NPASS Compound

Structure

NPC81530 OpenBabel07101718312D 27 30 0 0 1 0 0 0 0 0999 V2000 1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 0 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 1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1133 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2650 -1.0088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2472 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 0 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 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9793 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8885 -1.7907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6634 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1133 0.5000 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 20 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 14 1 0 0 0 0 8 16 2 0 0 0 0 10 15 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 23 2 0 0 0 0 12 27 1 0 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 14 24 1 6 0 0 0 15 18 1 0 0 0 0 15 27 1 1 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 1 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 22 1 0 0 0 0 19 26 2 0 0 0 0 21 5 1 1 0 0 0 22 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	388.248
LogP:	2.266
LogD:	1.959
LogS:	-3.742
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	6.244
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	2.2259777324507013e-05
Pgp-inhibitor:	0.109
Pgp-substrate:	0.329
Human Intestinal Absorption (HIA):	0.12
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.22

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	53.633583068847656%
Volume Distribution (VD):	0.622
Pgp-substrate:	49.02873611450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.514

ADMET: Excretion

Clearance (CL):	2.626
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.491
Carcinogencity:	0.71
Eye Corrosion:	0.013
Eye Irritation:	0.02
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: NPC81530

Natural Product ID:	NPC81530
*Common Name:**	OUOLSVCEHYECNL-JLBPZFPESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OUOLSVCEHYECNL-JLBPZFPESA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-11-13-9-22(19(11)26)10-15(27-12(2)23)18-20(3,4)7-6-17(25)21(18,5)16(22)8-14(13)24/h8,13-15,17-18,24-25H,1,6-7,9-10H2,2-5H3/t13-,14-,15+,17+,18-,21-,22+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@]23C[C@H](C(=C)C2=O)[C@@H](C=C3[C@]2([C@H]1C(C)(C)CC[C@@H]2O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497691
PubChem CID:	25019751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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[541938]

☑ 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 NPC81530 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	188
0.1-0.2	1095
0.2-0.3	3778
0.3-0.4	7907
0.4-0.5	13205
0.5-0.6	6198
0.6-0.7	5880
0.7-0.8	3642
0.8-0.85	714
0.85-0.9	83
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC136289
0.9271	High Similarity	NPC476274
0.9175	High Similarity	NPC224720
0.9175	High Similarity	NPC476240
0.9175	High Similarity	NPC476223
0.8969	High Similarity	NPC478056
0.8866	High Similarity	NPC474343
0.8866	High Similarity	NPC170131
0.8866	High Similarity	NPC226986
0.88	High Similarity	NPC159442
0.88	High Similarity	NPC236390
0.8776	High Similarity	NPC114274
0.8763	High Similarity	NPC328371
0.8725	High Similarity	NPC230541
0.8713	High Similarity	NPC96268
0.87	High Similarity	NPC119601
0.87	High Similarity	NPC204450
0.87	High Similarity	NPC195290
0.87	High Similarity	NPC308726
0.8687	High Similarity	NPC287833
0.8673	High Similarity	NPC253826
0.866	High Similarity	NPC470016
0.866	High Similarity	NPC134067
0.866	High Similarity	NPC98639
0.866	High Similarity	NPC317586
0.866	High Similarity	NPC173875
0.866	High Similarity	NPC174948
0.866	High Similarity	NPC469599
0.866	High Similarity	NPC469995
0.866	High Similarity	NPC318282
0.8646	High Similarity	NPC294263
0.8641	High Similarity	NPC275539
0.8641	High Similarity	NPC295244
0.8641	High Similarity	NPC189075
0.8614	High Similarity	NPC476237
0.8614	High Similarity	NPC90177
0.8602	High Similarity	NPC473226
0.86	High Similarity	NPC302537
0.86	High Similarity	NPC163372
0.8586	High Similarity	NPC197386
0.8586	High Similarity	NPC176845
0.8585	High Similarity	NPC250109
0.8585	High Similarity	NPC962
0.8571	High Similarity	NPC13949
0.8571	High Similarity	NPC29410
0.8571	High Similarity	NPC200054
0.8571	High Similarity	NPC104568
0.8558	High Similarity	NPC141350
0.8557	High Similarity	NPC166906
0.8557	High Similarity	NPC184870
0.8544	High Similarity	NPC475294
0.8544	High Similarity	NPC472925
0.8544	High Similarity	NPC110496
0.8544	High Similarity	NPC44063
0.8542	High Similarity	NPC186363
0.8542	High Similarity	NPC233345
0.8542	High Similarity	NPC250753
0.8542	High Similarity	NPC297265
0.8529	High Similarity	NPC118911
0.8529	High Similarity	NPC28656
0.8519	High Similarity	NPC471854
0.8515	High Similarity	NPC56498
0.8515	High Similarity	NPC293753
0.85	High Similarity	NPC218383
0.85	High Similarity	NPC117685
0.85	High Similarity	NPC51370
0.85	High Similarity	NPC477521
0.85	High Similarity	NPC205899
0.85	High Similarity	NPC266955
0.8491	Intermediate Similarity	NPC71348
0.8485	Intermediate Similarity	NPC84335
0.8485	Intermediate Similarity	NPC108078
0.8485	Intermediate Similarity	NPC121339
0.8485	Intermediate Similarity	NPC10864
0.8485	Intermediate Similarity	NPC18319
0.8485	Intermediate Similarity	NPC475894
0.8485	Intermediate Similarity	NPC254496
0.8485	Intermediate Similarity	NPC38530
0.8485	Intermediate Similarity	NPC23680
0.8485	Intermediate Similarity	NPC320306
0.8485	Intermediate Similarity	NPC107243
0.8476	Intermediate Similarity	NPC197428
0.8469	Intermediate Similarity	NPC53565
0.8469	Intermediate Similarity	NPC183012
0.8462	Intermediate Similarity	NPC469844
0.8454	Intermediate Similarity	NPC141497
0.8454	Intermediate Similarity	NPC470375
0.8454	Intermediate Similarity	NPC476416
0.8454	Intermediate Similarity	NPC107674
0.8454	Intermediate Similarity	NPC69454
0.8454	Intermediate Similarity	NPC38232
0.8454	Intermediate Similarity	NPC470254
0.8454	Intermediate Similarity	NPC170220
0.8454	Intermediate Similarity	NPC470224
0.8454	Intermediate Similarity	NPC470376
0.8447	Intermediate Similarity	NPC323834
0.8447	Intermediate Similarity	NPC102352
0.8447	Intermediate Similarity	NPC469607
0.8447	Intermediate Similarity	NPC278628
0.8447	Intermediate Similarity	NPC231530
0.8438	Intermediate Similarity	NPC48010
0.8438	Intermediate Similarity	NPC471896
0.8431	Intermediate Similarity	NPC95899
0.8431	Intermediate Similarity	NPC478057
0.8431	Intermediate Similarity	NPC264048
0.8431	Intermediate Similarity	NPC55872
0.8431	Intermediate Similarity	NPC140723
0.8426	Intermediate Similarity	NPC266728
0.8426	Intermediate Similarity	NPC49492
0.8426	Intermediate Similarity	NPC270929
0.8421	Intermediate Similarity	NPC48107
0.8421	Intermediate Similarity	NPC328539
0.8416	Intermediate Similarity	NPC115899
0.8416	Intermediate Similarity	NPC474327
0.8416	Intermediate Similarity	NPC472924
0.8416	Intermediate Similarity	NPC472637
0.8416	Intermediate Similarity	NPC115862
0.8411	Intermediate Similarity	NPC202889
0.8411	Intermediate Similarity	NPC25909
0.8411	Intermediate Similarity	NPC472929
0.8411	Intermediate Similarity	NPC122056
0.8411	Intermediate Similarity	NPC472926
0.8404	Intermediate Similarity	NPC322159
0.8404	Intermediate Similarity	NPC6979
0.8404	Intermediate Similarity	NPC82979
0.84	Intermediate Similarity	NPC28864
0.84	Intermediate Similarity	NPC20479
0.84	Intermediate Similarity	NPC316598
0.84	Intermediate Similarity	NPC38296
0.84	Intermediate Similarity	NPC471717
0.84	Intermediate Similarity	NPC98837
0.84	Intermediate Similarity	NPC162459
0.84	Intermediate Similarity	NPC10364
0.84	Intermediate Similarity	NPC471038
0.84	Intermediate Similarity	NPC48647
0.84	Intermediate Similarity	NPC89099
0.84	Intermediate Similarity	NPC222011
0.84	Intermediate Similarity	NPC38471
0.8396	Intermediate Similarity	NPC474315
0.8396	Intermediate Similarity	NPC472928
0.8396	Intermediate Similarity	NPC188738
0.8384	Intermediate Similarity	NPC7124
0.8384	Intermediate Similarity	NPC3772
0.8384	Intermediate Similarity	NPC250757
0.8384	Intermediate Similarity	NPC249954
0.8384	Intermediate Similarity	NPC235053
0.8384	Intermediate Similarity	NPC305483
0.8384	Intermediate Similarity	NPC301534
0.8384	Intermediate Similarity	NPC328162
0.8384	Intermediate Similarity	NPC472941
0.8384	Intermediate Similarity	NPC96859
0.8384	Intermediate Similarity	NPC456
0.8384	Intermediate Similarity	NPC117133
0.8381	Intermediate Similarity	NPC475941
0.8381	Intermediate Similarity	NPC2766
0.8381	Intermediate Similarity	NPC474901
0.8367	Intermediate Similarity	NPC119562
0.8367	Intermediate Similarity	NPC279410
0.8367	Intermediate Similarity	NPC472977
0.8367	Intermediate Similarity	NPC472976
0.8367	Intermediate Similarity	NPC159410
0.8367	Intermediate Similarity	NPC469406
0.8365	Intermediate Similarity	NPC3316
0.8365	Intermediate Similarity	NPC475060
0.8365	Intermediate Similarity	NPC220229
0.8365	Intermediate Similarity	NPC144854
0.8364	Intermediate Similarity	NPC61520
0.8364	Intermediate Similarity	NPC475041
0.8351	Intermediate Similarity	NPC473998
0.8351	Intermediate Similarity	NPC185936
0.8351	Intermediate Similarity	NPC107690
0.8351	Intermediate Similarity	NPC212301
0.8351	Intermediate Similarity	NPC154101
0.8351	Intermediate Similarity	NPC472978
0.8351	Intermediate Similarity	NPC110657
0.8351	Intermediate Similarity	NPC86266
0.8351	Intermediate Similarity	NPC26888
0.8351	Intermediate Similarity	NPC168027
0.8351	Intermediate Similarity	NPC63748
0.835	Intermediate Similarity	NPC189616
0.835	Intermediate Similarity	NPC235889
0.8349	Intermediate Similarity	NPC472927
0.8333	Intermediate Similarity	NPC262858
0.8333	Intermediate Similarity	NPC475921
0.8333	Intermediate Similarity	NPC473424
0.8333	Intermediate Similarity	NPC474704
0.8333	Intermediate Similarity	NPC243354
0.8333	Intermediate Similarity	NPC119416
0.8333	Intermediate Similarity	NPC67259
0.8333	Intermediate Similarity	NPC472973
0.8333	Intermediate Similarity	NPC146554
0.8333	Intermediate Similarity	NPC477915
0.8333	Intermediate Similarity	NPC147912
0.8333	Intermediate Similarity	NPC309603
0.8333	Intermediate Similarity	NPC234892
0.8333	Intermediate Similarity	NPC473999
0.8333	Intermediate Similarity	NPC472240
0.8318	Intermediate Similarity	NPC264634
0.8318	Intermediate Similarity	NPC194951
0.8318	Intermediate Similarity	NPC12046

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 NPC81530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1328
0.2-0.3	3558
0.3-0.4	2633
0.4-0.5	926
0.5-0.6	190
0.6-0.7	184
0.7-0.8	124
0.8-0.85	41
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8646	High Similarity	NPD6399	Phase 3
0.8544	High Similarity	NPD5697	Approved
0.8462	Intermediate Similarity	NPD6881	Approved
0.8462	Intermediate Similarity	NPD6899	Approved
0.8462	Intermediate Similarity	NPD6011	Approved
0.8447	Intermediate Similarity	NPD6402	Approved
0.8447	Intermediate Similarity	NPD5739	Approved
0.8447	Intermediate Similarity	NPD7128	Approved
0.8447	Intermediate Similarity	NPD6675	Approved
0.8396	Intermediate Similarity	NPD6649	Approved
0.8396	Intermediate Similarity	NPD6650	Approved
0.8381	Intermediate Similarity	NPD6013	Approved
0.8381	Intermediate Similarity	NPD6012	Approved
0.8381	Intermediate Similarity	NPD6014	Approved
0.8381	Intermediate Similarity	NPD6373	Approved
0.8381	Intermediate Similarity	NPD6372	Approved
0.8365	Intermediate Similarity	NPD5701	Approved
0.8351	Intermediate Similarity	NPD6079	Approved
0.8333	Intermediate Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD5211	Phase 2
0.8302	Intermediate Similarity	NPD6883	Approved
0.8302	Intermediate Similarity	NPD7102	Approved
0.8302	Intermediate Similarity	NPD7290	Approved
0.8286	Intermediate Similarity	NPD7320	Approved
0.8224	Intermediate Similarity	NPD8130	Phase 1
0.8224	Intermediate Similarity	NPD6869	Approved
0.8224	Intermediate Similarity	NPD6617	Approved
0.8224	Intermediate Similarity	NPD6847	Approved
0.8211	Intermediate Similarity	NPD3618	Phase 1
0.82	Intermediate Similarity	NPD5222	Approved
0.82	Intermediate Similarity	NPD5221	Approved
0.82	Intermediate Similarity	NPD4697	Phase 3
0.82	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7115	Discovery
0.8173	Intermediate Similarity	NPD5141	Approved
0.8148	Intermediate Similarity	NPD8297	Approved
0.8148	Intermediate Similarity	NPD6882	Approved
0.8137	Intermediate Similarity	NPD4696	Approved
0.8137	Intermediate Similarity	NPD5286	Approved
0.8137	Intermediate Similarity	NPD5285	Approved
0.8119	Intermediate Similarity	NPD7902	Approved
0.8119	Intermediate Similarity	NPD4755	Approved
0.8119	Intermediate Similarity	NPD5173	Approved
0.8095	Intermediate Similarity	NPD6008	Approved
0.8058	Intermediate Similarity	NPD5223	Approved
0.8056	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD7748	Approved
0.7981	Intermediate Similarity	NPD5224	Approved
0.7981	Intermediate Similarity	NPD5226	Approved
0.7981	Intermediate Similarity	NPD4633	Approved
0.7981	Intermediate Similarity	NPD5225	Approved
0.798	Intermediate Similarity	NPD7515	Phase 2
0.7979	Intermediate Similarity	NPD3667	Approved
0.7961	Intermediate Similarity	NPD7640	Approved
0.7961	Intermediate Similarity	NPD7639	Approved
0.7961	Intermediate Similarity	NPD4700	Approved
0.7928	Intermediate Similarity	NPD6274	Approved
0.7909	Intermediate Similarity	NPD4632	Approved
0.7905	Intermediate Similarity	NPD5175	Approved
0.7905	Intermediate Similarity	NPD5174	Approved
0.79	Intermediate Similarity	NPD4202	Approved
0.7864	Intermediate Similarity	NPD4225	Approved
0.7864	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD6317	Approved
0.7822	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD7900	Approved
0.78	Intermediate Similarity	NPD8035	Phase 2
0.78	Intermediate Similarity	NPD8034	Phase 2
0.7788	Intermediate Similarity	NPD6335	Approved
0.7788	Intermediate Similarity	NPD6314	Approved
0.7788	Intermediate Similarity	NPD6313	Approved
0.7768	Intermediate Similarity	NPD6868	Approved
0.7767	Intermediate Similarity	NPD6083	Phase 2
0.7767	Intermediate Similarity	NPD6084	Phase 2
0.7755	Intermediate Similarity	NPD3573	Approved
0.7739	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD4754	Approved
0.7719	Intermediate Similarity	NPD7100	Approved
0.7719	Intermediate Similarity	NPD7101	Approved
0.7699	Intermediate Similarity	NPD6009	Approved
0.7692	Intermediate Similarity	NPD5696	Approved
0.7677	Intermediate Similarity	NPD6672	Approved
0.7677	Intermediate Similarity	NPD5737	Approved
0.7653	Intermediate Similarity	NPD7521	Approved
0.7653	Intermediate Similarity	NPD7334	Approved
0.7653	Intermediate Similarity	NPD6684	Approved
0.7653	Intermediate Similarity	NPD6409	Approved
0.7653	Intermediate Similarity	NPD7146	Approved
0.7653	Intermediate Similarity	NPD5330	Approved
0.7652	Intermediate Similarity	NPD6319	Approved
0.7629	Intermediate Similarity	NPD3666	Approved
0.7629	Intermediate Similarity	NPD3133	Approved
0.7629	Intermediate Similarity	NPD3665	Phase 1
0.7615	Intermediate Similarity	NPD4729	Approved
0.7615	Intermediate Similarity	NPD5128	Approved
0.7615	Intermediate Similarity	NPD4730	Approved
0.7593	Intermediate Similarity	NPD4767	Approved
0.7593	Intermediate Similarity	NPD4768	Approved
0.7586	Intermediate Similarity	NPD5983	Phase 2
0.7573	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5695	Phase 3
0.7551	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5249	Phase 3
0.7477	Intermediate Similarity	NPD5248	Approved
0.7477	Intermediate Similarity	NPD5135	Approved
0.7477	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5250	Approved
0.7477	Intermediate Similarity	NPD5251	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7477	Intermediate Similarity	NPD5169	Approved
0.7477	Intermediate Similarity	NPD5247	Approved
0.7475	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7604	Phase 2
0.7455	Intermediate Similarity	NPD5168	Approved
0.7451	Intermediate Similarity	NPD5281	Approved
0.7451	Intermediate Similarity	NPD6411	Approved
0.7451	Intermediate Similarity	NPD5284	Approved
0.7449	Intermediate Similarity	NPD3668	Phase 3
0.7436	Intermediate Similarity	NPD6909	Approved
0.7436	Intermediate Similarity	NPD6908	Approved
0.7426	Intermediate Similarity	NPD4753	Phase 2
0.7423	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5217	Approved
0.7411	Intermediate Similarity	NPD5215	Approved
0.7411	Intermediate Similarity	NPD5127	Approved
0.7411	Intermediate Similarity	NPD5216	Approved
0.7404	Intermediate Similarity	NPD5210	Approved
0.7404	Intermediate Similarity	NPD4629	Approved
0.7395	Intermediate Similarity	NPD7492	Approved
0.7379	Intermediate Similarity	NPD5779	Approved
0.7379	Intermediate Similarity	NPD5778	Approved
0.735	Intermediate Similarity	NPD6054	Approved
0.7333	Intermediate Similarity	NPD6336	Discontinued
0.7333	Intermediate Similarity	NPD6616	Approved
0.7315	Intermediate Similarity	NPD7632	Discontinued
0.7308	Intermediate Similarity	NPD6001	Approved
0.73	Intermediate Similarity	NPD5279	Phase 3
0.7288	Intermediate Similarity	NPD6016	Approved
0.7288	Intermediate Similarity	NPD6015	Approved
0.7282	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD7078	Approved
0.7255	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6101	Approved
0.7255	Intermediate Similarity	NPD6904	Approved
0.7255	Intermediate Similarity	NPD6673	Approved
0.7255	Intermediate Similarity	NPD6080	Approved
0.7245	Intermediate Similarity	NPD4221	Approved
0.7245	Intermediate Similarity	NPD4223	Phase 3
0.7238	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5988	Approved
0.7227	Intermediate Similarity	NPD6370	Approved
0.7217	Intermediate Similarity	NPD5167	Approved
0.7216	Intermediate Similarity	NPD4695	Discontinued
0.7216	Intermediate Similarity	NPD7525	Registered
0.7213	Intermediate Similarity	NPD7736	Approved
0.7203	Intermediate Similarity	NPD6059	Approved
0.7193	Intermediate Similarity	NPD6053	Discontinued
0.719	Intermediate Similarity	NPD7507	Approved
0.7188	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5785	Approved
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD6686	Approved
0.7131	Intermediate Similarity	NPD8293	Discontinued
0.7129	Intermediate Similarity	NPD6098	Approved
0.7129	Intermediate Similarity	NPD4623	Approved
0.7129	Intermediate Similarity	NPD5786	Approved
0.7129	Intermediate Similarity	NPD4519	Discontinued
0.7115	Intermediate Similarity	NPD7637	Suspended
0.71	Intermediate Similarity	NPD4197	Approved
0.7083	Intermediate Similarity	NPD6116	Phase 1
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7053	Intermediate Similarity	NPD7339	Approved
0.7053	Intermediate Similarity	NPD6942	Approved
0.703	Intermediate Similarity	NPD5329	Approved
0.703	Intermediate Similarity	NPD5363	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.7019	Intermediate Similarity	NPD5692	Phase 3
0.7019	Intermediate Similarity	NPD5207	Approved
0.7016	Intermediate Similarity	NPD7319	Approved
0.7	Intermediate Similarity	NPD5362	Discontinued
0.7	Intermediate Similarity	NPD4788	Approved
0.6991	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6117	Approved
0.6961	Remote Similarity	NPD4688	Approved
0.6961	Remote Similarity	NPD5690	Phase 2
0.6961	Remote Similarity	NPD5205	Approved
0.6961	Remote Similarity	NPD4138	Approved
0.6961	Remote Similarity	NPD4693	Phase 3
0.6961	Remote Similarity	NPD4690	Approved
0.6961	Remote Similarity	NPD4689	Approved
0.6952	Remote Similarity	NPD6050	Approved
0.6952	Remote Similarity	NPD5694	Approved
0.693	Remote Similarity	NPD8132	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