Sesquichamaenol - Compound Card

Sesquichamaenol

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Sesquichamaenol

Structure
Zoomed Structure
  • Family: Plantae - Ptaeroxylaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(=O)CCC(c1cc(C)ccc1O)C(C)C
InChI InChI=1S/C15H22O2/c1-10(2)13(7-6-12(4)16)14-9-11(3)5-8-15(14)17/h5,8-10,13,17H,6-7H2,1-4H3
InChIKey UFWXDPOVAJYDEP-UHFFFAOYSA-N
Formula C15H22O2
HBA 2
HBD 1
MW 234.34
Rotatable Bonds 5
TPSA 37.3
LogP 3.81
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 234.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cedrelopsis microfoliolata Ptaeroxylaceae Plantae 1304322

Showing of synonyms

  • Koorbanally NA, Randrianarivelojosia M, et al. (2002). Bioactive Constituents of Cedrelopsis microfoliata. Journal of natural products, 2002, 65(9), 1349–1352. [View]
Pubchem: 11085721
Nmrshiftdb2: 70016185

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 234.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
37.85
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
9.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.59
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.66
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.17
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.13
Rat (Acute)
2.0
Rat (Chronic Oral)
2.18
Fathead Minnow
4.21
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
307.77
Hydration Free Energy
-6.4
Log(D) at pH=7.4
3.16
Log(P)
3.25
Log S
-3.77
Log(Vapor Pressure)
-4.46
Melting Point
43.7
pKa Acid
10.61
pKa Basic
9.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9512
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9008
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.8939
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8869
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8832
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8815
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8735
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8676
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8623
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8602
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.8509
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8485
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8459
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8413
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8399
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8385
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8310
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8247
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8233
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8222
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8190
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8173
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8157
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.8110
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8089
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8039
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.8025
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7991
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7968
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7962
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7950
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7948
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7897
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7895
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7879
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7811
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7746
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7738
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7691
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7691
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7666
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7659
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7649
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7639
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 4 0.7630
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7625
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7612
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7566
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7553
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7536
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7535
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7520
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 4 0.7517
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7514
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7500
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7496
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7495
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7450
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7444
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7439
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7436
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7407
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7403
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7397
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7386
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7383
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7372
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7364
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7354
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7350
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7329
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7297
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7277
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7275
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7269
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7250
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7240
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7238
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7230
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7225
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7224
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 2 0.7219
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7218
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7212
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7200
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7200
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7198
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7190
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7188
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7186
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7183
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7174
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7174
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7171
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7171
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7163
Deoxynucleoside kinase Q9XZT6 DNK_DROME Drosophila melanogaster 4 0.7156
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7147
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7139
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7137
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7137
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7130
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7130
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7127
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7125
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7123
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7122
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7117
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7111
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7111
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7110
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7101
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7101
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7095
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7095
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7094
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7089
Guanylate kinase P15454 KGUA_YEAST Saccharomyces cerevisiae 3 0.7072
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7061
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7056
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7055
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7055
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7052
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7051
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7049
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7043
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7042
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7032
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7030
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7027
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7021
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7014
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7010
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7003

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