NPASS Compound

Structure

NPC215987 OpenBabel07101718302D 26 26 0 0 1 0 0 0 0 0999 V2000 3.2462 -1.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8764 -3.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6175 -4.1049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0579 -0.8827 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 1.7626 -3.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0214 -2.8801 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 1.3143 -2.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7967 -4.1049 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 1.5731 -1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9873 -2.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3484 -2.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0896 -3.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6945 -3.3284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3587 -1.7247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 14 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 15 2 1 6 0 0 0 15 18 1 0 0 0 0 16 15 1 6 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 20 5 1 6 0 0 0 20 26 1 0 0 0 0 25 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.24
Volume:	390.752
LogP:	2.308
LogD:	2.356
LogS:	-2.4
# Rotatable Bonds:	11
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	4.186
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.664
MDCK Permeability:	2.0625726392609067e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.153
30% Bioavailability (F30%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	61.331695556640625%
Volume Distribution (VD):	0.815
Pgp-substrate:	52.064884185791016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.496
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.834
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	9.271
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.437
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.473
Carcinogencity:	0.059
Eye Corrosion:	0.106
Eye Irritation:	0.048
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC215987

Natural Product ID:	NPC215987
*Common Name:**	Diacarperoxide C
IUPAC Name:	methyl (2R)-2-[(3S,6S)-6-(4,4-dimethyl-3,8-dioxononyl)-6-methyldioxan-3-yl]propanoate
Synonyms:	Diacarperoxide C
Standard InCHIKey:	OQQQVWCMVDRPGR-GUXCAODWSA-N
Standard InCHI:	InChI=1S/C20H34O6/c1-14(21)8-7-11-19(3,4)17(22)10-13-20(5)12-9-16(25-26-20)15(2)18(23)24-6/h15-16H,7-13H2,1-6H3/t15-,16+,20+/m1/s1
SMILES:	CC(=O)CCCC(C)(C)C(=O)CC[C@]1(C)CC[C@@H]([C@@H](C)C(=O)OC)OO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498535
PubChem CID:	25018206
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO9347	Diacarnus megaspinorhabdosa	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18672931]
NPO9347	Diacarnus megaspinorhabdosa	Species	Podospongiidae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	EC50	>	10.0	ug.mL-1	PMID[543854]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	35.0	%	PMID[543854]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	55.0	%	PMID[543854]

☑ 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 NPC215987 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	422
0.1-0.2	4237
0.2-0.3	13531
0.3-0.4	11304
0.4-0.5	7993
0.5-0.6	4831
0.6-0.7	318
0.7-0.8	39
0.8-0.85	11
0.85-0.9	3
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC306805
0.9333	High Similarity	NPC472021
0.9167	High Similarity	NPC472019
0.9167	High Similarity	NPC472020
0.9167	High Similarity	NPC226602
0.875	High Similarity	NPC476330
0.873	High Similarity	NPC474552
0.8462	Intermediate Similarity	NPC469926
0.8254	Intermediate Similarity	NPC475821
0.8194	Intermediate Similarity	NPC476325
0.8194	Intermediate Similarity	NPC476264
0.8056	Intermediate Similarity	NPC59602
0.8056	Intermediate Similarity	NPC476987
0.8056	Intermediate Similarity	NPC475744
0.8056	Intermediate Similarity	NPC474316
0.8056	Intermediate Similarity	NPC152754
0.8056	Intermediate Similarity	NPC476985
0.7973	Intermediate Similarity	NPC268502
0.7973	Intermediate Similarity	NPC254996
0.7945	Intermediate Similarity	NPC122847
0.7778	Intermediate Similarity	NPC330016
0.7746	Intermediate Similarity	NPC470243
0.7733	Intermediate Similarity	NPC308545
0.7733	Intermediate Similarity	NPC82488
0.7639	Intermediate Similarity	NPC167145
0.7639	Intermediate Similarity	NPC474755
0.7632	Intermediate Similarity	NPC476265
0.7632	Intermediate Similarity	NPC274522
0.76	Intermediate Similarity	NPC476986
0.76	Intermediate Similarity	NPC470905
0.7532	Intermediate Similarity	NPC476988
0.7468	Intermediate Similarity	NPC475193
0.7468	Intermediate Similarity	NPC120158
0.7467	Intermediate Similarity	NPC469867
0.7467	Intermediate Similarity	NPC474003
0.7463	Intermediate Similarity	NPC469922
0.7436	Intermediate Similarity	NPC476984
0.7436	Intermediate Similarity	NPC475395
0.7429	Intermediate Similarity	NPC469925
0.7424	Intermediate Similarity	NPC469924
0.7333	Intermediate Similarity	NPC469514
0.7333	Intermediate Similarity	NPC474447
0.7308	Intermediate Similarity	NPC172309
0.7308	Intermediate Similarity	NPC117960
0.7308	Intermediate Similarity	NPC14044
0.7273	Intermediate Similarity	NPC474754
0.725	Intermediate Similarity	NPC471343
0.7246	Intermediate Similarity	NPC314103
0.7237	Intermediate Similarity	NPC471151
0.7215	Intermediate Similarity	NPC476292
0.7215	Intermediate Similarity	NPC474605
0.7206	Intermediate Similarity	NPC469923
0.72	Intermediate Similarity	NPC179922
0.7162	Intermediate Similarity	NPC109510
0.7125	Intermediate Similarity	NPC476100
0.7125	Intermediate Similarity	NPC476983
0.7105	Intermediate Similarity	NPC239127
0.7105	Intermediate Similarity	NPC266119
0.7083	Intermediate Similarity	NPC319007
0.7083	Intermediate Similarity	NPC119838
0.7073	Intermediate Similarity	NPC476104
0.7073	Intermediate Similarity	NPC475181
0.7042	Intermediate Similarity	NPC135043
0.7042	Intermediate Similarity	NPC315525
0.7037	Intermediate Similarity	NPC65133
0.7027	Intermediate Similarity	NPC96322
0.7013	Intermediate Similarity	NPC477918
0.7013	Intermediate Similarity	NPC281296
0.7	Intermediate Similarity	NPC13494
0.6984	Remote Similarity	NPC314084
0.6974	Remote Similarity	NPC474419
0.6974	Remote Similarity	NPC255060
0.6962	Remote Similarity	NPC1882
0.6962	Remote Similarity	NPC469920
0.6951	Remote Similarity	NPC471344
0.6933	Remote Similarity	NPC475230
0.6933	Remote Similarity	NPC238425
0.6933	Remote Similarity	NPC474543
0.6933	Remote Similarity	NPC472018
0.6923	Remote Similarity	NPC121200
0.6912	Remote Similarity	NPC470363
0.6901	Remote Similarity	NPC157518
0.6885	Remote Similarity	NPC249754
0.6883	Remote Similarity	NPC471046
0.6875	Remote Similarity	NPC475481
0.6875	Remote Similarity	NPC79277
0.6867	Remote Similarity	NPC262085
0.6867	Remote Similarity	NPC476982
0.6867	Remote Similarity	NPC477441
0.6857	Remote Similarity	NPC235788
0.6842	Remote Similarity	NPC474551
0.6842	Remote Similarity	NPC317212
0.6842	Remote Similarity	NPC55508
0.6842	Remote Similarity	NPC477867
0.6835	Remote Similarity	NPC113363
0.6829	Remote Similarity	NPC477434
0.6825	Remote Similarity	NPC305182
0.6824	Remote Similarity	NPC471342
0.6824	Remote Similarity	NPC469866
0.6812	Remote Similarity	NPC469921
0.6812	Remote Similarity	NPC478126
0.6806	Remote Similarity	NPC241949
0.68	Remote Similarity	NPC478227
0.6795	Remote Similarity	NPC307865
0.6795	Remote Similarity	NPC108014
0.6774	Remote Similarity	NPC13105
0.6769	Remote Similarity	NPC72722
0.6757	Remote Similarity	NPC178541
0.6753	Remote Similarity	NPC477934
0.6753	Remote Similarity	NPC179858
0.675	Remote Similarity	NPC125366
0.6747	Remote Similarity	NPC477205
0.6721	Remote Similarity	NPC308301
0.6714	Remote Similarity	NPC306750
0.6714	Remote Similarity	NPC253204
0.6712	Remote Similarity	NPC41542
0.6712	Remote Similarity	NPC328304
0.6712	Remote Similarity	NPC329466
0.6711	Remote Similarity	NPC248567
0.6707	Remote Similarity	NPC472847
0.6707	Remote Similarity	NPC475989
0.6707	Remote Similarity	NPC476721
0.6706	Remote Similarity	NPC471221
0.6706	Remote Similarity	NPC221993
0.6667	Remote Similarity	NPC329490
0.6667	Remote Similarity	NPC216137
0.6667	Remote Similarity	NPC477933
0.6667	Remote Similarity	NPC477932
0.6667	Remote Similarity	NPC328639
0.6667	Remote Similarity	NPC475951
0.6667	Remote Similarity	NPC474020
0.6667	Remote Similarity	NPC295256
0.6667	Remote Similarity	NPC69462
0.6667	Remote Similarity	NPC120395
0.6667	Remote Similarity	NPC476717
0.6629	Remote Similarity	NPC217329
0.6628	Remote Similarity	NPC477443
0.6628	Remote Similarity	NPC477440
0.6627	Remote Similarity	NPC25037
0.6627	Remote Similarity	NPC34984
0.6627	Remote Similarity	NPC319909
0.6627	Remote Similarity	NPC181871
0.6627	Remote Similarity	NPC9060
0.6625	Remote Similarity	NPC276647
0.6625	Remote Similarity	NPC622
0.6625	Remote Similarity	NPC73013
0.6623	Remote Similarity	NPC477930
0.6591	Remote Similarity	NPC228700
0.6591	Remote Similarity	NPC474379
0.6585	Remote Similarity	NPC248415
0.6585	Remote Similarity	NPC477935
0.6585	Remote Similarity	NPC477936
0.6582	Remote Similarity	NPC169389
0.6579	Remote Similarity	NPC197701
0.6575	Remote Similarity	NPC84562
0.6575	Remote Similarity	NPC473899
0.6571	Remote Similarity	NPC204173
0.6562	Remote Similarity	NPC90904
0.6562	Remote Similarity	NPC55678
0.6557	Remote Similarity	NPC287231
0.6557	Remote Similarity	NPC47363
0.6552	Remote Similarity	NPC477442
0.6552	Remote Similarity	NPC477433
0.6552	Remote Similarity	NPC477444
0.6548	Remote Similarity	NPC473350
0.6548	Remote Similarity	NPC477445
0.6548	Remote Similarity	NPC474572
0.6543	Remote Similarity	NPC134227
0.6538	Remote Similarity	NPC60718
0.6538	Remote Similarity	NPC199445
0.6538	Remote Similarity	NPC228411
0.6533	Remote Similarity	NPC107130
0.6517	Remote Similarity	NPC309127
0.6517	Remote Similarity	NPC247877
0.6517	Remote Similarity	NPC206878
0.6508	Remote Similarity	NPC324793
0.6508	Remote Similarity	NPC477878
0.6506	Remote Similarity	NPC69469
0.6506	Remote Similarity	NPC15821
0.65	Remote Similarity	NPC472608
0.6486	Remote Similarity	NPC469868
0.6486	Remote Similarity	NPC286842
0.6471	Remote Similarity	NPC92139
0.6471	Remote Similarity	NPC238593
0.6471	Remote Similarity	NPC104961
0.6471	Remote Similarity	NPC70555
0.6471	Remote Similarity	NPC83242
0.6471	Remote Similarity	NPC70422
0.6447	Remote Similarity	NPC472017
0.6438	Remote Similarity	NPC469791
0.6438	Remote Similarity	NPC19311
0.6438	Remote Similarity	NPC230047
0.6437	Remote Similarity	NPC67653
0.6437	Remote Similarity	NPC77001
0.6437	Remote Similarity	NPC471459
0.6437	Remote Similarity	NPC253618
0.6437	Remote Similarity	NPC200580
0.6429	Remote Similarity	NPC469407
0.6429	Remote Similarity	NPC101138
0.6429	Remote Similarity	NPC17935

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 NPC215987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	524
0.1-0.2	4090
0.2-0.3	3011
0.3-0.4	887
0.4-0.5	434
0.5-0.6	189
0.6-0.7	15
0.7-0.8	0
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
0.7188	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD229	Approved
0.6923	Remote Similarity	NPD4802	Phase 2
0.6923	Remote Similarity	NPD4238	Approved
0.68	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2699	Approved
0.6528	Remote Similarity	NPD7909	Approved
0.6508	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.65	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3198	Approved
0.6375	Remote Similarity	NPD6116	Phase 1
0.6329	Remote Similarity	NPD3702	Approved
0.6265	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD6117	Approved
0.625	Remote Similarity	NPD2266	Phase 2
0.6212	Remote Similarity	NPD9638	Phase 2
0.6203	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.619	Remote Similarity	NPD634	Phase 3
0.6176	Remote Similarity	NPD3730	Approved
0.6176	Remote Similarity	NPD3728	Approved
0.6154	Remote Similarity	NPD6081	Approved
0.6133	Remote Similarity	NPD4224	Phase 2
0.6119	Remote Similarity	NPD3186	Phase 1
0.6111	Remote Similarity	NPD6411	Approved
0.6104	Remote Similarity	NPD3726	Approved
0.6104	Remote Similarity	NPD3725	Approved
0.6098	Remote Similarity	NPD6115	Approved
0.6098	Remote Similarity	NPD6118	Approved
0.6098	Remote Similarity	NPD6114	Approved
0.6098	Remote Similarity	NPD6697	Approved
0.6071	Remote Similarity	NPD1780	Approved
0.6071	Remote Similarity	NPD1779	Approved
0.6026	Remote Similarity	NPD4245	Approved
0.6026	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD5282	Discontinued
0.5949	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD3698	Phase 2
0.5897	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6101	Approved
0.5876	Remote Similarity	NPD8138	Approved
0.5876	Remote Similarity	NPD8086	Approved
0.5876	Remote Similarity	NPD8083	Approved
0.5876	Remote Similarity	NPD8082	Approved
0.5876	Remote Similarity	NPD8139	Approved
0.5876	Remote Similarity	NPD8085	Approved
0.5876	Remote Similarity	NPD8084	Approved
0.587	Remote Similarity	NPD6399	Phase 3
0.5833	Remote Similarity	NPD3206	Approved
0.5824	Remote Similarity	NPD5785	Approved
0.5823	Remote Similarity	NPD4789	Approved
0.5816	Remote Similarity	NPD8276	Approved
0.5816	Remote Similarity	NPD8275	Approved
0.5814	Remote Similarity	NPD6435	Approved
0.5814	Remote Similarity	NPD4269	Approved
0.5814	Remote Similarity	NPD7345	Approved
0.5814	Remote Similarity	NPD4270	Approved
0.5806	Remote Similarity	NPD7900	Approved
0.5806	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5360	Phase 3
0.5769	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD5368	Approved
0.5761	Remote Similarity	NPD8034	Phase 2
0.5761	Remote Similarity	NPD8035	Phase 2
0.5758	Remote Similarity	NPD8081	Approved
0.5745	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD2257	Approved
0.573	Remote Similarity	NPD5786	Approved
0.573	Remote Similarity	NPD7521	Approved
0.573	Remote Similarity	NPD7146	Approved
0.573	Remote Similarity	NPD7334	Approved
0.573	Remote Similarity	NPD6684	Approved
0.573	Remote Similarity	NPD6409	Approved
0.573	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD8301	Approved
0.5714	Remote Similarity	NPD8300	Approved
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.57	Remote Similarity	NPD8393	Approved
0.5694	Remote Similarity	NPD4279	Approved
0.5667	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7902	Approved
0.5618	Remote Similarity	NPD5363	Approved
0.5618	Remote Similarity	NPD1694	Approved
0.5612	Remote Similarity	NPD1700	Approved
0.5604	Remote Similarity	NPD5737	Approved
0.5604	Remote Similarity	NPD6672	Approved
0.5604	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6903	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