NPASS Compound

Structure

NPC145898 OpenBabel07101718242D 28 28 0 0 1 0 0 0 0 0999 V2000 2.1271 14.0021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0919 0.3289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1285 13.9498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6745 13.0588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2191 12.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7651 11.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3098 10.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8558 9.5994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4004 8.7608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9464 7.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4911 7.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0371 6.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5817 5.3014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1277 4.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6724 3.5717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2184 2.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7630 1.8421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5743 -0.4158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 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 5 1 0 0 0 0 4 26 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 2 1 6 0 0 0 23 27 1 0 0 0 0 24 3 1 1 0 0 0 24 28 1 0 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.29
Volume:	439.719
LogP:	5.458
LogD:	3.886
LogS:	-4.892
# Rotatable Bonds:	15
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	4.032
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	3.234087853343226e-05
Pgp-inhibitor:	0.662
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.372
Plasma Protein Binding (PPB):	94.32208251953125%
Volume Distribution (VD):	0.665
Pgp-substrate:	2.4993133544921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.745
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.986
CYP3A4-substrate:	0.397

ADMET: Excretion

Clearance (CL):	5.201
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.932
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.677
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.346
Skin Sensitization:	0.969
Carcinogencity:	0.298
Eye Corrosion:	0.75
Eye Irritation:	0.248
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC145898

Natural Product ID:	NPC145898
*Common Name:**	Epiplakinic Acid F Methyl Ester
IUPAC Name:	methyl 2-[(3S,5R)-5-[(9E,11E,13E)-hexadeca-9,11,13-trienyl]-3,5-dimethyldioxolan-3-yl]acetate
Synonyms:	epiplakinic acid F methyl ester
Standard InCHIKey:	KQFXTDFWOPMDIE-MWCMNJBHSA-N
Standard InCHI:	InChI=1S/C24H40O4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(2)21-24(3,28-27-23)20-22(25)26-4/h6-11H,5,12-21H2,1-4H3/b7-6+,9-8+,11-10+/t23-,24-/m1/s1
SMILES:	CC/C=C/C=C/C=C/CCCCCCCC[C@@]1(C)OO[C@](C1)(C)CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270649
PubChem CID:	49831403
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid 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
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277739]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[12762801]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	Puerto Rican	n.a.	PMID[20923180]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277322]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882424]
NPO22559	Plakortis halichondrioides	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	4
Others	2

Activity Type	# Activity
Cell Line	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	92.0	%	PMID[468104]
NPT1383	Cell Line	A2058	Homo sapiens	Activity	=	86.0	%	PMID[468104]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	10000.0	nM	PMID[468104]
NPT1383	Cell Line	A2058	Homo sapiens	IC50	>	10000.0	nM	PMID[468104]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.0	ug.mL-1	PMID[468104]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	IC50	=	62.0	ug.mL-1	PMID[468104]

☑ 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 NPC145898 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	198
0.1-0.2	1296
0.2-0.3	6279
0.3-0.4	15424
0.4-0.5	11713
0.5-0.6	6291
0.6-0.7	1409
0.7-0.8	84
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC120776
0.9189	High Similarity	NPC240170
0.8125	Intermediate Similarity	NPC469920
0.8052	Intermediate Similarity	NPC330016
0.8028	Intermediate Similarity	NPC469922
0.7922	Intermediate Similarity	NPC167145
0.7848	Intermediate Similarity	NPC239127
0.7765	Intermediate Similarity	NPC477994
0.7765	Intermediate Similarity	NPC477993
0.7722	Intermediate Similarity	NPC255060
0.7692	Intermediate Similarity	NPC326024
0.7674	Intermediate Similarity	NPC477959
0.7625	Intermediate Similarity	NPC469514
0.7625	Intermediate Similarity	NPC474447
0.7561	Intermediate Similarity	NPC263574
0.7561	Intermediate Similarity	NPC469747
0.7553	Intermediate Similarity	NPC474112
0.7531	Intermediate Similarity	NPC476325
0.7531	Intermediate Similarity	NPC476264
0.75	Intermediate Similarity	NPC256902
0.75	Intermediate Similarity	NPC118193
0.7471	Intermediate Similarity	NPC86005
0.7468	Intermediate Similarity	NPC238425
0.7468	Intermediate Similarity	NPC472018
0.7468	Intermediate Similarity	NPC474543
0.7436	Intermediate Similarity	NPC69462
0.7416	Intermediate Similarity	NPC313670
0.7412	Intermediate Similarity	NPC170377
0.7381	Intermediate Similarity	NPC207188
0.7375	Intermediate Similarity	NPC474551
0.7356	Intermediate Similarity	NPC475753
0.7317	Intermediate Similarity	NPC281296
0.7312	Intermediate Similarity	NPC47834
0.7308	Intermediate Similarity	NPC107130
0.7297	Intermediate Similarity	NPC469923
0.7273	Intermediate Similarity	NPC471739
0.7241	Intermediate Similarity	NPC99395
0.7241	Intermediate Similarity	NPC197903
0.7229	Intermediate Similarity	NPC121200
0.7229	Intermediate Similarity	NPC218817
0.7229	Intermediate Similarity	NPC11796
0.7222	Intermediate Similarity	NPC475748
0.7215	Intermediate Similarity	NPC472017
0.7215	Intermediate Similarity	NPC475310
0.7209	Intermediate Similarity	NPC69469
0.7209	Intermediate Similarity	NPC11620
0.7209	Intermediate Similarity	NPC475989
0.7209	Intermediate Similarity	NPC272814
0.7195	Intermediate Similarity	NPC266119
0.7183	Intermediate Similarity	NPC228473
0.7176	Intermediate Similarity	NPC476988
0.7174	Intermediate Similarity	NPC140543
0.7174	Intermediate Similarity	NPC476267
0.7174	Intermediate Similarity	NPC5418
0.7162	Intermediate Similarity	NPC469921
0.7159	Intermediate Similarity	NPC70422
0.7159	Intermediate Similarity	NPC70555
0.7159	Intermediate Similarity	NPC164393
0.7159	Intermediate Similarity	NPC104961
0.7159	Intermediate Similarity	NPC284902
0.7143	Intermediate Similarity	NPC184463
0.7143	Intermediate Similarity	NPC308545
0.7143	Intermediate Similarity	NPC471740
0.7143	Intermediate Similarity	NPC82488
0.7143	Intermediate Similarity	NPC20713
0.7111	Intermediate Similarity	NPC307411
0.7111	Intermediate Similarity	NPC166919
0.7111	Intermediate Similarity	NPC151770
0.7111	Intermediate Similarity	NPC97577
0.7083	Intermediate Similarity	NPC94487
0.7083	Intermediate Similarity	NPC116139
0.7079	Intermediate Similarity	NPC475703
0.7079	Intermediate Similarity	NPC231889
0.7073	Intermediate Similarity	NPC471491
0.7073	Intermediate Similarity	NPC199445
0.7065	Intermediate Similarity	NPC476300
0.7059	Intermediate Similarity	NPC474510
0.7059	Intermediate Similarity	NPC472948
0.7059	Intermediate Similarity	NPC474981
0.7053	Intermediate Similarity	NPC470188
0.7045	Intermediate Similarity	NPC475206
0.7045	Intermediate Similarity	NPC137033
0.7045	Intermediate Similarity	NPC215364
0.7041	Intermediate Similarity	NPC471143
0.7041	Intermediate Similarity	NPC477510
0.7033	Intermediate Similarity	NPC51653
0.7033	Intermediate Similarity	NPC51004
0.7033	Intermediate Similarity	NPC474761
0.7033	Intermediate Similarity	NPC478004
0.7033	Intermediate Similarity	NPC476004
0.7033	Intermediate Similarity	NPC478003
0.7033	Intermediate Similarity	NPC158388
0.7011	Intermediate Similarity	NPC318468
0.701	Intermediate Similarity	NPC474820
0.701	Intermediate Similarity	NPC475978
0.701	Intermediate Similarity	NPC66110
0.7	Intermediate Similarity	NPC469631
0.7	Intermediate Similarity	NPC475906
0.7	Intermediate Similarity	NPC471047
0.7	Intermediate Similarity	NPC201046
0.7	Intermediate Similarity	NPC469653
0.7	Intermediate Similarity	NPC469628
0.7	Intermediate Similarity	NPC202672
0.6989	Remote Similarity	NPC476716
0.6989	Remote Similarity	NPC471147
0.6988	Remote Similarity	NPC476987
0.6988	Remote Similarity	NPC152754
0.6988	Remote Similarity	NPC59602
0.6979	Remote Similarity	NPC469871
0.6979	Remote Similarity	NPC469870
0.6977	Remote Similarity	NPC14044
0.6977	Remote Similarity	NPC475481
0.6977	Remote Similarity	NPC79277
0.6977	Remote Similarity	NPC286229
0.6977	Remote Similarity	NPC117960
0.6977	Remote Similarity	NPC172309
0.6966	Remote Similarity	NPC475491
0.6966	Remote Similarity	NPC122502
0.6966	Remote Similarity	NPC469626
0.6966	Remote Similarity	NPC50637
0.6966	Remote Similarity	NPC469676
0.6957	Remote Similarity	NPC472705
0.6957	Remote Similarity	NPC36491
0.6957	Remote Similarity	NPC207641
0.6957	Remote Similarity	NPC30515
0.6957	Remote Similarity	NPC233437
0.6947	Remote Similarity	NPC40812
0.6941	Remote Similarity	NPC113363
0.6941	Remote Similarity	NPC28319
0.6923	Remote Similarity	NPC154728
0.6923	Remote Similarity	NPC304665
0.6923	Remote Similarity	NPC126899
0.6915	Remote Similarity	NPC107476
0.6915	Remote Similarity	NPC474947
0.6915	Remote Similarity	NPC36954
0.6915	Remote Similarity	NPC475659
0.6914	Remote Similarity	NPC320119
0.6907	Remote Similarity	NPC474742
0.6907	Remote Similarity	NPC472753
0.6907	Remote Similarity	NPC62670
0.6907	Remote Similarity	NPC47880
0.6901	Remote Similarity	NPC309606
0.6901	Remote Similarity	NPC139545
0.6901	Remote Similarity	NPC39633
0.6889	Remote Similarity	NPC179659
0.6889	Remote Similarity	NPC248602
0.6882	Remote Similarity	NPC478037
0.6882	Remote Similarity	NPC478036
0.6882	Remote Similarity	NPC475912
0.6882	Remote Similarity	NPC212486
0.6882	Remote Similarity	NPC477615
0.6875	Remote Similarity	NPC308567
0.6875	Remote Similarity	NPC244411
0.6875	Remote Similarity	NPC261377
0.6875	Remote Similarity	NPC187761
0.6875	Remote Similarity	NPC317583
0.6875	Remote Similarity	NPC255592
0.6875	Remote Similarity	NPC199557
0.6875	Remote Similarity	NPC83895
0.6867	Remote Similarity	NPC60718
0.6867	Remote Similarity	NPC324762
0.6867	Remote Similarity	NPC217725
0.686	Remote Similarity	NPC103634
0.686	Remote Similarity	NPC200446
0.6854	Remote Similarity	NPC472686
0.6854	Remote Similarity	NPC50362
0.6854	Remote Similarity	NPC474369
0.6854	Remote Similarity	NPC319795
0.6854	Remote Similarity	NPC290329
0.6854	Remote Similarity	NPC38468
0.6854	Remote Similarity	NPC474547
0.6848	Remote Similarity	NPC329857
0.6848	Remote Similarity	NPC469718
0.6848	Remote Similarity	NPC253144
0.6848	Remote Similarity	NPC62815
0.6848	Remote Similarity	NPC312042
0.6842	Remote Similarity	NPC195645
0.6842	Remote Similarity	NPC476275
0.6842	Remote Similarity	NPC473859
0.6842	Remote Similarity	NPC125312
0.6842	Remote Similarity	NPC165332
0.6842	Remote Similarity	NPC476315
0.6842	Remote Similarity	NPC180722
0.6842	Remote Similarity	NPC174560
0.6837	Remote Similarity	NPC474747
0.6837	Remote Similarity	NPC475091
0.6837	Remote Similarity	NPC149371
0.6837	Remote Similarity	NPC478156
0.6837	Remote Similarity	NPC105725
0.6837	Remote Similarity	NPC49393
0.6837	Remote Similarity	NPC472754
0.6829	Remote Similarity	NPC470237
0.6818	Remote Similarity	NPC250315
0.6818	Remote Similarity	NPC474472
0.6818	Remote Similarity	NPC475842
0.6818	Remote Similarity	NPC257358
0.6818	Remote Similarity	NPC475947
0.6813	Remote Similarity	NPC474471
0.6813	Remote Similarity	NPC227379
0.6809	Remote Similarity	NPC473316

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 NPC145898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1901
0.2-0.3	4197
0.3-0.4	1961
0.4-0.5	607
0.5-0.6	271
0.6-0.7	35
0.7-0.8	5
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
0.7333	Intermediate Similarity	NPD7983	Approved
0.7253	Intermediate Similarity	NPD5779	Approved
0.7253	Intermediate Similarity	NPD5778	Approved
0.7111	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6101	Approved
0.6977	Remote Similarity	NPD5369	Approved
0.6957	Remote Similarity	NPD6411	Approved
0.6897	Remote Similarity	NPD6435	Approved
0.686	Remote Similarity	NPD5368	Approved
0.6854	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7839	Suspended
0.6778	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.662	Remote Similarity	NPD29	Approved
0.662	Remote Similarity	NPD28	Approved
0.6517	Remote Similarity	NPD4269	Approved
0.6517	Remote Similarity	NPD4270	Approved
0.65	Remote Similarity	NPD7331	Phase 2
0.6458	Remote Similarity	NPD5282	Discontinued
0.6444	Remote Similarity	NPD7154	Phase 3
0.642	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1695	Approved
0.6351	Remote Similarity	NPD3194	Approved
0.6351	Remote Similarity	NPD3195	Phase 2
0.6351	Remote Similarity	NPD3196	Approved
0.6351	Remote Similarity	NPD4266	Approved
0.6344	Remote Similarity	NPD4251	Approved
0.6344	Remote Similarity	NPD4250	Approved
0.6304	Remote Similarity	NPD5363	Approved
0.6292	Remote Similarity	NPD4819	Approved
0.6292	Remote Similarity	NPD4822	Approved
0.6292	Remote Similarity	NPD4821	Approved
0.6292	Remote Similarity	NPD4252	Approved
0.6292	Remote Similarity	NPD4820	Approved
0.6264	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3732	Approved
0.6237	Remote Similarity	NPD4249	Approved
0.6216	Remote Similarity	NPD3172	Approved
0.6173	Remote Similarity	NPD7341	Phase 2
0.6154	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD7838	Discovery
0.6146	Remote Similarity	NPD6698	Approved
0.6146	Remote Similarity	NPD46	Approved
0.6146	Remote Similarity	NPD5785	Approved
0.6146	Remote Similarity	NPD5207	Approved
0.6111	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD8513	Phase 3
0.6106	Remote Similarity	NPD8515	Approved
0.6106	Remote Similarity	NPD8517	Approved
0.6106	Remote Similarity	NPD8516	Approved
0.6082	Remote Similarity	NPD5694	Approved
0.6082	Remote Similarity	NPD6050	Approved
0.6067	Remote Similarity	NPD4271	Approved
0.6067	Remote Similarity	NPD4268	Approved
0.6049	Remote Similarity	NPD3197	Phase 1
0.6	Remote Similarity	NPD5048	Discontinued
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD3573	Approved
0.5979	Remote Similarity	NPD5692	Phase 3
0.5978	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6672	Approved
0.5938	Remote Similarity	NPD5737	Approved
0.5926	Remote Similarity	NPD6371	Approved
0.5918	Remote Similarity	NPD5284	Approved
0.5918	Remote Similarity	NPD5281	Approved
0.5915	Remote Similarity	NPD3174	Discontinued
0.59	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6684	Approved
0.5895	Remote Similarity	NPD6422	Discontinued
0.5895	Remote Similarity	NPD5330	Approved
0.5895	Remote Similarity	NPD6098	Approved
0.5895	Remote Similarity	NPD7521	Approved
0.5895	Remote Similarity	NPD6409	Approved
0.5895	Remote Similarity	NPD7146	Approved
0.5895	Remote Similarity	NPD7334	Approved
0.5876	Remote Similarity	NPD6904	Approved
0.5876	Remote Similarity	NPD5370	Suspended
0.5876	Remote Similarity	NPD6080	Approved
0.5876	Remote Similarity	NPD6673	Approved
0.5875	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8074	Phase 3
0.5818	Remote Similarity	NPD6053	Discontinued
0.5812	Remote Similarity	NPD7492	Approved
0.5812	Remote Similarity	NPD8340	Approved
0.5812	Remote Similarity	NPD8299	Approved
0.5812	Remote Similarity	NPD8341	Approved
0.5812	Remote Similarity	NPD8342	Approved
0.5806	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1694	Approved
0.5784	Remote Similarity	NPD6083	Phase 2
0.5784	Remote Similarity	NPD6084	Phase 2
0.5783	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD4756	Discovery
0.5773	Remote Similarity	NPD6903	Approved
0.5773	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6616	Approved
0.5763	Remote Similarity	NPD8451	Approved
0.5758	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD5343	Approved
0.5745	Remote Similarity	NPD5331	Approved
0.5745	Remote Similarity	NPD5332	Approved
0.5743	Remote Similarity	NPD5695	Phase 3
0.5741	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6881	Approved
0.5741	Remote Similarity	NPD6899	Approved
0.5739	Remote Similarity	NPD6054	Approved
0.5739	Remote Similarity	NPD6319	Approved
0.5728	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD7128	Approved
0.5701	Remote Similarity	NPD6675	Approved
0.5701	Remote Similarity	NPD5739	Approved
0.57	Remote Similarity	NPD6399	Phase 3
0.5699	Remote Similarity	NPD4790	Discontinued
0.569	Remote Similarity	NPD8444	Approved
0.5686	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3173	Approved
0.5673	Remote Similarity	NPD6648	Approved
0.5667	Remote Similarity	NPD7736	Approved
0.5663	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5697	Approved
0.5648	Remote Similarity	NPD6685	Approved
0.5641	Remote Similarity	NPD6370	Approved
0.5636	Remote Similarity	NPD7102	Approved
0.5636	Remote Similarity	NPD6883	Approved
0.5636	Remote Similarity	NPD7290	Approved
0.5625	Remote Similarity	NPD4632	Approved
0.5612	Remote Similarity	NPD5208	Approved
0.5603	Remote Similarity	NPD6059	Approved
0.56	Remote Similarity	NPD5693	Phase 1

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