Voucapane-18,19-diol - Compound Card

Voucapane-18,19-diol

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Voucapane-18,19-diol

Structure
Zoomed Structure
  • Family: Plantae - Caesalpiniaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Furanoditerpenoid
Canonical Smiles OCC1(CO)CCC[C@]2([C@H]1CC[C@@H]1[C@@H]2Cc2c([C@@H]1C)cco2)C
InChI InChI=1S/C20H30O3/c1-13-14-4-5-18-19(2,7-3-8-20(18,11-21)12-22)16(14)10-17-15(13)6-9-23-17/h6,9,13-14,16,18,21-22H,3-5,7-8,10-12H2,1-2H3/t13-,14+,16+,18-,19-/m1/s1
InChIKey CIDBCHWNEAJNCU-YSYIFYARSA-N
Formula C20H30O3
HBA 3
HBD 2
MW 318.46
Rotatable Bonds 2
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: 44606169

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)
-4.94
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
72.5
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.96
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.28
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.9
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-0.89
Rat (Acute)
2.42
Rat (Chronic Oral)
2.62
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
384.42
Hydration Free Energy
-6.25
Log(D) at pH=7.4
3.28
Log(P)
3.26
Log S
-4.02
Log(Vapor Pressure)
-8.64
Melting Point
168.0
pKa Acid
11.16
pKa Basic
7.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7707
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7707
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7586
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7586
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7512
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7512
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7440
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7440
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7385
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7385
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7367
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7367
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7361
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7361
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7317
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7317
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7301
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7301
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7275
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7275
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7213
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7213
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7141
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7141
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7086
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7086
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7048
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7048

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