NPASS Compound

Structure

NPC470939 OpenBabel07101719522D 39 44 0 0 1 0 0 0 0 0999 V2000 -4.2339 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0292 -1.5977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5181 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2804 -0.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9346 -1.3067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4893 -1.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 -3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6936 -1.9556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8468 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 -3.4222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 -3.4222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5403 -0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8468 0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6936 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 -2.4444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8468 -0.4889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0807 -3.9111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -5.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 1.9556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4457 -2.1535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 -3.9111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 0.4889 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 27 1 0 0 0 0 11 35 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 35 1 0 0 0 0 15 31 2 0 0 0 0 15 36 1 0 0 0 0 16 32 2 0 0 0 0 16 37 1 0 0 0 0 17 23 1 0 0 0 0 18 28 1 6 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 6 0 0 0 20 29 1 0 0 0 0 20 33 2 0 0 0 0 21 26 1 0 0 0 0 21 36 1 1 0 0 0 22 28 1 1 0 0 0 22 37 1 0 0 0 0 23 27 1 6 0 0 0 23 38 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 1 0 0 0 24 39 1 0 0 0 0 25 34 2 0 0 0 0 25 38 1 0 0 0 0 27 30 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.25
Volume:	539.391
LogP:	3.941
LogD:	2.958
LogS:	-4.93
# Rotatable Bonds:	5
TPSA:	121.64
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	5.641
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.251
MDCK Permeability:	5.35627368662972e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.836
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	73.92095947265625%
Volume Distribution (VD):	1.658
Pgp-substrate:	24.096315383911133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.523
CYP2C9-inhibitor:	0.297
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.493

ADMET: Excretion

Clearance (CL):	7.171
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.768
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.2
Carcinogencity:	0.192
Eye Corrosion:	0.343
Eye Irritation:	0.196
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC470939

Natural Product ID:	NPC470939
*Common Name:**	IKFXPERBVFYFMS-VUUTWSBUSA-N
IUPAC Name:	n.a.
Synonyms:	7-Oxokhivorin
Standard InCHIKey:	IKFXPERBVFYFMS-VUUTWSBUSA-N
Standard InCHI:	InChI=1S/C30H38O9/c1-15(31)36-21-13-22(37-16(2)32)28(6)18-8-10-27(5)23(17-9-11-35-14-17)38-25(34)24-30(27,39-24)29(18,7)20(33)12-19(28)26(21,3)4/h9,11,14,18-19,21-24H,8,10,12-13H2,1-7H3/t18-,19+,21-,22+,23-,24-,27+,28-,29+,30-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@H](OC(=O)C)C([C@H]2[C@@]1(C)[C@H]1CC[C@@]3([C@]4([C@@]1(C(=O)C2)C)O[C@@H]4C(=O)O[C@@H]3c1ccoc1)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332196
PubChem CID:	71718205
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23210623]
NPO6774	Khaya senegalensis	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[561878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[561878]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[561878]

☑ 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 NPC470939 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	451
0.1-0.2	1667
0.2-0.3	3601
0.3-0.4	6683
0.4-0.5	10522
0.5-0.6	9654
0.6-0.7	8464
0.7-0.8	1335
0.8-0.85	188
0.85-0.9	59
0.9-0.95	60
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC107646
0.9673	High Similarity	NPC475381
0.9671	High Similarity	NPC286722
0.9608	High Similarity	NPC475295
0.9608	High Similarity	NPC473473
0.9608	High Similarity	NPC237155
0.9605	High Similarity	NPC209364
0.9605	High Similarity	NPC60973
0.9554	High Similarity	NPC160651
0.9548	High Similarity	NPC302369
0.9548	High Similarity	NPC39986
0.9548	High Similarity	NPC469846
0.9548	High Similarity	NPC134254
0.9548	High Similarity	NPC476197
0.9545	High Similarity	NPC25255
0.9545	High Similarity	NPC305016
0.9542	High Similarity	NPC472283
0.949	High Similarity	NPC473766
0.949	High Similarity	NPC472282
0.949	High Similarity	NPC473753
0.949	High Similarity	NPC173516
0.9487	High Similarity	NPC476857
0.9487	High Similarity	NPC476858
0.9487	High Similarity	NPC476856
0.9484	High Similarity	NPC193798
0.9477	High Similarity	NPC126723
0.9477	High Similarity	NPC263265
0.943	High Similarity	NPC471397
0.9419	High Similarity	NPC335761
0.9412	High Similarity	NPC469850
0.9367	High Similarity	NPC476861
0.9367	High Similarity	NPC476853
0.9367	High Similarity	NPC476850
0.9363	High Similarity	NPC476860
0.9363	High Similarity	NPC123088
0.9359	High Similarity	NPC5079
0.9308	High Similarity	NPC271235
0.9304	High Similarity	NPC23387
0.9299	High Similarity	NPC292389
0.9299	High Similarity	NPC469338
0.9299	High Similarity	NPC477405
0.9299	High Similarity	NPC234660
0.9299	High Similarity	NPC51568
0.9295	High Similarity	NPC472653
0.929	High Similarity	NPC167142
0.9281	High Similarity	NPC476201
0.9276	High Similarity	NPC469335
0.9276	High Similarity	NPC196864
0.9276	High Similarity	NPC477404
0.9276	High Similarity	NPC159927
0.9241	High Similarity	NPC469849
0.9241	High Similarity	NPC276551
0.9241	High Similarity	NPC470940
0.9236	High Similarity	NPC69028
0.9236	High Similarity	NPC263432
0.9236	High Similarity	NPC82851
0.9231	High Similarity	NPC477403
0.9182	High Similarity	NPC470875
0.9172	High Similarity	NPC191828
0.9167	High Similarity	NPC249021
0.9161	High Similarity	NPC476262
0.915	High Similarity	NPC46551
0.915	High Similarity	NPC476122
0.9139	High Similarity	NPC262198
0.9136	High Similarity	NPC469848
0.913	High Similarity	NPC302392
0.9125	High Similarity	NPC472774
0.9125	High Similarity	NPC472775
0.9114	High Similarity	NPC329938
0.9114	High Similarity	NPC472771
0.9114	High Similarity	NPC290400
0.9114	High Similarity	NPC117986
0.9114	High Similarity	NPC96443
0.9108	High Similarity	NPC473368
0.9091	High Similarity	NPC18135
0.9057	High Similarity	NPC472773
0.9051	High Similarity	NPC477402
0.9045	High Similarity	NPC472772
0.9038	High Similarity	NPC469336
0.9006	High Similarity	NPC472651
0.9	High Similarity	NPC271657
0.8994	High Similarity	NPC18347
0.8994	High Similarity	NPC197596
0.8994	High Similarity	NPC149896
0.8974	High Similarity	NPC282445
0.8974	High Similarity	NPC178932
0.8954	High Similarity	NPC221809
0.8951	High Similarity	NPC472652
0.8924	High Similarity	NPC187149
0.8924	High Similarity	NPC299038
0.8917	High Similarity	NPC264943
0.891	High Similarity	NPC469503
0.8896	High Similarity	NPC470995
0.8889	High Similarity	NPC476224
0.8882	High Similarity	NPC86935
0.8875	High Similarity	NPC200782
0.8875	High Similarity	NPC471166
0.8875	High Similarity	NPC6326
0.8875	High Similarity	NPC471167
0.8868	High Similarity	NPC475967
0.8861	High Similarity	NPC469485
0.8831	High Similarity	NPC470941
0.8827	High Similarity	NPC475779
0.882	High Similarity	NPC471168
0.8805	High Similarity	NPC45101
0.8805	High Similarity	NPC261597
0.8805	High Similarity	NPC36655
0.8805	High Similarity	NPC173544
0.8797	High Similarity	NPC214541
0.8797	High Similarity	NPC281258
0.8797	High Similarity	NPC44675
0.879	High Similarity	NPC75906
0.8765	High Similarity	NPC470182
0.8758	High Similarity	NPC472668
0.8758	High Similarity	NPC188649
0.8758	High Similarity	NPC142113
0.875	High Similarity	NPC307383
0.8743	High Similarity	NPC478177
0.8742	High Similarity	NPC204663
0.8727	High Similarity	NPC169299
0.8727	High Similarity	NPC160818
0.872	High Similarity	NPC327922
0.8712	High Similarity	NPC121995
0.8706	High Similarity	NPC105395
0.8704	High Similarity	NPC224394
0.8704	High Similarity	NPC419
0.8704	High Similarity	NPC88841
0.8704	High Similarity	NPC288602
0.8704	High Similarity	NPC475039
0.8704	High Similarity	NPC476035
0.8704	High Similarity	NPC663
0.8704	High Similarity	NPC472669
0.8704	High Similarity	NPC14499
0.8688	High Similarity	NPC195131
0.8688	High Similarity	NPC469847
0.8683	High Similarity	NPC167340
0.8683	High Similarity	NPC262386
0.8667	High Similarity	NPC82602
0.8662	High Similarity	NPC156189
0.8659	High Similarity	NPC270312
0.8654	High Similarity	NPC19747
0.8642	High Similarity	NPC207978
0.8642	High Similarity	NPC18986
0.8642	High Similarity	NPC68848
0.8634	High Similarity	NPC474611
0.8625	High Similarity	NPC41880
0.8623	High Similarity	NPC236004
0.8623	High Similarity	NPC471437
0.8616	High Similarity	NPC30222
0.8616	High Similarity	NPC57998
0.8614	High Similarity	NPC159232
0.8609	High Similarity	NPC476943
0.8606	High Similarity	NPC296558
0.8598	High Similarity	NPC478178
0.8598	High Similarity	NPC97574
0.8598	High Similarity	NPC93172
0.8598	High Similarity	NPC149945
0.8596	High Similarity	NPC247563
0.8596	High Similarity	NPC242068
0.859	High Similarity	NPC255414
0.858	High Similarity	NPC287559
0.8571	High Similarity	NPC195954
0.8571	High Similarity	NPC88007
0.8562	High Similarity	NPC35000
0.8562	High Similarity	NPC75310
0.8553	High Similarity	NPC268905
0.8553	High Similarity	NPC44577
0.8545	High Similarity	NPC472764
0.8537	High Similarity	NPC56358
0.8528	High Similarity	NPC472767
0.8528	High Similarity	NPC211777
0.8519	High Similarity	NPC474932
0.8512	High Similarity	NPC94763
0.8503	High Similarity	NPC285227
0.8494	Intermediate Similarity	NPC242334
0.8494	Intermediate Similarity	NPC472766
0.8494	Intermediate Similarity	NPC472765
0.8491	Intermediate Similarity	NPC116717
0.8485	Intermediate Similarity	NPC472141
0.8481	Intermediate Similarity	NPC470791
0.8481	Intermediate Similarity	NPC470790
0.8481	Intermediate Similarity	NPC69647
0.8481	Intermediate Similarity	NPC125182
0.8476	Intermediate Similarity	NPC285567
0.8476	Intermediate Similarity	NPC198047
0.8476	Intermediate Similarity	NPC472139
0.8476	Intermediate Similarity	NPC165218
0.8471	Intermediate Similarity	NPC71821
0.8466	Intermediate Similarity	NPC470789
0.8462	Intermediate Similarity	NPC41182
0.8457	Intermediate Similarity	NPC472776
0.8457	Intermediate Similarity	NPC194499
0.8457	Intermediate Similarity	NPC472778
0.8457	Intermediate Similarity	NPC81405
0.8457	Intermediate Similarity	NPC472777
0.8452	Intermediate Similarity	NPC243577
0.8447	Intermediate Similarity	NPC471175
0.8443	Intermediate Similarity	NPC88593
0.8438	Intermediate Similarity	NPC475777
0.8434	Intermediate Similarity	NPC478179

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 NPC470939 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	1109
0.2-0.3	2327
0.3-0.4	2711
0.4-0.5	1728
0.5-0.6	663
0.6-0.7	228
0.7-0.8	16
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
0.8354	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5760	Phase 2
0.8221	Intermediate Similarity	NPD5761	Phase 2
0.8218	Intermediate Similarity	NPD8434	Phase 2
0.7627	Intermediate Similarity	NPD6764	Approved
0.7627	Intermediate Similarity	NPD6765	Approved
0.7574	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD6599	Discontinued
0.7459	Intermediate Similarity	NPD6785	Approved
0.7459	Intermediate Similarity	NPD6784	Approved
0.7457	Intermediate Similarity	NPD5494	Approved
0.7414	Intermediate Similarity	NPD1247	Approved
0.7407	Intermediate Similarity	NPD1471	Phase 3
0.7399	Intermediate Similarity	NPD919	Approved
0.7368	Intermediate Similarity	NPD7819	Suspended
0.7353	Intermediate Similarity	NPD7411	Suspended
0.7351	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD920	Approved
0.731	Intermediate Similarity	NPD6801	Discontinued
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6799	Approved
0.7241	Intermediate Similarity	NPD3749	Approved
0.7238	Intermediate Similarity	NPD6559	Discontinued
0.7225	Intermediate Similarity	NPD3817	Phase 2
0.7225	Intermediate Similarity	NPD5402	Approved
0.7202	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3226	Approved
0.712	Intermediate Similarity	NPD8285	Discontinued
0.7118	Intermediate Similarity	NPD5403	Approved
0.7111	Intermediate Similarity	NPD3751	Discontinued
0.7101	Intermediate Similarity	NPD5401	Approved
0.7095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3787	Discontinued
0.7072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5844	Phase 1
0.7066	Intermediate Similarity	NPD4628	Phase 3
0.7065	Intermediate Similarity	NPD8404	Phase 2
0.7056	Intermediate Similarity	NPD7473	Discontinued
0.7039	Intermediate Similarity	NPD3926	Phase 2
0.703	Intermediate Similarity	NPD2796	Approved
0.7017	Intermediate Similarity	NPD7799	Discontinued
0.7017	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4380	Phase 2
0.6989	Remote Similarity	NPD3882	Suspended
0.6982	Remote Similarity	NPD7236	Approved
0.6974	Remote Similarity	NPD7435	Discontinued
0.6973	Remote Similarity	NPD8312	Approved
0.6973	Remote Similarity	NPD8313	Approved
0.6952	Remote Similarity	NPD8150	Discontinued
0.6949	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8127	Discontinued
0.6927	Remote Similarity	NPD6959	Discontinued
0.6919	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1243	Approved
0.6902	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6232	Discontinued
0.6886	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7239	Suspended
0.6875	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3748	Approved
0.6865	Remote Similarity	NPD7251	Discontinued
0.6864	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6273	Approved
0.6839	Remote Similarity	NPD7458	Discontinued
0.6831	Remote Similarity	NPD3818	Discontinued
0.6828	Remote Similarity	NPD7808	Phase 3
0.6821	Remote Similarity	NPD4107	Approved
0.6818	Remote Similarity	NPD1934	Approved
0.6813	Remote Similarity	NPD2403	Approved
0.6811	Remote Similarity	NPD6797	Phase 2
0.6802	Remote Similarity	NPD2532	Approved
0.6802	Remote Similarity	NPD2534	Approved
0.6802	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2533	Approved
0.6798	Remote Similarity	NPD7768	Phase 2
0.679	Remote Similarity	NPD6832	Phase 2
0.6786	Remote Similarity	NPD2346	Discontinued
0.6766	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7874	Approved
0.6758	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7074	Phase 3
0.6755	Remote Similarity	NPD8407	Phase 2
0.6746	Remote Similarity	NPD1549	Phase 2
0.6743	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6777	Approved
0.6735	Remote Similarity	NPD6778	Approved
0.6735	Remote Similarity	NPD6776	Approved
0.6735	Remote Similarity	NPD6780	Approved
0.6735	Remote Similarity	NPD6782	Approved
0.6735	Remote Similarity	NPD6781	Approved
0.6735	Remote Similarity	NPD6779	Approved
0.6726	Remote Similarity	NPD6100	Approved
0.6726	Remote Similarity	NPD6099	Approved
0.6725	Remote Similarity	NPD3887	Approved
0.6723	Remote Similarity	NPD37	Approved
0.6721	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7696	Phase 3
0.6717	Remote Similarity	NPD7698	Approved
0.6717	Remote Similarity	NPD7697	Approved
0.6704	Remote Similarity	NPD4965	Approved
0.6704	Remote Similarity	NPD4967	Phase 2
0.6704	Remote Similarity	NPD4966	Approved
0.6703	Remote Similarity	NPD6808	Phase 2
0.6703	Remote Similarity	NPD7054	Approved
0.6701	Remote Similarity	NPD4482	Phase 3
0.6687	Remote Similarity	NPD6355	Discontinued
0.6686	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7685	Pre-registration
0.6684	Remote Similarity	NPD8368	Discontinued
0.6683	Remote Similarity	NPD8320	Phase 1
0.6683	Remote Similarity	NPD8319	Approved
0.6683	Remote Similarity	NPD7871	Phase 2
0.6683	Remote Similarity	NPD7870	Phase 2
0.6683	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6649	Remote Similarity	NPD7228	Approved
0.663	Remote Similarity	NPD6234	Discontinued
0.6627	Remote Similarity	NPD1551	Phase 2
0.6615	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD8435	Approved
0.6612	Remote Similarity	NPD7229	Phase 3
0.6608	Remote Similarity	NPD2800	Approved
0.6607	Remote Similarity	NPD7097	Phase 1
0.6605	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3267	Approved
0.6605	Remote Similarity	NPD3266	Approved
0.6592	Remote Similarity	NPD2801	Approved
0.6592	Remote Similarity	NPD1465	Phase 2
0.6587	Remote Similarity	NPD4111	Phase 1
0.6584	Remote Similarity	NPD7701	Phase 2
0.6582	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7801	Approved
0.6566	Remote Similarity	NPD4580	Approved
0.6557	Remote Similarity	NPD7199	Phase 2
0.655	Remote Similarity	NPD970	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7497	Discontinued
0.6545	Remote Similarity	NPD7095	Approved
0.654	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6190	Approved
0.6528	Remote Similarity	NPD8360	Approved
0.6528	Remote Similarity	NPD8361	Approved
0.6527	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7058	Phase 2
0.6519	Remote Similarity	NPD7057	Phase 3
0.651	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7240	Approved
0.6507	Remote Similarity	NPD4665	Approved
0.6506	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD6798	Discontinued
0.6506	Remote Similarity	NPD3268	Approved
0.6506	Remote Similarity	NPD2313	Discontinued
0.65	Remote Similarity	NPD8455	Phase 2
0.6497	Remote Similarity	NPD2973	Approved
0.6497	Remote Similarity	NPD2975	Approved
0.6497	Remote Similarity	NPD2974	Approved
0.6491	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2353	Approved
0.6491	Remote Similarity	NPD5763	Approved
0.6491	Remote Similarity	NPD5762	Approved
0.6491	Remote Similarity	NPD2344	Approved
0.6488	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1933	Approved
0.648	Remote Similarity	NPD6534	Approved
0.648	Remote Similarity	NPD5889	Approved
0.648	Remote Similarity	NPD5890	Approved
0.648	Remote Similarity	NPD6535	Approved
0.6477	Remote Similarity	NPD1512	Approved
0.6474	Remote Similarity	NPD7003	Approved
0.6471	Remote Similarity	NPD7033	Discontinued
0.6471	Remote Similarity	NPD1510	Phase 2
0.6467	Remote Similarity	NPD6233	Phase 2
0.6465	Remote Similarity	NPD7700	Phase 2
0.6465	Remote Similarity	NPD7699	Phase 2
0.6464	Remote Similarity	NPD5353	Approved
0.6464	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4287	Approved
0.644	Remote Similarity	NPD2971	Approved
0.644	Remote Similarity	NPD2968	Approved
0.6438	Remote Similarity	NPD17	Approved
0.6436	Remote Similarity	NPD4583	Approved
0.6436	Remote Similarity	NPD4582	Approved
0.6433	Remote Similarity	NPD2438	Suspended

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