NPASS Compound

Structure

NPC81137 OpenBabel07101719152D 38 41 0 0 0 0 0 0 0 0999 V2000 2.1241 -3.5793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7929 0.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6383 -1.4589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7929 -3.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1020 -3.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8108 -1.6363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9876 0.0453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7929 -0.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9474 -3.4113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4138 -0.7445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6383 0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4837 -0.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7929 -4.8756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1020 -4.8756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7817 -1.7383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9584 -0.0568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9474 -1.4589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4430 -0.6424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7898 -1.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4837 0.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9474 -5.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3555 -0.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1020 -0.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9927 -2.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9549 0.2030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6383 1.4696 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.3291 -1.4589 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.6383 -5.3637 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.7434 -5.3637 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.1787 -2.6301 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.5322 0.7330 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.3291 0.4934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9474 -6.3399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3263 -1.0506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2673 -2.9760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3519 1.0948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9211 -2.6244 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 1 37 1 0 0 0 0 2 8 2 0 0 0 0 2 11 1 0 0 0 0 3 8 1 0 0 0 0 3 12 2 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 5 14 2 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 20 2 0 0 0 0 11 26 1 0 0 0 0 12 20 1 0 0 0 0 12 27 1 0 0 0 0 13 21 2 0 0 0 0 13 28 1 0 0 0 0 14 21 1 0 0 0 0 14 29 1 0 0 0 0 15 22 2 0 0 0 0 15 30 1 0 0 0 0 16 22 1 0 0 0 0 16 31 1 0 0 0 0 17 23 2 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 38 1 0 0 0 0 24 35 2 0 0 0 0 24 37 1 0 0 0 0 25 36 2 0 0 0 0 25 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	897.57
Volume:	549.69
LogP:	6.672
LogD:	2.319
LogS:	-3.942
# Rotatable Bonds:	5
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	3.442
Fsp3:	0.04
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:	-6.14
MDCK Permeability:	1.789463021850679e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.951
20% Bioavailability (F20%):	0.718
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	108.45294189453125%
Volume Distribution (VD):	0.335
Pgp-substrate:	10.788813591003418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.812
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.706
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.548
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	-0.441
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.337
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.805
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.812
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.192
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC81137

Natural Product ID:	NPC81137
*Common Name:**	Cadiolide I
IUPAC Name:	methyl 2-[bis(3,5-dibromo-4-hydroxyphenyl)methylidene]-4-(3,5-dibromo-4-hydroxyphenyl)-5-oxofuran-3-carboxylate
Synonyms:	Cadiolide I
Standard InCHIKey:	BREHBFOCEMKNAS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H12Br6O7/c1-37-24(35)19-18(10-6-15(30)22(34)16(31)7-10)25(36)38-23(19)17(8-2-11(26)20(32)12(27)3-8)9-4-13(28)21(33)14(29)5-9/h2-7,32-34H,1H3
SMILES:	COC(=O)C1=C(c2cc(c(c(c2)Br)O)Br)C(=O)OC1=C(c1cc(c(c(c1)Br)O)Br)c1cc(c(c(c1)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204157
PubChem CID:	71461194
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22652254]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23145909]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747224]

☑ 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
IC50	4
MIC	8
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	2
NON-MOLECULAR	2
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	10800.0	nM	PMID[538827]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	52700.0	nM	PMID[538827]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	51200.0	nM	PMID[538827]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	10360.0	nM	PMID[538828]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[538827]
NPT2	Others	Unspecified		IC50	>	120000.0	nM	PMID[538827]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[538827]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	6.3	ug.mL-1	PMID[538827]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	1.6	ug.mL-1	PMID[538827]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	0.8	ug.mL-1	PMID[538827]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	0.8	ug.mL-1	PMID[538827]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.8	ug.mL-1	PMID[538827]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	MIC	=	50.0	ug.mL-1	PMID[538828]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	MIC	>	200.0	ug.mL-1	PMID[538828]

☑ 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 NPC81137 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	316
0.1-0.2	1649
0.2-0.3	4251
0.3-0.4	12106
0.4-0.5	7494
0.5-0.6	10562
0.6-0.7	6226
0.7-0.8	51
0.8-0.85	18
0.85-0.9	19
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9203	High Similarity	NPC147137
0.9071	High Similarity	NPC122599
0.9071	High Similarity	NPC270848
0.9071	High Similarity	NPC272868
0.8958	High Similarity	NPC235033
0.8958	High Similarity	NPC471235
0.8958	High Similarity	NPC470710
0.8958	High Similarity	NPC73132
0.8855	High Similarity	NPC105999
0.8841	High Similarity	NPC177967
0.8841	High Similarity	NPC471237
0.8647	High Similarity	NPC213414
0.8643	High Similarity	NPC197766
0.8643	High Similarity	NPC471236
0.854	High Similarity	NPC11449
0.8496	Intermediate Similarity	NPC296202
0.8421	Intermediate Similarity	NPC7830
0.8409	Intermediate Similarity	NPC180207
0.8333	Intermediate Similarity	NPC478071
0.8321	Intermediate Similarity	NPC78061
0.8321	Intermediate Similarity	NPC122359
0.8321	Intermediate Similarity	NPC159987
0.8222	Intermediate Similarity	NPC116562
0.7836	Intermediate Similarity	NPC128249
0.7832	Intermediate Similarity	NPC259017
0.7724	Intermediate Similarity	NPC471328
0.7721	Intermediate Similarity	NPC471033
0.7721	Intermediate Similarity	NPC311091
0.771	Intermediate Similarity	NPC54543
0.7537	Intermediate Similarity	NPC17693
0.7519	Intermediate Similarity	NPC473358
0.7518	Intermediate Similarity	NPC14141
0.7444	Intermediate Similarity	NPC79543
0.741	Intermediate Similarity	NPC100395
0.7372	Intermediate Similarity	NPC296526
0.7368	Intermediate Similarity	NPC471495
0.7343	Intermediate Similarity	NPC288945
0.7329	Intermediate Similarity	NPC214246
0.7305	Intermediate Similarity	NPC471486
0.7303	Intermediate Similarity	NPC19622
0.7303	Intermediate Similarity	NPC112789
0.7292	Intermediate Similarity	NPC137416
0.7267	Intermediate Similarity	NPC474535
0.726	Intermediate Similarity	NPC79332
0.726	Intermediate Similarity	NPC217431
0.7255	Intermediate Similarity	NPC275903
0.7246	Intermediate Similarity	NPC23402
0.7226	Intermediate Similarity	NPC471488
0.7222	Intermediate Similarity	NPC475697
0.7208	Intermediate Similarity	NPC184632
0.7172	Intermediate Similarity	NPC4164
0.7153	Intermediate Similarity	NPC473942
0.7152	Intermediate Similarity	NPC311742
0.7143	Intermediate Similarity	NPC2596
0.7143	Intermediate Similarity	NPC469930
0.7132	Intermediate Similarity	NPC183700
0.7114	Intermediate Similarity	NPC108553
0.7113	Intermediate Similarity	NPC233282
0.7111	Intermediate Similarity	NPC281604
0.7101	Intermediate Similarity	NPC33244
0.7071	Intermediate Similarity	NPC19290
0.7067	Intermediate Similarity	NPC173034
0.705	Intermediate Similarity	NPC285350
0.7042	Intermediate Similarity	NPC264976
0.7041	Intermediate Similarity	NPC470566
0.7037	Intermediate Similarity	NPC156648
0.7034	Intermediate Similarity	NPC236981
0.7032	Intermediate Similarity	NPC470986
0.702	Intermediate Similarity	NPC202743
0.7015	Intermediate Similarity	NPC127676
0.7007	Intermediate Similarity	NPC21162
0.7007	Intermediate Similarity	NPC63345
0.7007	Intermediate Similarity	NPC474476
0.7006	Intermediate Similarity	NPC271451
0.7	Intermediate Similarity	NPC470567
0.7	Intermediate Similarity	NPC51345
0.6993	Remote Similarity	NPC223616
0.6993	Remote Similarity	NPC243059
0.6993	Remote Similarity	NPC280827
0.6986	Remote Similarity	NPC89630
0.6985	Remote Similarity	NPC31274
0.6985	Remote Similarity	NPC206341
0.6981	Remote Similarity	NPC178097
0.6981	Remote Similarity	NPC25844
0.6978	Remote Similarity	NPC87069
0.6975	Remote Similarity	NPC135103
0.6974	Remote Similarity	NPC248150
0.6974	Remote Similarity	NPC106406
0.6972	Remote Similarity	NPC293424
0.6972	Remote Similarity	NPC94637
0.6968	Remote Similarity	NPC251681
0.6968	Remote Similarity	NPC243528
0.6966	Remote Similarity	NPC469927
0.6966	Remote Similarity	NPC283514
0.6966	Remote Similarity	NPC68167
0.6963	Remote Similarity	NPC70843
0.6957	Remote Similarity	NPC177576
0.6954	Remote Similarity	NPC186097
0.6954	Remote Similarity	NPC475009
0.6954	Remote Similarity	NPC475008
0.695	Remote Similarity	NPC128825
0.6948	Remote Similarity	NPC301915
0.6948	Remote Similarity	NPC261292
0.6934	Remote Similarity	NPC234639
0.6934	Remote Similarity	NPC88141
0.6933	Remote Similarity	NPC12694
0.6933	Remote Similarity	NPC470987
0.6933	Remote Similarity	NPC21378
0.6933	Remote Similarity	NPC30390
0.6929	Remote Similarity	NPC94217
0.6923	Remote Similarity	NPC183642
0.6923	Remote Similarity	NPC310370
0.6923	Remote Similarity	NPC328459
0.6923	Remote Similarity	NPC90522
0.6923	Remote Similarity	NPC9218
0.6923	Remote Similarity	NPC472801
0.6923	Remote Similarity	NPC170812
0.6923	Remote Similarity	NPC38483
0.6918	Remote Similarity	NPC97188
0.6918	Remote Similarity	NPC469953
0.6913	Remote Similarity	NPC196034
0.6913	Remote Similarity	NPC219923
0.6912	Remote Similarity	NPC260952
0.6901	Remote Similarity	NPC325295
0.6901	Remote Similarity	NPC76308
0.6899	Remote Similarity	NPC36181
0.6899	Remote Similarity	NPC66593
0.6899	Remote Similarity	NPC183824
0.6897	Remote Similarity	NPC198336
0.6894	Remote Similarity	NPC221352
0.6892	Remote Similarity	NPC110211
0.6892	Remote Similarity	NPC204579
0.6884	Remote Similarity	NPC321252
0.6884	Remote Similarity	NPC252544
0.6883	Remote Similarity	NPC90431
0.6875	Remote Similarity	NPC469498
0.6875	Remote Similarity	NPC470322
0.6875	Remote Similarity	NPC72977
0.6871	Remote Similarity	NPC265910
0.6871	Remote Similarity	NPC91475
0.6867	Remote Similarity	NPC99280
0.6867	Remote Similarity	NPC238309
0.6867	Remote Similarity	NPC477300
0.6867	Remote Similarity	NPC131684
0.6863	Remote Similarity	NPC204960
0.6863	Remote Similarity	NPC144051
0.6863	Remote Similarity	NPC28753
0.6863	Remote Similarity	NPC82225
0.6863	Remote Similarity	NPC159623
0.6863	Remote Similarity	NPC20560
0.6863	Remote Similarity	NPC18877
0.6863	Remote Similarity	NPC294593
0.6859	Remote Similarity	NPC71903
0.6857	Remote Similarity	NPC109241
0.6855	Remote Similarity	NPC470296
0.6855	Remote Similarity	NPC87609
0.6855	Remote Similarity	NPC94794
0.6855	Remote Similarity	NPC188632
0.6855	Remote Similarity	NPC112791
0.6855	Remote Similarity	NPC196459
0.6855	Remote Similarity	NPC470216
0.6855	Remote Similarity	NPC160839
0.6853	Remote Similarity	NPC27633
0.6853	Remote Similarity	NPC94298
0.6853	Remote Similarity	NPC249435
0.6852	Remote Similarity	NPC32197
0.6852	Remote Similarity	NPC52931
0.6842	Remote Similarity	NPC243404
0.6842	Remote Similarity	NPC185624
0.6842	Remote Similarity	NPC307289
0.6842	Remote Similarity	NPC76453
0.6842	Remote Similarity	NPC262359
0.6842	Remote Similarity	NPC52472
0.6839	Remote Similarity	NPC47815
0.6839	Remote Similarity	NPC231772
0.6839	Remote Similarity	NPC127447
0.6839	Remote Similarity	NPC22676
0.6839	Remote Similarity	NPC67349
0.6839	Remote Similarity	NPC475482
0.6839	Remote Similarity	NPC279676
0.6839	Remote Similarity	NPC194281
0.6839	Remote Similarity	NPC62907
0.6839	Remote Similarity	NPC473887
0.6839	Remote Similarity	NPC124784
0.6839	Remote Similarity	NPC216940
0.6839	Remote Similarity	NPC198621
0.6839	Remote Similarity	NPC29353
0.6839	Remote Similarity	NPC234133
0.6838	Remote Similarity	NPC69332
0.6838	Remote Similarity	NPC29989
0.6838	Remote Similarity	NPC95178
0.6838	Remote Similarity	NPC188677
0.6835	Remote Similarity	NPC285550
0.6835	Remote Similarity	NPC250755
0.6835	Remote Similarity	NPC26238
0.6832	Remote Similarity	NPC12305
0.6831	Remote Similarity	NPC131192
0.6831	Remote Similarity	NPC28951
0.6831	Remote Similarity	NPC325646
0.6824	Remote Similarity	NPC88403

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 NPC81137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	988
0.2-0.3	1492
0.3-0.4	3066
0.4-0.5	2110
0.5-0.6	1008
0.6-0.7	204
0.7-0.8	6
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
0.7707	Intermediate Similarity	NPD2296	Approved
0.7485	Intermediate Similarity	NPD4287	Approved
0.7375	Intermediate Similarity	NPD4288	Approved
0.7279	Intermediate Similarity	NPD3764	Approved
0.7211	Intermediate Similarity	NPD9718	Approved
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.6962	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.695	Remote Similarity	NPD9493	Approved
0.6939	Remote Similarity	NPD2797	Approved
0.6939	Remote Similarity	NPD1203	Approved
0.6933	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6233	Phase 2
0.6853	Remote Similarity	NPD1894	Discontinued
0.6853	Remote Similarity	NPD9545	Approved
0.6849	Remote Similarity	NPD1481	Phase 2
0.6821	Remote Similarity	NPD3268	Approved
0.6821	Remote Similarity	NPD2313	Discontinued
0.6816	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1535	Discovery
0.6774	Remote Similarity	NPD2799	Discontinued
0.6768	Remote Similarity	NPD7411	Suspended
0.6735	Remote Similarity	NPD9717	Approved
0.6732	Remote Similarity	NPD1240	Approved
0.6731	Remote Similarity	NPD5405	Approved
0.6731	Remote Similarity	NPD5404	Approved
0.6731	Remote Similarity	NPD5406	Approved
0.6731	Remote Similarity	NPD5408	Approved
0.6712	Remote Similarity	NPD3847	Discontinued
0.6711	Remote Similarity	NPD1164	Approved
0.6708	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7768	Phase 2
0.6691	Remote Similarity	NPD5909	Discontinued
0.6689	Remote Similarity	NPD6832	Phase 2
0.6688	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD5535	Approved
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1549	Phase 2
0.6645	Remote Similarity	NPD1607	Approved
0.6644	Remote Similarity	NPD1283	Approved
0.6605	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3266	Approved
0.66	Remote Similarity	NPD3267	Approved
0.6584	Remote Similarity	NPD7440	Discontinued
0.6582	Remote Similarity	NPD2346	Discontinued
0.6581	Remote Similarity	NPD6355	Discontinued
0.6573	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3749	Approved
0.6562	Remote Similarity	NPD4628	Phase 3
0.6562	Remote Similarity	NPD8166	Discontinued
0.6558	Remote Similarity	NPD6663	Approved
0.6556	Remote Similarity	NPD2798	Approved
0.6533	Remote Similarity	NPD3225	Approved
0.6522	Remote Similarity	NPD2309	Approved
0.6519	Remote Similarity	NPD1551	Phase 2
0.6513	Remote Similarity	NPD5736	Approved
0.651	Remote Similarity	NPD1608	Approved
0.6503	Remote Similarity	NPD1241	Discontinued
0.65	Remote Similarity	NPD74	Approved
0.65	Remote Similarity	NPD9266	Approved
0.6478	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1933	Approved
0.6471	Remote Similarity	NPD7075	Discontinued
0.6463	Remote Similarity	NPD6273	Approved
0.6452	Remote Similarity	NPD4062	Phase 3
0.645	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1281	Approved
0.6443	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1201	Approved
0.6442	Remote Similarity	NPD6799	Approved
0.6438	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9263	Approved
0.6429	Remote Similarity	NPD9264	Approved
0.6429	Remote Similarity	NPD7095	Approved
0.6429	Remote Similarity	NPD9267	Approved
0.6429	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1876	Approved
0.642	Remote Similarity	NPD6190	Approved
0.6419	Remote Similarity	NPD3019	Approved
0.6418	Remote Similarity	NPD2859	Approved
0.6418	Remote Similarity	NPD2860	Approved
0.6416	Remote Similarity	NPD6232	Discontinued
0.6412	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4307	Phase 2
0.6402	Remote Similarity	NPD2532	Approved
0.6402	Remote Similarity	NPD2534	Approved
0.6402	Remote Similarity	NPD2533	Approved
0.6402	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3972	Approved
0.6391	Remote Similarity	NPD7819	Suspended
0.6391	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1470	Approved
0.6375	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6971	Discontinued
0.6369	Remote Similarity	NPD230	Phase 1
0.6369	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD3748	Approved
0.6352	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD3226	Approved
0.6347	Remote Similarity	NPD7458	Discontinued
0.6347	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2934	Approved
0.6343	Remote Similarity	NPD2933	Approved
0.6338	Remote Similarity	NPD2067	Discontinued
0.6333	Remote Similarity	NPD422	Phase 1
0.6331	Remote Similarity	NPD6801	Discontinued
0.6331	Remote Similarity	NPD1934	Approved
0.6325	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2354	Approved
0.6312	Remote Similarity	NPD4476	Approved
0.6312	Remote Similarity	NPD2796	Approved
0.6312	Remote Similarity	NPD4477	Approved
0.631	Remote Similarity	NPD6502	Phase 2
0.631	Remote Similarity	NPD4380	Phase 2
0.631	Remote Similarity	NPD6599	Discontinued
0.6309	Remote Similarity	NPD2932	Approved
0.6309	Remote Similarity	NPD17	Approved
0.6307	Remote Similarity	NPD7473	Discontinued
0.6306	Remote Similarity	NPD2979	Phase 3
0.6301	Remote Similarity	NPD256	Approved
0.6301	Remote Similarity	NPD255	Approved
0.6294	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD411	Approved
0.6278	Remote Similarity	NPD2802	Phase 3
0.6277	Remote Similarity	NPD3020	Approved
0.6277	Remote Similarity	NPD1238	Approved
0.6266	Remote Similarity	NPD447	Suspended
0.6258	Remote Similarity	NPD4908	Phase 1
0.6258	Remote Similarity	NPD2614	Approved
0.6258	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6583	Phase 3
0.625	Remote Similarity	NPD6582	Phase 2
0.6242	Remote Similarity	NPD520	Approved
0.6242	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1511	Approved
0.6242	Remote Similarity	NPD7390	Discontinued
0.6242	Remote Similarity	NPD8032	Phase 2
0.6241	Remote Similarity	NPD3134	Approved
0.6234	Remote Similarity	NPD1019	Discontinued
0.6234	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD5647	Approved
0.6233	Remote Similarity	NPD9281	Approved
0.6233	Remote Similarity	NPD5951	Approved
0.6228	Remote Similarity	NPD5403	Approved
0.6224	Remote Similarity	NPD5451	Approved
0.6218	Remote Similarity	NPD7008	Discontinued
0.6214	Remote Similarity	NPD9244	Approved
0.6211	Remote Similarity	NPD2438	Suspended
0.6205	Remote Similarity	NPD5401	Approved
0.6205	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4060	Phase 1
0.6203	Remote Similarity	NPD943	Approved
0.62	Remote Similarity	NPD4626	Approved
0.6199	Remote Similarity	NPD2801	Approved
0.6197	Remote Similarity	NPD1358	Approved
0.6196	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD2800	Approved
0.6196	Remote Similarity	NPD1243	Approved
0.6188	Remote Similarity	NPD7097	Phase 1
0.6185	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7266	Discontinued
0.6173	Remote Similarity	NPD2353	Approved
0.6173	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD6959	Discontinued
0.617	Remote Similarity	NPD5048	Discontinued
0.6168	Remote Similarity	NPD1512	Approved
0.6168	Remote Similarity	NPD5049	Phase 3
0.6163	Remote Similarity	NPD3817	Phase 2
0.6163	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD4110	Phase 3
0.6158	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD6166	Phase 2
0.6158	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3455	Phase 2
0.6154	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD6234	Discontinued
0.6143	Remote Similarity	NPD9261	Approved
0.614	Remote Similarity	NPD37	Approved
0.6136	Remote Similarity	NPD1161	Approved
0.6135	Remote Similarity	NPD4534	Discontinued
0.6135	Remote Similarity	NPD5958	Discontinued
0.6133	Remote Similarity	NPD6559	Discontinued
0.6133	Remote Similarity	NPD1651	Approved
0.6131	Remote Similarity	NPD7427	Discontinued

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