NPASS Compound

Structure

CID71780 OpenBabel06191715412D 39 42 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1157 -2.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1498 -2.8270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 3.8228 -3.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8910 -3.7929 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 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5640 -4.2412 0.0000 C 0 0 0 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 1.7321 1.0000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 3 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 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2711 -4.9483 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3914 -5.1088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 2.5981 -0.5000 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 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 19 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 36 1 0 0 0 0 15 24 1 0 0 0 0 16 22 2 0 0 0 0 17 22 1 0 0 0 0 17 29 1 0 0 0 0 18 13 1 6 0 0 0 18 20 1 0 0 0 0 18 37 1 0 0 0 0 19 27 1 0 0 0 0 19 30 2 0 0 0 0 20 21 1 0 0 0 0 20 31 1 1 0 0 0 21 23 1 0 0 0 0 21 32 1 6 0 0 0 22 39 1 0 0 0 0 23 25 1 0 0 0 0 23 38 1 1 0 0 0 24 33 2 0 0 0 0 24 38 1 0 0 0 0 25 37 1 0 0 0 0 25 39 1 6 0 0 0 26 27 1 0 0 0 0 26 34 2 0 0 0 0 26 36 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.16
Volume:	520.44
LogP:	1.79
LogD:	1.281
LogS:	-2.908
# Rotatable Bonds:	10
TPSA:	189.28
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.172
Synthetic Accessibility Score:	4.383
Fsp3:	0.37
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.029
MDCK Permeability:	2.582785782578867e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.549
20% Bioavailability (F20%):	0.822
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	94.04195404052734%
Volume Distribution (VD):	0.602
Pgp-substrate:	5.464143753051758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	2.321
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.516
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.031
Carcinogencity:	0.321
Eye Corrosion:	0.003
Eye Irritation:	0.234
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC71780

Natural Product ID:	NPC71780
*Common Name:**	Cochinchiside B
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl)oxymethyl]phenoxy]-6-(hydroxymethyl)oxan-3-yl] benzoate
Synonyms:
Standard InCHIKey:	KAXLSURJPZQJPA-KELFPRCHSA-N
Standard InCHI:	InChI=1S/C27H28O12/c28-13-18-20(31)21(32)23(38-24(33)15-7-2-1-3-8-15)25(37-18)39-22-16(9-6-10-17(22)29)14-36-26(34)27(35)12-5-4-11-19(27)30/h1-3,5-10,12,18,20-21,23,25,28-29,31-32,35H,4,11,13-14H2/t18-,20-,21+,23-,25+,27?/m1/s1
SMILES:	c1ccc(cc1)C(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1c(cccc1O)COC(=O)C1(C=CCCC1=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463281
PubChem CID:	10370160
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
NPO30966	Homalium cochinchinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104498]
NPO30966	Homalium cochinchinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584406]
NPO30966	Homalium cochinchinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26516	Homalium cochinchinense	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26516	Homalium cochinchinense	Species	Salicaceae	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
EC50	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	=	76000.0	nM	PMID[529907]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	=	76000.0	nM	PMID[529907]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	18000.0	nM	PMID[529907]

☑ 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 NPC71780 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	383
0.1-0.2	1616
0.2-0.3	3974
0.3-0.4	8725
0.4-0.5	9330
0.5-0.6	4481
0.6-0.7	6502
0.7-0.8	6345
0.8-0.85	970
0.85-0.9	357
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC474398
0.9545	High Similarity	NPC474401
0.9545	High Similarity	NPC476026
0.9545	High Similarity	NPC474441
0.9408	High Similarity	NPC131874
0.9359	High Similarity	NPC57072
0.9359	High Similarity	NPC231475
0.9342	High Similarity	NPC471214
0.9276	High Similarity	NPC22137
0.9245	High Similarity	NPC475183
0.913	High Similarity	NPC475174
0.9068	High Similarity	NPC280923
0.9024	High Similarity	NPC153755
0.9012	High Similarity	NPC197285
0.9012	High Similarity	NPC21100
0.9	High Similarity	NPC217950
0.8981	High Similarity	NPC92153
0.8981	High Similarity	NPC299761
0.8981	High Similarity	NPC230439
0.8981	High Similarity	NPC279281
0.897	High Similarity	NPC4390
0.8963	High Similarity	NPC149011
0.8963	High Similarity	NPC116864
0.8963	High Similarity	NPC204937
0.8963	High Similarity	NPC20505
0.8963	High Similarity	NPC155763
0.8963	High Similarity	NPC235260
0.8963	High Similarity	NPC206123
0.8963	High Similarity	NPC244776
0.8961	High Similarity	NPC92054
0.8961	High Similarity	NPC140722
0.8961	High Similarity	NPC4958
0.8957	High Similarity	NPC116745
0.8951	High Similarity	NPC277205
0.8922	High Similarity	NPC217520
0.8922	High Similarity	NPC139571
0.8916	High Similarity	NPC477848
0.8916	High Similarity	NPC237435
0.8916	High Similarity	NPC115760
0.8916	High Similarity	NPC81042
0.8916	High Similarity	NPC49344
0.8916	High Similarity	NPC214621
0.8916	High Similarity	NPC135277
0.8916	High Similarity	NPC43211
0.8916	High Similarity	NPC210094
0.8916	High Similarity	NPC223426
0.8916	High Similarity	NPC34267
0.8916	High Similarity	NPC101191
0.891	High Similarity	NPC93619
0.8909	High Similarity	NPC190003
0.8909	High Similarity	NPC175107
0.8903	High Similarity	NPC111785
0.8902	High Similarity	NPC472133
0.8902	High Similarity	NPC225434
0.8902	High Similarity	NPC203050
0.8902	High Similarity	NPC223747
0.8902	High Similarity	NPC138927
0.8902	High Similarity	NPC120099
0.8902	High Similarity	NPC219904
0.8896	High Similarity	NPC145038
0.8896	High Similarity	NPC474422
0.8896	High Similarity	NPC274618
0.8896	High Similarity	NPC253662
0.8896	High Similarity	NPC281131
0.8896	High Similarity	NPC56077
0.8896	High Similarity	NPC88789
0.8896	High Similarity	NPC276222
0.8896	High Similarity	NPC179950
0.8896	High Similarity	NPC308404
0.8896	High Similarity	NPC118284
0.8889	High Similarity	NPC270335
0.8889	High Similarity	NPC168822
0.8889	High Similarity	NPC88043
0.8889	High Similarity	NPC127415
0.8889	High Similarity	NPC191306
0.8868	High Similarity	NPC471405
0.8862	High Similarity	NPC268533
0.8862	High Similarity	NPC472385
0.8862	High Similarity	NPC198324
0.8862	High Similarity	NPC211532
0.8862	High Similarity	NPC144097
0.8862	High Similarity	NPC61904
0.8862	High Similarity	NPC233994
0.8861	High Similarity	NPC191046
0.8861	High Similarity	NPC194095
0.8861	High Similarity	NPC327032
0.8855	High Similarity	NPC88560
0.8855	High Similarity	NPC172033
0.8855	High Similarity	NPC472993
0.8855	High Similarity	NPC175230
0.8848	High Similarity	NPC245014
0.8848	High Similarity	NPC285197
0.8848	High Similarity	NPC43434
0.8848	High Similarity	NPC72249
0.8848	High Similarity	NPC84265
0.8848	High Similarity	NPC472129
0.8848	High Similarity	NPC280385
0.8848	High Similarity	NPC282987
0.8841	High Similarity	NPC229729
0.8841	High Similarity	NPC265530
0.8841	High Similarity	NPC52550
0.8841	High Similarity	NPC173637
0.8841	High Similarity	NPC84362
0.8841	High Similarity	NPC160156
0.8841	High Similarity	NPC298847
0.8841	High Similarity	NPC317489
0.8841	High Similarity	NPC45400
0.8841	High Similarity	NPC149244
0.8841	High Similarity	NPC127546
0.8841	High Similarity	NPC226304
0.8841	High Similarity	NPC325555
0.8841	High Similarity	NPC48640
0.8841	High Similarity	NPC92565
0.8841	High Similarity	NPC223424
0.8834	High Similarity	NPC240431
0.8834	High Similarity	NPC472130
0.8834	High Similarity	NPC22832
0.8834	High Similarity	NPC472131
0.8834	High Similarity	NPC165720
0.8834	High Similarity	NPC19388
0.8834	High Similarity	NPC55786
0.8834	High Similarity	NPC311830
0.8827	High Similarity	NPC189142
0.8827	High Similarity	NPC77660
0.8827	High Similarity	NPC22324
0.882	High Similarity	NPC44507
0.8817	High Similarity	NPC170203
0.8816	High Similarity	NPC31081
0.8816	High Similarity	NPC245219
0.8812	High Similarity	NPC40920
0.8812	High Similarity	NPC223335
0.8812	High Similarity	NPC133984
0.881	High Similarity	NPC113836
0.881	High Similarity	NPC37668
0.881	High Similarity	NPC35167
0.881	High Similarity	NPC173837
0.881	High Similarity	NPC253521
0.881	High Similarity	NPC477895
0.8805	High Similarity	NPC10205
0.8802	High Similarity	NPC264735
0.8802	High Similarity	NPC253685
0.8797	High Similarity	NPC215811
0.8797	High Similarity	NPC157898
0.8795	High Similarity	NPC60735
0.8795	High Similarity	NPC254540
0.8795	High Similarity	NPC67134
0.8795	High Similarity	NPC211594
0.8795	High Similarity	NPC117260
0.8795	High Similarity	NPC476405
0.8795	High Similarity	NPC26230
0.8795	High Similarity	NPC245452
0.8795	High Similarity	NPC235575
0.8795	High Similarity	NPC172807
0.8795	High Similarity	NPC47140
0.8788	High Similarity	NPC52382
0.8788	High Similarity	NPC229687
0.8788	High Similarity	NPC270578
0.878	High Similarity	NPC135599
0.878	High Similarity	NPC113968
0.878	High Similarity	NPC236934
0.878	High Similarity	NPC328940
0.878	High Similarity	NPC5778
0.878	High Similarity	NPC254306
0.878	High Similarity	NPC73855
0.878	High Similarity	NPC277174
0.8773	High Similarity	NPC121290
0.8773	High Similarity	NPC309025
0.8773	High Similarity	NPC222936
0.8773	High Similarity	NPC29830
0.8773	High Similarity	NPC284960
0.8773	High Similarity	NPC243930
0.8773	High Similarity	NPC88023
0.8773	High Similarity	NPC19709
0.8765	High Similarity	NPC470718
0.8765	High Similarity	NPC36138
0.8758	High Similarity	NPC469654
0.8758	High Similarity	NPC160780
0.8758	High Similarity	NPC289811
0.875	High Similarity	NPC296018
0.875	High Similarity	NPC472384
0.875	High Similarity	NPC471669
0.875	High Similarity	NPC472382
0.875	High Similarity	NPC472991
0.875	High Similarity	NPC154741
0.875	High Similarity	NPC472380
0.875	High Similarity	NPC89127
0.875	High Similarity	NPC472992
0.8743	High Similarity	NPC45522
0.8743	High Similarity	NPC101026
0.8743	High Similarity	NPC24043
0.8743	High Similarity	NPC42773
0.8743	High Similarity	NPC470438
0.8743	High Similarity	NPC169977
0.8743	High Similarity	NPC21666
0.8742	High Similarity	NPC299435
0.8742	High Similarity	NPC260604
0.8742	High Similarity	NPC185103
0.8735	High Similarity	NPC259896
0.8735	High Similarity	NPC471416
0.8735	High Similarity	NPC255157

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 NPC71780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	905
0.2-0.3	1911
0.3-0.4	2601
0.4-0.5	1875
0.5-0.6	986
0.6-0.7	396
0.7-0.8	119
0.8-0.85	18
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD4338	Clinical (unspecified phase)
0.8683	High Similarity	NPD6797	Phase 2
0.8675	High Similarity	NPD7054	Approved
0.8631	High Similarity	NPD7251	Discontinued
0.8623	High Similarity	NPD7472	Approved
0.8623	High Similarity	NPD7074	Phase 3
0.8614	High Similarity	NPD3818	Discontinued
0.858	High Similarity	NPD7808	Phase 3
0.8466	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6166	Phase 2
0.8383	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5402	Approved
0.8293	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5403	Approved
0.8232	Intermediate Similarity	NPD3817	Phase 2
0.8221	Intermediate Similarity	NPD1934	Approved
0.8199	Intermediate Similarity	NPD1653	Approved
0.814	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5401	Approved
0.8103	Intermediate Similarity	NPD8313	Approved
0.8103	Intermediate Similarity	NPD8312	Approved
0.8092	Intermediate Similarity	NPD6559	Discontinued
0.8092	Intermediate Similarity	NPD7685	Pre-registration
0.8072	Intermediate Similarity	NPD3882	Suspended
0.8061	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1933	Approved
0.8024	Intermediate Similarity	NPD7075	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD3751	Discontinued
0.7963	Intermediate Similarity	NPD1512	Approved
0.7952	Intermediate Similarity	NPD2801	Approved
0.7911	Intermediate Similarity	NPD7266	Discontinued
0.7879	Intermediate Similarity	NPD4380	Phase 2
0.7844	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD6190	Approved
0.7821	Intermediate Similarity	NPD447	Suspended
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1465	Phase 2
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.773	Intermediate Similarity	NPD6799	Approved
0.7714	Intermediate Similarity	NPD5844	Phase 1
0.7657	Intermediate Similarity	NPD7228	Approved
0.7633	Intermediate Similarity	NPD8455	Phase 2
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7435	Discontinued
0.7558	Intermediate Similarity	NPD6234	Discontinued
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3750	Approved
0.7532	Intermediate Similarity	NPD1203	Approved
0.7531	Intermediate Similarity	NPD1549	Phase 2
0.7529	Intermediate Similarity	NPD7819	Suspended
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7411	Suspended
0.7514	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7471	Intermediate Similarity	NPD37	Approved
0.747	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6599	Discontinued
0.7442	Intermediate Similarity	NPD4965	Approved
0.7442	Intermediate Similarity	NPD4966	Approved
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7429	Intermediate Similarity	NPD6232	Discontinued
0.7421	Intermediate Similarity	NPD1613	Approved
0.7421	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2935	Discontinued
0.7401	Intermediate Similarity	NPD7473	Discontinued
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6832	Phase 2
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7294	Intermediate Similarity	NPD3226	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7698	Approved
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7262	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD919	Approved
0.7256	Intermediate Similarity	NPD2346	Discontinued
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.7247	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7768	Phase 2
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7239	Intermediate Similarity	NPD1510	Phase 2
0.7239	Intermediate Similarity	NPD3748	Approved
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7229	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD3749	Approved
0.7198	Intermediate Similarity	NPD7240	Approved
0.7195	Intermediate Similarity	NPD2796	Approved
0.7191	Intermediate Similarity	NPD3926	Phase 2
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7175	Intermediate Similarity	NPD6959	Discontinued
0.717	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8320	Phase 1
0.7165	Intermediate Similarity	NPD8319	Approved
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7134	Intermediate Similarity	NPD3225	Approved
0.7125	Intermediate Similarity	NPD3027	Phase 3
0.7121	Intermediate Similarity	NPD7801	Approved
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7107	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8151	Discontinued
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7092	Intermediate Similarity	NPD7584	Approved
0.7081	Intermediate Similarity	NPD411	Approved
0.7079	Intermediate Similarity	NPD8127	Discontinued
0.7073	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6844	Discontinued
0.7066	Intermediate Similarity	NPD6674	Discontinued
0.7056	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD2798	Approved
0.703	Intermediate Similarity	NPD2799	Discontinued
0.7011	Intermediate Similarity	NPD7038	Approved
0.7011	Intermediate Similarity	NPD7039	Approved
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9494	Approved
0.6994	Remote Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD943	Approved
0.6983	Remote Similarity	NPD1247	Approved
0.6981	Remote Similarity	NPD2797	Approved
0.6979	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3268	Approved
0.697	Remote Similarity	NPD7585	Approved
0.6937	Remote Similarity	NPD1019	Discontinued
0.6919	Remote Similarity	NPD7583	Approved
0.6911	Remote Similarity	NPD6212	Phase 3
0.6911	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6213	Phase 3
0.6909	Remote Similarity	NPD1607	Approved
0.6907	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4307	Phase 2
0.689	Remote Similarity	NPD4060	Phase 1
0.6885	Remote Similarity	NPD2163	Approved
0.6883	Remote Similarity	NPD9493	Approved
0.6867	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7097	Phase 1
0.6853	Remote Similarity	NPD7680	Approved
0.6839	Remote Similarity	NPD5536	Phase 2
0.6829	Remote Similarity	NPD4062	Phase 3
0.6826	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8166	Discontinued
0.6821	Remote Similarity	NPD5049	Phase 3
0.6821	Remote Similarity	NPD6273	Approved
0.6818	Remote Similarity	NPD6386	Approved
0.6818	Remote Similarity	NPD6385	Approved
0.681	Remote Similarity	NPD7095	Approved
0.68	Remote Similarity	NPD3455	Phase 2
0.6798	Remote Similarity	NPD5353	Approved
0.6793	Remote Similarity	NPD7799	Discontinued
0.6792	Remote Similarity	NPD1608	Approved
0.6786	Remote Similarity	NPD6099	Approved
0.6786	Remote Similarity	NPD6100	Approved
0.6784	Remote Similarity	NPD2354	Approved
0.6784	Remote Similarity	NPD3887	Approved
0.6774	Remote Similarity	NPD5953	Discontinued
0.6769	Remote Similarity	NPD4420	Approved
0.6768	Remote Similarity	NPD3764	Approved
0.6765	Remote Similarity	NPD1652	Phase 2
0.6765	Remote Similarity	NPD7930	Approved
0.6763	Remote Similarity	NPD4662	Approved
0.6763	Remote Similarity	NPD2533	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