NPASS Compound

Structure

NPC76844 OpenBabel07101719252D 25 25 0 0 0 0 0 0 0 0999 V2000 -10.9482 7.6050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3549 6.6915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7671 5.8825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7726 5.9870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1848 5.1780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1903 5.2825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6025 4.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6080 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0202 3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0257 3.8735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4379 3.0645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4434 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8556 2.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8611 2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2733 1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 -1.5878 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 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 20 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 21 2 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.28
Volume:	398.973
LogP:	8.16
LogD:	3.838
LogS:	-6.519
# Rotatable Bonds:	17
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	2.21
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.861
MDCK Permeability:	2.0743960703839548e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.8
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.35050201416016%
Volume Distribution (VD):	1.768
Pgp-substrate:	0.5569674372673035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.288
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.435
CYP2C19-substrate:	0.13
CYP2C9-inhibitor:	0.261
CYP2C9-substrate:	0.995
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.213
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	2.564
Half-life (T1/2):	0.434

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.751
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.867
Carcinogencity:	0.075
Eye Corrosion:	0.368
Eye Irritation:	0.724
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC76844

Natural Product ID:	NPC76844
*Common Name:**	Plakorsin B
IUPAC Name:	2-(5-hexadecylfuran-2-yl)acetic acid
Synonyms:
Standard InCHIKey:	MYKNDMTYMCTYAG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H38O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-17-18-21(25-20)19-22(23)24/h17-18H,2-16,19H2,1H3,(H,23,24)
SMILES:	CCCCCCCCCCCCCCCCc1ccc(o1)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478746
PubChem CID:	10473105
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0001989] Heterocyclic fatty acids [CHEMONTID:0001528] Furanoid fatty acids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.28	ug.mL-1	PMID[484294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.43	ug.mL-1	PMID[484294]

☑ 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 NPC76844 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	253
0.1-0.2	2053
0.2-0.3	5653
0.3-0.4	11524
0.4-0.5	7778
0.5-0.6	8912
0.6-0.7	6088
0.7-0.8	414
0.8-0.85	13
0.85-0.9	4
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC11821
0.8957	High Similarity	NPC254958
0.8957	High Similarity	NPC291619
0.8783	High Similarity	NPC476014
0.8783	High Similarity	NPC476031
0.8621	High Similarity	NPC474987
0.8393	Intermediate Similarity	NPC42471
0.8319	Intermediate Similarity	NPC187547
0.8319	Intermediate Similarity	NPC21831
0.8291	Intermediate Similarity	NPC292036
0.8217	Intermediate Similarity	NPC159786
0.8083	Intermediate Similarity	NPC144745
0.8083	Intermediate Similarity	NPC208906
0.8065	Intermediate Similarity	NPC118853
0.8056	Intermediate Similarity	NPC233791
0.8049	Intermediate Similarity	NPC270807
0.8049	Intermediate Similarity	NPC174915
0.8047	Intermediate Similarity	NPC136340
0.7951	Intermediate Similarity	NPC244862
0.7951	Intermediate Similarity	NPC67345
0.7946	Intermediate Similarity	NPC156768
0.7934	Intermediate Similarity	NPC312525
0.7934	Intermediate Similarity	NPC217180
0.7917	Intermediate Similarity	NPC205523
0.7913	Intermediate Similarity	NPC298087
0.7903	Intermediate Similarity	NPC323118
0.7863	Intermediate Similarity	NPC106247
0.7851	Intermediate Similarity	NPC328451
0.784	Intermediate Similarity	NPC311219
0.7836	Intermediate Similarity	NPC107571
0.782	Intermediate Similarity	NPC473268
0.7805	Intermediate Similarity	NPC473969
0.7795	Intermediate Similarity	NPC329694
0.7795	Intermediate Similarity	NPC474260
0.7795	Intermediate Similarity	NPC329922
0.7795	Intermediate Similarity	NPC81912
0.7787	Intermediate Similarity	NPC227660
0.776	Intermediate Similarity	NPC272487
0.7737	Intermediate Similarity	NPC254198
0.7734	Intermediate Similarity	NPC474830
0.7717	Intermediate Similarity	NPC71274
0.7717	Intermediate Similarity	NPC474829
0.7717	Intermediate Similarity	NPC75557
0.771	Intermediate Similarity	NPC473982
0.7698	Intermediate Similarity	NPC476351
0.7698	Intermediate Similarity	NPC104924
0.7687	Intermediate Similarity	NPC170604
0.7687	Intermediate Similarity	NPC215109
0.768	Intermediate Similarity	NPC1848
0.768	Intermediate Similarity	NPC79557
0.7674	Intermediate Similarity	NPC474279
0.7674	Intermediate Similarity	NPC474438
0.7667	Intermediate Similarity	NPC26157
0.7667	Intermediate Similarity	NPC1811
0.7656	Intermediate Similarity	NPC216810
0.7652	Intermediate Similarity	NPC474407
0.7652	Intermediate Similarity	NPC474426
0.7652	Intermediate Similarity	NPC474425
0.7642	Intermediate Similarity	NPC131801
0.7638	Intermediate Similarity	NPC243269
0.7619	Intermediate Similarity	NPC263870
0.7612	Intermediate Similarity	NPC303217
0.76	Intermediate Similarity	NPC230951
0.76	Intermediate Similarity	NPC474874
0.76	Intermediate Similarity	NPC470092
0.7597	Intermediate Similarity	NPC476016
0.7589	Intermediate Similarity	NPC146316
0.7583	Intermediate Similarity	NPC105249
0.7578	Intermediate Similarity	NPC221798
0.7576	Intermediate Similarity	NPC15083
0.7574	Intermediate Similarity	NPC202260
0.7574	Intermediate Similarity	NPC474615
0.7561	Intermediate Similarity	NPC470860
0.7561	Intermediate Similarity	NPC45536
0.7559	Intermediate Similarity	NPC475818
0.7557	Intermediate Similarity	NPC238309
0.754	Intermediate Similarity	NPC474136
0.752	Intermediate Similarity	NPC244293
0.7518	Intermediate Similarity	NPC282973
0.7518	Intermediate Similarity	NPC148374
0.7518	Intermediate Similarity	NPC308799
0.75	Intermediate Similarity	NPC65735
0.75	Intermediate Similarity	NPC229387
0.75	Intermediate Similarity	NPC183348
0.75	Intermediate Similarity	NPC217423
0.75	Intermediate Similarity	NPC282230
0.75	Intermediate Similarity	NPC188377
0.75	Intermediate Similarity	NPC475092
0.75	Intermediate Similarity	NPC472376
0.748	Intermediate Similarity	NPC289911
0.748	Intermediate Similarity	NPC188907
0.748	Intermediate Similarity	NPC283284
0.748	Intermediate Similarity	NPC28054
0.7479	Intermediate Similarity	NPC471521
0.7479	Intermediate Similarity	NPC473356
0.7465	Intermediate Similarity	NPC113428
0.7465	Intermediate Similarity	NPC61284
0.7463	Intermediate Similarity	NPC477536
0.7462	Intermediate Similarity	NPC473355
0.7462	Intermediate Similarity	NPC471573
0.7462	Intermediate Similarity	NPC471501
0.7462	Intermediate Similarity	NPC471554
0.746	Intermediate Similarity	NPC474817
0.7459	Intermediate Similarity	NPC311987
0.7444	Intermediate Similarity	NPC196979
0.7444	Intermediate Similarity	NPC470977
0.7444	Intermediate Similarity	NPC470976
0.7444	Intermediate Similarity	NPC324488
0.7442	Intermediate Similarity	NPC193805
0.7442	Intermediate Similarity	NPC471559
0.744	Intermediate Similarity	NPC293424
0.7424	Intermediate Similarity	NPC66246
0.7424	Intermediate Similarity	NPC187907
0.7424	Intermediate Similarity	NPC170546
0.7424	Intermediate Similarity	NPC473019
0.7422	Intermediate Similarity	NPC69403
0.7422	Intermediate Similarity	NPC291189
0.7417	Intermediate Similarity	NPC177331
0.7395	Intermediate Similarity	NPC219969
0.7388	Intermediate Similarity	NPC470740
0.7385	Intermediate Similarity	NPC4164
0.7385	Intermediate Similarity	NPC138139
0.7385	Intermediate Similarity	NPC46536
0.7381	Intermediate Similarity	NPC54243
0.7381	Intermediate Similarity	NPC264976
0.7381	Intermediate Similarity	NPC4898
0.7381	Intermediate Similarity	NPC328459
0.7381	Intermediate Similarity	NPC90522
0.7377	Intermediate Similarity	NPC22678
0.7372	Intermediate Similarity	NPC477534
0.7368	Intermediate Similarity	NPC477645
0.7368	Intermediate Similarity	NPC17681
0.7364	Intermediate Similarity	NPC93730
0.736	Intermediate Similarity	NPC240664
0.7357	Intermediate Similarity	NPC22248
0.7353	Intermediate Similarity	NPC204592
0.7344	Intermediate Similarity	NPC473379
0.7344	Intermediate Similarity	NPC471549
0.7344	Intermediate Similarity	NPC477967
0.7339	Intermediate Similarity	NPC51345
0.7333	Intermediate Similarity	NPC287533
0.7328	Intermediate Similarity	NPC474476
0.7328	Intermediate Similarity	NPC83178
0.7328	Intermediate Similarity	NPC319140
0.7328	Intermediate Similarity	NPC95567
0.7328	Intermediate Similarity	NPC184391
0.7323	Intermediate Similarity	NPC72977
0.7323	Intermediate Similarity	NPC246214
0.7313	Intermediate Similarity	NPC45358
0.7313	Intermediate Similarity	NPC97740
0.7308	Intermediate Similarity	NPC473885
0.7308	Intermediate Similarity	NPC470162
0.7308	Intermediate Similarity	NPC470163
0.7308	Intermediate Similarity	NPC471074
0.7302	Intermediate Similarity	NPC206007
0.7302	Intermediate Similarity	NPC94637
0.7302	Intermediate Similarity	NPC243704
0.7302	Intermediate Similarity	NPC32298
0.7299	Intermediate Similarity	NPC307401
0.7299	Intermediate Similarity	NPC278832
0.7299	Intermediate Similarity	NPC64157
0.7293	Intermediate Similarity	NPC939
0.728	Intermediate Similarity	NPC128825
0.728	Intermediate Similarity	NPC33717
0.7279	Intermediate Similarity	NPC265793
0.7273	Intermediate Similarity	NPC259554
0.7273	Intermediate Similarity	NPC112706
0.7273	Intermediate Similarity	NPC329707
0.7273	Intermediate Similarity	NPC207294
0.7273	Intermediate Similarity	NPC234639
0.7273	Intermediate Similarity	NPC209111
0.7266	Intermediate Similarity	NPC473983
0.7266	Intermediate Similarity	NPC473988
0.7266	Intermediate Similarity	NPC201370
0.7265	Intermediate Similarity	NPC217226
0.726	Intermediate Similarity	NPC474378
0.726	Intermediate Similarity	NPC474219
0.7259	Intermediate Similarity	NPC470160
0.7254	Intermediate Similarity	NPC37488
0.7254	Intermediate Similarity	NPC10302
0.7254	Intermediate Similarity	NPC105381
0.7254	Intermediate Similarity	NPC195920
0.7252	Intermediate Similarity	NPC52035
0.7244	Intermediate Similarity	NPC35744
0.7244	Intermediate Similarity	NPC61779
0.7244	Intermediate Similarity	NPC137710
0.7241	Intermediate Similarity	NPC212257
0.7239	Intermediate Similarity	NPC327457
0.7239	Intermediate Similarity	NPC89133
0.7239	Intermediate Similarity	NPC86774
0.7234	Intermediate Similarity	NPC110305
0.723	Intermediate Similarity	NPC474542
0.7226	Intermediate Similarity	NPC66705
0.7226	Intermediate Similarity	NPC298900
0.7222	Intermediate Similarity	NPC45104
0.7222	Intermediate Similarity	NPC107482
0.7218	Intermediate Similarity	NPC2596
0.7214	Intermediate Similarity	NPC477535
0.7214	Intermediate Similarity	NPC477537
0.7203	Intermediate Similarity	NPC475864

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 NPC76844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	1054
0.2-0.3	2062
0.3-0.4	2840
0.4-0.5	1873
0.5-0.6	837
0.6-0.7	220
0.7-0.8	25
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
0.784	Intermediate Similarity	NPD9717	Approved
0.7615	Intermediate Similarity	NPD6832	Phase 2
0.7519	Intermediate Similarity	NPD1203	Approved
0.7445	Intermediate Similarity	NPD2344	Approved
0.7426	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD2313	Discontinued
0.7319	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD9493	Approved
0.7252	Intermediate Similarity	NPD2797	Approved
0.7239	Intermediate Similarity	NPD411	Approved
0.7234	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD9092	Discovery
0.7206	Intermediate Similarity	NPD447	Suspended
0.7197	Intermediate Similarity	NPD1019	Discontinued
0.7197	Intermediate Similarity	NPD5647	Approved
0.7197	Intermediate Similarity	NPD2798	Approved
0.7177	Intermediate Similarity	NPD1241	Discontinued
0.7111	Intermediate Similarity	NPD3268	Approved
0.7092	Intermediate Similarity	NPD1243	Approved
0.7077	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2346	Discontinued
0.705	Intermediate Similarity	NPD4308	Phase 3
0.7014	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD2935	Discontinued
0.6992	Remote Similarity	NPD6362	Approved
0.6972	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1933	Approved
0.695	Remote Similarity	NPD1471	Phase 3
0.6899	Remote Similarity	NPD1894	Discontinued
0.6899	Remote Similarity	NPD9545	Approved
0.6894	Remote Similarity	NPD1608	Approved
0.6894	Remote Similarity	NPD3972	Approved
0.6884	Remote Similarity	NPD4307	Phase 2
0.6879	Remote Similarity	NPD1551	Phase 2
0.6866	Remote Similarity	NPD3266	Approved
0.6866	Remote Similarity	NPD3267	Approved
0.6861	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD9264	Approved
0.6829	Remote Similarity	NPD9263	Approved
0.6829	Remote Similarity	NPD9267	Approved
0.6828	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7819	Suspended
0.6806	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3750	Approved
0.6806	Remote Similarity	NPD4628	Phase 3
0.68	Remote Similarity	NPD7411	Suspended
0.68	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3749	Approved
0.6791	Remote Similarity	NPD1876	Approved
0.6774	Remote Similarity	NPD74	Approved
0.6774	Remote Similarity	NPD9266	Approved
0.6767	Remote Similarity	NPD1481	Phase 2
0.6763	Remote Similarity	NPD1240	Approved
0.6761	Remote Similarity	NPD2796	Approved
0.6759	Remote Similarity	NPD2354	Approved
0.6757	Remote Similarity	NPD920	Approved
0.6757	Remote Similarity	NPD5403	Approved
0.6748	Remote Similarity	NPD3134	Approved
0.6741	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5401	Approved
0.6735	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6599	Discontinued
0.6714	Remote Similarity	NPD6355	Discontinued
0.6712	Remote Similarity	NPD7440	Discontinued
0.6692	Remote Similarity	NPD1535	Discovery
0.6691	Remote Similarity	NPD6233	Phase 2
0.669	Remote Similarity	NPD3748	Approved
0.669	Remote Similarity	NPD7033	Discontinued
0.6689	Remote Similarity	NPD6273	Approved
0.6688	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD3225	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD9697	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6643	Remote Similarity	NPD3142	Approved
0.6643	Remote Similarity	NPD3140	Approved
0.6639	Remote Similarity	NPD9261	Approved
0.6624	Remote Similarity	NPD6808	Phase 2
0.6623	Remote Similarity	NPD7768	Phase 2
0.6622	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3764	Approved
0.6619	Remote Similarity	NPD6798	Discontinued
0.6617	Remote Similarity	NPD3496	Discontinued
0.6597	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2353	Approved
0.6597	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD2614	Approved
0.6589	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5049	Phase 3
0.6575	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4062	Phase 3
0.6571	Remote Similarity	NPD8032	Phase 2
0.6567	Remote Similarity	NPD422	Phase 1
0.6562	Remote Similarity	NPD5535	Approved
0.656	Remote Similarity	NPD1358	Approved
0.6552	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6653	Approved
0.6536	Remote Similarity	NPD6801	Discontinued
0.6536	Remote Similarity	NPD6279	Approved
0.6536	Remote Similarity	NPD6280	Approved
0.6531	Remote Similarity	NPD3887	Approved
0.6522	Remote Similarity	NPD454	Approved
0.6516	Remote Similarity	NPD3882	Suspended
0.6512	Remote Similarity	NPD9069	Phase 1
0.651	Remote Similarity	NPD4661	Approved
0.651	Remote Similarity	NPD4662	Approved
0.6508	Remote Similarity	NPD2182	Approved
0.6507	Remote Similarity	NPD2800	Approved
0.6493	Remote Similarity	NPD3847	Discontinued
0.6483	Remote Similarity	NPD6004	Phase 3
0.6483	Remote Similarity	NPD6005	Phase 3
0.6483	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6002	Phase 3
0.6483	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5585	Approved
0.6463	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7003	Approved
0.6462	Remote Similarity	NPD9281	Approved
0.646	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1510	Phase 2
0.6452	Remote Similarity	NPD5402	Approved
0.6452	Remote Similarity	NPD3817	Phase 2
0.6447	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD919	Approved
0.6429	Remote Similarity	NPD7095	Approved
0.6429	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6844	Discontinued
0.6424	Remote Similarity	NPD3869	Phase 3
0.6424	Remote Similarity	NPD3873	Phase 3
0.6423	Remote Similarity	NPD1283	Approved
0.6414	Remote Similarity	NPD4477	Approved
0.6414	Remote Similarity	NPD4476	Approved
0.6407	Remote Similarity	NPD8434	Phase 2
0.6405	Remote Similarity	NPD6585	Discontinued
0.6402	Remote Similarity	NPD6559	Discontinued
0.64	Remote Similarity	NPD2532	Approved
0.64	Remote Similarity	NPD2534	Approved
0.64	Remote Similarity	NPD2533	Approved
0.6393	Remote Similarity	NPD1238	Approved
0.6378	Remote Similarity	NPD2684	Approved
0.6378	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5889	Approved
0.6364	Remote Similarity	NPD5890	Approved
0.6364	Remote Similarity	NPD2366	Approved
0.6356	Remote Similarity	NPD9365	Approved
0.6346	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7458	Discontinued
0.6335	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1511	Approved
0.6333	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.632	Remote Similarity	NPD164	Approved
0.6316	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7843	Approved
0.6301	Remote Similarity	NPD5712	Approved
0.6299	Remote Similarity	NPD290	Approved
0.6296	Remote Similarity	NPD4626	Approved
0.629	Remote Similarity	NPD291	Approved
0.6288	Remote Similarity	NPD6671	Approved
0.6286	Remote Similarity	NPD9494	Approved
0.6284	Remote Similarity	NPD2654	Approved
0.6282	Remote Similarity	NPD5760	Phase 2
0.6282	Remote Similarity	NPD2801	Approved
0.6282	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5761	Phase 2
0.6273	Remote Similarity	NPD3926	Phase 2
0.6271	Remote Similarity	NPD9256	Approved
0.6271	Remote Similarity	NPD9258	Approved
0.6268	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD1296	Phase 2
0.6266	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD1164	Approved
0.6259	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1512	Approved
0.625	Remote Similarity	NPD4622	Approved
0.625	Remote Similarity	NPD1184	Approved
0.625	Remote Similarity	NPD4618	Approved
0.6242	Remote Similarity	NPD4110	Phase 3
0.6242	Remote Similarity	NPD7318	Phase 3
0.6242	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD4359	Approved
0.6231	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5691	Approved
0.622	Remote Similarity	NPD7286	Phase 2
0.6218	Remote Similarity	NPD1934	Approved
0.6218	Remote Similarity	NPD7577	Discontinued
0.6216	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5958	Discontinued

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