NPASS Compound

Structure

NPC472197 OpenBabel07101718332D 43 43 0 0 1 0 0 0 0 0999 V2000 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 17 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 20 2 0 0 0 0 14 21 2 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 15 26 1 0 0 0 0 16 34 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 32 1 0 0 0 0 24 32 1 0 0 0 0 25 16 1 1 0 0 0 25 29 1 0 0 0 0 25 42 1 0 0 0 0 26 35 2 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 30 1 0 0 0 0 29 39 1 6 0 0 0 30 31 1 0 0 0 0 30 40 1 1 0 0 0 31 33 1 0 0 0 0 31 41 1 1 0 0 0 32 43 1 0 0 0 0 33 42 1 0 0 0 0 33 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	700.48
Volume:	743.394
LogP:	4.111
LogD:	4.083
LogS:	-4.335
# Rotatable Bonds:	20
TPSA:	197.37
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.086
Synthetic Accessibility Score:	5.799
Fsp3:	0.816
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.908
MDCK Permeability:	0.00011609744979068637
Pgp-inhibitor:	0.759
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.172

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	86.4179458618164%
Volume Distribution (VD):	0.711
Pgp-substrate:	5.617717266082764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.673
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	5.996
Half-life (T1/2):	0.487

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.128
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC472197

Natural Product ID:	NPC472197
*Common Name:**	JZGZPCJLZNDPKD-BRBNDELHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JZGZPCJLZNDPKD-BRBNDELHSA-N
Standard InCHI:	InChI=1S/C33H60O10/c1-10-17(2)11-18(3)12-23(8)32(43-33-31(41)30(40)29(39)25(16-34)42-33)24(9)14-21(6)27(37)19(4)13-20(5)28(38)22(7)15-26(35)36/h13-14,17-19,22-25,27-34,37-41H,10-12,15-16H2,1-9H3,(H,35,36)/b20-13+,21-14+/t17?,18?,19?,22?,23?,24?,25-,27?,28?,29-,30+,31+,32?,33+/m1/s1
SMILES:	CCC(CC(CC(C(C(/C=C(/C(C(/C=C(/C(C(CC(=O)O)C)O)C)C)O)C)C)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@@H]1O)O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3344127
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO33169	bionectria ochroleuca	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302529]

☑ 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	2
Others	5

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	100000.0	nM	PMID[552024]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	5000.0	nM	PMID[552024]
NPT20	Organism	Candida albicans	Candida albicans	Ratio	=	0.25	n.a.	PMID[552024]
NPT20	Organism	Candida albicans	Candida albicans	MIC=>80	>	100.0	uM	PMID[552024]
NPT20	Organism	Candida albicans	Candida albicans	MIC=>80	=	5.0	uM	PMID[552024]
NPT20	Organism	Candida albicans	Candida albicans	Ratio	<	0.05	n.a.	PMID[552024]
NPT20	Organism	Candida albicans	Candida albicans	FICI	<	0.3	n.a.	PMID[552024]

☑ 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 NPC472197 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	195
0.1-0.2	1194
0.2-0.3	4451
0.3-0.4	9421
0.4-0.5	13491
0.5-0.6	7784
0.6-0.7	5291
0.7-0.8	828
0.8-0.85	32
0.85-0.9	6
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.954	High Similarity	NPC472199
0.9326	High Similarity	NPC472198
0.9	High Similarity	NPC472195
0.9	High Similarity	NPC320089
0.9	High Similarity	NPC238090
0.9	High Similarity	NPC472196
0.8901	High Similarity	NPC159698
0.8764	High Similarity	NPC137368
0.871	High Similarity	NPC54731
0.8511	High Similarity	NPC306041
0.8391	Intermediate Similarity	NPC236649
0.8391	Intermediate Similarity	NPC21693
0.828	Intermediate Similarity	NPC9447
0.8256	Intermediate Similarity	NPC133377
0.8229	Intermediate Similarity	NPC476612
0.8229	Intermediate Similarity	NPC476613
0.8222	Intermediate Similarity	NPC477747
0.8222	Intermediate Similarity	NPC477746
0.8202	Intermediate Similarity	NPC69469
0.8202	Intermediate Similarity	NPC473500
0.8202	Intermediate Similarity	NPC156089
0.8202	Intermediate Similarity	NPC38295
0.8202	Intermediate Similarity	NPC470313
0.8172	Intermediate Similarity	NPC313670
0.8163	Intermediate Similarity	NPC154127
0.8144	Intermediate Similarity	NPC203627
0.814	Intermediate Similarity	NPC110813
0.8125	Intermediate Similarity	NPC474297
0.8081	Intermediate Similarity	NPC201191
0.8081	Intermediate Similarity	NPC223834
0.8077	Intermediate Similarity	NPC174836
0.8061	Intermediate Similarity	NPC473146
0.8058	Intermediate Similarity	NPC83005
0.8041	Intermediate Similarity	NPC472290
0.8022	Intermediate Similarity	NPC471494
0.8021	Intermediate Similarity	NPC36954
0.7981	Intermediate Similarity	NPC297945
0.7981	Intermediate Similarity	NPC126897
0.798	Intermediate Similarity	NPC476611
0.798	Intermediate Similarity	NPC298255
0.798	Intermediate Similarity	NPC28304
0.7979	Intermediate Similarity	NPC202886
0.7959	Intermediate Similarity	NPC472015
0.7955	Intermediate Similarity	NPC321728
0.7941	Intermediate Similarity	NPC293512
0.7938	Intermediate Similarity	NPC143446
0.7938	Intermediate Similarity	NPC241911
0.7935	Intermediate Similarity	NPC311163
0.7925	Intermediate Similarity	NPC181145
0.7921	Intermediate Similarity	NPC470768
0.7921	Intermediate Similarity	NPC469869
0.7917	Intermediate Similarity	NPC71589
0.7912	Intermediate Similarity	NPC266718
0.7895	Intermediate Similarity	NPC235051
0.7895	Intermediate Similarity	NPC477749
0.7879	Intermediate Similarity	NPC306344
0.7879	Intermediate Similarity	NPC22149
0.7879	Intermediate Similarity	NPC255677
0.7872	Intermediate Similarity	NPC477748
0.787	Intermediate Similarity	NPC234522
0.7865	Intermediate Similarity	NPC163362
0.7865	Intermediate Similarity	NPC127295
0.7864	Intermediate Similarity	NPC392
0.7864	Intermediate Similarity	NPC177524
0.7864	Intermediate Similarity	NPC219900
0.7857	Intermediate Similarity	NPC263674
0.7857	Intermediate Similarity	NPC261372
0.7857	Intermediate Similarity	NPC474194
0.7857	Intermediate Similarity	NPC40812
0.7857	Intermediate Similarity	NPC236580
0.7857	Intermediate Similarity	NPC304445
0.7857	Intermediate Similarity	NPC58267
0.7849	Intermediate Similarity	NPC86005
0.7849	Intermediate Similarity	NPC477959
0.7843	Intermediate Similarity	NPC476740
0.7843	Intermediate Similarity	NPC476738
0.7835	Intermediate Similarity	NPC108141
0.783	Intermediate Similarity	NPC311592
0.783	Intermediate Similarity	NPC75167
0.783	Intermediate Similarity	NPC293658
0.783	Intermediate Similarity	NPC474410
0.7822	Intermediate Similarity	NPC234304
0.7822	Intermediate Similarity	NPC118761
0.7822	Intermediate Similarity	NPC197541
0.7822	Intermediate Similarity	NPC309398
0.7822	Intermediate Similarity	NPC267869
0.7822	Intermediate Similarity	NPC284929
0.7812	Intermediate Similarity	NPC476300
0.7812	Intermediate Similarity	NPC478036
0.7812	Intermediate Similarity	NPC475912
0.7812	Intermediate Similarity	NPC478037
0.7812	Intermediate Similarity	NPC61201
0.781	Intermediate Similarity	NPC191763
0.78	Intermediate Similarity	NPC475655
0.78	Intermediate Similarity	NPC67296
0.78	Intermediate Similarity	NPC57586
0.78	Intermediate Similarity	NPC154132
0.78	Intermediate Similarity	NPC20673
0.78	Intermediate Similarity	NPC471637
0.78	Intermediate Similarity	NPC2313
0.78	Intermediate Similarity	NPC475157
0.78	Intermediate Similarity	NPC473332
0.7789	Intermediate Similarity	NPC473904
0.7789	Intermediate Similarity	NPC303451
0.7789	Intermediate Similarity	NPC6414
0.7788	Intermediate Similarity	NPC118225
0.7788	Intermediate Similarity	NPC315836
0.7788	Intermediate Similarity	NPC313668
0.7778	Intermediate Similarity	NPC56071
0.7778	Intermediate Similarity	NPC187268
0.7778	Intermediate Similarity	NPC70733
0.7766	Intermediate Similarity	NPC470137
0.7757	Intermediate Similarity	NPC472274
0.7755	Intermediate Similarity	NPC165332
0.7755	Intermediate Similarity	NPC180722
0.7755	Intermediate Similarity	NPC476315
0.7755	Intermediate Similarity	NPC195645
0.7745	Intermediate Similarity	NPC86095
0.7745	Intermediate Similarity	NPC470104
0.7742	Intermediate Similarity	NPC47937
0.7742	Intermediate Similarity	NPC208473
0.7736	Intermediate Similarity	NPC46388
0.7736	Intermediate Similarity	NPC256798
0.7736	Intermediate Similarity	NPC116794
0.7736	Intermediate Similarity	NPC128925
0.7736	Intermediate Similarity	NPC37739
0.7732	Intermediate Similarity	NPC256368
0.7727	Intermediate Similarity	NPC48692
0.7723	Intermediate Similarity	NPC13171
0.7723	Intermediate Similarity	NPC222062
0.7723	Intermediate Similarity	NPC473596
0.7723	Intermediate Similarity	NPC261117
0.7723	Intermediate Similarity	NPC313569
0.7723	Intermediate Similarity	NPC310804
0.7723	Intermediate Similarity	NPC250545
0.7723	Intermediate Similarity	NPC195510
0.7717	Intermediate Similarity	NPC475035
0.7717	Intermediate Similarity	NPC288471
0.7714	Intermediate Similarity	NPC274507
0.7708	Intermediate Similarity	NPC470379
0.7708	Intermediate Similarity	NPC470373
0.7708	Intermediate Similarity	NPC30515
0.7708	Intermediate Similarity	NPC184463
0.77	Intermediate Similarity	NPC469870
0.77	Intermediate Similarity	NPC244878
0.77	Intermediate Similarity	NPC469871
0.7692	Intermediate Similarity	NPC295389
0.7684	Intermediate Similarity	NPC139418
0.7677	Intermediate Similarity	NPC278506
0.767	Intermediate Similarity	NPC470767
0.767	Intermediate Similarity	NPC315070
0.767	Intermediate Similarity	NPC470763
0.767	Intermediate Similarity	NPC472749
0.767	Intermediate Similarity	NPC472751
0.7667	Intermediate Similarity	NPC100697
0.7664	Intermediate Similarity	NPC189884
0.7664	Intermediate Similarity	NPC271138
0.7664	Intermediate Similarity	NPC264153
0.7664	Intermediate Similarity	NPC47063
0.7664	Intermediate Similarity	NPC204458
0.7664	Intermediate Similarity	NPC269315
0.7664	Intermediate Similarity	NPC138334
0.766	Intermediate Similarity	NPC179659
0.766	Intermediate Similarity	NPC475037
0.7658	Intermediate Similarity	NPC170880
0.7658	Intermediate Similarity	NPC183353
0.7658	Intermediate Similarity	NPC469812
0.7653	Intermediate Similarity	NPC14961
0.7653	Intermediate Similarity	NPC270013
0.7653	Intermediate Similarity	NPC471141
0.7653	Intermediate Similarity	NPC469543
0.7647	Intermediate Similarity	NPC151516
0.7647	Intermediate Similarity	NPC473816
0.7647	Intermediate Similarity	NPC197736
0.7647	Intermediate Similarity	NPC473148
0.7647	Intermediate Similarity	NPC474581
0.7647	Intermediate Similarity	NPC475367
0.7642	Intermediate Similarity	NPC297208
0.7642	Intermediate Similarity	NPC30397
0.7642	Intermediate Similarity	NPC235841
0.7642	Intermediate Similarity	NPC211798
0.7642	Intermediate Similarity	NPC108748
0.7642	Intermediate Similarity	NPC473481
0.7634	Intermediate Similarity	NPC182383
0.7634	Intermediate Similarity	NPC242233
0.7629	Intermediate Similarity	NPC320552
0.7629	Intermediate Similarity	NPC475173
0.7629	Intermediate Similarity	NPC473723
0.7629	Intermediate Similarity	NPC473663
0.7629	Intermediate Similarity	NPC473561
0.7624	Intermediate Similarity	NPC198992
0.7619	Intermediate Similarity	NPC204407
0.7619	Intermediate Similarity	NPC237503
0.7619	Intermediate Similarity	NPC137917
0.7619	Intermediate Similarity	NPC40728
0.7619	Intermediate Similarity	NPC306746
0.7619	Intermediate Similarity	NPC57362
0.7619	Intermediate Similarity	NPC167383
0.7615	Intermediate Similarity	NPC471547
0.7604	Intermediate Similarity	NPC476004

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 NPC472197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1637
0.2-0.3	3766
0.3-0.4	2286
0.4-0.5	875
0.5-0.6	315
0.6-0.7	91
0.7-0.8	14
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD46	Approved
0.837	Intermediate Similarity	NPD6698	Approved
0.828	Intermediate Similarity	NPD7983	Approved
0.8144	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD6686	Approved
0.7755	Intermediate Similarity	NPD7839	Suspended
0.7658	Intermediate Similarity	NPD8515	Approved
0.7658	Intermediate Similarity	NPD8517	Approved
0.7658	Intermediate Similarity	NPD8513	Phase 3
0.7658	Intermediate Similarity	NPD8516	Approved
0.7604	Intermediate Similarity	NPD7838	Discovery
0.7304	Intermediate Similarity	NPD8342	Approved
0.7304	Intermediate Similarity	NPD8340	Approved
0.7304	Intermediate Similarity	NPD8341	Approved
0.7304	Intermediate Similarity	NPD8299	Approved
0.729	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7154	Phase 3
0.7232	Intermediate Similarity	NPD7641	Discontinued
0.7193	Intermediate Similarity	NPD8444	Approved
0.7113	Intermediate Similarity	NPD4250	Approved
0.7113	Intermediate Similarity	NPD4251	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.7103	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5779	Approved
0.71	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8451	Approved
0.7069	Intermediate Similarity	NPD7830	Approved
0.7069	Intermediate Similarity	NPD7829	Approved
0.7034	Intermediate Similarity	NPD8448	Approved
0.7034	Intermediate Similarity	NPD8074	Phase 3
0.701	Intermediate Similarity	NPD4249	Approved
0.6991	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8328	Phase 3
0.6923	Remote Similarity	NPD7642	Approved
0.6915	Remote Similarity	NPD4820	Approved
0.6915	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD4821	Approved
0.6915	Remote Similarity	NPD4819	Approved
0.6909	Remote Similarity	NPD6371	Approved
0.6882	Remote Similarity	NPD4271	Approved
0.6882	Remote Similarity	NPD4268	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.6875	Remote Similarity	NPD5362	Discontinued
0.686	Remote Similarity	NPD8390	Approved
0.686	Remote Similarity	NPD8391	Approved
0.686	Remote Similarity	NPD8392	Approved
0.6842	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7507	Approved
0.6804	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5344	Discontinued
0.6771	Remote Similarity	NPD4269	Approved
0.6771	Remote Similarity	NPD4270	Approved
0.6752	Remote Similarity	NPD8033	Approved
0.6733	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD7319	Approved
0.6638	Remote Similarity	NPD7327	Approved
0.6638	Remote Similarity	NPD7328	Approved
0.6634	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6101	Approved
0.661	Remote Similarity	NPD8378	Approved
0.661	Remote Similarity	NPD8335	Approved
0.661	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8379	Approved
0.661	Remote Similarity	NPD8296	Approved
0.661	Remote Similarity	NPD8380	Approved
0.6607	Remote Similarity	NPD6421	Discontinued
0.6604	Remote Similarity	NPD4225	Approved
0.6598	Remote Similarity	NPD6435	Approved
0.6581	Remote Similarity	NPD7516	Approved
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5363	Approved
0.6566	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4252	Approved
0.6555	Remote Similarity	NPD8080	Discontinued
0.6531	Remote Similarity	NPD5331	Approved
0.6531	Remote Similarity	NPD5332	Approved
0.6529	Remote Similarity	NPD8273	Phase 1
0.6526	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6411	Approved
0.6495	Remote Similarity	NPD4790	Discontinued
0.6495	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD7503	Approved
0.6408	Remote Similarity	NPD5785	Approved
0.6392	Remote Similarity	NPD5368	Approved
0.6389	Remote Similarity	NPD6648	Approved
0.6389	Remote Similarity	NPD7639	Approved
0.6389	Remote Similarity	NPD7640	Approved
0.6381	Remote Similarity	NPD5282	Discontinued
0.6346	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5370	Suspended
0.6296	Remote Similarity	NPD7638	Approved
0.6286	Remote Similarity	NPD6399	Phase 3
0.6279	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7524	Approved
0.6273	Remote Similarity	NPD8086	Approved
0.6273	Remote Similarity	NPD8085	Approved
0.6273	Remote Similarity	NPD8139	Approved
0.6273	Remote Similarity	NPD8082	Approved
0.6273	Remote Similarity	NPD8084	Approved
0.6273	Remote Similarity	NPD8083	Approved
0.6273	Remote Similarity	NPD8138	Approved
0.6216	Remote Similarity	NPD8276	Approved
0.6216	Remote Similarity	NPD8275	Approved
0.6211	Remote Similarity	NPD8039	Approved
0.621	Remote Similarity	NPD8293	Discontinued
0.6207	Remote Similarity	NPD6053	Discontinued
0.6202	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3197	Phase 1
0.6176	Remote Similarity	NPD6422	Discontinued
0.6168	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8081	Approved
0.616	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD1695	Approved
0.6154	Remote Similarity	NPD896	Approved
0.6154	Remote Similarity	NPD897	Approved
0.6154	Remote Similarity	NPD898	Approved
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7115	Discovery
0.6134	Remote Similarity	NPD7500	Approved
0.6129	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD8393	Approved
0.6087	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8266	Approved
0.6066	Remote Similarity	NPD8269	Approved
0.6066	Remote Similarity	NPD8268	Approved
0.6066	Remote Similarity	NPD8267	Approved
0.6055	Remote Similarity	NPD7902	Approved
0.604	Remote Similarity	NPD6695	Phase 3
0.604	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3669	Approved
0.6034	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD8415	Approved
0.5963	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7750	Discontinued
0.596	Remote Similarity	NPD7329	Approved
0.5943	Remote Similarity	NPD3168	Discontinued
0.5932	Remote Similarity	NPD8297	Approved
0.5932	Remote Similarity	NPD6882	Approved
0.5929	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7748	Approved
0.592	Remote Similarity	NPD7492	Approved
0.5918	Remote Similarity	NPD4756	Discovery
0.5913	Remote Similarity	NPD8140	Approved
0.5913	Remote Similarity	NPD8307	Discontinued
0.5906	Remote Similarity	NPD8337	Approved
0.5906	Remote Similarity	NPD8336	Approved
0.5873	Remote Similarity	NPD6616	Approved
0.5868	Remote Similarity	NPD6009	Approved
0.5868	Remote Similarity	NPD7505	Discontinued
0.5854	Remote Similarity	NPD6054	Approved
0.5854	Remote Similarity	NPD6059	Approved
0.5854	Remote Similarity	NPD6319	Approved
0.5841	Remote Similarity	NPD7632	Discontinued
0.584	Remote Similarity	NPD6067	Discontinued
0.5833	Remote Similarity	NPD3181	Approved
0.5827	Remote Similarity	NPD7078	Approved
0.5826	Remote Similarity	NPD5048	Discontinued
0.5812	Remote Similarity	NPD6373	Approved
0.5812	Remote Similarity	NPD8305	Approved
0.5812	Remote Similarity	NPD8306	Approved
0.5812	Remote Similarity	NPD6372	Approved
0.58	Remote Similarity	NPD6929	Approved
0.5798	Remote Similarity	NPD6430	Approved
0.5798	Remote Similarity	NPD6429	Approved
0.5784	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7900	Approved
0.5778	Remote Similarity	NPD368	Approved
0.5776	Remote Similarity	NPD6685	Approved
0.5776	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7260	Phase 2
0.5766	Remote Similarity	NPD6083	Phase 2
0.5766	Remote Similarity	NPD6084	Phase 2
0.5763	Remote Similarity	NPD8087	Discontinued
0.5761	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6925	Approved
0.5758	Remote Similarity	NPD5776	Phase 2
0.575	Remote Similarity	NPD4632	Approved
0.5743	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7332	Phase 2
0.5743	Remote Similarity	NPD6931	Approved
0.5743	Remote Similarity	NPD7514	Phase 3
0.5743	Remote Similarity	NPD6930	Phase 2
0.5741	Remote Similarity	NPD8035	Phase 2
0.5741	Remote Similarity	NPD8034	Phase 2
0.5741	Remote Similarity	NPD7515	Phase 2
0.5739	Remote Similarity	NPD8170	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data