NPASS Compound

Structure

NPC4958 OpenBabel07101718302D 29 31 0 0 1 0 0 0 0 0999 V2000 -5.1962 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 -5.1962 1.0000 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 -4.3301 1.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -3.4641 1.0000 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 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 -2.5981 1.5000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 27 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 28 1 1 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.13
Volume:	389.464
LogP:	1.128
LogD:	0.972
LogS:	-2.623
# Rotatable Bonds:	7
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	3.513
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.134
MDCK Permeability:	1.8170783732784912e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.381
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.414
Plasma Protein Binding (PPB):	92.01589965820312%
Volume Distribution (VD):	0.548
Pgp-substrate:	7.219928741455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.385
CYP2D6-inhibitor:	0.599
CYP2D6-substrate:	0.227
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	5.766
Half-life (T1/2):	0.939

ADMET: Toxicity

hERG Blockers:	0.236
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.278
AMES Toxicity:	0.285
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.817
Carcinogencity:	0.228
Eye Corrosion:	0.003
Eye Irritation:	0.77
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC4958

Natural Product ID:	NPC4958
*Common Name:**	Poliothyrsoside
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-hydroxy-2-(hydroxymethyl)phenoxy]oxan-2-yl]methyl benzoate
Synonyms:	Poliothrysoside; Poliothyrsoside
Standard InCHIKey:	FLROYCKIIJCTDY-BFMVXSJESA-N
Standard InCHI:	InChI=1S/C20H22O9/c21-9-12-8-13(22)6-7-14(12)28-20-18(25)17(24)16(23)15(29-20)10-27-19(26)11-4-2-1-3-5-11/h1-8,15-18,20-25H,9-10H2/t15-,16-,17+,18-,20-/m1/s1
SMILES:	c1ccc(cc1)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2ccc(cc2CO)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512419
PubChem CID:	3084295
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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO22355	Flacourtia indica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23354072]
NPO22355	Flacourtia indica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	4
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	25.0	%	PMID[493252]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	136500.0	nM	PMID[493254]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[493253]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	IC50	>	50000.0	nM	PMID[493254]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	25000.0	nM	PMID[493254]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	16.8	n.a.	PMID[493254]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8100.0	nM	PMID[493254]

☑ 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 NPC4958 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	1446
0.2-0.3	3555
0.3-0.4	8223
0.4-0.5	10125
0.5-0.6	4210
0.6-0.7	6537
0.7-0.8	7366
0.8-0.85	725
0.85-0.9	128
0.9-0.95	27
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC140722
1.0	High Similarity	NPC92054
0.979	High Similarity	NPC93619
0.9589	High Similarity	NPC92153
0.9589	High Similarity	NPC279281
0.9589	High Similarity	NPC299761
0.9589	High Similarity	NPC230439
0.9571	High Similarity	NPC245219
0.9571	High Similarity	NPC31081
0.9571	High Similarity	NPC65833
0.9521	High Similarity	NPC215811
0.9456	High Similarity	NPC299435
0.9456	High Similarity	NPC260604
0.9444	High Similarity	NPC83975
0.9396	High Similarity	NPC476026
0.9396	High Similarity	NPC474401
0.9396	High Similarity	NPC474441
0.9396	High Similarity	NPC474398
0.9333	High Similarity	NPC57072
0.9333	High Similarity	NPC231475
0.9296	High Similarity	NPC145319
0.9257	High Similarity	NPC34965
0.9257	High Similarity	NPC183536
0.9195	High Similarity	NPC185103
0.9178	High Similarity	NPC302989
0.9116	High Similarity	NPC22137
0.9116	High Similarity	NPC111785
0.9091	High Similarity	NPC475183
0.9085	High Similarity	NPC132737
0.9085	High Similarity	NPC217950
0.9079	High Similarity	NPC287872
0.9079	High Similarity	NPC74319
0.9054	High Similarity	NPC182350
0.9032	High Similarity	NPC280923
0.9028	High Similarity	NPC164599
0.8993	High Similarity	NPC131874
0.8974	High Similarity	NPC475174
0.8973	High Similarity	NPC138915
0.8966	High Similarity	NPC242756
0.8961	High Similarity	NPC472859
0.8961	High Similarity	NPC25389
0.8961	High Similarity	NPC311803
0.8961	High Similarity	NPC71780
0.8944	High Similarity	NPC166180
0.894	High Similarity	NPC191046
0.894	High Similarity	NPC194095
0.894	High Similarity	NPC327032
0.8933	High Similarity	NPC134905
0.8933	High Similarity	NPC36130
0.8912	High Similarity	NPC291153
0.8904	High Similarity	NPC292443
0.8904	High Similarity	NPC471028
0.8903	High Similarity	NPC90905
0.8903	High Similarity	NPC4013
0.8896	High Similarity	NPC119125
0.8896	High Similarity	NPC328093
0.8896	High Similarity	NPC166277
0.8889	High Similarity	NPC177742
0.8882	High Similarity	NPC10205
0.8874	High Similarity	NPC157898
0.8867	High Similarity	NPC475890
0.8851	High Similarity	NPC474422
0.8846	High Similarity	NPC127415
0.8846	High Similarity	NPC121290
0.8831	High Similarity	NPC160780
0.8831	High Similarity	NPC289811
0.8828	High Similarity	NPC80098
0.8824	High Similarity	NPC471405
0.8816	High Similarity	NPC470331
0.8811	High Similarity	NPC471345
0.8805	High Similarity	NPC280385
0.88	High Similarity	NPC100818
0.8784	High Similarity	NPC199928
0.8782	High Similarity	NPC22324
0.8776	High Similarity	NPC232228
0.8774	High Similarity	NPC239966
0.8774	High Similarity	NPC203020
0.8774	High Similarity	NPC289346
0.8766	High Similarity	NPC43638
0.8766	High Similarity	NPC1913
0.8766	High Similarity	NPC133984
0.875	High Similarity	NPC259767
0.875	High Similarity	NPC137813
0.875	High Similarity	NPC88484
0.8701	High Similarity	NPC127406
0.8701	High Similarity	NPC261866
0.8699	High Similarity	NPC186406
0.8696	High Similarity	NPC470438
0.8696	High Similarity	NPC163165
0.8688	High Similarity	NPC210808
0.8688	High Similarity	NPC199079
0.8679	High Similarity	NPC116745
0.8671	High Similarity	NPC99216
0.8671	High Similarity	NPC178281
0.8662	High Similarity	NPC56735
0.8662	High Similarity	NPC61594
0.8662	High Similarity	NPC285108
0.8662	High Similarity	NPC33298
0.8645	High Similarity	NPC313163
0.8645	High Similarity	NPC156457
0.8645	High Similarity	NPC60966
0.8645	High Similarity	NPC161749
0.8645	High Similarity	NPC197896
0.8645	High Similarity	NPC472860
0.8645	High Similarity	NPC258035
0.8643	High Similarity	NPC40377
0.8643	High Similarity	NPC146540
0.8642	High Similarity	NPC169645
0.8642	High Similarity	NPC84482
0.8636	High Similarity	NPC99233
0.8634	High Similarity	NPC288152
0.8634	High Similarity	NPC254540
0.8634	High Similarity	NPC172807
0.8634	High Similarity	NPC137871
0.8634	High Similarity	NPC211594
0.8634	High Similarity	NPC9002
0.8634	High Similarity	NPC257011
0.8634	High Similarity	NPC472386
0.8627	High Similarity	NPC121001
0.8627	High Similarity	NPC259182
0.8625	High Similarity	NPC472133
0.8625	High Similarity	NPC95421
0.8625	High Similarity	NPC198125
0.8616	High Similarity	NPC70441
0.8611	High Similarity	NPC185778
0.8608	High Similarity	NPC17432
0.8608	High Similarity	NPC147596
0.8608	High Similarity	NPC168822
0.8608	High Similarity	NPC88043
0.8599	High Similarity	NPC477629
0.8599	High Similarity	NPC270675
0.8599	High Similarity	NPC195685
0.8599	High Similarity	NPC472994
0.8599	High Similarity	NPC210961
0.8599	High Similarity	NPC477628
0.859	High Similarity	NPC193749
0.859	High Similarity	NPC183402
0.859	High Similarity	NPC73511
0.859	High Similarity	NPC43761
0.8589	High Similarity	NPC472992
0.8589	High Similarity	NPC472991
0.8581	High Similarity	NPC149368
0.8581	High Similarity	NPC478239
0.8581	High Similarity	NPC170475
0.8581	High Similarity	NPC265480
0.8571	High Similarity	NPC143851
0.8571	High Similarity	NPC149011
0.8571	High Similarity	NPC471416
0.8571	High Similarity	NPC43434
0.8571	High Similarity	NPC105511
0.8571	High Similarity	NPC204937
0.8571	High Similarity	NPC39360
0.8571	High Similarity	NPC106625
0.8571	High Similarity	NPC34287
0.8571	High Similarity	NPC83283
0.8571	High Similarity	NPC210003
0.8571	High Similarity	NPC44558
0.8571	High Similarity	NPC472129
0.8571	High Similarity	NPC29763
0.8562	High Similarity	NPC45618
0.8562	High Similarity	NPC298847
0.8562	High Similarity	NPC146792
0.8562	High Similarity	NPC58716
0.8553	High Similarity	NPC472131
0.8553	High Similarity	NPC472130
0.8553	High Similarity	NPC88886
0.8553	High Similarity	NPC7752
0.8553	High Similarity	NPC165720
0.8553	High Similarity	NPC104172
0.8544	High Similarity	NPC146837
0.8544	High Similarity	NPC212099
0.8544	High Similarity	NPC472876
0.8544	High Similarity	NPC278329
0.8544	High Similarity	NPC216752
0.8544	High Similarity	NPC300537
0.8544	High Similarity	NPC77660
0.8544	High Similarity	NPC127782
0.8544	High Similarity	NPC101116
0.8544	High Similarity	NPC189142
0.8543	High Similarity	NPC478237
0.8542	High Similarity	NPC34456
0.8537	High Similarity	NPC476618
0.8537	High Similarity	NPC476620
0.8537	High Similarity	NPC476619
0.8537	High Similarity	NPC476622
0.8537	High Similarity	NPC476623
0.8537	High Similarity	NPC476621
0.8537	High Similarity	NPC472387
0.8535	High Similarity	NPC271479
0.8535	High Similarity	NPC472320
0.8531	High Similarity	NPC269421
0.8528	High Similarity	NPC115760
0.8528	High Similarity	NPC477848
0.8528	High Similarity	NPC237435
0.8528	High Similarity	NPC43211
0.8528	High Similarity	NPC264735
0.8528	High Similarity	NPC49344
0.8528	High Similarity	NPC210094
0.8528	High Similarity	NPC135277
0.8528	High Similarity	NPC101191

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 NPC4958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	823
0.2-0.3	1716
0.3-0.4	2591
0.4-0.5	1959
0.5-0.6	1149
0.6-0.7	454
0.7-0.8	155
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8645	High Similarity	NPD4381	Clinical (unspecified phase)
0.8528	High Similarity	NPD4338	Clinical (unspecified phase)
0.8516	High Similarity	NPD5402	Approved
0.8487	Intermediate Similarity	NPD1653	Approved
0.8354	Intermediate Similarity	NPD6559	Discontinued
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD7054	Approved
0.8253	Intermediate Similarity	NPD8312	Approved
0.8253	Intermediate Similarity	NPD8313	Approved
0.8232	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8182	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8143	Intermediate Similarity	NPD1091	Approved
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD8455	Phase 2
0.8084	Intermediate Similarity	NPD7808	Phase 3
0.8063	Intermediate Similarity	NPD7075	Discontinued
0.8061	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD5401	Approved
0.8026	Intermediate Similarity	NPD4628	Phase 3
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8023	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7973	Intermediate Similarity	NPD1933	Approved
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7947	Intermediate Similarity	NPD7266	Discontinued
0.7925	Intermediate Similarity	NPD1934	Approved
0.7917	Intermediate Similarity	NPD1203	Approved
0.7917	Intermediate Similarity	NPD7685	Pre-registration
0.7875	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2801	Approved
0.7875	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3817	Phase 2
0.7821	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7792	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7771	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6166	Phase 2
0.7764	Intermediate Similarity	NPD7819	Suspended
0.7756	Intermediate Similarity	NPD6799	Approved
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7742	Intermediate Similarity	NPD6190	Approved
0.7733	Intermediate Similarity	NPD447	Suspended
0.7733	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6233	Phase 2
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3751	Discontinued
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7643	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1511	Approved
0.764	Intermediate Similarity	NPD7411	Suspended
0.761	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3225	Approved
0.7593	Intermediate Similarity	NPD37	Approved
0.759	Intermediate Similarity	NPD7199	Phase 2
0.7586	Intermediate Similarity	NPD9717	Approved
0.7582	Intermediate Similarity	NPD7435	Discontinued
0.7582	Intermediate Similarity	NPD4308	Phase 3
0.7576	Intermediate Similarity	NPD6234	Discontinued
0.7574	Intermediate Similarity	NPD7228	Approved
0.7564	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4965	Approved
0.7561	Intermediate Similarity	NPD3882	Suspended
0.7561	Intermediate Similarity	NPD4967	Phase 2
0.7561	Intermediate Similarity	NPD4966	Approved
0.7551	Intermediate Similarity	NPD2797	Approved
0.755	Intermediate Similarity	NPD1613	Approved
0.755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1512	Approved
0.7545	Intermediate Similarity	NPD3787	Discontinued
0.7533	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2313	Discontinued
0.7533	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD1510	Phase 2
0.7468	Intermediate Similarity	NPD3748	Approved
0.7455	Intermediate Similarity	NPD7768	Phase 2
0.745	Intermediate Similarity	NPD2861	Phase 2
0.7448	Intermediate Similarity	NPD3496	Discontinued
0.7432	Intermediate Similarity	NPD6823	Phase 2
0.7429	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5494	Approved
0.7419	Intermediate Similarity	NPD2796	Approved
0.7417	Intermediate Similarity	NPD3268	Approved
0.7417	Intermediate Similarity	NPD411	Approved
0.7407	Intermediate Similarity	NPD7458	Discontinued
0.7403	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7783	Phase 2
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7386	Intermediate Similarity	NPD230	Phase 1
0.7378	Intermediate Similarity	NPD6844	Discontinued
0.7353	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1481	Phase 2
0.7347	Intermediate Similarity	NPD1608	Approved
0.734	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD6232	Discontinued
0.7325	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4307	Phase 2
0.7297	Intermediate Similarity	NPD7697	Approved
0.7297	Intermediate Similarity	NPD7696	Phase 3
0.7297	Intermediate Similarity	NPD7698	Approved
0.7285	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1535	Discovery
0.7278	Intermediate Similarity	NPD6959	Discontinued
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2798	Approved
0.726	Intermediate Similarity	NPD1778	Approved
0.7258	Intermediate Similarity	NPD7870	Phase 2
0.7258	Intermediate Similarity	NPD7871	Phase 2
0.7244	Intermediate Similarity	NPD2799	Discontinued
0.7241	Intermediate Similarity	NPD9545	Approved
0.7238	Intermediate Similarity	NPD6535	Approved
0.7238	Intermediate Similarity	NPD6534	Approved
0.7234	Intermediate Similarity	NPD7701	Phase 2
0.7234	Intermediate Similarity	NPD7585	Approved
0.7226	Intermediate Similarity	NPD6653	Approved
0.7222	Intermediate Similarity	NPD9493	Approved
0.7222	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7473	Discontinued
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.7208	Intermediate Similarity	NPD1240	Approved
0.7202	Intermediate Similarity	NPD3749	Approved
0.72	Intermediate Similarity	NPD7240	Approved
0.7191	Intermediate Similarity	NPD8150	Discontinued
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.719	Intermediate Similarity	NPD3764	Approved
0.7182	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6213	Phase 3
0.7182	Intermediate Similarity	NPD6212	Phase 3
0.7181	Intermediate Similarity	NPD7583	Approved
0.7179	Intermediate Similarity	NPD7097	Phase 1
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD7440	Discontinued
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7124	Intermediate Similarity	NPD3027	Phase 3
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7115	Intermediate Similarity	NPD1607	Approved
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8151	Discontinued
0.7102	Intermediate Similarity	NPD7039	Approved
0.7102	Intermediate Similarity	NPD7038	Approved
0.709	Intermediate Similarity	NPD7584	Approved
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD6032	Approved
0.7086	Intermediate Similarity	NPD3266	Approved
0.7086	Intermediate Similarity	NPD3267	Approved
0.7076	Intermediate Similarity	NPD8127	Discontinued
0.7075	Intermediate Similarity	NPD5585	Approved
0.7067	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6674	Discontinued
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7055	Intermediate Similarity	NPD2532	Approved
0.7055	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD2533	Approved
0.7051	Intermediate Similarity	NPD5124	Phase 1
0.7051	Intermediate Similarity	NPD4340	Discontinued
0.7051	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1610	Phase 2
0.7047	Intermediate Similarity	NPD422	Phase 1
0.7044	Intermediate Similarity	NPD5763	Approved
0.7044	Intermediate Similarity	NPD5762	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data