NPASS Compound

Structure

NPC90905 OpenBabel07101718192D 39 42 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 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 -2.5000 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 3.5000 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 -1.7321 3.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -6.0622 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 2 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 -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 1 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 -3.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 12 2 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 14 2 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 15 2 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 36 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 37 1 0 0 0 0 17 20 2 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 11 1 6 0 0 0 19 21 1 0 0 0 0 19 38 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 6 0 0 0 23 26 1 0 0 0 0 23 39 1 1 0 0 0 24 34 2 0 0 0 0 24 36 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 26 37 1 6 0 0 0 26 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.12
Volume:	509.298
LogP:	2.334
LogD:	1.189
LogS:	-3.362
# Rotatable Bonds:	9
TPSA:	212.67
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.164
Synthetic Accessibility Score:	3.887
Fsp3:	0.231
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.569
MDCK Permeability:	1.6879284885362722e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.682
20% Bioavailability (F20%):	0.53
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	98.73210906982422%
Volume Distribution (VD):	0.508
Pgp-substrate:	3.631533622741699%

ADMET: Metabolism

CYP1A2-inhibitor:	0.515
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.539
CYP2C9-substrate:	0.427
CYP2D6-inhibitor:	0.708
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.391
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	12.461
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.167
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.946
Carcinogencity:	0.256
Eye Corrosion:	0.003
Eye Irritation:	0.916
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC90905

Natural Product ID:	NPC90905
*Common Name:**	Hyemaloside B
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[(4-hydroxybenzoyl)oxymethyl]-2-(4-hydroxyphenoxy)oxan-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	LIANLIDDEFJTSX-XZWSAFPPSA-N
Standard InCHI:	InChI=1S/C26H24O13/c27-14-3-1-12(2-4-14)24(34)36-11-19-21(32)22(33)23(26(38-19)37-16-7-5-15(28)6-8-16)39-25(35)13-9-17(29)20(31)18(30)10-13/h1-10,19,21-23,26-33H,11H2/t19-,21-,22+,23-,26-/m1/s1
SMILES:	Oc1ccc(cc1)O[C@@H]1O[C@H](COC(=O)c2ccc(cc2)O)[C@H]([C@@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498793
PubChem CID:	25110931
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
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18763827]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18763827]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	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

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	>	18300.0	nM	PMID[449594]
NPT2	Others	Unspecified	IC50	=	3320.0	nM	PMID[449594]
NPT2	Others	Unspecified	IC50	=	2440.0	nM	PMID[449594]

☑ 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 NPC90905 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	390
0.1-0.2	1691
0.2-0.3	4273
0.3-0.4	9229
0.4-0.5	8745
0.5-0.6	4254
0.6-0.7	5731
0.7-0.8	6319
0.8-0.85	1384
0.85-0.9	571
0.9-0.95	92
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4013
0.9869	High Similarity	NPC289346
0.9804	High Similarity	NPC74319
0.9804	High Similarity	NPC287872
0.9742	High Similarity	NPC33298
0.9742	High Similarity	NPC285108
0.9684	High Similarity	NPC95421
0.9684	High Similarity	NPC198125
0.9677	High Similarity	NPC311803
0.9677	High Similarity	NPC472859
0.9677	High Similarity	NPC25389
0.9613	High Similarity	NPC166277
0.9613	High Similarity	NPC119125
0.9563	High Similarity	NPC5786
0.9563	High Similarity	NPC102851
0.9548	High Similarity	NPC289811
0.9548	High Similarity	NPC160780
0.9487	High Similarity	NPC239966
0.9487	High Similarity	NPC203020
0.9484	High Similarity	NPC1913
0.9484	High Similarity	NPC133984
0.9437	High Similarity	NPC658
0.9437	High Similarity	NPC197708
0.9387	High Similarity	NPC472992
0.9387	High Similarity	NPC472991
0.9379	High Similarity	NPC149011
0.9379	High Similarity	NPC204937
0.9359	High Similarity	NPC472860
0.9351	High Similarity	NPC3746
0.9351	High Similarity	NPC205037
0.9351	High Similarity	NPC44260
0.9351	High Similarity	NPC16024
0.9351	High Similarity	NPC61152
0.9329	High Similarity	NPC476622
0.9329	High Similarity	NPC476618
0.9329	High Similarity	NPC476620
0.9329	High Similarity	NPC476623
0.9329	High Similarity	NPC476619
0.9329	High Similarity	NPC476621
0.9308	High Similarity	NPC121290
0.929	High Similarity	NPC327032
0.929	High Similarity	NPC191046
0.929	High Similarity	NPC194095
0.9264	High Similarity	NPC175230
0.9264	High Similarity	NPC163165
0.9264	High Similarity	NPC172033
0.9264	High Similarity	NPC88560
0.9241	High Similarity	NPC24164
0.9236	High Similarity	NPC156818
0.9236	High Similarity	NPC68324
0.9236	High Similarity	NPC289322
0.9236	High Similarity	NPC38779
0.9236	High Similarity	NPC160512
0.9236	High Similarity	NPC114179
0.9226	High Similarity	NPC310661
0.9226	High Similarity	NPC105827
0.9221	High Similarity	NPC140151
0.9216	High Similarity	NPC92117
0.9212	High Similarity	NPC472387
0.9207	High Similarity	NPC84482
0.9207	High Similarity	NPC169645
0.9202	High Similarity	NPC47140
0.9202	High Similarity	NPC254540
0.9202	High Similarity	NPC172807
0.9202	High Similarity	NPC211594
0.9202	High Similarity	NPC67134
0.9198	High Similarity	NPC149300
0.9172	High Similarity	NPC471405
0.9172	High Similarity	NPC250436
0.9172	High Similarity	NPC300845
0.9172	High Similarity	NPC88803
0.9172	High Similarity	NPC104983
0.9172	High Similarity	NPC291948
0.9162	High Similarity	NPC36138
0.9161	High Similarity	NPC134905
0.9161	High Similarity	NPC36130
0.9152	High Similarity	NPC67629
0.9152	High Similarity	NPC79736
0.9152	High Similarity	NPC61904
0.9152	High Similarity	NPC144097
0.915	High Similarity	NPC120621
0.915	High Similarity	NPC248257
0.9146	High Similarity	NPC472993
0.9141	High Similarity	NPC34287
0.9141	High Similarity	NPC471416
0.9136	High Similarity	NPC473818
0.9136	High Similarity	NPC45618
0.9136	High Similarity	NPC116745
0.9136	High Similarity	NPC58716
0.9136	High Similarity	NPC146792
0.913	High Similarity	NPC142614
0.9125	High Similarity	NPC148273
0.9119	High Similarity	NPC53889
0.9114	High Similarity	NPC238419
0.9114	High Similarity	NPC172419
0.9108	High Similarity	NPC10205
0.9107	High Similarity	NPC470416
0.9103	High Similarity	NPC157898
0.9102	High Similarity	NPC8940
0.9097	High Similarity	NPC93619
0.9096	High Similarity	NPC113836
0.9096	High Similarity	NPC37668
0.9096	High Similarity	NPC253521
0.9096	High Similarity	NPC267549
0.9096	High Similarity	NPC35167
0.9091	High Similarity	NPC135277
0.9091	High Similarity	NPC34267
0.9091	High Similarity	NPC49344
0.9091	High Similarity	NPC210094
0.9091	High Similarity	NPC101191
0.9091	High Similarity	NPC477848
0.9091	High Similarity	NPC43211
0.9091	High Similarity	NPC237435
0.9091	High Similarity	NPC223426
0.9091	High Similarity	NPC81042
0.9091	High Similarity	NPC214621
0.9091	High Similarity	NPC115760
0.9085	High Similarity	NPC307518
0.9085	High Similarity	NPC48773
0.9085	High Similarity	NPC205076
0.9085	High Similarity	NPC472386
0.908	High Similarity	NPC201292
0.908	High Similarity	NPC226294
0.908	High Similarity	NPC186807
0.908	High Similarity	NPC170675
0.908	High Similarity	NPC112755
0.908	High Similarity	NPC93337
0.908	High Similarity	NPC471457
0.908	High Similarity	NPC45638
0.908	High Similarity	NPC105025
0.908	High Similarity	NPC58053
0.908	High Similarity	NPC475942
0.908	High Similarity	NPC469931
0.9068	High Similarity	NPC88043
0.9068	High Similarity	NPC168822
0.9062	High Similarity	NPC217950
0.9057	High Similarity	NPC87317
0.9051	High Similarity	NPC318432
0.9051	High Similarity	NPC247629
0.9051	High Similarity	NPC239019
0.9038	High Similarity	NPC75695
0.9036	High Similarity	NPC268533
0.9036	High Similarity	NPC211532
0.9036	High Similarity	NPC297574
0.9036	High Similarity	NPC472385
0.9036	High Similarity	NPC198324
0.9036	High Similarity	NPC154741
0.9036	High Similarity	NPC233994
0.9036	High Similarity	NPC296018
0.9026	High Similarity	NPC142528
0.9024	High Similarity	NPC183357
0.9024	High Similarity	NPC155763
0.9024	High Similarity	NPC245014
0.9024	High Similarity	NPC20505
0.9024	High Similarity	NPC235260
0.9024	High Similarity	NPC44558
0.9024	High Similarity	NPC21190
0.9024	High Similarity	NPC474434
0.9024	High Similarity	NPC84265
0.9024	High Similarity	NPC22195
0.9024	High Similarity	NPC282987
0.9024	High Similarity	NPC224462
0.9024	High Similarity	NPC105511
0.9018	High Similarity	NPC45400
0.9012	High Similarity	NPC165720
0.9006	High Similarity	NPC77660
0.9006	High Similarity	NPC189142
0.9006	High Similarity	NPC41009
0.9	High Similarity	NPC476373
0.8988	High Similarity	NPC53680
0.8988	High Similarity	NPC208797
0.8987	High Similarity	NPC145425
0.8982	High Similarity	NPC476773
0.8982	High Similarity	NPC217520
0.8982	High Similarity	NPC139571
0.8982	High Similarity	NPC196127
0.8982	High Similarity	NPC293626
0.8982	High Similarity	NPC217387
0.8982	High Similarity	NPC258044
0.8982	High Similarity	NPC267680
0.8981	High Similarity	NPC474656
0.8981	High Similarity	NPC137813
0.8976	High Similarity	NPC264735
0.897	High Similarity	NPC289396
0.897	High Similarity	NPC3583
0.897	High Similarity	NPC190003
0.897	High Similarity	NPC212038
0.897	High Similarity	NPC81332
0.897	High Similarity	NPC301683
0.897	High Similarity	NPC117260
0.897	High Similarity	NPC271848
0.897	High Similarity	NPC175107
0.897	High Similarity	NPC476405
0.897	High Similarity	NPC262580
0.897	High Similarity	NPC259152
0.8968	High Similarity	NPC111785
0.8963	High Similarity	NPC95855
0.8963	High Similarity	NPC229687
0.8963	High Similarity	NPC138927
0.8963	High Similarity	NPC472383

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 NPC90905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	903
0.2-0.3	1930
0.3-0.4	2655
0.4-0.5	1844
0.5-0.6	951
0.6-0.7	379
0.7-0.8	117
0.8-0.85	21
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9172	High Similarity	NPD4868	Clinical (unspecified phase)
0.9091	High Similarity	NPD4338	Clinical (unspecified phase)
0.8788	High Similarity	NPD3818	Discontinued
0.8735	High Similarity	NPD7054	Approved
0.8683	High Similarity	NPD7074	Phase 3
0.8683	High Similarity	NPD7472	Approved
0.8642	High Similarity	NPD4381	Clinical (unspecified phase)
0.8631	High Similarity	NPD6797	Phase 2
0.8631	High Similarity	NPD7993	Clinical (unspecified phase)
0.8608	High Similarity	NPD1653	Approved
0.858	High Similarity	NPD7251	Discontinued
0.8512	High Similarity	NPD5844	Phase 1
0.8443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6166	Phase 2
0.8421	Intermediate Similarity	NPD7808	Phase 3
0.8363	Intermediate Similarity	NPD7685	Pre-registration
0.8344	Intermediate Similarity	NPD6190	Approved
0.8344	Intermediate Similarity	NPD2801	Approved
0.8313	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD1934	Approved
0.8232	Intermediate Similarity	NPD1465	Phase 2
0.8232	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5402	Approved
0.815	Intermediate Similarity	NPD6559	Discontinued
0.8129	Intermediate Similarity	NPD7228	Approved
0.8117	Intermediate Similarity	NPD230	Phase 1
0.8089	Intermediate Similarity	NPD7266	Discontinued
0.8081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD3817	Phase 2
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8047	Intermediate Similarity	NPD7199	Phase 2
0.8036	Intermediate Similarity	NPD6234	Discontinued
0.8024	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7075	Discontinued
0.7966	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD37	Approved
0.7944	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4967	Phase 2
0.7917	Intermediate Similarity	NPD4966	Approved
0.7917	Intermediate Similarity	NPD4965	Approved
0.7914	Intermediate Similarity	NPD1512	Approved
0.7895	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD7411	Suspended
0.7882	Intermediate Similarity	NPD5494	Approved
0.7853	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD8313	Approved
0.7849	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4628	Phase 3
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7798	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD8455	Phase 2
0.7759	Intermediate Similarity	NPD7473	Discontinued
0.7758	Intermediate Similarity	NPD5403	Approved
0.7738	Intermediate Similarity	NPD6801	Discontinued
0.7707	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1613	Approved
0.7702	Intermediate Similarity	NPD1549	Phase 2
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7688	Intermediate Similarity	NPD3787	Discontinued
0.7683	Intermediate Similarity	NPD6799	Approved
0.7647	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7240	Approved
0.764	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5401	Approved
0.7607	Intermediate Similarity	NPD3750	Approved
0.76	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6233	Phase 2
0.753	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6959	Discontinued
0.7526	Intermediate Similarity	NPD7783	Phase 2
0.7526	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD9269	Phase 2
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7469	Intermediate Similarity	NPD1551	Phase 2
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6780	Approved
0.746	Intermediate Similarity	NPD6779	Approved
0.746	Intermediate Similarity	NPD6782	Approved
0.746	Intermediate Similarity	NPD6777	Approved
0.746	Intermediate Similarity	NPD6776	Approved
0.746	Intermediate Similarity	NPD6781	Approved
0.746	Intermediate Similarity	NPD6778	Approved
0.7452	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5353	Approved
0.7438	Intermediate Similarity	NPD1933	Approved
0.7425	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6599	Discontinued
0.7407	Intermediate Similarity	NPD1510	Phase 2
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD9494	Approved
0.7362	Intermediate Similarity	NPD2935	Discontinued
0.7362	Intermediate Similarity	NPD2796	Approved
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7680	Approved
0.7329	Intermediate Similarity	NPD447	Suspended
0.7316	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7871	Phase 2
0.7306	Intermediate Similarity	NPD7870	Phase 2
0.7301	Intermediate Similarity	NPD3748	Approved
0.7296	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7585	Approved
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD943	Approved
0.7255	Intermediate Similarity	NPD9268	Approved
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7254	Intermediate Similarity	NPD7698	Approved
0.7254	Intermediate Similarity	NPD7697	Approved
0.7253	Intermediate Similarity	NPD7039	Approved
0.7253	Intermediate Similarity	NPD7038	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7247	Intermediate Similarity	NPD5242	Approved
0.7231	Intermediate Similarity	NPD7583	Approved
0.7226	Intermediate Similarity	NPD1091	Approved
0.7202	Intermediate Similarity	NPD6823	Phase 2
0.7196	Intermediate Similarity	NPD6535	Approved
0.7196	Intermediate Similarity	NPD6534	Approved
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.7168	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD1240	Approved
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1247	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7134	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4908	Phase 1
0.712	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7119	Intermediate Similarity	NPD919	Approved
0.7118	Intermediate Similarity	NPD2532	Approved
0.7118	Intermediate Similarity	NPD2533	Approved
0.7118	Intermediate Similarity	NPD2534	Approved
0.7085	Intermediate Similarity	NPD7801	Approved
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7083	Intermediate Similarity	NPD7699	Phase 2
0.7078	Intermediate Similarity	NPD9545	Approved
0.7076	Intermediate Similarity	NPD6273	Approved
0.7073	Intermediate Similarity	NPD1607	Approved
0.7062	Intermediate Similarity	NPD6971	Discontinued
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7052	Intermediate Similarity	NPD3226	Approved
0.7044	Intermediate Similarity	NPD1203	Approved
0.7037	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7097	Phase 1
0.7024	Intermediate Similarity	NPD1652	Phase 2
0.7024	Intermediate Similarity	NPD6674	Discontinued
0.7024	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD7440	Discontinued
0.7	Intermediate Similarity	NPD7229	Phase 3
0.6981	Remote Similarity	NPD3225	Approved
0.6971	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6213	Phase 3
0.6963	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6212	Phase 3
0.6962	Remote Similarity	NPD1608	Approved
0.6962	Remote Similarity	NPD1481	Phase 2
0.6954	Remote Similarity	NPD8320	Phase 1
0.6954	Remote Similarity	NPD3455	Phase 2
0.6954	Remote Similarity	NPD8319	Approved
0.6936	Remote Similarity	NPD920	Approved
0.6919	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6832	Phase 2
0.6909	Remote Similarity	NPD5124	Phase 1
0.6909	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7286	Phase 2
0.6899	Remote Similarity	NPD1535	Discovery
0.6886	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7033	Discontinued
0.6882	Remote Similarity	NPD8166	Discontinued
0.686	Remote Similarity	NPD4357	Discontinued
0.6854	Remote Similarity	NPD4288	Approved
0.6852	Remote Similarity	NPD2861	Phase 2
0.6845	Remote Similarity	NPD6099	Approved
0.6845	Remote Similarity	NPD6100	Approved
0.6837	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6844	Discontinued
0.6829	Remote Similarity	NPD2313	Discontinued
0.6807	Remote Similarity	NPD6355	Discontinued
0.6805	Remote Similarity	NPD2346	Discontinued
0.6802	Remote Similarity	NPD643	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data