NPASS Compound

Structure

NPC470941 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 2.2971 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9201 3.1761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0355 3.4708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1670 0.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1317 0.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1992 4.9381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9466 -0.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6157 0.3121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6830 2.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6790 0.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1375 0.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0330 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.9757 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7521 1.9716 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0576 0.7687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8320 3.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9606 1.7134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1670 -0.5243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1870 2.4959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -0.0243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6945 1.2029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5651 -0.5243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7629 3.6911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9578 1.7882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -3.0243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0502 3.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1157 1.1781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1670 -1.5243 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 -0.5752 2.3810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 6 31 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 25 1 0 0 0 0 10 32 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 17 26 1 1 0 0 0 18 24 1 0 0 0 0 18 26 1 1 0 0 0 19 26 1 1 0 0 0 19 34 1 0 0 0 0 20 28 2 0 0 0 0 20 31 1 0 0 0 0 21 29 2 0 0 0 0 21 35 1 0 0 0 0 22 30 2 0 0 0 0 22 33 1 0 0 0 0 23 25 1 1 0 0 0 23 33 1 0 0 0 0 24 35 1 0 0 0 0 25 27 1 6 0 0 0 26 5 1 1 0 0 0 27 13 1 1 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.23
Volume:	487.269
LogP:	3.918
LogD:	2.711
LogS:	-4.958
# Rotatable Bonds:	4
TPSA:	101.27
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	6.207
Fsp3:	0.667
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:	-5.165
MDCK Permeability:	0.00012762074766214937
Pgp-inhibitor:	0.996
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.195
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	70.82147979736328%
Volume Distribution (VD):	0.871
Pgp-substrate:	26.68691635131836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.461
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.589
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.75
CYP3A4-substrate:	0.608

ADMET: Excretion

Clearance (CL):	11.744
Half-life (T1/2):	0.591

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.788
Skin Sensitization:	0.105
Carcinogencity:	0.691
Eye Corrosion:	0.047
Eye Irritation:	0.042
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC470941

Natural Product ID:	NPC470941
*Common Name:**	Methyl Ivorensate
IUPAC Name:	n.a.
Synonyms:	Methyl Ivorensate
Standard InCHIKey:	DPBKKUVQRJSGOO-GVNGGTBCSA-N
Standard InCHI:	InChI=1S/C27H34O8/c1-15-17-7-9-25(4)23(16-8-10-32-14-16)33-22(30)13-27(15,25)34-19-12-21(29)35-24(2,3)18(26(17,19)5)11-20(28)31-6/h8,10,14,17-19,23H,1,7,9,11-13H2,2-6H3/t17-,18-,19+,23+,25-,26+,27-/m1/s1
SMILES:	COC(=O)C[C@@H]1C(C)(C)OC(=O)C[C@H]2[C@@]1(C)[C@@H]1CC[C@]3([C@](O2)(C1=C)CC(=O)O[C@H]3c1cocc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332205
PubChem CID:	71720629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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	>	50.0	ug.mL-1	PMID[546983]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[546983]

☑ 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 NPC470941 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	395
0.1-0.2	1451
0.2-0.3	3115
0.3-0.4	6092
0.4-0.5	11103
0.5-0.6	10076
0.6-0.7	9045
0.7-0.8	1016
0.8-0.85	269
0.85-0.9	112
0.9-0.95	22
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9514	High Similarity	NPC476122
0.9392	High Similarity	NPC45101
0.9384	High Similarity	NPC476201
0.9379	High Similarity	NPC196864
0.9379	High Similarity	NPC477404
0.932	High Similarity	NPC282445
0.9262	High Similarity	NPC167142
0.9262	High Similarity	NPC472772
0.9257	High Similarity	NPC476262
0.9247	High Similarity	NPC156189
0.9247	High Similarity	NPC469335
0.9247	High Similarity	NPC159927
0.92	High Similarity	NPC237155
0.9195	High Similarity	NPC126723
0.9178	High Similarity	NPC470791
0.9178	High Similarity	NPC470790
0.9172	High Similarity	NPC221809
0.9143	High Similarity	NPC310830
0.9133	High Similarity	NPC249021
0.9128	High Similarity	NPC469850
0.9128	High Similarity	NPC264943
0.9122	High Similarity	NPC469503
0.9079	High Similarity	NPC472771
0.9078	High Similarity	NPC476943
0.9067	High Similarity	NPC204663
0.9054	High Similarity	NPC18135
0.902	High Similarity	NPC472773
0.9007	High Similarity	NPC286722
0.9007	High Similarity	NPC195131
0.9	High Similarity	NPC469336
0.8973	High Similarity	NPC346
0.8954	High Similarity	NPC200782
0.8954	High Similarity	NPC82851
0.8947	High Similarity	NPC475295
0.8947	High Similarity	NPC473473
0.8947	High Similarity	NPC477403
0.8944	High Similarity	NPC220094
0.894	High Similarity	NPC209364
0.894	High Similarity	NPC107646
0.894	High Similarity	NPC263265
0.8933	High Similarity	NPC57998
0.8933	High Similarity	NPC178932
0.8912	High Similarity	NPC250228
0.8897	High Similarity	NPC223415
0.8897	High Similarity	NPC470741
0.8896	High Similarity	NPC477405
0.8889	High Similarity	NPC475381
0.8889	High Similarity	NPC25255
0.8889	High Similarity	NPC472653
0.8889	High Similarity	NPC305016
0.8889	High Similarity	NPC477402
0.8882	High Similarity	NPC472283
0.8874	High Similarity	NPC214541
0.8874	High Similarity	NPC44675
0.8846	High Similarity	NPC472651
0.8846	High Similarity	NPC472774
0.8846	High Similarity	NPC476853
0.8846	High Similarity	NPC472775
0.8844	High Similarity	NPC262198
0.8839	High Similarity	NPC470182
0.8836	High Similarity	NPC142113
0.8836	High Similarity	NPC476944
0.8831	High Similarity	NPC470939
0.8831	High Similarity	NPC6326
0.8831	High Similarity	NPC207978
0.8831	High Similarity	NPC472767
0.8831	High Similarity	NPC193798
0.8831	High Similarity	NPC211777
0.8828	High Similarity	NPC121158
0.8816	High Similarity	NPC60973
0.8808	High Similarity	NPC30222
0.8792	High Similarity	NPC195325
0.8792	High Similarity	NPC472654
0.879	High Similarity	NPC472652
0.8774	High Similarity	NPC39986
0.8774	High Similarity	NPC302369
0.8774	High Similarity	NPC165218
0.8774	High Similarity	NPC292389
0.8774	High Similarity	NPC419
0.8774	High Similarity	NPC134254
0.8774	High Similarity	NPC198047
0.8774	High Similarity	NPC469846
0.8774	High Similarity	NPC476197
0.8774	High Similarity	NPC469338
0.8766	High Similarity	NPC335761
0.8758	High Similarity	NPC299038
0.8758	High Similarity	NPC36655
0.8758	High Similarity	NPC261597
0.875	High Similarity	NPC35000
0.8742	High Similarity	NPC44577
0.8742	High Similarity	NPC75906
0.8718	High Similarity	NPC123088
0.8718	High Similarity	NPC476858
0.8718	High Similarity	NPC476860
0.8718	High Similarity	NPC470940
0.8718	High Similarity	NPC476857
0.8718	High Similarity	NPC271657
0.8718	High Similarity	NPC469849
0.8718	High Similarity	NPC476856
0.8718	High Similarity	NPC276551
0.871	High Similarity	NPC149896
0.871	High Similarity	NPC329938
0.871	High Similarity	NPC18347
0.871	High Similarity	NPC263432
0.871	High Similarity	NPC69028
0.871	High Similarity	NPC5079
0.8707	High Similarity	NPC251865
0.8707	High Similarity	NPC86935
0.8701	High Similarity	NPC262872
0.8701	High Similarity	NPC475967
0.8701	High Similarity	NPC474932
0.8701	High Similarity	NPC307383
0.8693	High Similarity	NPC469485
0.8662	High Similarity	NPC478178
0.8662	High Similarity	NPC149945
0.8662	High Similarity	NPC93172
0.8662	High Similarity	NPC23387
0.8662	High Similarity	NPC470875
0.8662	High Similarity	NPC97574
0.8658	High Similarity	NPC255414
0.8654	High Similarity	NPC51568
0.8654	High Similarity	NPC472669
0.8654	High Similarity	NPC234660
0.8649	High Similarity	NPC41182
0.8645	High Similarity	NPC470789
0.8645	High Similarity	NPC191828
0.8636	High Similarity	NPC472777
0.8636	High Similarity	NPC187149
0.8636	High Similarity	NPC173544
0.8636	High Similarity	NPC472776
0.8636	High Similarity	NPC472778
0.863	High Similarity	NPC20500
0.8618	High Similarity	NPC29695
0.8618	High Similarity	NPC182427
0.8618	High Similarity	NPC476940
0.8618	High Similarity	NPC476939
0.8616	High Similarity	NPC82602
0.8611	High Similarity	NPC470742
0.8611	High Similarity	NPC310043
0.8609	High Similarity	NPC46551
0.8609	High Similarity	NPC476936
0.8608	High Similarity	NPC472764
0.8608	High Similarity	NPC473766
0.8608	High Similarity	NPC476861
0.8608	High Similarity	NPC476224
0.8608	High Similarity	NPC100333
0.8608	High Similarity	NPC476850
0.8608	High Similarity	NPC473753
0.8608	High Similarity	NPC173516
0.8608	High Similarity	NPC472282
0.8601	High Similarity	NPC92941
0.86	High Similarity	NPC19747
0.8591	High Similarity	NPC62799
0.859	High Similarity	NPC188649
0.859	High Similarity	NPC117986
0.859	High Similarity	NPC472668
0.8581	High Similarity	NPC474611
0.8571	High Similarity	NPC41880
0.8562	High Similarity	NPC160818
0.8562	High Similarity	NPC67003
0.8562	High Similarity	NPC169299
0.8553	High Similarity	NPC472765
0.8553	High Similarity	NPC471397
0.8553	High Similarity	NPC327922
0.8553	High Similarity	NPC472766
0.8553	High Similarity	NPC271235
0.8553	High Similarity	NPC160651
0.8544	High Similarity	NPC214600
0.8544	High Similarity	NPC472141
0.8543	High Similarity	NPC211625
0.8543	High Similarity	NPC125182
0.8543	High Similarity	NPC329180
0.8543	High Similarity	NPC69647
0.8542	High Similarity	NPC214572
0.8542	High Similarity	NPC46896
0.8535	High Similarity	NPC472139
0.8535	High Similarity	NPC224394
0.8535	High Similarity	NPC88841
0.8535	High Similarity	NPC663
0.8535	High Similarity	NPC288602
0.8491	Intermediate Similarity	NPC478179
0.8487	Intermediate Similarity	NPC212257
0.8477	Intermediate Similarity	NPC476942
0.8477	Intermediate Similarity	NPC476941
0.8472	Intermediate Similarity	NPC158525
0.8471	Intermediate Similarity	NPC96443
0.8471	Intermediate Similarity	NPC197596
0.8471	Intermediate Similarity	NPC290400
0.8462	Intermediate Similarity	NPC475226
0.8456	Intermediate Similarity	NPC84479
0.8435	Intermediate Similarity	NPC56197
0.8431	Intermediate Similarity	NPC116717
0.8421	Intermediate Similarity	NPC471001
0.8411	Intermediate Similarity	NPC476937
0.8411	Intermediate Similarity	NPC216755
0.8411	Intermediate Similarity	NPC71821
0.8411	Intermediate Similarity	NPC476938
0.8411	Intermediate Similarity	NPC10088
0.8411	Intermediate Similarity	NPC471174
0.8403	Intermediate Similarity	NPC471998

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 NPC470941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	977
0.2-0.3	2035
0.3-0.4	2733
0.4-0.5	1950
0.5-0.6	854
0.6-0.7	257
0.7-0.8	9
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8506	High Similarity	NPD5761	Phase 2
0.8506	High Similarity	NPD5760	Phase 2
0.795	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD8434	Phase 2
0.7547	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7421	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5494	Approved
0.7296	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6764	Approved
0.7241	Intermediate Similarity	NPD6765	Approved
0.7219	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4628	Phase 3
0.7169	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD3226	Approved
0.7134	Intermediate Similarity	NPD2796	Approved
0.7107	Intermediate Similarity	NPD1243	Approved
0.7101	Intermediate Similarity	NPD919	Approved
0.7099	Intermediate Similarity	NPD2533	Approved
0.7099	Intermediate Similarity	NPD2532	Approved
0.7099	Intermediate Similarity	NPD2534	Approved
0.7091	Intermediate Similarity	NPD6599	Discontinued
0.7089	Intermediate Similarity	NPD1471	Phase 3
0.7089	Intermediate Similarity	NPD2346	Discontinued
0.7079	Intermediate Similarity	NPD6784	Approved
0.7079	Intermediate Similarity	NPD6785	Approved
0.707	Intermediate Similarity	NPD2799	Discontinued
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8312	Approved
0.6966	Remote Similarity	NPD8313	Approved
0.6951	Remote Similarity	NPD6273	Approved
0.6928	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6959	Discontinued
0.6919	Remote Similarity	NPD1247	Approved
0.6918	Remote Similarity	NPD6100	Approved
0.6918	Remote Similarity	NPD6099	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6905	Remote Similarity	NPD6801	Discontinued
0.6894	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5844	Phase 1
0.6864	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7473	Discontinued
0.6855	Remote Similarity	NPD7033	Discontinued
0.6855	Remote Similarity	NPD3748	Approved
0.6846	Remote Similarity	NPD17	Approved
0.6832	Remote Similarity	NPD1549	Phase 2
0.6832	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6799	Approved
0.6824	Remote Similarity	NPD5402	Approved
0.6824	Remote Similarity	NPD3817	Phase 2
0.6821	Remote Similarity	NPD8127	Discontinued
0.6815	Remote Similarity	NPD4307	Phase 2
0.6802	Remote Similarity	NPD8404	Phase 2
0.68	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2313	Discontinued
0.6793	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2800	Approved
0.6788	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4380	Phase 2
0.6784	Remote Similarity	NPD7768	Phase 2
0.6782	Remote Similarity	NPD6232	Discontinued
0.677	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1019	Discontinued
0.6752	Remote Similarity	NPD8032	Phase 2
0.6744	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3926	Phase 2
0.6723	Remote Similarity	NPD3818	Discontinued
0.6711	Remote Similarity	NPD1608	Approved
0.6708	Remote Similarity	NPD2935	Discontinued
0.6707	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5403	Approved
0.6706	Remote Similarity	NPD1934	Approved
0.6688	Remote Similarity	NPD3266	Approved
0.6688	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3267	Approved
0.6688	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5401	Approved
0.6686	Remote Similarity	NPD5711	Approved
0.6686	Remote Similarity	NPD5710	Approved
0.6686	Remote Similarity	NPD7229	Phase 3
0.6686	Remote Similarity	NPD6808	Phase 2
0.6685	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD8285	Discontinued
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6648	Remote Similarity	NPD7074	Phase 3
0.6646	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD4308	Phase 3
0.6646	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7458	Discontinued
0.6611	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6166	Phase 2
0.661	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD37	Approved
0.6601	Remote Similarity	NPD9717	Approved
0.6601	Remote Similarity	NPD3972	Approved
0.6592	Remote Similarity	NPD7054	Approved
0.659	Remote Similarity	NPD4966	Approved
0.659	Remote Similarity	NPD4967	Phase 2
0.659	Remote Similarity	NPD3882	Suspended
0.659	Remote Similarity	NPD4965	Approved
0.6582	Remote Similarity	NPD3268	Approved
0.6582	Remote Similarity	NPD3764	Approved
0.6581	Remote Similarity	NPD2797	Approved
0.657	Remote Similarity	NPD1465	Phase 2
0.6568	Remote Similarity	NPD7239	Suspended
0.6562	Remote Similarity	NPD447	Suspended
0.6556	Remote Similarity	NPD5585	Approved
0.6556	Remote Similarity	NPD7472	Approved
0.6545	Remote Similarity	NPD7003	Approved
0.6545	Remote Similarity	NPD4107	Approved
0.6543	Remote Similarity	NPD1510	Phase 2
0.6538	Remote Similarity	NPD2798	Approved
0.6536	Remote Similarity	NPD7799	Discontinued
0.6536	Remote Similarity	NPD7228	Approved
0.6532	Remote Similarity	NPD5353	Approved
0.6514	Remote Similarity	NPD6234	Discontinued
0.6513	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1778	Approved
0.6507	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2309	Approved
0.6503	Remote Similarity	NPD2438	Suspended
0.65	Remote Similarity	NPD2979	Phase 3
0.6484	Remote Similarity	NPD7251	Discontinued
0.6484	Remote Similarity	NPD7685	Pre-registration
0.6481	Remote Similarity	NPD7097	Phase 1
0.6478	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD411	Approved
0.6474	Remote Similarity	NPD8455	Phase 2
0.6474	Remote Similarity	NPD1203	Approved
0.6474	Remote Similarity	NPD2801	Approved
0.6474	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6355	Discontinued
0.646	Remote Similarity	NPD4618	Approved
0.646	Remote Similarity	NPD4622	Approved
0.6453	Remote Similarity	NPD5889	Approved
0.6453	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5890	Approved
0.645	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7808	Phase 3
0.6448	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7177	Discontinued
0.6443	Remote Similarity	NPD7435	Discontinued
0.6441	Remote Similarity	NPD7199	Phase 2
0.6429	Remote Similarity	NPD5953	Discontinued
0.6429	Remote Similarity	NPD6797	Phase 2
0.6425	Remote Similarity	NPD4482	Phase 3
0.642	Remote Similarity	NPD6651	Approved
0.642	Remote Similarity	NPD1607	Approved
0.6417	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6279	Approved
0.6416	Remote Similarity	NPD6280	Approved
0.6409	Remote Similarity	NPD7286	Phase 2
0.6407	Remote Similarity	NPD3887	Approved
0.6398	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4140	Approved
0.6398	Remote Similarity	NPD1240	Approved
0.6395	Remote Similarity	NPD6585	Discontinued
0.6393	Remote Similarity	NPD7240	Approved
0.6382	Remote Similarity	NPD7783	Phase 2
0.6382	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.638	Remote Similarity	NPD5689	Approved
0.638	Remote Similarity	NPD5688	Approved
0.6378	Remote Similarity	NPD8407	Phase 2
0.6369	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5762	Approved
0.6364	Remote Similarity	NPD3496	Discontinued
0.6364	Remote Similarity	NPD5763	Approved
0.6359	Remote Similarity	NPD7698	Approved
0.6359	Remote Similarity	NPD7697	Approved
0.6359	Remote Similarity	NPD7497	Discontinued
0.6359	Remote Similarity	NPD7696	Phase 3
0.6359	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6386	Approved
0.6358	Remote Similarity	NPD5124	Phase 1
0.6358	Remote Similarity	NPD6385	Approved
0.6358	Remote Similarity	NPD5123	Clinical (unspecified phase)

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