NPASS Compound

Structure

NPC144745 OpenBabel07101719252D 24 24 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 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 -0.3660 9.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 10.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 8.5388 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 17 1 0 0 0 0 2 18 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 18 2 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 19 3 1 6 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.24
Volume:	376.404
LogP:	4.875
LogD:	4.546
LogS:	-4.719
# Rotatable Bonds:	12
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	3.282
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.87
MDCK Permeability:	1.833270289353095e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.353
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	99.6164321899414%
Volume Distribution (VD):	1.701
Pgp-substrate:	0.419277548789978%

ADMET: Metabolism

CYP1A2-inhibitor:	0.171
CYP1A2-substrate:	0.487
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.745
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	7.225
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.273
Skin Sensitization:	0.483
Carcinogencity:	0.78
Eye Corrosion:	0.02
Eye Irritation:	0.431
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC144745

Natural Product ID:	NPC144745
*Common Name:**	(R,6Z,10Z)-14-(Furan-3-Yl)-3,7,11-Trimethyltetradeca-6,10-Dienoic Acid
IUPAC Name:	(3R,6Z,10Z)-14-(furan-3-yl)-3,7,11-trimethyltetradeca-6,10-dienoic acid
Synonyms:
Standard InCHIKey:	PPIHVFQOURPZJE-WNULFKQXSA-N
Standard InCHI:	InChI=1S/C21H32O3/c1-17(9-5-11-19(3)15-21(22)23)7-4-8-18(2)10-6-12-20-13-14-24-16-20/h8-9,13-14,16,19H,4-7,10-12,15H2,1-3H3,(H,22,23)/b17-9-,18-8-/t19-/m1/s1
SMILES:	C[C@@H](CC(=O)O)CC/C=C(CC/C=C(CCCc1cocc1)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468820
PubChem CID:	24850053
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	=	80.0	ug.mL-1	PMID[548937]
NPT111	Cell Line	K562	Homo sapiens	LC50	>	100.0	ug.mL-1	PMID[548937]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[548937]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[548937]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[548937]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[548937]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	12.5	ug.mL-1	PMID[548937]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	25.0	ug.mL-1	PMID[548937]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[548937]

☑ 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 NPC144745 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	202
0.1-0.2	1240
0.2-0.3	3862
0.3-0.4	9579
0.4-0.5	11001
0.5-0.6	10904
0.6-0.7	5265
0.7-0.8	519
0.8-0.85	63
0.85-0.9	41
0.9-0.95	19
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208906
0.9237	High Similarity	NPC81912
0.9237	High Similarity	NPC329694
0.9237	High Similarity	NPC474260
0.9237	High Similarity	NPC329922
0.9231	High Similarity	NPC243269
0.9189	High Similarity	NPC1811
0.9189	High Similarity	NPC26157
0.916	High Similarity	NPC476016
0.916	High Similarity	NPC474830
0.9153	High Similarity	NPC71274
0.9153	High Similarity	NPC474829
0.9153	High Similarity	NPC75557
0.913	High Similarity	NPC473969
0.9099	High Similarity	NPC105249
0.9083	High Similarity	NPC474279
0.9083	High Similarity	NPC474438
0.9076	High Similarity	NPC46536
0.9076	High Similarity	NPC138139
0.906	High Similarity	NPC477967
0.9	High Similarity	NPC471521
0.9	High Similarity	NPC473356
0.9	High Similarity	NPC83178
0.8983	High Similarity	NPC476351
0.8983	High Similarity	NPC475818
0.8957	High Similarity	NPC131801
0.8926	High Similarity	NPC207294
0.8926	High Similarity	NPC112706
0.8919	High Similarity	NPC177331
0.8898	High Similarity	NPC289911
0.8898	High Similarity	NPC283284
0.8889	High Similarity	NPC474817
0.8862	High Similarity	NPC89133
0.8843	High Similarity	NPC471554
0.8843	High Similarity	NPC471573
0.8843	High Similarity	NPC473355
0.8843	High Similarity	NPC471501
0.8833	High Similarity	NPC471559
0.8824	High Similarity	NPC16922
0.8814	High Similarity	NPC474136
0.8783	High Similarity	NPC28054
0.875	High Similarity	NPC118853
0.872	High Similarity	NPC474407
0.872	High Similarity	NPC474425
0.872	High Similarity	NPC474426
0.8718	High Similarity	NPC21831
0.8718	High Similarity	NPC187547
0.871	High Similarity	NPC17681
0.8678	High Similarity	NPC179354
0.8655	High Similarity	NPC1848
0.864	High Similarity	NPC45358
0.864	High Similarity	NPC97740
0.8621	High Similarity	NPC150895
0.8607	High Similarity	NPC74612
0.8607	High Similarity	NPC23086
0.8595	High Similarity	NPC65735
0.8595	High Similarity	NPC477038
0.8595	High Similarity	NPC477965
0.8595	High Similarity	NPC188377
0.8583	High Similarity	NPC473379
0.8583	High Similarity	NPC317217
0.8583	High Similarity	NPC263870
0.8583	High Similarity	NPC471549
0.8559	High Similarity	NPC243704
0.8547	High Similarity	NPC45536
0.8537	High Similarity	NPC137570
0.85	High Similarity	NPC79557
0.8443	Intermediate Similarity	NPC130275
0.8403	Intermediate Similarity	NPC291619
0.8403	Intermediate Similarity	NPC254958
0.8346	Intermediate Similarity	NPC473982
0.8346	Intermediate Similarity	NPC471817
0.832	Intermediate Similarity	NPC477040
0.832	Intermediate Similarity	NPC477123
0.832	Intermediate Similarity	NPC477039
0.832	Intermediate Similarity	NPC477966
0.8319	Intermediate Similarity	NPC227660
0.8319	Intermediate Similarity	NPC217180
0.8319	Intermediate Similarity	NPC312525
0.8308	Intermediate Similarity	NPC215109
0.8308	Intermediate Similarity	NPC170604
0.8305	Intermediate Similarity	NPC205523
0.8279	Intermediate Similarity	NPC36255
0.8268	Intermediate Similarity	NPC298190
0.8268	Intermediate Similarity	NPC61788
0.8254	Intermediate Similarity	NPC120836
0.8254	Intermediate Similarity	NPC223063
0.824	Intermediate Similarity	NPC95567
0.824	Intermediate Similarity	NPC319140
0.8235	Intermediate Similarity	NPC476031
0.8235	Intermediate Similarity	NPC476014
0.8189	Intermediate Similarity	NPC476925
0.8182	Intermediate Similarity	NPC4898
0.8182	Intermediate Similarity	NPC202260
0.8182	Intermediate Similarity	NPC90953
0.8175	Intermediate Similarity	NPC476917
0.8175	Intermediate Similarity	NPC327527
0.8154	Intermediate Similarity	NPC14650
0.8154	Intermediate Similarity	NPC476947
0.8145	Intermediate Similarity	NPC83115
0.814	Intermediate Similarity	NPC470740
0.814	Intermediate Similarity	NPC218838
0.8134	Intermediate Similarity	NPC121158
0.8083	Intermediate Similarity	NPC474987
0.8083	Intermediate Similarity	NPC76844
0.808	Intermediate Similarity	NPC303010
0.808	Intermediate Similarity	NPC230979
0.8077	Intermediate Similarity	NPC288209
0.8077	Intermediate Similarity	NPC106247
0.8065	Intermediate Similarity	NPC272899
0.8062	Intermediate Similarity	NPC471545
0.8062	Intermediate Similarity	NPC473344
0.8062	Intermediate Similarity	NPC471544
0.8033	Intermediate Similarity	NPC137710
0.803	Intermediate Similarity	NPC473268
0.803	Intermediate Similarity	NPC186626
0.8015	Intermediate Similarity	NPC159786
0.8015	Intermediate Similarity	NPC158525
0.8015	Intermediate Similarity	NPC92941
0.8	Intermediate Similarity	NPC11821
0.7985	Intermediate Similarity	NPC148374
0.7984	Intermediate Similarity	NPC475092
0.7984	Intermediate Similarity	NPC477645
0.7955	Intermediate Similarity	NPC303217
0.7955	Intermediate Similarity	NPC46896
0.7955	Intermediate Similarity	NPC146872
0.7953	Intermediate Similarity	NPC246392
0.7953	Intermediate Similarity	NPC290955
0.7941	Intermediate Similarity	NPC267632
0.7937	Intermediate Similarity	NPC471074
0.7937	Intermediate Similarity	NPC473885
0.7907	Intermediate Similarity	NPC21460
0.7899	Intermediate Similarity	NPC22678
0.7895	Intermediate Similarity	NPC310830
0.7895	Intermediate Similarity	NPC307401
0.7895	Intermediate Similarity	NPC470742
0.7895	Intermediate Similarity	NPC42400
0.7891	Intermediate Similarity	NPC279877
0.7891	Intermediate Similarity	NPC26532
0.7891	Intermediate Similarity	NPC329707
0.7883	Intermediate Similarity	NPC476944
0.7883	Intermediate Similarity	NPC251865
0.7869	Intermediate Similarity	NPC212918
0.7852	Intermediate Similarity	NPC56197
0.7852	Intermediate Similarity	NPC473983
0.7852	Intermediate Similarity	NPC201370
0.7852	Intermediate Similarity	NPC67003
0.7846	Intermediate Similarity	NPC136340
0.7845	Intermediate Similarity	NPC42471
0.7842	Intermediate Similarity	NPC216755
0.7842	Intermediate Similarity	NPC471174
0.7842	Intermediate Similarity	NPC255414
0.7836	Intermediate Similarity	NPC236532
0.7836	Intermediate Similarity	NPC220094
0.7836	Intermediate Similarity	NPC476943
0.7829	Intermediate Similarity	NPC198904
0.7829	Intermediate Similarity	NPC208389
0.7805	Intermediate Similarity	NPC293424
0.7803	Intermediate Similarity	NPC471998
0.7795	Intermediate Similarity	NPC221798
0.7794	Intermediate Similarity	NPC205765
0.7778	Intermediate Similarity	NPC107571
0.7778	Intermediate Similarity	NPC140688
0.777	Intermediate Similarity	NPC346
0.7761	Intermediate Similarity	NPC64157
0.7761	Intermediate Similarity	NPC278832
0.776	Intermediate Similarity	NPC97566
0.7754	Intermediate Similarity	NPC267004
0.7754	Intermediate Similarity	NPC307346
0.7754	Intermediate Similarity	NPC261733
0.7754	Intermediate Similarity	NPC218712
0.7744	Intermediate Similarity	NPC265793
0.7734	Intermediate Similarity	NPC216810
0.773	Intermediate Similarity	NPC125182
0.773	Intermediate Similarity	NPC472654
0.773	Intermediate Similarity	NPC234494
0.773	Intermediate Similarity	NPC69647
0.7727	Intermediate Similarity	NPC293253
0.7727	Intermediate Similarity	NPC471006
0.7714	Intermediate Similarity	NPC476937
0.7714	Intermediate Similarity	NPC476938
0.7714	Intermediate Similarity	NPC250228
0.7704	Intermediate Similarity	NPC472376
0.7698	Intermediate Similarity	NPC270807
0.7698	Intermediate Similarity	NPC174915
0.7692	Intermediate Similarity	NPC59502
0.7681	Intermediate Similarity	NPC80635
0.7681	Intermediate Similarity	NPC476946
0.7676	Intermediate Similarity	NPC212257
0.7676	Intermediate Similarity	NPC470997
0.7674	Intermediate Similarity	NPC474476
0.7674	Intermediate Similarity	NPC141059
0.7661	Intermediate Similarity	NPC87466
0.7661	Intermediate Similarity	NPC206007
0.766	Intermediate Similarity	NPC476941
0.766	Intermediate Similarity	NPC113428
0.766	Intermediate Similarity	NPC476942
0.766	Intermediate Similarity	NPC93666
0.766	Intermediate Similarity	NPC61284
0.7656	Intermediate Similarity	NPC300098

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 NPC144745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	995
0.2-0.3	1901
0.3-0.4	2788
0.4-0.5	2045
0.5-0.6	965
0.6-0.7	256
0.7-0.8	14
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
0.791	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6832	Phase 2
0.7364	Intermediate Similarity	NPD9717	Approved
0.7328	Intermediate Similarity	NPD2797	Approved
0.7258	Intermediate Similarity	NPD1241	Discontinued
0.7246	Intermediate Similarity	NPD2799	Discontinued
0.7163	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7114	Intermediate Similarity	NPD5761	Phase 2
0.7114	Intermediate Similarity	NPD5760	Phase 2
0.7113	Intermediate Similarity	NPD4628	Phase 3
0.7109	Intermediate Similarity	NPD9545	Approved
0.7109	Intermediate Similarity	NPD1894	Discontinued
0.7107	Intermediate Similarity	NPD3134	Approved
0.7103	Intermediate Similarity	NPD6273	Approved
0.7099	Intermediate Similarity	NPD1608	Approved
0.7068	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD2313	Discontinued
0.7023	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2344	Approved
0.7015	Intermediate Similarity	NPD2798	Approved
0.7015	Intermediate Similarity	NPD1019	Discontinued
0.7	Intermediate Similarity	NPD4308	Phase 3
0.6953	Remote Similarity	NPD9493	Approved
0.695	Remote Similarity	NPD1551	Phase 2
0.694	Remote Similarity	NPD6362	Approved
0.6934	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6798	Discontinued
0.6897	Remote Similarity	NPD7440	Discontinued
0.6897	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5647	Approved
0.687	Remote Similarity	NPD17	Approved
0.687	Remote Similarity	NPD1778	Approved
0.6866	Remote Similarity	NPD1876	Approved
0.6855	Remote Similarity	NPD2182	Approved
0.6842	Remote Similarity	NPD3972	Approved
0.6835	Remote Similarity	NPD4307	Phase 2
0.6831	Remote Similarity	NPD2935	Discontinued
0.6828	Remote Similarity	NPD2309	Approved
0.6824	Remote Similarity	NPD920	Approved
0.6818	Remote Similarity	NPD3496	Discontinued
0.6815	Remote Similarity	NPD3267	Approved
0.6815	Remote Similarity	NPD3266	Approved
0.6812	Remote Similarity	NPD411	Approved
0.6803	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5585	Approved
0.6786	Remote Similarity	NPD447	Suspended
0.6786	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2346	Discontinued
0.6783	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6002	Phase 3
0.6783	Remote Similarity	NPD6005	Phase 3
0.6783	Remote Similarity	NPD6004	Phase 3
0.6774	Remote Similarity	NPD1358	Approved
0.6769	Remote Similarity	NPD9092	Discovery
0.6763	Remote Similarity	NPD6233	Phase 2
0.6763	Remote Similarity	NPD4062	Phase 3
0.6759	Remote Similarity	NPD7003	Approved
0.675	Remote Similarity	NPD1238	Approved
0.6741	Remote Similarity	NPD1283	Approved
0.6738	Remote Similarity	NPD6653	Approved
0.6735	Remote Similarity	NPD6799	Approved
0.6733	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2684	Approved
0.6716	Remote Similarity	NPD1481	Phase 2
0.6715	Remote Similarity	NPD454	Approved
0.6715	Remote Similarity	NPD9494	Approved
0.6714	Remote Similarity	NPD3142	Approved
0.6714	Remote Similarity	NPD3140	Approved
0.6713	Remote Similarity	NPD4476	Approved
0.6713	Remote Similarity	NPD4477	Approved
0.6712	Remote Similarity	NPD2354	Approved
0.6712	Remote Similarity	NPD3887	Approved
0.6692	Remote Similarity	NPD3847	Discontinued
0.6691	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3764	Approved
0.669	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD4618	Approved
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD2614	Approved
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4622	Approved
0.6667	Remote Similarity	NPD7819	Suspended
0.6645	Remote Similarity	NPD7411	Suspended
0.6644	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4110	Phase 3
0.6644	Remote Similarity	NPD3750	Approved
0.6643	Remote Similarity	NPD7033	Discontinued
0.6643	Remote Similarity	NPD8032	Phase 2
0.6642	Remote Similarity	NPD1535	Discovery
0.6641	Remote Similarity	NPD7843	Approved
0.6641	Remote Similarity	NPD5535	Approved
0.6623	Remote Similarity	NPD7458	Discontinued
0.6623	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5958	Discontinued
0.6613	Remote Similarity	NPD9697	Approved
0.6597	Remote Similarity	NPD2796	Approved
0.6587	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7768	Phase 2
0.6579	Remote Similarity	NPD6599	Discontinued
0.6573	Remote Similarity	NPD5688	Approved
0.6573	Remote Similarity	NPD5689	Approved
0.6573	Remote Similarity	NPD7097	Phase 1
0.6566	Remote Similarity	NPD8434	Phase 2
0.6564	Remote Similarity	NPD6764	Approved
0.6564	Remote Similarity	NPD6765	Approved
0.6552	Remote Similarity	NPD1471	Phase 3
0.6552	Remote Similarity	NPD2353	Approved
0.6552	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4359	Approved
0.6541	Remote Similarity	NPD5691	Approved
0.6538	Remote Similarity	NPD7075	Discontinued
0.6538	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5049	Phase 3
0.6532	Remote Similarity	NPD164	Approved
0.6531	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3748	Approved
0.6522	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1281	Approved
0.651	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4534	Discontinued
0.6507	Remote Similarity	NPD1549	Phase 2
0.65	Remote Similarity	NPD7095	Approved
0.65	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD919	Approved
0.6496	Remote Similarity	NPD3225	Approved
0.6494	Remote Similarity	NPD7577	Discontinued
0.6493	Remote Similarity	NPD4626	Approved
0.649	Remote Similarity	NPD5403	Approved
0.649	Remote Similarity	NPD3869	Phase 3
0.649	Remote Similarity	NPD3873	Phase 3
0.6489	Remote Similarity	NPD7157	Approved
0.6479	Remote Similarity	NPD2979	Phase 3
0.6479	Remote Similarity	NPD4140	Approved
0.6479	Remote Similarity	NPD1240	Approved
0.6467	Remote Similarity	NPD5401	Approved
0.6467	Remote Similarity	NPD4662	Approved
0.6467	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4661	Approved
0.6463	Remote Similarity	NPD6559	Discontinued
0.6452	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3749	Approved
0.6407	Remote Similarity	NPD6785	Approved
0.6407	Remote Similarity	NPD6784	Approved
0.6406	Remote Similarity	NPD2067	Discontinued
0.6405	Remote Similarity	NPD3226	Approved
0.64	Remote Similarity	NPD5909	Discontinued
0.6397	Remote Similarity	NPD422	Phase 1
0.6395	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1607	Approved
0.6387	Remote Similarity	NPD6801	Discontinued
0.6387	Remote Similarity	NPD6280	Approved
0.6387	Remote Similarity	NPD6279	Approved
0.6385	Remote Similarity	NPD821	Approved
0.6383	Remote Similarity	NPD5163	Phase 2
0.6378	Remote Similarity	NPD9267	Approved
0.6378	Remote Similarity	NPD290	Approved
0.6378	Remote Similarity	NPD9263	Approved
0.6378	Remote Similarity	NPD9264	Approved
0.6378	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6808	Phase 2
0.637	Remote Similarity	NPD2240	Approved
0.637	Remote Similarity	NPD2239	Approved
0.6364	Remote Similarity	NPD6671	Approved
0.6364	Remote Similarity	NPD4060	Phase 1
0.6358	Remote Similarity	NPD2533	Approved
0.6358	Remote Similarity	NPD2534	Approved
0.6358	Remote Similarity	NPD2532	Approved
0.6358	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD9258	Approved
0.6356	Remote Similarity	NPD9256	Approved
0.6351	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD987	Approved
0.6328	Remote Similarity	NPD74	Approved
0.6328	Remote Similarity	NPD9266	Approved
0.6327	Remote Similarity	NPD5763	Approved
0.6327	Remote Similarity	NPD5762	Approved
0.632	Remote Similarity	NPD6647	Phase 2
0.6319	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2186	Approved
0.6312	Remote Similarity	NPD8127	Discontinued
0.6306	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD2296	Approved
0.6304	Remote Similarity	NPD3685	Discontinued
0.6301	Remote Similarity	NPD1510	Phase 2
0.6299	Remote Similarity	NPD968	Approved
0.6296	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4870	Approved
0.6289	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2897	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