NPASS Compound

Structure

NPC472020 OpenBabel07101718222D 23 23 0 0 1 0 0 0 0 0999 V2000 -1.1942 4.0708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2553 1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5289 -2.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2283 3.8120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5482 0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 -1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0306 2.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6766 2.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4177 1.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 21 1 0 0 0 0 6 10 1 0 0 0 0 10 11 1 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 7 1 6 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 17 12 1 6 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 9 1 1 0 0 0 19 23 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.26
Volume:	361.148
LogP:	5.425
LogD:	4.722
LogS:	-4.857
# Rotatable Bonds:	11
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	4.307
Fsp3:	0.947
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.577
MDCK Permeability:	2.281613342347555e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.16

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	86.2182388305664%
Volume Distribution (VD):	0.609
Pgp-substrate:	4.734726428985596%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.839
CYP2C19-inhibitor:	0.306
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.587
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.296
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.378

ADMET: Excretion

Clearance (CL):	11.562
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.254
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.47
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.943
Carcinogencity:	0.484
Eye Corrosion:	0.524
Eye Irritation:	0.708
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC472020

Natural Product ID:	NPC472020
*Common Name:**	OIIWCRQNPNERAL-BMFAXAFESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OIIWCRQNPNERAL-BMFAXAFESA-N
Standard InCHI:	InChI=1S/C19H36O4/c1-6-10-11-15(7-2)13-19(9-4)14-16(8-3)17(22-23-19)12-18(20)21-5/h15-17H,6-14H2,1-5H3/t15-,16-,17+,19-/m0/s1
SMILES:	CCCC[C@@H](C[C@]1(CC)OO[C@@H]([C@H](C1)CC)CC(=O)OC)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3326158
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO26409	Plakortis simplex	Species	Plakinidae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	11400.0	nM	PMID[558412]

☑ 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 NPC472020 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	371
0.1-0.2	4429
0.2-0.3	14809
0.3-0.4	10913
0.4-0.5	9000
0.5-0.6	2911
0.6-0.7	198
0.7-0.8	49
0.8-0.85	3
0.85-0.9	1
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC226602
1.0	High Similarity	NPC472019
0.9821	High Similarity	NPC472021
0.9167	High Similarity	NPC306805
0.9167	High Similarity	NPC215987
0.9153	High Similarity	NPC474552
0.8966	High Similarity	NPC475821
0.8852	High Similarity	NPC469926
0.8254	Intermediate Similarity	NPC476330
0.8209	Intermediate Similarity	NPC167145
0.8088	Intermediate Similarity	NPC330016
0.7857	Intermediate Similarity	NPC152754
0.7857	Intermediate Similarity	NPC474447
0.7857	Intermediate Similarity	NPC475744
0.7857	Intermediate Similarity	NPC476987
0.7857	Intermediate Similarity	NPC59602
0.7857	Intermediate Similarity	NPC474316
0.7857	Intermediate Similarity	NPC476985
0.7778	Intermediate Similarity	NPC469922
0.7746	Intermediate Similarity	NPC122847
0.7746	Intermediate Similarity	NPC476264
0.7746	Intermediate Similarity	NPC476325
0.7742	Intermediate Similarity	NPC469924
0.7727	Intermediate Similarity	NPC469925
0.7606	Intermediate Similarity	NPC239127
0.7606	Intermediate Similarity	NPC469514
0.7538	Intermediate Similarity	NPC314103
0.7534	Intermediate Similarity	NPC254996
0.7534	Intermediate Similarity	NPC268502
0.75	Intermediate Similarity	NPC281296
0.75	Intermediate Similarity	NPC469923
0.75	Intermediate Similarity	NPC474003
0.75	Intermediate Similarity	NPC249754
0.7465	Intermediate Similarity	NPC255060
0.746	Intermediate Similarity	NPC470363
0.7432	Intermediate Similarity	NPC476265
0.7432	Intermediate Similarity	NPC274522
0.7429	Intermediate Similarity	NPC472018
0.7429	Intermediate Similarity	NPC474543
0.7429	Intermediate Similarity	NPC238425
0.7397	Intermediate Similarity	NPC121200
0.7397	Intermediate Similarity	NPC476986
0.7397	Intermediate Similarity	NPC470905
0.7361	Intermediate Similarity	NPC266119
0.7333	Intermediate Similarity	NPC79277
0.7333	Intermediate Similarity	NPC475481
0.7333	Intermediate Similarity	NPC476988
0.7324	Intermediate Similarity	NPC474551
0.7321	Intermediate Similarity	NPC308301
0.7313	Intermediate Similarity	NPC135043
0.7313	Intermediate Similarity	NPC315525
0.7297	Intermediate Similarity	NPC82488
0.7297	Intermediate Similarity	NPC308545
0.7288	Intermediate Similarity	NPC314084
0.7286	Intermediate Similarity	NPC96322
0.726	Intermediate Similarity	NPC469867
0.7237	Intermediate Similarity	NPC475395
0.7237	Intermediate Similarity	NPC476984
0.72	Intermediate Similarity	NPC469920
0.7143	Intermediate Similarity	NPC69462
0.7143	Intermediate Similarity	NPC47363
0.7143	Intermediate Similarity	NPC287231
0.7121	Intermediate Similarity	NPC235788
0.7119	Intermediate Similarity	NPC305182
0.7119	Intermediate Similarity	NPC90904
0.7119	Intermediate Similarity	NPC55678
0.7105	Intermediate Similarity	NPC14044
0.7105	Intermediate Similarity	NPC172309
0.7105	Intermediate Similarity	NPC117960
0.7077	Intermediate Similarity	NPC469921
0.7069	Intermediate Similarity	NPC324793
0.7069	Intermediate Similarity	NPC13105
0.7069	Intermediate Similarity	NPC477878
0.7059	Intermediate Similarity	NPC241949
0.7051	Intermediate Similarity	NPC120158
0.7051	Intermediate Similarity	NPC471343
0.7051	Intermediate Similarity	NPC475193
0.7049	Intermediate Similarity	NPC72722
0.7042	Intermediate Similarity	NPC470243
0.7013	Intermediate Similarity	NPC476292
0.7013	Intermediate Similarity	NPC474605
0.7	Intermediate Similarity	NPC107130
0.6986	Remote Similarity	NPC199445
0.6986	Remote Similarity	NPC60718
0.6964	Remote Similarity	NPC317128
0.6944	Remote Similarity	NPC474755
0.6923	Remote Similarity	NPC476100
0.6923	Remote Similarity	NPC476983
0.6923	Remote Similarity	NPC69469
0.6901	Remote Similarity	NPC472017
0.6897	Remote Similarity	NPC21844
0.6897	Remote Similarity	NPC326957
0.6892	Remote Similarity	NPC474020
0.6875	Remote Similarity	NPC476104
0.6857	Remote Similarity	NPC319007
0.6842	Remote Similarity	NPC113363
0.6842	Remote Similarity	NPC474754
0.68	Remote Similarity	NPC471151
0.68	Remote Similarity	NPC108014
0.6786	Remote Similarity	NPC203531
0.6786	Remote Similarity	NPC236579
0.678	Remote Similarity	NPC200618
0.678	Remote Similarity	NPC131770
0.678	Remote Similarity	NPC106872
0.6757	Remote Similarity	NPC228411
0.675	Remote Similarity	NPC471344
0.6727	Remote Similarity	NPC161097
0.6727	Remote Similarity	NPC28598
0.6724	Remote Similarity	NPC314679
0.6721	Remote Similarity	NPC287811
0.6714	Remote Similarity	NPC286842
0.6712	Remote Similarity	NPC109510
0.6709	Remote Similarity	NPC476721
0.6667	Remote Similarity	NPC470268
0.6667	Remote Similarity	NPC475181
0.6667	Remote Similarity	NPC320588
0.6667	Remote Similarity	NPC319589
0.6667	Remote Similarity	NPC262085
0.6667	Remote Similarity	NPC53463
0.6667	Remote Similarity	NPC23155
0.6667	Remote Similarity	NPC469937
0.6667	Remote Similarity	NPC295256
0.6667	Remote Similarity	NPC476982
0.6627	Remote Similarity	NPC471342
0.6627	Remote Similarity	NPC469866
0.6625	Remote Similarity	NPC65133
0.6623	Remote Similarity	NPC19841
0.6622	Remote Similarity	NPC477867
0.662	Remote Similarity	NPC119838
0.662	Remote Similarity	NPC82315
0.661	Remote Similarity	NPC324004
0.661	Remote Similarity	NPC328497
0.6607	Remote Similarity	NPC53541
0.6585	Remote Similarity	NPC51662
0.6585	Remote Similarity	NPC314364
0.6582	Remote Similarity	NPC248415
0.6582	Remote Similarity	NPC13494
0.6579	Remote Similarity	NPC477918
0.6579	Remote Similarity	NPC83108
0.6579	Remote Similarity	NPC214030
0.6575	Remote Similarity	NPC478227
0.6552	Remote Similarity	NPC55023
0.6545	Remote Similarity	NPC31551
0.6545	Remote Similarity	NPC219536
0.6533	Remote Similarity	NPC477934
0.6533	Remote Similarity	NPC179922
0.6528	Remote Similarity	NPC178541
0.6528	Remote Similarity	NPC98711
0.65	Remote Similarity	NPC475989
0.6479	Remote Similarity	NPC41542
0.6463	Remote Similarity	NPC477441
0.6463	Remote Similarity	NPC476717
0.6463	Remote Similarity	NPC477994
0.6463	Remote Similarity	NPC477993
0.6452	Remote Similarity	NPC291724
0.6452	Remote Similarity	NPC274261
0.6447	Remote Similarity	NPC477933
0.6447	Remote Similarity	NPC477932
0.6441	Remote Similarity	NPC282440
0.6441	Remote Similarity	NPC12438
0.6441	Remote Similarity	NPC105329
0.6441	Remote Similarity	NPC63182
0.6441	Remote Similarity	NPC52700
0.6441	Remote Similarity	NPC30195
0.6441	Remote Similarity	NPC145045
0.6438	Remote Similarity	NPC475310
0.6429	Remote Similarity	NPC12156
0.6429	Remote Similarity	NPC256163
0.6429	Remote Similarity	NPC165533
0.6429	Remote Similarity	NPC149299
0.6429	Remote Similarity	NPC250028
0.6429	Remote Similarity	NPC40597
0.642	Remote Similarity	NPC477434
0.6418	Remote Similarity	NPC17935
0.641	Remote Similarity	NPC276647
0.641	Remote Similarity	NPC622
0.64	Remote Similarity	NPC55508
0.64	Remote Similarity	NPC477930
0.6375	Remote Similarity	NPC477936
0.6375	Remote Similarity	NPC477935
0.6364	Remote Similarity	NPC307865
0.6364	Remote Similarity	NPC201622
0.6364	Remote Similarity	NPC22903
0.6364	Remote Similarity	NPC145898
0.6364	Remote Similarity	NPC305660
0.6364	Remote Similarity	NPC54980
0.6351	Remote Similarity	NPC185419
0.6351	Remote Similarity	NPC184550
0.6351	Remote Similarity	NPC474590
0.6351	Remote Similarity	NPC126061
0.6341	Remote Similarity	NPC477205
0.6329	Remote Similarity	NPC125366
0.6329	Remote Similarity	NPC1882
0.6329	Remote Similarity	NPC103634
0.6324	Remote Similarity	NPC204173
0.6324	Remote Similarity	NPC478126
0.6316	Remote Similarity	NPC471491
0.6316	Remote Similarity	NPC475861
0.6316	Remote Similarity	NPC474419
0.631	Remote Similarity	NPC471221

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 NPC472020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	477
0.1-0.2	4116
0.2-0.3	3019
0.3-0.4	884
0.4-0.5	497
0.5-0.6	139
0.6-0.7	18
0.7-0.8	0
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
0.7213	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2699	Approved
0.7069	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3198	Approved
0.6765	Remote Similarity	NPD7909	Approved
0.6724	Remote Similarity	NPD634	Phase 3
0.6711	Remote Similarity	NPD4238	Approved
0.6711	Remote Similarity	NPD4802	Phase 2
0.6667	Remote Similarity	NPD3730	Approved
0.6667	Remote Similarity	NPD3728	Approved
0.6667	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.662	Remote Similarity	NPD229	Approved
0.6613	Remote Similarity	NPD3186	Phase 1
0.6491	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3206	Approved
0.6351	Remote Similarity	NPD5777	Approved
0.625	Remote Similarity	NPD5369	Approved
0.619	Remote Similarity	NPD9638	Phase 2
0.6182	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7345	Approved
0.6154	Remote Similarity	NPD6116	Phase 1
0.6104	Remote Similarity	NPD3702	Approved
0.6081	Remote Similarity	NPD3725	Approved
0.6081	Remote Similarity	NPD3726	Approved
0.6049	Remote Similarity	NPD1780	Approved
0.6049	Remote Similarity	NPD1779	Approved
0.6047	Remote Similarity	NPD6101	Approved
0.6047	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD2270	Approved
0.6026	Remote Similarity	NPD6117	Approved
0.5976	Remote Similarity	NPD6435	Approved
0.5974	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD2266	Phase 2
0.5926	Remote Similarity	NPD5368	Approved
0.5909	Remote Similarity	NPD6411	Approved
0.5882	Remote Similarity	NPD4279	Approved
0.5875	Remote Similarity	NPD6118	Approved
0.5875	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD6115	Approved
0.5875	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD6697	Approved
0.5875	Remote Similarity	NPD6114	Approved
0.5867	Remote Similarity	NPD2697	Approved
0.5867	Remote Similarity	NPD2694	Approved
0.5867	Remote Similarity	NPD2695	Approved
0.5867	Remote Similarity	NPD2696	Approved
0.5862	Remote Similarity	NPD1460	Approved
0.5818	Remote Similarity	NPD9447	Approved
0.5795	Remote Similarity	NPD6698	Approved
0.5795	Remote Similarity	NPD46	Approved
0.5783	Remote Similarity	NPD4270	Approved
0.5783	Remote Similarity	NPD4269	Approved
0.5738	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4819	Approved
0.5732	Remote Similarity	NPD4820	Approved
0.5732	Remote Similarity	NPD4821	Approved
0.5732	Remote Similarity	NPD4822	Approved
0.573	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD6081	Approved
0.5714	Remote Similarity	NPD4280	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5698	Remote Similarity	NPD5786	Approved
0.5696	Remote Similarity	NPD2257	Approved
0.569	Remote Similarity	NPD9655	Approved
0.569	Remote Similarity	NPD9448	Phase 2
0.569	Remote Similarity	NPD633	Phase 3
0.569	Remote Similarity	NPD77	Approved
0.569	Remote Similarity	NPD9450	Approved
0.5684	Remote Similarity	NPD8083	Approved
0.5684	Remote Similarity	NPD8138	Approved
0.5684	Remote Similarity	NPD8301	Approved
0.5684	Remote Similarity	NPD8084	Approved
0.5684	Remote Similarity	NPD8086	Approved
0.5684	Remote Similarity	NPD8085	Approved
0.5684	Remote Similarity	NPD8300	Approved
0.5684	Remote Similarity	NPD8139	Approved
0.5684	Remote Similarity	NPD8082	Approved
0.5676	Remote Similarity	NPD4224	Phase 2
0.5667	Remote Similarity	NPD1462	Approved
0.5667	Remote Similarity	NPD5778	Approved
0.5667	Remote Similarity	NPD5779	Approved
0.5652	Remote Similarity	NPD7839	Suspended
0.5625	Remote Similarity	NPD8276	Approved
0.5625	Remote Similarity	NPD8275	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