NPASS Compound

Structure

NPC474281 OpenBabel07101719522D 35 40 0 0 1 0 0 0 0 0999 V2000 5.1488 5.6634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4601 4.6884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2432 -0.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7308 -0.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9931 2.2511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4601 0.7887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3044 0.3013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3237 2.1668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9931 4.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9931 3.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1488 1.7637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3044 1.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 3.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4619 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7715 -0.1862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1488 4.6884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3044 4.2010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4601 2.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7715 2.7386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3365 0.3580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 0.3013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.5775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3044 3.2260 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7715 1.7637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2817 0.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1488 2.7386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4601 1.7637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6158 1.2762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9272 1.2762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9272 0.3013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9272 3.2260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1253 -0.2150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4601 -0.1862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5730 0.7887 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 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 26 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 2 1 1 0 0 0 17 23 1 0 0 0 0 18 23 1 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 31 1 6 0 0 0 20 25 1 0 0 0 0 20 32 2 0 0 0 0 21 28 1 6 0 0 0 21 33 1 0 0 0 0 22 29 1 1 0 0 0 22 34 1 0 0 0 0 23 26 1 6 0 0 0 24 28 1 1 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 1 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 15 1 6 0 0 0 30 35 1 0 0 0 0 34 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	514.775
LogP:	4.57
LogD:	4.152
LogS:	-5.319
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	6.434
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.017
MDCK Permeability:	2.4059818315436132e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.869
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.32

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	84.13526153564453%
Volume Distribution (VD):	1.139
Pgp-substrate:	6.709025859832764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.805
CYP2C19-inhibitor:	0.16
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.322
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.886

ADMET: Excretion

Clearance (CL):	6.716
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.66
Human Hepatotoxicity (H-HT):	0.386
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.374
Carcinogencity:	0.543
Eye Corrosion:	0.031
Eye Irritation:	0.084
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC474281

Natural Product ID:	NPC474281
*Common Name:**	UBKYFSBPSQKPIB-CGPCQPRUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UBKYFSBPSQKPIB-CGPCQPRUSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-16-9-10-26(5)11-12-27(6)18(23(26)17(16)2)13-19(31)24-28(27,7)21(33)15-30-25(3,4)20(32)14-22(34-35-30)29(24,30)8/h13,16-17,19,21-24,31,33H,9-12,14-15H2,1-8H3/t16-,17+,19-,21-,22+,23+,24+,26-,27-,28-,29-,30-/m1/s1
SMILES:	C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=C[C@@H](O)[C@H]3[C@@]([C@@]1(CC2)C)(C)[C@H](O)C[C@@]12[C@]3(C)[C@@H](OO1)CC(=O)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464690
PubChem CID:	44567513
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
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	31900.0	nM	PMID[480364]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	31900.0	nM	PMID[480364]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	31900.0	nM	PMID[480364]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	31900.0	nM	PMID[480364]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	63800.0	nM	PMID[480364]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	14900.0	nM	PMID[480364]

☑ 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 NPC474281 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	212
0.1-0.2	1476
0.2-0.3	4809
0.3-0.4	9560
0.4-0.5	12455
0.5-0.6	6269
0.6-0.7	5025
0.7-0.8	2758
0.8-0.85	124
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8646	High Similarity	NPC69627
0.86	High Similarity	NPC189880
0.8586	High Similarity	NPC266899
0.8515	High Similarity	NPC174663
0.85	High Similarity	NPC476327
0.85	High Similarity	NPC476318
0.8485	Intermediate Similarity	NPC474529
0.8416	Intermediate Similarity	NPC472851
0.84	Intermediate Similarity	NPC272617
0.84	Intermediate Similarity	NPC473240
0.8365	Intermediate Similarity	NPC90177
0.835	Intermediate Similarity	NPC118964
0.8333	Intermediate Similarity	NPC164349
0.8333	Intermediate Similarity	NPC213412
0.8317	Intermediate Similarity	NPC132824
0.8317	Intermediate Similarity	NPC116457
0.83	Intermediate Similarity	NPC159365
0.8286	Intermediate Similarity	NPC201763
0.8283	Intermediate Similarity	NPC472978
0.8283	Intermediate Similarity	NPC155120
0.8283	Intermediate Similarity	NPC475708
0.8283	Intermediate Similarity	NPC471588
0.8283	Intermediate Similarity	NPC6255
0.8283	Intermediate Similarity	NPC288833
0.8283	Intermediate Similarity	NPC324341
0.8283	Intermediate Similarity	NPC228784
0.8283	Intermediate Similarity	NPC282616
0.8283	Intermediate Similarity	NPC966
0.8235	Intermediate Similarity	NPC190554
0.8229	Intermediate Similarity	NPC133954
0.8229	Intermediate Similarity	NPC274724
0.8218	Intermediate Similarity	NPC148523
0.8218	Intermediate Similarity	NPC139570
0.8218	Intermediate Similarity	NPC290481
0.82	Intermediate Similarity	NPC118490
0.8182	Intermediate Similarity	NPC130278
0.8182	Intermediate Similarity	NPC86372
0.8182	Intermediate Similarity	NPC172361
0.8182	Intermediate Similarity	NPC230332
0.8173	Intermediate Similarity	NPC256247
0.8155	Intermediate Similarity	NPC260149
0.8155	Intermediate Similarity	NPC58942
0.8144	Intermediate Similarity	NPC470955
0.8144	Intermediate Similarity	NPC74363
0.8144	Intermediate Similarity	NPC475862
0.8137	Intermediate Similarity	NPC307282
0.8137	Intermediate Similarity	NPC305464
0.8137	Intermediate Similarity	NPC25848
0.8137	Intermediate Similarity	NPC19376
0.8137	Intermediate Similarity	NPC98874
0.8137	Intermediate Similarity	NPC201657
0.8131	Intermediate Similarity	NPC83744
0.8131	Intermediate Similarity	NPC477916
0.8125	Intermediate Similarity	NPC227132
0.8119	Intermediate Similarity	NPC114159
0.8119	Intermediate Similarity	NPC6818
0.8119	Intermediate Similarity	NPC103527
0.8119	Intermediate Similarity	NPC222047
0.8119	Intermediate Similarity	NPC191412
0.8119	Intermediate Similarity	NPC469982
0.8119	Intermediate Similarity	NPC148964
0.8119	Intermediate Similarity	NPC471207
0.8113	Intermediate Similarity	NPC475036
0.8113	Intermediate Similarity	NPC284865
0.8108	Intermediate Similarity	NPC117712
0.81	Intermediate Similarity	NPC73457
0.81	Intermediate Similarity	NPC105189
0.8091	Intermediate Similarity	NPC90952
0.8081	Intermediate Similarity	NPC130520
0.8081	Intermediate Similarity	NPC270768
0.8081	Intermediate Similarity	NPC290972
0.8081	Intermediate Similarity	NPC59263
0.8081	Intermediate Similarity	NPC61543
0.8081	Intermediate Similarity	NPC293048
0.8081	Intermediate Similarity	NPC225585
0.8081	Intermediate Similarity	NPC127689
0.8081	Intermediate Similarity	NPC187785
0.8081	Intermediate Similarity	NPC25906
0.8081	Intermediate Similarity	NPC281524
0.8081	Intermediate Similarity	NPC472973
0.8081	Intermediate Similarity	NPC64872
0.8081	Intermediate Similarity	NPC259875
0.8081	Intermediate Similarity	NPC263393
0.8081	Intermediate Similarity	NPC234346
0.8081	Intermediate Similarity	NPC121798
0.8077	Intermediate Similarity	NPC154072
0.8077	Intermediate Similarity	NPC15390
0.8077	Intermediate Similarity	NPC35239
0.8061	Intermediate Similarity	NPC298904
0.8061	Intermediate Similarity	NPC73064
0.8058	Intermediate Similarity	NPC476879
0.8058	Intermediate Similarity	NPC170978
0.8058	Intermediate Similarity	NPC187933
0.8058	Intermediate Similarity	NPC261935
0.8058	Intermediate Similarity	NPC476878
0.8058	Intermediate Similarity	NPC106112
0.8056	Intermediate Similarity	NPC163216
0.8056	Intermediate Similarity	NPC329417
0.8039	Intermediate Similarity	NPC271195
0.8037	Intermediate Similarity	NPC214264
0.8037	Intermediate Similarity	NPC97202
0.8037	Intermediate Similarity	NPC166607
0.8037	Intermediate Similarity	NPC260268
0.8037	Intermediate Similarity	NPC48733
0.8037	Intermediate Similarity	NPC150531
0.8037	Intermediate Similarity	NPC80566
0.8037	Intermediate Similarity	NPC476027
0.8037	Intermediate Similarity	NPC50692
0.8037	Intermediate Similarity	NPC319077
0.8037	Intermediate Similarity	NPC202167
0.8037	Intermediate Similarity	NPC171137
0.8037	Intermediate Similarity	NPC152695
0.8037	Intermediate Similarity	NPC49958
0.8037	Intermediate Similarity	NPC85829
0.8037	Intermediate Similarity	NPC302607
0.8037	Intermediate Similarity	NPC296945
0.802	Intermediate Similarity	NPC118519
0.802	Intermediate Similarity	NPC158059
0.802	Intermediate Similarity	NPC298554
0.802	Intermediate Similarity	NPC202728
0.802	Intermediate Similarity	NPC229281
0.802	Intermediate Similarity	NPC477520
0.8019	Intermediate Similarity	NPC478057
0.8019	Intermediate Similarity	NPC95899
0.8019	Intermediate Similarity	NPC247957
0.8019	Intermediate Similarity	NPC249187
0.8019	Intermediate Similarity	NPC312900
0.8	Intermediate Similarity	NPC210037
0.8	Intermediate Similarity	NPC134321
0.8	Intermediate Similarity	NPC111110
0.8	Intermediate Similarity	NPC470589
0.8	Intermediate Similarity	NPC477872
0.8	Intermediate Similarity	NPC273621
0.8	Intermediate Similarity	NPC227467
0.8	Intermediate Similarity	NPC193750
0.8	Intermediate Similarity	NPC18872
0.8	Intermediate Similarity	NPC120968
0.8	Intermediate Similarity	NPC126369
0.8	Intermediate Similarity	NPC291028
0.8	Intermediate Similarity	NPC235142
0.8	Intermediate Similarity	NPC7260
0.8	Intermediate Similarity	NPC128672
0.8	Intermediate Similarity	NPC290614
0.7982	Intermediate Similarity	NPC285298
0.7982	Intermediate Similarity	NPC257082
0.7981	Intermediate Similarity	NPC111214
0.7981	Intermediate Similarity	NPC271614
0.7981	Intermediate Similarity	NPC29765
0.798	Intermediate Similarity	NPC52169
0.798	Intermediate Similarity	NPC182797
0.798	Intermediate Similarity	NPC193360
0.7965	Intermediate Similarity	NPC470775
0.7965	Intermediate Similarity	NPC176513
0.7963	Intermediate Similarity	NPC473165
0.7963	Intermediate Similarity	NPC220229
0.7963	Intermediate Similarity	NPC475060
0.7963	Intermediate Similarity	NPC263729
0.7961	Intermediate Similarity	NPC5532
0.7961	Intermediate Similarity	NPC62516
0.7961	Intermediate Similarity	NPC157113
0.7961	Intermediate Similarity	NPC469545
0.7961	Intermediate Similarity	NPC61369
0.7961	Intermediate Similarity	NPC249954
0.7959	Intermediate Similarity	NPC235341
0.7959	Intermediate Similarity	NPC472986
0.7959	Intermediate Similarity	NPC95594
0.7959	Intermediate Similarity	NPC472985
0.7959	Intermediate Similarity	NPC477579
0.7944	Intermediate Similarity	NPC72255
0.7944	Intermediate Similarity	NPC160843
0.7944	Intermediate Similarity	NPC209502
0.7944	Intermediate Similarity	NPC204833
0.7944	Intermediate Similarity	NPC222161
0.7941	Intermediate Similarity	NPC472976
0.7941	Intermediate Similarity	NPC88116
0.7941	Intermediate Similarity	NPC282395
0.7941	Intermediate Similarity	NPC231063
0.7941	Intermediate Similarity	NPC145667
0.7941	Intermediate Similarity	NPC196227
0.7941	Intermediate Similarity	NPC263548
0.7941	Intermediate Similarity	NPC20235
0.7941	Intermediate Similarity	NPC299996
0.7941	Intermediate Similarity	NPC78580
0.7941	Intermediate Similarity	NPC184006
0.7941	Intermediate Similarity	NPC472977
0.7941	Intermediate Similarity	NPC23621
0.7941	Intermediate Similarity	NPC91010
0.7941	Intermediate Similarity	NPC32407
0.7941	Intermediate Similarity	NPC470957
0.7941	Intermediate Similarity	NPC8993
0.7941	Intermediate Similarity	NPC470958
0.7941	Intermediate Similarity	NPC209868
0.7938	Intermediate Similarity	NPC180834
0.7928	Intermediate Similarity	NPC4573
0.7928	Intermediate Similarity	NPC277769
0.7928	Intermediate Similarity	NPC207251
0.7925	Intermediate Similarity	NPC476890
0.7925	Intermediate Similarity	NPC193934
0.7925	Intermediate Similarity	NPC271980
0.7921	Intermediate Similarity	NPC187722

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 NPC474281 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1708
0.2-0.3	4051
0.3-0.4	2139
0.4-0.5	611
0.5-0.6	189
0.6-0.7	182
0.7-0.8	87
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
0.7921	Intermediate Similarity	NPD7515	Phase 2
0.7757	Intermediate Similarity	NPD5211	Phase 2
0.7723	Intermediate Similarity	NPD5328	Approved
0.7714	Intermediate Similarity	NPD4755	Approved
0.7615	Intermediate Similarity	NPD5141	Approved
0.7596	Intermediate Similarity	NPD7748	Approved
0.7589	Intermediate Similarity	NPD4634	Approved
0.7573	Intermediate Similarity	NPD6079	Approved
0.757	Intermediate Similarity	NPD5286	Approved
0.757	Intermediate Similarity	NPD4696	Approved
0.757	Intermediate Similarity	NPD4700	Approved
0.757	Intermediate Similarity	NPD5285	Approved
0.7547	Intermediate Similarity	NPD7902	Approved
0.7431	Intermediate Similarity	NPD5224	Approved
0.7431	Intermediate Similarity	NPD5226	Approved
0.7431	Intermediate Similarity	NPD4633	Approved
0.7431	Intermediate Similarity	NPD5225	Approved
0.7426	Intermediate Similarity	NPD3618	Phase 1
0.7423	Intermediate Similarity	NPD7645	Phase 2
0.74	Intermediate Similarity	NPD4786	Approved
0.7387	Intermediate Similarity	NPD7128	Approved
0.7387	Intermediate Similarity	NPD6675	Approved
0.7387	Intermediate Similarity	NPD6402	Approved
0.7387	Intermediate Similarity	NPD5739	Approved
0.7374	Intermediate Similarity	NPD3667	Approved
0.7364	Intermediate Similarity	NPD5175	Approved
0.7364	Intermediate Similarity	NPD5174	Approved
0.7339	Intermediate Similarity	NPD5223	Approved
0.7333	Intermediate Similarity	NPD4202	Approved
0.7311	Intermediate Similarity	NPD6054	Approved
0.7311	Intermediate Similarity	NPD6059	Approved
0.729	Intermediate Similarity	NPD5222	Approved
0.729	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4697	Phase 3
0.729	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD8328	Phase 3
0.7264	Intermediate Similarity	NPD7900	Approved
0.7264	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7320	Approved
0.7257	Intermediate Similarity	NPD6899	Approved
0.7257	Intermediate Similarity	NPD6881	Approved
0.7248	Intermediate Similarity	NPD7640	Approved
0.7248	Intermediate Similarity	NPD7639	Approved
0.7232	Intermediate Similarity	NPD4768	Approved
0.7232	Intermediate Similarity	NPD4767	Approved
0.7222	Intermediate Similarity	NPD5173	Approved
0.7207	Intermediate Similarity	NPD4754	Approved
0.7203	Intermediate Similarity	NPD7115	Discovery
0.7193	Intermediate Similarity	NPD6372	Approved
0.7193	Intermediate Similarity	NPD6373	Approved
0.719	Intermediate Similarity	NPD6370	Approved
0.7177	Intermediate Similarity	NPD7736	Approved
0.7172	Intermediate Similarity	NPD7525	Registered
0.717	Intermediate Similarity	NPD5778	Approved
0.717	Intermediate Similarity	NPD5779	Approved
0.7168	Intermediate Similarity	NPD5701	Approved
0.7168	Intermediate Similarity	NPD5697	Approved
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7638	Approved
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.712	Intermediate Similarity	NPD7319	Approved
0.7107	Intermediate Similarity	NPD6016	Approved
0.7107	Intermediate Similarity	NPD6015	Approved
0.7105	Intermediate Similarity	NPD4730	Approved
0.7105	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5128	Approved
0.7105	Intermediate Similarity	NPD4729	Approved
0.7087	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7492	Approved
0.7069	Intermediate Similarity	NPD6649	Approved
0.7069	Intermediate Similarity	NPD8130	Phase 1
0.7069	Intermediate Similarity	NPD6847	Approved
0.7069	Intermediate Similarity	NPD6617	Approved
0.7069	Intermediate Similarity	NPD6650	Approved
0.7069	Intermediate Similarity	NPD6869	Approved
0.7059	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3666	Approved
0.7059	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7049	Intermediate Similarity	NPD5988	Approved
0.7048	Intermediate Similarity	NPD4753	Phase 2
0.7043	Intermediate Similarity	NPD6014	Approved
0.7043	Intermediate Similarity	NPD6013	Approved
0.7043	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD6319	Approved
0.7016	Intermediate Similarity	NPD6616	Approved
0.7009	Intermediate Similarity	NPD6399	Phase 3
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.6983	Remote Similarity	NPD5248	Approved
0.6983	Remote Similarity	NPD5250	Approved
0.6983	Remote Similarity	NPD5247	Approved
0.6983	Remote Similarity	NPD5251	Approved
0.6983	Remote Similarity	NPD5249	Phase 3
0.696	Remote Similarity	NPD7078	Approved
0.696	Remote Similarity	NPD8293	Discontinued
0.6957	Remote Similarity	NPD6011	Approved
0.6949	Remote Similarity	NPD4632	Approved
0.693	Remote Similarity	NPD6008	Approved
0.6923	Remote Similarity	NPD5217	Approved
0.6923	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4623	Approved
0.6923	Remote Similarity	NPD5216	Approved
0.6923	Remote Similarity	NPD4519	Discontinued
0.6916	Remote Similarity	NPD8034	Phase 2
0.6916	Remote Similarity	NPD6411	Approved
0.6916	Remote Similarity	NPD8035	Phase 2
0.6897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3668	Phase 3
0.688	Remote Similarity	NPD7507	Approved
0.687	Remote Similarity	NPD6412	Phase 2
0.6847	Remote Similarity	NPD4225	Approved
0.6838	Remote Similarity	NPD5135	Approved
0.6838	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5169	Approved
0.6837	Remote Similarity	NPD3703	Phase 2
0.6829	Remote Similarity	NPD8515	Approved
0.6829	Remote Similarity	NPD8517	Approved
0.6829	Remote Similarity	NPD8516	Approved
0.6829	Remote Similarity	NPD8513	Phase 3
0.678	Remote Similarity	NPD5127	Approved
0.6777	Remote Similarity	NPD6009	Approved
0.6772	Remote Similarity	NPD6033	Approved
0.6759	Remote Similarity	NPD7637	Suspended
0.6757	Remote Similarity	NPD6084	Phase 2
0.6757	Remote Similarity	NPD6083	Phase 2
0.6752	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6101	Approved
0.6727	Remote Similarity	NPD5210	Approved
0.6727	Remote Similarity	NPD4629	Approved
0.6699	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD4221	Approved
0.6698	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3573	Approved
0.6695	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6695	Phase 3
0.6635	Remote Similarity	NPD4788	Approved
0.6612	Remote Similarity	NPD5167	Approved
0.6604	Remote Similarity	NPD5279	Phase 3
0.6587	Remote Similarity	NPD7604	Phase 2
0.6585	Remote Similarity	NPD6335	Approved
0.6574	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4197	Approved
0.6569	Remote Similarity	NPD6929	Approved
0.656	Remote Similarity	NPD5983	Phase 2
0.656	Remote Similarity	NPD6908	Approved
0.656	Remote Similarity	NPD6909	Approved
0.6529	Remote Similarity	NPD8133	Approved
0.6525	Remote Similarity	NPD6686	Approved
0.6505	Remote Similarity	NPD4695	Discontinued
0.6505	Remote Similarity	NPD7332	Phase 2
0.6505	Remote Similarity	NPD7514	Phase 3
0.6504	Remote Similarity	NPD6317	Approved
0.65	Remote Similarity	NPD6942	Approved
0.65	Remote Similarity	NPD7339	Approved
0.6486	Remote Similarity	NPD5282	Discontinued
0.6484	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD6697	Approved
0.6471	Remote Similarity	NPD6115	Approved
0.6471	Remote Similarity	NPD6118	Approved
0.6471	Remote Similarity	NPD6114	Approved
0.6452	Remote Similarity	NPD7327	Approved
0.6452	Remote Similarity	NPD6314	Approved
0.6452	Remote Similarity	NPD6313	Approved
0.6452	Remote Similarity	NPD7328	Approved
0.6449	Remote Similarity	NPD5330	Approved
0.6449	Remote Similarity	NPD5205	Approved
0.6449	Remote Similarity	NPD4138	Approved
0.6449	Remote Similarity	NPD7334	Approved
0.6449	Remote Similarity	NPD4690	Approved
0.6449	Remote Similarity	NPD6409	Approved
0.6449	Remote Similarity	NPD4688	Approved
0.6449	Remote Similarity	NPD6684	Approved
0.6449	Remote Similarity	NPD7146	Approved
0.6449	Remote Similarity	NPD7521	Approved
0.6449	Remote Similarity	NPD4689	Approved
0.6449	Remote Similarity	NPD4693	Phase 3
0.6446	Remote Similarity	NPD6053	Discontinued
0.6441	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6921	Approved
0.6429	Remote Similarity	NPD8380	Approved
0.6429	Remote Similarity	NPD8335	Approved
0.6429	Remote Similarity	NPD8378	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