NPASS Compound

Structure

CID45365 OpenBabel06191715382D 30 34 0 0 1 0 0 0 0 0999 V2000 -8.2070 -4.6193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3113 -0.5737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1011 -0.9581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5660 0.5062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0305 -2.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6901 -1.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0699 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2252 -3.4144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4574 -2.1512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3800 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8455 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2252 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6904 0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6643 -3.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6339 -3.8306 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9148 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5353 -1.4635 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0704 -1.9518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3805 -1.9515 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5353 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4878 -2.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9755 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 -4.2252 -1.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6901 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0913 -3.1438 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8657 1.4755 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 5 10 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 7 22 2 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 1 1 1 0 0 0 17 2 1 1 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 6 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 6 0 0 0 21 27 1 6 0 0 0 22 25 1 0 0 0 0 22 27 1 0 0 0 0 23 28 2 0 0 0 0 24 25 1 0 0 0 0 24 29 1 6 0 0 0 25 30 1 6 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	413.33
Volume:	456.07
LogP:	5.58
LogD:	4.748
LogS:	-5.479
# Rotatable Bonds:	2
TPSA:	52.82
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	5.078
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.711
MDCK Permeability:	1.682377842371352e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.776
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.261

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.29
Plasma Protein Binding (PPB):	95.6896743774414%
Volume Distribution (VD):	1.078
Pgp-substrate:	1.939697504043579%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.245
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.678
CYP2C9-inhibitor:	0.208
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.327
CYP2D6-substrate:	0.674
CYP3A4-inhibitor:	0.866
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	8.089
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.899
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.622
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.648
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.91
Carcinogencity:	0.712
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC45365

Natural Product ID:	NPC45365
*Common Name:**	[(3S,4R,20S,25S)-22,26-Iminocholesta-5,22(N)-Dien-3,4-Diol
IUPAC Name:	(3S,4R,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(1S)-1-[(3S)-3-methyl-2,3,4,5-tetrahydropyridin-6-yl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
Synonyms:	4beta-hydroxyverazine
Standard InCHIKey:	BLVNKXGGFFUMSS-CGYGGFEXSA-N
Standard InCHI:	InChI=1S/C27H43NO2/c1-16-5-10-23(28-15-16)17(2)19-8-9-20-18-6-7-22-25(30)24(29)12-14-27(22,4)21(18)11-13-26(19,20)3/h7,16-21,24-25,29-30H,5-6,8-15H2,1-4H3/t16-,17-,18-,19+,20-,21-,24-,25+,26+,27+/m0/s1
SMILES:	C[C@H]1CCC(=NC1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517301
PubChem CID:	10597860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002732] 22,26-epiminocholestanes

*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
NPO33146	eclipta alba	Species	n.a.	Eukaryota	n.a.	suriname rainforest1	n.a.	PMID[9784152]
NPO15546	Herba ecliptae prostratae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	2
Others	3

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT726	Cell Line	M109	Mus musculus	IC50	=	15.5	ug.mL-1	PMID[556253]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	12.0	ug ml-1	PMID[556253]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	10.0	ug ml-1	PMID[556253]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	50.0	ug ml-1	PMID[556253]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	100.0	ug.mL-1	PMID[556253]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	200.0	ug.mL-1	PMID[556253]

☑ 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 NPC45365 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	98
0.1-0.2	767
0.2-0.3	5022
0.3-0.4	18699
0.4-0.5	9888
0.5-0.6	6466
0.6-0.7	1566
0.7-0.8	183
0.8-0.85	3
0.85-0.9	0
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC293299
0.9158	High Similarity	NPC243985
0.9158	High Similarity	NPC280710
0.9072	High Similarity	NPC240650
0.835	Intermediate Similarity	NPC50815
0.8173	Intermediate Similarity	NPC247060
0.8173	Intermediate Similarity	NPC471083
0.8105	Intermediate Similarity	NPC317458
0.7961	Intermediate Similarity	NPC140300
0.7925	Intermediate Similarity	NPC474583
0.7732	Intermediate Similarity	NPC474634
0.7708	Intermediate Similarity	NPC474531
0.7708	Intermediate Similarity	NPC192456
0.77	Intermediate Similarity	NPC474668
0.77	Intermediate Similarity	NPC34754
0.7684	Intermediate Similarity	NPC28862
0.7684	Intermediate Similarity	NPC109546
0.7684	Intermediate Similarity	NPC30986
0.7684	Intermediate Similarity	NPC47982
0.7684	Intermediate Similarity	NPC209430
0.7684	Intermediate Similarity	NPC84694
0.7684	Intermediate Similarity	NPC143182
0.7684	Intermediate Similarity	NPC81306
0.7653	Intermediate Similarity	NPC185568
0.7624	Intermediate Similarity	NPC477606
0.7615	Intermediate Similarity	NPC55462
0.7604	Intermediate Similarity	NPC236112
0.7604	Intermediate Similarity	NPC234193
0.76	Intermediate Similarity	NPC470620
0.7579	Intermediate Similarity	NPC474216
0.7545	Intermediate Similarity	NPC25340
0.7526	Intermediate Similarity	NPC23852
0.7526	Intermediate Similarity	NPC209620
0.7526	Intermediate Similarity	NPC264245
0.7525	Intermediate Similarity	NPC316186
0.7525	Intermediate Similarity	NPC133588
0.75	Intermediate Similarity	NPC328714
0.75	Intermediate Similarity	NPC472359
0.7455	Intermediate Similarity	NPC258130
0.7453	Intermediate Similarity	NPC474164
0.7451	Intermediate Similarity	NPC470361
0.7449	Intermediate Similarity	NPC49964
0.7449	Intermediate Similarity	NPC50964
0.7449	Intermediate Similarity	NPC189972
0.7449	Intermediate Similarity	NPC101462
0.7423	Intermediate Similarity	NPC209944
0.7423	Intermediate Similarity	NPC164840
0.7423	Intermediate Similarity	NPC241290
0.74	Intermediate Similarity	NPC75810
0.7396	Intermediate Similarity	NPC473943
0.7396	Intermediate Similarity	NPC167891
0.7396	Intermediate Similarity	NPC83351
0.7395	Intermediate Similarity	NPC469943
0.7387	Intermediate Similarity	NPC169375
0.7383	Intermediate Similarity	NPC91604
0.7379	Intermediate Similarity	NPC80561
0.7379	Intermediate Similarity	NPC204188
0.7379	Intermediate Similarity	NPC329596
0.7379	Intermediate Similarity	NPC11216
0.7379	Intermediate Similarity	NPC3345
0.7379	Intermediate Similarity	NPC291484
0.7374	Intermediate Similarity	NPC475789
0.7368	Intermediate Similarity	NPC321381
0.7368	Intermediate Similarity	NPC107059
0.7368	Intermediate Similarity	NPC321016
0.7368	Intermediate Similarity	NPC56796
0.7368	Intermediate Similarity	NPC247325
0.7368	Intermediate Similarity	NPC244488
0.7358	Intermediate Similarity	NPC476903
0.7353	Intermediate Similarity	NPC67872
0.7347	Intermediate Similarity	NPC474683
0.7347	Intermediate Similarity	NPC82986
0.7347	Intermediate Similarity	NPC474759
0.7347	Intermediate Similarity	NPC7505
0.7347	Intermediate Similarity	NPC474752
0.7347	Intermediate Similarity	NPC474731
0.7347	Intermediate Similarity	NPC47761
0.7345	Intermediate Similarity	NPC328052
0.7339	Intermediate Similarity	NPC176012
0.7333	Intermediate Similarity	NPC477605
0.7333	Intermediate Similarity	NPC473314
0.7327	Intermediate Similarity	NPC261266
0.7327	Intermediate Similarity	NPC477604
0.7327	Intermediate Similarity	NPC94462
0.7327	Intermediate Similarity	NPC6391
0.7308	Intermediate Similarity	NPC41554
0.7308	Intermediate Similarity	NPC97404
0.73	Intermediate Similarity	NPC474047
0.73	Intermediate Similarity	NPC238485
0.73	Intermediate Similarity	NPC205845
0.7292	Intermediate Similarity	NPC318495
0.7292	Intermediate Similarity	NPC155986
0.7292	Intermediate Similarity	NPC198968
0.7282	Intermediate Similarity	NPC105495
0.7273	Intermediate Similarity	NPC470049
0.7273	Intermediate Similarity	NPC87489
0.7273	Intermediate Similarity	NPC296701
0.7273	Intermediate Similarity	NPC90538
0.7273	Intermediate Similarity	NPC30166
0.7273	Intermediate Similarity	NPC218616
0.7273	Intermediate Similarity	NPC5985
0.7273	Intermediate Similarity	NPC202389
0.7263	Intermediate Similarity	NPC136188
0.7263	Intermediate Similarity	NPC304309
0.7263	Intermediate Similarity	NPC162742
0.7263	Intermediate Similarity	NPC28657
0.7263	Intermediate Similarity	NPC257347
0.7263	Intermediate Similarity	NPC288035
0.7263	Intermediate Similarity	NPC141071
0.7263	Intermediate Similarity	NPC230301
0.7263	Intermediate Similarity	NPC22105
0.7263	Intermediate Similarity	NPC134847
0.7263	Intermediate Similarity	NPC471723
0.7263	Intermediate Similarity	NPC285893
0.7245	Intermediate Similarity	NPC13554
0.7232	Intermediate Similarity	NPC46981
0.7228	Intermediate Similarity	NPC266511
0.7228	Intermediate Similarity	NPC274448
0.7216	Intermediate Similarity	NPC477522
0.7216	Intermediate Similarity	NPC275910
0.7216	Intermediate Similarity	NPC87604
0.7207	Intermediate Similarity	NPC212874
0.72	Intermediate Similarity	NPC246956
0.72	Intermediate Similarity	NPC470384
0.72	Intermediate Similarity	NPC207013
0.7196	Intermediate Similarity	NPC289140
0.7188	Intermediate Similarity	NPC300324
0.7188	Intermediate Similarity	NPC134330
0.7188	Intermediate Similarity	NPC129165
0.7188	Intermediate Similarity	NPC240604
0.7188	Intermediate Similarity	NPC113733
0.7188	Intermediate Similarity	NPC189883
0.7184	Intermediate Similarity	NPC471952
0.7184	Intermediate Similarity	NPC280556
0.7158	Intermediate Similarity	NPC469534
0.7158	Intermediate Similarity	NPC469593
0.7158	Intermediate Similarity	NPC469533
0.7157	Intermediate Similarity	NPC293287
0.7157	Intermediate Similarity	NPC152808
0.7156	Intermediate Similarity	NPC275686
0.7143	Intermediate Similarity	NPC1319
0.7129	Intermediate Similarity	NPC209802
0.7129	Intermediate Similarity	NPC231310
0.7129	Intermediate Similarity	NPC470077
0.7113	Intermediate Similarity	NPC34019
0.7113	Intermediate Similarity	NPC91594
0.7113	Intermediate Similarity	NPC214570
0.7107	Intermediate Similarity	NPC478138
0.7103	Intermediate Similarity	NPC476894
0.71	Intermediate Similarity	NPC248886
0.71	Intermediate Similarity	NPC224072
0.7087	Intermediate Similarity	NPC149224
0.7083	Intermediate Similarity	NPC477923
0.7083	Intermediate Similarity	NPC66566
0.7075	Intermediate Similarity	NPC310013
0.7075	Intermediate Similarity	NPC109305
0.7071	Intermediate Similarity	NPC22403
0.7071	Intermediate Similarity	NPC295131
0.7071	Intermediate Similarity	NPC26117
0.7059	Intermediate Similarity	NPC157257
0.7059	Intermediate Similarity	NPC470360
0.7059	Intermediate Similarity	NPC318390
0.7054	Intermediate Similarity	NPC119329
0.7048	Intermediate Similarity	NPC295668
0.7048	Intermediate Similarity	NPC14380
0.7041	Intermediate Similarity	NPC18603
0.7041	Intermediate Similarity	NPC102708
0.7041	Intermediate Similarity	NPC138621
0.7041	Intermediate Similarity	NPC476314
0.7041	Intermediate Similarity	NPC285761
0.7041	Intermediate Similarity	NPC167037
0.7041	Intermediate Similarity	NPC307965
0.7041	Intermediate Similarity	NPC244385
0.7041	Intermediate Similarity	NPC477514
0.7041	Intermediate Similarity	NPC76931
0.7041	Intermediate Similarity	NPC6978
0.7037	Intermediate Similarity	NPC288970
0.7037	Intermediate Similarity	NPC72204
0.703	Intermediate Similarity	NPC82623
0.7018	Intermediate Similarity	NPC159367
0.701	Intermediate Similarity	NPC470362
0.701	Intermediate Similarity	NPC202642
0.701	Intermediate Similarity	NPC477925
0.701	Intermediate Similarity	NPC73875
0.701	Intermediate Similarity	NPC237460
0.701	Intermediate Similarity	NPC46160
0.701	Intermediate Similarity	NPC274079
0.701	Intermediate Similarity	NPC96319
0.7009	Intermediate Similarity	NPC65402
0.7009	Intermediate Similarity	NPC127718
0.7	Intermediate Similarity	NPC470383
0.7	Intermediate Similarity	NPC6707
0.7	Intermediate Similarity	NPC476646
0.699	Remote Similarity	NPC24277
0.699	Remote Similarity	NPC166458
0.699	Remote Similarity	NPC125399
0.699	Remote Similarity	NPC269058
0.699	Remote Similarity	NPC299068
0.699	Remote Similarity	NPC71520
0.6981	Remote Similarity	NPC275671

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 NPC45365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	95
0.1-0.2	484
0.2-0.3	3063
0.3-0.4	4082
0.4-0.5	1041
0.5-0.6	299
0.6-0.7	79
0.7-0.8	7
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
0.767	Intermediate Similarity	NPD5771	Approved
0.7263	Intermediate Similarity	NPD7339	Approved
0.7263	Intermediate Similarity	NPD6942	Approved
0.701	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7525	Registered
0.6857	Remote Similarity	NPD4723	Approved
0.6857	Remote Similarity	NPD4722	Approved
0.6842	Remote Similarity	NPD6640	Phase 3
0.6837	Remote Similarity	NPD6933	Approved
0.6796	Remote Similarity	NPD4786	Approved
0.6697	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6404	Discontinued
0.6634	Remote Similarity	NPD7645	Phase 2
0.6634	Remote Similarity	NPD6929	Approved
0.6633	Remote Similarity	NPD6924	Approved
0.6633	Remote Similarity	NPD6926	Approved
0.6604	Remote Similarity	NPD7524	Approved
0.6602	Remote Similarity	NPD3667	Approved
0.6569	Remote Similarity	NPD6930	Phase 2
0.6569	Remote Similarity	NPD6931	Approved
0.65	Remote Similarity	NPD1346	Approved
0.6491	Remote Similarity	NPD4159	Approved
0.6481	Remote Similarity	NPD5328	Approved
0.6471	Remote Similarity	NPD6420	Discontinued
0.6465	Remote Similarity	NPD4785	Approved
0.6465	Remote Similarity	NPD4784	Approved
0.6436	Remote Similarity	NPD5776	Phase 2
0.6436	Remote Similarity	NPD6925	Approved
0.6429	Remote Similarity	NPD7152	Approved
0.6429	Remote Similarity	NPD7150	Approved
0.6429	Remote Similarity	NPD7151	Approved
0.6429	Remote Similarity	NPD4243	Approved
0.6408	Remote Similarity	NPD4748	Discontinued
0.6408	Remote Similarity	NPD7514	Phase 3
0.64	Remote Similarity	NPD8264	Approved
0.6392	Remote Similarity	NPD6923	Approved
0.6392	Remote Similarity	NPD6922	Approved
0.6381	Remote Similarity	NPD6695	Phase 3
0.6373	Remote Similarity	NPD7145	Approved
0.6373	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6079	Approved
0.6355	Remote Similarity	NPD3618	Phase 1
0.6346	Remote Similarity	NPD6902	Approved
0.6327	Remote Similarity	NPD7144	Approved
0.6327	Remote Similarity	NPD7143	Approved
0.6327	Remote Similarity	NPD6939	Phase 2
0.6327	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7115	Discovery
0.6289	Remote Similarity	NPD6705	Phase 1
0.6273	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7333	Discontinued
0.6262	Remote Similarity	NPD6893	Approved
0.625	Remote Similarity	NPD7509	Discontinued
0.625	Remote Similarity	NPD7332	Phase 2
0.625	Remote Similarity	NPD5707	Approved
0.6168	Remote Similarity	NPD3133	Approved
0.6168	Remote Similarity	NPD3665	Phase 1
0.6168	Remote Similarity	NPD3666	Approved
0.6161	Remote Similarity	NPD4202	Approved
0.6161	Remote Similarity	NPD6399	Phase 3
0.6147	Remote Similarity	NPD7750	Discontinued
0.6126	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6700	Approved
0.6121	Remote Similarity	NPD7640	Approved
0.6121	Remote Similarity	NPD8418	Phase 2
0.6121	Remote Similarity	NPD7639	Approved
0.6119	Remote Similarity	NPD8449	Approved
0.6117	Remote Similarity	NPD6932	Approved
0.6111	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5275	Approved
0.6078	Remote Similarity	NPD4190	Phase 3
0.6074	Remote Similarity	NPD8450	Suspended
0.6038	Remote Similarity	NPD6898	Phase 1
0.6034	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD3668	Phase 3
0.6017	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5357	Phase 1
0.6	Remote Similarity	NPD5221	Approved
0.5948	Remote Similarity	NPD4755	Approved
0.5948	Remote Similarity	NPD5173	Approved
0.5929	Remote Similarity	NPD6703	Approved
0.5929	Remote Similarity	NPD7087	Discontinued
0.5929	Remote Similarity	NPD7515	Phase 2
0.5929	Remote Similarity	NPD6702	Approved
0.5917	Remote Similarity	NPD5141	Approved
0.5909	Remote Similarity	NPD5279	Phase 3
0.5903	Remote Similarity	NPD7625	Phase 1
0.59	Remote Similarity	NPD15	Approved
0.59	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.59	Remote Similarity	NPD791	Approved
0.5897	Remote Similarity	NPD4225	Approved
0.5893	Remote Similarity	NPD4753	Phase 2
0.5893	Remote Similarity	NPD6051	Approved
0.5847	Remote Similarity	NPD4700	Approved
0.5847	Remote Similarity	NPD4696	Approved
0.5847	Remote Similarity	NPD5285	Approved
0.5847	Remote Similarity	NPD5286	Approved
0.5846	Remote Similarity	NPD6909	Approved
0.5846	Remote Similarity	NPD6908	Approved
0.5833	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD4223	Phase 3
0.5818	Remote Similarity	NPD5329	Approved
0.5814	Remote Similarity	NPD7516	Approved
0.5798	Remote Similarity	NPD5223	Approved
0.5789	Remote Similarity	NPD7637	Suspended
0.5772	Remote Similarity	NPD8174	Phase 2
0.5772	Remote Similarity	NPD6406	Approved
0.5763	Remote Similarity	NPD5290	Discontinued
0.575	Remote Similarity	NPD5224	Approved
0.575	Remote Similarity	NPD5225	Approved
0.575	Remote Similarity	NPD5226	Approved
0.575	Remote Similarity	NPD4633	Approved
0.5739	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6675	Approved
0.5738	Remote Similarity	NPD5739	Approved
0.5738	Remote Similarity	NPD7128	Approved
0.5738	Remote Similarity	NPD6402	Approved
0.5736	Remote Similarity	NPD7327	Approved
0.5736	Remote Similarity	NPD7328	Approved
0.5735	Remote Similarity	NPD6914	Discontinued
0.5727	Remote Similarity	NPD4197	Approved
0.5725	Remote Similarity	NPD7503	Approved
0.5725	Remote Similarity	NPD8033	Approved
0.5702	Remote Similarity	NPD5174	Approved
0.5702	Remote Similarity	NPD5175	Approved
0.5702	Remote Similarity	NPD4754	Approved
0.5692	Remote Similarity	NPD7522	Discontinued
0.5691	Remote Similarity	NPD6412	Phase 2
0.569	Remote Similarity	NPD7748	Approved
0.568	Remote Similarity	NPD4634	Approved
0.568	Remote Similarity	NPD6421	Discontinued
0.5678	Remote Similarity	NPD6084	Phase 2
0.5678	Remote Similarity	NPD6083	Phase 2
0.5674	Remote Similarity	NPD6334	Approved
0.5674	Remote Similarity	NPD6333	Approved
0.5664	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8034	Phase 2
0.5652	Remote Similarity	NPD8035	Phase 2
0.5649	Remote Similarity	NPD8377	Approved
0.5649	Remote Similarity	NPD8294	Approved
0.5645	Remote Similarity	NPD6899	Approved
0.5645	Remote Similarity	NPD6881	Approved
0.5645	Remote Similarity	NPD7320	Approved
0.5641	Remote Similarity	NPD5210	Approved
0.5641	Remote Similarity	NPD4629	Approved
0.5636	Remote Similarity	NPD4788	Approved
0.5625	Remote Similarity	NPD7521	Approved
0.5625	Remote Similarity	NPD4138	Approved
0.5625	Remote Similarity	NPD4519	Discontinued
0.5625	Remote Similarity	NPD7146	Approved
0.5625	Remote Similarity	NPD7334	Approved
0.5625	Remote Similarity	NPD4623	Approved
0.5625	Remote Similarity	NPD5330	Approved
0.5625	Remote Similarity	NPD6409	Approved
0.5625	Remote Similarity	NPD4689	Approved
0.5625	Remote Similarity	NPD6684	Approved
0.5625	Remote Similarity	NPD4690	Approved
0.5625	Remote Similarity	NPD4688	Approved
0.5625	Remote Similarity	NPD4693	Phase 3
0.5625	Remote Similarity	NPD5205	Approved
0.562	Remote Similarity	NPD7632	Discontinued
0.561	Remote Similarity	NPD4768	Approved
0.561	Remote Similarity	NPD4767	Approved
0.5606	Remote Similarity	NPD8378	Approved
0.5606	Remote Similarity	NPD8380	Approved
0.5606	Remote Similarity	NPD8296	Approved
0.5606	Remote Similarity	NPD8379	Approved
0.5606	Remote Similarity	NPD8335	Approved
0.56	Remote Similarity	NPD6373	Approved
0.56	Remote Similarity	NPD6372	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