Structure

Physi-Chem Properties

Molecular Weight:  514.22
Volume:  504.799
LogP:  3.321
LogD:  2.189
LogS:  -4.679
# Rotatable Bonds:  3
TPSA:  121.64
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.33
Synthetic Accessibility Score:  5.642
Fsp3:  0.714
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.28
MDCK Permeability:  2.6382916985312477e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.757
30% Bioavailability (F30%):  0.717

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.89
Plasma Protein Binding (PPB):  74.29451751708984%
Volume Distribution (VD):  0.99
Pgp-substrate:  23.094419479370117%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.081
CYP2C19-inhibitor:  0.042
CYP2C19-substrate:  0.486
CYP2C9-inhibitor:  0.148
CYP2C9-substrate:  0.018
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.086
CYP3A4-inhibitor:  0.585
CYP3A4-substrate:  0.543

ADMET: Excretion

Clearance (CL):  8.788
Half-life (T1/2):  0.696

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.594
Drug-inuced Liver Injury (DILI):  0.668
AMES Toxicity:  0.113
Rat Oral Acute Toxicity:  0.968
Maximum Recommended Daily Dose:  0.781
Skin Sensitization:  0.253
Carcinogencity:  0.121
Eye Corrosion:  0.561
Eye Irritation:  0.28
Respiratory Toxicity:  0.961

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

  Natural Product: NPC237155

Natural Product ID:  NPC237155
Common Name*:   Nomilin
IUPAC Name:   n.a.
Synonyms:   Nomilin
Standard InCHIKey:  KPDOJFFZKAUIOE-MFPNAYRGSA-N
Standard InCHI:  InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16-,17+,19+,21-,22-,25+,26-,27+,28-/m1/s1
SMILES:  CC(=O)O[C@H]1CC(=O)OC([C@H]2[C@@]1(C)[C@H]1CC[C@@]3([C@]4([C@@]1(C(=O)C2)C)O[C@@H]4C(=O)O[C@@H]3c1ccoc1)C)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL500167
PubChem CID:   12313416
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids
          • [CHEMONTID:0002380] Limonoids

*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
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. fruit n.a. PMID[25522543]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26062 Azadiractica indica n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO7371 Citrus tangemna Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30700 Cassia nodosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14994 Citrus erythrosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26062 Azadiractica indica n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19584 Pericarpium citri reticulatae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26426.1 Cassia javanica subsp. nodosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7371 Citrus tangemna Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14994 Citrus erythrosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5386 Citrus paradisi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14994 Citrus erythrosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26426.1 Cassia javanica subsp. nodosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27288 Citrus maxima Species Rutaceae 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 > 200.0 ug.mL-1 PMID[485073]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 0.00342 ug.mL-1 PMID[485074]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 0.00356 ug.mL-1 PMID[485074]
NPT927 Cell Line PBMC Homo sapiens CC50 = 691.56 ug.mL-1 PMID[485074]
NPT2 Others Unspecified IC50 = 0.0026 ug.mL-1 PMID[485074]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 13.0 ug.mL-1 PMID[485074]
NPT3954 Organism Human T-lymphotropic virus 1 Human T-lymphotropic virus 1 IC50 = 3.98 ug.mL-1 PMID[485074]
NPT27 Others Unspecified Ratio = 230.0 n.a. PMID[485074]
NPT27 Others Unspecified Ratio = 130.0 n.a. PMID[485074]
NPT27 Others Unspecified Ratio = 40.0 n.a. PMID[485074]
NPT27 Others Unspecified CC50 = 755.73 ug.mL-1 PMID[485074]
NPT1192 Organism Spodoptera frugiperda Spodoptera frugiperda AFI = 56.0 % PMID[485075]

☑ 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 NPC237155 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
0.9733 High Similarity NPC263265
0.9671 High Similarity NPC25255
0.9613 High Similarity NPC476853
0.9608 High Similarity NPC470939
0.9608 High Similarity NPC193798
0.9603 High Similarity NPC60973
0.9603 High Similarity NPC126723
0.9542 High Similarity NPC305016
0.9539 High Similarity NPC286722
0.9484 High Similarity NPC476857
0.9484 High Similarity NPC476858
0.9484 High Similarity NPC476856
0.9484 High Similarity NPC123088
0.9484 High Similarity NPC476860
0.9477 High Similarity NPC475295
0.9477 High Similarity NPC473473
0.9474 High Similarity NPC107646
0.9474 High Similarity NPC209364
0.9423 High Similarity NPC23387
0.9416 High Similarity NPC475381
0.9412 High Similarity NPC167142
0.9412 High Similarity NPC472283
0.9363 High Similarity NPC476861
0.9363 High Similarity NPC473753
0.9363 High Similarity NPC473766
0.9363 High Similarity NPC476850
0.9351 High Similarity NPC477403
0.929 High Similarity NPC472653
0.9281 High Similarity NPC469850
0.9241 High Similarity NPC173516
0.9241 High Similarity NPC472282
0.9241 High Similarity NPC472775
0.9241 High Similarity NPC472651
0.9241 High Similarity NPC472774
0.9231 High Similarity NPC5079
0.9231 High Similarity NPC472771
0.92 High Similarity NPC470941
0.9182 High Similarity NPC472652
0.9182 High Similarity NPC160651
0.9182 High Similarity NPC471397
0.9172 High Similarity NPC292389
0.9172 High Similarity NPC469846
0.9172 High Similarity NPC39986
0.9172 High Similarity NPC476197
0.9172 High Similarity NPC302369
0.9172 High Similarity NPC234660
0.9172 High Similarity NPC472773
0.9172 High Similarity NPC51568
0.9172 High Similarity NPC469338
0.9172 High Similarity NPC134254
0.9172 High Similarity NPC477405
0.9167 High Similarity NPC335761
0.9167 High Similarity NPC477402
0.9167 High Similarity NPC191828
0.9161 High Similarity NPC472772
0.9161 High Similarity NPC45101
0.9145 High Similarity NPC196864
0.9145 High Similarity NPC159927
0.9145 High Similarity NPC46551
0.9145 High Similarity NPC477404
0.9145 High Similarity NPC469335
0.9133 High Similarity NPC262198
0.9114 High Similarity NPC469849
0.9114 High Similarity NPC276551
0.9114 High Similarity NPC470940
0.9108 High Similarity NPC263432
0.9108 High Similarity NPC69028
0.9108 High Similarity NPC329938
0.9103 High Similarity NPC473368
0.9085 High Similarity NPC18135
0.9057 High Similarity NPC470875
0.9032 High Similarity NPC264943
0.9026 High Similarity NPC476201
0.9 High Similarity NPC476224
0.9 High Similarity NPC86935
0.8987 High Similarity NPC96443
0.8987 High Similarity NPC6326
0.8987 High Similarity NPC290400
0.8987 High Similarity NPC197596
0.8987 High Similarity NPC117986
0.8987 High Similarity NPC82851
0.8974 High Similarity NPC469485
0.8947 High Similarity NPC221809
0.8944 High Similarity NPC271235
0.8917 High Similarity NPC249021
0.8917 High Similarity NPC173544
0.891 High Similarity NPC469336
0.891 High Similarity NPC476262
0.8903 High Similarity NPC75906
0.8896 High Similarity NPC476122
0.8896 High Similarity NPC469848
0.8896 High Similarity NPC156189
0.8889 High Similarity NPC302392
0.8854 High Similarity NPC204663
0.8846 High Similarity NPC178932
0.8812 High Similarity NPC472669
0.8797 High Similarity NPC299038
0.8797 High Similarity NPC195131
0.8797 High Similarity NPC187149
0.879 High Similarity NPC44675
0.879 High Similarity NPC214541
0.879 High Similarity NPC281258
0.8758 High Similarity NPC271657
0.875 High Similarity NPC471167
0.875 High Similarity NPC149896
0.875 High Similarity NPC142113
0.875 High Similarity NPC18347
0.875 High Similarity NPC472668
0.875 High Similarity NPC471166
0.8742 High Similarity NPC475967
0.8726 High Similarity NPC282445
0.8725 High Similarity NPC476943
0.872 High Similarity NPC159232
0.871 High Similarity NPC470791
0.871 High Similarity NPC470790
0.8704 High Similarity NPC149945
0.8704 High Similarity NPC475779
0.8696 High Similarity NPC663
0.8696 High Similarity NPC471168
0.8696 High Similarity NPC224394
0.8688 High Similarity NPC470789
0.8679 High Similarity NPC261597
0.8679 High Similarity NPC36655
0.8662 High Similarity NPC469503
0.8659 High Similarity NPC470995
0.865 High Similarity NPC472764
0.8634 High Similarity NPC472767
0.8634 High Similarity NPC200782
0.8634 High Similarity NPC207978
0.8625 High Similarity NPC307383
0.8623 High Similarity NPC478177
0.8614 High Similarity NPC471437
0.8608 High Similarity NPC57998
0.8598 High Similarity NPC472766
0.8598 High Similarity NPC327922
0.8598 High Similarity NPC472765
0.8589 High Similarity NPC478178
0.858 High Similarity NPC419
0.8545 High Similarity NPC82602
0.8544 High Similarity NPC44577
0.8533 High Similarity NPC310830
0.8528 High Similarity NPC470182
0.8526 High Similarity NPC19747
0.8519 High Similarity NPC188649
0.8509 High Similarity NPC474932
0.8503 High Similarity NPC236004
0.8494 Intermediate Similarity NPC160818
0.8494 Intermediate Similarity NPC285227
0.8494 Intermediate Similarity NPC169299
0.8491 Intermediate Similarity NPC30222
0.8481 Intermediate Similarity NPC116717
0.848 Intermediate Similarity NPC242068
0.848 Intermediate Similarity NPC247563
0.848 Intermediate Similarity NPC105395
0.8477 Intermediate Similarity NPC220094
0.8476 Intermediate Similarity NPC121995
0.8466 Intermediate Similarity NPC475039
0.8466 Intermediate Similarity NPC88841
0.8466 Intermediate Similarity NPC288602
0.8466 Intermediate Similarity NPC476035
0.8466 Intermediate Similarity NPC14499
0.8462 Intermediate Similarity NPC255414
0.8457 Intermediate Similarity NPC287559
0.8452 Intermediate Similarity NPC262386
0.8452 Intermediate Similarity NPC167340
0.8447 Intermediate Similarity NPC469847
0.8438 Intermediate Similarity NPC35000
0.8438 Intermediate Similarity NPC75310
0.8434 Intermediate Similarity NPC472659
0.8428 Intermediate Similarity NPC268905
0.8428 Intermediate Similarity NPC182427
0.8428 Intermediate Similarity NPC29695
0.8424 Intermediate Similarity NPC478179
0.8424 Intermediate Similarity NPC270312
0.8415 Intermediate Similarity NPC261184
0.8405 Intermediate Similarity NPC211777
0.8405 Intermediate Similarity NPC68848
0.8405 Intermediate Similarity NPC18986
0.8397 Intermediate Similarity NPC346
0.8395 Intermediate Similarity NPC262872
0.8393 Intermediate Similarity NPC471632
0.8393 Intermediate Similarity NPC94763
0.8387 Intermediate Similarity NPC476944
0.8385 Intermediate Similarity NPC41880
0.8377 Intermediate Similarity NPC121158
0.8365 Intermediate Similarity NPC272590
0.8364 Intermediate Similarity NPC472141
0.8364 Intermediate Similarity NPC97574
0.8364 Intermediate Similarity NPC93172
0.8364 Intermediate Similarity NPC214600
0.8354 Intermediate Similarity NPC69647
0.8354 Intermediate Similarity NPC165218
0.8354 Intermediate Similarity NPC472654
0.8354 Intermediate Similarity NPC198047
0.8354 Intermediate Similarity NPC329180
0.8354 Intermediate Similarity NPC472139
0.8354 Intermediate Similarity NPC195325
0.8354 Intermediate Similarity NPC471001
0.8354 Intermediate Similarity NPC125182
0.8344 Intermediate Similarity NPC250228

  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 NPC237155 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
0.8344 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD8434 Phase 2
0.8098 Intermediate Similarity NPD5761 Phase 2
0.8098 Intermediate Similarity NPD5760 Phase 2
0.7614 Intermediate Similarity NPD6764 Approved
0.7614 Intermediate Similarity NPD6765 Approved
0.7456 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD6784 Approved
0.7444 Intermediate Similarity NPD6785 Approved
0.7427 Intermediate Similarity NPD7075 Discontinued
0.7391 Intermediate Similarity NPD1471 Phase 3
0.7381 Intermediate Similarity NPD6599 Discontinued
0.7299 Intermediate Similarity NPD1247 Approved
0.7283 Intermediate Similarity NPD919 Approved
0.7251 Intermediate Similarity NPD7819 Suspended
0.7241 Intermediate Similarity NPD5494 Approved
0.7202 Intermediate Similarity NPD920 Approved
0.7193 Intermediate Similarity NPD6801 Discontinued
0.7127 Intermediate Similarity NPD6559 Discontinued
0.7126 Intermediate Similarity NPD6799 Approved
0.7118 Intermediate Similarity NPD3226 Approved
0.711 Intermediate Similarity NPD5402 Approved
0.711 Intermediate Similarity NPD3817 Phase 2
0.7083 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD4628 Phase 3
0.7035 Intermediate Similarity NPD7411 Suspended
0.7016 Intermediate Similarity NPD8285 Discontinued
0.7011 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5403 Approved
0.6982 Remote Similarity NPD5401 Approved
0.697 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6965 Remote Similarity NPD8404 Phase 2
0.6964 Remote Similarity NPD643 Clinical (unspecified phase)
0.6932 Remote Similarity NPD3749 Approved
0.6927 Remote Similarity NPD3926 Phase 2
0.6909 Remote Similarity NPD2796 Approved
0.6886 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6882 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6832 Phase 2
0.6875 Remote Similarity NPD3882 Suspended
0.6868 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6867 Remote Similarity NPD2346 Discontinued
0.6865 Remote Similarity NPD8313 Approved
0.6865 Remote Similarity NPD8312 Approved
0.6851 Remote Similarity NPD7473 Discontinued
0.6848 Remote Similarity NPD2799 Discontinued
0.6845 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6845 Remote Similarity NPD8150 Discontinued
0.6813 Remote Similarity NPD3751 Discontinued
0.6813 Remote Similarity NPD7799 Discontinued
0.6796 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1243 Approved
0.6784 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4380 Phase 2
0.678 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6778 Remote Similarity NPD3787 Discontinued
0.6776 Remote Similarity NPD5844 Phase 1
0.6765 Remote Similarity NPD7236 Approved
0.6761 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6742 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6722 Remote Similarity NPD8127 Discontinued
0.6721 Remote Similarity NPD3818 Discontinued
0.672 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6718 Remote Similarity NPD4107 Approved
0.6707 Remote Similarity NPD6100 Approved
0.6707 Remote Similarity NPD6099 Approved
0.6706 Remote Similarity NPD3887 Approved
0.6705 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6705 Remote Similarity NPD1934 Approved
0.6703 Remote Similarity NPD2403 Approved
0.6703 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6703 Remote Similarity NPD6166 Phase 2
0.6703 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6703 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7435 Discontinued
0.6687 Remote Similarity NPD3266 Approved
0.6687 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6687 Remote Similarity NPD3267 Approved
0.6686 Remote Similarity NPD2534 Approved
0.6686 Remote Similarity NPD2532 Approved
0.6686 Remote Similarity NPD2533 Approved
0.6685 Remote Similarity NPD6232 Discontinued
0.6685 Remote Similarity NPD6808 Phase 2
0.6667 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD7251 Discontinued
0.6667 Remote Similarity NPD7239 Suspended
0.6649 Remote Similarity NPD8407 Phase 2
0.6647 Remote Similarity NPD3748 Approved
0.6647 Remote Similarity NPD6273 Approved
0.6631 Remote Similarity NPD7808 Phase 3
0.663 Remote Similarity NPD6959 Discontinued
0.6629 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7458 Discontinued
0.6627 Remote Similarity NPD1549 Phase 2
0.6613 Remote Similarity NPD6797 Phase 2
0.6612 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6607 Remote Similarity NPD1551 Phase 2
0.6606 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6599 Remote Similarity NPD4482 Phase 3
0.6585 Remote Similarity NPD2313 Discontinued
0.6585 Remote Similarity NPD3268 Approved
0.6578 Remote Similarity NPD8368 Discontinued
0.6578 Remote Similarity NPD7685 Pre-registration
0.6568 Remote Similarity NPD5762 Approved
0.6568 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6568 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6568 Remote Similarity NPD5763 Approved
0.6566 Remote Similarity NPD1933 Approved
0.6566 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6559 Remote Similarity NPD7074 Phase 3
0.6557 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6548 Remote Similarity NPD7033 Discontinued
0.6545 Remote Similarity NPD8032 Phase 2
0.6541 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6519 Remote Similarity NPD17 Approved
0.6517 Remote Similarity NPD37 Approved
0.6507 Remote Similarity NPD7907 Approved
0.6506 Remote Similarity NPD4307 Phase 2
0.6505 Remote Similarity NPD7054 Approved
0.6502 Remote Similarity NPD7874 Approved
0.6502 Remote Similarity NPD7875 Clinical (unspecified phase)
0.65 Remote Similarity NPD7768 Phase 2
0.65 Remote Similarity NPD4965 Approved
0.65 Remote Similarity NPD4967 Phase 2
0.65 Remote Similarity NPD4966 Approved
0.6494 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6491 Remote Similarity NPD2800 Approved
0.648 Remote Similarity NPD2801 Approved
0.6471 Remote Similarity NPD2344 Approved
0.6471 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7472 Approved
0.6471 Remote Similarity NPD2353 Approved
0.6465 Remote Similarity NPD6777 Approved
0.6465 Remote Similarity NPD6780 Approved
0.6465 Remote Similarity NPD6778 Approved
0.6465 Remote Similarity NPD6781 Approved
0.6465 Remote Similarity NPD6779 Approved
0.6465 Remote Similarity NPD6782 Approved
0.6465 Remote Similarity NPD6776 Approved
0.6461 Remote Similarity NPD5889 Approved
0.6461 Remote Similarity NPD5890 Approved
0.6453 Remote Similarity NPD3750 Approved
0.645 Remote Similarity NPD7697 Approved
0.645 Remote Similarity NPD7696 Phase 3
0.645 Remote Similarity NPD7698 Approved
0.6445 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6444 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6433 Remote Similarity NPD2897 Discontinued
0.6433 Remote Similarity NPD970 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6234 Discontinued
0.6425 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6424 Remote Similarity NPD7095 Approved
0.6418 Remote Similarity NPD7870 Phase 2
0.6418 Remote Similarity NPD8319 Approved
0.6418 Remote Similarity NPD7871 Phase 2
0.6418 Remote Similarity NPD8320 Phase 1
0.6413 Remote Similarity NPD7229 Phase 3
0.6412 Remote Similarity NPD2935 Discontinued
0.6412 Remote Similarity NPD2438 Suspended
0.6411 Remote Similarity NPD4111 Phase 1
0.6404 Remote Similarity NPD6585 Discontinued
0.6398 Remote Similarity NPD3972 Approved
0.6398 Remote Similarity NPD1608 Approved
0.6391 Remote Similarity NPD7097 Phase 1
0.6389 Remote Similarity NPD1465 Phase 2
0.6386 Remote Similarity NPD6798 Discontinued
0.6386 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6369 Remote Similarity NPD447 Suspended
0.6364 Remote Similarity NPD7228 Approved
0.6364 Remote Similarity NPD2163 Approved
0.6364 Remote Similarity NPD1512 Approved
0.6359 Remote Similarity NPD7199 Phase 2
0.6358 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6354 Remote Similarity NPD5353 Approved
0.6353 Remote Similarity NPD1510 Phase 2
0.6353 Remote Similarity NPD4308 Phase 3
0.6352 Remote Similarity NPD5585 Approved
0.6347 Remote Similarity NPD6233 Phase 2
0.6341 Remote Similarity NPD2798 Approved
0.6341 Remote Similarity NPD1019 Discontinued
0.634 Remote Similarity NPD8435 Approved
0.6333 Remote Similarity NPD4665 Approved
0.6324 Remote Similarity NPD5711 Approved
0.6324 Remote Similarity NPD7701 Phase 2
0.6324 Remote Similarity NPD5710 Approved
0.6322 Remote Similarity NPD6190 Approved
0.6322 Remote Similarity NPD2354 Approved
0.6322 Remote Similarity NPD2309 Approved
0.6321 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6319 Remote Similarity NPD7058 Phase 2
0.6319 Remote Similarity NPD7057 Phase 3
0.6318 Remote Similarity NPD3057 Approved
0.6316 Remote Similarity NPD5980 Discovery
0.6313 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6312 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7801 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