6'-hydroxycalactin - Compound Card

6'-hydroxycalactin

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6'-hydroxycalactin

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)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C=O)O
InChI InChI=1S/C29H40O10/c1-26-6-4-19-20(28(26,34)7-5-18(26)15-8-24(33)36-13-15)3-2-16-9-21-22(11-27(16,19)14-31)39-29(35)23(32)10-17(12-30)37-25(29)38-21/h8,14,16-23,25,30,32,34-35H,2-7,9-13H2,1H3/t16-,17-,18+,19-,20+,21+,22+,23+,25-,26+,27+,28-,29-/m0/s1
InChIKey NXCIXUFRIWJEEC-KQERWQABSA-N
Formula C29H40O10
HBA 10
HBD 4
MW 548.63
Rotatable Bonds 3
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: 44179786
Nmrshiftdb2: 70053210

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)
-5.54
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.940
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.550
Plasma Protein Binding
60.29
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
0.990
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.870
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.740
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.570
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-5087.830
Rat (Acute)
4.720
Rat (Chronic Oral)
1.980
Fathead Minnow
13.950
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
403.520
Hydration Free Energy
-2.910
Log(D) at pH=7.4
2.170
Log(P)
0.22
Log S
-3.09
Log(Vapor Pressure)
-10.42
Melting Point
240.68
pKa Acid
6.03
pKa Basic
5.51
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 0.9158
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9158
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7366
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7366

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