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 COc1cc(C)c(c2c1[nH]c1c2cccc1)CC=C(C)C
InChI InChI=1S/C19H21NO/c1-12(2)9-10-14-13(3)11-17(21-4)19-18(14)15-7-5-6-8-16(15)20-19/h5-9,11,20H,10H2,1-4H3
InChIKey DUEVFSJVIWADPZ-UHFFFAOYSA-N
Formula C19H21NO
HBA 1
HBD 1
MW 279.38
Rotatable Bonds 3
TPSA 25.02
LogP 5.15
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 279.16
Number of Lipinski Rule Violations 1
# 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]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 279.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.350
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.770
Plasma Protein Binding
37.64
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
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.710
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.500
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.030
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.100
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
4.230
Rat (Acute)
2.050
Rat (Chronic Oral)
2.120
Fathead Minnow
5.110
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
414.650
Hydration Free Energy
-8.020
Log(D) at pH=7.4
4.350
Log(P)
6.14
Log S
-6.39
Log(Vapor Pressure)
-6.74
Melting Point
140.61
pKa Acid
12.8
pKa Basic
7.31
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 0.9316
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9098
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.9003
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.8993
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8970
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.8898
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8889
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8871
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.8846
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8839
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8837
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8776
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.8766
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.8740
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8669
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8625
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8533
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8472
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8445
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8441
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8426
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8375
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8359
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8345
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8292
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8275
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8272
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.8217
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8215
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8213
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8177
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8174
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8125
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8104
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8018
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8016
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 4 0.7893
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7890
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7887
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7865
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7856
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7844
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7840
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7826
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7815
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7812
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7791
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7785
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7763
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7759
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7754
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7749
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7747
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7735
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7728
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7715
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7685
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7679
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7666
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7660
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7643
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7640
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7635
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7626
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7625
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7599
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7582
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7578
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7560
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7557
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7549
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7542
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7527
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7511
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7503
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7490
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7483
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7470
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7470
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7464
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7462
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7459
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7456
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7451
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7442
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7423
Cyclin-dependent kinase 2 homolog Q07785 CDC2H_PLAFK Plasmodium falciparum 4 0.7417
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7412
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7407
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7402
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7389
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7387
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7382
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7358
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7357
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7352
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7344
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7328
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7305
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7299
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7293
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7281
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7273
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7267
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7259
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7251
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7247
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7246
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7243
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7209
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7205
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7204
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7203
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7203
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7200
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7194
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7193
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7183
Toll-like receptor 8 Q9NR97 TLR8_HUMAN Homo sapiens 3 0.7178
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7176
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7171
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7170
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7158
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7155
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7144
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7135
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7133
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7125
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7121
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7092
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7091
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7090
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7086
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7064
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7061
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7060
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7041
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7036
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7031
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7030
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7025
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7019
Choline kinase alpha P35790 CHKA_HUMAN Homo sapiens 3 0.7013
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7011

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