NPASS Compound

Structure

CID240650 OpenBabel06191716042D 30 34 0 0 1 0 0 0 0 0999 V2000 4.6247 0.5746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8397 4.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8766 -0.5061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4136 0.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8458 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3823 2.9295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5370 3.4175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8453 -1.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6912 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4045 3.1466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9780 3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5370 0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6914 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3452 2.9427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2279 1.4659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8458 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 -0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3829 1.9538 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6917 1.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8014 2.2553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9484 3.8340 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 2.5370 1.4654 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7717 2.1533 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5571 -1.4757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0503 4.8043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 6 1 0 0 0 0 5 18 2 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 25 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 1 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 29 1 6 0 0 0 20 6 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 6 0 0 0 22 27 1 6 0 0 0 23 26 1 6 0 0 0 24 28 2 0 0 0 0 25 2 1 6 0 0 0 25 30 1 0 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:	5.266
LogD:	4.483
LogS:	-5.519
# 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:	0.583
Synthetic Accessibility Score:	4.997
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:	-4.708
MDCK Permeability:	1.4556975656887516e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.764
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.46
Plasma Protein Binding (PPB):	95.48931884765625%
Volume Distribution (VD):	1.224
Pgp-substrate:	2.038857936859131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.164
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.479
CYP3A4-inhibitor:	0.916
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	10.865
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.294
Human Hepatotoxicity (H-HT):	0.352
Drug-inuced Liver Injury (DILI):	0.226
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.329
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.93
Carcinogencity:	0.879
Eye Corrosion:	0.005
Eye Irritation:	0.026
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC240650

Natural Product ID:	NPC240650
*Common Name:**	[(3S,20S,25R)-22,26-Iminocholesta-5,22(N)-Diene-3,25-Diol
IUPAC Name:	(3R)-6-[(1S)-1-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-methyl-4,5-dihydro-2H-pyridin-3-ol
Synonyms:
Standard InCHIKey:	YCTLKNVWQFQYLE-RRKPGTBZSA-N
Standard InCHI:	InChI=1S/C27H43NO2/c1-17(24-11-12-25(2,30)16-28-24)21-7-8-22-20-6-5-18-15-19(29)9-13-26(18,3)23(20)10-14-27(21,22)4/h5,17,19-23,29-30H,6-16H2,1-4H3/t17-,19-,20-,21+,22-,23-,25+,26-,27+/m0/s1
SMILES:	C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)C1=NC[C@@](C)(CC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463129
PubChem CID:	10549683
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	=	31.2	ug.mL-1	PMID[533972]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	0.35	ug ml-1	PMID[533972]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	2.5	ug ml-1	PMID[533972]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	4.0	ug ml-1	PMID[533972]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	6.25	ug.mL-1	PMID[533972]
NPT20	Organism	Candida albicans	Candida albicans	MIC	<	3.1	ug.mL-1	PMID[533972]

☑ 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 NPC240650 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	82
0.1-0.2	770
0.2-0.3	8940
0.3-0.4	16728
0.4-0.5	8771
0.5-0.6	5878
0.6-0.7	1338
0.7-0.8	182
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC280710
0.9667	High Similarity	NPC243985
0.9072	High Similarity	NPC45365
0.9072	High Similarity	NPC293299
0.84	Intermediate Similarity	NPC50815
0.8317	Intermediate Similarity	NPC474583
0.8218	Intermediate Similarity	NPC247060
0.8039	Intermediate Similarity	NPC471083
0.7935	Intermediate Similarity	NPC192456
0.7905	Intermediate Similarity	NPC25340
0.7889	Intermediate Similarity	NPC155986
0.7889	Intermediate Similarity	NPC318495
0.7889	Intermediate Similarity	NPC198968
0.7822	Intermediate Similarity	NPC474164
0.7789	Intermediate Similarity	NPC75810
0.7778	Intermediate Similarity	NPC321381
0.7778	Intermediate Similarity	NPC107059
0.7778	Intermediate Similarity	NPC321016
0.7745	Intermediate Similarity	NPC91604
0.7723	Intermediate Similarity	NPC476903
0.7717	Intermediate Similarity	NPC328714
0.7706	Intermediate Similarity	NPC56796
0.7692	Intermediate Similarity	NPC176012
0.7667	Intermediate Similarity	NPC162742
0.7667	Intermediate Similarity	NPC134847
0.7667	Intermediate Similarity	NPC28657
0.7667	Intermediate Similarity	NPC136188
0.7667	Intermediate Similarity	NPC22105
0.7667	Intermediate Similarity	NPC285893
0.7667	Intermediate Similarity	NPC230301
0.7667	Intermediate Similarity	NPC288035
0.7667	Intermediate Similarity	NPC304309
0.766	Intermediate Similarity	NPC5985
0.7647	Intermediate Similarity	NPC140300
0.7634	Intermediate Similarity	NPC241290
0.7634	Intermediate Similarity	NPC209944
0.7634	Intermediate Similarity	NPC164840
0.7609	Intermediate Similarity	NPC477522
0.7609	Intermediate Similarity	NPC87604
0.7609	Intermediate Similarity	NPC473943
0.7609	Intermediate Similarity	NPC474216
0.7582	Intermediate Similarity	NPC240604
0.7582	Intermediate Similarity	NPC113733
0.7582	Intermediate Similarity	NPC300324
0.757	Intermediate Similarity	NPC169375
0.7553	Intermediate Similarity	NPC47761
0.7553	Intermediate Similarity	NPC264245
0.7551	Intermediate Similarity	NPC34754
0.7549	Intermediate Similarity	NPC289140
0.7547	Intermediate Similarity	NPC212874
0.7527	Intermediate Similarity	NPC84694
0.7527	Intermediate Similarity	NPC81306
0.7527	Intermediate Similarity	NPC109546
0.7527	Intermediate Similarity	NPC28862
0.7527	Intermediate Similarity	NPC47982
0.7527	Intermediate Similarity	NPC143182
0.75	Intermediate Similarity	NPC275686
0.75	Intermediate Similarity	NPC34019
0.7477	Intermediate Similarity	NPC55462
0.7474	Intermediate Similarity	NPC49964
0.7473	Intermediate Similarity	NPC257347
0.7473	Intermediate Similarity	NPC141071
0.7473	Intermediate Similarity	NPC471723
0.7447	Intermediate Similarity	NPC26117
0.7447	Intermediate Similarity	NPC234193
0.7419	Intermediate Similarity	NPC307965
0.7419	Intermediate Similarity	NPC285761
0.7419	Intermediate Similarity	NPC18603
0.7419	Intermediate Similarity	NPC76931
0.7419	Intermediate Similarity	NPC275910
0.7407	Intermediate Similarity	NPC46981
0.7396	Intermediate Similarity	NPC475789
0.7396	Intermediate Similarity	NPC474634
0.7396	Intermediate Similarity	NPC246956
0.7391	Intermediate Similarity	NPC129165
0.7391	Intermediate Similarity	NPC96319
0.7391	Intermediate Similarity	NPC189883
0.7391	Intermediate Similarity	NPC134330
0.7383	Intermediate Similarity	NPC119329
0.7368	Intermediate Similarity	NPC474759
0.7368	Intermediate Similarity	NPC23852
0.7368	Intermediate Similarity	NPC7505
0.7368	Intermediate Similarity	NPC470383
0.7368	Intermediate Similarity	NPC474752
0.7368	Intermediate Similarity	NPC209620
0.7368	Intermediate Similarity	NPC474683
0.7368	Intermediate Similarity	NPC474531
0.7368	Intermediate Similarity	NPC474731
0.7368	Intermediate Similarity	NPC82986
0.7364	Intermediate Similarity	NPC472359
0.7353	Intermediate Similarity	NPC473314
0.734	Intermediate Similarity	NPC273410
0.734	Intermediate Similarity	NPC1319
0.734	Intermediate Similarity	NPC209430
0.734	Intermediate Similarity	NPC80530
0.734	Intermediate Similarity	NPC30986
0.7339	Intermediate Similarity	NPC159367
0.7321	Intermediate Similarity	NPC478137
0.732	Intermediate Similarity	NPC209802
0.732	Intermediate Similarity	NPC205845
0.7315	Intermediate Similarity	NPC258130
0.7312	Intermediate Similarity	NPC214570
0.73	Intermediate Similarity	NPC249312
0.7292	Intermediate Similarity	NPC1272
0.7292	Intermediate Similarity	NPC101462
0.7292	Intermediate Similarity	NPC189972
0.7292	Intermediate Similarity	NPC30166
0.7292	Intermediate Similarity	NPC470614
0.7292	Intermediate Similarity	NPC248886
0.7292	Intermediate Similarity	NPC50964
0.729	Intermediate Similarity	NPC241879
0.7273	Intermediate Similarity	NPC147835
0.7273	Intermediate Similarity	NPC95920
0.7273	Intermediate Similarity	NPC85001
0.7273	Intermediate Similarity	NPC253645
0.7263	Intermediate Similarity	NPC102253
0.7263	Intermediate Similarity	NPC236112
0.7263	Intermediate Similarity	NPC322313
0.7263	Intermediate Similarity	NPC13554
0.7263	Intermediate Similarity	NPC236237
0.7255	Intermediate Similarity	NPC93027
0.7253	Intermediate Similarity	NPC474140
0.7253	Intermediate Similarity	NPC471799
0.7245	Intermediate Similarity	NPC157257
0.7245	Intermediate Similarity	NPC474349
0.7245	Intermediate Similarity	NPC274448
0.7245	Intermediate Similarity	NPC474189
0.7234	Intermediate Similarity	NPC138621
0.7234	Intermediate Similarity	NPC6978
0.7234	Intermediate Similarity	NPC244385
0.7234	Intermediate Similarity	NPC477514
0.7234	Intermediate Similarity	NPC167037
0.7228	Intermediate Similarity	NPC84171
0.7216	Intermediate Similarity	NPC317458
0.7204	Intermediate Similarity	NPC73875
0.7204	Intermediate Similarity	NPC244488
0.7204	Intermediate Similarity	NPC247325
0.7204	Intermediate Similarity	NPC470362
0.7204	Intermediate Similarity	NPC46160
0.7204	Intermediate Similarity	NPC202642
0.7204	Intermediate Similarity	NPC237460
0.7174	Intermediate Similarity	NPC471797
0.7174	Intermediate Similarity	NPC27395
0.7174	Intermediate Similarity	NPC329090
0.7172	Intermediate Similarity	NPC94462
0.7172	Intermediate Similarity	NPC152808
0.7172	Intermediate Similarity	NPC24277
0.7172	Intermediate Similarity	NPC293287
0.7172	Intermediate Similarity	NPC6391
0.7172	Intermediate Similarity	NPC261266
0.7158	Intermediate Similarity	NPC291379
0.7143	Intermediate Similarity	NPC185568
0.7143	Intermediate Similarity	NPC470077
0.7143	Intermediate Similarity	NPC124172
0.7143	Intermediate Similarity	NPC472265
0.7143	Intermediate Similarity	NPC474047
0.7143	Intermediate Similarity	NPC221758
0.7143	Intermediate Similarity	NPC59453
0.7143	Intermediate Similarity	NPC238485
0.7143	Intermediate Similarity	NPC33913
0.713	Intermediate Similarity	NPC90538
0.7119	Intermediate Similarity	NPC469943
0.7115	Intermediate Similarity	NPC311164
0.7115	Intermediate Similarity	NPC272732
0.7113	Intermediate Similarity	NPC20853
0.7113	Intermediate Similarity	NPC296701
0.7113	Intermediate Similarity	NPC87489
0.7113	Intermediate Similarity	NPC224072
0.7113	Intermediate Similarity	NPC218616
0.7113	Intermediate Similarity	NPC470049
0.7113	Intermediate Similarity	NPC201852
0.71	Intermediate Similarity	NPC149224
0.7097	Intermediate Similarity	NPC118508
0.7097	Intermediate Similarity	NPC328104
0.7097	Intermediate Similarity	NPC319090
0.7097	Intermediate Similarity	NPC322353
0.7097	Intermediate Similarity	NPC121744
0.7071	Intermediate Similarity	NPC318390
0.7071	Intermediate Similarity	NPC266511
0.7064	Intermediate Similarity	NPC475239
0.7059	Intermediate Similarity	NPC14380
0.7054	Intermediate Similarity	NPC328052
0.7053	Intermediate Similarity	NPC85346
0.7053	Intermediate Similarity	NPC474989
0.7053	Intermediate Similarity	NPC205455
0.7053	Intermediate Similarity	NPC22955
0.7053	Intermediate Similarity	NPC186191
0.7053	Intermediate Similarity	NPC470396
0.7053	Intermediate Similarity	NPC65897
0.7053	Intermediate Similarity	NPC99168
0.7053	Intermediate Similarity	NPC302041
0.7043	Intermediate Similarity	NPC304646
0.7043	Intermediate Similarity	NPC28280
0.7041	Intermediate Similarity	NPC207013
0.7033	Intermediate Similarity	NPC475728
0.703	Intermediate Similarity	NPC474668
0.703	Intermediate Similarity	NPC316186
0.703	Intermediate Similarity	NPC470542
0.7021	Intermediate Similarity	NPC106364
0.7021	Intermediate Similarity	NPC315261

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 NPC240650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	86
0.1-0.2	435
0.2-0.3	3256
0.3-0.4	3998
0.4-0.5	981
0.5-0.6	272
0.6-0.7	106
0.7-0.8	16
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
0.7667	Intermediate Similarity	NPD7339	Approved
0.7667	Intermediate Similarity	NPD6942	Approved
0.7525	Intermediate Similarity	NPD5771	Approved
0.7391	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4723	Approved
0.7374	Intermediate Similarity	NPD4722	Approved
0.7263	Intermediate Similarity	NPD7525	Registered
0.7174	Intermediate Similarity	NPD6926	Approved
0.7174	Intermediate Similarity	NPD6924	Approved
0.7143	Intermediate Similarity	NPD4786	Approved
0.7021	Intermediate Similarity	NPD6933	Approved
0.6989	Remote Similarity	NPD4784	Approved
0.6989	Remote Similarity	NPD4785	Approved
0.6957	Remote Similarity	NPD4243	Approved
0.6939	Remote Similarity	NPD3667	Approved
0.6931	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1346	Approved
0.6804	Remote Similarity	NPD7645	Phase 2
0.6774	Remote Similarity	NPD7150	Approved
0.6774	Remote Similarity	NPD7151	Approved
0.6774	Remote Similarity	NPD7152	Approved
0.6739	Remote Similarity	NPD6923	Approved
0.6739	Remote Similarity	NPD6922	Approved
0.6735	Remote Similarity	NPD4748	Discontinued
0.6735	Remote Similarity	NPD6930	Phase 2
0.6735	Remote Similarity	NPD6931	Approved
0.6731	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5707	Approved
0.6667	Remote Similarity	NPD6939	Phase 2
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7143	Approved
0.6635	Remote Similarity	NPD5328	Approved
0.6633	Remote Similarity	NPD6929	Approved
0.663	Remote Similarity	NPD6705	Phase 1
0.6598	Remote Similarity	NPD6932	Approved
0.6566	Remote Similarity	NPD7509	Discontinued
0.6562	Remote Similarity	NPD5275	Approved
0.6562	Remote Similarity	NPD4190	Phase 3
0.6545	Remote Similarity	NPD6404	Discontinued
0.6542	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6695	Phase 3
0.6509	Remote Similarity	NPD6079	Approved
0.6505	Remote Similarity	NPD3618	Phase 1
0.6471	Remote Similarity	NPD3665	Phase 1
0.6471	Remote Similarity	NPD3133	Approved
0.6471	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3666	Approved
0.6465	Remote Similarity	NPD6683	Phase 2
0.6465	Remote Similarity	NPD4195	Approved
0.6449	Remote Similarity	NPD4202	Approved
0.6449	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD5776	Phase 2
0.6429	Remote Similarity	NPD6925	Approved
0.6408	Remote Similarity	NPD6893	Approved
0.6404	Remote Similarity	NPD6640	Phase 3
0.64	Remote Similarity	NPD7514	Phase 3
0.6364	Remote Similarity	NPD7145	Approved
0.6364	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6420	Discontinued
0.6321	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD3668	Phase 3
0.6286	Remote Similarity	NPD7524	Approved
0.6286	Remote Similarity	NPD7750	Discontinued
0.6275	Remote Similarity	NPD4223	Phase 3
0.6275	Remote Similarity	NPD4221	Approved
0.6262	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6700	Approved
0.6261	Remote Similarity	NPD7333	Discontinued
0.625	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8418	Phase 2
0.6238	Remote Similarity	NPD7332	Phase 2
0.6216	Remote Similarity	NPD4755	Approved
0.6211	Remote Similarity	NPD791	Approved
0.6211	Remote Similarity	NPD15	Approved
0.621	Remote Similarity	NPD6909	Approved
0.621	Remote Similarity	NPD6908	Approved
0.619	Remote Similarity	NPD5279	Phase 3
0.6176	Remote Similarity	NPD6902	Approved
0.6176	Remote Similarity	NPD6898	Phase 1
0.6154	Remote Similarity	NPD4197	Approved
0.6126	Remote Similarity	NPD4697	Phase 3
0.6126	Remote Similarity	NPD5221	Approved
0.6126	Remote Similarity	NPD5222	Approved
0.6126	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5357	Phase 1
0.6107	Remote Similarity	NPD8449	Approved
0.6106	Remote Similarity	NPD4700	Approved
0.6106	Remote Similarity	NPD5286	Approved
0.6106	Remote Similarity	NPD5285	Approved
0.6106	Remote Similarity	NPD4696	Approved
0.6071	Remote Similarity	NPD6084	Phase 2
0.6071	Remote Similarity	NPD5173	Approved
0.6071	Remote Similarity	NPD6083	Phase 2
0.6061	Remote Similarity	NPD8450	Suspended
0.6061	Remote Similarity	NPD8264	Approved
0.6058	Remote Similarity	NPD4788	Approved
0.6055	Remote Similarity	NPD6703	Approved
0.6055	Remote Similarity	NPD7515	Phase 2
0.6055	Remote Similarity	NPD6702	Approved
0.6055	Remote Similarity	NPD7087	Discontinued
0.6053	Remote Similarity	NPD5223	Approved
0.6053	Remote Similarity	NPD4159	Approved
0.6048	Remote Similarity	NPD7522	Discontinued
0.6038	Remote Similarity	NPD4693	Phase 3
0.6038	Remote Similarity	NPD4689	Approved
0.6038	Remote Similarity	NPD5205	Approved
0.6038	Remote Similarity	NPD4138	Approved
0.6038	Remote Similarity	NPD4690	Approved
0.6038	Remote Similarity	NPD4688	Approved
0.6036	Remote Similarity	NPD5210	Approved
0.6036	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5983	Remote Similarity	NPD6675	Approved
0.5983	Remote Similarity	NPD5739	Approved
0.5983	Remote Similarity	NPD7128	Approved
0.5983	Remote Similarity	NPD6402	Approved
0.5963	Remote Similarity	NPD4096	Approved
0.595	Remote Similarity	NPD7335	Phase 2
0.595	Remote Similarity	NPD7336	Phase 2
0.595	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5175	Approved
0.5948	Remote Similarity	NPD4754	Approved
0.5948	Remote Similarity	NPD5174	Approved
0.5926	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5141	Approved
0.5888	Remote Similarity	NPD5690	Phase 2
0.5888	Remote Similarity	NPD7521	Approved
0.5888	Remote Similarity	NPD6409	Approved
0.5888	Remote Similarity	NPD5280	Approved
0.5888	Remote Similarity	NPD7334	Approved
0.5888	Remote Similarity	NPD5330	Approved
0.5888	Remote Similarity	NPD7146	Approved
0.5888	Remote Similarity	NPD4694	Approved
0.5888	Remote Similarity	NPD6684	Approved
0.5887	Remote Similarity	NPD7115	Discovery
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD6334	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD8174	Phase 2
0.5882	Remote Similarity	NPD6333	Approved
0.5877	Remote Similarity	NPD7638	Approved
0.5877	Remote Similarity	NPD5290	Discontinued
0.5876	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1082	Approved
0.5847	Remote Similarity	NPD4768	Approved
0.5847	Remote Similarity	NPD4767	Approved
0.5841	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD7639	Approved
0.5826	Remote Similarity	NPD7640	Approved
0.5816	Remote Similarity	NPD4787	Phase 1
0.5804	Remote Similarity	NPD7748	Approved
0.5798	Remote Similarity	NPD5701	Approved
0.5798	Remote Similarity	NPD5697	Approved
0.5785	Remote Similarity	NPD6883	Approved
0.5785	Remote Similarity	NPD7290	Approved
0.5785	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD6903	Approved
0.578	Remote Similarity	NPD6672	Approved
0.578	Remote Similarity	NPD5737	Approved
0.5772	Remote Similarity	NPD8298	Phase 2
0.5766	Remote Similarity	NPD8034	Phase 2
0.5766	Remote Similarity	NPD8035	Phase 2
0.5752	Remote Similarity	NPD5695	Phase 3
0.5752	Remote Similarity	NPD4814	Discontinued
0.575	Remote Similarity	NPD4729	Approved
0.575	Remote Similarity	NPD6011	Approved
0.575	Remote Similarity	NPD5128	Approved
0.575	Remote Similarity	NPD4730	Approved
0.5741	Remote Similarity	NPD6098	Approved
0.5741	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5696	Approved
0.5738	Remote Similarity	NPD6847	Approved
0.5738	Remote Similarity	NPD6650	Approved
0.5738	Remote Similarity	NPD6649	Approved
0.5738	Remote Similarity	NPD8130	Phase 1
0.5738	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6869	Approved
0.5738	Remote Similarity	NPD6617	Approved
0.5728	Remote Similarity	NPD3617	Approved
0.5714	Remote Similarity	NPD4139	Approved
0.5714	Remote Similarity	NPD6920	Discontinued
0.5714	Remote Similarity	NPD6914	Discontinued
0.5714	Remote Similarity	NPD4692	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD8297	Approved
0.5691	Remote Similarity	NPD6882	Approved
0.568	Remote Similarity	NPD7754	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