NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	173.01
Volume:	151.743
LogP:	-1.682
LogD:	-0.771
LogS:	-1.224
# Rotatable Bonds:	1
TPSA:	80.39
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	1.774
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.422
MDCK Permeability:	0.0004773933906108141
Pgp-inhibitor:	0.0
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.193
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	35.66998291015625%
Volume Distribution (VD):	0.32
Pgp-substrate:	68.44319915771484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.845
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	3.345
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.121
Carcinogencity:	0.101
Eye Corrosion:	0.973
Eye Irritation:	0.984
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC107130

Natural Product ID:	NPC107130
*Common Name:**	Methyl (3R,6S,Z)-4,6-Diethyl-3,6-Epidioxyundeca-4-Enoate
IUPAC Name:	methyl 2-[(3R,6S)-4,6-diethyl-6-pentyl-3H-1,2-dioxin-3-yl]acetate
Synonyms:
Standard InCHIKey:	GPYRVTKLZXIKRF-ZBFHGGJFSA-N
Standard InCHI:	InChI=1S/C16H28O4/c1-5-8-9-10-16(7-3)12-13(6-2)14(19-20-16)11-15(17)18-4/h12,14H,5-11H2,1-4H3/t14-,16+/m1/s1
SMILES:	CCCCC[C@]1(CC)OO[C@@H](C(=C1)CC)CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464767
PubChem CID:	11369629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters [CHEMONTID:0003416] Methyl esters

*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
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO26409	Plakortis simplex	Species	Plakinidae	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	12

Activity Type	# Activity
NON-MOLECULAR	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[544656]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[544657]

☑ 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 NPC107130 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	191
0.1-0.2	1371
0.2-0.3	6965
0.3-0.4	17446
0.4-0.5	8823
0.5-0.6	6172
0.6-0.7	1599
0.7-0.8	108
0.8-0.85	9
0.85-0.9	5
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC69462
0.9552	High Similarity	NPC474543
0.9552	High Similarity	NPC238425
0.9552	High Similarity	NPC472018
0.9412	High Similarity	NPC474551
0.9254	High Similarity	NPC472017
0.9	High Similarity	NPC199445
0.8873	High Similarity	NPC474447
0.8841	High Similarity	NPC126061
0.8472	Intermediate Similarity	NPC60718
0.8451	Intermediate Similarity	NPC167145
0.8378	Intermediate Similarity	NPC121200
0.8333	Intermediate Similarity	NPC330016
0.8289	Intermediate Similarity	NPC475481
0.8289	Intermediate Similarity	NPC79277
0.8243	Intermediate Similarity	NPC476325
0.8243	Intermediate Similarity	NPC476264
0.8243	Intermediate Similarity	NPC281296
0.8219	Intermediate Similarity	NPC255060
0.8108	Intermediate Similarity	NPC239127
0.7867	Intermediate Similarity	NPC469514
0.7867	Intermediate Similarity	NPC266119
0.7857	Intermediate Similarity	NPC284447
0.7848	Intermediate Similarity	NPC69469
0.7821	Intermediate Similarity	NPC476988
0.7792	Intermediate Similarity	NPC82488
0.7792	Intermediate Similarity	NPC308545
0.7692	Intermediate Similarity	NPC469920
0.7632	Intermediate Similarity	NPC476987
0.7632	Intermediate Similarity	NPC59602
0.7632	Intermediate Similarity	NPC152754
0.7625	Intermediate Similarity	NPC475989
0.76	Intermediate Similarity	NPC474758
0.7595	Intermediate Similarity	NPC117960
0.7595	Intermediate Similarity	NPC14044
0.7595	Intermediate Similarity	NPC172309
0.7561	Intermediate Similarity	NPC476982
0.7561	Intermediate Similarity	NPC476104
0.7532	Intermediate Similarity	NPC474760
0.75	Intermediate Similarity	NPC85772
0.7439	Intermediate Similarity	NPC471344
0.7436	Intermediate Similarity	NPC127526
0.7436	Intermediate Similarity	NPC474341
0.7432	Intermediate Similarity	NPC475310
0.7407	Intermediate Similarity	NPC476983
0.7407	Intermediate Similarity	NPC16488
0.7407	Intermediate Similarity	NPC475947
0.7403	Intermediate Similarity	NPC476985
0.7403	Intermediate Similarity	NPC474316
0.7403	Intermediate Similarity	NPC475744
0.7397	Intermediate Similarity	NPC276290
0.7375	Intermediate Similarity	NPC141810
0.7349	Intermediate Similarity	NPC472009
0.7342	Intermediate Similarity	NPC113363
0.7342	Intermediate Similarity	NPC471740
0.7342	Intermediate Similarity	NPC268502
0.7342	Intermediate Similarity	NPC471299
0.7342	Intermediate Similarity	NPC254996
0.7324	Intermediate Similarity	NPC34883
0.7317	Intermediate Similarity	NPC295799
0.7308	Intermediate Similarity	NPC107668
0.7308	Intermediate Similarity	NPC122847
0.7308	Intermediate Similarity	NPC145898
0.7297	Intermediate Similarity	NPC477448
0.7297	Intermediate Similarity	NPC477449
0.7284	Intermediate Similarity	NPC475936
0.7284	Intermediate Similarity	NPC475690
0.7273	Intermediate Similarity	NPC475861
0.7273	Intermediate Similarity	NPC329852
0.7262	Intermediate Similarity	NPC472007
0.7262	Intermediate Similarity	NPC86005
0.7237	Intermediate Similarity	NPC135703
0.7231	Intermediate Similarity	NPC216407
0.7229	Intermediate Similarity	NPC474369
0.7229	Intermediate Similarity	NPC261380
0.7215	Intermediate Similarity	NPC128276
0.7215	Intermediate Similarity	NPC478122
0.72	Intermediate Similarity	NPC469660
0.72	Intermediate Similarity	NPC472955
0.7195	Intermediate Similarity	NPC170286
0.7195	Intermediate Similarity	NPC318468
0.7195	Intermediate Similarity	NPC53867
0.7183	Intermediate Similarity	NPC217940
0.7176	Intermediate Similarity	NPC475906
0.7176	Intermediate Similarity	NPC471047
0.7176	Intermediate Similarity	NPC469653
0.7176	Intermediate Similarity	NPC469628
0.7176	Intermediate Similarity	NPC472008
0.7176	Intermediate Similarity	NPC469631
0.716	Intermediate Similarity	NPC286229
0.716	Intermediate Similarity	NPC301477
0.716	Intermediate Similarity	NPC25684
0.716	Intermediate Similarity	NPC281949
0.716	Intermediate Similarity	NPC471325
0.7143	Intermediate Similarity	NPC259599
0.7143	Intermediate Similarity	NPC262085
0.7143	Intermediate Similarity	NPC469483
0.7143	Intermediate Similarity	NPC315395
0.7143	Intermediate Similarity	NPC476355
0.7143	Intermediate Similarity	NPC279859
0.7143	Intermediate Similarity	NPC15499
0.7143	Intermediate Similarity	NPC294434
0.7143	Intermediate Similarity	NPC140287
0.7143	Intermediate Similarity	NPC117746
0.7143	Intermediate Similarity	NPC316426
0.7143	Intermediate Similarity	NPC38576
0.7143	Intermediate Similarity	NPC160540
0.7125	Intermediate Similarity	NPC473981
0.7125	Intermediate Similarity	NPC617
0.7125	Intermediate Similarity	NPC473980
0.7125	Intermediate Similarity	NPC178277
0.7108	Intermediate Similarity	NPC477576
0.7108	Intermediate Similarity	NPC243618
0.7108	Intermediate Similarity	NPC477575
0.7108	Intermediate Similarity	NPC70424
0.7105	Intermediate Similarity	NPC477084
0.7105	Intermediate Similarity	NPC129665
0.7105	Intermediate Similarity	NPC163003
0.7093	Intermediate Similarity	NPC469866
0.7093	Intermediate Similarity	NPC471342
0.7093	Intermediate Similarity	NPC475971
0.7089	Intermediate Similarity	NPC470240
0.7089	Intermediate Similarity	NPC141789
0.7089	Intermediate Similarity	NPC187568
0.7089	Intermediate Similarity	NPC476794
0.7089	Intermediate Similarity	NPC41780
0.7089	Intermediate Similarity	NPC97516
0.7089	Intermediate Similarity	NPC171204
0.7089	Intermediate Similarity	NPC469867
0.7089	Intermediate Similarity	NPC57744
0.7089	Intermediate Similarity	NPC476028
0.7073	Intermediate Similarity	NPC474252
0.7073	Intermediate Similarity	NPC475395
0.7073	Intermediate Similarity	NPC476984
0.7067	Intermediate Similarity	NPC144511
0.7067	Intermediate Similarity	NPC101622
0.7067	Intermediate Similarity	NPC199557
0.7067	Intermediate Similarity	NPC269841
0.7067	Intermediate Similarity	NPC296522
0.7059	Intermediate Similarity	NPC477959
0.7059	Intermediate Similarity	NPC471738
0.7051	Intermediate Similarity	NPC244166
0.7051	Intermediate Similarity	NPC228978
0.7051	Intermediate Similarity	NPC469414
0.7051	Intermediate Similarity	NPC329826
0.7051	Intermediate Similarity	NPC324762
0.7037	Intermediate Similarity	NPC476265
0.7037	Intermediate Similarity	NPC103634
0.7037	Intermediate Similarity	NPC233377
0.7037	Intermediate Similarity	NPC274522
0.7027	Intermediate Similarity	NPC194871
0.7027	Intermediate Similarity	NPC472266
0.7024	Intermediate Similarity	NPC125290
0.7013	Intermediate Similarity	NPC222244
0.7013	Intermediate Similarity	NPC16349
0.7011	Intermediate Similarity	NPC51653
0.7	Intermediate Similarity	NPC218817
0.7	Intermediate Similarity	NPC472019
0.7	Intermediate Similarity	NPC226602
0.7	Intermediate Similarity	NPC11796
0.7	Intermediate Similarity	NPC475699
0.7	Intermediate Similarity	NPC253749
0.7	Intermediate Similarity	NPC472020
0.7	Intermediate Similarity	NPC470905
0.7	Intermediate Similarity	NPC471220
0.7	Intermediate Similarity	NPC476986
0.6988	Remote Similarity	NPC170377
0.6988	Remote Similarity	NPC222358
0.6988	Remote Similarity	NPC475842
0.6988	Remote Similarity	NPC474703
0.6986	Remote Similarity	NPC326268
0.6986	Remote Similarity	NPC318420
0.6977	Remote Similarity	NPC475902
0.6974	Remote Similarity	NPC4299
0.697	Remote Similarity	NPC170167
0.6962	Remote Similarity	NPC27205
0.6962	Remote Similarity	NPC12740
0.6962	Remote Similarity	NPC123360
0.6962	Remote Similarity	NPC279537
0.6962	Remote Similarity	NPC235906
0.6962	Remote Similarity	NPC110461
0.6962	Remote Similarity	NPC301525
0.6962	Remote Similarity	NPC61863
0.6957	Remote Similarity	NPC165808
0.6951	Remote Similarity	NPC275507
0.6951	Remote Similarity	NPC47031
0.6951	Remote Similarity	NPC470241
0.6944	Remote Similarity	NPC54925
0.6941	Remote Similarity	NPC261721
0.6941	Remote Similarity	NPC116575
0.6941	Remote Similarity	NPC50637
0.6933	Remote Similarity	NPC209327
0.6933	Remote Similarity	NPC218477
0.6933	Remote Similarity	NPC469688
0.6933	Remote Similarity	NPC273508
0.6932	Remote Similarity	NPC166110
0.6932	Remote Similarity	NPC472705
0.6914	Remote Similarity	NPC201225
0.6914	Remote Similarity	NPC270126
0.6914	Remote Similarity	NPC325869

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 NPC107130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	2004
0.2-0.3	4082
0.3-0.4	2034
0.4-0.5	640
0.5-0.6	176
0.6-0.7	47
0.7-0.8	3
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
0.7465	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD8039	Approved
0.6988	Remote Similarity	NPD7154	Phase 3
0.6951	Remote Similarity	NPD5369	Approved
0.6867	Remote Similarity	NPD4270	Approved
0.6867	Remote Similarity	NPD4269	Approved
0.6867	Remote Similarity	NPD5209	Approved
0.6854	Remote Similarity	NPD5778	Approved
0.6854	Remote Similarity	NPD5779	Approved
0.6829	Remote Similarity	NPD4252	Approved
0.6829	Remote Similarity	NPD4822	Approved
0.6829	Remote Similarity	NPD4820	Approved
0.6829	Remote Similarity	NPD4821	Approved
0.6829	Remote Similarity	NPD4819	Approved
0.679	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5362	Discontinued
0.6744	Remote Similarity	NPD5786	Approved
0.6742	Remote Similarity	NPD7983	Approved
0.6705	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7839	Suspended
0.6629	Remote Similarity	NPD6698	Approved
0.6629	Remote Similarity	NPD46	Approved
0.6628	Remote Similarity	NPD5363	Approved
0.6627	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4268	Approved
0.6585	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD7637	Suspended
0.6556	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD6435	Approved
0.6447	Remote Similarity	NPD7331	Phase 2
0.6444	Remote Similarity	NPD5785	Approved
0.6438	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5368	Approved
0.64	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5332	Approved
0.6395	Remote Similarity	NPD5331	Approved
0.6374	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4790	Discontinued
0.6333	Remote Similarity	NPD5370	Suspended
0.6324	Remote Similarity	NPD6927	Phase 3
0.6324	Remote Similarity	NPD28	Approved
0.6324	Remote Similarity	NPD29	Approved
0.6322	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD3174	Discontinued
0.6265	Remote Similarity	NPD4756	Discovery
0.625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1694	Approved
0.619	Remote Similarity	NPD3732	Approved
0.6184	Remote Similarity	NPD3197	Phase 1
0.618	Remote Similarity	NPD6422	Discontinued
0.618	Remote Similarity	NPD5330	Approved
0.618	Remote Similarity	NPD7334	Approved
0.618	Remote Similarity	NPD7146	Approved
0.618	Remote Similarity	NPD6409	Approved
0.618	Remote Similarity	NPD6684	Approved
0.618	Remote Similarity	NPD7521	Approved
0.618	Remote Similarity	NPD4249	Approved
0.617	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1695	Approved
0.6154	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4225	Approved
0.6143	Remote Similarity	NPD3172	Approved
0.6133	Remote Similarity	NPD368	Approved
0.6119	Remote Similarity	NPD5343	Approved
0.6111	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4250	Approved
0.61	Remote Similarity	NPD5048	Discontinued
0.6064	Remote Similarity	NPD5282	Discontinued
0.6056	Remote Similarity	NPD3196	Approved
0.6056	Remote Similarity	NPD3194	Approved
0.6056	Remote Similarity	NPD3195	Phase 2
0.6056	Remote Similarity	NPD4266	Approved
0.6044	Remote Similarity	NPD6903	Approved
0.6044	Remote Similarity	NPD6672	Approved
0.6044	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5737	Approved
0.604	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3173	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.5978	Remote Similarity	NPD6051	Approved
0.5957	Remote Similarity	NPD6399	Phase 3
0.5921	Remote Similarity	NPD4194	Approved
0.5921	Remote Similarity	NPD4191	Approved
0.5921	Remote Similarity	NPD4193	Approved
0.5921	Remote Similarity	NPD4192	Approved
0.5914	Remote Similarity	NPD7838	Discovery
0.5897	Remote Similarity	NPD7341	Phase 2
0.5895	Remote Similarity	NPD7748	Approved
0.5895	Remote Similarity	NPD7900	Approved
0.5895	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6083	Phase 2
0.5876	Remote Similarity	NPD6084	Phase 2
0.5865	Remote Similarity	NPD6371	Approved
0.5862	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7515	Phase 2
0.5851	Remote Similarity	NPD5693	Phase 1
0.5833	Remote Similarity	NPD7115	Discovery
0.5824	Remote Similarity	NPD6098	Approved
0.5823	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5696	Approved
0.5816	Remote Similarity	NPD7638	Approved
0.5816	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.581	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6673	Approved
0.5806	Remote Similarity	NPD6904	Approved
0.5806	Remote Similarity	NPD6080	Approved
0.5778	Remote Similarity	NPD3668	Phase 3
0.5761	Remote Similarity	NPD3573	Approved
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.5755	Remote Similarity	NPD6053	Discontinued
0.5745	Remote Similarity	NPD5692	Phase 3
0.573	Remote Similarity	NPD3667	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5699	Remote Similarity	NPD5208	Approved
0.5684	Remote Similarity	NPD5694	Approved
0.5684	Remote Similarity	NPD6050	Approved
0.5673	Remote Similarity	NPD6686	Approved
0.5672	Remote Similarity	NPD6097	Approved
0.5672	Remote Similarity	NPD6096	Approved
0.567	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6110	Phase 1
0.5641	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4753	Phase 2
0.5631	Remote Similarity	NPD6675	Approved
0.5631	Remote Similarity	NPD5739	Approved
0.5631	Remote Similarity	NPD7128	Approved
0.5631	Remote Similarity	NPD6402	Approved
0.5625	Remote Similarity	NPD3704	Approved
0.5625	Remote Similarity	NPD8513	Phase 3
0.5616	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD4228	Discovery
0.5604	Remote Similarity	NPD4786	Approved
0.5604	Remote Similarity	NPD3133	Approved
0.5604	Remote Similarity	NPD3666	Approved
0.5604	Remote Similarity	NPD3665	Phase 1
0.56	Remote Similarity	NPD6648	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