Structure

Physi-Chem Properties

Molecular Weight:  642.43
Volume:  659.036
LogP:  3.896
LogD:  4.3
LogS:  -3.005
# Rotatable Bonds:  10
TPSA:  169.3
# H-Bond Aceptor:  10
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.187
Synthetic Accessibility Score:  5.673
Fsp3:  1.0
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.256
MDCK Permeability:  7.736670522717759e-05
Pgp-inhibitor:  0.886
Pgp-substrate:  0.881
Human Intestinal Absorption (HIA):  0.635
20% Bioavailability (F20%):  0.434
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  92.82952117919922%
Volume Distribution (VD):  0.432
Pgp-substrate:  4.202897071838379%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.438
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.635
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.021
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.067
CYP3A4-inhibitor:  0.029
CYP3A4-substrate:  0.066

ADMET: Excretion

Clearance (CL):  1.223
Half-life (T1/2):  0.552

ADMET: Toxicity

hERG Blockers:  0.887
Human Hepatotoxicity (H-HT):  0.146
Drug-inuced Liver Injury (DILI):  0.133
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.005
Skin Sensitization:  0.944
Carcinogencity:  0.016
Eye Corrosion:  0.037
Eye Irritation:  0.018
Respiratory Toxicity:  0.955

Download Data

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

  Natural Product: NPC223125

Natural Product ID:  NPC223125
Common Name*:   Ungeremine
IUPAC Name:   n.a.
Synonyms:   Ungeremine
Standard InCHIKey:  DFQOXFIPAAMFAU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H11NO3/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17/h3-7H,1-2,8H2
SMILES:  O=c1cc2CCn3c2c(c1)c1cc2OCOc2cc1c3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479291
PubChem CID:   3738100
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0001908] Benzoquinolines
          • [CHEMONTID:0000100] Phenanthridines 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
NPO9263 Brachystola magna n.a. n.a. n.a. n.a. n.a. n.a. PMID[16124772]
NPO13784 Dalbergia candenatensis Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[19653666]
NPO12711 Ligularia altaica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[20073490]
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[21314165]
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[21314165]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[21510636]
NPO4576 Corynandra viscosa Species Cleomaceae Eukaryota n.a. leaf n.a. PMID[28135851]
NPO13784 Dalbergia candenatensis Species Fabaceae Eukaryota n.a. Thai n.a. PMID[3430167]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2127 Ungernia minor Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4576 Corynandra viscosa Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9927.2 Crinum asiaticum var. sinicum Varieties Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2127 Ungernia minor Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11473 Viburnum lantana Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10319 Calycodendron milnei n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25680 Ramalina siliquosa Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13784 Dalbergia candenatensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9612 Dryopteris dilatata Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4576 Corynandra viscosa Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2127 Ungernia minor Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9263 Brachystola magna n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10342 Crinum americanum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1412 Artemisia juncea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19776 Hesperocyparis arizonica Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9485 Haplopappus deserticola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27843 Lycoris radiata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11000 Eupatorium laevigatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9144 Atriplex parvifolia Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12711 Ligularia altaica Species Asteraceae 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 3850.0 nM PMID[474413]
NPT168 Cell Line P388 Mus musculus ED50 = 1.2 ug ml-1 PMID[474414]
NPT1081 Cell Line BXPC-3 Homo sapiens ED50 = 0.87 ug ml-1 PMID[474414]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 0.48 ug ml-1 PMID[474414]
NPT395 Cell Line SF-268 Homo sapiens ED50 = 0.057 ug ml-1 PMID[474414]
NPT397 Cell Line NCI-H460 Homo sapiens ED50 = 0.65 ug ml-1 PMID[474414]
NPT575 Cell Line KM-20L2 Homo sapiens ED50 = 0.5 ug ml-1 PMID[474414]
NPT90 Cell Line DU-145 Homo sapiens ED50 = 0.029 ug ml-1 PMID[474414]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[474416]
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 > 10000.0 nM PMID[474416]
NPT169 Cell Line B16-F10 Mus musculus IC50 > 10000.0 nM PMID[474416]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[474417]
NPT916 Cell Line SK-MEL Homo sapiens IC50 > 10000.0 nM PMID[474417]
NPT169 Cell Line B16-F10 Mus musculus IC50 > 10000.0 nM PMID[474417]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens IC50 = 25800.0 nM PMID[474418]
NPT143 Individual Protein DNA topoisomerase I Homo sapiens IC50 = 6100.0 nM PMID[474418]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 1400.0 nM PMID[474418]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[474418]
NPT168 Cell Line P388 Mus musculus T/C = 152.0 % PMID[474419]
NPT168 Cell Line P388 Mus musculus T/C = 148.0 % PMID[474419]
NPT168 Cell Line P388 Mus musculus T/C = 136.0 % PMID[474419]
NPT168 Cell Line P388 Mus musculus T/C = 133.0 % PMID[474419]
NPT5026 Organism Rhodococcus fascians Rhodococcus fascians IZ = 15.0 mm PMID[474415]
NPT5026 Organism Rhodococcus fascians Rhodococcus fascians IZ = 14.0 mm PMID[474415]
NPT5026 Organism Rhodococcus fascians Rhodococcus fascians IZ = 0.0 mm PMID[474415]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 8300.0 nM PMID[474416]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[474416]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[474417]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 83000.0 nM PMID[474417]
NPT2 Others Unspecified IC50 = 7300.0 nM PMID[474418]
NPT2 Others Unspecified IC50 = 15000.0 nM PMID[474418]
NPT2 Others Unspecified FC = 250.0 n.a. PMID[474418]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 31.25 ug.mL-1 PMID[474418]
NPT1242 Organism Salmonella typhi Salmonella enterica subsp. enterica serovar Typhi MIC = 125.0 ug.mL-1 PMID[474418]
NPT32 Organism Mus musculus Mus musculus Activity = -3.9 g PMID[474419]
NPT32 Organism Mus musculus Mus musculus Activity = -2.1 g PMID[474419]
NPT32 Organism Mus musculus Mus musculus Activity = -1.9 g PMID[474419]
NPT32 Organism Mus musculus Mus musculus Activity = -0.7 g PMID[474419]
NPT5026 Organism Rhodococcus fascians Rhodococcus fascians IZ = 15.0 mm PMID[474420]
NPT25178 ORGANISM Edwardsiella ictaluri Edwardsiella ictaluri MIC = 3.0 ug.mL-1 PMID[474420]
NPT19 Organism Escherichia coli Escherichia coli MIC = 25.0 ug.mL-1 PMID[474420]
NPT24393 ORGANISM Flavobacterium columnare Flavobacterium columnare MIC = 3.0 ug.mL-1 PMID[474420]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 125.0 ug.mL-1 PMID[474420]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 25.0 ug.mL-1 PMID[474420]
NPT24393 ORGANISM Flavobacterium columnare Flavobacterium columnare MIC = 1000.0 nM PMID[474420]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 0.97 ug.mL-1 PMID[474421]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 > 30.0 ug.mL-1 PMID[474421]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 0.85 ug.mL-1 PMID[474421]

☑ 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 NPC223125 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
0.986 High Similarity NPC223124
0.9139 High Similarity NPC106786
0.9067 High Similarity NPC78733
0.8961 High Similarity NPC59567
0.8944 High Similarity NPC7018
0.8933 High Similarity NPC148898
0.8933 High Similarity NPC233029
0.8933 High Similarity NPC210148
0.8919 High Similarity NPC475959
0.8903 High Similarity NPC231198
0.8831 High Similarity NPC97072
0.8831 High Similarity NPC215829
0.879 High Similarity NPC474324
0.879 High Similarity NPC57812
0.8758 High Similarity NPC31311
0.8758 High Similarity NPC234392
0.8734 High Similarity NPC475845
0.8718 High Similarity NPC320104
0.8679 High Similarity NPC474708
0.8662 High Similarity NPC306669
0.8662 High Similarity NPC247972
0.8645 High Similarity NPC477080
0.8618 High Similarity NPC476579
0.8571 High Similarity NPC138487
0.8571 High Similarity NPC216459
0.8571 High Similarity NPC41178
0.8553 High Similarity NPC100566
0.8553 High Similarity NPC190332
0.8553 High Similarity NPC181653
0.8519 High Similarity NPC304675
0.8516 High Similarity NPC146288
0.8503 High Similarity NPC314682
0.85 High Similarity NPC158148
0.85 High Similarity NPC82533
0.85 High Similarity NPC475686
0.85 High Similarity NPC266176
0.85 High Similarity NPC58766
0.85 High Similarity NPC290759
0.8467 Intermediate Similarity NPC130926
0.8466 Intermediate Similarity NPC237044
0.8466 Intermediate Similarity NPC474470
0.8452 Intermediate Similarity NPC76079
0.8447 Intermediate Similarity NPC474475
0.8447 Intermediate Similarity NPC75958
0.8446 Intermediate Similarity NPC188163
0.8446 Intermediate Similarity NPC213206
0.8446 Intermediate Similarity NPC328750
0.8446 Intermediate Similarity NPC474915
0.8415 Intermediate Similarity NPC474325
0.8408 Intermediate Similarity NPC111485
0.8408 Intermediate Similarity NPC118804
0.8395 Intermediate Similarity NPC477640
0.8395 Intermediate Similarity NPC470739
0.8395 Intermediate Similarity NPC225597
0.8392 Intermediate Similarity NPC160193
0.8364 Intermediate Similarity NPC474745
0.8354 Intermediate Similarity NPC160298
0.8354 Intermediate Similarity NPC477559
0.8354 Intermediate Similarity NPC232924
0.8354 Intermediate Similarity NPC306902
0.8354 Intermediate Similarity NPC266753
0.8344 Intermediate Similarity NPC4669
0.8333 Intermediate Similarity NPC136860
0.8333 Intermediate Similarity NPC93593
0.8333 Intermediate Similarity NPC311991
0.8333 Intermediate Similarity NPC476567
0.8333 Intermediate Similarity NPC128019
0.8323 Intermediate Similarity NPC476580
0.8323 Intermediate Similarity NPC210918
0.8313 Intermediate Similarity NPC168409
0.8301 Intermediate Similarity NPC37144
0.8301 Intermediate Similarity NPC59907
0.8299 Intermediate Similarity NPC416184
0.8294 Intermediate Similarity NPC63152
0.8282 Intermediate Similarity NPC65403
0.8272 Intermediate Similarity NPC241055
0.8272 Intermediate Similarity NPC86469
0.8263 Intermediate Similarity NPC102760
0.8261 Intermediate Similarity NPC476002
0.8243 Intermediate Similarity NPC95366
0.8243 Intermediate Similarity NPC252107
0.8243 Intermediate Similarity NPC248505
0.8224 Intermediate Similarity NPC185838
0.8214 Intermediate Similarity NPC475981
0.8214 Intermediate Similarity NPC474746
0.8199 Intermediate Similarity NPC225774
0.8199 Intermediate Similarity NPC232514
0.8199 Intermediate Similarity NPC302527
0.8199 Intermediate Similarity NPC276944
0.8199 Intermediate Similarity NPC167546
0.8199 Intermediate Similarity NPC238530
0.8199 Intermediate Similarity NPC16805
0.8194 Intermediate Similarity NPC274026
0.8187 Intermediate Similarity NPC24954
0.8176 Intermediate Similarity NPC137172
0.8176 Intermediate Similarity NPC99078
0.8176 Intermediate Similarity NPC145446
0.8165 Intermediate Similarity NPC147091
0.8165 Intermediate Similarity NPC57512
0.8148 Intermediate Similarity NPC219341
0.8148 Intermediate Similarity NPC476432
0.8148 Intermediate Similarity NPC24264
0.8144 Intermediate Similarity NPC27887
0.8144 Intermediate Similarity NPC244554
0.8141 Intermediate Similarity NPC85747
0.8141 Intermediate Similarity NPC8337
0.8137 Intermediate Similarity NPC476569
0.8137 Intermediate Similarity NPC189470
0.8129 Intermediate Similarity NPC219162
0.8121 Intermediate Similarity NPC253429
0.8121 Intermediate Similarity NPC220923
0.8118 Intermediate Similarity NPC230098
0.8117 Intermediate Similarity NPC51957
0.8117 Intermediate Similarity NPC179825
0.8117 Intermediate Similarity NPC476144
0.8117 Intermediate Similarity NPC210437
0.8117 Intermediate Similarity NPC16107
0.8117 Intermediate Similarity NPC321505
0.8117 Intermediate Similarity NPC106295
0.8117 Intermediate Similarity NPC191376
0.8108 Intermediate Similarity NPC196609
0.8108 Intermediate Similarity NPC73883
0.8108 Intermediate Similarity NPC255817
0.8108 Intermediate Similarity NPC136330
0.8108 Intermediate Similarity NPC96406
0.8108 Intermediate Similarity NPC230698
0.8108 Intermediate Similarity NPC251454
0.8108 Intermediate Similarity NPC205178
0.8108 Intermediate Similarity NPC277042
0.8098 Intermediate Similarity NPC247389
0.8098 Intermediate Similarity NPC298979
0.8095 Intermediate Similarity NPC160692
0.8089 Intermediate Similarity NPC133011
0.8089 Intermediate Similarity NPC82285
0.8086 Intermediate Similarity NPC39103
0.8086 Intermediate Similarity NPC2770
0.8084 Intermediate Similarity NPC15919
0.8072 Intermediate Similarity NPC308267
0.8065 Intermediate Similarity NPC24233
0.8065 Intermediate Similarity NPC428
0.8065 Intermediate Similarity NPC130941
0.8065 Intermediate Similarity NPC135538
0.8065 Intermediate Similarity NPC7467
0.8065 Intermediate Similarity NPC147390
0.8065 Intermediate Similarity NPC476571
0.8065 Intermediate Similarity NPC246587
0.8054 Intermediate Similarity NPC131204
0.8054 Intermediate Similarity NPC301050
0.8049 Intermediate Similarity NPC470324
0.8041 Intermediate Similarity NPC167096
0.8041 Intermediate Similarity NPC94280
0.8041 Intermediate Similarity NPC103947
0.8041 Intermediate Similarity NPC159150
0.8041 Intermediate Similarity NPC328419
0.8041 Intermediate Similarity NPC193673
0.8041 Intermediate Similarity NPC45783
0.8037 Intermediate Similarity NPC86144
0.8037 Intermediate Similarity NPC304659
0.8036 Intermediate Similarity NPC149285
0.8027 Intermediate Similarity NPC217574
0.8025 Intermediate Similarity NPC218614
0.8012 Intermediate Similarity NPC205167
0.8012 Intermediate Similarity NPC249274
0.8 Intermediate Similarity NPC83511
0.8 Intermediate Similarity NPC253883
0.8 Intermediate Similarity NPC470707
0.8 Intermediate Similarity NPC95075
0.8 Intermediate Similarity NPC476151
0.8 Intermediate Similarity NPC90844
0.7977 Intermediate Similarity NPC226708
0.7976 Intermediate Similarity NPC294790
0.7976 Intermediate Similarity NPC118633
0.7976 Intermediate Similarity NPC148693
0.7964 Intermediate Similarity NPC187678
0.7962 Intermediate Similarity NPC192768
0.7962 Intermediate Similarity NPC220858
0.7962 Intermediate Similarity NPC88249
0.7962 Intermediate Similarity NPC97221
0.7962 Intermediate Similarity NPC151895
0.7952 Intermediate Similarity NPC149090
0.7952 Intermediate Similarity NPC303581
0.7952 Intermediate Similarity NPC67978
0.7952 Intermediate Similarity NPC19520
0.7911 Intermediate Similarity NPC326316
0.7911 Intermediate Similarity NPC476568
0.7911 Intermediate Similarity NPC81733
0.7907 Intermediate Similarity NPC169387
0.7907 Intermediate Similarity NPC477259
0.7904 Intermediate Similarity NPC2314
0.7901 Intermediate Similarity NPC4304
0.7901 Intermediate Similarity NPC165797
0.7898 Intermediate Similarity NPC60538
0.7898 Intermediate Similarity NPC470088
0.7898 Intermediate Similarity NPC477565
0.7898 Intermediate Similarity NPC207824
0.7898 Intermediate Similarity NPC103379
0.7892 Intermediate Similarity NPC6152
0.7892 Intermediate Similarity NPC152212
0.7879 Intermediate Similarity NPC252960
0.7877 Intermediate Similarity NPC172403

  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 NPC223125 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
0.8446 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD3639 Approved
0.8366 Intermediate Similarity NPD3641 Approved
0.8366 Intermediate Similarity NPD3640 Phase 3
0.8117 Intermediate Similarity NPD4584 Approved
0.8108 Intermediate Similarity NPD2492 Phase 1
0.8049 Intermediate Similarity NPD2898 Approved
0.7987 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD4166 Phase 2
0.7911 Intermediate Similarity NPD4017 Approved
0.7891 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD4773 Phase 2
0.7812 Intermediate Similarity NPD4772 Phase 2
0.7785 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5977 Approved
0.7778 Intermediate Similarity NPD5978 Approved
0.7764 Intermediate Similarity NPD7298 Approved
0.7758 Intermediate Similarity NPD6107 Approved
0.7753 Intermediate Similarity NPD4420 Approved
0.7674 Intermediate Similarity NPD7280 Phase 3
0.7674 Intermediate Similarity NPD7281 Phase 3
0.7673 Intermediate Similarity NPD6030 Approved
0.7673 Intermediate Similarity NPD6031 Approved
0.76 Intermediate Similarity NPD5718 Phase 2
0.7582 Intermediate Similarity NPD5006 Approved
0.7582 Intermediate Similarity NPD5005 Approved
0.7515 Intermediate Similarity NPD4481 Phase 3
0.75 Intermediate Similarity NPD6071 Discontinued
0.7485 Intermediate Similarity NPD5312 Approved
0.7485 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD5313 Approved
0.7473 Intermediate Similarity NPD4859 Phase 1
0.7455 Intermediate Similarity NPD2560 Approved
0.7455 Intermediate Similarity NPD2563 Approved
0.7419 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4010 Discontinued
0.7375 Intermediate Similarity NPD3124 Discontinued
0.7358 Intermediate Similarity NPD5241 Discontinued
0.7351 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6297 Approved
0.7262 Intermediate Similarity NPD5604 Discontinued
0.7262 Intermediate Similarity NPD7833 Phase 2
0.7262 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD7831 Phase 2
0.7251 Intermediate Similarity NPD2969 Approved
0.7251 Intermediate Similarity NPD2970 Approved
0.7244 Intermediate Similarity NPD6895 Approved
0.7244 Intermediate Similarity NPD6896 Approved
0.7241 Intermediate Similarity NPD3885 Approved
0.7235 Intermediate Similarity NPD7802 Discontinued
0.7225 Intermediate Similarity NPD8251 Approved
0.7225 Intermediate Similarity NPD8252 Approved
0.7225 Intermediate Similarity NPD8099 Discontinued
0.7209 Intermediate Similarity NPD27 Approved
0.7209 Intermediate Similarity NPD2489 Approved
0.7202 Intermediate Similarity NPD6788 Approved
0.7195 Intermediate Similarity NPD4210 Discontinued
0.7193 Intermediate Similarity NPD3051 Approved
0.7186 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD8156 Discontinued
0.7182 Intermediate Similarity NPD7296 Approved
0.7169 Intermediate Similarity NPD7110 Phase 1
0.7169 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5582 Discontinued
0.7152 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6851 Approved
0.7135 Intermediate Similarity NPD6853 Approved
0.7127 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD1424 Approved
0.7111 Intermediate Similarity NPD7291 Discontinued
0.7111 Intermediate Similarity NPD3349 Phase 2
0.7097 Intermediate Similarity NPD5457 Discontinued
0.7095 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2978 Approved
0.7083 Intermediate Similarity NPD4585 Approved
0.7083 Intermediate Similarity NPD2977 Approved
0.7081 Intermediate Similarity NPD5754 Discontinued
0.7079 Intermediate Similarity NPD2971 Approved
0.7079 Intermediate Similarity NPD2968 Approved
0.7079 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD5297 Approved
0.7052 Intermediate Similarity NPD6687 Approved
0.7052 Intermediate Similarity NPD6688 Approved
0.7051 Intermediate Similarity NPD3109 Approved
0.7051 Intermediate Similarity NPD3110 Approved
0.7039 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD6618 Phase 2
0.7037 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4727 Phase 1
0.7027 Intermediate Similarity NPD5564 Approved
0.7006 Intermediate Similarity NPD6875 Approved
0.7006 Intermediate Similarity NPD6876 Approved
0.7 Intermediate Similarity NPD3705 Approved
0.6987 Remote Similarity NPD2674 Phase 3
0.6983 Remote Similarity NPD5917 Clinical (unspecified phase)
0.6977 Remote Similarity NPD5677 Discontinued
0.6962 Remote Similarity NPD2653 Approved
0.6962 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6946 Remote Similarity NPD824 Approved
0.6944 Remote Similarity NPD8053 Approved
0.6944 Remote Similarity NPD8054 Approved
0.6923 Remote Similarity NPD7248 Discontinued
0.6923 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6365 Clinical (unspecified phase)
0.6914 Remote Similarity NPD4236 Phase 3
0.6914 Remote Similarity NPD4237 Approved
0.6914 Remote Similarity NPD5177 Phase 3
0.6911 Remote Similarity NPD7607 Clinical (unspecified phase)
0.6908 Remote Similarity NPD1421 Approved
0.6908 Remote Similarity NPD1420 Approved
0.6894 Remote Similarity NPD3656 Approved
0.6893 Remote Similarity NPD5600 Discontinued
0.689 Remote Similarity NPD2120 Phase 2
0.689 Remote Similarity NPD3845 Phase 1
0.689 Remote Similarity NPD7124 Phase 2
0.6885 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6882 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6879 Remote Similarity NPD4474 Approved
0.6879 Remote Similarity NPD4475 Approved
0.6871 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5089 Approved
0.6864 Remote Similarity NPD6386 Approved
0.6864 Remote Similarity NPD6873 Phase 2
0.6864 Remote Similarity NPD6385 Approved
0.6864 Remote Similarity NPD5090 Approved
0.6852 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6848 Remote Similarity NPD2421 Approved
0.6848 Remote Similarity NPD2420 Approved
0.6848 Remote Similarity NPD2490 Approved
0.6848 Remote Similarity NPD2488 Approved
0.6842 Remote Similarity NPD2358 Clinical (unspecified phase)
0.6832 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6832 Remote Similarity NPD2161 Phase 2
0.6828 Remote Similarity NPD6493 Phase 3
0.6826 Remote Similarity NPD5976 Discontinued
0.6826 Remote Similarity NPD1914 Approved
0.6825 Remote Similarity NPD4107 Approved
0.6824 Remote Similarity NPD3382 Approved
0.6824 Remote Similarity NPD3383 Approved
0.6824 Remote Similarity NPD3384 Approved
0.6821 Remote Similarity NPD7400 Phase 3
0.6815 Remote Similarity NPD3144 Approved
0.6815 Remote Similarity NPD3145 Approved
0.6813 Remote Similarity NPD743 Approved
0.6813 Remote Similarity NPD6111 Discontinued
0.6796 Remote Similarity NPD7312 Approved
0.6796 Remote Similarity NPD7313 Approved
0.6796 Remote Similarity NPD7310 Approved
0.6796 Remote Similarity NPD7311 Approved
0.6796 Remote Similarity NPD4578 Approved
0.6796 Remote Similarity NPD4577 Approved
0.6793 Remote Similarity NPD3408 Clinical (unspecified phase)
0.679 Remote Similarity NPD1375 Discontinued
0.6788 Remote Similarity NPD2422 Clinical (unspecified phase)
0.6784 Remote Similarity NPD5773 Approved
0.6784 Remote Similarity NPD5772 Approved
0.6774 Remote Similarity NPD7905 Discontinued
0.6774 Remote Similarity NPD7247 Discontinued
0.677 Remote Similarity NPD4108 Discontinued
0.6768 Remote Similarity NPD6748 Discontinued
0.6761 Remote Similarity NPD5242 Approved
0.676 Remote Similarity NPD3920 Phase 2
0.6758 Remote Similarity NPD7309 Approved
0.6755 Remote Similarity NPD2667 Approved
0.6755 Remote Similarity NPD2668 Approved
0.6753 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6746 Remote Similarity NPD3866 Clinical (unspecified phase)
0.6743 Remote Similarity NPD3983 Phase 3
0.6743 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7906 Approved
0.6726 Remote Similarity NPD1670 Discontinued
0.6725 Remote Similarity NPD5720 Discontinued
0.6724 Remote Similarity NPD4796 Discontinued
0.671 Remote Similarity NPD4098 Discontinued
0.6707 Remote Similarity NPD4162 Approved
0.6707 Remote Similarity NPD7019 Approved
0.6707 Remote Similarity NPD3060 Approved
0.6707 Remote Similarity NPD7020 Approved
0.6706 Remote Similarity NPD7028 Phase 2
0.6705 Remote Similarity NPD19 Approved
0.6705 Remote Similarity NPD1743 Approved
0.6705 Remote Similarity NPD1742 Approved
0.6704 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6702 Remote Similarity NPD4482 Phase 3
0.6701 Remote Similarity NPD3816 Phase 1
0.6701 Remote Similarity NPD3815 Phase 1
0.6685 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6685 Remote Similarity NPD4663 Approved
0.6667 Remote Similarity NPD1307 Phase 2
0.6667 Remote Similarity NPD1309 Phase 2
0.6667 Remote Similarity NPD3448 Approved
0.6667 Remote Similarity NPD3763 Approved
0.6667 Remote Similarity NPD1753 Discontinued

  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