 276.52
LogP -0.77
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 58
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 828.45
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: 162817419
Nmrshiftdb2: 70078204

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CCCC7

Level: 2

Mol. Weight: 828.99 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 828.99 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 828.99 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 828.99 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 828.99 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.47
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
52.24
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
7639.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
72.82
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
Non-Inhibitor

Excretion

Clearance
1.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-180.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.09
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-13863433.94
Rat (Acute)
3.95
Rat (Chronic Oral)
4.42
Fathead Minnow
17506.77
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
1555656.38
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.5
Log(P)
0.47
Log S
-3.02
Log(Vapor Pressure)
-51082.71
Melting Point
241.26
pKa Acid
-314.36
pKa Basic
5.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7277
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7277
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7137
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7137

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