Structure

Physi-Chem Properties

Molecular Weight:  522.21
Volume:  498.98
LogP:  1.522
LogD:  0.906
LogS:  -4.383
# Rotatable Bonds:  6
TPSA:  162.73
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.29
Synthetic Accessibility Score:  6.49
Fsp3:  0.808
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.364
MDCK Permeability:  7.807582733221352e-05
Pgp-inhibitor:  0.992
Pgp-substrate:  0.109
Human Intestinal Absorption (HIA):  0.047
20% Bioavailability (F20%):  0.044
30% Bioavailability (F30%):  0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.214
Plasma Protein Binding (PPB):  53.94878387451172%
Volume Distribution (VD):  0.342
Pgp-substrate:  42.41682434082031%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.451
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.598
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.016
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.086
CYP3A4-inhibitor:  0.318
CYP3A4-substrate:  0.189

ADMET: Excretion

Clearance (CL):  5.929
Half-life (T1/2):  0.342

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.549
Drug-inuced Liver Injury (DILI):  0.92
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.227
Maximum Recommended Daily Dose:  0.457
Skin Sensitization:  0.14
Carcinogencity:  0.121
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.574

Download Data

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

  Natural Product: NPC16081

Natural Product ID:  NPC16081
Common Name*:   Bruceine A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  LPZSTPCYWWRQFU-VILODJCFSA-N
Standard InCHI:  InChI=1S/C26H34O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h10,12,14,17-21,29-31H,6-9H2,1-5H3/t12-,14+,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1
SMILES:  COC(=O)[C@@]12OC[C@]34[C@H]2[C@@H](OC(=O)CC(C)C)C(=O)O[C@@H]4C[C@@H]2[C@]([C@H]3[C@H]([C@@H]1O)O)(C)CC(=O)C(=C2C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL250451
PubChem CID:   160006
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0002119] Quassinoids

*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
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. seed n.a. DOI[10.1016/0031-9422(96)00258-0]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S1383-5769(99)00023-9]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[10086989]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[1512598]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[15165151]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[15949825]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota fruit Indonesia n.a. PMID[17896817]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[18723353]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. Vietnam n.a. PMID[19026551]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota seeds n.a. n.a. PMID[20050684]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[22506620]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[26522747]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6481366]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7561896]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[8350091]
NPO25589 Brucea amarissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25589 Brucea amarissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12717 Parmelia metastrigosa Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9203 Cephalonomia gallicola Species Bethylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26718 Chelidonura fulvipunctata Species Aglajidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11084 Asplenium normale Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14150 Solanum jamaicense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14749 Lippia carviodora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11637 Psilostrophe cooperi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5303 Castanea crenata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12944 Sideritis tragoriganum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14528 Pneumatospora obcoronata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3164 Yponomeuta malinellus Species Yponomeutidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14845 Ceratophyllum submersum Species Ceratophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10818 Carpobrotus edulis Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25589 Brucea amarissima Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1641 Amycolatopsis azurea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11873 Oecophylla smaragdina Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11432 Centrolobium tomentosum Species Fabaceae 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
NPT83 Cell Line MCF7 Homo sapiens Ratio ED50 = 10.0 n.a. PMID[489581]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 15.0 nM PMID[489581]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 96.0 nM PMID[489581]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 79.0 nM PMID[489581]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 1.5 nM PMID[489581]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 82.0 nM PMID[489583]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 130.0 nM PMID[489583]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 3100.0 nM PMID[489583]
NPT165 Cell Line HeLa Homo sapiens IC50 = 1100.0 nM PMID[489583]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 180.0 nM PMID[489583]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 230.0 nM PMID[489583]
NPT1355 Organism Babesia gibsoni Babesia gibsoni IC50 = 0.004 ug.mL-1 PMID[489579]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.011 ug.mL-1 PMID[489580]
NPT474 Organism Plasmodium berghei Plasmodium berghei ED50 = 3.36 mg/kg/day PMID[489580]
NPT474 Organism Plasmodium berghei Plasmodium berghei ED90 = 26.72 mg/kg/day PMID[489580]
NPT474 Organism Plasmodium berghei Plasmodium berghei Inhibition = 72.0 % PMID[489580]
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 0.097 ug.mL-1 PMID[489582]

☑ 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 NPC16081 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
1.0 High Similarity NPC173686
0.9906 High Similarity NPC268238
0.9906 High Similarity NPC323821
0.9906 High Similarity NPC45218
0.9906 High Similarity NPC143268
0.9545 High Similarity NPC470777
0.9455 High Similarity NPC17772
0.9381 High Similarity NPC91693
0.9381 High Similarity NPC105926
0.9381 High Similarity NPC18945
0.9381 High Similarity NPC265557
0.9298 High Similarity NPC476729
0.9292 High Similarity NPC312833
0.9273 High Similarity NPC328374
0.9273 High Similarity NPC96312
0.9273 High Similarity NPC40632
0.9273 High Similarity NPC251236
0.9217 High Similarity NPC87662
0.9189 High Similarity NPC470854
0.9189 High Similarity NPC287343
0.9189 High Similarity NPC474654
0.9189 High Similarity NPC97908
0.9189 High Similarity NPC122033
0.9182 High Similarity NPC473798
0.913 High Similarity NPC24651
0.9107 High Similarity NPC297179
0.9091 High Similarity NPC49451
0.9043 High Similarity NPC67251
0.9035 High Similarity NPC470779
0.8938 High Similarity NPC204552
0.8938 High Similarity NPC188667
0.8938 High Similarity NPC470776
0.8929 High Similarity NPC152199
0.8929 High Similarity NPC235539
0.8929 High Similarity NPC134869
0.8919 High Similarity NPC198539
0.8919 High Similarity NPC208998
0.8919 High Similarity NPC7921
0.8898 High Similarity NPC475636
0.8898 High Similarity NPC295220
0.8889 High Similarity NPC202524
0.8889 High Similarity NPC477745
0.887 High Similarity NPC102822
0.887 High Similarity NPC477046
0.8839 High Similarity NPC18547
0.8839 High Similarity NPC474906
0.8824 High Similarity NPC54614
0.8824 High Similarity NPC309096
0.8814 High Similarity NPC476008
0.8796 High Similarity NPC181357
0.8783 High Similarity NPC112038
0.8772 High Similarity NPC251310
0.8761 High Similarity NPC207217
0.8761 High Similarity NPC474734
0.8739 High Similarity NPC171888
0.8739 High Similarity NPC146945
0.8727 High Similarity NPC27814
0.8718 High Similarity NPC227397
0.8704 High Similarity NPC65523
0.8696 High Similarity NPC469488
0.8684 High Similarity NPC146432
0.8684 High Similarity NPC473590
0.8684 High Similarity NPC470775
0.8684 High Similarity NPC470778
0.8684 High Similarity NPC176513
0.8661 High Similarity NPC474516
0.8661 High Similarity NPC11252
0.8661 High Similarity NPC289312
0.8644 High Similarity NPC470922
0.8636 High Similarity NPC293850
0.8618 High Similarity NPC262813
0.8596 High Similarity NPC89929
0.8596 High Similarity NPC190185
0.8596 High Similarity NPC213084
0.8584 High Similarity NPC94509
0.8583 High Similarity NPC188291
0.8571 High Similarity NPC34315
0.8571 High Similarity NPC201992
0.8548 High Similarity NPC471089
0.8548 High Similarity NPC141215
0.8548 High Similarity NPC190065
0.8548 High Similarity NPC251998
0.8547 High Similarity NPC275675
0.8545 High Similarity NPC144854
0.8545 High Similarity NPC3316
0.8534 High Similarity NPC258592
0.8534 High Similarity NPC178548
0.8525 High Similarity NPC254614
0.8525 High Similarity NPC102316
0.8525 High Similarity NPC100390
0.8509 High Similarity NPC299849
0.8496 Intermediate Similarity NPC90769
0.8496 Intermediate Similarity NPC193948
0.8482 Intermediate Similarity NPC100908
0.848 Intermediate Similarity NPC596
0.848 Intermediate Similarity NPC295885
0.848 Intermediate Similarity NPC140045
0.8468 Intermediate Similarity NPC192813
0.8468 Intermediate Similarity NPC277017
0.8468 Intermediate Similarity NPC94942
0.8468 Intermediate Similarity NPC154608
0.8462 Intermediate Similarity NPC109607
0.8462 Intermediate Similarity NPC478051
0.8462 Intermediate Similarity NPC107338
0.8435 Intermediate Similarity NPC259306
0.8435 Intermediate Similarity NPC474046
0.8435 Intermediate Similarity NPC470628
0.8421 Intermediate Similarity NPC51978
0.8417 Intermediate Similarity NPC285091
0.8407 Intermediate Similarity NPC157476
0.8393 Intermediate Similarity NPC474242
0.839 Intermediate Similarity NPC169727
0.839 Intermediate Similarity NPC187950
0.839 Intermediate Similarity NPC278163
0.839 Intermediate Similarity NPC194310
0.839 Intermediate Similarity NPC412
0.839 Intermediate Similarity NPC131841
0.839 Intermediate Similarity NPC47567
0.839 Intermediate Similarity NPC258815
0.839 Intermediate Similarity NPC258789
0.839 Intermediate Similarity NPC241310
0.8376 Intermediate Similarity NPC279143
0.8376 Intermediate Similarity NPC475775
0.8376 Intermediate Similarity NPC473920
0.8376 Intermediate Similarity NPC476529
0.8376 Intermediate Similarity NPC127530
0.8361 Intermediate Similarity NPC264192
0.8348 Intermediate Similarity NPC469877
0.8348 Intermediate Similarity NPC247069
0.8348 Intermediate Similarity NPC470919
0.8333 Intermediate Similarity NPC177820
0.8333 Intermediate Similarity NPC473255
0.8333 Intermediate Similarity NPC30188
0.8333 Intermediate Similarity NPC472002
0.8319 Intermediate Similarity NPC474567
0.8319 Intermediate Similarity NPC471965
0.8306 Intermediate Similarity NPC168879
0.8305 Intermediate Similarity NPC251226
0.8291 Intermediate Similarity NPC240509
0.8288 Intermediate Similarity NPC292588
0.8288 Intermediate Similarity NPC102352
0.8254 Intermediate Similarity NPC243014
0.825 Intermediate Similarity NPC14617
0.825 Intermediate Similarity NPC262199
0.825 Intermediate Similarity NPC471964
0.825 Intermediate Similarity NPC471961
0.825 Intermediate Similarity NPC202666
0.8246 Intermediate Similarity NPC472003
0.8235 Intermediate Similarity NPC4021
0.8235 Intermediate Similarity NPC159456
0.823 Intermediate Similarity NPC310546
0.8226 Intermediate Similarity NPC33378
0.8226 Intermediate Similarity NPC254146
0.8226 Intermediate Similarity NPC6274
0.822 Intermediate Similarity NPC319570
0.822 Intermediate Similarity NPC268958
0.822 Intermediate Similarity NPC230513
0.8214 Intermediate Similarity NPC166993
0.8205 Intermediate Similarity NPC27999
0.8205 Intermediate Similarity NPC309433
0.8205 Intermediate Similarity NPC55296
0.8205 Intermediate Similarity NPC477116
0.8198 Intermediate Similarity NPC475036
0.8197 Intermediate Similarity NPC470780
0.8197 Intermediate Similarity NPC470882
0.819 Intermediate Similarity NPC117712
0.819 Intermediate Similarity NPC243354
0.8182 Intermediate Similarity NPC7850
0.8182 Intermediate Similarity NPC471963
0.8182 Intermediate Similarity NPC6615
0.8182 Intermediate Similarity NPC469841
0.8182 Intermediate Similarity NPC247315
0.8182 Intermediate Similarity NPC469842
0.8182 Intermediate Similarity NPC471962
0.8174 Intermediate Similarity NPC302146
0.8174 Intermediate Similarity NPC269530
0.8167 Intermediate Similarity NPC40775
0.8167 Intermediate Similarity NPC235438
0.8167 Intermediate Similarity NPC222688
0.8167 Intermediate Similarity NPC107966
0.8167 Intermediate Similarity NPC249848
0.8167 Intermediate Similarity NPC65858
0.8158 Intermediate Similarity NPC137104
0.8158 Intermediate Similarity NPC320383
0.8158 Intermediate Similarity NPC474786
0.8158 Intermediate Similarity NPC85391
0.8158 Intermediate Similarity NPC210005
0.8151 Intermediate Similarity NPC476849
0.8151 Intermediate Similarity NPC268530
0.8151 Intermediate Similarity NPC109973
0.8151 Intermediate Similarity NPC154491
0.8142 Intermediate Similarity NPC208461
0.8142 Intermediate Similarity NPC273155
0.8142 Intermediate Similarity NPC289702
0.8136 Intermediate Similarity NPC106644
0.8136 Intermediate Similarity NPC286347
0.8131 Intermediate Similarity NPC477438
0.8131 Intermediate Similarity NPC477437
0.8125 Intermediate Similarity NPC470587
0.8125 Intermediate Similarity NPC138908

  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 NPC16081 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
0.825 Intermediate Similarity NPD8328 Phase 3
0.8205 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD6319 Approved
0.8142 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7913 Intermediate Similarity NPD6372 Approved
0.7913 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7913 Intermediate Similarity NPD6373 Approved
0.7886 Intermediate Similarity NPD7492 Approved
0.7863 Intermediate Similarity NPD8297 Approved
0.7851 Intermediate Similarity NPD6054 Approved
0.7851 Intermediate Similarity NPD6059 Approved
0.784 Intermediate Similarity NPD7736 Approved
0.7823 Intermediate Similarity NPD6616 Approved
0.7807 Intermediate Similarity NPD6402 Approved
0.7807 Intermediate Similarity NPD5739 Approved
0.7807 Intermediate Similarity NPD6675 Approved
0.7807 Intermediate Similarity NPD7128 Approved
0.7778 Intermediate Similarity NPD6650 Approved
0.7778 Intermediate Similarity NPD6649 Approved
0.776 Intermediate Similarity NPD8293 Discontinued
0.776 Intermediate Similarity NPD7078 Approved
0.7759 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD6370 Approved
0.7692 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD7320 Approved
0.7672 Intermediate Similarity NPD6881 Approved
0.7672 Intermediate Similarity NPD6899 Approved
0.7647 Intermediate Similarity NPD4632 Approved
0.7642 Intermediate Similarity NPD6016 Approved
0.7642 Intermediate Similarity NPD6015 Approved
0.7586 Intermediate Similarity NPD5697 Approved
0.7586 Intermediate Similarity NPD5701 Approved
0.7581 Intermediate Similarity NPD5988 Approved
0.7563 Intermediate Similarity NPD6882 Approved
0.7542 Intermediate Similarity NPD7102 Approved
0.7542 Intermediate Similarity NPD7290 Approved
0.7542 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD6921 Approved
0.75 Intermediate Similarity NPD7319 Approved
0.7479 Intermediate Similarity NPD6617 Approved
0.7479 Intermediate Similarity NPD6869 Approved
0.7479 Intermediate Similarity NPD6847 Approved
0.7479 Intermediate Similarity NPD8130 Phase 1
0.7459 Intermediate Similarity NPD6009 Approved
0.7458 Intermediate Similarity NPD6013 Approved
0.7458 Intermediate Similarity NPD6014 Approved
0.7458 Intermediate Similarity NPD6012 Approved
0.7436 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD4634 Approved
0.7381 Intermediate Similarity NPD7604 Phase 2
0.7373 Intermediate Similarity NPD6011 Approved
0.736 Intermediate Similarity NPD5983 Phase 2
0.7333 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7115 Discovery
0.7288 Intermediate Similarity NPD6412 Phase 2
0.7287 Intermediate Similarity NPD6033 Approved
0.7266 Intermediate Similarity NPD7507 Approved
0.7266 Intermediate Similarity NPD6336 Discontinued
0.7203 Intermediate Similarity NPD6008 Approved
0.7193 Intermediate Similarity NPD4755 Approved
0.7193 Intermediate Similarity NPD6083 Phase 2
0.7193 Intermediate Similarity NPD6084 Phase 2
0.7193 Intermediate Similarity NPD7902 Approved
0.713 Intermediate Similarity NPD5696 Approved
0.7097 Intermediate Similarity NPD6274 Approved
0.7083 Intermediate Similarity NPD6686 Approved
0.708 Intermediate Similarity NPD7748 Approved
0.7069 Intermediate Similarity NPD4700 Approved
0.7069 Intermediate Similarity NPD5286 Approved
0.7069 Intermediate Similarity NPD4696 Approved
0.7069 Intermediate Similarity NPD5285 Approved
0.7063 Intermediate Similarity NPD7101 Approved
0.7063 Intermediate Similarity NPD7100 Approved
0.7054 Intermediate Similarity NPD7515 Phase 2
0.6984 Remote Similarity NPD6335 Approved
0.6983 Remote Similarity NPD4225 Approved
0.6957 Remote Similarity NPD4697 Phase 3
0.6953 Remote Similarity NPD8516 Approved
0.6953 Remote Similarity NPD8515 Approved
0.6953 Remote Similarity NPD8513 Phase 3
0.6953 Remote Similarity NPD6909 Approved
0.6953 Remote Similarity NPD6908 Approved
0.6953 Remote Similarity NPD8517 Approved
0.6949 Remote Similarity NPD5225 Approved
0.6949 Remote Similarity NPD5224 Approved
0.6949 Remote Similarity NPD5226 Approved
0.6949 Remote Similarity NPD5211 Phase 2
0.6949 Remote Similarity NPD4633 Approved
0.693 Remote Similarity NPD7901 Clinical (unspecified phase)
0.693 Remote Similarity NPD5282 Discontinued
0.693 Remote Similarity NPD7900 Approved
0.6929 Remote Similarity NPD7516 Approved
0.6917 Remote Similarity NPD4767 Approved
0.6917 Remote Similarity NPD4768 Approved
0.6905 Remote Similarity NPD6317 Approved
0.6891 Remote Similarity NPD5174 Approved
0.6891 Remote Similarity NPD5175 Approved
0.6875 Remote Similarity NPD5328 Approved
0.687 Remote Similarity NPD5695 Phase 3
0.6864 Remote Similarity NPD5223 Approved
0.6864 Remote Similarity NPD1700 Approved
0.685 Remote Similarity NPD6313 Approved
0.685 Remote Similarity NPD6314 Approved
0.685 Remote Similarity NPD7328 Approved
0.685 Remote Similarity NPD7327 Approved
0.6847 Remote Similarity NPD3573 Approved
0.6842 Remote Similarity NPD6399 Phase 3
0.6838 Remote Similarity NPD7638 Approved
0.6833 Remote Similarity NPD5141 Approved
0.6825 Remote Similarity NPD6868 Approved
0.6822 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6845 Suspended
0.681 Remote Similarity NPD5220 Clinical (unspecified phase)
0.681 Remote Similarity NPD5222 Approved
0.681 Remote Similarity NPD5221 Approved
0.6803 Remote Similarity NPD4729 Approved
0.6803 Remote Similarity NPD4730 Approved
0.68 Remote Similarity NPD8133 Approved
0.6786 Remote Similarity NPD6672 Approved
0.6786 Remote Similarity NPD5737 Approved
0.678 Remote Similarity NPD7640 Approved
0.678 Remote Similarity NPD7639 Approved
0.6757 Remote Similarity NPD3618 Phase 1
0.6754 Remote Similarity NPD6079 Approved
0.6754 Remote Similarity NPD6411 Approved
0.6752 Remote Similarity NPD5173 Approved
0.675 Remote Similarity NPD4754 Approved
0.6741 Remote Similarity NPD7260 Phase 2
0.6694 Remote Similarity NPD5248 Approved
0.6694 Remote Similarity NPD5249 Phase 3
0.6694 Remote Similarity NPD5251 Approved
0.6694 Remote Similarity NPD5247 Approved
0.6694 Remote Similarity NPD5250 Approved
0.6692 Remote Similarity NPD8380 Approved
0.6692 Remote Similarity NPD8296 Approved
0.6692 Remote Similarity NPD8379 Approved
0.6692 Remote Similarity NPD8335 Approved
0.6692 Remote Similarity NPD8378 Approved
0.6692 Remote Similarity NPD7503 Approved
0.6667 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD5128 Approved
0.6641 Remote Similarity NPD8080 Discontinued
0.6615 Remote Similarity NPD8377 Approved
0.6615 Remote Similarity NPD8294 Approved
0.6609 Remote Similarity NPD8035 Phase 2
0.6609 Remote Similarity NPD8034 Phase 2
0.6607 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6585 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6581 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6581 Remote Similarity NPD4629 Approved
0.6581 Remote Similarity NPD5210 Approved
0.6579 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6080 Approved
0.6579 Remote Similarity NPD6101 Approved
0.6579 Remote Similarity NPD4753 Phase 2
0.6579 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6904 Approved
0.6579 Remote Similarity NPD6673 Approved
0.6567 Remote Similarity NPD8074 Phase 3
0.6565 Remote Similarity NPD8033 Approved
0.6557 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6552 Remote Similarity NPD4202 Approved
0.6544 Remote Similarity NPD5956 Approved
0.6508 Remote Similarity NPD5215 Approved
0.6508 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6508 Remote Similarity NPD5217 Approved
0.6508 Remote Similarity NPD5216 Approved
0.6491 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6481 Remote Similarity NPD3617 Approved
0.6466 Remote Similarity NPD6067 Discontinued
0.646 Remote Similarity NPD7521 Approved
0.646 Remote Similarity NPD6684 Approved
0.646 Remote Similarity NPD5330 Approved
0.646 Remote Similarity NPD7334 Approved
0.646 Remote Similarity NPD7146 Approved
0.646 Remote Similarity NPD6409 Approved
0.6457 Remote Similarity NPD6053 Discontinued
0.6454 Remote Similarity NPD6334 Approved
0.6454 Remote Similarity NPD6333 Approved
0.6439 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6371 Approved
0.6429 Remote Similarity NPD5135 Approved
0.6429 Remote Similarity NPD5169 Approved
0.6429 Remote Similarity NPD5134 Clinical (unspecified phase)
0.641 Remote Similarity NPD5778 Approved
0.641 Remote Similarity NPD5779 Approved
0.6383 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6379 Remote Similarity NPD6698 Approved
0.6379 Remote Similarity NPD46 Approved
0.6378 Remote Similarity NPD5127 Approved
0.6372 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6348 Remote Similarity NPD6903 Approved
0.6325 Remote Similarity NPD7983 Approved
0.6325 Remote Similarity NPD6050 Approved
0.6325 Remote Similarity NPD5693 Phase 1
0.6316 Remote Similarity NPD6098 Approved
0.6311 Remote Similarity NPD5344 Discontinued
0.6303 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6288 Remote Similarity NPD4522 Approved
0.6283 Remote Similarity NPD3133 Approved

  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