NPASS Compound

Structure

CID272590 OpenBabel06191716082D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.9740 2.7169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4072 -0.9567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4073 -1.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0306 -1.9673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5628 -0.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8437 -1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 -2.9235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3016 0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 -0.9745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8440 -2.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8743 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3759 -0.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7713 1.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3756 0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6884 -0.9749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5321 -2.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 0.4874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5321 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 1.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5323 -1.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 -1.4622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6879 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4957 1.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4007 -2.9378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3974 1.9618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4290 2.9146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3021 -1.2733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 33 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 33 1 0 0 0 0 15 29 2 0 0 0 0 15 34 1 0 0 0 0 16 21 1 0 0 0 0 17 26 1 6 0 0 0 17 28 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 6 0 0 0 19 25 1 0 0 0 0 19 30 2 0 0 0 0 20 28 1 1 0 0 0 20 34 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 23 1 0 0 0 0 22 31 2 0 0 0 0 23 24 2 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.24
Volume:	484.348
LogP:	3.29
LogD:	2.693
LogS:	-4.653
# Rotatable Bonds:	3
TPSA:	90.65
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	5.13
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.162
MDCK Permeability:	6.748257874278352e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.433
30% Bioavailability (F30%):	0.738

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	93.49514770507812%
Volume Distribution (VD):	1.739
Pgp-substrate:	7.310441017150879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.453
CYP2C19-substrate:	0.593
CYP2C9-inhibitor:	0.767
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.602

ADMET: Excretion

Clearance (CL):	3.718
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.885
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.107
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC272590

Natural Product ID:	NPC272590
*Common Name:**	15-Hydroxyazadiradione
IUPAC Name:	[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-15-hydroxy-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
Synonyms:	15-Hydroxyazadiradione
Standard InCHIKey:	LZENOAGERLXZPK-RRVWWXAYSA-N
Standard InCHI:	InChI=1S/C28H34O6/c1-15(29)34-20-13-18-25(2,3)19(30)8-11-26(18,4)17-7-10-27(5)21(16-9-12-33-14-16)22(31)23(32)24(27)28(17,20)6/h8-9,11-12,14,17-18,20-21,32H,7,10,13H2,1-6H3/t17-,18+,20-,21-,26-,27+,28+/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@H](c4ccoc4)C(=O)C(=C3[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774402
PubChem CID:	52951756
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	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
IC50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	20000.0	nM	PMID[448191]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[448191]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[448191]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[448191]

☑ 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 NPC272590 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	318
0.1-0.2	1345
0.2-0.3	2857
0.3-0.4	5643
0.4-0.5	11176
0.5-0.6	10332
0.6-0.7	9500
0.7-0.8	1110
0.8-0.85	275
0.85-0.9	124
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC246164
0.951	High Similarity	NPC199044
0.951	High Similarity	NPC238843
0.9448	High Similarity	NPC471174
0.9444	High Similarity	NPC185456
0.9408	High Similarity	NPC224394
0.9408	High Similarity	NPC663
0.9396	High Similarity	NPC92979
0.9379	High Similarity	NPC471292
0.9315	High Similarity	NPC216755
0.9231	High Similarity	NPC56197
0.9189	High Similarity	NPC234494
0.9184	High Similarity	NPC302987
0.9139	High Similarity	NPC141538
0.9139	High Similarity	NPC296807
0.9139	High Similarity	NPC155939
0.9128	High Similarity	NPC470997
0.906	High Similarity	NPC471001
0.906	High Similarity	NPC472654
0.9007	High Similarity	NPC33938
0.8968	High Similarity	NPC197596
0.8947	High Similarity	NPC178932
0.8896	High Similarity	NPC197137
0.8889	High Similarity	NPC469336
0.8889	High Similarity	NPC25351
0.8882	High Similarity	NPC470996
0.8874	High Similarity	NPC196846
0.8859	High Similarity	NPC470999
0.8851	High Similarity	NPC251865
0.8846	High Similarity	NPC69028
0.8844	High Similarity	NPC121158
0.8816	High Similarity	NPC291150
0.8816	High Similarity	NPC116717
0.8808	High Similarity	NPC470998
0.8792	High Similarity	NPC34056
0.879	High Similarity	NPC469338
0.879	High Similarity	NPC292389
0.8784	High Similarity	NPC243577
0.8774	High Similarity	NPC470118
0.8774	High Similarity	NPC469847
0.8758	High Similarity	NPC471002
0.875	High Similarity	NPC156189
0.875	High Similarity	NPC159927
0.875	High Similarity	NPC469335
0.875	High Similarity	NPC5180
0.8742	High Similarity	NPC478179
0.8734	High Similarity	NPC276551
0.8734	High Similarity	NPC470940
0.8734	High Similarity	NPC469849
0.8726	High Similarity	NPC329938
0.8718	High Similarity	NPC477403
0.871	High Similarity	NPC104736
0.871	High Similarity	NPC41880
0.8701	High Similarity	NPC30222
0.8696	High Similarity	NPC285227
0.8693	High Similarity	NPC471000
0.8679	High Similarity	NPC470875
0.8679	High Similarity	NPC478178
0.8671	High Similarity	NPC477405
0.8662	High Similarity	NPC470789
0.8662	High Similarity	NPC477402
0.8662	High Similarity	NPC25255
0.8658	High Similarity	NPC267632
0.8654	High Similarity	NPC472772
0.8654	High Similarity	NPC249021
0.8654	High Similarity	NPC472283
0.8654	High Similarity	NPC304692
0.8645	High Similarity	NPC214541
0.8645	High Similarity	NPC44675
0.8645	High Similarity	NPC264943
0.8645	High Similarity	NPC35000
0.8636	High Similarity	NPC75906
0.8636	High Similarity	NPC472672
0.8636	High Similarity	NPC469503
0.8634	High Similarity	NPC470995
0.8627	High Similarity	NPC212257
0.8627	High Similarity	NPC477404
0.8627	High Similarity	NPC196864
0.8625	High Similarity	NPC476861
0.8625	High Similarity	NPC476850
0.8625	High Similarity	NPC173516
0.8616	High Similarity	NPC123088
0.8616	High Similarity	NPC476858
0.8616	High Similarity	NPC476856
0.8616	High Similarity	NPC476857
0.8609	High Similarity	NPC262198
0.8608	High Similarity	NPC470792
0.8608	High Similarity	NPC5079
0.8608	High Similarity	NPC193798
0.859	High Similarity	NPC469485
0.8581	High Similarity	NPC253201
0.8581	High Similarity	NPC67003
0.8581	High Similarity	NPC237259
0.8581	High Similarity	NPC302054
0.8581	High Similarity	NPC34421
0.8581	High Similarity	NPC98206
0.8571	High Similarity	NPC471397
0.8562	High Similarity	NPC475779
0.8562	High Similarity	NPC470790
0.8562	High Similarity	NPC149945
0.8562	High Similarity	NPC470791
0.8562	High Similarity	NPC195325
0.8553	High Similarity	NPC51568
0.8553	High Similarity	NPC255414
0.8553	High Similarity	NPC165218
0.8553	High Similarity	NPC234660
0.8544	High Similarity	NPC287559
0.8542	High Similarity	NPC471817
0.8535	High Similarity	NPC261597
0.8535	High Similarity	NPC81405
0.8535	High Similarity	NPC173544
0.8526	High Similarity	NPC469850
0.8526	High Similarity	NPC281258
0.8516	High Similarity	NPC294511
0.8516	High Similarity	NPC121615
0.8514	High Similarity	NPC90953
0.8509	High Similarity	NPC472282
0.8509	High Similarity	NPC476853
0.8509	High Similarity	NPC472774
0.8509	High Similarity	NPC472775
0.85	High Similarity	NPC476860
0.8497	Intermediate Similarity	NPC93666
0.8497	Intermediate Similarity	NPC471007
0.8491	Intermediate Similarity	NPC471003
0.8491	Intermediate Similarity	NPC82851
0.8491	Intermediate Similarity	NPC472767
0.8491	Intermediate Similarity	NPC472771
0.8491	Intermediate Similarity	NPC263432
0.8491	Intermediate Similarity	NPC68848
0.8487	Intermediate Similarity	NPC346
0.8485	Intermediate Similarity	NPC478177
0.8481	Intermediate Similarity	NPC475226
0.8481	Intermediate Similarity	NPC140952
0.8481	Intermediate Similarity	NPC475967
0.8477	Intermediate Similarity	NPC476944
0.8477	Intermediate Similarity	NPC142113
0.8476	Intermediate Similarity	NPC471437
0.8472	Intermediate Similarity	NPC89133
0.8471	Intermediate Similarity	NPC209364
0.8471	Intermediate Similarity	NPC60973
0.8462	Intermediate Similarity	NPC57998
0.8462	Intermediate Similarity	NPC282445
0.8457	Intermediate Similarity	NPC160651
0.8456	Intermediate Similarity	NPC90296
0.8456	Intermediate Similarity	NPC148374
0.8447	Intermediate Similarity	NPC23387
0.8446	Intermediate Similarity	NPC471996
0.8442	Intermediate Similarity	NPC69647
0.8442	Intermediate Similarity	NPC125182
0.8438	Intermediate Similarity	NPC419
0.8438	Intermediate Similarity	NPC285567
0.8438	Intermediate Similarity	NPC283209
0.8438	Intermediate Similarity	NPC472773
0.8435	Intermediate Similarity	NPC46896
0.8431	Intermediate Similarity	NPC250228
0.8431	Intermediate Similarity	NPC71821
0.8428	Intermediate Similarity	NPC335761
0.8428	Intermediate Similarity	NPC472653
0.8428	Intermediate Similarity	NPC191828
0.8424	Intermediate Similarity	NPC167340
0.8418	Intermediate Similarity	NPC214495
0.8418	Intermediate Similarity	NPC187149
0.8418	Intermediate Similarity	NPC36655
0.8418	Intermediate Similarity	NPC475066
0.8418	Intermediate Similarity	NPC470119
0.8418	Intermediate Similarity	NPC286722
0.8415	Intermediate Similarity	NPC469848
0.8414	Intermediate Similarity	NPC471995
0.8408	Intermediate Similarity	NPC75310
0.8397	Intermediate Similarity	NPC268905
0.8389	Intermediate Similarity	NPC202260
0.8387	Intermediate Similarity	NPC46551
0.8387	Intermediate Similarity	NPC228842
0.8385	Intermediate Similarity	NPC472664
0.8378	Intermediate Similarity	NPC42400
0.8378	Intermediate Similarity	NPC310043
0.8375	Intermediate Similarity	NPC6326
0.8375	Intermediate Similarity	NPC470939
0.8375	Intermediate Similarity	NPC18986
0.8367	Intermediate Similarity	NPC158525
0.8366	Intermediate Similarity	NPC233763
0.8365	Intermediate Similarity	NPC472671
0.8365	Intermediate Similarity	NPC473473
0.8365	Intermediate Similarity	NPC474932
0.8365	Intermediate Similarity	NPC307383
0.8365	Intermediate Similarity	NPC475295
0.8365	Intermediate Similarity	NPC84349
0.8365	Intermediate Similarity	NPC237155
0.8365	Intermediate Similarity	NPC474611
0.8364	Intermediate Similarity	NPC94763
0.8364	Intermediate Similarity	NPC236004
0.8356	Intermediate Similarity	NPC471006
0.8354	Intermediate Similarity	NPC204663
0.8354	Intermediate Similarity	NPC107646
0.8354	Intermediate Similarity	NPC263265
0.8345	Intermediate Similarity	NPC61788
0.8345	Intermediate Similarity	NPC298190
0.8344	Intermediate Similarity	NPC473152
0.8344	Intermediate Similarity	NPC263337
0.8343	Intermediate Similarity	NPC242068

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 NPC272590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	940
0.2-0.3	1927
0.3-0.4	2620
0.4-0.5	2071
0.5-0.6	994
0.6-0.7	302
0.7-0.8	18
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8408	Intermediate Similarity	NPD5760	Phase 2
0.8408	Intermediate Similarity	NPD5761	Phase 2
0.8204	Intermediate Similarity	NPD6765	Approved
0.8204	Intermediate Similarity	NPD6764	Approved
0.807	Intermediate Similarity	NPD8434	Phase 2
0.8012	Intermediate Similarity	NPD6785	Approved
0.8012	Intermediate Similarity	NPD6784	Approved
0.7975	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1471	Phase 3
0.7564	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD6273	Approved
0.7329	Intermediate Similarity	NPD7236	Approved
0.7273	Intermediate Similarity	NPD3226	Approved
0.7202	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6599	Discontinued
0.7111	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7239	Suspended
0.7107	Intermediate Similarity	NPD2799	Discontinued
0.7076	Intermediate Similarity	NPD7075	Discontinued
0.7066	Intermediate Similarity	NPD7458	Discontinued
0.7052	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD2346	Discontinued
0.7019	Intermediate Similarity	NPD2344	Approved
0.7006	Intermediate Similarity	NPD8032	Phase 2
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7411	Suspended
0.6959	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD920	Approved
0.6943	Remote Similarity	NPD3268	Approved
0.6919	Remote Similarity	NPD8404	Phase 2
0.6914	Remote Similarity	NPD5762	Approved
0.6914	Remote Similarity	NPD5763	Approved
0.689	Remote Similarity	NPD3750	Approved
0.689	Remote Similarity	NPD7003	Approved
0.6879	Remote Similarity	NPD3749	Approved
0.6867	Remote Similarity	NPD6799	Approved
0.6864	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1608	Approved
0.6855	Remote Similarity	NPD4140	Approved
0.6854	Remote Similarity	NPD7799	Discontinued
0.6848	Remote Similarity	NPD2309	Approved
0.6842	Remote Similarity	NPD6801	Discontinued
0.6839	Remote Similarity	NPD919	Approved
0.6835	Remote Similarity	NPD2313	Discontinued
0.6826	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6808	Phase 2
0.6807	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6559	Discontinued
0.679	Remote Similarity	NPD3748	Approved
0.678	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1876	Approved
0.6761	Remote Similarity	NPD1247	Approved
0.6753	Remote Similarity	NPD3972	Approved
0.6748	Remote Similarity	NPD6100	Approved
0.6748	Remote Similarity	NPD6099	Approved
0.6748	Remote Similarity	NPD2796	Approved
0.6742	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3267	Approved
0.6731	Remote Similarity	NPD3266	Approved
0.673	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3764	Approved
0.673	Remote Similarity	NPD6798	Discontinued
0.6726	Remote Similarity	NPD2533	Approved
0.6726	Remote Similarity	NPD2534	Approved
0.6726	Remote Similarity	NPD2532	Approved
0.6725	Remote Similarity	NPD7028	Phase 2
0.6724	Remote Similarity	NPD7057	Phase 3
0.6724	Remote Similarity	NPD7058	Phase 2
0.6724	Remote Similarity	NPD3882	Suspended
0.6722	Remote Similarity	NPD5844	Phase 1
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5494	Approved
0.6704	Remote Similarity	NPD7473	Discontinued
0.6687	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD8166	Discontinued
0.6687	Remote Similarity	NPD4110	Phase 3
0.6687	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7199	Phase 2
0.6649	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3887	Approved
0.6646	Remote Similarity	NPD1551	Phase 2
0.6629	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7768	Phase 2
0.6629	Remote Similarity	NPD7229	Phase 3
0.6627	Remote Similarity	NPD2800	Approved
0.6627	Remote Similarity	NPD1243	Approved
0.6624	Remote Similarity	NPD2797	Approved
0.6609	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5735	Approved
0.6604	Remote Similarity	NPD6832	Phase 2
0.6592	Remote Similarity	NPD3926	Phase 2
0.6585	Remote Similarity	NPD7033	Discontinued
0.6585	Remote Similarity	NPD4308	Phase 3
0.6584	Remote Similarity	NPD7961	Discontinued
0.6582	Remote Similarity	NPD2798	Approved
0.6575	Remote Similarity	NPD7177	Discontinued
0.6571	Remote Similarity	NPD5402	Approved
0.6566	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6353	Approved
0.6562	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1283	Approved
0.655	Remote Similarity	NPD5403	Approved
0.6548	Remote Similarity	NPD2354	Approved
0.6546	Remote Similarity	NPD4482	Phase 3
0.6545	Remote Similarity	NPD2935	Discontinued
0.6543	Remote Similarity	NPD4060	Phase 1
0.6541	Remote Similarity	NPD5736	Approved
0.6541	Remote Similarity	NPD8313	Approved
0.6541	Remote Similarity	NPD8312	Approved
0.6536	Remote Similarity	NPD6232	Discontinued
0.6534	Remote Similarity	NPD4967	Phase 2
0.6534	Remote Similarity	NPD4966	Approved
0.6534	Remote Similarity	NPD4965	Approved
0.6529	Remote Similarity	NPD5401	Approved
0.6524	Remote Similarity	NPD7097	Phase 1
0.6519	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD3057	Approved
0.6497	Remote Similarity	NPD5327	Phase 3
0.6485	Remote Similarity	NPD1510	Phase 2
0.6484	Remote Similarity	NPD3818	Discontinued
0.6481	Remote Similarity	NPD6233	Phase 2
0.648	Remote Similarity	NPD6959	Discontinued
0.648	Remote Similarity	NPD7497	Discontinued
0.6478	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4534	Discontinued
0.6464	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6234	Discontinued
0.6457	Remote Similarity	NPD6279	Approved
0.6457	Remote Similarity	NPD1934	Approved
0.6457	Remote Similarity	NPD6280	Approved
0.6457	Remote Similarity	NPD37	Approved
0.6455	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4476	Approved
0.6446	Remote Similarity	NPD4477	Approved
0.6444	Remote Similarity	NPD7315	Approved
0.6442	Remote Similarity	NPD2979	Phase 3
0.6442	Remote Similarity	NPD4307	Phase 2
0.6437	Remote Similarity	NPD4380	Phase 2
0.6436	Remote Similarity	NPD8150	Discontinued
0.6433	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7685	Pre-registration
0.6429	Remote Similarity	NPD9545	Approved
0.6429	Remote Similarity	NPD3533	Approved
0.6429	Remote Similarity	NPD2972	Approved
0.6424	Remote Similarity	NPD1241	Discontinued
0.6417	Remote Similarity	NPD8407	Phase 2
0.641	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2353	Approved
0.6407	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5049	Phase 3
0.6393	Remote Similarity	NPD2163	Approved
0.6393	Remote Similarity	NPD3751	Discontinued
0.6391	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5585	Approved
0.6384	Remote Similarity	NPD2296	Approved
0.638	Remote Similarity	NPD4062	Phase 3
0.6378	Remote Similarity	NPD5953	Discontinued
0.6375	Remote Similarity	NPD5647	Approved
0.6374	Remote Similarity	NPD6166	Phase 2
0.6374	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5958	Discontinued
0.6369	Remote Similarity	NPD1281	Approved
0.6364	Remote Similarity	NPD1607	Approved
0.6352	Remote Similarity	NPD3225	Approved
0.6347	Remote Similarity	NPD2438	Suspended
0.6346	Remote Similarity	NPD2932	Approved
0.6345	Remote Similarity	NPD2491	Approved
0.6344	Remote Similarity	NPD8368	Discontinued
0.6341	Remote Similarity	NPD1240	Approved
0.6333	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD9717	Approved
0.6328	Remote Similarity	NPD2801	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