NPASS Compound

Structure

CID60589 OpenBabel06191715392D 21 22 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 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 4.3301 0.5000 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 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 4.3301 1.5000 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 -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 -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 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 2 2 0 0 0 0 2 3 1 0 0 0 0 3 9 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 10 1 0 0 0 0 8 16 1 0 0 0 0 10 20 1 0 0 0 0 11 8 1 6 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 1 0 0 0 13 14 1 0 0 0 0 13 18 1 6 0 0 0 14 15 1 0 0 0 0 14 19 1 1 0 0 0 15 20 1 6 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	270.1
Volume:	272.236
LogP:	2.071
LogD:	1.789
LogS:	-3.748
# Rotatable Bonds:	4
TPSA:	75.21
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.764
Synthetic Accessibility Score:	2.27
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.755
MDCK Permeability:	9.590738955012057e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.18

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	91.13409423828125%
Volume Distribution (VD):	0.445
Pgp-substrate:	7.3469648361206055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.68
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.146
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.178
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	2.912
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.902
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.847
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.162
Carcinogencity:	0.73
Eye Corrosion:	0.004
Eye Irritation:	0.289
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC60589

Natural Product ID:	NPC60589
*Common Name:**	(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-Prop-2-Enylphenoxy)Oxane-3,4,5-Triol
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-prop-2-enylphenoxy)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	BGWWYZXBGAKMRB-UXXRCYHCSA-N
Standard InCHI:	InChI=1S/C15H20O6/c1-2-3-9-4-6-10(7-5-9)20-15-14(19)13(18)12(17)11(8-16)21-15/h2,4-7,11-19H,1,3,8H2/t11-,12-,13+,14-,15-/m1/s1
SMILES:	C=CCc1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL179783
PubChem CID:	44390556
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
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31419126]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28679	Prunus mume	Species	Rosaceae	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	3
Others	1

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[468239]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	18300.0	nM	PMID[468240]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[468238]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	6.0	%	PMID[468238]

☑ 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 NPC60589 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	322
0.1-0.2	1429
0.2-0.3	4179
0.3-0.4	11076
0.4-0.5	7602
0.5-0.6	6557
0.6-0.7	8687
0.7-0.8	2478
0.8-0.85	268
0.85-0.9	72
0.9-0.95	20
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469708
0.9737	High Similarity	NPC469412
0.9737	High Similarity	NPC269242
0.9737	High Similarity	NPC198734
0.9573	High Similarity	NPC287429
0.9402	High Similarity	NPC476142
0.9333	High Similarity	NPC198798
0.9316	High Similarity	NPC226712
0.918	High Similarity	NPC270849
0.918	High Similarity	NPC26653
0.913	High Similarity	NPC175771
0.9123	High Similarity	NPC313193
0.9106	High Similarity	NPC472024
0.9106	High Similarity	NPC80600
0.9098	High Similarity	NPC302378
0.9032	High Similarity	NPC9912
0.9024	High Similarity	NPC295970
0.9024	High Similarity	NPC248355
0.9024	High Similarity	NPC166040
0.9008	High Similarity	NPC470510
0.8957	High Similarity	NPC157338
0.888	High Similarity	NPC121376
0.8871	High Similarity	NPC97326
0.8852	High Similarity	NPC12308
0.8819	High Similarity	NPC476411
0.8819	High Similarity	NPC187194
0.881	High Similarity	NPC85799
0.881	High Similarity	NPC165686
0.881	High Similarity	NPC162093
0.881	High Similarity	NPC26080
0.881	High Similarity	NPC303422
0.8803	High Similarity	NPC148055
0.88	High Similarity	NPC474491
0.8793	High Similarity	NPC142319
0.879	High Similarity	NPC40377
0.879	High Similarity	NPC146540
0.875	High Similarity	NPC79957
0.874	High Similarity	NPC294166
0.874	High Similarity	NPC49074
0.874	High Similarity	NPC25821
0.874	High Similarity	NPC215833
0.874	High Similarity	NPC115022
0.874	High Similarity	NPC69513
0.873	High Similarity	NPC248307
0.873	High Similarity	NPC65942
0.872	High Similarity	NPC307110
0.872	High Similarity	NPC218003
0.8689	High Similarity	NPC212176
0.8682	High Similarity	NPC294470
0.8672	High Similarity	NPC471029
0.8672	High Similarity	NPC188555
0.8672	High Similarity	NPC13745
0.8672	High Similarity	NPC251981
0.8672	High Similarity	NPC130496
0.8672	High Similarity	NPC48863
0.8661	High Similarity	NPC299144
0.8661	High Similarity	NPC269421
0.8651	High Similarity	NPC262606
0.8615	High Similarity	NPC138738
0.8615	High Similarity	NPC262328
0.8615	High Similarity	NPC87777
0.8615	High Similarity	NPC470413
0.8609	High Similarity	NPC46844
0.8605	High Similarity	NPC238243
0.8605	High Similarity	NPC470236
0.8605	High Similarity	NPC212729
0.8605	High Similarity	NPC55040
0.8583	High Similarity	NPC166168
0.8571	High Similarity	NPC9248
0.8538	High Similarity	NPC164857
0.8538	High Similarity	NPC166180
0.8538	High Similarity	NPC186418
0.8538	High Similarity	NPC203230
0.8538	High Similarity	NPC242028
0.8538	High Similarity	NPC103409
0.8538	High Similarity	NPC40664
0.8538	High Similarity	NPC197723
0.8538	High Similarity	NPC138350
0.8538	High Similarity	NPC3293
0.8538	High Similarity	NPC165482
0.8538	High Similarity	NPC37468
0.8527	High Similarity	NPC470881
0.8527	High Similarity	NPC34456
0.8527	High Similarity	NPC35731
0.8525	High Similarity	NPC11724
0.8516	High Similarity	NPC252833
0.8512	High Similarity	NPC469702
0.8512	High Similarity	NPC282409
0.85	High Similarity	NPC228907
0.8496	Intermediate Similarity	NPC37714
0.8496	Intermediate Similarity	NPC152384
0.8485	Intermediate Similarity	NPC195814
0.8485	Intermediate Similarity	NPC106944
0.8473	Intermediate Similarity	NPC65530
0.8473	Intermediate Similarity	NPC124149
0.8473	Intermediate Similarity	NPC59324
0.8473	Intermediate Similarity	NPC36434
0.8455	Intermediate Similarity	NPC52097
0.845	Intermediate Similarity	NPC132895
0.845	Intermediate Similarity	NPC6836
0.8443	Intermediate Similarity	NPC476872
0.8443	Intermediate Similarity	NPC469548
0.8443	Intermediate Similarity	NPC160854
0.8443	Intermediate Similarity	NPC469703
0.8443	Intermediate Similarity	NPC476448
0.8443	Intermediate Similarity	NPC201402
0.8443	Intermediate Similarity	NPC476445
0.8443	Intermediate Similarity	NPC469704
0.8438	Intermediate Similarity	NPC475067
0.8421	Intermediate Similarity	NPC76871
0.8421	Intermediate Similarity	NPC108674
0.8421	Intermediate Similarity	NPC79908
0.8421	Intermediate Similarity	NPC469661
0.8421	Intermediate Similarity	NPC210192
0.8409	Intermediate Similarity	NPC100389
0.8409	Intermediate Similarity	NPC212770
0.8409	Intermediate Similarity	NPC98777
0.8409	Intermediate Similarity	NPC298821
0.84	Intermediate Similarity	NPC278552
0.84	Intermediate Similarity	NPC167571
0.84	Intermediate Similarity	NPC207179
0.8397	Intermediate Similarity	NPC475628
0.8397	Intermediate Similarity	NPC172818
0.8397	Intermediate Similarity	NPC177035
0.8397	Intermediate Similarity	NPC52277
0.8397	Intermediate Similarity	NPC25695
0.8397	Intermediate Similarity	NPC199459
0.839	Intermediate Similarity	NPC301735
0.8385	Intermediate Similarity	NPC87696
0.8385	Intermediate Similarity	NPC107478
0.8374	Intermediate Similarity	NPC55608
0.8374	Intermediate Similarity	NPC469686
0.8374	Intermediate Similarity	NPC266045
0.8372	Intermediate Similarity	NPC470270
0.8358	Intermediate Similarity	NPC469559
0.8358	Intermediate Similarity	NPC139976
0.8358	Intermediate Similarity	NPC49542
0.8358	Intermediate Similarity	NPC230718
0.8358	Intermediate Similarity	NPC128337
0.8358	Intermediate Similarity	NPC60249
0.8358	Intermediate Similarity	NPC246947
0.8358	Intermediate Similarity	NPC84207
0.8358	Intermediate Similarity	NPC472353
0.8358	Intermediate Similarity	NPC189115
0.8358	Intermediate Similarity	NPC5253
0.8348	Intermediate Similarity	NPC251306
0.8346	Intermediate Similarity	NPC123761
0.8346	Intermediate Similarity	NPC72529
0.8346	Intermediate Similarity	NPC202700
0.8346	Intermediate Similarity	NPC210478
0.8333	Intermediate Similarity	NPC301651
0.8333	Intermediate Similarity	NPC304152
0.8333	Intermediate Similarity	NPC473556
0.8333	Intermediate Similarity	NPC8302
0.8333	Intermediate Similarity	NPC134260
0.8321	Intermediate Similarity	NPC185778
0.832	Intermediate Similarity	NPC109822
0.832	Intermediate Similarity	NPC94276
0.8308	Intermediate Similarity	NPC215037
0.8306	Intermediate Similarity	NPC71090
0.8306	Intermediate Similarity	NPC471067
0.8305	Intermediate Similarity	NPC115379
0.8296	Intermediate Similarity	NPC469367
0.8296	Intermediate Similarity	NPC116922
0.8296	Intermediate Similarity	NPC185307
0.8296	Intermediate Similarity	NPC46092
0.8296	Intermediate Similarity	NPC473044
0.8296	Intermediate Similarity	NPC470950
0.8284	Intermediate Similarity	NPC215512
0.8284	Intermediate Similarity	NPC80098
0.8284	Intermediate Similarity	NPC186406
0.8284	Intermediate Similarity	NPC89686
0.8284	Intermediate Similarity	NPC476442
0.8284	Intermediate Similarity	NPC273932
0.8284	Intermediate Similarity	NPC257095
0.8281	Intermediate Similarity	NPC86030
0.8281	Intermediate Similarity	NPC5851
0.8279	Intermediate Similarity	NPC135961
0.8271	Intermediate Similarity	NPC156376
0.8268	Intermediate Similarity	NPC288416
0.8268	Intermediate Similarity	NPC41706
0.8268	Intermediate Similarity	NPC111247
0.8268	Intermediate Similarity	NPC319625
0.8268	Intermediate Similarity	NPC118787
0.8268	Intermediate Similarity	NPC183181
0.8268	Intermediate Similarity	NPC163332
0.8268	Intermediate Similarity	NPC292056
0.8268	Intermediate Similarity	NPC147821
0.8258	Intermediate Similarity	NPC157554
0.8258	Intermediate Similarity	NPC469383
0.8258	Intermediate Similarity	NPC104167
0.8254	Intermediate Similarity	NPC83218
0.8254	Intermediate Similarity	NPC126991
0.8246	Intermediate Similarity	NPC108875
0.8246	Intermediate Similarity	NPC38079
0.824	Intermediate Similarity	NPC470907
0.824	Intermediate Similarity	NPC178449
0.824	Intermediate Similarity	NPC232454
0.8235	Intermediate Similarity	NPC469313
0.8235	Intermediate Similarity	NPC168579

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 NPC60589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	818
0.2-0.3	1758
0.3-0.4	2795
0.4-0.5	1775
0.5-0.6	1051
0.6-0.7	612
0.7-0.8	63
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9316	High Similarity	NPD1091	Approved
0.8276	Intermediate Similarity	NPD2684	Approved
0.819	Intermediate Similarity	NPD290	Approved
0.8151	Intermediate Similarity	NPD7843	Approved
0.7971	Intermediate Similarity	NPD5058	Phase 3
0.7955	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1613	Approved
0.7951	Intermediate Similarity	NPD7157	Approved
0.784	Intermediate Similarity	NPD1357	Approved
0.7817	Intermediate Similarity	NPD1653	Approved
0.7795	Intermediate Similarity	NPD3705	Approved
0.7778	Intermediate Similarity	NPD4536	Approved
0.7778	Intermediate Similarity	NPD4538	Approved
0.7778	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD1548	Phase 1
0.7754	Intermediate Similarity	NPD6674	Discontinued
0.7754	Intermediate Similarity	NPD1652	Phase 2
0.7727	Intermediate Similarity	NPD3027	Phase 3
0.7721	Intermediate Similarity	NPD5588	Approved
0.7721	Intermediate Similarity	NPD5960	Phase 3
0.7674	Intermediate Similarity	NPD3685	Discontinued
0.7671	Intermediate Similarity	NPD8455	Phase 2
0.7656	Intermediate Similarity	NPD1610	Phase 2
0.7652	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD968	Approved
0.7638	Intermediate Similarity	NPD5846	Approved
0.7638	Intermediate Similarity	NPD6516	Phase 2
0.7615	Intermediate Similarity	NPD8651	Approved
0.7612	Intermediate Similarity	NPD6233	Phase 2
0.7609	Intermediate Similarity	NPD7266	Discontinued
0.7607	Intermediate Similarity	NPD291	Approved
0.7589	Intermediate Similarity	NPD9365	Approved
0.7583	Intermediate Similarity	NPD1358	Approved
0.7576	Intermediate Similarity	NPD2861	Phase 2
0.7576	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD821	Approved
0.7519	Intermediate Similarity	NPD4908	Phase 1
0.7518	Intermediate Similarity	NPD7097	Phase 1
0.7517	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3179	Approved
0.7463	Intermediate Similarity	NPD3180	Approved
0.7459	Intermediate Similarity	NPD556	Approved
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6798	Discontinued
0.7385	Intermediate Similarity	NPD422	Phase 1
0.7372	Intermediate Similarity	NPD4340	Discontinued
0.7364	Intermediate Similarity	NPD5125	Phase 3
0.7364	Intermediate Similarity	NPD5126	Approved
0.7353	Intermediate Similarity	NPD4062	Phase 3
0.7339	Intermediate Similarity	NPD228	Approved
0.7324	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD2424	Discontinued
0.7293	Intermediate Similarity	NPD1819	Approved
0.7293	Intermediate Similarity	NPD1820	Approved
0.7293	Intermediate Similarity	NPD1818	Approved
0.7293	Intermediate Similarity	NPD1817	Approved
0.728	Intermediate Similarity	NPD5535	Approved
0.7246	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6355	Discontinued
0.7246	Intermediate Similarity	NPD5124	Phase 1
0.7244	Intermediate Similarity	NPD6671	Approved
0.7234	Intermediate Similarity	NPD1375	Discontinued
0.7213	Intermediate Similarity	NPD3134	Approved
0.7209	Intermediate Similarity	NPD1894	Discontinued
0.7203	Intermediate Similarity	NPD4535	Phase 3
0.72	Intermediate Similarity	NPD969	Suspended
0.7197	Intermediate Similarity	NPD2235	Phase 2
0.7197	Intermediate Similarity	NPD2231	Phase 2
0.7194	Intermediate Similarity	NPD6653	Approved
0.7174	Intermediate Similarity	NPD4060	Phase 1
0.7154	Intermediate Similarity	NPD9552	Approved
0.7153	Intermediate Similarity	NPD2677	Approved
0.7122	Intermediate Similarity	NPD5735	Approved
0.7121	Intermediate Similarity	NPD1535	Discovery
0.7113	Intermediate Similarity	NPD5762	Approved
0.7113	Intermediate Similarity	NPD5763	Approved
0.7111	Intermediate Similarity	NPD5647	Approved
0.7111	Intermediate Similarity	NPD558	Phase 2
0.7109	Intermediate Similarity	NPD191	Approved
0.7101	Intermediate Similarity	NPD1423	Approved
0.7099	Intermediate Similarity	NPD1778	Approved
0.7092	Intermediate Similarity	NPD4108	Discontinued
0.7092	Intermediate Similarity	NPD7033	Discontinued
0.7089	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7054	Approved
0.7087	Intermediate Similarity	NPD1241	Discontinued
0.7087	Intermediate Similarity	NPD5283	Phase 1
0.708	Intermediate Similarity	NPD3166	Approved
0.708	Intermediate Similarity	NPD7095	Approved
0.708	Intermediate Similarity	NPD3164	Approved
0.708	Intermediate Similarity	NPD3165	Approved
0.708	Intermediate Similarity	NPD3167	Approved
0.7068	Intermediate Similarity	NPD1481	Phase 2
0.705	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3496	Discontinued
0.7044	Intermediate Similarity	NPD7074	Phase 3
0.7044	Intermediate Similarity	NPD7472	Approved
0.7037	Intermediate Similarity	NPD1794	Approved
0.7037	Intermediate Similarity	NPD6362	Approved
0.7029	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3818	Discontinued
0.7021	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4749	Approved
0.7015	Intermediate Similarity	NPD6582	Phase 2
0.7015	Intermediate Similarity	NPD2983	Phase 2
0.7015	Intermediate Similarity	NPD6583	Phase 3
0.7015	Intermediate Similarity	NPD2982	Phase 2
0.7008	Intermediate Similarity	NPD1138	Approved
0.7007	Intermediate Similarity	NPD3536	Discontinued
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD776	Approved
0.6987	Remote Similarity	NPD3787	Discontinued
0.6986	Remote Similarity	NPD5756	Phase 2
0.6985	Remote Similarity	NPD3691	Phase 2
0.6985	Remote Similarity	NPD3690	Phase 2
0.6978	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7251	Discontinued
0.6957	Remote Similarity	NPD6559	Discontinued
0.695	Remote Similarity	NPD3054	Approved
0.695	Remote Similarity	NPD3052	Approved
0.6947	Remote Similarity	NPD1182	Approved
0.6944	Remote Similarity	NPD1549	Phase 2
0.694	Remote Similarity	NPD2981	Phase 2
0.694	Remote Similarity	NPD1608	Approved
0.6939	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1774	Approved
0.6939	Remote Similarity	NPD6799	Approved
0.6929	Remote Similarity	NPD1558	Phase 1
0.6929	Remote Similarity	NPD1137	Approved
0.6929	Remote Similarity	NPD1139	Approved
0.6929	Remote Similarity	NPD4140	Approved
0.6923	Remote Similarity	NPD7199	Phase 2
0.6923	Remote Similarity	NPD2240	Approved
0.6923	Remote Similarity	NPD2239	Approved
0.6923	Remote Similarity	NPD3596	Phase 2
0.6917	Remote Similarity	NPD3847	Discontinued
0.6914	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7808	Phase 3
0.6912	Remote Similarity	NPD987	Approved
0.6911	Remote Similarity	NPD9501	Approved
0.6908	Remote Similarity	NPD37	Approved
0.6906	Remote Similarity	NPD1048	Approved
0.6905	Remote Similarity	NPD5451	Approved
0.6897	Remote Similarity	NPD4237	Approved
0.6897	Remote Similarity	NPD4236	Phase 3
0.6889	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4380	Phase 2
0.6883	Remote Similarity	NPD4967	Phase 2
0.6883	Remote Similarity	NPD4966	Approved
0.6883	Remote Similarity	NPD4965	Approved
0.6875	Remote Similarity	NPD6004	Phase 3
0.6875	Remote Similarity	NPD6002	Phase 3
0.6875	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6005	Phase 3
0.6867	Remote Similarity	NPD3686	Approved
0.6867	Remote Similarity	NPD3687	Approved
0.6863	Remote Similarity	NPD2978	Approved
0.6863	Remote Similarity	NPD2977	Approved
0.6863	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6584	Phase 3
0.6855	Remote Similarity	NPD9697	Approved
0.6838	Remote Similarity	NPD3225	Approved
0.6835	Remote Similarity	NPD4625	Phase 3
0.6835	Remote Similarity	NPD5163	Phase 2
0.6828	Remote Similarity	NPD4534	Discontinued
0.6828	Remote Similarity	NPD5958	Discontinued
0.6824	Remote Similarity	NPD7212	Phase 2
0.6824	Remote Similarity	NPD7213	Phase 3
0.6818	Remote Similarity	NPD6581	Approved
0.6818	Remote Similarity	NPD6580	Approved
0.6815	Remote Similarity	NPD1840	Phase 2
0.6813	Remote Similarity	NPD7228	Approved
0.6812	Remote Similarity	NPD3018	Phase 2
0.6809	Remote Similarity	NPD2238	Phase 2
0.6809	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2933	Approved
0.6807	Remote Similarity	NPD2934	Approved
0.6806	Remote Similarity	NPD6032	Approved
0.68	Remote Similarity	NPD5403	Approved
0.6797	Remote Similarity	NPD1934	Approved
0.6795	Remote Similarity	NPD6234	Discontinued
0.679	Remote Similarity	NPD7007	Discovery
0.6788	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5061	Approved
0.6781	Remote Similarity	NPD4162	Approved
0.6781	Remote Similarity	NPD5062	Approved
0.6781	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6419	Discontinued
0.6779	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5401	Approved
0.6774	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6382	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