Structure

Physi-Chem Properties

Molecular Weight:  867.29
Volume:  833.255
LogP:  2.16
LogD:  1.154
LogS:  -4.198
# Rotatable Bonds:  14
TPSA:  252.75
# H-Bond Aceptor:  19
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.295
Synthetic Accessibility Score:  7.525
Fsp3:  0.558
Lipinski Rule-of-5:  Rejected
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:  -5.242
MDCK Permeability:  0.00015440948482137173
Pgp-inhibitor:  1.0
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.809
20% Bioavailability (F20%):  0.993
30% Bioavailability (F30%):  0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  37.3662109375%
Volume Distribution (VD):  1.587
Pgp-substrate:  23.170257568359375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.09
CYP1A2-substrate:  0.012
CYP2C19-inhibitor:  0.042
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.056
CYP2C9-substrate:  0.01
CYP2D6-inhibitor:  0.945
CYP2D6-substrate:  0.028
CYP3A4-inhibitor:  0.799
CYP3A4-substrate:  0.25

ADMET: Excretion

Clearance (CL):  3.003
Half-life (T1/2):  0.587

ADMET: Toxicity

hERG Blockers:  0.073
Human Hepatotoxicity (H-HT):  0.979
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.16
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.292
Carcinogencity:  0.052
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.027

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

  Natural Product: NPC228377

Natural Product ID:  NPC228377
Common Name*:   ZOCKGJZEUVPPPI-QSNSFFMXSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ZOCKGJZEUVPPPI-QSNSFFMXSA-N
Standard InCHI:  InChI=1S/C43H49NO18/c1-21-16-17-29-28(15-12-18-44-29)39(52)55-19-40(7)30-31(56-23(3)46)35(58-25(5)48)42(20-54-22(2)45)36(59-26(6)49)32(60-38(51)27-13-10-9-11-14-27)34(61-37(21)50)41(8,53)43(42,62-40)33(30)57-24(4)47/h9-15,18,21,30-36,53H,16-17,19-20H2,1-8H3/t21-,30+,31+,32-,33+,34-,35+,36-,40-,41-,42+,43-/m0/s1
SMILES:  CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)c3ccccc3)[C@H]3[C@]([C@@]42O[C@@]([C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)[C@H]4OC(=O)C)(C)COC(=O)c1cccnc1CC[C@@H](C(=O)O3)C)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL502742
PubChem CID:   3002219
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO7869 Peritassa campestris Species Celastraceae Eukaryota n.a. root n.a. PMID[11738408]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7869 Peritassa campestris Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13661 Tripterygium wilfordii Species Celastraceae 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
NPT927 Cell Line PBMC Homo sapiens Inhibition = 79.0 % PMID[462823]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 64.0 % PMID[462823]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 1.0 % PMID[462823]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 67.0 % PMID[462823]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 16.0 % PMID[462823]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 41.0 % PMID[462823]

☑ 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 NPC228377 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 NPC477787
1.0 High Similarity NPC122968
1.0 High Similarity NPC328186
0.9853 High Similarity NPC316841
0.9853 High Similarity NPC292416
0.9853 High Similarity NPC473689
0.9851 High Similarity NPC250807
0.9851 High Similarity NPC57797
0.9805 High Similarity NPC244839
0.9805 High Similarity NPC320324
0.9805 High Similarity NPC319880
0.9803 High Similarity NPC475600
0.9803 High Similarity NPC476110
0.9803 High Similarity NPC87152
0.9803 High Similarity NPC475631
0.9802 High Similarity NPC473850
0.9801 High Similarity NPC477788
0.9757 High Similarity NPC237702
0.9755 High Similarity NPC471190
0.9755 High Similarity NPC470486
0.9755 High Similarity NPC475644
0.9755 High Similarity NPC471977
0.971 High Similarity NPC475406
0.9706 High Similarity NPC146824
0.9663 High Similarity NPC38959
0.9663 High Similarity NPC327904
0.966 High Similarity NPC475303
0.966 High Similarity NPC475596
0.9659 High Similarity NPC475362
0.9657 High Similarity NPC473506
0.9655 High Similarity NPC76565
0.9652 High Similarity NPC84815
0.9652 High Similarity NPC301368
0.9614 High Similarity NPC30456
0.9608 High Similarity NPC475137
0.9608 High Similarity NPC475498
0.9552 High Similarity NPC6981
0.9552 High Similarity NPC471016
0.9526 High Similarity NPC253482
0.9522 High Similarity NPC327769
0.9512 High Similarity NPC328154
0.951 High Similarity NPC127026
0.951 High Similarity NPC127720
0.9505 High Similarity NPC144779
0.9505 High Similarity NPC294579
0.9502 High Similarity NPC470306
0.9463 High Similarity NPC471980
0.9455 High Similarity NPC475408
0.9455 High Similarity NPC471014
0.9453 High Similarity NPC4421
0.9409 High Similarity NPC62367
0.9393 High Similarity NPC475648
0.9363 High Similarity NPC216428
0.9336 High Similarity NPC170751
0.9314 High Similarity NPC75600
0.9314 High Similarity NPC158020
0.9314 High Similarity NPC473115
0.9314 High Similarity NPC6576
0.9314 High Similarity NPC212768
0.9314 High Similarity NPC473089
0.931 High Similarity NPC42678
0.931 High Similarity NPC477909
0.931 High Similarity NPC477907
0.9272 High Similarity NPC477912
0.9245 High Similarity NPC475426
0.9245 High Similarity NPC35208
0.9234 High Similarity NPC211920
0.9231 High Similarity NPC477902
0.9194 High Similarity NPC96801
0.9194 High Similarity NPC150698
0.9163 High Similarity NPC472553
0.9143 High Similarity NPC124029
0.9143 High Similarity NPC475601
0.9095 High Similarity NPC148860
0.9087 High Similarity NPC477903
0.9082 High Similarity NPC472555
0.9015 High Similarity NPC304179
0.9015 High Similarity NPC472550
0.9015 High Similarity NPC48042
0.8986 High Similarity NPC477908
0.8986 High Similarity NPC206343
0.8981 High Similarity NPC264674
0.8981 High Similarity NPC319128
0.8972 High Similarity NPC469748
0.8952 High Similarity NPC477911
0.8937 High Similarity NPC477910
0.8925 High Similarity NPC477906
0.8889 High Similarity NPC228331
0.8873 High Similarity NPC63041
0.8868 High Similarity NPC477899
0.8868 High Similarity NPC477900
0.8863 High Similarity NPC235364
0.8844 High Similarity NPC85879
0.8844 High Similarity NPC53255
0.8805 High Similarity NPC13603
0.8779 High Similarity NPC26881
0.8768 High Similarity NPC477901
0.8678 High Similarity NPC326930
0.8678 High Similarity NPC475301
0.8618 High Similarity NPC91125
0.8615 High Similarity NPC471978
0.8612 High Similarity NPC476467
0.8534 High Similarity NPC328928
0.8533 High Similarity NPC475533
0.8528 High Similarity NPC473833
0.8525 High Similarity NPC285411
0.8525 High Similarity NPC14116
0.8504 High Similarity NPC471979
0.8496 Intermediate Similarity NPC475315
0.8496 Intermediate Similarity NPC324619
0.8486 Intermediate Similarity NPC134384
0.8486 Intermediate Similarity NPC311196
0.8436 Intermediate Similarity NPC280473
0.8436 Intermediate Similarity NPC323551
0.8416 Intermediate Similarity NPC238278
0.8407 Intermediate Similarity NPC148896
0.8407 Intermediate Similarity NPC476090
0.8407 Intermediate Similarity NPC471013
0.8407 Intermediate Similarity NPC180668
0.8396 Intermediate Similarity NPC51008
0.8396 Intermediate Similarity NPC41724
0.8371 Intermediate Similarity NPC213143
0.8365 Intermediate Similarity NPC289086
0.8312 Intermediate Similarity NPC471015
0.8294 Intermediate Similarity NPC472752
0.8265 Intermediate Similarity NPC233727
0.8261 Intermediate Similarity NPC10904
0.8233 Intermediate Similarity NPC30570
0.8194 Intermediate Similarity NPC162812
0.8178 Intermediate Similarity NPC292517
0.814 Intermediate Similarity NPC165837
0.8113 Intermediate Similarity NPC475835
0.8073 Intermediate Similarity NPC187494
0.8065 Intermediate Similarity NPC193361
0.8065 Intermediate Similarity NPC62844
0.8047 Intermediate Similarity NPC40919
0.8047 Intermediate Similarity NPC470189
0.8 Intermediate Similarity NPC470279
0.7991 Intermediate Similarity NPC319556
0.7991 Intermediate Similarity NPC470190
0.79 Intermediate Similarity NPC207531
0.7897 Intermediate Similarity NPC309498
0.7799 Intermediate Similarity NPC103230
0.7725 Intermediate Similarity NPC37473
0.7723 Intermediate Similarity NPC253314
0.7682 Intermediate Similarity NPC111732
0.7652 Intermediate Similarity NPC471004
0.757 Intermediate Similarity NPC320748
0.757 Intermediate Similarity NPC324245
0.7546 Intermediate Similarity NPC328559
0.7546 Intermediate Similarity NPC32451
0.7543 Intermediate Similarity NPC70155
0.7521 Intermediate Similarity NPC107123
0.7511 Intermediate Similarity NPC314834
0.75 Intermediate Similarity NPC79223
0.75 Intermediate Similarity NPC470280
0.7488 Intermediate Similarity NPC249614
0.7455 Intermediate Similarity NPC156044
0.7454 Intermediate Similarity NPC123395
0.7451 Intermediate Similarity NPC191310
0.7445 Intermediate Similarity NPC140311
0.7442 Intermediate Similarity NPC329024
0.7416 Intermediate Similarity NPC207851
0.7411 Intermediate Similarity NPC317752
0.7397 Intermediate Similarity NPC183537
0.7395 Intermediate Similarity NPC109922
0.738 Intermediate Similarity NPC106593
0.7376 Intermediate Similarity NPC314297
0.7376 Intermediate Similarity NPC315545
0.7366 Intermediate Similarity NPC318299
0.7364 Intermediate Similarity NPC25442
0.7364 Intermediate Similarity NPC12944
0.7364 Intermediate Similarity NPC15406
0.7358 Intermediate Similarity NPC44354
0.7357 Intermediate Similarity NPC141385
0.7355 Intermediate Similarity NPC476516
0.7353 Intermediate Similarity NPC210296
0.735 Intermediate Similarity NPC233334
0.7349 Intermediate Similarity NPC135950
0.7348 Intermediate Similarity NPC473667
0.7339 Intermediate Similarity NPC24019
0.7336 Intermediate Similarity NPC473441
0.7336 Intermediate Similarity NPC131273
0.7333 Intermediate Similarity NPC124313
0.7331 Intermediate Similarity NPC108342
0.733 Intermediate Similarity NPC315638
0.733 Intermediate Similarity NPC314855
0.733 Intermediate Similarity NPC313345
0.733 Intermediate Similarity NPC313796
0.7327 Intermediate Similarity NPC317672
0.7327 Intermediate Similarity NPC59033
0.7325 Intermediate Similarity NPC77878
0.7316 Intermediate Similarity NPC235885
0.7311 Intermediate Similarity NPC471782
0.7311 Intermediate Similarity NPC471583
0.73 Intermediate Similarity NPC182907
0.73 Intermediate Similarity NPC189903
0.7294 Intermediate Similarity NPC103361
0.7288 Intermediate Similarity NPC90875
0.7273 Intermediate Similarity NPC317010

  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 NPC228377 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
0.837 Intermediate Similarity NPD8468 Phase 2
0.8019 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7685 Intermediate Similarity NPD7396 Approved
0.7647 Intermediate Similarity NPD3794 Approved
0.7647 Intermediate Similarity NPD3795 Approved
0.7593 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD5891 Approved
0.7535 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1483 Discontinued
0.7443 Intermediate Similarity NPD3947 Discontinued
0.7399 Intermediate Similarity NPD4417 Approved
0.7366 Intermediate Similarity NPD7069 Discontinued
0.7364 Intermediate Similarity NPD6987 Phase 1
0.7358 Intermediate Similarity NPD7233 Approved
0.7358 Intermediate Similarity NPD7234 Approved
0.7309 Intermediate Similarity NPD4506 Discontinued
0.7293 Intermediate Similarity NPD3280 Approved
0.7269 Intermediate Similarity NPD3389 Approved
0.7269 Intermediate Similarity NPD3394 Approved
0.7269 Intermediate Similarity NPD3393 Approved
0.7265 Intermediate Similarity NPD2510 Approved
0.7265 Intermediate Similarity NPD2509 Approved
0.7258 Intermediate Similarity NPD7708 Approved
0.7252 Intermediate Similarity NPD7010 Phase 3
0.7249 Intermediate Similarity NPD6770 Approved
0.7237 Intermediate Similarity NPD8325 Phase 3
0.7237 Intermediate Similarity NPD8326 Phase 3
0.7237 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD820 Phase 3
0.7212 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7803 Approved
0.7207 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD6529 Discontinued
0.715 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD7955 Approved
0.7149 Intermediate Similarity NPD7956 Approved
0.713 Intermediate Similarity NPD7878 Phase 2
0.7093 Intermediate Similarity NPD5475 Discontinued
0.7091 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7778 Approved
0.7091 Intermediate Similarity NPD7777 Approved
0.7091 Intermediate Similarity NPD53 Approved
0.7083 Intermediate Similarity NPD8063 Discontinued
0.7073 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6635 Approved
0.7069 Intermediate Similarity NPD8479 Phase 2
0.7054 Intermediate Similarity NPD5901 Discontinued
0.7051 Intermediate Similarity NPD2336 Approved
0.7032 Intermediate Similarity NPD4427 Phase 2
0.7025 Intermediate Similarity NPD7886 Phase 2
0.7025 Intermediate Similarity NPD7885 Phase 2
0.7022 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD6641 Approved
0.7014 Intermediate Similarity NPD6642 Approved
0.6996 Remote Similarity NPD7417 Discontinued
0.6966 Remote Similarity NPD4301 Approved
0.6964 Remote Similarity NPD7187 Phase 2
0.6934 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6926 Remote Similarity NPD7707 Approved
0.6926 Remote Similarity NPD6790 Phase 1
0.6923 Remote Similarity NPD2307 Discontinued
0.6923 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6913 Remote Similarity NPD5866 Approved
0.6912 Remote Similarity NPD4948 Discontinued
0.6905 Remote Similarity NPD8091 Phase 3
0.6904 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6892 Remote Similarity NPD8485 Approved
0.689 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6889 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6883 Remote Similarity NPD7571 Clinical (unspecified phase)
0.688 Remote Similarity NPD7404 Approved
0.6878 Remote Similarity NPD3925 Approved
0.6875 Remote Similarity NPD6962 Phase 2
0.6875 Remote Similarity NPD4601 Approved
0.6875 Remote Similarity NPD4600 Approved
0.6875 Remote Similarity NPD7688 Phase 1
0.6872 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6872 Remote Similarity NPD5805 Approved
0.687 Remote Similarity NPD7470 Discontinued
0.6867 Remote Similarity NPD5482 Discontinued
0.6867 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6866 Remote Similarity NPD9271 Approved
0.6864 Remote Similarity NPD4376 Phase 3
0.6864 Remote Similarity NPD6995 Phase 1
0.6853 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6849 Remote Similarity NPD6281 Approved
0.6849 Remote Similarity NPD8289 Discontinued
0.6838 Remote Similarity NPD7395 Discontinued
0.6833 Remote Similarity NPD5022 Discontinued
0.6832 Remote Similarity NPD8465 Approved
0.6832 Remote Similarity NPD8466 Approved
0.6832 Remote Similarity NPD8467 Approved
0.6829 Remote Similarity NPD6716 Phase 1
0.6826 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6826 Remote Similarity NPD7998 Clinical (unspecified phase)
0.682 Remote Similarity NPD4889 Approved
0.6818 Remote Similarity NPD4373 Phase 2
0.6816 Remote Similarity NPD5003 Discontinued
0.68 Remote Similarity NPD8248 Clinical (unspecified phase)
0.68 Remote Similarity NPD4396 Clinical (unspecified phase)
0.68 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7001 Phase 3
0.6798 Remote Similarity NPD7957 Phase 1
0.6798 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6795 Remote Similarity NPD4989 Phase 2
0.6793 Remote Similarity NPD8356 Approved
0.6787 Remote Similarity NPD3921 Approved
0.6787 Remote Similarity NPD3922 Approved
0.6787 Remote Similarity NPD3924 Approved
0.6787 Remote Similarity NPD3923 Approved
0.6778 Remote Similarity NPD7426 Phase 1
0.6774 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6773 Remote Similarity NPD8435 Approved
0.6773 Remote Similarity NPD8360 Approved
0.6773 Remote Similarity NPD8361 Approved
0.6762 Remote Similarity NPD3006 Discontinued
0.6758 Remote Similarity NPD6791 Phase 2
0.6757 Remote Similarity NPD4526 Approved
0.6757 Remote Similarity NPD4528 Approved
0.6757 Remote Similarity NPD4529 Approved
0.6756 Remote Similarity NPD6999 Discontinued
0.6756 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6754 Remote Similarity NPD2831 Approved
0.675 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6026 Approved
0.6746 Remote Similarity NPD5088 Discontinued
0.6746 Remote Similarity NPD1631 Approved
0.6739 Remote Similarity NPD7191 Phase 2
0.6736 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6731 Remote Similarity NPD8364 Approved
0.6731 Remote Similarity NPD8363 Approved
0.6729 Remote Similarity NPD8460 Approved
0.6729 Remote Similarity NPD8425 Approved
0.6729 Remote Similarity NPD8459 Approved
0.6729 Remote Similarity NPD8426 Approved
0.6726 Remote Similarity NPD4501 Approved
0.6726 Remote Similarity NPD4500 Approved
0.6726 Remote Similarity NPD6479 Discontinued
0.6723 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6715 Remote Similarity NPD2582 Approved
0.6715 Remote Similarity NPD2581 Approved
0.6711 Remote Similarity NPD6176 Phase 1
0.6709 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6708 Remote Similarity NPD5640 Discontinued
0.6705 Remote Similarity NPD8427 Approved
0.6705 Remote Similarity NPD8429 Approved
0.6705 Remote Similarity NPD8428 Approved
0.6696 Remote Similarity NPD5429 Discontinued
0.6696 Remote Similarity NPD7562 Approved
0.6695 Remote Similarity NPD3815 Phase 1
0.6695 Remote Similarity NPD3816 Phase 1
0.6694 Remote Similarity NPD4952 Phase 3
0.6683 Remote Similarity NPD9075 Approved
0.6683 Remote Similarity NPD9074 Approved
0.6682 Remote Similarity NPD3178 Discontinued
0.6682 Remote Similarity NPD6361 Phase 2
0.6682 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6681 Remote Similarity NPD8160 Phase 2
0.668 Remote Similarity NPD5488 Discontinued
0.668 Remote Similarity NPD6494 Phase 2
0.668 Remote Similarity NPD2921 Clinical (unspecified phase)
0.668 Remote Similarity NPD6553 Clinical (unspecified phase)
0.668 Remote Similarity NPD8430 Approved
0.668 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6679 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7424 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8101 Phase 3
0.6667 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6654 Remote Similarity NPD6228 Discontinued
0.6654 Remote Similarity NPD8463 Approved
0.6653 Remote Similarity NPD7576 Discontinued
0.6653 Remote Similarity NPD6276 Discontinued
0.6652 Remote Similarity NPD7944 Discontinued
0.6651 Remote Similarity NPD6375 Clinical (unspecified phase)
0.6651 Remote Similarity NPD5100 Phase 3
0.6641 Remote Similarity NPD7169 Suspended
0.6639 Remote Similarity NPD1996 Discontinued
0.6637 Remote Similarity NPD6665 Discontinued
0.6627 Remote Similarity NPD8412 Phase 1
0.6627 Remote Similarity NPD8102 Discontinued
0.6624 Remote Similarity NPD4429 Discontinued
0.6624 Remote Similarity NPD3354 Phase 2
0.6622 Remote Similarity NPD2564 Approved
0.6622 Remote Similarity NPD2565 Phase 2
0.662 Remote Similarity NPD7474 Suspended
0.662 Remote Similarity NPD1575 Approved
0.662 Remote Similarity NPD1573 Approved
0.662 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6615 Remote Similarity NPD5450 Discontinued
0.6612 Remote Similarity NPD4086 Phase 1
0.6612 Remote Similarity NPD3259 Approved
0.6612 Remote Similarity NPD7558 Phase 2
0.6611 Remote Similarity NPD6298 Discontinued
0.6609 Remote Similarity NPD3946 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data