NPASS Compound

Structure

CID61011 OpenBabel06191715392D 24 26 0 0 0 0 0 0 0 0999 V2000 -2.3465 -3.1261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9868 -2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5623 3.0750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0815 2.7260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2421 0.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5213 1.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3616 0.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5219 -1.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9517 -2.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8412 2.4260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6807 0.9711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5217 -0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6809 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8410 1.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6809 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 1.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 0.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3618 0.0007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8403 2.4561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 1.4703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5210 -0.4856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 5 24 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.16
Volume:	341.42
LogP:	3.431
LogD:	2.593
LogS:	-5.051
# Rotatable Bonds:	4
TPSA:	61.19
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	3.089
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.649
MDCK Permeability:	2.3370939743472263e-05
Pgp-inhibitor:	0.154
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.353

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	93.56780242919922%
Volume Distribution (VD):	1.151
Pgp-substrate:	3.702522039413452%

ADMET: Metabolism

CYP1A2-inhibitor:	0.403
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.902
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.938
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.761
CYP3A4-substrate:	0.854

ADMET: Excretion

Clearance (CL):	1.241
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.713
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.078
Carcinogencity:	0.735
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC61011

Natural Product ID:	NPC61011
*Common Name:**	Pterocellin D
IUPAC Name:	8-methoxy-1-(2-methylpropyl)-6-propan-2-ylpyrido[4,3-b]indolizine-5,7-dione
Synonyms:	Pterocellin D
Standard InCHIKey:	YQHVSSSUUIVBQC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22N2O3/c1-10(2)8-13-16-12(6-7-20-13)18(22)17-15(11(3)4)19(23)14(24-5)9-21(16)17/h6-7,9-11H,8H2,1-5H3
SMILES:	COc1cn2c3c(nccc3C(=O)c2c(c1=O)C(C)C)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257382
PubChem CID:	24770102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001322] Pyridinecarboxylic 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
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	Alderman Islands off the North Island of New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19220033]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26055	Relhania fruticosa	Species	Asteraceae	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
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	4.773	ug.mL-1	PMID[545852]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.5	ug	PMID[545852]

☑ 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 NPC61011 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	492
0.1-0.2	3585
0.2-0.3	12876
0.3-0.4	6759
0.4-0.5	14475
0.5-0.6	2820
0.6-0.7	1509
0.7-0.8	168
0.8-0.85	6
0.85-0.9	2
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC83774
0.9816	High Similarity	NPC46895
0.9512	High Similarity	NPC73994
0.904	High Similarity	NPC121327
0.8939	High Similarity	NPC143977
0.8667	High Similarity	NPC81535
0.7955	Intermediate Similarity	NPC469529
0.7933	Intermediate Similarity	NPC191415
0.7917	Intermediate Similarity	NPC470679
0.7917	Intermediate Similarity	NPC217021
0.7917	Intermediate Similarity	NPC70406
0.7765	Intermediate Similarity	NPC251391
0.7759	Intermediate Similarity	NPC265100
0.7749	Intermediate Similarity	NPC472062
0.7749	Intermediate Similarity	NPC472063
0.7749	Intermediate Similarity	NPC472069
0.7738	Intermediate Similarity	NPC105811
0.7725	Intermediate Similarity	NPC467188
0.7722	Intermediate Similarity	NPC12649
0.7701	Intermediate Similarity	NPC326422
0.7701	Intermediate Similarity	NPC242116
0.7692	Intermediate Similarity	NPC123906
0.7692	Intermediate Similarity	NPC102755
0.7672	Intermediate Similarity	NPC106824
0.767	Intermediate Similarity	NPC114637
0.7663	Intermediate Similarity	NPC118084
0.7647	Intermediate Similarity	NPC473878
0.7647	Intermediate Similarity	NPC313889
0.7644	Intermediate Similarity	NPC100104
0.7644	Intermediate Similarity	NPC470680
0.7629	Intermediate Similarity	NPC472064
0.7629	Intermediate Similarity	NPC472065
0.7627	Intermediate Similarity	NPC70949
0.7619	Intermediate Similarity	NPC472116
0.7616	Intermediate Similarity	NPC209362
0.7592	Intermediate Similarity	NPC284338
0.7586	Intermediate Similarity	NPC80681
0.7577	Intermediate Similarity	NPC472259
0.7569	Intermediate Similarity	NPC284775
0.7557	Intermediate Similarity	NPC478182
0.7554	Intermediate Similarity	NPC477003
0.7539	Intermediate Similarity	NPC474916
0.7529	Intermediate Similarity	NPC100726
0.7526	Intermediate Similarity	NPC317701
0.7513	Intermediate Similarity	NPC267343
0.75	Intermediate Similarity	NPC237414
0.7487	Intermediate Similarity	NPC167710
0.7486	Intermediate Similarity	NPC474492
0.7486	Intermediate Similarity	NPC65080
0.7447	Intermediate Similarity	NPC154339
0.7429	Intermediate Similarity	NPC213914
0.7424	Intermediate Similarity	NPC472070
0.7419	Intermediate Similarity	NPC282103
0.7416	Intermediate Similarity	NPC233380
0.7414	Intermediate Similarity	NPC229055
0.7407	Intermediate Similarity	NPC476460
0.7407	Intermediate Similarity	NPC114974
0.7399	Intermediate Similarity	NPC472260
0.7391	Intermediate Similarity	NPC471997
0.7386	Intermediate Similarity	NPC293487
0.7377	Intermediate Similarity	NPC157583
0.7374	Intermediate Similarity	NPC266249
0.7371	Intermediate Similarity	NPC74357
0.7368	Intermediate Similarity	NPC216550
0.7366	Intermediate Similarity	NPC258480
0.7358	Intermediate Similarity	NPC168911
0.7354	Intermediate Similarity	NPC324091
0.7344	Intermediate Similarity	NPC128244
0.7344	Intermediate Similarity	NPC472293
0.7344	Intermediate Similarity	NPC102592
0.7344	Intermediate Similarity	NPC79356
0.7322	Intermediate Similarity	NPC151635
0.732	Intermediate Similarity	NPC74413
0.7318	Intermediate Similarity	NPC42372
0.7316	Intermediate Similarity	NPC117244
0.7316	Intermediate Similarity	NPC473763
0.7305	Intermediate Similarity	NPC65408
0.73	Intermediate Similarity	NPC123839
0.7296	Intermediate Similarity	NPC57398
0.7292	Intermediate Similarity	NPC135950
0.7292	Intermediate Similarity	NPC202812
0.7283	Intermediate Similarity	NPC234987
0.7278	Intermediate Similarity	NPC41717
0.7278	Intermediate Similarity	NPC478183
0.7278	Intermediate Similarity	NPC56233
0.7277	Intermediate Similarity	NPC472292
0.7277	Intermediate Similarity	NPC47190
0.7273	Intermediate Similarity	NPC238457
0.7273	Intermediate Similarity	NPC228835
0.7268	Intermediate Similarity	NPC293216
0.7268	Intermediate Similarity	NPC212213
0.7263	Intermediate Similarity	NPC478184
0.7263	Intermediate Similarity	NPC469489
0.7257	Intermediate Similarity	NPC281094
0.7241	Intermediate Similarity	NPC471655
0.724	Intermediate Similarity	NPC304203
0.7234	Intermediate Similarity	NPC133003
0.7231	Intermediate Similarity	NPC103361
0.7231	Intermediate Similarity	NPC472297
0.7231	Intermediate Similarity	NPC472296
0.7225	Intermediate Similarity	NPC138370
0.7219	Intermediate Similarity	NPC159125
0.7213	Intermediate Similarity	NPC252572
0.7208	Intermediate Similarity	NPC260900
0.7207	Intermediate Similarity	NPC478185
0.7204	Intermediate Similarity	NPC477042
0.7198	Intermediate Similarity	NPC32534
0.7196	Intermediate Similarity	NPC66210
0.7189	Intermediate Similarity	NPC237188
0.7179	Intermediate Similarity	NPC239954
0.7171	Intermediate Similarity	NPC27041
0.715	Intermediate Similarity	NPC81802
0.715	Intermediate Similarity	NPC472295
0.715	Intermediate Similarity	NPC198673
0.715	Intermediate Similarity	NPC247735
0.715	Intermediate Similarity	NPC269886
0.715	Intermediate Similarity	NPC472210
0.7143	Intermediate Similarity	NPC295158
0.7143	Intermediate Similarity	NPC123395
0.7136	Intermediate Similarity	NPC88115
0.7129	Intermediate Similarity	NPC122436
0.7121	Intermediate Similarity	NPC106757
0.712	Intermediate Similarity	NPC255909
0.7118	Intermediate Similarity	NPC471574
0.7112	Intermediate Similarity	NPC24864
0.7104	Intermediate Similarity	NPC471943
0.7104	Intermediate Similarity	NPC91895
0.7101	Intermediate Similarity	NPC472288
0.709	Intermediate Similarity	NPC207851
0.709	Intermediate Similarity	NPC467063
0.7086	Intermediate Similarity	NPC102664
0.7083	Intermediate Similarity	NPC472112
0.7081	Intermediate Similarity	NPC469938
0.7081	Intermediate Similarity	NPC139763
0.7077	Intermediate Similarity	NPC109922
0.7074	Intermediate Similarity	NPC470677
0.7074	Intermediate Similarity	NPC113626
0.7072	Intermediate Similarity	NPC21174
0.7072	Intermediate Similarity	NPC271797
0.7072	Intermediate Similarity	NPC274981
0.7065	Intermediate Similarity	NPC249614
0.7065	Intermediate Similarity	NPC262338
0.7059	Intermediate Similarity	NPC11126
0.7059	Intermediate Similarity	NPC118940
0.7059	Intermediate Similarity	NPC248462
0.7056	Intermediate Similarity	NPC477004
0.7053	Intermediate Similarity	NPC476341
0.7051	Intermediate Similarity	NPC101350
0.705	Intermediate Similarity	NPC327592
0.7048	Intermediate Similarity	NPC229893
0.7041	Intermediate Similarity	NPC78767
0.7041	Intermediate Similarity	NPC227582
0.7041	Intermediate Similarity	NPC473814
0.7037	Intermediate Similarity	NPC143533
0.7035	Intermediate Similarity	NPC328318
0.7035	Intermediate Similarity	NPC328596
0.7033	Intermediate Similarity	NPC115232
0.703	Intermediate Similarity	NPC471589
0.703	Intermediate Similarity	NPC116555
0.703	Intermediate Similarity	NPC313823
0.7029	Intermediate Similarity	NPC470111
0.7026	Intermediate Similarity	NPC93390
0.7026	Intermediate Similarity	NPC19692
0.7026	Intermediate Similarity	NPC220151
0.7024	Intermediate Similarity	NPC221100
0.7024	Intermediate Similarity	NPC234078
0.7021	Intermediate Similarity	NPC15840
0.7016	Intermediate Similarity	NPC311858
0.7015	Intermediate Similarity	NPC317373
0.7005	Intermediate Similarity	NPC28848
0.7005	Intermediate Similarity	NPC235685
0.7005	Intermediate Similarity	NPC14325
0.7005	Intermediate Similarity	NPC149708
0.7	Intermediate Similarity	NPC21429
0.6995	Remote Similarity	NPC472752
0.6994	Remote Similarity	NPC136002
0.699	Remote Similarity	NPC292361
0.6979	Remote Similarity	NPC17059
0.6979	Remote Similarity	NPC278434
0.6976	Remote Similarity	NPC471194
0.6976	Remote Similarity	NPC471193
0.6976	Remote Similarity	NPC153980
0.6976	Remote Similarity	NPC6865
0.697	Remote Similarity	NPC474767
0.6966	Remote Similarity	NPC107287
0.6965	Remote Similarity	NPC477043
0.6957	Remote Similarity	NPC470894
0.6954	Remote Similarity	NPC159630
0.6954	Remote Similarity	NPC230085
0.6947	Remote Similarity	NPC243058
0.6943	Remote Similarity	NPC103119
0.6943	Remote Similarity	NPC209917
0.6939	Remote Similarity	NPC157828
0.6939	Remote Similarity	NPC195239
0.6935	Remote Similarity	NPC477976
0.6935	Remote Similarity	NPC252338
0.6932	Remote Similarity	NPC112741
0.6931	Remote Similarity	NPC182940
0.6927	Remote Similarity	NPC90415
0.6927	Remote Similarity	NPC94752

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 NPC61011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	665
0.2-0.3	890
0.3-0.4	1492
0.4-0.5	2904
0.5-0.6	2109
0.6-0.7	750
0.7-0.8	54
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
0.7833	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1343	Approved
0.7814	Intermediate Similarity	NPD4988	Discontinued
0.768	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD5088	Discontinued
0.7633	Intermediate Similarity	NPD1270	Approved
0.75	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2479	Phase 3
0.7486	Intermediate Similarity	NPD2481	Approved
0.7485	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD4848	Phase 1
0.7425	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD460	Discontinued
0.7416	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4524	Discontinued
0.7386	Intermediate Similarity	NPD1630	Approved
0.7376	Intermediate Similarity	NPD3393	Approved
0.7376	Intermediate Similarity	NPD3389	Approved
0.7376	Intermediate Similarity	NPD3394	Approved
0.7374	Intermediate Similarity	NPD2509	Approved
0.7374	Intermediate Similarity	NPD2510	Approved
0.7347	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD3905	Phase 3
0.7316	Intermediate Similarity	NPD2336	Approved
0.731	Intermediate Similarity	NPD6987	Phase 1
0.731	Intermediate Similarity	NPD3947	Discontinued
0.7305	Intermediate Similarity	NPD200	Phase 2
0.7305	Intermediate Similarity	NPD201	Phase 2
0.7296	Intermediate Similarity	NPD2879	Approved
0.7296	Intermediate Similarity	NPD2881	Approved
0.7293	Intermediate Similarity	NPD1575	Approved
0.7293	Intermediate Similarity	NPD1573	Approved
0.7291	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1631	Approved
0.7216	Intermediate Similarity	NPD1952	Discontinued
0.7212	Intermediate Similarity	NPD6173	Approved
0.7207	Intermediate Similarity	NPD5400	Approved
0.72	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6787	Phase 2
0.7186	Intermediate Similarity	NPD272	Approved
0.7182	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2307	Discontinued
0.7157	Intermediate Similarity	NPD5017	Discontinued
0.7152	Intermediate Similarity	NPD3475	Approved
0.7152	Intermediate Similarity	NPD3476	Approved
0.7151	Intermediate Similarity	NPD2511	Approved
0.7151	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4051	Discontinued
0.7127	Intermediate Similarity	NPD2915	Discontinued
0.71	Intermediate Similarity	NPD2008	Discontinued
0.7097	Intermediate Similarity	NPD2753	Discontinued
0.7095	Intermediate Similarity	NPD2214	Approved
0.7095	Intermediate Similarity	NPD2213	Approved
0.709	Intermediate Similarity	NPD1096	Discontinued
0.7088	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2118	Approved
0.7073	Intermediate Similarity	NPD2119	Approved
0.7068	Intermediate Similarity	NPD2770	Discontinued
0.7065	Intermediate Similarity	NPD3839	Phase 2
0.7065	Intermediate Similarity	NPD3840	Phase 2
0.7059	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2896	Discontinued
0.7059	Intermediate Similarity	NPD2411	Approved
0.705	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1658	Discontinued
0.7047	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3238	Discontinued
0.7035	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7187	Phase 2
0.7016	Intermediate Similarity	NPD5444	Phase 1
0.7015	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3431	Approved
0.701	Intermediate Similarity	NPD5475	Discontinued
0.701	Intermediate Similarity	NPD3430	Approved
0.701	Intermediate Similarity	NPD4922	Phase 2
0.7005	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5755	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7482	Phase 2
0.7	Intermediate Similarity	NPD7483	Phase 2
0.6995	Remote Similarity	NPD3321	Discontinued
0.6995	Remote Similarity	NPD1600	Suspended
0.699	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4883	Approved
0.6989	Remote Similarity	NPD1586	Approved
0.6984	Remote Similarity	NPD3178	Discontinued
0.6981	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3583	Phase 2
0.6976	Remote Similarity	NPD6954	Phase 2
0.697	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6999	Discontinued
0.6965	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5072	Discontinued
0.6961	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD715	Phase 3
0.6944	Remote Similarity	NPD820	Phase 3
0.6943	Remote Similarity	NPD5016	Approved
0.6942	Remote Similarity	NPD5888	Phase 2
0.6939	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5020	Approved
0.6932	Remote Similarity	NPD9271	Approved
0.6931	Remote Similarity	NPD3927	Phase 2
0.6931	Remote Similarity	NPD7568	Phase 1
0.6931	Remote Similarity	NPD3967	Approved
0.6931	Remote Similarity	NPD5473	Discontinued
0.6927	Remote Similarity	NPD3315	Phase 3
0.6927	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4940	Approved
0.6923	Remote Similarity	NPD4030	Approved
0.6923	Remote Similarity	NPD4028	Approved
0.6923	Remote Similarity	NPD4376	Phase 3
0.6923	Remote Similarity	NPD5505	Discontinued
0.6923	Remote Similarity	NPD4029	Approved
0.6919	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5513	Phase 2
0.6914	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7564	Discontinued
0.6911	Remote Similarity	NPD721	Approved
0.6911	Remote Similarity	NPD6178	Phase 3
0.6907	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5685	Approved
0.6907	Remote Similarity	NPD5686	Approved
0.6905	Remote Similarity	NPD6242	Discontinued
0.6905	Remote Similarity	NPD1996	Discontinued
0.6902	Remote Similarity	NPD6446	Discontinued
0.69	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3246	Discontinued
0.6884	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD107	Approved
0.6878	Remote Similarity	NPD1587	Approved
0.6875	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4639	Approved
0.6865	Remote Similarity	NPD4638	Approved
0.6865	Remote Similarity	NPD4640	Approved
0.6863	Remote Similarity	NPD7191	Phase 2
0.6862	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5104	Approved
0.6857	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7234	Approved
0.6856	Remote Similarity	NPD7233	Approved
0.6856	Remote Similarity	NPD4334	Discontinued
0.6853	Remote Similarity	NPD7944	Discontinued
0.6851	Remote Similarity	NPD2581	Approved
0.6851	Remote Similarity	NPD2582	Approved
0.6845	Remote Similarity	NPD6152	Phase 1
0.6845	Remote Similarity	NPD750	Phase 2
0.6842	Remote Similarity	NPD1618	Phase 2
0.6837	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4702	Approved
0.6836	Remote Similarity	NPD1661	Suspended
0.6836	Remote Similarity	NPD4703	Approved
0.6833	Remote Similarity	NPD6790	Phase 1
0.6833	Remote Similarity	NPD2809	Approved
0.6829	Remote Similarity	NPD3968	Approved
0.6825	Remote Similarity	NPD5827	Discontinued
0.6821	Remote Similarity	NPD4804	Approved
0.6821	Remote Similarity	NPD4499	Approved
0.6818	Remote Similarity	NPD2289	Phase 3
0.6818	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2290	Phase 3
0.681	Remote Similarity	NPD270	Clinical (unspecified phase)
0.681	Remote Similarity	NPD268	Approved
0.681	Remote Similarity	NPD271	Approved
0.68	Remote Similarity	NPD6239	Discontinued
0.68	Remote Similarity	NPD3717	Discontinued
0.6798	Remote Similarity	NPD5901	Discontinued
0.6798	Remote Similarity	NPD4299	Phase 1
0.6786	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6206	Phase 1
0.6782	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2442	Approved
0.678	Remote Similarity	NPD7665	Phase 2
0.678	Remote Similarity	NPD7666	Phase 3
0.678	Remote Similarity	NPD2443	Approved
0.678	Remote Similarity	NPD7469	Discontinued
0.6768	Remote Similarity	NPD7619	Phase 3
0.6768	Remote Similarity	NPD7618	Phase 3
0.6768	Remote Similarity	NPD4602	Approved
0.6766	Remote Similarity	NPD6479	Discontinued
0.6765	Remote Similarity	NPD7001	Phase 3
0.6762	Remote Similarity	NPD4989	Phase 2
0.6762	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6017	Discontinued

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