NPASS Compound

Structure

CID212176 OpenBabel06191716002D 22 23 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 2.5981 1.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 7 2 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 8 1 0 0 0 0 5 15 3 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 8 17 1 0 0 0 0 9 5 1 1 0 0 0 9 21 1 0 0 0 0 10 6 1 6 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 14 1 0 0 0 0 13 20 1 1 0 0 0 14 21 1 6 0 0 0 14 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.1
Volume:	292.933
LogP:	-0.833
LogD:	-0.613
LogS:	-1.189
# Rotatable Bonds:	4
TPSA:	143.4
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	3.936
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:	-5.618
MDCK Permeability:	7.465850649168715e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.851
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.27
Plasma Protein Binding (PPB):	28.82135772705078%
Volume Distribution (VD):	0.398
Pgp-substrate:	73.22180938720703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.559
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	2.353
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.727
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.696
Rat Oral Acute Toxicity:	0.733
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.803
Carcinogencity:	0.059
Eye Corrosion:	0.009
Eye Irritation:	0.749
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC212176

Natural Product ID:	NPC212176
*Common Name:**	Taxiphyllin
IUPAC Name:	(2R)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
Synonyms:	taxiphyllin
Standard InCHIKey:	NVLTYOJHPBMILU-GMDXDWKASA-N
Standard InCHI:	InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1
SMILES:	c1cc(ccc1[C@H](C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469825
PubChem CID:	107721
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:0002365] Cyanogenic 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
NPO32690	salsola tetrandra	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989538]
NPO29976	Triglochin maritimum	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30499	Taxus spp	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29976	Triglochin maritimum	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29466	Triglochin maritima	Species	Juncaginaceae	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
ED50	1
MIC	5
Others	4

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	ED50	=	0.96	uM	PMID[567406]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	600.0	ug.mL-1	PMID[567406]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	500.0	ug.mL-1	PMID[567406]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	>	700.0	ug ml-1	PMID[567406]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	200.0	ug.mL-1	PMID[567406]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	>	700.0	ug ml-1	PMID[567406]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	400.0	ug.mL-1	PMID[567406]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	500.0	ug ml-1	PMID[567406]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	700.0	ug.mL-1	PMID[567406]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	700.0	ug ml-1	PMID[567406]

☑ 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 NPC212176 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	244
0.1-0.2	1276
0.2-0.3	3907
0.3-0.4	11001
0.4-0.5	8255
0.5-0.6	9820
0.6-0.7	6841
0.7-0.8	1224
0.8-0.85	99
0.85-0.9	22
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC175771
0.9187	High Similarity	NPC198798
0.9138	High Similarity	NPC313193
0.9138	High Similarity	NPC157338
0.9052	High Similarity	NPC120217
0.8983	High Similarity	NPC148055
0.877	High Similarity	NPC269242
0.875	High Similarity	NPC122245
0.875	High Similarity	NPC266389
0.875	High Similarity	NPC216605
0.8689	High Similarity	NPC469708
0.8689	High Similarity	NPC282409
0.8689	High Similarity	NPC60589
0.8689	High Similarity	NPC469702
0.8629	High Similarity	NPC476142
0.8618	High Similarity	NPC160854
0.8618	High Similarity	NPC201402
0.8618	High Similarity	NPC469703
0.8618	High Similarity	NPC476448
0.8618	High Similarity	NPC469412
0.8618	High Similarity	NPC198734
0.8618	High Similarity	NPC469704
0.8618	High Similarity	NPC476445
0.8618	High Similarity	NPC469548
0.8548	High Similarity	NPC469686
0.8548	High Similarity	NPC266045
0.8548	High Similarity	NPC55608
0.8548	High Similarity	NPC11724
0.8512	High Similarity	NPC473556
0.8512	High Similarity	NPC301651
0.848	Intermediate Similarity	NPC471067
0.848	Intermediate Similarity	NPC52097
0.8468	Intermediate Similarity	NPC476872
0.8438	Intermediate Similarity	NPC288416
0.8413	Intermediate Similarity	NPC232454
0.8413	Intermediate Similarity	NPC178449
0.8413	Intermediate Similarity	NPC470907
0.84	Intermediate Similarity	NPC226712
0.8362	Intermediate Similarity	NPC37714
0.8362	Intermediate Similarity	NPC152384
0.8346	Intermediate Similarity	NPC287429
0.8321	Intermediate Similarity	NPC248307
0.8321	Intermediate Similarity	NPC65942
0.8306	Intermediate Similarity	NPC477803
0.8281	Intermediate Similarity	NPC126991
0.8281	Intermediate Similarity	NPC90318
0.8281	Intermediate Similarity	NPC83218
0.8258	Intermediate Similarity	NPC254275
0.8217	Intermediate Similarity	NPC471157
0.8217	Intermediate Similarity	NPC252114
0.8182	Intermediate Similarity	NPC46137
0.8182	Intermediate Similarity	NPC42911
0.8182	Intermediate Similarity	NPC225384
0.8182	Intermediate Similarity	NPC478255
0.8182	Intermediate Similarity	NPC138777
0.8182	Intermediate Similarity	NPC153795
0.8182	Intermediate Similarity	NPC290353
0.8182	Intermediate Similarity	NPC235294
0.8182	Intermediate Similarity	NPC246869
0.8168	Intermediate Similarity	NPC307110
0.8168	Intermediate Similarity	NPC166040
0.8168	Intermediate Similarity	NPC97326
0.8168	Intermediate Similarity	NPC26653
0.8168	Intermediate Similarity	NPC270849
0.8154	Intermediate Similarity	NPC106677
0.8154	Intermediate Similarity	NPC45224
0.8154	Intermediate Similarity	NPC469687
0.8154	Intermediate Similarity	NPC108659
0.8154	Intermediate Similarity	NPC264900
0.8154	Intermediate Similarity	NPC471881
0.8154	Intermediate Similarity	NPC471882
0.8154	Intermediate Similarity	NPC156692
0.8154	Intermediate Similarity	NPC35288
0.8154	Intermediate Similarity	NPC231607
0.8154	Intermediate Similarity	NPC79715
0.8154	Intermediate Similarity	NPC173150
0.814	Intermediate Similarity	NPC470510
0.8134	Intermediate Similarity	NPC470881
0.8134	Intermediate Similarity	NPC35731
0.8106	Intermediate Similarity	NPC80600
0.8106	Intermediate Similarity	NPC472024
0.8092	Intermediate Similarity	NPC148982
0.8092	Intermediate Similarity	NPC232880
0.8092	Intermediate Similarity	NPC40377
0.8092	Intermediate Similarity	NPC225307
0.8083	Intermediate Similarity	NPC276061
0.8083	Intermediate Similarity	NPC474148
0.8077	Intermediate Similarity	NPC94179
0.8077	Intermediate Similarity	NPC61181
0.8074	Intermediate Similarity	NPC79957
0.806	Intermediate Similarity	NPC114116
0.806	Intermediate Similarity	NPC6836
0.8045	Intermediate Similarity	NPC9912
0.8045	Intermediate Similarity	NPC121376
0.803	Intermediate Similarity	NPC253595
0.803	Intermediate Similarity	NPC229784
0.803	Intermediate Similarity	NPC184092
0.803	Intermediate Similarity	NPC477293
0.803	Intermediate Similarity	NPC469549
0.803	Intermediate Similarity	NPC477294
0.803	Intermediate Similarity	NPC248355
0.8017	Intermediate Similarity	NPC264784
0.8017	Intermediate Similarity	NPC30563
0.8016	Intermediate Similarity	NPC14950
0.8015	Intermediate Similarity	NPC471345
0.8015	Intermediate Similarity	NPC52277
0.8015	Intermediate Similarity	NPC103533
0.8015	Intermediate Similarity	NPC177035
0.8015	Intermediate Similarity	NPC476873
0.8015	Intermediate Similarity	NPC199459
0.8	Intermediate Similarity	NPC107478
0.8	Intermediate Similarity	NPC287597
0.8	Intermediate Similarity	NPC34293
0.8	Intermediate Similarity	NPC886
0.8	Intermediate Similarity	NPC169398
0.8	Intermediate Similarity	NPC12308
0.8	Intermediate Similarity	NPC123704
0.7986	Intermediate Similarity	NPC63628
0.7986	Intermediate Similarity	NPC178466
0.7985	Intermediate Similarity	NPC165686
0.7985	Intermediate Similarity	NPC252833
0.7985	Intermediate Similarity	NPC85799
0.7985	Intermediate Similarity	NPC470270
0.7985	Intermediate Similarity	NPC303422
0.7985	Intermediate Similarity	NPC26080
0.7971	Intermediate Similarity	NPC195814
0.797	Intermediate Similarity	NPC17968
0.797	Intermediate Similarity	NPC262606
0.797	Intermediate Similarity	NPC469705
0.797	Intermediate Similarity	NPC470122
0.7966	Intermediate Similarity	NPC148060
0.7956	Intermediate Similarity	NPC262328
0.7956	Intermediate Similarity	NPC87777
0.7956	Intermediate Similarity	NPC304152
0.7956	Intermediate Similarity	NPC138738
0.7956	Intermediate Similarity	NPC78363
0.7956	Intermediate Similarity	NPC470413
0.7955	Intermediate Similarity	NPC158673
0.7955	Intermediate Similarity	NPC302378
0.7955	Intermediate Similarity	NPC146540
0.7941	Intermediate Similarity	NPC263829
0.7926	Intermediate Similarity	NPC294166
0.7926	Intermediate Similarity	NPC25821
0.7926	Intermediate Similarity	NPC115022
0.7926	Intermediate Similarity	NPC132895
0.791	Intermediate Similarity	NPC475067
0.791	Intermediate Similarity	NPC166168
0.791	Intermediate Similarity	NPC281798
0.791	Intermediate Similarity	NPC219677
0.791	Intermediate Similarity	NPC254819
0.7903	Intermediate Similarity	NPC142319
0.7895	Intermediate Similarity	NPC295970
0.7895	Intermediate Similarity	NPC218003
0.7883	Intermediate Similarity	NPC166180
0.7868	Intermediate Similarity	NPC130496
0.7868	Intermediate Similarity	NPC48863
0.7868	Intermediate Similarity	NPC188555
0.7868	Intermediate Similarity	NPC251981
0.7868	Intermediate Similarity	NPC187194
0.7868	Intermediate Similarity	NPC476411
0.7868	Intermediate Similarity	NPC13745
0.7857	Intermediate Similarity	NPC476266
0.7852	Intermediate Similarity	NPC473924
0.7852	Intermediate Similarity	NPC299144
0.7852	Intermediate Similarity	NPC471066
0.7852	Intermediate Similarity	NPC471095
0.7852	Intermediate Similarity	NPC473285
0.7845	Intermediate Similarity	NPC262826
0.7842	Intermediate Similarity	NPC106944
0.7836	Intermediate Similarity	NPC474491
0.7829	Intermediate Similarity	NPC470804
0.7826	Intermediate Similarity	NPC469364
0.7826	Intermediate Similarity	NPC65262
0.7826	Intermediate Similarity	NPC36434
0.7826	Intermediate Similarity	NPC260425
0.7826	Intermediate Similarity	NPC101686
0.781	Intermediate Similarity	NPC238243
0.781	Intermediate Similarity	NPC184938
0.781	Intermediate Similarity	NPC101624
0.7794	Intermediate Similarity	NPC28637
0.7794	Intermediate Similarity	NPC254398
0.7794	Intermediate Similarity	NPC49074
0.7794	Intermediate Similarity	NPC69513
0.7794	Intermediate Similarity	NPC164172
0.7794	Intermediate Similarity	NPC215833
0.7787	Intermediate Similarity	NPC265211
0.7787	Intermediate Similarity	NPC306045
0.7786	Intermediate Similarity	NPC476385
0.7786	Intermediate Similarity	NPC472711
0.7786	Intermediate Similarity	NPC134405
0.7786	Intermediate Similarity	NPC210192
0.7786	Intermediate Similarity	NPC469661
0.7778	Intermediate Similarity	NPC475824
0.7778	Intermediate Similarity	NPC476407
0.777	Intermediate Similarity	NPC321638
0.777	Intermediate Similarity	NPC171134
0.777	Intermediate Similarity	NPC68092
0.777	Intermediate Similarity	NPC472350
0.777	Intermediate Similarity	NPC205195
0.777	Intermediate Similarity	NPC328273

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 NPC212176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	762
0.2-0.3	1543
0.3-0.4	2943
0.4-0.5	1967
0.5-0.6	1224
0.6-0.7	504
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD1091	Approved
0.777	Intermediate Similarity	NPD7266	Discontinued
0.7372	Intermediate Similarity	NPD3027	Phase 3
0.7343	Intermediate Similarity	NPD2424	Discontinued
0.7338	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1613	Approved
0.728	Intermediate Similarity	NPD2684	Approved
0.7273	Intermediate Similarity	NPD5125	Phase 3
0.7273	Intermediate Similarity	NPD5126	Approved
0.7248	Intermediate Similarity	NPD1653	Approved
0.7222	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3847	Discontinued
0.72	Intermediate Similarity	NPD290	Approved
0.7197	Intermediate Similarity	NPD1357	Approved
0.7188	Intermediate Similarity	NPD7843	Approved
0.7185	Intermediate Similarity	NPD3685	Discontinued
0.7183	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD5058	Phase 3
0.7121	Intermediate Similarity	NPD1548	Phase 1
0.7109	Intermediate Similarity	NPD969	Suspended
0.7054	Intermediate Similarity	NPD821	Approved
0.705	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1610	Phase 2
0.7034	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7157	Approved
0.7015	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9381	Approved
0.7015	Intermediate Similarity	NPD9384	Approved
0.7	Intermediate Similarity	NPD2934	Approved
0.7	Intermediate Similarity	NPD3180	Approved
0.7	Intermediate Similarity	NPD2933	Approved
0.7	Intermediate Similarity	NPD3179	Approved
0.6992	Remote Similarity	NPD1182	Approved
0.6987	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD968	Approved
0.6978	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2861	Phase 2
0.6977	Remote Similarity	NPD228	Approved
0.6944	Remote Similarity	NPD4538	Approved
0.6944	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4536	Approved
0.6942	Remote Similarity	NPD2859	Approved
0.6942	Remote Similarity	NPD2860	Approved
0.6939	Remote Similarity	NPD6674	Discontinued
0.6939	Remote Similarity	NPD1652	Phase 2
0.6935	Remote Similarity	NPD846	Approved
0.6935	Remote Similarity	NPD940	Approved
0.6933	Remote Similarity	NPD7007	Discovery
0.6933	Remote Similarity	NPD3985	Discontinued
0.6929	Remote Similarity	NPD4908	Phase 1
0.6917	Remote Similarity	NPD16	Approved
0.6917	Remote Similarity	NPD856	Approved
0.6913	Remote Similarity	NPD5756	Phase 2
0.6903	Remote Similarity	NPD2978	Approved
0.6903	Remote Similarity	NPD8455	Phase 2
0.6903	Remote Similarity	NPD2977	Approved
0.6897	Remote Similarity	NPD5588	Approved
0.6897	Remote Similarity	NPD4108	Discontinued
0.6897	Remote Similarity	NPD5960	Phase 3
0.6866	Remote Similarity	NPD9545	Approved
0.6861	Remote Similarity	NPD2231	Phase 2
0.6861	Remote Similarity	NPD2235	Phase 2
0.6861	Remote Similarity	NPD1840	Phase 2
0.6835	Remote Similarity	NPD1817	Approved
0.6835	Remote Similarity	NPD1819	Approved
0.6835	Remote Similarity	NPD1820	Approved
0.6835	Remote Similarity	NPD1818	Approved
0.6831	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3536	Discontinued
0.6812	Remote Similarity	NPD6583	Phase 3
0.6812	Remote Similarity	NPD4659	Approved
0.6812	Remote Similarity	NPD9622	Approved
0.6812	Remote Similarity	NPD6582	Phase 2
0.6803	Remote Similarity	NPD1375	Discontinued
0.6797	Remote Similarity	NPD1358	Approved
0.6791	Remote Similarity	NPD318	Approved
0.6791	Remote Similarity	NPD317	Approved
0.6788	Remote Similarity	NPD422	Phase 1
0.6783	Remote Similarity	NPD6233	Phase 2
0.6783	Remote Similarity	NPD6405	Approved
0.6783	Remote Similarity	NPD6407	Approved
0.6779	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4110	Phase 3
0.6774	Remote Similarity	NPD3020	Approved
0.6769	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6516	Phase 2
0.6765	Remote Similarity	NPD5846	Approved
0.6763	Remote Similarity	NPD8651	Approved
0.6759	Remote Similarity	NPD3054	Approved
0.6759	Remote Similarity	NPD3052	Approved
0.6739	Remote Similarity	NPD2562	Approved
0.6739	Remote Similarity	NPD2561	Approved
0.6736	Remote Similarity	NPD1558	Phase 1
0.6736	Remote Similarity	NPD3059	Approved
0.6736	Remote Similarity	NPD3062	Approved
0.6736	Remote Similarity	NPD3061	Approved
0.6736	Remote Similarity	NPD2238	Phase 2
0.6733	Remote Similarity	NPD2677	Approved
0.6733	Remote Similarity	NPD6190	Approved
0.6731	Remote Similarity	NPD4433	Discontinued
0.6721	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1242	Phase 1
0.6714	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3094	Phase 2
0.6714	Remote Similarity	NPD4103	Phase 2
0.6712	Remote Similarity	NPD7097	Phase 1
0.6711	Remote Similarity	NPD3060	Approved
0.6711	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4236	Phase 3
0.6711	Remote Similarity	NPD4237	Approved
0.6692	Remote Similarity	NPD556	Approved
0.6692	Remote Similarity	NPD3022	Approved
0.6692	Remote Similarity	NPD3021	Approved
0.669	Remote Similarity	NPD4340	Discontinued
0.6689	Remote Similarity	NPD5295	Discontinued
0.6667	Remote Similarity	NPD9621	Approved
0.6667	Remote Similarity	NPD558	Phase 2
0.6667	Remote Similarity	NPD1423	Approved
0.6667	Remote Similarity	NPD9620	Approved
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD6584	Phase 3
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD9619	Approved
0.6646	Remote Similarity	NPD2415	Discontinued
0.6645	Remote Similarity	NPD7213	Phase 3
0.6645	Remote Similarity	NPD7212	Phase 2
0.6644	Remote Similarity	NPD817	Approved
0.6644	Remote Similarity	NPD823	Approved
0.6644	Remote Similarity	NPD5314	Approved
0.6643	Remote Similarity	NPD3166	Approved
0.6643	Remote Similarity	NPD3167	Approved
0.6643	Remote Similarity	NPD3164	Approved
0.6643	Remote Similarity	NPD3165	Approved
0.6642	Remote Similarity	NPD6671	Approved
0.6621	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4060	Phase 1
0.6606	Remote Similarity	NPD7054	Approved
0.6606	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4380	Phase 2
0.6601	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5289	Phase 2
0.6597	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD597	Approved
0.6597	Remote Similarity	NPD601	Approved
0.6597	Remote Similarity	NPD1048	Approved
0.6597	Remote Similarity	NPD6798	Discontinued
0.6597	Remote Similarity	NPD598	Approved
0.6596	Remote Similarity	NPD1131	Approved
0.6596	Remote Similarity	NPD1794	Approved
0.6596	Remote Similarity	NPD1134	Approved
0.6596	Remote Similarity	NPD1135	Approved
0.6596	Remote Similarity	NPD1129	Approved
0.6596	Remote Similarity	NPD1133	Approved
0.6581	Remote Similarity	NPD3686	Approved
0.6581	Remote Similarity	NPD3687	Approved
0.6579	Remote Similarity	NPD3122	Phase 3
0.6575	Remote Similarity	NPD230	Phase 1
0.6575	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5124	Phase 1
0.6567	Remote Similarity	NPD9618	Approved
0.6567	Remote Similarity	NPD9614	Approved
0.6566	Remote Similarity	NPD7472	Approved
0.6566	Remote Similarity	NPD7074	Phase 3
0.6562	Remote Similarity	NPD9610	Approved
0.6562	Remote Similarity	NPD9608	Approved
0.6554	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1753	Discontinued
0.6552	Remote Similarity	NPD4062	Phase 3
0.6552	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1130	Approved
0.6552	Remote Similarity	NPD1136	Approved
0.6552	Remote Similarity	NPD1132	Approved
0.6549	Remote Similarity	NPD3691	Phase 2
0.6549	Remote Similarity	NPD3690	Phase 2
0.6547	Remote Similarity	NPD1535	Discovery
0.6547	Remote Similarity	NPD3092	Approved
0.6545	Remote Similarity	NPD3818	Discontinued
0.6545	Remote Similarity	NPD7228	Approved
0.6541	Remote Similarity	NPD9379	Approved
0.6541	Remote Similarity	NPD9377	Approved
0.6538	Remote Similarity	NPD6056	Approved
0.6538	Remote Similarity	NPD6057	Approved
0.6538	Remote Similarity	NPD9532	Phase 3
0.6536	Remote Similarity	NPD1774	Approved
0.6536	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD291	Approved
0.6531	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2568	Approved
0.6531	Remote Similarity	NPD6653	Approved
0.6527	Remote Similarity	NPD6797	Phase 2
0.6522	Remote Similarity	NPD6234	Discontinued
0.6522	Remote Similarity	NPD2667	Approved
0.6522	Remote Similarity	NPD2668	Approved
0.6522	Remote Similarity	NPD2286	Discontinued
0.6519	Remote Similarity	NPD37	Approved
0.651	Remote Similarity	NPD2239	Approved
0.651	Remote Similarity	NPD2240	Approved
0.651	Remote Similarity	NPD9570	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