7,8-dehydrocalotropin - Compound Card

7,8-dehydrocalotropin

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7,8-dehydrocalotropin

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=C1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
InChI InChI=1S/C29H38O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h4,10,14-15,17-19,21-23,25,31,33-34H,3,5-9,11-13H2,1-2H3/t15-,17+,18-,19+,21-,22-,23+,25+,26-,27-,28+,29+/m1/s1
InChIKey LYTOHESBUGTAQI-XUJBKRNKSA-N
Formula C29H38O9
HBA 9
HBD 3
MW 530.61
Rotatable Bonds 2
TPSA 131.75
LogP 1.92
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 530.25
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Gomphocarpus sinaicus Apocynaceae Plantae 2291033

Showing of synonyms

  • Abdel-Azim NS, Hammouda FM, et al. (1996). Re-investigation of the cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1996,42(2),523-529. [View]
Pubchem: 390666
Nmrshiftdb2: 70013527

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7

Level: 1

Mol. Weight: 530.61 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2=CCC4C3CC5C(C4)OC6C(O5)CCCO6

Level: 0

Mol. Weight: 530.61 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 530.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.27
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
53.49
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
4.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.87
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.54
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.2
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
-2939.81
Rat (Acute)
4.87
Rat (Chronic Oral)
1.72
Fathead Minnow
9.76
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
439.81
Hydration Free Energy
-2.91
Log(D) at pH=7.4
2.49
Log(P)
0.8
Log S
-3.88
Log(Vapor Pressure)
-10.25
Melting Point
251.66
pKa Acid
5.95
pKa Basic
4.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8504
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8504
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8020
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8020
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7074
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7074

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