Structure

Physi-Chem Properties

Molecular Weight:  809.49
Volume:  849.005
LogP:  5.694
LogD:  4.281
LogS:  -4.78
# Rotatable Bonds:  11
TPSA:  180.52
# H-Bond Aceptor:  14
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.169
Synthetic Accessibility Score:  5.77
Fsp3:  0.659
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:  -4.873
MDCK Permeability:  2.6533221898716874e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.287
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  88.58622741699219%
Volume Distribution (VD):  0.491
Pgp-substrate:  2.4266445636749268%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.021
CYP2C19-inhibitor:  0.182
CYP2C19-substrate:  0.328
CYP2C9-inhibitor:  0.463
CYP2C9-substrate:  0.044
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.118
CYP3A4-inhibitor:  0.969
CYP3A4-substrate:  0.582

ADMET: Excretion

Clearance (CL):  7.285
Half-life (T1/2):  0.065

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.959
Drug-inuced Liver Injury (DILI):  0.502
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.868
Maximum Recommended Daily Dose:  0.805
Skin Sensitization:  0.05
Carcinogencity:  0.094
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.038

Download Data

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

  Natural Product: NPC5620

Natural Product ID:  NPC5620
Common Name*:   Pitipeptolide B
IUPAC Name:   (3S,6S,9S,13S,19S,22S)-6-benzyl-3,19-bis[(2S)-butan-2-yl]-7,12,12-trimethyl-13-pent-4-enyl-9-propan-2-yl-4,14-dioxa-1,7,10,17,20-pentazabicyclo[20.3.0]pentacosane-2,5,8,11,15,18,21-heptone
Synonyms:  
Standard InCHIKey:  WXTNWSNJAHRKRT-XXMTWPQQSA-N
Standard InCHI:  InChI=1S/C44H67N5O9/c1-11-14-16-23-33-44(8,9)43(56)47-35(27(4)5)40(53)48(10)32(25-30-20-17-15-18-21-30)42(55)58-37(29(7)13-3)41(54)49-24-19-22-31(49)38(51)46-36(28(6)12-2)39(52)45-26-34(50)57-33/h11,15,17-18,20-21,27-29,31-33,35-37H,1,12-14,16,19,22-26H2,2-10H3,(H,45,52)(H,46,51)(H,47,56)/t28-,29-,31-,32-,33-,35-,36-,37-/m0/s1
SMILES:  C=CCCC[C@@H]1OC(=O)CN=C(O)[C@@H](N=C(O)[C@@H]2CCCN2C(=O)[C@@H](OC(=O)[C@@H](N(C(=O)[C@@H](N=C(C1(C)C)O)C(C)C)C)Cc1ccccc1)[C@H](CC)C)[C@H](CC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL505027
PubChem CID:   10819182
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10514329]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10654420]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10691708]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. palauan n.a. PMID[10691729]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10843570]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10924172]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10978206]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076571]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076573]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076574]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11277744]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11389621]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11430000]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11473443]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11922791]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762816]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[12828459]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14575437]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[1517734]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[16643028]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17125217]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17441769]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18444683]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Singapore n.a. PMID[19093843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19489598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. eastern Caribbean n.a. PMID[19739598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19839606]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20030365]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. panamanian n.a. PMID[20158242]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Floridian n.a. PMID[20166701]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20936843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21138309]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[2128518]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21341718]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21539315]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21806011]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21999614]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[22035372]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[29792428]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[3924698]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[7623050]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9584405]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599278]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599279]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9784156]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria 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
NPT114 Cell Line LoVo Homo sapiens IC50 = 1.95 ug.mL-1 PMID[485005]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis IZ = 15.0 mm PMID[485005]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis IZ = 10.0 mm PMID[485005]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis IZ = 30.0 mm PMID[485005]
NPT2 Others Unspecified FC = 2.55 n.a. PMID[485005]

☑ 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 NPC5620 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9708 High Similarity NPC129666
0.9338 High Similarity NPC263493
0.9338 High Similarity NPC269398
0.9333 High Similarity NPC98424
0.9333 High Similarity NPC178662
0.9333 High Similarity NPC476133
0.9333 High Similarity NPC92784
0.9333 High Similarity NPC470884
0.9275 High Similarity NPC209509
0.927 High Similarity NPC161069
0.9259 High Similarity NPC471264
0.9259 High Similarity NPC471265
0.9203 High Similarity NPC476978
0.9143 High Similarity NPC145113
0.9143 High Similarity NPC329761
0.9143 High Similarity NPC225648
0.9021 High Similarity NPC162104
0.9007 High Similarity NPC138775
0.8993 High Similarity NPC139326
0.8973 High Similarity NPC297145
0.8973 High Similarity NPC197743
0.8944 High Similarity NPC240848
0.8944 High Similarity NPC471821
0.8944 High Similarity NPC471820
0.8881 High Similarity NPC2501
0.8841 High Similarity NPC68865
0.8714 High Similarity NPC307357
0.8714 High Similarity NPC46098
0.8714 High Similarity NPC239762
0.8714 High Similarity NPC268841
0.8714 High Similarity NPC163392
0.8699 High Similarity NPC122590
0.8696 High Similarity NPC248283
0.8662 High Similarity NPC52748
0.8542 High Similarity NPC262077
0.8507 High Similarity NPC6975
0.8507 High Similarity NPC46427
0.8478 Intermediate Similarity NPC130309
0.8472 Intermediate Similarity NPC313867
0.8472 Intermediate Similarity NPC316008
0.8462 Intermediate Similarity NPC197682
0.8433 Intermediate Similarity NPC252878
0.8425 Intermediate Similarity NPC105717
0.8421 Intermediate Similarity NPC200964
0.8414 Intermediate Similarity NPC314358
0.8403 Intermediate Similarity NPC314388
0.8403 Intermediate Similarity NPC315283
0.8392 Intermediate Similarity NPC168113
0.8358 Intermediate Similarity NPC202521
0.8356 Intermediate Similarity NPC135121
0.8333 Intermediate Similarity NPC176226
0.8311 Intermediate Similarity NPC7817
0.8311 Intermediate Similarity NPC475168
0.831 Intermediate Similarity NPC127741
0.8284 Intermediate Similarity NPC476990
0.8271 Intermediate Similarity NPC310467
0.8227 Intermediate Similarity NPC287401
0.8219 Intermediate Similarity NPC201244
0.8219 Intermediate Similarity NPC477217
0.8214 Intermediate Similarity NPC255447
0.82 Intermediate Similarity NPC286551
0.8195 Intermediate Similarity NPC169328
0.8194 Intermediate Similarity NPC476259
0.8146 Intermediate Similarity NPC470902
0.8138 Intermediate Similarity NPC469427
0.8138 Intermediate Similarity NPC469426
0.8129 Intermediate Similarity NPC105114
0.8129 Intermediate Similarity NPC319766
0.8129 Intermediate Similarity NPC71933
0.8129 Intermediate Similarity NPC239990
0.8129 Intermediate Similarity NPC152850
0.8129 Intermediate Similarity NPC89923
0.8095 Intermediate Similarity NPC315266
0.8079 Intermediate Similarity NPC473341
0.8071 Intermediate Similarity NPC473322
0.8058 Intermediate Similarity NPC136453
0.8028 Intermediate Similarity NPC246079
0.8 Intermediate Similarity NPC283783
0.7986 Intermediate Similarity NPC101719
0.7973 Intermediate Similarity NPC322878
0.7958 Intermediate Similarity NPC157311
0.795 Intermediate Similarity NPC318930
0.795 Intermediate Similarity NPC26108
0.795 Intermediate Similarity NPC317362
0.795 Intermediate Similarity NPC477462
0.7914 Intermediate Similarity NPC222466
0.7902 Intermediate Similarity NPC44805
0.7902 Intermediate Similarity NPC8761
0.7898 Intermediate Similarity NPC471051
0.7898 Intermediate Similarity NPC471053
0.7898 Intermediate Similarity NPC471052
0.7888 Intermediate Similarity NPC137627
0.7887 Intermediate Similarity NPC300315
0.7887 Intermediate Similarity NPC200589
0.7868 Intermediate Similarity NPC470546
0.7842 Intermediate Similarity NPC474082
0.7842 Intermediate Similarity NPC175726
0.784 Intermediate Similarity NPC317725
0.784 Intermediate Similarity NPC326407
0.7821 Intermediate Similarity NPC62104
0.7821 Intermediate Similarity NPC1390
0.7805 Intermediate Similarity NPC475421
0.7794 Intermediate Similarity NPC470545
0.7771 Intermediate Similarity NPC471527
0.7764 Intermediate Similarity NPC475123
0.7764 Intermediate Similarity NPC475204
0.7755 Intermediate Similarity NPC132636
0.7754 Intermediate Similarity NPC478016
0.7754 Intermediate Similarity NPC478014
0.7754 Intermediate Similarity NPC478015
0.7737 Intermediate Similarity NPC237420
0.7736 Intermediate Similarity NPC472923
0.7721 Intermediate Similarity NPC285926
0.7721 Intermediate Similarity NPC470544
0.7721 Intermediate Similarity NPC315276
0.7721 Intermediate Similarity NPC14672
0.7692 Intermediate Similarity NPC111428
0.7665 Intermediate Similarity NPC470903
0.7665 Intermediate Similarity NPC167763
0.7665 Intermediate Similarity NPC470112
0.7658 Intermediate Similarity NPC469901
0.7654 Intermediate Similarity NPC196091
0.764 Intermediate Similarity NPC473502
0.7628 Intermediate Similarity NPC469903
0.7626 Intermediate Similarity NPC477061
0.7626 Intermediate Similarity NPC45777
0.7626 Intermediate Similarity NPC190663
0.7625 Intermediate Similarity NPC210377
0.7625 Intermediate Similarity NPC5719
0.7625 Intermediate Similarity NPC217804
0.7625 Intermediate Similarity NPC22883
0.7613 Intermediate Similarity NPC262166
0.76 Intermediate Similarity NPC77905
0.7591 Intermediate Similarity NPC239357
0.7578 Intermediate Similarity NPC15068
0.7574 Intermediate Similarity NPC299806
0.7574 Intermediate Similarity NPC33742
0.7561 Intermediate Similarity NPC306804
0.7551 Intermediate Similarity NPC141050
0.7531 Intermediate Similarity NPC107938
0.7531 Intermediate Similarity NPC294516
0.7531 Intermediate Similarity NPC63040
0.7518 Intermediate Similarity NPC160493
0.7516 Intermediate Similarity NPC16188
0.7515 Intermediate Similarity NPC279871
0.7515 Intermediate Similarity NPC471165
0.7515 Intermediate Similarity NPC155506
0.7515 Intermediate Similarity NPC476227
0.7515 Intermediate Similarity NPC159767
0.75 Intermediate Similarity NPC35850
0.75 Intermediate Similarity NPC80150
0.75 Intermediate Similarity NPC276949
0.7485 Intermediate Similarity NPC4910
0.7483 Intermediate Similarity NPC47667
0.7451 Intermediate Similarity NPC81026
0.745 Intermediate Similarity NPC43755
0.7447 Intermediate Similarity NPC71684
0.7439 Intermediate Similarity NPC40234
0.7439 Intermediate Similarity NPC46009
0.7438 Intermediate Similarity NPC469902
0.7436 Intermediate Similarity NPC300443
0.7413 Intermediate Similarity NPC22746
0.7407 Intermediate Similarity NPC63931
0.74 Intermediate Similarity NPC89489
0.7394 Intermediate Similarity NPC89831
0.7394 Intermediate Similarity NPC230611
0.7389 Intermediate Similarity NPC202198
0.7386 Intermediate Similarity NPC266741
0.7384 Intermediate Similarity NPC329731
0.7381 Intermediate Similarity NPC269750
0.7381 Intermediate Similarity NPC194671
0.7378 Intermediate Similarity NPC473000
0.7375 Intermediate Similarity NPC469898
0.7365 Intermediate Similarity NPC469900
0.7349 Intermediate Similarity NPC273755
0.7342 Intermediate Similarity NPC39431
0.733 Intermediate Similarity NPC59827
0.733 Intermediate Similarity NPC184933
0.7325 Intermediate Similarity NPC233702
0.7313 Intermediate Similarity NPC171734
0.7312 Intermediate Similarity NPC324850
0.7305 Intermediate Similarity NPC473354
0.7305 Intermediate Similarity NPC473402
0.7299 Intermediate Similarity NPC474584
0.7299 Intermediate Similarity NPC273814
0.729 Intermediate Similarity NPC311658
0.7284 Intermediate Similarity NPC73655
0.7278 Intermediate Similarity NPC261934
0.7278 Intermediate Similarity NPC5194
0.7273 Intermediate Similarity NPC471680
0.7273 Intermediate Similarity NPC186617
0.7262 Intermediate Similarity NPC50016
0.7261 Intermediate Similarity NPC473491
0.7256 Intermediate Similarity NPC254700
0.7229 Intermediate Similarity NPC473693
0.7229 Intermediate Similarity NPC471568
0.7212 Intermediate Similarity NPC302597
0.7209 Intermediate Similarity NPC471049
0.7209 Intermediate Similarity NPC294951
0.7209 Intermediate Similarity NPC471048

  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 NPC5620 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
0.8841 High Similarity NPD8172 Phase 2
0.8841 High Similarity NPD8173 Phase 2
0.8633 High Similarity NPD7113 Clinical (unspecified phase)
0.8507 High Similarity NPD2584 Suspended
0.8169 Intermediate Similarity NPD8416 Discontinued
0.8071 Intermediate Similarity NPD4177 Approved
0.8071 Intermediate Similarity NPD4175 Approved
0.7987 Intermediate Similarity NPD8323 Discontinued
0.7986 Intermediate Similarity NPD8643 Discontinued
0.7931 Intermediate Similarity NPD5725 Approved
0.7931 Intermediate Similarity NPD6073 Approved
0.7929 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD4125 Approved
0.7872 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD5747 Discontinued
0.7724 Intermediate Similarity NPD7634 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD3071 Approved
0.7714 Intermediate Similarity NPD3073 Approved
0.7714 Intermediate Similarity NPD3072 Approved
0.7643 Intermediate Similarity NPD4761 Approved
0.7643 Intermediate Similarity NPD4762 Approved
0.7635 Intermediate Similarity NPD6852 Discontinued
0.7622 Intermediate Similarity NPD3608 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD8417 Discontinued
0.7568 Intermediate Similarity NPD4782 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD4153 Approved
0.7548 Intermediate Similarity NPD7613 Discontinued
0.7517 Intermediate Similarity NPD5263 Approved
0.7517 Intermediate Similarity NPD4676 Approved
0.7483 Intermediate Similarity NPD8076 Discontinued
0.7467 Intermediate Similarity NPD7728 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD4794 Discontinued
0.7455 Intermediate Similarity NPD8124 Phase 3
0.7455 Intermediate Similarity NPD8126 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD8265 Approved
0.7432 Intermediate Similarity NPD6623 Phase 3
0.7432 Intermediate Similarity NPD4791 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6631 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD7512 Approved
0.7417 Intermediate Similarity NPD7511 Approved
0.74 Intermediate Similarity NPD6901 Phase 3
0.7394 Intermediate Similarity NPD4706 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD5264 Approved
0.7386 Intermediate Similarity NPD5265 Approved
0.7358 Intermediate Similarity NPD7267 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD5759 Approved
0.7329 Intermediate Similarity NPD7599 Phase 2
0.732 Intermediate Similarity NPD2436 Approved
0.732 Intermediate Similarity NPD2437 Approved
0.7315 Intermediate Similarity NPD5296 Approved
0.7308 Intermediate Similarity NPD6088 Approved
0.7284 Intermediate Similarity NPD7600 Phase 2
0.7279 Intermediate Similarity NPD7979 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD8303 Discontinued
0.7246 Intermediate Similarity NPD7964 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7965 Phase 2
0.7233 Intermediate Similarity NPD8315 Phase 1
0.723 Intermediate Similarity NPD4738 Phase 2
0.7222 Intermediate Similarity NPD4557 Approved
0.7219 Intermediate Similarity NPD7510 Approved
0.7211 Intermediate Similarity NPD3040 Approved
0.7211 Intermediate Similarity NPD3626 Phase 3
0.7208 Intermediate Similarity NPD5341 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD7749 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD7892 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD1329 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD4621 Approved
0.7181 Intermediate Similarity NPD4619 Approved
0.7181 Intermediate Similarity NPD1330 Phase 2
0.7181 Intermediate Similarity NPD3632 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD4677 Discontinued
0.7171 Intermediate Similarity NPD6294 Approved
0.7171 Intermediate Similarity NPD6295 Approved
0.7162 Intermediate Similarity NPD2613 Approved
0.7153 Intermediate Similarity NPD3131 Approved
0.7153 Intermediate Similarity NPD4215 Approved
0.7153 Intermediate Similarity NPD4218 Approved
0.7153 Intermediate Similarity NPD4217 Approved
0.7153 Intermediate Similarity NPD4216 Approved
0.7153 Intermediate Similarity NPD2612 Approved
0.7153 Intermediate Similarity NPD2609 Approved
0.7153 Intermediate Similarity NPD2608 Approved
0.7153 Intermediate Similarity NPD3132 Approved
0.7153 Intermediate Similarity NPD2610 Approved
0.7153 Intermediate Similarity NPD2611 Approved
0.7143 Intermediate Similarity NPD2022 Approved
0.7143 Intermediate Similarity NPD4152 Approved
0.7143 Intermediate Similarity NPD3604 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD3616 Approved
0.7133 Intermediate Similarity NPD3089 Approved
0.7133 Intermediate Similarity NPD2572 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD3090 Approved
0.7133 Intermediate Similarity NPD2571 Approved
0.7133 Intermediate Similarity NPD3088 Approved
0.7133 Intermediate Similarity NPD4745 Approved
0.7133 Intermediate Similarity NPD2574 Discontinued
0.7133 Intermediate Similarity NPD2573 Approved
0.7133 Intermediate Similarity NPD3615 Approved
0.7133 Intermediate Similarity NPD2570 Approved
0.7133 Intermediate Similarity NPD2566 Approved
0.7133 Intermediate Similarity NPD3614 Approved
0.7133 Intermediate Similarity NPD4746 Phase 3
0.7133 Intermediate Similarity NPD3087 Approved
0.7125 Intermediate Similarity NPD4646 Approved
0.7125 Intermediate Similarity NPD4647 Approved
0.7125 Intermediate Similarity NPD4648 Approved
0.7124 Intermediate Similarity NPD3480 Approved
0.7115 Intermediate Similarity NPD5298 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD2050 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD2045 Approved
0.7114 Intermediate Similarity NPD2046 Approved
0.7114 Intermediate Similarity NPD2043 Approved
0.7114 Intermediate Similarity NPD2044 Approved
0.7114 Intermediate Similarity NPD2047 Approved
0.7114 Intermediate Similarity NPD2048 Approved
0.7114 Intermediate Similarity NPD21 Approved
0.7114 Intermediate Similarity NPD2051 Approved
0.7114 Intermediate Similarity NPD2049 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD6343 Approved
0.7113 Intermediate Similarity NPD6345 Approved
0.7107 Intermediate Similarity NPD5230 Approved
0.7107 Intermediate Similarity NPD5229 Approved
0.7097 Intermediate Similarity NPD6681 Discovery
0.7086 Intermediate Similarity NPD5323 Approved
0.7067 Intermediate Similarity NPD2078 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD4504 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4126 Approved
0.7039 Intermediate Similarity NPD4685 Phase 3
0.7039 Intermediate Similarity NPD4686 Approved
0.7039 Intermediate Similarity NPD4684 Phase 3
0.7032 Intermediate Similarity NPD2088 Approved
0.7032 Intermediate Similarity NPD2087 Approved
0.7032 Intermediate Similarity NPD7720 Phase 2
0.703 Intermediate Similarity NPD8351 Phase 2
0.7029 Intermediate Similarity NPD3642 Approved
0.7029 Intermediate Similarity NPD3643 Approved
0.7029 Intermediate Similarity NPD3644 Approved
0.7027 Intermediate Similarity NPD3588 Discontinued
0.7021 Intermediate Similarity NPD1348 Approved
0.702 Intermediate Similarity NPD3561 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD3125 Approved
0.7007 Intermediate Similarity NPD6792 Phase 3
0.6993 Remote Similarity NPD2217 Approved
0.6993 Remote Similarity NPD2218 Phase 2
0.6989 Remote Similarity NPD8103 Clinical (unspecified phase)
0.698 Remote Similarity NPD3661 Approved
0.698 Remote Similarity NPD3663 Approved
0.698 Remote Similarity NPD3662 Phase 3
0.698 Remote Similarity NPD3664 Approved
0.6962 Remote Similarity NPD6552 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5299 Approved
0.6944 Remote Similarity NPD5981 Approved
0.6923 Remote Similarity NPD5991 Approved
0.6923 Remote Similarity NPD5990 Approved
0.6913 Remote Similarity NPD4151 Approved
0.6903 Remote Similarity NPD5301 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7342 Discontinued
0.6892 Remote Similarity NPD5367 Discontinued
0.6879 Remote Similarity NPD2652 Approved
0.6879 Remote Similarity NPD3598 Phase 3
0.6879 Remote Similarity NPD2650 Approved
0.6875 Remote Similarity NPD5613 Approved
0.6875 Remote Similarity NPD5614 Approved
0.6875 Remote Similarity NPD3987 Approved
0.6875 Remote Similarity NPD3988 Approved
0.6867 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6867 Remote Similarity NPD5204 Approved
0.6846 Remote Similarity NPD2626 Approved
0.6846 Remote Similarity NPD2159 Approved
0.6846 Remote Similarity NPD2625 Approved
0.6846 Remote Similarity NPD2627 Approved
0.6846 Remote Similarity NPD2628 Approved
0.6846 Remote Similarity NPD2160 Approved
0.6842 Remote Similarity NPD5581 Approved
0.6831 Remote Similarity NPD747 Discontinued
0.6818 Remote Similarity NPD3908 Approved
0.6813 Remote Similarity NPD8290 Clinical (unspecified phase)
0.6806 Remote Similarity NPD7522 Discontinued
0.6803 Remote Similarity NPD5338 Clinical (unspecified phase)
0.6792 Remote Similarity NPD2575 Approved
0.6792 Remote Similarity NPD6676 Phase 2
0.679 Remote Similarity NPD6078 Clinical (unspecified phase)
0.679 Remote Similarity NPD5638 Approved
0.6788 Remote Similarity NPD7105 Phase 1
0.6779 Remote Similarity NPD2031 Discontinued
0.6772 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7485 Phase 3
0.6765 Remote Similarity NPD7484 Phase 3
0.6763 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6757 Remote Similarity NPD7814 Approved
0.6752 Remote Similarity NPD6897 Clinical (unspecified phase)
0.675 Remote Similarity NPD7602 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7131 Phase 3
0.6747 Remote Similarity NPD7011 Discontinued
0.6739 Remote Similarity NPD7130 Phase 3
0.6736 Remote Similarity NPD4576 Approved
0.6736 Remote Similarity NPD5291 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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