NPASS Compound

Structure

NPC129004 OpenBabel07101718192D 24 27 0 0 1 0 0 0 0 0999 V2000 2.1662 1.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3417 -1.8455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3001 -1.8311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1810 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 0.0358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4009 -0.6543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7878 0.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6851 1.0379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6131 -1.0262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2547 0.9116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2082 1.5368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2056 -0.6722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5925 0.3540 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0103 -0.6901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4792 1.4749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9585 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2962 0.9116 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8085 -1.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1953 0.0179 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 -0.5450 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8125 -1.1817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5219 -0.7754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1193 1.5039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 6 0 0 0 12 18 1 0 0 0 0 12 19 1 6 0 0 0 13 19 1 6 0 0 0 13 20 1 0 0 0 0 14 20 1 6 0 0 0 14 22 1 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 16 23 2 0 0 0 0 17 20 1 6 0 0 0 17 24 1 0 0 0 0 19 4 1 6 0 0 0 20 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	1.978
LogD:	2.203
LogS:	-2.995
# Rotatable Bonds:	0
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	5.939
Fsp3:	0.85
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:	-4.802
MDCK Permeability:	5.5512948165414855e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.147

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.524
Plasma Protein Binding (PPB):	66.8985366821289%
Volume Distribution (VD):	0.839
Pgp-substrate:	43.58080291748047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.732
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.288
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	3.604
Half-life (T1/2):	0.499

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.785
Carcinogencity:	0.039
Eye Corrosion:	0.054
Eye Irritation:	0.268
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC129004

Natural Product ID:	NPC129004
*Common Name:**	Isoscoparin L
IUPAC Name:	n.a.
Synonyms:	isoscoparin L
Standard InCHIKey:	UWJKFPFMTSZKRY-ANQHUWQMSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-10-15-11(21)8-13-19(4)7-5-6-18(2,3)12(19)9-14(22)20(13,16(10)23)17(15)24/h11-15,17,21-22,24H,1,5-9H2,2-4H3/t11-,12+,13-,14+,15+,17+,19+,20-/m0/s1
SMILES:	C=C1[C@@H]2[C@H](C[C@H]3[C@]4(C)CCCC(C)(C)[C@H]4C[C@H]([C@@]3(C1=O)[C@@H]2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560643
PubChem CID:	25195034
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
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072209]
NPO15942	Isodon wikstroemioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697496]
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28654256]
NPO15942	Isodon wikstroemioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18028	Isodon scoparius	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	11

Activity Type	# Activity
Cell Line	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	=	700.0	nM	PMID[506845]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6400.0	nM	PMID[506845]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	=	6800.0	nM	PMID[506845]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[506845]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2200.0	nM	PMID[506845]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	400.0	nM	PMID[506846]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	500.0	nM	PMID[506846]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	600.0	nM	PMID[506846]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	800.0	nM	PMID[506846]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	800.0	nM	PMID[506846]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	1200.0	nM	PMID[506846]

☑ 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 NPC129004 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	216
0.1-0.2	1714
0.2-0.3	5988
0.3-0.4	10973
0.4-0.5	10592
0.5-0.6	5983
0.6-0.7	5240
0.7-0.8	1711
0.8-0.85	133
0.85-0.9	73
0.9-0.95	46
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC111524
1.0	High Similarity	NPC104371
1.0	High Similarity	NPC153775
1.0	High Similarity	NPC261333
1.0	High Similarity	NPC29247
1.0	High Similarity	NPC91772
1.0	High Similarity	NPC215271
1.0	High Similarity	NPC292374
1.0	High Similarity	NPC289539
1.0	High Similarity	NPC101233
0.9885	High Similarity	NPC144739
0.9885	High Similarity	NPC181594
0.9775	High Similarity	NPC264979
0.9775	High Similarity	NPC135548
0.977	High Similarity	NPC299185
0.977	High Similarity	NPC476168
0.9663	High Similarity	NPC138245
0.9663	High Similarity	NPC231060
0.9663	High Similarity	NPC84018
0.9655	High Similarity	NPC149761
0.9655	High Similarity	NPC80401
0.9655	High Similarity	NPC261994
0.9655	High Similarity	NPC470378
0.9655	High Similarity	NPC180849
0.9556	High Similarity	NPC140242
0.9551	High Similarity	NPC191094
0.9551	High Similarity	NPC302008
0.9457	High Similarity	NPC156324
0.9457	High Similarity	NPC127408
0.9457	High Similarity	NPC55503
0.9457	High Similarity	NPC291785
0.9438	High Similarity	NPC59170
0.9438	High Similarity	NPC59350
0.9355	High Similarity	NPC471790
0.9333	High Similarity	NPC64006
0.931	High Similarity	NPC153604
0.931	High Similarity	NPC259009
0.931	High Similarity	NPC165895
0.931	High Similarity	NPC174619
0.9255	High Similarity	NPC88203
0.9255	High Similarity	NPC214946
0.9255	High Similarity	NPC246736
0.9255	High Similarity	NPC286519
0.9255	High Similarity	NPC76866
0.9255	High Similarity	NPC304832
0.9255	High Similarity	NPC148628
0.9231	High Similarity	NPC29112
0.9149	High Similarity	NPC289148
0.9149	High Similarity	NPC52899
0.9149	High Similarity	NPC163963
0.913	High Similarity	NPC13949
0.9111	High Similarity	NPC198242
0.9111	High Similarity	NPC211403
0.9111	High Similarity	NPC278106
0.908	High Similarity	NPC190704
0.908	High Similarity	NPC102292
0.908	High Similarity	NPC471034
0.9062	High Similarity	NPC84928
0.9053	High Similarity	NPC475803
0.9053	High Similarity	NPC309388
0.9043	High Similarity	NPC287676
0.9011	High Similarity	NPC82138
0.8969	High Similarity	NPC4115
0.8966	High Similarity	NPC146683
0.8958	High Similarity	NPC87927
0.8958	High Similarity	NPC216114
0.8947	High Similarity	NPC46848
0.8936	High Similarity	NPC78427
0.8936	High Similarity	NPC16911
0.8913	High Similarity	NPC280804
0.8913	High Similarity	NPC470385
0.8913	High Similarity	NPC470386
0.8866	High Similarity	NPC13149
0.8866	High Similarity	NPC98603
0.8854	High Similarity	NPC272472
0.8854	High Similarity	NPC275990
0.8851	High Similarity	NPC291320
0.8851	High Similarity	NPC118800
0.8851	High Similarity	NPC471036
0.883	High Similarity	NPC170978
0.883	High Similarity	NPC10864
0.8817	High Similarity	NPC210214
0.8817	High Similarity	NPC470232
0.8817	High Similarity	NPC41070
0.8791	High Similarity	NPC100313
0.8788	High Similarity	NPC231278
0.8788	High Similarity	NPC218123
0.8788	High Similarity	NPC112895
0.8776	High Similarity	NPC12823
0.875	High Similarity	NPC60947
0.875	High Similarity	NPC71706
0.8737	High Similarity	NPC38296
0.8737	High Similarity	NPC162459
0.8737	High Similarity	NPC38471
0.8737	High Similarity	NPC20479
0.8737	High Similarity	NPC471038
0.8737	High Similarity	NPC28864
0.8737	High Similarity	NPC98837
0.8737	High Similarity	NPC89099
0.8736	High Similarity	NPC110780
0.8723	High Similarity	NPC470387
0.8723	High Similarity	NPC329910
0.871	High Similarity	NPC475118
0.8696	High Similarity	NPC250753
0.8673	High Similarity	NPC474558
0.8673	High Similarity	NPC202793
0.8667	High Similarity	NPC472497
0.8646	High Similarity	NPC293866
0.8646	High Similarity	NPC470388
0.8617	High Similarity	NPC263135
0.8617	High Similarity	NPC470229
0.8617	High Similarity	NPC288906
0.8617	High Similarity	NPC98639
0.8602	High Similarity	NPC294263
0.86	High Similarity	NPC469729
0.86	High Similarity	NPC55973
0.86	High Similarity	NPC273155
0.86	High Similarity	NPC469733
0.8587	High Similarity	NPC46758
0.8586	High Similarity	NPC138908
0.8586	High Similarity	NPC200957
0.8586	High Similarity	NPC37600
0.8571	High Similarity	NPC470310
0.8571	High Similarity	NPC139347
0.8557	High Similarity	NPC14634
0.8542	High Similarity	NPC474793
0.8526	High Similarity	NPC200054
0.8526	High Similarity	NPC234564
0.8526	High Similarity	NPC29410
0.8511	High Similarity	NPC47853
0.85	High Similarity	NPC176949
0.85	High Similarity	NPC471461
0.85	High Similarity	NPC201908
0.85	High Similarity	NPC166993
0.85	High Similarity	NPC469746
0.85	High Similarity	NPC67745
0.8462	Intermediate Similarity	NPC57469
0.8462	Intermediate Similarity	NPC472495
0.8438	Intermediate Similarity	NPC111187
0.8438	Intermediate Similarity	NPC190080
0.8431	Intermediate Similarity	NPC471093
0.8431	Intermediate Similarity	NPC473324
0.8421	Intermediate Similarity	NPC142352
0.8416	Intermediate Similarity	NPC189663
0.8416	Intermediate Similarity	NPC89860
0.8416	Intermediate Similarity	NPC211224
0.8404	Intermediate Similarity	NPC472496
0.8404	Intermediate Similarity	NPC224060
0.8404	Intermediate Similarity	NPC244356
0.84	Intermediate Similarity	NPC295366
0.8384	Intermediate Similarity	NPC159442
0.8384	Intermediate Similarity	NPC277074
0.8384	Intermediate Similarity	NPC312900
0.8384	Intermediate Similarity	NPC122811
0.8384	Intermediate Similarity	NPC96217
0.8384	Intermediate Similarity	NPC209298
0.8367	Intermediate Similarity	NPC253886
0.8367	Intermediate Similarity	NPC121218
0.8367	Intermediate Similarity	NPC295276
0.8367	Intermediate Similarity	NPC148279
0.8367	Intermediate Similarity	NPC236585
0.8351	Intermediate Similarity	NPC288
0.8351	Intermediate Similarity	NPC109059
0.835	Intermediate Similarity	NPC29505
0.835	Intermediate Similarity	NPC122339
0.835	Intermediate Similarity	NPC329953
0.8333	Intermediate Similarity	NPC252679
0.8333	Intermediate Similarity	NPC469744
0.8333	Intermediate Similarity	NPC104568
0.8333	Intermediate Similarity	NPC118721
0.83	Intermediate Similarity	NPC301787
0.83	Intermediate Similarity	NPC96268
0.8298	Intermediate Similarity	NPC470230
0.8283	Intermediate Similarity	NPC193934
0.8283	Intermediate Similarity	NPC271980
0.8283	Intermediate Similarity	NPC170615
0.8269	Intermediate Similarity	NPC471245
0.8269	Intermediate Similarity	NPC473303
0.8265	Intermediate Similarity	NPC41971
0.8265	Intermediate Similarity	NPC94906
0.8265	Intermediate Similarity	NPC267921
0.8265	Intermediate Similarity	NPC37047
0.8265	Intermediate Similarity	NPC180733
0.8252	Intermediate Similarity	NPC471476
0.8247	Intermediate Similarity	NPC190554
0.8242	Intermediate Similarity	NPC76518
0.8235	Intermediate Similarity	NPC9013
0.8235	Intermediate Similarity	NPC63841
0.8229	Intermediate Similarity	NPC472485
0.8229	Intermediate Similarity	NPC266431
0.8222	Intermediate Similarity	NPC472498
0.8218	Intermediate Similarity	NPC222833
0.8218	Intermediate Similarity	NPC307660
0.8218	Intermediate Similarity	NPC130511
0.8218	Intermediate Similarity	NPC265127
0.82	Intermediate Similarity	NPC266
0.819	Intermediate Similarity	NPC471248
0.819	Intermediate Similarity	NPC471252
0.8182	Intermediate Similarity	NPC252614
0.8173	Intermediate Similarity	NPC213320

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 NPC129004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	2126
0.2-0.3	4138
0.3-0.4	1767
0.4-0.5	491
0.5-0.6	161
0.6-0.7	159
0.7-0.8	110
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7917	Intermediate Similarity	NPD6079	Approved
0.7905	Intermediate Similarity	NPD4634	Approved
0.79	Intermediate Similarity	NPD5285	Approved
0.79	Intermediate Similarity	NPD5286	Approved
0.79	Intermediate Similarity	NPD4696	Approved
0.7895	Intermediate Similarity	NPD5328	Approved
0.7879	Intermediate Similarity	NPD4755	Approved
0.7826	Intermediate Similarity	NPD4788	Approved
0.7778	Intermediate Similarity	NPD5222	Approved
0.7778	Intermediate Similarity	NPD4697	Phase 3
0.7778	Intermediate Similarity	NPD5221	Approved
0.7778	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD3618	Phase 1
0.7745	Intermediate Similarity	NPD5211	Phase 2
0.7745	Intermediate Similarity	NPD5226	Approved
0.7745	Intermediate Similarity	NPD4633	Approved
0.7745	Intermediate Similarity	NPD5225	Approved
0.7745	Intermediate Similarity	NPD5224	Approved
0.7727	Intermediate Similarity	NPD3703	Phase 2
0.7723	Intermediate Similarity	NPD4700	Approved
0.77	Intermediate Similarity	NPD5173	Approved
0.767	Intermediate Similarity	NPD5174	Approved
0.767	Intermediate Similarity	NPD5175	Approved
0.766	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5223	Approved
0.7596	Intermediate Similarity	NPD5141	Approved
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4786	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7475	Intermediate Similarity	NPD4202	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7383	Intermediate Similarity	NPD4729	Approved
0.7383	Intermediate Similarity	NPD6881	Approved
0.7383	Intermediate Similarity	NPD5128	Approved
0.7383	Intermediate Similarity	NPD6899	Approved
0.7383	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3133	Approved
0.7358	Intermediate Similarity	NPD6675	Approved
0.7358	Intermediate Similarity	NPD6402	Approved
0.7358	Intermediate Similarity	NPD4767	Approved
0.7358	Intermediate Similarity	NPD4768	Approved
0.7358	Intermediate Similarity	NPD7128	Approved
0.7358	Intermediate Similarity	NPD5739	Approved
0.7347	Intermediate Similarity	NPD4753	Phase 2
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7333	Intermediate Similarity	NPD4754	Approved
0.7327	Intermediate Similarity	NPD5210	Approved
0.7327	Intermediate Similarity	NPD4629	Approved
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6372	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7315	Intermediate Similarity	NPD6373	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7283	Intermediate Similarity	NPD6697	Approved
0.7283	Intermediate Similarity	NPD6118	Approved
0.7283	Intermediate Similarity	NPD6114	Approved
0.7283	Intermediate Similarity	NPD6115	Approved
0.7281	Intermediate Similarity	NPD6054	Approved
0.7281	Intermediate Similarity	NPD6319	Approved
0.7248	Intermediate Similarity	NPD6883	Approved
0.7248	Intermediate Similarity	NPD5247	Approved
0.7248	Intermediate Similarity	NPD7290	Approved
0.7248	Intermediate Similarity	NPD5249	Phase 3
0.7248	Intermediate Similarity	NPD5250	Approved
0.7248	Intermediate Similarity	NPD5248	Approved
0.7248	Intermediate Similarity	NPD5251	Approved
0.7248	Intermediate Similarity	NPD7102	Approved
0.7222	Intermediate Similarity	NPD7320	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7217	Intermediate Similarity	NPD6015	Approved
0.7217	Intermediate Similarity	NPD6016	Approved
0.7207	Intermediate Similarity	NPD4632	Approved
0.72	Intermediate Similarity	NPD7515	Phase 2
0.7196	Intermediate Similarity	NPD6008	Approved
0.7191	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5215	Approved
0.7182	Intermediate Similarity	NPD5216	Approved
0.7182	Intermediate Similarity	NPD6617	Approved
0.7182	Intermediate Similarity	NPD5217	Approved
0.7182	Intermediate Similarity	NPD8130	Phase 1
0.7182	Intermediate Similarity	NPD6847	Approved
0.7182	Intermediate Similarity	NPD6869	Approved
0.7159	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5988	Approved
0.7155	Intermediate Similarity	NPD6370	Approved
0.713	Intermediate Similarity	NPD6059	Approved
0.7129	Intermediate Similarity	NPD6399	Phase 3
0.7117	Intermediate Similarity	NPD6882	Approved
0.7117	Intermediate Similarity	NPD8297	Approved
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5169	Approved
0.7091	Intermediate Similarity	NPD5135	Approved
0.7065	Intermediate Similarity	NPD6117	Approved
0.7064	Intermediate Similarity	NPD5168	Approved
0.7064	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7492	Approved
0.7027	Intermediate Similarity	NPD5127	Approved
0.7018	Intermediate Similarity	NPD6009	Approved
0.7018	Intermediate Similarity	NPD7115	Discovery
0.701	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD7736	Approved
0.6989	Remote Similarity	NPD6116	Phase 1
0.6979	Remote Similarity	NPD4223	Phase 3
0.6979	Remote Similarity	NPD4221	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.6966	Remote Similarity	NPD3698	Phase 2
0.6952	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD7525	Registered
0.693	Remote Similarity	NPD6274	Approved
0.6917	Remote Similarity	NPD7078	Approved
0.6893	Remote Similarity	NPD7748	Approved
0.6889	Remote Similarity	NPD4245	Approved
0.6889	Remote Similarity	NPD4244	Approved
0.6887	Remote Similarity	NPD7639	Approved
0.6887	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5279	Phase 3
0.6857	Remote Similarity	NPD6083	Phase 2
0.6857	Remote Similarity	NPD7902	Approved
0.6857	Remote Similarity	NPD6084	Phase 2
0.6848	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5167	Approved
0.6837	Remote Similarity	NPD4197	Approved
0.6803	Remote Similarity	NPD7319	Approved
0.6792	Remote Similarity	NPD4225	Approved
0.6792	Remote Similarity	NPD5696	Approved
0.678	Remote Similarity	NPD5983	Phase 2
0.6777	Remote Similarity	NPD8293	Discontinued
0.6771	Remote Similarity	NPD4695	Discontinued
0.6768	Remote Similarity	NPD5329	Approved
0.6752	Remote Similarity	NPD7100	Approved
0.6752	Remote Similarity	NPD7101	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.6705	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4789	Approved
0.6702	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4688	Approved
0.67	Remote Similarity	NPD4689	Approved
0.67	Remote Similarity	NPD5690	Phase 2
0.67	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD4138	Approved
0.67	Remote Similarity	NPD4690	Approved
0.67	Remote Similarity	NPD4693	Phase 3
0.6699	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6639	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6868	Approved
0.661	Remote Similarity	NPD4522	Approved
0.6596	Remote Similarity	NPD7339	Approved
0.6596	Remote Similarity	NPD6942	Approved
0.6585	Remote Similarity	NPD6033	Approved
0.6581	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7900	Approved
0.6571	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3617	Approved
0.6562	Remote Similarity	NPD3671	Phase 1
0.6557	Remote Similarity	NPD7507	Approved
0.6557	Remote Similarity	NPD6336	Discontinued
0.6538	Remote Similarity	NPD5284	Approved
0.6538	Remote Similarity	NPD7637	Suspended
0.6538	Remote Similarity	NPD5281	Approved
0.6535	Remote Similarity	NPD7521	Approved
0.6535	Remote Similarity	NPD5330	Approved
0.6535	Remote Similarity	NPD4694	Approved
0.6535	Remote Similarity	NPD7334	Approved
0.6535	Remote Similarity	NPD5280	Approved
0.6535	Remote Similarity	NPD6684	Approved
0.6535	Remote Similarity	NPD6409	Approved
0.6535	Remote Similarity	NPD7146	Approved
0.6509	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD6909	Approved
0.65	Remote Similarity	NPD6908	Approved
0.6495	Remote Similarity	NPD4195	Approved
0.6495	Remote Similarity	NPD7645	Phase 2
0.6495	Remote Similarity	NPD6929	Approved
0.6476	Remote Similarity	NPD5778	Approved
0.6476	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3573	Approved
0.6466	Remote Similarity	NPD8133	Approved
0.6455	Remote Similarity	NPD7632	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