1beta,6beta-dihydroxyvoucapane 19beta-methyl ester - Compound Card

1beta,6beta-dihydroxyvoucapane 19beta-methyl ester

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1beta,6beta-dihydroxyvoucapane 19beta-methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Furanoditerpene
Canonical Smiles COC(=O)C1(C)CCC([C@@]2([C@@H]1C(O)C[C@H]1[C@H]2Cc2c([C@H]1C)cco2)C)O
InChI InChI=1S/C21H30O5/c1-11-12-6-8-26-16(12)10-14-13(11)9-15(22)18-20(2,19(24)25-4)7-5-17(23)21(14,18)3/h6,8,11,13-15,17-18,22-23H,5,7,9-10H2,1-4H3/t11-,13-,14-,15?,17?,18-,20?,21-/m1/s1
InChIKey JFROLRTYTSCKNK-LVQCUNDNSA-N
Formula C21H30O5
HBA 5
HBD 2
MW 362.47
Rotatable Bonds 1
TPSA 79.9
LogP 2.89
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 362.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Caesalpinia volkensii Leguminosae/Fabaceae Plantae 1387603

Showing of synonyms

  • Ochieng' CO, Owuor PO, et al. (2012). Antinociceptive and antiplasmodial activities of cassane furanoditerpenes from Caesalpinia volkensii H. root bark.. Fitoterapia,2012,83(1),74-80. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)CC3C4C(CCC3C2)CCCC4

Level: 0

Mol. Weight: 362.47 g/mol

Antinociceptive

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.810
Plasma Protein Binding
56.58
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.810
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.700
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.260
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.740
Micronucleos
Toxic
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
-4.410
Rat (Acute)
4.300
Rat (Chronic Oral)
2.210
Fathead Minnow
3.950
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
399.930
Hydration Free Energy
-6.160
Log(D) at pH=7.4
2.660
Log(P)
3.05
Log S
-3.55
Log(Vapor Pressure)
-7.67
Melting Point
162.93
pKa Acid
9.48
pKa Basic
5.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8868
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8868
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8622
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8622
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7652
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7652
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7644
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7644
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7613
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7613
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7545
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7545
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7544
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7544
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7429
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7429
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7414
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7414
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7384
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7384
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7303
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7303
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7282
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7282
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7256
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7256
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7220
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7220
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7195
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7195
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7124
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7124
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7034
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7034

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