NPASS Compound

Structure

NPC260832 OpenBabel07101719512D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 23 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 1 0 0 0 17 20 1 0 0 0 0 17 21 1 1 0 0 0 18 19 1 0 0 0 0 21 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.24
Volume:	355.774
LogP:	5.877
LogD:	4.445
LogS:	-5.514
# Rotatable Bonds:	2
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	3.964
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.778
MDCK Permeability:	1.5377790987258777e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.294
Plasma Protein Binding (PPB):	97.257568359375%
Volume Distribution (VD):	2.417
Pgp-substrate:	3.2171413898468018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.2
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.225
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.36
CYP2D6-substrate:	0.689
CYP3A4-inhibitor:	0.424
CYP3A4-substrate:	0.692

ADMET: Excretion

Clearance (CL):	7.754
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.406
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.498
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.922
Carcinogencity:	0.21
Eye Corrosion:	0.107
Eye Irritation:	0.901
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC260832

Natural Product ID:	NPC260832
*Common Name:**	Nootkastatin 1
IUPAC Name:	(4bS,8aS,10S)-10-methoxy-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
Synonyms:	Nootkastatin 1
Standard InCHIKey:	KEZJULFFBNQVPA-XGHQBKJUSA-N
Standard InCHI:	InChI=1S/C21H32O2/c1-13(2)18-15(22)9-8-14-19(18)16(23-6)12-17-20(3,4)10-7-11-21(14,17)5/h8-9,13,16-17,22H,7,10-12H2,1-6H3/t16-,17-,21+/m0/s1
SMILES:	CO[C@H]1C[C@H]2C(C)(C)CCC[C@@]2(c2c1c(C(C)C)c(O)cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510002
PubChem CID:	11415828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO29845	Chamaecyparis nootkatensis	Species	Cupressaceae	Eukaryota	n.a.	Alaskan	n.a.	PMID[15387645]
NPO29845	Chamaecyparis nootkatensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
ED50	1
GI50	6
MIC	24
Others	5

Activity Type	# Activity
Cell Line	7
Organism	29

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.5	ug ml-1	PMID[560060]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	2.1	ug.mL-1	PMID[560060]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.85	ug.mL-1	PMID[560060]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.75	ug.mL-1	PMID[560060]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.98	ug.mL-1	PMID[560060]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	1.1	ug.mL-1	PMID[560060]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	2.0	ug.mL-1	PMID[560060]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	64.0	ug.mL-1	PMID[560060]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[560060]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	32.0	ug ml-1	PMID[560060]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	64.0	ug.mL-1	PMID[560060]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	64.0	ug ml-1	PMID[560060]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[560060]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	=	16.0	ug ml-1	PMID[560060]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2.0	ug.mL-1	PMID[560060]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	8.0	ug ml-1	PMID[560060]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	2.0	ug.mL-1	PMID[560060]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MBC	=	4.0	ug ml-1	PMID[560060]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT1521	Organism	Stenotrophomonas maltophilia	Stenotrophomonas maltophilia	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	64.0	ug.mL-1	PMID[560060]
NPT3649	Organism	Rhodococcus sp.	Rhodococcus sp.	MIC	>	64.0	ug.mL-1	PMID[560060]

☑ 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 NPC260832 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	298
0.1-0.2	1479
0.2-0.3	2972
0.3-0.4	8914
0.4-0.5	10280
0.5-0.6	7669
0.6-0.7	8613
0.7-0.8	2255
0.8-0.85	154
0.85-0.9	36
0.9-0.95	24
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135467
0.9469	High Similarity	NPC308828
0.9381	High Similarity	NPC147179
0.9304	High Similarity	NPC469609
0.9298	High Similarity	NPC219112
0.9292	High Similarity	NPC268160
0.913	High Similarity	NPC92
0.913	High Similarity	NPC477137
0.913	High Similarity	NPC308311
0.913	High Similarity	NPC38893
0.913	High Similarity	NPC469663
0.9107	High Similarity	NPC141782
0.906	High Similarity	NPC469644
0.9052	High Similarity	NPC477136
0.9043	High Similarity	NPC192948
0.9043	High Similarity	NPC35797
0.9016	High Similarity	NPC471077
0.8974	High Similarity	NPC471671
0.8947	High Similarity	NPC228425
0.8917	High Similarity	NPC152946
0.8889	High Similarity	NPC304510
0.8889	High Similarity	NPC172219
0.886	High Similarity	NPC260323
0.886	High Similarity	NPC176279
0.8852	High Similarity	NPC124030
0.8852	High Similarity	NPC4286
0.8852	High Similarity	NPC76119
0.8803	High Similarity	NPC471668
0.8793	High Similarity	NPC195922
0.8783	High Similarity	NPC250323
0.8772	High Similarity	NPC13482
0.876	High Similarity	NPC471794
0.873	High Similarity	NPC312341
0.8729	High Similarity	NPC16030
0.8696	High Similarity	NPC95716
0.8696	High Similarity	NPC77772
0.8678	High Similarity	NPC253627
0.8661	High Similarity	NPC85595
0.8655	High Similarity	NPC48342
0.8655	High Similarity	NPC164649
0.8655	High Similarity	NPC154030
0.8644	High Similarity	NPC257540
0.8644	High Similarity	NPC141001
0.8644	High Similarity	NPC474387
0.8644	High Similarity	NPC474358
0.8644	High Similarity	NPC137496
0.8644	High Similarity	NPC154511
0.8644	High Similarity	NPC247858
0.8632	High Similarity	NPC471534
0.8621	High Similarity	NPC177962
0.8621	High Similarity	NPC46940
0.8621	High Similarity	NPC62867
0.8609	High Similarity	NPC132720
0.8607	High Similarity	NPC478058
0.8596	High Similarity	NPC11554
0.8595	High Similarity	NPC129176
0.8595	High Similarity	NPC328504
0.8583	High Similarity	NPC323074
0.8583	High Similarity	NPC126002
0.8583	High Similarity	NPC151197
0.8583	High Similarity	NPC93071
0.856	High Similarity	NPC186889
0.8548	High Similarity	NPC87985
0.8547	High Similarity	NPC715
0.8537	High Similarity	NPC471187
0.8537	High Similarity	NPC198014
0.8534	High Similarity	NPC266937
0.8534	High Similarity	NPC322753
0.8534	High Similarity	NPC470770
0.8516	High Similarity	NPC27578
0.8516	High Similarity	NPC321086
0.8516	High Similarity	NPC289624
0.8512	High Similarity	NPC103916
0.8512	High Similarity	NPC477037
0.8512	High Similarity	NPC318581
0.8512	High Similarity	NPC325544
0.8509	High Similarity	NPC151477
0.8504	High Similarity	NPC99795
0.8504	High Similarity	NPC196193
0.8492	Intermediate Similarity	NPC201069
0.8487	Intermediate Similarity	NPC312105
0.8468	Intermediate Similarity	NPC265413
0.8468	Intermediate Similarity	NPC10154
0.8468	Intermediate Similarity	NPC181334
0.8455	Intermediate Similarity	NPC11250
0.845	Intermediate Similarity	NPC227719
0.8448	Intermediate Similarity	NPC296683
0.8438	Intermediate Similarity	NPC153019
0.8438	Intermediate Similarity	NPC78575
0.8413	Intermediate Similarity	NPC108164
0.8403	Intermediate Similarity	NPC469719
0.8397	Intermediate Similarity	NPC68292
0.8374	Intermediate Similarity	NPC142198
0.8374	Intermediate Similarity	NPC77569
0.8372	Intermediate Similarity	NPC59239
0.8372	Intermediate Similarity	NPC165612
0.8362	Intermediate Similarity	NPC58865
0.8361	Intermediate Similarity	NPC68339
0.8361	Intermediate Similarity	NPC282255
0.8361	Intermediate Similarity	NPC3239
0.8359	Intermediate Similarity	NPC249425
0.8348	Intermediate Similarity	NPC320439
0.8346	Intermediate Similarity	NPC47288
0.8333	Intermediate Similarity	NPC321822
0.8333	Intermediate Similarity	NPC117115
0.8333	Intermediate Similarity	NPC325294
0.8333	Intermediate Similarity	NPC43000
0.8333	Intermediate Similarity	NPC470724
0.8333	Intermediate Similarity	NPC100414
0.832	Intermediate Similarity	NPC248557
0.8308	Intermediate Similarity	NPC211352
0.8306	Intermediate Similarity	NPC121168
0.8306	Intermediate Similarity	NPC71094
0.8305	Intermediate Similarity	NPC228452
0.8293	Intermediate Similarity	NPC32322
0.8293	Intermediate Similarity	NPC259703
0.8281	Intermediate Similarity	NPC206028
0.8281	Intermediate Similarity	NPC86257
0.8276	Intermediate Similarity	NPC262365
0.8268	Intermediate Similarity	NPC476536
0.8264	Intermediate Similarity	NPC25648
0.8264	Intermediate Similarity	NPC299180
0.8261	Intermediate Similarity	NPC21594
0.8261	Intermediate Similarity	NPC271274
0.8254	Intermediate Similarity	NPC470726
0.8254	Intermediate Similarity	NPC137750
0.825	Intermediate Similarity	NPC474486
0.8235	Intermediate Similarity	NPC141003
0.8235	Intermediate Similarity	NPC35344
0.8226	Intermediate Similarity	NPC249340
0.8226	Intermediate Similarity	NPC474115
0.8226	Intermediate Similarity	NPC162935
0.822	Intermediate Similarity	NPC151537
0.8205	Intermediate Similarity	NPC314187
0.8203	Intermediate Similarity	NPC307050
0.8203	Intermediate Similarity	NPC277458
0.8203	Intermediate Similarity	NPC176590
0.8203	Intermediate Similarity	NPC223912
0.8197	Intermediate Similarity	NPC206
0.819	Intermediate Similarity	NPC27252
0.819	Intermediate Similarity	NPC472979
0.8189	Intermediate Similarity	NPC170485
0.8189	Intermediate Similarity	NPC71610
0.8182	Intermediate Similarity	NPC33900
0.8175	Intermediate Similarity	NPC474532
0.8174	Intermediate Similarity	NPC138942
0.8174	Intermediate Similarity	NPC243601
0.816	Intermediate Similarity	NPC176208
0.816	Intermediate Similarity	NPC321402
0.816	Intermediate Similarity	NPC30462
0.8154	Intermediate Similarity	NPC258073
0.8151	Intermediate Similarity	NPC98372
0.8151	Intermediate Similarity	NPC302371
0.8145	Intermediate Similarity	NPC241001
0.8142	Intermediate Similarity	NPC225506
0.8142	Intermediate Similarity	NPC211885
0.813	Intermediate Similarity	NPC121866
0.813	Intermediate Similarity	NPC42657
0.812	Intermediate Similarity	NPC472982
0.812	Intermediate Similarity	NPC149455
0.812	Intermediate Similarity	NPC64642
0.811	Intermediate Similarity	NPC105718
0.811	Intermediate Similarity	NPC266705
0.811	Intermediate Similarity	NPC278955
0.811	Intermediate Similarity	NPC29008
0.811	Intermediate Similarity	NPC105031
0.811	Intermediate Similarity	NPC228771
0.8103	Intermediate Similarity	NPC155072
0.8092	Intermediate Similarity	NPC321502
0.8088	Intermediate Similarity	NPC186033
0.8087	Intermediate Similarity	NPC288411
0.8087	Intermediate Similarity	NPC475225
0.8083	Intermediate Similarity	NPC317869
0.8083	Intermediate Similarity	NPC123175
0.8083	Intermediate Similarity	NPC176730
0.8083	Intermediate Similarity	NPC322239
0.808	Intermediate Similarity	NPC154696
0.808	Intermediate Similarity	NPC475166
0.808	Intermediate Similarity	NPC475839
0.808	Intermediate Similarity	NPC168707
0.808	Intermediate Similarity	NPC48623
0.8077	Intermediate Similarity	NPC470727
0.8077	Intermediate Similarity	NPC472793
0.8074	Intermediate Similarity	NPC221134
0.807	Intermediate Similarity	NPC252105
0.8067	Intermediate Similarity	NPC469912
0.8067	Intermediate Similarity	NPC275627
0.8067	Intermediate Similarity	NPC308689
0.8067	Intermediate Similarity	NPC470723
0.8065	Intermediate Similarity	NPC99734
0.8065	Intermediate Similarity	NPC190501
0.8065	Intermediate Similarity	NPC318552
0.8065	Intermediate Similarity	NPC478121
0.8062	Intermediate Similarity	NPC215300
0.8062	Intermediate Similarity	NPC471064
0.8062	Intermediate Similarity	NPC38017
0.8053	Intermediate Similarity	NPC252821
0.8053	Intermediate Similarity	NPC122005
0.8049	Intermediate Similarity	NPC63010
0.8034	Intermediate Similarity	NPC472980

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 NPC260832 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	931
0.2-0.3	1364
0.3-0.4	2685
0.4-0.5	2044
0.5-0.6	1183
0.6-0.7	534
0.7-0.8	120
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD3091	Approved
0.8374	Intermediate Similarity	NPD3092	Approved
0.8305	Intermediate Similarity	NPD7635	Approved
0.8268	Intermediate Similarity	NPD5736	Approved
0.8254	Intermediate Similarity	NPD3094	Phase 2
0.824	Intermediate Similarity	NPD5327	Phase 3
0.824	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD3095	Discontinued
0.8106	Intermediate Similarity	NPD4097	Suspended
0.8092	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD3620	Phase 2
0.8065	Intermediate Similarity	NPD4059	Approved
0.8065	Intermediate Similarity	NPD3019	Approved
0.8047	Intermediate Similarity	NPD4624	Approved
0.8034	Intermediate Similarity	NPD2342	Discontinued
0.803	Intermediate Similarity	NPD5735	Approved
0.8015	Intermediate Similarity	NPD6663	Approved
0.797	Intermediate Similarity	NPD6353	Approved
0.7955	Intermediate Similarity	NPD4140	Approved
0.792	Intermediate Similarity	NPD2932	Approved
0.792	Intermediate Similarity	NPD4626	Approved
0.7895	Intermediate Similarity	NPD3020	Approved
0.7891	Intermediate Similarity	NPD6696	Suspended
0.7846	Intermediate Similarity	NPD2861	Phase 2
0.7826	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD4060	Phase 1
0.7788	Intermediate Similarity	NPD1809	Phase 2
0.7769	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7340	Approved
0.7719	Intermediate Similarity	NPD288	Approved
0.7699	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5691	Approved
0.7669	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6671	Approved
0.766	Intermediate Similarity	NPD7041	Phase 2
0.766	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2860	Approved
0.7632	Intermediate Similarity	NPD2859	Approved
0.7632	Intermediate Similarity	NPD844	Approved
0.7623	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD845	Approved
0.7606	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3021	Approved
0.7603	Intermediate Similarity	NPD3022	Approved
0.7594	Intermediate Similarity	NPD4625	Phase 3
0.7591	Intermediate Similarity	NPD7743	Approved
0.7591	Intermediate Similarity	NPD7742	Approved
0.7559	Intermediate Similarity	NPD4093	Discontinued
0.7544	Intermediate Similarity	NPD2934	Approved
0.7544	Intermediate Similarity	NPD2933	Approved
0.7519	Intermediate Similarity	NPD4908	Phase 1
0.7519	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2286	Discontinued
0.75	Intermediate Similarity	NPD1751	Approved
0.75	Intermediate Similarity	NPD1398	Phase 1
0.7481	Intermediate Similarity	NPD1283	Approved
0.748	Intermediate Similarity	NPD7741	Discontinued
0.7462	Intermediate Similarity	NPD2233	Approved
0.7462	Intermediate Similarity	NPD2232	Approved
0.7462	Intermediate Similarity	NPD2230	Approved
0.7459	Intermediate Similarity	NPD4750	Phase 3
0.7447	Intermediate Similarity	NPD7003	Approved
0.7447	Intermediate Similarity	NPD8166	Discontinued
0.7442	Intermediate Similarity	NPD3023	Approved
0.7442	Intermediate Similarity	NPD3026	Approved
0.7422	Intermediate Similarity	NPD3025	Approved
0.7422	Intermediate Similarity	NPD1651	Approved
0.7422	Intermediate Similarity	NPD3024	Approved
0.7388	Intermediate Similarity	NPD2606	Approved
0.7388	Intermediate Similarity	NPD2605	Approved
0.7385	Intermediate Similarity	NPD1610	Phase 2
0.7381	Intermediate Similarity	NPD7157	Approved
0.7376	Intermediate Similarity	NPD6674	Discontinued
0.7372	Intermediate Similarity	NPD3657	Discovery
0.7368	Intermediate Similarity	NPD6584	Phase 3
0.736	Intermediate Similarity	NPD5283	Phase 1
0.7357	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8032	Phase 2
0.7348	Intermediate Similarity	NPD8651	Approved
0.7333	Intermediate Similarity	NPD5156	Approved
0.7333	Intermediate Similarity	NPD5155	Approved
0.7323	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3636	Approved
0.7313	Intermediate Similarity	NPD3635	Approved
0.7313	Intermediate Similarity	NPD3637	Approved
0.7305	Intermediate Similarity	NPD7037	Approved
0.7299	Intermediate Similarity	NPD2238	Phase 2
0.7273	Intermediate Similarity	NPD1669	Approved
0.7273	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4749	Approved
0.7259	Intermediate Similarity	NPD3595	Approved
0.7259	Intermediate Similarity	NPD3594	Approved
0.7254	Intermediate Similarity	NPD3638	Discontinued
0.7252	Intermediate Similarity	NPD1281	Approved
0.725	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2195	Approved
0.7239	Intermediate Similarity	NPD2194	Approved
0.7234	Intermediate Similarity	NPD5763	Approved
0.7234	Intermediate Similarity	NPD5762	Approved
0.7231	Intermediate Similarity	NPD4589	Approved
0.7222	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1753	Discontinued
0.7206	Intermediate Similarity	NPD7095	Approved
0.7206	Intermediate Similarity	NPD3027	Phase 3
0.72	Intermediate Similarity	NPD228	Approved
0.7194	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2157	Approved
0.7192	Intermediate Similarity	NPD6273	Approved
0.7177	Intermediate Similarity	NPD1792	Phase 2
0.7177	Intermediate Similarity	NPD5451	Approved
0.7174	Intermediate Similarity	NPD2979	Phase 3
0.7174	Intermediate Similarity	NPD3110	Approved
0.7174	Intermediate Similarity	NPD3109	Approved
0.7167	Intermediate Similarity	NPD940	Approved
0.7167	Intermediate Similarity	NPD846	Approved
0.7165	Intermediate Similarity	NPD497	Approved
0.7163	Intermediate Similarity	NPD6099	Approved
0.7163	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7294	Phase 1
0.7143	Intermediate Similarity	NPD5699	Approved
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7121	Intermediate Similarity	NPD1201	Approved
0.7121	Intermediate Similarity	NPD1611	Approved
0.7109	Intermediate Similarity	NPD709	Approved
0.7099	Intermediate Similarity	NPD2667	Approved
0.7099	Intermediate Similarity	NPD2668	Approved
0.7097	Intermediate Similarity	NPD2684	Approved
0.7092	Intermediate Similarity	NPD4108	Discontinued
0.7087	Intermediate Similarity	NPD2234	Approved
0.7087	Intermediate Similarity	NPD498	Approved
0.7087	Intermediate Similarity	NPD2228	Approved
0.7087	Intermediate Similarity	NPD496	Approved
0.7087	Intermediate Similarity	NPD2229	Approved
0.7087	Intermediate Similarity	NPD495	Approved
0.7077	Intermediate Similarity	NPD5303	Approved
0.7077	Intermediate Similarity	NPD5304	Approved
0.7077	Intermediate Similarity	NPD1548	Phase 1
0.7075	Intermediate Similarity	NPD6090	Discontinued
0.7073	Intermediate Similarity	NPD968	Approved
0.7068	Intermediate Similarity	NPD2235	Phase 2
0.7068	Intermediate Similarity	NPD2231	Phase 2
0.705	Intermediate Similarity	NPD1613	Approved
0.705	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD3496	Discontinued
0.7042	Intermediate Similarity	NPD2935	Discontinued
0.7037	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5585	Approved
0.7023	Intermediate Similarity	NPD1357	Approved
0.7021	Intermediate Similarity	NPD7097	Phase 1
0.7008	Intermediate Similarity	NPD7843	Approved
0.7007	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD7644	Approved
0.6993	Remote Similarity	NPD4725	Approved
0.6993	Remote Similarity	NPD4726	Approved
0.6993	Remote Similarity	NPD4721	Approved
0.6977	Remote Similarity	NPD4198	Discontinued
0.6977	Remote Similarity	NPD6387	Discontinued
0.6974	Remote Similarity	NPD5929	Approved
0.697	Remote Similarity	NPD5125	Phase 3
0.697	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1778	Approved
0.697	Remote Similarity	NPD5126	Approved
0.6948	Remote Similarity	NPD7833	Phase 2
0.6948	Remote Similarity	NPD7831	Phase 2
0.6948	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7330	Discontinued
0.6947	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1242	Phase 1
0.6935	Remote Similarity	NPD1445	Approved
0.6935	Remote Similarity	NPD1444	Approved
0.6934	Remote Similarity	NPD1712	Approved
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4476	Approved
0.6923	Remote Similarity	NPD4477	Approved
0.6923	Remote Similarity	NPD2438	Suspended
0.6912	Remote Similarity	NPD1470	Approved
0.6908	Remote Similarity	NPD37	Approved
0.6906	Remote Similarity	NPD6798	Discontinued
0.6903	Remote Similarity	NPD111	Approved
0.6894	Remote Similarity	NPD3443	Approved
0.6894	Remote Similarity	NPD3444	Approved
0.6894	Remote Similarity	NPD3445	Approved
0.6892	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3645	Discontinued
0.6884	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.688	Remote Similarity	NPD290	Approved
0.6875	Remote Similarity	NPD5535	Approved
0.6875	Remote Similarity	NPD1138	Approved
0.6861	Remote Similarity	NPD3690	Phase 2
0.6861	Remote Similarity	NPD3691	Phase 2
0.6857	Remote Similarity	NPD6405	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