NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	279.11
Volume:	275.353
LogP:	0.459
LogD:	0.117
LogS:	-2.426
# Rotatable Bonds:	3
TPSA:	102.94
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	3.507
Fsp3:	0.5
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:	-5.244
MDCK Permeability:	3.087434743065387e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.322
Human Intestinal Absorption (HIA):	0.8
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.8

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	58.78048324584961%
Volume Distribution (VD):	0.846
Pgp-substrate:	37.19247817993164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.153
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	3.216
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.218
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.23
Carcinogencity:	0.832
Eye Corrosion:	0.035
Eye Irritation:	0.458
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC198798

Natural Product ID:	NPC198798
*Common Name:**	Niazirin
IUPAC Name:	2-[4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenyl]acetonitrile
Synonyms:	Niazirin
Standard InCHIKey:	OBJREHLZEIEGDU-CNJBRALLSA-N
Standard InCHI:	InChI=1S/C14H17NO5/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-7-15/h2-5,8,11-14,16-18H,6H2,1H3/t8-,11-,12+,13+,14-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1ccc(cc1)CC#N)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446981
PubChem CID:	129556
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)83306-8]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932128]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24024688]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798960]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO823	Senecio cathcartensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8703	Monopteryx uaucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4221	Fusarium sacchari	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7963	Excoecaria acerifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8339	Lithothamnion corallioides	Species	Hapalidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7266	Goupia glabra	Species	Goupiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1585	Onobrychis bobrovii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2501	Trifolium strepens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5937	Garrya laurifolia	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2703	Petteria ramentacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4858	Helipterum gnaphaloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5021	Podospora curvicolla	Species	Lasiosphaeriaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	45000.0	nM	PMID[549642]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	1.0	%	PMID[549642]

☑ 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 NPC198798 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	228
0.1-0.2	1334
0.2-0.3	4329
0.3-0.4	11974
0.4-0.5	6985
0.5-0.6	8535
0.6-0.7	7527
0.7-0.8	1629
0.8-0.85	126
0.85-0.9	21
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC469708
0.9333	High Similarity	NPC60589
0.9187	High Similarity	NPC212176
0.9098	High Similarity	NPC469412
0.9098	High Similarity	NPC198734
0.9098	High Similarity	NPC269242
0.896	High Similarity	NPC287429
0.8952	High Similarity	NPC476142
0.876	High Similarity	NPC26653
0.876	High Similarity	NPC270849
0.872	High Similarity	NPC226712
0.8692	High Similarity	NPC80600
0.8692	High Similarity	NPC472024
0.8682	High Similarity	NPC302378
0.8615	High Similarity	NPC248355
0.8615	High Similarity	NPC166040
0.8615	High Similarity	NPC295970
0.8595	High Similarity	NPC120217
0.8537	High Similarity	NPC175771
0.8529	High Similarity	NPC195814
0.8525	High Similarity	NPC313193
0.8519	High Similarity	NPC36434
0.8485	Intermediate Similarity	NPC9912
0.8473	Intermediate Similarity	NPC97326
0.8456	Intermediate Similarity	NPC298821
0.845	Intermediate Similarity	NPC470510
0.845	Intermediate Similarity	NPC12308
0.8433	Intermediate Similarity	NPC187194
0.8421	Intermediate Similarity	NPC162093
0.8409	Intermediate Similarity	NPC474491
0.8394	Intermediate Similarity	NPC123761
0.8387	Intermediate Similarity	NPC148055
0.8374	Intermediate Similarity	NPC157338
0.8358	Intermediate Similarity	NPC215833
0.8358	Intermediate Similarity	NPC294166
0.8358	Intermediate Similarity	NPC49074
0.8358	Intermediate Similarity	NPC69513
0.8358	Intermediate Similarity	NPC25821
0.8358	Intermediate Similarity	NPC115022
0.8346	Intermediate Similarity	NPC121376
0.8346	Intermediate Similarity	NPC248307
0.8346	Intermediate Similarity	NPC65942
0.8333	Intermediate Similarity	NPC307110
0.832	Intermediate Similarity	NPC122245
0.832	Intermediate Similarity	NPC266389
0.832	Intermediate Similarity	NPC216605
0.8309	Intermediate Similarity	NPC294470
0.8296	Intermediate Similarity	NPC471029
0.8296	Intermediate Similarity	NPC13745
0.8296	Intermediate Similarity	NPC48863
0.8296	Intermediate Similarity	NPC476411
0.8296	Intermediate Similarity	NPC251981
0.8284	Intermediate Similarity	NPC303422
0.8284	Intermediate Similarity	NPC299144
0.8284	Intermediate Similarity	NPC26080
0.8284	Intermediate Similarity	NPC85799
0.8284	Intermediate Similarity	NPC165686
0.8271	Intermediate Similarity	NPC262606
0.8258	Intermediate Similarity	NPC146540
0.8258	Intermediate Similarity	NPC40377
0.8248	Intermediate Similarity	NPC138738
0.8248	Intermediate Similarity	NPC470413
0.8248	Intermediate Similarity	NPC262328
0.8248	Intermediate Similarity	NPC87777
0.8235	Intermediate Similarity	NPC55040
0.8235	Intermediate Similarity	NPC470236
0.8235	Intermediate Similarity	NPC79957
0.8235	Intermediate Similarity	NPC238243
0.8226	Intermediate Similarity	NPC142319
0.8214	Intermediate Similarity	NPC136951
0.8214	Intermediate Similarity	NPC161155
0.8214	Intermediate Similarity	NPC97004
0.8197	Intermediate Similarity	NPC46844
0.8195	Intermediate Similarity	NPC218003
0.8175	Intermediate Similarity	NPC138350
0.8175	Intermediate Similarity	NPC40664
0.8175	Intermediate Similarity	NPC164857
0.8175	Intermediate Similarity	NPC37468
0.8175	Intermediate Similarity	NPC3293
0.8175	Intermediate Similarity	NPC165482
0.8175	Intermediate Similarity	NPC197723
0.8162	Intermediate Similarity	NPC35731
0.8162	Intermediate Similarity	NPC34456
0.8162	Intermediate Similarity	NPC470881
0.8162	Intermediate Similarity	NPC188555
0.8162	Intermediate Similarity	NPC130496
0.8156	Intermediate Similarity	NPC97282
0.8148	Intermediate Similarity	NPC269421
0.8148	Intermediate Similarity	NPC252833
0.8143	Intermediate Similarity	NPC178466
0.8143	Intermediate Similarity	NPC63628
0.8125	Intermediate Similarity	NPC469702
0.8125	Intermediate Similarity	NPC282409
0.8116	Intermediate Similarity	NPC124149
0.8102	Intermediate Similarity	NPC212729
0.8088	Intermediate Similarity	NPC6836
0.8088	Intermediate Similarity	NPC132895
0.8074	Intermediate Similarity	NPC475067
0.8074	Intermediate Similarity	NPC166168
0.8071	Intermediate Similarity	NPC76871
0.8071	Intermediate Similarity	NPC108674
0.8071	Intermediate Similarity	NPC79908
0.8071	Intermediate Similarity	NPC210192
0.8062	Intermediate Similarity	NPC476445
0.8062	Intermediate Similarity	NPC476448
0.8062	Intermediate Similarity	NPC469548
0.8058	Intermediate Similarity	NPC98777
0.8058	Intermediate Similarity	NPC100389
0.8058	Intermediate Similarity	NPC212770
0.8056	Intermediate Similarity	NPC139699
0.8056	Intermediate Similarity	NPC114659
0.8043	Intermediate Similarity	NPC172818
0.8043	Intermediate Similarity	NPC199459
0.8043	Intermediate Similarity	NPC242028
0.8043	Intermediate Similarity	NPC186418
0.8043	Intermediate Similarity	NPC203230
0.8043	Intermediate Similarity	NPC52277
0.8043	Intermediate Similarity	NPC166180
0.8043	Intermediate Similarity	NPC475628
0.8043	Intermediate Similarity	NPC25695
0.8043	Intermediate Similarity	NPC177035
0.8043	Intermediate Similarity	NPC103409
0.8031	Intermediate Similarity	NPC9248
0.8029	Intermediate Similarity	NPC107478
0.8015	Intermediate Similarity	NPC470270
0.8014	Intermediate Similarity	NPC469559
0.8014	Intermediate Similarity	NPC139976
0.8014	Intermediate Similarity	NPC246947
0.8014	Intermediate Similarity	NPC128337
0.8014	Intermediate Similarity	NPC230718
0.8014	Intermediate Similarity	NPC60249
0.8014	Intermediate Similarity	NPC49542
0.8014	Intermediate Similarity	NPC5253
0.8014	Intermediate Similarity	NPC189115
0.8014	Intermediate Similarity	NPC84207
0.8	Intermediate Similarity	NPC55608
0.8	Intermediate Similarity	NPC11724
0.8	Intermediate Similarity	NPC210478
0.8	Intermediate Similarity	NPC106944
0.7986	Intermediate Similarity	NPC134260
0.7986	Intermediate Similarity	NPC304152
0.7986	Intermediate Similarity	NPC65530
0.7986	Intermediate Similarity	NPC59324
0.7971	Intermediate Similarity	NPC185778
0.7969	Intermediate Similarity	NPC228907
0.7958	Intermediate Similarity	NPC185307
0.7958	Intermediate Similarity	NPC473044
0.7958	Intermediate Similarity	NPC469367
0.7958	Intermediate Similarity	NPC116922
0.7958	Intermediate Similarity	NPC470950
0.7958	Intermediate Similarity	NPC46092
0.7956	Intermediate Similarity	NPC215037
0.7955	Intermediate Similarity	NPC109822
0.7955	Intermediate Similarity	NPC94276
0.7951	Intermediate Similarity	NPC251306
0.7943	Intermediate Similarity	NPC469661
0.7943	Intermediate Similarity	NPC273932
0.7943	Intermediate Similarity	NPC89686
0.7943	Intermediate Similarity	NPC257095
0.7939	Intermediate Similarity	NPC71090
0.7939	Intermediate Similarity	NPC52097
0.7934	Intermediate Similarity	NPC37714
0.7934	Intermediate Similarity	NPC152384
0.7926	Intermediate Similarity	NPC86030
0.7926	Intermediate Similarity	NPC5851
0.7923	Intermediate Similarity	NPC160854
0.7923	Intermediate Similarity	NPC201402
0.7923	Intermediate Similarity	NPC469703
0.7923	Intermediate Similarity	NPC469704
0.7923	Intermediate Similarity	NPC476872
0.792	Intermediate Similarity	NPC115379
0.7914	Intermediate Similarity	NPC157554
0.7914	Intermediate Similarity	NPC469383
0.7914	Intermediate Similarity	NPC104167
0.791	Intermediate Similarity	NPC111247
0.791	Intermediate Similarity	NPC118787
0.791	Intermediate Similarity	NPC147821
0.791	Intermediate Similarity	NPC41706
0.791	Intermediate Similarity	NPC163332
0.791	Intermediate Similarity	NPC183181
0.791	Intermediate Similarity	NPC319625
0.791	Intermediate Similarity	NPC292056
0.7907	Intermediate Similarity	NPC135961
0.7902	Intermediate Similarity	NPC79429
0.7902	Intermediate Similarity	NPC471063
0.7902	Intermediate Similarity	NPC129417
0.7902	Intermediate Similarity	NPC217635
0.7902	Intermediate Similarity	NPC25292
0.7902	Intermediate Similarity	NPC471667
0.7902	Intermediate Similarity	NPC283995
0.7902	Intermediate Similarity	NPC473045
0.7902	Intermediate Similarity	NPC470235
0.7902	Intermediate Similarity	NPC177597
0.7902	Intermediate Similarity	NPC225445
0.7899	Intermediate Similarity	NPC87696
0.7895	Intermediate Similarity	NPC207179
0.7895	Intermediate Similarity	NPC278552
0.7895	Intermediate Similarity	NPC167571
0.7887	Intermediate Similarity	NPC157816
0.7887	Intermediate Similarity	NPC472353

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 NPC198798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	806
0.2-0.3	1581
0.3-0.4	2847
0.4-0.5	1915
0.5-0.6	1154
0.6-0.7	602
0.7-0.8	63
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.872	High Similarity	NPD1091	Approved
0.7886	Intermediate Similarity	NPD2684	Approved
0.7872	Intermediate Similarity	NPD2424	Discontinued
0.7805	Intermediate Similarity	NPD290	Approved
0.7778	Intermediate Similarity	NPD7843	Approved
0.7744	Intermediate Similarity	NPD3685	Discontinued
0.7655	Intermediate Similarity	NPD5058	Phase 3
0.7638	Intermediate Similarity	NPD821	Approved
0.7597	Intermediate Similarity	NPD7157	Approved
0.7536	Intermediate Similarity	NPD3180	Approved
0.7536	Intermediate Similarity	NPD3179	Approved
0.7534	Intermediate Similarity	NPD5756	Phase 2
0.7519	Intermediate Similarity	NPD3847	Discontinued
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7465	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4538	Approved
0.7465	Intermediate Similarity	NPD4536	Approved
0.7463	Intermediate Similarity	NPD3705	Approved
0.7448	Intermediate Similarity	NPD1652	Phase 2
0.7448	Intermediate Similarity	NPD6674	Discontinued
0.7424	Intermediate Similarity	NPD1182	Approved
0.741	Intermediate Similarity	NPD3027	Phase 3
0.7402	Intermediate Similarity	NPD556	Approved
0.74	Intermediate Similarity	NPD1653	Approved
0.7372	Intermediate Similarity	NPD1817	Approved
0.7372	Intermediate Similarity	NPD1820	Approved
0.7372	Intermediate Similarity	NPD1819	Approved
0.7372	Intermediate Similarity	NPD1818	Approved
0.731	Intermediate Similarity	NPD1375	Discontinued
0.731	Intermediate Similarity	NPD7266	Discontinued
0.7305	Intermediate Similarity	NPD6233	Phase 2
0.7299	Intermediate Similarity	NPD8651	Approved
0.7297	Intermediate Similarity	NPD5295	Discontinued
0.7293	Intermediate Similarity	NPD1548	Phase 1
0.7292	Intermediate Similarity	NPD5960	Phase 3
0.7292	Intermediate Similarity	NPD5588	Approved
0.7284	Intermediate Similarity	NPD7007	Discovery
0.7279	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4110	Phase 3
0.7279	Intermediate Similarity	NPD1840	Phase 2
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7258	Intermediate Similarity	NPD291	Approved
0.7244	Intermediate Similarity	NPD1358	Approved
0.723	Intermediate Similarity	NPD2677	Approved
0.7222	Intermediate Similarity	NPD7097	Phase 1
0.7214	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4908	Phase 1
0.7211	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5289	Phase 2
0.7208	Intermediate Similarity	NPD4433	Discontinued
0.7206	Intermediate Similarity	NPD1610	Phase 2
0.7185	Intermediate Similarity	NPD6516	Phase 2
0.7185	Intermediate Similarity	NPD5846	Approved
0.7183	Intermediate Similarity	NPD1423	Approved
0.7172	Intermediate Similarity	NPD4108	Discontinued
0.7172	Intermediate Similarity	NPD3152	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD968	Approved
0.7163	Intermediate Similarity	NPD3165	Approved
0.7163	Intermediate Similarity	NPD3167	Approved
0.7163	Intermediate Similarity	NPD3164	Approved
0.7163	Intermediate Similarity	NPD3166	Approved
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1794	Approved
0.7115	Intermediate Similarity	NPD2415	Discontinued
0.7113	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6798	Discontinued
0.7101	Intermediate Similarity	NPD6582	Phase 2
0.7101	Intermediate Similarity	NPD6583	Phase 3
0.7086	Intermediate Similarity	NPD3536	Discontinued
0.7086	Intermediate Similarity	NPD3985	Discontinued
0.7083	Intermediate Similarity	NPD9365	Approved
0.708	Intermediate Similarity	NPD776	Approved
0.708	Intermediate Similarity	NPD422	Phase 1
0.7071	Intermediate Similarity	NPD3691	Phase 2
0.7071	Intermediate Similarity	NPD3690	Phase 2
0.7071	Intermediate Similarity	NPD558	Phase 2
0.7063	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4062	Phase 3
0.7059	Intermediate Similarity	NPD5125	Phase 3
0.7059	Intermediate Similarity	NPD5126	Approved
0.7047	Intermediate Similarity	NPD4628	Phase 3
0.7034	Intermediate Similarity	NPD3052	Approved
0.7034	Intermediate Similarity	NPD3054	Approved
0.7023	Intermediate Similarity	NPD228	Approved
0.702	Intermediate Similarity	NPD1774	Approved
0.7015	Intermediate Similarity	NPD3596	Phase 2
0.7014	Intermediate Similarity	NPD1558	Phase 1
0.7007	Intermediate Similarity	NPD2240	Approved
0.7007	Intermediate Similarity	NPD2239	Approved
0.6993	Remote Similarity	NPD1048	Approved
0.698	Remote Similarity	NPD4236	Phase 3
0.698	Remote Similarity	NPD4237	Approved
0.6972	Remote Similarity	NPD682	Discontinued
0.697	Remote Similarity	NPD5535	Approved
0.6966	Remote Similarity	NPD5124	Phase 1
0.6966	Remote Similarity	NPD6355	Discontinued
0.6966	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4340	Discontinued
0.6959	Remote Similarity	NPD521	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6584	Phase 3
0.6948	Remote Similarity	NPD3687	Approved
0.6948	Remote Similarity	NPD3686	Approved
0.6944	Remote Similarity	NPD4870	Approved
0.6943	Remote Similarity	NPD2977	Approved
0.6943	Remote Similarity	NPD2978	Approved
0.694	Remote Similarity	NPD191	Approved
0.694	Remote Similarity	NPD6671	Approved
0.6933	Remote Similarity	NPD4535	Phase 3
0.6923	Remote Similarity	NPD5163	Phase 2
0.6918	Remote Similarity	NPD6653	Approved
0.6912	Remote Similarity	NPD6581	Approved
0.6912	Remote Similarity	NPD6580	Approved
0.6908	Remote Similarity	NPD7213	Phase 3
0.6908	Remote Similarity	NPD7212	Phase 2
0.6899	Remote Similarity	NPD3134	Approved
0.6897	Remote Similarity	NPD2238	Phase 2
0.6897	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4060	Phase 1
0.6892	Remote Similarity	NPD6032	Approved
0.6875	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4162	Approved
0.6861	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5735	Approved
0.6848	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7054	Approved
0.6846	Remote Similarity	NPD5763	Approved
0.6846	Remote Similarity	NPD5762	Approved
0.6842	Remote Similarity	NPD3122	Phase 3
0.6835	Remote Similarity	NPD5773	Approved
0.6835	Remote Similarity	NPD5772	Approved
0.6831	Remote Similarity	NPD5647	Approved
0.6828	Remote Similarity	NPD3163	Approved
0.6828	Remote Similarity	NPD3162	Approved
0.6824	Remote Similarity	NPD7033	Discontinued
0.6818	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2557	Approved
0.6815	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2668	Approved
0.6812	Remote Similarity	NPD2667	Approved
0.6812	Remote Similarity	NPD1778	Approved
0.6807	Remote Similarity	NPD7472	Approved
0.6807	Remote Similarity	NPD7074	Phase 3
0.6806	Remote Similarity	NPD7095	Approved
0.6803	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1241	Discontinued
0.6791	Remote Similarity	NPD5283	Phase 1
0.6788	Remote Similarity	NPD1894	Discontinued
0.6779	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD969	Suspended
0.6766	Remote Similarity	NPD6797	Phase 2
0.6763	Remote Similarity	NPD3496	Discontinued
0.6761	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6362	Approved
0.6759	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3060	Approved
0.6755	Remote Similarity	NPD5062	Approved
0.6755	Remote Similarity	NPD5061	Approved
0.6753	Remote Similarity	NPD7447	Phase 1
0.6753	Remote Similarity	NPD4123	Phase 3
0.6753	Remote Similarity	NPD6419	Discontinued
0.6752	Remote Similarity	NPD4972	Discontinued
0.6739	Remote Similarity	NPD6382	Discontinued
0.6738	Remote Similarity	NPD2429	Approved
0.6738	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4749	Approved
0.6738	Remote Similarity	NPD2983	Phase 2
0.6738	Remote Similarity	NPD2982	Phase 2
0.6738	Remote Similarity	NPD2428	Approved
0.6736	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2614	Approved
0.6732	Remote Similarity	NPD6667	Approved
0.6732	Remote Similarity	NPD6666	Approved
0.6728	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6559	Discontinued
0.6726	Remote Similarity	NPD7251	Discontinued
0.6718	Remote Similarity	NPD9552	Approved
0.6716	Remote Similarity	NPD1138	Approved
0.6715	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1535	Discovery
0.6712	Remote Similarity	NPD5745	Approved
0.6712	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2154	Approved
0.6711	Remote Similarity	NPD2155	Approved
0.6711	Remote Similarity	NPD2156	Approved
0.671	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.671	Remote Similarity	NPD52	Approved
0.671	Remote Similarity	NPD7526	Approved
0.6709	Remote Similarity	NPD6072	Discontinued
0.6708	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2556	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