NPASS Compound

Structure

CID310661 OpenBabel06191716122D 24 25 0 0 1 0 0 0 0 0999 V2000 6.0622 -0.5000 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 2.5981 -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 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -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 1.7321 1.0000 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 -0.0000 1.0000 0.0000 C 0 0 1 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 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 -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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 5 1 0 0 0 0 3 7 2 0 0 0 0 4 15 1 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 4 1 6 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 1 0 0 0 10 11 1 0 0 0 0 10 19 1 6 0 0 0 11 14 1 0 0 0 0 11 20 1 1 0 0 0 12 24 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.09
Volume:	310.944
LogP:	-0.456
LogD:	-0.241
LogS:	-1.323
# Rotatable Bonds:	5
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	3.723
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.309
MDCK Permeability:	5.2813615184277296e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.15
Human Intestinal Absorption (HIA):	0.825
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.509
Plasma Protein Binding (PPB):	56.078407287597656%
Volume Distribution (VD):	0.502
Pgp-substrate:	35.43546676635742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.104
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.191
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	5.595
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.663
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.344
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.099
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC310661

Natural Product ID:	NPC310661
*Common Name:**	Methyl Gallate 4-O-Beta-D-Glucopyranoside
IUPAC Name:	methyl 3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
Synonyms:
Standard InCHIKey:	JUPHZGHVZWMVHU-QEGBUVANSA-N
Standard InCHI:	InChI=1S/C14H18O10/c1-22-13(21)5-2-6(16)12(7(17)3-5)24-14-11(20)10(19)9(18)8(4-15)23-14/h2-3,8-11,14-20H,4H2,1H3/t8-,9-,10+,11-,14+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(O)cc(cc2O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485255
PubChem CID:	5317705
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
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12848	Carpinus cordata	Species	Betulaceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	100.0	ug.mL-1	PMID[524120]

☑ 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 NPC310661 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	344
0.1-0.2	1570
0.2-0.3	4066
0.3-0.4	8863
0.4-0.5	9200
0.5-0.6	4124
0.6-0.7	5444
0.7-0.8	7043
0.8-0.85	1620
0.85-0.9	353
0.9-0.95	57
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC105827
0.9732	High Similarity	NPC1913
0.9667	High Similarity	NPC160780
0.9667	High Similarity	NPC289811
0.9603	High Similarity	NPC119125
0.9603	High Similarity	NPC239966
0.9603	High Similarity	NPC166277
0.9603	High Similarity	NPC203020
0.9539	High Similarity	NPC311803
0.9539	High Similarity	NPC472859
0.9539	High Similarity	NPC25389
0.9477	High Similarity	NPC285108
0.9477	High Similarity	NPC41009
0.9477	High Similarity	NPC33298
0.947	High Similarity	NPC472860
0.9448	High Similarity	NPC108455
0.9408	High Similarity	NPC74319
0.9408	High Similarity	NPC287872
0.94	High Similarity	NPC327032
0.94	High Similarity	NPC194095
0.94	High Similarity	NPC191046
0.9392	High Similarity	NPC205054
0.9379	High Similarity	NPC229036
0.9346	High Similarity	NPC289346
0.9276	High Similarity	NPC471405
0.9267	High Similarity	NPC75695
0.9267	High Similarity	NPC134905
0.9267	High Similarity	NPC36130
0.9236	High Similarity	NPC116745
0.9226	High Similarity	NPC90905
0.9226	High Similarity	NPC4013
0.9216	High Similarity	NPC133984
0.9211	High Similarity	NPC10205
0.9195	High Similarity	NPC92117
0.9177	High Similarity	NPC197708
0.9177	High Similarity	NPC658
0.9133	High Similarity	NPC473091
0.9128	High Similarity	NPC248257
0.9128	High Similarity	NPC120621
0.9103	High Similarity	NPC225036
0.9103	High Similarity	NPC75763
0.9103	High Similarity	NPC148273
0.9103	High Similarity	NPC105525
0.9103	High Similarity	NPC12218
0.9079	High Similarity	NPC157898
0.9079	High Similarity	NPC137813
0.9073	High Similarity	NPC140151
0.9067	High Similarity	NPC111785
0.9062	High Similarity	NPC102851
0.9062	High Similarity	NPC5786
0.9045	High Similarity	NPC88043
0.9045	High Similarity	NPC94777
0.9013	High Similarity	NPC289438
0.9006	High Similarity	NPC163165
0.9006	High Similarity	NPC172033
0.9006	High Similarity	NPC88560
0.9006	High Similarity	NPC175230
0.9	High Similarity	NPC204937
0.9	High Similarity	NPC149011
0.9	High Similarity	NPC472969
0.8987	High Similarity	NPC165720
0.8986	High Similarity	NPC134975
0.8968	High Similarity	NPC226759
0.8966	High Similarity	NPC125417
0.8966	High Similarity	NPC110899
0.8966	High Similarity	NPC25305
0.8966	High Similarity	NPC112068
0.8966	High Similarity	NPC95679
0.8961	High Similarity	NPC172920
0.8961	High Similarity	NPC156624
0.8954	High Similarity	NPC16024
0.8954	High Similarity	NPC205037
0.8954	High Similarity	NPC61152
0.8954	High Similarity	NPC3746
0.8954	High Similarity	NPC44260
0.8951	High Similarity	NPC84482
0.8951	High Similarity	NPC169645
0.8944	High Similarity	NPC211594
0.8944	High Similarity	NPC254540
0.8944	High Similarity	NPC172807
0.894	High Similarity	NPC98809
0.894	High Similarity	NPC476394
0.894	High Similarity	NPC75945
0.8938	High Similarity	NPC95421
0.8938	High Similarity	NPC149300
0.8938	High Similarity	NPC198125
0.8938	High Similarity	NPC229687
0.8931	High Similarity	NPC99957
0.8931	High Similarity	NPC181616
0.8924	High Similarity	NPC222936
0.8924	High Similarity	NPC284960
0.8917	High Similarity	NPC217950
0.891	High Similarity	NPC87317
0.8904	High Similarity	NPC207516
0.8904	High Similarity	NPC239943
0.8896	High Similarity	NPC43872
0.8896	High Similarity	NPC67629
0.8896	High Similarity	NPC291510
0.8896	High Similarity	NPC238672
0.8896	High Similarity	NPC144801
0.8896	High Similarity	NPC116850
0.8896	High Similarity	NPC79736
0.8896	High Similarity	NPC197188
0.8889	High Similarity	NPC34436
0.8889	High Similarity	NPC219600
0.8889	High Similarity	NPC166674
0.8889	High Similarity	NPC46640
0.8889	High Similarity	NPC263119
0.8889	High Similarity	NPC472993
0.8889	High Similarity	NPC4390
0.8882	High Similarity	NPC224462
0.8882	High Similarity	NPC212748
0.8882	High Similarity	NPC227980
0.8875	High Similarity	NPC45400
0.8875	High Similarity	NPC229729
0.8868	High Similarity	NPC22832
0.8868	High Similarity	NPC311830
0.8868	High Similarity	NPC475738
0.8867	High Similarity	NPC473867
0.8861	High Similarity	NPC300537
0.8861	High Similarity	NPC127782
0.8861	High Similarity	NPC473043
0.8859	High Similarity	NPC121573
0.8859	High Similarity	NPC226738
0.8859	High Similarity	NPC190587
0.8859	High Similarity	NPC22176
0.8854	High Similarity	NPC53889
0.8846	High Similarity	NPC104275
0.8846	High Similarity	NPC4747
0.8841	High Similarity	NPC267549
0.8839	High Similarity	NPC145425
0.8834	High Similarity	NPC477848
0.8827	High Similarity	NPC153755
0.8827	High Similarity	NPC190003
0.8827	High Similarity	NPC205076
0.8827	High Similarity	NPC48773
0.8827	High Similarity	NPC472386
0.8827	High Similarity	NPC175107
0.8827	High Similarity	NPC307518
0.882	High Similarity	NPC58053
0.882	High Similarity	NPC45638
0.882	High Similarity	NPC469931
0.882	High Similarity	NPC93337
0.882	High Similarity	NPC226294
0.882	High Similarity	NPC201292
0.882	High Similarity	NPC186807
0.882	High Similarity	NPC105025
0.882	High Similarity	NPC183036
0.882	High Similarity	NPC475942
0.882	High Similarity	NPC138927
0.8816	High Similarity	NPC106138
0.8812	High Similarity	NPC5778
0.8812	High Similarity	NPC236934
0.8808	High Similarity	NPC41844
0.8805	High Similarity	NPC191306
0.8805	High Similarity	NPC168822
0.8805	High Similarity	NPC88023
0.8805	High Similarity	NPC270335
0.8805	High Similarity	NPC19709
0.8805	High Similarity	NPC243930
0.8805	High Similarity	NPC121290
0.8805	High Similarity	NPC309025
0.8782	High Similarity	NPC250436
0.8782	High Similarity	NPC291948
0.8782	High Similarity	NPC300845
0.8782	High Similarity	NPC88803
0.8782	High Similarity	NPC104983
0.878	High Similarity	NPC198324
0.878	High Similarity	NPC473713
0.878	High Similarity	NPC472385
0.878	High Similarity	NPC472991
0.878	High Similarity	NPC233994
0.878	High Similarity	NPC211532
0.878	High Similarity	NPC472992
0.878	High Similarity	NPC297574
0.8776	High Similarity	NPC100389
0.8774	High Similarity	NPC281477
0.8773	High Similarity	NPC473550
0.8767	High Similarity	NPC186418
0.8765	High Similarity	NPC155763
0.8765	High Similarity	NPC105511
0.8765	High Similarity	NPC183357
0.8765	High Similarity	NPC471416
0.8765	High Similarity	NPC116864
0.8765	High Similarity	NPC72249
0.8765	High Similarity	NPC51326
0.8765	High Similarity	NPC235260
0.8765	High Similarity	NPC474434
0.8765	High Similarity	NPC34287
0.8765	High Similarity	NPC21190
0.8765	High Similarity	NPC20505
0.8765	High Similarity	NPC231194
0.8765	High Similarity	NPC244776
0.8765	High Similarity	NPC22195
0.8765	High Similarity	NPC181778
0.8765	High Similarity	NPC44558
0.8765	High Similarity	NPC206123
0.8759	High Similarity	NPC155098
0.8758	High Similarity	NPC226304
0.8758	High Similarity	NPC473818

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 NPC310661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	909
0.2-0.3	2051
0.3-0.4	2566
0.4-0.5	1821
0.5-0.6	965
0.6-0.7	408
0.7-0.8	118
0.8-0.85	20
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8782	High Similarity	NPD4868	Clinical (unspecified phase)
0.8758	High Similarity	NPD3818	Discontinued
0.872	High Similarity	NPD4338	Clinical (unspecified phase)
0.8704	High Similarity	NPD7054	Approved
0.8693	High Similarity	NPD1653	Approved
0.869	High Similarity	NPD230	Phase 1
0.865	High Similarity	NPD7074	Phase 3
0.865	High Similarity	NPD7472	Approved
0.8485	Intermediate Similarity	NPD6797	Phase 2
0.8434	Intermediate Similarity	NPD7251	Discontinued
0.8383	Intermediate Similarity	NPD7808	Phase 3
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD1934	Approved
0.8323	Intermediate Similarity	NPD7685	Pre-registration
0.8302	Intermediate Similarity	NPD1465	Phase 2
0.8263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD3882	Suspended
0.8187	Intermediate Similarity	NPD2801	Approved
0.8187	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3817	Phase 2
0.8098	Intermediate Similarity	NPD6234	Discontinued
0.8084	Intermediate Similarity	NPD7228	Approved
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD4965	Approved
0.7975	Intermediate Similarity	NPD4967	Phase 2
0.7975	Intermediate Similarity	NPD4966	Approved
0.7962	Intermediate Similarity	NPD1511	Approved
0.7949	Intermediate Similarity	NPD6190	Approved
0.7931	Intermediate Similarity	NPD9269	Phase 2
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7075	Discontinued
0.7922	Intermediate Similarity	NPD7266	Discontinued
0.7914	Intermediate Similarity	NPD5353	Approved
0.7905	Intermediate Similarity	NPD9494	Approved
0.7892	Intermediate Similarity	NPD7199	Phase 2
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.7862	Intermediate Similarity	NPD1512	Approved
0.7848	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD447	Suspended
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.7756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7736	Intermediate Similarity	NPD6799	Approved
0.7714	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6801	Discontinued
0.7682	Intermediate Similarity	NPD3027	Phase 3
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD9268	Approved
0.7647	Intermediate Similarity	NPD1613	Approved
0.7647	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1549	Phase 2
0.7636	Intermediate Similarity	NPD7819	Suspended
0.7619	Intermediate Similarity	NPD5494	Approved
0.7602	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD7240	Approved
0.758	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5403	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7469	Intermediate Similarity	NPD2532	Approved
0.7469	Intermediate Similarity	NPD2534	Approved
0.7469	Intermediate Similarity	NPD2533	Approved
0.7466	Intermediate Similarity	NPD9545	Approved
0.7456	Intermediate Similarity	NPD919	Approved
0.7455	Intermediate Similarity	NPD6599	Discontinued
0.7434	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5242	Approved
0.7362	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5401	Approved
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7342	Intermediate Similarity	NPD1510	Phase 2
0.7329	Intermediate Similarity	NPD3750	Approved
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD1240	Approved
0.7305	Intermediate Similarity	NPD6386	Approved
0.7305	Intermediate Similarity	NPD6385	Approved
0.7296	Intermediate Similarity	NPD2796	Approved
0.7285	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7267	Intermediate Similarity	NPD1652	Phase 2
0.7267	Intermediate Similarity	NPD6959	Discontinued
0.7267	Intermediate Similarity	NPD1247	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3787	Discontinued
0.7215	Intermediate Similarity	NPD1607	Approved
0.7188	Intermediate Similarity	NPD2935	Discontinued
0.7184	Intermediate Similarity	NPD3926	Phase 2
0.7169	Intermediate Similarity	NPD920	Approved
0.7167	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7135	Intermediate Similarity	NPD7768	Phase 2
0.7135	Intermediate Similarity	NPD7585	Approved
0.7125	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD7680	Approved
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7105	Intermediate Similarity	NPD9717	Approved
0.7095	Intermediate Similarity	NPD7039	Approved
0.7095	Intermediate Similarity	NPD7038	Approved
0.7093	Intermediate Similarity	NPD3749	Approved
0.7083	Intermediate Similarity	NPD7583	Approved
0.7078	Intermediate Similarity	NPD1203	Approved
0.7069	Intermediate Similarity	NPD8127	Discontinued
0.7067	Intermediate Similarity	NPD1357	Approved
0.7055	Intermediate Similarity	NPD1243	Approved
0.7055	Intermediate Similarity	NPD6674	Discontinued
0.7055	Intermediate Similarity	NPD2800	Approved
0.7049	Intermediate Similarity	NPD6843	Phase 3
0.7049	Intermediate Similarity	NPD6841	Approved
0.7049	Intermediate Similarity	NPD6842	Approved
0.7048	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5953	Discontinued
0.7039	Intermediate Similarity	NPD3705	Approved
0.7037	Intermediate Similarity	NPD6780	Approved
0.7037	Intermediate Similarity	NPD6777	Approved
0.7037	Intermediate Similarity	NPD6779	Approved
0.7037	Intermediate Similarity	NPD6781	Approved
0.7037	Intermediate Similarity	NPD6776	Approved
0.7037	Intermediate Similarity	NPD6778	Approved
0.7037	Intermediate Similarity	NPD6782	Approved
0.7029	Intermediate Similarity	NPD5710	Approved
0.7029	Intermediate Similarity	NPD5711	Approved
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD3748	Approved
0.7012	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4110	Phase 3
0.6995	Remote Similarity	NPD8434	Phase 2
0.6995	Remote Similarity	NPD7584	Approved
0.6988	Remote Similarity	NPD4357	Discontinued
0.6982	Remote Similarity	NPD3455	Phase 2
0.6982	Remote Similarity	NPD7458	Discontinued
0.6975	Remote Similarity	NPD6100	Approved
0.6975	Remote Similarity	NPD6099	Approved
0.6962	Remote Similarity	NPD411	Approved
0.6946	Remote Similarity	NPD3146	Approved
0.6946	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6832	Phase 2
0.6937	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5124	Phase 1
0.6928	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7286	Phase 2
0.6919	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1778	Approved
0.6908	Remote Similarity	NPD17	Approved
0.6901	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6653	Approved
0.6888	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7874	Approved
0.6882	Remote Similarity	NPD3226	Approved
0.6882	Remote Similarity	NPD824	Approved
0.6882	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD228	Approved
0.6862	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6798	Discontinued
0.6852	Remote Similarity	NPD7097	Phase 1
0.6839	Remote Similarity	NPD2983	Phase 2
0.6839	Remote Similarity	NPD7697	Approved
0.6839	Remote Similarity	NPD2982	Phase 2
0.6839	Remote Similarity	NPD7696	Phase 3
0.6839	Remote Similarity	NPD7698	Approved
0.6832	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD3686	Approved
0.6824	Remote Similarity	NPD3687	Approved
0.6821	Remote Similarity	NPD5536	Phase 2
0.6815	Remote Similarity	NPD1019	Discontinued
0.6814	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4062	Phase 3
0.681	Remote Similarity	NPD2799	Discontinued
0.681	Remote Similarity	NPD7033	Discontinued
0.6805	Remote Similarity	NPD6273	Approved
0.6804	Remote Similarity	NPD7871	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data