NPASS Compound

Structure

CID276676 OpenBabel06191716082D 25 29 0 0 1 0 0 0 0 0999 V2000 0.3761 3.3419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4725 -0.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4844 2.0351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9797 2.0354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9137 2.3253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2518 2.4381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2518 1.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4160 1.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3599 2.5569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6493 1.6209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4932 1.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9962 1.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6435 1.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 2.2588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3360 1.2279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4166 1.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7861 0.6267 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7864 2.4381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9800 0.2239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7864 1.6320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7773 0.9867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3109 2.3659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7180 2.2042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4165 1.1292 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 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 18 1 0 0 0 0 8 19 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 13 21 2 0 0 0 0 14 18 1 1 0 0 0 14 20 1 0 0 0 0 15 19 1 6 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 17 25 1 0 0 0 0 18 1 1 1 0 0 0 19 2 1 6 0 0 0 19 25 1 0 0 0 0 20 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	342.463
LogP:	2.498
LogD:	2.156
LogS:	-4.51
# 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:	6.355
Fsp3:	0.6
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:	-5.166
MDCK Permeability:	2.1522697352338582e-05
Pgp-inhibitor:	0.877
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.451

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	86.52422332763672%
Volume Distribution (VD):	1.165
Pgp-substrate:	15.863466262817383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.747
CYP2C19-inhibitor:	0.262
CYP2C19-substrate:	0.419
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	12.135
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.05
Carcinogencity:	0.684
Eye Corrosion:	0.021
Eye Irritation:	0.117
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC276676

Natural Product ID:	NPC276676
*Common Name:**	Hypopurin C
IUPAC Name:	n.a.
Synonyms:	Hypopurin C
Standard InCHIKey:	RRIAXHHOQKFFCN-VRHQPAJFSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-18-6-3-7-20-14(18)4-8-19(2,25-17(20)24-16(18)22)15(20)10-13(21)12-5-9-23-11-12/h4-5,8-9,11,14-15,17H,3,6-7,10H2,1-2H3/t14-,15-,17?,18-,19-,20+/m0/s1
SMILES:	C[C@]12CCC[C@@]34[C@H]1C=C[C@@](C)([C@@H]3CC(=O)c1ccoc1)OC4OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484232
PubChem CID:	11221552
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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[458865]

☑ 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 NPC276676 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	382
0.1-0.2	1435
0.2-0.3	2977
0.3-0.4	6636
0.4-0.5	12475
0.5-0.6	9867
0.6-0.7	7946
0.7-0.8	807
0.8-0.85	144
0.85-0.9	22
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC10088
0.9103	High Similarity	NPC476938
0.9103	High Similarity	NPC476937
0.9048	High Similarity	NPC476936
0.9041	High Similarity	NPC476942
0.9041	High Similarity	NPC476941
0.9	High Similarity	NPC146872
0.8936	High Similarity	NPC42400
0.88	High Similarity	NPC476939
0.88	High Similarity	NPC476940
0.8759	High Similarity	NPC473152
0.8741	High Similarity	NPC236532
0.8671	High Similarity	NPC310830
0.8652	High Similarity	NPC470740
0.8611	High Similarity	NPC220094
0.8611	High Similarity	NPC476943
0.8591	High Similarity	NPC250228
0.8571	High Similarity	NPC223415
0.8531	High Similarity	NPC92941
0.8523	High Similarity	NPC346
0.8516	High Similarity	NPC262872
0.8514	High Similarity	NPC142113
0.8446	Intermediate Similarity	NPC470741
0.8446	Intermediate Similarity	NPC267632
0.8435	Intermediate Similarity	NPC20500
0.8425	Intermediate Similarity	NPC90953
0.8417	Intermediate Similarity	NPC74612
0.8414	Intermediate Similarity	NPC470742
0.8411	Intermediate Similarity	NPC7388
0.8377	Intermediate Similarity	NPC57998
0.8345	Intermediate Similarity	NPC179354
0.8344	Intermediate Similarity	NPC221809
0.8344	Intermediate Similarity	NPC470941
0.8323	Intermediate Similarity	NPC44675
0.8323	Intermediate Similarity	NPC214541
0.8313	Intermediate Similarity	NPC100333
0.831	Intermediate Similarity	NPC21460
0.8302	Intermediate Similarity	NPC472664
0.8301	Intermediate Similarity	NPC196864
0.8301	Intermediate Similarity	NPC469335
0.8301	Intermediate Similarity	NPC477404
0.8301	Intermediate Similarity	NPC159927
0.8291	Intermediate Similarity	NPC211777
0.8291	Intermediate Similarity	NPC207978
0.8276	Intermediate Similarity	NPC158525
0.8272	Intermediate Similarity	NPC169299
0.8272	Intermediate Similarity	NPC160818
0.8267	Intermediate Similarity	NPC251865
0.8264	Intermediate Similarity	NPC471006
0.8258	Intermediate Similarity	NPC30222
0.8252	Intermediate Similarity	NPC298190
0.8247	Intermediate Similarity	NPC471000
0.8239	Intermediate Similarity	NPC198047
0.8239	Intermediate Similarity	NPC419
0.8227	Intermediate Similarity	NPC319140
0.8227	Intermediate Similarity	NPC95567
0.8217	Intermediate Similarity	NPC261597
0.821	Intermediate Similarity	NPC82602
0.8205	Intermediate Similarity	NPC35000
0.8205	Intermediate Similarity	NPC469850
0.8205	Intermediate Similarity	NPC264943
0.8201	Intermediate Similarity	NPC16922
0.8194	Intermediate Similarity	NPC147168
0.8194	Intermediate Similarity	NPC75906
0.8187	Intermediate Similarity	NPC146991
0.8182	Intermediate Similarity	NPC156189
0.8182	Intermediate Similarity	NPC46551
0.8182	Intermediate Similarity	NPC476122
0.8176	Intermediate Similarity	NPC474722
0.8165	Intermediate Similarity	NPC474932
0.8165	Intermediate Similarity	NPC307383
0.8158	Intermediate Similarity	NPC233763
0.8158	Intermediate Similarity	NPC471292
0.8158	Intermediate Similarity	NPC262198
0.8153	Intermediate Similarity	NPC60973
0.8153	Intermediate Similarity	NPC209364
0.8146	Intermediate Similarity	NPC476944
0.8146	Intermediate Similarity	NPC199044
0.8146	Intermediate Similarity	NPC86935
0.8146	Intermediate Similarity	NPC238843
0.8141	Intermediate Similarity	NPC178932
0.8129	Intermediate Similarity	NPC240214
0.8129	Intermediate Similarity	NPC18135
0.8125	Intermediate Similarity	NPC89133
0.8121	Intermediate Similarity	NPC56197
0.8117	Intermediate Similarity	NPC195325
0.8117	Intermediate Similarity	NPC471001
0.8117	Intermediate Similarity	NPC329180
0.8113	Intermediate Similarity	NPC305016
0.8105	Intermediate Similarity	NPC224418
0.8101	Intermediate Similarity	NPC299038
0.8101	Intermediate Similarity	NPC286722
0.8101	Intermediate Similarity	NPC36655
0.8101	Intermediate Similarity	NPC187149
0.8095	Intermediate Similarity	NPC46896
0.8089	Intermediate Similarity	NPC469336
0.8077	Intermediate Similarity	NPC476201
0.8077	Intermediate Similarity	NPC469503
0.8077	Intermediate Similarity	NPC44577
0.8069	Intermediate Similarity	NPC471817
0.8063	Intermediate Similarity	NPC197596
0.805	Intermediate Similarity	NPC473473
0.805	Intermediate Similarity	NPC475967
0.805	Intermediate Similarity	NPC477403
0.805	Intermediate Similarity	NPC475295
0.8042	Intermediate Similarity	NPC112706
0.8042	Intermediate Similarity	NPC207294
0.8041	Intermediate Similarity	NPC186626
0.8038	Intermediate Similarity	NPC107646
0.8038	Intermediate Similarity	NPC104736
0.8038	Intermediate Similarity	NPC263265
0.8038	Intermediate Similarity	NPC204663
0.8028	Intermediate Similarity	NPC46536
0.8028	Intermediate Similarity	NPC138139
0.8025	Intermediate Similarity	NPC282445
0.8025	Intermediate Similarity	NPC93172
0.8025	Intermediate Similarity	NPC97574
0.8025	Intermediate Similarity	NPC214600
0.8014	Intermediate Similarity	NPC65735
0.8014	Intermediate Similarity	NPC188377
0.8013	Intermediate Similarity	NPC272590
0.8013	Intermediate Similarity	NPC52412
0.8013	Intermediate Similarity	NPC121158
0.8013	Intermediate Similarity	NPC116717
0.8012	Intermediate Similarity	NPC663
0.8012	Intermediate Similarity	NPC165218
0.8012	Intermediate Similarity	NPC224394
0.8	Intermediate Similarity	NPC470790
0.8	Intermediate Similarity	NPC472654
0.8	Intermediate Similarity	NPC90296
0.8	Intermediate Similarity	NPC477402
0.8	Intermediate Similarity	NPC470791
0.8	Intermediate Similarity	NPC191828
0.7987	Intermediate Similarity	NPC472776
0.7987	Intermediate Similarity	NPC249021
0.7987	Intermediate Similarity	NPC472778
0.7987	Intermediate Similarity	NPC470118
0.7987	Intermediate Similarity	NPC472777
0.7987	Intermediate Similarity	NPC471174
0.7987	Intermediate Similarity	NPC195131
0.7987	Intermediate Similarity	NPC472772
0.7987	Intermediate Similarity	NPC167142
0.7987	Intermediate Similarity	NPC81405
0.7987	Intermediate Similarity	NPC472283
0.7987	Intermediate Similarity	NPC304692
0.7975	Intermediate Similarity	NPC281258
0.7975	Intermediate Similarity	NPC476262
0.7972	Intermediate Similarity	NPC83178
0.7971	Intermediate Similarity	NPC243704
0.7964	Intermediate Similarity	NPC472665
0.7963	Intermediate Similarity	NPC123088
0.7963	Intermediate Similarity	NPC276735
0.7963	Intermediate Similarity	NPC470182
0.7962	Intermediate Similarity	NPC471002
0.7961	Intermediate Similarity	NPC80635
0.7959	Intermediate Similarity	NPC471998
0.7958	Intermediate Similarity	NPC230979
0.795	Intermediate Similarity	NPC5079
0.7949	Intermediate Similarity	NPC5180
0.7945	Intermediate Similarity	NPC471995
0.7937	Intermediate Similarity	NPC237155
0.7937	Intermediate Similarity	NPC140952
0.7925	Intermediate Similarity	NPC469485
0.7925	Intermediate Similarity	NPC126723
0.7922	Intermediate Similarity	NPC470999
0.7922	Intermediate Similarity	NPC62799
0.7919	Intermediate Similarity	NPC307401
0.7914	Intermediate Similarity	NPC472141
0.7914	Intermediate Similarity	NPC478178
0.7911	Intermediate Similarity	NPC471863
0.7908	Intermediate Similarity	NPC84479
0.7904	Intermediate Similarity	NPC262386
0.7901	Intermediate Similarity	NPC234660
0.7901	Intermediate Similarity	NPC292389
0.7901	Intermediate Similarity	NPC51568
0.7901	Intermediate Similarity	NPC469338
0.7901	Intermediate Similarity	NPC469846
0.7901	Intermediate Similarity	NPC472139
0.7898	Intermediate Similarity	NPC291150
0.7888	Intermediate Similarity	NPC475381
0.7888	Intermediate Similarity	NPC25255
0.7888	Intermediate Similarity	NPC287559
0.7881	Intermediate Similarity	NPC148374
0.7879	Intermediate Similarity	NPC472660
0.7875	Intermediate Similarity	NPC45101
0.7875	Intermediate Similarity	NPC469847
0.7875	Intermediate Similarity	NPC173544
0.7871	Intermediate Similarity	NPC216755
0.7866	Intermediate Similarity	NPC476850
0.7866	Intermediate Similarity	NPC476861
0.7862	Intermediate Similarity	NPC296807
0.7862	Intermediate Similarity	NPC92979
0.7862	Intermediate Similarity	NPC155939
0.7862	Intermediate Similarity	NPC141538
0.7862	Intermediate Similarity	NPC208389
0.7853	Intermediate Similarity	NPC469849
0.7853	Intermediate Similarity	NPC470940
0.7853	Intermediate Similarity	NPC276551
0.7853	Intermediate Similarity	NPC56358
0.7848	Intermediate Similarity	NPC246164

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 NPC276676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	923
0.2-0.3	2059
0.3-0.4	2838
0.4-0.5	1999
0.5-0.6	785
0.6-0.7	215
0.7-0.8	9
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
0.7669	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5761	Phase 2
0.764	Intermediate Similarity	NPD5760	Phase 2
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD920	Approved
0.7181	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7086	Intermediate Similarity	NPD6764	Approved
0.7086	Intermediate Similarity	NPD6765	Approved
0.7086	Intermediate Similarity	NPD6559	Discontinued
0.7025	Intermediate Similarity	NPD2346	Discontinued
0.7019	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.697	Remote Similarity	NPD3226	Approved
0.6948	Remote Similarity	NPD2313	Discontinued
0.6927	Remote Similarity	NPD6785	Approved
0.6927	Remote Similarity	NPD6784	Approved
0.6918	Remote Similarity	NPD2344	Approved
0.6908	Remote Similarity	NPD2798	Approved
0.6905	Remote Similarity	NPD7819	Suspended
0.6882	Remote Similarity	NPD3749	Approved
0.6857	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1243	Approved
0.6818	Remote Similarity	NPD6832	Phase 2
0.6816	Remote Similarity	NPD8312	Approved
0.6816	Remote Similarity	NPD8313	Approved
0.6815	Remote Similarity	NPD1933	Approved
0.6802	Remote Similarity	NPD5494	Approved
0.68	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4628	Phase 3
0.6784	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7458	Discontinued
0.675	Remote Similarity	NPD2796	Approved
0.6748	Remote Similarity	NPD2309	Approved
0.6744	Remote Similarity	NPD919	Approved
0.6728	Remote Similarity	NPD2800	Approved
0.6728	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6599	Discontinued
0.6724	Remote Similarity	NPD6808	Phase 2
0.6706	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6273	Approved
0.6687	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3748	Approved
0.6686	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6279	Approved
0.6647	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6280	Approved
0.6645	Remote Similarity	NPD3972	Approved
0.6604	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7075	Discontinued
0.6582	Remote Similarity	NPD8032	Phase 2
0.6581	Remote Similarity	NPD1019	Discontinued
0.6571	Remote Similarity	NPD1247	Approved
0.6566	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6799	Approved
0.6561	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD17	Approved
0.6543	Remote Similarity	NPD1551	Phase 2
0.6536	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1241	Discontinued
0.6529	Remote Similarity	NPD7028	Phase 2
0.6527	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2532	Approved
0.6527	Remote Similarity	NPD2534	Approved
0.6527	Remote Similarity	NPD2533	Approved
0.6519	Remote Similarity	NPD3764	Approved
0.6516	Remote Similarity	NPD3267	Approved
0.6516	Remote Similarity	NPD3266	Approved
0.65	Remote Similarity	NPD8404	Phase 2
0.6497	Remote Similarity	NPD3926	Phase 2
0.649	Remote Similarity	NPD5585	Approved
0.6485	Remote Similarity	NPD3750	Approved
0.648	Remote Similarity	NPD7799	Discontinued
0.6474	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1549	Phase 2
0.6461	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6801	Discontinued
0.6442	Remote Similarity	NPD2935	Discontinued
0.6438	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4307	Phase 2
0.6437	Remote Similarity	NPD4966	Approved
0.6437	Remote Similarity	NPD4967	Phase 2
0.6437	Remote Similarity	NPD7768	Phase 2
0.6437	Remote Similarity	NPD4965	Approved
0.6429	Remote Similarity	NPD9717	Approved
0.6429	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1608	Approved
0.642	Remote Similarity	NPD7097	Phase 1
0.6416	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3268	Approved
0.6414	Remote Similarity	NPD2182	Approved
0.6409	Remote Similarity	NPD7074	Phase 3
0.6402	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6002	Phase 3
0.6402	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6005	Phase 3
0.6402	Remote Similarity	NPD6004	Phase 3
0.6398	Remote Similarity	NPD4618	Approved
0.6398	Remote Similarity	NPD4622	Approved
0.6395	Remote Similarity	NPD5889	Approved
0.6395	Remote Similarity	NPD5890	Approved
0.6393	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7003	Approved
0.638	Remote Similarity	NPD7033	Discontinued
0.6379	Remote Similarity	NPD3817	Phase 2
0.6379	Remote Similarity	NPD5402	Approved
0.6374	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6234	Discontinued
0.6364	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7054	Approved
0.6353	Remote Similarity	NPD5403	Approved
0.6348	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD3887	Approved
0.6339	Remote Similarity	NPD7685	Pre-registration
0.6337	Remote Similarity	NPD4380	Phase 2
0.6337	Remote Similarity	NPD6585	Discontinued
0.6335	Remote Similarity	NPD2979	Phase 3
0.6333	Remote Similarity	NPD7473	Discontinued
0.6331	Remote Similarity	NPD5401	Approved
0.6331	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD8455	Phase 2
0.6319	Remote Similarity	NPD7472	Approved
0.6319	Remote Similarity	NPD5689	Approved
0.6319	Remote Similarity	NPD5688	Approved
0.6308	Remote Similarity	NPD7435	Discontinued
0.6306	Remote Similarity	NPD2797	Approved
0.6306	Remote Similarity	NPD1203	Approved
0.6298	Remote Similarity	NPD7228	Approved
0.6298	Remote Similarity	NPD3751	Discontinued
0.6296	Remote Similarity	NPD447	Suspended
0.6292	Remote Similarity	NPD7199	Phase 2
0.6286	Remote Similarity	NPD2296	Approved
0.6284	Remote Similarity	NPD6797	Phase 2
0.6284	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4359	Approved
0.628	Remote Similarity	NPD4308	Phase 3
0.628	Remote Similarity	NPD1510	Phase 2
0.6266	Remote Similarity	NPD5647	Approved
0.6264	Remote Similarity	NPD37	Approved
0.6264	Remote Similarity	NPD1934	Approved
0.6257	Remote Similarity	NPD6232	Discontinued
0.625	Remote Similarity	NPD7251	Discontinued
0.625	Remote Similarity	NPD3882	Suspended
0.6242	Remote Similarity	NPD6099	Approved
0.6242	Remote Similarity	NPD6100	Approved
0.6237	Remote Similarity	NPD6781	Approved
0.6237	Remote Similarity	NPD6778	Approved
0.6237	Remote Similarity	NPD6780	Approved
0.6237	Remote Similarity	NPD4107	Approved
0.6237	Remote Similarity	NPD6776	Approved
0.6237	Remote Similarity	NPD6782	Approved
0.6237	Remote Similarity	NPD6779	Approved
0.6237	Remote Similarity	NPD6777	Approved
0.6235	Remote Similarity	NPD3140	Approved
0.6235	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3142	Approved
0.6234	Remote Similarity	NPD1778	Approved
0.6232	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4420	Approved
0.6216	Remote Similarity	NPD7808	Phase 3
0.6213	Remote Similarity	NPD7236	Approved
0.6205	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2353	Approved
0.6201	Remote Similarity	NPD6959	Discontinued
0.6201	Remote Similarity	NPD8127	Discontinued
0.6196	Remote Similarity	NPD6355	Discontinued
0.6196	Remote Similarity	NPD5953	Discontinued
0.6194	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD2403	Approved
0.6175	Remote Similarity	NPD5844	Phase 1
0.6171	Remote Similarity	NPD6844	Discontinued
0.6167	Remote Similarity	NPD5711	Approved
0.6167	Remote Similarity	NPD5710	Approved
0.6164	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7240	Approved
0.6159	Remote Similarity	NPD6651	Approved
0.6158	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1281	Approved
0.6142	Remote Similarity	NPD7696	Phase 3
0.6142	Remote Similarity	NPD7697	Approved
0.6142	Remote Similarity	NPD7698	Approved
0.6138	Remote Similarity	NPD164	Approved
0.6136	Remote Similarity	NPD2801	Approved
0.6135	Remote Similarity	NPD4140	Approved
0.6135	Remote Similarity	NPD1240	Approved
0.6122	Remote Similarity	NPD4482	Phase 3
0.6119	Remote Similarity	NPD7874	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