NPASS Compound

Structure

NPC79736 OpenBabel07101718222D 48 52 0 0 1 0 0 0 0 0999 V2000 -5.8216 0.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8174 -0.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4345 0.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 0.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7682 1.1747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5208 -0.4666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0659 -1.0729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6313 -0.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4751 -1.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2812 0.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1764 -0.0275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8719 1.5152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1495 -1.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4897 -1.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5789 -0.7768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2812 1.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3196 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9237 -0.9008 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8262 0.8645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4233 1.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8787 1.0073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1495 -2.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4897 -2.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 0.4791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3196 -2.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 1.4374 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.9166 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8299 1.4374 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3196 0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2355 0.8202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7443 0.6687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3196 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 0.4791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3839 -1.6926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5286 1.8994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9794 -2.8749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 -2.8749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3196 -3.8331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 1.9166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6598 1.9166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1495 0.4791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8873 0.1178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6015 -0.2789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4897 0.4791 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 -1.6598 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 44 1 0 0 0 0 2 45 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 17 1 0 0 0 0 6 19 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 2 0 0 0 0 15 46 1 0 0 0 0 17 30 1 0 0 0 0 18 33 1 0 0 0 0 19 35 1 1 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 31 2 0 0 0 0 22 36 1 0 0 0 0 23 26 2 0 0 0 0 23 37 1 0 0 0 0 24 26 1 0 0 0 0 24 38 1 0 0 0 0 25 15 1 1 0 0 0 25 27 1 0 0 0 0 25 47 1 0 0 0 0 26 39 1 0 0 0 0 27 28 1 0 0 0 0 27 40 1 6 0 0 0 28 29 1 0 0 0 0 28 41 1 1 0 0 0 29 34 1 0 0 0 0 29 42 1 6 0 0 0 30 32 2 0 0 0 0 30 48 1 0 0 0 0 31 32 1 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 43 2 0 0 0 0 33 46 1 0 0 0 0 34 47 1 0 0 0 0 34 48 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	672.24
Volume:	650.536
LogP:	3.142
LogD:	1.882
LogS:	-4.059
# Rotatable Bonds:	8
TPSA:	225.06
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	6.045
Fsp3:	0.441
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.388
MDCK Permeability:	1.1076100236095954e-05
Pgp-inhibitor:	0.233
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.456
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.725

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	98.9098892211914%
Volume Distribution (VD):	0.415
Pgp-substrate:	2.8143155574798584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.307
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.35
CYP2C9-substrate:	0.383
CYP2D6-inhibitor:	0.455
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	8.32
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.399
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.321
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.965
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.588
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC79736

Natural Product ID:	NPC79736
*Common Name:**	PXTKHOHAJHGCKB-CMCWUMRESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PXTKHOHAJHGCKB-CMCWUMRESA-N
Standard InCHI:	InChI=1S/C34H40O14/c1-44-31-21-12-17(5-3-4-6-19(35)9-7-16-8-10-22(36)20(21)11-16)30(32(31)45-2)48-34-29(42)28(41)27(40)25(47-34)15-46-33(43)18-13-23(37)26(39)24(38)14-18/h8,10-14,19,25,27-29,34-42H,3-7,9,15H2,1-2H3/t19-,25-,27-,28+,29-,34+/m1/s1
SMILES:	COc1c(O[C@@H]2O[C@H](COC(=O)c3cc(O)c(c(c3)O)O)[C@H]([C@@H]([C@H]2O)O)O)c2CCCC[C@H](CCc3cc(c(c1OC)c2)c(O)cc3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152657
PubChem CID:	14031380
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	barks	n.a.	n.a.	PMID[23066712]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	90.5	ug.mL-1	PMID[560185]

☑ 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 NPC79736 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	390
0.1-0.2	1575
0.2-0.3	3403
0.3-0.4	7867
0.4-0.5	9615
0.5-0.6	4869
0.6-0.7	4902
0.7-0.8	6649
0.8-0.85	2342
0.85-0.9	927
0.9-0.95	150
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67629
0.9939	High Similarity	NPC267549
0.9518	High Similarity	NPC316539
0.9401	High Similarity	NPC175230
0.9401	High Similarity	NPC88560
0.9401	High Similarity	NPC172033
0.9387	High Similarity	NPC285108
0.9387	High Similarity	NPC33298
0.9353	High Similarity	NPC208797
0.9353	High Similarity	NPC53680
0.9337	High Similarity	NPC658
0.9337	High Similarity	NPC197708
0.931	High Similarity	NPC264302
0.9294	High Similarity	NPC80956
0.929	High Similarity	NPC297574
0.929	High Similarity	NPC472723
0.9281	High Similarity	NPC204937
0.9281	High Similarity	NPC149011
0.9264	High Similarity	NPC289346
0.9264	High Similarity	NPC239966
0.9264	High Similarity	NPC53889
0.9264	High Similarity	NPC203020
0.9226	High Similarity	NPC102851
0.9226	High Similarity	NPC5786
0.9212	High Similarity	NPC121290
0.9202	High Similarity	NPC289811
0.9202	High Similarity	NPC160780
0.9202	High Similarity	NPC87317
0.9186	High Similarity	NPC123259
0.9186	High Similarity	NPC129533
0.9181	High Similarity	NPC471030
0.9172	High Similarity	NPC472993
0.9172	High Similarity	NPC46640
0.9172	High Similarity	NPC263119
0.9172	High Similarity	NPC34436
0.9172	High Similarity	NPC166674
0.9172	High Similarity	NPC219600
0.9167	High Similarity	NPC180768
0.9162	High Similarity	NPC116745
0.9162	High Similarity	NPC473818
0.9152	High Similarity	NPC90905
0.9152	High Similarity	NPC476372
0.9152	High Similarity	NPC4013
0.9152	High Similarity	NPC148273
0.9152	High Similarity	NPC476371
0.9146	High Similarity	NPC24164
0.9141	High Similarity	NPC114179
0.9141	High Similarity	NPC68324
0.9141	High Similarity	NPC472860
0.9141	High Similarity	NPC38779
0.9141	High Similarity	NPC1913
0.9141	High Similarity	NPC289322
0.9141	High Similarity	NPC160512
0.9141	High Similarity	NPC133984
0.9141	High Similarity	NPC156818
0.9138	High Similarity	NPC65489
0.9138	High Similarity	NPC105591
0.9133	High Similarity	NPC231254
0.9128	High Similarity	NPC8940
0.9123	High Similarity	NPC472387
0.9123	High Similarity	NPC476618
0.9123	High Similarity	NPC476619
0.9123	High Similarity	NPC476621
0.9123	High Similarity	NPC476622
0.9123	High Similarity	NPC476623
0.9123	High Similarity	NPC476620
0.9112	High Similarity	NPC67134
0.9112	High Similarity	NPC47140
0.9107	High Similarity	NPC229687
0.9091	High Similarity	NPC311803
0.9091	High Similarity	NPC472859
0.9091	High Similarity	NPC25389
0.9086	High Similarity	NPC269046
0.9086	High Similarity	NPC473618
0.908	High Similarity	NPC261623
0.908	High Similarity	NPC291948
0.908	High Similarity	NPC250436
0.908	High Similarity	NPC300845
0.908	High Similarity	NPC104983
0.908	High Similarity	NPC88803
0.908	High Similarity	NPC111490
0.9075	High Similarity	NPC35924
0.9075	High Similarity	NPC199172
0.907	High Similarity	NPC212290
0.9064	High Similarity	NPC472991
0.9064	High Similarity	NPC472992
0.9059	High Similarity	NPC208668
0.9059	High Similarity	NPC98583
0.9059	High Similarity	NPC473550
0.9059	High Similarity	NPC163165
0.9053	High Similarity	NPC52598
0.9053	High Similarity	NPC76047
0.9053	High Similarity	NPC181778
0.9048	High Similarity	NPC45400
0.9048	High Similarity	NPC477502
0.9048	High Similarity	NPC229729
0.9042	High Similarity	NPC165720
0.9042	High Similarity	NPC471788
0.9036	High Similarity	NPC291957
0.9036	High Similarity	NPC14030
0.9034	High Similarity	NPC469652
0.9034	High Similarity	NPC160543
0.9034	High Similarity	NPC472724
0.9034	High Similarity	NPC472720
0.9034	High Similarity	NPC93065
0.9034	High Similarity	NPC472721
0.9034	High Similarity	NPC31208
0.903	High Similarity	NPC476373
0.903	High Similarity	NPC166277
0.903	High Similarity	NPC119125
0.9029	High Similarity	NPC260521
0.9029	High Similarity	NPC237202
0.9029	High Similarity	NPC179947
0.9029	High Similarity	NPC469649
0.9023	High Similarity	NPC470416
0.9023	High Similarity	NPC25946
0.9023	High Similarity	NPC460984
0.9023	High Similarity	NPC21359
0.9023	High Similarity	NPC470713
0.9023	High Similarity	NPC470720
0.9023	High Similarity	NPC470717
0.9023	High Similarity	NPC49690
0.9017	High Similarity	NPC469371
0.9012	High Similarity	NPC217520
0.9012	High Similarity	NPC477895
0.9012	High Similarity	NPC139571
0.9012	High Similarity	NPC35167
0.9006	High Similarity	NPC193377
0.9006	High Similarity	NPC469354
0.9006	High Similarity	NPC169645
0.9006	High Similarity	NPC108202
0.9006	High Similarity	NPC84482
0.9	High Similarity	NPC100251
0.9	High Similarity	NPC254540
0.9	High Similarity	NPC48773
0.9	High Similarity	NPC256760
0.9	High Similarity	NPC172807
0.9	High Similarity	NPC211594
0.9	High Similarity	NPC205076
0.9	High Similarity	NPC307518
0.9	High Similarity	NPC472386
0.9	High Similarity	NPC65333
0.8994	High Similarity	NPC95421
0.8994	High Similarity	NPC198125
0.8994	High Similarity	NPC149300
0.8989	High Similarity	NPC476358
0.8988	High Similarity	NPC236934
0.8988	High Similarity	NPC43065
0.8988	High Similarity	NPC5778
0.8982	High Similarity	NPC470898
0.8982	High Similarity	NPC88043
0.8977	High Similarity	NPC223534
0.8977	High Similarity	NPC142291
0.8977	High Similarity	NPC119094
0.8977	High Similarity	NPC173872
0.8977	High Similarity	NPC7839
0.8977	High Similarity	NPC290289
0.8977	High Similarity	NPC240200
0.8977	High Similarity	NPC158214
0.8971	High Similarity	NPC295625
0.8971	High Similarity	NPC470719
0.8971	High Similarity	NPC104910
0.8971	High Similarity	NPC473554
0.8971	High Similarity	NPC474093
0.8971	High Similarity	NPC469650
0.897	High Similarity	NPC74319
0.897	High Similarity	NPC287872
0.8966	High Similarity	NPC162394
0.8966	High Similarity	NPC321916
0.8966	High Similarity	NPC132111
0.8966	High Similarity	NPC36138
0.8966	High Similarity	NPC241781
0.8966	High Similarity	NPC470718
0.8966	High Similarity	NPC156785
0.8963	High Similarity	NPC318432
0.8963	High Similarity	NPC165483
0.8963	High Similarity	NPC471405
0.8957	High Similarity	NPC327032
0.8957	High Similarity	NPC194095
0.8957	High Similarity	NPC191046
0.8953	High Similarity	NPC61904
0.8953	High Similarity	NPC144097
0.8953	High Similarity	NPC255799
0.8953	High Similarity	NPC473713
0.8947	High Similarity	NPC4390
0.8947	High Similarity	NPC25724
0.8941	High Similarity	NPC150767
0.8941	High Similarity	NPC474434
0.8941	High Similarity	NPC177731
0.8941	High Similarity	NPC470272
0.8941	High Similarity	NPC471416
0.8941	High Similarity	NPC105095
0.8941	High Similarity	NPC231194
0.8941	High Similarity	NPC79056
0.8941	High Similarity	NPC44558
0.8941	High Similarity	NPC78734
0.8941	High Similarity	NPC51326
0.8941	High Similarity	NPC224462
0.8941	High Similarity	NPC21190
0.8941	High Similarity	NPC212748

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 NPC79736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	911
0.2-0.3	1773
0.3-0.4	2596
0.4-0.5	1923
0.5-0.6	977
0.6-0.7	434
0.7-0.8	141
0.8-0.85	35
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD4868	Clinical (unspecified phase)
0.8941	High Similarity	NPD7074	Phase 3
0.8882	High Similarity	NPD5844	Phase 1
0.8882	High Similarity	NPD7054	Approved
0.883	High Similarity	NPD7472	Approved
0.8824	High Similarity	NPD3818	Discontinued
0.8786	High Similarity	NPD4338	Clinical (unspecified phase)
0.8678	High Similarity	NPD7808	Phase 3
0.8671	High Similarity	NPD7993	Clinical (unspecified phase)
0.8621	High Similarity	NPD7251	Discontinued
0.8596	High Similarity	NPD6166	Phase 2
0.8596	High Similarity	NPD6168	Clinical (unspecified phase)
0.8596	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8563	High Similarity	NPD6797	Phase 2
0.8555	High Similarity	NPD7804	Clinical (unspecified phase)
0.8514	High Similarity	NPD6559	Discontinued
0.8503	High Similarity	NPD2393	Clinical (unspecified phase)
0.8503	High Similarity	NPD1465	Phase 2
0.8497	Intermediate Similarity	NPD7228	Approved
0.848	Intermediate Similarity	NPD6232	Discontinued
0.8443	Intermediate Similarity	NPD1934	Approved
0.8439	Intermediate Similarity	NPD7473	Discontinued
0.8409	Intermediate Similarity	NPD7685	Pre-registration
0.8393	Intermediate Similarity	NPD8455	Phase 2
0.8389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7075	Discontinued
0.8324	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD8312	Approved
0.8315	Intermediate Similarity	NPD8313	Approved
0.8314	Intermediate Similarity	NPD7199	Phase 2
0.8304	Intermediate Similarity	NPD6234	Discontinued
0.8297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7819	Suspended
0.8253	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD37	Approved
0.8214	Intermediate Similarity	NPD4380	Phase 2
0.8204	Intermediate Similarity	NPD1653	Approved
0.8187	Intermediate Similarity	NPD4965	Approved
0.8187	Intermediate Similarity	NPD7768	Phase 2
0.8187	Intermediate Similarity	NPD4967	Phase 2
0.8187	Intermediate Similarity	NPD4966	Approved
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2801	Approved
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7411	Suspended
0.815	Intermediate Similarity	NPD5494	Approved
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD8151	Discontinued
0.8114	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD7240	Approved
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7964	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7783	Phase 2
0.7927	Intermediate Similarity	NPD7266	Discontinued
0.7857	Intermediate Similarity	NPD1511	Approved
0.7831	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD5402	Approved
0.7811	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD3751	Discontinued
0.7772	Intermediate Similarity	NPD7435	Discontinued
0.7772	Intermediate Similarity	NPD7680	Approved
0.7765	Intermediate Similarity	NPD1512	Approved
0.7738	Intermediate Similarity	NPD6190	Approved
0.7733	Intermediate Similarity	NPD7458	Discontinued
0.7733	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD230	Phase 1
0.7727	Intermediate Similarity	NPD3749	Approved
0.7706	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3750	Approved
0.7669	Intermediate Similarity	NPD1613	Approved
0.7669	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1549	Phase 2
0.7656	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3787	Discontinued
0.7647	Intermediate Similarity	NPD6799	Approved
0.7641	Intermediate Similarity	NPD7870	Phase 2
0.7641	Intermediate Similarity	NPD7871	Phase 2
0.7626	Intermediate Similarity	NPD7874	Approved
0.7626	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6674	Discontinued
0.7617	Intermediate Similarity	NPD6776	Approved
0.7617	Intermediate Similarity	NPD6781	Approved
0.7617	Intermediate Similarity	NPD6779	Approved
0.7617	Intermediate Similarity	NPD6780	Approved
0.7617	Intermediate Similarity	NPD6782	Approved
0.7617	Intermediate Similarity	NPD6778	Approved
0.7617	Intermediate Similarity	NPD6777	Approved
0.7616	Intermediate Similarity	NPD5403	Approved
0.7614	Intermediate Similarity	NPD7585	Approved
0.7605	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8127	Discontinued
0.759	Intermediate Similarity	NPD7697	Approved
0.759	Intermediate Similarity	NPD7698	Approved
0.759	Intermediate Similarity	NPD7696	Phase 3
0.7586	Intermediate Similarity	NPD6599	Discontinued
0.7584	Intermediate Similarity	NPD919	Approved
0.7563	Intermediate Similarity	NPD7583	Approved
0.7556	Intermediate Similarity	NPD7229	Phase 3
0.7552	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7701	Phase 2
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD3027	Phase 3
0.7475	Intermediate Similarity	NPD7584	Approved
0.7471	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD8319	Approved
0.7462	Intermediate Similarity	NPD8320	Phase 1
0.7449	Intermediate Similarity	NPD6823	Phase 2
0.744	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD2796	Approved
0.7439	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3226	Approved
0.7423	Intermediate Similarity	NPD7700	Phase 2
0.7423	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7699	Phase 2
0.7413	Intermediate Similarity	NPD7801	Approved
0.741	Intermediate Similarity	NPD1933	Approved
0.7407	Intermediate Similarity	NPD8434	Phase 2
0.7403	Intermediate Similarity	NPD1247	Approved
0.7394	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1510	Phase 2
0.7381	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6534	Approved
0.7358	Intermediate Similarity	NPD6535	Approved
0.7353	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5242	Approved
0.7318	Intermediate Similarity	NPD5353	Approved
0.7317	Intermediate Similarity	NPD4908	Phase 1
0.7314	Intermediate Similarity	NPD920	Approved
0.7305	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.7258	Intermediate Similarity	NPD7286	Phase 2
0.7246	Intermediate Similarity	NPD943	Approved
0.7246	Intermediate Similarity	NPD1240	Approved
0.7235	Intermediate Similarity	NPD1551	Phase 2
0.7229	Intermediate Similarity	NPD6798	Discontinued
0.722	Intermediate Similarity	NPD7930	Approved
0.7219	Intermediate Similarity	NPD7097	Phase 1
0.7204	Intermediate Similarity	NPD7177	Discontinued
0.7202	Intermediate Similarity	NPD5124	Phase 1
0.7202	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7549	Discontinued
0.7193	Intermediate Similarity	NPD2346	Discontinued
0.7176	Intermediate Similarity	NPD2799	Discontinued
0.7168	Intermediate Similarity	NPD8166	Discontinued
0.7168	Intermediate Similarity	NPD7003	Approved
0.716	Intermediate Similarity	NPD1607	Approved
0.7159	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD9494	Approved
0.7151	Intermediate Similarity	NPD6385	Approved
0.7151	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD7039	Approved
0.7135	Intermediate Similarity	NPD6099	Approved
0.7135	Intermediate Similarity	NPD6100	Approved
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1243	Approved
0.711	Intermediate Similarity	NPD2800	Approved
0.7109	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7093	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6233	Phase 2
0.7081	Intermediate Similarity	NPD5711	Approved
0.7081	Intermediate Similarity	NPD5710	Approved
0.7079	Intermediate Similarity	NPD7999	Approved
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.7041	Intermediate Similarity	NPD4060	Phase 1
0.7035	Intermediate Similarity	NPD5408	Approved
0.7035	Intermediate Similarity	NPD5405	Approved
0.7035	Intermediate Similarity	NPD5404	Approved
0.7035	Intermediate Similarity	NPD5406	Approved
0.7024	Intermediate Similarity	NPD2313	Discontinued
0.7024	Intermediate Similarity	NPD3764	Approved
0.7011	Intermediate Similarity	NPD1652	Phase 2
0.701	Intermediate Similarity	NPD6842	Approved
0.701	Intermediate Similarity	NPD6841	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