NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.24
Volume:	329.555
LogP:	6.13
LogD:	3.196
LogS:	-5.179
# Rotatable Bonds:	13
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	2.208
Fsp3:	0.833
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:	-4.899
MDCK Permeability:	1.8588840248412453e-05
Pgp-inhibitor:	0.127
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	97.825927734375%
Volume Distribution (VD):	0.884
Pgp-substrate:	0.7303761839866638%

ADMET: Metabolism

CYP1A2-inhibitor:	0.43
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.608
CYP2C19-substrate:	0.174
CYP2C9-inhibitor:	0.326
CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.122
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	2.781
Half-life (T1/2):	0.69

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.942
Carcinogencity:	0.104
Eye Corrosion:	0.974
Eye Irritation:	0.964
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC8219

Natural Product ID:	NPC8219
*Common Name:**	9-Octadecynoic Acid
IUPAC Name:	octadec-9-ynoic acid
Synonyms:	9-Octadecynoic Acid
Standard InCHIKey:	RGTIBVZDHOMOKC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-8,11-17H2,1H3,(H,19,20)
SMILES:	CCCCCCCCC#CCCCCCCCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482804
PubChem CID:	68167
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO28265.1	Morus alba var. atropurpurea	Varieties	Moraceae	Eukaryota	n.a.	twig	n.a.	PMID[19149258]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO28265.1	Morus alba var. atropurpurea	Varieties	Moraceae	Eukaryota	Fruits	Zhenjiang, Jiangsu Province, China		PMID[23060696]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO21299	Porcelia macrocarpa	Species	n.a.	n.a.	Seeds	n.a.	n.a.	PMID[31046273]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3779	Sassafras tzumu	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3779	Sassafras tzumu	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7353	Euphorbia paralias	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3779	Sassafras tzumu	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4678	Galanthus caucasicus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21299	Porcelia macrocarpa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25591	Vexibia alopecuroides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7353	Euphorbia paralias	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6282	Pestalotia ramulosa	Species	Amphisphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12793	Clibadium glomeratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3158	Linum album	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3779	Sassafras tzumu	Species	Lauraceae	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
NPO28265.1	NPC8219	n.a.	Fruits	0.32	n.a.	n.a.	%	PMID[23060696]

☑ 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	7
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT253	Individual Protein	HMG-CoA reductase	Homo sapiens	IC50	=	5000.0	nM	PMID[484761]
NPT1460	Cell Line	L929	Mus musculus	CC50	>	200000.0	nM	PMID[484763]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	IC50	=	80200.0	nM	PMID[484762]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	178600.0	nM	PMID[484762]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IC50	>	178600.0	nM	PMID[484762]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	IC50	>	178600.0	nM	PMID[484762]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IC50	>	178700.0	nM	PMID[484762]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	27600.0	nM	PMID[484763]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	7.2	n.a.	PMID[484763]

☑ 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 NPC8219 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	910
0.1-0.2	14503
0.2-0.3	16172
0.3-0.4	8696
0.4-0.5	1872
0.5-0.6	338
0.6-0.7	109
0.7-0.8	54
0.8-0.85	15
0.85-0.9	13
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC255837
0.9756	High Similarity	NPC19305
0.9512	High Similarity	NPC301528
0.9512	High Similarity	NPC129972
0.9512	High Similarity	NPC71317
0.9268	High Similarity	NPC103286
0.9268	High Similarity	NPC196924
0.9268	High Similarity	NPC216630
0.9268	High Similarity	NPC307783
0.9268	High Similarity	NPC149184
0.9268	High Similarity	NPC171736
0.9268	High Similarity	NPC163746
0.9268	High Similarity	NPC209970
0.9048	High Similarity	NPC67462
0.8837	High Similarity	NPC74845
0.878	High Similarity	NPC301585
0.878	High Similarity	NPC14227
0.878	High Similarity	NPC201844
0.878	High Similarity	NPC261080
0.878	High Similarity	NPC113928
0.878	High Similarity	NPC154186
0.878	High Similarity	NPC301696
0.878	High Similarity	NPC279026
0.8696	High Similarity	NPC304162
0.8537	High Similarity	NPC73245
0.8444	Intermediate Similarity	NPC12438
0.8444	Intermediate Similarity	NPC30195
0.8333	Intermediate Similarity	NPC470410
0.8333	Intermediate Similarity	NPC118968
0.8333	Intermediate Similarity	NPC294085
0.8333	Intermediate Similarity	NPC183424
0.8333	Intermediate Similarity	NPC214610
0.8333	Intermediate Similarity	NPC470412
0.8293	Intermediate Similarity	NPC158179
0.8261	Intermediate Similarity	NPC328497
0.8261	Intermediate Similarity	NPC324004
0.8261	Intermediate Similarity	NPC21844
0.814	Intermediate Similarity	NPC161097
0.814	Intermediate Similarity	NPC28598
0.814	Intermediate Similarity	NPC12156
0.8095	Intermediate Similarity	NPC268826
0.8085	Intermediate Similarity	NPC477878
0.8085	Intermediate Similarity	NPC106872
0.8085	Intermediate Similarity	NPC324793
0.8049	Intermediate Similarity	NPC155263
0.7959	Intermediate Similarity	NPC100096
0.7826	Intermediate Similarity	NPC55023
0.7805	Intermediate Similarity	NPC156630
0.78	Intermediate Similarity	NPC18357
0.7778	Intermediate Similarity	NPC236579
0.7778	Intermediate Similarity	NPC203531
0.7755	Intermediate Similarity	NPC90904
0.7674	Intermediate Similarity	NPC22903
0.7674	Intermediate Similarity	NPC54980
0.7674	Intermediate Similarity	NPC201622
0.7674	Intermediate Similarity	NPC305660
0.766	Intermediate Similarity	NPC314679
0.7619	Intermediate Similarity	NPC134782
0.7609	Intermediate Similarity	NPC317128
0.7551	Intermediate Similarity	NPC26253
0.7547	Intermediate Similarity	NPC187777
0.7547	Intermediate Similarity	NPC179764
0.75	Intermediate Similarity	NPC31551
0.75	Intermediate Similarity	NPC219536
0.7447	Intermediate Similarity	NPC469781
0.7447	Intermediate Similarity	NPC47363
0.7447	Intermediate Similarity	NPC287231
0.7358	Intermediate Similarity	NPC473863
0.7358	Intermediate Similarity	NPC274290
0.7358	Intermediate Similarity	NPC54766
0.7347	Intermediate Similarity	NPC131770
0.7347	Intermediate Similarity	NPC200618
0.7333	Intermediate Similarity	NPC40597
0.7333	Intermediate Similarity	NPC250028
0.7333	Intermediate Similarity	NPC256163
0.7333	Intermediate Similarity	NPC165533
0.7333	Intermediate Similarity	NPC149299
0.7317	Intermediate Similarity	NPC175342
0.7308	Intermediate Similarity	NPC72722
0.7174	Intermediate Similarity	NPC325452
0.7174	Intermediate Similarity	NPC53541
0.7174	Intermediate Similarity	NPC248763
0.717	Intermediate Similarity	NPC53463
0.717	Intermediate Similarity	NPC469937
0.717	Intermediate Similarity	NPC85813
0.717	Intermediate Similarity	NPC87394
0.717	Intermediate Similarity	NPC424
0.717	Intermediate Similarity	NPC25417
0.717	Intermediate Similarity	NPC261831
0.717	Intermediate Similarity	NPC281972
0.717	Intermediate Similarity	NPC6095
0.717	Intermediate Similarity	NPC154245
0.717	Intermediate Similarity	NPC290563
0.717	Intermediate Similarity	NPC32467
0.717	Intermediate Similarity	NPC320588
0.717	Intermediate Similarity	NPC23155
0.717	Intermediate Similarity	NPC87564
0.717	Intermediate Similarity	NPC88966
0.7115	Intermediate Similarity	NPC161366
0.7111	Intermediate Similarity	NPC223249
0.7111	Intermediate Similarity	NPC80234
0.7091	Intermediate Similarity	NPC225929
0.7021	Intermediate Similarity	NPC289686
0.7	Intermediate Similarity	NPC180534
0.6981	Remote Similarity	NPC1813
0.6981	Remote Similarity	NPC321062
0.6981	Remote Similarity	NPC294548
0.6981	Remote Similarity	NPC70387
0.6981	Remote Similarity	NPC36061
0.6981	Remote Similarity	NPC139029
0.6939	Remote Similarity	NPC166287
0.6923	Remote Similarity	NPC284212
0.6909	Remote Similarity	NPC18951
0.6909	Remote Similarity	NPC477201
0.6905	Remote Similarity	NPC18224
0.6905	Remote Similarity	NPC328710
0.6875	Remote Similarity	NPC76051
0.6792	Remote Similarity	NPC92114
0.6792	Remote Similarity	NPC281245
0.6739	Remote Similarity	NPC3531
0.6731	Remote Similarity	NPC55678
0.6731	Remote Similarity	NPC50457
0.6724	Remote Similarity	NPC235242
0.6667	Remote Similarity	NPC267817
0.6667	Remote Similarity	NPC109026
0.6667	Remote Similarity	NPC252843
0.6667	Remote Similarity	NPC226592
0.6667	Remote Similarity	NPC128996
0.6604	Remote Similarity	NPC262968
0.6604	Remote Similarity	NPC28205
0.6604	Remote Similarity	NPC287811
0.6604	Remote Similarity	NPC470411
0.66	Remote Similarity	NPC52700
0.66	Remote Similarity	NPC63182
0.66	Remote Similarity	NPC145045
0.66	Remote Similarity	NPC105329
0.6591	Remote Similarity	NPC317203
0.6585	Remote Similarity	NPC174368
0.6552	Remote Similarity	NPC106851
0.6552	Remote Similarity	NPC469924
0.6552	Remote Similarity	NPC470363
0.6552	Remote Similarity	NPC274927
0.6545	Remote Similarity	NPC289979
0.6522	Remote Similarity	NPC326532
0.6508	Remote Similarity	NPC82315
0.6481	Remote Similarity	NPC310746
0.6471	Remote Similarity	NPC326957
0.6471	Remote Similarity	NPC249754
0.6444	Remote Similarity	NPC154642
0.6444	Remote Similarity	NPC80641
0.6444	Remote Similarity	NPC80396
0.6441	Remote Similarity	NPC243532
0.6415	Remote Similarity	NPC59051
0.6415	Remote Similarity	NPC224227
0.64	Remote Similarity	NPC273545
0.6393	Remote Similarity	NPC470320
0.6383	Remote Similarity	NPC471282
0.6364	Remote Similarity	NPC57499
0.6364	Remote Similarity	NPC309606
0.6364	Remote Similarity	NPC39633
0.6364	Remote Similarity	NPC139545
0.6346	Remote Similarity	NPC216130
0.6333	Remote Similarity	NPC469923
0.6333	Remote Similarity	NPC201939
0.6304	Remote Similarity	NPC74352
0.6279	Remote Similarity	NPC149101
0.6279	Remote Similarity	NPC76608
0.6279	Remote Similarity	NPC225318
0.6279	Remote Similarity	NPC16578
0.6275	Remote Similarity	NPC308301
0.623	Remote Similarity	NPC235788
0.623	Remote Similarity	NPC474552
0.6226	Remote Similarity	NPC5413
0.6226	Remote Similarity	NPC149821
0.6226	Remote Similarity	NPC476469
0.6222	Remote Similarity	NPC86545
0.6222	Remote Similarity	NPC196442
0.6222	Remote Similarity	NPC223374
0.6222	Remote Similarity	NPC301398
0.6167	Remote Similarity	NPC174447
0.6167	Remote Similarity	NPC251042
0.6167	Remote Similarity	NPC469921
0.6167	Remote Similarity	NPC122521
0.6154	Remote Similarity	NPC42304
0.614	Remote Similarity	NPC10316
0.614	Remote Similarity	NPC200845
0.614	Remote Similarity	NPC45626
0.614	Remote Similarity	NPC228473
0.614	Remote Similarity	NPC128061
0.614	Remote Similarity	NPC223677
0.614	Remote Similarity	NPC28779
0.6136	Remote Similarity	NPC185538
0.6136	Remote Similarity	NPC139131
0.6136	Remote Similarity	NPC291158
0.6136	Remote Similarity	NPC205141
0.6136	Remote Similarity	NPC181516
0.6136	Remote Similarity	NPC152759
0.6136	Remote Similarity	NPC12231
0.6136	Remote Similarity	NPC272998
0.6129	Remote Similarity	NPC328089

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 NPC8219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1446
0.1-0.2	5124
0.2-0.3	1723
0.3-0.4	600
0.4-0.5	188
0.5-0.6	36
0.6-0.7	23
0.7-0.8	4
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9268	High Similarity	NPD2270	Approved
0.878	High Similarity	NPD633	Phase 3
0.878	High Similarity	NPD9448	Phase 2
0.8636	High Similarity	NPD3199	Clinical (unspecified phase)
0.8537	High Similarity	NPD3206	Approved
0.8333	Intermediate Similarity	NPD9655	Approved
0.766	Intermediate Similarity	NPD634	Phase 3
0.7451	Intermediate Similarity	NPD3186	Phase 1
0.7447	Intermediate Similarity	NPD2699	Approved
0.717	Intermediate Similarity	NPD4266	Approved
0.717	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3195	Phase 2
0.717	Intermediate Similarity	NPD3730	Approved
0.717	Intermediate Similarity	NPD3194	Approved
0.717	Intermediate Similarity	NPD3728	Approved
0.717	Intermediate Similarity	NPD3196	Approved
0.7021	Intermediate Similarity	NPD387	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD622	Approved
0.6981	Remote Similarity	NPD3172	Approved
0.6957	Remote Similarity	NPD9635	Discontinued
0.6939	Remote Similarity	NPD9431	Approved
0.6939	Remote Similarity	NPD9430	Approved
0.6739	Remote Similarity	NPD9450	Approved
0.6739	Remote Similarity	NPD77	Approved
0.6667	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD28	Approved
0.6604	Remote Similarity	NPD29	Approved
0.6552	Remote Similarity	NPD3198	Approved
0.6545	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9513	Phase 1
0.6346	Remote Similarity	NPD2266	Phase 2
0.6304	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD9638	Phase 2
0.6226	Remote Similarity	NPD3173	Approved
0.6136	Remote Similarity	NPD2272	Approved
0.6136	Remote Similarity	NPD5383	Approved
0.6129	Remote Similarity	NPD3197	Phase 1
0.6129	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD8857	Approved
0.587	Remote Similarity	NPD9447	Approved
0.5806	Remote Similarity	NPD9676	Phase 3
0.5692	Remote Similarity	NPD4224	Phase 2
0.566	Remote Similarity	NPD39	Approved
0.566	Remote Similarity	NPD3174	Discontinued
0.566	Remote Similarity	NPD4222	Approved
0.5645	Remote Similarity	NPD9656	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