NPASS Compound

Structure

NPC179354 OpenBabel07101719252D 26 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7321 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 0.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.9945 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 2.2321 0.8660 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 3.7321 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 17 1 0 0 0 0 4 10 1 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 14 23 2 0 0 0 0 15 21 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 19 22 1 6 0 0 0 20 21 1 6 0 0 0 20 22 1 0 0 0 0 21 3 1 1 0 0 0 22 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	3.28
LogD:	3.64
LogS:	-4.431
# Rotatable Bonds:	7
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	4.498
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.959
MDCK Permeability:	3.2840292988112196e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.178
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.516
Plasma Protein Binding (PPB):	74.23519134521484%
Volume Distribution (VD):	1.895
Pgp-substrate:	15.085209846496582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.352
CYP2C19-substrate:	0.228
CYP2C9-inhibitor:	0.388
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.927
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	5.393
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.752
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.37
Carcinogencity:	0.244
Eye Corrosion:	0.096
Eye Irritation:	0.917
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC179354

Natural Product ID:	NPC179354
*Common Name:**	Potamogetonyde
IUPAC Name:	[(1R,4aR,5R,8aR)-4a-formyl-5-[2-(furan-3-yl)ethyl]-1-methyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl acetate
Synonyms:	Potamogetonyde
Standard InCHIKey:	OPDQOKREXYCJHD-YUMYIRISSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-16-5-8-20-21(3,15-26-17(2)24)10-4-11-22(20,14-23)19(16)7-6-18-9-12-25-13-18/h9,12-14,19-20H,1,4-8,10-11,15H2,2-3H3/t19-,20-,21+,22-/m1/s1
SMILES:	O=C[C@]12CCC[C@@]([C@H]2CCC(=C)[C@H]1CCc1cocc1)(C)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504334
PubChem CID:	485584
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO1270	Potamogeton malaianus	Species	Potamogetonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277765]
NPO1270	Potamogeton malaianus	Species	Potamogetonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
MIC	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[465050]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	31.0	ug.mL-1	PMID[465050]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	8.0	ug.mL-1	PMID[465050]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11.0	ug.mL-1	PMID[465050]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30.0	ug.mL-1	PMID[465050]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[465050]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	100.0	ug.mL-1	PMID[465050]

☑ 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 NPC179354 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	268
0.1-0.2	1424
0.2-0.3	2863
0.3-0.4	6973
0.4-0.5	12958
0.5-0.6	11006
0.6-0.7	6259
0.7-0.8	736
0.8-0.85	143
0.85-0.9	50
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9829	High Similarity	NPC16922
0.9748	High Similarity	NPC74612
0.9583	High Similarity	NPC138139
0.9583	High Similarity	NPC46536
0.9355	High Similarity	NPC89133
0.9268	High Similarity	NPC112706
0.9268	High Similarity	NPC207294
0.9187	High Similarity	NPC83178
0.9145	High Similarity	NPC150895
0.9113	High Similarity	NPC477040
0.9113	High Similarity	NPC476917
0.9113	High Similarity	NPC327527
0.9091	High Similarity	NPC36255
0.907	High Similarity	NPC42400
0.9024	High Similarity	NPC230979
0.9	High Similarity	NPC476943
0.8976	High Similarity	NPC471817
0.8968	High Similarity	NPC476925
0.896	High Similarity	NPC477966
0.896	High Similarity	NPC477123
0.8952	High Similarity	NPC23086
0.8943	High Similarity	NPC130275
0.8943	High Similarity	NPC83115
0.8934	High Similarity	NPC317217
0.8923	High Similarity	NPC310830
0.8917	High Similarity	NPC243704
0.8898	High Similarity	NPC298190
0.8864	High Similarity	NPC56197
0.8846	High Similarity	NPC146872
0.8833	High Similarity	NPC212918
0.881	High Similarity	NPC477039
0.879	High Similarity	NPC477038
0.879	High Similarity	NPC477965
0.879	High Similarity	NPC243269
0.878	High Similarity	NPC477967
0.8779	High Similarity	NPC307401
0.8769	High Similarity	NPC92941
0.876	High Similarity	NPC470740
0.874	High Similarity	NPC223063
0.874	High Similarity	NPC198904
0.874	High Similarity	NPC120836
0.874	High Similarity	NPC208389
0.8731	High Similarity	NPC121158
0.8712	High Similarity	NPC220094
0.8678	High Similarity	NPC208906
0.8678	High Similarity	NPC144745
0.8667	High Similarity	NPC267632
0.8657	High Similarity	NPC20500
0.8647	High Similarity	NPC202260
0.8647	High Similarity	NPC90953
0.8636	High Similarity	NPC470742
0.8615	High Similarity	NPC471006
0.8605	High Similarity	NPC61788
0.8603	High Similarity	NPC476944
0.8603	High Similarity	NPC238843
0.8603	High Similarity	NPC251865
0.8603	High Similarity	NPC142113
0.8603	High Similarity	NPC199044
0.8571	High Similarity	NPC236532
0.8561	High Similarity	NPC46896
0.856	High Similarity	NPC272899
0.855	High Similarity	NPC471998
0.8547	High Similarity	NPC471521
0.8547	High Similarity	NPC473356
0.8537	High Similarity	NPC473969
0.8529	High Similarity	NPC223415
0.8492	Intermediate Similarity	NPC65735
0.8492	Intermediate Similarity	NPC188377
0.8487	Intermediate Similarity	NPC105249
0.8485	Intermediate Similarity	NPC158525
0.8485	Intermediate Similarity	NPC476947
0.8478	Intermediate Similarity	NPC471292
0.8478	Intermediate Similarity	NPC262198
0.8473	Intermediate Similarity	NPC293253
0.8473	Intermediate Similarity	NPC218838
0.845	Intermediate Similarity	NPC59502
0.8444	Intermediate Similarity	NPC148374
0.8444	Intermediate Similarity	NPC67003
0.8438	Intermediate Similarity	NPC319140
0.8438	Intermediate Similarity	NPC95567
0.8425	Intermediate Similarity	NPC473885
0.8425	Intermediate Similarity	NPC303010
0.8425	Intermediate Similarity	NPC471074
0.8417	Intermediate Similarity	NPC216755
0.8417	Intermediate Similarity	NPC71821
0.8417	Intermediate Similarity	NPC221809
0.8417	Intermediate Similarity	NPC471174
0.8417	Intermediate Similarity	NPC255414
0.84	Intermediate Similarity	NPC97566
0.8394	Intermediate Similarity	NPC470741
0.8385	Intermediate Similarity	NPC21460
0.8374	Intermediate Similarity	NPC131801
0.8372	Intermediate Similarity	NPC26532
0.8358	Intermediate Similarity	NPC310043
0.8358	Intermediate Similarity	NPC170604
0.8358	Intermediate Similarity	NPC215109
0.8345	Intermediate Similarity	NPC233763
0.8345	Intermediate Similarity	NPC346
0.8345	Intermediate Similarity	NPC276676
0.8333	Intermediate Similarity	NPC277525
0.8306	Intermediate Similarity	NPC87466
0.8298	Intermediate Similarity	NPC471001
0.8298	Intermediate Similarity	NPC69647
0.8298	Intermediate Similarity	NPC472654
0.8298	Intermediate Similarity	NPC195325
0.8298	Intermediate Similarity	NPC125182
0.8298	Intermediate Similarity	NPC234494
0.8298	Intermediate Similarity	NPC470791
0.8298	Intermediate Similarity	NPC470790
0.8295	Intermediate Similarity	NPC476016
0.8295	Intermediate Similarity	NPC246392
0.8295	Intermediate Similarity	NPC290955
0.8286	Intermediate Similarity	NPC10088
0.8286	Intermediate Similarity	NPC470941
0.8286	Intermediate Similarity	NPC250228
0.8284	Intermediate Similarity	NPC214572
0.8281	Intermediate Similarity	NPC75557
0.8281	Intermediate Similarity	NPC71274
0.8281	Intermediate Similarity	NPC471559
0.8281	Intermediate Similarity	NPC474829
0.8273	Intermediate Similarity	NPC56731
0.8264	Intermediate Similarity	NPC26157
0.8264	Intermediate Similarity	NPC1811
0.8261	Intermediate Similarity	NPC243577
0.8258	Intermediate Similarity	NPC471995
0.8248	Intermediate Similarity	NPC205765
0.8239	Intermediate Similarity	NPC156189
0.8239	Intermediate Similarity	NPC159927
0.8239	Intermediate Similarity	NPC476122
0.8239	Intermediate Similarity	NPC228842
0.8239	Intermediate Similarity	NPC469335
0.8239	Intermediate Similarity	NPC477404
0.8239	Intermediate Similarity	NPC470997
0.8239	Intermediate Similarity	NPC46551
0.8239	Intermediate Similarity	NPC212257
0.8239	Intermediate Similarity	NPC196864
0.8231	Intermediate Similarity	NPC474279
0.8231	Intermediate Similarity	NPC474438
0.8217	Intermediate Similarity	NPC81912
0.8217	Intermediate Similarity	NPC329694
0.8217	Intermediate Similarity	NPC329922
0.8217	Intermediate Similarity	NPC474260
0.8211	Intermediate Similarity	NPC28054
0.8203	Intermediate Similarity	NPC178382
0.8188	Intermediate Similarity	NPC473152
0.8188	Intermediate Similarity	NPC263337
0.8188	Intermediate Similarity	NPC52412
0.8182	Intermediate Similarity	NPC272590
0.8182	Intermediate Similarity	NPC18135
0.8175	Intermediate Similarity	NPC90296
0.8156	Intermediate Similarity	NPC476938
0.8156	Intermediate Similarity	NPC476937
0.8154	Intermediate Similarity	NPC474830
0.8154	Intermediate Similarity	NPC137570
0.8143	Intermediate Similarity	NPC34056
0.8143	Intermediate Similarity	NPC290038
0.8143	Intermediate Similarity	NPC5676
0.8143	Intermediate Similarity	NPC185456
0.814	Intermediate Similarity	NPC300098
0.814	Intermediate Similarity	NPC290193
0.8129	Intermediate Similarity	NPC476946
0.8129	Intermediate Similarity	NPC80635
0.8125	Intermediate Similarity	NPC268905
0.8125	Intermediate Similarity	NPC33938
0.8125	Intermediate Similarity	NPC476201
0.8125	Intermediate Similarity	NPC469503
0.8125	Intermediate Similarity	NPC29695
0.8125	Intermediate Similarity	NPC476351
0.8125	Intermediate Similarity	NPC75906
0.8125	Intermediate Similarity	NPC294511
0.8125	Intermediate Similarity	NPC471002
0.8125	Intermediate Similarity	NPC121615
0.8125	Intermediate Similarity	NPC182427
0.8125	Intermediate Similarity	NPC308205
0.8125	Intermediate Similarity	NPC322546
0.8125	Intermediate Similarity	NPC246164
0.812	Intermediate Similarity	NPC473982
0.8112	Intermediate Similarity	NPC5180
0.811	Intermediate Similarity	NPC1848
0.8102	Intermediate Similarity	NPC474722
0.8099	Intermediate Similarity	NPC93666
0.8099	Intermediate Similarity	NPC476942
0.8099	Intermediate Similarity	NPC476941
0.8092	Intermediate Similarity	NPC279877
0.8092	Intermediate Similarity	NPC329707
0.8085	Intermediate Similarity	NPC62799
0.8085	Intermediate Similarity	NPC470999
0.8071	Intermediate Similarity	NPC86935
0.8069	Intermediate Similarity	NPC282445
0.8069	Intermediate Similarity	NPC178932
0.8069	Intermediate Similarity	NPC30222
0.8069	Intermediate Similarity	NPC471863
0.8062	Intermediate Similarity	NPC118853
0.806	Intermediate Similarity	NPC474426
0.806	Intermediate Similarity	NPC474407
0.806	Intermediate Similarity	NPC474425
0.8056	Intermediate Similarity	NPC116717
0.8056	Intermediate Similarity	NPC291150
0.8047	Intermediate Similarity	NPC289911
0.8047	Intermediate Similarity	NPC283284

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 NPC179354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	993
0.2-0.3	1597
0.3-0.4	2741
0.4-0.5	2198
0.5-0.6	1105
0.6-0.7	246
0.7-0.8	17
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
0.7971	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5761	Phase 2
0.7651	Intermediate Similarity	NPD5760	Phase 2
0.7552	Intermediate Similarity	NPD4628	Phase 3
0.7534	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7447	Intermediate Similarity	NPD2799	Discontinued
0.7444	Intermediate Similarity	NPD3972	Approved
0.7405	Intermediate Similarity	NPD5585	Approved
0.7348	Intermediate Similarity	NPD17	Approved
0.7343	Intermediate Similarity	NPD1471	Phase 3
0.7338	Intermediate Similarity	NPD8032	Phase 2
0.7333	Intermediate Similarity	NPD1876	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7279	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD920	Approved
0.7244	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1241	Discontinued
0.7192	Intermediate Similarity	NPD7003	Approved
0.7185	Intermediate Similarity	NPD1608	Approved
0.7163	Intermediate Similarity	NPD4307	Phase 2
0.7163	Intermediate Similarity	NPD2979	Phase 3
0.716	Intermediate Similarity	NPD6764	Approved
0.716	Intermediate Similarity	NPD6765	Approved
0.7153	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4359	Approved
0.7114	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6355	Discontinued
0.7111	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1281	Approved
0.7103	Intermediate Similarity	NPD2346	Discontinued
0.7103	Intermediate Similarity	NPD2344	Approved
0.7101	Intermediate Similarity	NPD2798	Approved
0.7087	Intermediate Similarity	NPD2182	Approved
0.7083	Intermediate Similarity	NPD3748	Approved
0.7071	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8434	Phase 2
0.7039	Intermediate Similarity	NPD7458	Discontinued
0.7039	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3887	Approved
0.7007	Intermediate Similarity	NPD1243	Approved
0.7006	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6599	Discontinued
0.6988	Remote Similarity	NPD6785	Approved
0.6988	Remote Similarity	NPD6784	Approved
0.6978	Remote Similarity	NPD1019	Discontinued
0.6968	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD4308	Phase 3
0.6959	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1283	Approved
0.6934	Remote Similarity	NPD9717	Approved
0.6929	Remote Similarity	NPD3134	Approved
0.6923	Remote Similarity	NPD4140	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD2531	Phase 2
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD2796	Approved
0.6918	Remote Similarity	NPD2438	Suspended
0.6918	Remote Similarity	NPD2935	Discontinued
0.6913	Remote Similarity	NPD2309	Approved
0.6906	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1203	Approved
0.6901	Remote Similarity	NPD3764	Approved
0.6899	Remote Similarity	NPD919	Approved
0.6889	Remote Similarity	NPD5691	Approved
0.6887	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6808	Phase 2
0.6875	Remote Similarity	NPD4618	Approved
0.6875	Remote Similarity	NPD1933	Approved
0.6875	Remote Similarity	NPD4622	Approved
0.6871	Remote Similarity	NPD2353	Approved
0.6871	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5535	Approved
0.6855	Remote Similarity	NPD1238	Approved
0.6853	Remote Similarity	NPD4870	Approved
0.6846	Remote Similarity	NPD3750	Approved
0.6846	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1778	Approved
0.6821	Remote Similarity	NPD6799	Approved
0.6818	Remote Similarity	NPD3226	Approved
0.6815	Remote Similarity	NPD1894	Discontinued
0.681	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3142	Approved
0.6806	Remote Similarity	NPD3140	Approved
0.6795	Remote Similarity	NPD6279	Approved
0.6795	Remote Similarity	NPD6280	Approved
0.6788	Remote Similarity	NPD3496	Discontinued
0.6783	Remote Similarity	NPD6798	Discontinued
0.6783	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5689	Approved
0.6781	Remote Similarity	NPD5688	Approved
0.6772	Remote Similarity	NPD164	Approved
0.6765	Remote Similarity	NPD1651	Approved
0.6763	Remote Similarity	NPD5327	Phase 3
0.6757	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6002	Phase 3
0.6757	Remote Similarity	NPD6004	Phase 3
0.6757	Remote Similarity	NPD6005	Phase 3
0.6752	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1358	Approved
0.6739	Remote Similarity	NPD6287	Discontinued
0.6731	Remote Similarity	NPD7411	Suspended
0.6731	Remote Similarity	NPD6873	Phase 2
0.673	Remote Similarity	NPD3749	Approved
0.6713	Remote Similarity	NPD7095	Approved
0.6711	Remote Similarity	NPD4534	Discontinued
0.6711	Remote Similarity	NPD2897	Discontinued
0.6708	Remote Similarity	NPD8127	Discontinued
0.6692	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD9545	Approved
0.669	Remote Similarity	NPD4060	Phase 1
0.6689	Remote Similarity	NPD2354	Approved
0.6688	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3869	Phase 3
0.6688	Remote Similarity	NPD3873	Phase 3
0.6667	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD5494	Approved
0.6645	Remote Similarity	NPD7440	Discontinued
0.6643	Remote Similarity	NPD2614	Approved
0.6642	Remote Similarity	NPD5951	Approved
0.6625	Remote Similarity	NPD7075	Discontinued
0.6624	Remote Similarity	NPD5890	Approved
0.6624	Remote Similarity	NPD5889	Approved
0.6623	Remote Similarity	NPD8166	Discontinued
0.6622	Remote Similarity	NPD7033	Discontinued
0.6621	Remote Similarity	NPD4062	Phase 3
0.6621	Remote Similarity	NPD6233	Phase 2
0.662	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5647	Approved
0.6619	Remote Similarity	NPD1611	Approved
0.6601	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5958	Discontinued
0.66	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7008	Discontinued
0.6594	Remote Similarity	NPD4626	Approved
0.6593	Remote Similarity	NPD7157	Approved
0.6589	Remote Similarity	NPD9697	Approved
0.6582	Remote Similarity	NPD6801	Discontinued
0.6571	Remote Similarity	NPD1481	Phase 2
0.6558	Remote Similarity	NPD2532	Approved
0.6558	Remote Similarity	NPD2533	Approved
0.6558	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD2534	Approved
0.6552	Remote Similarity	NPD411	Approved
0.6549	Remote Similarity	NPD6362	Approved
0.6548	Remote Similarity	NPD6559	Discontinued
0.6547	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD3847	Discontinued
0.6541	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7236	Approved
0.6533	Remote Similarity	NPD5763	Approved
0.6533	Remote Similarity	NPD5762	Approved
0.6531	Remote Similarity	NPD447	Suspended
0.6519	Remote Similarity	NPD6677	Suspended
0.6516	Remote Similarity	NPD5049	Phase 3
0.6507	Remote Similarity	NPD6663	Approved
0.6506	Remote Similarity	NPD7177	Discontinued
0.6503	Remote Similarity	NPD1247	Approved
0.65	Remote Similarity	NPD1535	Discovery
0.65	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1549	Phase 2
0.6486	Remote Similarity	NPD6653	Approved
0.6485	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3225	Approved
0.6474	Remote Similarity	NPD7427	Discontinued
0.6474	Remote Similarity	NPD5403	Approved
0.6467	Remote Similarity	NPD6100	Approved
0.6467	Remote Similarity	NPD5844	Phase 1
0.6467	Remote Similarity	NPD6099	Approved
0.6458	Remote Similarity	NPD5736	Approved
0.6458	Remote Similarity	NPD9494	Approved
0.6456	Remote Similarity	NPD6585	Discontinued
0.6456	Remote Similarity	NPD7028	Phase 2
0.6452	Remote Similarity	NPD5401	Approved
0.6447	Remote Similarity	NPD2800	Approved
0.6443	Remote Similarity	NPD7097	Phase 1
0.6429	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3926	Phase 2
0.6424	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD9493	Approved
0.6415	Remote Similarity	NPD6386	Approved
0.6415	Remote Similarity	NPD6385	Approved
0.641	Remote Similarity	NPD2186	Approved
0.6405	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD3024	Approved
0.6403	Remote Similarity	NPD3025	Approved
0.64	Remote Similarity	NPD1510	Phase 2
0.6398	Remote Similarity	NPD3817	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