Structure

Physi-Chem Properties

Molecular Weight:  643.23
Volume:  618.151
LogP:  2.306
LogD:  1.578
LogS:  -3.642
# Rotatable Bonds:  13
TPSA:  186.99
# H-Bond Aceptor:  14
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.327
Synthetic Accessibility Score:  6.105
Fsp3:  0.562
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:  -5.398
MDCK Permeability:  7.649812323506922e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.867
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.686
Plasma Protein Binding (PPB):  57.64508056640625%
Volume Distribution (VD):  1.567
Pgp-substrate:  21.46022605895996%

ADMET: Metabolism

CYP1A2-inhibitor:  0.084
CYP1A2-substrate:  0.035
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.016
CYP2D6-inhibitor:  0.194
CYP2D6-substrate:  0.043
CYP3A4-inhibitor:  0.814
CYP3A4-substrate:  0.263

ADMET: Excretion

Clearance (CL):  4.774
Half-life (T1/2):  0.588

ADMET: Toxicity

hERG Blockers:  0.361
Human Hepatotoxicity (H-HT):  0.844
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.154
Rat Oral Acute Toxicity:  0.82
Maximum Recommended Daily Dose:  0.149
Skin Sensitization:  0.114
Carcinogencity:  0.558
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.974

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

  Natural Product: NPC148896

Natural Product ID:  NPC148896
Common Name*:   Triptersinin F
IUPAC Name:   n.a.
Synonyms:   Triptersinin F
Standard InCHIKey:  VTQQVEFTDPJJAG-OWFKIMCMSA-N
Standard InCHI:  InChI=1S/C32H37NO13/c1-17(34)41-16-31-22(42-18(2)35)9-11-30(6,39)32(31)25(44-27(37)20-8-7-12-33-14-20)23(29(4,5)46-32)24(43-19(3)36)26(31)45-28(38)21-10-13-40-15-21/h7-8,10,12-15,22-26,39H,9,11,16H2,1-6H3/t22-,23+,24+,25+,26+,30-,31-,32-/m0/s1
SMILES:  CC(=O)OC[C@]12[C@H](CC[C@@](C)([C@]32[C@@H]([C@@H]([C@H]([C@H]1OC(=O)c1ccoc1)OC(=O)C)C(C)(C)O3)OC(=O)c1cccnc1)O)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2335695
PubChem CID:   71524359
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
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]
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 n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. 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]
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
NPT179 Cell Line A2780 Homo sapiens IC50 > 1000.0 nM PMID[524809]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 1000.0 nM PMID[524809]
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 1000.0 nM PMID[524809]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 1000.0 nM PMID[524809]
NPT81 Cell Line A549 Homo sapiens IC50 > 1000.0 nM PMID[524809]

☑ 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 NPC148896 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 NPC471013
1.0 High Similarity NPC180668
0.9817 High Similarity NPC10904
0.9685 High Similarity NPC471015
0.9389 High Similarity NPC471978
0.9327 High Similarity NPC475533
0.9286 High Similarity NPC475315
0.9286 High Similarity NPC324619
0.9267 High Similarity NPC471979
0.9134 High Similarity NPC473833
0.9043 High Similarity NPC326930
0.9043 High Similarity NPC53255
0.9043 High Similarity NPC475301
0.9043 High Similarity NPC85879
0.9004 High Similarity NPC13603
0.8814 High Similarity NPC328928
0.8756 High Similarity NPC6981
0.8716 High Similarity NPC294579
0.8716 High Similarity NPC144779
0.871 High Similarity NPC470306
0.8676 High Similarity NPC84815
0.8676 High Similarity NPC301368
0.867 High Similarity NPC471014
0.867 High Similarity NPC475408
0.867 High Similarity NPC471016
0.8649 High Similarity NPC477902
0.8584 High Similarity NPC469748
0.8571 High Similarity NPC472553
0.8571 High Similarity NPC475601
0.8571 High Similarity NPC211920
0.8571 High Similarity NPC124029
0.8559 High Similarity NPC127026
0.8559 High Similarity NPC127720
0.8545 High Similarity NPC62367
0.854 High Similarity NPC96801
0.854 High Similarity NPC150698
0.8527 High Similarity NPC148860
0.852 High Similarity NPC471980
0.8514 High Similarity NPC477912
0.8509 High Similarity NPC475426
0.8507 High Similarity NPC216428
0.8507 High Similarity NPC472555
0.8493 Intermediate Similarity NPC4421
0.8482 Intermediate Similarity NPC328154
0.8475 Intermediate Similarity NPC477911
0.8458 Intermediate Similarity NPC477906
0.8455 Intermediate Similarity NPC42678
0.8455 Intermediate Similarity NPC477909
0.8455 Intermediate Similarity NPC477907
0.8455 Intermediate Similarity NPC477910
0.8438 Intermediate Similarity NPC76565
0.8438 Intermediate Similarity NPC57797
0.8438 Intermediate Similarity NPC250807
0.8433 Intermediate Similarity NPC48042
0.8433 Intermediate Similarity NPC304179
0.8433 Intermediate Similarity NPC472550
0.843 Intermediate Similarity NPC477903
0.8421 Intermediate Similarity NPC471004
0.8416 Intermediate Similarity NPC477908
0.8416 Intermediate Similarity NPC206343
0.8409 Intermediate Similarity NPC319128
0.8409 Intermediate Similarity NPC264674
0.8407 Intermediate Similarity NPC122968
0.8407 Intermediate Similarity NPC87152
0.8407 Intermediate Similarity NPC475600
0.8407 Intermediate Similarity NPC476110
0.8407 Intermediate Similarity NPC477787
0.8407 Intermediate Similarity NPC328186
0.8407 Intermediate Similarity NPC228377
0.8407 Intermediate Similarity NPC475631
0.84 Intermediate Similarity NPC475137
0.84 Intermediate Similarity NPC473850
0.84 Intermediate Similarity NPC475498
0.84 Intermediate Similarity NPC477899
0.84 Intermediate Similarity NPC477900
0.8393 Intermediate Similarity NPC235364
0.8378 Intermediate Similarity NPC158020
0.8378 Intermediate Similarity NPC6576
0.8378 Intermediate Similarity NPC473115
0.8378 Intermediate Similarity NPC212768
0.8378 Intermediate Similarity NPC75600
0.8378 Intermediate Similarity NPC473089
0.837 Intermediate Similarity NPC471190
0.837 Intermediate Similarity NPC470486
0.837 Intermediate Similarity NPC475644
0.837 Intermediate Similarity NPC471977
0.8348 Intermediate Similarity NPC35208
0.8326 Intermediate Similarity NPC146824
0.8326 Intermediate Similarity NPC228331
0.8319 Intermediate Similarity NPC26881
0.8304 Intermediate Similarity NPC477901
0.8303 Intermediate Similarity NPC63041
0.8297 Intermediate Similarity NPC475596
0.8297 Intermediate Similarity NPC292416
0.8297 Intermediate Similarity NPC475303
0.8297 Intermediate Similarity NPC473689
0.8297 Intermediate Similarity NPC316841
0.8289 Intermediate Similarity NPC475362
0.8283 Intermediate Similarity NPC253482
0.8282 Intermediate Similarity NPC473506
0.8268 Intermediate Similarity NPC327769
0.8261 Intermediate Similarity NPC244839
0.8261 Intermediate Similarity NPC320324
0.8261 Intermediate Similarity NPC30456
0.8261 Intermediate Similarity NPC319880
0.823 Intermediate Similarity NPC477788
0.8225 Intermediate Similarity NPC237702
0.819 Intermediate Similarity NPC475406
0.8178 Intermediate Similarity NPC475648
0.8174 Intermediate Similarity NPC91125
0.8155 Intermediate Similarity NPC327904
0.8155 Intermediate Similarity NPC38959
0.8112 Intermediate Similarity NPC170751
0.8069 Intermediate Similarity NPC238278
0.8026 Intermediate Similarity NPC213143
0.8 Intermediate Similarity NPC289086
0.7931 Intermediate Similarity NPC14116
0.7931 Intermediate Similarity NPC285411
0.7922 Intermediate Similarity NPC233727
0.7911 Intermediate Similarity NPC476467
0.7897 Intermediate Similarity NPC311196
0.7897 Intermediate Similarity NPC134384
0.7885 Intermediate Similarity NPC30570
0.7884 Intermediate Similarity NPC107123
0.7851 Intermediate Similarity NPC162812
0.7832 Intermediate Similarity NPC280473
0.7832 Intermediate Similarity NPC323551
0.7832 Intermediate Similarity NPC292517
0.7797 Intermediate Similarity NPC165837
0.7797 Intermediate Similarity NPC41724
0.7797 Intermediate Similarity NPC51008
0.7729 Intermediate Similarity NPC62844
0.7729 Intermediate Similarity NPC193361
0.7716 Intermediate Similarity NPC253314
0.7662 Intermediate Similarity NPC187494
0.7621 Intermediate Similarity NPC472752
0.7611 Intermediate Similarity NPC475835
0.7511 Intermediate Similarity NPC319556
0.75 Intermediate Similarity NPC470279
0.7478 Intermediate Similarity NPC40919
0.7478 Intermediate Similarity NPC470189
0.7429 Intermediate Similarity NPC119134
0.7425 Intermediate Similarity NPC207531
0.7424 Intermediate Similarity NPC470190
0.7387 Intermediate Similarity NPC289786
0.7381 Intermediate Similarity NPC478045
0.736 Intermediate Similarity NPC134637
0.7339 Intermediate Similarity NPC476090
0.7336 Intermediate Similarity NPC309498
0.7313 Intermediate Similarity NPC155792
0.7309 Intermediate Similarity NPC103230
0.73 Intermediate Similarity NPC54066
0.7257 Intermediate Similarity NPC324245
0.7257 Intermediate Similarity NPC320748
0.7244 Intermediate Similarity NPC473053
0.7237 Intermediate Similarity NPC32451
0.7229 Intermediate Similarity NPC75179
0.7229 Intermediate Similarity NPC188400
0.7194 Intermediate Similarity NPC183537
0.7193 Intermediate Similarity NPC79223
0.7162 Intermediate Similarity NPC328559
0.716 Intermediate Similarity NPC15406
0.7137 Intermediate Similarity NPC329024
0.7132 Intermediate Similarity NPC191489
0.7131 Intermediate Similarity NPC124313
0.713 Intermediate Similarity NPC44354
0.7126 Intermediate Similarity NPC77878
0.711 Intermediate Similarity NPC294512
0.7093 Intermediate Similarity NPC472436
0.7088 Intermediate Similarity NPC315634
0.7088 Intermediate Similarity NPC100734
0.7088 Intermediate Similarity NPC88923
0.7085 Intermediate Similarity NPC90875
0.7083 Intermediate Similarity NPC86800
0.7082 Intermediate Similarity NPC156044
0.708 Intermediate Similarity NPC37473
0.7076 Intermediate Similarity NPC111732
0.7071 Intermediate Similarity NPC473822
0.7071 Intermediate Similarity NPC141385
0.7068 Intermediate Similarity NPC166722
0.7061 Intermediate Similarity NPC24019
0.7061 Intermediate Similarity NPC470042
0.7059 Intermediate Similarity NPC302807
0.7052 Intermediate Similarity NPC84164
0.7052 Intermediate Similarity NPC207283
0.7045 Intermediate Similarity NPC96584
0.7045 Intermediate Similarity NPC255800
0.7035 Intermediate Similarity NPC56170
0.7031 Intermediate Similarity NPC59033
0.7031 Intermediate Similarity NPC317672
0.7028 Intermediate Similarity NPC189903
0.7028 Intermediate Similarity NPC182907
0.7027 Intermediate Similarity NPC284685
0.7025 Intermediate Similarity NPC122463
0.7017 Intermediate Similarity NPC146976
0.7014 Intermediate Similarity NPC56953
0.7014 Intermediate Similarity NPC176413
0.7012 Intermediate Similarity NPC210296
0.7004 Intermediate Similarity NPC233334
0.7 Intermediate Similarity NPC314222

  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 NPC148896 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
0.7833 Intermediate Similarity NPD1483 Discontinued
0.743 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD8468 Phase 2
0.7371 Intermediate Similarity NPD7069 Discontinued
0.7247 Intermediate Similarity NPD7886 Phase 2
0.7247 Intermediate Similarity NPD7885 Phase 2
0.7235 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD6361 Phase 2
0.7217 Intermediate Similarity NPD2831 Approved
0.7217 Intermediate Similarity NPD7396 Approved
0.7155 Intermediate Similarity NPD8479 Phase 2
0.7132 Intermediate Similarity NPD7708 Approved
0.713 Intermediate Similarity NPD6477 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD4989 Phase 2
0.7088 Intermediate Similarity NPD7803 Approved
0.7085 Intermediate Similarity NPD6257 Clinical (unspecified phase)
0.7038 Intermediate Similarity NPD7862 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD8404 Phase 2
0.7027 Intermediate Similarity NPD7955 Approved
0.7027 Intermediate Similarity NPD7956 Approved
0.6996 Remote Similarity NPD4889 Approved
0.697 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6967 Remote Similarity NPD3925 Approved
0.6929 Remote Similarity NPD1926 Approved
0.6929 Remote Similarity NPD7967 Discontinued
0.6926 Remote Similarity NPD6874 Approved
0.6923 Remote Similarity NPD8052 Clinical (unspecified phase)
0.692 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6298 Discontinued
0.69 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6887 Remote Similarity NPD5482 Discontinued
0.6878 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6877 Remote Similarity NPD6790 Phase 1
0.6877 Remote Similarity NPD7417 Discontinued
0.6862 Remote Similarity NPD5866 Approved
0.6855 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6844 Remote Similarity NPD5147 Discontinued
0.6814 Remote Similarity NPD4375 Approved
0.6797 Remote Similarity NPD5483 Clinical (unspecified phase)
0.679 Remote Similarity NPD8465 Approved
0.679 Remote Similarity NPD8467 Approved
0.679 Remote Similarity NPD8466 Approved
0.6787 Remote Similarity NPD5022 Discontinued
0.6786 Remote Similarity NPD5891 Approved
0.6786 Remote Similarity NPD3006 Discontinued
0.6783 Remote Similarity NPD4551 Phase 2
0.6776 Remote Similarity NPD4923 Phase 1
0.6774 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6773 Remote Similarity NPD4373 Phase 2
0.6766 Remote Similarity NPD5922 Phase 3
0.6763 Remote Similarity NPD3795 Approved
0.6763 Remote Similarity NPD3794 Approved
0.676 Remote Similarity NPD6962 Phase 2
0.6752 Remote Similarity NPD5228 Phase 3
0.6752 Remote Similarity NPD8459 Approved
0.6752 Remote Similarity NPD8460 Approved
0.6752 Remote Similarity NPD6219 Discontinued
0.6749 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6746 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6744 Remote Similarity NPD820 Phase 3
0.6739 Remote Similarity NPD3924 Approved
0.6739 Remote Similarity NPD3923 Approved
0.6739 Remote Similarity NPD3921 Approved
0.6739 Remote Similarity NPD3922 Approved
0.6734 Remote Similarity NPD5640 Discontinued
0.6732 Remote Similarity NPD6825 Phase 1
0.6721 Remote Similarity NPD7395 Discontinued
0.6718 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6711 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3386 Phase 2
0.6708 Remote Similarity NPD5726 Clinical (unspecified phase)
0.6696 Remote Similarity NPD1620 Clinical (unspecified phase)
0.6695 Remote Similarity NPD7467 Discontinued
0.6694 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6691 Remote Similarity NPD8425 Approved
0.6691 Remote Similarity NPD8426 Approved
0.6681 Remote Similarity NPD4021 Phase 2
0.668 Remote Similarity NPD7927 Clinical (unspecified phase)
0.668 Remote Similarity NPD8327 Clinical (unspecified phase)
0.668 Remote Similarity NPD8326 Phase 3
0.668 Remote Similarity NPD8325 Phase 3
0.6667 Remote Similarity NPD8428 Approved
0.6667 Remote Similarity NPD6569 Phase 2
0.6667 Remote Similarity NPD5513 Phase 2
0.6667 Remote Similarity NPD8429 Approved
0.6667 Remote Similarity NPD8091 Phase 3
0.6667 Remote Similarity NPD8427 Approved
0.6654 Remote Similarity NPD4369 Phase 2
0.6653 Remote Similarity NPD4952 Phase 3
0.6653 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6642 Remote Similarity NPD5450 Discontinued
0.6641 Remote Similarity NPD2921 Clinical (unspecified phase)
0.664 Remote Similarity NPD6494 Phase 2
0.664 Remote Similarity NPD7268 Clinical (unspecified phase)
0.664 Remote Similarity NPD7558 Phase 2
0.663 Remote Similarity NPD8364 Approved
0.663 Remote Similarity NPD8363 Approved
0.6628 Remote Similarity NPD8101 Phase 3
0.6627 Remote Similarity NPD5805 Approved
0.6626 Remote Similarity NPD6955 Clinical (unspecified phase)
0.6626 Remote Similarity NPD6974 Phase 3
0.6624 Remote Similarity NPD7123 Suspended
0.6618 Remote Similarity NPD7053 Clinical (unspecified phase)
0.6617 Remote Similarity NPD6530 Approved
0.6617 Remote Similarity NPD6531 Approved
0.6615 Remote Similarity NPD6276 Discontinued
0.6612 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6604 Remote Similarity NPD7169 Suspended
0.66 Remote Similarity NPD3263 Phase 3
0.66 Remote Similarity NPD7426 Phase 1
0.6594 Remote Similarity NPD7416 Clinical (unspecified phase)
0.6593 Remote Similarity NPD7925 Phase 2
0.6593 Remote Similarity NPD7924 Phase 2
0.6589 Remote Similarity NPD6716 Phase 1
0.6588 Remote Similarity NPD7853 Phase 2
0.6584 Remote Similarity NPD3815 Phase 1
0.6584 Remote Similarity NPD3816 Phase 1
0.6583 Remote Similarity NPD5429 Discontinued
0.6581 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6581 Remote Similarity NPD5512 Phase 3
0.658 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6578 Remote Similarity NPD7859 Phase 2
0.6577 Remote Similarity NPD5488 Discontinued
0.6574 Remote Similarity NPD7826 Clinical (unspecified phase)
0.6569 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6556 Remote Similarity NPD2509 Approved
0.6556 Remote Similarity NPD2510 Approved
0.6555 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6963 Approved
0.6549 Remote Similarity NPD6964 Approved
0.6545 Remote Similarity NPD6635 Approved
0.6545 Remote Similarity NPD3217 Phase 2
0.654 Remote Similarity NPD6503 Clinical (unspecified phase)
0.654 Remote Similarity NPD4491 Clinical (unspecified phase)
0.6538 Remote Similarity NPD3396 Approved
0.6538 Remote Similarity NPD3395 Approved
0.6535 Remote Similarity NPD5015 Clinical (unspecified phase)
0.6532 Remote Similarity NPD7180 Phase 3
0.6531 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6531 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6531 Remote Similarity NPD5293 Phase 2
0.6529 Remote Similarity NPD4437 Phase 3
0.6525 Remote Similarity NPD3322 Phase 1
0.652 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6518 Remote Similarity NPD3354 Phase 2
0.6518 Remote Similarity NPD2011 Clinical (unspecified phase)
0.6513 Remote Similarity NPD8100 Phase 3
0.6504 Remote Similarity NPD1032 Phase 2
0.6494 Remote Similarity NPD8434 Phase 2
0.6493 Remote Similarity NPD6228 Discontinued
0.6493 Remote Similarity NPD5867 Clinical (unspecified phase)
0.6491 Remote Similarity NPD8370 Discontinued
0.6491 Remote Similarity NPD5532 Phase 2
0.6483 Remote Similarity NPD7238 Clinical (unspecified phase)
0.648 Remote Similarity NPD8356 Approved
0.6475 Remote Similarity NPD5416 Discontinued
0.6475 Remote Similarity NPD4417 Approved
0.6473 Remote Similarity NPD1078 Clinical (unspecified phase)
0.6473 Remote Similarity NPD7010 Phase 3
0.6471 Remote Similarity NPD7796 Approved
0.6471 Remote Similarity NPD7797 Approved
0.6466 Remote Similarity NPD8442 Discontinued
0.6466 Remote Similarity NPD3280 Approved
0.6461 Remote Similarity NPD6529 Discontinued
0.646 Remote Similarity NPD7689 Approved
0.6452 Remote Similarity NPD6198 Phase 1
0.6452 Remote Similarity NPD4429 Discontinued
0.6452 Remote Similarity NPD5632 Approved
0.645 Remote Similarity NPD8359 Phase 2
0.6448 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6443 Remote Similarity NPD3259 Approved
0.6443 Remote Similarity NPD4086 Phase 1
0.6441 Remote Similarity NPD6550 Discontinued
0.6437 Remote Similarity NPD5612 Discontinued
0.6434 Remote Similarity NPD7673 Phase 3
0.6434 Remote Similarity NPD8489 Phase 1
0.6432 Remote Similarity NPD4122 Approved
0.6432 Remote Similarity NPD3947 Discontinued
0.6432 Remote Similarity NPD32 Approved
0.6432 Remote Similarity NPD4034 Approved
0.6432 Remote Similarity NPD4033 Approved
0.6432 Remote Similarity NPD4039 Approved
0.6432 Remote Similarity NPD4036 Approved
0.6432 Remote Similarity NPD4038 Approved
0.6432 Remote Similarity NPD31 Approved
0.6432 Remote Similarity NPD4035 Approved
0.6432 Remote Similarity NPD4037 Approved
0.6426 Remote Similarity NPD3763 Approved
0.6423 Remote Similarity NPD7816 Clinical (unspecified phase)
0.6421 Remote Similarity NPD4894 Discontinued
0.6419 Remote Similarity NPD9271 Approved
0.6417 Remote Similarity NPD5005 Approved
0.6417 Remote Similarity NPD5006 Approved
0.6414 Remote Similarity NPD2952 Discontinued
0.641 Remote Similarity NPD2336 Approved
0.6408 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6406 Remote Similarity NPD7031 Phase 1
0.6405 Remote Similarity NPD6728 Phase 3
0.6405 Remote Similarity NPD5601 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