18,19-dibenzoyloxyvoucapane - Compound Card

18,19-dibenzoyloxyvoucapane

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18,19-dibenzoyloxyvoucapane

Structure
Zoomed Structure
  • Family: Plantae - Caesalpiniaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Furanoditerpenoid
Canonical Smiles O=C(c1ccccc1)OC1(CCC[C@]2([C@H]1CC[C@@H]1[C@@H]2Cc2c([C@@H]1C)cco2)C)OC(=O)c1ccccc1
InChI InChI=1S/C32H34O5/c1-21-24-14-15-28-31(2,26(24)20-27-25(21)16-19-35-27)17-9-18-32(28,36-29(33)22-10-5-3-6-11-22)37-30(34)23-12-7-4-8-13-23/h3-8,10-13,16,19,21,24,26,28H,9,14-15,17-18,20H2,1-2H3/t21-,24+,26+,28-,31-/m1/s1
InChIKey NIVLRKUUSCNENR-MKNFNCEUSA-N
Formula C32H34O5
HBA 5
HBD 0
MW 498.62
Rotatable Bonds 4
TPSA 65.74
LogP 7.18
Number Rings 6
Number Aromatic Rings 3
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 498.24
Number of Lipinski Rule Violations 1
# 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]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(CCC2)(C(CCC3C4)C2C3Cc(c45)occ5)OC(=O)c6ccccc6

Level: 2

Mol. Weight: 498.62 g/mol

Structure

SMILES: c1ccccc1C(=O)OC(CCC2)C(CCC3C4)C2C3Cc(c45)occ5

Level: 1

Mol. Weight: 498.62 g/mol

Structure

SMILES: c1coc(c12)CC3C4C(CCC3C2)CCCC4

Level: 0

Mol. Weight: 498.62 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 498.62 g/mol

Anti-proliferative
Antibacterial
Antifungal
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.88
Plasma Protein Binding
93.68
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.12
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.23
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2388.66
Rat (Acute)
1.89
Rat (Chronic Oral)
2.75
Fathead Minnow
13.07
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
461.5
Hydration Free Energy
-2.78
Log(D) at pH=7.4
5.89
Log(P)
8.25
Log S
-6.61
Log(Vapor Pressure)
-8.37
Melting Point
148.83
pKa Acid
9.38
pKa Basic
5.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.8881
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.8881
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8762
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8762
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.8523
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.8523
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8390
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8390
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8048
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8048
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8030
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8030
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7934
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7934
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7869
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7869
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7850
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7850
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7812
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7812
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7671
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7671
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7660
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7660
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7625
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7625
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7622
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7622
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7578
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7578
Tryptase alpha/beta-1 Q15661 TRYB1_HUMAN Homo sapiens 3 0.7568
Tryptase alpha/beta-1 Q15661 TRYB1_HUMAN Homo sapiens 3 0.7568
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7561
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7561
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7553
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7553
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7510
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7510
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7480
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7480
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7479
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7479
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7474
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7474
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7464
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7464
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7463
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7463
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7430
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7430
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7427
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7427
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7403
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7403
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7367
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7367
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7353
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7353
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7325
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7325
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7321
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7321
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7316
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7316
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7308
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7308
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7304
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7304
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7297
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7297
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7297
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7297
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7269
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7269
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7259
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7259
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7197
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7197
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7188
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7188
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7170
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7170
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7152
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7152
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7130
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7130
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7112
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7112
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7112
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7112
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7110
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7110
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7090
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7090
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7085
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7085
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7079
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7079
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7073
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7073
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7052
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7052
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7052
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7052
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7049
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7049
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7044
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7044
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7040
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7040
Nociceptin receptor P41146 OPRX_HUMAN Homo sapiens 3 0.7021
Nociceptin receptor P41146 OPRX_HUMAN Homo sapiens 3 0.7021

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