NPASS Compound

Structure

NPC471559 OpenBabel07101718312D 27 28 0 0 1 0 0 0 0 0999 V2000 2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -6.9757 -4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6449 -4.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -3.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1449 -3.2976 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 25 1 0 0 0 0 4 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 13 26 1 0 0 0 0 14 15 2 0 0 0 0 14 26 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 1 0 0 0 18 27 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.19
Volume:	391.582
LogP:	3.486
LogD:	2.988
LogS:	-3.764
# Rotatable Bonds:	9
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	4.311
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.522
MDCK Permeability:	2.6324785721953958e-05
Pgp-inhibitor:	0.714
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.344
30% Bioavailability (F30%):	0.803

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	94.29290008544922%
Volume Distribution (VD):	1.738
Pgp-substrate:	5.4561285972595215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.142
CYP2C19-inhibitor:	0.76
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.521
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.598
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	9.944
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.216
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.373
Carcinogencity:	0.738
Eye Corrosion:	0.004
Eye Irritation:	0.09
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC471559

Natural Product ID:	NPC471559
*Common Name:**	Methyl (E)-5-(Furan-3-Yl)-2-[(3E)-3-[(6R)-6-(2-Hydroxypropan-2-Yl)-2-Oxooxan-3-Ylidene]Propyl]Pent-2-Enoate
IUPAC Name:	methyl (E)-5-(furan-3-yl)-2-[(3E)-3-[(6R)-6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]propyl]pent-2-enoate
Synonyms:
Standard InCHIKey:	JZDFXSMOBHIZBC-WKDFDSEUSA-N
Standard InCHI:	InChI=1S/C21H28O6/c1-21(2,24)18-11-10-17(20(23)27-18)9-5-8-16(19(22)25-3)7-4-6-15-12-13-26-14-15/h7,9,12-14,18,24H,4-6,8,10-11H2,1-3H3/b16-7+,17-9+/t18-/m1/s1
SMILES:	COC(=O)/C(=C/CCc1cocc1)/CC/C=C/1CC[C@@H](OC1=O)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257117
PubChem CID:	24799329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO12372	Baccharis thymifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18232640]
NPO12372	Baccharis thymifolia	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	11.2	day	PMID[551323]

☑ 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 NPC471559 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	231
0.1-0.2	1008
0.2-0.3	3188
0.3-0.4	7346
0.4-0.5	12373
0.5-0.6	8302
0.6-0.7	9126
0.7-0.8	1022
0.8-0.85	68
0.85-0.9	25
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9344	High Similarity	NPC471501
0.9344	High Similarity	NPC473355
0.9344	High Similarity	NPC471573
0.9344	High Similarity	NPC471554
0.925	High Similarity	NPC471549
0.925	High Similarity	NPC473379
0.92	High Similarity	NPC17681
0.9187	High Similarity	NPC476016
0.9127	High Similarity	NPC97740
0.9106	High Similarity	NPC329694
0.9106	High Similarity	NPC474260
0.9106	High Similarity	NPC329922
0.9106	High Similarity	NPC81912
0.9032	High Similarity	NPC474830
0.9024	High Similarity	NPC474829
0.9016	High Similarity	NPC475818
0.8976	High Similarity	NPC473344
0.8976	High Similarity	NPC471544
0.8976	High Similarity	NPC45358
0.896	High Similarity	NPC474279
0.896	High Similarity	NPC474438
0.8926	High Similarity	NPC474817
0.888	High Similarity	NPC137570
0.8871	High Similarity	NPC75557
0.8871	High Similarity	NPC71274
0.8862	High Similarity	NPC476351
0.8833	High Similarity	NPC208906
0.8833	High Similarity	NPC144745
0.878	High Similarity	NPC289911
0.878	High Similarity	NPC283284
0.8729	High Similarity	NPC1811
0.8729	High Similarity	NPC26157
0.8699	High Similarity	NPC474136
0.8682	High Similarity	NPC471545
0.8615	High Similarity	NPC474426
0.8615	High Similarity	NPC474425
0.8615	High Similarity	NPC474407
0.8547	High Similarity	NPC471521
0.8547	High Similarity	NPC473356
0.8487	Intermediate Similarity	NPC105249
0.8387	Intermediate Similarity	NPC473969
0.8374	Intermediate Similarity	NPC131801
0.8359	Intermediate Similarity	NPC138139
0.8359	Intermediate Similarity	NPC46536
0.8346	Intermediate Similarity	NPC243269
0.8346	Intermediate Similarity	NPC14650
0.8333	Intermediate Similarity	NPC137295
0.8319	Intermediate Similarity	NPC177331
0.8306	Intermediate Similarity	NPC21831
0.8306	Intermediate Similarity	NPC187547
0.8295	Intermediate Similarity	NPC83178
0.8284	Intermediate Similarity	NPC303217
0.8281	Intermediate Similarity	NPC179354
0.8271	Intermediate Similarity	NPC288209
0.8254	Intermediate Similarity	NPC1848
0.8231	Intermediate Similarity	NPC207294
0.8231	Intermediate Similarity	NPC112706
0.8222	Intermediate Similarity	NPC170604
0.8222	Intermediate Similarity	NPC215109
0.8217	Intermediate Similarity	NPC74612
0.8211	Intermediate Similarity	NPC28054
0.8203	Intermediate Similarity	NPC118853
0.8203	Intermediate Similarity	NPC65735
0.8203	Intermediate Similarity	NPC188377
0.8189	Intermediate Similarity	NPC477967
0.8188	Intermediate Similarity	NPC121158
0.8182	Intermediate Similarity	NPC89133
0.8169	Intermediate Similarity	NPC69647
0.8169	Intermediate Similarity	NPC125182
0.816	Intermediate Similarity	NPC243704
0.8156	Intermediate Similarity	NPC255414
0.8125	Intermediate Similarity	NPC16922
0.8125	Intermediate Similarity	NPC44577
0.812	Intermediate Similarity	NPC471817
0.811	Intermediate Similarity	NPC79557
0.8106	Intermediate Similarity	NPC21460
0.8102	Intermediate Similarity	NPC107571
0.8095	Intermediate Similarity	NPC4898
0.8088	Intermediate Similarity	NPC310830
0.8085	Intermediate Similarity	NPC346
0.808	Intermediate Similarity	NPC312525
0.808	Intermediate Similarity	NPC217180
0.8074	Intermediate Similarity	NPC476947
0.8071	Intermediate Similarity	NPC476944
0.8071	Intermediate Similarity	NPC251865
0.8065	Intermediate Similarity	NPC205523
0.806	Intermediate Similarity	NPC218838
0.8047	Intermediate Similarity	NPC263870
0.8043	Intermediate Similarity	NPC90296
0.8042	Intermediate Similarity	NPC234494
0.8029	Intermediate Similarity	NPC476943
0.8029	Intermediate Similarity	NPC220094
0.8015	Intermediate Similarity	NPC319140
0.8015	Intermediate Similarity	NPC95567
0.8014	Intermediate Similarity	NPC214541
0.8014	Intermediate Similarity	NPC44675
0.8	Intermediate Similarity	NPC80635
0.8	Intermediate Similarity	NPC268905
0.7986	Intermediate Similarity	NPC228842
0.7972	Intermediate Similarity	NPC7388
0.7971	Intermediate Similarity	NPC90953
0.7956	Intermediate Similarity	NPC473268
0.7956	Intermediate Similarity	NPC186626
0.7943	Intermediate Similarity	NPC307346
0.7943	Intermediate Similarity	NPC218712
0.7943	Intermediate Similarity	NPC267004
0.7943	Intermediate Similarity	NPC86935
0.7943	Intermediate Similarity	NPC261733
0.7941	Intermediate Similarity	NPC158525
0.7939	Intermediate Similarity	NPC23086
0.7937	Intermediate Similarity	NPC227660
0.7929	Intermediate Similarity	NPC184053
0.7923	Intermediate Similarity	NPC477965
0.7923	Intermediate Similarity	NPC477038
0.792	Intermediate Similarity	NPC150895
0.7914	Intermediate Similarity	NPC67003
0.791	Intermediate Similarity	NPC61788
0.791	Intermediate Similarity	NPC298190
0.7907	Intermediate Similarity	NPC317217
0.7905	Intermediate Similarity	NPC261597
0.7905	Intermediate Similarity	NPC36655
0.7905	Intermediate Similarity	NPC187149
0.7905	Intermediate Similarity	NPC299038
0.7905	Intermediate Similarity	NPC45101
0.7902	Intermediate Similarity	NPC250228
0.7891	Intermediate Similarity	NPC281258
0.7891	Intermediate Similarity	NPC264943
0.7887	Intermediate Similarity	NPC5676
0.7883	Intermediate Similarity	NPC46896
0.7877	Intermediate Similarity	NPC294511
0.7877	Intermediate Similarity	NPC33938
0.7877	Intermediate Similarity	NPC121615
0.7872	Intermediate Similarity	NPC267632
0.7863	Intermediate Similarity	NPC221798
0.7862	Intermediate Similarity	NPC470997
0.7857	Intermediate Similarity	NPC45536
0.7852	Intermediate Similarity	NPC473982
0.7852	Intermediate Similarity	NPC475967
0.7838	Intermediate Similarity	NPC469485
0.7826	Intermediate Similarity	NPC42400
0.781	Intermediate Similarity	NPC92941
0.7801	Intermediate Similarity	NPC52412
0.78	Intermediate Similarity	NPC477402
0.7794	Intermediate Similarity	NPC470740
0.7786	Intermediate Similarity	NPC56197
0.7786	Intermediate Similarity	NPC130275
0.7786	Intermediate Similarity	NPC148374
0.7785	Intermediate Similarity	NPC194499
0.7785	Intermediate Similarity	NPC173544
0.7785	Intermediate Similarity	NPC88007
0.7785	Intermediate Similarity	NPC7059
0.7778	Intermediate Similarity	NPC183348
0.7778	Intermediate Similarity	NPC282230
0.7778	Intermediate Similarity	NPC216755
0.7778	Intermediate Similarity	NPC471174
0.777	Intermediate Similarity	NPC296807
0.777	Intermediate Similarity	NPC141538
0.777	Intermediate Similarity	NPC155939
0.7762	Intermediate Similarity	NPC34056
0.7755	Intermediate Similarity	NPC147168
0.7755	Intermediate Similarity	NPC474378
0.7755	Intermediate Similarity	NPC474219
0.7754	Intermediate Similarity	NPC146872
0.7748	Intermediate Similarity	NPC149896
0.7748	Intermediate Similarity	NPC18347
0.7748	Intermediate Similarity	NPC200782
0.7748	Intermediate Similarity	NPC263432
0.7746	Intermediate Similarity	NPC254198
0.7746	Intermediate Similarity	NPC242756
0.7746	Intermediate Similarity	NPC243577
0.7746	Intermediate Similarity	NPC476946
0.774	Intermediate Similarity	NPC212257
0.7737	Intermediate Similarity	NPC106247
0.7734	Intermediate Similarity	NPC254958
0.7734	Intermediate Similarity	NPC291619
0.7733	Intermediate Similarity	NPC262872
0.7733	Intermediate Similarity	NPC477403
0.7733	Intermediate Similarity	NPC472779
0.7721	Intermediate Similarity	NPC196979
0.7721	Intermediate Similarity	NPC15083
0.7721	Intermediate Similarity	NPC470976
0.7721	Intermediate Similarity	NPC470977
0.7721	Intermediate Similarity	NPC104854
0.7714	Intermediate Similarity	NPC202260
0.771	Intermediate Similarity	NPC291189
0.771	Intermediate Similarity	NPC69403
0.7708	Intermediate Similarity	NPC104924
0.7704	Intermediate Similarity	NPC66246
0.7704	Intermediate Similarity	NPC170546
0.7703	Intermediate Similarity	NPC282445
0.7703	Intermediate Similarity	NPC57998
0.7698	Intermediate Similarity	NPC470742
0.7697	Intermediate Similarity	NPC477405
0.7697	Intermediate Similarity	NPC292389
0.7697	Intermediate Similarity	NPC472773
0.7697	Intermediate Similarity	NPC469338
0.7692	Intermediate Similarity	NPC142113
0.7687	Intermediate Similarity	NPC477039
0.7687	Intermediate Similarity	NPC477966
0.7687	Intermediate Similarity	NPC477040

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 NPC471559 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	785
0.2-0.3	1999
0.3-0.4	2634
0.4-0.5	2133
0.5-0.6	1065
0.6-0.7	318
0.7-0.8	21
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
0.7676	Intermediate Similarity	NPD4628	Phase 3
0.7465	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD9717	Approved
0.7266	Intermediate Similarity	NPD6798	Discontinued
0.726	Intermediate Similarity	NPD3887	Approved
0.726	Intermediate Similarity	NPD2354	Approved
0.7241	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6355	Discontinued
0.7197	Intermediate Similarity	NPD9545	Approved
0.719	Intermediate Similarity	NPD5761	Phase 2
0.719	Intermediate Similarity	NPD5760	Phase 2
0.719	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9494	Approved
0.7162	Intermediate Similarity	NPD6799	Approved
0.7122	Intermediate Similarity	NPD6832	Phase 2
0.7121	Intermediate Similarity	NPD9092	Discovery
0.7101	Intermediate Similarity	NPD5647	Approved
0.7092	Intermediate Similarity	NPD4062	Phase 3
0.7092	Intermediate Similarity	NPD6233	Phase 2
0.7051	Intermediate Similarity	NPD7075	Discontinued
0.7029	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1203	Approved
0.7008	Intermediate Similarity	NPD1358	Approved
0.6993	Remote Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD6599	Discontinued
0.6993	Remote Similarity	NPD1933	Approved
0.6986	Remote Similarity	NPD2344	Approved
0.6986	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2353	Approved
0.6985	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1019	Discontinued
0.6977	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4308	Phase 3
0.6966	Remote Similarity	NPD7033	Discontinued
0.6966	Remote Similarity	NPD2799	Discontinued
0.6951	Remote Similarity	NPD6765	Approved
0.6951	Remote Similarity	NPD6764	Approved
0.6947	Remote Similarity	NPD1241	Discontinued
0.6946	Remote Similarity	NPD8434	Phase 2
0.6934	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6908	Remote Similarity	NPD920	Approved
0.6906	Remote Similarity	NPD2797	Approved
0.6903	Remote Similarity	NPD6801	Discontinued
0.6901	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2313	Discontinued
0.6901	Remote Similarity	NPD3268	Approved
0.6894	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6559	Discontinued
0.6842	Remote Similarity	NPD6273	Approved
0.6842	Remote Similarity	NPD5049	Phase 3
0.6839	Remote Similarity	NPD7411	Suspended
0.6838	Remote Similarity	NPD1778	Approved
0.6828	Remote Similarity	NPD6653	Approved
0.6824	Remote Similarity	NPD1549	Phase 2
0.6822	Remote Similarity	NPD2684	Approved
0.6821	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1894	Discontinued
0.6812	Remote Similarity	NPD3972	Approved
0.6806	Remote Similarity	NPD3142	Approved
0.6806	Remote Similarity	NPD4307	Phase 2
0.6806	Remote Similarity	NPD3140	Approved
0.68	Remote Similarity	NPD2309	Approved
0.6797	Remote Similarity	NPD5403	Approved
0.6797	Remote Similarity	NPD3134	Approved
0.6792	Remote Similarity	NPD919	Approved
0.6791	Remote Similarity	NPD9493	Approved
0.6786	Remote Similarity	NPD6784	Approved
0.6786	Remote Similarity	NPD6785	Approved
0.6783	Remote Similarity	NPD411	Approved
0.6781	Remote Similarity	NPD7097	Phase 1
0.6776	Remote Similarity	NPD5401	Approved
0.6776	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2346	Discontinued
0.6757	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7819	Suspended
0.6744	Remote Similarity	NPD290	Approved
0.6742	Remote Similarity	NPD7843	Approved
0.6733	Remote Similarity	NPD4110	Phase 3
0.6733	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3749	Approved
0.673	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD17	Approved
0.6713	Remote Similarity	NPD7095	Approved
0.6711	Remote Similarity	NPD5958	Discontinued
0.6711	Remote Similarity	NPD2424	Discontinued
0.6711	Remote Similarity	NPD4534	Discontinued
0.671	Remote Similarity	NPD7458	Discontinued
0.671	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2239	Approved
0.6689	Remote Similarity	NPD2796	Approved
0.6689	Remote Similarity	NPD2240	Approved
0.6689	Remote Similarity	NPD2935	Discontinued
0.6688	Remote Similarity	NPD1934	Approved
0.6687	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4661	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD4662	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3267	Approved
0.6646	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7440	Discontinued
0.6644	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6004	Phase 3
0.6644	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6005	Phase 3
0.6644	Remote Similarity	NPD6002	Phase 3
0.6644	Remote Similarity	NPD230	Phase 1
0.6644	Remote Similarity	NPD1471	Phase 3
0.6641	Remote Similarity	NPD2067	Discontinued
0.6624	Remote Similarity	NPD958	Approved
0.662	Remote Similarity	NPD2798	Approved
0.6604	Remote Similarity	NPD3817	Phase 2
0.6597	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3225	Approved
0.6593	Remote Similarity	NPD7157	Approved
0.6581	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1481	Phase 2
0.6566	Remote Similarity	NPD5844	Phase 1
0.6565	Remote Similarity	NPD2182	Approved
0.6564	Remote Similarity	NPD6808	Phase 2
0.6547	Remote Similarity	NPD3847	Discontinued
0.6541	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5585	Approved
0.6516	Remote Similarity	NPD2186	Approved
0.6513	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD3750	Approved
0.6506	Remote Similarity	NPD2163	Approved
0.6506	Remote Similarity	NPD3818	Discontinued
0.65	Remote Similarity	NPD5402	Approved
0.65	Remote Similarity	NPD1535	Discovery
0.6493	Remote Similarity	NPD5535	Approved
0.649	Remote Similarity	NPD2897	Discontinued
0.6489	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD1876	Approved
0.6478	Remote Similarity	NPD7577	Discontinued
0.6474	Remote Similarity	NPD1670	Discontinued
0.6467	Remote Similarity	NPD4477	Approved
0.6467	Remote Similarity	NPD6032	Approved
0.6467	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4476	Approved
0.6463	Remote Similarity	NPD4060	Phase 1
0.6463	Remote Similarity	NPD1240	Approved
0.6462	Remote Similarity	NPD9697	Approved
0.6458	Remote Similarity	NPD454	Approved
0.6457	Remote Similarity	NPD1238	Approved
0.6452	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2534	Approved
0.6452	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2533	Approved
0.6452	Remote Similarity	NPD2532	Approved
0.645	Remote Similarity	NPD7685	Pre-registration
0.6442	Remote Similarity	NPD5494	Approved
0.6434	Remote Similarity	NPD987	Approved
0.6433	Remote Similarity	NPD957	Approved
0.6424	Remote Similarity	NPD5762	Approved
0.6424	Remote Similarity	NPD5763	Approved
0.6424	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4622	Approved
0.6419	Remote Similarity	NPD4618	Approved
0.6414	Remote Similarity	NPD2614	Approved
0.6408	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7003	Approved
0.6405	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1247	Approved
0.64	Remote Similarity	NPD3748	Approved
0.64	Remote Similarity	NPD1510	Phase 2
0.6398	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2651	Approved
0.6392	Remote Similarity	NPD3226	Approved
0.6392	Remote Similarity	NPD2649	Approved
0.6391	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3823	Discontinued
0.6389	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6166	Phase 2
0.6386	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1091	Approved
0.6382	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1607	Approved
0.6375	Remote Similarity	NPD6280	Approved
0.6375	Remote Similarity	NPD6279	Approved
0.6369	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1283	Approved
0.6364	Remote Similarity	NPD6190	Approved
0.6358	Remote Similarity	NPD7768	Phase 2

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