NPASS Compound

Structure

NPC229252 OpenBabel07101718322D 23 22 0 0 0 0 0 0 0 0999 V2000 -12.9904 1.5000 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 -12.9904 0.5000 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 -12.1244 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -5.1962 0.0000 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 -4.3301 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 23 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.27
Volume:	372.937
LogP:	5.757
LogD:	4.417
LogS:	-4.869
# Rotatable Bonds:	17
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.206
Synthetic Accessibility Score:	2.314
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.628
MDCK Permeability:	2.0270601453376003e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.877
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.719
Plasma Protein Binding (PPB):	97.03182983398438%
Volume Distribution (VD):	0.716
Pgp-substrate:	1.7701542377471924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.759
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.538
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.638
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	8.366
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.925
Carcinogencity:	0.187
Eye Corrosion:	0.932
Eye Irritation:	0.929
Respiratory Toxicity:	0.365

Download Data

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

Natural Product: NPC229252

Natural Product ID:	NPC229252
*Common Name:**	Ethyl (E)-8-Oxooctadec-9-Enoate
IUPAC Name:	ethyl (E)-8-oxooctadec-9-enoate
Synonyms:
Standard InCHIKey:	KQGOGACAZUWACN-DTQAZKPQSA-N
Standard InCHI:	InChI=1S/C20H36O3/c1-3-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23-4-2/h13,16H,3-12,14-15,17-18H2,1-2H3/b16-13+
SMILES:	CCCCCCCC/C=C/C(=O)CCCCCCC(=O)OCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465239
PubChem CID:	11088644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO33018	clitocybe clavipes	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444711]

☑ 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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6555	Individual Protein	Aldehyde dehydrogenase 1, mitochondrial	Saccharomyces cerevisiae	IC50	=	430000.0	nM	PMID[490471]

☑ 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 NPC229252 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	174
0.1-0.2	2499
0.2-0.3	12450
0.3-0.4	15287
0.4-0.5	7352
0.5-0.6	3664
0.6-0.7	1073
0.7-0.8	170
0.8-0.85	14
0.85-0.9	7
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC143857
0.9107	High Similarity	NPC200845
0.9107	High Similarity	NPC128061
0.9107	High Similarity	NPC10316
0.9107	High Similarity	NPC223677
0.9107	High Similarity	NPC28779
0.8814	High Similarity	NPC274927
0.8814	High Similarity	NPC106851
0.875	High Similarity	NPC71761
0.875	High Similarity	NPC139545
0.875	High Similarity	NPC309606
0.875	High Similarity	NPC39633
0.8448	Intermediate Similarity	NPC228473
0.8393	Intermediate Similarity	NPC262968
0.8387	Intermediate Similarity	NPC54925
0.8361	Intermediate Similarity	NPC174447
0.8361	Intermediate Similarity	NPC251042
0.8361	Intermediate Similarity	NPC122521
0.8361	Intermediate Similarity	NPC235242
0.8308	Intermediate Similarity	NPC218477
0.8305	Intermediate Similarity	NPC477201
0.8254	Intermediate Similarity	NPC328089
0.8254	Intermediate Similarity	NPC68343
0.8235	Intermediate Similarity	NPC474321
0.8226	Intermediate Similarity	NPC201939
0.8226	Intermediate Similarity	NPC40082
0.8214	Intermediate Similarity	NPC224227
0.8088	Intermediate Similarity	NPC474705
0.8065	Intermediate Similarity	NPC243532
0.8036	Intermediate Similarity	NPC207815
0.7966	Intermediate Similarity	NPC6095
0.7966	Intermediate Similarity	NPC424
0.7966	Intermediate Similarity	NPC32467
0.7966	Intermediate Similarity	NPC85813
0.7966	Intermediate Similarity	NPC290563
0.7966	Intermediate Similarity	NPC87564
0.7966	Intermediate Similarity	NPC88966
0.7966	Intermediate Similarity	NPC25417
0.7966	Intermediate Similarity	NPC154245
0.7966	Intermediate Similarity	NPC261831
0.7966	Intermediate Similarity	NPC281972
0.7941	Intermediate Similarity	NPC84038
0.7937	Intermediate Similarity	NPC328776
0.7937	Intermediate Similarity	NPC320305
0.791	Intermediate Similarity	NPC143396
0.7879	Intermediate Similarity	NPC127091
0.7879	Intermediate Similarity	NPC22101
0.7879	Intermediate Similarity	NPC104537
0.7879	Intermediate Similarity	NPC475443
0.7879	Intermediate Similarity	NPC148192
0.7879	Intermediate Similarity	NPC330426
0.7879	Intermediate Similarity	NPC473829
0.7879	Intermediate Similarity	NPC271921
0.7857	Intermediate Similarity	NPC216130
0.7797	Intermediate Similarity	NPC70387
0.7797	Intermediate Similarity	NPC1813
0.7797	Intermediate Similarity	NPC36061
0.7797	Intermediate Similarity	NPC321062
0.7797	Intermediate Similarity	NPC294548
0.7797	Intermediate Similarity	NPC139029
0.7794	Intermediate Similarity	NPC42526
0.7761	Intermediate Similarity	NPC324981
0.7761	Intermediate Similarity	NPC141481
0.7761	Intermediate Similarity	NPC473559
0.7761	Intermediate Similarity	NPC134385
0.7761	Intermediate Similarity	NPC48218
0.7727	Intermediate Similarity	NPC16119
0.7719	Intermediate Similarity	NPC163345
0.7705	Intermediate Similarity	NPC18951
0.7705	Intermediate Similarity	NPC325977
0.7681	Intermediate Similarity	NPC186531
0.7647	Intermediate Similarity	NPC317583
0.7647	Intermediate Similarity	NPC473772
0.7627	Intermediate Similarity	NPC281245
0.7627	Intermediate Similarity	NPC310746
0.7627	Intermediate Similarity	NPC92114
0.7627	Intermediate Similarity	NPC161366
0.7612	Intermediate Similarity	NPC474619
0.7606	Intermediate Similarity	NPC469414
0.7606	Intermediate Similarity	NPC329826
0.7576	Intermediate Similarity	NPC98897
0.7576	Intermediate Similarity	NPC255863
0.7576	Intermediate Similarity	NPC326268
0.7576	Intermediate Similarity	NPC296436
0.7576	Intermediate Similarity	NPC176215
0.7576	Intermediate Similarity	NPC318420
0.7576	Intermediate Similarity	NPC136164
0.7576	Intermediate Similarity	NPC245947
0.7571	Intermediate Similarity	NPC470237
0.7571	Intermediate Similarity	NPC472956
0.7541	Intermediate Similarity	NPC52264
0.7536	Intermediate Similarity	NPC476660
0.75	Intermediate Similarity	NPC45097
0.75	Intermediate Similarity	NPC472967
0.75	Intermediate Similarity	NPC476614
0.75	Intermediate Similarity	NPC266119
0.75	Intermediate Similarity	NPC266159
0.7465	Intermediate Similarity	NPC227396
0.7463	Intermediate Similarity	NPC83965
0.746	Intermediate Similarity	NPC34416
0.7458	Intermediate Similarity	NPC477458
0.7424	Intermediate Similarity	NPC474400
0.7424	Intermediate Similarity	NPC470320
0.7424	Intermediate Similarity	NPC34622
0.7419	Intermediate Similarity	NPC179764
0.7419	Intermediate Similarity	NPC187777
0.7385	Intermediate Similarity	NPC321838
0.7377	Intermediate Similarity	NPC137538
0.7377	Intermediate Similarity	NPC322461
0.7361	Intermediate Similarity	NPC244166
0.7361	Intermediate Similarity	NPC260396
0.7353	Intermediate Similarity	NPC99619
0.7353	Intermediate Similarity	NPC26500
0.7344	Intermediate Similarity	NPC329550
0.7344	Intermediate Similarity	NPC159650
0.7344	Intermediate Similarity	NPC22897
0.7313	Intermediate Similarity	NPC133904
0.7302	Intermediate Similarity	NPC323597
0.7302	Intermediate Similarity	NPC225929
0.7302	Intermediate Similarity	NPC323498
0.7302	Intermediate Similarity	NPC211752
0.7297	Intermediate Similarity	NPC128276
0.7297	Intermediate Similarity	NPC192006
0.7288	Intermediate Similarity	NPC474391
0.7288	Intermediate Similarity	NPC59051
0.7286	Intermediate Similarity	NPC291062
0.7286	Intermediate Similarity	NPC477455
0.7286	Intermediate Similarity	NPC475310
0.7286	Intermediate Similarity	NPC94743
0.7273	Intermediate Similarity	NPC151728
0.7273	Intermediate Similarity	NPC57463
0.7273	Intermediate Similarity	NPC477707
0.726	Intermediate Similarity	NPC40353
0.726	Intermediate Similarity	NPC27205
0.7258	Intermediate Similarity	NPC473863
0.7258	Intermediate Similarity	NPC274290
0.7258	Intermediate Similarity	NPC54766
0.7241	Intermediate Similarity	NPC324812
0.7237	Intermediate Similarity	NPC471325
0.7237	Intermediate Similarity	NPC286229
0.7231	Intermediate Similarity	NPC79756
0.7222	Intermediate Similarity	NPC476355
0.7222	Intermediate Similarity	NPC140287
0.7206	Intermediate Similarity	NPC304665
0.7206	Intermediate Similarity	NPC126899
0.7206	Intermediate Similarity	NPC248125
0.7206	Intermediate Similarity	NPC154728
0.72	Intermediate Similarity	NPC469690
0.72	Intermediate Similarity	NPC63649
0.72	Intermediate Similarity	NPC264227
0.72	Intermediate Similarity	NPC471740
0.72	Intermediate Similarity	NPC472965
0.7183	Intermediate Similarity	NPC163003
0.7167	Intermediate Similarity	NPC234829
0.7164	Intermediate Similarity	NPC226592
0.7162	Intermediate Similarity	NPC57744
0.7143	Intermediate Similarity	NPC327388
0.7143	Intermediate Similarity	NPC94488
0.7143	Intermediate Similarity	NPC199557
0.7143	Intermediate Similarity	NPC477449
0.7143	Intermediate Similarity	NPC476059
0.7143	Intermediate Similarity	NPC262673
0.7143	Intermediate Similarity	NPC473603
0.7143	Intermediate Similarity	NPC85772
0.7143	Intermediate Similarity	NPC296522
0.7143	Intermediate Similarity	NPC144511
0.7143	Intermediate Similarity	NPC477448
0.7123	Intermediate Similarity	NPC193351
0.7123	Intermediate Similarity	NPC155587
0.7123	Intermediate Similarity	NPC138408
0.7123	Intermediate Similarity	NPC226669
0.7121	Intermediate Similarity	NPC151648
0.7119	Intermediate Similarity	NPC5413
0.7119	Intermediate Similarity	NPC149821
0.7119	Intermediate Similarity	NPC250919
0.7105	Intermediate Similarity	NPC304795
0.7101	Intermediate Similarity	NPC203335
0.7083	Intermediate Similarity	NPC167145
0.7077	Intermediate Similarity	NPC474267
0.7069	Intermediate Similarity	NPC44363
0.7069	Intermediate Similarity	NPC163751
0.7069	Intermediate Similarity	NPC110234
0.7067	Intermediate Similarity	NPC471220
0.7067	Intermediate Similarity	NPC182292
0.7059	Intermediate Similarity	NPC476654
0.7059	Intermediate Similarity	NPC476657
0.7059	Intermediate Similarity	NPC476655
0.7051	Intermediate Similarity	NPC144415
0.7051	Intermediate Similarity	NPC253801
0.7042	Intermediate Similarity	NPC469660
0.7042	Intermediate Similarity	NPC318766
0.7027	Intermediate Similarity	NPC474527
0.7027	Intermediate Similarity	NPC471726
0.7027	Intermediate Similarity	NPC472959
0.7027	Intermediate Similarity	NPC123360
0.7018	Intermediate Similarity	NPC287231
0.7018	Intermediate Similarity	NPC47363
0.7015	Intermediate Similarity	NPC474774
0.7015	Intermediate Similarity	NPC477830
0.7013	Intermediate Similarity	NPC42470

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 NPC229252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	3051
0.2-0.3	4012
0.3-0.4	1360
0.4-0.5	394
0.5-0.6	142
0.6-0.7	27
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8393	Intermediate Similarity	NPD29	Approved
0.8393	Intermediate Similarity	NPD28	Approved
0.7966	Intermediate Similarity	NPD3195	Phase 2
0.7966	Intermediate Similarity	NPD4266	Approved
0.7966	Intermediate Similarity	NPD3194	Approved
0.7966	Intermediate Similarity	NPD3196	Approved
0.7857	Intermediate Similarity	NPD5343	Approved
0.7797	Intermediate Similarity	NPD3172	Approved
0.7727	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3197	Phase 1
0.75	Intermediate Similarity	NPD3174	Discontinued
0.7321	Intermediate Similarity	NPD6097	Approved
0.7321	Intermediate Similarity	NPD6096	Approved
0.7119	Intermediate Similarity	NPD3173	Approved
0.7018	Intermediate Similarity	NPD2699	Approved
0.697	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD622	Approved
0.6933	Remote Similarity	NPD4756	Discovery
0.6892	Remote Similarity	NPD8039	Approved
0.6765	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7331	Phase 2
0.6709	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD6109	Phase 1
0.6613	Remote Similarity	NPD6927	Phase 3
0.661	Remote Similarity	NPD4222	Approved
0.661	Remote Similarity	NPD39	Approved
0.6585	Remote Similarity	NPD7521	Approved
0.6585	Remote Similarity	NPD7334	Approved
0.6585	Remote Similarity	NPD7146	Approved
0.6585	Remote Similarity	NPD6409	Approved
0.6585	Remote Similarity	NPD6684	Approved
0.6585	Remote Similarity	NPD5330	Approved
0.6582	Remote Similarity	NPD5369	Approved
0.6571	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5209	Approved
0.6479	Remote Similarity	NPD3704	Approved
0.6471	Remote Similarity	NPD5785	Approved
0.6463	Remote Similarity	NPD1694	Approved
0.6456	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD5737	Approved
0.6429	Remote Similarity	NPD6672	Approved
0.6429	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7154	Phase 3
0.641	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3573	Approved
0.6296	Remote Similarity	NPD4269	Approved
0.6296	Remote Similarity	NPD4270	Approved
0.6271	Remote Similarity	NPD5326	Phase 3
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD3206	Approved
0.622	Remote Similarity	NPD5362	Discontinued
0.6212	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3732	Approved
0.619	Remote Similarity	NPD5786	Approved
0.6111	Remote Similarity	NPD7341	Phase 2
0.6092	Remote Similarity	NPD46	Approved
0.6092	Remote Similarity	NPD6698	Approved
0.6071	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7900	Approved
0.6067	Remote Similarity	NPD7748	Approved
0.6061	Remote Similarity	NPD3730	Approved
0.6061	Remote Similarity	NPD3728	Approved
0.6029	Remote Similarity	NPD8779	Phase 3
0.6	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4271	Approved
0.6	Remote Similarity	NPD6422	Discontinued
0.5977	Remote Similarity	NPD6101	Approved
0.5977	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6080	Approved
0.5977	Remote Similarity	NPD6904	Approved
0.5977	Remote Similarity	NPD6673	Approved
0.5932	Remote Similarity	NPD2270	Approved
0.5909	Remote Similarity	NPD5207	Approved
0.587	Remote Similarity	NPD6083	Phase 2
0.587	Remote Similarity	NPD6084	Phase 2
0.587	Remote Similarity	NPD7902	Approved
0.5862	Remote Similarity	NPD5783	Phase 3
0.5862	Remote Similarity	NPD5208	Approved
0.5854	Remote Similarity	NPD4821	Approved
0.5854	Remote Similarity	NPD4820	Approved
0.5854	Remote Similarity	NPD4819	Approved
0.5854	Remote Similarity	NPD4822	Approved
0.5843	Remote Similarity	NPD7515	Phase 2
0.5843	Remote Similarity	NPD7983	Approved
0.5843	Remote Similarity	NPD6411	Approved
0.5843	Remote Similarity	NPD6050	Approved
0.5843	Remote Similarity	NPD5694	Approved
0.5824	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD5695	Phase 3
0.5814	Remote Similarity	NPD6098	Approved
0.5795	Remote Similarity	NPD1695	Approved
0.5795	Remote Similarity	NPD5370	Suspended
0.5778	Remote Similarity	NPD5779	Approved
0.5778	Remote Similarity	NPD6399	Phase 3
0.5778	Remote Similarity	NPD5778	Approved
0.5753	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD4250	Approved
0.5747	Remote Similarity	NPD4251	Approved
0.573	Remote Similarity	NPD7838	Discovery
0.573	Remote Similarity	NPD5692	Phase 3
0.5694	Remote Similarity	NPD3205	Discontinued
0.5667	Remote Similarity	NPD5693	Phase 1
0.5667	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6079	Approved
0.5663	Remote Similarity	NPD4695	Discontinued
0.5663	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6899	Approved
0.5657	Remote Similarity	NPD6881	Approved
0.5647	Remote Similarity	NPD5332	Approved
0.5647	Remote Similarity	NPD5331	Approved
0.5645	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5696	Approved
0.5632	Remote Similarity	NPD4249	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