NPASS Compound

Structure

NPC236585 OpenBabel07101719512D 32 35 0 0 1 0 0 0 0 0999 V2000 2.6546 2.1337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2550 4.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9547 -0.3402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8587 3.1680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3868 2.4480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0688 1.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1415 1.0210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1278 1.9363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3027 1.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6559 3.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7740 3.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5659 0.3381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7840 1.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4692 5.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1688 -0.8097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0433 2.3889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0197 1.3183 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5423 1.9126 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3556 0.5514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5011 0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5758 0.3210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3282 2.3821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5856 0.9802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5560 0.9972 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3045 3.9675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4828 5.9723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1825 -1.7251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0392 0.2395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3616 -0.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6696 4.6112 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 -1.3693 -0.3639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 6 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 10 30 1 0 0 0 0 11 22 1 0 0 0 0 11 25 1 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 26 2 0 0 0 0 14 30 1 0 0 0 0 15 27 2 0 0 0 0 15 32 1 0 0 0 0 16 5 1 1 0 0 0 17 23 1 6 0 0 0 17 24 1 0 0 0 0 18 22 1 1 0 0 0 18 24 1 0 0 0 0 19 24 1 1 0 0 0 19 32 1 0 0 0 0 20 23 1 0 0 0 0 20 28 2 0 0 0 0 21 23 1 0 0 0 0 21 29 2 0 0 0 0 21 31 1 0 0 0 0 22 4 1 6 0 0 0 23 9 1 6 0 0 0 24 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.21
Volume:	446.574
LogP:	1.722
LogD:	1.244
LogS:	-4.032
# Rotatable Bonds:	6
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	6.32
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.387
MDCK Permeability:	3.226458647986874e-05
Pgp-inhibitor:	0.938
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.819
Plasma Protein Binding (PPB):	61.835609436035156%
Volume Distribution (VD):	0.912
Pgp-substrate:	53.20345687866211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.332
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	2.704
Half-life (T1/2):	0.553

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.528
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.282
Carcinogencity:	0.508
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC236585

Natural Product ID:	NPC236585
*Common Name:**	WUJRTWPLVYPKCG-QITKAHHGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WUJRTWPLVYPKCG-QITKAHHGSA-N
Standard InCHI:	InChI=1S/C24H32O8/c1-13-16-5-6-17-23(9-16,20(13)28)21(29)31-12-24(17)18(10-30-14(2)26)22(4,11-25)8-7-19(24)32-15(3)27/h16-19,25H,1,5-12H2,2-4H3/t16-,17-,18-,19+,22+,23+,24+/m1/s1
SMILES:	OC[C@]1(C)CC[C@@H]([C@@]2([C@@H]1COC(=O)C)COC(=O)[C@]13[C@H]2CC[C@H](C1)C(=C)C3=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483515
PubChem CID:	24899919
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO26266	Isodon japonicus	Species	Lamiaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	8700.0	nM	PMID[448460]

☑ 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 NPC236585 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	228
0.1-0.2	1683
0.2-0.3	5592
0.3-0.4	9374
0.4-0.5	11175
0.5-0.6	5894
0.6-0.7	5439
0.7-0.8	2830
0.8-0.85	298
0.85-0.9	98
0.9-0.95	77
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC474793
0.9583	High Similarity	NPC96217
0.9479	High Similarity	NPC275990
0.9375	High Similarity	NPC46848
0.9375	High Similarity	NPC148279
0.9368	High Similarity	NPC471038
0.9362	High Similarity	NPC329910
0.9271	High Similarity	NPC267921
0.9255	High Similarity	NPC470232
0.9255	High Similarity	NPC470229
0.92	High Similarity	NPC232133
0.9192	High Similarity	NPC138908
0.9192	High Similarity	NPC200957
0.9184	High Similarity	NPC139347
0.9184	High Similarity	NPC87927
0.9184	High Similarity	NPC122811
0.9175	High Similarity	NPC289148
0.9175	High Similarity	NPC52899
0.9175	High Similarity	NPC163963
0.9167	High Similarity	NPC38471
0.9167	High Similarity	NPC98837
0.9167	High Similarity	NPC28864
0.9167	High Similarity	NPC26270
0.9167	High Similarity	NPC162459
0.9167	High Similarity	NPC20479
0.9167	High Similarity	NPC38296
0.9158	High Similarity	NPC29410
0.9158	High Similarity	NPC200054
0.9149	High Similarity	NPC475118
0.9149	High Similarity	NPC470386
0.9149	High Similarity	NPC47853
0.9149	High Similarity	NPC470385
0.9109	High Similarity	NPC469983
0.91	High Similarity	NPC166993
0.91	High Similarity	NPC96333
0.91	High Similarity	NPC176949
0.91	High Similarity	NPC88833
0.91	High Similarity	NPC61071
0.91	High Similarity	NPC201908
0.9091	High Similarity	NPC101842
0.9082	High Similarity	NPC76866
0.9082	High Similarity	NPC148628
0.9082	High Similarity	NPC246736
0.9082	High Similarity	NPC214946
0.9082	High Similarity	NPC88203
0.9082	High Similarity	NPC304832
0.9082	High Similarity	NPC286519
0.9072	High Similarity	NPC287676
0.9072	High Similarity	NPC293866
0.9062	High Similarity	NPC96839
0.9053	High Similarity	NPC98639
0.902	High Similarity	NPC320383
0.902	High Similarity	NPC474786
0.902	High Similarity	NPC137104
0.901	High Similarity	NPC273155
0.899	High Similarity	NPC277074
0.899	High Similarity	NPC209298
0.898	High Similarity	NPC252614
0.898	High Similarity	NPC14634
0.8969	High Similarity	NPC16911
0.8969	High Similarity	NPC78427
0.8969	High Similarity	NPC89099
0.8958	High Similarity	NPC470387
0.8936	High Similarity	NPC198242
0.8936	High Similarity	NPC211403
0.8936	High Similarity	NPC470230
0.8922	High Similarity	NPC131903
0.8922	High Similarity	NPC274827
0.89	High Similarity	NPC474558
0.89	High Similarity	NPC98603
0.89	High Similarity	NPC202793
0.89	High Similarity	NPC301787
0.8878	High Similarity	NPC470388
0.8866	High Similarity	NPC10864
0.8846	High Similarity	NPC474927
0.8842	High Similarity	NPC294263
0.8835	High Similarity	NPC98069
0.8835	High Similarity	NPC49730
0.8835	High Similarity	NPC85391
0.8824	High Similarity	NPC473410
0.8824	High Similarity	NPC231278
0.8824	High Similarity	NPC112895
0.8824	High Similarity	NPC63841
0.8824	High Similarity	NPC471094
0.8824	High Similarity	NPC469984
0.8824	High Similarity	NPC218123
0.8817	High Similarity	NPC56413
0.8812	High Similarity	NPC103172
0.8812	High Similarity	NPC164600
0.8812	High Similarity	NPC295366
0.8812	High Similarity	NPC222833
0.88	High Similarity	NPC216114
0.8763	High Similarity	NPC13949
0.8762	High Similarity	NPC471252
0.875	High Similarity	NPC213320
0.875	High Similarity	NPC329953
0.8737	High Similarity	NPC250753
0.8725	High Similarity	NPC471474
0.8725	High Similarity	NPC186054
0.8723	High Similarity	NPC471043
0.8713	High Similarity	NPC96268
0.8713	High Similarity	NPC84928
0.87	High Similarity	NPC475803
0.87	High Similarity	NPC309388
0.8687	High Similarity	NPC293890
0.8687	High Similarity	NPC94906
0.8673	High Similarity	NPC253586
0.8667	High Similarity	NPC473397
0.866	High Similarity	NPC210214
0.8654	High Similarity	NPC471093
0.8627	High Similarity	NPC56656
0.8627	High Similarity	NPC4115
0.8627	High Similarity	NPC307660
0.8627	High Similarity	NPC130511
0.8627	High Similarity	NPC37600
0.8614	High Similarity	NPC159442
0.8614	High Similarity	NPC469985
0.86	High Similarity	NPC39683
0.86	High Similarity	NPC471790
0.86	High Similarity	NPC71706
0.86	High Similarity	NPC253886
0.86	High Similarity	NPC121218
0.86	High Similarity	NPC75941
0.8598	High Similarity	NPC88945
0.8586	High Similarity	NPC472028
0.8585	High Similarity	NPC132668
0.8571	High Similarity	NPC470281
0.8571	High Similarity	NPC29505
0.8571	High Similarity	NPC219353
0.8558	High Similarity	NPC102741
0.8558	High Similarity	NPC469744
0.8544	High Similarity	NPC469746
0.8529	High Similarity	NPC244247
0.8529	High Similarity	NPC47281
0.8529	High Similarity	NPC13149
0.8519	High Similarity	NPC473304
0.8515	High Similarity	NPC124544
0.8515	High Similarity	NPC170615
0.8511	High Similarity	NPC259009
0.85	High Similarity	NPC108371
0.85	High Similarity	NPC180733
0.85	High Similarity	NPC37047
0.85	High Similarity	NPC41971
0.8491	Intermediate Similarity	NPC473352
0.8491	Intermediate Similarity	NPC476964
0.8485	Intermediate Similarity	NPC111187
0.8485	Intermediate Similarity	NPC190080
0.8469	Intermediate Similarity	NPC138245
0.8469	Intermediate Similarity	NPC84018
0.8469	Intermediate Similarity	NPC263135
0.8469	Intermediate Similarity	NPC288906
0.8469	Intermediate Similarity	NPC231060
0.8462	Intermediate Similarity	NPC469733
0.8462	Intermediate Similarity	NPC89860
0.8462	Intermediate Similarity	NPC189663
0.8462	Intermediate Similarity	NPC55973
0.8462	Intermediate Similarity	NPC469729
0.8462	Intermediate Similarity	NPC211224
0.8454	Intermediate Similarity	NPC181594
0.8454	Intermediate Similarity	NPC144739
0.8447	Intermediate Similarity	NPC12823
0.8447	Intermediate Similarity	NPC285927
0.8447	Intermediate Similarity	NPC50535
0.8447	Intermediate Similarity	NPC265127
0.8447	Intermediate Similarity	NPC28791
0.8438	Intermediate Similarity	NPC80401
0.8431	Intermediate Similarity	NPC470310
0.8411	Intermediate Similarity	NPC73986
0.8411	Intermediate Similarity	NPC52634
0.84	Intermediate Similarity	NPC109059
0.84	Intermediate Similarity	NPC288
0.8396	Intermediate Similarity	NPC471251
0.8384	Intermediate Similarity	NPC234564
0.8381	Intermediate Similarity	NPC118721
0.8381	Intermediate Similarity	NPC252679
0.8381	Intermediate Similarity	NPC471250
0.8367	Intermediate Similarity	NPC153775
0.8367	Intermediate Similarity	NPC169751
0.8367	Intermediate Similarity	NPC272635
0.8367	Intermediate Similarity	NPC302008
0.8367	Intermediate Similarity	NPC29247
0.8367	Intermediate Similarity	NPC289539
0.8367	Intermediate Similarity	NPC261333
0.8367	Intermediate Similarity	NPC191094
0.8367	Intermediate Similarity	NPC111524
0.8367	Intermediate Similarity	NPC91772
0.8367	Intermediate Similarity	NPC101233
0.8367	Intermediate Similarity	NPC129004
0.8367	Intermediate Similarity	NPC104371
0.8367	Intermediate Similarity	NPC215271
0.8367	Intermediate Similarity	NPC292374
0.8365	Intermediate Similarity	NPC471246
0.8365	Intermediate Similarity	NPC471461
0.8365	Intermediate Similarity	NPC67745
0.8365	Intermediate Similarity	NPC251824
0.8365	Intermediate Similarity	NPC86852
0.8351	Intermediate Similarity	NPC476934
0.8351	Intermediate Similarity	NPC476168
0.8351	Intermediate Similarity	NPC299185
0.8333	Intermediate Similarity	NPC243354

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 NPC236585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	2099
0.2-0.3	3956
0.3-0.4	1838
0.4-0.5	553
0.5-0.6	227
0.6-0.7	137
0.7-0.8	122
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7965	Intermediate Similarity	NPD6319	Approved
0.7944	Intermediate Similarity	NPD6881	Approved
0.7944	Intermediate Similarity	NPD6899	Approved
0.7925	Intermediate Similarity	NPD5739	Approved
0.7925	Intermediate Similarity	NPD7128	Approved
0.7925	Intermediate Similarity	NPD6675	Approved
0.7925	Intermediate Similarity	NPD6402	Approved
0.789	Intermediate Similarity	NPD6650	Approved
0.789	Intermediate Similarity	NPD6649	Approved
0.787	Intermediate Similarity	NPD6373	Approved
0.787	Intermediate Similarity	NPD6372	Approved
0.785	Intermediate Similarity	NPD5697	Approved
0.7818	Intermediate Similarity	NPD8297	Approved
0.7818	Intermediate Similarity	NPD6882	Approved
0.78	Intermediate Similarity	NPD8035	Phase 2
0.78	Intermediate Similarity	NPD8034	Phase 2
0.7798	Intermediate Similarity	NPD7290	Approved
0.7798	Intermediate Similarity	NPD6883	Approved
0.7798	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6869	Approved
0.7727	Intermediate Similarity	NPD8130	Phase 1
0.7727	Intermediate Similarity	NPD6847	Approved
0.7727	Intermediate Similarity	NPD6617	Approved
0.7706	Intermediate Similarity	NPD6012	Approved
0.7706	Intermediate Similarity	NPD6013	Approved
0.7706	Intermediate Similarity	NPD6014	Approved
0.7692	Intermediate Similarity	NPD7492	Approved
0.7685	Intermediate Similarity	NPD5701	Approved
0.7652	Intermediate Similarity	NPD6054	Approved
0.7627	Intermediate Similarity	NPD6616	Approved
0.7624	Intermediate Similarity	NPD6079	Approved
0.7615	Intermediate Similarity	NPD6011	Approved
0.76	Intermediate Similarity	NPD5328	Approved
0.7589	Intermediate Similarity	NPD4632	Approved
0.7563	Intermediate Similarity	NPD7078	Approved
0.7549	Intermediate Similarity	NPD6399	Phase 3
0.7524	Intermediate Similarity	NPD7638	Approved
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7458	Intermediate Similarity	NPD8328	Phase 3
0.7453	Intermediate Similarity	NPD4696	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7438	Intermediate Similarity	NPD7319	Approved
0.7436	Intermediate Similarity	NPD6015	Approved
0.7436	Intermediate Similarity	NPD6016	Approved
0.7434	Intermediate Similarity	NPD8133	Approved
0.7431	Intermediate Similarity	NPD6008	Approved
0.7429	Intermediate Similarity	NPD4755	Approved
0.7417	Intermediate Similarity	NPD8293	Discontinued
0.7411	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6009	Approved
0.7373	Intermediate Similarity	NPD5988	Approved
0.7368	Intermediate Similarity	NPD6115	Approved
0.7368	Intermediate Similarity	NPD6697	Approved
0.7368	Intermediate Similarity	NPD6118	Approved
0.7368	Intermediate Similarity	NPD6114	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7311	Intermediate Similarity	NPD7604	Phase 2
0.7308	Intermediate Similarity	NPD7748	Approved
0.7304	Intermediate Similarity	NPD6274	Approved
0.7297	Intermediate Similarity	NPD6686	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.7288	Intermediate Similarity	NPD5983	Phase 2
0.7282	Intermediate Similarity	NPD7515	Phase 2
0.7282	Intermediate Similarity	NPD6411	Approved
0.7265	Intermediate Similarity	NPD7101	Approved
0.7265	Intermediate Similarity	NPD7100	Approved
0.7264	Intermediate Similarity	NPD7902	Approved
0.7264	Intermediate Similarity	NPD6083	Phase 2
0.7264	Intermediate Similarity	NPD5173	Approved
0.7264	Intermediate Similarity	NPD6084	Phase 2
0.7263	Intermediate Similarity	NPD6116	Phase 1
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7241	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7115	Discovery
0.7232	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5223	Approved
0.7207	Intermediate Similarity	NPD6412	Phase 2
0.719	Intermediate Similarity	NPD6336	Discontinued
0.7182	Intermediate Similarity	NPD5141	Approved
0.7179	Intermediate Similarity	NPD6335	Approved
0.7172	Intermediate Similarity	NPD4788	Approved
0.717	Intermediate Similarity	NPD4697	Phase 3
0.7158	Intermediate Similarity	NPD6117	Approved
0.7155	Intermediate Similarity	NPD6868	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD6921	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7129	Intermediate Similarity	NPD3618	Phase 1
0.7117	Intermediate Similarity	NPD4768	Approved
0.7117	Intermediate Similarity	NPD4767	Approved
0.71	Intermediate Similarity	NPD4786	Approved
0.7094	Intermediate Similarity	NPD6317	Approved
0.7087	Intermediate Similarity	NPD6101	Approved
0.7087	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3573	Approved
0.7053	Intermediate Similarity	NPD3703	Phase 2
0.7048	Intermediate Similarity	NPD4202	Approved
0.7034	Intermediate Similarity	NPD6313	Approved
0.7034	Intermediate Similarity	NPD6314	Approved
0.7018	Intermediate Similarity	NPD5249	Phase 3
0.7018	Intermediate Similarity	NPD5250	Approved
0.7018	Intermediate Similarity	NPD5251	Approved
0.7018	Intermediate Similarity	NPD5247	Approved
0.7018	Intermediate Similarity	NPD5248	Approved
0.7	Intermediate Similarity	NPD6908	Approved
0.7	Intermediate Similarity	NPD6909	Approved
0.7	Intermediate Similarity	NPD7632	Discontinued
0.6991	Remote Similarity	NPD5128	Approved
0.699	Remote Similarity	NPD6672	Approved
0.699	Remote Similarity	NPD5737	Approved
0.6981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7900	Approved
0.6961	Remote Similarity	NPD5330	Approved
0.6961	Remote Similarity	NPD7521	Approved
0.6961	Remote Similarity	NPD7146	Approved
0.6961	Remote Similarity	NPD6684	Approved
0.6961	Remote Similarity	NPD7334	Approved
0.6961	Remote Similarity	NPD6409	Approved
0.6947	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4754	Approved
0.6935	Remote Similarity	NPD6033	Approved
0.693	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5695	Phase 3
0.69	Remote Similarity	NPD3667	Approved
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.6881	Remote Similarity	NPD5696	Approved
0.6881	Remote Similarity	NPD4225	Approved
0.6875	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6903	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.681	Remote Similarity	NPD5217	Approved
0.6796	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7637	Suspended
0.6765	Remote Similarity	NPD3666	Approved
0.6765	Remote Similarity	NPD3665	Phase 1
0.6765	Remote Similarity	NPD3133	Approved
0.6762	Remote Similarity	NPD4753	Phase 2
0.6759	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6053	Discontinued
0.675	Remote Similarity	NPD7328	Approved
0.675	Remote Similarity	NPD7327	Approved
0.6737	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5135	Approved
0.6724	Remote Similarity	NPD5169	Approved
0.6718	Remote Similarity	NPD6334	Approved
0.6718	Remote Similarity	NPD6333	Approved
0.6701	Remote Similarity	NPD3702	Approved
0.67	Remote Similarity	NPD7525	Registered
0.6696	Remote Similarity	NPD5168	Approved
0.6694	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6639	Remote Similarity	NPD8377	Approved
0.6639	Remote Similarity	NPD8294	Approved
0.6609	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5210	Approved
0.6606	Remote Similarity	NPD4629	Approved
0.6604	Remote Similarity	NPD6904	Approved
0.6604	Remote Similarity	NPD6673	Approved
0.6604	Remote Similarity	NPD6080	Approved
0.6585	Remote Similarity	NPD8033	Approved
0.6585	Remote Similarity	NPD8379	Approved
0.6585	Remote Similarity	NPD8335	Approved
0.6585	Remote Similarity	NPD8378	Approved
0.6585	Remote Similarity	NPD7503	Approved
0.6585	Remote Similarity	NPD8380	Approved
0.6585	Remote Similarity	NPD8296	Approved
0.6569	Remote Similarity	NPD6435	Approved
0.6526	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5282	Discontinued
0.65	Remote Similarity	NPD5167	Approved
0.6481	Remote Similarity	NPD7983	Approved
0.6481	Remote Similarity	NPD5281	Approved
0.6481	Remote Similarity	NPD5284	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