NPASS Compound

Structure

NPC100389 OpenBabel07101719512D 25 26 0 0 1 0 0 0 0 0999 V2000 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 -1.7321 0.0000 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 3.4641 -0.0000 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 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 -0.0000 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 -0.0000 -3.0000 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 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 1 23 1 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 17 1 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 7 1 1 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 19 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 6 0 0 0 14 15 1 0 0 0 0 14 21 1 1 0 0 0 15 16 1 0 0 0 0 15 22 1 6 0 0 0 16 24 1 1 0 0 0 16 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.11
Volume:	334.109
LogP:	-0.276
LogD:	-0.126
LogS:	-1.812
# Rotatable Bonds:	6
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	3.666
Fsp3:	0.438
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:	-5.8
MDCK Permeability:	5.372305531636812e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.844
Human Intestinal Absorption (HIA):	0.718
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.412
Plasma Protein Binding (PPB):	64.5893325805664%
Volume Distribution (VD):	0.288
Pgp-substrate:	28.829002380371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	3.538
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.27
AMES Toxicity:	0.34
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.3
Carcinogencity:	0.043
Eye Corrosion:	0.004
Eye Irritation:	0.109
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC100389

Natural Product ID:	NPC100389
*Common Name:**	Methyl 4-O-Beta-D-Glucopyranosylcaffeate
IUPAC Name:	methyl (E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
Synonyms:
Standard InCHIKey:	RHLLCIWGXNNMLI-BJGSYIFTSA-N
Standard InCHI:	InChI=1S/C16H20O9/c1-23-12(19)5-3-8-2-4-10(9(18)6-8)24-16-15(22)14(21)13(20)11(7-17)25-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16-/m1/s1
SMILES:	COC(=O)/C=C/c1ccc(c(c1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482045
PubChem CID:	12311282
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
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844940]
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.89	mM	PMID[479807]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	486.2	ug.mL-1	PMID[479807]

☑ 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 NPC100389 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	301
0.1-0.2	1471
0.2-0.3	4260
0.3-0.4	9530
0.4-0.5	8590
0.5-0.6	4943
0.6-0.7	8276
0.7-0.8	4398
0.8-0.85	621
0.85-0.9	247
0.9-0.95	51
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC37468
0.9847	High Similarity	NPC157554
0.9847	High Similarity	NPC186418
0.9776	High Similarity	NPC157816
0.9774	High Similarity	NPC202700
0.9704	High Similarity	NPC478239
0.9699	High Similarity	NPC226005
0.9556	High Similarity	NPC186406
0.9493	High Similarity	NPC199928
0.9493	High Similarity	NPC476865
0.9489	High Similarity	NPC232228
0.9485	High Similarity	NPC140502
0.9474	High Similarity	NPC55040
0.942	High Similarity	NPC476868
0.942	High Similarity	NPC476864
0.942	High Similarity	NPC476869
0.942	High Similarity	NPC476866
0.9357	High Similarity	NPC478237
0.9348	High Similarity	NPC476867
0.9348	High Similarity	NPC292443
0.9348	High Similarity	NPC110063
0.9348	High Similarity	NPC297342
0.9313	High Similarity	NPC307110
0.9313	High Similarity	NPC477294
0.9313	High Similarity	NPC477293
0.9313	High Similarity	NPC229784
0.9313	High Similarity	NPC248355
0.9291	High Similarity	NPC106138
0.9281	High Similarity	NPC216819
0.9281	High Similarity	NPC476382
0.9281	High Similarity	NPC262182
0.9281	High Similarity	NPC83743
0.9281	High Similarity	NPC252292
0.9281	High Similarity	NPC34927
0.9281	High Similarity	NPC287615
0.9281	High Similarity	NPC100998
0.9281	High Similarity	NPC34587
0.9248	High Similarity	NPC473285
0.9237	High Similarity	NPC232880
0.9237	High Similarity	NPC302378
0.9197	High Similarity	NPC210478
0.9191	High Similarity	NPC126206
0.9185	High Similarity	NPC185778
0.9179	High Similarity	NPC254398
0.9173	High Similarity	NPC65942
0.9173	High Similarity	NPC248307
0.9173	High Similarity	NPC219677
0.9167	High Similarity	NPC166040
0.9161	High Similarity	NPC213197
0.916	High Similarity	NPC476873
0.9149	High Similarity	NPC41844
0.9149	High Similarity	NPC232992
0.9118	High Similarity	NPC471664
0.9118	High Similarity	NPC471665
0.9111	High Similarity	NPC135127
0.9111	High Similarity	NPC471883
0.9104	High Similarity	NPC252833
0.9104	High Similarity	NPC473924
0.9098	High Similarity	NPC472024
0.9098	High Similarity	NPC80600
0.9091	High Similarity	NPC476871
0.9085	High Similarity	NPC261122
0.9085	High Similarity	NPC3460
0.9085	High Similarity	NPC28651
0.9085	High Similarity	NPC80732
0.9085	High Similarity	NPC201148
0.9085	High Similarity	NPC300262
0.9085	High Similarity	NPC210611
0.9085	High Similarity	NPC192763
0.9085	High Similarity	NPC215095
0.9085	High Similarity	NPC199311
0.9051	High Similarity	NPC470413
0.9051	High Similarity	NPC138738
0.9044	High Similarity	NPC476870
0.9037	High Similarity	NPC49074
0.9037	High Similarity	NPC6836
0.9037	High Similarity	NPC25821
0.9037	High Similarity	NPC132895
0.9023	High Similarity	NPC295970
0.9023	High Similarity	NPC26653
0.9023	High Similarity	NPC270849
0.9021	High Similarity	NPC476398
0.9021	High Similarity	NPC94871
0.9021	High Similarity	NPC313334
0.9021	High Similarity	NPC478242
0.9021	High Similarity	NPC259347
0.9021	High Similarity	NPC206264
0.9021	High Similarity	NPC90896
0.9021	High Similarity	NPC473427
0.9021	High Similarity	NPC212670
0.9021	High Similarity	NPC306890
0.9021	High Similarity	NPC283839
0.9021	High Similarity	NPC476386
0.9021	High Similarity	NPC111785
0.9021	High Similarity	NPC471062
0.9021	High Similarity	NPC470933
0.8986	High Similarity	NPC212770
0.8986	High Similarity	NPC98777
0.8973	High Similarity	NPC194095
0.8973	High Similarity	NPC327032
0.8973	High Similarity	NPC191046
0.8971	High Similarity	NPC886
0.8971	High Similarity	NPC35731
0.8971	High Similarity	NPC287597
0.8971	High Similarity	NPC470881
0.8971	High Similarity	NPC34293
0.8963	High Similarity	NPC162093
0.8958	High Similarity	NPC470927
0.8958	High Similarity	NPC257970
0.8958	High Similarity	NPC188393
0.8958	High Similarity	NPC470934
0.8951	High Similarity	NPC96294
0.8951	High Similarity	NPC93924
0.8929	High Similarity	NPC145319
0.8913	High Similarity	NPC476376
0.8913	High Similarity	NPC124149
0.8913	High Similarity	NPC78363
0.8913	High Similarity	NPC59324
0.8913	High Similarity	NPC65530
0.8904	High Similarity	NPC150442
0.8904	High Similarity	NPC157898
0.8897	High Similarity	NPC478249
0.8897	High Similarity	NPC7145
0.8897	High Similarity	NPC125823
0.8897	High Similarity	NPC85192
0.8897	High Similarity	NPC143480
0.8897	High Similarity	NPC269914
0.8889	High Similarity	NPC166168
0.8889	High Similarity	NPC9912
0.8881	High Similarity	NPC52740
0.8857	High Similarity	NPC476385
0.8857	High Similarity	NPC134405
0.8851	High Similarity	NPC471405
0.8851	High Similarity	NPC11411
0.8849	High Similarity	NPC197316
0.8849	High Similarity	NPC220942
0.8849	High Similarity	NPC472350
0.8849	High Similarity	NPC476383
0.8849	High Similarity	NPC64141
0.8849	High Similarity	NPC68092
0.8849	High Similarity	NPC89105
0.8849	High Similarity	NPC81515
0.8841	High Similarity	NPC164857
0.8841	High Similarity	NPC203230
0.8841	High Similarity	NPC52277
0.8841	High Similarity	NPC177035
0.8841	High Similarity	NPC199459
0.8841	High Similarity	NPC242028
0.8841	High Similarity	NPC470572
0.8841	High Similarity	NPC166180
0.8836	High Similarity	NPC289967
0.8836	High Similarity	NPC36130
0.8836	High Similarity	NPC478268
0.8836	High Similarity	NPC472611
0.8836	High Similarity	NPC203664
0.8836	High Similarity	NPC176186
0.8836	High Similarity	NPC169404
0.8836	High Similarity	NPC472612
0.8836	High Similarity	NPC53587
0.8836	High Similarity	NPC134905
0.8832	High Similarity	NPC237594
0.8832	High Similarity	NPC48863
0.8832	High Similarity	NPC187194
0.8832	High Similarity	NPC249791
0.8832	High Similarity	NPC251981
0.8832	High Similarity	NPC13745
0.8832	High Similarity	NPC476387
0.8832	High Similarity	NPC119060
0.8832	High Similarity	NPC87696
0.8832	High Similarity	NPC107478
0.8828	High Similarity	NPC205054
0.8828	High Similarity	NPC114740
0.8824	High Similarity	NPC299144
0.8824	High Similarity	NPC470270
0.8806	High Similarity	NPC146540
0.8797	High Similarity	NPC471157
0.8794	High Similarity	NPC222433
0.8794	High Similarity	NPC469559
0.8794	High Similarity	NPC189115
0.8794	High Similarity	NPC475084
0.8794	High Similarity	NPC265648
0.8792	High Similarity	NPC133984
0.8786	High Similarity	NPC106944
0.8784	High Similarity	NPC10205
0.8779	High Similarity	NPC52097
0.8777	High Similarity	NPC260425
0.8777	High Similarity	NPC304152
0.8777	High Similarity	NPC195196
0.8776	High Similarity	NPC105827
0.8776	High Similarity	NPC89693
0.8776	High Similarity	NPC310661
0.8776	High Similarity	NPC478241
0.8776	High Similarity	NPC229548
0.8768	High Similarity	NPC470236
0.8768	High Similarity	NPC214729
0.8759	High Similarity	NPC69513
0.8759	High Similarity	NPC215833
0.8741	High Similarity	NPC143120
0.8741	High Similarity	NPC274960
0.8741	High Similarity	NPC473909

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 NPC100389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	831
0.2-0.3	1922
0.3-0.4	2795
0.4-0.5	1740
0.5-0.6	985
0.6-0.7	545
0.7-0.8	81
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD1653	Approved
0.8849	High Similarity	NPD7266	Discontinued
0.8148	Intermediate Similarity	NPD1091	Approved
0.8071	Intermediate Similarity	NPD3027	Phase 3
0.8029	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7054	Approved
0.7926	Intermediate Similarity	NPD1357	Approved
0.7914	Intermediate Similarity	NPD7685	Pre-registration
0.7902	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1613	Approved
0.7901	Intermediate Similarity	NPD7074	Phase 3
0.7901	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD3705	Approved
0.7748	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6797	Phase 2
0.7733	Intermediate Similarity	NPD6190	Approved
0.7718	Intermediate Similarity	NPD6674	Discontinued
0.7697	Intermediate Similarity	NPD7251	Discontinued
0.7673	Intermediate Similarity	NPD6234	Discontinued
0.7669	Intermediate Similarity	NPD7228	Approved
0.7651	Intermediate Similarity	NPD7808	Phase 3
0.7622	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD228	Approved
0.758	Intermediate Similarity	NPD37	Approved
0.758	Intermediate Similarity	NPD1934	Approved
0.7557	Intermediate Similarity	NPD1358	Approved
0.7552	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4628	Phase 3
0.7547	Intermediate Similarity	NPD4966	Approved
0.7547	Intermediate Similarity	NPD4967	Phase 2
0.7547	Intermediate Similarity	NPD4965	Approved
0.7518	Intermediate Similarity	NPD5536	Phase 2
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7483	Intermediate Similarity	NPD1652	Phase 2
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7469	Intermediate Similarity	NPD7199	Phase 2
0.7439	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6166	Phase 2
0.7439	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3687	Approved
0.7436	Intermediate Similarity	NPD3686	Approved
0.7431	Intermediate Similarity	NPD9494	Approved
0.7429	Intermediate Similarity	NPD3496	Discontinued
0.7421	Intermediate Similarity	NPD8455	Phase 2
0.7421	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4060	Phase 1
0.7412	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD422	Phase 1
0.7375	Intermediate Similarity	NPD3817	Phase 2
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD447	Suspended
0.7348	Intermediate Similarity	NPD3134	Approved
0.7329	Intermediate Similarity	NPD3882	Suspended
0.7321	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6653	Approved
0.7312	Intermediate Similarity	NPD2801	Approved
0.7305	Intermediate Similarity	NPD5844	Phase 1
0.7279	Intermediate Similarity	NPD7843	Approved
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2982	Phase 2
0.7273	Intermediate Similarity	NPD2983	Phase 2
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7256	Intermediate Similarity	NPD8127	Discontinued
0.7248	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1933	Approved
0.7248	Intermediate Similarity	NPD5124	Phase 1
0.7248	Intermediate Similarity	NPD4340	Discontinued
0.7246	Intermediate Similarity	NPD7157	Approved
0.7239	Intermediate Similarity	NPD2684	Approved
0.723	Intermediate Similarity	NPD6233	Phase 2
0.7226	Intermediate Similarity	NPD5058	Phase 3
0.7225	Intermediate Similarity	NPD6841	Approved
0.7225	Intermediate Similarity	NPD6842	Approved
0.7225	Intermediate Similarity	NPD6843	Phase 3
0.7208	Intermediate Similarity	NPD4110	Phase 3
0.7208	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.7205	Intermediate Similarity	NPD2978	Approved
0.7205	Intermediate Similarity	NPD2977	Approved
0.7203	Intermediate Similarity	NPD2981	Phase 2
0.7202	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8312	Approved
0.7193	Intermediate Similarity	NPD8313	Approved
0.7192	Intermediate Similarity	NPD2861	Phase 2
0.7181	Intermediate Similarity	NPD1558	Phase 1
0.7178	Intermediate Similarity	NPD7075	Discontinued
0.7176	Intermediate Similarity	NPD7240	Approved
0.7176	Intermediate Similarity	NPD291	Approved
0.7164	Intermediate Similarity	NPD290	Approved
0.7124	Intermediate Similarity	NPD1375	Discontinued
0.7124	Intermediate Similarity	NPD5763	Approved
0.7124	Intermediate Similarity	NPD5762	Approved
0.7113	Intermediate Similarity	NPD1778	Approved
0.7101	Intermediate Similarity	NPD5283	Phase 1
0.7095	Intermediate Similarity	NPD7095	Approved
0.7089	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2492	Phase 1
0.7078	Intermediate Similarity	NPD2424	Discontinued
0.7075	Intermediate Similarity	NPD3018	Phase 2
0.707	Intermediate Similarity	NPD1511	Approved
0.707	Intermediate Similarity	NPD4357	Discontinued
0.7067	Intermediate Similarity	NPD3620	Phase 2
0.7067	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD556	Approved
0.7055	Intermediate Similarity	NPD5402	Approved
0.7047	Intermediate Similarity	NPD6798	Discontinued
0.7047	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4536	Approved
0.7039	Intermediate Similarity	NPD4538	Approved
0.7032	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4908	Phase 1
0.702	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD6671	Approved
0.6994	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4626	Approved
0.6987	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1512	Approved
0.6977	Remote Similarity	NPD7038	Approved
0.6977	Remote Similarity	NPD7039	Approved
0.6972	Remote Similarity	NPD9545	Approved
0.6962	Remote Similarity	NPD6799	Approved
0.6957	Remote Similarity	NPD969	Suspended
0.6954	Remote Similarity	NPD4140	Approved
0.6951	Remote Similarity	NPD5353	Approved
0.6948	Remote Similarity	NPD2935	Discontinued
0.6941	Remote Similarity	NPD3751	Discontinued
0.6937	Remote Similarity	NPD5403	Approved
0.6936	Remote Similarity	NPD7549	Discontinued
0.6933	Remote Similarity	NPD6801	Discontinued
0.6933	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4237	Approved
0.6923	Remote Similarity	NPD5585	Approved
0.6923	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD4236	Phase 3
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3060	Approved
0.6918	Remote Similarity	NPD4123	Phase 3
0.6918	Remote Similarity	NPD3536	Discontinued
0.691	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5535	Approved
0.6905	Remote Similarity	NPD6232	Discontinued
0.6897	Remote Similarity	NPD1610	Phase 2
0.6892	Remote Similarity	NPD5647	Approved
0.689	Remote Similarity	NPD7819	Suspended
0.689	Remote Similarity	NPD5772	Approved
0.689	Remote Similarity	NPD5773	Approved
0.6887	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5588	Approved
0.6883	Remote Similarity	NPD5960	Phase 3
0.6883	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD8166	Discontinued
0.6871	Remote Similarity	NPD6385	Approved
0.6871	Remote Similarity	NPD6386	Approved
0.6871	Remote Similarity	NPD3225	Approved
0.6871	Remote Similarity	NPD8651	Approved
0.6868	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1774	Approved
0.6853	Remote Similarity	NPD1548	Phase 1
0.6852	Remote Similarity	NPD3455	Phase 2
0.6852	Remote Similarity	NPD3111	Phase 1
0.6852	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1608	Approved
0.6839	Remote Similarity	NPD6032	Approved
0.6839	Remote Similarity	NPD1551	Phase 2
0.6838	Remote Similarity	NPD968	Approved
0.6835	Remote Similarity	NPD2677	Approved
0.6821	Remote Similarity	NPD3144	Approved
0.6821	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3145	Approved
0.6818	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4162	Approved
0.6813	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5401	Approved
0.6813	Remote Similarity	NPD3146	Approved
0.6812	Remote Similarity	NPD3022	Approved
0.6812	Remote Similarity	NPD3021	Approved
0.6811	Remote Similarity	NPD7680	Approved
0.681	Remote Similarity	NPD4675	Approved
0.681	Remote Similarity	NPD4678	Approved
0.6805	Remote Similarity	NPD3787	Discontinued
0.6803	Remote Similarity	NPD3685	Discontinued
0.6803	Remote Similarity	NPD4749	Approved
0.6795	Remote Similarity	NPD6005	Phase 3
0.6795	Remote Similarity	NPD6004	Phase 3
0.6795	Remote Similarity	NPD6002	Phase 3
0.6795	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5494	Approved
0.6784	Remote Similarity	NPD7473	Discontinued

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