Clausamine H - Compound Card

Clausamine H

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Clausamine H

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Carbazole Alkaloid
Canonical Smiles COC(=O)c1cc(OC)c2c(c1CC=C(C)C)c1ccccc1[nH]2
InChI InChI=1S/C20H21NO3/c1-12(2)9-10-13-15(20(22)24-4)11-17(23-3)19-18(13)14-7-5-6-8-16(14)21-19/h5-9,11,21H,10H2,1-4H3
InChIKey YTUBOXOSIHCYQX-UHFFFAOYSA-N
Formula C20H21NO3
HBA 3
HBD 1
MW 323.39
Rotatable Bonds 4
TPSA 51.32
LogP 4.63
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 323.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clausena anisata Rutaceae Plantae 159034

Showing of synonyms

  • Tatsimo SJN, Tamokou JDD, et al. (2015). LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata. Med Chem Res, 2015, 24, 1468–1479. [View]
Pubchem: 10041876
Nmrshiftdb2: 70016664

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 323.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.440
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.820
Plasma Protein Binding
51.61
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.700
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.460
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.930
Micronucleos
Toxic
NR-AhR
Toxic
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
2.290
Rat (Acute)
2.100
Rat (Chronic Oral)
2.280
Fathead Minnow
5.360
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
427.790
Hydration Free Energy
-9.070
Log(D) at pH=7.4
5.030
Log(P)
5.72
Log S
-5.98
Log(Vapor Pressure)
-6.92
Melting Point
140.05
pKa Acid
11.1
pKa Basic
6.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9419
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9332
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9146
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.9079
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9060
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9039
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8989
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8973
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8964
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8940
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8616
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8530
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8523
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8519
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8496
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8456
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8448
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8331
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8319
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8133
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8095
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8068
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8061
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7981
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7977
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7971
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7937
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7923
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7868
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7860
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7851
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7839
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7833
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7817
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7817
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7790
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7784
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7776
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7772
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7767
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7715
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7691
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7644
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7629
Cyclin-dependent kinase 2 homolog Q07785 CDC2H_PLAFK Plasmodium falciparum 4 0.7625
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7618
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7608
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7586
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7563
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7535
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7527
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7526
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7518
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7512
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7492
Serine/threonine-protein kinase PAK 4 O96013 PAK4_HUMAN Homo sapiens 4 0.7484
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7481
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7480
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7472
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7466
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7457
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7445
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7430
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7408
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7398
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7393
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7387
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7370
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7351
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7323
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7322
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7320
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7319
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7316
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7315
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7306
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7299
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7299
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7294
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7292
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7289
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7285
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7269
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7264
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7261
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7260
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7260
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 4 0.7250
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7249
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7248
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7241
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7233
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7226
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7214
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7210
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7209
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7191
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7168
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7164
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7154
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7141
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7125
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7113
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7109
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7100
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7100
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7097
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7094
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7094
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7094
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7089
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7089
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform Q8BTI9 PK3CB_MOUSE Mus musculus 4 0.7088
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7085
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7082
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7079
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7075
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7059
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7058
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7053
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7050
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7045
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7038
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7026
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7024
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7015
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7014
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7006

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