NPASS Compound

Structure

NPC268954 OpenBabel07101718222D 42 47 0 0 1 0 0 0 0 0999 V2000 4.1534 -7.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6454 -7.6735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2943 -2.5265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7739 -3.3571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3103 -2.2695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7899 -1.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8307 -4.3163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6614 -3.8367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9841 -7.6735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3227 -1.9184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4920 -1.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8307 -3.3571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4920 -4.3163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8307 -0.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3227 -4.7959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9841 -2.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8307 -0.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8147 -7.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3227 -2.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1534 -3.3571 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.9184 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6614 -1.9184 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8147 -4.3163 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9841 -4.7959 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8147 -6.2347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1534 -6.2347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8147 -3.3571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8307 -1.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4920 -3.3571 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6614 -2.8776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8307 -1.4388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1534 -4.3163 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8307 -0.4796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6454 -4.7959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6454 -5.7551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9841 -6.7143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3227 -6.7143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7899 -0.4796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9841 -5.7551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 20 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 9 20 2 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 16 34 1 0 0 0 0 18 22 1 0 0 0 0 18 29 1 0 0 0 0 19 33 1 0 0 0 0 19 41 1 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 22 34 1 6 0 0 0 23 30 1 0 0 0 0 23 33 1 1 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 25 36 1 6 0 0 0 26 34 1 1 0 0 0 26 42 1 0 0 0 0 27 37 2 0 0 0 0 27 42 1 0 0 0 0 28 38 2 0 0 0 0 28 39 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 1 0 0 0 32 8 1 1 0 0 0 33 15 1 6 0 0 0 34 28 1 1 0 0 0 35 17 1 6 0 0 0 35 40 1 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.37
Volume:	613.563
LogP:	5.128
LogD:	4.156
LogS:	-4.551
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	6.652
Fsp3:	0.829
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.447
MDCK Permeability:	2.3487316866521724e-05
Pgp-inhibitor:	0.357
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.495
30% Bioavailability (F30%):	0.159

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.771
Plasma Protein Binding (PPB):	87.78038787841797%
Volume Distribution (VD):	0.822
Pgp-substrate:	9.907417297363281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.66
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.66
CYP2C9-inhibitor:	0.231
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	10.402
Half-life (T1/2):	0.052

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.526
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.13
Carcinogencity:	0.702
Eye Corrosion:	0.01
Eye Irritation:	0.014
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC268954

Natural Product ID:	NPC268954
*Common Name:**	CTQRAHWNNVEBTE-SJKNEWIFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CTQRAHWNNVEBTE-SJKNEWIFSA-N
Standard InCHI:	InChI=1S/C35H52O7/c1-9-20(2)27(37)42-26-25(36)29(3,4)18-22-21-10-11-24-32(8,31(21,7)14-16-34(22,26)28(38)39)13-12-23-30(5,6)35(40)17-15-33(23,24)19-41-35/h9-10,22-26,36,40H,11-19H2,1-8H3,(H,38,39)/b20-9-/t22-,23-,24-,25+,26+,31+,32+,33+,34-,35-/m0/s1
SMILES:	C/C=C(C(=O)O[C@@H]1[C@@H](O)C(C)(C)C[C@@H]2[C@]1(CC[C@@]1(C2=CC[C@H]2[C@@]1(C)CC[C@@H]1[C@@]32CC[C@@](C1(C)C)(OC3)O)C)C(=O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502375
PubChem CID:	21592382
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO6442	Lippia turbinata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170663]
NPO6442	Lippia turbinata	Species	Verbenaceae	Eukaryota	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

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	64000.0	nM	PMID[447914]

☑ 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 NPC268954 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	1615
0.2-0.3	4378
0.3-0.4	7700
0.4-0.5	12913
0.5-0.6	7578
0.6-0.7	5149
0.7-0.8	2187
0.8-0.85	441
0.85-0.9	415
0.9-0.95	47
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9906	High Similarity	NPC110861
0.9813	High Similarity	NPC44170
0.9159	High Similarity	NPC473483
0.9138	High Similarity	NPC470516
0.9065	High Similarity	NPC475570
0.8983	High Similarity	NPC477196
0.8972	High Similarity	NPC88349
0.8908	High Similarity	NPC477197
0.8898	High Similarity	NPC477193
0.8898	High Similarity	NPC477194
0.8898	High Similarity	NPC477191
0.8898	High Similarity	NPC477192
0.8868	High Similarity	NPC258547
0.8868	High Similarity	NPC283343
0.885	High Similarity	NPC473405
0.8833	High Similarity	NPC476776
0.8833	High Similarity	NPC477195
0.8829	High Similarity	NPC48249
0.8824	High Similarity	NPC470518
0.8824	High Similarity	NPC88311
0.8824	High Similarity	NPC11577
0.8824	High Similarity	NPC470913
0.8824	High Similarity	NPC477079
0.8824	High Similarity	NPC252289
0.8824	High Similarity	NPC115656
0.8824	High Similarity	NPC477076
0.8824	High Similarity	NPC280029
0.8824	High Similarity	NPC107536
0.8824	High Similarity	NPC97918
0.8824	High Similarity	NPC252657
0.8824	High Similarity	NPC305793
0.8824	High Similarity	NPC141600
0.8824	High Similarity	NPC244296
0.8824	High Similarity	NPC82380
0.8824	High Similarity	NPC1314
0.8824	High Similarity	NPC273878
0.8824	High Similarity	NPC9470
0.8824	High Similarity	NPC269484
0.8824	High Similarity	NPC472267
0.8824	High Similarity	NPC477077
0.8807	High Similarity	NPC475263
0.8785	High Similarity	NPC476889
0.8783	High Similarity	NPC476150
0.8783	High Similarity	NPC476127
0.8774	High Similarity	NPC473160
0.8772	High Similarity	NPC471548
0.875	High Similarity	NPC271610
0.875	High Similarity	NPC222951
0.875	High Similarity	NPC478155
0.875	High Similarity	NPC43589
0.875	High Similarity	NPC300655
0.875	High Similarity	NPC238935
0.875	High Similarity	NPC25998
0.875	High Similarity	NPC476775
0.875	High Similarity	NPC476780
0.875	High Similarity	NPC311178
0.875	High Similarity	NPC475208
0.875	High Similarity	NPC476774
0.8739	High Similarity	NPC23020
0.8739	High Similarity	NPC472268
0.8739	High Similarity	NPC475281
0.8739	High Similarity	NPC472270
0.8739	High Similarity	NPC472269
0.8739	High Similarity	NPC31839
0.8739	High Similarity	NPC329923
0.8739	High Similarity	NPC477075
0.8739	High Similarity	NPC112492
0.8739	High Similarity	NPC477078
0.8716	High Similarity	NPC473586
0.8707	High Similarity	NPC476204
0.8707	High Similarity	NPC170084
0.8696	High Similarity	NPC473636
0.8696	High Similarity	NPC473839
0.8696	High Similarity	NPC77689
0.8696	High Similarity	NPC211093
0.8692	High Similarity	NPC273668
0.8692	High Similarity	NPC476890
0.8692	High Similarity	NPC40918
0.8689	High Similarity	NPC476778
0.8689	High Similarity	NPC476777
0.8684	High Similarity	NPC473968
0.8684	High Similarity	NPC474483
0.8684	High Similarity	NPC300419
0.8678	High Similarity	NPC473679
0.8678	High Similarity	NPC324933
0.8678	High Similarity	NPC277212
0.8678	High Similarity	NPC178264
0.8678	High Similarity	NPC192765
0.8678	High Similarity	NPC478150
0.8678	High Similarity	NPC233223
0.8678	High Similarity	NPC473918
0.8678	High Similarity	NPC475177
0.8678	High Similarity	NPC478154
0.8678	High Similarity	NPC183816
0.8678	High Similarity	NPC475444
0.8678	High Similarity	NPC46823
0.8678	High Similarity	NPC322904
0.8678	High Similarity	NPC196874
0.8678	High Similarity	NPC478153
0.8678	High Similarity	NPC30279
0.8678	High Similarity	NPC312650
0.8678	High Similarity	NPC478152
0.8678	High Similarity	NPC71391
0.8678	High Similarity	NPC319719
0.8667	High Similarity	NPC476966
0.8667	High Similarity	NPC470912
0.8667	High Similarity	NPC47995
0.8667	High Similarity	NPC265841
0.8661	High Similarity	NPC471967
0.8661	High Similarity	NPC80843
0.8661	High Similarity	NPC1046
0.8661	High Similarity	NPC116794
0.8649	High Similarity	NPC108709
0.8649	High Similarity	NPC110139
0.8649	High Similarity	NPC7870
0.8649	High Similarity	NPC75747
0.8649	High Similarity	NPC242611
0.8649	High Similarity	NPC68419
0.8649	High Similarity	NPC199457
0.8649	High Similarity	NPC102914
0.8618	High Similarity	NPC110700
0.8618	High Similarity	NPC279915
0.8609	High Similarity	NPC470515
0.8607	High Similarity	NPC476779
0.8607	High Similarity	NPC478151
0.8607	High Similarity	NPC225791
0.8598	High Similarity	NPC476888
0.8598	High Similarity	NPC93744
0.8596	High Similarity	NPC37134
0.8596	High Similarity	NPC291903
0.8595	High Similarity	NPC301639
0.8595	High Similarity	NPC45346
0.8595	High Similarity	NPC329993
0.8595	High Similarity	NPC134914
0.8595	High Similarity	NPC172374
0.8595	High Similarity	NPC475377
0.8595	High Similarity	NPC264566
0.8595	High Similarity	NPC173435
0.8595	High Similarity	NPC478064
0.8595	High Similarity	NPC475167
0.8595	High Similarity	NPC478065
0.8595	High Similarity	NPC476074
0.8595	High Similarity	NPC262796
0.8584	High Similarity	NPC271138
0.8584	High Similarity	NPC269315
0.8583	High Similarity	NPC220838
0.8583	High Similarity	NPC45606
0.8571	High Similarity	NPC179434
0.8571	High Similarity	NPC191763
0.8571	High Similarity	NPC297950
0.8559	High Similarity	NPC127853
0.8559	High Similarity	NPC204407
0.8559	High Similarity	NPC167383
0.8559	High Similarity	NPC57362
0.8559	High Similarity	NPC310546
0.8559	High Similarity	NPC237503
0.8559	High Similarity	NPC306746
0.8545	High Similarity	NPC283849
0.8534	High Similarity	NPC470914
0.8534	High Similarity	NPC470517
0.8534	High Similarity	NPC470911
0.8534	High Similarity	NPC475775
0.8534	High Similarity	NPC470915
0.8534	High Similarity	NPC476529
0.8522	High Similarity	NPC471547
0.8522	High Similarity	NPC475809
0.8522	High Similarity	NPC473824
0.8522	High Similarity	NPC134430
0.8522	High Similarity	NPC475119
0.8509	High Similarity	NPC164389
0.8509	High Similarity	NPC475633
0.8509	High Similarity	NPC475486
0.8505	High Similarity	NPC474190
0.8505	High Similarity	NPC475156
0.8505	High Similarity	NPC473576
0.8496	Intermediate Similarity	NPC46388
0.8496	Intermediate Similarity	NPC139894
0.8496	Intermediate Similarity	NPC473383
0.8496	Intermediate Similarity	NPC256798
0.8496	Intermediate Similarity	NPC37739
0.8496	Intermediate Similarity	NPC128925
0.8496	Intermediate Similarity	NPC100383
0.8491	Intermediate Similarity	NPC261935
0.8491	Intermediate Similarity	NPC106112
0.8487	Intermediate Similarity	NPC470922
0.8482	Intermediate Similarity	NPC270667
0.8482	Intermediate Similarity	NPC476882
0.8482	Intermediate Similarity	NPC29069
0.8482	Intermediate Similarity	NPC56713
0.8482	Intermediate Similarity	NPC136877
0.8482	Intermediate Similarity	NPC474589
0.8482	Intermediate Similarity	NPC476885
0.8482	Intermediate Similarity	NPC220984
0.8482	Intermediate Similarity	NPC164194
0.8482	Intermediate Similarity	NPC476884
0.8482	Intermediate Similarity	NPC279554
0.8482	Intermediate Similarity	NPC476881
0.8482	Intermediate Similarity	NPC476883
0.8482	Intermediate Similarity	NPC127056
0.8482	Intermediate Similarity	NPC174679

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 NPC268954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	1847
0.2-0.3	3620
0.3-0.4	2219
0.4-0.5	763
0.5-0.6	274
0.6-0.7	133
0.7-0.8	36
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8403	Intermediate Similarity	NPD8328	Phase 3
0.8148	Intermediate Similarity	NPD7902	Approved
0.8142	Intermediate Similarity	NPD6686	Approved
0.807	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD7115	Discovery
0.8051	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7748	Approved
0.792	Intermediate Similarity	NPD7319	Approved
0.7909	Intermediate Similarity	NPD4225	Approved
0.787	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7900	Approved
0.785	Intermediate Similarity	NPD7515	Phase 2
0.7823	Intermediate Similarity	NPD7507	Approved
0.7759	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7638	Approved
0.7705	Intermediate Similarity	NPD8294	Approved
0.7705	Intermediate Similarity	NPD8377	Approved
0.7679	Intermediate Similarity	NPD7640	Approved
0.7679	Intermediate Similarity	NPD7639	Approved
0.7672	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8133	Approved
0.7642	Intermediate Similarity	NPD8296	Approved
0.7642	Intermediate Similarity	NPD8033	Approved
0.7642	Intermediate Similarity	NPD8380	Approved
0.7642	Intermediate Similarity	NPD8335	Approved
0.7642	Intermediate Similarity	NPD8379	Approved
0.7642	Intermediate Similarity	NPD8378	Approved
0.7623	Intermediate Similarity	NPD7516	Approved
0.7586	Intermediate Similarity	NPD6412	Phase 2
0.7559	Intermediate Similarity	NPD7736	Approved
0.7542	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7327	Approved
0.7541	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD8513	Phase 3
0.75	Intermediate Similarity	NPD8516	Approved
0.75	Intermediate Similarity	NPD8515	Approved
0.75	Intermediate Similarity	NPD8517	Approved
0.7323	Intermediate Similarity	NPD7492	Approved
0.7288	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6319	Approved
0.728	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7266	Intermediate Similarity	NPD6616	Approved
0.7209	Intermediate Similarity	NPD7078	Approved
0.7209	Intermediate Similarity	NPD8293	Discontinued
0.7207	Intermediate Similarity	NPD8035	Phase 2
0.7207	Intermediate Similarity	NPD8034	Phase 2
0.7165	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7131	Intermediate Similarity	NPD6882	Approved
0.7117	Intermediate Similarity	NPD6698	Approved
0.7117	Intermediate Similarity	NPD46	Approved
0.7094	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD6016	Approved
0.7087	Intermediate Similarity	NPD6015	Approved
0.7083	Intermediate Similarity	NPD6899	Approved
0.7083	Intermediate Similarity	NPD6881	Approved
0.7073	Intermediate Similarity	NPD4632	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7049	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6650	Approved
0.7049	Intermediate Similarity	NPD6649	Approved
0.7049	Intermediate Similarity	NPD8130	Phase 1
0.704	Intermediate Similarity	NPD6009	Approved
0.7031	Intermediate Similarity	NPD5988	Approved
0.7025	Intermediate Similarity	NPD6373	Approved
0.7025	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD5344	Discontinued
0.7	Intermediate Similarity	NPD5697	Approved
0.6991	Remote Similarity	NPD6399	Phase 3
0.6967	Remote Similarity	NPD7102	Approved
0.6967	Remote Similarity	NPD4634	Approved
0.6967	Remote Similarity	NPD6883	Approved
0.6967	Remote Similarity	NPD6371	Approved
0.6967	Remote Similarity	NPD7290	Approved
0.6953	Remote Similarity	NPD6921	Approved
0.6947	Remote Similarity	NPD8074	Phase 3
0.6942	Remote Similarity	NPD7320	Approved
0.6911	Remote Similarity	NPD6617	Approved
0.6911	Remote Similarity	NPD6847	Approved
0.6911	Remote Similarity	NPD6869	Approved
0.6909	Remote Similarity	NPD3618	Phase 1
0.6903	Remote Similarity	NPD6411	Approved
0.6887	Remote Similarity	NPD7645	Phase 2
0.6885	Remote Similarity	NPD6012	Approved
0.6885	Remote Similarity	NPD6014	Approved
0.6885	Remote Similarity	NPD6013	Approved
0.686	Remote Similarity	NPD5701	Approved
0.686	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3573	Approved
0.6842	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD5778	Approved
0.6838	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1694	Approved
0.6803	Remote Similarity	NPD6011	Approved
0.6786	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6079	Approved
0.6752	Remote Similarity	NPD6084	Phase 2
0.6752	Remote Similarity	NPD6083	Phase 2
0.6726	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6101	Approved
0.6726	Remote Similarity	NPD5328	Approved
0.6718	Remote Similarity	NPD7604	Phase 2
0.6692	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7838	Discovery
0.6642	Remote Similarity	NPD6033	Approved
0.664	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD6008	Approved
0.6639	Remote Similarity	NPD5285	Approved
0.6639	Remote Similarity	NPD6648	Approved
0.6639	Remote Similarity	NPD5286	Approved
0.6617	Remote Similarity	NPD6336	Discontinued
0.661	Remote Similarity	NPD4755	Approved
0.6609	Remote Similarity	NPD7983	Approved
0.6607	Remote Similarity	NPD7334	Approved
0.6607	Remote Similarity	NPD6684	Approved
0.6607	Remote Similarity	NPD6409	Approved
0.6607	Remote Similarity	NPD5330	Approved
0.6607	Remote Similarity	NPD7521	Approved
0.6607	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7146	Approved
0.6591	Remote Similarity	NPD6067	Discontinued
0.6587	Remote Similarity	NPD6053	Discontinued
0.6581	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6274	Approved
0.6557	Remote Similarity	NPD5141	Approved
0.6555	Remote Similarity	NPD5696	Approved
0.6552	Remote Similarity	NPD4202	Approved
0.6538	Remote Similarity	NPD7100	Approved
0.6538	Remote Similarity	NPD7101	Approved
0.6529	Remote Similarity	NPD5225	Approved
0.6529	Remote Similarity	NPD4633	Approved
0.6529	Remote Similarity	NPD5224	Approved
0.6529	Remote Similarity	NPD5226	Approved
0.6525	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5221	Approved
0.6525	Remote Similarity	NPD5222	Approved
0.6525	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD5785	Approved
0.65	Remote Similarity	NPD4700	Approved
0.6496	Remote Similarity	NPD7260	Phase 2
0.6491	Remote Similarity	NPD6903	Approved
0.6491	Remote Similarity	NPD6672	Approved
0.6491	Remote Similarity	NPD5737	Approved
0.6475	Remote Similarity	NPD5174	Approved
0.6475	Remote Similarity	NPD5175	Approved
0.6471	Remote Similarity	NPD5173	Approved
0.6466	Remote Similarity	NPD7637	Suspended
0.6462	Remote Similarity	NPD6335	Approved
0.6446	Remote Similarity	NPD5223	Approved
0.6441	Remote Similarity	NPD5695	Phase 3
0.6441	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD3666	Approved
0.6429	Remote Similarity	NPD3133	Approved
0.6429	Remote Similarity	NPD4786	Approved
0.6396	Remote Similarity	NPD3667	Approved
0.6387	Remote Similarity	NPD7732	Phase 3
0.6387	Remote Similarity	NPD7839	Suspended
0.6387	Remote Similarity	NPD7614	Phase 1
0.6385	Remote Similarity	NPD6317	Approved
0.6383	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8415	Approved
0.6343	Remote Similarity	NPD7830	Approved
0.6343	Remote Similarity	NPD7829	Approved
0.6336	Remote Similarity	NPD6313	Approved
0.6336	Remote Similarity	NPD6314	Approved
0.6327	Remote Similarity	NPD7625	Phase 1
0.6325	Remote Similarity	NPD5693	Phase 1
0.6316	Remote Similarity	NPD6909	Approved
0.6316	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6908	Approved
0.6312	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5956	Approved
0.6303	Remote Similarity	NPD4629	Approved
0.6303	Remote Similarity	NPD5210	Approved
0.6293	Remote Similarity	NPD4753	Phase 2
0.629	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5128	Approved
0.627	Remote Similarity	NPD4730	Approved
0.627	Remote Similarity	NPD4729	Approved
0.624	Remote Similarity	NPD4767	Approved
0.624	Remote Similarity	NPD4768	Approved
0.6218	Remote Similarity	NPD5282	Discontinued
0.6216	Remote Similarity	NPD4695	Discontinued
0.6216	Remote Similarity	NPD7525	Registered
0.6216	Remote Similarity	NPD8166	Discontinued
0.6214	Remote Similarity	NPD6845	Suspended
0.621	Remote Similarity	NPD4754	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