NPASS Compound

Structure

CID663 OpenBabel06191715322D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.7919 1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9388 -1.4443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9389 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5013 -2.4549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0306 -0.9924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5319 0.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6883 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2196 -3.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7694 -0.1854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3758 -2.9241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 -1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3420 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2202 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8437 -1.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3494 1.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8434 -0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5319 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2202 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6878 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0637 -2.9236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3760 -0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0640 -1.9494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3761 -1.9498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8441 -0.4874 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5319 -0.4877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8803 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9324 -3.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8680 1.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7699 -1.7609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3760 0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 33 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 33 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 28 1 0 0 0 0 18 25 1 6 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 25 1 6 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 28 1 0 0 0 0 22 31 2 0 0 0 0 23 27 1 1 0 0 0 23 34 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 6 0 0 0 27 6 1 6 0 0 0 28 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.24
Volume:	484.348
LogP:	2.644
LogD:	2.095
LogS:	-4.636
# Rotatable Bonds:	3
TPSA:	93.81
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	5.114
Fsp3:	0.607
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:	-5.22
MDCK Permeability:	2.926446177298203e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	86.2693862915039%
Volume Distribution (VD):	2.262
Pgp-substrate:	9.705434799194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.252
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.697
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	2.469
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.398
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.786
Carcinogencity:	0.207
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC663

Natural Product ID:	NPC663
*Common Name:**	17-Epi-17-Hydroxyazadiradione
IUPAC Name:	[(5R,7R,8R,9R,10R,13R,17R)-17-(furan-3-yl)-17-hydroxy-4,4,8,10,13-pentamethyl-3,16-dioxo-5,6,7,9,11,12-hexahydrocyclopenta[a]phenanthren-7-yl] acetate
Synonyms:
Standard InCHIKey:	QXKHBVSTPRHRQV-CMBOGFGBSA-N
Standard InCHI:	InChI=1S/C28H34O6/c1-16(29)34-23-14-19-24(2,3)21(30)8-10-25(19,4)18-7-11-26(5)20(27(18,23)6)13-22(31)28(26,32)17-9-12-33-15-17/h8-10,12-13,15,18-19,23,32H,7,11,14H2,1-6H3/t18-,19+,23-,25-,26-,27-,28-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC(=O)[C@]([C@@]1(CC3)C)(O)c1ccoc1)(C)C=CC(=O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774393
PubChem CID:	52951894
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.	bark	n.a.	PMID[9134742]
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.	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[448123]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[448123]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[448123]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19100.0	nM	PMID[448123]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[448123]

☑ 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 NPC663 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	341
0.1-0.2	1380
0.2-0.3	2990
0.3-0.4	5612
0.4-0.5	10623
0.5-0.6	9957
0.6-0.7	8659
0.7-0.8	2652
0.8-0.85	269
0.85-0.9	178
0.9-0.95	34
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224394
0.9408	High Similarity	NPC272590
0.9299	High Similarity	NPC197596
0.9187	High Similarity	NPC478179
0.9182	High Similarity	NPC470940
0.9177	High Similarity	NPC329938
0.9172	High Similarity	NPC477403
0.9161	High Similarity	NPC178932
0.915	High Similarity	NPC472654
0.9125	High Similarity	NPC478178
0.9125	High Similarity	NPC149945
0.9119	High Similarity	NPC469338
0.9119	High Similarity	NPC292389
0.9114	High Similarity	NPC477402
0.9108	High Similarity	NPC249021
0.9103	High Similarity	NPC92979
0.9103	High Similarity	NPC469336
0.9097	High Similarity	NPC246164
0.9062	High Similarity	NPC469849
0.9062	High Similarity	NPC276551
0.9057	High Similarity	NPC69028
0.9057	High Similarity	NPC193798
0.9045	High Similarity	NPC469485
0.9038	High Similarity	NPC30222
0.903	High Similarity	NPC478177
0.9024	High Similarity	NPC471437
0.902	High Similarity	NPC471174
0.9018	High Similarity	NPC285227
0.9006	High Similarity	NPC470875
0.9	High Similarity	NPC477405
0.9	High Similarity	NPC165218
0.8994	High Similarity	NPC25255
0.8987	High Similarity	NPC261597
0.8987	High Similarity	NPC173544
0.8987	High Similarity	NPC472772
0.8981	High Similarity	NPC35000
0.8981	High Similarity	NPC214541
0.8981	High Similarity	NPC44675
0.8981	High Similarity	NPC264943
0.8974	High Similarity	NPC75906
0.8968	High Similarity	NPC477404
0.8968	High Similarity	NPC156189
0.8968	High Similarity	NPC196864
0.8968	High Similarity	NPC159927
0.8968	High Similarity	NPC469335
0.8954	High Similarity	NPC471292
0.8951	High Similarity	NPC173516
0.8951	High Similarity	NPC476861
0.8951	High Similarity	NPC476850
0.8947	High Similarity	NPC238843
0.8947	High Similarity	NPC199044
0.8944	High Similarity	NPC476856
0.8944	High Similarity	NPC476857
0.8944	High Similarity	NPC123088
0.8944	High Similarity	NPC476858
0.8938	High Similarity	NPC472767
0.8938	High Similarity	NPC5079
0.8938	High Similarity	NPC82851
0.8917	High Similarity	NPC282445
0.8896	High Similarity	NPC471397
0.8896	High Similarity	NPC216755
0.8889	High Similarity	NPC185456
0.8882	High Similarity	NPC234660
0.8882	High Similarity	NPC51568
0.8875	High Similarity	NPC470789
0.8868	High Similarity	NPC472283
0.8868	High Similarity	NPC470118
0.8868	High Similarity	NPC36655
0.8861	High Similarity	NPC469850
0.8854	High Similarity	NPC469503
0.8854	High Similarity	NPC33938
0.8846	High Similarity	NPC470997
0.8841	High Similarity	NPC470995
0.8834	High Similarity	NPC472774
0.8834	High Similarity	NPC476853
0.8834	High Similarity	NPC472775
0.8834	High Similarity	NPC472282
0.8831	High Similarity	NPC346
0.8827	High Similarity	NPC476860
0.882	High Similarity	NPC263432
0.882	High Similarity	NPC6326
0.882	High Similarity	NPC472771
0.8812	High Similarity	NPC475967
0.8805	High Similarity	NPC60973
0.8805	High Similarity	NPC204663
0.8805	High Similarity	NPC209364
0.8797	High Similarity	NPC57998
0.8795	High Similarity	NPC94763
0.8795	High Similarity	NPC236004
0.8782	High Similarity	NPC470790
0.8782	High Similarity	NPC470791
0.8782	High Similarity	NPC470998
0.8782	High Similarity	NPC195325
0.878	High Similarity	NPC160651
0.8774	High Similarity	NPC250228
0.8773	High Similarity	NPC23387
0.8773	High Similarity	NPC214600
0.8765	High Similarity	NPC419
0.8765	High Similarity	NPC472773
0.8758	High Similarity	NPC267632
0.8758	High Similarity	NPC472653
0.8758	High Similarity	NPC335761
0.8758	High Similarity	NPC191828
0.875	High Similarity	NPC187149
0.875	High Similarity	NPC286722
0.875	High Similarity	NPC195131
0.8743	High Similarity	NPC167340
0.8742	High Similarity	NPC141538
0.8742	High Similarity	NPC296807
0.8742	High Similarity	NPC155939
0.8735	High Similarity	NPC469848
0.872	High Similarity	NPC472764
0.871	High Similarity	NPC262198
0.8704	High Similarity	NPC470939
0.8701	High Similarity	NPC476944
0.8701	High Similarity	NPC251865
0.8696	High Similarity	NPC474932
0.8696	High Similarity	NPC473473
0.8696	High Similarity	NPC475295
0.8696	High Similarity	NPC237155
0.8693	High Similarity	NPC121158
0.8688	High Similarity	NPC104736
0.8688	High Similarity	NPC41880
0.8688	High Similarity	NPC107646
0.8688	High Similarity	NPC263265
0.8684	High Similarity	NPC56197
0.8683	High Similarity	NPC469576
0.8683	High Similarity	NPC471632
0.8667	High Similarity	NPC472766
0.8667	High Similarity	NPC472765
0.8662	High Similarity	NPC471001
0.8662	High Similarity	NPC234494
0.8655	High Similarity	NPC242068
0.8655	High Similarity	NPC247563
0.8654	High Similarity	NPC302987
0.8654	High Similarity	NPC221809
0.865	High Similarity	NPC39986
0.865	High Similarity	NPC134254
0.865	High Similarity	NPC302369
0.8642	High Similarity	NPC305016
0.8642	High Similarity	NPC287559
0.8636	High Similarity	NPC243577
0.8634	High Similarity	NPC45101
0.8634	High Similarity	NPC469847
0.8634	High Similarity	NPC81405
0.8634	High Similarity	NPC197137
0.8634	High Similarity	NPC304692
0.8634	High Similarity	NPC299038
0.8634	High Similarity	NPC167142
0.8631	High Similarity	NPC469633
0.8625	High Similarity	NPC281258
0.8625	High Similarity	NPC75310
0.8616	High Similarity	NPC44577
0.8608	High Similarity	NPC476122
0.8606	High Similarity	NPC473766
0.8606	High Similarity	NPC472651
0.8606	High Similarity	NPC476224
0.8606	High Similarity	NPC473753
0.8598	High Similarity	NPC261184
0.8598	High Similarity	NPC470182
0.8589	High Similarity	NPC200782
0.8589	High Similarity	NPC96443
0.8589	High Similarity	NPC471167
0.8589	High Similarity	NPC471166
0.8589	High Similarity	NPC149896
0.8589	High Similarity	NPC290400
0.8589	High Similarity	NPC117986
0.8589	High Similarity	NPC470792
0.8581	High Similarity	NPC142113
0.858	High Similarity	NPC475226
0.858	High Similarity	NPC474611
0.858	High Similarity	NPC307383
0.858	High Similarity	NPC140952
0.8571	High Similarity	NPC126723
0.8563	High Similarity	NPC159232
0.8554	High Similarity	NPC327922
0.8554	High Similarity	NPC271235
0.8554	High Similarity	NPC472652
0.8553	High Similarity	NPC116717
0.8553	High Similarity	NPC18135
0.8547	High Similarity	NPC105395
0.8545	High Similarity	NPC121995
0.8545	High Similarity	NPC475779
0.8544	High Similarity	NPC211625
0.8537	High Similarity	NPC88841
0.8537	High Similarity	NPC471168
0.8537	High Similarity	NPC288602
0.8535	High Similarity	NPC255414
0.8535	High Similarity	NPC470941
0.8528	High Similarity	NPC475381
0.8526	High Similarity	NPC41182
0.8519	High Similarity	NPC472776
0.8519	High Similarity	NPC472777
0.8519	High Similarity	NPC472778
0.8516	High Similarity	NPC223415
0.8509	High Similarity	NPC472785
0.8506	High Similarity	NPC205765
0.8503	High Similarity	NPC82602
0.85	High Similarity	NPC470996
0.85	High Similarity	NPC472672

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 NPC663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	998
0.2-0.3	2019
0.3-0.4	2647
0.4-0.5	1943
0.5-0.6	923
0.6-0.7	282
0.7-0.8	40
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8981	High Similarity	NPD5761	Phase 2
0.8981	High Similarity	NPD5760	Phase 2
0.8382	Intermediate Similarity	NPD8434	Phase 2
0.8193	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6764	Approved
0.8092	Intermediate Similarity	NPD6765	Approved
0.791	Intermediate Similarity	NPD6785	Approved
0.791	Intermediate Similarity	NPD6784	Approved
0.7396	Intermediate Similarity	NPD3226	Approved
0.7362	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD7236	Approved
0.7326	Intermediate Similarity	NPD7819	Suspended
0.7326	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6599	Discontinued
0.7229	Intermediate Similarity	NPD4628	Phase 3
0.7209	Intermediate Similarity	NPD7411	Suspended
0.72	Intermediate Similarity	NPD3749	Approved
0.72	Intermediate Similarity	NPD8404	Phase 2
0.7184	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD920	Approved
0.7167	Intermediate Similarity	NPD7799	Discontinued
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7239	Suspended
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6273	Approved
0.7104	Intermediate Similarity	NPD6559	Discontinued
0.7072	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6801	Discontinued
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7059	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD6799	Approved
0.6983	Remote Similarity	NPD1247	Approved
0.6966	Remote Similarity	NPD919	Approved
0.6964	Remote Similarity	NPD2800	Approved
0.6961	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3882	Suspended
0.6946	Remote Similarity	NPD2344	Approved
0.6946	Remote Similarity	NPD2346	Discontinued
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2799	Discontinued
0.6927	Remote Similarity	NPD5494	Approved
0.6923	Remote Similarity	NPD3750	Approved
0.6905	Remote Similarity	NPD1549	Phase 2
0.6893	Remote Similarity	NPD5402	Approved
0.6893	Remote Similarity	NPD3817	Phase 2
0.6889	Remote Similarity	NPD8127	Discontinued
0.6886	Remote Similarity	NPD1551	Phase 2
0.6886	Remote Similarity	NPD6100	Approved
0.6886	Remote Similarity	NPD2796	Approved
0.6886	Remote Similarity	NPD6099	Approved
0.6871	Remote Similarity	NPD3268	Approved
0.6854	Remote Similarity	NPD7768	Phase 2
0.6851	Remote Similarity	NPD6232	Discontinued
0.6848	Remote Similarity	NPD5844	Phase 1
0.6845	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6002	Phase 3
0.6845	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6005	Phase 3
0.6845	Remote Similarity	NPD6004	Phase 3
0.6845	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7033	Discontinued
0.6825	Remote Similarity	NPD8150	Discontinued
0.6805	Remote Similarity	NPD970	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7458	Discontinued
0.68	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6959	Discontinued
0.6793	Remote Similarity	NPD3818	Discontinued
0.6793	Remote Similarity	NPD3751	Discontinued
0.6786	Remote Similarity	NPD2935	Discontinued
0.6784	Remote Similarity	NPD2309	Approved
0.6782	Remote Similarity	NPD5403	Approved
0.678	Remote Similarity	NPD1934	Approved
0.6768	Remote Similarity	NPD2313	Discontinued
0.6765	Remote Similarity	NPD1243	Approved
0.6763	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4380	Phase 2
0.676	Remote Similarity	NPD7057	Phase 3
0.676	Remote Similarity	NPD7058	Phase 2
0.676	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6808	Phase 2
0.6757	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD8312	Approved
0.6755	Remote Similarity	NPD8313	Approved
0.6746	Remote Similarity	NPD5762	Approved
0.6746	Remote Similarity	NPD5763	Approved
0.6726	Remote Similarity	NPD3748	Approved
0.6726	Remote Similarity	NPD1510	Phase 2
0.6722	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3926	Phase 2
0.6721	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6166	Phase 2
0.6685	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7685	Pre-registration
0.6648	Remote Similarity	NPD2801	Approved
0.6647	Remote Similarity	NPD6355	Discontinued
0.6646	Remote Similarity	NPD6832	Phase 2
0.6632	Remote Similarity	NPD8407	Phase 2
0.6629	Remote Similarity	NPD1512	Approved
0.6628	Remote Similarity	NPD7003	Approved
0.6628	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8032	Phase 2
0.6627	Remote Similarity	NPD4308	Phase 3
0.6626	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7199	Phase 2
0.6607	Remote Similarity	NPD1607	Approved
0.66	Remote Similarity	NPD7497	Discontinued
0.6596	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5953	Discontinued
0.6593	Remote Similarity	NPD6234	Discontinued
0.6592	Remote Similarity	NPD37	Approved
0.6587	Remote Similarity	NPD4140	Approved
0.6587	Remote Similarity	NPD1240	Approved
0.6584	Remote Similarity	NPD1608	Approved
0.658	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7286	Phase 2
0.6576	Remote Similarity	NPD5711	Approved
0.6576	Remote Similarity	NPD5710	Approved
0.6573	Remote Similarity	NPD7028	Phase 2
0.6564	Remote Similarity	NPD3266	Approved
0.6564	Remote Similarity	NPD2797	Approved
0.6564	Remote Similarity	NPD3267	Approved
0.6561	Remote Similarity	NPD7251	Discontinued
0.6561	Remote Similarity	NPD8368	Discontinued
0.6543	Remote Similarity	NPD7074	Phase 3
0.6533	Remote Similarity	NPD6779	Approved
0.6533	Remote Similarity	NPD6781	Approved
0.6533	Remote Similarity	NPD6780	Approved
0.6533	Remote Similarity	NPD6778	Approved
0.6533	Remote Similarity	NPD6782	Approved
0.6533	Remote Similarity	NPD6776	Approved
0.6533	Remote Similarity	NPD6777	Approved
0.6527	Remote Similarity	NPD6663	Approved
0.6526	Remote Similarity	NPD7808	Phase 3
0.6517	Remote Similarity	NPD7697	Approved
0.6517	Remote Similarity	NPD7696	Phase 3
0.6517	Remote Similarity	NPD7698	Approved
0.6514	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD1511	Approved
0.6509	Remote Similarity	NPD6651	Approved
0.6508	Remote Similarity	NPD6797	Phase 2
0.6505	Remote Similarity	NPD2403	Approved
0.6493	Remote Similarity	NPD7907	Approved
0.6489	Remote Similarity	NPD7054	Approved
0.6488	Remote Similarity	NPD7874	Approved
0.6488	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3787	Discontinued
0.6485	Remote Similarity	NPD7870	Phase 2
0.6485	Remote Similarity	NPD7871	Phase 2
0.6482	Remote Similarity	NPD8285	Discontinued
0.6481	Remote Similarity	NPD9717	Approved
0.6476	Remote Similarity	NPD4111	Phase 1
0.6476	Remote Similarity	NPD4665	Approved
0.6467	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1203	Approved
0.6455	Remote Similarity	NPD7472	Approved
0.645	Remote Similarity	NPD4107	Approved
0.645	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.645	Remote Similarity	NPD447	Suspended
0.6444	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.644	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD8166	Discontinued
0.6436	Remote Similarity	NPD7177	Discontinued
0.6436	Remote Similarity	NPD7228	Approved
0.6432	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7961	Discontinued
0.6424	Remote Similarity	NPD2798	Approved
0.6424	Remote Similarity	NPD5647	Approved
0.6412	Remote Similarity	NPD6353	Approved
0.641	Remote Similarity	NPD8360	Approved
0.641	Remote Similarity	NPD4287	Approved
0.641	Remote Similarity	NPD8361	Approved
0.6407	Remote Similarity	NPD7095	Approved
0.6404	Remote Similarity	NPD8320	Phase 1
0.6404	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8319	Approved
0.6402	Remote Similarity	NPD1876	Approved
0.64	Remote Similarity	NPD3887	Approved
0.6398	Remote Similarity	NPD7315	Approved
0.6398	Remote Similarity	NPD17	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