NPASS Compound

Structure

NPC471787 OpenBabel07101719252D 39 42 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 1.7321 -0.0000 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 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 0.8660 -1.5000 0.0000 C 0 0 2 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 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 -1.7321 -3.0000 0.0000 C 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 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 6 1 0 0 0 0 2 12 2 0 0 0 0 3 7 2 0 0 0 0 3 12 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 28 1 0 0 0 0 12 21 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 31 1 0 0 0 0 17 20 2 0 0 0 0 17 37 1 0 0 0 0 18 11 1 6 0 0 0 18 22 1 0 0 0 0 18 38 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 23 1 0 0 0 0 21 32 2 0 0 0 0 22 24 1 0 0 0 0 22 33 1 1 0 0 0 23 34 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 6 0 0 0 25 20 1 6 0 0 0 25 26 1 0 0 0 0 25 38 1 0 0 0 0 26 39 1 1 0 0 0 27 36 2 0 0 0 0 27 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.14
Volume:	517.804
LogP:	2.696
LogD:	1.347
LogS:	-3.5
# Rotatable Bonds:	8
TPSA:	203.44
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	3.978
Fsp3:	0.259
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.475
MDCK Permeability:	7.002574875514256e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.788
20% Bioavailability (F20%):	0.152
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	100.49406433105469%
Volume Distribution (VD):	0.574
Pgp-substrate:	2.789686918258667%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.538
CYP2C9-substrate:	0.615
CYP2D6-inhibitor:	0.354
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	11.965
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.616
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.101
Carcinogencity:	0.234
Eye Corrosion:	0.003
Eye Irritation:	0.208
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC471787

Natural Product ID:	NPC471787
*Common Name:**	Foliamangiferoside A1
IUPAC Name:	[(2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxyphenyl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 4-hydroxybenzoate
Synonyms:
Standard InCHIKey:	QAGIFLJVFGOXJD-BDEJEHHJSA-N
Standard InCHI:	InChI=1S/C27H26O12/c1-37-17-10-16(31)19(21(32)12-2-6-14(29)7-3-12)23(34)20(17)25-26(24(35)22(33)18(11-28)38-25)39-27(36)13-4-8-15(30)9-5-13/h2-10,18,22,24-26,28-31,33-35H,11H2,1H3/t18-,22-,24+,25+,26-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)OC(=O)c1ccc(cc1)O)c1c(OC)cc(c(c1O)C(=O)c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3233508
PubChem CID:	56653525
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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO33051	mango tree	n.a.	n.a.	n.a.	stem bark	n.a.	n.a.	PMID[24613627]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3084	Individual Protein	Neuraminidase	Influenza A virus	Inhibition	=	39.0	%	PMID[470755]
NPT24971	SINGLE PROTEIN	Genome polyprotein	Coxsackievirus B3 (strain Nancy)	Inhibition	=	27.2	%	PMID[470755]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	PC50	>	100.0	uM	PMID[470756]

☑ 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 NPC471787 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	350
0.1-0.2	1373
0.2-0.3	3100
0.3-0.4	7262
0.4-0.5	10641
0.5-0.6	4717
0.6-0.7	4966
0.7-0.8	5800
0.8-0.85	3100
0.85-0.9	1302
0.9-0.95	83
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC89442
0.9548	High Similarity	NPC471788
0.953	High Similarity	NPC124478
0.953	High Similarity	NPC177308
0.9481	High Similarity	NPC97812
0.9474	High Similarity	NPC208152
0.9474	High Similarity	NPC78492
0.9404	High Similarity	NPC150123
0.9404	High Similarity	NPC10807
0.9404	High Similarity	NPC161881
0.9404	High Similarity	NPC244583
0.9404	High Similarity	NPC56232
0.9355	High Similarity	NPC92589
0.9342	High Similarity	NPC20907
0.9342	High Similarity	NPC472583
0.9342	High Similarity	NPC223701
0.9342	High Similarity	NPC244250
0.9342	High Similarity	NPC7989
0.9338	High Similarity	NPC209846
0.9338	High Similarity	NPC328740
0.9338	High Similarity	NPC244577
0.9338	High Similarity	NPC472422
0.9338	High Similarity	NPC471676
0.9338	High Similarity	NPC289774
0.9338	High Similarity	NPC472420
0.9338	High Similarity	NPC263384
0.9338	High Similarity	NPC477897
0.9308	High Similarity	NPC76047
0.9281	High Similarity	NPC477958
0.9281	High Similarity	NPC470681
0.9281	High Similarity	NPC111341
0.9281	High Similarity	NPC304745
0.9276	High Similarity	NPC475790
0.9276	High Similarity	NPC256141
0.9276	High Similarity	NPC171651
0.9276	High Similarity	NPC35567
0.9276	High Similarity	NPC243171
0.9262	High Similarity	NPC316769
0.9231	High Similarity	NPC142252
0.9226	High Similarity	NPC123544
0.9216	High Similarity	NPC469405
0.9216	High Similarity	NPC268193
0.9216	High Similarity	NPC109594
0.9216	High Similarity	NPC326592
0.9216	High Similarity	NPC112701
0.9216	High Similarity	NPC293286
0.9211	High Similarity	NPC474021
0.9211	High Similarity	NPC471677
0.9211	High Similarity	NPC204561
0.9211	High Similarity	NPC278476
0.9211	High Similarity	NPC309512
0.9211	High Similarity	NPC474023
0.9211	High Similarity	NPC316960
0.9211	High Similarity	NPC148945
0.9211	High Similarity	NPC262038
0.9211	High Similarity	NPC262039
0.9211	High Similarity	NPC319910
0.9211	High Similarity	NPC254412
0.9211	High Similarity	NPC78835
0.9211	High Similarity	NPC317715
0.92	High Similarity	NPC222298
0.92	High Similarity	NPC51070
0.9172	High Similarity	NPC476247
0.9172	High Similarity	NPC472876
0.9167	High Similarity	NPC472320
0.9161	High Similarity	NPC43638
0.9161	High Similarity	NPC222689
0.9161	High Similarity	NPC23817
0.9161	High Similarity	NPC35598
0.9156	High Similarity	NPC48579
0.9156	High Similarity	NPC259710
0.9156	High Similarity	NPC217706
0.9156	High Similarity	NPC304207
0.9156	High Similarity	NPC207809
0.915	High Similarity	NPC138288
0.915	High Similarity	NPC473996
0.915	High Similarity	NPC217149
0.915	High Similarity	NPC216035
0.9145	High Similarity	NPC105136
0.9145	High Similarity	NPC180351
0.9139	High Similarity	NPC10097
0.9133	High Similarity	NPC25844
0.9133	High Similarity	NPC470132
0.9133	High Similarity	NPC472629
0.9133	High Similarity	NPC228779
0.9133	High Similarity	NPC470131
0.9133	High Similarity	NPC470134
0.9133	High Similarity	NPC473078
0.9133	High Similarity	NPC470133
0.9133	High Similarity	NPC109183
0.913	High Similarity	NPC289396
0.913	High Similarity	NPC212038
0.913	High Similarity	NPC271848
0.913	High Similarity	NPC81332
0.913	High Similarity	NPC262580
0.9128	High Similarity	NPC117836
0.9128	High Similarity	NPC51887
0.9128	High Similarity	NPC475705
0.9128	High Similarity	NPC476178
0.9122	High Similarity	NPC321980
0.9122	High Similarity	NPC470087
0.9119	High Similarity	NPC207575
0.9119	High Similarity	NPC13481
0.9108	High Similarity	NPC195685
0.9108	High Similarity	NPC270675
0.9108	High Similarity	NPC472994
0.9108	High Similarity	NPC477629
0.9108	High Similarity	NPC210961
0.9108	High Similarity	NPC477628
0.9103	High Similarity	NPC73511
0.9103	High Similarity	NPC43761
0.9097	High Similarity	NPC215917
0.9097	High Similarity	NPC20530
0.9097	High Similarity	NPC10754
0.9097	High Similarity	NPC127406
0.9091	High Similarity	NPC248793
0.9091	High Similarity	NPC180301
0.9085	High Similarity	NPC472636
0.9085	High Similarity	NPC474772
0.9085	High Similarity	NPC474744
0.9085	High Similarity	NPC472580
0.9085	High Similarity	NPC472423
0.9079	High Similarity	NPC472628
0.9079	High Similarity	NPC164299
0.9079	High Similarity	NPC307052
0.9079	High Similarity	NPC139966
0.9073	High Similarity	NPC472627
0.9067	High Similarity	NPC470890
0.9067	High Similarity	NPC470135
0.9067	High Similarity	NPC124780
0.9067	High Similarity	NPC470136
0.9067	High Similarity	NPC87486
0.9067	High Similarity	NPC39045
0.9057	High Similarity	NPC139060
0.9051	High Similarity	NPC259834
0.9051	High Similarity	NPC131745
0.9051	High Similarity	NPC44947
0.9045	High Similarity	NPC471976
0.9045	High Similarity	NPC306978
0.9038	High Similarity	NPC475184
0.9038	High Similarity	NPC161749
0.9038	High Similarity	NPC313163
0.9038	High Similarity	NPC197896
0.9038	High Similarity	NPC208258
0.9038	High Similarity	NPC156457
0.9038	High Similarity	NPC258035
0.9032	High Similarity	NPC108937
0.9032	High Similarity	NPC477530
0.9032	High Similarity	NPC99233
0.9032	High Similarity	NPC279218
0.9032	High Similarity	NPC79375
0.9032	High Similarity	NPC37253
0.9026	High Similarity	NPC327269
0.9026	High Similarity	NPC477957
0.9026	High Similarity	NPC43345
0.9026	High Similarity	NPC31627
0.9026	High Similarity	NPC285623
0.9026	High Similarity	NPC476238
0.902	High Similarity	NPC474735
0.902	High Similarity	NPC472421
0.9	High Similarity	NPC39329
0.9	High Similarity	NPC150408
0.9	High Similarity	NPC169591
0.9	High Similarity	NPC301751
0.9	High Similarity	NPC175504
0.9	High Similarity	NPC68104
0.9	High Similarity	NPC310130
0.9	High Similarity	NPC149026
0.9	High Similarity	NPC91560
0.9	High Similarity	NPC143896
0.9	High Similarity	NPC221432
0.9	High Similarity	NPC257097
0.9	High Similarity	NPC75049
0.9	High Similarity	NPC164980
0.9	High Similarity	NPC245482
0.8994	High Similarity	NPC66087
0.8994	High Similarity	NPC80068
0.8994	High Similarity	NPC63438
0.8994	High Similarity	NPC183672
0.8994	High Similarity	NPC179198
0.8994	High Similarity	NPC124155
0.8994	High Similarity	NPC278419
0.8994	High Similarity	NPC257566
0.8993	High Similarity	NPC470089
0.8993	High Similarity	NPC469404
0.8987	High Similarity	NPC158188
0.8987	High Similarity	NPC26326
0.8987	High Similarity	NPC47923
0.8987	High Similarity	NPC3629
0.8987	High Similarity	NPC303913
0.8986	High Similarity	NPC470211
0.8986	High Similarity	NPC275903
0.8986	High Similarity	NPC64664
0.8981	High Similarity	NPC53545
0.8981	High Similarity	NPC117418
0.8981	High Similarity	NPC15815
0.8974	High Similarity	NPC474738
0.8974	High Similarity	NPC129053
0.8974	High Similarity	NPC170475
0.8974	High Similarity	NPC45165

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 NPC471787 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	834
0.2-0.3	1600
0.3-0.4	2529
0.4-0.5	2072
0.5-0.6	1169
0.6-0.7	420
0.7-0.8	166
0.8-0.85	42
0.85-0.9	20
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.953	High Similarity	NPD4380	Phase 2
0.9286	High Similarity	NPD7075	Discontinued
0.9211	High Similarity	NPD7411	Suspended
0.9091	High Similarity	NPD7096	Clinical (unspecified phase)
0.9038	High Similarity	NPD4381	Clinical (unspecified phase)
0.9026	High Similarity	NPD6801	Discontinued
0.891	High Similarity	NPD8443	Clinical (unspecified phase)
0.8854	High Similarity	NPD4868	Clinical (unspecified phase)
0.8846	High Similarity	NPD2393	Clinical (unspecified phase)
0.882	High Similarity	NPD7852	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8816	High Similarity	NPD7410	Clinical (unspecified phase)
0.8773	High Similarity	NPD7804	Clinical (unspecified phase)
0.8726	High Similarity	NPD7819	Suspended
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8667	High Similarity	NPD1549	Phase 2
0.8662	High Similarity	NPD1934	Approved
0.8627	High Similarity	NPD6799	Approved
0.8616	High Similarity	NPD7768	Phase 2
0.8614	High Similarity	NPD6559	Discontinued
0.86	High Similarity	NPD1550	Clinical (unspecified phase)
0.86	High Similarity	NPD1552	Clinical (unspecified phase)
0.8591	High Similarity	NPD1510	Phase 2
0.8581	High Similarity	NPD5403	Approved
0.858	High Similarity	NPD6232	Discontinued
0.8545	High Similarity	NPD5844	Phase 1
0.8537	High Similarity	NPD7473	Discontinued
0.8519	High Similarity	NPD6959	Discontinued
0.8494	Intermediate Similarity	NPD7074	Phase 3
0.8487	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD5401	Approved
0.8446	Intermediate Similarity	NPD1240	Approved
0.8443	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5402	Approved
0.8438	Intermediate Similarity	NPD3817	Phase 2
0.8434	Intermediate Similarity	NPD7054	Approved
0.8418	Intermediate Similarity	NPD6599	Discontinued
0.8411	Intermediate Similarity	NPD2796	Approved
0.8383	Intermediate Similarity	NPD7472	Approved
0.8373	Intermediate Similarity	NPD3818	Discontinued
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD6797	Phase 2
0.8289	Intermediate Similarity	NPD2935	Discontinued
0.8284	Intermediate Similarity	NPD7251	Discontinued
0.8276	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2801	Approved
0.8235	Intermediate Similarity	NPD7808	Phase 3
0.8232	Intermediate Similarity	NPD5494	Approved
0.8194	Intermediate Similarity	NPD4628	Phase 3
0.8194	Intermediate Similarity	NPD3750	Approved
0.8192	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD3882	Suspended
0.8153	Intermediate Similarity	NPD1511	Approved
0.8101	Intermediate Similarity	NPD2533	Approved
0.8101	Intermediate Similarity	NPD2534	Approved
0.8101	Intermediate Similarity	NPD2532	Approved
0.8081	Intermediate Similarity	NPD8313	Approved
0.8081	Intermediate Similarity	NPD8312	Approved
0.8077	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1551	Phase 2
0.805	Intermediate Similarity	NPD1512	Approved
0.8012	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD920	Approved
0.7955	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD8455	Phase 2
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7903	Intermediate Similarity	NPD8151	Discontinued
0.7901	Intermediate Similarity	NPD3226	Approved
0.7901	Intermediate Similarity	NPD7458	Discontinued
0.7898	Intermediate Similarity	NPD1243	Approved
0.7895	Intermediate Similarity	NPD7286	Phase 2
0.7875	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2799	Discontinued
0.7871	Intermediate Similarity	NPD3748	Approved
0.7862	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6651	Approved
0.7841	Intermediate Similarity	NPD8150	Discontinued
0.7829	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2313	Discontinued
0.7826	Intermediate Similarity	NPD7435	Discontinued
0.7812	Intermediate Similarity	NPD7390	Discontinued
0.7791	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2800	Approved
0.7764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD6780	Approved
0.776	Intermediate Similarity	NPD6777	Approved
0.776	Intermediate Similarity	NPD6776	Approved
0.776	Intermediate Similarity	NPD6779	Approved
0.776	Intermediate Similarity	NPD6781	Approved
0.776	Intermediate Similarity	NPD6778	Approved
0.776	Intermediate Similarity	NPD6782	Approved
0.7738	Intermediate Similarity	NPD919	Approved
0.7712	Intermediate Similarity	NPD6798	Discontinued
0.7701	Intermediate Similarity	NPD7584	Approved
0.7697	Intermediate Similarity	NPD6832	Phase 2
0.7697	Intermediate Similarity	NPD4908	Phase 1
0.7688	Intermediate Similarity	NPD6190	Approved
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5124	Phase 1
0.7677	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD2346	Discontinued
0.7651	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD7033	Discontinued
0.7643	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.763	Intermediate Similarity	NPD3751	Discontinued
0.763	Intermediate Similarity	NPD7228	Approved
0.7625	Intermediate Similarity	NPD7003	Approved
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD4965	Approved
0.7619	Intermediate Similarity	NPD4966	Approved
0.7616	Intermediate Similarity	NPD1203	Approved
0.7614	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD943	Approved
0.7602	Intermediate Similarity	NPD5710	Approved
0.7602	Intermediate Similarity	NPD5711	Approved
0.7595	Intermediate Similarity	NPD5408	Approved
0.7595	Intermediate Similarity	NPD5405	Approved
0.7595	Intermediate Similarity	NPD5404	Approved
0.7595	Intermediate Similarity	NPD5406	Approved
0.7594	Intermediate Similarity	NPD7871	Phase 2
0.7594	Intermediate Similarity	NPD7870	Phase 2
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4360	Phase 2
0.7582	Intermediate Similarity	NPD4363	Phase 3
0.7579	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7874	Approved
0.7548	Intermediate Similarity	NPD6233	Phase 2
0.7547	Intermediate Similarity	NPD2344	Approved
0.7542	Intermediate Similarity	NPD8434	Phase 2
0.754	Intermediate Similarity	NPD7698	Approved
0.754	Intermediate Similarity	NPD7696	Phase 3
0.754	Intermediate Similarity	NPD7697	Approved
0.7539	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7783	Phase 2
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7487	Intermediate Similarity	NPD6823	Phase 2
0.7486	Intermediate Similarity	NPD6535	Approved
0.7486	Intermediate Similarity	NPD6534	Approved
0.7484	Intermediate Similarity	NPD3764	Approved
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7474	Intermediate Similarity	NPD7585	Approved
0.7467	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3926	Phase 2
0.7453	Intermediate Similarity	NPD1652	Phase 2
0.7452	Intermediate Similarity	NPD1933	Approved
0.7451	Intermediate Similarity	NPD2798	Approved
0.7442	Intermediate Similarity	NPD1247	Approved
0.7432	Intermediate Similarity	NPD9545	Approved
0.7421	Intermediate Similarity	NPD7583	Approved
0.7419	Intermediate Similarity	NPD3027	Phase 3
0.7417	Intermediate Similarity	NPD9717	Approved
0.7414	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1653	Approved
0.7407	Intermediate Similarity	NPD8319	Approved
0.7407	Intermediate Similarity	NPD8320	Phase 1
0.7399	Intermediate Similarity	NPD7229	Phase 3
0.7372	Intermediate Similarity	NPD3268	Approved
0.7366	Intermediate Similarity	NPD7700	Phase 2
0.7366	Intermediate Similarity	NPD7699	Phase 2
0.7363	Intermediate Similarity	NPD4287	Approved
0.7362	Intermediate Similarity	NPD2309	Approved
0.7358	Intermediate Similarity	NPD7801	Approved
0.7342	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD447	Suspended
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7266	Discontinued
0.7312	Intermediate Similarity	NPD4308	Phase 3
0.7297	Intermediate Similarity	NPD9493	Approved
0.7289	Intermediate Similarity	NPD6273	Approved
0.7287	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2424	Discontinued
0.7278	Intermediate Similarity	NPD5889	Approved
0.7278	Intermediate Similarity	NPD5890	Approved
0.7273	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD1164	Approved
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD6099	Approved
0.7263	Intermediate Similarity	NPD7240	Approved
0.7251	Intermediate Similarity	NPD4288	Approved
0.725	Intermediate Similarity	NPD7097	Phase 1
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6214	Clinical (unspecified phase)

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