Structure

Physi-Chem Properties

Molecular Weight:  291.1
Volume:  280.928
LogP:  1.107
LogD:  1.064
LogS:  -1.022
# Rotatable Bonds:  2
TPSA:  62.3
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.903
Synthetic Accessibility Score:  2.826
Fsp3:  0.357
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.32
MDCK Permeability:  8.943903594627045e-06
Pgp-inhibitor:  0.007
Pgp-substrate:  0.486
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.977
Plasma Protein Binding (PPB):  81.26045989990234%
Volume Distribution (VD):  1.605
Pgp-substrate:  24.97129249572754%

ADMET: Metabolism

CYP1A2-inhibitor:  0.286
CYP1A2-substrate:  0.402
CYP2C19-inhibitor:  0.301
CYP2C19-substrate:  0.918
CYP2C9-inhibitor:  0.156
CYP2C9-substrate:  0.44
CYP2D6-inhibitor:  0.794
CYP2D6-substrate:  0.628
CYP3A4-inhibitor:  0.933
CYP3A4-substrate:  0.797

ADMET: Excretion

Clearance (CL):  7.804
Half-life (T1/2):  0.48

ADMET: Toxicity

hERG Blockers:  0.442
Human Hepatotoxicity (H-HT):  0.964
Drug-inuced Liver Injury (DILI):  0.988
AMES Toxicity:  0.053
Rat Oral Acute Toxicity:  0.21
Maximum Recommended Daily Dose:  0.902
Skin Sensitization:  0.175
Carcinogencity:  0.09
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.892

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC469897

Natural Product ID:  NPC469897
Common Name*:   1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine
IUPAC Name:   5-[(2S)-2-methylpiperazin-1-yl]sulfonylisoquinoline
Synonyms:  
Standard InCHIKey:  BDVFVCGFMNCYPV-NSHDSACASA-N
Standard InCHI:  InChI=1S/C14H17N3O2S/c1-11-9-16-7-8-17(11)20(18,19)14-4-2-3-12-10-15-6-5-13(12)14/h2-6,10-11,16H,7-9H2,1H3/t11-/m0/s1
SMILES:  C[C@H]1CNCCN1S(=O)(=O)c1cccc2c1ccnc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1233654
PubChem CID:   449240
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO1859 Lantana camara Species Verbenaceae Eukaryota aerial parts n.a. n.a. PMID[10869197]
NPO31561 Micromonospora Genus Micromonosporaceae Bacteria n.a. n.a. n.a. PMID[12027749]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. PMID[1812212]
NPO31561 Micromonospora Genus Micromonosporaceae Bacteria n.a. n.a. n.a. PMID[9531992]
NPO1859 Lantana camara Species Verbenaceae Eukaryota leaves n.a. n.a. PMID[9834145]
NPO31561 Micromonospora Genus Micromonosporaceae Bacteria n.a. n.a. n.a. PMID[9917009]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1859 Lantana camara Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2733 Individual Protein Protein kinase Pfmrk Plasmodium falciparum IC50 > 500000.0 nM PMID[513938]
NPT137 Cell Line L1210 Mus musculus IC50 = 23500.0 nM PMID[513939]
NPT519 Cell Line SH-SY5Y Homo sapiens IC50 = 40000.0 nM PMID[513941]
NPT519 Cell Line SH-SY5Y Homo sapiens IC50 = 80000.0 nM PMID[513941]
NPT3107 Individual Protein Rho-associated protein kinase 2 Homo sapiens Activity = 16.0 % PMID[513942]
NPT3106 Individual Protein Ribosomal protein S6 kinase alpha 1 Homo sapiens Activity = 25.0 % PMID[513942]
NPT1614 Individual Protein MAP kinase p38 delta Homo sapiens Activity = 81.0 % PMID[513942]
NPT1615 Individual Protein MAP kinase p38 gamma Homo sapiens Activity = 86.0 % PMID[513942]
NPT1695 Individual Protein Serine/threonine-protein kinase PAK 4 Homo sapiens Activity = 92.0 % PMID[513942]
NPT1696 Individual Protein Serine/threonine-protein kinase PAK7 Homo sapiens Activity = 89.0 % PMID[513942]
NPT1697 Individual Protein Serine/threonine-protein kinase PAK6 Homo sapiens Activity = 84.0 % PMID[513942]
NPT1699 Individual Protein 3-phosphoinositide dependent protein kinase-1 Homo sapiens Activity = 80.0 % PMID[513942]
NPT1265 Individual Protein Serine/threonine-protein kinase PIM1 Homo sapiens Activity = 99.0 % PMID[513942]
NPT1700 Individual Protein Serine/threonine-protein kinase PIM2 Homo sapiens Activity = 87.0 % PMID[513942]
NPT1701 Individual Protein Serine/threonine-protein kinase PIM3 Homo sapiens Activity = 83.0 % PMID[513942]
NPT1703 Individual Protein cAMP-dependent protein kinase alpha-catalytic subunit Homo sapiens Activity = 46.0 % PMID[513942]
NPT1430 Individual Protein Serine/threonine-protein kinase AKT2 Homo sapiens Activity = 81.0 % PMID[513942]
NPT182 Individual Protein Protein kinase C alpha Homo sapiens Activity = 60.0 % PMID[513942]
NPT3455 Individual Protein Protein kinase C zeta Homo sapiens Activity = 60.0 % PMID[513942]
NPT3364 Individual Protein Protein kinase C mu Homo sapiens Activity = 31.0 % PMID[513942]
NPT3291 Individual Protein Serine/threonine-protein kinase SRPK1 Homo sapiens Activity = 86.0 % PMID[513942]
NPT1705 Individual Protein Ribosomal protein S6 kinase alpha 3 Homo sapiens Activity = 45.0 % PMID[513942]
NPT1611 Individual Protein Ribosomal protein S6 kinase 1 Homo sapiens Activity = 43.0 % PMID[513942]
NPT2543 Individual Protein cAMP-dependent protein kinase alpha-catalytic subunit Oryctolagus cuniculus Ki = 3000.0 nM PMID[513943]
NPT3325 Individual Protein Myosin light chain kinase, smooth muscle Gallus gallus Ki = 97000.0 nM PMID[513943]
NPT1448 Individual Protein Serine/threonine-protein kinase Sgk1 Homo sapiens Activity = 69.0 % PMID[513942]
NPT2626 Individual Protein Myosin light chain kinase, smooth muscle Homo sapiens Activity = 83.0 % PMID[513942]
NPT3813 Individual Protein Tyrosine-protein kinase SRC Gallus gallus Activity = 87.0 % PMID[513942]
NPT1433 Individual Protein Serine/threonine-protein kinase Aurora-B Homo sapiens Activity = 78.0 % PMID[513942]
NPT3206 Individual Protein Serine/threonine-protein kinase Aurora-C Homo sapiens Activity = 83.0 % PMID[513942]
NPT3344 Individual Protein BR serine/threonine-protein kinase 2 Homo sapiens Activity = 64.0 % PMID[513942]
NPT3232 Individual Protein CaM kinase I alpha Homo sapiens Activity = 64.0 % PMID[513942]
NPT3248 Individual Protein CaM-kinase kinase alpha Homo sapiens Activity = 85.0 % PMID[513942]
NPT1678 Individual Protein CaM-kinase kinase beta Homo sapiens Activity = 99.0 % PMID[513942]
NPT1608 Individual Protein Serine/threonine-protein kinase Chk1 Homo sapiens Activity = 90.0 % PMID[513942]
NPT1680 Individual Protein Serine/threonine-protein kinase Chk2 Homo sapiens Activity = 90.0 % PMID[513942]
NPT3266 Individual Protein Casein kinase I delta Homo sapiens Activity = 82.0 % PMID[513942]
NPT3113 Individual Protein Tyrosine-protein kinase CSK Homo sapiens Activity = 85.0 % PMID[513942]
NPT3114 Individual Protein Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens Activity = 86.0 % PMID[513942]
NPT3399 Individual Protein Dual-specificity tyrosine-phosphorylation regulated kinase 2 Homo sapiens Activity = 102.0 % PMID[513942]
NPT3460 Individual Protein Dual-specificity tyrosine-phosphorylation regulated kinase 3 Homo sapiens Activity = 50.0 % PMID[513942]
NPT1344 Individual Protein Serine/threonine-protein kinase EEF2K Homo sapiens Activity = 87.0 % PMID[513942]
NPT281 Individual Protein MAP kinase ERK1 Homo sapiens Activity = 98.0 % PMID[513942]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Activity = 84.0 % PMID[513942]
NPT3363 Individual Protein Mitogen-activated protein kinase 15 Homo sapiens Activity = 79.0 % PMID[513942]
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens Activity = 76.0 % PMID[513942]
NPT3331 Individual Protein Serine/threonine-protein kinase MST2 Homo sapiens Activity = 69.0 % PMID[513942]
NPT1658 Individual Protein Serine/threonine-protein kinase NEK2 Homo sapiens Activity = 87.0 % PMID[513942]
NPT1657 Individual Protein Serine/threonine-protein kinase NEK6 Homo sapiens Activity = 102.0 % PMID[513942]
NPT3284 Individual Protein Serine/threonine-protein kinase NEK7 Homo sapiens Activity = 93.0 % PMID[513942]
NPT283 Individual Protein MAP kinase p38 alpha Homo sapiens Activity = 85.0 % PMID[513942]
NPT1616 Individual Protein MAP kinase p38 beta Homo sapiens Activity = 93.0 % PMID[513942]
NPT3432 Individual Protein Homeodomain-interacting protein kinase 2 Homo sapiens Activity = 97.0 % PMID[513942]
NPT3409 Individual Protein Homeodomain-interacting protein kinase 3 Homo sapiens Activity = 101.0 % PMID[513942]
NPT1426 Individual Protein c-Jun N-terminal kinase 1 Homo sapiens Activity = 84.0 % PMID[513942]
NPT1427 Individual Protein c-Jun N-terminal kinase 2 Homo sapiens Activity = 95.0 % PMID[513942]
NPT3207 Individual Protein c-Jun N-terminal kinase 3 Homo sapiens Activity = 84.0 % PMID[513942]
NPT3815 Individual Protein Tyrosine-protein kinase LCK Mus musculus Activity = 75.0 % PMID[513942]
NPT1441 Individual Protein MAP kinase-activated protein kinase 2 Homo sapiens Activity = 82.0 % PMID[513942]
NPT3461 Individual Protein MAP kinase-activated protein kinase 3 Homo sapiens Activity = 98.0 % PMID[513942]
NPT3280 Individual Protein Serine/threonine-protein kinase c-TAK1 Homo sapiens Activity = 93.0 % PMID[513942]
NPT3282 Individual Protein Maternal embryonic leucine zipper kinase Homo sapiens Activity = 37.0 % PMID[513942]
NPT491 Individual Protein Dual specificity mitogen-activated protein kinase kinase 1 Homo sapiens Activity = 88.0 % PMID[513942]
NPT3283 Individual Protein MAP kinase-interacting serine/threonine-protein kinase MNK1 Homo sapiens Activity = 65.0 % PMID[513942]
NPT3213 Individual Protein MAP kinase signal-integrating kinase 2 Homo sapiens Activity = 80.0 % PMID[513942]
NPT1613 Individual Protein Ribosomal protein S6 kinase alpha 5 Homo sapiens Activity = 36.0 % PMID[513942]
NPT1612 Individual Protein MAP kinase-activated protein kinase 5 Homo sapiens Activity = 96.0 % PMID[513942]
NPT3357 Individual Protein Protein kinase N2 Homo sapiens Activity = 7.0 % PMID[513942]
NPT316 Protein Family Protein kinase C (PKC) Homo sapiens IC50 = 6000.0 nM PMID[513937]
NPT321 Protein Family cAMP-dependent protein kinase (PKA) Homo sapiens IC50 = 3000.0 nM PMID[513937]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 69000.0 nM PMID[513938]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 5400.0 nM PMID[513938]
NPT1284 Protein Family Protein kinase C (PKC) Rattus norvegicus IC50 = 38.4 ug.mL-1 PMID[513940]
NPT2 Others Unspecified Activity = 72.0 % PMID[513942]
NPT728 Individual Protein Serine/threonine-protein kinase AKT Homo sapiens Activity = 87.0 % PMID[513942]
NPT2 Others Unspecified Ki = 5800.0 nM PMID[513943]
NPT316 Protein Family Protein kinase C (PKC) Homo sapiens Ki = 6000.0 nM PMID[513943]
NPT2 Others Unspecified Ki = 100000.0 nM PMID[513943]
NPT1609 Protein Complex Casein kinase II Homo sapiens Ki = 780000.0 nM PMID[513943]
NPT2 Others Unspecified Activity = 67.0 % PMID[513942]
NPT3814 Protein Complex Cyclin-dependent kinase 2/cyclin A Homo sapiens Activity = 54.0 % PMID[513942]
NPT1609 Protein Complex Casein kinase II Homo sapiens Activity = 89.0 % PMID[513942]
NPT981 Individual Protein Inhibitor of nuclear factor kappa B kinase beta subunit Homo sapiens Activity = 86.0 % PMID[513942]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Activity = 88.0 % PMID[513942]
NPT2 Others Unspecified Ki = 49000.0 nM PMID[513944]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC469897 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.7891 Intermediate Similarity NPC166424
0.7891 Intermediate Similarity NPC245244
0.7891 Intermediate Similarity NPC146373
0.7748 Intermediate Similarity NPC282398
0.7655 Intermediate Similarity NPC143603
0.7584 Intermediate Similarity NPC27740
0.7534 Intermediate Similarity NPC91958
0.7468 Intermediate Similarity NPC101165
0.7386 Intermediate Similarity NPC89490
0.7351 Intermediate Similarity NPC476322
0.7338 Intermediate Similarity NPC475090
0.7338 Intermediate Similarity NPC475105
0.7338 Intermediate Similarity NPC329896
0.7333 Intermediate Similarity NPC470233
0.7321 Intermediate Similarity NPC56765
0.7317 Intermediate Similarity NPC321911
0.7273 Intermediate Similarity NPC40070
0.7267 Intermediate Similarity NPC48564
0.7267 Intermediate Similarity NPC265605
0.7267 Intermediate Similarity NPC182570
0.7256 Intermediate Similarity NPC179787
0.7256 Intermediate Similarity NPC201380
0.7256 Intermediate Similarity NPC469811
0.725 Intermediate Similarity NPC88097
0.725 Intermediate Similarity NPC73767
0.7233 Intermediate Similarity NPC314102
0.7233 Intermediate Similarity NPC84911
0.7233 Intermediate Similarity NPC251722
0.7226 Intermediate Similarity NPC476131
0.7222 Intermediate Similarity NPC477977
0.7205 Intermediate Similarity NPC469768
0.7205 Intermediate Similarity NPC469783
0.7205 Intermediate Similarity NPC469779
0.7205 Intermediate Similarity NPC469784
0.7205 Intermediate Similarity NPC469761
0.7205 Intermediate Similarity NPC469780
0.7205 Intermediate Similarity NPC469767
0.7195 Intermediate Similarity NPC63545
0.7186 Intermediate Similarity NPC325903
0.7179 Intermediate Similarity NPC69914
0.7171 Intermediate Similarity NPC290094
0.7171 Intermediate Similarity NPC46358
0.717 Intermediate Similarity NPC325252
0.717 Intermediate Similarity NPC29886
0.717 Intermediate Similarity NPC96102
0.717 Intermediate Similarity NPC261195
0.716 Intermediate Similarity NPC469766
0.7152 Intermediate Similarity NPC471957
0.7143 Intermediate Similarity NPC110126
0.7134 Intermediate Similarity NPC86288
0.7134 Intermediate Similarity NPC314372
0.7134 Intermediate Similarity NPC471322
0.7125 Intermediate Similarity NPC105127
0.7118 Intermediate Similarity NPC41257
0.7118 Intermediate Similarity NPC206819
0.7118 Intermediate Similarity NPC318065
0.7117 Intermediate Similarity NPC190296
0.7114 Intermediate Similarity NPC297486
0.7114 Intermediate Similarity NPC240136
0.7114 Intermediate Similarity NPC471402
0.7105 Intermediate Similarity NPC329825
0.7103 Intermediate Similarity NPC27802
0.7083 Intermediate Similarity NPC200214
0.7081 Intermediate Similarity NPC169433
0.7059 Intermediate Similarity NPC286427
0.7059 Intermediate Similarity NPC236711
0.7048 Intermediate Similarity NPC470111
0.7032 Intermediate Similarity NPC135488
0.7032 Intermediate Similarity NPC169625
0.7032 Intermediate Similarity NPC202957
0.7025 Intermediate Similarity NPC82295
0.7024 Intermediate Similarity NPC216713
0.7024 Intermediate Similarity NPC470823
0.7012 Intermediate Similarity NPC20144
0.7 Intermediate Similarity NPC476464
0.7 Intermediate Similarity NPC198988
0.6994 Remote Similarity NPC90723
0.6994 Remote Similarity NPC279081
0.6989 Remote Similarity NPC201634
0.6982 Remote Similarity NPC138842
0.6977 Remote Similarity NPC44773
0.6977 Remote Similarity NPC122141
0.6977 Remote Similarity NPC215584
0.6977 Remote Similarity NPC470204
0.6966 Remote Similarity NPC280852
0.6964 Remote Similarity NPC53947
0.6964 Remote Similarity NPC24678
0.6964 Remote Similarity NPC105818
0.6959 Remote Similarity NPC167635
0.6959 Remote Similarity NPC193740
0.6951 Remote Similarity NPC476454
0.6941 Remote Similarity NPC476219
0.6936 Remote Similarity NPC225018
0.6936 Remote Similarity NPC470203
0.6933 Remote Similarity NPC316811
0.6933 Remote Similarity NPC315348
0.6933 Remote Similarity NPC32002
0.6932 Remote Similarity NPC194411
0.6928 Remote Similarity NPC159856
0.6918 Remote Similarity NPC256893
0.6897 Remote Similarity NPC76540
0.6897 Remote Similarity NPC317105
0.689 Remote Similarity NPC230002
0.6886 Remote Similarity NPC143872
0.6886 Remote Similarity NPC288838
0.6882 Remote Similarity NPC73952
0.6882 Remote Similarity NPC25008
0.6882 Remote Similarity NPC469760
0.6882 Remote Similarity NPC469763
0.6882 Remote Similarity NPC469786
0.6882 Remote Similarity NPC469765
0.6882 Remote Similarity NPC259644
0.6879 Remote Similarity NPC471311
0.6879 Remote Similarity NPC471313
0.6852 Remote Similarity NPC218268
0.6845 Remote Similarity NPC21605
0.6842 Remote Similarity NPC80597
0.6842 Remote Similarity NPC212376
0.6842 Remote Similarity NPC70922
0.6842 Remote Similarity NPC75540
0.6842 Remote Similarity NPC211572
0.6839 Remote Similarity NPC282231
0.6833 Remote Similarity NPC68354
0.6826 Remote Similarity NPC204141
0.6821 Remote Similarity NPC221786
0.6821 Remote Similarity NPC474791
0.6821 Remote Similarity NPC475990
0.6821 Remote Similarity NPC474880
0.6818 Remote Similarity NPC474561
0.6818 Remote Similarity NPC49954
0.6816 Remote Similarity NPC275305
0.6816 Remote Similarity NPC37423
0.6815 Remote Similarity NPC476140
0.6813 Remote Similarity NPC324611
0.681 Remote Similarity NPC150259
0.6802 Remote Similarity NPC51054
0.6788 Remote Similarity NPC115611
0.6782 Remote Similarity NPC279918
0.678 Remote Similarity NPC63751
0.6778 Remote Similarity NPC474958
0.6765 Remote Similarity NPC33421
0.6763 Remote Similarity NPC469762
0.6763 Remote Similarity NPC216643
0.6747 Remote Similarity NPC63157
0.6747 Remote Similarity NPC473868
0.6746 Remote Similarity NPC477974
0.6742 Remote Similarity NPC91895
0.6742 Remote Similarity NPC116961
0.674 Remote Similarity NPC248454
0.6733 Remote Similarity NPC473901
0.6726 Remote Similarity NPC470440
0.6726 Remote Similarity NPC285731
0.6724 Remote Similarity NPC92796
0.6724 Remote Similarity NPC135141
0.6723 Remote Similarity NPC160105
0.6707 Remote Similarity NPC65408
0.6705 Remote Similarity NPC21174
0.6705 Remote Similarity NPC469813
0.6705 Remote Similarity NPC469785
0.6705 Remote Similarity NPC271797
0.6705 Remote Similarity NPC478182
0.6705 Remote Similarity NPC311276
0.6705 Remote Similarity NPC478184
0.6705 Remote Similarity NPC476446
0.6705 Remote Similarity NPC78375
0.6704 Remote Similarity NPC82331
0.6703 Remote Similarity NPC176199
0.6703 Remote Similarity NPC215795
0.6703 Remote Similarity NPC11126
0.6701 Remote Similarity NPC66699
0.6687 Remote Similarity NPC59084
0.6687 Remote Similarity NPC2949
0.6686 Remote Similarity NPC229173
0.6686 Remote Similarity NPC141926
0.6667 Remote Similarity NPC235843
0.6667 Remote Similarity NPC81561
0.6667 Remote Similarity NPC274229
0.665 Remote Similarity NPC175916
0.6649 Remote Similarity NPC467063
0.6649 Remote Similarity NPC469308
0.6647 Remote Similarity NPC476297
0.6647 Remote Similarity NPC105811
0.6647 Remote Similarity NPC34844
0.6646 Remote Similarity NPC22079
0.663 Remote Similarity NPC471579
0.6629 Remote Similarity NPC293487
0.6629 Remote Similarity NPC54988
0.6629 Remote Similarity NPC56233
0.6627 Remote Similarity NPC467188
0.661 Remote Similarity NPC194640
0.661 Remote Similarity NPC40779
0.6601 Remote Similarity NPC148140
0.66 Remote Similarity NPC124636
0.6596 Remote Similarity NPC103119
0.6595 Remote Similarity NPC163055
0.6592 Remote Similarity NPC201700
0.6581 Remote Similarity NPC11863
0.6575 Remote Similarity NPC161861
0.6575 Remote Similarity NPC314603
0.6571 Remote Similarity NPC316910

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC469897 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9329 High Similarity NPD1328 Approved
0.9205 High Similarity NPD2145 Clinical (unspecified phase)
0.9145 High Similarity NPD1679 Approved
0.8571 High Similarity NPD4641 Discontinued
0.8086 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD3348 Phase 2
0.7712 Intermediate Similarity NPD3944 Approved
0.7712 Intermediate Similarity NPD3942 Approved
0.7679 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD2640 Approved
0.7679 Intermediate Similarity NPD2641 Approved
0.767 Intermediate Similarity NPD2310 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD991 Phase 2
0.7613 Intermediate Similarity NPD792 Discontinued
0.759 Intermediate Similarity NPD1403 Approved
0.759 Intermediate Similarity NPD1404 Approved
0.7572 Intermediate Similarity NPD2084 Discontinued
0.75 Intermediate Similarity NPD3583 Phase 2
0.75 Intermediate Similarity NPD3859 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD461 Approved
0.7483 Intermediate Similarity NPD9583 Approved
0.7471 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD2089 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD9357 Approved
0.7455 Intermediate Similarity NPD976 Approved
0.7455 Intermediate Similarity NPD975 Approved
0.7455 Intermediate Similarity NPD977 Approved
0.7448 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD4510 Discontinued
0.7438 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD2119 Approved
0.7434 Intermediate Similarity NPD2118 Approved
0.7412 Intermediate Similarity NPD2642 Approved
0.7412 Intermediate Similarity NPD2639 Approved
0.7394 Intermediate Similarity NPD3339 Approved
0.7378 Intermediate Similarity NPD2466 Phase 3
0.7378 Intermediate Similarity NPD2465 Approved
0.7378 Intermediate Similarity NPD2462 Phase 3
0.7375 Intermediate Similarity NPD1722 Approved
0.7372 Intermediate Similarity NPD4029 Approved
0.7372 Intermediate Similarity NPD4028 Approved
0.7372 Intermediate Similarity NPD4030 Approved
0.7358 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD786 Approved
0.7356 Intermediate Similarity NPD2771 Approved
0.7356 Intermediate Similarity NPD6044 Discontinued
0.7345 Intermediate Similarity NPD5105 Approved
0.7345 Intermediate Similarity NPD5106 Approved
0.732 Intermediate Similarity NPD1598 Discontinued
0.7301 Intermediate Similarity NPD7469 Discontinued
0.729 Intermediate Similarity NPD715 Phase 3
0.7284 Intermediate Similarity NPD1918 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD3610 Approved
0.7283 Intermediate Similarity NPD3609 Approved
0.7278 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD271 Approved
0.7267 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD268 Approved
0.7256 Intermediate Similarity NPD1661 Suspended
0.7247 Intermediate Similarity NPD5092 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD6194 Discontinued
0.7243 Intermediate Similarity NPD4473 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6771 Discontinued
0.7232 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD4650 Approved
0.7225 Intermediate Similarity NPD2620 Phase 2
0.7225 Intermediate Similarity NPD2619 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD3323 Discontinued
0.7186 Intermediate Similarity NPD2837 Discontinued
0.7179 Intermediate Similarity NPD3475 Approved
0.7179 Intermediate Similarity NPD3476 Approved
0.717 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD1227 Phase 2
0.7151 Intermediate Similarity NPD5213 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD4181 Approved
0.7114 Intermediate Similarity NPD9392 Approved
0.7114 Intermediate Similarity NPD9396 Approved
0.711 Intermediate Similarity NPD5636 Discontinued
0.7101 Intermediate Similarity NPD2580 Discontinued
0.7101 Intermediate Similarity NPD2748 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD1570 Approved
0.7091 Intermediate Similarity NPD1683 Approved
0.7083 Intermediate Similarity NPD2815 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD3082 Discontinued
0.7048 Intermediate Similarity NPD4547 Phase 3
0.7048 Intermediate Similarity NPD4702 Approved
0.7048 Intermediate Similarity NPD4703 Approved
0.7035 Intermediate Similarity NPD8026 Phase 1
0.7035 Intermediate Similarity NPD5315 Discontinued
0.7025 Intermediate Similarity NPD803 Phase 1
0.7022 Intermediate Similarity NPD4398 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD3929 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD162 Approved
0.7006 Intermediate Similarity NPD426 Approved
0.7006 Intermediate Similarity NPD3100 Discontinued
0.7006 Intermediate Similarity NPD4128 Approved
0.7006 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD428 Approved
0.7006 Intermediate Similarity NPD427 Approved
0.7 Intermediate Similarity NPD2141 Approved
0.7 Intermediate Similarity NPD2140 Approved
0.7 Intermediate Similarity NPD3115 Approved
0.7 Intermediate Similarity NPD3112 Approved
0.7 Intermediate Similarity NPD3113 Approved
0.7 Intermediate Similarity NPD3114 Approved
0.7 Intermediate Similarity NPD2142 Approved
0.6994 Remote Similarity NPD1395 Clinical (unspecified phase)
0.6993 Remote Similarity NPD5787 Discontinued
0.6988 Remote Similarity NPD6148 Clinical (unspecified phase)
0.6984 Remote Similarity NPD2405 Phase 3
0.6982 Remote Similarity NPD491 Approved
0.6981 Remote Similarity NPD1994 Approved
0.6981 Remote Similarity NPD1995 Approved
0.6981 Remote Similarity NPD1993 Approved
0.6959 Remote Similarity NPD5300 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5043 Discontinued
0.6941 Remote Similarity NPD2165 Phase 1
0.6933 Remote Similarity NPD2069 Approved
0.6933 Remote Similarity NPD2068 Approved
0.6933 Remote Similarity NPD2073 Approved
0.6933 Remote Similarity NPD2074 Approved
0.6933 Remote Similarity NPD2072 Approved
0.6933 Remote Similarity NPD2075 Approved
0.6933 Remote Similarity NPD2071 Approved
0.6933 Remote Similarity NPD2070 Approved
0.6932 Remote Similarity NPD4024 Phase 3
0.6906 Remote Similarity NPD4399 Phase 2
0.6901 Remote Similarity NPD6574 Clinical (unspecified phase)
0.689 Remote Similarity NPD1649 Discontinued
0.6875 Remote Similarity NPD3015 Discontinued
0.6867 Remote Similarity NPD3813 Approved
0.6864 Remote Similarity NPD2172 Phase 1
0.6863 Remote Similarity NPD4811 Discontinued
0.686 Remote Similarity NPD2865 Clinical (unspecified phase)
0.686 Remote Similarity NPD6497 Approved
0.6857 Remote Similarity NPD2720 Phase 1
0.6857 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4384 Clinical (unspecified phase)
0.6839 Remote Similarity NPD1853 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4304 Discovery
0.6837 Remote Similarity NPD4471 Approved
0.6837 Remote Similarity NPD4472 Approved
0.6836 Remote Similarity NPD5412 Discontinued
0.6833 Remote Similarity NPD3506 Approved
0.6833 Remote Similarity NPD3505 Approved
0.6824 Remote Similarity NPD2103 Approved
0.6821 Remote Similarity NPD5255 Approved
0.6818 Remote Similarity NPD9598 Discontinued
0.6807 Remote Similarity NPD2006 Phase 2
0.6796 Remote Similarity NPD4076 Approved
0.6796 Remote Similarity NPD4079 Approved
0.6796 Remote Similarity NPD3341 Clinical (unspecified phase)
0.6791 Remote Similarity NPD3517 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7561 Approved
0.6784 Remote Similarity NPD1917 Discontinued
0.6779 Remote Similarity NPD4823 Approved
0.6779 Remote Similarity NPD4824 Approved
0.6778 Remote Similarity NPD4075 Phase 2
0.6774 Remote Similarity NPD748 Clinical (unspecified phase)
0.677 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6152 Phase 1
0.6768 Remote Similarity NPD2896 Discontinued
0.6766 Remote Similarity NPD3401 Clinical (unspecified phase)
0.6758 Remote Similarity NPD2481 Approved
0.6758 Remote Similarity NPD2479 Phase 3
0.6752 Remote Similarity NPD572 Clinical (unspecified phase)
0.6742 Remote Similarity NPD5436 Phase 1
0.6742 Remote Similarity NPD4973 Approved
0.6739 Remote Similarity NPD6178 Phase 3
0.6739 Remote Similarity NPD7564 Discontinued
0.6728 Remote Similarity NPD3385 Approved
0.6727 Remote Similarity NPD5518 Clinical (unspecified phase)
0.6723 Remote Similarity NPD4643 Clinical (unspecified phase)
0.6722 Remote Similarity NPD5065 Approved
0.672 Remote Similarity NPD3961 Discontinued
0.672 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6708 Remote Similarity NPD809 Discontinued
0.6707 Remote Similarity NPD201 Phase 2
0.6707 Remote Similarity NPD200 Phase 2
0.6706 Remote Similarity NPD2430 Phase 2
0.6705 Remote Similarity NPD473 Clinical (unspecified phase)
0.6704 Remote Similarity NPD3117 Approved
0.6704 Remote Similarity NPD3116 Approved
0.6703 Remote Similarity NPD1327 Discontinued
0.6687 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6686 Remote Similarity NPD1528 Clinical (unspecified phase)
0.6684 Remote Similarity NPD7175 Phase 1
0.6667 Remote Similarity NPD3039 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1988 Phase 1
0.6667 Remote Similarity NPD4509 Discontinued
0.6667 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3378 Clinical (unspecified phase)
0.665 Remote Similarity NPD7562 Approved
0.665 Remote Similarity NPD4913 Phase 3
0.6649 Remote Similarity NPD4318 Clinical (unspecified phase)
0.6649 Remote Similarity NPD2818 Discontinued
0.6648 Remote Similarity NPD6203 Clinical (unspecified phase)
0.6648 Remote Similarity NPD4184 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data