NPASS Compound

Structure

NPC474722 OpenBabel07101718202D 26 29 0 0 1 0 0 0 0 0999 V2000 0.8856 -3.2160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6899 -2.7239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2679 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 -1.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -1.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -2.2272 0.0000 C 0 0 2 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 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 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 1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 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 13 1 0 0 0 0 3 20 1 0 0 0 0 4 24 1 0 0 0 0 5 7 1 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 8 25 1 0 0 0 0 9 15 1 0 0 0 0 9 17 2 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 25 1 0 0 0 0 13 19 1 1 0 0 0 14 16 1 0 0 0 0 15 22 2 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 2 1 1 0 0 0 20 21 1 6 0 0 0 21 7 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	365.679
LogP:	2.853
LogD:	3.156
LogS:	-4.611
# Rotatable Bonds:	3
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	5.543
Fsp3:	0.524
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:	-5.157
MDCK Permeability:	3.220958387828432e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	90.745361328125%
Volume Distribution (VD):	1.597
Pgp-substrate:	10.201959609985352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.472
CYP1A2-substrate:	0.799
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.149
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	9.867
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.245
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC474722

Natural Product ID:	NPC474722
*Common Name:**	VXAWMXLXZCKLAP-JTMTTYTKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VXAWMXLXZCKLAP-JTMTTYTKSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-13-5-7-21-17(9-15(22)10-20(21,3)18(23)24-4)19(13,2)11-16(26-21)14-6-8-25-12-14/h6,8-9,11-13H,5,7,10H2,1-4H3/t13-,19+,20-,21-/m1/s1
SMILES:	COC(=O)[C@@]1(C)CC(=O)C=C2[C@@]31CC[C@H]([C@@]2(C=C(O3)c1ccoc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480276
PubChem CID:	11187407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15679308]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	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
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[466001]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	<	12.5	ug.mL-1	PMID[466001]

☑ 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 NPC474722 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	327
0.1-0.2	1395
0.2-0.3	2952
0.3-0.4	6433
0.4-0.5	11594
0.5-0.6	10094
0.6-0.7	8775
0.7-0.8	1024
0.8-0.85	99
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8806	High Similarity	NPC208389
0.8705	High Similarity	NPC310830
0.8705	High Similarity	NPC307401
0.8705	High Similarity	NPC470742
0.8643	High Similarity	NPC476943
0.8643	High Similarity	NPC220094
0.8593	High Similarity	NPC279877
0.8561	High Similarity	NPC92941
0.8552	High Similarity	NPC62799
0.8552	High Similarity	NPC233763
0.8552	High Similarity	NPC346
0.8551	High Similarity	NPC470740
0.8514	High Similarity	NPC240214
0.8511	High Similarity	NPC236532
0.85	High Similarity	NPC146872
0.8456	Intermediate Similarity	NPC26532
0.8451	Intermediate Similarity	NPC202260
0.8446	Intermediate Similarity	NPC469335
0.8446	Intermediate Similarity	NPC196864
0.8446	Intermediate Similarity	NPC477404
0.8446	Intermediate Similarity	NPC159927
0.8435	Intermediate Similarity	NPC19747
0.8425	Intermediate Similarity	NPC262198
0.8414	Intermediate Similarity	NPC476944
0.8414	Intermediate Similarity	NPC142113
0.84	Intermediate Similarity	NPC30222
0.8397	Intermediate Similarity	NPC87466
0.8394	Intermediate Similarity	NPC59502
0.8382	Intermediate Similarity	NPC290955
0.8382	Intermediate Similarity	NPC246392
0.8378	Intermediate Similarity	NPC211625
0.8367	Intermediate Similarity	NPC224418
0.8367	Intermediate Similarity	NPC221809
0.8367	Intermediate Similarity	NPC470941
0.8345	Intermediate Similarity	NPC267632
0.8345	Intermediate Similarity	NPC223415
0.8344	Intermediate Similarity	NPC35000
0.8344	Intermediate Similarity	NPC469850
0.8322	Intermediate Similarity	NPC476122
0.831	Intermediate Similarity	NPC42400
0.8301	Intermediate Similarity	NPC474611
0.8299	Intermediate Similarity	NPC471292
0.8289	Intermediate Similarity	NPC104736
0.8289	Intermediate Similarity	NPC209364
0.8289	Intermediate Similarity	NPC41880
0.8288	Intermediate Similarity	NPC238843
0.8288	Intermediate Similarity	NPC84479
0.8288	Intermediate Similarity	NPC199044
0.8278	Intermediate Similarity	NPC57998
0.8278	Intermediate Similarity	NPC178932
0.8276	Intermediate Similarity	NPC475519
0.8273	Intermediate Similarity	NPC298190
0.8264	Intermediate Similarity	NPC56197
0.8247	Intermediate Similarity	NPC287559
0.8235	Intermediate Similarity	NPC81405
0.8235	Intermediate Similarity	NPC304692
0.8235	Intermediate Similarity	NPC286722
0.8224	Intermediate Similarity	NPC469336
0.8224	Intermediate Similarity	NPC214541
0.8224	Intermediate Similarity	NPC44675
0.8224	Intermediate Similarity	NPC264943
0.8219	Intermediate Similarity	NPC476946
0.8219	Intermediate Similarity	NPC470741
0.8217	Intermediate Similarity	NPC473766
0.8217	Intermediate Similarity	NPC473753
0.8212	Intermediate Similarity	NPC476201
0.8212	Intermediate Similarity	NPC469503
0.8207	Intermediate Similarity	NPC20500
0.8205	Intermediate Similarity	NPC276735
0.82	Intermediate Similarity	NPC476936
0.82	Intermediate Similarity	NPC212257
0.82	Intermediate Similarity	NPC472298
0.82	Intermediate Similarity	NPC156189
0.8194	Intermediate Similarity	NPC188649
0.8188	Intermediate Similarity	NPC243165
0.8182	Intermediate Similarity	NPC140952
0.8182	Intermediate Similarity	NPC307383
0.8182	Intermediate Similarity	NPC475295
0.8182	Intermediate Similarity	NPC473473
0.8176	Intermediate Similarity	NPC276676
0.817	Intermediate Similarity	NPC60973
0.817	Intermediate Similarity	NPC107646
0.8158	Intermediate Similarity	NPC114880
0.8158	Intermediate Similarity	NPC282445
0.8156	Intermediate Similarity	NPC293253
0.8153	Intermediate Similarity	NPC121995
0.8151	Intermediate Similarity	NPC52412
0.8146	Intermediate Similarity	NPC18135
0.8143	Intermediate Similarity	NPC61788
0.8141	Intermediate Similarity	NPC224394
0.8141	Intermediate Similarity	NPC663
0.8141	Intermediate Similarity	NPC288602
0.8141	Intermediate Similarity	NPC88841
0.8138	Intermediate Similarity	NPC156077
0.8133	Intermediate Similarity	NPC95526
0.8133	Intermediate Similarity	NPC195325
0.8129	Intermediate Similarity	NPC198904
0.8121	Intermediate Similarity	NPC250228
0.8121	Intermediate Similarity	NPC10088
0.8121	Intermediate Similarity	NPC71821
0.8117	Intermediate Similarity	NPC472772
0.8117	Intermediate Similarity	NPC472778
0.8117	Intermediate Similarity	NPC472776
0.8117	Intermediate Similarity	NPC167142
0.8117	Intermediate Similarity	NPC472283
0.8117	Intermediate Similarity	NPC249021
0.8117	Intermediate Similarity	NPC261597
0.8117	Intermediate Similarity	NPC472777
0.8116	Intermediate Similarity	NPC95567
0.8116	Intermediate Similarity	NPC319140
0.8113	Intermediate Similarity	NPC302392
0.8108	Intermediate Similarity	NPC56731
0.8105	Intermediate Similarity	NPC476262
0.8105	Intermediate Similarity	NPC25351
0.8102	Intermediate Similarity	NPC290193
0.8102	Intermediate Similarity	NPC179354
0.8101	Intermediate Similarity	NPC478179
0.8095	Intermediate Similarity	NPC205071
0.8092	Intermediate Similarity	NPC75906
0.8092	Intermediate Similarity	NPC246164
0.8092	Intermediate Similarity	NPC476939
0.8092	Intermediate Similarity	NPC476940
0.8089	Intermediate Similarity	NPC56358
0.8088	Intermediate Similarity	NPC16922
0.8079	Intermediate Similarity	NPC470997
0.8079	Intermediate Similarity	NPC46551
0.8079	Intermediate Similarity	NPC228842
0.8077	Intermediate Similarity	NPC68848
0.8077	Intermediate Similarity	NPC329938
0.8077	Intermediate Similarity	NPC5079
0.8077	Intermediate Similarity	NPC197596
0.8077	Intermediate Similarity	NPC18986
0.8071	Intermediate Similarity	NPC21460
0.8067	Intermediate Similarity	NPC476941
0.8067	Intermediate Similarity	NPC476942
0.8065	Intermediate Similarity	NPC473368
0.8065	Intermediate Similarity	NPC474932
0.8065	Intermediate Similarity	NPC477403
0.8058	Intermediate Similarity	NPC112706
0.8058	Intermediate Similarity	NPC207294
0.8052	Intermediate Similarity	NPC469485
0.8052	Intermediate Similarity	NPC126723
0.8052	Intermediate Similarity	NPC263265
0.805	Intermediate Similarity	NPC296558
0.8043	Intermediate Similarity	NPC74612
0.8042	Intermediate Similarity	NPC158525
0.8041	Intermediate Similarity	NPC251865
0.8029	Intermediate Similarity	NPC65735
0.8029	Intermediate Similarity	NPC188377
0.8027	Intermediate Similarity	NPC121158
0.8027	Intermediate Similarity	NPC263337
0.8026	Intermediate Similarity	NPC144010
0.8025	Intermediate Similarity	NPC165218
0.8025	Intermediate Similarity	NPC292389
0.8025	Intermediate Similarity	NPC51568
0.8025	Intermediate Similarity	NPC469338
0.8025	Intermediate Similarity	NPC283209
0.8025	Intermediate Similarity	NPC285567
0.8025	Intermediate Similarity	NPC234660
0.8013	Intermediate Similarity	NPC470790
0.8013	Intermediate Similarity	NPC477402
0.8013	Intermediate Similarity	NPC475381
0.8013	Intermediate Similarity	NPC472654
0.8013	Intermediate Similarity	NPC470791
0.8	Intermediate Similarity	NPC195954
0.8	Intermediate Similarity	NPC88007
0.8	Intermediate Similarity	NPC472376
0.8	Intermediate Similarity	NPC173544
0.8	Intermediate Similarity	NPC194499
0.8	Intermediate Similarity	NPC299038
0.8	Intermediate Similarity	NPC476938
0.8	Intermediate Similarity	NPC476937
0.8	Intermediate Similarity	NPC187149
0.8	Intermediate Similarity	NPC36655
0.7987	Intermediate Similarity	NPC290038
0.7987	Intermediate Similarity	NPC75310
0.7987	Intermediate Similarity	NPC270312
0.7986	Intermediate Similarity	NPC46896
0.7986	Intermediate Similarity	NPC83178
0.7975	Intermediate Similarity	NPC469849
0.7975	Intermediate Similarity	NPC472664
0.7975	Intermediate Similarity	NPC276551
0.7975	Intermediate Similarity	NPC470940
0.7974	Intermediate Similarity	NPC33938
0.7971	Intermediate Similarity	NPC300098
0.7962	Intermediate Similarity	NPC82851
0.7962	Intermediate Similarity	NPC470939
0.7962	Intermediate Similarity	NPC472771
0.7962	Intermediate Similarity	NPC149896
0.7962	Intermediate Similarity	NPC69028
0.795	Intermediate Similarity	NPC294512
0.7949	Intermediate Similarity	NPC475967
0.7949	Intermediate Similarity	NPC237155
0.7947	Intermediate Similarity	NPC93666
0.7945	Intermediate Similarity	NPC90953
0.7935	Intermediate Similarity	NPC204663
0.7925	Intermediate Similarity	NPC470875
0.7925	Intermediate Similarity	NPC478178
0.7922	Intermediate Similarity	NPC471863
0.7922	Intermediate Similarity	NPC44606

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 NPC474722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	1005
0.2-0.3	1988
0.3-0.4	2665
0.4-0.5	1975
0.5-0.6	947
0.6-0.7	267
0.7-0.8	15
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
0.7785	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5760	Phase 2
0.7756	Intermediate Similarity	NPD5761	Phase 2
0.7703	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8434	Phase 2
0.7597	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1471	Phase 3
0.7351	Intermediate Similarity	NPD2346	Discontinued
0.7338	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7279	Intermediate Similarity	NPD2313	Discontinued
0.7278	Intermediate Similarity	NPD6765	Approved
0.7278	Intermediate Similarity	NPD6764	Approved
0.726	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD3748	Approved
0.7197	Intermediate Similarity	NPD6273	Approved
0.7181	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD1243	Approved
0.7134	Intermediate Similarity	NPD919	Approved
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8032	Phase 2
0.711	Intermediate Similarity	NPD6785	Approved
0.711	Intermediate Similarity	NPD6784	Approved
0.7099	Intermediate Similarity	NPD7819	Suspended
0.7097	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3226	Approved
0.7059	Intermediate Similarity	NPD2796	Approved
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7055	Intermediate Similarity	NPD3267	Approved
0.7055	Intermediate Similarity	NPD3266	Approved
0.7019	Intermediate Similarity	NPD6599	Discontinued
0.7013	Intermediate Similarity	NPD2344	Approved
0.7007	Intermediate Similarity	NPD1019	Discontinued
0.7007	Intermediate Similarity	NPD2798	Approved
0.6993	Remote Similarity	NPD4308	Phase 3
0.6988	Remote Similarity	NPD5494	Approved
0.6987	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD6559	Discontinued
0.697	Remote Similarity	NPD3749	Approved
0.6957	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1247	Approved
0.6939	Remote Similarity	NPD2797	Approved
0.6933	Remote Similarity	NPD3268	Approved
0.6918	Remote Similarity	NPD2534	Approved
0.6918	Remote Similarity	NPD2533	Approved
0.6918	Remote Similarity	NPD2532	Approved
0.6905	Remote Similarity	NPD6808	Phase 2
0.6897	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7003	Approved
0.6879	Remote Similarity	NPD4628	Phase 3
0.6875	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1876	Approved
0.6857	Remote Similarity	NPD1241	Discontinued
0.6849	Remote Similarity	NPD3972	Approved
0.6849	Remote Similarity	NPD9717	Approved
0.6842	Remote Similarity	NPD2979	Phase 3
0.6842	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1551	Phase 2
0.6835	Remote Similarity	NPD2309	Approved
0.6815	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2800	Approved
0.6813	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5585	Approved
0.6797	Remote Similarity	NPD1933	Approved
0.6797	Remote Similarity	NPD447	Suspended
0.6792	Remote Similarity	NPD7236	Approved
0.6788	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7411	Suspended
0.6752	Remote Similarity	NPD970	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6799	Approved
0.6748	Remote Similarity	NPD7458	Discontinued
0.6747	Remote Similarity	NPD3817	Phase 2
0.6747	Remote Similarity	NPD5402	Approved
0.6727	Remote Similarity	NPD6279	Approved
0.6727	Remote Similarity	NPD6801	Discontinued
0.6727	Remote Similarity	NPD6280	Approved
0.6711	Remote Similarity	NPD1203	Approved
0.6711	Remote Similarity	NPD411	Approved
0.6708	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7768	Phase 2
0.669	Remote Similarity	NPD5691	Approved
0.6686	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD5890	Approved
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD5889	Approved
0.6667	Remote Similarity	NPD1281	Approved
0.6649	Remote Similarity	NPD8404	Phase 2
0.6647	Remote Similarity	NPD8127	Discontinued
0.6643	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5403	Approved
0.6624	Remote Similarity	NPD2438	Suspended
0.6623	Remote Similarity	NPD4140	Approved
0.6619	Remote Similarity	NPD2182	Approved
0.6608	Remote Similarity	NPD6232	Discontinued
0.6606	Remote Similarity	NPD6585	Discontinued
0.6605	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5401	Approved
0.6601	Remote Similarity	NPD3764	Approved
0.6596	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7239	Suspended
0.6581	Remote Similarity	NPD4622	Approved
0.6581	Remote Similarity	NPD4618	Approved
0.6581	Remote Similarity	NPD6355	Discontinued
0.6577	Remote Similarity	NPD4359	Approved
0.6562	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4110	Phase 3
0.6562	Remote Similarity	NPD8166	Discontinued
0.6561	Remote Similarity	NPD1510	Phase 2
0.6561	Remote Similarity	NPD7033	Discontinued
0.6552	Remote Similarity	NPD3818	Discontinued
0.6548	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1549	Phase 2
0.6536	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1283	Approved
0.6532	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD17	Approved
0.6524	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3887	Approved
0.6519	Remote Similarity	NPD2531	Phase 2
0.6519	Remote Similarity	NPD6099	Approved
0.6519	Remote Similarity	NPD6100	Approved
0.6517	Remote Similarity	NPD8312	Approved
0.6517	Remote Similarity	NPD8313	Approved
0.6514	Remote Similarity	NPD5844	Phase 1
0.6509	Remote Similarity	NPD3882	Suspended
0.6506	Remote Similarity	NPD4380	Phase 2
0.6506	Remote Similarity	NPD7028	Phase 2
0.6497	Remote Similarity	NPD5688	Approved
0.6497	Remote Similarity	NPD7097	Phase 1
0.6497	Remote Similarity	NPD5689	Approved
0.6494	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2801	Approved
0.6486	Remote Similarity	NPD3496	Discontinued
0.6478	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6004	Phase 3
0.6478	Remote Similarity	NPD6005	Phase 3
0.6478	Remote Similarity	NPD6002	Phase 3
0.6478	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5327	Phase 3
0.6463	Remote Similarity	NPD1651	Approved
0.6453	Remote Similarity	NPD6959	Discontinued
0.6448	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5647	Approved
0.6438	Remote Similarity	NPD2424	Discontinued
0.6429	Remote Similarity	NPD37	Approved
0.6429	Remote Similarity	NPD7095	Approved
0.6429	Remote Similarity	NPD6844	Discontinued
0.6429	Remote Similarity	NPD1934	Approved
0.6419	Remote Similarity	NPD4626	Approved
0.6419	Remote Similarity	NPD1778	Approved
0.6416	Remote Similarity	NPD5710	Approved
0.6416	Remote Similarity	NPD5711	Approved
0.6416	Remote Similarity	NPD7229	Phase 3
0.6415	Remote Similarity	NPD4477	Approved
0.6415	Remote Similarity	NPD4476	Approved
0.6412	Remote Similarity	NPD4967	Phase 2
0.6412	Remote Similarity	NPD4965	Approved
0.6412	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4966	Approved
0.64	Remote Similarity	NPD1608	Approved
0.6387	Remote Similarity	NPD6798	Discontinued
0.6387	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4107	Approved
0.6376	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2353	Approved
0.6375	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.637	Remote Similarity	NPD9493	Approved
0.6357	Remote Similarity	NPD3134	Approved
0.6354	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4288	Approved
0.6353	Remote Similarity	NPD2296	Approved
0.6348	Remote Similarity	NPD5953	Discontinued
0.6346	Remote Similarity	NPD4870	Approved
0.6346	Remote Similarity	NPD6233	Phase 2
0.6343	Remote Similarity	NPD2403	Approved
0.6341	Remote Similarity	NPD1511	Approved
0.6337	Remote Similarity	NPD6234	Discontinued
0.6333	Remote Similarity	NPD1611	Approved
0.6331	Remote Similarity	NPD164	Approved
0.633	Remote Similarity	NPD8285	Discontinued
0.6329	Remote Similarity	NPD1607	Approved
0.6319	Remote Similarity	NPD5535	Approved
0.6316	Remote Similarity	NPD7058	Phase 2
0.6316	Remote Similarity	NPD7057	Phase 3
0.6306	Remote Similarity	NPD4060	Phase 1
0.6306	Remote Similarity	NPD3140	Approved
0.6306	Remote Similarity	NPD3142	Approved
0.6306	Remote Similarity	NPD1240	Approved
0.6282	Remote Similarity	NPD7985	Registered
0.6282	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD1296	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