NPASS Compound

Structure

CID10088 OpenBabel06191715332D 25 29 0 0 1 0 0 0 0 0999 V2000 0.0168 -0.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0728 0.1126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3817 0.9742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8569 0.9707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9942 0.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 1.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4990 0.4341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9869 0.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7135 0.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3523 -0.2856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3117 0.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1483 0.5259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1606 0.9451 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3718 0.8377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4695 0.9276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4667 0.9542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0954 -0.5426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4359 0.4998 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.2603 0.1336 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1534 1.6203 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2537 1.6661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3582 -1.3118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1871 -0.3423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4647 0.4998 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 11 1 0 0 0 0 3 5 1 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 19 1 0 0 0 0 7 23 1 0 0 0 0 8 11 2 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 20 1 1 0 0 0 14 21 2 0 0 0 0 15 8 1 6 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 2 1 1 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	342.463
LogP:	3.454
LogD:	2.759
LogS:	-4.664
# Rotatable Bonds:	3
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	6.039
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.16
MDCK Permeability:	1.4339191693579778e-05
Pgp-inhibitor:	0.579
Pgp-substrate:	0.296
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.81

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	84.55110931396484%
Volume Distribution (VD):	2.984
Pgp-substrate:	13.931215286254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.43
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.582
CYP2C19-substrate:	0.245
CYP2C9-inhibitor:	0.211
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	15.035
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.421
Skin Sensitization:	0.054
Carcinogencity:	0.783
Eye Corrosion:	0.007
Eye Irritation:	0.017
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC10088

Natural Product ID:	NPC10088
*Common Name:**	Hypopurin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WRANWQZSRYWETI-OGBBPFAWSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-11-8-15-16-19(2)5-3-6-20(16,18(24-15)25-17(19)22)13(11)9-14(21)12-4-7-23-10-12/h4,7-8,10,13,15-16,18H,3,5-6,9H2,1-2H3/t13-,15+,16-,18?,19-,20-/m0/s1
SMILES:	CC1=C[C@@H]2[C@H]3[C@]4(C)CCC[C@@]3([C@H]1CC(=O)c1ccoc1)C(O2)OC4=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484231
PubChem CID:	11393708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0003671] Aryl alkyl ketones

*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
NPO8188	Hypoestes purpurea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568798]
NPO8188	Hypoestes purpurea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8188	Hypoestes purpurea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8188	Hypoestes purpurea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[461137]

☑ 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 NPC10088 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	378
0.1-0.2	1400
0.2-0.3	2965
0.3-0.4	6537
0.4-0.5	12241
0.5-0.6	9969
0.6-0.7	8188
0.7-0.8	827
0.8-0.85	155
0.85-0.9	27
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC276676
0.9241	High Similarity	NPC476941
0.9241	High Similarity	NPC476942
0.9209	High Similarity	NPC146872
0.9172	High Similarity	NPC476938
0.9172	High Similarity	NPC476937
0.9116	High Similarity	NPC476936
0.8958	High Similarity	NPC473152
0.8944	High Similarity	NPC236532
0.8873	High Similarity	NPC310830
0.8873	High Similarity	NPC42400
0.8867	High Similarity	NPC476939
0.8867	High Similarity	NPC476940
0.8811	High Similarity	NPC220094
0.8811	High Similarity	NPC476943
0.8784	High Similarity	NPC250228
0.8732	High Similarity	NPC92941
0.8723	High Similarity	NPC470740
0.8707	High Similarity	NPC142113
0.8701	High Similarity	NPC262872
0.8639	High Similarity	NPC223415
0.8639	High Similarity	NPC470741
0.8639	High Similarity	NPC267632
0.8621	High Similarity	NPC90953
0.8611	High Similarity	NPC470742
0.8591	High Similarity	NPC346
0.8503	High Similarity	NPC20500
0.8491	Intermediate Similarity	NPC100333
0.8487	Intermediate Similarity	NPC159927
0.8487	Intermediate Similarity	NPC469335
0.8481	Intermediate Similarity	NPC472664
0.8477	Intermediate Similarity	NPC7388
0.8471	Intermediate Similarity	NPC207978
0.8471	Intermediate Similarity	NPC211777
0.8451	Intermediate Similarity	NPC298190
0.8442	Intermediate Similarity	NPC30222
0.8442	Intermediate Similarity	NPC57998
0.8431	Intermediate Similarity	NPC471000
0.8418	Intermediate Similarity	NPC198047
0.8411	Intermediate Similarity	NPC470941
0.8411	Intermediate Similarity	NPC221809
0.8387	Intermediate Similarity	NPC35000
0.8387	Intermediate Similarity	NPC214541
0.8387	Intermediate Similarity	NPC44675
0.838	Intermediate Similarity	NPC21460
0.8366	Intermediate Similarity	NPC196864
0.8366	Intermediate Similarity	NPC46551
0.8366	Intermediate Similarity	NPC477404
0.8357	Intermediate Similarity	NPC74612
0.8344	Intermediate Similarity	NPC471292
0.8344	Intermediate Similarity	NPC307383
0.8344	Intermediate Similarity	NPC262198
0.8333	Intermediate Similarity	NPC169299
0.8333	Intermediate Similarity	NPC199044
0.8333	Intermediate Similarity	NPC238843
0.8333	Intermediate Similarity	NPC471006
0.8333	Intermediate Similarity	NPC251865
0.8333	Intermediate Similarity	NPC476944
0.8333	Intermediate Similarity	NPC160818
0.8323	Intermediate Similarity	NPC178932
0.8311	Intermediate Similarity	NPC56197
0.8302	Intermediate Similarity	NPC419
0.8301	Intermediate Similarity	NPC195325
0.8301	Intermediate Similarity	NPC471001
0.8298	Intermediate Similarity	NPC319140
0.8298	Intermediate Similarity	NPC95567
0.8286	Intermediate Similarity	NPC179354
0.828	Intermediate Similarity	NPC261597
0.8272	Intermediate Similarity	NPC82602
0.8269	Intermediate Similarity	NPC469336
0.8269	Intermediate Similarity	NPC469850
0.8269	Intermediate Similarity	NPC264943
0.8258	Intermediate Similarity	NPC469503
0.8258	Intermediate Similarity	NPC75906
0.8258	Intermediate Similarity	NPC147168
0.825	Intermediate Similarity	NPC146991
0.8247	Intermediate Similarity	NPC156189
0.8247	Intermediate Similarity	NPC476122
0.8228	Intermediate Similarity	NPC474932
0.8224	Intermediate Similarity	NPC233763
0.8219	Intermediate Similarity	NPC158525
0.8217	Intermediate Similarity	NPC209364
0.8217	Intermediate Similarity	NPC60973
0.8199	Intermediate Similarity	NPC93172
0.8199	Intermediate Similarity	NPC97574
0.8194	Intermediate Similarity	NPC18135
0.8194	Intermediate Similarity	NPC272590
0.8194	Intermediate Similarity	NPC240214
0.8194	Intermediate Similarity	NPC116717
0.8182	Intermediate Similarity	NPC329180
0.8182	Intermediate Similarity	NPC472654
0.8176	Intermediate Similarity	NPC305016
0.817	Intermediate Similarity	NPC471174
0.817	Intermediate Similarity	NPC224418
0.8165	Intermediate Similarity	NPC472283
0.8165	Intermediate Similarity	NPC299038
0.8165	Intermediate Similarity	NPC187149
0.8165	Intermediate Similarity	NPC286722
0.8165	Intermediate Similarity	NPC36655
0.8153	Intermediate Similarity	NPC281258
0.8143	Intermediate Similarity	NPC16922
0.8141	Intermediate Similarity	NPC476201
0.8141	Intermediate Similarity	NPC471002
0.8141	Intermediate Similarity	NPC44577
0.8138	Intermediate Similarity	NPC471817
0.8129	Intermediate Similarity	NPC5180
0.8125	Intermediate Similarity	NPC197596
0.8121	Intermediate Similarity	NPC474722
0.8113	Intermediate Similarity	NPC477403
0.8113	Intermediate Similarity	NPC473473
0.8113	Intermediate Similarity	NPC475967
0.8113	Intermediate Similarity	NPC475295
0.8112	Intermediate Similarity	NPC112706
0.8112	Intermediate Similarity	NPC207294
0.8108	Intermediate Similarity	NPC186626
0.8105	Intermediate Similarity	NPC470999
0.8105	Intermediate Similarity	NPC62799
0.8101	Intermediate Similarity	NPC263265
0.8101	Intermediate Similarity	NPC104736
0.8101	Intermediate Similarity	NPC107646
0.8092	Intermediate Similarity	NPC86935
0.8092	Intermediate Similarity	NPC84479
0.8089	Intermediate Similarity	NPC471863
0.8089	Intermediate Similarity	NPC282445
0.8086	Intermediate Similarity	NPC214600
0.8079	Intermediate Similarity	NPC52412
0.8079	Intermediate Similarity	NPC121158
0.8077	Intermediate Similarity	NPC291150
0.8075	Intermediate Similarity	NPC663
0.8075	Intermediate Similarity	NPC165218
0.8075	Intermediate Similarity	NPC224394
0.8069	Intermediate Similarity	NPC89133
0.8065	Intermediate Similarity	NPC470790
0.8065	Intermediate Similarity	NPC470791
0.8063	Intermediate Similarity	NPC191828
0.8063	Intermediate Similarity	NPC477402
0.8052	Intermediate Similarity	NPC216755
0.805	Intermediate Similarity	NPC304692
0.805	Intermediate Similarity	NPC472776
0.805	Intermediate Similarity	NPC472777
0.805	Intermediate Similarity	NPC470118
0.805	Intermediate Similarity	NPC167142
0.805	Intermediate Similarity	NPC81405
0.805	Intermediate Similarity	NPC469847
0.805	Intermediate Similarity	NPC472772
0.805	Intermediate Similarity	NPC472778
0.805	Intermediate Similarity	NPC249021
0.8049	Intermediate Similarity	NPC472660
0.8042	Intermediate Similarity	NPC83178
0.8041	Intermediate Similarity	NPC46896
0.8038	Intermediate Similarity	NPC296807
0.8038	Intermediate Similarity	NPC155939
0.8038	Intermediate Similarity	NPC476262
0.8038	Intermediate Similarity	NPC92979
0.8038	Intermediate Similarity	NPC141538
0.8028	Intermediate Similarity	NPC230979
0.8027	Intermediate Similarity	NPC471998
0.8025	Intermediate Similarity	NPC470182
0.8025	Intermediate Similarity	NPC276735
0.8025	Intermediate Similarity	NPC123088
0.8025	Intermediate Similarity	NPC246164
0.8024	Intermediate Similarity	NPC472665
0.8014	Intermediate Similarity	NPC471995
0.8013	Intermediate Similarity	NPC470997
0.8012	Intermediate Similarity	NPC5079
0.8012	Intermediate Similarity	NPC69028
0.8	Intermediate Similarity	NPC237155
0.8	Intermediate Similarity	NPC140952
0.7987	Intermediate Similarity	NPC310043
0.7987	Intermediate Similarity	NPC469485
0.7987	Intermediate Similarity	NPC126723
0.7987	Intermediate Similarity	NPC204663
0.7975	Intermediate Similarity	NPC472141
0.7975	Intermediate Similarity	NPC478178
0.7972	Intermediate Similarity	NPC138139
0.7972	Intermediate Similarity	NPC46536
0.7964	Intermediate Similarity	NPC262386
0.7963	Intermediate Similarity	NPC234660
0.7963	Intermediate Similarity	NPC469338
0.7963	Intermediate Similarity	NPC292389
0.7963	Intermediate Similarity	NPC51568
0.7963	Intermediate Similarity	NPC472139
0.7963	Intermediate Similarity	NPC469846
0.795	Intermediate Similarity	NPC25255
0.795	Intermediate Similarity	NPC287559
0.795	Intermediate Similarity	NPC475381
0.7949	Intermediate Similarity	NPC234494
0.7947	Intermediate Similarity	NPC148374
0.7947	Intermediate Similarity	NPC90296
0.7945	Intermediate Similarity	NPC61788
0.7937	Intermediate Similarity	NPC45101
0.7937	Intermediate Similarity	NPC197137
0.7937	Intermediate Similarity	NPC195131
0.7937	Intermediate Similarity	NPC173544
0.7935	Intermediate Similarity	NPC71821
0.7931	Intermediate Similarity	NPC208389
0.7927	Intermediate Similarity	NPC476861
0.7927	Intermediate Similarity	NPC476850
0.7922	Intermediate Similarity	NPC185456
0.7922	Intermediate Similarity	NPC34056

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 NPC10088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	911
0.2-0.3	2044
0.3-0.4	2807
0.4-0.5	2045
0.5-0.6	801
0.6-0.7	216
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.784	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5760	Phase 2
0.7702	Intermediate Similarity	NPD5761	Phase 2
0.733	Intermediate Similarity	NPD8434	Phase 2
0.7308	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6559	Discontinued
0.7222	Intermediate Similarity	NPD920	Approved
0.7197	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD6764	Approved
0.7143	Intermediate Similarity	NPD6765	Approved
0.7133	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2346	Discontinued
0.703	Intermediate Similarity	NPD3226	Approved
0.7011	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6785	Approved
0.6983	Remote Similarity	NPD6784	Approved
0.6975	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8312	Approved
0.6966	Remote Similarity	NPD8313	Approved
0.6962	Remote Similarity	NPD2799	Discontinued
0.6957	Remote Similarity	NPD4628	Phase 3
0.6903	Remote Similarity	NPD2313	Discontinued
0.6875	Remote Similarity	NPD2344	Approved
0.6867	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7819	Suspended
0.6863	Remote Similarity	NPD2798	Approved
0.686	Remote Similarity	NPD5494	Approved
0.6848	Remote Similarity	NPD6273	Approved
0.6842	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7458	Discontinued
0.6813	Remote Similarity	NPD2796	Approved
0.679	Remote Similarity	NPD1243	Approved
0.6786	Remote Similarity	NPD6599	Discontinued
0.6782	Remote Similarity	NPD6808	Phase 2
0.6774	Remote Similarity	NPD6832	Phase 2
0.6772	Remote Similarity	NPD1933	Approved
0.6765	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3749	Approved
0.6733	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3818	Discontinued
0.6711	Remote Similarity	NPD3972	Approved
0.6707	Remote Similarity	NPD2309	Approved
0.6705	Remote Similarity	NPD919	Approved
0.6703	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2800	Approved
0.6687	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7075	Discontinued
0.6647	Remote Similarity	NPD7411	Suspended
0.6646	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3748	Approved
0.6646	Remote Similarity	NPD8032	Phase 2
0.6624	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1876	Approved
0.6608	Remote Similarity	NPD6279	Approved
0.6608	Remote Similarity	NPD6280	Approved
0.6607	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1551	Phase 2
0.6592	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4966	Approved
0.659	Remote Similarity	NPD4967	Phase 2
0.659	Remote Similarity	NPD4965	Approved
0.6587	Remote Similarity	NPD2533	Approved
0.6587	Remote Similarity	NPD2534	Approved
0.6587	Remote Similarity	NPD2532	Approved
0.6587	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8404	Phase 2
0.6538	Remote Similarity	NPD1019	Discontinued
0.6536	Remote Similarity	NPD7799	Discontinued
0.6534	Remote Similarity	NPD1247	Approved
0.6532	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6799	Approved
0.6524	Remote Similarity	NPD1549	Phase 2
0.6522	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6234	Discontinued
0.6513	Remote Similarity	NPD17	Approved
0.6512	Remote Similarity	NPD6801	Discontinued
0.6507	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7028	Phase 2
0.6488	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1241	Discontinued
0.6474	Remote Similarity	NPD3266	Approved
0.6474	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3267	Approved
0.6464	Remote Similarity	NPD7074	Phase 3
0.6463	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6004	Phase 3
0.6463	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6002	Phase 3
0.6463	Remote Similarity	NPD6005	Phase 3
0.6461	Remote Similarity	NPD3926	Phase 2
0.6448	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5585	Approved
0.6446	Remote Similarity	NPD3750	Approved
0.6446	Remote Similarity	NPD7003	Approved
0.6444	Remote Similarity	NPD7228	Approved
0.6437	Remote Similarity	NPD5402	Approved
0.6425	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD37	Approved
0.6412	Remote Similarity	NPD5403	Approved
0.6409	Remote Similarity	NPD7054	Approved
0.6402	Remote Similarity	NPD2935	Discontinued
0.64	Remote Similarity	NPD7768	Phase 2
0.6398	Remote Similarity	NPD4307	Phase 2
0.6398	Remote Similarity	NPD2979	Phase 3
0.6395	Remote Similarity	NPD4380	Phase 2
0.6391	Remote Similarity	NPD5401	Approved
0.6389	Remote Similarity	NPD7473	Discontinued
0.6387	Remote Similarity	NPD1608	Approved
0.6387	Remote Similarity	NPD9717	Approved
0.638	Remote Similarity	NPD7097	Phase 1
0.6379	Remote Similarity	NPD8455	Phase 2
0.6375	Remote Similarity	NPD3268	Approved
0.6375	Remote Similarity	NPD3764	Approved
0.6374	Remote Similarity	NPD7472	Approved
0.6373	Remote Similarity	NPD4107	Approved
0.637	Remote Similarity	NPD2182	Approved
0.6359	Remote Similarity	NPD7435	Discontinued
0.6359	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5890	Approved
0.6358	Remote Similarity	NPD4622	Approved
0.6358	Remote Similarity	NPD4618	Approved
0.6358	Remote Similarity	NPD5889	Approved
0.6348	Remote Similarity	NPD8127	Discontinued
0.6348	Remote Similarity	NPD6959	Discontinued
0.6343	Remote Similarity	NPD3817	Phase 2
0.6341	Remote Similarity	NPD7033	Discontinued
0.6339	Remote Similarity	NPD6797	Phase 2
0.6329	Remote Similarity	NPD5647	Approved
0.6325	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD1934	Approved
0.6319	Remote Similarity	NPD5844	Phase 1
0.6313	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6232	Discontinued
0.631	Remote Similarity	NPD3887	Approved
0.6304	Remote Similarity	NPD7240	Approved
0.6304	Remote Similarity	NPD7685	Pre-registration
0.6304	Remote Similarity	NPD7251	Discontinued
0.6299	Remote Similarity	NPD1778	Approved
0.6296	Remote Similarity	NPD4140	Approved
0.6289	Remote Similarity	NPD6776	Approved
0.6289	Remote Similarity	NPD6779	Approved
0.6289	Remote Similarity	NPD6781	Approved
0.6289	Remote Similarity	NPD6782	Approved
0.6289	Remote Similarity	NPD6777	Approved
0.6289	Remote Similarity	NPD6780	Approved
0.6289	Remote Similarity	NPD6778	Approved
0.628	Remote Similarity	NPD5688	Approved
0.628	Remote Similarity	NPD5689	Approved
0.6273	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7236	Approved
0.627	Remote Similarity	NPD7808	Phase 3
0.6269	Remote Similarity	NPD4420	Approved
0.6266	Remote Similarity	NPD2797	Approved
0.6266	Remote Similarity	NPD1203	Approved
0.6264	Remote Similarity	NPD3751	Discontinued
0.6258	Remote Similarity	NPD6355	Discontinued
0.6258	Remote Similarity	NPD447	Suspended
0.6257	Remote Similarity	NPD7199	Phase 2
0.6256	Remote Similarity	NPD4482	Phase 3
0.625	Remote Similarity	NPD2296	Approved
0.625	Remote Similarity	NPD4110	Phase 3
0.625	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1510	Phase 2
0.6242	Remote Similarity	NPD4359	Approved
0.6242	Remote Similarity	NPD4308	Phase 3
0.6229	Remote Similarity	NPD6844	Discontinued
0.6226	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5711	Approved
0.6222	Remote Similarity	NPD5710	Approved
0.6218	Remote Similarity	NPD1281	Approved
0.6215	Remote Similarity	NPD3882	Suspended
0.6215	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6585	Discontinued
0.6205	Remote Similarity	NPD2438	Suspended
0.6205	Remote Similarity	NPD6100	Approved
0.6205	Remote Similarity	NPD6099	Approved
0.6199	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3142	Approved
0.6196	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3140	Approved
0.6193	Remote Similarity	NPD7696	Phase 3
0.6193	Remote Similarity	NPD7698	Approved
0.6193	Remote Similarity	NPD7697	Approved
0.6188	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD411	Approved
0.6169	Remote Similarity	NPD7874	Approved
0.6169	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7871	Phase 2
0.6162	Remote Similarity	NPD5953	Discontinued
0.6162	Remote Similarity	NPD7870	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data