18,19-di-acetoxyvoucapane - Compound Card

18,19-di-acetoxyvoucapane

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18,19-di-acetoxyvoucapane

Structure
Zoomed Structure
  • Family: Plantae - Caesalpiniaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Furanoditerpenoid
Canonical Smiles CC(=O)OCC1(CCC[C@]2([C@H]1CC[C@@H]1[C@@H]2Cc2c([C@@H]1C)cco2)C)COC(=O)C
InChI InChI=1S/C24H34O5/c1-15-18-6-7-22-23(4,20(18)12-21-19(15)8-11-27-21)9-5-10-24(22,13-28-16(2)25)14-29-17(3)26/h8,11,15,18,20,22H,5-7,9-10,12-14H2,1-4H3/t15-,18+,20+,22-,23-/m1/s1
InChIKey WCUQSUMSQVCOON-WWQQZRQXSA-N
Formula C24H34O5
HBA 5
HBD 0
MW 402.53
Rotatable Bonds 4
TPSA 65.74
LogP 4.88
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 402.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Stuhlmannia moavi Caesalpiniaceae Plantae 191956

Showing of synonyms

  • Odalo JO, Joseph CC, et al. (2009). Cytotoxic, anti-proliferative and antimicrobial furanoditerpenoids from Stuhlmania moavi. Phytochemistry,2009,70(17-18),2047-2052. [View] [PubMed]
Pubchem: 44606346

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)CC3C4C(CCC3C2)CCCC4

Level: 0

Mol. Weight: 402.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.45
Plasma Protein Binding
73.46
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
13.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.1
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.85
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
-20.6
Rat (Acute)
2.09
Rat (Chronic Oral)
2.28
Fathead Minnow
3.93
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
435.63
Hydration Free Energy
-4.25
Log(D) at pH=7.4
4.26
Log(P)
3.49
Log S
-5.52
Log(Vapor Pressure)
-7.72
Melting Point
135.85
pKa Acid
11.76
pKa Basic
5.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8543
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8543
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7977
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7977
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7901
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7901
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7867
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7867
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7858
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7858
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7758
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7758
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7733
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7733
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7710
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7710
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7677
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7677
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7637
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7637
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7589
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7589
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7588
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7588
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7586
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7586
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7560
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7560
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7548
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7548
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7542
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7542
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7520
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7520
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7500
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7500
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7479
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7479
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7464
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7464
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7423
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7423
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7421
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7421
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7405
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7405
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7403
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7403
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7398
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7398
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7396
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7396
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7385
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7385
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7377
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7377
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7353
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7353
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7342
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7342
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7338
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7338
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7336
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7336
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7331
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7331
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7321
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7321
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7303
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7303
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7277
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7277
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7197
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7197
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7194
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7194
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7185
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7185
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7168
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7168
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7154
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7154
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7143
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7143
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7135
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7135
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7106
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7106
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7098
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7098
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7093
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7093
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7060
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7060
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7034
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7034
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7030
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7030
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7004
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7004
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7004
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7004

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