NPASS Compound

Structure

NPC472778 OpenBabel07101718182D 35 39 0 0 1 0 0 0 0 0999 V2000 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2103 -3.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2967 -3.6306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0446 -5.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3581 -3.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0491 -4.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -3.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7401 -3.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 -2.5316 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2257 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.8271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2202 -4.3587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3621 -5.0632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0491 -4.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 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 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 32 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 33 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 26 1 0 0 0 0 12 14 2 0 0 0 0 12 33 1 0 0 0 0 13 15 1 0 0 0 0 13 21 2 0 0 0 0 14 23 1 0 0 0 0 15 26 1 0 0 0 0 16 21 1 0 0 0 0 16 27 1 6 0 0 0 17 25 1 0 0 0 0 17 27 1 1 0 0 0 18 28 2 0 0 0 0 18 32 1 0 0 0 0 19 29 2 0 0 0 0 19 34 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 20 30 1 6 0 0 0 21 35 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 1 0 0 0 23 34 1 0 0 0 0 24 27 1 6 0 0 0 24 35 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.23
Volume:	487.269
LogP:	3.64
LogD:	3.029
LogS:	-4.368
# Rotatable Bonds:	4
TPSA:	115.43
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	5.377
Fsp3:	0.63
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.161
MDCK Permeability:	3.46E-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.058
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.764
Plasma Protein Binding (PPB):	88.80%
Volume Distribution (VD):	2.114
Pgp-substrate:	14.07%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.504
CYP2C19-substrate:	0.457
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.527

ADMET: Excretion

Clearance (CL):	10.455
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.643
Human Hepatotoxicity (H-HT):	0.539
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.816
Skin Sensitization:	0.081
Carcinogencity:	0.137
Eye Corrosion:	0.004
Eye Irritation:	0.009
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC472778

Natural Product ID:	NPC472778
*Common Name:**	JUAVPAROZHLADF-YRBANECFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JUAVPAROZHLADF-YRBANECFSA-N
Standard InCHI:	InChI=1S/C27H34O8/c1-13-15-9-19(29)34-23(14-7-8-33-12-14)26(15,4)11-16-21(13)35-24-20(30)22(31)25(2,3)17(27(16,24)5)10-18(28)32-6/h7-9,12,16-17,20,22-24,30-31H,10-11H2,1-6H3/t16-,17-,20-,22+,23-,24-,26+,27+/m0/s1
SMILES:	COC(=O)C[C@@H]1[C@]2(C)[C@@H](OC3=C(C4=CC(=O)O[C@H]([C@@]4(C[C@H]23)C)c2cocc2)C)[C@H]([C@H](C1(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582107
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[514307]

☑ 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 NPC472778 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	322
0.1-0.2	1164
0.2-0.3	2886
0.3-0.4	5271
0.4-0.5	9789
0.5-0.6	9840
0.6-0.7	8703
0.7-0.8	4215
0.8-0.85	339
0.85-0.9	147
0.9-0.95	18
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472777
1.0	High Similarity	NPC472776
0.9286	High Similarity	NPC475967
0.9236	High Similarity	NPC472141
0.9221	High Similarity	NPC36655
0.9221	High Similarity	NPC261597
0.9221	High Similarity	NPC299038
0.9216	High Similarity	NPC44675
0.9216	High Similarity	NPC214541
0.9211	High Similarity	NPC469503
0.9167	High Similarity	NPC200782
0.9161	High Similarity	NPC475226
0.9161	High Similarity	NPC307383
0.9119	High Similarity	NPC271235
0.9108	High Similarity	NPC472773
0.9097	High Similarity	NPC187149
0.9091	High Similarity	NPC264943
0.9057	High Similarity	NPC472651
0.9057	High Similarity	NPC100333
0.9051	High Similarity	NPC276551
0.9051	High Similarity	NPC470182
0.9045	High Similarity	NPC69028
0.9045	High Similarity	NPC470792
0.9045	High Similarity	NPC472771
0.9045	High Similarity	NPC211777
0.9045	High Similarity	NPC188649
0.9026	High Similarity	NPC57998
0.902	High Similarity	NPC18135
0.9013	High Similarity	NPC125182
0.9013	High Similarity	NPC69647
0.9013	High Similarity	NPC195325
0.9007	High Similarity	NPC250228
0.9006	High Similarity	NPC169299
0.9006	High Similarity	NPC160818
0.9	High Similarity	NPC472652
0.9	High Similarity	NPC471397
0.8994	High Similarity	NPC93172
0.8994	High Similarity	NPC97574
0.8994	High Similarity	NPC470875
0.8987	High Similarity	NPC198047
0.8987	High Similarity	NPC469338
0.8987	High Similarity	NPC88841
0.8987	High Similarity	NPC292389
0.8987	High Similarity	NPC288602
0.8987	High Similarity	NPC472139
0.8981	High Similarity	NPC477402
0.8974	High Similarity	NPC45101
0.8974	High Similarity	NPC197137
0.8968	High Similarity	NPC155939
0.8968	High Similarity	NPC296807
0.8968	High Similarity	NPC35000
0.8968	High Similarity	NPC469336
0.8968	High Similarity	NPC141538
0.8961	High Similarity	NPC476201
0.8961	High Similarity	NPC268905
0.8961	High Similarity	NPC476939
0.8961	High Similarity	NPC476940
0.8944	High Similarity	NPC82602
0.8938	High Similarity	NPC472775
0.8938	High Similarity	NPC173516
0.8938	High Similarity	NPC472774
0.8931	High Similarity	NPC271657
0.8931	High Similarity	NPC470940
0.8931	High Similarity	NPC469849
0.8924	High Similarity	NPC329938
0.8924	High Similarity	NPC82851
0.8924	High Similarity	NPC149896
0.8917	High Similarity	NPC472671
0.891	High Similarity	NPC469485
0.8903	High Similarity	NPC178932
0.8903	High Similarity	NPC34421
0.8903	High Similarity	NPC237259
0.8903	High Similarity	NPC253201
0.8903	High Similarity	NPC98206
0.8903	High Similarity	NPC302054
0.8903	High Similarity	NPC30222
0.8903	High Similarity	NPC282445
0.8896	High Similarity	NPC469576
0.8889	High Similarity	NPC475237
0.8889	High Similarity	NPC475641
0.8889	High Similarity	NPC472654
0.8882	High Similarity	NPC472766
0.8882	High Similarity	NPC472765
0.8882	High Similarity	NPC255414
0.8875	High Similarity	NPC121995
0.8868	High Similarity	NPC283209
0.8868	High Similarity	NPC285567
0.8868	High Similarity	NPC302369
0.8868	High Similarity	NPC477405
0.8868	High Similarity	NPC134254
0.8868	High Similarity	NPC39986
0.8867	High Similarity	NPC223415
0.8861	High Similarity	NPC472653
0.8854	High Similarity	NPC470119
0.8854	High Similarity	NPC214495
0.8854	High Similarity	NPC470118
0.8854	High Similarity	NPC173544
0.8854	High Similarity	NPC88007
0.8854	High Similarity	NPC194499
0.8854	High Similarity	NPC472772
0.8854	High Similarity	NPC475066
0.8846	High Similarity	NPC92979
0.8846	High Similarity	NPC476262
0.8841	High Similarity	NPC469633
0.8839	High Similarity	NPC472672
0.8839	High Similarity	NPC33938
0.8831	High Similarity	NPC470997
0.882	High Similarity	NPC476861
0.882	High Similarity	NPC476850
0.882	High Similarity	NPC472764
0.8816	High Similarity	NPC346
0.8812	High Similarity	NPC123088
0.8805	High Similarity	NPC68848
0.8805	High Similarity	NPC5079
0.8805	High Similarity	NPC18986
0.8805	High Similarity	NPC18347
0.8805	High Similarity	NPC207978
0.8797	High Similarity	NPC477403
0.8797	High Similarity	NPC474611
0.8797	High Similarity	NPC262872
0.878	High Similarity	NPC236004
0.878	High Similarity	NPC94763
0.8773	High Similarity	NPC294512
0.8766	High Similarity	NPC234494
0.8765	High Similarity	NPC160651
0.8765	High Similarity	NPC296558
0.8758	High Similarity	NPC221809
0.875	High Similarity	NPC234660
0.875	High Similarity	NPC165218
0.875	High Similarity	NPC51568
0.875	High Similarity	NPC469846
0.875	High Similarity	NPC5676
0.8742	High Similarity	NPC470789
0.8742	High Similarity	NPC335761
0.8734	High Similarity	NPC195954
0.8734	High Similarity	NPC249021
0.8734	High Similarity	NPC167142
0.8718	High Similarity	NPC75906
0.8718	High Similarity	NPC121615
0.8718	High Similarity	NPC294511
0.8718	High Similarity	NPC147168
0.8712	High Similarity	NPC470995
0.871	High Similarity	NPC196846
0.871	High Similarity	NPC159927
0.871	High Similarity	NPC469335
0.871	High Similarity	NPC476122
0.8704	High Similarity	NPC472282
0.8704	High Similarity	NPC478179
0.8701	High Similarity	NPC7388
0.8696	High Similarity	NPC476858
0.8696	High Similarity	NPC476856
0.8696	High Similarity	NPC476857
0.8688	High Similarity	NPC472767
0.8688	High Similarity	NPC263432
0.8684	High Similarity	NPC476944
0.8684	High Similarity	NPC137295
0.8684	High Similarity	NPC251865
0.8683	High Similarity	NPC470938
0.8675	High Similarity	NPC478177
0.8667	High Similarity	NPC471437
0.8654	High Similarity	NPC116717
0.8645	High Similarity	NPC471001
0.8642	High Similarity	NPC472670
0.8642	High Similarity	NPC86800
0.8642	High Similarity	NPC475779
0.8642	High Similarity	NPC307781
0.8636	High Similarity	NPC476938
0.8636	High Similarity	NPC476937
0.8636	High Similarity	NPC470941
0.8636	High Similarity	NPC471174
0.8627	High Similarity	NPC41182
0.8625	High Similarity	NPC287559
0.8625	High Similarity	NPC25255
0.8618	High Similarity	NPC476946
0.8618	High Similarity	NPC470741
0.8616	High Similarity	NPC472283
0.8616	High Similarity	NPC286722
0.8616	High Similarity	NPC304692
0.8614	High Similarity	NPC176413
0.8614	High Similarity	NPC56953
0.8614	High Similarity	NPC262386
0.8608	High Similarity	NPC281258
0.86	High Similarity	NPC90953
0.8599	High Similarity	NPC29695
0.8599	High Similarity	NPC182427
0.8599	High Similarity	NPC44577
0.8599	High Similarity	NPC322546
0.8599	High Similarity	NPC470996
0.8599	High Similarity	NPC308205
0.8598	High Similarity	NPC118086
0.8591	High Similarity	NPC186626
0.8589	High Similarity	NPC270312
0.8589	High Similarity	NPC476853
0.8581	High Similarity	NPC476942
0.8581	High Similarity	NPC471007
0.8581	High Similarity	NPC476941
0.858	High Similarity	NPC276735
0.8571	High Similarity	NPC290400
0.8571	High Similarity	NPC117986
0.8571	High Similarity	NPC79571

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 NPC472778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	841
0.2-0.3	2070
0.3-0.4	2581
0.4-0.5	2007
0.5-0.6	1001
0.6-0.7	323
0.7-0.8	48
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8491	Intermediate Similarity	NPD5761	Phase 2
0.8491	Intermediate Similarity	NPD5760	Phase 2
0.8471	Intermediate Similarity	NPD8434	Phase 2
0.7952	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6764	Approved
0.7657	Intermediate Similarity	NPD6765	Approved
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7605	Intermediate Similarity	NPD7819	Suspended
0.7605	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7075	Discontinued
0.7561	Intermediate Similarity	NPD920	Approved
0.7557	Intermediate Similarity	NPD6559	Discontinued
0.7545	Intermediate Similarity	NPD6801	Discontinued
0.7529	Intermediate Similarity	NPD3818	Discontinued
0.7486	Intermediate Similarity	NPD6784	Approved
0.7486	Intermediate Similarity	NPD6785	Approved
0.7456	Intermediate Similarity	NPD3817	Phase 2
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD919	Approved
0.7425	Intermediate Similarity	NPD4380	Phase 2
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.7412	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5494	Approved
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5402	Approved
0.7347	Intermediate Similarity	NPD8404	Phase 2
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4965	Approved
0.7294	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD7473	Discontinued
0.7246	Intermediate Similarity	NPD5403	Approved
0.7241	Intermediate Similarity	NPD8127	Discontinued
0.7241	Intermediate Similarity	NPD7199	Phase 2
0.7241	Intermediate Similarity	NPD1247	Approved
0.7235	Intermediate Similarity	NPD1934	Approved
0.7229	Intermediate Similarity	NPD2533	Approved
0.7229	Intermediate Similarity	NPD2534	Approved
0.7229	Intermediate Similarity	NPD5401	Approved
0.7229	Intermediate Similarity	NPD2532	Approved
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3882	Suspended
0.72	Intermediate Similarity	NPD6232	Discontinued
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2801	Approved
0.7191	Intermediate Similarity	NPD7054	Approved
0.7191	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7411	Suspended
0.7168	Intermediate Similarity	NPD3749	Approved
0.716	Intermediate Similarity	NPD2796	Approved
0.7151	Intermediate Similarity	NPD7074	Phase 3
0.7151	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7472	Approved
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD1243	Approved
0.7134	Intermediate Similarity	NPD2800	Approved
0.7127	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6166	Phase 2
0.7119	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3750	Approved
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD6273	Approved
0.7072	Intermediate Similarity	NPD7251	Discontinued
0.7062	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3226	Approved
0.7033	Intermediate Similarity	NPD7808	Phase 3
0.703	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6797	Phase 2
0.7017	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7768	Phase 2
0.6994	Remote Similarity	NPD1465	Phase 2
0.6994	Remote Similarity	NPD3748	Approved
0.6994	Remote Similarity	NPD2799	Discontinued
0.6994	Remote Similarity	NPD7033	Discontinued
0.6978	Remote Similarity	NPD7685	Pre-registration
0.6978	Remote Similarity	NPD7240	Approved
0.6973	Remote Similarity	NPD8150	Discontinued
0.697	Remote Similarity	NPD1549	Phase 2
0.6966	Remote Similarity	NPD3926	Phase 2
0.6964	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD8407	Phase 2
0.6951	Remote Similarity	NPD1551	Phase 2
0.6944	Remote Similarity	NPD7799	Discontinued
0.6944	Remote Similarity	NPD3751	Discontinued
0.6941	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2313	Discontinued
0.6927	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6832	Phase 2
0.6914	Remote Similarity	NPD6355	Discontinued
0.6914	Remote Similarity	NPD447	Suspended
0.691	Remote Similarity	NPD7229	Phase 3
0.6909	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2346	Discontinued
0.6909	Remote Similarity	NPD6004	Phase 3
0.6909	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6002	Phase 3
0.6909	Remote Similarity	NPD6005	Phase 3
0.6898	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1510	Phase 2
0.6886	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8368	Discontinued
0.6882	Remote Similarity	NPD1512	Approved
0.6864	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7458	Discontinued
0.686	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6959	Discontinued
0.6848	Remote Similarity	NPD2935	Discontinued
0.6816	Remote Similarity	NPD3787	Discontinued
0.681	Remote Similarity	NPD230	Phase 1
0.6807	Remote Similarity	NPD1471	Phase 3
0.6807	Remote Similarity	NPD2344	Approved
0.6805	Remote Similarity	NPD7236	Approved
0.68	Remote Similarity	NPD8455	Phase 2
0.6768	Remote Similarity	NPD6651	Approved
0.6758	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1608	Approved
0.6747	Remote Similarity	NPD6100	Approved
0.6747	Remote Similarity	NPD6099	Approved
0.6746	Remote Similarity	NPD6190	Approved
0.6735	Remote Similarity	NPD7497	Discontinued
0.6735	Remote Similarity	NPD7435	Discontinued
0.673	Remote Similarity	NPD2797	Approved
0.6728	Remote Similarity	NPD3268	Approved
0.6722	Remote Similarity	NPD5711	Approved
0.6722	Remote Similarity	NPD5710	Approved
0.6715	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5763	Approved
0.6707	Remote Similarity	NPD5762	Approved
0.6705	Remote Similarity	NPD7239	Suspended
0.6699	Remote Similarity	NPD7907	Approved
0.6687	Remote Similarity	NPD5647	Approved
0.6686	Remote Similarity	NPD4110	Phase 3
0.6686	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4665	Approved
0.6683	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5353	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.6649	Remote Similarity	NPD5953	Discontinued
0.6647	Remote Similarity	NPD2309	Approved
0.6646	Remote Similarity	NPD1240	Approved
0.6646	Remote Similarity	NPD9717	Approved
0.6646	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8361	Approved
0.6632	Remote Similarity	NPD8360	Approved
0.6632	Remote Similarity	NPD8435	Approved
0.663	Remote Similarity	NPD7315	Approved
0.663	Remote Similarity	NPD7286	Phase 2
0.6627	Remote Similarity	NPD1652	Phase 2
0.6627	Remote Similarity	NPD7097	Phase 1
0.6626	Remote Similarity	NPD3764	Approved
0.6626	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6798	Discontinued
0.6609	Remote Similarity	NPD1653	Approved
0.6606	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5124	Phase 1
0.6606	Remote Similarity	NPD1933	Approved
0.6599	Remote Similarity	NPD3057	Approved
0.6591	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7003	Approved
0.6588	Remote Similarity	NPD8166	Discontinued
0.6587	Remote Similarity	NPD4308	Phase 3
0.6585	Remote Similarity	NPD6233	Phase 2
0.6584	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2798	Approved
0.6582	Remote Similarity	NPD6777	Approved
0.6582	Remote Similarity	NPD6781	Approved
0.6582	Remote Similarity	NPD6776	Approved
0.6582	Remote Similarity	NPD6778	Approved
0.6582	Remote Similarity	NPD6782	Approved
0.6582	Remote Similarity	NPD4107	Approved
0.6582	Remote Similarity	NPD6780	Approved
0.6582	Remote Similarity	NPD6779	Approved
0.6568	Remote Similarity	NPD2424	Discontinued
0.6567	Remote Similarity	NPD8151	Discontinued
0.6566	Remote Similarity	NPD1607	Approved
0.6564	Remote Similarity	NPD7095	Approved
0.6562	Remote Similarity	NPD8651	Approved
0.6561	Remote Similarity	NPD17	Approved
0.6557	Remote Similarity	NPD2403	Approved
0.6545	Remote Similarity	NPD4140	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