Structure

Physi-Chem Properties

Molecular Weight:  291.15
Volume:  295.235
LogP:  1.315
LogD:  1.132
LogS:  -1.946
# Rotatable Bonds:  4
TPSA:  70.0
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.786
Synthetic Accessibility Score:  4.318
Fsp3:  0.562
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.09
MDCK Permeability:  0.00017527792078908533
Pgp-inhibitor:  0.002
Pgp-substrate:  0.434
Human Intestinal Absorption (HIA):  0.108
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.29

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.278
Plasma Protein Binding (PPB):  27.803218841552734%
Volume Distribution (VD):  1.997
Pgp-substrate:  65.52196502685547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.054
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.525
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.16
CYP2D6-inhibitor:  0.751
CYP2D6-substrate:  0.476
CYP3A4-inhibitor:  0.047
CYP3A4-substrate:  0.463

ADMET: Excretion

Clearance (CL):  11.762
Half-life (T1/2):  0.867

ADMET: Toxicity

hERG Blockers:  0.165
Human Hepatotoxicity (H-HT):  0.244
Drug-inuced Liver Injury (DILI):  0.211
AMES Toxicity:  0.049
Rat Oral Acute Toxicity:  0.055
Maximum Recommended Daily Dose:  0.912
Skin Sensitization:  0.229
Carcinogencity:  0.279
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.833

Download Data

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

  Natural Product: NPC474847

Natural Product ID:  NPC474847
Common Name*:   GAWZPEGNIUXWSW-OWRMTOLYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  GAWZPEGNIUXWSW-OWRMTOLYSA-N
Standard InCHI:  InChI=1S/C16H21NO4/c1-17-12-8-11(9-13(17)16(20)15(12)19)21-14(18)7-10-5-3-2-4-6-10/h2-6,11-13,15-16,19-20H,7-9H2,1H3/t11-,12?,13?,15-,16+
SMILES:  O[C@@H]1[C@H](O)C2N(C1C[C@@H](C2)OC(=O)Cc1ccccc1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL484859
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000492] Tropane alkaloids

*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
NPO33258 erythroxylum pervillei Species Erythroxylaceae Eukaryota n.a. n.a. n.a. PMID[11754602]

☑ 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
NPT1034 Cell Line Lu1 Homo sapiens ED50 > 20.0 ug ml-1 PMID[482644]
NPT1851 Cell Line Col2 Homo sapiens ED50 > 20.0 ug ml-1 PMID[482644]
NPT91 Cell Line KB Homo sapiens ED50 > 20.0 ug ml-1 PMID[482644]
NPT858 Cell Line LNCaP Homo sapiens ED50 > 20.0 ug ml-1 PMID[482644]
NPT2345 Cell Line SW626 Homo sapiens ED50 > 20.0 ug ml-1 PMID[482644]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 20.0 ug ml-1 PMID[482644]

☑ 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 NPC474847 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
0.935 High Similarity NPC69496
0.9127 High Similarity NPC245836
0.9127 High Similarity NPC233910
0.88 High Similarity NPC65310
0.878 High Similarity NPC291027
0.878 High Similarity NPC317474
0.878 High Similarity NPC213126
0.878 High Similarity NPC84281
0.878 High Similarity NPC169485
0.7907 Intermediate Similarity NPC26285
0.7724 Intermediate Similarity NPC158854
0.7589 Intermediate Similarity NPC57976
0.7519 Intermediate Similarity NPC285394
0.75 Intermediate Similarity NPC281104
0.7357 Intermediate Similarity NPC260045
0.7357 Intermediate Similarity NPC476102
0.7357 Intermediate Similarity NPC474811
0.7357 Intermediate Similarity NPC79465
0.7357 Intermediate Similarity NPC118099
0.7357 Intermediate Similarity NPC151706
0.7357 Intermediate Similarity NPC293377
0.7357 Intermediate Similarity NPC475318
0.7357 Intermediate Similarity NPC49577
0.7357 Intermediate Similarity NPC9687
0.7357 Intermediate Similarity NPC273907
0.7357 Intermediate Similarity NPC474855
0.7357 Intermediate Similarity NPC475598
0.7357 Intermediate Similarity NPC474787
0.7357 Intermediate Similarity NPC76785
0.7357 Intermediate Similarity NPC90194
0.7348 Intermediate Similarity NPC190663
0.7333 Intermediate Similarity NPC322598
0.7333 Intermediate Similarity NPC47667
0.7313 Intermediate Similarity NPC35996
0.7305 Intermediate Similarity NPC127741
0.7302 Intermediate Similarity NPC65855
0.7302 Intermediate Similarity NPC292758
0.7297 Intermediate Similarity NPC162104
0.7273 Intermediate Similarity NPC269398
0.7273 Intermediate Similarity NPC263493
0.726 Intermediate Similarity NPC145113
0.7258 Intermediate Similarity NPC476198
0.7252 Intermediate Similarity NPC169328
0.7244 Intermediate Similarity NPC35345
0.7241 Intermediate Similarity NPC209509
0.7239 Intermediate Similarity NPC160493
0.7222 Intermediate Similarity NPC161069
0.7214 Intermediate Similarity NPC313663
0.7197 Intermediate Similarity NPC310467
0.7197 Intermediate Similarity NPC237420
0.7197 Intermediate Similarity NPC314992
0.7185 Intermediate Similarity NPC175726
0.7185 Intermediate Similarity NPC108286
0.7185 Intermediate Similarity NPC474082
0.7183 Intermediate Similarity NPC471264
0.7183 Intermediate Similarity NPC471265
0.7172 Intermediate Similarity NPC476978
0.7172 Intermediate Similarity NPC52748
0.7162 Intermediate Similarity NPC94602
0.7162 Intermediate Similarity NPC2501
0.7153 Intermediate Similarity NPC136453
0.7143 Intermediate Similarity NPC329761
0.7143 Intermediate Similarity NPC225648
0.7143 Intermediate Similarity NPC246079
0.7133 Intermediate Similarity NPC98424
0.7133 Intermediate Similarity NPC178662
0.7133 Intermediate Similarity NPC470884
0.7133 Intermediate Similarity NPC92784
0.7133 Intermediate Similarity NPC122590
0.7133 Intermediate Similarity NPC476133
0.712 Intermediate Similarity NPC67043
0.7103 Intermediate Similarity NPC251439
0.7101 Intermediate Similarity NPC152850
0.7101 Intermediate Similarity NPC239990
0.7101 Intermediate Similarity NPC89923
0.7101 Intermediate Similarity NPC105114
0.7101 Intermediate Similarity NPC71933
0.7099 Intermediate Similarity NPC101139
0.7095 Intermediate Similarity NPC471820
0.7095 Intermediate Similarity NPC471821
0.709 Intermediate Similarity NPC80150
0.7089 Intermediate Similarity NPC474858
0.7083 Intermediate Similarity NPC239762
0.7083 Intermediate Similarity NPC163392
0.7075 Intermediate Similarity NPC262077
0.7073 Intermediate Similarity NPC214200
0.7073 Intermediate Similarity NPC228400
0.7073 Intermediate Similarity NPC473562
0.7059 Intermediate Similarity NPC197743
0.7059 Intermediate Similarity NPC297145
0.7055 Intermediate Similarity NPC329816
0.705 Intermediate Similarity NPC469666
0.705 Intermediate Similarity NPC213969
0.705 Intermediate Similarity NPC165726
0.7045 Intermediate Similarity NPC2265
0.704 Intermediate Similarity NPC19136
0.7027 Intermediate Similarity NPC138775
0.7007 Intermediate Similarity NPC315266
0.7007 Intermediate Similarity NPC5620
0.6992 Remote Similarity NPC12730
0.6986 Remote Similarity NPC197682
0.6975 Remote Similarity NPC317645
0.697 Remote Similarity NPC197470
0.6966 Remote Similarity NPC268841
0.6966 Remote Similarity NPC307357
0.6966 Remote Similarity NPC46098
0.6963 Remote Similarity NPC478015
0.6963 Remote Similarity NPC478014
0.6963 Remote Similarity NPC478016
0.696 Remote Similarity NPC160382
0.6957 Remote Similarity NPC57607
0.6957 Remote Similarity NPC477462
0.6957 Remote Similarity NPC317163
0.6957 Remote Similarity NPC4974
0.6954 Remote Similarity NPC214239
0.695 Remote Similarity NPC157311
0.6944 Remote Similarity NPC68865
0.6939 Remote Similarity NPC204546
0.6934 Remote Similarity NPC6975
0.6923 Remote Similarity NPC248283
0.6923 Remote Similarity NPC269340
0.6918 Remote Similarity NPC168113
0.6913 Remote Similarity NPC135121
0.6905 Remote Similarity NPC47286
0.6901 Remote Similarity NPC44805
0.6901 Remote Similarity NPC8761
0.6894 Remote Similarity NPC33742
0.6892 Remote Similarity NPC477217
0.6892 Remote Similarity NPC201244
0.6884 Remote Similarity NPC307020
0.6884 Remote Similarity NPC138798
0.6875 Remote Similarity NPC329717
0.6871 Remote Similarity NPC139326
0.6871 Remote Similarity NPC176226
0.6863 Remote Similarity NPC68967
0.6861 Remote Similarity NPC252878
0.6852 Remote Similarity NPC471165
0.6849 Remote Similarity NPC476259
0.6842 Remote Similarity NPC188010
0.6842 Remote Similarity NPC210531
0.6838 Remote Similarity NPC45777
0.6838 Remote Similarity NPC477061
0.6838 Remote Similarity NPC476183
0.6835 Remote Similarity NPC244454
0.6835 Remote Similarity NPC26353
0.6832 Remote Similarity NPC89831
0.6829 Remote Similarity NPC122493
0.6829 Remote Similarity NPC10781
0.6829 Remote Similarity NPC293628
0.6829 Remote Similarity NPC324569
0.6828 Remote Similarity NPC478140
0.6824 Remote Similarity NPC475128
0.6821 Remote Similarity NPC129666
0.6818 Remote Similarity NPC276949
0.6818 Remote Similarity NPC35850
0.6812 Remote Similarity NPC46427
0.681 Remote Similarity NPC129624
0.6809 Remote Similarity NPC81092
0.6809 Remote Similarity NPC103605
0.6807 Remote Similarity NPC9822
0.68 Remote Similarity NPC260194
0.6797 Remote Similarity NPC474111
0.6797 Remote Similarity NPC329705
0.6794 Remote Similarity NPC329011
0.6792 Remote Similarity NPC469479
0.6788 Remote Similarity NPC476184
0.6788 Remote Similarity NPC202521
0.6788 Remote Similarity NPC476281
0.6786 Remote Similarity NPC79608
0.6786 Remote Similarity NPC475566
0.6786 Remote Similarity NPC476033
0.6783 Remote Similarity NPC45191
0.6774 Remote Similarity NPC210529
0.6774 Remote Similarity NPC160548
0.6774 Remote Similarity NPC262826
0.6774 Remote Similarity NPC175852
0.6772 Remote Similarity NPC224610
0.6772 Remote Similarity NPC194390
0.6772 Remote Similarity NPC113326
0.6772 Remote Similarity NPC88267
0.6768 Remote Similarity NPC329992
0.6755 Remote Similarity NPC473541
0.6755 Remote Similarity NPC105717
0.6755 Remote Similarity NPC240848
0.6752 Remote Similarity NPC294134
0.6742 Remote Similarity NPC474584
0.6738 Remote Similarity NPC210950
0.6738 Remote Similarity NPC199738
0.6736 Remote Similarity NPC287401
0.6733 Remote Similarity NPC314358
0.673 Remote Similarity NPC63931
0.6719 Remote Similarity NPC167336
0.6718 Remote Similarity NPC319579
0.6715 Remote Similarity NPC476990
0.6715 Remote Similarity NPC200964
0.6714 Remote Similarity NPC477248
0.6714 Remote Similarity NPC246166
0.6714 Remote Similarity NPC477249
0.6711 Remote Similarity NPC315283
0.6711 Remote Similarity NPC314388

  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 NPC474847 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
0.935 High Similarity NPD2613 Approved
0.9127 High Similarity NPD4745 Approved
0.9127 High Similarity NPD2566 Approved
0.9127 High Similarity NPD3614 Approved
0.9127 High Similarity NPD2574 Discontinued
0.9127 High Similarity NPD3615 Approved
0.9127 High Similarity NPD2572 Clinical (unspecified phase)
0.9127 High Similarity NPD2573 Approved
0.9127 High Similarity NPD2571 Approved
0.9127 High Similarity NPD3088 Approved
0.9127 High Similarity NPD3090 Approved
0.9127 High Similarity NPD4746 Phase 3
0.9127 High Similarity NPD3616 Approved
0.9127 High Similarity NPD3089 Approved
0.9127 High Similarity NPD3087 Approved
0.9127 High Similarity NPD2570 Approved
0.8984 High Similarity NPD4686 Approved
0.8984 High Similarity NPD4685 Phase 3
0.8984 High Similarity NPD4684 Phase 3
0.88 High Similarity NPD2159 Approved
0.88 High Similarity NPD2160 Approved
0.88 High Similarity NPD2627 Approved
0.88 High Similarity NPD2626 Approved
0.88 High Similarity NPD2625 Approved
0.88 High Similarity NPD2628 Approved
0.878 High Similarity NPD2611 Approved
0.878 High Similarity NPD4218 Approved
0.878 High Similarity NPD2609 Approved
0.878 High Similarity NPD2610 Approved
0.878 High Similarity NPD3132 Approved
0.878 High Similarity NPD4215 Approved
0.878 High Similarity NPD2608 Approved
0.878 High Similarity NPD4217 Approved
0.878 High Similarity NPD4216 Approved
0.878 High Similarity NPD2612 Approved
0.878 High Similarity NPD3131 Approved
0.8731 High Similarity NPD2575 Approved
0.8092 Intermediate Similarity NPD5204 Approved
0.806 Intermediate Similarity NPD6309 Approved
0.806 Intermediate Similarity NPD6311 Approved
0.806 Intermediate Similarity NPD6310 Approved
0.8045 Intermediate Similarity NPD4621 Approved
0.8045 Intermediate Similarity NPD4619 Approved
0.803 Intermediate Similarity NPD5202 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4576 Approved
0.8 Intermediate Similarity NPD4574 Approved
0.7955 Intermediate Similarity NPD3662 Phase 3
0.7955 Intermediate Similarity NPD3663 Approved
0.7955 Intermediate Similarity NPD3661 Approved
0.7955 Intermediate Similarity NPD3664 Approved
0.7895 Intermediate Similarity NPD5201 Approved
0.7895 Intermediate Similarity NPD4617 Approved
0.7895 Intermediate Similarity NPD4620 Approved
0.7895 Intermediate Similarity NPD5203 Approved
0.7724 Intermediate Similarity NPD1756 Approved
0.7724 Intermediate Similarity NPD1752 Approved
0.7708 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD2607 Approved
0.7664 Intermediate Similarity NPD5119 Approved
0.7664 Intermediate Similarity NPD5121 Approved
0.7664 Intermediate Similarity NPD5120 Approved
0.7619 Intermediate Similarity NPD2650 Approved
0.7619 Intermediate Similarity NPD2652 Approved
0.7581 Intermediate Similarity NPD4233 Approved
0.7581 Intermediate Similarity NPD4234 Approved
0.7581 Intermediate Similarity NPD3646 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD2584 Suspended
0.7574 Intermediate Similarity NPD4738 Phase 2
0.7557 Intermediate Similarity NPD4135 Approved
0.7557 Intermediate Similarity NPD4106 Approved
0.7557 Intermediate Similarity NPD4136 Approved
0.7519 Intermediate Similarity NPD2117 Pre-registration
0.7519 Intermediate Similarity NPD5158 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD5159 Phase 2
0.7519 Intermediate Similarity NPD2115 Approved
0.7519 Intermediate Similarity NPD5157 Phase 1
0.7519 Intermediate Similarity NPD2116 Approved
0.75 Intermediate Similarity NPD4806 Approved
0.75 Intermediate Similarity NPD4807 Approved
0.75 Intermediate Similarity NPD4706 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2569 Approved
0.75 Intermediate Similarity NPD2567 Approved
0.748 Intermediate Similarity NPD1373 Approved
0.748 Intermediate Similarity NPD1370 Approved
0.748 Intermediate Similarity NPD1371 Approved
0.748 Intermediate Similarity NPD1374 Approved
0.7463 Intermediate Similarity NPD5667 Approved
0.7462 Intermediate Similarity NPD2994 Approved
0.7447 Intermediate Similarity NPD3648 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD4175 Approved
0.7426 Intermediate Similarity NPD4177 Approved
0.7405 Intermediate Similarity NPD4105 Approved
0.7405 Intermediate Similarity NPD3030 Approved
0.7405 Intermediate Similarity NPD3032 Approved
0.7405 Intermediate Similarity NPD4102 Approved
0.7405 Intermediate Similarity NPD3031 Approved
0.7383 Intermediate Similarity NPD6591 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD6852 Discontinued
0.7348 Intermediate Similarity NPD5305 Approved
0.7348 Intermediate Similarity NPD5306 Approved
0.7339 Intermediate Similarity NPD5705 Approved
0.7339 Intermediate Similarity NPD5706 Approved
0.7339 Intermediate Similarity NPD5704 Approved
0.7293 Intermediate Similarity NPD2946 Phase 2
0.7286 Intermediate Similarity NPD4153 Approved
0.7286 Intermediate Similarity NPD8416 Discontinued
0.7252 Intermediate Similarity NPD6065 Approved
0.7214 Intermediate Similarity NPD7714 Approved
0.7214 Intermediate Similarity NPD7715 Approved
0.7208 Intermediate Similarity NPD3494 Approved
0.7208 Intermediate Similarity NPD3492 Approved
0.7208 Intermediate Similarity NPD3493 Approved
0.7206 Intermediate Similarity NPD2198 Approved
0.7206 Intermediate Similarity NPD2199 Approved
0.7197 Intermediate Similarity NPD2218 Phase 2
0.7197 Intermediate Similarity NPD2217 Approved
0.7192 Intermediate Similarity NPD7488 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4572 Approved
0.7188 Intermediate Similarity NPD4571 Approved
0.7188 Intermediate Similarity NPD4573 Approved
0.7185 Intermediate Similarity NPD3072 Approved
0.7185 Intermediate Similarity NPD3073 Approved
0.7185 Intermediate Similarity NPD3071 Approved
0.7183 Intermediate Similarity NPD6073 Approved
0.7183 Intermediate Similarity NPD3528 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD4766 Approved
0.7154 Intermediate Similarity NPD854 Approved
0.7154 Intermediate Similarity NPD855 Approved
0.7143 Intermediate Similarity NPD5979 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD4677 Discontinued
0.7111 Intermediate Similarity NPD7437 Approved
0.7111 Intermediate Similarity NPD7436 Approved
0.7111 Intermediate Similarity NPD4762 Approved
0.7111 Intermediate Similarity NPD4761 Approved
0.7109 Intermediate Similarity NPD2201 Approved
0.7105 Intermediate Similarity NPD8417 Discontinued
0.7103 Intermediate Similarity NPD7702 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD5723 Approved
0.708 Intermediate Similarity NPD6792 Phase 3
0.7077 Intermediate Similarity NPD3598 Phase 3
0.7068 Intermediate Similarity NPD6345 Approved
0.7068 Intermediate Similarity NPD6343 Approved
0.7067 Intermediate Similarity NPD7613 Discontinued
0.7063 Intermediate Similarity NPD811 Approved
0.7063 Intermediate Similarity NPD810 Approved
0.7063 Intermediate Similarity NPD5725 Approved
0.7063 Intermediate Similarity NPD1654 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD812 Approved
0.705 Intermediate Similarity NPD3040 Approved
0.7042 Intermediate Similarity NPD5296 Approved
0.7034 Intermediate Similarity NPD7511 Approved
0.7034 Intermediate Similarity NPD2239 Approved
0.7034 Intermediate Similarity NPD2240 Approved
0.7034 Intermediate Similarity NPD7512 Approved
0.7029 Intermediate Similarity NPD6564 Approved
0.7029 Intermediate Similarity NPD6563 Approved
0.7029 Intermediate Similarity NPD6565 Approved
0.7023 Intermediate Similarity NPD747 Discontinued
0.7016 Intermediate Similarity NPD4719 Phase 2
0.7015 Intermediate Similarity NPD4504 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD5981 Approved
0.7015 Intermediate Similarity NPD6994 Approved
0.7015 Intermediate Similarity NPD6993 Approved
0.7014 Intermediate Similarity NPD6295 Approved
0.7014 Intermediate Similarity NPD6294 Approved
0.7 Intermediate Similarity NPD5263 Approved
0.6993 Remote Similarity NPD8643 Discontinued
0.6986 Remote Similarity NPD4152 Approved
0.697 Remote Similarity NPD1348 Approved
0.6944 Remote Similarity NPD8172 Phase 2
0.6944 Remote Similarity NPD8173 Phase 2
0.694 Remote Similarity NPD4479 Discontinued
0.6929 Remote Similarity NPD5759 Approved
0.6923 Remote Similarity NPD6623 Phase 3
0.6913 Remote Similarity NPD8323 Discontinued
0.6906 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6906 Remote Similarity NPD4103 Phase 2
0.6901 Remote Similarity NPD5299 Approved
0.6894 Remote Similarity NPD1711 Phase 2
0.6892 Remote Similarity NPD4237 Approved
0.6892 Remote Similarity NPD4236 Phase 3
0.6884 Remote Similarity NPD4659 Approved
0.6879 Remote Similarity NPD4125 Approved
0.6879 Remote Similarity NPD4676 Approved
0.6875 Remote Similarity NPD3577 Discontinued
0.6875 Remote Similarity NPD7113 Clinical (unspecified phase)
0.6866 Remote Similarity NPD5991 Approved
0.6866 Remote Similarity NPD5990 Approved
0.6853 Remote Similarity NPD7634 Clinical (unspecified phase)
0.6853 Remote Similarity NPD5747 Discontinued
0.6846 Remote Similarity NPD3644 Approved
0.6846 Remote Similarity NPD3643 Approved
0.6846 Remote Similarity NPD6676 Phase 2
0.6846 Remote Similarity NPD3642 Approved
0.6842 Remote Similarity NPD7508 Discontinued
0.6839 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6831 Remote Similarity NPD4794 Discontinued
0.6831 Remote Similarity NPD6039 Approved
0.6829 Remote Similarity NPD9566 Approved
0.6828 Remote Similarity NPD7510 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