NPASS Compound

Structure

NPC473124 OpenBabel07101718202D 45 50 0 0 1 0 0 0 0 0999 V2000 -8.4904 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1883 -3.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2079 -3.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8864 2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9060 2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6414 1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6981 -0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5471 1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6981 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2452 1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6414 0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7924 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9433 0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6981 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9433 1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6981 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8490 0.4902 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 1.6981 -0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3962 -0.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4904 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 -0.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 32 1 0 0 0 0 3 32 1 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 7 35 1 0 0 0 0 9 43 1 0 0 0 0 10 13 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 34 1 0 0 0 0 13 35 1 0 0 0 0 14 15 1 0 0 0 0 14 32 1 0 0 0 0 15 37 1 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 17 32 1 0 0 0 0 18 25 1 0 0 0 0 18 36 1 0 0 0 0 19 38 1 0 0 0 0 20 1 1 1 0 0 0 20 27 1 0 0 0 0 20 44 1 0 0 0 0 21 22 1 0 0 0 0 21 36 1 0 0 0 0 22 37 1 1 0 0 0 23 30 1 0 0 0 0 23 43 1 1 0 0 0 24 33 1 0 0 0 0 24 34 1 6 0 0 0 25 37 1 6 0 0 0 25 39 1 0 0 0 0 26 33 1 0 0 0 0 26 45 1 6 0 0 0 27 28 1 0 0 0 0 27 40 1 1 0 0 0 28 29 1 0 0 0 0 28 41 1 1 0 0 0 29 31 1 0 0 0 0 29 42 1 6 0 0 0 30 34 1 6 0 0 0 30 35 1 0 0 0 0 31 44 1 0 0 0 0 31 45 1 1 0 0 0 34 6 1 6 0 0 0 35 36 1 1 0 0 0 36 8 1 1 0 0 0 37 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.44
Volume:	664.855
LogP:	5.445
LogD:	4.185
LogS:	-4.692
# Rotatable Bonds:	4
TPSA:	128.84
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	5.628
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:	-5.203
MDCK Permeability:	7.057818493194645e-06
Pgp-inhibitor:	0.984
Pgp-substrate:	0.912
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.175
30% Bioavailability (F30%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	82.52043151855469%
Volume Distribution (VD):	0.951
Pgp-substrate:	12.328190803527832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.414
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.641
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	2.628
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.56
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.081
Carcinogencity:	0.089
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC473124

Natural Product ID:	NPC473124
*Common Name:**	SGNHYMIAMMFDCI-RSRZKSLTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SGNHYMIAMMFDCI-RSRZKSLTSA-N
Standard InCHI:	InChI=1S/C37H62O8/c1-20-27(40)28(41)29(42)31(44-20)45-26-11-12-34(6)24(33(26,4)5)10-13-35(7)30(34)23(43-9)16-21-22-17-32(2,3)14-15-37(22,19-38)25(39)18-36(21,35)8/h16,20,22-31,38-42H,10-15,17-19H2,1-9H3/t20-,22+,23-,24+,25+,26+,27+,28+,29-,30-,31+,34+,35-,36-,37-/m1/s1
SMILES:	CO[C@@H]1C=C2[C@@H]3CC(C)(C)CC[C@]3(CO)[C@H](C[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O)O)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3613714
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
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	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

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[486708]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[486708]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	>	50000.0	nM	PMID[486708]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[486708]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[486708]

☑ 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 NPC473124 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	2062
0.2-0.3	5370
0.3-0.4	12459
0.4-0.5	10873
0.5-0.6	5942
0.6-0.7	3181
0.7-0.8	1502
0.8-0.85	613
0.85-0.9	360
0.9-0.95	31
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473123
0.9896	High Similarity	NPC473127
0.9896	High Similarity	NPC110656
0.9896	High Similarity	NPC203354
0.9694	High Similarity	NPC281939
0.9588	High Similarity	NPC162354
0.94	High Similarity	NPC38376
0.94	High Similarity	NPC80210
0.9381	High Similarity	NPC117714
0.9381	High Similarity	NPC263756
0.9307	High Similarity	NPC285253
0.9307	High Similarity	NPC195116
0.9307	High Similarity	NPC221110
0.9307	High Similarity	NPC180459
0.9286	High Similarity	NPC76497
0.9286	High Similarity	NPC30289
0.9286	High Similarity	NPC213674
0.9286	High Similarity	NPC256133
0.9192	High Similarity	NPC123796
0.9126	High Similarity	NPC157474
0.9126	High Similarity	NPC110494
0.9118	High Similarity	NPC157530
0.9118	High Similarity	NPC14630
0.9118	High Similarity	NPC250089
0.91	High Similarity	NPC93352
0.91	High Similarity	NPC173583
0.91	High Similarity	NPC471435
0.91	High Similarity	NPC230948
0.91	High Similarity	NPC473734
0.91	High Similarity	NPC471434
0.91	High Similarity	NPC148603
0.9082	High Similarity	NPC64348
0.9072	High Similarity	NPC240372
0.9038	High Similarity	NPC476305
0.9038	High Similarity	NPC473125
0.901	High Similarity	NPC173859
0.901	High Similarity	NPC470512
0.901	High Similarity	NPC138057
0.9	High Similarity	NPC99627
0.9	High Similarity	NPC473129
0.8969	High Similarity	NPC90583
0.8958	High Similarity	NPC305160
0.8958	High Similarity	NPC72817
0.8958	High Similarity	NPC477927
0.8952	High Similarity	NPC290608
0.8952	High Similarity	NPC40133
0.8952	High Similarity	NPC473128
0.8952	High Similarity	NPC49413
0.8952	High Similarity	NPC44298
0.8942	High Similarity	NPC472987
0.8942	High Similarity	NPC473021
0.8932	High Similarity	NPC472901
0.8922	High Similarity	NPC33053
0.8922	High Similarity	NPC231340
0.8922	High Similarity	NPC78034
0.8911	High Similarity	NPC54521
0.8911	High Similarity	NPC75608
0.8911	High Similarity	NPC57065
0.8911	High Similarity	NPC109792
0.89	High Similarity	NPC288694
0.89	High Similarity	NPC312553
0.89	High Similarity	NPC159036
0.8889	High Similarity	NPC473200
0.8889	High Similarity	NPC7341
0.8889	High Similarity	NPC473790
0.8879	High Similarity	NPC473405
0.8846	High Similarity	NPC103627
0.8846	High Similarity	NPC170974
0.8846	High Similarity	NPC191439
0.8824	High Similarity	NPC472899
0.8824	High Similarity	NPC472900
0.8824	High Similarity	NPC472898
0.8812	High Similarity	NPC472252
0.8812	High Similarity	NPC16573
0.8812	High Similarity	NPC189852
0.8812	High Similarity	NPC245280
0.8812	High Similarity	NPC473020
0.8812	High Similarity	NPC131479
0.8812	High Similarity	NPC114874
0.8812	High Similarity	NPC286969
0.8812	High Similarity	NPC155010
0.8812	High Similarity	NPC473198
0.8812	High Similarity	NPC120123
0.8812	High Similarity	NPC16520
0.8812	High Similarity	NPC8039
0.8812	High Similarity	NPC211879
0.8812	High Similarity	NPC157659
0.8812	High Similarity	NPC31907
0.88	High Similarity	NPC129372
0.88	High Similarity	NPC21568
0.88	High Similarity	NPC88000
0.88	High Similarity	NPC285231
0.88	High Similarity	NPC4831
0.88	High Similarity	NPC309425
0.88	High Similarity	NPC47566
0.88	High Similarity	NPC472023
0.88	High Similarity	NPC160734
0.8796	High Similarity	NPC470515
0.8796	High Similarity	NPC471548
0.8788	High Similarity	NPC280825
0.8788	High Similarity	NPC234287
0.8774	High Similarity	NPC473159
0.875	High Similarity	NPC204407
0.875	High Similarity	NPC57362
0.875	High Similarity	NPC473328
0.875	High Similarity	NPC28844
0.875	High Similarity	NPC473318
0.875	High Similarity	NPC237503
0.875	High Similarity	NPC306746
0.875	High Similarity	NPC167383
0.8738	High Similarity	NPC257964
0.8725	High Similarity	NPC470885
0.8725	High Similarity	NPC221562
0.8725	High Similarity	NPC273879
0.8725	High Similarity	NPC165033
0.8725	High Similarity	NPC187400
0.8725	High Similarity	NPC470768
0.8716	High Similarity	NPC470517
0.8716	High Similarity	NPC470914
0.8716	High Similarity	NPC470911
0.8716	High Similarity	NPC470915
0.8713	High Similarity	NPC136816
0.87	High Similarity	NPC282669
0.8679	High Similarity	NPC473567
0.8679	High Similarity	NPC231797
0.8679	High Similarity	NPC216595
0.8673	High Similarity	NPC135224
0.8673	High Similarity	NPC100892
0.8673	High Similarity	NPC477970
0.8673	High Similarity	NPC477969
0.8667	High Similarity	NPC199457
0.8667	High Similarity	NPC127056
0.8667	High Similarity	NPC476886
0.8667	High Similarity	NPC108709
0.8667	High Similarity	NPC110139
0.8667	High Similarity	NPC7870
0.8667	High Similarity	NPC476887
0.8667	High Similarity	NPC476884
0.8667	High Similarity	NPC59804
0.8667	High Similarity	NPC136877
0.8667	High Similarity	NPC56713
0.8667	High Similarity	NPC476882
0.8667	High Similarity	NPC174679
0.8667	High Similarity	NPC102914
0.8667	High Similarity	NPC476885
0.8667	High Similarity	NPC476881
0.8667	High Similarity	NPC270667
0.8667	High Similarity	NPC474589
0.8667	High Similarity	NPC164194
0.8667	High Similarity	NPC65155
0.8667	High Similarity	NPC279554
0.8667	High Similarity	NPC476880
0.8667	High Similarity	NPC274507
0.8667	High Similarity	NPC75747
0.8667	High Similarity	NPC90856
0.8667	High Similarity	NPC476883
0.8667	High Similarity	NPC29069
0.8667	High Similarity	NPC475296
0.8667	High Similarity	NPC68419
0.866	High Similarity	NPC91654
0.866	High Similarity	NPC474792
0.866	High Similarity	NPC67398
0.8654	High Similarity	NPC284807
0.8654	High Similarity	NPC177246
0.8654	High Similarity	NPC472897
0.8654	High Similarity	NPC126147
0.8654	High Similarity	NPC472896
0.8654	High Similarity	NPC476123
0.8654	High Similarity	NPC28198
0.8641	High Similarity	NPC242748
0.8641	High Similarity	NPC160816
0.8641	High Similarity	NPC127801
0.8641	High Similarity	NPC208477
0.8641	High Similarity	NPC208594
0.8641	High Similarity	NPC194842
0.8641	High Similarity	NPC152584
0.8641	High Similarity	NPC69737
0.8641	High Similarity	NPC269627
0.8627	High Similarity	NPC213190
0.8614	High Similarity	NPC470434
0.86	High Similarity	NPC477928
0.8585	High Similarity	NPC108748
0.8585	High Similarity	NPC211798
0.8585	High Similarity	NPC208189
0.8585	High Similarity	NPC65034
0.8585	High Similarity	NPC191763
0.8585	High Similarity	NPC235841
0.8585	High Similarity	NPC13190
0.8585	High Similarity	NPC297208
0.8585	High Similarity	NPC179434
0.8585	High Similarity	NPC473481
0.8585	High Similarity	NPC31839
0.8585	High Similarity	NPC30397
0.8585	High Similarity	NPC164419
0.8571	High Similarity	NPC137917
0.8571	High Similarity	NPC127853
0.8571	High Similarity	NPC189513
0.8558	High Similarity	NPC63368
0.8558	High Similarity	NPC208650
0.8558	High Similarity	NPC472390

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 NPC473124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	2228
0.2-0.3	3889
0.3-0.4	1901
0.4-0.5	554
0.5-0.6	275
0.6-0.7	34
0.7-0.8	18
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8304	Intermediate Similarity	NPD8294	Approved
0.8304	Intermediate Similarity	NPD8377	Approved
0.823	Intermediate Similarity	NPD8378	Approved
0.823	Intermediate Similarity	NPD8033	Approved
0.823	Intermediate Similarity	NPD8296	Approved
0.823	Intermediate Similarity	NPD8380	Approved
0.823	Intermediate Similarity	NPD8379	Approved
0.823	Intermediate Similarity	NPD8335	Approved
0.8125	Intermediate Similarity	NPD7327	Approved
0.8125	Intermediate Similarity	NPD7328	Approved
0.8053	Intermediate Similarity	NPD7516	Approved
0.7913	Intermediate Similarity	NPD7503	Approved
0.789	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6686	Approved
0.7778	Intermediate Similarity	NPD8328	Phase 3
0.7768	Intermediate Similarity	NPD8133	Approved
0.7719	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7645	Phase 2
0.7647	Intermediate Similarity	NPD7507	Approved
0.7545	Intermediate Similarity	NPD6412	Phase 2
0.7459	Intermediate Similarity	NPD7319	Approved
0.7238	Intermediate Similarity	NPD8171	Discontinued
0.7222	Intermediate Similarity	NPD7638	Approved
0.7167	Intermediate Similarity	NPD8515	Approved
0.7167	Intermediate Similarity	NPD8513	Phase 3
0.7167	Intermediate Similarity	NPD8516	Approved
0.7167	Intermediate Similarity	NPD8517	Approved
0.7156	Intermediate Similarity	NPD7640	Approved
0.7156	Intermediate Similarity	NPD7639	Approved
0.7009	Intermediate Similarity	NPD7748	Approved
0.6972	Remote Similarity	NPD7902	Approved
0.69	Remote Similarity	NPD7525	Registered
0.6825	Remote Similarity	NPD7736	Approved
0.6822	Remote Similarity	NPD7515	Phase 2
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4225	Approved
0.6744	Remote Similarity	NPD8449	Approved
0.6697	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7900	Approved
0.6695	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6370	Approved
0.6692	Remote Similarity	NPD8450	Suspended
0.6637	Remote Similarity	NPD5344	Discontinued
0.6614	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7524	Approved
0.6594	Remote Similarity	NPD7625	Phase 1
0.6581	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7632	Discontinued
0.6557	Remote Similarity	NPD7115	Discovery
0.6532	Remote Similarity	NPD6059	Approved
0.6532	Remote Similarity	NPD6054	Approved
0.6508	Remote Similarity	NPD6067	Discontinued
0.6476	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7838	Discovery
0.6422	Remote Similarity	NPD46	Approved
0.6422	Remote Similarity	NPD6698	Approved
0.6408	Remote Similarity	NPD6928	Phase 2
0.64	Remote Similarity	NPD6942	Approved
0.64	Remote Similarity	NPD7339	Approved
0.6381	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6882	Approved
0.6357	Remote Similarity	NPD8074	Phase 3
0.6356	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6015	Approved
0.6349	Remote Similarity	NPD6016	Approved
0.6348	Remote Similarity	NPD4159	Approved
0.6337	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7492	Approved
0.6321	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.63	Remote Similarity	NPD1811	Approved
0.63	Remote Similarity	NPD1810	Approved
0.6299	Remote Similarity	NPD5988	Approved
0.6296	Remote Similarity	NPD7750	Discontinued
0.6296	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6009	Approved
0.6279	Remote Similarity	NPD6616	Approved
0.6273	Remote Similarity	NPD3168	Discontinued
0.627	Remote Similarity	NPD6319	Approved
0.6261	Remote Similarity	NPD6648	Approved
0.6238	Remote Similarity	NPD8264	Approved
0.6231	Remote Similarity	NPD7078	Approved
0.6182	Remote Similarity	NPD6051	Approved
0.6179	Remote Similarity	NPD4632	Approved
0.6172	Remote Similarity	NPD5125	Phase 3
0.6172	Remote Similarity	NPD5126	Approved
0.617	Remote Similarity	NPD6674	Discontinued
0.6161	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD6929	Approved
0.6134	Remote Similarity	NPD5739	Approved
0.6134	Remote Similarity	NPD6675	Approved
0.6134	Remote Similarity	NPD7128	Approved
0.6134	Remote Similarity	NPD6402	Approved
0.6116	Remote Similarity	NPD6372	Approved
0.6116	Remote Similarity	NPD6373	Approved
0.6111	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6931	Approved
0.6095	Remote Similarity	NPD6930	Phase 2
0.6094	Remote Similarity	NPD6921	Approved
0.6061	Remote Similarity	NPD6033	Approved
0.6055	Remote Similarity	NPD3618	Phase 1
0.6036	Remote Similarity	NPD5328	Approved
0.6033	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD7320	Approved
0.6033	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD6933	Approved
0.6016	Remote Similarity	NPD6650	Approved
0.6016	Remote Similarity	NPD8130	Phase 1
0.6016	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6640	Phase 3
0.6	Remote Similarity	NPD2686	Approved
0.6	Remote Similarity	NPD2687	Approved
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2254	Approved
0.5982	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD3667	Approved
0.5968	Remote Similarity	NPD6430	Approved
0.5968	Remote Similarity	NPD6429	Approved
0.5962	Remote Similarity	NPD5776	Phase 2
0.5962	Remote Similarity	NPD6925	Approved
0.595	Remote Similarity	NPD5701	Approved
0.595	Remote Similarity	NPD5697	Approved
0.5948	Remote Similarity	NPD4755	Approved
0.5943	Remote Similarity	NPD7514	Phase 3
0.5943	Remote Similarity	NPD7332	Phase 2
0.5935	Remote Similarity	NPD7290	Approved
0.5935	Remote Similarity	NPD7102	Approved
0.5935	Remote Similarity	NPD4634	Approved
0.5935	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD6079	Approved
0.5929	Remote Similarity	NPD6411	Approved
0.5929	Remote Similarity	NPD7087	Discontinued
0.5929	Remote Similarity	NPD7637	Suspended
0.5929	Remote Similarity	NPD7983	Approved
0.5926	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3669	Approved
0.5905	Remote Similarity	NPD7145	Approved
0.59	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6902	Approved
0.5887	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD6847	Approved
0.5887	Remote Similarity	NPD6869	Approved
0.5882	Remote Similarity	NPD5211	Phase 2
0.5878	Remote Similarity	NPD7604	Phase 2
0.5877	Remote Similarity	NPD5779	Approved
0.5877	Remote Similarity	NPD4202	Approved
0.5877	Remote Similarity	NPD5778	Approved
0.5868	Remote Similarity	NPD5357	Phase 1
0.5854	Remote Similarity	NPD6014	Approved
0.5854	Remote Similarity	NPD6013	Approved
0.5854	Remote Similarity	NPD6012	Approved
0.5847	Remote Similarity	NPD5286	Approved
0.5847	Remote Similarity	NPD4700	Approved
0.5847	Remote Similarity	NPD4696	Approved
0.5847	Remote Similarity	NPD5285	Approved
0.5846	Remote Similarity	NPD5983	Phase 2
0.584	Remote Similarity	NPD6053	Discontinued
0.5825	Remote Similarity	NPD6926	Approved
0.5825	Remote Similarity	NPD6924	Approved
0.5818	Remote Similarity	NPD6893	Approved
0.5812	Remote Similarity	NPD6084	Phase 2
0.5812	Remote Similarity	NPD6083	Phase 2
0.581	Remote Similarity	NPD6932	Approved
0.5804	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7509	Discontinued
0.5789	Remote Similarity	NPD8451	Approved
0.5789	Remote Similarity	NPD6336	Discontinued
0.5785	Remote Similarity	NPD5141	Approved
0.5784	Remote Similarity	NPD4243	Approved
0.5776	Remote Similarity	NPD7991	Discontinued
0.5772	Remote Similarity	NPD6011	Approved
0.5769	Remote Similarity	NPD7741	Discontinued
0.576	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7829	Approved
0.5758	Remote Similarity	NPD7830	Approved
0.5752	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6101	Approved
0.575	Remote Similarity	NPD5225	Approved
0.575	Remote Similarity	NPD5224	Approved
0.575	Remote Similarity	NPD5226	Approved
0.575	Remote Similarity	NPD4633	Approved
0.5746	Remote Similarity	NPD8448	Approved
0.5741	Remote Similarity	NPD6898	Phase 1
0.5738	Remote Similarity	NPD4767	Approved
0.5738	Remote Similarity	NPD6008	Approved
0.5738	Remote Similarity	NPD4768	Approved
0.5735	Remote Similarity	NPD8391	Approved
0.5735	Remote Similarity	NPD8392	Approved
0.5735	Remote Similarity	NPD8390	Approved
0.5727	Remote Similarity	NPD3665	Phase 1
0.5727	Remote Similarity	NPD3666	Approved
0.5727	Remote Similarity	NPD3133	Approved
0.5726	Remote Similarity	NPD4697	Phase 3
0.5726	Remote Similarity	NPD5220	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