Structure

Physi-Chem Properties

Molecular Weight:  1044.55
Volume:  1004.341
LogP:  2.047
LogD:  2.3
LogS:  -3.7
# Rotatable Bonds:  10
TPSA:  322.67
# H-Bond Aceptor:  21
# H-Bond Donor:  11
# Rings:  10
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.119
Synthetic Accessibility Score:  7.958
Fsp3:  0.981
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:  -5.914
MDCK Permeability:  3.826841202680953e-05
Pgp-inhibitor:  0.936
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.99
20% Bioavailability (F20%):  0.023
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.082
Plasma Protein Binding (PPB):  71.46143341064453%
Volume Distribution (VD):  0.09
Pgp-substrate:  13.207480430603027%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.963
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.205
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.003
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.052
CYP3A4-inhibitor:  0.035
CYP3A4-substrate:  0.013

ADMET: Excretion

Clearance (CL):  0.306
Half-life (T1/2):  0.799

ADMET: Toxicity

hERG Blockers:  0.297
Human Hepatotoxicity (H-HT):  0.178
Drug-inuced Liver Injury (DILI):  0.006
AMES Toxicity:  0.089
Rat Oral Acute Toxicity:  0.143
Maximum Recommended Daily Dose:  0.196
Skin Sensitization:  0.53
Carcinogencity:  0.016
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.561

Download Data

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

  Natural Product: NPC273189

Natural Product ID:  NPC273189
Common Name*:   Clethroidoside D
IUPAC Name:   n.a.
Synonyms:   Clethroidoside D
Standard InCHIKey:  LXYNMISGVPYMHU-LGZUVIOGSA-N
Standard InCHI:  InChI=1S/C52H84O21/c1-46(2)14-15-51-22-67-52(29(51)16-46)13-9-28-48(5)11-10-31(47(3,4)27(48)8-12-49(28,6)50(52,7)17-30(51)56)71-44-40(73-43-39(64)36(61)33(58)24(18-53)68-43)35(60)26(21-66-44)70-45-41(37(62)34(59)25(19-54)69-45)72-42-38(63)32(57)23(55)20-65-42/h23-29,31-45,53-55,57-64H,8-22H2,1-7H3/t23-,24-,25-,26+,27+,28-,29-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,48+,49-,50+,51-,52+/m1/s1
SMILES:  CC1(C)CC[C@@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@@H](C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)CC3=O)O[C@H]3[C@@H]([C@H]([C@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@@H]2C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1927849
PubChem CID:   56598062
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO21278 Lysimachia clethroides Species Primulaceae Eukaryota n.a. aerial part n.a. PMID[21928797]
NPO21278 Lysimachia clethroides Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21278 Lysimachia clethroides Species Primulaceae 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
NPT139 Cell Line HT-29 Homo sapiens IC50 = 1980.0 nM PMID[489219]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 1730.0 nM PMID[489219]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 1360.0 nM PMID[489219]
NPT81 Cell Line A549 Homo sapiens IC50 = 2360.0 nM PMID[489219]
NPT1083 Cell Line A-375 Homo sapiens IC50 = 1910.0 nM PMID[489219]

☑ 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 NPC273189 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 NPC184805
0.9898 High Similarity NPC471430
0.9897 High Similarity NPC267637
0.9691 High Similarity NPC80640
0.9604 High Similarity NPC470622
0.9604 High Similarity NPC66513
0.96 High Similarity NPC207693
0.9505 High Similarity NPC87393
0.9505 High Similarity NPC22709
0.9485 High Similarity NPC80417
0.9231 High Similarity NPC157571
0.9118 High Similarity NPC138219
0.9118 High Similarity NPC126753
0.9118 High Similarity NPC475630
0.9118 High Similarity NPC40716
0.9118 High Similarity NPC475234
0.9029 High Similarity NPC473688
0.9029 High Similarity NPC471626
0.9029 High Similarity NPC231566
0.9029 High Similarity NPC262567
0.902 High Similarity NPC119628
0.902 High Similarity NPC158051
0.902 High Similarity NPC158367
0.8922 High Similarity NPC469827
0.8879 High Similarity NPC477465
0.8857 High Similarity NPC471431
0.8846 High Similarity NPC469826
0.88 High Similarity NPC209798
0.88 High Similarity NPC471374
0.88 High Similarity NPC471375
0.8776 High Similarity NPC77717
0.8776 High Similarity NPC471373
0.8776 High Similarity NPC148593
0.8776 High Similarity NPC267238
0.8776 High Similarity NPC253611
0.8774 High Similarity NPC469824
0.8762 High Similarity NPC469825
0.8725 High Similarity NPC80191
0.8725 High Similarity NPC310031
0.8713 High Similarity NPC471428
0.8713 High Similarity NPC51579
0.8713 High Similarity NPC471426
0.8713 High Similarity NPC471427
0.8687 High Similarity NPC189575
0.8687 High Similarity NPC205129
0.8687 High Similarity NPC106701
0.8687 High Similarity NPC471425
0.8687 High Similarity NPC471424
0.8687 High Similarity NPC471429
0.8673 High Similarity NPC224003
0.8673 High Similarity NPC171741
0.8673 High Similarity NPC323231
0.8673 High Similarity NPC470623
0.8673 High Similarity NPC18724
0.8667 High Similarity NPC475319
0.8667 High Similarity NPC202898
0.8667 High Similarity NPC92890
0.8627 High Similarity NPC477172
0.8585 High Similarity NPC220836
0.8585 High Similarity NPC273002
0.8585 High Similarity NPC473817
0.8585 High Similarity NPC92297
0.8585 High Similarity NPC94086
0.8585 High Similarity NPC233433
0.8545 High Similarity NPC179429
0.8529 High Similarity NPC20028
0.8476 Intermediate Similarity NPC215408
0.8411 Intermediate Similarity NPC236753
0.8411 Intermediate Similarity NPC228190
0.8393 Intermediate Similarity NPC207738
0.8349 Intermediate Similarity NPC477492
0.8319 Intermediate Similarity NPC267694
0.8319 Intermediate Similarity NPC153673
0.8319 Intermediate Similarity NPC110385
0.8319 Intermediate Similarity NPC142151
0.8319 Intermediate Similarity NPC37860
0.8319 Intermediate Similarity NPC144644
0.8319 Intermediate Similarity NPC473645
0.8304 Intermediate Similarity NPC105800
0.8304 Intermediate Similarity NPC470513
0.8304 Intermediate Similarity NPC470514
0.8304 Intermediate Similarity NPC232237
0.8288 Intermediate Similarity NPC472718
0.8286 Intermediate Similarity NPC34562
0.8286 Intermediate Similarity NPC107385
0.8273 Intermediate Similarity NPC146563
0.8257 Intermediate Similarity NPC473062
0.8246 Intermediate Similarity NPC68767
0.8246 Intermediate Similarity NPC275225
0.8246 Intermediate Similarity NPC51099
0.8246 Intermediate Similarity NPC293031
0.8224 Intermediate Similarity NPC203974
0.8218 Intermediate Similarity NPC305418
0.8214 Intermediate Similarity NPC475119
0.8214 Intermediate Similarity NPC473824
0.8208 Intermediate Similarity NPC470167
0.8173 Intermediate Similarity NPC41843
0.8158 Intermediate Similarity NPC473130
0.8142 Intermediate Similarity NPC475899
0.8125 Intermediate Similarity NPC75287
0.8125 Intermediate Similarity NPC51465
0.8125 Intermediate Similarity NPC305267
0.8125 Intermediate Similarity NPC288205
0.8125 Intermediate Similarity NPC476992
0.8125 Intermediate Similarity NPC469823
0.8125 Intermediate Similarity NPC469820
0.8125 Intermediate Similarity NPC137414
0.8125 Intermediate Similarity NPC26626
0.8125 Intermediate Similarity NPC37134
0.8125 Intermediate Similarity NPC291903
0.81 Intermediate Similarity NPC18536
0.81 Intermediate Similarity NPC50443
0.8091 Intermediate Similarity NPC275668
0.8091 Intermediate Similarity NPC11035
0.8091 Intermediate Similarity NPC240734
0.8091 Intermediate Similarity NPC1876
0.8091 Intermediate Similarity NPC204392
0.8091 Intermediate Similarity NPC91838
0.8091 Intermediate Similarity NPC274833
0.8087 Intermediate Similarity NPC470478
0.807 Intermediate Similarity NPC477464
0.807 Intermediate Similarity NPC25663
0.807 Intermediate Similarity NPC135849
0.807 Intermediate Similarity NPC471577
0.807 Intermediate Similarity NPC51564
0.8058 Intermediate Similarity NPC203434
0.8058 Intermediate Similarity NPC238796
0.8058 Intermediate Similarity NPC304011
0.8058 Intermediate Similarity NPC237071
0.8058 Intermediate Similarity NPC139271
0.8053 Intermediate Similarity NPC473452
0.8053 Intermediate Similarity NPC8524
0.8053 Intermediate Similarity NPC85154
0.8053 Intermediate Similarity NPC309223
0.8053 Intermediate Similarity NPC471580
0.8053 Intermediate Similarity NPC470876
0.8053 Intermediate Similarity NPC68175
0.8053 Intermediate Similarity NPC286457
0.8053 Intermediate Similarity NPC475514
0.8053 Intermediate Similarity NPC102505
0.8053 Intermediate Similarity NPC191827
0.8053 Intermediate Similarity NPC475209
0.8053 Intermediate Similarity NPC33012
0.8053 Intermediate Similarity NPC220160
0.8053 Intermediate Similarity NPC104137
0.8053 Intermediate Similarity NPC69811
0.8053 Intermediate Similarity NPC300419
0.8053 Intermediate Similarity NPC123522
0.8041 Intermediate Similarity NPC34984
0.8041 Intermediate Similarity NPC25037
0.8036 Intermediate Similarity NPC79193
0.8036 Intermediate Similarity NPC475486
0.8036 Intermediate Similarity NPC54395
0.8036 Intermediate Similarity NPC469821
0.8036 Intermediate Similarity NPC164389
0.802 Intermediate Similarity NPC307167
0.802 Intermediate Similarity NPC229801
0.802 Intermediate Similarity NPC210759
0.8018 Intermediate Similarity NPC472719
0.8018 Intermediate Similarity NPC477489
0.8018 Intermediate Similarity NPC207845
0.8 Intermediate Similarity NPC131466
0.8 Intermediate Similarity NPC476991
0.7982 Intermediate Similarity NPC473459
0.7982 Intermediate Similarity NPC469822
0.7982 Intermediate Similarity NPC237191
0.7982 Intermediate Similarity NPC36831
0.7982 Intermediate Similarity NPC472079
0.7981 Intermediate Similarity NPC472273
0.7981 Intermediate Similarity NPC470591
0.7981 Intermediate Similarity NPC476112
0.7981 Intermediate Similarity NPC307534
0.7981 Intermediate Similarity NPC274200
0.7966 Intermediate Similarity NPC181066
0.7966 Intermediate Similarity NPC469947
0.7966 Intermediate Similarity NPC470218
0.7965 Intermediate Similarity NPC160415
0.7965 Intermediate Similarity NPC58448
0.7965 Intermediate Similarity NPC161674
0.7965 Intermediate Similarity NPC471384
0.7961 Intermediate Similarity NPC206003
0.7961 Intermediate Similarity NPC94582
0.7961 Intermediate Similarity NPC107962
0.7961 Intermediate Similarity NPC6295
0.7961 Intermediate Similarity NPC107188
0.7961 Intermediate Similarity NPC473727
0.7961 Intermediate Similarity NPC211354
0.7961 Intermediate Similarity NPC19400
0.7961 Intermediate Similarity NPC477494
0.7961 Intermediate Similarity NPC473610
0.7961 Intermediate Similarity NPC475351
0.7961 Intermediate Similarity NPC57964
0.7949 Intermediate Similarity NPC281148
0.7949 Intermediate Similarity NPC235405
0.7949 Intermediate Similarity NPC30735
0.7946 Intermediate Similarity NPC114287
0.7946 Intermediate Similarity NPC323341
0.7946 Intermediate Similarity NPC295823
0.7946 Intermediate Similarity NPC241909
0.7946 Intermediate Similarity NPC475467

  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 NPC273189 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
0.8381 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD8133 Approved
0.7767 Intermediate Similarity NPD8171 Discontinued
0.7739 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD8328 Phase 3
0.7589 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.6911 Remote Similarity NPD8515 Approved
0.6911 Remote Similarity NPD8516 Approved
0.6911 Remote Similarity NPD8517 Approved
0.6893 Remote Similarity NPD3669 Approved
0.6893 Remote Similarity NPD3670 Clinical (unspecified phase)
0.681 Remote Similarity NPD6412 Phase 2
0.6774 Remote Similarity NPD8513 Phase 3
0.6752 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7736 Approved
0.6699 Remote Similarity NPD1779 Approved
0.6699 Remote Similarity NPD1780 Approved
0.6694 Remote Similarity NPD8377 Approved
0.6694 Remote Similarity NPD8294 Approved
0.6667 Remote Similarity NPD7319 Approved
0.664 Remote Similarity NPD8379 Approved
0.664 Remote Similarity NPD8378 Approved
0.664 Remote Similarity NPD8335 Approved
0.664 Remote Similarity NPD8380 Approved
0.664 Remote Similarity NPD8296 Approved
0.6639 Remote Similarity NPD6940 Discontinued
0.6602 Remote Similarity NPD6928 Phase 2
0.6587 Remote Similarity NPD6370 Approved
0.6569 Remote Similarity NPD6115 Approved
0.6569 Remote Similarity NPD6118 Approved
0.6569 Remote Similarity NPD6114 Approved
0.6569 Remote Similarity NPD6697 Approved
0.6562 Remote Similarity NPD7507 Approved
0.6512 Remote Similarity NPD8293 Discontinued
0.6508 Remote Similarity NPD8033 Approved
0.65 Remote Similarity NPD1811 Approved
0.65 Remote Similarity NPD1810 Approved
0.6471 Remote Similarity NPD6686 Approved
0.6471 Remote Similarity NPD6116 Phase 1
0.6466 Remote Similarity NPD8138 Approved
0.6466 Remote Similarity NPD8139 Approved
0.6466 Remote Similarity NPD8085 Approved
0.6466 Remote Similarity NPD8086 Approved
0.6466 Remote Similarity NPD8084 Approved
0.6466 Remote Similarity NPD8082 Approved
0.6466 Remote Similarity NPD8083 Approved
0.6441 Remote Similarity NPD8393 Approved
0.6436 Remote Similarity NPD3703 Phase 2
0.6429 Remote Similarity NPD6054 Approved
0.6429 Remote Similarity NPD6059 Approved
0.641 Remote Similarity NPD8276 Approved
0.641 Remote Similarity NPD8275 Approved
0.6396 Remote Similarity NPD8035 Phase 2
0.6396 Remote Similarity NPD8034 Phase 2
0.6373 Remote Similarity NPD6117 Approved
0.6356 Remote Similarity NPD8081 Approved
0.6346 Remote Similarity NPD7329 Approved
0.6311 Remote Similarity NPD8413 Clinical (unspecified phase)
0.63 Remote Similarity NPD4809 Clinical (unspecified phase)
0.63 Remote Similarity NPD4808 Clinical (unspecified phase)
0.627 Remote Similarity NPD7328 Approved
0.627 Remote Similarity NPD7327 Approved
0.6263 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6263 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7902 Approved
0.625 Remote Similarity NPD6016 Approved
0.625 Remote Similarity NPD6015 Approved
0.625 Remote Similarity NPD6921 Approved
0.6231 Remote Similarity NPD7492 Approved
0.622 Remote Similarity NPD7516 Approved
0.6202 Remote Similarity NPD5988 Approved
0.62 Remote Similarity NPD2687 Approved
0.62 Remote Similarity NPD2254 Approved
0.62 Remote Similarity NPD2686 Approved
0.6183 Remote Similarity NPD6616 Approved
0.6176 Remote Similarity NPD6113 Clinical (unspecified phase)
0.614 Remote Similarity NPD7748 Approved
0.6136 Remote Similarity NPD7078 Approved
0.6102 Remote Similarity NPD1700 Approved
0.61 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6083 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6083 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6047 Remote Similarity NPD6319 Approved
0.604 Remote Similarity NPD4244 Approved
0.604 Remote Similarity NPD7532 Clinical (unspecified phase)
0.604 Remote Similarity NPD4245 Approved
0.6031 Remote Similarity NPD6067 Discontinued
0.6016 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6 Remote Similarity NPD7503 Approved
0.6 Remote Similarity NPD7900 Approved
0.6 Remote Similarity NPD5360 Phase 3
0.6 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5984 Remote Similarity NPD8307 Discontinued
0.5984 Remote Similarity NPD8140 Approved
0.597 Remote Similarity NPD6033 Approved
0.5968 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5965 Remote Similarity NPD7515 Phase 2
0.5948 Remote Similarity NPD7991 Discontinued
0.5941 Remote Similarity NPD3698 Phase 2
0.5938 Remote Similarity NPD7115 Discovery
0.5922 Remote Similarity NPD3181 Approved
0.5896 Remote Similarity NPD8074 Phase 3
0.5887 Remote Similarity NPD8305 Approved
0.5887 Remote Similarity NPD8306 Approved
0.5882 Remote Similarity NPD4789 Approved
0.5873 Remote Similarity NPD8297 Approved
0.5873 Remote Similarity NPD6882 Approved
0.584 Remote Similarity NPD8087 Discontinued
0.5825 Remote Similarity NPD5777 Approved
0.5814 Remote Similarity NPD6009 Approved
0.581 Remote Similarity NPD3702 Approved
0.5794 Remote Similarity NPD4802 Phase 2
0.5794 Remote Similarity NPD3671 Phase 1
0.5794 Remote Similarity NPD4238 Approved
0.5773 Remote Similarity NPD6123 Approved
0.576 Remote Similarity NPD6372 Approved
0.576 Remote Similarity NPD6373 Approved
0.5758 Remote Similarity NPD371 Approved
0.5755 Remote Similarity NPD8450 Suspended
0.5726 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4634 Approved
0.5703 Remote Similarity NPD4632 Approved
0.57 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5692 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5683 Remote Similarity NPD8449 Approved
0.5682 Remote Similarity NPD8347 Approved
0.5682 Remote Similarity NPD8346 Approved
0.5682 Remote Similarity NPD8345 Approved
0.568 Remote Similarity NPD8174 Phase 2
0.5673 Remote Similarity NPD4758 Discontinued
0.5673 Remote Similarity NPD6081 Approved
0.5669 Remote Similarity NPD6650 Approved
0.5669 Remote Similarity NPD6649 Approved
0.5667 Remote Similarity NPD7638 Approved
0.5667 Remote Similarity NPD4225 Approved
0.5656 Remote Similarity NPD8301 Approved
0.5656 Remote Similarity NPD8300 Approved
0.5648 Remote Similarity NPD5364 Discontinued
0.5645 Remote Similarity NPD7128 Approved
0.5645 Remote Similarity NPD6675 Approved
0.5645 Remote Similarity NPD5739 Approved
0.5645 Remote Similarity NPD6402 Approved
0.5644 Remote Similarity NPD4224 Phase 2
0.5641 Remote Similarity NPD6399 Phase 3
0.5639 Remote Similarity NPD8269 Approved
0.5639 Remote Similarity NPD8268 Approved
0.5639 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5639 Remote Similarity NPD8267 Approved
0.5639 Remote Similarity NPD8266 Approved
0.562 Remote Similarity NPD7639 Approved
0.562 Remote Similarity NPD7640 Approved
0.562 Remote Similarity NPD8418 Phase 2

  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