NPASS Compound

Structure

NPC139724 OpenBabel07101718312D 31 34 0 0 1 0 0 0 0 0999 V2000 3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1727 -2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1945 -1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5254 -2.6270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 -3.5780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 16 3 1 1 0 0 0 16 20 1 0 0 0 0 17 28 1 6 0 0 0 18 13 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 6 0 0 0 20 27 1 6 0 0 0 21 23 1 0 0 0 0 21 26 1 6 0 0 0 22 29 1 1 0 0 0 23 30 1 1 0 0 0 24 25 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.34
Volume:	473.847
LogP:	4.405
LogD:	4.434
LogS:	-4.159
# Rotatable Bonds:	4
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	5.016
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.994
MDCK Permeability:	6.876856059534475e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.515
20% Bioavailability (F20%):	0.762
30% Bioavailability (F30%):	0.872

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	82.24969482421875%
Volume Distribution (VD):	0.923
Pgp-substrate:	1.8634666204452515%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.294
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.164
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.222
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	2.979
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.361
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.862
Carcinogencity:	0.019
Eye Corrosion:	0.008
Eye Irritation:	0.109
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC139724

Natural Product ID:	NPC139724
*Common Name:**	Certonardosterol G
IUPAC Name:	(3S,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(E,2R,5R)-5-hydroxy-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,15-triol
Synonyms:	Certonardosterol G
Standard InCHIKey:	PNJDDNGAXOYFJN-JMNWVQTPSA-N
Standard InCHI:	InChI=1S/C27H46O4/c1-15(2)22(29)7-6-16(3)20-14-24(31)25-18-13-23(30)21-12-17(28)8-10-26(21,4)19(18)9-11-27(20,25)5/h6-7,15-25,28-31H,8-14H2,1-5H3/b7-6+/t16-,17+,18-,19+,20-,21-,22+,23+,24-,25-,26-,27-/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@H](C1)[C@@H](O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@H](O)C[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479151
PubChem CID:	21629550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ 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
ED50	5
MIC	20

Activity Type	# Activity
Cell Line	5
Organism	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[535815]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[535815]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.4	ug ml-1	PMID[535815]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[535815]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[535815]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	12.5	ug.mL-1	PMID[535815]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	12.5	ug.mL-1	PMID[535815]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[535815]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	25.0	ug.mL-1	PMID[535815]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25.0	ug.mL-1	PMID[535815]

☑ 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 NPC139724 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	173
0.1-0.2	1458
0.2-0.3	5597
0.3-0.4	15168
0.4-0.5	8520
0.5-0.6	5320
0.6-0.7	4719
0.7-0.8	1493
0.8-0.85	164
0.85-0.9	69
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC193870
0.9625	High Similarity	NPC141941
0.9506	High Similarity	NPC127606
0.9506	High Similarity	NPC475798
0.9383	High Similarity	NPC110778
0.9383	High Similarity	NPC477818
0.9277	High Similarity	NPC6605
0.9167	High Similarity	NPC474657
0.9167	High Similarity	NPC186145
0.9059	High Similarity	NPC475664
0.9048	High Similarity	NPC261266
0.9048	High Similarity	NPC299068
0.9048	High Similarity	NPC24277
0.9048	High Similarity	NPC201273
0.9036	High Similarity	NPC124172
0.9024	High Similarity	NPC218616
0.9024	High Similarity	NPC296701
0.8953	High Similarity	NPC109744
0.8929	High Similarity	NPC318390
0.8929	High Similarity	NPC470360
0.8916	High Similarity	NPC82623
0.8889	High Similarity	NPC24504
0.8889	High Similarity	NPC477226
0.8851	High Similarity	NPC473956
0.8851	High Similarity	NPC475751
0.8837	High Similarity	NPC133588
0.8824	High Similarity	NPC6391
0.8824	High Similarity	NPC152808
0.8824	High Similarity	NPC293287
0.881	High Similarity	NPC209802
0.8795	High Similarity	NPC1272
0.8795	High Similarity	NPC50964
0.8795	High Similarity	NPC470614
0.878	High Similarity	NPC47149
0.878	High Similarity	NPC102253
0.878	High Similarity	NPC322313
0.878	High Similarity	NPC78545
0.878	High Similarity	NPC236237
0.878	High Similarity	NPC71535
0.8765	High Similarity	NPC472499
0.8765	High Similarity	NPC475
0.8765	High Similarity	NPC244385
0.8765	High Similarity	NPC11908
0.8765	High Similarity	NPC138621
0.8765	High Similarity	NPC6978
0.8765	High Similarity	NPC472500
0.8765	High Similarity	NPC167037
0.8765	High Similarity	NPC472502
0.8765	High Similarity	NPC477817
0.8765	High Similarity	NPC477819
0.875	High Similarity	NPC41554
0.875	High Similarity	NPC97404
0.875	High Similarity	NPC275671
0.8736	High Similarity	NPC105495
0.869	High Similarity	NPC470558
0.869	High Similarity	NPC134481
0.8675	High Similarity	NPC209620
0.8675	High Similarity	NPC23852
0.8675	High Similarity	NPC476646
0.8659	High Similarity	NPC273410
0.8659	High Similarity	NPC1319
0.8659	High Similarity	NPC209430
0.8659	High Similarity	NPC476316
0.8659	High Similarity	NPC80530
0.8659	High Similarity	NPC30986
0.8642	High Similarity	NPC138502
0.8636	High Similarity	NPC80561
0.8636	High Similarity	NPC329596
0.8636	High Similarity	NPC11216
0.8636	High Similarity	NPC204188
0.8636	High Similarity	NPC291484
0.8636	High Similarity	NPC3345
0.8636	High Similarity	NPC295668
0.8625	High Similarity	NPC103822
0.8621	High Similarity	NPC212596
0.8621	High Similarity	NPC471952
0.8621	High Similarity	NPC67872
0.8621	High Similarity	NPC475605
0.8621	High Similarity	NPC4574
0.8621	High Similarity	NPC474668
0.8621	High Similarity	NPC470542
0.8588	High Similarity	NPC205845
0.8588	High Similarity	NPC256567
0.8571	High Similarity	NPC87489
0.8571	High Similarity	NPC101462
0.8571	High Similarity	NPC49964
0.8554	High Similarity	NPC234193
0.8554	High Similarity	NPC96362
0.8554	High Similarity	NPC26117
0.8537	High Similarity	NPC285761
0.8537	High Similarity	NPC301707
0.8523	High Similarity	NPC101886
0.8523	High Similarity	NPC470361
0.8519	High Similarity	NPC38141
0.8519	High Similarity	NPC237460
0.8506	High Similarity	NPC470620
0.8506	High Similarity	NPC304083
0.8471	Intermediate Similarity	NPC113978
0.8471	Intermediate Similarity	NPC232023
0.8471	Intermediate Similarity	NPC207013
0.8452	Intermediate Similarity	NPC157655
0.8452	Intermediate Similarity	NPC264245
0.8434	Intermediate Similarity	NPC143182
0.8434	Intermediate Similarity	NPC28862
0.8434	Intermediate Similarity	NPC47982
0.8434	Intermediate Similarity	NPC472463
0.8434	Intermediate Similarity	NPC84694
0.8434	Intermediate Similarity	NPC109546
0.8434	Intermediate Similarity	NPC81306
0.8415	Intermediate Similarity	NPC470711
0.8415	Intermediate Similarity	NPC260301
0.8415	Intermediate Similarity	NPC470758
0.8415	Intermediate Similarity	NPC307336
0.8395	Intermediate Similarity	NPC185536
0.8372	Intermediate Similarity	NPC470077
0.8372	Intermediate Similarity	NPC474493
0.8372	Intermediate Similarity	NPC185568
0.8372	Intermediate Similarity	NPC231310
0.8372	Intermediate Similarity	NPC255882
0.837	Intermediate Similarity	NPC288970
0.8353	Intermediate Similarity	NPC470049
0.8353	Intermediate Similarity	NPC248886
0.8353	Intermediate Similarity	NPC202389
0.8333	Intermediate Similarity	NPC241290
0.8333	Intermediate Similarity	NPC13554
0.8333	Intermediate Similarity	NPC164840
0.8333	Intermediate Similarity	NPC209944
0.8315	Intermediate Similarity	NPC138974
0.8313	Intermediate Similarity	NPC85346
0.8313	Intermediate Similarity	NPC302041
0.8313	Intermediate Similarity	NPC65897
0.8313	Intermediate Similarity	NPC474216
0.8313	Intermediate Similarity	NPC472501
0.8313	Intermediate Similarity	NPC148977
0.8313	Intermediate Similarity	NPC477514
0.8313	Intermediate Similarity	NPC477522
0.8313	Intermediate Similarity	NPC87604
0.8298	Intermediate Similarity	NPC154072
0.8295	Intermediate Similarity	NPC149224
0.8295	Intermediate Similarity	NPC271967
0.8293	Intermediate Similarity	NPC470749
0.8293	Intermediate Similarity	NPC247325
0.8293	Intermediate Similarity	NPC189883
0.8293	Intermediate Similarity	NPC129165
0.8293	Intermediate Similarity	NPC253190
0.8293	Intermediate Similarity	NPC244488
0.8293	Intermediate Similarity	NPC134330
0.828	Intermediate Similarity	NPC476893
0.8276	Intermediate Similarity	NPC266511
0.8276	Intermediate Similarity	NPC274448
0.8272	Intermediate Similarity	NPC308440
0.8272	Intermediate Similarity	NPC306727
0.8272	Intermediate Similarity	NPC472503
0.8261	Intermediate Similarity	NPC476894
0.8256	Intermediate Similarity	NPC474634
0.8256	Intermediate Similarity	NPC317458
0.8242	Intermediate Similarity	NPC310013
0.8242	Intermediate Similarity	NPC27531
0.8235	Intermediate Similarity	NPC249423
0.8235	Intermediate Similarity	NPC47761
0.8235	Intermediate Similarity	NPC470383
0.8222	Intermediate Similarity	NPC245410
0.8222	Intermediate Similarity	NPC470390
0.8222	Intermediate Similarity	NPC192437
0.8222	Intermediate Similarity	NPC270511
0.8222	Intermediate Similarity	NPC14380
0.8214	Intermediate Similarity	NPC5604
0.8202	Intermediate Similarity	NPC2158
0.8202	Intermediate Similarity	NPC160304
0.8202	Intermediate Similarity	NPC280556
0.8193	Intermediate Similarity	NPC257191
0.8193	Intermediate Similarity	NPC119355
0.8193	Intermediate Similarity	NPC202540
0.8193	Intermediate Similarity	NPC212241
0.8193	Intermediate Similarity	NPC471798
0.8193	Intermediate Similarity	NPC331618
0.8193	Intermediate Similarity	NPC91594
0.8193	Intermediate Similarity	NPC248830
0.8193	Intermediate Similarity	NPC214570
0.8191	Intermediate Similarity	NPC476895
0.8182	Intermediate Similarity	NPC71520
0.8182	Intermediate Similarity	NPC269058
0.8182	Intermediate Similarity	NPC121981
0.8172	Intermediate Similarity	NPC304899
0.8172	Intermediate Similarity	NPC253115
0.8171	Intermediate Similarity	NPC471723
0.8171	Intermediate Similarity	NPC257347
0.8171	Intermediate Similarity	NPC141071
0.8171	Intermediate Similarity	NPC32832
0.8171	Intermediate Similarity	NPC3403
0.8161	Intermediate Similarity	NPC238485
0.8161	Intermediate Similarity	NPC15534
0.8161	Intermediate Similarity	NPC469878
0.8161	Intermediate Similarity	NPC478102
0.8161	Intermediate Similarity	NPC474047
0.8152	Intermediate Similarity	NPC144202
0.8152	Intermediate Similarity	NPC127718
0.8152	Intermediate Similarity	NPC111015
0.8152	Intermediate Similarity	NPC65402
0.8148	Intermediate Similarity	NPC472506

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 NPC139724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1641
0.2-0.3	4305
0.3-0.4	2157
0.4-0.5	436
0.5-0.6	178
0.6-0.7	191
0.7-0.8	76
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD7525	Registered
0.8295	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6942	Approved
0.7952	Intermediate Similarity	NPD7339	Approved
0.7917	Intermediate Similarity	NPD7639	Approved
0.7917	Intermediate Similarity	NPD7640	Approved
0.7812	Intermediate Similarity	NPD7638	Approved
0.7791	Intermediate Similarity	NPD6929	Approved
0.7753	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6930	Phase 2
0.7701	Intermediate Similarity	NPD6931	Approved
0.7701	Intermediate Similarity	NPD7514	Phase 3
0.7674	Intermediate Similarity	NPD7145	Approved
0.764	Intermediate Similarity	NPD6695	Phase 3
0.7619	Intermediate Similarity	NPD4784	Approved
0.7619	Intermediate Similarity	NPD4785	Approved
0.7614	Intermediate Similarity	NPD6902	Approved
0.759	Intermediate Similarity	NPD4243	Approved
0.7586	Intermediate Similarity	NPD7645	Phase 2
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7558	Intermediate Similarity	NPD5776	Phase 2
0.7558	Intermediate Similarity	NPD6925	Approved
0.75	Intermediate Similarity	NPD7332	Phase 2
0.7474	Intermediate Similarity	NPD4202	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7412	Intermediate Similarity	NPD6926	Approved
0.7412	Intermediate Similarity	NPD6924	Approved
0.7381	Intermediate Similarity	NPD7151	Approved
0.7381	Intermediate Similarity	NPD7150	Approved
0.7381	Intermediate Similarity	NPD7152	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7368	Intermediate Similarity	NPD6079	Approved
0.7363	Intermediate Similarity	NPD4786	Approved
0.7356	Intermediate Similarity	NPD6932	Approved
0.7347	Intermediate Similarity	NPD4755	Approved
0.734	Intermediate Similarity	NPD5328	Approved
0.7312	Intermediate Similarity	NPD7524	Approved
0.7312	Intermediate Similarity	NPD7750	Discontinued
0.7303	Intermediate Similarity	NPD4748	Discontinued
0.73	Intermediate Similarity	NPD5223	Approved
0.7283	Intermediate Similarity	NPD6893	Approved
0.7273	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7144	Approved
0.7262	Intermediate Similarity	NPD7143	Approved
0.7241	Intermediate Similarity	NPD6933	Approved
0.7228	Intermediate Similarity	NPD7632	Discontinued
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD4700	Approved
0.7191	Intermediate Similarity	NPD4195	Approved
0.7174	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD3666	Approved
0.7174	Intermediate Similarity	NPD3133	Approved
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6923	Approved
0.7143	Intermediate Similarity	NPD6922	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7126	Intermediate Similarity	NPD5275	Approved
0.7126	Intermediate Similarity	NPD8264	Approved
0.7126	Intermediate Similarity	NPD4190	Phase 3
0.7111	Intermediate Similarity	NPD7509	Discontinued
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7327	Approved
0.7091	Intermediate Similarity	NPD7328	Approved
0.7075	Intermediate Similarity	NPD4634	Approved
0.7071	Intermediate Similarity	NPD5221	Approved
0.7071	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5222	Approved
0.7059	Intermediate Similarity	NPD4787	Phase 1
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7033	Intermediate Similarity	NPD6898	Phase 1
0.7027	Intermediate Similarity	NPD7516	Approved
0.7019	Intermediate Similarity	NPD7128	Approved
0.7019	Intermediate Similarity	NPD5739	Approved
0.7019	Intermediate Similarity	NPD6402	Approved
0.7019	Intermediate Similarity	NPD6675	Approved
0.701	Intermediate Similarity	NPD7637	Suspended
0.701	Intermediate Similarity	NPD7087	Discontinued
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD6683	Phase 2
0.699	Remote Similarity	NPD4754	Approved
0.6979	Remote Similarity	NPD6051	Approved
0.6979	Remote Similarity	NPD4753	Phase 2
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6939	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD6928	Phase 2
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6903	Remote Similarity	NPD8033	Approved
0.6903	Remote Similarity	NPD8378	Approved
0.6903	Remote Similarity	NPD8335	Approved
0.6903	Remote Similarity	NPD8380	Approved
0.6903	Remote Similarity	NPD8379	Approved
0.6903	Remote Similarity	NPD8296	Approved
0.69	Remote Similarity	NPD4697	Phase 3
0.6889	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD6115	Approved
0.6889	Remote Similarity	NPD6114	Approved
0.6889	Remote Similarity	NPD6697	Approved
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.6887	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD7320	Approved
0.6882	Remote Similarity	NPD4788	Approved
0.6881	Remote Similarity	NPD4632	Approved
0.6857	Remote Similarity	NPD4768	Approved
0.6857	Remote Similarity	NPD4767	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6837	Remote Similarity	NPD8035	Phase 2
0.6837	Remote Similarity	NPD8034	Phase 2
0.6837	Remote Similarity	NPD7515	Phase 2
0.6822	Remote Similarity	NPD6373	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6372	Approved
0.68	Remote Similarity	NPD5210	Approved
0.68	Remote Similarity	NPD4629	Approved
0.6792	Remote Similarity	NPD5701	Approved
0.6789	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6778	Remote Similarity	NPD6116	Phase 1
0.6774	Remote Similarity	NPD4223	Phase 3
0.6774	Remote Similarity	NPD4221	Approved
0.6759	Remote Similarity	NPD5249	Phase 3
0.6759	Remote Similarity	NPD5247	Approved
0.6759	Remote Similarity	NPD5169	Approved
0.6759	Remote Similarity	NPD5135	Approved
0.6759	Remote Similarity	NPD5250	Approved
0.6759	Remote Similarity	NPD5251	Approved
0.6759	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5248	Approved
0.6754	Remote Similarity	NPD7503	Approved
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4820	Approved
0.6739	Remote Similarity	NPD4822	Approved
0.6737	Remote Similarity	NPD5329	Approved
0.6735	Remote Similarity	NPD7136	Phase 2
0.6729	Remote Similarity	NPD5128	Approved
0.6703	Remote Similarity	NPD4271	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4268	Approved
0.6697	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD5215	Approved
0.6697	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5216	Approved
0.6697	Remote Similarity	NPD5127	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6632	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD4197	Approved
0.6602	Remote Similarity	NPD5290	Discontinued
0.6591	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3703	Phase 2
0.6552	Remote Similarity	NPD6370	Approved
0.6549	Remote Similarity	NPD7115	Discovery
0.6542	Remote Similarity	NPD6008	Approved
0.6535	Remote Similarity	NPD7748	Approved
0.6531	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5362	Discontinued
0.6526	Remote Similarity	NPD5331	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6522	Remote Similarity	NPD6059	Approved
0.6518	Remote Similarity	NPD5167	Approved
0.6506	Remote Similarity	NPD368	Approved
0.6505	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD5284	Approved
0.65	Remote Similarity	NPD7319	Approved
0.6496	Remote Similarity	NPD7604	Phase 2
0.6495	Remote Similarity	NPD5279	Phase 3
0.6495	Remote Similarity	NPD4689	Approved
0.6495	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6409	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