NPASS Compound

Structure

NPC474426 OpenBabel07101718222D 34 34 0 0 1 0 0 0 0 0999 V2000 3.9641 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 10.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 9.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 12.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 7.3068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 7.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 8.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 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 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 8.5388 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 3.0981 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 9.0388 0.0000 C 0 0 2 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 -1.2321 10.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 8.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 9.5388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3660 9.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3660 11.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 8.1728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 8.6728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 9.9049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 11.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 7.3068 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 20 1 0 0 0 0 2 21 1 0 0 0 0 4 26 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 20 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 34 1 0 0 0 0 18 22 1 0 0 0 0 18 27 1 0 0 0 0 19 23 2 0 0 0 0 19 34 1 0 0 0 0 22 3 1 6 0 0 0 24 26 1 0 0 0 0 24 28 2 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 29 2 0 0 0 0 25 33 1 0 0 0 0 26 27 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.29
Volume:	512.704
LogP:	4.325
LogD:	4.523
LogS:	-4.995
# Rotatable Bonds:	17
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	4.268
Fsp3:	0.63
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.706
MDCK Permeability:	3.781552004511468e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.67
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.504
Plasma Protein Binding (PPB):	98.54933166503906%
Volume Distribution (VD):	2.348
Pgp-substrate:	0.8539421558380127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.392
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.843
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.96
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.703
CYP2D6-substrate:	0.635
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.671

ADMET: Excretion

Clearance (CL):	7.218
Half-life (T1/2):	0.648

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.745
Maximum Recommended Daily Dose:	0.148
Skin Sensitization:	0.152
Carcinogencity:	0.837
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.111

Download Data

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

Natural Product: NPC474426

Natural Product ID:	NPC474426
*Common Name:**	(2R)-Dimethyl 2-((R,5Z,9Z)-13-(Furan-3-Yl)-2,6,10-Trimethyltrideca-5,9-Dienyl)-2,3-Dihydroxy-3-Methylsuccinate
IUPAC Name:	dimethyl (2R)-2-[(2R,5Z,9Z)-13-(furan-3-yl)-2,6,10-trimethyltrideca-5,9-dienyl]-2,3-dihydroxy-3-methylbutanedioate
Synonyms:
Standard InCHIKey:	JKWBGEZEBFVNFX-JLQRJSBNSA-N
Standard InCHI:	InChI=1S/C27H42O7/c1-20(10-7-11-21(2)13-9-15-23-16-17-34-19-23)12-8-14-22(3)18-27(31,25(29)33-6)26(4,30)24(28)32-5/h11-12,16-17,19,22,30-31H,7-10,13-15,18H2,1-6H3/b20-12-,21-11-/t22-,26?,27+/m1/s1
SMILES:	COC(=O)[C@](C(C(=O)OC)(O)C)(C[C@@H](CC/C=C(CC/C=C(CCCc1cocc1)/C)/C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468142
PubChem CID:	44577397
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678655]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350153]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341287]

☑ 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	1
MIC	9
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	90.0	ug.mL-1	PMID[479162]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	34.0	ug.mL-1	PMID[479162]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[479162]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[479162]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[479162]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[479162]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[479162]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[479162]

☑ 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 NPC474426 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	257
0.1-0.2	1153
0.2-0.3	3487
0.3-0.4	7729
0.4-0.5	11839
0.5-0.6	8188
0.6-0.7	9008
0.7-0.8	920
0.8-0.85	98
0.85-0.9	15
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474425
1.0	High Similarity	NPC474407
0.9062	High Similarity	NPC474830
0.9062	High Similarity	NPC476016
0.8992	High Similarity	NPC474438
0.8992	High Similarity	NPC474279
0.8906	High Similarity	NPC474829
0.8837	High Similarity	NPC329922
0.8837	High Similarity	NPC329694
0.8837	High Similarity	NPC474260
0.8837	High Similarity	NPC81912
0.876	High Similarity	NPC71274
0.876	High Similarity	NPC75557
0.872	High Similarity	NPC208906
0.872	High Similarity	NPC144745
0.8676	High Similarity	NPC473268
0.8647	High Similarity	NPC17681
0.8615	High Similarity	NPC471559
0.8605	High Similarity	NPC476351
0.8605	High Similarity	NPC475818
0.8594	High Similarity	NPC1848
0.8582	High Similarity	NPC97740
0.8527	High Similarity	NPC471549
0.8527	High Similarity	NPC473379
0.8527	High Similarity	NPC283284
0.8527	High Similarity	NPC289911
0.8516	High Similarity	NPC474817
0.8485	Intermediate Similarity	NPC471501
0.8485	Intermediate Similarity	NPC473355
0.8485	Intermediate Similarity	NPC471573
0.8485	Intermediate Similarity	NPC471554
0.845	Intermediate Similarity	NPC474136
0.8444	Intermediate Similarity	NPC45358
0.8425	Intermediate Similarity	NPC44577
0.8397	Intermediate Similarity	NPC243269
0.8385	Intermediate Similarity	NPC263870
0.838	Intermediate Similarity	NPC137295
0.8378	Intermediate Similarity	NPC469485
0.8357	Intermediate Similarity	NPC282973
0.8346	Intermediate Similarity	NPC137570
0.8322	Intermediate Similarity	NPC173544
0.8322	Intermediate Similarity	NPC45101
0.8321	Intermediate Similarity	NPC106247
0.8311	Intermediate Similarity	NPC281258
0.8311	Intermediate Similarity	NPC214541
0.8311	Intermediate Similarity	NPC44675
0.831	Intermediate Similarity	NPC267632
0.831	Intermediate Similarity	NPC476946
0.8309	Intermediate Similarity	NPC471544
0.8309	Intermediate Similarity	NPC473344
0.8309	Intermediate Similarity	NPC471545
0.8308	Intermediate Similarity	NPC79557
0.8299	Intermediate Similarity	NPC474378
0.8299	Intermediate Similarity	NPC474219
0.8295	Intermediate Similarity	NPC473969
0.8286	Intermediate Similarity	NPC107571
0.8271	Intermediate Similarity	NPC138139
0.8271	Intermediate Similarity	NPC46536
0.8267	Intermediate Similarity	NPC472779
0.8261	Intermediate Similarity	NPC159786
0.8261	Intermediate Similarity	NPC92941
0.8258	Intermediate Similarity	NPC118853
0.8248	Intermediate Similarity	NPC470740
0.8235	Intermediate Similarity	NPC89133
0.8212	Intermediate Similarity	NPC477402
0.8209	Intermediate Similarity	NPC319140
0.8209	Intermediate Similarity	NPC95567
0.8209	Intermediate Similarity	NPC83178
0.8203	Intermediate Similarity	NPC45536
0.82	Intermediate Similarity	NPC261597
0.8194	Intermediate Similarity	NPC195920
0.8176	Intermediate Similarity	NPC147168
0.8175	Intermediate Similarity	NPC1811
0.8175	Intermediate Similarity	NPC471817
0.8175	Intermediate Similarity	NPC26157
0.8158	Intermediate Similarity	NPC329938
0.8158	Intermediate Similarity	NPC263432
0.8148	Intermediate Similarity	NPC207294
0.8148	Intermediate Similarity	NPC112706
0.8146	Intermediate Similarity	NPC475967
0.8146	Intermediate Similarity	NPC477403
0.8143	Intermediate Similarity	NPC186626
0.8143	Intermediate Similarity	NPC170604
0.8143	Intermediate Similarity	NPC470742
0.8143	Intermediate Similarity	NPC310830
0.8143	Intermediate Similarity	NPC215109
0.814	Intermediate Similarity	NPC131801
0.8138	Intermediate Similarity	NPC104924
0.8138	Intermediate Similarity	NPC346
0.8138	Intermediate Similarity	NPC475864
0.8129	Intermediate Similarity	NPC14650
0.8125	Intermediate Similarity	NPC476944
0.8125	Intermediate Similarity	NPC86935
0.812	Intermediate Similarity	NPC188377
0.812	Intermediate Similarity	NPC65735
0.8112	Intermediate Similarity	NPC52412
0.8106	Intermediate Similarity	NPC477967
0.8105	Intermediate Similarity	NPC292389
0.8105	Intermediate Similarity	NPC477405
0.8105	Intermediate Similarity	NPC469338
0.8102	Intermediate Similarity	NPC136340
0.8099	Intermediate Similarity	NPC90296
0.8095	Intermediate Similarity	NPC474270
0.8095	Intermediate Similarity	NPC475904
0.8095	Intermediate Similarity	NPC69647
0.8095	Intermediate Similarity	NPC125182
0.8092	Intermediate Similarity	NPC25255
0.8092	Intermediate Similarity	NPC472653
0.8092	Intermediate Similarity	NPC335761
0.8092	Intermediate Similarity	NPC470789
0.8085	Intermediate Similarity	NPC476943
0.8085	Intermediate Similarity	NPC220094
0.8082	Intermediate Similarity	NPC255414
0.8079	Intermediate Similarity	NPC36655
0.8079	Intermediate Similarity	NPC187149
0.8071	Intermediate Similarity	NPC146872
0.8071	Intermediate Similarity	NPC303217
0.8067	Intermediate Similarity	NPC264943
0.806	Intermediate Similarity	NPC179354
0.8058	Intermediate Similarity	NPC288209
0.8056	Intermediate Similarity	NPC254198
0.8052	Intermediate Similarity	NPC469849
0.8052	Intermediate Similarity	NPC276551
0.8052	Intermediate Similarity	NPC470940
0.8045	Intermediate Similarity	NPC16922
0.8041	Intermediate Similarity	NPC46551
0.8039	Intermediate Similarity	NPC82851
0.8039	Intermediate Similarity	NPC69028
0.8039	Intermediate Similarity	NPC18347
0.8039	Intermediate Similarity	NPC5079
0.8039	Intermediate Similarity	NPC149896
0.8039	Intermediate Similarity	NPC193798
0.8029	Intermediate Similarity	NPC21460
0.8028	Intermediate Similarity	NPC90953
0.8027	Intermediate Similarity	NPC474255
0.8027	Intermediate Similarity	NPC471618
0.8027	Intermediate Similarity	NPC7388
0.8027	Intermediate Similarity	NPC474220
0.8014	Intermediate Similarity	NPC42400
0.8	Intermediate Similarity	NPC471521
0.8	Intermediate Similarity	NPC470875
0.8	Intermediate Similarity	NPC476947
0.8	Intermediate Similarity	NPC473356
0.7987	Intermediate Similarity	NPC39986
0.7987	Intermediate Similarity	NPC51568
0.7987	Intermediate Similarity	NPC234660
0.7987	Intermediate Similarity	NPC302369
0.7987	Intermediate Similarity	NPC134254
0.7986	Intermediate Similarity	NPC121158
0.7973	Intermediate Similarity	NPC472654
0.7961	Intermediate Similarity	NPC472776
0.7961	Intermediate Similarity	NPC472778
0.7961	Intermediate Similarity	NPC249021
0.7961	Intermediate Similarity	NPC299038
0.7961	Intermediate Similarity	NPC472777
0.7959	Intermediate Similarity	NPC476938
0.7959	Intermediate Similarity	NPC476937
0.7959	Intermediate Similarity	NPC250228
0.7958	Intermediate Similarity	NPC236532
0.7953	Intermediate Similarity	NPC105249
0.7949	Intermediate Similarity	NPC472774
0.7949	Intermediate Similarity	NPC472775
0.7949	Intermediate Similarity	NPC472282
0.7949	Intermediate Similarity	NPC173516
0.7949	Intermediate Similarity	NPC472651
0.7945	Intermediate Similarity	NPC37488
0.7935	Intermediate Similarity	NPC271657
0.7935	Intermediate Similarity	NPC476857
0.7935	Intermediate Similarity	NPC146991
0.7935	Intermediate Similarity	NPC476858
0.7935	Intermediate Similarity	NPC476856
0.7935	Intermediate Similarity	NPC123088
0.7933	Intermediate Similarity	NPC268905
0.7933	Intermediate Similarity	NPC33938
0.7931	Intermediate Similarity	NPC110305
0.7931	Intermediate Similarity	NPC80635
0.7929	Intermediate Similarity	NPC471998
0.7922	Intermediate Similarity	NPC200782
0.7919	Intermediate Similarity	NPC470997
0.7917	Intermediate Similarity	NPC205765
0.7914	Intermediate Similarity	NPC473982
0.7908	Intermediate Similarity	NPC262872
0.7905	Intermediate Similarity	NPC476941
0.7905	Intermediate Similarity	NPC476942
0.7898	Intermediate Similarity	NPC472652
0.7898	Intermediate Similarity	NPC160651
0.7898	Intermediate Similarity	NPC471397
0.7898	Intermediate Similarity	NPC271235
0.7895	Intermediate Similarity	NPC126723
0.7895	Intermediate Similarity	NPC209364
0.7895	Intermediate Similarity	NPC107646
0.7891	Intermediate Similarity	NPC262198
0.7881	Intermediate Similarity	NPC282445
0.7877	Intermediate Similarity	NPC267004
0.7877	Intermediate Similarity	NPC218712
0.7877	Intermediate Similarity	NPC142113
0.7877	Intermediate Similarity	NPC251865
0.7877	Intermediate Similarity	NPC307346
0.7877	Intermediate Similarity	NPC261733
0.7872	Intermediate Similarity	NPC158525

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 NPC474426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	1008
0.2-0.3	2110
0.3-0.4	2593
0.4-0.5	1992
0.5-0.6	915
0.6-0.7	287
0.7-0.8	12
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
0.7778	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD5761	Phase 2
0.7484	Intermediate Similarity	NPD5760	Phase 2
0.7431	Intermediate Similarity	NPD6355	Discontinued
0.7279	Intermediate Similarity	NPD2799	Discontinued
0.7203	Intermediate Similarity	NPD6832	Phase 2
0.7192	Intermediate Similarity	NPD447	Suspended
0.7183	Intermediate Similarity	NPD5647	Approved
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD9717	Approved
0.7124	Intermediate Similarity	NPD6799	Approved
0.7103	Intermediate Similarity	NPD2313	Discontinued
0.7081	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6599	Discontinued
0.7067	Intermediate Similarity	NPD2344	Approved
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.7027	Intermediate Similarity	NPD6653	Approved
0.7019	Intermediate Similarity	NPD7075	Discontinued
0.6987	Remote Similarity	NPD920	Approved
0.6986	Remote Similarity	NPD6798	Discontinued
0.6954	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD1471	Phase 3
0.6944	Remote Similarity	NPD1019	Discontinued
0.6923	Remote Similarity	NPD6765	Approved
0.6923	Remote Similarity	NPD6764	Approved
0.6918	Remote Similarity	NPD7095	Approved
0.6894	Remote Similarity	NPD5402	Approved
0.6887	Remote Similarity	NPD1551	Phase 2
0.6887	Remote Similarity	NPD2935	Discontinued
0.6883	Remote Similarity	NPD2309	Approved
0.6883	Remote Similarity	NPD2354	Approved
0.6879	Remote Similarity	NPD5403	Approved
0.6875	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD1203	Approved
0.6871	Remote Similarity	NPD919	Approved
0.6861	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5401	Approved
0.6859	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3882	Suspended
0.6846	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7972	Discontinued
0.6828	Remote Similarity	NPD2798	Approved
0.6824	Remote Similarity	NPD6559	Discontinued
0.6824	Remote Similarity	NPD4062	Phase 3
0.6821	Remote Similarity	NPD4308	Phase 3
0.6797	Remote Similarity	NPD5958	Discontinued
0.679	Remote Similarity	NPD3817	Phase 2
0.6779	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3887	Approved
0.677	Remote Similarity	NPD6801	Discontinued
0.6763	Remote Similarity	NPD6784	Approved
0.6763	Remote Similarity	NPD6785	Approved
0.6759	Remote Similarity	NPD6362	Approved
0.6757	Remote Similarity	NPD411	Approved
0.6757	Remote Similarity	NPD3268	Approved
0.6755	Remote Similarity	NPD7097	Phase 1
0.6733	Remote Similarity	NPD1933	Approved
0.6732	Remote Similarity	NPD6005	Phase 3
0.6732	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6004	Phase 3
0.6732	Remote Similarity	NPD6002	Phase 3
0.6731	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7819	Suspended
0.6714	Remote Similarity	NPD9092	Discovery
0.671	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6273	Approved
0.6709	Remote Similarity	NPD5049	Phase 3
0.6707	Remote Similarity	NPD3749	Approved
0.6691	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4534	Discontinued
0.6687	Remote Similarity	NPD1247	Approved
0.6687	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD9494	Approved
0.6647	Remote Similarity	NPD6808	Phase 2
0.6646	Remote Similarity	NPD2534	Approved
0.6646	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD2532	Approved
0.6646	Remote Similarity	NPD2533	Approved
0.6646	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD987	Approved
0.6644	Remote Similarity	NPD3764	Approved
0.6644	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD9493	Approved
0.6623	Remote Similarity	NPD2353	Approved
0.6623	Remote Similarity	NPD5763	Approved
0.6623	Remote Similarity	NPD5762	Approved
0.6623	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2067	Discontinued
0.6607	Remote Similarity	NPD3926	Phase 2
0.6603	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4110	Phase 3
0.6603	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7033	Discontinued
0.6597	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7458	Discontinued
0.6584	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2424	Discontinued
0.6575	Remote Similarity	NPD1876	Approved
0.6571	Remote Similarity	NPD7157	Approved
0.6552	Remote Similarity	NPD8312	Approved
0.6552	Remote Similarity	NPD8313	Approved
0.6547	Remote Similarity	NPD1241	Discontinued
0.6545	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1243	Approved
0.6533	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3266	Approved
0.6531	Remote Similarity	NPD3267	Approved
0.6528	Remote Similarity	NPD3496	Discontinued
0.6527	Remote Similarity	NPD5494	Approved
0.6519	Remote Similarity	NPD7440	Discontinued
0.651	Remote Similarity	NPD8404	Phase 2
0.6506	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7411	Suspended
0.6503	Remote Similarity	NPD5585	Approved
0.6497	Remote Similarity	NPD3750	Approved
0.6491	Remote Similarity	NPD3818	Discontinued
0.6491	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7843	Approved
0.6474	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1358	Approved
0.6471	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6280	Approved
0.6463	Remote Similarity	NPD1934	Approved
0.6463	Remote Similarity	NPD6279	Approved
0.6458	Remote Similarity	NPD17	Approved
0.6453	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6032	Approved
0.6452	Remote Similarity	NPD2796	Approved
0.6442	Remote Similarity	NPD4380	Phase 2
0.6438	Remote Similarity	NPD4661	Approved
0.6438	Remote Similarity	NPD4662	Approved
0.6434	Remote Similarity	NPD9545	Approved
0.6434	Remote Similarity	NPD1894	Discontinued
0.6433	Remote Similarity	NPD7473	Discontinued
0.6424	Remote Similarity	NPD2801	Approved
0.6424	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7985	Registered
0.6424	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD2684	Approved
0.6405	Remote Similarity	NPD230	Phase 1
0.6405	Remote Similarity	NPD4618	Approved
0.6405	Remote Similarity	NPD4622	Approved
0.6397	Remote Similarity	NPD3134	Approved
0.6392	Remote Similarity	NPD7003	Approved
0.6391	Remote Similarity	NPD8127	Discontinued
0.6387	Remote Similarity	NPD3748	Approved
0.6386	Remote Similarity	NPD2296	Approved
0.6386	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6166	Phase 2
0.6374	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.637	Remote Similarity	NPD164	Approved
0.6369	Remote Similarity	NPD1549	Phase 2
0.6369	Remote Similarity	NPD2897	Discontinued
0.6364	Remote Similarity	NPD6844	Discontinued
0.6353	Remote Similarity	NPD6232	Discontinued
0.6351	Remote Similarity	NPD1283	Approved
0.6346	Remote Similarity	NPD2438	Suspended
0.6346	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4477	Approved
0.6346	Remote Similarity	NPD5712	Approved
0.6346	Remote Similarity	NPD4476	Approved
0.6345	Remote Similarity	NPD1778	Approved
0.6343	Remote Similarity	NPD7685	Pre-registration
0.634	Remote Similarity	NPD2979	Phase 3
0.6335	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD2800	Approved
0.6327	Remote Similarity	NPD1481	Phase 2
0.6327	Remote Similarity	NPD3972	Approved
0.6325	Remote Similarity	NPD8455	Phase 2
0.6325	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5688	Approved
0.6323	Remote Similarity	NPD5689	Approved
0.6316	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7236	Approved
0.6307	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD958	Approved
0.6301	Remote Similarity	NPD3751	Discontinued
0.6296	Remote Similarity	NPD1512	Approved
0.6291	Remote Similarity	NPD2614	Approved
0.6289	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4359	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