NPASS Compound

Structure

NPC259791 OpenBabel07101718182D 49 54 0 0 1 0 0 0 0 0999 V2000 -0.6762 -2.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0607 -0.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1458 3.5165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2373 -2.6809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0730 3.1966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2234 3.6871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0603 4.2947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9503 -1.5905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9189 4.7692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8089 -1.1159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0420 3.3138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1100 -1.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7592 4.2629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8272 -0.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3696 0.7550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2635 1.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0516 -0.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6505 1.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5300 -1.0596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7023 0.0358 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8742 2.5738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0560 -2.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6983 1.1589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8823 2.8075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1283 -0.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4606 1.8571 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2234 1.7250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7409 3.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9869 0.3713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3738 2.2156 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1714 0.9197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1200 -0.7223 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5891 0.4348 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8639 1.8267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2880 0.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2234 2.7061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7241 0.1091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5812 2.7758 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0053 1.3521 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5548 1.8673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9334 -2.5793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7687 0.6273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7042 1.3204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3064 1.3839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0819 0.9776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9221 2.3377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9974 -1.1612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4294 -0.0715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 36 1 0 0 0 0 6 36 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 24 2 0 0 0 0 12 25 2 0 0 0 0 13 28 2 0 0 0 0 14 29 2 0 0 0 0 15 20 1 0 0 0 0 16 23 2 0 0 0 0 17 19 2 0 0 0 0 17 37 1 0 0 0 0 18 23 1 0 0 0 0 18 47 1 0 0 0 0 19 32 1 0 0 0 0 20 37 1 6 0 0 0 21 41 2 0 0 0 0 21 47 1 0 0 0 0 22 42 2 0 0 0 0 22 48 1 0 0 0 0 23 33 1 0 0 0 0 24 28 1 0 0 0 0 24 34 1 0 0 0 0 25 29 1 0 0 0 0 25 35 1 0 0 0 0 26 16 1 6 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 27 15 1 1 0 0 0 27 30 1 0 0 0 0 27 36 1 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 36 1 1 0 0 0 31 37 1 0 0 0 0 31 43 2 0 0 0 0 32 38 1 1 0 0 0 32 48 1 0 0 0 0 33 38 1 1 0 0 0 33 49 1 0 0 0 0 34 40 2 3 0 0 0 34 44 1 0 0 0 0 35 45 2 0 0 0 0 35 49 1 0 0 0 0 37 38 1 1 0 0 0 38 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	670.29
Volume:	681.297
LogP:	5.021
LogD:	3.509
LogS:	-5.505
# Rotatable Bonds:	11
TPSA:	171.32
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	6.066
Fsp3:	0.447
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:	-5.282
MDCK Permeability:	2.4641567506478168e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.523
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	84.53167724609375%
Volume Distribution (VD):	1.836
Pgp-substrate:	10.042710304260254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.836
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.339
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	3.427
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.908
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.737
Skin Sensitization:	0.693
Carcinogencity:	0.154
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC259791

Natural Product ID:	NPC259791
*Common Name:**	XGDQLBVXHZZHMQ-OXHJOSHZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XGDQLBVXHZZHMQ-OXHJOSHZSA-N
Standard InCHI:	InChI=1S/C38H42N2O9/c1-19-17-37-20(2)15-27-30(36(27,5)6)26(31(37)43)16-23(18-47-21(3)41)33(38(37,46)32(19)48-22(4)42)49-35(45)25-12-8-10-14-29(25)40-34(44)24-11-7-9-13-28(24)39/h7-14,16-17,20,26-27,30,32-33,46H,15,18,39H2,1-6H3,(H,40,44)/t20-,26+,27-,30+,32+,33-,37+,38-/m1/s1
SMILES:	CC1=C[C@]23[C@H](C)C[C@@H]4[C@H]([C@H](C=C(COC(=O)C)[C@H]([C@@]3([C@H]1OC(=O)C)O)OC(=O)c1ccccc1N=C(c1ccccc1N)O)C2=O)C4(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556121
PubChem CID:	44139664
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3469	Organism	Biomphalaria glabrata	Biomphalaria glabrata	LC50	=	0.0183	ug.mL-1	PMID[530427]

☑ 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 NPC259791 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	253
0.1-0.2	1107
0.2-0.3	3473
0.3-0.4	9506
0.4-0.5	14630
0.5-0.6	12604
0.6-0.7	1085
0.7-0.8	21
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476212
1.0	High Similarity	NPC476129
1.0	High Similarity	NPC476206
1.0	High Similarity	NPC476207
1.0	High Similarity	NPC476256
1.0	High Similarity	NPC476205
1.0	High Similarity	NPC476257
0.9942	High Similarity	NPC476218
0.9942	High Similarity	NPC108804
0.8229	Intermediate Similarity	NPC136573
0.8229	Intermediate Similarity	NPC176371
0.822	Intermediate Similarity	NPC90358
0.822	Intermediate Similarity	NPC107828
0.8105	Intermediate Similarity	NPC198205
0.8105	Intermediate Similarity	NPC21483
0.8073	Intermediate Similarity	NPC311054
0.8073	Intermediate Similarity	NPC112752
0.8021	Intermediate Similarity	NPC198390
0.7803	Intermediate Similarity	NPC134131
0.7803	Intermediate Similarity	NPC25043
0.755	Intermediate Similarity	NPC475223
0.7512	Intermediate Similarity	NPC246983
0.7512	Intermediate Similarity	NPC475448
0.7341	Intermediate Similarity	NPC52523
0.7341	Intermediate Similarity	NPC217673
0.729	Intermediate Similarity	NPC473667
0.7243	Intermediate Similarity	NPC106593
0.7222	Intermediate Similarity	NPC453583
0.7222	Intermediate Similarity	NPC473300
0.7222	Intermediate Similarity	NPC475336
0.7186	Intermediate Similarity	NPC67246
0.7186	Intermediate Similarity	NPC33372
0.7183	Intermediate Similarity	NPC223590
0.7175	Intermediate Similarity	NPC242355
0.7164	Intermediate Similarity	NPC321072
0.7164	Intermediate Similarity	NPC215892
0.7164	Intermediate Similarity	NPC242662
0.7164	Intermediate Similarity	NPC191193
0.715	Intermediate Similarity	NPC140311
0.7143	Intermediate Similarity	NPC476467
0.7136	Intermediate Similarity	NPC317882
0.7136	Intermediate Similarity	NPC471754
0.7135	Intermediate Similarity	NPC11410
0.7129	Intermediate Similarity	NPC471606
0.7129	Intermediate Similarity	NPC208553
0.7129	Intermediate Similarity	NPC181964
0.712	Intermediate Similarity	NPC477100
0.712	Intermediate Similarity	NPC477098
0.7097	Intermediate Similarity	NPC233727
0.7094	Intermediate Similarity	NPC473490
0.7094	Intermediate Similarity	NPC473558
0.7089	Intermediate Similarity	NPC473837
0.7062	Intermediate Similarity	NPC473301
0.7056	Intermediate Similarity	NPC187494
0.705	Intermediate Similarity	NPC275170
0.705	Intermediate Similarity	NPC473400
0.705	Intermediate Similarity	NPC206211
0.705	Intermediate Similarity	NPC306001
0.705	Intermediate Similarity	NPC471629
0.705	Intermediate Similarity	NPC324251
0.7049	Intermediate Similarity	NPC25484
0.7049	Intermediate Similarity	NPC232583
0.7042	Intermediate Similarity	NPC193361
0.7042	Intermediate Similarity	NPC62844
0.7035	Intermediate Similarity	NPC327699
0.7033	Intermediate Similarity	NPC132652
0.7033	Intermediate Similarity	NPC205389
0.7032	Intermediate Similarity	NPC14116
0.7032	Intermediate Similarity	NPC285411
0.7029	Intermediate Similarity	NPC153617
0.7027	Intermediate Similarity	NPC114808
0.7	Intermediate Similarity	NPC134384
0.7	Intermediate Similarity	NPC311196
0.6981	Remote Similarity	NPC323551
0.6981	Remote Similarity	NPC280473
0.6977	Remote Similarity	NPC122235
0.6973	Remote Similarity	NPC22571
0.6973	Remote Similarity	NPC283875
0.6973	Remote Similarity	NPC469648
0.6973	Remote Similarity	NPC138641
0.6973	Remote Similarity	NPC233581
0.6973	Remote Similarity	NPC145649
0.6973	Remote Similarity	NPC469647
0.6957	Remote Similarity	NPC477099
0.6957	Remote Similarity	NPC477101
0.6957	Remote Similarity	NPC477097
0.6951	Remote Similarity	NPC238278
0.6948	Remote Similarity	NPC51008
0.6948	Remote Similarity	NPC41724
0.6944	Remote Similarity	NPC192658
0.6942	Remote Similarity	NPC472392
0.6932	Remote Similarity	NPC28836
0.6927	Remote Similarity	NPC316202
0.6927	Remote Similarity	NPC162613
0.6927	Remote Similarity	NPC87934
0.6927	Remote Similarity	NPC476749
0.6923	Remote Similarity	NPC289383
0.6915	Remote Similarity	NPC471623
0.6914	Remote Similarity	NPC233860
0.6908	Remote Similarity	NPC472391
0.6906	Remote Similarity	NPC95449
0.6906	Remote Similarity	NPC45307
0.6906	Remote Similarity	NPC82467
0.6898	Remote Similarity	NPC251139
0.689	Remote Similarity	NPC116862
0.6889	Remote Similarity	NPC474303
0.6889	Remote Similarity	NPC473497
0.6889	Remote Similarity	NPC475413
0.6889	Remote Similarity	NPC266374
0.6889	Remote Similarity	NPC187566
0.6885	Remote Similarity	NPC477095
0.6875	Remote Similarity	NPC472248
0.6872	Remote Similarity	NPC9905
0.6868	Remote Similarity	NPC34943
0.6866	Remote Similarity	NPC216428
0.6864	Remote Similarity	NPC477902
0.686	Remote Similarity	NPC472375
0.6851	Remote Similarity	NPC314287
0.6837	Remote Similarity	NPC9475
0.6836	Remote Similarity	NPC311492
0.683	Remote Similarity	NPC213143
0.6828	Remote Similarity	NPC472398
0.682	Remote Similarity	NPC62367
0.682	Remote Similarity	NPC319556
0.6818	Remote Similarity	NPC233692
0.6818	Remote Similarity	NPC239358
0.6816	Remote Similarity	NPC327511
0.6816	Remote Similarity	NPC205305
0.6816	Remote Similarity	NPC27721
0.6806	Remote Similarity	NPC189116
0.6802	Remote Similarity	NPC211920
0.6802	Remote Similarity	NPC475601
0.6802	Remote Similarity	NPC124029
0.6798	Remote Similarity	NPC200154
0.6793	Remote Similarity	NPC240115
0.6793	Remote Similarity	NPC170668
0.6793	Remote Similarity	NPC20255
0.6791	Remote Similarity	NPC165837
0.6789	Remote Similarity	NPC84815
0.6789	Remote Similarity	NPC301368
0.6786	Remote Similarity	NPC96801
0.6786	Remote Similarity	NPC150698
0.6782	Remote Similarity	NPC316405
0.6778	Remote Similarity	NPC53361
0.6778	Remote Similarity	NPC276652
0.6778	Remote Similarity	NPC121268
0.6776	Remote Similarity	NPC470189
0.6776	Remote Similarity	NPC40919
0.6774	Remote Similarity	NPC471016
0.6774	Remote Similarity	NPC125033
0.6771	Remote Similarity	NPC55744
0.677	Remote Similarity	NPC35208
0.677	Remote Similarity	NPC475426
0.676	Remote Similarity	NPC202729
0.6758	Remote Similarity	NPC183540
0.6754	Remote Similarity	NPC476750
0.6744	Remote Similarity	NPC226794
0.6742	Remote Similarity	NPC324898
0.6742	Remote Similarity	NPC298547
0.6742	Remote Similarity	NPC134937
0.6742	Remote Similarity	NPC250807
0.6742	Remote Similarity	NPC76565
0.6742	Remote Similarity	NPC57797
0.674	Remote Similarity	NPC475660
0.6739	Remote Similarity	NPC125882
0.6739	Remote Similarity	NPC92867
0.6739	Remote Similarity	NPC311825
0.6734	Remote Similarity	NPC475962
0.6729	Remote Similarity	NPC314834
0.6728	Remote Similarity	NPC42678
0.6728	Remote Similarity	NPC470306
0.6728	Remote Similarity	NPC477907
0.6728	Remote Similarity	NPC207531
0.6728	Remote Similarity	NPC477909
0.6727	Remote Similarity	NPC477912
0.6726	Remote Similarity	NPC476110
0.6726	Remote Similarity	NPC87152
0.6726	Remote Similarity	NPC228377
0.6726	Remote Similarity	NPC477787
0.6726	Remote Similarity	NPC328186
0.6726	Remote Similarity	NPC475600
0.6726	Remote Similarity	NPC122968
0.6726	Remote Similarity	NPC475631
0.6725	Remote Similarity	NPC253482
0.6722	Remote Similarity	NPC86772
0.6721	Remote Similarity	NPC477094
0.6721	Remote Similarity	NPC191387
0.6721	Remote Similarity	NPC153214
0.6721	Remote Similarity	NPC131966
0.6721	Remote Similarity	NPC477096
0.672	Remote Similarity	NPC93343
0.6714	Remote Similarity	NPC470190
0.6712	Remote Similarity	NPC475137
0.6712	Remote Similarity	NPC475498
0.6712	Remote Similarity	NPC473850
0.6711	Remote Similarity	NPC477906
0.6705	Remote Similarity	NPC316746
0.6704	Remote Similarity	NPC79699
0.6704	Remote Similarity	NPC472247
0.6704	Remote Similarity	NPC279637

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 NPC259791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	547
0.2-0.3	871
0.3-0.4	1857
0.4-0.5	3620
0.5-0.6	1940
0.6-0.7	135
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7129	Intermediate Similarity	NPD8485	Approved
0.7081	Intermediate Similarity	NPD2672	Discontinued
0.7024	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD8146	Phase 2
0.7	Intermediate Similarity	NPD8360	Approved
0.7	Intermediate Similarity	NPD8361	Approved
0.6985	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8435	Approved
0.6898	Remote Similarity	NPD2836	Approved
0.6875	Remote Similarity	NPD2821	Approved
0.6829	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7546	Discontinued
0.6667	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6874	Approved
0.6635	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8407	Phase 2
0.6605	Remote Similarity	NPD4506	Discontinued
0.6597	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4888	Discontinued
0.6576	Remote Similarity	NPD1625	Approved
0.6567	Remote Similarity	NPD8368	Discontinued
0.6488	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3795	Approved
0.6484	Remote Similarity	NPD3794	Approved
0.6477	Remote Similarity	NPD1593	Approved
0.6455	Remote Similarity	NPD4513	Discontinued
0.6442	Remote Similarity	NPD7570	Approved
0.6442	Remote Similarity	NPD5937	Approved
0.6442	Remote Similarity	NPD7569	Approved
0.642	Remote Similarity	NPD1574	Approved
0.6418	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8150	Discontinued
0.6406	Remote Similarity	NPD1514	Discontinued
0.6383	Remote Similarity	NPD4607	Approved
0.6368	Remote Similarity	NPD7878	Phase 2
0.6364	Remote Similarity	NPD8462	Phase 1
0.6359	Remote Similarity	NPD3154	Approved
0.6359	Remote Similarity	NPD6296	Discontinued
0.6359	Remote Similarity	NPD3170	Approved
0.6359	Remote Similarity	NPD3153	Approved
0.6359	Remote Similarity	NPD1626	Approved
0.6351	Remote Similarity	NPD5411	Discontinued
0.6351	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6758	Approved
0.6345	Remote Similarity	NPD5430	Discontinued
0.6344	Remote Similarity	NPD1189	Approved
0.6338	Remote Similarity	NPD7565	Approved
0.6337	Remote Similarity	NPD3965	Phase 1
0.6329	Remote Similarity	NPD4948	Discontinued
0.6323	Remote Similarity	NPD8404	Phase 2
0.6321	Remote Similarity	NPD3684	Discontinued
0.6321	Remote Similarity	NPD5003	Discontinued
0.6321	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7528	Approved
0.6303	Remote Similarity	NPD7256	Discontinued
0.6298	Remote Similarity	NPD2792	Approved
0.6298	Remote Similarity	NPD1898	Discontinued
0.6296	Remote Similarity	NPD6176	Phase 1
0.6292	Remote Similarity	NPD9567	Approved
0.6292	Remote Similarity	NPD553	Approved
0.6292	Remote Similarity	NPD552	Approved
0.6289	Remote Similarity	NPD2366	Approved
0.6277	Remote Similarity	NPD8067	Phase 3
0.6277	Remote Similarity	NPD2387	Approved
0.6269	Remote Similarity	NPD5086	Approved
0.625	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6287	Discontinued
0.625	Remote Similarity	NPD7795	Phase 2
0.625	Remote Similarity	NPD8325	Phase 3
0.625	Remote Similarity	NPD8326	Phase 3
0.6244	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6104	Discontinued
0.6243	Remote Similarity	NPD6185	Discontinued
0.6243	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3280	Approved
0.6234	Remote Similarity	NPD8468	Phase 2
0.6224	Remote Similarity	NPD7599	Phase 2
0.6218	Remote Similarity	NPD3399	Approved
0.6215	Remote Similarity	NPD4668	Phase 2
0.6211	Remote Similarity	NPD4041	Approved
0.6207	Remote Similarity	NPD7799	Discontinued
0.6204	Remote Similarity	NPD7476	Discontinued
0.6203	Remote Similarity	NPD9477	Approved
0.6203	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7600	Phase 2
0.6188	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5811	Approved
0.6183	Remote Similarity	NPD1109	Approved
0.6183	Remote Similarity	NPD1110	Approved
0.6182	Remote Similarity	NPD2510	Approved
0.6182	Remote Similarity	NPD2509	Approved
0.6178	Remote Similarity	NPD3352	Approved
0.6176	Remote Similarity	NPD6642	Approved
0.6176	Remote Similarity	NPD6641	Approved
0.6175	Remote Similarity	NPD6863	Phase 2
0.6175	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD5416	Discontinued
0.617	Remote Similarity	NPD2923	Approved
0.6166	Remote Similarity	NPD1230	Approved
0.6166	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5042	Phase 1
0.6158	Remote Similarity	NPD5466	Approved
0.6154	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.615	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.615	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.614	Remote Similarity	NPD53	Approved
0.614	Remote Similarity	NPD7778	Approved
0.614	Remote Similarity	NPD7777	Approved
0.6133	Remote Similarity	NPD3394	Approved
0.6133	Remote Similarity	NPD8160	Phase 2
0.6133	Remote Similarity	NPD3393	Approved
0.6133	Remote Similarity	NPD3389	Approved
0.613	Remote Similarity	NPD3925	Approved
0.6123	Remote Similarity	NPD6770	Approved
0.6119	Remote Similarity	NPD3947	Discontinued
0.6119	Remote Similarity	NPD7891	Discontinued
0.6119	Remote Similarity	NPD2034	Discontinued
0.6117	Remote Similarity	NPD6879	Phase 2
0.6117	Remote Similarity	NPD6878	Phase 2
0.6117	Remote Similarity	NPD3823	Discontinued
0.6114	Remote Similarity	NPD2565	Phase 2
0.6114	Remote Similarity	NPD4259	Approved
0.6114	Remote Similarity	NPD2564	Approved
0.6114	Remote Similarity	NPD4258	Approved
0.6114	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7244	Discontinued
0.6106	Remote Similarity	NPD3436	Approved
0.6105	Remote Similarity	NPD2435	Approved
0.6105	Remote Similarity	NPD2575	Approved
0.6103	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD6823	Phase 2
0.6099	Remote Similarity	NPD7801	Approved
0.6099	Remote Similarity	NPD4493	Discontinued
0.6089	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6519	Phase 2
0.6082	Remote Similarity	NPD7606	Phase 3
0.6073	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6962	Phase 2
0.6063	Remote Similarity	NPD7584	Approved
0.6061	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD6870	Phase 1
0.6054	Remote Similarity	NPD5182	Approved
0.6054	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5184	Approved
0.6054	Remote Similarity	NPD5185	Approved
0.6051	Remote Similarity	NPD7239	Suspended
0.6051	Remote Similarity	NPD4003	Phase 3
0.605	Remote Similarity	NPD8008	Approved
0.605	Remote Similarity	NPD955	Approved
0.605	Remote Similarity	NPD8007	Approved
0.6043	Remote Similarity	NPD1532	Approved
0.6043	Remote Similarity	NPD2670	Approved
0.6042	Remote Similarity	NPD7236	Approved
0.6038	Remote Similarity	NPD5928	Phase 1
0.6037	Remote Similarity	NPD5609	Approved
0.6037	Remote Similarity	NPD5608	Approved
0.6036	Remote Similarity	NPD4082	Approved
0.6034	Remote Similarity	NPD7853	Phase 2
0.6034	Remote Similarity	NPD7186	Phase 3
0.6029	Remote Similarity	NPD43	Approved
0.6029	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6182	Approved
0.6029	Remote Similarity	NPD3952	Approved
0.6029	Remote Similarity	NPD3951	Phase 3
0.6029	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD7560	Approved
0.6017	Remote Similarity	NPD4373	Phase 2
0.601	Remote Similarity	NPD3435	Discontinued
0.6009	Remote Similarity	NPD6529	Discontinued
0.6009	Remote Similarity	NPD5076	Approved
0.6009	Remote Similarity	NPD5077	Approved
0.6	Remote Similarity	NPD1908	Phase 2
0.6	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7583	Approved
0.5991	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7496	Phase 2
0.599	Remote Similarity	NPD7295	Approved
0.5989	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7962	Phase 2
0.5981	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7972	Discontinued
0.5978	Remote Similarity	NPD4738	Phase 2
0.5978	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD1195	Approved
0.5967	Remote Similarity	NPD1036	Approved
0.5964	Remote Similarity	NPD7302	Phase 3
0.5964	Remote Similarity	NPD8423	Phase 2
0.5964	Remote Similarity	NPD7300	Phase 3
0.5964	Remote Similarity	NPD8399	Phase 1

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