NPASS Compound

Structure

NPC96268 OpenBabel07101718242D 30 33 0 0 1 0 0 0 0 0999 V2000 0.4238 2.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 3.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7472 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1866 1.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8977 1.5031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4896 2.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8886 1.3689 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1866 -0.0889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4638 0.6021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0672 0.3849 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3557 3.0801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.7201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5201 0.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9682 -0.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4896 1.5801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.2201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 25 2 0 0 0 0 12 29 1 0 0 0 0 13 26 2 0 0 0 0 13 30 1 0 0 0 0 14 19 2 0 0 0 0 15 9 1 1 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 16 29 1 1 0 0 0 17 24 1 1 0 0 0 17 30 1 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 1 0 0 0 0 20 27 2 0 0 0 0 21 28 1 6 0 0 0 22 23 1 0 0 0 0 22 24 1 1 0 0 0 24 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	428.993
LogP:	2.978
LogD:	2.459
LogS:	-4.394
# Rotatable Bonds:	4
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	5.683
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	3.738994928426109e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	80.67411041259766%
Volume Distribution (VD):	1.124
Pgp-substrate:	25.406774520874023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.358
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.384

ADMET: Excretion

Clearance (CL):	2.388
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.614
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.68
Carcinogencity:	0.19
Eye Corrosion:	0.018
Eye Irritation:	0.028
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC96268

Natural Product ID:	NPC96268
*Common Name:**	QPXTVGNCBLYFBX-GPMMHRFPSA-N
IUPAC Name:	n.a.
Synonyms:	1Alpha,6Alpha-Diacetoxyjungermannenone C
Standard InCHIKey:	QPXTVGNCBLYFBX-GPMMHRFPSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-11-15-9-14-10-16(29-12(2)25)22-23(4,5)8-7-17(30-13(3)26)24(22,6)19(14)18(20(11)27)21(15)28/h15-18,21-22,28H,1,7-10H2,2-6H3/t15-,16+,17+,18+,21+,22-,24+/m1/s1
SMILES:	CC(=O)O[C@H]1CC2=C([C@]3([C@H]1C(C)(C)CC[C@@H]3OC(=O)C)C)[C@@H]1[C@H]([C@H](C2)C(=C)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457851
PubChem CID:	25019494
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic 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
NPO33117	jungermannia atrobrunnea	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18665642]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128.0	ug.mL-1	PMID[475308]

☑ 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 NPC96268 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	205
0.1-0.2	1323
0.2-0.3	4598
0.3-0.4	8276
0.4-0.5	12646
0.5-0.6	6394
0.6-0.7	6365
0.7-0.8	2547
0.8-0.85	295
0.85-0.9	46
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC159442
0.91	High Similarity	NPC87927
0.9091	High Similarity	NPC289148
0.9091	High Similarity	NPC52899
0.9091	High Similarity	NPC163963
0.9082	High Similarity	NPC471038
0.9	High Similarity	NPC88203
0.9	High Similarity	NPC286519
0.9	High Similarity	NPC304832
0.9	High Similarity	NPC76866
0.9	High Similarity	NPC214946
0.9	High Similarity	NPC148628
0.9	High Similarity	NPC246736
0.899	High Similarity	NPC287676
0.8942	High Similarity	NPC197428
0.89	High Similarity	NPC46848
0.8889	High Similarity	NPC16911
0.8889	High Similarity	NPC474793
0.8889	High Similarity	NPC78427
0.8878	High Similarity	NPC200054
0.8878	High Similarity	NPC329910
0.8878	High Similarity	NPC29410
0.8824	High Similarity	NPC98603
0.8812	High Similarity	NPC136289
0.8812	High Similarity	NPC275990
0.8785	High Similarity	NPC243354
0.8776	High Similarity	NPC470232
0.8776	High Similarity	NPC98639
0.8776	High Similarity	NPC470229
0.8776	High Similarity	NPC470016
0.8776	High Similarity	NPC317586
0.8776	High Similarity	NPC48330
0.875	High Similarity	NPC218123
0.875	High Similarity	NPC112895
0.875	High Similarity	NPC231278
0.8738	High Similarity	NPC278628
0.8738	High Similarity	NPC231530
0.8725	High Similarity	NPC216114
0.8725	High Similarity	NPC209298
0.8725	High Similarity	NPC122811
0.8725	High Similarity	NPC277074
0.8725	High Similarity	NPC140723
0.8713	High Similarity	NPC81530
0.8713	High Similarity	NPC236585
0.8713	High Similarity	NPC473514
0.87	High Similarity	NPC28864
0.87	High Similarity	NPC20479
0.87	High Similarity	NPC38296
0.87	High Similarity	NPC98837
0.87	High Similarity	NPC162459
0.87	High Similarity	NPC38471
0.8692	High Similarity	NPC194273
0.8692	High Similarity	NPC202889
0.8692	High Similarity	NPC52634
0.8692	High Similarity	NPC472926
0.8687	High Similarity	NPC42042
0.8687	High Similarity	NPC13949
0.8687	High Similarity	NPC173272
0.8673	High Similarity	NPC475118
0.8673	High Similarity	NPC470385
0.8673	High Similarity	NPC470386
0.8673	High Similarity	NPC47853
0.8673	High Similarity	NPC166906
0.8654	High Similarity	NPC472925
0.8641	High Similarity	NPC202793
0.8641	High Similarity	NPC84928
0.8641	High Similarity	NPC28656
0.8641	High Similarity	NPC474558
0.8627	High Similarity	NPC475558
0.8627	High Similarity	NPC473788
0.8624	High Similarity	NPC472927
0.8614	High Similarity	NPC267921
0.8614	High Similarity	NPC470388
0.8614	High Similarity	NPC293866
0.8598	High Similarity	NPC71348
0.8586	High Similarity	NPC184848
0.8586	High Similarity	NPC69548
0.8586	High Similarity	NPC210214
0.8571	High Similarity	NPC273155
0.8571	High Similarity	NPC94529
0.8571	High Similarity	NPC206810
0.8571	High Similarity	NPC211224
0.8558	High Similarity	NPC138908
0.8558	High Similarity	NPC200957
0.8558	High Similarity	NPC37600
0.8544	High Similarity	NPC96217
0.8544	High Similarity	NPC55872
0.8544	High Similarity	NPC139347
0.8532	High Similarity	NPC270958
0.8529	High Similarity	NPC252614
0.8529	High Similarity	NPC472924
0.8529	High Similarity	NPC471790
0.8529	High Similarity	NPC148279
0.8515	High Similarity	NPC26270
0.8515	High Similarity	NPC114274
0.8515	High Similarity	NPC89099
0.8505	High Similarity	NPC329953
0.8505	High Similarity	NPC470281
0.8505	High Similarity	NPC471243
0.8505	High Similarity	NPC472928
0.85	High Similarity	NPC305483
0.85	High Similarity	NPC328162
0.85	High Similarity	NPC95565
0.85	High Similarity	NPC120708
0.85	High Similarity	NPC96859
0.85	High Similarity	NPC470387
0.8485	Intermediate Similarity	NPC302008
0.8485	Intermediate Similarity	NPC191094
0.8476	Intermediate Similarity	NPC176949
0.8476	Intermediate Similarity	NPC166993
0.8476	Intermediate Similarity	NPC201908
0.8469	Intermediate Similarity	NPC297265
0.8469	Intermediate Similarity	NPC470230
0.8469	Intermediate Similarity	NPC476168
0.8469	Intermediate Similarity	NPC211403
0.8469	Intermediate Similarity	NPC250753
0.8469	Intermediate Similarity	NPC198242
0.8469	Intermediate Similarity	NPC23434
0.8468	Intermediate Similarity	NPC472933
0.8462	Intermediate Similarity	NPC13149
0.8462	Intermediate Similarity	NPC29705
0.8462	Intermediate Similarity	NPC477812
0.8447	Intermediate Similarity	NPC22388
0.8447	Intermediate Similarity	NPC475803
0.8447	Intermediate Similarity	NPC309388
0.844	Intermediate Similarity	NPC470953
0.8431	Intermediate Similarity	NPC476274
0.8431	Intermediate Similarity	NPC218383
0.8431	Intermediate Similarity	NPC476933
0.8431	Intermediate Similarity	NPC316964
0.8426	Intermediate Similarity	NPC474927
0.8416	Intermediate Similarity	NPC320306
0.8416	Intermediate Similarity	NPC108078
0.8416	Intermediate Similarity	NPC10864
0.8411	Intermediate Similarity	NPC471093
0.84	Intermediate Similarity	NPC84018
0.84	Intermediate Similarity	NPC138245
0.84	Intermediate Similarity	NPC231060
0.84	Intermediate Similarity	NPC469599
0.8396	Intermediate Similarity	NPC189075
0.8396	Intermediate Similarity	NPC275539
0.8384	Intermediate Similarity	NPC144739
0.8384	Intermediate Similarity	NPC294263
0.8384	Intermediate Similarity	NPC181594
0.8381	Intermediate Similarity	NPC323834
0.8381	Intermediate Similarity	NPC295366
0.8381	Intermediate Similarity	NPC102352
0.8381	Intermediate Similarity	NPC4115
0.8378	Intermediate Similarity	NPC118638
0.8367	Intermediate Similarity	NPC80401
0.8365	Intermediate Similarity	NPC95899
0.8365	Intermediate Similarity	NPC95585
0.8365	Intermediate Similarity	NPC236390
0.8365	Intermediate Similarity	NPC282233
0.8365	Intermediate Similarity	NPC469985
0.8365	Intermediate Similarity	NPC470310
0.8364	Intermediate Similarity	NPC476963
0.8351	Intermediate Similarity	NPC242864
0.8351	Intermediate Similarity	NPC471724
0.835	Intermediate Similarity	NPC14634
0.835	Intermediate Similarity	NPC476240
0.835	Intermediate Similarity	NPC476223
0.835	Intermediate Similarity	NPC253886
0.835	Intermediate Similarity	NPC121218
0.835	Intermediate Similarity	NPC224720
0.8349	Intermediate Similarity	NPC471252
0.8349	Intermediate Similarity	NPC962
0.8349	Intermediate Similarity	NPC320118
0.8333	Intermediate Similarity	NPC213320
0.8333	Intermediate Similarity	NPC118860
0.8333	Intermediate Similarity	NPC477813
0.8333	Intermediate Similarity	NPC29505
0.8333	Intermediate Similarity	NPC214797
0.8333	Intermediate Similarity	NPC231589
0.8333	Intermediate Similarity	NPC477854
0.8319	Intermediate Similarity	NPC46570
0.8318	Intermediate Similarity	NPC469744
0.8318	Intermediate Similarity	NPC304495
0.8318	Intermediate Similarity	NPC286174
0.8318	Intermediate Similarity	NPC77947
0.8318	Intermediate Similarity	NPC241927
0.8318	Intermediate Similarity	NPC258543
0.8318	Intermediate Similarity	NPC102741
0.8317	Intermediate Similarity	NPC7124
0.8317	Intermediate Similarity	NPC328371
0.8304	Intermediate Similarity	NPC473203
0.8304	Intermediate Similarity	NPC476960
0.8302	Intermediate Similarity	NPC144854
0.8302	Intermediate Similarity	NPC469746
0.8302	Intermediate Similarity	NPC3316
0.8302	Intermediate Similarity	NPC96333
0.8302	Intermediate Similarity	NPC220974
0.8302	Intermediate Similarity	NPC88833
0.8302	Intermediate Similarity	NPC471474
0.8302	Intermediate Similarity	NPC59530
0.8302	Intermediate Similarity	NPC186054
0.8302	Intermediate Similarity	NPC110496
0.83	Intermediate Similarity	NPC261333
0.83	Intermediate Similarity	NPC91772
0.83	Intermediate Similarity	NPC289539

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 NPC96268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1694
0.2-0.3	3832
0.3-0.4	2232
0.4-0.5	684
0.5-0.6	253
0.6-0.7	161
0.7-0.8	125
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
0.8224	Intermediate Similarity	NPD6881	Approved
0.8224	Intermediate Similarity	NPD6899	Approved
0.8208	Intermediate Similarity	NPD6008	Approved
0.8208	Intermediate Similarity	NPD6402	Approved
0.8208	Intermediate Similarity	NPD6675	Approved
0.8208	Intermediate Similarity	NPD5739	Approved
0.8208	Intermediate Similarity	NPD7128	Approved
0.82	Intermediate Similarity	NPD6399	Phase 3
0.8165	Intermediate Similarity	NPD6649	Approved
0.8165	Intermediate Similarity	NPD6650	Approved
0.8148	Intermediate Similarity	NPD6372	Approved
0.8148	Intermediate Similarity	NPD6373	Approved
0.8131	Intermediate Similarity	NPD5697	Approved
0.8073	Intermediate Similarity	NPD7290	Approved
0.8073	Intermediate Similarity	NPD7102	Approved
0.8073	Intermediate Similarity	NPD6883	Approved
0.807	Intermediate Similarity	NPD6319	Approved
0.8056	Intermediate Similarity	NPD6011	Approved
0.8056	Intermediate Similarity	NPD7320	Approved
0.8018	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6013	Approved
0.7982	Intermediate Similarity	NPD6014	Approved
0.7982	Intermediate Similarity	NPD6012	Approved
0.7963	Intermediate Similarity	NPD5701	Approved
0.7949	Intermediate Similarity	NPD7492	Approved
0.7928	Intermediate Similarity	NPD6882	Approved
0.7928	Intermediate Similarity	NPD8297	Approved
0.7921	Intermediate Similarity	NPD6079	Approved
0.7913	Intermediate Similarity	NPD6054	Approved
0.79	Intermediate Similarity	NPD5328	Approved
0.7881	Intermediate Similarity	NPD6616	Approved
0.7838	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD7078	Approved
0.7807	Intermediate Similarity	NPD6009	Approved
0.7778	Intermediate Similarity	NPD6370	Approved
0.7759	Intermediate Similarity	NPD6059	Approved
0.775	Intermediate Similarity	NPD7736	Approved
0.7748	Intermediate Similarity	NPD4634	Approved
0.7745	Intermediate Similarity	NPD6411	Approved
0.7736	Intermediate Similarity	NPD4696	Approved
0.7736	Intermediate Similarity	NPD5285	Approved
0.7736	Intermediate Similarity	NPD5286	Approved
0.7714	Intermediate Similarity	NPD4755	Approved
0.7714	Intermediate Similarity	NPD7902	Approved
0.7712	Intermediate Similarity	NPD7604	Phase 2
0.7692	Intermediate Similarity	NPD6015	Approved
0.7692	Intermediate Similarity	NPD5983	Phase 2
0.7692	Intermediate Similarity	NPD6016	Approved
0.7667	Intermediate Similarity	NPD8293	Discontinued
0.7664	Intermediate Similarity	NPD5223	Approved
0.7652	Intermediate Similarity	NPD7115	Discovery
0.7642	Intermediate Similarity	NPD7638	Approved
0.7627	Intermediate Similarity	NPD5988	Approved
0.7619	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5221	Approved
0.7619	Intermediate Similarity	NPD5222	Approved
0.7619	Intermediate Similarity	NPD4697	Phase 3
0.76	Intermediate Similarity	NPD3618	Phase 1
0.7596	Intermediate Similarity	NPD7748	Approved
0.7593	Intermediate Similarity	NPD5224	Approved
0.7593	Intermediate Similarity	NPD5225	Approved
0.7593	Intermediate Similarity	NPD4633	Approved
0.7593	Intermediate Similarity	NPD5226	Approved
0.7593	Intermediate Similarity	NPD5211	Phase 2
0.7586	Intermediate Similarity	NPD6335	Approved
0.7583	Intermediate Similarity	NPD6336	Discontinued
0.7576	Intermediate Similarity	NPD4786	Approved
0.7573	Intermediate Similarity	NPD7515	Phase 2
0.7573	Intermediate Similarity	NPD8034	Phase 2
0.7573	Intermediate Similarity	NPD8035	Phase 2
0.757	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD7640	Approved
0.757	Intermediate Similarity	NPD4700	Approved
0.7565	Intermediate Similarity	NPD6274	Approved
0.7549	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6101	Approved
0.7547	Intermediate Similarity	NPD6083	Phase 2
0.7547	Intermediate Similarity	NPD5173	Approved
0.7547	Intermediate Similarity	NPD6084	Phase 2
0.7524	Intermediate Similarity	NPD5695	Phase 3
0.7523	Intermediate Similarity	NPD5174	Approved
0.7523	Intermediate Similarity	NPD5175	Approved
0.7521	Intermediate Similarity	NPD7101	Approved
0.7521	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7455	Intermediate Similarity	NPD5141	Approved
0.7436	Intermediate Similarity	NPD6314	Approved
0.7436	Intermediate Similarity	NPD6313	Approved
0.7429	Intermediate Similarity	NPD7900	Approved
0.7429	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7146	Approved
0.7426	Intermediate Similarity	NPD5330	Approved
0.7426	Intermediate Similarity	NPD6409	Approved
0.7426	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6684	Approved
0.7426	Intermediate Similarity	NPD7334	Approved
0.7426	Intermediate Similarity	NPD7521	Approved
0.7417	Intermediate Similarity	NPD8328	Phase 3
0.7414	Intermediate Similarity	NPD6868	Approved
0.7404	Intermediate Similarity	NPD5284	Approved
0.7404	Intermediate Similarity	NPD5281	Approved
0.7395	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3667	Approved
0.7364	Intermediate Similarity	NPD4754	Approved
0.7358	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6412	Phase 2
0.7317	Intermediate Similarity	NPD6033	Approved
0.7315	Intermediate Similarity	NPD5696	Approved
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.7282	Intermediate Similarity	NPD6903	Approved
0.7282	Intermediate Similarity	NPD6672	Approved
0.7282	Intermediate Similarity	NPD5737	Approved
0.7282	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7319	Approved
0.7257	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5128	Approved
0.7257	Intermediate Similarity	NPD4730	Approved
0.7257	Intermediate Similarity	NPD4729	Approved
0.725	Intermediate Similarity	NPD6908	Approved
0.725	Intermediate Similarity	NPD6909	Approved
0.7232	Intermediate Similarity	NPD4767	Approved
0.7232	Intermediate Similarity	NPD4768	Approved
0.7228	Intermediate Similarity	NPD3133	Approved
0.7228	Intermediate Similarity	NPD3665	Phase 1
0.7228	Intermediate Similarity	NPD3666	Approved
0.7184	Intermediate Similarity	NPD3573	Approved
0.7156	Intermediate Similarity	NPD4225	Approved
0.7154	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5169	Approved
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.713	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5135	Approved
0.7117	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD5279	Phase 3
0.7077	Intermediate Similarity	NPD6334	Approved
0.7077	Intermediate Similarity	NPD6333	Approved
0.7075	Intermediate Similarity	NPD6050	Approved
0.7069	Intermediate Similarity	NPD5215	Approved
0.7069	Intermediate Similarity	NPD5216	Approved
0.7069	Intermediate Similarity	NPD5127	Approved
0.7069	Intermediate Similarity	NPD5217	Approved
0.7048	Intermediate Similarity	NPD6673	Approved
0.7048	Intermediate Similarity	NPD4753	Phase 2
0.7048	Intermediate Similarity	NPD6904	Approved
0.7048	Intermediate Similarity	NPD6080	Approved
0.7043	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4629	Approved
0.7037	Intermediate Similarity	NPD5210	Approved
0.6983	Remote Similarity	NPD6371	Approved
0.6983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5692	Phase 3
0.6981	Remote Similarity	NPD5785	Approved
0.6981	Remote Similarity	NPD5207	Approved
0.697	Remote Similarity	NPD6115	Approved
0.697	Remote Similarity	NPD6118	Approved
0.697	Remote Similarity	NPD6697	Approved
0.697	Remote Similarity	NPD6114	Approved
0.6961	Remote Similarity	NPD4788	Approved
0.6957	Remote Similarity	NPD5168	Approved
0.6957	Remote Similarity	NPD6686	Approved
0.6944	Remote Similarity	NPD6001	Approved
0.6931	Remote Similarity	NPD5369	Approved
0.6923	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD5786	Approved
0.6923	Remote Similarity	NPD6098	Approved
0.6916	Remote Similarity	NPD5694	Approved
0.6916	Remote Similarity	NPD7637	Suspended
0.6893	Remote Similarity	NPD3668	Phase 3
0.6891	Remote Similarity	NPD5167	Approved
0.6875	Remote Similarity	NPD7260	Phase 2
0.6869	Remote Similarity	NPD6116	Phase 1
0.6863	Remote Similarity	NPD4221	Approved
0.6863	Remote Similarity	NPD6435	Approved
0.6863	Remote Similarity	NPD4223	Phase 3
0.6855	Remote Similarity	NPD6067	Discontinued
0.6832	Remote Similarity	NPD7525	Registered
0.6827	Remote Similarity	NPD1694	Approved
0.6827	Remote Similarity	NPD5363	Approved
0.6827	Remote Similarity	NPD5329	Approved
0.6792	Remote Similarity	NPD5208	Approved
0.6789	Remote Similarity	NPD5282	Discontinued
0.6768	Remote Similarity	NPD6117	Approved
0.6762	Remote Similarity	NPD5280	Approved
0.6762	Remote Similarity	NPD4694	Approved
0.6759	Remote Similarity	NPD5693	Phase 1

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