Structure

Physi-Chem Properties

Molecular Weight:  736.44
Volume:  777.33
LogP:  4.552
LogD:  3.044
LogS:  -4.92
# Rotatable Bonds:  9
TPSA:  142.63
# H-Bond Aceptor:  12
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.228
Synthetic Accessibility Score:  5.535
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:  -4.965
MDCK Permeability:  1.954703839146532e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.066
20% Bioavailability (F20%):  0.929
30% Bioavailability (F30%):  0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  95.40187072753906%
Volume Distribution (VD):  1.038
Pgp-substrate:  0.982718288898468%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.06
CYP2C19-inhibitor:  0.228
CYP2C19-substrate:  0.798
CYP2C9-inhibitor:  0.233
CYP2C9-substrate:  0.069
CYP2D6-inhibitor:  0.17
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.955
CYP3A4-substrate:  0.917

ADMET: Excretion

Clearance (CL):  6.066
Half-life (T1/2):  0.109

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.993
Drug-inuced Liver Injury (DILI):  0.969
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.648
Maximum Recommended Daily Dose:  0.628
Skin Sensitization:  0.042
Carcinogencity:  0.049
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.025

Download Data

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

  Natural Product: NPC329761

Natural Product ID:  NPC329761
Common Name*:   Hantupeptin A
IUPAC Name:   (3S,6S,9S,13S,16S,19S)-3-benzyl-6-[(2S)-butan-2-yl]-7,12,17-trimethyl-13-pent-4-ynyl-9,16-di(propan-2-yl)-4,14-dioxa-1,7,10,17-tetrazabicyclo[17.3.0]docosane-2,5,8,11,15,18-hexone
Synonyms:   Hantupeptin A
Standard InCHIKey:  QEERUAVEBIAUIV-QUIBGUPGSA-N
Standard InCHI:  InChI=1S/C41H60N4O8/c1-11-13-15-22-31-28(8)36(46)42-33(25(3)4)39(49)44(10)35(27(7)12-2)41(51)53-32(24-29-19-16-14-17-20-29)38(48)45-23-18-21-30(45)37(47)43(9)34(26(5)6)40(50)52-31/h1,14,16-17,19-20,25-28,30-35H,12-13,15,18,21-24H2,2-10H3,(H,42,46)/t27-,28?,30-,31-,32-,33-,34-,35-/m0/s1
SMILES:  C#CCCC[C@@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](OC(=O)[C@@H](N(C(=O)[C@@H](N=C(C1C)O)C(C)C)C)[C@H](CC)C)Cc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL554992
PubChem CID:   25210138
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
NPT112 Cell Line MOLT-4 Homo sapiens IC50 = 32.0 nM PMID[498580]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4000.0 nM PMID[498580]
NPT112 Cell Line MOLT-4 Homo sapiens IC50 = 32.0 nM PMID[498581]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4000.0 nM PMID[498581]
NPT140 Organism Artemia Artemia Activity = 100.0 % PMID[498580]

☑ 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 NPC329761 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 NPC225648
0.9429 High Similarity NPC129666
0.9275 High Similarity NPC139326
0.9203 High Similarity NPC263493
0.9203 High Similarity NPC269398
0.9149 High Similarity NPC145113
0.9149 High Similarity NPC138775
0.9143 High Similarity NPC5620
0.8897 High Similarity NPC162104
0.8865 High Similarity NPC161069
0.8786 High Similarity NPC98424
0.8786 High Similarity NPC470884
0.8786 High Similarity NPC178662
0.8786 High Similarity NPC476133
0.8786 High Similarity NPC92784
0.8741 High Similarity NPC209509
0.8714 High Similarity NPC471265
0.8714 High Similarity NPC471264
0.869 High Similarity NPC240848
0.8671 High Similarity NPC476978
0.86 High Similarity NPC197743
0.86 High Similarity NPC297145
0.8582 High Similarity NPC68865
0.8562 High Similarity NPC471820
0.8562 High Similarity NPC471821
0.8503 High Similarity NPC2501
0.8462 Intermediate Similarity NPC268841
0.8462 Intermediate Similarity NPC46098
0.8462 Intermediate Similarity NPC307357
0.8451 Intermediate Similarity NPC127741
0.8333 Intermediate Similarity NPC239762
0.8333 Intermediate Similarity NPC122590
0.8333 Intermediate Similarity NPC163392
0.8288 Intermediate Similarity NPC52748
0.8261 Intermediate Similarity NPC101719
0.8243 Intermediate Similarity NPC135121
0.8188 Intermediate Similarity NPC222466
0.8188 Intermediate Similarity NPC105717
0.8182 Intermediate Similarity NPC248283
0.8176 Intermediate Similarity NPC262077
0.8108 Intermediate Similarity NPC201244
0.8108 Intermediate Similarity NPC313867
0.8108 Intermediate Similarity NPC316008
0.8108 Intermediate Similarity NPC477217
0.8101 Intermediate Similarity NPC473502
0.8099 Intermediate Similarity NPC130309
0.8075 Intermediate Similarity NPC318930
0.8075 Intermediate Similarity NPC317362
0.8054 Intermediate Similarity NPC314358
0.8041 Intermediate Similarity NPC315283
0.8041 Intermediate Similarity NPC314388
0.8015 Intermediate Similarity NPC310467
0.7986 Intermediate Similarity NPC46427
0.7986 Intermediate Similarity NPC6975
0.7974 Intermediate Similarity NPC286551
0.7973 Intermediate Similarity NPC197682
0.7963 Intermediate Similarity NPC326407
0.7963 Intermediate Similarity NPC317725
0.7958 Intermediate Similarity NPC473322
0.7941 Intermediate Similarity NPC169328
0.7927 Intermediate Similarity NPC475421
0.7917 Intermediate Similarity NPC246079
0.7914 Intermediate Similarity NPC252878
0.7905 Intermediate Similarity NPC168113
0.7905 Intermediate Similarity NPC469426
0.7905 Intermediate Similarity NPC469427
0.7899 Intermediate Similarity NPC200964
0.7887 Intermediate Similarity NPC239990
0.7887 Intermediate Similarity NPC71933
0.7887 Intermediate Similarity NPC89923
0.7887 Intermediate Similarity NPC319766
0.7887 Intermediate Similarity NPC105114
0.7887 Intermediate Similarity NPC152850
0.7862 Intermediate Similarity NPC472923
0.7853 Intermediate Similarity NPC26108
0.7852 Intermediate Similarity NPC176226
0.7843 Intermediate Similarity NPC7817
0.7843 Intermediate Similarity NPC475168
0.7842 Intermediate Similarity NPC202521
0.7817 Intermediate Similarity NPC136453
0.7791 Intermediate Similarity NPC137627
0.7784 Intermediate Similarity NPC167763
0.7784 Intermediate Similarity NPC470903
0.7784 Intermediate Similarity NPC470112
0.777 Intermediate Similarity NPC476990
0.7748 Intermediate Similarity NPC315266
0.7742 Intermediate Similarity NPC473341
0.774 Intermediate Similarity NPC287401
0.7724 Intermediate Similarity NPC157311
0.7724 Intermediate Similarity NPC255447
0.7718 Intermediate Similarity NPC476259
0.7692 Intermediate Similarity NPC299806
0.7692 Intermediate Similarity NPC470902
0.7676 Intermediate Similarity NPC22746
0.7671 Intermediate Similarity NPC8761
0.7671 Intermediate Similarity NPC44805
0.7669 Intermediate Similarity NPC196091
0.7669 Intermediate Similarity NPC475204
0.7669 Intermediate Similarity NPC475123
0.764 Intermediate Similarity NPC63931
0.7626 Intermediate Similarity NPC470546
0.7578 Intermediate Similarity NPC471051
0.7578 Intermediate Similarity NPC471052
0.7578 Intermediate Similarity NPC471053
0.7554 Intermediate Similarity NPC470545
0.7548 Intermediate Similarity NPC283783
0.7533 Intermediate Similarity NPC132636
0.753 Intermediate Similarity NPC477462
0.7518 Intermediate Similarity NPC478015
0.7518 Intermediate Similarity NPC478014
0.7518 Intermediate Similarity NPC478016
0.7518 Intermediate Similarity NPC190663
0.7516 Intermediate Similarity NPC262166
0.7516 Intermediate Similarity NPC322878
0.75 Intermediate Similarity NPC237420
0.75 Intermediate Similarity NPC62104
0.75 Intermediate Similarity NPC47667
0.75 Intermediate Similarity NPC1390
0.7482 Intermediate Similarity NPC470544
0.7482 Intermediate Similarity NPC239357
0.747 Intermediate Similarity NPC306804
0.7468 Intermediate Similarity NPC81026
0.7453 Intermediate Similarity NPC471527
0.7452 Intermediate Similarity NPC233702
0.7439 Intermediate Similarity NPC107938
0.7439 Intermediate Similarity NPC294516
0.7425 Intermediate Similarity NPC155506
0.7425 Intermediate Similarity NPC476227
0.7425 Intermediate Similarity NPC159767
0.7425 Intermediate Similarity NPC279871
0.7415 Intermediate Similarity NPC200589
0.7415 Intermediate Similarity NPC300315
0.7413 Intermediate Similarity NPC160493
0.7403 Intermediate Similarity NPC266741
0.7394 Intermediate Similarity NPC45777
0.7394 Intermediate Similarity NPC477061
0.7391 Intermediate Similarity NPC287757
0.7391 Intermediate Similarity NPC319320
0.7361 Intermediate Similarity NPC175726
0.7361 Intermediate Similarity NPC474082
0.7358 Intermediate Similarity NPC39431
0.7351 Intermediate Similarity NPC43755
0.7349 Intermediate Similarity NPC46009
0.7349 Intermediate Similarity NPC40234
0.7346 Intermediate Similarity NPC469901
0.7342 Intermediate Similarity NPC300443
0.7333 Intermediate Similarity NPC171734
0.7321 Intermediate Similarity NPC471165
0.7317 Intermediate Similarity NPC22883
0.7317 Intermediate Similarity NPC5719
0.7317 Intermediate Similarity NPC217804
0.7317 Intermediate Similarity NPC210377
0.7308 Intermediate Similarity NPC16188
0.7305 Intermediate Similarity NPC230611
0.7297 Intermediate Similarity NPC69496
0.7294 Intermediate Similarity NPC194671
0.7294 Intermediate Similarity NPC269750
0.7292 Intermediate Similarity NPC169485
0.7292 Intermediate Similarity NPC291027
0.7292 Intermediate Similarity NPC84281
0.7292 Intermediate Similarity NPC317474
0.7292 Intermediate Similarity NPC213126
0.7273 Intermediate Similarity NPC15068
0.7273 Intermediate Similarity NPC80150
0.7267 Intermediate Similarity NPC233910
0.7267 Intermediate Similarity NPC245836
0.7266 Intermediate Similarity NPC35850
0.7266 Intermediate Similarity NPC276949
0.7262 Intermediate Similarity NPC273755
0.7234 Intermediate Similarity NPC14672
0.7234 Intermediate Similarity NPC315276
0.7234 Intermediate Similarity NPC285926
0.723 Intermediate Similarity NPC469666
0.723 Intermediate Similarity NPC111428
0.7229 Intermediate Similarity NPC63040
0.7222 Intermediate Similarity NPC71684
0.7219 Intermediate Similarity NPC473354
0.7219 Intermediate Similarity NPC473402
0.7214 Intermediate Similarity NPC33742
0.7205 Intermediate Similarity NPC469903
0.7205 Intermediate Similarity NPC473580
0.7202 Intermediate Similarity NPC89831
0.72 Intermediate Similarity NPC4910
0.7197 Intermediate Similarity NPC311658
0.7194 Intermediate Similarity NPC273814
0.7188 Intermediate Similarity NPC202198
0.7188 Intermediate Similarity NPC261934
0.7188 Intermediate Similarity NPC5194
0.7178 Intermediate Similarity NPC24617
0.7176 Intermediate Similarity NPC50016
0.7161 Intermediate Similarity NPC77905
0.716 Intermediate Similarity NPC248670
0.7143 Intermediate Similarity NPC474847
0.7134 Intermediate Similarity NPC469902
0.7134 Intermediate Similarity NPC114806
0.7126 Intermediate Similarity NPC294951
0.7126 Intermediate Similarity NPC471050
0.7126 Intermediate Similarity NPC302597
0.7126 Intermediate Similarity NPC471049
0.7126 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 NPC329761 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
0.8322 Intermediate Similarity NPD8172 Phase 2
0.8322 Intermediate Similarity NPD8173 Phase 2
0.8125 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD2584 Suspended
0.7832 Intermediate Similarity NPD4177 Approved
0.7832 Intermediate Similarity NPD4175 Approved
0.7808 Intermediate Similarity NPD8416 Discontinued
0.7703 Intermediate Similarity NPD6073 Approved
0.7703 Intermediate Similarity NPD5725 Approved
0.7692 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD8323 Discontinued
0.7635 Intermediate Similarity NPD8643 Discontinued
0.7619 Intermediate Similarity NPD5747 Discontinued
0.7595 Intermediate Similarity NPD8417 Discontinued
0.7517 Intermediate Similarity NPD3608 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7634 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3072 Approved
0.7483 Intermediate Similarity NPD3073 Approved
0.7483 Intermediate Similarity NPD3071 Approved
0.7451 Intermediate Similarity NPD2437 Approved
0.7451 Intermediate Similarity NPD2436 Approved
0.745 Intermediate Similarity NPD4153 Approved
0.7417 Intermediate Similarity NPD6852 Discontinued
0.7415 Intermediate Similarity NPD4125 Approved
0.7413 Intermediate Similarity NPD4762 Approved
0.7413 Intermediate Similarity NPD4761 Approved
0.7413 Intermediate Similarity NPD4706 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD7613 Discontinued
0.7329 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4676 Approved
0.7297 Intermediate Similarity NPD2613 Approved
0.7297 Intermediate Similarity NPD5263 Approved
0.7292 Intermediate Similarity NPD2609 Approved
0.7292 Intermediate Similarity NPD3132 Approved
0.7292 Intermediate Similarity NPD4218 Approved
0.7292 Intermediate Similarity NPD2610 Approved
0.7292 Intermediate Similarity NPD4215 Approved
0.7292 Intermediate Similarity NPD4216 Approved
0.7292 Intermediate Similarity NPD2612 Approved
0.7292 Intermediate Similarity NPD2611 Approved
0.7292 Intermediate Similarity NPD3131 Approved
0.7292 Intermediate Similarity NPD2608 Approved
0.7292 Intermediate Similarity NPD4217 Approved
0.7267 Intermediate Similarity NPD4746 Phase 3
0.7267 Intermediate Similarity NPD3614 Approved
0.7267 Intermediate Similarity NPD3616 Approved
0.7267 Intermediate Similarity NPD4745 Approved
0.7267 Intermediate Similarity NPD2572 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD3089 Approved
0.7267 Intermediate Similarity NPD2566 Approved
0.7267 Intermediate Similarity NPD3087 Approved
0.7267 Intermediate Similarity NPD3090 Approved
0.7267 Intermediate Similarity NPD3088 Approved
0.7267 Intermediate Similarity NPD2573 Approved
0.7267 Intermediate Similarity NPD3615 Approved
0.7267 Intermediate Similarity NPD2571 Approved
0.7267 Intermediate Similarity NPD2570 Approved
0.7267 Intermediate Similarity NPD2574 Discontinued
0.7255 Intermediate Similarity NPD3480 Approved
0.725 Intermediate Similarity NPD8315 Phase 1
0.7248 Intermediate Similarity NPD2050 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2046 Approved
0.7248 Intermediate Similarity NPD2047 Approved
0.7248 Intermediate Similarity NPD2044 Approved
0.7248 Intermediate Similarity NPD2049 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2045 Approved
0.7248 Intermediate Similarity NPD4794 Discontinued
0.7248 Intermediate Similarity NPD21 Approved
0.7248 Intermediate Similarity NPD2048 Approved
0.7248 Intermediate Similarity NPD2051 Approved
0.7248 Intermediate Similarity NPD2043 Approved
0.7248 Intermediate Similarity NPD4738 Phase 2
0.7239 Intermediate Similarity NPD4557 Approved
0.7237 Intermediate Similarity NPD4782 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6681 Discovery
0.7219 Intermediate Similarity NPD8265 Approved
0.7219 Intermediate Similarity NPD6623 Phase 3
0.7219 Intermediate Similarity NPD5323 Approved
0.7208 Intermediate Similarity NPD7511 Approved
0.7208 Intermediate Similarity NPD7512 Approved
0.72 Intermediate Similarity NPD1329 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1330 Phase 2
0.7181 Intermediate Similarity NPD7979 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD5264 Approved
0.7179 Intermediate Similarity NPD5265 Approved
0.7171 Intermediate Similarity NPD4685 Phase 3
0.7171 Intermediate Similarity NPD4684 Phase 3
0.7171 Intermediate Similarity NPD4686 Approved
0.7161 Intermediate Similarity NPD8076 Discontinued
0.7161 Intermediate Similarity NPD2022 Approved
0.7143 Intermediate Similarity NPD4646 Approved
0.7143 Intermediate Similarity NPD4648 Approved
0.7143 Intermediate Similarity NPD4647 Approved
0.7133 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD3664 Approved
0.7114 Intermediate Similarity NPD3040 Approved
0.7114 Intermediate Similarity NPD3661 Approved
0.7114 Intermediate Similarity NPD3663 Approved
0.7114 Intermediate Similarity NPD3662 Phase 3
0.7114 Intermediate Similarity NPD5759 Approved
0.7107 Intermediate Similarity NPD6088 Approved
0.7105 Intermediate Similarity NPD5296 Approved
0.7086 Intermediate Similarity NPD4621 Approved
0.7086 Intermediate Similarity NPD5299 Approved
0.7086 Intermediate Similarity NPD4619 Approved
0.7075 Intermediate Similarity NPD4677 Discontinued
0.7051 Intermediate Similarity NPD2088 Approved
0.7051 Intermediate Similarity NPD2087 Approved
0.7048 Intermediate Similarity NPD8351 Phase 2
0.7032 Intermediate Similarity NPD7728 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD3125 Approved
0.7021 Intermediate Similarity NPD2650 Approved
0.7021 Intermediate Similarity NPD2652 Approved
0.7019 Intermediate Similarity NPD5229 Approved
0.7019 Intermediate Similarity NPD5230 Approved
0.7013 Intermediate Similarity NPD7510 Approved
0.7012 Intermediate Similarity NPD7749 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3626 Phase 3
0.7 Intermediate Similarity NPD5204 Approved
0.7 Intermediate Similarity NPD7892 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6631 Clinical (unspecified phase)
0.6993 Remote Similarity NPD4791 Clinical (unspecified phase)
0.698 Remote Similarity NPD2626 Approved
0.698 Remote Similarity NPD2627 Approved
0.698 Remote Similarity NPD2625 Approved
0.698 Remote Similarity NPD2159 Approved
0.698 Remote Similarity NPD2628 Approved
0.698 Remote Similarity NPD2160 Approved
0.6968 Remote Similarity NPD6294 Approved
0.6968 Remote Similarity NPD6901 Phase 3
0.6968 Remote Similarity NPD6295 Approved
0.6964 Remote Similarity NPD8303 Discontinued
0.6951 Remote Similarity NPD7267 Clinical (unspecified phase)
0.6943 Remote Similarity NPD4152 Approved
0.6933 Remote Similarity NPD3588 Discontinued
0.6933 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6928 Remote Similarity NPD3561 Clinical (unspecified phase)
0.6928 Remote Similarity NPD7599 Phase 2
0.6918 Remote Similarity NPD2575 Approved
0.6918 Remote Similarity NPD6676 Phase 2
0.6918 Remote Similarity NPD5298 Clinical (unspecified phase)
0.691 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6894 Remote Similarity NPD5613 Approved
0.6894 Remote Similarity NPD3988 Approved
0.6894 Remote Similarity NPD3987 Approved
0.6894 Remote Similarity NPD5614 Approved
0.6886 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7600 Phase 2
0.6879 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5291 Approved
0.6875 Remote Similarity NPD5292 Approved
0.6875 Remote Similarity NPD4574 Approved
0.6875 Remote Similarity NPD4576 Approved
0.6863 Remote Similarity NPD3632 Clinical (unspecified phase)
0.686 Remote Similarity NPD7965 Phase 2
0.686 Remote Similarity NPD8126 Clinical (unspecified phase)
0.686 Remote Similarity NPD7964 Clinical (unspecified phase)
0.686 Remote Similarity NPD8124 Phase 3
0.6859 Remote Similarity NPD4126 Approved
0.6849 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6835 Remote Similarity NPD7720 Phase 2
0.6824 Remote Similarity NPD4807 Approved
0.6824 Remote Similarity NPD4806 Approved
0.6824 Remote Similarity NPD5338 Clinical (unspecified phase)
0.6809 Remote Similarity NPD3643 Approved
0.6809 Remote Similarity NPD3644 Approved
0.6809 Remote Similarity NPD3642 Approved
0.6807 Remote Similarity NPD7105 Phase 1
0.6806 Remote Similarity NPD1348 Approved
0.68 Remote Similarity NPD6792 Phase 3
0.6792 Remote Similarity NPD5341 Clinical (unspecified phase)
0.6783 Remote Similarity NPD3598 Phase 3
0.6781 Remote Similarity NPD2218 Phase 2
0.6781 Remote Similarity NPD2217 Approved
0.677 Remote Similarity NPD6552 Clinical (unspecified phase)
0.677 Remote Similarity NPD7602 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7131 Phase 3
0.6759 Remote Similarity NPD3123 Discovery
0.6753 Remote Similarity NPD2078 Clinical (unspecified phase)
0.6736 Remote Similarity NPD747 Discontinued
0.6735 Remote Similarity NPD5981 Approved
0.6732 Remote Similarity NPD5203 Approved
0.6732 Remote Similarity NPD4620 Approved
0.6732 Remote Similarity NPD5201 Approved
0.6732 Remote Similarity NPD4617 Approved
0.6711 Remote Similarity NPD4151 Approved
0.6709 Remote Similarity NPD5301 Clinical (unspecified phase)
0.6708 Remote Similarity NPD1967 Approved
0.6708 Remote Similarity NPD1968 Approved
0.6689 Remote Similarity NPD5305 Approved
0.6689 Remote Similarity NPD5367 Discontinued
0.6689 Remote Similarity NPD5306 Approved
0.6688 Remote Similarity NPD4497 Clinical (unspecified phase)
0.6686 Remote Similarity NPD7485 Phase 3
0.6686 Remote Similarity NPD6304 Approved
0.6686 Remote Similarity NPD8022 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