NPASS Compound

Structure

NPC276061 OpenBabel07101719152D 29 31 0 0 1 0 0 0 0 0999 V2000 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 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 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 2 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 0.8660 2.5000 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 0.0000 -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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 27 1 0 0 0 0 9 13 1 0 0 0 0 9 26 1 0 0 0 0 11 6 1 1 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 7 1 6 0 0 0 12 16 1 0 0 0 0 12 28 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 6 0 0 0 14 15 1 0 0 0 0 14 22 1 6 0 0 0 15 23 1 1 0 0 0 16 18 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 1 0 0 0 18 27 1 6 0 0 0 19 28 1 0 0 0 0 19 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.17
Volume:	391.504
LogP:	-0.611
LogD:	-1.007
LogS:	-1.58
# Rotatable Bonds:	7
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	4.168
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.675
MDCK Permeability:	7.519281643908471e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.87
Human Intestinal Absorption (HIA):	0.978
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	26.646835327148438%
Volume Distribution (VD):	0.491
Pgp-substrate:	45.80167770385742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.021

ADMET: Excretion

Clearance (CL):	1.07
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.422
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.24
AMES Toxicity:	0.337
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.926
Carcinogencity:	0.045
Eye Corrosion:	0.004
Eye Irritation:	0.373
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC276061

Natural Product ID:	NPC276061
*Common Name:**	Polygalatenoside B
IUPAC Name:	(2S,3S,4R,5R,6S)-2-[(3R,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)-4-phenylmethoxyoxane-3,5-diol
Synonyms:	polygalatenoside B
Standard InCHIKey:	PBKBHCJPMCMBCZ-GDLYOHBGSA-N
Standard InCHI:	InChI=1S/C19H28O10/c20-6-11-14(22)15(23)13(9-26-11)29-19-17(25)18(16(24)12(7-21)28-19)27-8-10-4-2-1-3-5-10/h1-5,11-25H,6-9H2/t11-,12-,13+,14-,15-,16+,17-,18+,19-/m0/s1
SMILES:	c1ccc(cc1)CO[C@@H]1[C@@H]([C@H](CO)O[C@H]([C@H]1O)O[C@@H]1CO[C@@H](CO)[C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462805
PubChem CID:	44559130
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT228	Individual Protein	Norepinephrine transporter	Homo sapiens	IC50	=	6040.0	nM	PMID[526051]

☑ 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 NPC276061 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	277
0.1-0.2	1165
0.2-0.3	2974
0.3-0.4	8725
0.4-0.5	12001
0.5-0.6	12626
0.6-0.7	4254
0.7-0.8	603
0.8-0.85	53
0.85-0.9	8
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474148
0.9902	High Similarity	NPC30563
0.9604	High Similarity	NPC37714
0.9604	High Similarity	NPC152384
0.9519	High Similarity	NPC264784
0.9406	High Similarity	NPC469527
0.9266	High Similarity	NPC266389
0.9266	High Similarity	NPC122245
0.9266	High Similarity	NPC216605
0.9126	High Similarity	NPC148060
0.8899	High Similarity	NPC120217
0.8824	High Similarity	NPC262826
0.8772	High Similarity	NPC229600
0.8762	High Similarity	NPC47286
0.8716	High Similarity	NPC470825
0.8661	High Similarity	NPC175771
0.8632	High Similarity	NPC57607
0.8621	High Similarity	NPC476142
0.8611	High Similarity	NPC184633
0.8487	Intermediate Similarity	NPC114096
0.8482	Intermediate Similarity	NPC313193
0.8448	Intermediate Similarity	NPC469412
0.8448	Intermediate Similarity	NPC198734
0.8435	Intermediate Similarity	NPC14950
0.8417	Intermediate Similarity	NPC148026
0.8393	Intermediate Similarity	NPC474641
0.8376	Intermediate Similarity	NPC55608
0.8333	Intermediate Similarity	NPC148055
0.8319	Intermediate Similarity	NPC157338
0.8291	Intermediate Similarity	NPC201402
0.8291	Intermediate Similarity	NPC469704
0.8291	Intermediate Similarity	NPC269242
0.8291	Intermediate Similarity	NPC469703
0.8291	Intermediate Similarity	NPC160854
0.8288	Intermediate Similarity	NPC43584
0.825	Intermediate Similarity	NPC470510
0.822	Intermediate Similarity	NPC469686
0.822	Intermediate Similarity	NPC226712
0.8205	Intermediate Similarity	NPC469708
0.8205	Intermediate Similarity	NPC469702
0.8205	Intermediate Similarity	NPC282409
0.8205	Intermediate Similarity	NPC60589
0.8197	Intermediate Similarity	NPC301857
0.8167	Intermediate Similarity	NPC287429
0.8158	Intermediate Similarity	NPC29607
0.8151	Intermediate Similarity	NPC52097
0.8151	Intermediate Similarity	NPC471067
0.8145	Intermediate Similarity	NPC9912
0.8145	Intermediate Similarity	NPC225384
0.8145	Intermediate Similarity	NPC246869
0.8145	Intermediate Similarity	NPC138777
0.8136	Intermediate Similarity	NPC469548
0.8136	Intermediate Similarity	NPC476448
0.8136	Intermediate Similarity	NPC476445
0.8115	Intermediate Similarity	NPC106677
0.8115	Intermediate Similarity	NPC288416
0.8099	Intermediate Similarity	NPC126991
0.8099	Intermediate Similarity	NPC83218
0.8083	Intermediate Similarity	NPC212176
0.8083	Intermediate Similarity	NPC178449
0.8083	Intermediate Similarity	NPC470907
0.8083	Intermediate Similarity	NPC232454
0.808	Intermediate Similarity	NPC254275
0.8067	Intermediate Similarity	NPC11724
0.8033	Intermediate Similarity	NPC252114
0.8033	Intermediate Similarity	NPC471157
0.8017	Intermediate Similarity	NPC473556
0.8017	Intermediate Similarity	NPC301651
0.8	Intermediate Similarity	NPC141970
0.8	Intermediate Similarity	NPC475067
0.8	Intermediate Similarity	NPC46137
0.8	Intermediate Similarity	NPC140561
0.8	Intermediate Similarity	NPC235294
0.7984	Intermediate Similarity	NPC295970
0.7984	Intermediate Similarity	NPC27712
0.7983	Intermediate Similarity	NPC476872
0.7953	Intermediate Similarity	NPC87696
0.7953	Intermediate Similarity	NPC35731
0.7934	Intermediate Similarity	NPC138798
0.792	Intermediate Similarity	NPC80600
0.792	Intermediate Similarity	NPC472024
0.7917	Intermediate Similarity	NPC266045
0.7903	Intermediate Similarity	NPC146540
0.7903	Intermediate Similarity	NPC225307
0.7903	Intermediate Similarity	NPC40377
0.7903	Intermediate Similarity	NPC302378
0.7881	Intermediate Similarity	NPC228907
0.7869	Intermediate Similarity	NPC87153
0.7869	Intermediate Similarity	NPC162925
0.7869	Intermediate Similarity	NPC145287
0.7857	Intermediate Similarity	NPC65942
0.7857	Intermediate Similarity	NPC478255
0.7857	Intermediate Similarity	NPC248307
0.784	Intermediate Similarity	NPC26653
0.784	Intermediate Similarity	NPC166040
0.784	Intermediate Similarity	NPC97326
0.784	Intermediate Similarity	NPC248355
0.784	Intermediate Similarity	NPC253595
0.784	Intermediate Similarity	NPC270849
0.784	Intermediate Similarity	NPC218003
0.784	Intermediate Similarity	NPC307110
0.784	Intermediate Similarity	NPC184092
0.7829	Intermediate Similarity	NPC469383
0.7826	Intermediate Similarity	NPC265002
0.7823	Intermediate Similarity	NPC35288
0.7823	Intermediate Similarity	NPC156692
0.7823	Intermediate Similarity	NPC108659
0.7823	Intermediate Similarity	NPC173150
0.7823	Intermediate Similarity	NPC469687
0.7823	Intermediate Similarity	NPC231607
0.7823	Intermediate Similarity	NPC79715
0.7823	Intermediate Similarity	NPC471882
0.7823	Intermediate Similarity	NPC264900
0.7823	Intermediate Similarity	NPC45224
0.7823	Intermediate Similarity	NPC471881
0.7812	Intermediate Similarity	NPC476411
0.7812	Intermediate Similarity	NPC130496
0.7812	Intermediate Similarity	NPC188555
0.7812	Intermediate Similarity	NPC187194
0.7805	Intermediate Similarity	NPC90318
0.7805	Intermediate Similarity	NPC28069
0.7805	Intermediate Similarity	NPC77651
0.7795	Intermediate Similarity	NPC85799
0.7795	Intermediate Similarity	NPC165686
0.7795	Intermediate Similarity	NPC473285
0.7795	Intermediate Similarity	NPC303422
0.7795	Intermediate Similarity	NPC26080
0.7778	Intermediate Similarity	NPC289415
0.7778	Intermediate Similarity	NPC319995
0.7769	Intermediate Similarity	NPC87777
0.7769	Intermediate Similarity	NPC304152
0.7769	Intermediate Similarity	NPC262328
0.7769	Intermediate Similarity	NPC78363
0.7768	Intermediate Similarity	NPC472315
0.7768	Intermediate Similarity	NPC475203
0.7768	Intermediate Similarity	NPC474376
0.7768	Intermediate Similarity	NPC472316
0.776	Intermediate Similarity	NPC148982
0.7759	Intermediate Similarity	NPC172525
0.7752	Intermediate Similarity	NPC263829
0.7752	Intermediate Similarity	NPC238243
0.7752	Intermediate Similarity	NPC470236
0.7752	Intermediate Similarity	NPC79957
0.775	Intermediate Similarity	NPC146673
0.775	Intermediate Similarity	NPC233923
0.7742	Intermediate Similarity	NPC35338
0.7742	Intermediate Similarity	NPC124878
0.7742	Intermediate Similarity	NPC10883
0.7742	Intermediate Similarity	NPC204214
0.7742	Intermediate Similarity	NPC267733
0.7742	Intermediate Similarity	NPC10121
0.7742	Intermediate Similarity	NPC61181
0.7742	Intermediate Similarity	NPC92283
0.7742	Intermediate Similarity	NPC94179
0.7742	Intermediate Similarity	NPC290276
0.7742	Intermediate Similarity	NPC276047
0.7742	Intermediate Similarity	NPC231888
0.7742	Intermediate Similarity	NPC198918
0.7742	Intermediate Similarity	NPC63404
0.7739	Intermediate Similarity	NPC185840
0.7739	Intermediate Similarity	NPC234376
0.7734	Intermediate Similarity	NPC294166
0.7734	Intermediate Similarity	NPC25821
0.7734	Intermediate Similarity	NPC6836
0.7734	Intermediate Similarity	NPC115022
0.7724	Intermediate Similarity	NPC244454
0.7717	Intermediate Similarity	NPC254819
0.7717	Intermediate Similarity	NPC121376
0.7717	Intermediate Similarity	NPC166168
0.7698	Intermediate Similarity	NPC477294
0.7698	Intermediate Similarity	NPC229784
0.7698	Intermediate Similarity	NPC477293
0.7692	Intermediate Similarity	NPC177035
0.7692	Intermediate Similarity	NPC164857
0.7692	Intermediate Similarity	NPC199459
0.7692	Intermediate Similarity	NPC138350
0.7692	Intermediate Similarity	NPC3293
0.7692	Intermediate Similarity	NPC165482
0.7692	Intermediate Similarity	NPC197723
0.7692	Intermediate Similarity	NPC166180
0.7692	Intermediate Similarity	NPC52277
0.7692	Intermediate Similarity	NPC471345
0.7692	Intermediate Similarity	NPC40664
0.768	Intermediate Similarity	NPC198798
0.768	Intermediate Similarity	NPC103533
0.768	Intermediate Similarity	NPC471025
0.768	Intermediate Similarity	NPC231627
0.768	Intermediate Similarity	NPC175333
0.7674	Intermediate Similarity	NPC34456
0.7674	Intermediate Similarity	NPC470881
0.7674	Intermediate Similarity	NPC169398
0.7674	Intermediate Similarity	NPC886
0.7674	Intermediate Similarity	NPC471029
0.7674	Intermediate Similarity	NPC287597
0.7674	Intermediate Similarity	NPC34293
0.7672	Intermediate Similarity	NPC153795
0.7672	Intermediate Similarity	NPC42911
0.7672	Intermediate Similarity	NPC290353
0.7661	Intermediate Similarity	NPC12308
0.7661	Intermediate Similarity	NPC123704

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 NPC276061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	748
0.2-0.3	1446
0.3-0.4	3316
0.4-0.5	2072
0.5-0.6	1180
0.6-0.7	156
0.7-0.8	7
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
0.8362	Intermediate Similarity	NPD5126	Approved
0.8362	Intermediate Similarity	NPD5125	Phase 3
0.822	Intermediate Similarity	NPD1091	Approved
0.7895	Intermediate Similarity	NPD969	Suspended
0.7576	Intermediate Similarity	NPD7266	Discontinued
0.7319	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7741	Discontinued
0.7094	Intermediate Similarity	NPD290	Approved
0.7049	Intermediate Similarity	NPD4198	Discontinued
0.6963	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7876	Discontinued
0.6942	Remote Similarity	NPD7843	Approved
0.6929	Remote Similarity	NPD5058	Phase 3
0.6923	Remote Similarity	NPD1653	Approved
0.6918	Remote Similarity	NPD8455	Phase 2
0.6917	Remote Similarity	NPD4404	Approved
0.6891	Remote Similarity	NPD2684	Approved
0.6866	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD9294	Approved
0.6835	Remote Similarity	NPD6674	Discontinued
0.6807	Remote Similarity	NPD9532	Phase 3
0.6797	Remote Similarity	NPD3705	Approved
0.6774	Remote Similarity	NPD7157	Approved
0.6772	Remote Similarity	NPD5723	Approved
0.6767	Remote Similarity	NPD3027	Phase 3
0.6741	Remote Similarity	NPD1613	Approved
0.6741	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD689	Discontinued
0.672	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD41	Approved
0.6715	Remote Similarity	NPD5886	Approved
0.6715	Remote Similarity	NPD4536	Approved
0.6715	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4538	Approved
0.6696	Remote Similarity	NPD9495	Approved
0.6694	Remote Similarity	NPD2629	Approved
0.6693	Remote Similarity	NPD1357	Approved
0.6667	Remote Similarity	NPD5588	Approved
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5960	Phase 3
0.6639	Remote Similarity	NPD5048	Discontinued
0.6596	Remote Similarity	NPD1652	Phase 2
0.6594	Remote Similarity	NPD7097	Phase 1
0.6583	Remote Similarity	NPD3526	Approved
0.6583	Remote Similarity	NPD968	Approved
0.6583	Remote Similarity	NPD3524	Approved
0.6581	Remote Similarity	NPD2549	Approved
0.6581	Remote Similarity	NPD2552	Approved
0.6581	Remote Similarity	NPD2558	Approved
0.6581	Remote Similarity	NPD2555	Approved
0.6581	Remote Similarity	NPD2550	Approved
0.6581	Remote Similarity	NPD2553	Approved
0.6557	Remote Similarity	NPD9713	Approved
0.6544	Remote Similarity	NPD6233	Phase 2
0.6525	Remote Similarity	NPD4188	Approved
0.6525	Remote Similarity	NPD4189	Approved
0.6519	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD8651	Approved
0.6512	Remote Similarity	NPD5846	Approved
0.6512	Remote Similarity	NPD6516	Phase 2
0.6503	Remote Similarity	NPD6190	Approved
0.65	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2861	Phase 2
0.6486	Remote Similarity	NPD531	Approved
0.6484	Remote Similarity	NPD1548	Phase 1
0.648	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5291	Approved
0.6457	Remote Similarity	NPD5292	Approved
0.6446	Remote Similarity	NPD6685	Approved
0.6444	Remote Similarity	NPD4908	Phase 1
0.6444	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3685	Discontinued
0.6423	Remote Similarity	NPD2067	Discontinued
0.6418	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD3047	Approved
0.6417	Remote Similarity	NPD3046	Approved
0.6417	Remote Similarity	NPD3048	Approved
0.6412	Remote Similarity	NPD1610	Phase 2
0.6397	Remote Similarity	NPD3179	Approved
0.6397	Remote Similarity	NPD3180	Approved
0.6396	Remote Similarity	NPD1282	Approved
0.6393	Remote Similarity	NPD1358	Approved
0.6393	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7054	Approved
0.6392	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD291	Approved
0.637	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7798	Approved
0.6356	Remote Similarity	NPD1238	Approved
0.6352	Remote Similarity	NPD7472	Approved
0.6352	Remote Similarity	NPD7074	Phase 3
0.635	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6798	Discontinued
0.6349	Remote Similarity	NPD6010	Discontinued
0.6345	Remote Similarity	NPD3122	Phase 3
0.6341	Remote Similarity	NPD2182	Approved
0.6333	Remote Similarity	NPD6647	Phase 2
0.6333	Remote Similarity	NPD5765	Approved
0.6333	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5124	Phase 1
0.6331	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD4340	Discontinued
0.6329	Remote Similarity	NPD7228	Approved
0.632	Remote Similarity	NPD4571	Approved
0.632	Remote Similarity	NPD6912	Phase 3
0.632	Remote Similarity	NPD4572	Approved
0.632	Remote Similarity	NPD4573	Approved
0.6316	Remote Similarity	NPD9365	Approved
0.6312	Remote Similarity	NPD6797	Phase 2
0.6312	Remote Similarity	NPD7033	Discontinued
0.6312	Remote Similarity	NPD4108	Discontinued
0.6311	Remote Similarity	NPD2559	Approved
0.6311	Remote Similarity	NPD812	Approved
0.6311	Remote Similarity	NPD810	Approved
0.6311	Remote Similarity	NPD2551	Approved
0.6311	Remote Similarity	NPD811	Approved
0.6296	Remote Similarity	NPD7247	Discontinued
0.6293	Remote Similarity	NPD2933	Approved
0.6293	Remote Similarity	NPD2934	Approved
0.6291	Remote Similarity	NPD37	Approved
0.629	Remote Similarity	NPD556	Approved
0.6289	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6653	Approved
0.6275	Remote Similarity	NPD4966	Approved
0.6275	Remote Similarity	NPD4967	Phase 2
0.6275	Remote Similarity	NPD4965	Approved
0.6273	Remote Similarity	NPD7251	Discontinued
0.627	Remote Similarity	NPD1138	Approved
0.6267	Remote Similarity	NPD4380	Phase 2
0.625	Remote Similarity	NPD6671	Approved
0.6241	Remote Similarity	NPD7250	Approved
0.6241	Remote Similarity	NPD2231	Phase 2
0.6241	Remote Similarity	NPD2235	Phase 2
0.6241	Remote Similarity	NPD7249	Approved
0.624	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.624	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD2859	Approved
0.6239	Remote Similarity	NPD2860	Approved
0.6235	Remote Similarity	NPD7808	Phase 3
0.6232	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD9545	Approved
0.6226	Remote Similarity	NPD3818	Discontinued
0.6224	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5762	Approved
0.6224	Remote Similarity	NPD5763	Approved
0.6222	Remote Similarity	NPD2628	Approved
0.6222	Remote Similarity	NPD2625	Approved
0.6222	Remote Similarity	NPD2626	Approved
0.6222	Remote Similarity	NPD2160	Approved
0.6222	Remote Similarity	NPD2159	Approved
0.6222	Remote Similarity	NPD2627	Approved
0.6222	Remote Similarity	NPD3094	Phase 2
0.6207	Remote Similarity	NPD4535	Phase 3
0.6207	Remote Similarity	NPD4628	Phase 3
0.6207	Remote Similarity	NPD2575	Approved
0.6196	Remote Similarity	NPD8312	Approved
0.6196	Remote Similarity	NPD8313	Approved
0.6194	Remote Similarity	NPD4749	Approved
0.6194	Remote Similarity	NPD2982	Phase 2
0.6194	Remote Similarity	NPD6234	Discontinued
0.6194	Remote Similarity	NPD2983	Phase 2
0.619	Remote Similarity	NPD228	Approved
0.619	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1139	Approved
0.619	Remote Similarity	NPD1137	Approved
0.6187	Remote Similarity	NPD4062	Phase 3
0.6183	Remote Similarity	NPD770	Discontinued
0.6181	Remote Similarity	NPD2424	Discontinued
0.6179	Remote Similarity	NPD3134	Approved
0.6178	Remote Similarity	NPD3787	Discontinued
0.6174	Remote Similarity	NPD5403	Approved
0.6173	Remote Similarity	NPD6559	Discontinued
0.6173	Remote Similarity	NPD7685	Pre-registration
0.6173	Remote Similarity	NPD7240	Approved
0.6172	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2677	Approved
0.6149	Remote Similarity	NPD5401	Approved
0.6148	Remote Similarity	NPD1237	Approved
0.6148	Remote Similarity	NPD3225	Approved
0.6148	Remote Similarity	NPD5667	Approved
0.6147	Remote Similarity	NPD9250	Approved
0.6144	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD821	Approved
0.6142	Remote Similarity	NPD5535	Approved
0.6138	Remote Similarity	NPD5061	Approved
0.6138	Remote Similarity	NPD5062	Approved
0.6136	Remote Similarity	NPD5306	Approved
0.6136	Remote Similarity	NPD5305	Approved
0.6136	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1778	Approved
0.6135	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD9609	Approved
0.6134	Remote Similarity	NPD9612	Approved
0.6134	Remote Similarity	NPD9611	Approved
0.6131	Remote Similarity	NPD3018	Phase 2
0.6129	Remote Similarity	NPD6406	Approved
0.6125	Remote Similarity	NPD7799	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data