Structure

Physi-Chem Properties

Molecular Weight:  768.34
Volume:  754.459
LogP:  2.18
LogD:  1.631
LogS:  -2.792
# Rotatable Bonds:  8
TPSA:  165.74
# H-Bond Aceptor:  14
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.314
Synthetic Accessibility Score:  5.625
Fsp3:  0.639
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.435
MDCK Permeability:  6.717675569234416e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.405
Human Intestinal Absorption (HIA):  0.664
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.147
Plasma Protein Binding (PPB):  80.89838409423828%
Volume Distribution (VD):  0.724
Pgp-substrate:  12.832818984985352%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.026
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.685
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.015
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.082
CYP3A4-inhibitor:  0.794
CYP3A4-substrate:  0.914

ADMET: Excretion

Clearance (CL):  6.053
Half-life (T1/2):  0.452

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.975
Drug-inuced Liver Injury (DILI):  0.96
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.006
Maximum Recommended Daily Dose:  0.058
Skin Sensitization:  0.034
Carcinogencity:  0.003
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.082

Download Data

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

  Natural Product: NPC469426

Natural Product ID:  NPC469426
Common Name*:   Itralamide A
IUPAC Name:   N-[(3S,6R,9S,12R,15S,18S,19R)-6-benzyl-3,7,9,10,12,16,19-heptamethyl-2,5,8,11,14,17-hexaoxo-15-propan-2-yl-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]-4,4-dichloro-N,3-dimethylbutanamide
Synonyms:  
Standard InCHIKey:  KCTXBLDAYCJREC-AQWYKPIYSA-N
Standard InCHI:  InChI=1S/C36H54Cl2N6O8/c1-19(2)28-32(47)39-21(4)33(48)41(8)23(6)34(49)42(9)26(18-25-15-13-12-14-16-25)31(46)40-22(5)36(51)52-24(7)29(35(50)44(28)11)43(10)27(45)17-20(3)30(37)38/h12-16,19-24,26,28-30H,17-18H2,1-11H3,(H,39,47)(H,40,46)/t20?,21-,22+,23+,24-,26-,28+,29+/m1/s1
SMILES:  ClC(C(CC(=O)N([C@H]1[C@@H](C)OC(=O)[C@H](C)N=C(O)[C@@H](Cc2ccccc2)N(C)C(=O)[C@@H](N(C(=O)[C@H](N=C([C@@H](N(C1=O)C)C(C)C)O)C)C)C)C)C)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1078517
PubChem CID:   44479219
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
NPT71 Cell Line HEK293 Homo sapiens IC50 = 54000.0 nM PMID[448632]

☑ 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 NPC469426 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 NPC469427
0.8582 High Similarity NPC319766
0.8511 High Similarity NPC176226
0.838 Intermediate Similarity NPC139326
0.8369 Intermediate Similarity NPC476259
0.8369 Intermediate Similarity NPC239762
0.8369 Intermediate Similarity NPC163392
0.8357 Intermediate Similarity NPC471265
0.8357 Intermediate Similarity NPC471264
0.8357 Intermediate Similarity NPC127741
0.8357 Intermediate Similarity NPC68865
0.831 Intermediate Similarity NPC168113
0.831 Intermediate Similarity NPC269398
0.831 Intermediate Similarity NPC263493
0.8264 Intermediate Similarity NPC316008
0.8264 Intermediate Similarity NPC313867
0.8252 Intermediate Similarity NPC197682
0.8239 Intermediate Similarity NPC307357
0.8239 Intermediate Similarity NPC46098
0.8239 Intermediate Similarity NPC268841
0.8207 Intermediate Similarity NPC314358
0.8194 Intermediate Similarity NPC315283
0.8194 Intermediate Similarity NPC314388
0.8169 Intermediate Similarity NPC178662
0.8169 Intermediate Similarity NPC476133
0.8169 Intermediate Similarity NPC92784
0.8169 Intermediate Similarity NPC470884
0.8169 Intermediate Similarity NPC98424
0.8143 Intermediate Similarity NPC287401
0.8138 Intermediate Similarity NPC209509
0.8138 Intermediate Similarity NPC5620
0.8125 Intermediate Similarity NPC161069
0.8071 Intermediate Similarity NPC246079
0.8069 Intermediate Similarity NPC476978
0.8027 Intermediate Similarity NPC145113
0.7973 Intermediate Similarity NPC105717
0.7933 Intermediate Similarity NPC162104
0.7926 Intermediate Similarity NPC45777
0.7926 Intermediate Similarity NPC477061
0.7919 Intermediate Similarity NPC129666
0.791 Intermediate Similarity NPC470546
0.7905 Intermediate Similarity NPC135121
0.7905 Intermediate Similarity NPC225648
0.7905 Intermediate Similarity NPC329761
0.7905 Intermediate Similarity NPC138775
0.7895 Intermediate Similarity NPC470544
0.7891 Intermediate Similarity NPC201244
0.7891 Intermediate Similarity NPC477217
0.7883 Intermediate Similarity NPC46427
0.7836 Intermediate Similarity NPC470545
0.7836 Intermediate Similarity NPC169328
0.7823 Intermediate Similarity NPC52748
0.781 Intermediate Similarity NPC252878
0.78 Intermediate Similarity NPC2501
0.7778 Intermediate Similarity NPC237420
0.7778 Intermediate Similarity NPC310467
0.7763 Intermediate Similarity NPC286551
0.7763 Intermediate Similarity NPC473341
0.7754 Intermediate Similarity NPC6975
0.7748 Intermediate Similarity NPC7817
0.7748 Intermediate Similarity NPC475168
0.7746 Intermediate Similarity NPC130309
0.7737 Intermediate Similarity NPC202521
0.7733 Intermediate Similarity NPC240848
0.7733 Intermediate Similarity NPC471820
0.7733 Intermediate Similarity NPC471821
0.7718 Intermediate Similarity NPC262077
0.7708 Intermediate Similarity NPC248283
0.7677 Intermediate Similarity NPC197743
0.7677 Intermediate Similarity NPC297145
0.7673 Intermediate Similarity NPC209463
0.7664 Intermediate Similarity NPC476990
0.7651 Intermediate Similarity NPC315266
0.7647 Intermediate Similarity NPC122590
0.7643 Intermediate Similarity NPC101719
0.763 Intermediate Similarity NPC239357
0.76 Intermediate Similarity NPC81026
0.7597 Intermediate Similarity NPC470902
0.7571 Intermediate Similarity NPC22746
0.7571 Intermediate Similarity NPC222466
0.7551 Intermediate Similarity NPC132636
0.7536 Intermediate Similarity NPC478014
0.7536 Intermediate Similarity NPC200964
0.7536 Intermediate Similarity NPC478015
0.7536 Intermediate Similarity NPC478016
0.7535 Intermediate Similarity NPC89923
0.7535 Intermediate Similarity NPC152850
0.7535 Intermediate Similarity NPC105114
0.7535 Intermediate Similarity NPC71933
0.7535 Intermediate Similarity NPC239990
0.7533 Intermediate Similarity NPC322878
0.7533 Intermediate Similarity NPC266741
0.7516 Intermediate Similarity NPC62104
0.7516 Intermediate Similarity NPC1390
0.7483 Intermediate Similarity NPC473322
0.7482 Intermediate Similarity NPC71684
0.7468 Intermediate Similarity NPC471527
0.7465 Intermediate Similarity NPC136453
0.7431 Intermediate Similarity NPC300315
0.7399 Intermediate Similarity NPC328763
0.7379 Intermediate Similarity NPC157311
0.7379 Intermediate Similarity NPC255447
0.7375 Intermediate Similarity NPC471052
0.7375 Intermediate Similarity NPC471051
0.7375 Intermediate Similarity NPC471053
0.7362 Intermediate Similarity NPC473693
0.7362 Intermediate Similarity NPC471568
0.7333 Intermediate Similarity NPC273814
0.7329 Intermediate Similarity NPC5719
0.7329 Intermediate Similarity NPC22883
0.7329 Intermediate Similarity NPC217804
0.7329 Intermediate Similarity NPC8761
0.7329 Intermediate Similarity NPC44805
0.7329 Intermediate Similarity NPC210377
0.7329 Intermediate Similarity NPC472923
0.7286 Intermediate Similarity NPC80150
0.7286 Intermediate Similarity NPC190663
0.7284 Intermediate Similarity NPC15068
0.7279 Intermediate Similarity NPC35850
0.7279 Intermediate Similarity NPC276949
0.7273 Intermediate Similarity NPC47667
0.7261 Intermediate Similarity NPC39431
0.7256 Intermediate Similarity NPC475204
0.7256 Intermediate Similarity NPC196091
0.7256 Intermediate Similarity NPC40234
0.7256 Intermediate Similarity NPC475123
0.7244 Intermediate Similarity NPC300443
0.7241 Intermediate Similarity NPC111428
0.7239 Intermediate Similarity NPC107938
0.7239 Intermediate Similarity NPC294516
0.7239 Intermediate Similarity NPC63040
0.7232 Intermediate Similarity NPC323662
0.7229 Intermediate Similarity NPC158277
0.7226 Intermediate Similarity NPC33742
0.7195 Intermediate Similarity NPC186617
0.7183 Intermediate Similarity NPC160493
0.7179 Intermediate Similarity NPC473491
0.7169 Intermediate Similarity NPC248670
0.7152 Intermediate Similarity NPC46009
0.7143 Intermediate Similarity NPC314992
0.7134 Intermediate Similarity NPC473502
0.7133 Intermediate Similarity NPC175726
0.7133 Intermediate Similarity NPC474082
0.7126 Intermediate Similarity NPC326407
0.7126 Intermediate Similarity NPC318930
0.7126 Intermediate Similarity NPC317725
0.7126 Intermediate Similarity NPC476227
0.7126 Intermediate Similarity NPC477462
0.7126 Intermediate Similarity NPC317362
0.7125 Intermediate Similarity NPC324850
0.7123 Intermediate Similarity NPC469666
0.7122 Intermediate Similarity NPC2265
0.7121 Intermediate Similarity NPC88267
0.7121 Intermediate Similarity NPC194390
0.7121 Intermediate Similarity NPC224610
0.7121 Intermediate Similarity NPC113326
0.7119 Intermediate Similarity NPC473371
0.7115 Intermediate Similarity NPC283783
0.7114 Intermediate Similarity NPC141050
0.7108 Intermediate Similarity NPC230611
0.7101 Intermediate Similarity NPC475421
0.7083 Intermediate Similarity NPC476260
0.7083 Intermediate Similarity NPC50016
0.7083 Intermediate Similarity NPC476241
0.708 Intermediate Similarity NPC474584
0.7075 Intermediate Similarity NPC200589
0.7066 Intermediate Similarity NPC137627
0.7066 Intermediate Similarity NPC273755
0.7066 Intermediate Similarity NPC306804
0.7059 Intermediate Similarity NPC77905
0.7037 Intermediate Similarity NPC469901
0.7034 Intermediate Similarity NPC476125
0.7034 Intermediate Similarity NPC476179
0.7024 Intermediate Similarity NPC471165
0.7024 Intermediate Similarity NPC473354
0.7024 Intermediate Similarity NPC473402
0.7024 Intermediate Similarity NPC159767
0.7024 Intermediate Similarity NPC155506
0.7024 Intermediate Similarity NPC26108
0.7024 Intermediate Similarity NPC279871
0.702 Intermediate Similarity NPC43755
0.7 Intermediate Similarity NPC244509
0.6994 Remote Similarity NPC73655
0.6988 Remote Similarity NPC473000
0.6981 Remote Similarity NPC262166
0.6977 Remote Similarity NPC167763
0.6977 Remote Similarity NPC470903
0.6977 Remote Similarity NPC470112
0.6975 Remote Similarity NPC469898
0.6975 Remote Similarity NPC24617
0.6933 Remote Similarity NPC114806
0.6929 Remote Similarity NPC197470
0.6923 Remote Similarity NPC475439
0.6923 Remote Similarity NPC476183
0.6923 Remote Similarity NPC473501
0.6909 Remote Similarity NPC63931
0.6908 Remote Similarity NPC6570
0.6901 Remote Similarity NPC194671
0.6901 Remote Similarity NPC45037
0.6901 Remote Similarity NPC269750

  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 NPC469426 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
0.8099 Intermediate Similarity NPD8173 Phase 2
0.8099 Intermediate Similarity NPD8172 Phase 2
0.7655 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD2584 Suspended
0.755 Intermediate Similarity NPD8323 Discontinued
0.7466 Intermediate Similarity NPD8416 Discontinued
0.74 Intermediate Similarity NPD8076 Discontinued
0.7379 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD8265 Approved
0.7343 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD3608 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4175 Approved
0.7241 Intermediate Similarity NPD4177 Approved
0.72 Intermediate Similarity NPD6852 Discontinued
0.7181 Intermediate Similarity NPD4757 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD8643 Discontinued
0.7143 Intermediate Similarity NPD1968 Approved
0.7143 Intermediate Similarity NPD1967 Approved
0.7143 Intermediate Similarity NPD2218 Phase 2
0.7143 Intermediate Similarity NPD2217 Approved
0.7133 Intermediate Similarity NPD5725 Approved
0.7133 Intermediate Similarity NPD6073 Approved
0.7124 Intermediate Similarity NPD6681 Discovery
0.7115 Intermediate Similarity NPD6088 Approved
0.7114 Intermediate Similarity NPD6623 Phase 3
0.7114 Intermediate Similarity NPD4153 Approved
0.7095 Intermediate Similarity NPD2078 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD6901 Phase 3
0.7075 Intermediate Similarity NPD4125 Approved
0.7055 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD8315 Phase 1
0.7034 Intermediate Similarity NPD5367 Discontinued
0.7007 Intermediate Similarity NPD3626 Phase 3
0.7006 Intermediate Similarity NPD7892 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5292 Approved
0.7 Intermediate Similarity NPD5291 Approved
0.6974 Remote Similarity NPD6295 Approved
0.6974 Remote Similarity NPD6294 Approved
0.6972 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4677 Discontinued
0.6959 Remote Similarity NPD7979 Clinical (unspecified phase)
0.6957 Remote Similarity NPD8417 Discontinued
0.6948 Remote Similarity NPD2022 Approved
0.6948 Remote Similarity NPD4152 Approved
0.6937 Remote Similarity NPD4646 Approved
0.6937 Remote Similarity NPD4648 Approved
0.6937 Remote Similarity NPD4647 Approved
0.6933 Remote Similarity NPD4557 Approved
0.6933 Remote Similarity NPD7634 Clinical (unspecified phase)
0.6933 Remote Similarity NPD5747 Discontinued
0.6933 Remote Similarity NPD3561 Clinical (unspecified phase)
0.6929 Remote Similarity NPD1348 Approved
0.6928 Remote Similarity NPD7728 Clinical (unspecified phase)
0.6928 Remote Similarity NPD3480 Approved
0.6918 Remote Similarity NPD4731 Phase 3
0.6914 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6913 Remote Similarity NPD2049 Clinical (unspecified phase)
0.6913 Remote Similarity NPD2045 Approved
0.6913 Remote Similarity NPD2047 Approved
0.6913 Remote Similarity NPD21 Approved
0.6913 Remote Similarity NPD2044 Approved
0.6913 Remote Similarity NPD2051 Approved
0.6913 Remote Similarity NPD2046 Approved
0.6913 Remote Similarity NPD2048 Approved
0.6913 Remote Similarity NPD2050 Clinical (unspecified phase)
0.6913 Remote Similarity NPD2043 Approved
0.6903 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6897 Remote Similarity NPD3073 Approved
0.6897 Remote Similarity NPD3071 Approved
0.6897 Remote Similarity NPD3072 Approved
0.6887 Remote Similarity NPD5296 Approved
0.6864 Remote Similarity NPD8124 Phase 3
0.6864 Remote Similarity NPD8126 Clinical (unspecified phase)
0.6859 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6839 Remote Similarity NPD2088 Approved
0.6839 Remote Similarity NPD2087 Approved
0.6828 Remote Similarity NPD4706 Clinical (unspecified phase)
0.6828 Remote Similarity NPD4761 Approved
0.6828 Remote Similarity NPD4762 Approved
0.6824 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6813 Remote Similarity NPD5230 Approved
0.6813 Remote Similarity NPD5229 Approved
0.681 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6806 Remote Similarity NPD7342 Discontinued
0.6803 Remote Similarity NPD3125 Approved
0.68 Remote Similarity NPD4738 Phase 2
0.6797 Remote Similarity NPD4782 Clinical (unspecified phase)
0.6795 Remote Similarity NPD2436 Approved
0.6795 Remote Similarity NPD2437 Approved
0.6779 Remote Similarity NPD3040 Approved
0.6776 Remote Similarity NPD5323 Approved
0.6765 Remote Similarity NPD7130 Phase 3
0.6747 Remote Similarity NPD8351 Phase 2
0.6733 Remote Similarity NPD2613 Approved
0.6733 Remote Similarity NPD5263 Approved
0.6733 Remote Similarity NPD4676 Approved
0.6731 Remote Similarity NPD7978 Discontinued
0.6731 Remote Similarity NPD7720 Phase 2
0.673 Remote Similarity NPD5308 Clinical (unspecified phase)
0.6727 Remote Similarity NPD7599 Phase 2
0.6712 Remote Similarity NPD4215 Approved
0.6712 Remote Similarity NPD2608 Approved
0.6712 Remote Similarity NPD2612 Approved
0.6712 Remote Similarity NPD4216 Approved
0.6712 Remote Similarity NPD4217 Approved
0.6712 Remote Similarity NPD3132 Approved
0.6712 Remote Similarity NPD4218 Approved
0.6712 Remote Similarity NPD2611 Approved
0.6712 Remote Similarity NPD3131 Approved
0.6712 Remote Similarity NPD2610 Approved
0.6712 Remote Similarity NPD2609 Approved
0.6711 Remote Similarity NPD3614 Approved
0.6711 Remote Similarity NPD3088 Approved
0.6711 Remote Similarity NPD3087 Approved
0.6711 Remote Similarity NPD2571 Approved
0.6711 Remote Similarity NPD2570 Approved
0.6711 Remote Similarity NPD2573 Approved
0.6711 Remote Similarity NPD3615 Approved
0.6711 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3089 Approved
0.6711 Remote Similarity NPD2574 Discontinued
0.6711 Remote Similarity NPD4745 Approved
0.6711 Remote Similarity NPD5729 Clinical (unspecified phase)
0.6711 Remote Similarity NPD4746 Phase 3
0.6711 Remote Similarity NPD2566 Approved
0.6711 Remote Similarity NPD3616 Approved
0.6711 Remote Similarity NPD3090 Approved
0.671 Remote Similarity NPD5301 Clinical (unspecified phase)
0.6709 Remote Similarity NPD5298 Clinical (unspecified phase)
0.6708 Remote Similarity NPD7613 Discontinued
0.6708 Remote Similarity NPD6078 Clinical (unspecified phase)
0.6691 Remote Similarity NPD3642 Approved
0.6691 Remote Similarity NPD3644 Approved
0.6691 Remote Similarity NPD3643 Approved
0.6689 Remote Similarity NPD2031 Discontinued
0.6687 Remote Similarity NPD3987 Approved
0.6687 Remote Similarity NPD5613 Approved
0.6687 Remote Similarity NPD7600 Phase 2
0.6687 Remote Similarity NPD3988 Approved
0.6687 Remote Similarity NPD5614 Approved
0.6687 Remote Similarity NPD6631 Clinical (unspecified phase)
0.6686 Remote Similarity NPD7485 Phase 3
0.6686 Remote Similarity NPD7484 Phase 3
0.6667 Remote Similarity NPD4791 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5309 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7814 Approved
0.6667 Remote Similarity NPD7965 Phase 2
0.6667 Remote Similarity NPD7964 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6552 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5982 Phase 2
0.6646 Remote Similarity NPD7267 Clinical (unspecified phase)
0.6646 Remote Similarity NPD2891 Approved
0.6646 Remote Similarity NPD5264 Approved
0.6646 Remote Similarity NPD5265 Approved
0.6645 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6645 Remote Similarity NPD5299 Approved
0.6645 Remote Similarity NPD1330 Phase 2
0.6645 Remote Similarity NPD5581 Approved
0.6626 Remote Similarity NPD6670 Clinical (unspecified phase)
0.6623 Remote Similarity NPD4684 Phase 3
0.6623 Remote Similarity NPD3577 Discontinued
0.6623 Remote Similarity NPD4686 Approved
0.6623 Remote Similarity NPD6359 Clinical (unspecified phase)
0.6623 Remote Similarity NPD4685 Phase 3
0.6621 Remote Similarity NPD4209 Clinical (unspecified phase)
0.6621 Remote Similarity NPD5981 Approved
0.6604 Remote Similarity NPD6676 Phase 2
0.66 Remote Similarity NPD3588 Discontinued
0.6597 Remote Similarity NPD7522 Discontinued
0.6587 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6579 Remote Similarity NPD4794 Discontinued
0.6573 Remote Similarity NPD7508 Discontinued
0.6568 Remote Similarity NPD8303 Discontinued
0.6564 Remote Similarity NPD7131 Phase 3
0.6561 Remote Similarity NPD7512 Approved
0.6561 Remote Similarity NPD7511 Approved
0.6554 Remote Similarity NPD5335 Discontinued
0.6549 Remote Similarity NPD2650 Approved
0.6549 Remote Similarity NPD2652 Approved
0.6531 Remote Similarity NPD7813 Approved
0.6531 Remote Similarity NPD7815 Approved
0.6528 Remote Similarity NPD3123 Discovery
0.6522 Remote Similarity NPD8290 Clinical (unspecified phase)
0.6506 Remote Similarity NPD7105 Phase 1
0.6503 Remote Similarity NPD3820 Approved
0.6503 Remote Similarity NPD3821 Clinical (unspecified phase)
0.6503 Remote Similarity NPD3822 Approved
0.6494 Remote Similarity NPD8118 Discontinued
0.6494 Remote Similarity NPD5745 Approved
0.6491 Remote Similarity NPD6303 Approved
0.6491 Remote Similarity NPD6304 Approved
0.649 Remote Similarity NPD4151 Approved
0.6486 Remote Similarity NPD3603 Phase 3
0.6486 Remote Similarity NPD5338 Clinical (unspecified phase)
0.6481 Remote Similarity NPD1582 Approved
0.6481 Remote Similarity NPD2014 Approved
0.6481 Remote Similarity NPD2016 Approved
0.6481 Remote Similarity NPD2013 Approved
0.6481 Remote Similarity NPD1581 Approved
0.6478 Remote Similarity NPD5341 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