6'-hydroxy-16alpha-acetoxycalactin - Compound Card

6'-hydroxy-16alpha-acetoxycalactin

Select a section from the left sidebar

6'-hydroxy-16alpha-acetoxycalactin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Cardenolide Glycoside
Canonical Smiles OC[C@@H]1C[C@@H](O)[C@]2([C@@H](O1)O[C@H]1[C@H](O2)C[C@]2([C@H](C1)CCC1C2CC[C@]2([C@]1(O)C[C@H]([C@@H]2C1=CC(=O)OC1)OC(=O)C)C)C=O)O
InChI InChI=1S/C31H42O12/c1-15(34)40-23-11-30(37)20-4-3-17-8-21-22(43-31(38)24(35)9-18(12-32)41-27(31)42-21)10-29(17,14-33)19(20)5-6-28(30,2)26(23)16-7-25(36)39-13-16/h7,14,17-24,26-27,32,35,37-38H,3-6,8-13H2,1-2H3/t17-,18-,19?,20?,21+,22+,23+,24+,26-,27-,28+,29+,30-,31-/m0/s1
InChIKey VKBDXZRKAYVFOV-AYZKNJJHSA-N
Formula C31H42O12
HBA 12
HBD 4
MW 606.67
Rotatable Bonds 4
TPSA 178.28
LogP 0.51
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.84
Exact Mass 606.27
Number of Lipinski Rule Violations 2
# 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: 162882801
Nmrshiftdb2: 70121405

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: 606.67 g/mol

Structure

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

Level: 0

Mol. Weight: 606.67 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 606.67 g/mol

Antiproliferative
Na+/k+-atpase inhibitory

Absorption

Caco-2 (logPapp)
-5.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.960
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
12.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.420
Plasma Protein Binding
55.96
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
0.530
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.770
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.780
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.600
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-26731.360
Rat (Acute)
5.150
Rat (Chronic Oral)
2.250
Fathead Minnow
49.460
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
594.770
Hydration Free Energy
-2.920
Log(D) at pH=7.4
1.690
Log(P)
-0.42
Log S
-2.97
Log(Vapor Pressure)
-10.33
Melting Point
244.78
pKa Acid
5.17
pKa Basic
4.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9251
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9251
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7337
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7337

Download SDF