NPASS Compound

Structure

CID220293 OpenBabel06191716012D 46 50 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4248 5.7025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0181 4.7889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2395 -4.1192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5485 -3.1682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4604 -1.7799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2068 0.7410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4819 -0.1326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7258 4.0156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0832 3.4279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8977 -0.7506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1056 -1.7288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7387 2.1546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2524 -0.8017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8762 -3.7362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 5.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6683 -2.7580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3265 1.3455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0445 0.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9710 -0.7759 0.0000 C 0 0 0 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 0.0213 2.4333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7877 1.8455 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2035 -1.1108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9466 -0.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7801 -0.1881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3625 -2.3979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8272 -4.0452 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6755 0.8064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7620 1.2131 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9349 2.0266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9530 0.6253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4303 5.5979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5704 -3.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4114 -2.0889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7877 0.8455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7387 0.5365 0.0000 C 0 0 2 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 4.6936 -0.5949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4845 1.3942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6574 2.2076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7439 2.6144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3258 6.5925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0575 -0.3692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0394 1.0321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 33 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 7 36 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 27 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 33 1 0 0 0 0 17 35 1 0 0 0 0 18 37 1 0 0 0 0 19 36 1 0 0 0 0 20 26 1 0 0 0 0 20 44 1 0 0 0 0 21 38 2 0 0 0 0 21 45 1 0 0 0 0 22 10 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 36 1 6 0 0 0 24 25 2 0 0 0 0 24 35 1 0 0 0 0 25 37 1 0 0 0 0 26 29 1 0 0 0 0 26 39 1 6 0 0 0 27 34 1 0 0 0 0 27 35 1 6 0 0 0 28 34 1 0 0 0 0 28 45 1 1 0 0 0 29 30 1 0 0 0 0 29 40 1 1 0 0 0 30 32 1 0 0 0 0 30 41 1 6 0 0 0 31 42 2 0 0 0 0 31 46 1 0 0 0 0 32 44 1 0 0 0 0 32 46 1 1 0 0 0 33 43 1 0 0 0 0 35 6 1 6 0 0 0 36 37 1 6 0 0 0 37 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	646.41
Volume:	674.292
LogP:	4.067
LogD:	3.656
LogS:	-4.481
# Rotatable Bonds:	9
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.222
Synthetic Accessibility Score:	5.505
Fsp3:	0.838
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.081
MDCK Permeability:	7.16593349352479e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.12
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.327

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	91.15522003173828%
Volume Distribution (VD):	0.886
Pgp-substrate:	3.4409663677215576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.732
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.284
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	1.711
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.121
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.458
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.716

Download Data

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

Natural Product: NPC220293

Natural Product ID:	NPC220293
*Common Name:**	Fomitoside E
IUPAC Name:	[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl] (E,2R)-2-[(3R,5R,10S,13R,14R,17R)-3-acetyloxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-6-methylhept-4-enoate
Synonyms:	fomitoside E
Standard InCHIKey:	SZJHDEBBAHZWAS-JYUDEBFNSA-N
Standard InCHI:	InChI=1S/C37H58O9/c1-21(38)45-28-15-17-35(6)24-14-19-36(7)23(13-18-37(36,8)25(24)11-12-27(35)34(28,4)5)22(10-9-16-33(2,3)43)31(42)46-32-30(41)29(40)26(39)20-44-32/h9,16,22-23,26-30,32,39-41,43H,10-15,17-20H2,1-8H3/b16-9+/t22-,23-,26-,27+,28-,29+,30-,32+,35-,36-,37+/m1/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2(C)C3=C(CC[C@H]2C1(C)C)[C@]1(C)CC[C@H]([C@@H](C/C=C/C(C)(C)O)C(=O)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)[C@@]1(C)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447689
PubChem CID:	11158025
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	fruit bodies	Tokushima, Japan	1999-Autumn	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	57.2	%	PMID[537762]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	150.0	nM	PMID[537762]

☑ 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 NPC220293 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	214
0.1-0.2	1232
0.2-0.3	4129
0.3-0.4	9095
0.4-0.5	11756
0.5-0.6	6641
0.6-0.7	5633
0.7-0.8	3650
0.8-0.85	286
0.85-0.9	46
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC265655
0.9434	High Similarity	NPC129340
0.9429	High Similarity	NPC195708
0.9346	High Similarity	NPC292196
0.9266	High Similarity	NPC116024
0.9174	High Similarity	NPC251309
0.9167	High Similarity	NPC263827
0.9167	High Similarity	NPC250481
0.9167	High Similarity	NPC285410
0.9159	High Similarity	NPC477069
0.9159	High Similarity	NPC477070
0.9115	High Similarity	NPC202051
0.9083	High Similarity	NPC233003
0.9057	High Similarity	NPC162033
0.8991	High Similarity	NPC477073
0.8962	High Similarity	NPC223741
0.8957	High Similarity	NPC41129
0.8938	High Similarity	NPC477071
0.8919	High Similarity	NPC473882
0.8899	High Similarity	NPC475317
0.8899	High Similarity	NPC154856
0.8899	High Similarity	NPC52241
0.8899	High Similarity	NPC101450
0.8889	High Similarity	NPC295389
0.885	High Similarity	NPC45475
0.8839	High Similarity	NPC244127
0.8829	High Similarity	NPC477074
0.8807	High Similarity	NPC137917
0.875	High Similarity	NPC472274
0.8739	High Similarity	NPC130427
0.8739	High Similarity	NPC474265
0.8739	High Similarity	NPC174836
0.8739	High Similarity	NPC210420
0.8727	High Similarity	NPC27551
0.8727	High Similarity	NPC269095
0.8727	High Similarity	NPC220984
0.8727	High Similarity	NPC114961
0.8727	High Similarity	NPC78046
0.8716	High Similarity	NPC472217
0.8716	High Similarity	NPC472218
0.8716	High Similarity	NPC284807
0.8716	High Similarity	NPC177246
0.8716	High Similarity	NPC28198
0.8716	High Similarity	NPC476123
0.8716	High Similarity	NPC472219
0.8707	High Similarity	NPC28532
0.8704	High Similarity	NPC470763
0.8704	High Similarity	NPC470767
0.8704	High Similarity	NPC473199
0.8696	High Similarity	NPC471406
0.8696	High Similarity	NPC470312
0.8684	High Similarity	NPC473828
0.8684	High Similarity	NPC473617
0.8673	High Similarity	NPC146652
0.8661	High Similarity	NPC73455
0.8661	High Similarity	NPC260665
0.8661	High Similarity	NPC200944
0.8655	High Similarity	NPC245094
0.8649	High Similarity	NPC269466
0.8636	High Similarity	NPC167383
0.8636	High Similarity	NPC237503
0.8636	High Similarity	NPC127853
0.8636	High Similarity	NPC57362
0.8636	High Similarity	NPC306746
0.8636	High Similarity	NPC204407
0.8636	High Similarity	NPC118225
0.8624	High Similarity	NPC283849
0.8624	High Similarity	NPC473538
0.8624	High Similarity	NPC293512
0.8621	High Similarity	NPC129434
0.8611	High Similarity	NPC470768
0.8611	High Similarity	NPC75608
0.8596	High Similarity	NPC471547
0.8595	High Similarity	NPC231240
0.8584	High Similarity	NPC181145
0.8584	High Similarity	NPC474557
0.8583	High Similarity	NPC477235
0.8583	High Similarity	NPC476966
0.8583	High Similarity	NPC471407
0.8571	High Similarity	NPC37739
0.8571	High Similarity	NPC46388
0.8559	High Similarity	NPC476880
0.8559	High Similarity	NPC164194
0.8559	High Similarity	NPC7870
0.8559	High Similarity	NPC90856
0.8559	High Similarity	NPC199457
0.8559	High Similarity	NPC127056
0.8559	High Similarity	NPC242611
0.8559	High Similarity	NPC29069
0.8559	High Similarity	NPC476886
0.8559	High Similarity	NPC475296
0.8559	High Similarity	NPC476883
0.8559	High Similarity	NPC270667
0.8559	High Similarity	NPC75747
0.8559	High Similarity	NPC110139
0.8559	High Similarity	NPC136877
0.8559	High Similarity	NPC56713
0.8559	High Similarity	NPC274507
0.8559	High Similarity	NPC476885
0.8559	High Similarity	NPC474589
0.8559	High Similarity	NPC68419
0.8559	High Similarity	NPC174679
0.8559	High Similarity	NPC279554
0.8559	High Similarity	NPC476882
0.8559	High Similarity	NPC476884
0.8559	High Similarity	NPC102914
0.8559	High Similarity	NPC108709
0.8559	High Similarity	NPC476887
0.8559	High Similarity	NPC476881
0.8559	High Similarity	NPC59804
0.8545	High Similarity	NPC258323
0.8545	High Similarity	NPC88744
0.8545	High Similarity	NPC472988
0.8545	High Similarity	NPC38217
0.8534	High Similarity	NPC472257
0.8534	High Similarity	NPC129393
0.8532	High Similarity	NPC475611
0.8532	High Similarity	NPC472899
0.8532	High Similarity	NPC472900
0.8532	High Similarity	NPC472898
0.8525	High Similarity	NPC316915
0.8522	High Similarity	NPC239293
0.8522	High Similarity	NPC291564
0.8522	High Similarity	NPC234522
0.8509	High Similarity	NPC279638
0.8505	High Similarity	NPC21064
0.8505	High Similarity	NPC121072
0.8496	Intermediate Similarity	NPC189884
0.8496	Intermediate Similarity	NPC75167
0.8496	Intermediate Similarity	NPC269315
0.8496	Intermediate Similarity	NPC204458
0.8496	Intermediate Similarity	NPC271138
0.8496	Intermediate Similarity	NPC47063
0.8496	Intermediate Similarity	NPC138334
0.8496	Intermediate Similarity	NPC311592
0.8482	Intermediate Similarity	NPC179434
0.8482	Intermediate Similarity	NPC31839
0.8482	Intermediate Similarity	NPC30397
0.8482	Intermediate Similarity	NPC272242
0.8482	Intermediate Similarity	NPC191763
0.8482	Intermediate Similarity	NPC235841
0.8482	Intermediate Similarity	NPC190837
0.8482	Intermediate Similarity	NPC108748
0.8482	Intermediate Similarity	NPC211798
0.8482	Intermediate Similarity	NPC473481
0.8482	Intermediate Similarity	NPC164419
0.8482	Intermediate Similarity	NPC297208
0.8475	Intermediate Similarity	NPC27363
0.8468	Intermediate Similarity	NPC125361
0.8468	Intermediate Similarity	NPC173905
0.8468	Intermediate Similarity	NPC473844
0.8468	Intermediate Similarity	NPC51947
0.8468	Intermediate Similarity	NPC91583
0.8468	Intermediate Similarity	NPC51925
0.8468	Intermediate Similarity	NPC43976
0.8468	Intermediate Similarity	NPC154085
0.8468	Intermediate Similarity	NPC284828
0.8468	Intermediate Similarity	NPC472216
0.8468	Intermediate Similarity	NPC296761
0.8468	Intermediate Similarity	NPC218853
0.8468	Intermediate Similarity	NPC475364
0.8468	Intermediate Similarity	NPC240125
0.8468	Intermediate Similarity	NPC5475
0.8455	Intermediate Similarity	NPC33053
0.8455	Intermediate Similarity	NPC234160
0.8455	Intermediate Similarity	NPC231340
0.8448	Intermediate Similarity	NPC232258
0.8448	Intermediate Similarity	NPC122971
0.8443	Intermediate Similarity	NPC471855
0.844	Intermediate Similarity	NPC31430
0.844	Intermediate Similarity	NPC85593
0.8435	Intermediate Similarity	NPC473405
0.8426	Intermediate Similarity	NPC94919
0.8426	Intermediate Similarity	NPC470571
0.8426	Intermediate Similarity	NPC154452
0.8421	Intermediate Similarity	NPC469821
0.8421	Intermediate Similarity	NPC74727
0.8421	Intermediate Similarity	NPC475163
0.8417	Intermediate Similarity	NPC240070
0.8417	Intermediate Similarity	NPC329784
0.8407	Intermediate Similarity	NPC477253
0.8407	Intermediate Similarity	NPC324875
0.8407	Intermediate Similarity	NPC139044
0.8407	Intermediate Similarity	NPC473567
0.8407	Intermediate Similarity	NPC64106
0.8407	Intermediate Similarity	NPC48249
0.8407	Intermediate Similarity	NPC471383
0.8407	Intermediate Similarity	NPC216595
0.8407	Intermediate Similarity	NPC100383
0.8407	Intermediate Similarity	NPC116794
0.8407	Intermediate Similarity	NPC109079
0.8407	Intermediate Similarity	NPC104400
0.8407	Intermediate Similarity	NPC10320
0.8407	Intermediate Similarity	NPC79718
0.8407	Intermediate Similarity	NPC257468
0.8407	Intermediate Similarity	NPC473373
0.8407	Intermediate Similarity	NPC469946
0.8407	Intermediate Similarity	NPC1046
0.8407	Intermediate Similarity	NPC276093
0.8407	Intermediate Similarity	NPC65590

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 NPC220293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1457
0.2-0.3	3798
0.3-0.4	2442
0.4-0.5	711
0.5-0.6	265
0.6-0.7	198
0.7-0.8	99
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
0.8333	Intermediate Similarity	NPD7507	Approved
0.8304	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8174	Intermediate Similarity	NPD8133	Approved
0.813	Intermediate Similarity	NPD7319	Approved
0.8125	Intermediate Similarity	NPD6412	Phase 2
0.8067	Intermediate Similarity	NPD8294	Approved
0.8067	Intermediate Similarity	NPD8377	Approved
0.8053	Intermediate Similarity	NPD6686	Approved
0.8051	Intermediate Similarity	NPD7328	Approved
0.8051	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD8335	Approved
0.8	Intermediate Similarity	NPD8033	Approved
0.8	Intermediate Similarity	NPD8296	Approved
0.8	Intermediate Similarity	NPD7503	Approved
0.8	Intermediate Similarity	NPD8378	Approved
0.8	Intermediate Similarity	NPD8380	Approved
0.8	Intermediate Similarity	NPD8379	Approved
0.7983	Intermediate Similarity	NPD7516	Approved
0.7903	Intermediate Similarity	NPD7736	Approved
0.7851	Intermediate Similarity	NPD8516	Approved
0.7851	Intermediate Similarity	NPD8513	Phase 3
0.7851	Intermediate Similarity	NPD8517	Approved
0.7851	Intermediate Similarity	NPD8515	Approved
0.7815	Intermediate Similarity	NPD7115	Discovery
0.7778	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7724	Intermediate Similarity	NPD8328	Phase 3
0.768	Intermediate Similarity	NPD8293	Discontinued
0.7667	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6370	Approved
0.7521	Intermediate Similarity	NPD6009	Approved
0.752	Intermediate Similarity	NPD7492	Approved
0.748	Intermediate Similarity	NPD6319	Approved
0.748	Intermediate Similarity	NPD6054	Approved
0.746	Intermediate Similarity	NPD6616	Approved
0.7436	Intermediate Similarity	NPD6881	Approved
0.7436	Intermediate Similarity	NPD6899	Approved
0.7434	Intermediate Similarity	NPD7640	Approved
0.7434	Intermediate Similarity	NPD7639	Approved
0.7417	Intermediate Similarity	NPD4632	Approved
0.7414	Intermediate Similarity	NPD6675	Approved
0.7414	Intermediate Similarity	NPD7128	Approved
0.7414	Intermediate Similarity	NPD6402	Approved
0.7414	Intermediate Similarity	NPD5739	Approved
0.7402	Intermediate Similarity	NPD7078	Approved
0.7395	Intermediate Similarity	NPD8130	Phase 1
0.7395	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6649	Approved
0.7395	Intermediate Similarity	NPD6650	Approved
0.7373	Intermediate Similarity	NPD6373	Approved
0.7373	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD6399	Phase 3
0.735	Intermediate Similarity	NPD5697	Approved
0.7345	Intermediate Similarity	NPD7638	Approved
0.7339	Intermediate Similarity	NPD6059	Approved
0.7311	Intermediate Similarity	NPD6883	Approved
0.7311	Intermediate Similarity	NPD7290	Approved
0.7311	Intermediate Similarity	NPD7102	Approved
0.7288	Intermediate Similarity	NPD7320	Approved
0.728	Intermediate Similarity	NPD6015	Approved
0.728	Intermediate Similarity	NPD6016	Approved
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.725	Intermediate Similarity	NPD6869	Approved
0.725	Intermediate Similarity	NPD6617	Approved
0.725	Intermediate Similarity	NPD6847	Approved
0.7227	Intermediate Similarity	NPD6014	Approved
0.7227	Intermediate Similarity	NPD6012	Approved
0.7227	Intermediate Similarity	NPD6013	Approved
0.7227	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5988	Approved
0.7203	Intermediate Similarity	NPD5701	Approved
0.7155	Intermediate Similarity	NPD5211	Phase 2
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7132	Intermediate Similarity	NPD8074	Phase 3
0.7105	Intermediate Similarity	NPD6084	Phase 2
0.7105	Intermediate Similarity	NPD6083	Phase 2
0.7105	Intermediate Similarity	NPD7902	Approved
0.708	Intermediate Similarity	NPD5695	Phase 3
0.7037	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5141	Approved
0.7031	Intermediate Similarity	NPD6067	Discontinued
0.7031	Intermediate Similarity	NPD7604	Phase 2
0.7025	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5983	Phase 2
0.7	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5286	Approved
0.6983	Remote Similarity	NPD5285	Approved
0.6983	Remote Similarity	NPD4696	Approved
0.6967	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7515	Phase 2
0.6964	Remote Similarity	NPD6411	Approved
0.6964	Remote Similarity	NPD6079	Approved
0.6957	Remote Similarity	NPD4755	Approved
0.6944	Remote Similarity	NPD4786	Approved
0.6937	Remote Similarity	NPD5328	Approved
0.6923	Remote Similarity	NPD6336	Discontinued
0.6903	Remote Similarity	NPD5779	Approved
0.6903	Remote Similarity	NPD4202	Approved
0.6903	Remote Similarity	NPD5778	Approved
0.6897	Remote Similarity	NPD4225	Approved
0.6885	Remote Similarity	NPD4634	Approved
0.6864	Remote Similarity	NPD5224	Approved
0.6864	Remote Similarity	NPD7632	Discontinued
0.6864	Remote Similarity	NPD5225	Approved
0.6864	Remote Similarity	NPD4633	Approved
0.6864	Remote Similarity	NPD5226	Approved
0.685	Remote Similarity	NPD7101	Approved
0.685	Remote Similarity	NPD7100	Approved
0.6842	Remote Similarity	NPD7900	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4700	Approved
0.6833	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD3618	Phase 1
0.6818	Remote Similarity	NPD6033	Approved
0.6814	Remote Similarity	NPD7637	Suspended
0.6814	Remote Similarity	NPD5281	Approved
0.6814	Remote Similarity	NPD5284	Approved
0.6814	Remote Similarity	NPD7983	Approved
0.6807	Remote Similarity	NPD5175	Approved
0.6807	Remote Similarity	NPD5174	Approved
0.6786	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6101	Approved
0.678	Remote Similarity	NPD5223	Approved
0.6777	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6053	Discontinued
0.6772	Remote Similarity	NPD6335	Approved
0.6759	Remote Similarity	NPD3667	Approved
0.6752	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5696	Approved
0.6746	Remote Similarity	NPD6274	Approved
0.6729	Remote Similarity	NPD7525	Registered
0.6726	Remote Similarity	NPD46	Approved
0.6726	Remote Similarity	NPD6698	Approved
0.6724	Remote Similarity	NPD5221	Approved
0.6724	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5222	Approved
0.6721	Remote Similarity	NPD4730	Approved
0.6721	Remote Similarity	NPD4729	Approved
0.6698	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5737	Approved
0.6696	Remote Similarity	NPD6672	Approved
0.6696	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4768	Approved
0.6694	Remote Similarity	NPD4767	Approved
0.6693	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6641	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD5344	Discontinued
0.6638	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4753	Phase 2
0.6615	Remote Similarity	NPD6909	Approved
0.6615	Remote Similarity	NPD6908	Approved
0.6614	Remote Similarity	NPD6868	Approved
0.6613	Remote Similarity	NPD5249	Phase 3
0.6613	Remote Similarity	NPD5247	Approved
0.6613	Remote Similarity	NPD5251	Approved
0.6613	Remote Similarity	NPD5250	Approved
0.6613	Remote Similarity	NPD5248	Approved
0.6609	Remote Similarity	NPD8171	Discontinued
0.6607	Remote Similarity	NPD7524	Approved
0.6607	Remote Similarity	NPD3573	Approved
0.6581	Remote Similarity	NPD4697	Phase 3
0.6549	Remote Similarity	NPD6903	Approved
0.6545	Remote Similarity	NPD5362	Discontinued
0.6544	Remote Similarity	NPD7260	Phase 2
0.6529	Remote Similarity	NPD4754	Approved
0.6522	Remote Similarity	NPD6050	Approved
0.6522	Remote Similarity	NPD5694	Approved
0.6518	Remote Similarity	NPD6098	Approved
0.6518	Remote Similarity	NPD5279	Phase 3
0.6496	Remote Similarity	NPD8338	Approved
0.6496	Remote Similarity	NPD4629	Approved
0.6496	Remote Similarity	NPD5210	Approved
0.6491	Remote Similarity	NPD6051	Approved
0.6491	Remote Similarity	NPD6080	Approved
0.6491	Remote Similarity	NPD6673	Approved
0.6491	Remote Similarity	NPD6904	Approved
0.6489	Remote Similarity	NPD6921	Approved
0.6489	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3133	Approved
0.6486	Remote Similarity	NPD3665	Phase 1
0.6486	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3666	Approved
0.6484	Remote Similarity	NPD6940	Discontinued
0.6483	Remote Similarity	NPD7625	Phase 1
0.648	Remote Similarity	NPD6371	Approved
0.6471	Remote Similarity	NPD5956	Approved
0.6466	Remote Similarity	NPD8342	Approved
0.6466	Remote Similarity	NPD8340	Approved
0.6466	Remote Similarity	NPD8299	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