17alpha-hydroxy-7,8-dehydrocalotropin - Compound Card

17alpha-hydroxy-7,8-dehydrocalotropin

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17alpha-hydroxy-7,8-dehydrocalotropin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Cardenolide Glycoside
Canonical Smiles OC[C@]12CC[C@@H](C[C@@H]1CC=C1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)O[C@@H]1OC(O)[C@@H](C([C@@H]1O)O)O
InChI InChI=1S/C28H40O10/c1-26-7-5-18-19(28(26,35)9-6-17(26)14-10-20(30)36-12-14)3-2-15-11-16(4-8-27(15,18)13-29)37-25-23(33)21(31)22(32)24(34)38-25/h3,10,15-18,21-25,29,31-35H,2,4-9,11-13H2,1H3/t15-,16-,17+,18-,21?,22+,23-,24?,25+,26+,27+,28-/m0/s1
InChIKey FQCNSQJHPSOGHM-CKORDJMKSA-N
Formula C28H40O10
HBA 10
HBD 6
MW 536.62
Rotatable Bonds 4
TPSA 166.14
LogP 0.28
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 536.26
Number of Lipinski Rule Violations 2
# 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: 162817531
Nmrshiftdb2: 70013531

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 2

Mol. Weight: 536.62 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 536.62 g/mol

Structure

SMILES: C1OC(=O)C=C1C2CCC(C23)C=4C(CC3)C5C(CC4)CCCC5

Level: 1

Mol. Weight: 536.62 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCCC4

Level: 0

Mol. Weight: 536.62 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 536.62 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 536.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.2
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
69.12
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
0.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.28
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.13
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.97
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
-2469.79
Rat (Acute)
3.64
Rat (Chronic Oral)
3.1
Fathead Minnow
5.62
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
521.9
Hydration Free Energy
-2.95
Log(D) at pH=7.4
1.82
Log(P)
-0.72
Log S
-2.2
Log(Vapor Pressure)
-12.36
Melting Point
225.95
pKa Acid
6.29
pKa Basic
7.13
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 0.9329
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9329
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8388
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8388
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8107
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8107
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7832
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7832
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7689
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7689
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7429
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7429

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