Dihydro-20-epi-isoiguesterinol triacetate - Compound Card

Dihydro-20-epi-isoiguesterinol triacetate

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Dihydro-20-epi-isoiguesterinol triacetate

Structure
Zoomed Structure
  • Family: Plantae - Celastraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Bisnortriterpenoid
Canonical Smiles CC(=O)OC[C@@H]1CC[C@]2(C(C1)[C@]1(C)CC[C@@]3(C(=CCc4c3cc(OC(=O)C)c(c4C)OC(=O)C)[C@]1(CC2)C)C)C
InChI InChI=1S/C34H46O6/c1-20-25-9-10-28-32(6,26(25)18-27(39-22(3)36)30(20)40-23(4)37)14-16-34(8)29-17-24(19-38-21(2)35)11-12-31(29,5)13-15-33(28,34)7/h10,18,24,29H,9,11-17,19H2,1-8H3/t24-,29?,31-,32+,33-,34+/m1/s1
InChIKey MBWBXAHKZIFOMI-SAIRVCPBSA-N
Formula C34H46O6
HBA 6
HBD 0
MW 550.74
Rotatable Bonds 4
TPSA 78.9
LogP 7.17
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 550.33
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Salacia madagascariensis Celastraceae Plantae 670374

Showing of synonyms

  • Thiem DA, Sneden AT, et al. (2005). Bisnortriterpenes from Salacia madagascariensis. Journal of Natural Products,2005,68(2),251-254. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CC=C3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 550.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.0
Plasma Protein Binding
97.77
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor

Excretion

Clearance
7.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.52
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.53
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2337.14
Rat (Acute)
1.8
Rat (Chronic Oral)
2.14
Fathead Minnow
12.82
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
471.72
Hydration Free Energy
-2.78
Log(D) at pH=7.4
5.32
Log(P)
6.84
Log S
-6.48
Log(Vapor Pressure)
-8.23
Melting Point
190.44
pKa Acid
11.69
pKa Basic
5.59
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 0.9533
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9533
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9042
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9042
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9013
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9013
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8395
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8395
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8173
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8173
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8172
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8172
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7958
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7958
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7912
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7912
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7648
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7648
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7601
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7601
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7536
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7536
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7463
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7463
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7435
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7435
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7386
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7386
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7381
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7381
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7355
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7355
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7336
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7336
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7247
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7247
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7236
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7236
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7213
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7213
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7185
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7185
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.7166
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.7166
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7094
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7094
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7072
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7072
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7062
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7062
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7030
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7030

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