NPASS Compound

Structure

NPC471790 OpenBabel07101718312D 28 31 0 0 1 0 0 0 0 0999 V2000 2.1796 1.2152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3500 -1.8569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1883 0.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4054 0.0360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4158 -0.6584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7988 0.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6894 1.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6169 -1.0326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3142 -1.8424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2624 0.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2095 1.5463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2131 -0.6764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5961 0.3562 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0104 -0.6944 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4822 1.4840 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9644 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2980 0.9172 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8031 -2.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8196 -1.0146 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2027 0.0180 0.0000 C 0 0 1 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 -1.8446 -2.6848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5483 2.4492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5312 -0.7802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1324 1.5132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6309 -2.6479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0392 -2.6229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8175 -1.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 23 1 6 0 0 0 12 19 1 6 0 0 0 12 20 1 0 0 0 0 13 20 1 6 0 0 0 13 21 1 0 0 0 0 14 21 1 6 0 0 0 14 28 1 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 16 24 2 0 0 0 0 17 21 1 6 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 27 1 0 0 0 0 18 28 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 6 0 0 0 21 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.2
Volume:	391.169
LogP:	-0.042
LogD:	0.391
LogS:	-2.931
# Rotatable Bonds:	3
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	6.201
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.731
MDCK Permeability:	3.909576480509713e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.782

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	28.145414352416992%
Volume Distribution (VD):	0.375
Pgp-substrate:	63.263999938964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.364
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	2.908
Half-life (T1/2):	0.834

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.213
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.616
Skin Sensitization:	0.447
Carcinogencity:	0.591
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC471790

Natural Product ID:	NPC471790
*Common Name:**	QSVARWSZUOBURA-VXTMCFFMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QSVARWSZUOBURA-VXTMCFFMSA-N
Standard InCHI:	InChI=1S/C21H30O7/c1-10-15-11(23)7-13-20(3)6-4-5-19(2,9-22)12(20)8-14(28-18(26)27)21(13,16(10)24)17(15)25/h11-15,17,22-23,25H,1,4-9H2,2-3H3,(H,26,27)/t11-,12+,13-,14+,15+,17+,19+,20+,21-/m0/s1
SMILES:	CC1(CCCC2(C1CC(C34C2CC(C(C3O)C(=C)C4=O)O)OC(=O)O)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3233963
PubChem CID:	90670207
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
NPO15942	Isodon wikstroemioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697496]
NPO15942	Isodon wikstroemioides	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	6900.0	nM	PMID[495356]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16800.0	nM	PMID[495356]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[495356]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[495356]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[495356]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[495356]

☑ 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 NPC471790 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	230
0.1-0.2	1716
0.2-0.3	5645
0.3-0.4	9701
0.4-0.5	11295
0.5-0.6	6082
0.6-0.7	5646
0.7-0.8	2034
0.8-0.85	168
0.85-0.9	102
0.9-0.95	67
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC76866
0.9479	High Similarity	NPC246736
0.9479	High Similarity	NPC214946
0.9479	High Similarity	NPC309388
0.9479	High Similarity	NPC148628
0.9479	High Similarity	NPC88203
0.9479	High Similarity	NPC475803
0.9479	High Similarity	NPC286519
0.9479	High Similarity	NPC304832
0.9388	High Similarity	NPC4115
0.9375	High Similarity	NPC289148
0.9375	High Similarity	NPC163963
0.9375	High Similarity	NPC52899
0.9355	High Similarity	NPC292374
0.9355	High Similarity	NPC101233
0.9355	High Similarity	NPC111524
0.9355	High Similarity	NPC104371
0.9355	High Similarity	NPC261333
0.9355	High Similarity	NPC215271
0.9355	High Similarity	NPC153775
0.9355	High Similarity	NPC29247
0.9355	High Similarity	NPC289539
0.9355	High Similarity	NPC91772
0.9355	High Similarity	NPC129004
0.9286	High Similarity	NPC202793
0.9286	High Similarity	NPC84928
0.9286	High Similarity	NPC13149
0.9271	High Similarity	NPC287676
0.9247	High Similarity	NPC144739
0.9247	High Similarity	NPC181594
0.9192	High Similarity	NPC12823
0.9184	High Similarity	NPC139347
0.9184	High Similarity	NPC216114
0.9184	High Similarity	NPC87927
0.9175	High Similarity	NPC46848
0.9167	High Similarity	NPC16911
0.9167	High Similarity	NPC78427
0.9158	High Similarity	NPC13949
0.9158	High Similarity	NPC135548
0.9158	High Similarity	NPC264979
0.9149	High Similarity	NPC470385
0.9149	High Similarity	NPC470386
0.914	High Similarity	NPC476168
0.914	High Similarity	NPC299185
0.9091	High Similarity	NPC98603
0.9082	High Similarity	NPC275990
0.9053	High Similarity	NPC84018
0.9053	High Similarity	NPC138245
0.9053	High Similarity	NPC470232
0.9053	High Similarity	NPC231060
0.9032	High Similarity	NPC149761
0.9032	High Similarity	NPC80401
0.9032	High Similarity	NPC470378
0.9032	High Similarity	NPC261994
0.9032	High Similarity	NPC180849
0.902	High Similarity	NPC471093
0.901	High Similarity	NPC112895
0.901	High Similarity	NPC469729
0.901	High Similarity	NPC469733
0.901	High Similarity	NPC55973
0.901	High Similarity	NPC231278
0.901	High Similarity	NPC218123
0.898	High Similarity	NPC14634
0.8969	High Similarity	NPC38296
0.8969	High Similarity	NPC162459
0.8969	High Similarity	NPC471038
0.8969	High Similarity	NPC89099
0.8969	High Similarity	NPC38471
0.8969	High Similarity	NPC28864
0.8969	High Similarity	NPC98837
0.8969	High Similarity	NPC20479
0.8958	High Similarity	NPC140242
0.8958	High Similarity	NPC470387
0.8958	High Similarity	NPC329910
0.8947	High Similarity	NPC191094
0.8947	High Similarity	NPC475118
0.8947	High Similarity	NPC302008
0.8936	High Similarity	NPC198242
0.8936	High Similarity	NPC211403
0.8932	High Similarity	NPC29505
0.8932	High Similarity	NPC329953
0.8911	High Similarity	NPC471461
0.8911	High Similarity	NPC67745
0.8911	High Similarity	NPC469746
0.89	High Similarity	NPC474558
0.8878	High Similarity	NPC291785
0.8878	High Similarity	NPC156324
0.8878	High Similarity	NPC55503
0.8878	High Similarity	NPC127408
0.8878	High Similarity	NPC470388
0.8878	High Similarity	NPC293866
0.8866	High Similarity	NPC10864
0.8854	High Similarity	NPC210214
0.8854	High Similarity	NPC470229
0.8842	High Similarity	NPC59350
0.8842	High Similarity	NPC59170
0.8835	High Similarity	NPC473324
0.8824	High Similarity	NPC189663
0.8824	High Similarity	NPC273155
0.8824	High Similarity	NPC63841
0.8824	High Similarity	NPC89860
0.8812	High Similarity	NPC37600
0.8812	High Similarity	NPC138908
0.8812	High Similarity	NPC200957
0.8776	High Similarity	NPC474793
0.8763	High Similarity	NPC29410
0.8763	High Similarity	NPC200054
0.8762	High Similarity	NPC471252
0.875	High Similarity	NPC213320
0.875	High Similarity	NPC47853
0.875	High Similarity	NPC122339
0.875	High Similarity	NPC64006
0.8738	High Similarity	NPC102741
0.8738	High Similarity	NPC118721
0.8738	High Similarity	NPC252679
0.8738	High Similarity	NPC469983
0.8738	High Similarity	NPC469744
0.8737	High Similarity	NPC250753
0.8725	High Similarity	NPC201908
0.8725	High Similarity	NPC88833
0.8725	High Similarity	NPC166993
0.8725	High Similarity	NPC96333
0.8725	High Similarity	NPC186054
0.8725	High Similarity	NPC61071
0.8725	High Similarity	NPC176949
0.871	High Similarity	NPC153604
0.871	High Similarity	NPC165895
0.871	High Similarity	NPC259009
0.871	High Similarity	NPC174619
0.8667	High Similarity	NPC474927
0.8667	High Similarity	NPC473303
0.8667	High Similarity	NPC471245
0.8667	High Similarity	NPC473397
0.8667	High Similarity	NPC473352
0.866	High Similarity	NPC98639
0.866	High Similarity	NPC29112
0.8654	High Similarity	NPC471476
0.8654	High Similarity	NPC85391
0.8646	High Similarity	NPC294263
0.8641	High Similarity	NPC473410
0.8641	High Similarity	NPC471094
0.8641	High Similarity	NPC232133
0.8641	High Similarity	NPC469984
0.8627	High Similarity	NPC295366
0.8627	High Similarity	NPC307660
0.8627	High Similarity	NPC130511
0.8614	High Similarity	NPC209298
0.8614	High Similarity	NPC159442
0.8614	High Similarity	NPC470310
0.8614	High Similarity	NPC96217
0.8614	High Similarity	NPC122811
0.8614	High Similarity	NPC277074
0.86	High Similarity	NPC71706
0.86	High Similarity	NPC295276
0.86	High Similarity	NPC148279
0.86	High Similarity	NPC253886
0.86	High Similarity	NPC236585
0.86	High Similarity	NPC121218
0.8585	High Similarity	NPC471248
0.8585	High Similarity	NPC132668
0.8571	High Similarity	NPC63244
0.8544	High Similarity	NPC471474
0.8542	High Similarity	NPC278106
0.8542	High Similarity	NPC470230
0.8529	High Similarity	NPC101842
0.8529	High Similarity	NPC301787
0.8529	High Similarity	NPC96268
0.8519	High Similarity	NPC473304
0.8515	High Similarity	NPC170615
0.8505	High Similarity	NPC243354
0.85	High Similarity	NPC180733
0.85	High Similarity	NPC267921
0.85	High Similarity	NPC37047
0.85	High Similarity	NPC94906
0.85	High Similarity	NPC41971
0.8495	Intermediate Similarity	NPC471034
0.8495	Intermediate Similarity	NPC190704
0.8495	Intermediate Similarity	NPC102292
0.8491	Intermediate Similarity	NPC471244
0.8491	Intermediate Similarity	NPC145625
0.8476	Intermediate Similarity	NPC320383
0.8476	Intermediate Similarity	NPC49730
0.8476	Intermediate Similarity	NPC137104
0.8476	Intermediate Similarity	NPC474786
0.8476	Intermediate Similarity	NPC98069
0.8469	Intermediate Similarity	NPC263135
0.8469	Intermediate Similarity	NPC288906
0.8462	Intermediate Similarity	NPC211224
0.8454	Intermediate Similarity	NPC82138
0.8447	Intermediate Similarity	NPC103172
0.8447	Intermediate Similarity	NPC164600
0.8447	Intermediate Similarity	NPC56656
0.8447	Intermediate Similarity	NPC222833
0.8426	Intermediate Similarity	NPC229752
0.8426	Intermediate Similarity	NPC88945
0.8416	Intermediate Similarity	NPC252614
0.8411	Intermediate Similarity	NPC94141
0.84	Intermediate Similarity	NPC472028
0.84	Intermediate Similarity	NPC26270
0.8396	Intermediate Similarity	NPC470281

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 NPC471790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2139
0.2-0.3	4001
0.3-0.4	1822
0.4-0.5	505
0.5-0.6	207
0.6-0.7	167
0.7-0.8	89
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
0.7652	Intermediate Similarity	NPD6054	Approved
0.7586	Intermediate Similarity	NPD6015	Approved
0.7586	Intermediate Similarity	NPD6016	Approved
0.7551	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6009	Approved
0.7542	Intermediate Similarity	NPD7492	Approved
0.7523	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD5988	Approved
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7479	Intermediate Similarity	NPD6616	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7455	Intermediate Similarity	NPD6899	Approved
0.7455	Intermediate Similarity	NPD6881	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD8035	Phase 2
0.7451	Intermediate Similarity	NPD6079	Approved
0.7451	Intermediate Similarity	NPD8034	Phase 2
0.7434	Intermediate Similarity	NPD4632	Approved
0.7431	Intermediate Similarity	NPD6402	Approved
0.7431	Intermediate Similarity	NPD5739	Approved
0.7431	Intermediate Similarity	NPD6675	Approved
0.7431	Intermediate Similarity	NPD7128	Approved
0.7431	Intermediate Similarity	NPD6008	Approved
0.7429	Intermediate Similarity	NPD4755	Approved
0.7426	Intermediate Similarity	NPD5328	Approved
0.7417	Intermediate Similarity	NPD7078	Approved
0.7411	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD6649	Approved
0.7387	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD6013	Approved
0.7387	Intermediate Similarity	NPD6012	Approved
0.7387	Intermediate Similarity	NPD6372	Approved
0.7387	Intermediate Similarity	NPD6014	Approved
0.7364	Intermediate Similarity	NPD5701	Approved
0.7347	Intermediate Similarity	NPD4788	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD4697	Phase 3
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7102	Approved
0.7321	Intermediate Similarity	NPD7290	Approved
0.7321	Intermediate Similarity	NPD6883	Approved
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
0.73	Intermediate Similarity	NPD3618	Phase 1
0.7297	Intermediate Similarity	NPD7320	Approved
0.7297	Intermediate Similarity	NPD6011	Approved
0.7297	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7319	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.7273	Intermediate Similarity	NPD8293	Discontinued
0.7264	Intermediate Similarity	NPD5173	Approved
0.7257	Intermediate Similarity	NPD8130	Phase 1
0.7257	Intermediate Similarity	NPD6617	Approved
0.7257	Intermediate Similarity	NPD6869	Approved
0.7257	Intermediate Similarity	NPD6847	Approved
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7234	Intermediate Similarity	NPD3703	Phase 2
0.7222	Intermediate Similarity	NPD5223	Approved
0.7212	Intermediate Similarity	NPD6399	Phase 3
0.7196	Intermediate Similarity	NPD7638	Approved
0.7193	Intermediate Similarity	NPD8297	Approved
0.7188	Intermediate Similarity	NPD6114	Approved
0.7188	Intermediate Similarity	NPD6697	Approved
0.7188	Intermediate Similarity	NPD6118	Approved
0.7188	Intermediate Similarity	NPD6115	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7167	Intermediate Similarity	NPD8328	Phase 3
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.7129	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7515	Phase 2
0.71	Intermediate Similarity	NPD4786	Approved
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7094	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3667	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7049	Intermediate Similarity	NPD7507	Approved
0.7048	Intermediate Similarity	NPD4202	Approved
0.7009	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD5983	Phase 2
0.6991	Remote Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD4729	Approved
0.6991	Remote Similarity	NPD5128	Approved
0.6983	Remote Similarity	NPD8133	Approved
0.6981	Remote Similarity	NPD7748	Approved
0.6979	Remote Similarity	NPD6117	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6957	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6084	Phase 2
0.6944	Remote Similarity	NPD6083	Phase 2
0.6944	Remote Similarity	NPD7902	Approved
0.6937	Remote Similarity	NPD4754	Approved
0.6935	Remote Similarity	NPD6033	Approved
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD4753	Phase 2
0.6916	Remote Similarity	NPD4629	Approved
0.6916	Remote Similarity	NPD5210	Approved
0.6907	Remote Similarity	NPD6116	Phase 1
0.6885	Remote Similarity	NPD7604	Phase 2
0.6881	Remote Similarity	NPD5696	Approved
0.6881	Remote Similarity	NPD4225	Approved
0.687	Remote Similarity	NPD5250	Approved
0.687	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD5249	Phase 3
0.687	Remote Similarity	NPD5247	Approved
0.6833	Remote Similarity	NPD7101	Approved
0.6833	Remote Similarity	NPD7100	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.6807	Remote Similarity	NPD6317	Approved
0.6792	Remote Similarity	NPD6411	Approved
0.6783	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6336	Discontinued
0.6771	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5695	Phase 3
0.675	Remote Similarity	NPD6335	Approved
0.675	Remote Similarity	NPD6313	Approved
0.675	Remote Similarity	NPD6314	Approved
0.6737	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5135	Approved
0.6724	Remote Similarity	NPD5169	Approved
0.6723	Remote Similarity	NPD6868	Approved
0.6721	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5168	Approved
0.6696	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6638	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7637	Suspended
0.6635	Remote Similarity	NPD5330	Approved
0.6635	Remote Similarity	NPD7146	Approved
0.6635	Remote Similarity	NPD6409	Approved
0.6635	Remote Similarity	NPD6684	Approved
0.6635	Remote Similarity	NPD7521	Approved
0.6635	Remote Similarity	NPD7334	Approved
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.6606	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6101	Approved
0.6602	Remote Similarity	NPD3668	Phase 3
0.6585	Remote Similarity	NPD6921	Approved
0.6585	Remote Similarity	NPD6908	Approved
0.6585	Remote Similarity	NPD6909	Approved
0.6581	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5779	Approved
0.6574	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD3573	Approved
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6557	Remote Similarity	NPD7516	Approved
0.6535	Remote Similarity	NPD7525	Registered
0.6526	Remote Similarity	NPD3698	Phase 2
0.6509	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD6903	Approved
0.6509	Remote Similarity	NPD5737	Approved
0.65	Remote Similarity	NPD5167	Approved
0.6481	Remote Similarity	NPD5281	Approved
0.6481	Remote Similarity	NPD5284	Approved
0.648	Remote Similarity	NPD6067	Discontinued
0.6476	Remote Similarity	NPD5279	Phase 3
0.6471	Remote Similarity	NPD6053	Discontinued
0.6466	Remote Similarity	NPD6333	Approved
0.6466	Remote Similarity	NPD6334	Approved
0.646	Remote Similarity	NPD1700	Approved
0.6458	Remote Similarity	NPD4245	Approved
0.6458	Remote Similarity	NPD4244	Approved
0.6455	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8380	Approved
0.6452	Remote Similarity	NPD8335	Approved
0.6452	Remote Similarity	NPD8033	Approved
0.6452	Remote Similarity	NPD8379	Approved
0.6452	Remote Similarity	NPD8378	Approved
0.6452	Remote Similarity	NPD8296	Approved
0.6442	Remote Similarity	NPD4197	Approved
0.6434	Remote Similarity	NPD5956	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