Serotobenine - Compound Card

Serotobenine

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Serotobenine

Structure
Zoomed Structure
  • Family: Plantae - Onagraceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COc1cc(ccc1O)[C@H]1Oc2c3[C@@H]1C(=O)NCCc1c3c(cc2)[nH]c1
InChI InChI=1S/C20H18N2O4/c1-25-15-8-10(2-4-13(15)23)19-18-17-14(26-19)5-3-12-16(17)11(9-22-12)6-7-21-20(18)24/h2-5,8-9,18-19,22-23H,6-7H2,1H3,(H,21,24)/t18-,19+/m0/s1
InChIKey GEJUXZYANAYHRZ-RBUKOAKNSA-N
Formula C20H18N2O4
HBA 4
HBD 3
MW 350.37
Rotatable Bonds 2
TPSA 83.58
LogP 2.77
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 350.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Campylospermum calanthum Ochnaceae Plantae 1321790
2 Campylospermum oliverianum Ochnaceae Plantae 2708701
3 Campylospermum densiflorum Onagraceae Plantae 1321789

Showing of synonyms

  • Bikobo DSN, Nkot JL, et al. (2011). Acylsteryl glycosides and other constituents from Campylospermum densiflorum (Ochnaceae).. RASAYAN J. Chem. 2011, 4(4),753-763. [View]
  • Zintchem AAA, Ndongo JT, et al. (2014). Biological studies on nitrogen-containing compounds from Campylospermum oliverianum and Campylospermum sulcatum (Ochnaceae).. International Journal of Pharmacy and Pharmaceutical Sciences, 2014, 6, 252-256. [View]
  • Njock GBB, Bartholomeusz TA, et al. (2013). Structure and Dynamic of Three Indole Alkaloids from the Campylospermum Genus (Ochnaceae). HCA, 2013, 96, 1298-1304. [View]
Pubchem: 11725426
Nmrshiftdb2: 70131758

No compound-protein relationship available.

Structure

SMILES: c12c3c4ccc2[nH]cc1CCNC(=O)C3C(O4)c5ccccc5

Level: 1

Mol. Weight: 350.37 g/mol

Structure

SMILES: c12c3c4ccc2[nH]cc1CCNC(=O)C3CO4

Level: 0

Mol. Weight: 350.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 350.37 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.940
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
84.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
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
6.960
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.150
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.260
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.390
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
-7.780
Rat (Acute)
2.210
Rat (Chronic Oral)
2.500
Fathead Minnow
4.420
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
490.200
Hydration Free Energy
-8.930
Log(D) at pH=7.4
2.360
Log(P)
1.61
Log S
-4.97
Log(Vapor Pressure)
-10.03
Melting Point
237.77
pKa Acid
8.61
pKa Basic
5.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9076
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8955
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8753
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8715
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8666
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8649
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8647
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8489
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8382
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8253
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8178
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8175
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7987
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7943
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 4 0.7905
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7867
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.7825
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7777
Cytochrome P450 I6YD01 I6YD01_MYCTU Mycobacterium tuberculosis 4 0.7771
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7704
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7678
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7662
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7645
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7638
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7637
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7625
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7579
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7548
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7548
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7521
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7513
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7448
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7442
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7417
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7400
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7392
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7382
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7379
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7371
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7357
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7356
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7354
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 4 0.7332
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7328
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7297
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7290
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7275
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7273
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7273
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7237
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7230
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7226
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7201
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7191
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7185
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7183
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7181
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7119
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7117
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7108
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7088
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7081
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7078
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7069
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7067
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7027
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7026
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7020
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7001

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