NPASS Compound

Structure

NPC166761 OpenBabel07101718322D 21 21 0 0 0 0 0 0 0 0999 V2000 -4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 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 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.21
Volume:	333.022
LogP:	3.995
LogD:	4.162
LogS:	-3.157
# Rotatable Bonds:	10
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	2.554
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.944
MDCK Permeability:	4.1499053622828797e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	98.63457489013672%
Volume Distribution (VD):	3.617
Pgp-substrate:	0.8649062514305115%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.78
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.627
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.976
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	7.404
Half-life (T1/2):	0.959

ADMET: Toxicity

hERG Blockers:	0.178
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.191
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.968
Carcinogencity:	0.14
Eye Corrosion:	0.447
Eye Irritation:	0.964
Respiratory Toxicity:	0.636

Download Data

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

Natural Product: NPC166761

Natural Product ID:	NPC166761
*Common Name:**	(Z,Z)-5-(Trideca-4,7-Dienyl)-Resorcinol
IUPAC Name:	5-[(4Z,7Z)-trideca-4,7-dienyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	DWGFCVWXMWMPHS-HZJYTTRNSA-N
Standard InCHI:	InChI=1S/C19H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-14-18(20)16-19(21)15-17/h6-7,9-10,14-16,20-21H,2-5,8,11-13H2,1H3/b7-6-,10-9-
SMILES:	CCCCC/C=CC/C=CCCCc1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2147166
PubChem CID:	643751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO1528	Dalea elegans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21561780]
NPO1528	Dalea elegans	Species	Fabaceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	51870.0	nM	PMID[505815]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	1700.0	nM	PMID[505815]

☑ 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 NPC166761 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	240
0.1-0.2	1630
0.2-0.3	5523
0.3-0.4	14002
0.4-0.5	5002
0.5-0.6	8895
0.6-0.7	5603
0.7-0.8	1480
0.8-0.85	179
0.85-0.9	73
0.9-0.95	44
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC24404
0.9789	High Similarity	NPC146798
0.9789	High Similarity	NPC302219
0.9789	High Similarity	NPC106396
0.9789	High Similarity	NPC242342
0.9789	High Similarity	NPC85479
0.9789	High Similarity	NPC94351
0.9789	High Similarity	NPC168303
0.9789	High Similarity	NPC222522
0.9789	High Similarity	NPC71002
0.9789	High Similarity	NPC53051
0.9789	High Similarity	NPC249828
0.9789	High Similarity	NPC313030
0.9787	High Similarity	NPC10588
0.9684	High Similarity	NPC284011
0.9684	High Similarity	NPC147310
0.9684	High Similarity	NPC72947
0.9684	High Similarity	NPC166313
0.9684	High Similarity	NPC192032
0.9684	High Similarity	NPC137415
0.9684	High Similarity	NPC11280
0.9684	High Similarity	NPC294186
0.9684	High Similarity	NPC24407
0.9485	High Similarity	NPC241891
0.9394	High Similarity	NPC158253
0.9394	High Similarity	NPC61033
0.9394	High Similarity	NPC232523
0.9394	High Similarity	NPC305603
0.9394	High Similarity	NPC204901
0.9388	High Similarity	NPC134829
0.9388	High Similarity	NPC37802
0.9355	High Similarity	NPC295295
0.9293	High Similarity	NPC201662
0.9293	High Similarity	NPC99836
0.9293	High Similarity	NPC39664
0.9293	High Similarity	NPC118286
0.9293	High Similarity	NPC109691
0.9293	High Similarity	NPC470700
0.9293	High Similarity	NPC302681
0.9293	High Similarity	NPC39097
0.9293	High Similarity	NPC12640
0.9286	High Similarity	NPC218879
0.9286	High Similarity	NPC244513
0.9286	High Similarity	NPC227458
0.9278	High Similarity	NPC143659
0.9278	High Similarity	NPC100340
0.9208	High Similarity	NPC33728
0.9208	High Similarity	NPC19808
0.92	High Similarity	NPC54844
0.9192	High Similarity	NPC246056
0.9167	High Similarity	NPC291789
0.9109	High Similarity	NPC174981
0.9091	High Similarity	NPC102216
0.9091	High Similarity	NPC30506
0.9072	High Similarity	NPC80027
0.9029	High Similarity	NPC476632
0.9029	High Similarity	NPC224527
0.9029	High Similarity	NPC4493
0.9029	High Similarity	NPC165770
0.9029	High Similarity	NPC225679
0.902	High Similarity	NPC186385
0.902	High Similarity	NPC299568
0.898	High Similarity	NPC275053
0.898	High Similarity	NPC161571
0.898	High Similarity	NPC248573
0.8947	High Similarity	NPC3358
0.8947	High Similarity	NPC162314
0.8947	High Similarity	NPC210497
0.8947	High Similarity	NPC94139
0.8947	High Similarity	NPC306884
0.8947	High Similarity	NPC147284
0.8942	High Similarity	NPC43525
0.8942	High Similarity	NPC166995
0.8936	High Similarity	NPC192
0.8925	High Similarity	NPC27974
0.8857	High Similarity	NPC117846
0.8812	High Similarity	NPC292452
0.8812	High Similarity	NPC474839
0.8776	High Similarity	NPC152097
0.8774	High Similarity	NPC107240
0.875	High Similarity	NPC168657
0.8738	High Similarity	NPC63698
0.8738	High Similarity	NPC61885
0.8713	High Similarity	NPC119860
0.8692	High Similarity	NPC84999
0.8692	High Similarity	NPC246760
0.8692	High Similarity	NPC53906
0.8687	High Similarity	NPC260775
0.8679	High Similarity	NPC162113
0.8679	High Similarity	NPC319803
0.8679	High Similarity	NPC261343
0.8679	High Similarity	NPC263753
0.8679	High Similarity	NPC62546
0.8679	High Similarity	NPC23804
0.866	High Similarity	NPC76938
0.8654	High Similarity	NPC202647
0.8632	High Similarity	NPC177420
0.8632	High Similarity	NPC280347
0.8627	High Similarity	NPC471350
0.8614	High Similarity	NPC315022
0.8611	High Similarity	NPC123559
0.8602	High Similarity	NPC150837
0.86	High Similarity	NPC70677
0.86	High Similarity	NPC48730
0.86	High Similarity	NPC130756
0.86	High Similarity	NPC12931
0.86	High Similarity	NPC248396
0.86	High Similarity	NPC129373
0.8598	High Similarity	NPC276737
0.8598	High Similarity	NPC22610
0.8586	High Similarity	NPC475078
0.8586	High Similarity	NPC474073
0.8585	High Similarity	NPC473521
0.8571	High Similarity	NPC242178
0.8571	High Similarity	NPC32714
0.8571	High Similarity	NPC224870
0.8557	High Similarity	NPC55903
0.8544	High Similarity	NPC248904
0.8544	High Similarity	NPC164576
0.8542	High Similarity	NPC55561
0.8532	High Similarity	NPC69261
0.8532	High Similarity	NPC33270
0.8532	High Similarity	NPC127894
0.8532	High Similarity	NPC470759
0.8532	High Similarity	NPC219070
0.8532	High Similarity	NPC474933
0.8532	High Similarity	NPC15860
0.8529	High Similarity	NPC315936
0.8526	High Similarity	NPC113460
0.8526	High Similarity	NPC25493
0.8519	High Similarity	NPC808
0.8491	Intermediate Similarity	NPC268032
0.8469	Intermediate Similarity	NPC245187
0.8462	Intermediate Similarity	NPC176527
0.8455	Intermediate Similarity	NPC190514
0.8455	Intermediate Similarity	NPC144343
0.8454	Intermediate Similarity	NPC231150
0.844	Intermediate Similarity	NPC141090
0.844	Intermediate Similarity	NPC114064
0.844	Intermediate Similarity	NPC150624
0.8438	Intermediate Similarity	NPC242240
0.8438	Intermediate Similarity	NPC318325
0.8438	Intermediate Similarity	NPC123273
0.8431	Intermediate Similarity	NPC196479
0.8431	Intermediate Similarity	NPC168393
0.8431	Intermediate Similarity	NPC108497
0.8426	Intermediate Similarity	NPC228287
0.8426	Intermediate Similarity	NPC180508
0.8421	Intermediate Similarity	NPC23167
0.8421	Intermediate Similarity	NPC307235
0.8421	Intermediate Similarity	NPC407
0.8416	Intermediate Similarity	NPC294741
0.8416	Intermediate Similarity	NPC130103
0.8416	Intermediate Similarity	NPC72729
0.84	Intermediate Similarity	NPC6597
0.84	Intermediate Similarity	NPC79241
0.8396	Intermediate Similarity	NPC475018
0.8396	Intermediate Similarity	NPC94045
0.8384	Intermediate Similarity	NPC274678
0.8384	Intermediate Similarity	NPC26244
0.8384	Intermediate Similarity	NPC313650
0.8384	Intermediate Similarity	NPC222146
0.8381	Intermediate Similarity	NPC105727
0.8381	Intermediate Similarity	NPC34864
0.8381	Intermediate Similarity	NPC114392
0.8381	Intermediate Similarity	NPC58427
0.8378	Intermediate Similarity	NPC217174
0.8378	Intermediate Similarity	NPC184302
0.8367	Intermediate Similarity	NPC29373
0.8365	Intermediate Similarity	NPC469913
0.8364	Intermediate Similarity	NPC470760
0.8364	Intermediate Similarity	NPC277588
0.8351	Intermediate Similarity	NPC312304
0.8349	Intermediate Similarity	NPC167934
0.8333	Intermediate Similarity	NPC19680
0.8333	Intermediate Similarity	NPC252105
0.8333	Intermediate Similarity	NPC477685
0.8333	Intermediate Similarity	NPC80800
0.8318	Intermediate Similarity	NPC296920
0.8318	Intermediate Similarity	NPC90520
0.8317	Intermediate Similarity	NPC33675
0.8317	Intermediate Similarity	NPC299762
0.8316	Intermediate Similarity	NPC155393
0.8316	Intermediate Similarity	NPC197783
0.8304	Intermediate Similarity	NPC223451
0.83	Intermediate Similarity	NPC473388
0.83	Intermediate Similarity	NPC259512
0.83	Intermediate Similarity	NPC312132
0.8288	Intermediate Similarity	NPC9592
0.8288	Intermediate Similarity	NPC48781
0.8288	Intermediate Similarity	NPC206
0.8286	Intermediate Similarity	NPC66834
0.8283	Intermediate Similarity	NPC152415
0.8283	Intermediate Similarity	NPC316301
0.8283	Intermediate Similarity	NPC151715
0.8283	Intermediate Similarity	NPC27323
0.8273	Intermediate Similarity	NPC115808
0.8269	Intermediate Similarity	NPC47284
0.8265	Intermediate Similarity	NPC270547
0.8265	Intermediate Similarity	NPC304541

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 NPC166761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	1036
0.2-0.3	1527
0.3-0.4	2984
0.4-0.5	1842
0.5-0.6	1076
0.6-0.7	379
0.7-0.8	51
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9082	High Similarity	NPD940	Approved
0.9082	High Similarity	NPD846	Approved
0.902	High Similarity	NPD4750	Phase 3
0.898	High Similarity	NPD1242	Phase 1
0.8571	High Similarity	NPD844	Approved
0.8469	Intermediate Similarity	NPD2933	Approved
0.8469	Intermediate Similarity	NPD2934	Approved
0.8384	Intermediate Similarity	NPD2859	Approved
0.8384	Intermediate Similarity	NPD2860	Approved
0.8317	Intermediate Similarity	NPD3020	Approved
0.83	Intermediate Similarity	NPD288	Approved
0.8283	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD9089	Approved
0.8105	Intermediate Similarity	NPD111	Approved
0.8065	Intermediate Similarity	NPD9093	Approved
0.8	Intermediate Similarity	NPD845	Approved
0.7963	Intermediate Similarity	NPD3022	Approved
0.7963	Intermediate Similarity	NPD3021	Approved
0.7863	Intermediate Similarity	NPD4749	Approved
0.785	Intermediate Similarity	NPD1445	Approved
0.785	Intermediate Similarity	NPD1444	Approved
0.7677	Intermediate Similarity	NPD9094	Approved
0.767	Intermediate Similarity	NPD1809	Phase 2
0.7636	Intermediate Similarity	NPD1792	Phase 2
0.7623	Intermediate Similarity	NPD4625	Phase 3
0.7623	Intermediate Similarity	NPD3027	Phase 3
0.7589	Intermediate Similarity	NPD7635	Approved
0.7544	Intermediate Similarity	NPD6671	Approved
0.7524	Intermediate Similarity	NPD9273	Approved
0.7521	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD602	Approved
0.7521	Intermediate Similarity	NPD858	Approved
0.7521	Intermediate Similarity	NPD859	Approved
0.7521	Intermediate Similarity	NPD599	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7455	Intermediate Similarity	NPD2342	Discontinued
0.7419	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD9500	Approved
0.7398	Intermediate Similarity	NPD4908	Phase 1
0.7395	Intermediate Similarity	NPD1610	Phase 2
0.7395	Intermediate Similarity	NPD422	Phase 1
0.7383	Intermediate Similarity	NPD3028	Approved
0.7368	Intermediate Similarity	NPD2228	Approved
0.7368	Intermediate Similarity	NPD2229	Approved
0.7368	Intermediate Similarity	NPD2234	Approved
0.735	Intermediate Similarity	NPD3091	Approved
0.7339	Intermediate Similarity	NPD9610	Approved
0.7339	Intermediate Similarity	NPD9608	Approved
0.7323	Intermediate Similarity	NPD2568	Approved
0.7321	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9087	Approved
0.7304	Intermediate Similarity	NPD9614	Approved
0.7304	Intermediate Similarity	NPD1793	Approved
0.7304	Intermediate Similarity	NPD1791	Approved
0.7304	Intermediate Similarity	NPD9618	Approved
0.7281	Intermediate Similarity	NPD9379	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.728	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3092	Approved
0.7227	Intermediate Similarity	NPD3019	Approved
0.7227	Intermediate Similarity	NPD2932	Approved
0.7227	Intermediate Similarity	NPD4059	Approved
0.7203	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9088	Approved
0.7177	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3094	Phase 2
0.7154	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7131	Intermediate Similarity	NPD2982	Phase 2
0.7131	Intermediate Similarity	NPD2983	Phase 2
0.7119	Intermediate Similarity	NPD9615	Approved
0.7119	Intermediate Similarity	NPD9616	Approved
0.7119	Intermediate Similarity	NPD9613	Approved
0.7119	Intermediate Similarity	NPD856	Approved
0.7119	Intermediate Similarity	NPD16	Approved
0.7107	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9381	Approved
0.7083	Intermediate Similarity	NPD9384	Approved
0.7083	Intermediate Similarity	NPD9294	Approved
0.7083	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2684	Approved
0.7059	Intermediate Similarity	NPD316	Approved
0.7054	Intermediate Similarity	NPD968	Approved
0.7049	Intermediate Similarity	NPD9269	Phase 2
0.7049	Intermediate Similarity	NPD2981	Phase 2
0.7043	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3018	Phase 2
0.7031	Intermediate Similarity	NPD943	Approved
0.7031	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1613	Approved
0.7023	Intermediate Similarity	NPD6100	Approved
0.7023	Intermediate Similarity	NPD6099	Approved
0.7009	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9268	Approved
0.6992	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9622	Approved
0.6991	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD290	Approved
0.6975	Remote Similarity	NPD317	Approved
0.6975	Remote Similarity	NPD318	Approved
0.6967	Remote Similarity	NPD1201	Approved
0.6942	Remote Similarity	NPD4626	Approved
0.6942	Remote Similarity	NPD1751	Approved
0.6942	Remote Similarity	NPD3095	Discontinued
0.6942	Remote Similarity	NPD2286	Discontinued
0.6935	Remote Similarity	NPD6696	Suspended
0.693	Remote Similarity	NPD9266	Approved
0.693	Remote Similarity	NPD74	Approved
0.6923	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5283	Phase 1
0.6917	Remote Similarity	NPD1759	Phase 1
0.6911	Remote Similarity	NPD2562	Approved
0.6911	Remote Similarity	NPD2230	Approved
0.6911	Remote Similarity	NPD2561	Approved
0.6911	Remote Similarity	NPD2233	Approved
0.6911	Remote Similarity	NPD2232	Approved
0.6905	Remote Similarity	NPD2861	Phase 2
0.6899	Remote Similarity	NPD2238	Phase 2
0.6891	Remote Similarity	NPD9493	Approved
0.6891	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3496	Discontinued
0.688	Remote Similarity	NPD3055	Approved
0.688	Remote Similarity	NPD3053	Approved
0.688	Remote Similarity	NPD1135	Approved
0.688	Remote Similarity	NPD1133	Approved
0.688	Remote Similarity	NPD1129	Approved
0.688	Remote Similarity	NPD1131	Approved
0.688	Remote Similarity	NPD1134	Approved
0.6875	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4659	Approved
0.6855	Remote Similarity	NPD1755	Approved
0.6846	Remote Similarity	NPD230	Phase 1
0.6842	Remote Similarity	NPD9267	Approved
0.6842	Remote Similarity	NPD9263	Approved
0.6842	Remote Similarity	NPD9264	Approved
0.6838	Remote Similarity	NPD821	Approved
0.6838	Remote Similarity	NPD7843	Approved
0.6833	Remote Similarity	NPD1758	Phase 1
0.6825	Remote Similarity	NPD6584	Phase 3
0.6825	Remote Similarity	NPD9621	Approved
0.6825	Remote Similarity	NPD9620	Approved
0.6825	Remote Similarity	NPD9619	Approved
0.6818	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD256	Approved
0.6807	Remote Similarity	NPD7157	Approved
0.6807	Remote Similarity	NPD709	Approved
0.6807	Remote Similarity	NPD255	Approved
0.6803	Remote Similarity	NPD1778	Approved
0.6803	Remote Similarity	NPD4589	Approved
0.68	Remote Similarity	NPD5311	Approved
0.68	Remote Similarity	NPD5310	Approved
0.6777	Remote Similarity	NPD5303	Approved
0.6777	Remote Similarity	NPD9545	Approved
0.6777	Remote Similarity	NPD5304	Approved
0.6774	Remote Similarity	NPD2231	Phase 2
0.6774	Remote Similarity	NPD2235	Phase 2
0.6774	Remote Similarity	NPD1608	Approved
0.6772	Remote Similarity	NPD5736	Approved
0.6769	Remote Similarity	NPD1240	Approved
0.6762	Remote Similarity	NPD9295	Approved
0.675	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1981	Approved
0.6748	Remote Similarity	NPD1983	Approved
0.6748	Remote Similarity	NPD1980	Approved
0.6746	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4103	Phase 2
0.6746	Remote Similarity	NPD1470	Approved
0.6744	Remote Similarity	NPD601	Approved
0.6744	Remote Similarity	NPD597	Approved
0.6744	Remote Similarity	NPD598	Approved
0.6726	Remote Similarity	NPD9244	Approved
0.6724	Remote Similarity	NPD5451	Approved
0.6723	Remote Similarity	NPD497	Approved
0.6723	Remote Similarity	NPD475	Phase 2
0.6721	Remote Similarity	NPD1357	Approved
0.672	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD600	Approved
0.6719	Remote Similarity	NPD596	Approved
0.6694	Remote Similarity	NPD1091	Approved
0.6693	Remote Similarity	NPD2194	Approved
0.6693	Remote Similarity	NPD2195	Approved
0.6692	Remote Similarity	NPD6407	Approved
0.6692	Remote Similarity	NPD1136	Approved
0.6692	Remote Similarity	NPD6405	Approved
0.6692	Remote Similarity	NPD1132	Approved
0.6692	Remote Similarity	NPD1130	Approved
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD2668	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2667	Approved
0.6641	Remote Similarity	NPD1555	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