Voucapane-6alpha,7alpha-diol - Compound Card

Voucapane-6alpha,7alpha-diol

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Voucapane-6alpha,7alpha-diol

Structure
Zoomed Structure
  • Family: Plantae - Caesalpiniaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Furanoditerpenoid
Canonical Smiles O[C@@H]1[C@H](O)[C@H]2C(C)(C)CCC[C@@]2([C@@H]2[C@@H]1[C@@H](C)c1ccoc1C2)C
InChI InChI=1S/C20H30O3/c1-11-12-6-9-23-14(12)10-13-15(11)16(21)17(22)18-19(2,3)7-5-8-20(13,18)4/h6,9,11,13,15-18,21-22H,5,7-8,10H2,1-4H3/t11-,13-,15-,16-,17-,18-,20+/m0/s1
InChIKey LMOVGTPTUFELOS-JHDXISRPSA-N
Formula C20H30O3
HBA 3
HBD 2
MW 318.46
Rotatable Bonds 0
TPSA 53.6
LogP 3.74
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 318.22
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: 44606168

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)CC3C4C(CCC3C2)CCCC4

Level: 0

Mol. Weight: 318.46 g/mol

Anti-proliferative
Antibacterial
Antifungal
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.08
Plasma Protein Binding
78.09
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
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
17.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.64
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.29
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.68
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-0.43
Rat (Acute)
2.71
Rat (Chronic Oral)
2.45
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
362.88
Hydration Free Energy
-6.19
Log(D) at pH=7.4
3.85
Log(P)
4.37
Log S
-4.3
Log(Vapor Pressure)
-8.37
Melting Point
170.28
pKa Acid
10.73
pKa Basic
6.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7876
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7876
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7688
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7688
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7649
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7649
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7539
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7539
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7459
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7459
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7426
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7426
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7284
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7284
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7219
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7219
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7205
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7205
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7133
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7133
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7110
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7110
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7044
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7044

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