Caesaldekarin C - Compound Card

Caesaldekarin C

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Caesaldekarin C

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Furanoditerpene
Canonical Smiles COC(=O)[C@@]1(C)CCC[C@]2([C@@]1(O)CC[C@@H]1[C@@H]2Cc2c([C@@H]1C)cco2)C
InChI InChI=1S/C21H30O4/c1-13-14-6-10-21(23)19(2,8-5-9-20(21,3)18(22)24-4)16(14)12-17-15(13)7-11-25-17/h7,11,13-14,16,23H,5-6,8-10,12H2,1-4H3/t13-,14+,16+,19-,20-,21+/m1/s1
InChIKey GMCXIFIKPROBFX-ZOJTVGBFSA-N
Formula C21H30O4
HBA 4
HBD 1
MW 346.47
Rotatable Bonds 1
TPSA 59.67
LogP 4.07
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 346.21
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]
Pubchem: 10712612
Nmrshiftdb2: 60063341

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)CC3C4C(CCC3C2)CCCC4

Level: 0

Mol. Weight: 346.47 g/mol

Antinociceptive

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
66.69
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.890
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.220
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.850
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
-3.460
Rat (Acute)
2.470
Rat (Chronic Oral)
1.810
Fathead Minnow
3.920
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
382.820
Hydration Free Energy
-5.380
Log(D) at pH=7.4
3.800
Log(P)
4.47
Log S
-4.42
Log(Vapor Pressure)
-6.99
Melting Point
168.06
pKa Acid
10.51
pKa Basic
6.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8564
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8564
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7797
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7797
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7714
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7714
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7625
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7625
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7608
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7608
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7483
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7483
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7409
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7409
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7391
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7391
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7382
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7382
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7366
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7366
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7341
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7341
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7316
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7316
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7302
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7302
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7291
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7291
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7259
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7259
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7210
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7210
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7202
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7202
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7135
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7135
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7135
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7135
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7133
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7133
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7129
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7129
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7090
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7090
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7050
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7050

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