NPASS Compound

Structure

NPC476014 OpenBabel07101719252D 27 27 0 0 0 0 0 0 0 0999 V2000 -16.1465 -4.4463 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 -7.6025 -4.4735 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 -8.1903 -5.2825 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 -9.1848 -5.1780 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 -9.7726 -5.9870 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 -10.7671 -5.8825 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 -11.7617 -5.7779 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 -12.7562 -5.6734 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 -13.3440 -6.4824 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 -0.2788 -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 -14.3385 -6.3779 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 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7452 -5.4644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.1574 -4.6553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.7397 -5.3598 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 26 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 3 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 20 23 2 0 0 0 0 21 24 1 0 0 0 0 22 27 1 0 0 0 0 23 27 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.28
Volume:	428.292
LogP:	7.494
LogD:	4.47
LogS:	-6.78
# Rotatable Bonds:	17
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.18
Synthetic Accessibility Score:	2.456
Fsp3:	0.708
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:	-4.828
MDCK Permeability:	1.2865014468843583e-05
Pgp-inhibitor:	0.36
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	96.3405990600586%
Volume Distribution (VD):	2.932
Pgp-substrate:	0.8501262664794922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.508
CYP1A2-substrate:	0.194
CYP2C19-inhibitor:	0.7
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.571
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.332
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	6.155
Half-life (T1/2):	0.268

ADMET: Toxicity

hERG Blockers:	0.614
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.413
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.236
Skin Sensitization:	0.963
Carcinogencity:	0.104
Eye Corrosion:	0.463
Eye Irritation:	0.819
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC476014

Natural Product ID:	NPC476014
*Common Name:**	Methyl 19-(Furan-2-Yl)Nonadec-5-Ynoate
IUPAC Name:	methyl 19-(furan-2-yl)nonadec-5-ynoate
Synonyms:
Standard InCHIKey:	AQNHEYASQIWORC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H38O3/c1-26-24(25)21-17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-19-23-20-18-22-27-23/h18,20,22H,2-10,12,14-17,19,21H2,1H3
SMILES:	COC(=O)CCCC#CCCCCCCCCCCCCCc1ccco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521615
PubChem CID:	11566977
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters [CHEMONTID:0003417] Fatty acid 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
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16441071]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[16441071]
NPO6522	Polyalthia evecta	Species	Annonaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	3.1	ug.mL-1	PMID[453370]

☑ 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 NPC476014 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	275
0.1-0.2	2301
0.2-0.3	6910
0.3-0.4	11582
0.4-0.5	7776
0.5-0.6	10471
0.6-0.7	3049
0.7-0.8	303
0.8-0.85	16
0.85-0.9	8
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476031
0.964	High Similarity	NPC254958
0.964	High Similarity	NPC291619
0.9286	High Similarity	NPC474987
0.9074	High Similarity	NPC42471
0.8783	High Similarity	NPC76844
0.8696	High Similarity	NPC11821
0.8611	High Similarity	NPC156768
0.8547	High Similarity	NPC217180
0.8547	High Similarity	NPC312525
0.8534	High Similarity	NPC205523
0.8475	Intermediate Similarity	NPC21831
0.8475	Intermediate Similarity	NPC187547
0.8448	Intermediate Similarity	NPC292036
0.8403	Intermediate Similarity	NPC473969
0.839	Intermediate Similarity	NPC227660
0.8241	Intermediate Similarity	NPC146316
0.8235	Intermediate Similarity	NPC208906
0.8235	Intermediate Similarity	NPC144745
0.8235	Intermediate Similarity	NPC131801
0.8211	Intermediate Similarity	NPC118853
0.819	Intermediate Similarity	NPC105249
0.8103	Intermediate Similarity	NPC229387
0.8087	Intermediate Similarity	NPC473356
0.8087	Intermediate Similarity	NPC471521
0.8067	Intermediate Similarity	NPC28054
0.8065	Intermediate Similarity	NPC65735
0.8065	Intermediate Similarity	NPC188377
0.8056	Intermediate Similarity	NPC233791
0.8047	Intermediate Similarity	NPC475092
0.8	Intermediate Similarity	NPC71274
0.8	Intermediate Similarity	NPC219969
0.8	Intermediate Similarity	NPC75557
0.7984	Intermediate Similarity	NPC476351
0.7966	Intermediate Similarity	NPC22678
0.7955	Intermediate Similarity	NPC215109
0.7955	Intermediate Similarity	NPC170604
0.7951	Intermediate Similarity	NPC244862
0.7951	Intermediate Similarity	NPC67345
0.7951	Intermediate Similarity	NPC4898
0.7937	Intermediate Similarity	NPC474260
0.7937	Intermediate Similarity	NPC81912
0.7937	Intermediate Similarity	NPC329694
0.7937	Intermediate Similarity	NPC329922
0.7913	Intermediate Similarity	NPC298087
0.7876	Intermediate Similarity	NPC217226
0.7874	Intermediate Similarity	NPC474830
0.7869	Intermediate Similarity	NPC243704
0.7869	Intermediate Similarity	NPC206007
0.7857	Intermediate Similarity	NPC473885
0.7857	Intermediate Similarity	NPC474829
0.7857	Intermediate Similarity	NPC471074
0.7846	Intermediate Similarity	NPC473982
0.7823	Intermediate Similarity	NPC1848
0.7823	Intermediate Similarity	NPC474136
0.782	Intermediate Similarity	NPC307401
0.7815	Intermediate Similarity	NPC1811
0.7815	Intermediate Similarity	NPC26157
0.7812	Intermediate Similarity	NPC474279
0.7812	Intermediate Similarity	NPC474438
0.7805	Intermediate Similarity	NPC137710
0.7795	Intermediate Similarity	NPC216810
0.7778	Intermediate Similarity	NPC243269
0.7769	Intermediate Similarity	NPC136340
0.776	Intermediate Similarity	NPC283284
0.776	Intermediate Similarity	NPC289911
0.7734	Intermediate Similarity	NPC137570
0.7734	Intermediate Similarity	NPC476016
0.7734	Intermediate Similarity	NPC141059
0.7724	Intermediate Similarity	NPC293424
0.771	Intermediate Similarity	NPC15083
0.7705	Intermediate Similarity	NPC45536
0.7704	Intermediate Similarity	NPC202260
0.7698	Intermediate Similarity	NPC475818
0.7698	Intermediate Similarity	NPC16922
0.768	Intermediate Similarity	NPC97566
0.7656	Intermediate Similarity	NPC83301
0.7652	Intermediate Similarity	NPC293253
0.7647	Intermediate Similarity	NPC148374
0.7634	Intermediate Similarity	NPC183348
0.7634	Intermediate Similarity	NPC282230
0.7619	Intermediate Similarity	NPC272487
0.7619	Intermediate Similarity	NPC174915
0.7619	Intermediate Similarity	NPC270807
0.7615	Intermediate Similarity	NPC59502
0.7603	Intermediate Similarity	NPC311987
0.76	Intermediate Similarity	NPC474817
0.7597	Intermediate Similarity	NPC471501
0.7597	Intermediate Similarity	NPC471554
0.7597	Intermediate Similarity	NPC473355
0.7597	Intermediate Similarity	NPC471573
0.7594	Intermediate Similarity	NPC106247
0.7578	Intermediate Similarity	NPC179354
0.7578	Intermediate Similarity	NPC471559
0.7576	Intermediate Similarity	NPC196979
0.7576	Intermediate Similarity	NPC470976
0.7576	Intermediate Similarity	NPC470977
0.7576	Intermediate Similarity	NPC471817
0.7563	Intermediate Similarity	NPC177331
0.7561	Intermediate Similarity	NPC470860
0.7561	Intermediate Similarity	NPC79202
0.7561	Intermediate Similarity	NPC59035
0.7557	Intermediate Similarity	NPC170546
0.7557	Intermediate Similarity	NPC66246
0.7556	Intermediate Similarity	NPC473268
0.7541	Intermediate Similarity	NPC252004
0.7537	Intermediate Similarity	NPC159786
0.7519	Intermediate Similarity	NPC470740
0.7519	Intermediate Similarity	NPC138139
0.7519	Intermediate Similarity	NPC46536
0.7519	Intermediate Similarity	NPC74612
0.75	Intermediate Similarity	NPC477645
0.75	Intermediate Similarity	NPC17681
0.7481	Intermediate Similarity	NPC303217
0.7481	Intermediate Similarity	NPC208389
0.748	Intermediate Similarity	NPC317217
0.748	Intermediate Similarity	NPC477967
0.748	Intermediate Similarity	NPC150895
0.7462	Intermediate Similarity	NPC83178
0.7462	Intermediate Similarity	NPC319140
0.7462	Intermediate Similarity	NPC95567
0.7462	Intermediate Similarity	NPC184391
0.7444	Intermediate Similarity	NPC45358
0.7444	Intermediate Similarity	NPC97740
0.7442	Intermediate Similarity	NPC221798
0.7429	Intermediate Similarity	NPC218712
0.7429	Intermediate Similarity	NPC261733
0.7429	Intermediate Similarity	NPC307346
0.7429	Intermediate Similarity	NPC267004
0.7426	Intermediate Similarity	NPC64157
0.7426	Intermediate Similarity	NPC278832
0.7419	Intermediate Similarity	NPC328451
0.7417	Intermediate Similarity	NPC209111
0.7407	Intermediate Similarity	NPC265793
0.7405	Intermediate Similarity	NPC161322
0.7405	Intermediate Similarity	NPC112706
0.7405	Intermediate Similarity	NPC329707
0.7405	Intermediate Similarity	NPC207294
0.7402	Intermediate Similarity	NPC79557
0.7402	Intermediate Similarity	NPC115859
0.7394	Intermediate Similarity	NPC71821
0.7391	Intermediate Similarity	NPC282973
0.7391	Intermediate Similarity	NPC473983
0.7391	Intermediate Similarity	NPC201370
0.7388	Intermediate Similarity	NPC474425
0.7388	Intermediate Similarity	NPC474426
0.7388	Intermediate Similarity	NPC474407
0.7385	Intermediate Similarity	NPC470858
0.7385	Intermediate Similarity	NPC52035
0.7381	Intermediate Similarity	NPC244293
0.7376	Intermediate Similarity	NPC56731
0.7368	Intermediate Similarity	NPC89133
0.7368	Intermediate Similarity	NPC298190
0.7364	Intermediate Similarity	NPC477038
0.7364	Intermediate Similarity	NPC477965
0.7364	Intermediate Similarity	NPC141252
0.7364	Intermediate Similarity	NPC11799
0.736	Intermediate Similarity	NPC45104
0.736	Intermediate Similarity	NPC217423
0.736	Intermediate Similarity	NPC107482
0.7348	Intermediate Similarity	NPC50583
0.7344	Intermediate Similarity	NPC473379
0.7344	Intermediate Similarity	NPC471549
0.7344	Intermediate Similarity	NPC263870
0.7323	Intermediate Similarity	NPC246214
0.7323	Intermediate Similarity	NPC230951
0.7319	Intermediate Similarity	NPC474615
0.7319	Intermediate Similarity	NPC107571
0.7317	Intermediate Similarity	NPC53953
0.7302	Intermediate Similarity	NPC87466
0.7299	Intermediate Similarity	NPC286130
0.7295	Intermediate Similarity	NPC23332
0.7295	Intermediate Similarity	NPC57879
0.7295	Intermediate Similarity	NPC54626
0.7293	Intermediate Similarity	NPC21460
0.7293	Intermediate Similarity	NPC238309
0.7287	Intermediate Similarity	NPC291189
0.7287	Intermediate Similarity	NPC69403
0.728	Intermediate Similarity	NPC316062
0.7279	Intermediate Similarity	NPC14650
0.7279	Intermediate Similarity	NPC209858
0.7273	Intermediate Similarity	NPC259554
0.7273	Intermediate Similarity	NPC308799
0.7258	Intermediate Similarity	NPC210092
0.7254	Intermediate Similarity	NPC290038
0.7254	Intermediate Similarity	NPC195920
0.725	Intermediate Similarity	NPC157473
0.725	Intermediate Similarity	NPC151530
0.725	Intermediate Similarity	NPC140688
0.7246	Intermediate Similarity	NPC472376
0.7246	Intermediate Similarity	NPC130976
0.7241	Intermediate Similarity	NPC212257
0.7234	Intermediate Similarity	NPC22248
0.7231	Intermediate Similarity	NPC178382
0.7226	Intermediate Similarity	NPC146872
0.7222	Intermediate Similarity	NPC113428
0.7222	Intermediate Similarity	NPC469954
0.7222	Intermediate Similarity	NPC93666
0.7222	Intermediate Similarity	NPC61284
0.7213	Intermediate Similarity	NPC183648

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 NPC476014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	1146
0.2-0.3	2175
0.3-0.4	2875
0.4-0.5	1768
0.5-0.6	752
0.6-0.7	169
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7481	Intermediate Similarity	NPD6832	Phase 2
0.7459	Intermediate Similarity	NPD1241	Discontinued
0.7445	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD9092	Discovery
0.7121	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1019	Discontinued
0.7025	Intermediate Similarity	NPD3134	Approved
0.7023	Intermediate Similarity	NPD9717	Approved
0.6944	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3972	Approved
0.6884	Remote Similarity	NPD3142	Approved
0.6884	Remote Similarity	NPD3140	Approved
0.6871	Remote Similarity	NPD920	Approved
0.6853	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1358	Approved
0.6815	Remote Similarity	NPD5647	Approved
0.6809	Remote Similarity	NPD2799	Discontinued
0.6791	Remote Similarity	NPD1876	Approved
0.6774	Remote Similarity	NPD2182	Approved
0.6769	Remote Similarity	NPD9545	Approved
0.6769	Remote Similarity	NPD1894	Discontinued
0.6763	Remote Similarity	NPD4307	Phase 2
0.6759	Remote Similarity	NPD3887	Approved
0.6741	Remote Similarity	NPD3266	Approved
0.6741	Remote Similarity	NPD1203	Approved
0.6741	Remote Similarity	NPD2797	Approved
0.6741	Remote Similarity	NPD3267	Approved
0.6741	Remote Similarity	NPD6362	Approved
0.6739	Remote Similarity	NPD2313	Discontinued
0.6736	Remote Similarity	NPD1243	Approved
0.6718	Remote Similarity	NPD5585	Approved
0.6714	Remote Similarity	NPD1933	Approved
0.6713	Remote Similarity	NPD2344	Approved
0.6691	Remote Similarity	NPD2798	Approved
0.669	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD9697	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD6799	Approved
0.6643	Remote Similarity	NPD1551	Phase 2
0.6643	Remote Similarity	NPD2796	Approved
0.6619	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3268	Approved
0.6617	Remote Similarity	NPD3496	Discontinued
0.6615	Remote Similarity	NPD9493	Approved
0.6599	Remote Similarity	NPD7440	Discontinued
0.6597	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6005	Phase 3
0.6597	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2353	Approved
0.6597	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6004	Phase 3
0.6597	Remote Similarity	NPD1471	Phase 3
0.6597	Remote Similarity	NPD6002	Phase 3
0.6596	Remote Similarity	NPD6355	Discontinued
0.6577	Remote Similarity	NPD6273	Approved
0.6575	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3748	Approved
0.6573	Remote Similarity	NPD4308	Phase 3
0.6571	Remote Similarity	NPD8032	Phase 2
0.6562	Remote Similarity	NPD5535	Approved
0.6558	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1778	Approved
0.6538	Remote Similarity	NPD919	Approved
0.6533	Remote Similarity	NPD3869	Phase 3
0.6533	Remote Similarity	NPD3873	Phase 3
0.6531	Remote Similarity	NPD2309	Approved
0.6519	Remote Similarity	NPD1608	Approved
0.6512	Remote Similarity	NPD9069	Phase 1
0.65	Remote Similarity	NPD411	Approved
0.65	Remote Similarity	NPD6798	Discontinued
0.6483	Remote Similarity	NPD2346	Discontinued
0.6479	Remote Similarity	NPD4622	Approved
0.6479	Remote Similarity	NPD447	Suspended
0.6479	Remote Similarity	NPD4618	Approved
0.6471	Remote Similarity	NPD4359	Approved
0.6466	Remote Similarity	NPD5691	Approved
0.6454	Remote Similarity	NPD6233	Phase 2
0.6454	Remote Similarity	NPD4062	Phase 3
0.6452	Remote Similarity	NPD164	Approved
0.6429	Remote Similarity	NPD6279	Approved
0.6429	Remote Similarity	NPD6280	Approved
0.6424	Remote Similarity	NPD5403	Approved
0.6419	Remote Similarity	NPD2354	Approved
0.6415	Remote Similarity	NPD6808	Phase 2
0.6414	Remote Similarity	NPD2935	Discontinued
0.6405	Remote Similarity	NPD6599	Discontinued
0.6403	Remote Similarity	NPD454	Approved
0.6403	Remote Similarity	NPD9494	Approved
0.64	Remote Similarity	NPD5401	Approved
0.6397	Remote Similarity	NPD1481	Phase 2
0.6389	Remote Similarity	NPD5689	Approved
0.6389	Remote Similarity	NPD5688	Approved
0.6387	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7819	Suspended
0.6378	Remote Similarity	NPD2684	Approved
0.6364	Remote Similarity	NPD7411	Suspended
0.6358	Remote Similarity	NPD2186	Approved
0.6358	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD9365	Approved
0.6351	Remote Similarity	NPD3750	Approved
0.6351	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD2067	Discontinued
0.6324	Remote Similarity	NPD1281	Approved
0.6324	Remote Similarity	NPD1535	Discovery
0.6319	Remote Similarity	NPD6653	Approved
0.6316	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD769	Approved
0.6308	Remote Similarity	NPD7843	Approved
0.6303	Remote Similarity	NPD6764	Approved
0.6303	Remote Similarity	NPD6765	Approved
0.6301	Remote Similarity	NPD4477	Approved
0.6301	Remote Similarity	NPD4476	Approved
0.6299	Remote Similarity	NPD5374	Approved
0.6299	Remote Similarity	NPD5373	Approved
0.6294	Remote Similarity	NPD2979	Phase 3
0.6291	Remote Similarity	NPD4662	Approved
0.6291	Remote Similarity	NPD4661	Approved
0.6275	Remote Similarity	NPD957	Approved
0.6268	Remote Similarity	NPD3764	Approved
0.6266	Remote Similarity	NPD7075	Discontinued
0.6258	Remote Similarity	NPD5890	Approved
0.6258	Remote Similarity	NPD5889	Approved
0.625	Remote Similarity	NPD3847	Discontinued
0.625	Remote Similarity	NPD5049	Phase 3
0.6242	Remote Similarity	NPD7003	Approved
0.6241	Remote Similarity	NPD2614	Approved
0.624	Remote Similarity	NPD9261	Approved
0.6234	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7458	Discontinued
0.6233	Remote Similarity	NPD7033	Discontinued
0.6231	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4870	Approved
0.6222	Remote Similarity	NPD1651	Approved
0.6218	Remote Similarity	NPD6801	Discontinued
0.6216	Remote Similarity	NPD1549	Phase 2
0.6216	Remote Similarity	NPD2897	Discontinued
0.6213	Remote Similarity	NPD8434	Phase 2
0.6209	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6559	Discontinued
0.6204	Remote Similarity	NPD6287	Discontinued
0.6203	Remote Similarity	NPD7768	Phase 2
0.6194	Remote Similarity	NPD5536	Phase 2
0.619	Remote Similarity	NPD2240	Approved
0.619	Remote Similarity	NPD2239	Approved
0.6187	Remote Similarity	NPD1283	Approved
0.6187	Remote Similarity	NPD3225	Approved
0.6181	Remote Similarity	NPD1240	Approved
0.6178	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4626	Approved
0.6165	Remote Similarity	NPD7157	Approved
0.6164	Remote Similarity	NPD3749	Approved
0.6154	Remote Similarity	NPD1296	Phase 2
0.6154	Remote Similarity	NPD6785	Approved
0.6154	Remote Similarity	NPD6784	Approved
0.6154	Remote Similarity	NPD958	Approved
0.6154	Remote Similarity	NPD6386	Approved
0.6154	Remote Similarity	NPD6385	Approved
0.6149	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1247	Approved
0.6149	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3817	Phase 2
0.6139	Remote Similarity	NPD5402	Approved
0.6133	Remote Similarity	NPD4110	Phase 3
0.6133	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3226	Approved
0.6129	Remote Similarity	NPD2651	Approved
0.6129	Remote Similarity	NPD2649	Approved
0.6118	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6844	Discontinued
0.6115	Remote Similarity	NPD7317	Phase 3
0.6115	Remote Similarity	NPD7577	Discontinued
0.6111	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD5958	Discontinued
0.6107	Remote Similarity	NPD4534	Discontinued
0.6103	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD3882	Suspended
0.6096	Remote Similarity	NPD1607	Approved
0.609	Remote Similarity	NPD6585	Discontinued
0.6087	Remote Similarity	NPD422	Phase 1
0.6084	Remote Similarity	NPD7095	Approved
0.6084	Remote Similarity	NPD5163	Phase 2
0.6084	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD2438	Suspended
0.6081	Remote Similarity	NPD2531	Phase 2
0.6078	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD5761	Phase 2
0.6076	Remote Similarity	NPD5760	Phase 2
0.6068	Remote Similarity	NPD9259	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