NPASS Compound

Structure

NPC472901 OpenBabel07101718292D 47 52 0 0 1 0 0 0 0 0999 V2000 3.6914 -0.4806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5302 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 -0.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0689 3.6262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1358 3.3230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1261 0.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6511 -0.6846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0294 1.5528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 -2.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0537 1.4503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0447 1.1816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 3.4340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3882 0.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4285 0.6565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6994 -0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0044 0.9777 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6994 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3987 2.9434 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5491 -2.4528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6994 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5491 3.4340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6994 2.9434 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6994 1.9623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6994 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6609 1.7068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5491 1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5491 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8649 2.6665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -1.4717 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8497 0.4906 0.0000 C 0 0 1 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 -4.2484 4.4151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 -1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3987 -2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 4.4151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 3.4340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3076 0.0445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3987 1.9623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5940 2.0100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 33 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 7 36 1 0 0 0 0 9 44 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 35 1 0 0 0 0 13 36 1 0 0 0 0 14 18 2 0 0 0 0 15 20 1 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 16 37 1 0 0 0 0 17 38 1 0 0 0 0 19 18 1 6 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 20 39 1 6 0 0 0 21 14 1 1 0 0 0 21 44 1 0 0 0 0 22 30 1 0 0 0 0 22 45 1 1 0 0 0 23 17 1 6 0 0 0 23 27 1 0 0 0 0 23 46 1 0 0 0 0 24 35 1 6 0 0 0 24 37 1 0 0 0 0 25 33 1 0 0 0 0 25 40 1 6 0 0 0 26 36 1 1 0 0 0 27 28 1 0 0 0 0 27 41 1 1 0 0 0 28 29 1 0 0 0 0 28 42 1 6 0 0 0 29 32 1 0 0 0 0 29 43 1 1 0 0 0 30 33 1 0 0 0 0 30 35 1 6 0 0 0 31 21 1 1 0 0 0 31 34 1 0 0 0 0 31 47 1 0 0 0 0 32 45 1 6 0 0 0 32 46 1 0 0 0 0 34 47 1 0 0 0 0 35 6 1 6 0 0 0 36 37 1 6 0 0 0 37 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	666.43
Volume:	682.435
LogP:	3.616
LogD:	4.091
LogS:	-3.871
# Rotatable Bonds:	7
TPSA:	161.6
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.135
Synthetic Accessibility Score:	5.844
Fsp3:	0.946
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:	-5.082
MDCK Permeability:	5.100698763271794e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.628
Human Intestinal Absorption (HIA):	0.907
20% Bioavailability (F20%):	0.099
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	83.11202239990234%
Volume Distribution (VD):	0.553
Pgp-substrate:	7.167900562286377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.676
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.258

ADMET: Excretion

Clearance (CL):	1.669
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.394
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.673
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC472901

Natural Product ID:	NPC472901
*Common Name:**	UWWGFPDRXDYTKI-FSNJYKGBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UWWGFPDRXDYTKI-FSNJYKGBSA-N
Standard InCHI:	InChI=1S/C37H62O10/c1-18(14-21(44-9)31-34(4,5)47-31)19-10-13-36(7)26(19)20(39)15-24-35(6)12-11-25(40)33(2,3)30(35)22(16-37(24,36)8)45-32-29(43)28(42)27(41)23(17-38)46-32/h14,19-32,38-43H,10-13,15-17H2,1-9H3/b18-14+/t19-,20-,21+,22+,23-,24-,25+,26+,27-,28+,29-,30+,31+,32-,35-,36-,37-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C[C@]3(C)[C@@H]([C@@]4([C@@H]2C(C)(C)[C@@H](O)CC4)C)C[C@H]([C@H]2[C@@]3(C)CC[C@@H]2/C(=C/[C@@H]([C@@H]2OC2(C)C)OC)/C)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593737
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:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[12880307]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Stems	n.a.	n.a.	PMID[17663584]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[18186611]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Steamed Roots	n.a.	n.a.	PMID[26200131]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21891	Panax notoginseng	Species	Araliaceae	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
IC50	5
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	11.6	%	PMID[497471]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[497471]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[497471]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[497471]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[497471]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[497471]

☑ 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 NPC472901 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	290
0.1-0.2	1922
0.2-0.3	5395
0.3-0.4	12342
0.4-0.5	9687
0.5-0.6	6175
0.6-0.7	4145
0.7-0.8	2149
0.8-0.85	384
0.85-0.9	182
0.9-0.95	23
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC473021
0.9804	High Similarity	NPC472987
0.9505	High Similarity	NPC472899
0.9505	High Similarity	NPC472898
0.9505	High Similarity	NPC472900
0.9412	High Similarity	NPC33053
0.9406	High Similarity	NPC93352
0.94	High Similarity	NPC136816
0.9307	High Similarity	NPC473198
0.93	High Similarity	NPC4831
0.93	High Similarity	NPC47566
0.93	High Similarity	NPC88000
0.93	High Similarity	NPC472023
0.93	High Similarity	NPC129372
0.93	High Similarity	NPC160734
0.93	High Similarity	NPC309425
0.9223	High Similarity	NPC231340
0.9216	High Similarity	NPC75608
0.92	High Similarity	NPC7341
0.92	High Similarity	NPC473200
0.9143	High Similarity	NPC191439
0.9143	High Similarity	NPC103627
0.9143	High Similarity	NPC170974
0.9135	High Similarity	NPC472896
0.9135	High Similarity	NPC472897
0.9118	High Similarity	NPC131479
0.9118	High Similarity	NPC213190
0.9118	High Similarity	NPC31907
0.9118	High Similarity	NPC16520
0.9118	High Similarity	NPC189852
0.9118	High Similarity	NPC286969
0.9118	High Similarity	NPC157659
0.9118	High Similarity	NPC211879
0.9118	High Similarity	NPC245280
0.9118	High Similarity	NPC8039
0.9118	High Similarity	NPC155010
0.9118	High Similarity	NPC114874
0.9118	High Similarity	NPC473020
0.9118	High Similarity	NPC120123
0.9118	High Similarity	NPC472252
0.9109	High Similarity	NPC476896
0.91	High Similarity	NPC234287
0.91	High Similarity	NPC280825
0.9048	High Similarity	NPC157530
0.9048	High Similarity	NPC250089
0.9048	High Similarity	NPC28844
0.9048	High Similarity	NPC473318
0.9048	High Similarity	NPC14630
0.9048	High Similarity	NPC473328
0.9029	High Similarity	NPC221562
0.9029	High Similarity	NPC165033
0.9029	High Similarity	NPC470885
0.9029	High Similarity	NPC273879
0.9029	High Similarity	NPC187400
0.902	High Similarity	NPC288694
0.902	High Similarity	NPC159036
0.902	High Similarity	NPC312553
0.8972	High Similarity	NPC473567
0.8972	High Similarity	NPC216595
0.8972	High Similarity	NPC231797
0.8972	High Similarity	NPC475354
0.8962	High Similarity	NPC65155
0.8962	High Similarity	NPC472717
0.8952	High Similarity	NPC7213
0.8942	High Similarity	NPC160816
0.8942	High Similarity	NPC269627
0.8942	High Similarity	NPC208477
0.8942	High Similarity	NPC152584
0.8942	High Similarity	NPC127801
0.8942	High Similarity	NPC69737
0.8942	High Similarity	NPC208594
0.8942	High Similarity	NPC473199
0.8942	High Similarity	NPC194842
0.8932	High Similarity	NPC473123
0.8932	High Similarity	NPC473124
0.8932	High Similarity	NPC16573
0.8922	High Similarity	NPC285231
0.8922	High Similarity	NPC470434
0.8922	High Similarity	NPC21568
0.8911	High Similarity	NPC476895
0.89	High Similarity	NPC472989
0.8879	High Similarity	NPC472715
0.8879	High Similarity	NPC65034
0.8879	High Similarity	NPC208189
0.8857	High Similarity	NPC473469
0.8857	High Similarity	NPC208650
0.8857	High Similarity	NPC63368
0.8857	High Similarity	NPC14946
0.8857	High Similarity	NPC181467
0.8857	High Similarity	NPC190395
0.8846	High Similarity	NPC110656
0.8846	High Similarity	NPC203354
0.8846	High Similarity	NPC473127
0.8829	High Similarity	NPC29639
0.8829	High Similarity	NPC5883
0.8829	High Similarity	NPC304260
0.8829	High Similarity	NPC44899
0.8824	High Similarity	NPC469942
0.8824	High Similarity	NPC282669
0.8818	High Similarity	NPC290693
0.8818	High Similarity	NPC93883
0.8818	High Similarity	NPC476690
0.8818	High Similarity	NPC100048
0.8818	High Similarity	NPC20979
0.8812	High Similarity	NPC243728
0.8812	High Similarity	NPC476893
0.8812	High Similarity	NPC473890
0.8796	High Similarity	NPC472716
0.8774	High Similarity	NPC159005
0.8774	High Similarity	NPC38376
0.8774	High Similarity	NPC220427
0.8774	High Similarity	NPC180183
0.8774	High Similarity	NPC38217
0.8774	High Similarity	NPC246124
0.8774	High Similarity	NPC6931
0.8774	High Similarity	NPC80210
0.8774	High Similarity	NPC235824
0.8774	High Similarity	NPC472988
0.8762	High Similarity	NPC242748
0.8762	High Similarity	NPC309448
0.8761	High Similarity	NPC115349
0.8739	High Similarity	NPC10366
0.8727	High Similarity	NPC99620
0.8727	High Similarity	NPC199428
0.8727	High Similarity	NPC5311
0.8727	High Similarity	NPC193382
0.8727	High Similarity	NPC310341
0.8725	High Similarity	NPC158088
0.8713	High Similarity	NPC90583
0.8704	High Similarity	NPC13190
0.8692	High Similarity	NPC125361
0.8692	High Similarity	NPC154085
0.8692	High Similarity	NPC43976
0.8692	High Similarity	NPC296761
0.8692	High Similarity	NPC195116
0.8692	High Similarity	NPC285253
0.8692	High Similarity	NPC51925
0.8692	High Similarity	NPC302057
0.8692	High Similarity	NPC221110
0.8692	High Similarity	NPC180459
0.8679	High Similarity	NPC281939
0.8679	High Similarity	NPC226642
0.8679	High Similarity	NPC234160
0.8673	High Similarity	NPC231518
0.8673	High Similarity	NPC475219
0.8667	High Similarity	NPC475365
0.8667	High Similarity	NPC312774
0.8661	High Similarity	NPC236973
0.8661	High Similarity	NPC30483
0.8661	High Similarity	NPC470897
0.8661	High Similarity	NPC153085
0.8661	High Similarity	NPC32177
0.8661	High Similarity	NPC292467
0.8661	High Similarity	NPC268326
0.8661	High Similarity	NPC55532
0.8661	High Similarity	NPC469756
0.8654	High Similarity	NPC272015
0.8649	High Similarity	NPC471354
0.8649	High Similarity	NPC244402
0.8649	High Similarity	NPC203862
0.8649	High Similarity	NPC34390
0.8649	High Similarity	NPC50305
0.8649	High Similarity	NPC196429
0.8649	High Similarity	NPC474418
0.8649	High Similarity	NPC84987
0.8649	High Similarity	NPC142066
0.8649	High Similarity	NPC77319
0.8649	High Similarity	NPC158344
0.8649	High Similarity	NPC471351
0.8649	High Similarity	NPC309034
0.8649	High Similarity	NPC157376
0.8649	High Similarity	NPC471355
0.8649	High Similarity	NPC152615
0.8649	High Similarity	NPC471353
0.8649	High Similarity	NPC473852
0.8649	High Similarity	NPC99728
0.8649	High Similarity	NPC243196
0.8649	High Similarity	NPC87250
0.8649	High Similarity	NPC27507
0.8641	High Similarity	NPC64348
0.8641	High Similarity	NPC324598
0.8636	High Similarity	NPC84949
0.8636	High Similarity	NPC69576
0.8636	High Similarity	NPC31354
0.8636	High Similarity	NPC471633
0.8624	High Similarity	NPC112274
0.8598	High Similarity	NPC476513
0.8596	High Similarity	NPC193893
0.8585	High Similarity	NPC474569
0.8585	High Similarity	NPC165405
0.8585	High Similarity	NPC473476
0.8585	High Similarity	NPC473923
0.8585	High Similarity	NPC26798
0.8584	High Similarity	NPC135369
0.8584	High Similarity	NPC72260
0.8584	High Similarity	NPC475556
0.8584	High Similarity	NPC475629
0.8571	High Similarity	NPC471888
0.8571	High Similarity	NPC471885
0.8571	High Similarity	NPC472080

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 NPC472901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	2008
0.2-0.3	4071
0.3-0.4	1910
0.4-0.5	528
0.5-0.6	277
0.6-0.7	100
0.7-0.8	13
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8673	High Similarity	NPD8033	Approved
0.8584	High Similarity	NPD8294	Approved
0.8584	High Similarity	NPD8377	Approved
0.8571	High Similarity	NPD7328	Approved
0.8571	High Similarity	NPD7327	Approved
0.8509	High Similarity	NPD8378	Approved
0.8509	High Similarity	NPD8379	Approved
0.8509	High Similarity	NPD8380	Approved
0.8509	High Similarity	NPD8296	Approved
0.8509	High Similarity	NPD8335	Approved
0.8496	Intermediate Similarity	NPD7516	Approved
0.8067	Intermediate Similarity	NPD7507	Approved
0.8034	Intermediate Similarity	NPD7503	Approved
0.7895	Intermediate Similarity	NPD8133	Approved
0.7869	Intermediate Similarity	NPD7319	Approved
0.7611	Intermediate Similarity	NPD6686	Approved
0.7522	Intermediate Similarity	NPD6412	Phase 2
0.74	Intermediate Similarity	NPD7525	Registered
0.7383	Intermediate Similarity	NPD8171	Discontinued
0.7364	Intermediate Similarity	NPD7638	Approved
0.7297	Intermediate Similarity	NPD7640	Approved
0.7297	Intermediate Similarity	NPD7639	Approved
0.725	Intermediate Similarity	NPD7115	Discovery
0.7241	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7524	Approved
0.7115	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7736	Approved
0.704	Intermediate Similarity	NPD8328	Phase 3
0.7019	Intermediate Similarity	NPD6695	Phase 3
0.7016	Intermediate Similarity	NPD8517	Approved
0.7016	Intermediate Similarity	NPD8513	Phase 3
0.7016	Intermediate Similarity	NPD8515	Approved
0.7016	Intermediate Similarity	NPD8516	Approved
0.696	Remote Similarity	NPD6370	Approved
0.6949	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5344	Discontinued
0.693	Remote Similarity	NPD4159	Approved
0.6916	Remote Similarity	NPD7750	Discontinued
0.6875	Remote Similarity	NPD8293	Discontinued
0.687	Remote Similarity	NPD8449	Approved
0.6835	Remote Similarity	NPD7625	Phase 1
0.6818	Remote Similarity	NPD8450	Suspended
0.68	Remote Similarity	NPD6059	Approved
0.68	Remote Similarity	NPD6054	Approved
0.6796	Remote Similarity	NPD7645	Phase 2
0.6759	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4225	Approved
0.6752	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6942	Approved
0.6733	Remote Similarity	NPD7339	Approved
0.6731	Remote Similarity	NPD6928	Phase 2
0.6731	Remote Similarity	NPD6930	Phase 2
0.6731	Remote Similarity	NPD6931	Approved
0.6724	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6933	Approved
0.6639	Remote Similarity	NPD6882	Approved
0.6639	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD6929	Approved
0.6614	Remote Similarity	NPD6015	Approved
0.6614	Remote Similarity	NPD6016	Approved
0.6589	Remote Similarity	NPD7492	Approved
0.6577	Remote Similarity	NPD46	Approved
0.6577	Remote Similarity	NPD6698	Approved
0.6577	Remote Similarity	NPD3168	Discontinued
0.6577	Remote Similarity	NPD7838	Discovery
0.6571	Remote Similarity	NPD7514	Phase 3
0.6562	Remote Similarity	NPD5988	Approved
0.656	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD6616	Approved
0.6535	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD8034	Phase 2
0.6518	Remote Similarity	NPD8035	Phase 2
0.6518	Remote Similarity	NPD7087	Discontinued
0.6512	Remote Similarity	NPD6067	Discontinued
0.6509	Remote Similarity	NPD6902	Approved
0.6505	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7078	Approved
0.6486	Remote Similarity	NPD6051	Approved
0.6471	Remote Similarity	NPD6924	Approved
0.6471	Remote Similarity	NPD6926	Approved
0.6466	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6399	Phase 3
0.6452	Remote Similarity	NPD4632	Approved
0.6446	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6925	Approved
0.6442	Remote Similarity	NPD6932	Approved
0.6442	Remote Similarity	NPD5776	Phase 2
0.6422	Remote Similarity	NPD6893	Approved
0.6417	Remote Similarity	NPD7128	Approved
0.6417	Remote Similarity	NPD5739	Approved
0.6417	Remote Similarity	NPD6675	Approved
0.6417	Remote Similarity	NPD6008	Approved
0.6417	Remote Similarity	NPD6402	Approved
0.6415	Remote Similarity	NPD7332	Phase 2
0.64	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6373	Approved
0.6393	Remote Similarity	NPD6372	Approved
0.6381	Remote Similarity	NPD7145	Approved
0.6372	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD8074	Phase 3
0.633	Remote Similarity	NPD4786	Approved
0.6321	Remote Similarity	NPD6683	Phase 2
0.6316	Remote Similarity	NPD6033	Approved
0.6311	Remote Similarity	NPD6899	Approved
0.6311	Remote Similarity	NPD6881	Approved
0.6311	Remote Similarity	NPD7320	Approved
0.629	Remote Similarity	NPD6649	Approved
0.629	Remote Similarity	NPD8130	Phase 1
0.629	Remote Similarity	NPD6650	Approved
0.6281	Remote Similarity	NPD6640	Phase 3
0.6279	Remote Similarity	NPD7741	Discontinued
0.6273	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7509	Discontinued
0.6261	Remote Similarity	NPD7748	Approved
0.626	Remote Similarity	NPD7604	Phase 2
0.624	Remote Similarity	NPD6053	Discontinued
0.6239	Remote Similarity	NPD7902	Approved
0.6239	Remote Similarity	NPD4755	Approved
0.623	Remote Similarity	NPD5697	Approved
0.623	Remote Similarity	NPD5701	Approved
0.621	Remote Similarity	NPD7290	Approved
0.621	Remote Similarity	NPD4634	Approved
0.621	Remote Similarity	NPD6883	Approved
0.621	Remote Similarity	NPD7102	Approved
0.6204	Remote Similarity	NPD6898	Phase 1
0.6195	Remote Similarity	NPD5328	Approved
0.6183	Remote Similarity	NPD5125	Phase 3
0.6183	Remote Similarity	NPD5126	Approved
0.6182	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4202	Approved
0.6167	Remote Similarity	NPD5211	Phase 2
0.616	Remote Similarity	NPD6847	Approved
0.616	Remote Similarity	NPD6869	Approved
0.616	Remote Similarity	NPD6617	Approved
0.6154	Remote Similarity	NPD1811	Approved
0.6154	Remote Similarity	NPD4784	Approved
0.6154	Remote Similarity	NPD1810	Approved
0.6154	Remote Similarity	NPD4785	Approved
0.6148	Remote Similarity	NPD5357	Phase 1
0.6147	Remote Similarity	NPD3667	Approved
0.6134	Remote Similarity	NPD5286	Approved
0.6134	Remote Similarity	NPD4700	Approved
0.6134	Remote Similarity	NPD5285	Approved
0.6134	Remote Similarity	NPD4696	Approved
0.6129	Remote Similarity	NPD6014	Approved
0.6129	Remote Similarity	NPD6012	Approved
0.6129	Remote Similarity	NPD6013	Approved
0.6117	Remote Similarity	NPD7152	Approved
0.6117	Remote Similarity	NPD7150	Approved
0.6117	Remote Similarity	NPD7151	Approved
0.6117	Remote Similarity	NPD4243	Approved
0.6111	Remote Similarity	NPD4748	Discontinued
0.6107	Remote Similarity	NPD5983	Phase 2
0.6102	Remote Similarity	NPD6084	Phase 2
0.6102	Remote Similarity	NPD6083	Phase 2
0.6087	Remote Similarity	NPD7515	Phase 2
0.6087	Remote Similarity	NPD6079	Approved
0.608	Remote Similarity	NPD6371	Approved
0.6078	Remote Similarity	NPD6923	Approved
0.6078	Remote Similarity	NPD6922	Approved
0.6075	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3618	Phase 1
0.6069	Remote Similarity	NPD6674	Discontinued
0.6068	Remote Similarity	NPD7991	Discontinued
0.6066	Remote Similarity	NPD5141	Approved
0.6048	Remote Similarity	NPD6011	Approved
0.6045	Remote Similarity	NPD6336	Discontinued
0.6033	Remote Similarity	NPD5224	Approved
0.6033	Remote Similarity	NPD5226	Approved
0.6033	Remote Similarity	NPD4633	Approved
0.6033	Remote Similarity	NPD5225	Approved
0.6032	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7143	Approved
0.6019	Remote Similarity	NPD7144	Approved
0.6016	Remote Similarity	NPD4768	Approved
0.6016	Remote Similarity	NPD4767	Approved
0.5985	Remote Similarity	NPD6921	Approved
0.5984	Remote Similarity	NPD5174	Approved
0.5984	Remote Similarity	NPD5175	Approved
0.5983	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7900	Approved
0.5969	Remote Similarity	NPD6940	Discontinued
0.5968	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7799	Discontinued
0.595	Remote Similarity	NPD5223	Approved
0.5943	Remote Similarity	NPD8264	Approved
0.592	Remote Similarity	NPD4729	Approved
0.592	Remote Similarity	NPD8174	Phase 2
0.592	Remote Similarity	NPD4730	Approved
0.5913	Remote Similarity	NPD4753	Phase 2
0.5896	Remote Similarity	NPD7829	Approved
0.5896	Remote Similarity	NPD7830	Approved
0.5882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4697	Phase 3
0.5882	Remote Similarity	NPD5221	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