NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.14
Volume:	243.309
LogP:	2.172
LogD:	1.518
LogS:	-3.185
# Rotatable Bonds:	6
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.532
Synthetic Accessibility Score:	3.446
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.478
MDCK Permeability:	4.199550312478095e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.898
Plasma Protein Binding (PPB):	81.25911712646484%
Volume Distribution (VD):	0.166
Pgp-substrate:	11.191241264343262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.405
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.757
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	7.531
Half-life (T1/2):	0.921

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.218
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.814
Skin Sensitization:	0.14
Carcinogencity:	0.646
Eye Corrosion:	0.276
Eye Irritation:	0.431
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC304665

Natural Product ID:	NPC304665
*Common Name:**	Methyl 2-[3-Oxo-2-[(E)-Pent-2-Enyl]Cyclopentyl]Acetate
IUPAC Name:	methyl 2-[3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetate
Synonyms:
Standard InCHIKey:	GEWDNTWNSAZUDX-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4+
SMILES:	CC/C=C/CC1C(CCC1=O)CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL184827
PubChem CID:	5367719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives [CHEMONTID:0000512] Jasmonic 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
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	29.2	mg/g DW	PMID[457269]
NPT2	Others	Unspecified		Activity	=	386.0	mg l-1	PMID[457269]

☑ 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 NPC304665 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	167
0.1-0.2	1547
0.2-0.3	11204
0.3-0.4	15210
0.4-0.5	8320
0.5-0.6	4965
0.6-0.7	1180
0.7-0.8	96
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126899
1.0	High Similarity	NPC154728
0.9219	High Similarity	NPC60120
0.7903	Intermediate Similarity	NPC319589
0.7857	Intermediate Similarity	NPC296522
0.7857	Intermediate Similarity	NPC144511
0.7857	Intermediate Similarity	NPC199557
0.7778	Intermediate Similarity	NPC321017
0.7714	Intermediate Similarity	NPC476614
0.7703	Intermediate Similarity	NPC279537
0.7632	Intermediate Similarity	NPC469690
0.7595	Intermediate Similarity	NPC238197
0.7581	Intermediate Similarity	NPC216407
0.7534	Intermediate Similarity	NPC470237
0.7534	Intermediate Similarity	NPC472956
0.75	Intermediate Similarity	NPC472955
0.7467	Intermediate Similarity	NPC266159
0.7467	Intermediate Similarity	NPC472967
0.746	Intermediate Similarity	NPC39633
0.746	Intermediate Similarity	NPC139545
0.746	Intermediate Similarity	NPC309606
0.7429	Intermediate Similarity	NPC18252
0.7403	Intermediate Similarity	NPC469620
0.7403	Intermediate Similarity	NPC28319
0.7368	Intermediate Similarity	NPC195785
0.7368	Intermediate Similarity	NPC15975
0.7353	Intermediate Similarity	NPC125312
0.7353	Intermediate Similarity	NPC174560
0.7297	Intermediate Similarity	NPC92909
0.7297	Intermediate Similarity	NPC107783
0.7273	Intermediate Similarity	NPC474056
0.7258	Intermediate Similarity	NPC224227
0.725	Intermediate Similarity	NPC65350
0.7237	Intermediate Similarity	NPC473223
0.7237	Intermediate Similarity	NPC226242
0.7237	Intermediate Similarity	NPC472959
0.7231	Intermediate Similarity	NPC128061
0.7231	Intermediate Similarity	NPC200845
0.7231	Intermediate Similarity	NPC223677
0.7231	Intermediate Similarity	NPC228473
0.7231	Intermediate Similarity	NPC10316
0.7231	Intermediate Similarity	NPC28779
0.7215	Intermediate Similarity	NPC191711
0.7215	Intermediate Similarity	NPC47031
0.7213	Intermediate Similarity	NPC216130
0.7206	Intermediate Similarity	NPC229252
0.7206	Intermediate Similarity	NPC143857
0.72	Intermediate Similarity	NPC472966
0.72	Intermediate Similarity	NPC469641
0.72	Intermediate Similarity	NPC469643
0.72	Intermediate Similarity	NPC167049
0.72	Intermediate Similarity	NPC55527
0.72	Intermediate Similarity	NPC469691
0.7195	Intermediate Similarity	NPC6247
0.7188	Intermediate Similarity	NPC71761
0.7179	Intermediate Similarity	NPC182550
0.7179	Intermediate Similarity	NPC164308
0.7179	Intermediate Similarity	NPC201225
0.7162	Intermediate Similarity	NPC29328
0.7162	Intermediate Similarity	NPC129665
0.716	Intermediate Similarity	NPC149869
0.716	Intermediate Similarity	NPC320801
0.7143	Intermediate Similarity	NPC107668
0.7143	Intermediate Similarity	NPC475932
0.7143	Intermediate Similarity	NPC122264
0.7143	Intermediate Similarity	NPC473902
0.7143	Intermediate Similarity	NPC262968
0.7125	Intermediate Similarity	NPC7414
0.7125	Intermediate Similarity	NPC173609
0.7125	Intermediate Similarity	NPC100297
0.7125	Intermediate Similarity	NPC240302
0.7123	Intermediate Similarity	NPC5714
0.7121	Intermediate Similarity	NPC477201
0.7105	Intermediate Similarity	NPC193351
0.7105	Intermediate Similarity	NPC475861
0.7105	Intermediate Similarity	NPC138408
0.7105	Intermediate Similarity	NPC244166
0.7105	Intermediate Similarity	NPC155587
0.7105	Intermediate Similarity	NPC324762
0.7105	Intermediate Similarity	NPC226669
0.7101	Intermediate Similarity	NPC475795
0.7089	Intermediate Similarity	NPC115418
0.7089	Intermediate Similarity	NPC47747
0.7083	Intermediate Similarity	NPC476626
0.7073	Intermediate Similarity	NPC28887
0.7073	Intermediate Similarity	NPC142649
0.7067	Intermediate Similarity	NPC135703
0.7067	Intermediate Similarity	NPC300940
0.7067	Intermediate Similarity	NPC167145
0.7059	Intermediate Similarity	NPC259261
0.7051	Intermediate Similarity	NPC299235
0.7051	Intermediate Similarity	NPC471220
0.7051	Intermediate Similarity	NPC192006
0.7051	Intermediate Similarity	NPC128276
0.7051	Intermediate Similarity	NPC63445
0.7051	Intermediate Similarity	NPC222210
0.7037	Intermediate Similarity	NPC39588
0.7037	Intermediate Similarity	NPC108045
0.7037	Intermediate Similarity	NPC475622
0.7031	Intermediate Similarity	NPC170167
0.7031	Intermediate Similarity	NPC281245
0.7027	Intermediate Similarity	NPC475310
0.7015	Intermediate Similarity	NPC55004
0.7015	Intermediate Similarity	NPC230823
0.7015	Intermediate Similarity	NPC49575
0.7015	Intermediate Similarity	NPC193695
0.7015	Intermediate Similarity	NPC267626
0.7013	Intermediate Similarity	NPC469646
0.7013	Intermediate Similarity	NPC12740
0.7013	Intermediate Similarity	NPC110461
0.7013	Intermediate Similarity	NPC471726
0.7013	Intermediate Similarity	NPC474527
0.7013	Intermediate Similarity	NPC266119
0.7013	Intermediate Similarity	NPC41017
0.7013	Intermediate Similarity	NPC40353
0.7011	Intermediate Similarity	NPC56525
0.7	Intermediate Similarity	NPC88735
0.7	Intermediate Similarity	NPC255580
0.7	Intermediate Similarity	NPC39411
0.7	Intermediate Similarity	NPC32285
0.6986	Remote Similarity	NPC476629
0.6974	Remote Similarity	NPC166797
0.6974	Remote Similarity	NPC330016
0.697	Remote Similarity	NPC477984
0.6962	Remote Similarity	NPC63649
0.6962	Remote Similarity	NPC264227
0.6962	Remote Similarity	NPC472965
0.6962	Remote Similarity	NPC477371
0.6951	Remote Similarity	NPC475796
0.6944	Remote Similarity	NPC197089
0.6933	Remote Similarity	NPC163003
0.6933	Remote Similarity	NPC469737
0.6933	Remote Similarity	NPC288667
0.6923	Remote Similarity	NPC139029
0.6923	Remote Similarity	NPC294548
0.6923	Remote Similarity	NPC472300
0.6923	Remote Similarity	NPC103987
0.6923	Remote Similarity	NPC57744
0.6923	Remote Similarity	NPC1813
0.6923	Remote Similarity	NPC65603
0.6923	Remote Similarity	NPC145898
0.6923	Remote Similarity	NPC53581
0.6923	Remote Similarity	NPC36061
0.6914	Remote Similarity	NPC221231
0.6914	Remote Similarity	NPC302661
0.6914	Remote Similarity	NPC471326
0.6914	Remote Similarity	NPC327969
0.6914	Remote Similarity	NPC238991
0.6914	Remote Similarity	NPC321289
0.6912	Remote Similarity	NPC266295
0.6912	Remote Similarity	NPC94991
0.6901	Remote Similarity	NPC469723
0.6901	Remote Similarity	NPC234767
0.6892	Remote Similarity	NPC469677
0.6892	Remote Similarity	NPC162867
0.6892	Remote Similarity	NPC61702
0.6892	Remote Similarity	NPC67608
0.6892	Remote Similarity	NPC22301
0.6883	Remote Similarity	NPC469669
0.6883	Remote Similarity	NPC469678
0.6883	Remote Similarity	NPC255060
0.6883	Remote Similarity	NPC216791
0.6883	Remote Similarity	NPC475771
0.6875	Remote Similarity	NPC200446
0.6875	Remote Similarity	NPC164218
0.6875	Remote Similarity	NPC244452
0.6875	Remote Similarity	NPC26139
0.6875	Remote Similarity	NPC276356
0.6875	Remote Similarity	NPC302426
0.6875	Remote Similarity	NPC69271
0.6875	Remote Similarity	NPC74673
0.6867	Remote Similarity	NPC472686
0.6867	Remote Similarity	NPC290329
0.6867	Remote Similarity	NPC323765
0.6867	Remote Similarity	NPC470223
0.6867	Remote Similarity	NPC161957
0.6857	Remote Similarity	NPC201939
0.6857	Remote Similarity	NPC97322
0.6849	Remote Similarity	NPC475523
0.6842	Remote Similarity	NPC58956
0.6842	Remote Similarity	NPC177826
0.6842	Remote Similarity	NPC269206
0.6842	Remote Similarity	NPC295633
0.6835	Remote Similarity	NPC27949
0.6835	Remote Similarity	NPC35574
0.6835	Remote Similarity	NPC218817
0.6835	Remote Similarity	NPC474341
0.6835	Remote Similarity	NPC260814
0.6835	Remote Similarity	NPC469495
0.6835	Remote Similarity	NPC11796
0.6835	Remote Similarity	NPC39547
0.6835	Remote Similarity	NPC323249
0.6829	Remote Similarity	NPC469561
0.6829	Remote Similarity	NPC271784
0.6824	Remote Similarity	NPC190718
0.6818	Remote Similarity	NPC202850
0.6818	Remote Similarity	NPC424
0.6818	Remote Similarity	NPC25417
0.6818	Remote Similarity	NPC290563
0.6818	Remote Similarity	NPC32467

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 NPC304665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	2266
0.2-0.3	4296
0.3-0.4	1648
0.4-0.5	473
0.5-0.6	240
0.6-0.7	57
0.7-0.8	9
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
0.7564	Intermediate Similarity	NPD6435	Approved
0.7532	Intermediate Similarity	NPD5368	Approved
0.7436	Intermediate Similarity	NPD5369	Approved
0.7273	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5786	Approved
0.7143	Intermediate Similarity	NPD29	Approved
0.7143	Intermediate Similarity	NPD28	Approved
0.7125	Intermediate Similarity	NPD4269	Approved
0.7125	Intermediate Similarity	NPD4270	Approved
0.7089	Intermediate Similarity	NPD4252	Approved
0.7037	Intermediate Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD3172	Approved
0.6875	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5363	Approved
0.6835	Remote Similarity	NPD4271	Approved
0.6835	Remote Similarity	NPD4268	Approved
0.6818	Remote Similarity	NPD3196	Approved
0.6818	Remote Similarity	NPD3195	Phase 2
0.6818	Remote Similarity	NPD4266	Approved
0.6818	Remote Similarity	NPD3194	Approved
0.6786	Remote Similarity	NPD6684	Approved
0.6786	Remote Similarity	NPD7334	Approved
0.6786	Remote Similarity	NPD7521	Approved
0.6786	Remote Similarity	NPD7146	Approved
0.6786	Remote Similarity	NPD5330	Approved
0.6786	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6628	Remote Similarity	NPD6672	Approved
0.6628	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6903	Approved
0.6628	Remote Similarity	NPD5737	Approved
0.6627	Remote Similarity	NPD7154	Phase 3
0.6613	Remote Similarity	NPD3174	Discontinued
0.6588	Remote Similarity	NPD6098	Approved
0.6567	Remote Similarity	NPD9298	Approved
0.6486	Remote Similarity	NPD7331	Phase 2
0.6477	Remote Similarity	NPD5207	Approved
0.6471	Remote Similarity	NPD1694	Approved
0.6456	Remote Similarity	NPD8039	Approved
0.6438	Remote Similarity	NPD3197	Phase 1
0.6437	Remote Similarity	NPD5208	Approved
0.6429	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD5331	Approved
0.6406	Remote Similarity	NPD622	Approved
0.6404	Remote Similarity	NPD5694	Approved
0.6395	Remote Similarity	NPD4249	Approved
0.6386	Remote Similarity	NPD4790	Discontinued
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6344	Remote Similarity	NPD5696	Approved
0.6333	Remote Similarity	NPD6399	Phase 3
0.6322	Remote Similarity	NPD3573	Approved
0.6322	Remote Similarity	NPD4251	Approved
0.6322	Remote Similarity	NPD4250	Approved
0.631	Remote Similarity	NPD5209	Approved
0.631	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3667	Approved
0.6308	Remote Similarity	NPD3173	Approved
0.6292	Remote Similarity	NPD5692	Phase 3
0.6279	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4137	Phase 3
0.6222	Remote Similarity	NPD6050	Approved
0.6222	Remote Similarity	NPD5281	Approved
0.6222	Remote Similarity	NPD5284	Approved
0.6222	Remote Similarity	NPD5693	Phase 1
0.6196	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5695	Phase 3
0.6196	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.618	Remote Similarity	NPD1695	Approved
0.618	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6101	Approved
0.618	Remote Similarity	NPD5370	Suspended
0.6163	Remote Similarity	NPD3665	Phase 1
0.6163	Remote Similarity	NPD3133	Approved
0.6163	Remote Similarity	NPD4786	Approved
0.6163	Remote Similarity	NPD3666	Approved
0.6163	Remote Similarity	NPD3668	Phase 3
0.6154	Remote Similarity	NPD4691	Approved
0.6154	Remote Similarity	NPD5343	Approved
0.6154	Remote Similarity	NPD4747	Approved
0.6133	Remote Similarity	NPD7341	Phase 2
0.6125	Remote Similarity	NPD4687	Approved
0.6125	Remote Similarity	NPD4058	Approved
0.6118	Remote Similarity	NPD4221	Approved
0.6118	Remote Similarity	NPD4223	Phase 3
0.6111	Remote Similarity	NPD3198	Approved
0.6104	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6001	Approved
0.6076	Remote Similarity	NPD5276	Approved
0.6064	Remote Similarity	NPD6084	Phase 2
0.6064	Remote Similarity	NPD6083	Phase 2
0.6044	Remote Similarity	NPD6079	Approved
0.6044	Remote Similarity	NPD6411	Approved
0.6044	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3618	Phase 1
0.6023	Remote Similarity	NPD5279	Phase 3
0.6023	Remote Similarity	NPD5690	Phase 2
0.6023	Remote Similarity	NPD6422	Discontinued
0.6022	Remote Similarity	NPD4629	Approved
0.6022	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD857	Phase 3
0.5978	Remote Similarity	NPD5779	Approved
0.5978	Remote Similarity	NPD5778	Approved
0.5977	Remote Similarity	NPD4197	Approved
0.5977	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7732	Phase 3
0.5926	Remote Similarity	NPD5733	Approved
0.5921	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5329	Approved
0.5904	Remote Similarity	NPD4756	Discovery
0.59	Remote Similarity	NPD6614	Approved
0.59	Remote Similarity	NPD5697	Approved
0.5889	Remote Similarity	NPD4518	Approved
0.587	Remote Similarity	NPD7983	Approved
0.5851	Remote Similarity	NPD5654	Approved
0.5851	Remote Similarity	NPD1693	Approved
0.5846	Remote Similarity	NPD4222	Approved
0.5846	Remote Similarity	NPD634	Phase 3
0.5843	Remote Similarity	NPD5280	Approved
0.5843	Remote Similarity	NPD4690	Approved
0.5843	Remote Similarity	NPD4693	Phase 3
0.5843	Remote Similarity	NPD4694	Approved
0.5843	Remote Similarity	NPD4688	Approved
0.5843	Remote Similarity	NPD4689	Approved
0.5843	Remote Similarity	NPD5205	Approved
0.5843	Remote Similarity	NPD4138	Approved
0.5842	Remote Similarity	NPD6011	Approved
0.5842	Remote Similarity	NPD6899	Approved
0.5842	Remote Similarity	NPD6881	Approved
0.5833	Remote Similarity	NPD3732	Approved
0.5833	Remote Similarity	NPD3617	Approved
0.5824	Remote Similarity	NPD4753	Phase 2
0.5811	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD6008	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6675	Approved
0.5789	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5222	Approved
0.5789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5221	Approved
0.5784	Remote Similarity	NPD6014	Approved
0.5784	Remote Similarity	NPD6013	Approved
0.5784	Remote Similarity	NPD6012	Approved
0.5761	Remote Similarity	NPD3672	Approved
0.5761	Remote Similarity	NPD3673	Approved
0.5745	Remote Similarity	NPD7900	Approved
0.5745	Remote Similarity	NPD7748	Approved
0.5745	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5701	Approved
0.573	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5959	Approved
0.5729	Remote Similarity	NPD5173	Approved
0.5728	Remote Similarity	NPD7102	Approved
0.5728	Remote Similarity	NPD7290	Approved
0.5728	Remote Similarity	NPD6883	Approved
0.5699	Remote Similarity	NPD7637	Suspended
0.5699	Remote Similarity	NPD7515	Phase 2
0.5698	Remote Similarity	NPD4695	Discontinued
0.5692	Remote Similarity	NPD6096	Approved
0.5692	Remote Similarity	NPD6097	Approved
0.5686	Remote Similarity	NPD7320	Approved
0.5679	Remote Similarity	NPD5777	Approved
0.5679	Remote Similarity	NPD6081	Approved
0.5673	Remote Similarity	NPD6869	Approved
0.5673	Remote Similarity	NPD6847	Approved
0.5673	Remote Similarity	NPD6650	Approved
0.5673	Remote Similarity	NPD6617	Approved
0.5673	Remote Similarity	NPD6649	Approved
0.5673	Remote Similarity	NPD8130	Phase 1
0.5667	Remote Similarity	NPD4519	Discontinued
0.5667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD4623	Approved
0.5658	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4202	Approved
0.5634	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD4692	Approved
0.5632	Remote Similarity	NPD4139	Approved
0.5631	Remote Similarity	NPD6372	Approved
0.5631	Remote Similarity	NPD6373	Approved
0.5625	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7839	Suspended
0.5625	Remote Similarity	NPD7614	Phase 1
0.5625	Remote Similarity	NPD4697	Phase 3
0.5619	Remote Similarity	NPD8297	Approved
0.5619	Remote Similarity	NPD6882	Approved
0.5612	Remote Similarity	NPD5286	Approved
0.5612	Remote Similarity	NPD4696	Approved
0.5612	Remote Similarity	NPD5285	Approved
0.5606	Remote Similarity	NPD39	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