Structure

Physi-Chem Properties

Molecular Weight:  245.09
Volume:  229.888
LogP:  -1.266
LogD:  -0.568
LogS:  -1.891
# Rotatable Bonds:  1
TPSA:  112.9
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.511
Synthetic Accessibility Score:  4.02
Fsp3:  0.182
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:  -5.661
MDCK Permeability:  3.0769608656555647e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.081
Human Intestinal Absorption (HIA):  0.038
20% Bioavailability (F20%):  0.131
30% Bioavailability (F30%):  0.783

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.746
Plasma Protein Binding (PPB):  16.776758193969727%
Volume Distribution (VD):  1.454
Pgp-substrate:  84.8583755493164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.398
CYP2C19-inhibitor:  0.047
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.309
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.15
CYP3A4-inhibitor:  0.007
CYP3A4-substrate:  0.035

ADMET: Excretion

Clearance (CL):  2.085
Half-life (T1/2):  0.646

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.822
Drug-inuced Liver Injury (DILI):  0.3
AMES Toxicity:  0.247
Rat Oral Acute Toxicity:  0.025
Maximum Recommended Daily Dose:  0.857
Skin Sensitization:  0.256
Carcinogencity:  0.144
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.931

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC162268

Natural Product ID:  NPC162268
Common Name*:   Debromohymenialdisine
IUPAC Name:   (4Z)-4-(2-amino-4-oxo-1H-imidazol-5-ylidene)-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one
Synonyms:   (Z)-2-Debromohymenialdisine; Debromohymenialdisine
Standard InCHIKey:  JYRJOQGKGMHTOO-VURMDHGXSA-N
Standard InCHI:  InChI=1S/C11H11N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/b8-6-
SMILES:  c1c[nH]c2c1/C(=C1/C(=NC(=N)N1)O)/CCN=C2O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL255465
PubChem CID:   5288032
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001990] Pyrroloazepines

*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
NPO7079 Stylissa massa Species Axinellidae Eukaryota n.a. Philippine n.a. PMID[11784156]
NPO7079 Stylissa massa Species Axinellidae Eukaryota n.a. n.a. n.a. PMID[12816422]
NPO24195 Stylissa carteri Species Axinellidae Eukaryota n.a. n.a. n.a. PMID[15043426]
NPO33061 pseudaxinella sp. Species Axinellidae Eukaryota n.a. Republic of Palau 1979 PMID[18327911]
NPO7079 Stylissa massa Species Axinellidae Eukaryota n.a. n.a. n.a. PMID[23684893]
NPO32942 phakellia mauritiana Species Bubaridae Eukaryota n.a. Indian ocean n.a. PMID[9051914]
NPO24195 Stylissa carteri Species Axinellidae Eukaryota n.a. indopacific n.a. PMID[9917317]
NPO6961 Vernonia arctioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3926 Ptilometra australis Species Ptilometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24195 Stylissa carteri Species Axinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8562 Echinocystis fabacea Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7079 Stylissa massa Species Axinellidae 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
NPT491 Individual Protein Dual specificity mitogen-activated protein kinase kinase 1 Homo sapiens IC50 = 2500.0 nM PMID[524324]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens IC50 = 824.0 nM PMID[524324]
NPT492 Cell Line Caco-2 Homo sapiens IC50 > 10000.0 nM PMID[524324]
NPT114 Cell Line LoVo Homo sapiens IC50 > 10000.0 nM PMID[524324]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens IC50 = 824.0 nM PMID[524325]
NPT1608 Individual Protein Serine/threonine-protein kinase Chk1 Homo sapiens IC50 = 725.0 nM PMID[524325]
NPT1680 Individual Protein Serine/threonine-protein kinase Chk2 Homo sapiens IC50 = 183.0 nM PMID[524325]
NPT1608 Individual Protein Serine/threonine-protein kinase Chk1 Homo sapiens IC50 = 3000.0 nM PMID[524326]
NPT1680 Individual Protein Serine/threonine-protein kinase Chk2 Homo sapiens IC50 = 3500.0 nM PMID[524326]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 25000.0 nM PMID[524326]
NPT168 Cell Line P388 Mus musculus Activity = 5.0 ug ml-1 PMID[524327]
NPT377 Cell Line OVCAR-3 Homo sapiens ED50 = 1.8 ug ml-1 PMID[524328]
NPT399 Cell Line SF-295 Homo sapiens ED50 = 38.9 ug ml-1 PMID[524328]
NPT376 Cell Line A498 Homo sapiens ED50 = 24.7 ug ml-1 PMID[524328]
NPT397 Cell Line NCI-H460 Homo sapiens ED50 = 42.0 ug ml-1 PMID[524328]
NPT575 Cell Line KM-20L2 Homo sapiens ED50 = 8.5 ug ml-1 PMID[524328]
NPT373 Cell Line SK-MEL-5 Homo sapiens ED50 = 5.7 ug ml-1 PMID[524328]
NPT1608 Individual Protein Serine/threonine-protein kinase Chk1 Homo sapiens IC50 = 330.0 nM PMID[524329]
NPT1608 Individual Protein Serine/threonine-protein kinase Chk1 Homo sapiens IC50 = 725.0 nM PMID[524331]
NPT1680 Individual Protein Serine/threonine-protein kinase Chk2 Homo sapiens IC50 = 183.0 nM PMID[524331]
NPT4886 Individual Protein Ubiquitin carboxyl-terminal hydrolase 7 Homo sapiens Inhibition = 20.0 % PMID[524332]
NPT1671 Individual Protein AMP-activated protein kinase, alpha-2 subunit Homo sapiens Thermal melting change = -0.5 degrees C PMID[524333]
NPT1672 Individual Protein CaM kinase I delta Homo sapiens Thermal melting change = 0.0 degrees C PMID[524333]
NPT1673 Individual Protein CaM kinase I gamma Homo sapiens Thermal melting change = 0.2 degrees C PMID[524333]
NPT1674 Individual Protein CaM kinase II alpha Homo sapiens Thermal melting change = 0.1 degrees C PMID[524333]
NPT1630 Individual Protein CaM kinase II beta Homo sapiens Thermal melting change = 0.7 degrees C PMID[524333]
NPT1675 Individual Protein CaM kinase II delta Homo sapiens Thermal melting change = 0.1 degrees C PMID[524333]
NPT1676 Individual Protein CaM kinase II gamma Homo sapiens Thermal melting change = 0.3 degrees C PMID[524333]
NPT1677 Individual Protein CaM kinase IV Homo sapiens Thermal melting change = 0.0 degrees C PMID[524333]
NPT1678 Individual Protein CaM-kinase kinase beta Homo sapiens Thermal melting change = 1.4 degrees C PMID[524333]
NPT1371 Individual Protein Cyclin-dependent kinase 2 Homo sapiens Thermal melting change = 0.7 degrees C PMID[524333]
NPT1571 Individual Protein Cyclin-dependent kinase 6 Homo sapiens Thermal melting change = 0.6 degrees C PMID[524333]
NPT1679 Individual Protein Cyclin-dependent kinase-like 1 Homo sapiens Thermal melting change = 0.3 degrees C PMID[524333]
NPT1680 Individual Protein Serine/threonine-protein kinase Chk2 Homo sapiens Thermal melting change = 1.7 degrees C PMID[524333]
NPT1681 Individual Protein Dual specificty protein kinase CLK1 Homo sapiens Thermal melting change = 6.0 degrees C PMID[524333]
NPT1682 Individual Protein Dual specificity protein kinase CLK2 Homo sapiens Thermal melting change = 3.7 degrees C PMID[524333]
NPT1683 Individual Protein Dual specificity protein kinase CLK3 Homo sapiens Thermal melting change = 4.5 degrees C PMID[524333]
NPT1684 Individual Protein Casein kinase I gamma 1 Homo sapiens Thermal melting change = 3.6 degrees C PMID[524333]
NPT1685 Individual Protein Casein kinase I gamma 2 Homo sapiens Thermal melting change = 3.5 degrees C PMID[524333]
NPT1686 Individual Protein Casein kinase I isoform gamma-3 Homo sapiens Thermal melting change = 2.4 degrees C PMID[524333]
NPT1687 Individual Protein Death-associated protein kinase 3 Homo sapiens Thermal melting change = 5.2 degrees C PMID[524333]
NPT1688 Individual Protein Myotonin-protein kinase Homo sapiens Thermal melting change = 2.3 degrees C PMID[524333]
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens Thermal melting change = 5.0 degrees C PMID[524333]
NPT1689 Individual Protein Tyrosine-protein kinase JAK1 Homo sapiens Thermal melting change = -0.2 degrees C PMID[524333]
NPT1690 Individual Protein Dual specificity mitogen-activated protein kinase kinase 2 Homo sapiens Thermal melting change = 0.4 degrees C PMID[524333]
NPT1691 Individual Protein Dual specificity mitogen-activated protein kinase kinase 6 Homo sapiens Thermal melting change = 0.3 degrees C PMID[524333]
NPT1431 Individual Protein Mitogen-activated protein kinase kinase kinase 5 Homo sapiens Thermal melting change = 4.6 degrees C PMID[524333]
NPT1616 Individual Protein MAP kinase p38 beta Homo sapiens Thermal melting change = -0.4 degrees C PMID[524333]
NPT281 Individual Protein MAP kinase ERK1 Homo sapiens Thermal melting change = 0.6 degrees C PMID[524333]
NPT1692 Individual Protein Mitogen-activated protein kinase 6 Homo sapiens Thermal melting change = 0.3 degrees C PMID[524333]
NPT1693 Individual Protein Serine/threonine-protein kinase MST4 Homo sapiens Thermal melting change = 1.3 degrees C PMID[524333]
NPT1658 Individual Protein Serine/threonine-protein kinase NEK2 Homo sapiens Thermal melting change = 1.1 degrees C PMID[524333]
NPT1657 Individual Protein Serine/threonine-protein kinase NEK6 Homo sapiens Thermal melting change = -0.5 degrees C PMID[524333]
NPT1694 Individual Protein Serine/threonine-protein kinase OSR1 Homo sapiens Thermal melting change = 0.4 degrees C PMID[524333]
NPT1695 Individual Protein Serine/threonine-protein kinase PAK 4 Homo sapiens Thermal melting change = 0.9 degrees C PMID[524333]
NPT1696 Individual Protein Serine/threonine-protein kinase PAK7 Homo sapiens Thermal melting change = 0.2 degrees C PMID[524333]
NPT1697 Individual Protein Serine/threonine-protein kinase PAK6 Homo sapiens Thermal melting change = 0.1 degrees C PMID[524333]
NPT1698 Individual Protein Serine/threonine-protein kinase PCTAIRE-1 Homo sapiens Thermal melting change = 0.0 degrees C PMID[524333]
NPT1699 Individual Protein 3-phosphoinositide dependent protein kinase-1 Homo sapiens Thermal melting change = 0.0 degrees C PMID[524333]
NPT1265 Individual Protein Serine/threonine-protein kinase PIM1 Homo sapiens Thermal melting change = 0.7 degrees C PMID[524333]
NPT1700 Individual Protein Serine/threonine-protein kinase PIM2 Homo sapiens Thermal melting change = 2.5 degrees C PMID[524333]
NPT1701 Individual Protein Serine/threonine-protein kinase PIM3 Homo sapiens Thermal melting change = 2.4 degrees C PMID[524333]
NPT1702 Individual Protein Serine/threonine-protein kinase PLK4 Homo sapiens Thermal melting change = 0.9 degrees C PMID[524333]
NPT1703 Individual Protein cAMP-dependent protein kinase alpha-catalytic subunit Homo sapiens Thermal melting change = 0.0 degrees C PMID[524333]
NPT1704 Individual Protein Serine/threonine-protein kinase RIO2 Homo sapiens Thermal melting change = -0.3 degrees C PMID[524333]
NPT1705 Individual Protein Ribosomal protein S6 kinase alpha 3 Homo sapiens Thermal melting change = 2.6 degrees C PMID[524333]
NPT1705 Individual Protein Ribosomal protein S6 kinase alpha 3 Homo sapiens Thermal melting change = 6.4 degrees C PMID[524333]
NPT1706 Individual Protein Serine/threonine-protein kinase 2 Homo sapiens Thermal melting change = 0.6 degrees C PMID[524333]
NPT1707 Individual Protein Serine/threonine-protein kinase 10 Homo sapiens Thermal melting change = 1.7 degrees C PMID[524333]
NPT1708 Individual Protein Serine/threonine-protein kinase 16 Homo sapiens Thermal melting change = 0.4 degrees C PMID[524333]
NPT1709 Individual Protein Serine/threonine-protein kinase 17A Homo sapiens Thermal melting change = 10.2 degrees C PMID[524333]
NPT1710 Individual Protein Serine/threonine-protein kinase 38 Homo sapiens Thermal melting change = 0.7 degrees C PMID[524333]
NPT1693 Individual Protein Serine/threonine-protein kinase MST4 Homo sapiens Thermal melting change = 0.7 degrees C PMID[524333]
NPT1711 Individual Protein Serine/threonine-protein kinase MST1 Homo sapiens Thermal melting change = 2.6 degrees C PMID[524333]
NPT1712 Individual Protein TRAF2- and NCK-interacting kinase Homo sapiens Thermal melting change = 1.6 degrees C PMID[524333]
NPT1713 Individual Protein PDZ-binding kinase Homo sapiens Thermal melting change = -0.4 degrees C PMID[524333]
NPT1715 Individual Protein Serine/threonine-protein kinase VRK2 Homo sapiens Thermal melting change = 0.7 degrees C PMID[524333]
NPT1717 Individual Protein Serine/threonine-protein kinase 25 Homo sapiens Thermal melting change = 1.7 degrees C PMID[524333]
NPT1680 Individual Protein Serine/threonine-protein kinase Chk2 Homo sapiens IC50 = 183.0 nM PMID[524334]
NPT1608 Individual Protein Serine/threonine-protein kinase Chk1 Homo sapiens IC50 = 725.0 nM PMID[524334]
NPT490 Protein Family Serine/threonine-protein kinase RAF and Dual specificity mitogen-activated protein kinase kinase 1 (Raf/MEK) Homo sapiens IC50 = 881.0 nM PMID[524324]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2.4 ug.mL-1 PMID[524330]
NPT2 Others Unspecified Ratio IC50 = 4.0 n.a. PMID[524331]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Thermal melting change = 2.4 degrees C PMID[524333]
NPT22960 SINGLE PROTEIN Serine/threonine-protein kinase VRK1 Homo sapiens Thermal melting change = 1.3 degrees C PMID[524333]
NPT22961 SINGLE PROTEIN Inactive serine/threonine-protein kinase VRK3 Homo sapiens Thermal melting change = 0.5 degrees C PMID[524333]

☑ 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 NPC162268 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
0.96 High Similarity NPC212742
0.8726 High Similarity NPC475870
0.8072 Intermediate Similarity NPC49217
0.7831 Intermediate Similarity NPC131718
0.7633 Intermediate Similarity NPC102423
0.7485 Intermediate Similarity NPC159856
0.744 Intermediate Similarity NPC141353
0.7432 Intermediate Similarity NPC304187
0.7432 Intermediate Similarity NPC477166
0.7412 Intermediate Similarity NPC279918
0.7405 Intermediate Similarity NPC242209
0.7389 Intermediate Similarity NPC188387
0.7389 Intermediate Similarity NPC163421
0.7381 Intermediate Similarity NPC33229
0.7374 Intermediate Similarity NPC48938
0.7371 Intermediate Similarity NPC313791
0.7368 Intermediate Similarity NPC282231
0.7353 Intermediate Similarity NPC230869
0.7341 Intermediate Similarity NPC160105
0.7329 Intermediate Similarity NPC104049
0.7326 Intermediate Similarity NPC476118
0.7321 Intermediate Similarity NPC73952
0.7321 Intermediate Similarity NPC469765
0.7321 Intermediate Similarity NPC469760
0.7321 Intermediate Similarity NPC259644
0.7321 Intermediate Similarity NPC25008
0.7321 Intermediate Similarity NPC469763
0.7321 Intermediate Similarity NPC469786
0.7312 Intermediate Similarity NPC328029
0.7305 Intermediate Similarity NPC105818
0.7305 Intermediate Similarity NPC24678
0.7294 Intermediate Similarity NPC469762
0.7293 Intermediate Similarity NPC314002
0.7278 Intermediate Similarity NPC220765
0.7278 Intermediate Similarity NPC80597
0.7278 Intermediate Similarity NPC477815
0.7278 Intermediate Similarity NPC211572
0.7278 Intermediate Similarity NPC75540
0.7278 Intermediate Similarity NPC70922
0.7278 Intermediate Similarity NPC212376
0.7273 Intermediate Similarity NPC314372
0.7256 Intermediate Similarity NPC190296
0.7247 Intermediate Similarity NPC96890
0.7247 Intermediate Similarity NPC184964
0.7244 Intermediate Similarity NPC306397
0.7243 Intermediate Similarity NPC477167
0.7243 Intermediate Similarity NPC473342
0.7241 Intermediate Similarity NPC49954
0.7241 Intermediate Similarity NPC474561
0.7241 Intermediate Similarity NPC54988
0.7238 Intermediate Similarity NPC204717
0.7235 Intermediate Similarity NPC469785
0.7229 Intermediate Similarity NPC143872
0.7225 Intermediate Similarity NPC311276
0.7216 Intermediate Similarity NPC302647
0.7213 Intermediate Similarity NPC46580
0.7207 Intermediate Similarity NPC42979
0.72 Intermediate Similarity NPC63751
0.7191 Intermediate Similarity NPC224764
0.7181 Intermediate Similarity NPC77555
0.7175 Intermediate Similarity NPC314603
0.7158 Intermediate Similarity NPC171171
0.7157 Intermediate Similarity NPC282247
0.7151 Intermediate Similarity NPC135141
0.7151 Intermediate Similarity NPC92796
0.7151 Intermediate Similarity NPC59269
0.7134 Intermediate Similarity NPC212125
0.7127 Intermediate Similarity NPC184932
0.7127 Intermediate Similarity NPC472861
0.7119 Intermediate Similarity NPC470498
0.7104 Intermediate Similarity NPC15102
0.71 Intermediate Similarity NPC469717
0.7099 Intermediate Similarity NPC29702
0.7086 Intermediate Similarity NPC41333
0.7059 Intermediate Similarity NPC99666
0.7041 Intermediate Similarity NPC282531
0.7039 Intermediate Similarity NPC203468
0.7039 Intermediate Similarity NPC110500
0.7039 Intermediate Similarity NPC149155
0.7029 Intermediate Similarity NPC194640
0.7029 Intermediate Similarity NPC40779
0.7017 Intermediate Similarity NPC126709
0.7017 Intermediate Similarity NPC248041
0.7017 Intermediate Similarity NPC283219
0.7011 Intermediate Similarity NPC470204
0.701 Intermediate Similarity NPC473376
0.7006 Intermediate Similarity NPC78020
0.7 Intermediate Similarity NPC267885
0.6994 Remote Similarity NPC96102
0.6989 Remote Similarity NPC32771
0.6982 Remote Similarity NPC471957
0.6971 Remote Similarity NPC470203
0.6963 Remote Similarity NPC131887
0.6961 Remote Similarity NPC248454
0.6961 Remote Similarity NPC473380
0.6961 Remote Similarity NPC111275
0.6961 Remote Similarity NPC240088
0.6957 Remote Similarity NPC324611
0.6957 Remote Similarity NPC82295
0.6957 Remote Similarity NPC284678
0.6952 Remote Similarity NPC83111
0.6951 Remote Similarity NPC105127
0.6951 Remote Similarity NPC84911
0.6951 Remote Similarity NPC125746
0.694 Remote Similarity NPC233936
0.6935 Remote Similarity NPC278434
0.6923 Remote Similarity NPC141377
0.6918 Remote Similarity NPC165370
0.6914 Remote Similarity NPC322976
0.6914 Remote Similarity NPC324203
0.6914 Remote Similarity NPC63338
0.6912 Remote Similarity NPC473317
0.6911 Remote Similarity NPC156704
0.6898 Remote Similarity NPC472289
0.6898 Remote Similarity NPC213629
0.6897 Remote Similarity NPC138018
0.6891 Remote Similarity NPC315491
0.6891 Remote Similarity NPC45459
0.689 Remote Similarity NPC29886
0.689 Remote Similarity NPC261195
0.6878 Remote Similarity NPC324149
0.6875 Remote Similarity NPC192315
0.6867 Remote Similarity NPC110126
0.6867 Remote Similarity NPC73767
0.686 Remote Similarity NPC216713
0.6854 Remote Similarity NPC41717
0.685 Remote Similarity NPC128084
0.6848 Remote Similarity NPC71037
0.6842 Remote Similarity NPC307963
0.6839 Remote Similarity NPC476167
0.6835 Remote Similarity NPC27740
0.6831 Remote Similarity NPC265710
0.6828 Remote Similarity NPC311282
0.6826 Remote Similarity NPC469783
0.6826 Remote Similarity NPC469767
0.6826 Remote Similarity NPC469779
0.6826 Remote Similarity NPC469761
0.6826 Remote Similarity NPC469768
0.6826 Remote Similarity NPC469780
0.6826 Remote Similarity NPC469784
0.6826 Remote Similarity NPC279081
0.6818 Remote Similarity NPC476465
0.6818 Remote Similarity NPC122141
0.6816 Remote Similarity NPC201700
0.6812 Remote Similarity NPC125597
0.6811 Remote Similarity NPC163055
0.6809 Remote Similarity NPC321708
0.6806 Remote Similarity NPC326634
0.68 Remote Similarity NPC320968
0.68 Remote Similarity NPC82370
0.6793 Remote Similarity NPC16659
0.6791 Remote Similarity NPC94752
0.6791 Remote Similarity NPC476527
0.6786 Remote Similarity NPC469766
0.6784 Remote Similarity NPC80596
0.6776 Remote Similarity NPC84827
0.6776 Remote Similarity NPC145885
0.6776 Remote Similarity NPC14113
0.6771 Remote Similarity NPC251090
0.6768 Remote Similarity NPC62151
0.6766 Remote Similarity NPC471603
0.6765 Remote Similarity NPC204141
0.6765 Remote Similarity NPC475736
0.6763 Remote Similarity NPC130570
0.6758 Remote Similarity NPC37268
0.6755 Remote Similarity NPC317030
0.6755 Remote Similarity NPC17059
0.6754 Remote Similarity NPC106937
0.6751 Remote Similarity NPC470500
0.6748 Remote Similarity NPC256893
0.6748 Remote Similarity NPC471322
0.6744 Remote Similarity NPC37548
0.6742 Remote Similarity NPC78375
0.6742 Remote Similarity NPC476446
0.6742 Remote Similarity NPC469813
0.674 Remote Similarity NPC89562
0.6739 Remote Similarity NPC55772
0.6738 Remote Similarity NPC280290
0.6733 Remote Similarity NPC54744
0.6726 Remote Similarity NPC230002
0.6725 Remote Similarity NPC288838
0.672 Remote Similarity NPC209917
0.672 Remote Similarity NPC296527
0.672 Remote Similarity NPC469358
0.6719 Remote Similarity NPC133366
0.6718 Remote Similarity NPC213308
0.6716 Remote Similarity NPC477114
0.6714 Remote Similarity NPC156003
0.6707 Remote Similarity NPC314646
0.6704 Remote Similarity NPC17751
0.6704 Remote Similarity NPC280864
0.6702 Remote Similarity NPC474707
0.6702 Remote Similarity NPC315555
0.6702 Remote Similarity NPC235684
0.6701 Remote Similarity NPC470499
0.6687 Remote Similarity NPC315320
0.6686 Remote Similarity NPC63562
0.6685 Remote Similarity NPC151939
0.6685 Remote Similarity NPC256828
0.6685 Remote Similarity NPC194411

  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 NPC162268 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
0.815 Intermediate Similarity NPD706 Phase 1
0.7514 Intermediate Similarity NPD3178 Discontinued
0.7429 Intermediate Similarity NPD5065 Approved
0.7407 Intermediate Similarity NPD1592 Phase 3
0.7337 Intermediate Similarity NPD2127 Suspended
0.7326 Intermediate Similarity NPD5140 Approved
0.7326 Intermediate Similarity NPD5138 Approved
0.7267 Intermediate Similarity NPD8026 Phase 1
0.7257 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD9080 Approved
0.7232 Intermediate Similarity NPD2928 Phase 2
0.7213 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD6595 Phase 3
0.7134 Intermediate Similarity NPD9284 Approved
0.711 Intermediate Similarity NPD687 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD7948 Phase 1
0.7079 Intermediate Similarity NPD1599 Approved
0.7056 Intermediate Similarity NPD2144 Approved
0.7055 Intermediate Similarity NPD9506 Approved
0.7052 Intermediate Similarity NPD5255 Approved
0.7052 Intermediate Similarity NPD704 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD1043 Phase 3
0.7039 Intermediate Similarity NPD482 Approved
0.7037 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD276 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD1649 Discontinued
0.7006 Intermediate Similarity NPD1352 Discontinued
0.7005 Intermediate Similarity NPD459 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD3013 Phase 3
0.7005 Intermediate Similarity NPD3014 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.6995 Remote Similarity NPD5596 Phase 2
0.6994 Remote Similarity NPD198 Clinical (unspecified phase)
0.6984 Remote Similarity NPD4999 Phase 3
0.6984 Remote Similarity NPD4998 Phase 3
0.6966 Remote Similarity NPD1325 Approved
0.6966 Remote Similarity NPD1326 Approved
0.6961 Remote Similarity NPD6203 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6545 Clinical (unspecified phase)
0.6954 Remote Similarity NPD604 Clinical (unspecified phase)
0.694 Remote Similarity NPD3038 Discontinued
0.6939 Remote Similarity NPD8493 Clinical (unspecified phase)
0.6935 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6927 Remote Similarity NPD3814 Phase 1
0.6914 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6909 Remote Similarity NPD203 Clinical (unspecified phase)
0.6905 Remote Similarity NPD3813 Approved
0.6904 Remote Similarity NPD4612 Discontinued
0.6891 Remote Similarity NPD484 Approved
0.6885 Remote Similarity NPD6452 Discontinued
0.6882 Remote Similarity NPD2872 Phase 2
0.6867 Remote Similarity NPD786 Approved
0.6865 Remote Similarity NPD1096 Discontinued
0.6862 Remote Similarity NPD3870 Clinical (unspecified phase)
0.6862 Remote Similarity NPD5117 Phase 2
0.6862 Remote Similarity NPD3871 Clinical (unspecified phase)
0.6857 Remote Similarity NPD1554 Clinical (unspecified phase)
0.6854 Remote Similarity NPD425 Approved
0.6854 Remote Similarity NPD424 Approved
0.6854 Remote Similarity NPD1248 Discontinued
0.6845 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1038 Approved
0.6842 Remote Similarity NPD5428 Discontinued
0.6837 Remote Similarity NPD1915 Phase 1
0.6834 Remote Similarity NPD7809 Clinical (unspecified phase)
0.6831 Remote Similarity NPD8386 Phase 2
0.6828 Remote Similarity NPD6610 Clinical (unspecified phase)
0.6825 Remote Similarity NPD1235 Phase 3
0.6818 Remote Similarity NPD2189 Approved
0.6818 Remote Similarity NPD2187 Approved
0.6811 Remote Similarity NPD2092 Phase 2
0.6811 Remote Similarity NPD2095 Phase 2
0.6811 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6811 Remote Similarity NPD2094 Phase 2
0.6811 Remote Similarity NPD2391 Clinical (unspecified phase)
0.6807 Remote Similarity NPD9076 Clinical (unspecified phase)
0.68 Remote Similarity NPD949 Phase 1
0.6789 Remote Similarity NPD1234 Discontinued
0.6789 Remote Similarity NPD3404 Approved
0.6786 Remote Similarity NPD1722 Approved
0.6784 Remote Similarity NPD4703 Approved
0.6784 Remote Similarity NPD4702 Approved
0.6774 Remote Similarity NPD2096 Phase 2
0.6774 Remote Similarity NPD2091 Phase 2
0.6772 Remote Similarity NPD3439 Approved
0.6772 Remote Similarity NPD2544 Clinical (unspecified phase)
0.6768 Remote Similarity NPD8410 Clinical (unspecified phase)
0.676 Remote Similarity NPD5611 Phase 2
0.6758 Remote Similarity NPD4128 Approved
0.6757 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6755 Remote Similarity NPD8431 Approved
0.6754 Remote Similarity NPD802 Phase 2
0.6746 Remote Similarity NPD3717 Discontinued
0.6739 Remote Similarity NPD4076 Approved
0.6739 Remote Similarity NPD4079 Approved
0.6738 Remote Similarity NPD2814 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6022 Clinical (unspecified phase)
0.6737 Remote Similarity NPD4699 Discontinued
0.6722 Remote Similarity NPD2844 Phase 3
0.672 Remote Similarity NPD8110 Clinical (unspecified phase)
0.6716 Remote Similarity NPD7470 Discontinued
0.6705 Remote Similarity NPD2581 Approved
0.6705 Remote Similarity NPD2582 Approved
0.6705 Remote Similarity NPD4462 Approved
0.6705 Remote Similarity NPD4463 Approved
0.6704 Remote Similarity NPD926 Approved
0.6704 Remote Similarity NPD925 Approved
0.6703 Remote Similarity NPD966 Clinical (unspecified phase)
0.6703 Remote Similarity NPD750 Phase 2
0.6702 Remote Similarity NPD6665 Discontinued
0.6702 Remote Similarity NPD4615 Phase 2
0.6702 Remote Similarity NPD6887 Clinical (unspecified phase)
0.67 Remote Similarity NPD7970 Approved
0.67 Remote Similarity NPD7971 Clinical (unspecified phase)
0.6687 Remote Similarity NPD9207 Approved
0.6687 Remote Similarity NPD9206 Approved
0.6686 Remote Similarity NPD3834 Clinical (unspecified phase)
0.6685 Remote Similarity NPD4181 Approved
0.6685 Remote Similarity NPD3505 Approved
0.6685 Remote Similarity NPD3506 Approved
0.6683 Remote Similarity NPD796 Phase 2
0.6683 Remote Similarity NPD8458 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8321 Discontinued
0.6667 Remote Similarity NPD1173 Approved
0.6667 Remote Similarity NPD6164 Phase 2
0.6667 Remote Similarity NPD5901 Discontinued
0.6667 Remote Similarity NPD6165 Phase 2
0.6667 Remote Similarity NPD1315 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1570 Approved
0.665 Remote Similarity NPD8094 Discontinued
0.665 Remote Similarity NPD537 Phase 2
0.665 Remote Similarity NPD8488 Clinical (unspecified phase)
0.665 Remote Similarity NPD534 Phase 2
0.6649 Remote Similarity NPD5082 Clinical (unspecified phase)
0.6649 Remote Similarity NPD5081 Phase 1
0.6649 Remote Similarity NPD3082 Discontinued
0.6647 Remote Similarity NPD4374 Clinical (unspecified phase)
0.6646 Remote Similarity NPD9726 Discontinued
0.6632 Remote Similarity NPD1912 Approved
0.6632 Remote Similarity NPD6965 Clinical (unspecified phase)
0.6629 Remote Similarity NPD1917 Discontinued
0.6615 Remote Similarity NPD994 Phase 2
0.6615 Remote Similarity NPD996 Phase 2
0.6615 Remote Similarity NPD3406 Suspended
0.6612 Remote Similarity NPD3224 Phase 2
0.661 Remote Similarity NPD9382 Approved
0.661 Remote Similarity NPD9383 Approved
0.6609 Remote Similarity NPD2172 Phase 1
0.6605 Remote Similarity NPD992 Clinical (unspecified phase)
0.6605 Remote Similarity NPD991 Phase 2
0.6603 Remote Similarity NPD7202 Clinical (unspecified phase)
0.6601 Remote Similarity NPD3976 Clinical (unspecified phase)
0.6601 Remote Similarity NPD3917 Approved
0.6601 Remote Similarity NPD8093 Discontinued
0.6601 Remote Similarity NPD3916 Clinical (unspecified phase)
0.6601 Remote Similarity NPD3918 Approved
0.66 Remote Similarity NPD1392 Approved
0.66 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6595 Remote Similarity NPD1272 Clinical (unspecified phase)
0.6593 Remote Similarity NPD565 Phase 2
0.6591 Remote Similarity NPD3405 Phase 3
0.6588 Remote Similarity NPD416 Approved
0.6585 Remote Similarity NPD5612 Discontinued
0.6582 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6581 Remote Similarity NPD269 Clinical (unspecified phase)
0.658 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6578 Remote Similarity NPD2526 Phase 2
0.6578 Remote Similarity NPD2523 Phase 2
0.657 Remote Similarity NPD4555 Clinical (unspecified phase)
0.6566 Remote Similarity NPD6132 Phase 1
0.6564 Remote Similarity NPD3830 Phase 1
0.6556 Remote Similarity NPD8129 Discovery
0.6556 Remote Similarity NPD5925 Phase 1
0.6552 Remote Similarity NPD3915 Approved
0.6552 Remote Similarity NPD3100 Discontinued
0.6552 Remote Similarity NPD8013 Clinical (unspecified phase)
0.655 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6545 Remote Similarity NPD803 Phase 1
0.6541 Remote Similarity NPD5100 Phase 3
0.6531 Remote Similarity NPD3469 Phase 3
0.6522 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6522 Remote Similarity NPD9357 Approved
0.652 Remote Similarity NPD3330 Phase 1
0.6503 Remote Similarity NPD2619 Clinical (unspecified phase)
0.6503 Remote Similarity NPD2620 Phase 2
0.6503 Remote Similarity NPD1598 Discontinued
0.65 Remote Similarity NPD5426 Phase 3
0.6497 Remote Similarity NPD9392 Approved
0.6497 Remote Similarity NPD9396 Approved
0.6497 Remote Similarity NPD4548 Discontinued
0.6495 Remote Similarity NPD3403 Clinical (unspecified phase)
0.6489 Remote Similarity NPD1708 Approved
0.6489 Remote Similarity NPD1895 Discontinued
0.6489 Remote Similarity NPD4649 Clinical (unspecified phase)
0.6489 Remote Similarity NPD1707 Approved
0.6486 Remote Similarity NPD9690 Approved
0.6477 Remote Similarity NPD3262 Approved
0.6471 Remote Similarity NPD2930 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