NPASS Compound

Structure

NPC63588 OpenBabel07101718332D 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 1 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:	436.36
Volume:	476.483
LogP:	4.787
LogD:	4.898
LogS:	-4.196
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.515
Synthetic Accessibility Score:	4.851
Fsp3:	1.0
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:	-4.813
MDCK Permeability:	4.2325787944719195e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	93.67281341552734%
Volume Distribution (VD):	0.968
Pgp-substrate:	2.1677348613739014%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	9.113
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.505
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.096
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.948
Carcinogencity:	0.061
Eye Corrosion:	0.888
Eye Irritation:	0.468
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC63588

Natural Product ID:	NPC63588
*Common Name:**	Certonardosterol F
IUPAC Name:	(3S,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(2R,5S)-5-hydroxy-6-methylheptan-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 F
Standard InCHIKey:	GAVMUEBNINHFDC-WADCUEKASA-N
Standard InCHI:	InChI=1S/C27H48O4/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/h15-25,28-31H,6-14H2,1-5H3/t16-,17+,18-,19+,20-,21-,22+,23+,24-,25-,26-,27-/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1C[C@H]([C@H]2[C@@H]3C[C@@H]([C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478979
PubChem CID:	21629549
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001110] Tetrahydroxy bile acids, alcohols 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	=	3.8	ug ml-1	PMID[564240]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	4.4	ug ml-1	PMID[564240]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.8	ug ml-1	PMID[564240]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	4.3	ug ml-1	PMID[564240]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[564240]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	25.0	ug.mL-1	PMID[564240]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[564240]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[564240]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[564240]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[564240]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[564240]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	25.0	ug.mL-1	PMID[564240]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	>	25.0	ug.mL-1	PMID[564240]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	25.0	ug.mL-1	PMID[564240]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25.0	ug.mL-1	PMID[564240]

☑ 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 NPC63588 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	373
0.1-0.2	4397
0.2-0.3	16019
0.3-0.4	9562
0.4-0.5	4702
0.5-0.6	4374
0.6-0.7	2410
0.7-0.8	644
0.8-0.85	124
0.85-0.9	48
0.9-0.95	32
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232925
1.0	High Similarity	NPC251201
0.9846	High Similarity	NPC477820
0.9701	High Similarity	NPC470610
0.9559	High Similarity	NPC304499
0.9559	High Similarity	NPC48795
0.9545	High Similarity	NPC66407
0.942	High Similarity	NPC317242
0.9412	High Similarity	NPC153719
0.9385	High Similarity	NPC44122
0.9286	High Similarity	NPC163597
0.9265	High Similarity	NPC470071
0.9265	High Similarity	NPC252182
0.9265	High Similarity	NPC127094
0.9265	High Similarity	NPC187471
0.9265	High Similarity	NPC1340
0.9155	High Similarity	NPC192046
0.9155	High Similarity	NPC477227
0.9155	High Similarity	NPC128951
0.9155	High Similarity	NPC185915
0.9155	High Similarity	NPC105208
0.9155	High Similarity	NPC302578
0.9118	High Similarity	NPC192192
0.9077	High Similarity	NPC159654
0.9077	High Similarity	NPC167995
0.9077	High Similarity	NPC118937
0.9077	High Similarity	NPC281540
0.9028	High Similarity	NPC67657
0.9028	High Similarity	NPC18857
0.8971	High Similarity	NPC129829
0.8971	High Similarity	NPC254037
0.8923	High Similarity	NPC249078
0.8923	High Similarity	NPC114891
0.8923	High Similarity	NPC236099
0.8923	High Similarity	NPC209686
0.8904	High Similarity	NPC287452
0.8889	High Similarity	NPC476233
0.8873	High Similarity	NPC243027
0.8873	High Similarity	NPC158208
0.8873	High Similarity	NPC196136
0.8824	High Similarity	NPC474756
0.8824	High Similarity	NPC472741
0.8806	High Similarity	NPC142712
0.8784	High Similarity	NPC78545
0.8784	High Similarity	NPC71535
0.8769	High Similarity	NPC148174
0.8769	High Similarity	NPC71460
0.8769	High Similarity	NPC218585
0.8767	High Similarity	NPC471045
0.8767	High Similarity	NPC477817
0.8767	High Similarity	NPC477819
0.8732	High Similarity	NPC10476
0.8732	High Similarity	NPC192501
0.8732	High Similarity	NPC228994
0.8732	High Similarity	NPC475458
0.8714	High Similarity	NPC157422
0.8714	High Similarity	NPC100586
0.8714	High Similarity	NPC109457
0.8714	High Similarity	NPC478103
0.8696	High Similarity	NPC107919
0.8676	High Similarity	NPC63190
0.8676	High Similarity	NPC473230
0.8676	High Similarity	NPC48079
0.8676	High Similarity	NPC475884
0.8667	High Similarity	NPC469745
0.8657	High Similarity	NPC473276
0.8657	High Similarity	NPC474380
0.8657	High Similarity	NPC41577
0.8649	High Similarity	NPC476176
0.863	High Similarity	NPC64081
0.863	High Similarity	NPC474574
0.8571	High Similarity	NPC282454
0.8553	High Similarity	NPC296734
0.8553	High Similarity	NPC470611
0.8553	High Similarity	NPC475388
0.8514	High Similarity	NPC147993
0.8507	High Similarity	NPC69149
0.8493	Intermediate Similarity	NPC473916
0.8493	Intermediate Similarity	NPC477601
0.8493	Intermediate Similarity	NPC477602
0.8472	Intermediate Similarity	NPC477508
0.8442	Intermediate Similarity	NPC110778
0.8442	Intermediate Similarity	NPC232023
0.8442	Intermediate Similarity	NPC193870
0.8442	Intermediate Similarity	NPC478054
0.8442	Intermediate Similarity	NPC141941
0.8429	Intermediate Similarity	NPC470833
0.8429	Intermediate Similarity	NPC299948
0.8429	Intermediate Similarity	NPC241085
0.8429	Intermediate Similarity	NPC470830
0.84	Intermediate Similarity	NPC477282
0.84	Intermediate Similarity	NPC269333
0.84	Intermediate Similarity	NPC81074
0.84	Intermediate Similarity	NPC24504
0.8382	Intermediate Similarity	NPC475943
0.8382	Intermediate Similarity	NPC243469
0.8382	Intermediate Similarity	NPC190827
0.8378	Intermediate Similarity	NPC133596
0.8378	Intermediate Similarity	NPC11907
0.8356	Intermediate Similarity	NPC91387
0.8356	Intermediate Similarity	NPC270306
0.8356	Intermediate Similarity	NPC231680
0.8333	Intermediate Similarity	NPC475798
0.8333	Intermediate Similarity	NPC255882
0.8333	Intermediate Similarity	NPC127606
0.831	Intermediate Similarity	NPC231945
0.8308	Intermediate Similarity	NPC476735
0.8289	Intermediate Similarity	NPC470609
0.8289	Intermediate Similarity	NPC7479
0.8289	Intermediate Similarity	NPC257296
0.8289	Intermediate Similarity	NPC248944
0.8289	Intermediate Similarity	NPC47149
0.8267	Intermediate Similarity	NPC324700
0.8267	Intermediate Similarity	NPC472502
0.8267	Intermediate Similarity	NPC472499
0.8267	Intermediate Similarity	NPC34046
0.8267	Intermediate Similarity	NPC472500
0.8267	Intermediate Similarity	NPC475
0.8267	Intermediate Similarity	NPC224802
0.8267	Intermediate Similarity	NPC471769
0.8267	Intermediate Similarity	NPC171426
0.8267	Intermediate Similarity	NPC80089
0.8243	Intermediate Similarity	NPC470145
0.8228	Intermediate Similarity	NPC232044
0.8228	Intermediate Similarity	NPC266651
0.8228	Intermediate Similarity	NPC273290
0.8219	Intermediate Similarity	NPC308440
0.8219	Intermediate Similarity	NPC478130
0.8219	Intermediate Similarity	NPC472503
0.8205	Intermediate Similarity	NPC477818
0.8194	Intermediate Similarity	NPC324984
0.8194	Intermediate Similarity	NPC473279
0.8194	Intermediate Similarity	NPC195530
0.8194	Intermediate Similarity	NPC477822
0.8194	Intermediate Similarity	NPC157777
0.8194	Intermediate Similarity	NPC323900
0.8194	Intermediate Similarity	NPC477823
0.8194	Intermediate Similarity	NPC473552
0.8194	Intermediate Similarity	NPC477821
0.8194	Intermediate Similarity	NPC131506
0.8182	Intermediate Similarity	NPC73515
0.8169	Intermediate Similarity	NPC99264
0.8158	Intermediate Similarity	NPC220379
0.8158	Intermediate Similarity	NPC476316
0.8158	Intermediate Similarity	NPC201276
0.8158	Intermediate Similarity	NPC80891
0.8133	Intermediate Similarity	NPC212453
0.8133	Intermediate Similarity	NPC207010
0.8133	Intermediate Similarity	NPC202540
0.8133	Intermediate Similarity	NPC317913
0.8133	Intermediate Similarity	NPC138502
0.8125	Intermediate Similarity	NPC121981
0.8125	Intermediate Similarity	NPC201273
0.8125	Intermediate Similarity	NPC6605
0.8125	Intermediate Similarity	NPC139724
0.8125	Intermediate Similarity	NPC476727
0.8125	Intermediate Similarity	NPC471240
0.8125	Intermediate Similarity	NPC476726
0.8125	Intermediate Similarity	NPC24277
0.8125	Intermediate Similarity	NPC472272
0.8116	Intermediate Similarity	NPC472946
0.8108	Intermediate Similarity	NPC139765
0.8108	Intermediate Similarity	NPC131584
0.8108	Intermediate Similarity	NPC3403
0.8108	Intermediate Similarity	NPC103822
0.8101	Intermediate Similarity	NPC227260
0.8101	Intermediate Similarity	NPC256567
0.8101	Intermediate Similarity	NPC124172
0.8082	Intermediate Similarity	NPC473238
0.8082	Intermediate Similarity	NPC472341
0.8082	Intermediate Similarity	NPC232112
0.8077	Intermediate Similarity	NPC202688
0.8077	Intermediate Similarity	NPC60018
0.8077	Intermediate Similarity	NPC154043
0.8077	Intermediate Similarity	NPC121121
0.8052	Intermediate Similarity	NPC16449
0.8052	Intermediate Similarity	NPC475679
0.8052	Intermediate Similarity	NPC474714
0.8028	Intermediate Similarity	NPC469987
0.8026	Intermediate Similarity	NPC31828
0.8026	Intermediate Similarity	NPC301707
0.8026	Intermediate Similarity	NPC42853
0.8025	Intermediate Similarity	NPC210658
0.8025	Intermediate Similarity	NPC161928
0.8025	Intermediate Similarity	NPC474657
0.8025	Intermediate Similarity	NPC186145
0.8	Intermediate Similarity	NPC4209
0.8	Intermediate Similarity	NPC86305
0.8	Intermediate Similarity	NPC38141
0.8	Intermediate Similarity	NPC14112
0.7975	Intermediate Similarity	NPC327451
0.7975	Intermediate Similarity	NPC216420
0.7975	Intermediate Similarity	NPC211135
0.7975	Intermediate Similarity	NPC111582
0.7975	Intermediate Similarity	NPC470070
0.7975	Intermediate Similarity	NPC477285
0.7975	Intermediate Similarity	NPC85095
0.7949	Intermediate Similarity	NPC157655
0.7945	Intermediate Similarity	NPC111234
0.7945	Intermediate Similarity	NPC156277

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 NPC63588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	4348
0.2-0.3	3143
0.3-0.4	717
0.4-0.5	223
0.5-0.6	196
0.6-0.7	101
0.7-0.8	22
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD4267	Clinical (unspecified phase)
0.8571	High Similarity	NPD4787	Phase 1
0.8289	Intermediate Similarity	NPD6928	Phase 2
0.8267	Intermediate Similarity	NPD6118	Approved
0.8267	Intermediate Similarity	NPD6697	Approved
0.8267	Intermediate Similarity	NPD6115	Approved
0.8267	Intermediate Similarity	NPD6114	Approved
0.8133	Intermediate Similarity	NPD6116	Phase 1
0.8	Intermediate Similarity	NPD6117	Approved
0.7945	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3703	Phase 2
0.7821	Intermediate Similarity	NPD7525	Registered
0.7808	Intermediate Similarity	NPD4244	Approved
0.7808	Intermediate Similarity	NPD4245	Approved
0.7733	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3698	Phase 2
0.7671	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8171	Discontinued
0.7333	Intermediate Similarity	NPD4789	Approved
0.7297	Intermediate Similarity	NPD5360	Phase 3
0.7297	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6701	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6700	Approved
0.7123	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6703	Approved
0.7045	Intermediate Similarity	NPD6702	Approved
0.7	Intermediate Similarity	NPD7991	Discontinued
0.6962	Remote Similarity	NPD6942	Approved
0.6962	Remote Similarity	NPD7339	Approved
0.6951	Remote Similarity	NPD4748	Discontinued
0.6941	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3671	Phase 1
0.6842	Remote Similarity	NPD6705	Phase 1
0.6795	Remote Similarity	NPD6081	Approved
0.6795	Remote Similarity	NPD4758	Discontinued
0.6795	Remote Similarity	NPD5777	Approved
0.6782	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3702	Approved
0.6707	Remote Similarity	NPD5364	Discontinued
0.6706	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6627	Remote Similarity	NPD7645	Phase 2
0.6615	Remote Similarity	NPD385	Approved
0.6615	Remote Similarity	NPD384	Approved
0.6598	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7638	Approved
0.6593	Remote Similarity	NPD4202	Approved
0.6582	Remote Similarity	NPD4243	Approved
0.6579	Remote Similarity	NPD4224	Phase 2
0.6533	Remote Similarity	NPD371	Approved
0.6526	Remote Similarity	NPD7640	Approved
0.6526	Remote Similarity	NPD7639	Approved
0.6526	Remote Similarity	NPD8418	Phase 2
0.6489	Remote Similarity	NPD4755	Approved
0.6477	Remote Similarity	NPD8308	Discontinued
0.6444	Remote Similarity	NPD5328	Approved
0.6437	Remote Similarity	NPD4786	Approved
0.6437	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6929	Approved
0.642	Remote Similarity	NPD4784	Approved
0.642	Remote Similarity	NPD6926	Approved
0.642	Remote Similarity	NPD6924	Approved
0.642	Remote Similarity	NPD4785	Approved
0.6392	Remote Similarity	NPD7632	Discontinued
0.6354	Remote Similarity	NPD5286	Approved
0.6354	Remote Similarity	NPD4700	Approved
0.6354	Remote Similarity	NPD5285	Approved
0.6354	Remote Similarity	NPD4696	Approved
0.6353	Remote Similarity	NPD6931	Approved
0.6353	Remote Similarity	NPD6930	Phase 2
0.6322	Remote Similarity	NPD6695	Phase 3
0.6316	Remote Similarity	NPD7920	Phase 3
0.6316	Remote Similarity	NPD7919	Phase 3
0.6304	Remote Similarity	NPD6079	Approved
0.6292	Remote Similarity	NPD3618	Phase 1
0.6289	Remote Similarity	NPD5223	Approved
0.6265	Remote Similarity	NPD6933	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD8088	Phase 1
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.6224	Remote Similarity	NPD5224	Approved
0.6224	Remote Similarity	NPD5226	Approved
0.6224	Remote Similarity	NPD5225	Approved
0.6224	Remote Similarity	NPD5211	Phase 2
0.6224	Remote Similarity	NPD4633	Approved
0.622	Remote Similarity	NPD1810	Approved
0.622	Remote Similarity	NPD1811	Approved
0.6212	Remote Similarity	NPD386	Approved
0.6212	Remote Similarity	NPD388	Approved
0.6207	Remote Similarity	NPD3667	Approved
0.62	Remote Similarity	NPD5739	Approved
0.62	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD7128	Approved
0.62	Remote Similarity	NPD6675	Approved
0.619	Remote Similarity	NPD6925	Approved
0.619	Remote Similarity	NPD5776	Phase 2
0.619	Remote Similarity	NPD6932	Approved
0.6173	Remote Similarity	NPD7152	Approved
0.6173	Remote Similarity	NPD7150	Approved
0.6173	Remote Similarity	NPD7151	Approved
0.6163	Remote Similarity	NPD7509	Discontinued
0.6162	Remote Similarity	NPD5175	Approved
0.6162	Remote Similarity	NPD5174	Approved
0.6162	Remote Similarity	NPD4754	Approved
0.6145	Remote Similarity	NPD5275	Approved
0.6145	Remote Similarity	NPD4190	Phase 3
0.6125	Remote Similarity	NPD6923	Approved
0.6125	Remote Similarity	NPD6922	Approved
0.6118	Remote Similarity	NPD7145	Approved
0.6117	Remote Similarity	NPD4634	Approved
0.61	Remote Similarity	NPD5141	Approved
0.6087	Remote Similarity	NPD4753	Phase 2
0.6078	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD6881	Approved
0.6064	Remote Similarity	NPD6399	Phase 3
0.6049	Remote Similarity	NPD7143	Approved
0.6049	Remote Similarity	NPD7144	Approved
0.6047	Remote Similarity	NPD4195	Approved
0.6047	Remote Similarity	NPD6683	Phase 2
0.6044	Remote Similarity	NPD7524	Approved
0.6044	Remote Similarity	NPD7750	Discontinued
0.6042	Remote Similarity	NPD5221	Approved
0.6042	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4697	Phase 3
0.6042	Remote Similarity	NPD5222	Approved
0.604	Remote Similarity	NPD4767	Approved
0.604	Remote Similarity	NPD4768	Approved
0.6019	Remote Similarity	NPD6373	Approved
0.6019	Remote Similarity	NPD7328	Approved
0.6019	Remote Similarity	NPD7327	Approved
0.6019	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD3198	Approved
0.598	Remote Similarity	NPD5701	Approved
0.598	Remote Similarity	NPD5697	Approved
0.5979	Remote Similarity	NPD5173	Approved
0.5977	Remote Similarity	NPD7514	Phase 3
0.5963	Remote Similarity	NPD7516	Approved
0.5962	Remote Similarity	NPD7102	Approved
0.5962	Remote Similarity	NPD7290	Approved
0.5962	Remote Similarity	NPD6883	Approved
0.5957	Remote Similarity	NPD7515	Phase 2
0.5943	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD6011	Approved
0.5922	Remote Similarity	NPD4729	Approved
0.5922	Remote Similarity	NPD4730	Approved
0.5922	Remote Similarity	NPD5128	Approved
0.5909	Remote Similarity	NPD8377	Approved
0.5909	Remote Similarity	NPD6902	Approved
0.5909	Remote Similarity	NPD8294	Approved
0.5905	Remote Similarity	NPD6650	Approved
0.5905	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6617	Approved
0.5905	Remote Similarity	NPD6847	Approved
0.5905	Remote Similarity	NPD8130	Phase 1
0.5905	Remote Similarity	NPD6649	Approved
0.5905	Remote Similarity	NPD6869	Approved
0.5865	Remote Similarity	NPD6012	Approved
0.5865	Remote Similarity	NPD6014	Approved
0.5865	Remote Similarity	NPD6013	Approved
0.5856	Remote Similarity	NPD8380	Approved
0.5856	Remote Similarity	NPD8378	Approved
0.5856	Remote Similarity	NPD8379	Approved
0.5856	Remote Similarity	NPD8033	Approved
0.5856	Remote Similarity	NPD8296	Approved
0.5856	Remote Similarity	NPD8335	Approved
0.5854	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD2687	Approved
0.5854	Remote Similarity	NPD2254	Approved
0.5854	Remote Similarity	NPD2686	Approved
0.5849	Remote Similarity	NPD6882	Approved
0.5849	Remote Similarity	NPD8297	Approved
0.5843	Remote Similarity	NPD4223	Phase 3
0.5843	Remote Similarity	NPD4221	Approved
0.5825	Remote Similarity	NPD6412	Phase 2
0.5825	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD5329	Approved
0.5816	Remote Similarity	NPD6084	Phase 2
0.5816	Remote Similarity	NPD6083	Phase 2
0.5811	Remote Similarity	NPD586	Phase 1
0.581	Remote Similarity	NPD5250	Approved
0.581	Remote Similarity	NPD5169	Approved
0.581	Remote Similarity	NPD5251	Approved
0.581	Remote Similarity	NPD5135	Approved
0.581	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5247	Approved
0.581	Remote Similarity	NPD5248	Approved
0.581	Remote Similarity	NPD5249	Phase 3
0.58	Remote Similarity	NPD1700	Approved
0.58	Remote Similarity	NPD4159	Approved
0.5795	Remote Similarity	NPD7332	Phase 2
0.5794	Remote Similarity	NPD8133	Approved
0.5789	Remote Similarity	NPD7087	Discontinued
0.578	Remote Similarity	NPD6009	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