Phenowithanolide - Compound Card

Phenowithanolide

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Phenowithanolide

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Withanolide-Type Steroid
Canonical Smiles Cc1cccc2c1CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]1CO[C@@]2(C[C@H]1OC(=O)C2=C)C)C
InChI InChI=1S/C28H36O3/c1-16-6-5-7-19-18(16)8-9-21-20(19)12-13-27(3)23(21)10-11-24(27)22-15-30-28(4)14-25(22)31-26(29)17(28)2/h5-7,20-25H,2,8-15H2,1,3-4H3/t20-,21-,22+,23+,24-,25-,27+,28-/m1/s1
InChIKey KBBDYZLRNLANGR-NOPKTSJSSA-N
Formula C28H36O3
HBA 3
HBD 0
MW 420.59
Rotatable Bonds 1
TPSA 35.53
LogP 5.74
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 420.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Datura metel Solanaceae Plantae 35625

Showing of synonyms

  • Bellila A, Tremblay C, et al. (2011). Cytotoxic activity of withanolides isolated from Tunisian Datura metel L.. Phytochemistry,2011,72(16),2031-2036. [View] [PubMed]
Pubchem: 163093210
Nmrshiftdb2: 70035768

No compound-protein relationship available.

Structure

SMILES: C=C(C12)C(=O)OC(C1)C(CO2)C3CCC(C34)C5C(CC4)c6c(CC5)cccc6

Level: 1

Mol. Weight: 420.59 g/mol

Structure

SMILES: C1CCC(C12)CCC3c4c(CCC23)cccc4

Level: 0

Mol. Weight: 420.59 g/mol

Structure

SMILES: C=C(C12)C(=O)OC(C1)CCO2

Level: 0

Mol. Weight: 420.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.92
Plasma Protein Binding
83.92
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
7.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.17
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.05
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-97.97
Rat (Acute)
2.32
Rat (Chronic Oral)
2.05
Fathead Minnow
4.06
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
491.09
Hydration Free Energy
-2.17
Log(D) at pH=7.4
5.15
Log(P)
5.6
Log S
-6.26
Log(Vapor Pressure)
-8.53
Melting Point
176.03
pKa Acid
11.49
pKa Basic
5.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8842
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8842
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8485
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8485
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8211
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8211
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8016
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8016
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7990
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7990
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7982
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7982
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7843
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7843
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7805
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7805
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7758
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7758
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7716
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7716
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7644
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7644
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7615
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7615
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7529
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7529
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7525
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7525
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7399
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7399
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7343
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7343
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7323
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7323
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7306
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7306
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7250
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7250
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7238
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7238
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7219
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7219
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7182
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7182
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7147
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7147
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7115
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7115
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7059
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7059
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7029
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7029
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7019
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7019

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