16alpha-hydroxycalactin - Compound Card

16alpha-hydroxycalactin

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16alpha-hydroxycalactin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Cardenolide Glycoside
Canonical Smiles O=C[C@]12C[C@H]3O[C@@]4(O)[C@H](O)C[C@H](O[C@H]4O[C@@H]3C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)C[C@H]([C@@H]2C1=CC(=O)OC1)O)C)C
InChI InChI=1S/C29H40O10/c1-14-7-22(32)29(35)25(37-14)38-20-9-16-3-4-18-17(27(16,13-30)11-21(20)39-29)5-6-26(2)24(15-8-23(33)36-12-15)19(31)10-28(18,26)34/h8,13-14,16-22,24-25,31-32,34-35H,3-7,9-12H2,1-2H3/t14-,16+,17+,18-,19-,20-,21-,22-,24+,25+,26-,27-,28+,29+/m1/s1
InChIKey MZUKFJRNNJXADZ-RZYUKCEPSA-N
Formula C29H40O10
HBA 10
HBD 4
MW 548.63
Rotatable Bonds 2
TPSA 151.98
LogP 0.97
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 548.26
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pergularia tomentosa Apocynaceae Plantae 264979

Showing of synonyms

  • Piacente S, Masullo M, et al. (2009). Cardenolides from Pergularia tomentosa display cytotoxic activity resulting from their potent inhibition of Na+/K+-ATPase. Journal of Natural Products,2009,72(2),1087-1091. [View] [PubMed]
Pubchem: 45270717
Nmrshiftdb2: 70053211

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7

Level: 1

Mol. Weight: 548.63 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)CCCO6

Level: 0

Mol. Weight: 548.63 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 548.63 g/mol

Antiproliferative
Na+/k+-atpase inhibitory

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.94
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
60.36
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
1.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.71
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.5
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.02
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Toxic
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4110.9
Rat (Acute)
5.12
Rat (Chronic Oral)
1.95
Fathead Minnow
12.38
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
420.95
Hydration Free Energy
-2.91
Log(D) at pH=7.4
2.2
Log(P)
-0.04
Log S
-3.25
Log(Vapor Pressure)
-10.67
Melting Point
257.21
pKa Acid
5.44
pKa Basic
4.8

No predicted protein targets found for this compound.

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