Structure

Physi-Chem Properties

Molecular Weight:  925.3
Volume:  882.791
LogP:  2.288
LogD:  1.281
LogS:  -4.183
# Rotatable Bonds:  16
TPSA:  279.05
# H-Bond Aceptor:  21
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.277
Synthetic Accessibility Score:  7.733
Fsp3:  0.556
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:  -5.266
MDCK Permeability:  0.00018473740783520043
Pgp-inhibitor:  0.998
Pgp-substrate:  0.033
Human Intestinal Absorption (HIA):  0.886
20% Bioavailability (F20%):  0.997
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.068
Plasma Protein Binding (PPB):  27.6481990814209%
Volume Distribution (VD):  1.45
Pgp-substrate:  24.546947479248047%

ADMET: Metabolism

CYP1A2-inhibitor:  0.04
CYP1A2-substrate:  0.01
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.003
CYP2D6-inhibitor:  0.973
CYP2D6-substrate:  0.015
CYP3A4-inhibitor:  0.768
CYP3A4-substrate:  0.256

ADMET: Excretion

Clearance (CL):  2.664
Half-life (T1/2):  0.423

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.973
Drug-inuced Liver Injury (DILI):  0.964
AMES Toxicity:  0.055
Rat Oral Acute Toxicity:  0.171
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.259
Carcinogencity:  0.091
Eye Corrosion:  0.003
Eye Irritation:  0.034
Respiratory Toxicity:  0.029

Download Data

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

  Natural Product: NPC319880

Natural Product ID:  NPC319880
Common Name*:   Mekongensine
IUPAC Name:   n.a.
Synonyms:   mekongensine
Standard InCHIKey:  ZOOHSIOMIRBBDY-DLKMHDBTSA-N
Standard InCHI:  InChI=1S/C45H51NO20/c1-22(47)57-21-44-36(61-25(4)50)32(59-23(2)48)31-34(63-38(53)28-14-11-10-12-15-28)45(44)43(9,56)35(33(60-24(3)49)37(44)62-26(5)51)64-40(55)41(7,65-27(6)52)18-17-30-29(16-13-19-46-30)39(54)58-20-42(31,8)66-45/h10-16,19,31-37,56H,17-18,20-21H2,1-9H3/t31-,32-,33+,34-,35+,36-,37+,41+,42+,43+,44+,45+/m1/s1
SMILES:  CC(=O)OC[C@@]12[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@H]3[C@]([C@@]42O[C@@]([C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)[C@H]4OC(=O)c1ccccc1)(C)COC(=O)c1cccnc1CC[C@](C(=O)O3)(C)OC(=O)C)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1813068
PubChem CID:   56669673
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
NPO30152 Maytenus mekongensis Species Celastraceae Eukaryota n.a. root n.a. PMID[21634414]

☑ 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
NPT91 Cell Line KB Homo sapiens IC50 = 28.2 ug.mL-1 PMID[564414]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 3100.0 nM PMID[564414]

☑ 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 NPC319880 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 NPC244839
1.0 High Similarity NPC320324
0.9951 High Similarity NPC473689
0.9951 High Similarity NPC292416
0.9951 High Similarity NPC237702
0.9856 High Similarity NPC38959
0.9856 High Similarity NPC327904
0.9808 High Similarity NPC475406
0.9805 High Similarity NPC328186
0.9805 High Similarity NPC477787
0.9805 High Similarity NPC122968
0.9805 High Similarity NPC146824
0.9805 High Similarity NPC228377
0.9757 High Similarity NPC475362
0.9716 High Similarity NPC253482
0.9709 High Similarity NPC476110
0.9709 High Similarity NPC475631
0.9709 High Similarity NPC475600
0.9709 High Similarity NPC87152
0.9663 High Similarity NPC316841
0.9662 High Similarity NPC471190
0.9662 High Similarity NPC475644
0.9662 High Similarity NPC471977
0.9662 High Similarity NPC470486
0.9659 High Similarity NPC57797
0.9659 High Similarity NPC250807
0.9612 High Similarity NPC473850
0.961 High Similarity NPC477788
0.9579 High Similarity NPC475648
0.9569 High Similarity NPC475303
0.9569 High Similarity NPC475596
0.9565 High Similarity NPC473506
0.9563 High Similarity NPC76565
0.9524 High Similarity NPC30456
0.9517 High Similarity NPC475137
0.9517 High Similarity NPC475498
0.9517 High Similarity NPC328154
0.9463 High Similarity NPC301368
0.9463 High Similarity NPC84815
0.9434 High Similarity NPC327769
0.9434 High Similarity NPC35208
0.9366 High Similarity NPC6981
0.9366 High Similarity NPC471016
0.9327 High Similarity NPC127720
0.9327 High Similarity NPC127026
0.932 High Similarity NPC294579
0.932 High Similarity NPC144779
0.9317 High Similarity NPC470306
0.9292 High Similarity NPC150698
0.9292 High Similarity NPC96801
0.9282 High Similarity NPC471980
0.9279 High Similarity NPC477912
0.9272 High Similarity NPC475408
0.9272 High Similarity NPC471014
0.9268 High Similarity NPC4421
0.9252 High Similarity NPC170751
0.9242 High Similarity NPC475601
0.9227 High Similarity NPC62367
0.9194 High Similarity NPC148860
0.9183 High Similarity NPC216428
0.9163 High Similarity NPC475426
0.9135 High Similarity NPC473115
0.9135 High Similarity NPC75600
0.9135 High Similarity NPC158020
0.9135 High Similarity NPC6576
0.9135 High Similarity NPC473089
0.9135 High Similarity NPC212768
0.913 High Similarity NPC42678
0.913 High Similarity NPC477909
0.913 High Similarity NPC477907
0.9082 High Similarity NPC319128
0.9061 High Similarity NPC211920
0.9057 High Similarity NPC477902
0.899 High Similarity NPC228331
0.8986 High Similarity NPC472553
0.8982 High Similarity NPC13603
0.8981 High Similarity NPC469748
0.8972 High Similarity NPC124029
0.8962 High Similarity NPC477911
0.8947 High Similarity NPC477910
0.8938 High Similarity NPC85879
0.8938 High Similarity NPC53255
0.8915 High Similarity NPC477903
0.891 High Similarity NPC472555
0.8855 High Similarity NPC326930
0.8855 High Similarity NPC475301
0.8841 High Similarity NPC48042
0.8841 High Similarity NPC472550
0.8841 High Similarity NPC304179
0.8815 High Similarity NPC477908
0.8815 High Similarity NPC206343
0.881 High Similarity NPC264674
0.8788 High Similarity NPC471978
0.8761 High Similarity NPC477906
0.8707 High Similarity NPC328928
0.8704 High Similarity NPC477899
0.8704 High Similarity NPC477900
0.8702 High Similarity NPC63041
0.8701 High Similarity NPC473833
0.8698 High Similarity NPC235364
0.8675 High Similarity NPC471979
0.8628 High Similarity NPC475533
0.8618 High Similarity NPC26881
0.8605 High Similarity NPC477901
0.859 High Similarity NPC475315
0.859 High Similarity NPC324619
0.8584 High Similarity NPC311196
0.8584 High Similarity NPC134384
0.8539 High Similarity NPC285411
0.8539 High Similarity NPC14116
0.8514 High Similarity NPC238278
0.8468 Intermediate Similarity NPC213143
0.8462 Intermediate Similarity NPC91125
0.8451 Intermediate Similarity NPC476467
0.8396 Intermediate Similarity NPC472752
0.8364 Intermediate Similarity NPC233727
0.8326 Intermediate Similarity NPC471015
0.8279 Intermediate Similarity NPC280473
0.8279 Intermediate Similarity NPC323551
0.8261 Intermediate Similarity NPC148896
0.8261 Intermediate Similarity NPC476090
0.8261 Intermediate Similarity NPC180668
0.8261 Intermediate Similarity NPC471013
0.8241 Intermediate Similarity NPC51008
0.8241 Intermediate Similarity NPC41724
0.8208 Intermediate Similarity NPC289086
0.8174 Intermediate Similarity NPC187494
0.8148 Intermediate Similarity NPC40919
0.8148 Intermediate Similarity NPC470189
0.812 Intermediate Similarity NPC10904
0.8093 Intermediate Similarity NPC470190
0.8091 Intermediate Similarity NPC319556
0.8082 Intermediate Similarity NPC30570
0.8045 Intermediate Similarity NPC162812
0.8028 Intermediate Similarity NPC292517
0.8 Intermediate Similarity NPC207531
0.7991 Intermediate Similarity NPC165837
0.7963 Intermediate Similarity NPC475835
0.7934 Intermediate Similarity NPC470279
0.7919 Intermediate Similarity NPC62844
0.7919 Intermediate Similarity NPC193361
0.7752 Intermediate Similarity NPC309498
0.7665 Intermediate Similarity NPC253314
0.7653 Intermediate Similarity NPC103230
0.7597 Intermediate Similarity NPC471004
0.7595 Intermediate Similarity NPC37473
0.7545 Intermediate Similarity NPC111732
0.75 Intermediate Similarity NPC109922
0.7489 Intermediate Similarity NPC70155
0.7489 Intermediate Similarity NPC32451
0.7489 Intermediate Similarity NPC328559
0.7489 Intermediate Similarity NPC235885
0.7455 Intermediate Similarity NPC314834
0.7431 Intermediate Similarity NPC320748
0.7431 Intermediate Similarity NPC324245
0.7397 Intermediate Similarity NPC107123
0.7391 Intermediate Similarity NPC140311
0.7366 Intermediate Similarity NPC470280
0.7364 Intermediate Similarity NPC79223
0.7352 Intermediate Similarity NPC149708
0.7347 Intermediate Similarity NPC183537
0.7343 Intermediate Similarity NPC249614
0.7339 Intermediate Similarity NPC141428
0.7328 Intermediate Similarity NPC106593
0.7321 Intermediate Similarity NPC156044
0.7321 Intermediate Similarity NPC315545
0.7321 Intermediate Similarity NPC314297
0.7318 Intermediate Similarity NPC123395
0.7314 Intermediate Similarity NPC15406
0.7308 Intermediate Similarity NPC191310
0.7306 Intermediate Similarity NPC329024
0.7306 Intermediate Similarity NPC476516
0.7304 Intermediate Similarity NPC141385
0.7303 Intermediate Similarity NPC210296
0.73 Intermediate Similarity NPC233334
0.7299 Intermediate Similarity NPC471997
0.7296 Intermediate Similarity NPC473667
0.7288 Intermediate Similarity NPC24019
0.7287 Intermediate Similarity NPC131273
0.7287 Intermediate Similarity NPC473441
0.7284 Intermediate Similarity NPC2395
0.7284 Intermediate Similarity NPC124313
0.7281 Intermediate Similarity NPC317752
0.728 Intermediate Similarity NPC108342
0.7277 Intermediate Similarity NPC313345
0.7277 Intermediate Similarity NPC313796
0.7277 Intermediate Similarity NPC314855
0.7277 Intermediate Similarity NPC315638
0.7277 Intermediate Similarity NPC57690
0.7277 Intermediate Similarity NPC207851
0.7276 Intermediate Similarity NPC77878
0.7273 Intermediate Similarity NPC317672
0.7261 Intermediate Similarity NPC471782
0.7261 Intermediate Similarity NPC471583
0.725 Intermediate Similarity NPC189903
0.725 Intermediate Similarity NPC182907
0.7238 Intermediate Similarity NPC90875
0.7237 Intermediate Similarity NPC318299
0.7232 Intermediate Similarity NPC12944
0.7232 Intermediate Similarity NPC25442

  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 NPC319880 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
0.8465 Intermediate Similarity NPD8468 Phase 2
0.7867 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7396 Approved
0.7511 Intermediate Similarity NPD3794 Approved
0.7511 Intermediate Similarity NPD3795 Approved
0.75 Intermediate Similarity NPD5891 Approved
0.7466 Intermediate Similarity NPD6987 Phase 1
0.7455 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD1483 Discontinued
0.7309 Intermediate Similarity NPD3947 Discontinued
0.7288 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7269 Intermediate Similarity NPD4417 Approved
0.7237 Intermediate Similarity NPD7069 Discontinued
0.7222 Intermediate Similarity NPD7234 Approved
0.7222 Intermediate Similarity NPD7233 Approved
0.7217 Intermediate Similarity NPD3394 Approved
0.7217 Intermediate Similarity NPD3389 Approved
0.7217 Intermediate Similarity NPD3393 Approved
0.7212 Intermediate Similarity NPD2509 Approved
0.7212 Intermediate Similarity NPD2510 Approved
0.7211 Intermediate Similarity NPD7708 Approved
0.7181 Intermediate Similarity NPD4506 Discontinued
0.7167 Intermediate Similarity NPD3280 Approved
0.7165 Intermediate Similarity NPD7803 Approved
0.7124 Intermediate Similarity NPD7010 Phase 3
0.7124 Intermediate Similarity NPD6770 Approved
0.7112 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD8325 Phase 3
0.7112 Intermediate Similarity NPD8326 Phase 3
0.7111 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD7956 Approved
0.7103 Intermediate Similarity NPD7955 Approved
0.7087 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD820 Phase 3
0.704 Intermediate Similarity NPD7777 Approved
0.704 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD53 Approved
0.704 Intermediate Similarity NPD7778 Approved
0.7031 Intermediate Similarity NPD6529 Discontinued
0.7026 Intermediate Similarity NPD7707 Approved
0.7014 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7878 Phase 2
0.7 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.6996 Remote Similarity NPD8485 Approved
0.6991 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6983 Remote Similarity NPD4373 Phase 2
0.6982 Remote Similarity NPD4427 Phase 2
0.6975 Remote Similarity NPD3925 Approved
0.6974 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6974 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6971 Remote Similarity NPD6962 Phase 2
0.697 Remote Similarity NPD5475 Discontinued
0.696 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6955 Remote Similarity NPD8063 Discontinued
0.6951 Remote Similarity NPD7417 Discontinued
0.6949 Remote Similarity NPD8479 Phase 2
0.6938 Remote Similarity NPD6635 Approved
0.693 Remote Similarity NPD5901 Discontinued
0.6923 Remote Similarity NPD2336 Approved
0.692 Remote Similarity NPD8465 Approved
0.692 Remote Similarity NPD8467 Approved
0.692 Remote Similarity NPD8466 Approved
0.6911 Remote Similarity NPD7885 Phase 2
0.6911 Remote Similarity NPD7886 Phase 2
0.6903 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6884 Remote Similarity NPD6641 Approved
0.6884 Remote Similarity NPD6642 Approved
0.6878 Remote Similarity NPD8435 Approved
0.6875 Remote Similarity NPD5640 Discontinued
0.6863 Remote Similarity NPD8091 Phase 3
0.686 Remote Similarity NPD4952 Phase 3
0.6857 Remote Similarity NPD5088 Discontinued
0.6856 Remote Similarity NPD2831 Approved
0.6849 Remote Similarity NPD4301 Approved
0.6842 Remote Similarity NPD7187 Phase 2
0.6838 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6825 Remote Similarity NPD5482 Discontinued
0.6822 Remote Similarity NPD4989 Phase 2
0.6822 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6816 Remote Similarity NPD8459 Approved
0.6816 Remote Similarity NPD8425 Approved
0.6816 Remote Similarity NPD8460 Approved
0.6816 Remote Similarity NPD8426 Approved
0.6815 Remote Similarity NPD6790 Phase 1
0.6806 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6805 Remote Similarity NPD8289 Discontinued
0.6802 Remote Similarity NPD8361 Approved
0.6802 Remote Similarity NPD8360 Approved
0.68 Remote Similarity NPD2307 Discontinued
0.68 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6795 Remote Similarity NPD5866 Approved
0.6792 Remote Similarity NPD8428 Approved
0.6792 Remote Similarity NPD8429 Approved
0.6792 Remote Similarity NPD8427 Approved
0.679 Remote Similarity NPD8052 Clinical (unspecified phase)
0.679 Remote Similarity NPD5022 Discontinued
0.6787 Remote Similarity NPD4948 Discontinued
0.6787 Remote Similarity NPD6716 Phase 1
0.6787 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6783 Remote Similarity NPD7862 Clinical (unspecified phase)
0.677 Remote Similarity NPD5003 Discontinued
0.6767 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7404 Approved
0.6762 Remote Similarity NPD7688 Phase 1
0.6761 Remote Similarity NPD5805 Approved
0.6754 Remote Similarity NPD4601 Approved
0.6754 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6754 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6754 Remote Similarity NPD4600 Approved
0.6753 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6753 Remote Similarity NPD7001 Phase 3
0.6752 Remote Similarity NPD7470 Discontinued
0.6751 Remote Similarity NPD8000 Clinical (unspecified phase)
0.675 Remote Similarity NPD6995 Phase 1
0.675 Remote Similarity NPD8356 Approved
0.6741 Remote Similarity NPD3921 Approved
0.6741 Remote Similarity NPD3924 Approved
0.6741 Remote Similarity NPD3923 Approved
0.6741 Remote Similarity NPD3922 Approved
0.6741 Remote Similarity NPD4376 Phase 3
0.6737 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6732 Remote Similarity NPD9271 Approved
0.6726 Remote Similarity NPD6281 Approved
0.6723 Remote Similarity NPD7395 Discontinued
0.6721 Remote Similarity NPD3006 Discontinued
0.6711 Remote Similarity NPD4529 Approved
0.6711 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6711 Remote Similarity NPD4528 Approved
0.6711 Remote Similarity NPD4526 Approved
0.6711 Remote Similarity NPD6999 Discontinued
0.671 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6709 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6708 Remote Similarity NPD4328 Approved
0.6708 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6697 Remote Similarity NPD4889 Approved
0.6692 Remote Similarity NPD8363 Approved
0.6692 Remote Similarity NPD8364 Approved
0.6681 Remote Similarity NPD7957 Phase 1
0.6681 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6681 Remote Similarity NPD4602 Approved
0.6667 Remote Similarity NPD7426 Phase 1
0.6667 Remote Similarity NPD4897 Phase 2
0.6653 Remote Similarity NPD3816 Phase 1
0.6653 Remote Similarity NPD3815 Phase 1
0.6651 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6642 Remote Similarity NPD8365 Clinical (unspecified phase)
0.664 Remote Similarity NPD5488 Discontinued
0.664 Remote Similarity NPD6494 Phase 2
0.664 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6639 Remote Similarity NPD8160 Phase 2
0.6639 Remote Similarity NPD5507 Approved
0.6639 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6639 Remote Similarity NPD8430 Approved
0.6639 Remote Similarity NPD5506 Approved
0.6639 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6791 Phase 2
0.6627 Remote Similarity NPD8101 Phase 3
0.6626 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6624 Remote Similarity NPD7191 Phase 2
0.6623 Remote Similarity NPD6206 Phase 1
0.6622 Remote Similarity NPD8407 Phase 2
0.6621 Remote Similarity NPD5398 Clinical (unspecified phase)
0.662 Remote Similarity NPD1631 Approved
0.6619 Remote Similarity NPD6026 Approved
0.6615 Remote Similarity NPD8463 Approved
0.6615 Remote Similarity NPD6228 Discontinued
0.6614 Remote Similarity NPD6276 Discontinued
0.6614 Remote Similarity NPD7576 Discontinued
0.6613 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6609 Remote Similarity NPD4501 Approved
0.6609 Remote Similarity NPD4500 Approved
0.6609 Remote Similarity NPD6479 Discontinued
0.6602 Remote Similarity NPD7169 Suspended
0.6597 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6597 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6595 Remote Similarity NPD6176 Phase 1
0.6588 Remote Similarity NPD8102 Discontinued
0.6588 Remote Similarity NPD2581 Approved
0.6588 Remote Similarity NPD2582 Approved
0.6587 Remote Similarity NPD8412 Phase 1
0.6583 Remote Similarity NPD4429 Discontinued
0.6583 Remote Similarity NPD3354 Phase 2
0.6581 Remote Similarity NPD5429 Discontinued
0.6581 Remote Similarity NPD7562 Approved
0.6578 Remote Similarity NPD2565 Phase 2
0.6578 Remote Similarity NPD5450 Discontinued
0.6578 Remote Similarity NPD2564 Approved
0.6574 Remote Similarity NPD1575 Approved
0.6574 Remote Similarity NPD1573 Approved
0.6573 Remote Similarity NPD7558 Phase 2
0.6571 Remote Similarity NPD4086 Phase 1
0.6567 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6564 Remote Similarity NPD6361 Phase 2
0.6561 Remote Similarity NPD3178 Discontinued

  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