NPASS Compound

Structure

NPC59170 OpenBabel07101719242D 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 -0.2082 1.5368 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 0.4792 1.4749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6851 1.0379 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 -0.0103 -0.6901 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 0.9585 -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 1 0 0 0 0 0 0 0 0 0 -1.5967 1.3341 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 12 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 8 1 1 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 1 0 0 0 13 18 1 0 0 0 0 13 19 1 6 0 0 0 14 20 1 6 0 0 0 14 22 1 0 0 0 0 15 19 1 6 0 0 0 15 20 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:	2.056
LogD:	2.43
LogS:	-3.346
# 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:	5.954
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:	-4.818
MDCK Permeability:	3.160059713991359e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.212
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.542
Plasma Protein Binding (PPB):	61.90814971923828%
Volume Distribution (VD):	0.902
Pgp-substrate:	46.694480895996094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.439
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	3.899
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.215
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.676
Carcinogencity:	0.036
Eye Corrosion:	0.059
Eye Irritation:	0.106
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC59170

Natural Product ID:	NPC59170
*Common Name:**	Phyllostachysin F
IUPAC Name:	n.a.
Synonyms:	Phyllostachysin F
Standard InCHIKey:	JHBXJYSJVIFEFY-FPARTEGVSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-10-11-8-12(21)15-19(4)7-5-6-18(2,3)13(19)9-14(22)20(15,16(10)23)17(11)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]2C[C@@H]([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:	CHEMBL1163642
PubChem CID:	16081680
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
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575445]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20521771]
NPO15942	Isodon wikstroemioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697496]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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	11

Activity Type	# Activity
Cell Line	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	850.0	nM	PMID[526232]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3300.0	nM	PMID[526232]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	3300.0	nM	PMID[526232]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	4500.0	nM	PMID[526232]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	5500.0	nM	PMID[526232]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1000.0	nM	PMID[526233]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	1100.0	nM	PMID[526233]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1500.0	nM	PMID[526233]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	2100.0	nM	PMID[526233]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2300.0	nM	PMID[526233]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3300.0	nM	PMID[526233]

☑ 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 NPC59170 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	212
0.1-0.2	1707
0.2-0.3	6243
0.3-0.4	12425
0.4-0.5	9164
0.5-0.6	5890
0.6-0.7	5061
0.7-0.8	1737
0.8-0.85	134
0.85-0.9	69
0.9-0.95	42
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC84018
0.9773	High Similarity	NPC231060
0.9773	High Similarity	NPC29112
0.9773	High Similarity	NPC138245
0.9767	High Similarity	NPC180849
0.9659	High Similarity	NPC302008
0.9659	High Similarity	NPC191094
0.9655	High Similarity	NPC278106
0.9545	High Similarity	NPC181594
0.9545	High Similarity	NPC59350
0.9545	High Similarity	NPC144739
0.9438	High Similarity	NPC91772
0.9438	High Similarity	NPC153775
0.9438	High Similarity	NPC29247
0.9438	High Similarity	NPC292374
0.9438	High Similarity	NPC289539
0.9438	High Similarity	NPC111524
0.9438	High Similarity	NPC129004
0.9438	High Similarity	NPC104371
0.9438	High Similarity	NPC261333
0.9438	High Similarity	NPC101233
0.9438	High Similarity	NPC215271
0.9432	High Similarity	NPC476168
0.9432	High Similarity	NPC299185
0.9419	High Similarity	NPC165895
0.9419	High Similarity	NPC174619
0.9348	High Similarity	NPC127408
0.9348	High Similarity	NPC291785
0.9318	High Similarity	NPC149761
0.9318	High Similarity	NPC261994
0.9318	High Similarity	NPC470378
0.9318	High Similarity	NPC80401
0.9247	High Similarity	NPC60947
0.9231	High Similarity	NPC135548
0.9231	High Similarity	NPC140242
0.9231	High Similarity	NPC264979
0.9231	High Similarity	NPC13949
0.9186	High Similarity	NPC102292
0.9111	High Similarity	NPC82138
0.907	High Similarity	NPC146683
0.9053	High Similarity	NPC87927
0.9011	High Similarity	NPC64006
0.8977	High Similarity	NPC153604
0.8977	High Similarity	NPC259009
0.8958	High Similarity	NPC13149
0.8953	High Similarity	NPC471036
0.8953	High Similarity	NPC118800
0.8953	High Similarity	NPC291320
0.8947	High Similarity	NPC272472
0.8936	High Similarity	NPC156324
0.8936	High Similarity	NPC55503
0.8913	High Similarity	NPC210214
0.8842	High Similarity	NPC52899
0.8842	High Similarity	NPC471790
0.8842	High Similarity	NPC163963
0.8842	High Similarity	NPC289148
0.8837	High Similarity	NPC110780
0.8804	High Similarity	NPC280804
0.8791	High Similarity	NPC198242
0.8791	High Similarity	NPC250753
0.8791	High Similarity	NPC211403
0.8764	High Similarity	NPC472497
0.8764	High Similarity	NPC472495
0.875	High Similarity	NPC214946
0.875	High Similarity	NPC471034
0.875	High Similarity	NPC286519
0.875	High Similarity	NPC475803
0.875	High Similarity	NPC76866
0.875	High Similarity	NPC246736
0.875	High Similarity	NPC190704
0.875	High Similarity	NPC309388
0.875	High Similarity	NPC304832
0.875	High Similarity	NPC148628
0.875	High Similarity	NPC88203
0.8737	High Similarity	NPC287676
0.871	High Similarity	NPC142352
0.871	High Similarity	NPC41070
0.8696	High Similarity	NPC294263
0.8696	High Similarity	NPC472496
0.8687	High Similarity	NPC231278
0.8687	High Similarity	NPC469733
0.8687	High Similarity	NPC112895
0.8687	High Similarity	NPC218123
0.8687	High Similarity	NPC469729
0.8681	High Similarity	NPC100313
0.866	High Similarity	NPC216114
0.866	High Similarity	NPC470310
0.8646	High Similarity	NPC46848
0.8632	High Similarity	NPC78427
0.8632	High Similarity	NPC16911
0.8632	High Similarity	NPC471038
0.8632	High Similarity	NPC109059
0.8632	High Similarity	NPC288
0.8602	High Similarity	NPC470386
0.8602	High Similarity	NPC470385
0.8586	High Similarity	NPC469746
0.8571	High Similarity	NPC98603
0.8571	High Similarity	NPC84928
0.8557	High Similarity	NPC275990
0.8556	High Similarity	NPC57469
0.8542	High Similarity	NPC470388
0.8526	High Similarity	NPC170978
0.8526	High Similarity	NPC10864
0.8511	High Similarity	NPC98639
0.8511	High Similarity	NPC470232
0.85	High Similarity	NPC55973
0.8485	Intermediate Similarity	NPC265127
0.8485	Intermediate Similarity	NPC4115
0.8485	Intermediate Similarity	NPC12823
0.8469	Intermediate Similarity	NPC139347
0.8454	Intermediate Similarity	NPC14634
0.8454	Intermediate Similarity	NPC148279
0.8444	Intermediate Similarity	NPC34190
0.8438	Intermediate Similarity	NPC38471
0.8438	Intermediate Similarity	NPC20479
0.8438	Intermediate Similarity	NPC98837
0.8438	Intermediate Similarity	NPC38296
0.8438	Intermediate Similarity	NPC162459
0.8438	Intermediate Similarity	NPC474793
0.8438	Intermediate Similarity	NPC28864
0.8438	Intermediate Similarity	NPC89099
0.8431	Intermediate Similarity	NPC29505
0.8431	Intermediate Similarity	NPC329953
0.8421	Intermediate Similarity	NPC200054
0.8421	Intermediate Similarity	NPC329910
0.8421	Intermediate Similarity	NPC29410
0.8421	Intermediate Similarity	NPC470387
0.8421	Intermediate Similarity	NPC104568
0.8416	Intermediate Similarity	NPC252679
0.8416	Intermediate Similarity	NPC118721
0.8416	Intermediate Similarity	NPC469744
0.8404	Intermediate Similarity	NPC475118
0.84	Intermediate Similarity	NPC471461
0.84	Intermediate Similarity	NPC67745
0.8384	Intermediate Similarity	NPC202793
0.8384	Intermediate Similarity	NPC474558
0.8351	Intermediate Similarity	NPC293866
0.835	Intermediate Similarity	NPC473303
0.8333	Intermediate Similarity	NPC76518
0.8333	Intermediate Similarity	NPC471093
0.8333	Intermediate Similarity	NPC473324
0.8317	Intermediate Similarity	NPC273155
0.8317	Intermediate Similarity	NPC189663
0.8317	Intermediate Similarity	NPC89860
0.8317	Intermediate Similarity	NPC9013
0.8317	Intermediate Similarity	NPC211224
0.8316	Intermediate Similarity	NPC470229
0.8316	Intermediate Similarity	NPC266431
0.8315	Intermediate Similarity	NPC472498
0.83	Intermediate Similarity	NPC37600
0.83	Intermediate Similarity	NPC138908
0.83	Intermediate Similarity	NPC200957
0.8283	Intermediate Similarity	NPC159442
0.8283	Intermediate Similarity	NPC96217
0.8283	Intermediate Similarity	NPC209298
0.8283	Intermediate Similarity	NPC122811
0.8283	Intermediate Similarity	NPC277074
0.8269	Intermediate Similarity	NPC471248
0.8269	Intermediate Similarity	NPC471252
0.8265	Intermediate Similarity	NPC71706
0.8265	Intermediate Similarity	NPC236585
0.8261	Intermediate Similarity	NPC472739
0.8256	Intermediate Similarity	NPC106078
0.8252	Intermediate Similarity	NPC122339
0.8247	Intermediate Similarity	NPC26270
0.8229	Intermediate Similarity	NPC234564
0.8229	Intermediate Similarity	NPC165616
0.8222	Intermediate Similarity	NPC474482
0.8222	Intermediate Similarity	NPC475745
0.8218	Intermediate Similarity	NPC166993
0.8218	Intermediate Similarity	NPC201908
0.8218	Intermediate Similarity	NPC176949
0.8211	Intermediate Similarity	NPC47853
0.8202	Intermediate Similarity	NPC46881
0.82	Intermediate Similarity	NPC96268
0.8182	Intermediate Similarity	NPC164999
0.8173	Intermediate Similarity	NPC473397
0.8173	Intermediate Similarity	NPC471245
0.8172	Intermediate Similarity	NPC57954
0.8172	Intermediate Similarity	NPC213832
0.8163	Intermediate Similarity	NPC267921
0.8163	Intermediate Similarity	NPC144956
0.8155	Intermediate Similarity	NPC471476
0.8152	Intermediate Similarity	NPC4643
0.8144	Intermediate Similarity	NPC190080
0.8144	Intermediate Similarity	NPC111187
0.8144	Intermediate Similarity	NPC190554
0.8144	Intermediate Similarity	NPC18509
0.8137	Intermediate Similarity	NPC63841
0.8125	Intermediate Similarity	NPC205173
0.8125	Intermediate Similarity	NPC472485
0.8125	Intermediate Similarity	NPC288906
0.8125	Intermediate Similarity	NPC263135
0.8119	Intermediate Similarity	NPC295366
0.8119	Intermediate Similarity	NPC130511
0.8119	Intermediate Similarity	NPC307660
0.8111	Intermediate Similarity	NPC475726
0.8111	Intermediate Similarity	NPC472743
0.8105	Intermediate Similarity	NPC244356
0.8105	Intermediate Similarity	NPC224060

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 NPC59170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	2104
0.2-0.3	4162
0.3-0.4	1803
0.4-0.5	455
0.5-0.6	174
0.6-0.7	148
0.7-0.8	106
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
0.8163	Intermediate Similarity	NPD5286	Approved
0.8163	Intermediate Similarity	NPD5285	Approved
0.8163	Intermediate Similarity	NPD4696	Approved
0.8144	Intermediate Similarity	NPD4755	Approved
0.8	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD4633	Approved
0.8	Intermediate Similarity	NPD5226	Approved
0.8	Intermediate Similarity	NPD5225	Approved
0.8	Intermediate Similarity	NPD5211	Phase 2
0.8	Intermediate Similarity	NPD5224	Approved
0.798	Intermediate Similarity	NPD4700	Approved
0.7979	Intermediate Similarity	NPD5328	Approved
0.7921	Intermediate Similarity	NPD5175	Approved
0.7921	Intermediate Similarity	NPD5174	Approved
0.7912	Intermediate Similarity	NPD4788	Approved
0.79	Intermediate Similarity	NPD5223	Approved
0.7857	Intermediate Similarity	NPD5221	Approved
0.7857	Intermediate Similarity	NPD4697	Phase 3
0.7857	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5222	Approved
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.7843	Intermediate Similarity	NPD5141	Approved
0.781	Intermediate Similarity	NPD4634	Approved
0.7778	Intermediate Similarity	NPD5173	Approved
0.7742	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD5697	Approved
0.766	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4786	Approved
0.7629	Intermediate Similarity	NPD8035	Phase 2
0.7629	Intermediate Similarity	NPD8034	Phase 2
0.7619	Intermediate Similarity	NPD6881	Approved
0.7619	Intermediate Similarity	NPD4730	Approved
0.7619	Intermediate Similarity	NPD4729	Approved
0.7619	Intermediate Similarity	NPD6899	Approved
0.7619	Intermediate Similarity	NPD5128	Approved
0.7609	Intermediate Similarity	NPD3667	Approved
0.7596	Intermediate Similarity	NPD6675	Approved
0.7596	Intermediate Similarity	NPD4767	Approved
0.7596	Intermediate Similarity	NPD4768	Approved
0.7596	Intermediate Similarity	NPD5739	Approved
0.7596	Intermediate Similarity	NPD6402	Approved
0.7596	Intermediate Similarity	NPD7128	Approved
0.7573	Intermediate Similarity	NPD4754	Approved
0.757	Intermediate Similarity	NPD6650	Approved
0.757	Intermediate Similarity	NPD6649	Approved
0.7547	Intermediate Similarity	NPD6373	Approved
0.7547	Intermediate Similarity	NPD6012	Approved
0.7547	Intermediate Similarity	NPD6014	Approved
0.7547	Intermediate Similarity	NPD6372	Approved
0.7547	Intermediate Similarity	NPD6013	Approved
0.7524	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD5249	Phase 3
0.7477	Intermediate Similarity	NPD5248	Approved
0.7477	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7290	Approved
0.7477	Intermediate Similarity	NPD5250	Approved
0.7477	Intermediate Similarity	NPD5251	Approved
0.7477	Intermediate Similarity	NPD7102	Approved
0.7477	Intermediate Similarity	NPD5247	Approved
0.7453	Intermediate Similarity	NPD7320	Approved
0.7453	Intermediate Similarity	NPD6011	Approved
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.7423	Intermediate Similarity	NPD4753	Phase 2
0.7416	Intermediate Similarity	NPD3703	Phase 2
0.7407	Intermediate Similarity	NPD8130	Phase 1
0.7407	Intermediate Similarity	NPD6869	Approved
0.7407	Intermediate Similarity	NPD6617	Approved
0.7407	Intermediate Similarity	NPD6847	Approved
0.7407	Intermediate Similarity	NPD5217	Approved
0.7407	Intermediate Similarity	NPD5216	Approved
0.7407	Intermediate Similarity	NPD5215	Approved
0.74	Intermediate Similarity	NPD4629	Approved
0.74	Intermediate Similarity	NPD5210	Approved
0.7374	Intermediate Similarity	NPD6399	Phase 3
0.7339	Intermediate Similarity	NPD6882	Approved
0.7339	Intermediate Similarity	NPD8297	Approved
0.7315	Intermediate Similarity	NPD5135	Approved
0.7315	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5169	Approved
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7273	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7248	Intermediate Similarity	NPD5127	Approved
0.7241	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7525	Registered
0.7193	Intermediate Similarity	NPD6054	Approved
0.7193	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD6117	Approved
0.713	Intermediate Similarity	NPD6016	Approved
0.713	Intermediate Similarity	NPD6015	Approved
0.713	Intermediate Similarity	NPD5168	Approved
0.7117	Intermediate Similarity	NPD4632	Approved
0.7103	Intermediate Similarity	NPD6008	Approved
0.7091	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7902	Approved
0.7083	Intermediate Similarity	NPD3668	Phase 3
0.708	Intermediate Similarity	NPD7115	Discovery
0.7069	Intermediate Similarity	NPD6370	Approved
0.7069	Intermediate Similarity	NPD5988	Approved
0.7054	Intermediate Similarity	NPD5167	Approved
0.7053	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD4223	Phase 3
0.7045	Intermediate Similarity	NPD3698	Phase 2
0.7043	Intermediate Similarity	NPD6059	Approved
0.6989	Remote Similarity	NPD6115	Approved
0.6989	Remote Similarity	NPD6114	Approved
0.6989	Remote Similarity	NPD6118	Approved
0.6989	Remote Similarity	NPD6697	Approved
0.6972	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4244	Approved
0.6966	Remote Similarity	NPD4245	Approved
0.6961	Remote Similarity	NPD7748	Approved
0.6957	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD7101	Approved
0.6949	Remote Similarity	NPD7492	Approved
0.6939	Remote Similarity	NPD5279	Phase 3
0.693	Remote Similarity	NPD6009	Approved
0.693	Remote Similarity	NPD6317	Approved
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7736	Approved
0.6907	Remote Similarity	NPD4197	Approved
0.6891	Remote Similarity	NPD6616	Approved
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD6314	Approved
0.687	Remote Similarity	NPD6335	Approved
0.6857	Remote Similarity	NPD4225	Approved
0.6857	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD4695	Discontinued
0.6838	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5329	Approved
0.6833	Remote Similarity	NPD7078	Approved
0.6796	Remote Similarity	NPD7900	Approved
0.6796	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4789	Approved
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4690	Approved
0.6768	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD5205	Approved
0.6768	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD4138	Approved
0.6768	Remote Similarity	NPD5690	Phase 2
0.6768	Remote Similarity	NPD4688	Approved
0.6765	Remote Similarity	NPD5284	Approved
0.6765	Remote Similarity	NPD6411	Approved
0.6765	Remote Similarity	NPD5281	Approved
0.6742	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5360	Phase 3
0.6731	Remote Similarity	NPD5695	Phase 3
0.6698	Remote Similarity	NPD7638	Approved
0.6696	Remote Similarity	NPD6868	Approved
0.6695	Remote Similarity	NPD6909	Approved
0.6695	Remote Similarity	NPD6908	Approved
0.6695	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6636	Remote Similarity	NPD7639	Approved
0.6636	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3671	Phase 1
0.6632	Remote Similarity	NPD3617	Approved
0.66	Remote Similarity	NPD7334	Approved
0.66	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD6409	Approved
0.66	Remote Similarity	NPD5280	Approved
0.66	Remote Similarity	NPD4694	Approved
0.66	Remote Similarity	NPD6684	Approved
0.66	Remote Similarity	NPD7146	Approved
0.66	Remote Similarity	NPD5330	Approved
0.6585	Remote Similarity	NPD7319	Approved
0.6583	Remote Similarity	NPD7604	Phase 2
0.6583	Remote Similarity	NPD8328	Phase 3
0.6577	Remote Similarity	NPD6412	Phase 2
0.6571	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6101	Approved
0.6569	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7645	Phase 2
0.6562	Remote Similarity	NPD4195	Approved
0.6535	Remote Similarity	NPD3573	Approved
0.6525	Remote Similarity	NPD4522	Approved
0.6522	Remote Similarity	NPD4758	Discontinued
0.6517	Remote Similarity	NPD4224	Phase 2
0.6504	Remote Similarity	NPD6033	Approved
0.6496	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7507	Approved
0.6475	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD6672	Approved
0.6471	Remote Similarity	NPD5737	Approved
0.6471	Remote Similarity	NPD6903	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