NPASS Compound

Structure

NPC210214 OpenBabel07101718192D 26 29 0 0 1 0 0 0 0 0999 V2000 1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3201 2.6376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0976 1.6627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8307 0.9825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6634 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1420 1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 8 15 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 23 2 0 0 0 0 13 26 1 0 0 0 0 14 7 1 6 0 0 0 14 19 1 0 0 0 0 15 21 1 1 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 1 0 0 0 17 22 1 1 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 19 22 1 6 0 0 0 19 26 1 0 0 0 0 21 5 1 1 0 0 0 22 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	382.094
LogP:	3.132
LogD:	3.109
LogS:	-3.959
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	5.718
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.801
MDCK Permeability:	5.9423626225907356e-05
Pgp-inhibitor:	0.204
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.346

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	80.25171661376953%
Volume Distribution (VD):	1.314
Pgp-substrate:	31.243303298950195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.185
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.281
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	3.572
Half-life (T1/2):	0.563

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.661
Carcinogencity:	0.031
Eye Corrosion:	0.157
Eye Irritation:	0.72
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC210214

Natural Product ID:	NPC210214
*Common Name:**	JSFOHQVKKXRNJH-NBTROFBBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JSFOHQVKKXRNJH-NBTROFBBSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-12-14-7-8-15-21(5)10-6-9-20(3,4)16(21)11-17(24)22(15,18(12)25)19(14)26-13(2)23/h14-17,19,24H,1,6-11H2,2-5H3/t14-,15+,16-,17-,19-,21+,22+/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@@H]2CC[C@@H]3[C@]1([C@H](O)C[C@H]1[C@@]3(C)CCCC1(C)C)C(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337570
PubChem CID:	10618528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510600]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18161942]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19899773]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22197145]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	whole plants	Vietnam	2009-Aug	PMID[23347584]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	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
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2360.0	nM	PMID[473149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1120.0	nM	PMID[473149]

☑ 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 NPC210214 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	210
0.1-0.2	1546
0.2-0.3	5494
0.3-0.4	11839
0.4-0.5	9234
0.5-0.6	5947
0.6-0.7	5439
0.7-0.8	2559
0.8-0.85	267
0.85-0.9	115
0.9-0.95	42
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.967	High Similarity	NPC78427
0.967	High Similarity	NPC16911
0.9667	High Similarity	NPC13949
0.9565	High Similarity	NPC287676
0.9462	High Similarity	NPC163963
0.9462	High Similarity	NPC289148
0.9462	High Similarity	NPC52899
0.9362	High Similarity	NPC304832
0.9362	High Similarity	NPC76866
0.9362	High Similarity	NPC148628
0.9362	High Similarity	NPC286519
0.9362	High Similarity	NPC88203
0.9362	High Similarity	NPC214946
0.9362	High Similarity	NPC246736
0.9333	High Similarity	NPC294263
0.9263	High Similarity	NPC87927
0.9263	High Similarity	NPC470310
0.9231	High Similarity	NPC47853
0.9222	High Similarity	NPC250753
0.9205	High Similarity	NPC165895
0.9167	High Similarity	NPC98603
0.9111	High Similarity	NPC470378
0.9111	High Similarity	NPC180849
0.9111	High Similarity	NPC261994
0.9111	High Similarity	NPC149761
0.9062	High Similarity	NPC216114
0.9053	High Similarity	NPC46848
0.9043	High Similarity	NPC471038
0.9032	High Similarity	NPC329910
0.9011	High Similarity	NPC299185
0.8977	High Similarity	NPC102292
0.8969	High Similarity	NPC84928
0.8958	High Similarity	NPC275990
0.8925	High Similarity	NPC205173
0.8925	High Similarity	NPC98639
0.8925	High Similarity	NPC470232
0.8925	High Similarity	NPC470229
0.8913	High Similarity	NPC59170
0.8913	High Similarity	NPC473690
0.8913	High Similarity	NPC144739
0.8913	High Similarity	NPC471902
0.8913	High Similarity	NPC59350
0.8913	High Similarity	NPC181594
0.8913	High Similarity	NPC287118
0.8889	High Similarity	NPC112895
0.8889	High Similarity	NPC231278
0.8889	High Similarity	NPC218123
0.8878	High Similarity	NPC265127
0.8854	High Similarity	NPC471790
0.8842	High Similarity	NPC162459
0.8842	High Similarity	NPC20479
0.8842	High Similarity	NPC38471
0.8842	High Similarity	NPC38296
0.8842	High Similarity	NPC98837
0.8842	High Similarity	NPC474793
0.8842	High Similarity	NPC28864
0.883	High Similarity	NPC104568
0.883	High Similarity	NPC29410
0.883	High Similarity	NPC200054
0.8817	High Similarity	NPC470386
0.8817	High Similarity	NPC29247
0.8817	High Similarity	NPC261333
0.8817	High Similarity	NPC111524
0.8817	High Similarity	NPC101233
0.8817	High Similarity	NPC91772
0.8817	High Similarity	NPC153775
0.8817	High Similarity	NPC104371
0.8817	High Similarity	NPC129004
0.8817	High Similarity	NPC289539
0.8817	High Similarity	NPC475118
0.8817	High Similarity	NPC215271
0.8817	High Similarity	NPC470385
0.8817	High Similarity	NPC292374
0.8817	High Similarity	NPC64006
0.8804	High Similarity	NPC471901
0.8804	High Similarity	NPC198242
0.8804	High Similarity	NPC475416
0.8804	High Similarity	NPC211403
0.8804	High Similarity	NPC476168
0.8791	High Similarity	NPC471043
0.8791	High Similarity	NPC57954
0.8791	High Similarity	NPC213832
0.8778	High Similarity	NPC134197
0.8778	High Similarity	NPC174619
0.8776	High Similarity	NPC474558
0.8776	High Similarity	NPC202793
0.8763	High Similarity	NPC309388
0.8763	High Similarity	NPC475803
0.875	High Similarity	NPC291320
0.875	High Similarity	NPC471036
0.875	High Similarity	NPC293866
0.875	High Similarity	NPC471037
0.8737	High Similarity	NPC10864
0.8723	High Similarity	NPC231060
0.8723	High Similarity	NPC29112
0.8723	High Similarity	NPC138245
0.8723	High Similarity	NPC84018
0.87	High Similarity	NPC273155
0.87	High Similarity	NPC211224
0.8696	High Similarity	NPC80401
0.8687	High Similarity	NPC200957
0.8687	High Similarity	NPC4115
0.8687	High Similarity	NPC138908
0.8687	High Similarity	NPC37600
0.8681	High Similarity	NPC474719
0.8681	High Similarity	NPC146937
0.8681	High Similarity	NPC471900
0.8673	High Similarity	NPC209298
0.8673	High Similarity	NPC277074
0.8673	High Similarity	NPC139347
0.8673	High Similarity	NPC122811
0.8667	High Similarity	NPC471042
0.866	High Similarity	NPC473514
0.866	High Similarity	NPC148279
0.866	High Similarity	NPC236585
0.8646	High Similarity	NPC89099
0.8636	High Similarity	NPC110780
0.8632	High Similarity	NPC470387
0.8632	High Similarity	NPC135548
0.8632	High Similarity	NPC264979
0.8632	High Similarity	NPC140242
0.8627	High Similarity	NPC329953
0.8617	High Similarity	NPC302008
0.8617	High Similarity	NPC191094
0.8602	High Similarity	NPC278106
0.8602	High Similarity	NPC470230
0.86	High Similarity	NPC176949
0.86	High Similarity	NPC201908
0.86	High Similarity	NPC166993
0.8586	High Similarity	NPC96268
0.8586	High Similarity	NPC13149
0.8571	High Similarity	NPC33768
0.8571	High Similarity	NPC259009
0.8571	High Similarity	NPC269360
0.8571	High Similarity	NPC264005
0.8557	High Similarity	NPC470388
0.8557	High Similarity	NPC108371
0.8556	High Similarity	NPC471034
0.8556	High Similarity	NPC190704
0.8542	High Similarity	NPC253586
0.8529	High Similarity	NPC471093
0.8526	High Similarity	NPC266431
0.8511	High Similarity	NPC82138
0.85	High Similarity	NPC295366
0.85	High Similarity	NPC12823
0.8495	Intermediate Similarity	NPC169933
0.8485	Intermediate Similarity	NPC96217
0.8485	Intermediate Similarity	NPC159442
0.8478	Intermediate Similarity	NPC183374
0.8478	Intermediate Similarity	NPC211162
0.8478	Intermediate Similarity	NPC56413
0.8478	Intermediate Similarity	NPC4309
0.8469	Intermediate Similarity	NPC252614
0.8469	Intermediate Similarity	NPC71706
0.8469	Intermediate Similarity	NPC121218
0.8469	Intermediate Similarity	NPC253886
0.8462	Intermediate Similarity	NPC471252
0.8462	Intermediate Similarity	NPC12774
0.8462	Intermediate Similarity	NPC2783
0.8454	Intermediate Similarity	NPC26270
0.8447	Intermediate Similarity	NPC470281
0.8447	Intermediate Similarity	NPC29505
0.8444	Intermediate Similarity	NPC146683
0.8438	Intermediate Similarity	NPC234564
0.8438	Intermediate Similarity	NPC120708
0.8438	Intermediate Similarity	NPC327788
0.8431	Intermediate Similarity	NPC102741
0.8421	Intermediate Similarity	NPC169751
0.8421	Intermediate Similarity	NPC272635
0.8416	Intermediate Similarity	NPC67745
0.8416	Intermediate Similarity	NPC471461
0.8404	Intermediate Similarity	NPC160506
0.84	Intermediate Similarity	NPC301787
0.8387	Intermediate Similarity	NPC77001
0.8387	Intermediate Similarity	NPC253618
0.8384	Intermediate Similarity	NPC136289
0.8384	Intermediate Similarity	NPC170615
0.837	Intermediate Similarity	NPC153604
0.8367	Intermediate Similarity	NPC94906
0.8367	Intermediate Similarity	NPC291785
0.8367	Intermediate Similarity	NPC156324
0.8367	Intermediate Similarity	NPC127408
0.8367	Intermediate Similarity	NPC55503
0.8367	Intermediate Similarity	NPC267921
0.8365	Intermediate Similarity	NPC474927
0.8352	Intermediate Similarity	NPC76518
0.8352	Intermediate Similarity	NPC264317
0.8352	Intermediate Similarity	NPC294438
0.8352	Intermediate Similarity	NPC201655
0.8351	Intermediate Similarity	NPC89225
0.8333	Intermediate Similarity	NPC469729
0.8333	Intermediate Similarity	NPC469733
0.8333	Intermediate Similarity	NPC469599
0.8333	Intermediate Similarity	NPC288906
0.8333	Intermediate Similarity	NPC63841
0.8333	Intermediate Similarity	NPC263135
0.8333	Intermediate Similarity	NPC55973
0.8333	Intermediate Similarity	NPC118800
0.8333	Intermediate Similarity	NPC245866
0.8317	Intermediate Similarity	NPC222833

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 NPC210214 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1896
0.2-0.3	3926
0.3-0.4	2083
0.4-0.5	554
0.5-0.6	204
0.6-0.7	164
0.7-0.8	129
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8404	Intermediate Similarity	NPD8035	Phase 2
0.8404	Intermediate Similarity	NPD8034	Phase 2
0.8352	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6399	Phase 3
0.7981	Intermediate Similarity	NPD6881	Approved
0.7981	Intermediate Similarity	NPD6899	Approved
0.7961	Intermediate Similarity	NPD6402	Approved
0.7961	Intermediate Similarity	NPD7128	Approved
0.7961	Intermediate Similarity	NPD5739	Approved
0.7961	Intermediate Similarity	NPD6675	Approved
0.7935	Intermediate Similarity	NPD4788	Approved
0.7925	Intermediate Similarity	NPD6650	Approved
0.7925	Intermediate Similarity	NPD6649	Approved
0.7905	Intermediate Similarity	NPD6373	Approved
0.7905	Intermediate Similarity	NPD6372	Approved
0.789	Intermediate Similarity	NPD7115	Discovery
0.7885	Intermediate Similarity	NPD5697	Approved
0.7857	Intermediate Similarity	NPD7748	Approved
0.7835	Intermediate Similarity	NPD7515	Phase 2
0.783	Intermediate Similarity	NPD7102	Approved
0.783	Intermediate Similarity	NPD7290	Approved
0.783	Intermediate Similarity	NPD6883	Approved
0.781	Intermediate Similarity	NPD7320	Approved
0.78	Intermediate Similarity	NPD6084	Phase 2
0.78	Intermediate Similarity	NPD6083	Phase 2
0.78	Intermediate Similarity	NPD7902	Approved
0.7757	Intermediate Similarity	NPD6869	Approved
0.7757	Intermediate Similarity	NPD6617	Approved
0.7757	Intermediate Similarity	NPD6847	Approved
0.7757	Intermediate Similarity	NPD8130	Phase 1
0.7753	Intermediate Similarity	NPD6117	Approved
0.7736	Intermediate Similarity	NPD6013	Approved
0.7736	Intermediate Similarity	NPD6012	Approved
0.7736	Intermediate Similarity	NPD6014	Approved
0.7714	Intermediate Similarity	NPD5701	Approved
0.7685	Intermediate Similarity	NPD6882	Approved
0.7685	Intermediate Similarity	NPD8297	Approved
0.7684	Intermediate Similarity	NPD3618	Phase 1
0.7667	Intermediate Similarity	NPD6116	Phase 1
0.766	Intermediate Similarity	NPD4786	Approved
0.7653	Intermediate Similarity	NPD6079	Approved
0.7642	Intermediate Similarity	NPD6011	Approved
0.7629	Intermediate Similarity	NPD5328	Approved
0.7582	Intermediate Similarity	NPD6118	Approved
0.7582	Intermediate Similarity	NPD6115	Approved
0.7582	Intermediate Similarity	NPD6114	Approved
0.7582	Intermediate Similarity	NPD6697	Approved
0.7549	Intermediate Similarity	NPD7638	Approved
0.7549	Intermediate Similarity	NPD4225	Approved
0.7549	Intermediate Similarity	NPD5696	Approved
0.7528	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7476	Intermediate Similarity	NPD7640	Approved
0.7476	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD5285	Approved
0.7476	Intermediate Similarity	NPD5286	Approved
0.7476	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD4755	Approved
0.7447	Intermediate Similarity	NPD3667	Approved
0.7431	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5695	Phase 3
0.74	Intermediate Similarity	NPD4202	Approved
0.7368	Intermediate Similarity	NPD6319	Approved
0.7353	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4697	Phase 3
0.7353	Intermediate Similarity	NPD5222	Approved
0.7353	Intermediate Similarity	NPD5221	Approved
0.7347	Intermediate Similarity	NPD6672	Approved
0.7347	Intermediate Similarity	NPD5737	Approved
0.7347	Intermediate Similarity	NPD6903	Approved
0.7333	Intermediate Similarity	NPD5226	Approved
0.7333	Intermediate Similarity	NPD5225	Approved
0.7333	Intermediate Similarity	NPD5224	Approved
0.7333	Intermediate Similarity	NPD4633	Approved
0.7333	Intermediate Similarity	NPD5211	Phase 2
0.7321	Intermediate Similarity	NPD6274	Approved
0.7308	Intermediate Similarity	NPD4700	Approved
0.7303	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6411	Approved
0.7292	Intermediate Similarity	NPD3666	Approved
0.7292	Intermediate Similarity	NPD3665	Phase 1
0.7292	Intermediate Similarity	NPD3133	Approved
0.729	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD5173	Approved
0.7281	Intermediate Similarity	NPD7101	Approved
0.7281	Intermediate Similarity	NPD7100	Approved
0.7273	Intermediate Similarity	NPD4753	Phase 2
0.7265	Intermediate Similarity	NPD7492	Approved
0.7264	Intermediate Similarity	NPD5174	Approved
0.7264	Intermediate Similarity	NPD5175	Approved
0.7255	Intermediate Similarity	NPD4629	Approved
0.7255	Intermediate Similarity	NPD5210	Approved
0.7238	Intermediate Similarity	NPD5223	Approved
0.7227	Intermediate Similarity	NPD7736	Approved
0.7217	Intermediate Similarity	NPD6054	Approved
0.7203	Intermediate Similarity	NPD6616	Approved
0.7196	Intermediate Similarity	NPD5141	Approved
0.7193	Intermediate Similarity	NPD6335	Approved
0.7182	Intermediate Similarity	NPD4634	Approved
0.7168	Intermediate Similarity	NPD6868	Approved
0.7156	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.7111	Intermediate Similarity	NPD5777	Approved
0.7105	Intermediate Similarity	NPD6317	Approved
0.71	Intermediate Similarity	NPD6904	Approved
0.71	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD6080	Approved
0.71	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6673	Approved
0.7094	Intermediate Similarity	NPD6370	Approved
0.7079	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6059	Approved
0.7053	Intermediate Similarity	NPD7525	Registered
0.7043	Intermediate Similarity	NPD6313	Approved
0.7043	Intermediate Similarity	NPD6314	Approved
0.703	Intermediate Similarity	NPD5785	Approved
0.7009	Intermediate Similarity	NPD6016	Approved
0.7009	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD6908	Approved
0.7009	Intermediate Similarity	NPD6909	Approved
0.7009	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD4245	Approved
0.7	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD4729	Approved
0.7	Intermediate Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD8133	Approved
0.699	Remote Similarity	NPD6001	Approved
0.6979	Remote Similarity	NPD5369	Approved
0.6972	Remote Similarity	NPD4768	Approved
0.6972	Remote Similarity	NPD4767	Approved
0.697	Remote Similarity	NPD6098	Approved
0.6961	Remote Similarity	NPD7637	Suspended
0.6961	Remote Similarity	NPD5281	Approved
0.6961	Remote Similarity	NPD5284	Approved
0.6957	Remote Similarity	NPD6009	Approved
0.6949	Remote Similarity	NPD5988	Approved
0.6944	Remote Similarity	NPD4754	Approved
0.6939	Remote Similarity	NPD3668	Phase 3
0.6932	Remote Similarity	NPD4224	Phase 2
0.6923	Remote Similarity	NPD6081	Approved
0.6909	Remote Similarity	NPD6412	Phase 2
0.6907	Remote Similarity	NPD4221	Approved
0.6907	Remote Similarity	NPD4223	Phase 3
0.69	Remote Similarity	NPD3573	Approved
0.6891	Remote Similarity	NPD7604	Phase 2
0.6891	Remote Similarity	NPD8328	Phase 3
0.6889	Remote Similarity	NPD3698	Phase 2
0.6885	Remote Similarity	NPD7319	Approved
0.6882	Remote Similarity	NPD3703	Phase 2
0.6882	Remote Similarity	NPD3702	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5248	Approved
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5251	Approved
0.6869	Remote Similarity	NPD5363	Approved
0.6869	Remote Similarity	NPD5329	Approved
0.6864	Remote Similarity	NPD5983	Phase 2
0.6832	Remote Similarity	NPD5208	Approved
0.6814	Remote Similarity	NPD5215	Approved
0.6814	Remote Similarity	NPD5217	Approved
0.6814	Remote Similarity	NPD5216	Approved
0.6813	Remote Similarity	NPD4789	Approved
0.681	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5279	Phase 3
0.6796	Remote Similarity	NPD6050	Approved
0.6796	Remote Similarity	NPD5693	Phase 1
0.6786	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5360	Phase 3
0.6777	Remote Similarity	NPD7507	Approved
0.6777	Remote Similarity	NPD6336	Discontinued
0.6771	Remote Similarity	NPD7645	Phase 2
0.6768	Remote Similarity	NPD4197	Approved
0.6765	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4270	Approved
0.6735	Remote Similarity	NPD4269	Approved
0.6735	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD5779	Approved
0.6726	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5135	Approved
0.6726	Remote Similarity	NPD5169	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