NPASS Compound

Structure

NPC255882 OpenBabel07101718242D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 -1.7321 2.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7852 5.6132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -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 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0724 6.7722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 28 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 16 2 1 1 0 0 0 16 20 1 0 0 0 0 17 3 1 1 0 0 0 18 12 1 1 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 6 0 0 0 20 28 1 6 0 0 0 21 26 1 0 0 0 0 21 30 1 6 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 28 1 6 0 0 0 25 26 1 0 0 0 0 25 27 1 6 0 0 0 26 33 1 6 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.35
Volume:	499.933
LogP:	3.924
LogD:	4.222
LogS:	-3.717
# Rotatable Bonds:	6
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	5.155
Fsp3:	0.929
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:	-4.903
MDCK Permeability:	2.6414394596940838e-05
Pgp-inhibitor:	0.196
Pgp-substrate:	0.879
Human Intestinal Absorption (HIA):	0.155
20% Bioavailability (F20%):	0.432
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	89.31917572021484%
Volume Distribution (VD):	0.68
Pgp-substrate:	4.5024590492248535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	6.37
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.333
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.347
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.531
Carcinogencity:	0.061
Eye Corrosion:	0.009
Eye Irritation:	0.045
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC255882

Natural Product ID:	NPC255882
*Common Name:**	Certonardosterol B
IUPAC Name:	(3S,4R,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(2R,6S)-7-hydroxy-6-methyl-5-methylideneheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,6,15-tetrol
Synonyms:	Certonardosterol B
Standard InCHIKey:	NJTYOAHMFCPZLI-GFJGGNKHSA-N
Standard InCHI:	InChI=1S/C28H48O5/c1-15(17(3)14-29)6-7-16(2)20-13-23(32)24-18-12-22(31)25-26(33)21(30)9-11-27(25,4)19(18)8-10-28(20,24)5/h16-26,29-33H,1,6-14H2,2-5H3/t16-,17-,18-,19+,20-,21+,22+,23-,24-,25+,26+,27-,28-/m1/s1
SMILES:	C=C(CC[C@@H](C)[C@H]1C[C@H]([C@H]2[C@@H]3C[C@@H]([C@H]4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O)[C@H](C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475490
PubChem CID:	21629545
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:0002198] Pentahydroxy 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	=	3.6	ug ml-1	PMID[491799]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	6.9	ug ml-1	PMID[491799]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.9	ug ml-1	PMID[491799]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	4.7	ug ml-1	PMID[491799]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	6.4	ug ml-1	PMID[491799]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	25.0	ug.mL-1	PMID[491799]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[491799]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	25.0	ug.mL-1	PMID[491799]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25.0	ug.mL-1	PMID[491799]

☑ 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 NPC255882 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	206
0.1-0.2	2112
0.2-0.3	7368
0.3-0.4	15442
0.4-0.5	6988
0.5-0.6	4539
0.6-0.7	4277
0.7-0.8	1510
0.8-0.85	177
0.85-0.9	60
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC121981
0.9487	High Similarity	NPC71535
0.9487	High Similarity	NPC78545
0.9375	High Similarity	NPC232023
0.9375	High Similarity	NPC85095
0.9375	High Similarity	NPC216420
0.9375	High Similarity	NPC211135
0.9277	High Similarity	NPC475664
0.9231	High Similarity	NPC477817
0.9231	High Similarity	NPC477819
0.9167	High Similarity	NPC105495
0.9157	High Similarity	NPC474657
0.9157	High Similarity	NPC186145
0.9059	High Similarity	NPC473956
0.9059	High Similarity	NPC475751
0.9024	High Similarity	NPC256567
0.9	High Similarity	NPC47149
0.8941	High Similarity	NPC109744
0.8902	High Similarity	NPC110778
0.8889	High Similarity	NPC157655
0.8875	High Similarity	NPC24504
0.8875	High Similarity	NPC476316
0.881	High Similarity	NPC24277
0.881	High Similarity	NPC201273
0.8795	High Similarity	NPC127606
0.8795	High Similarity	NPC124172
0.8795	High Similarity	NPC475798
0.8765	High Similarity	NPC475679
0.875	High Similarity	NPC472499
0.875	High Similarity	NPC472500
0.875	High Similarity	NPC472502
0.875	High Similarity	NPC475
0.875	High Similarity	NPC31828
0.875	High Similarity	NPC102708
0.8734	High Similarity	NPC91573
0.8734	High Similarity	NPC163597
0.8718	High Similarity	NPC308440
0.8718	High Similarity	NPC472503
0.8706	High Similarity	NPC477600
0.8675	High Similarity	NPC141941
0.8675	High Similarity	NPC193870
0.8675	High Similarity	NPC207013
0.8675	High Similarity	NPC477818
0.8642	High Similarity	NPC80297
0.8642	High Similarity	NPC5604
0.8642	High Similarity	NPC116119
0.8642	High Similarity	NPC472742
0.8642	High Similarity	NPC475727
0.8625	High Similarity	NPC202540
0.8625	High Similarity	NPC138502
0.8625	High Similarity	NPC307336
0.8625	High Similarity	NPC477227
0.8625	High Similarity	NPC192046
0.8625	High Similarity	NPC105208
0.8625	High Similarity	NPC260301
0.8625	High Similarity	NPC128951
0.8625	High Similarity	NPC302578
0.8608	High Similarity	NPC3403
0.8608	High Similarity	NPC317242
0.8605	High Similarity	NPC473436
0.859	High Similarity	NPC470610
0.8588	High Similarity	NPC6605
0.8588	High Similarity	NPC269058
0.8588	High Similarity	NPC145245
0.8588	High Similarity	NPC71520
0.8571	High Similarity	NPC209802
0.8571	High Similarity	NPC242016
0.8554	High Similarity	NPC470614
0.8554	High Similarity	NPC1272
0.8554	High Similarity	NPC477599
0.8523	High Similarity	NPC219516
0.8519	High Similarity	NPC472501
0.8519	High Similarity	NPC67657
0.8519	High Similarity	NPC18857
0.8519	High Similarity	NPC42853
0.8519	High Similarity	NPC301707
0.85	High Similarity	NPC93662
0.85	High Similarity	NPC14112
0.85	High Similarity	NPC278091
0.85	High Similarity	NPC78067
0.85	High Similarity	NPC38141
0.85	High Similarity	NPC86305
0.8481	Intermediate Similarity	NPC48795
0.8462	Intermediate Similarity	NPC111234
0.8452	Intermediate Similarity	NPC470929
0.8444	Intermediate Similarity	NPC30477
0.8434	Intermediate Similarity	NPC474531
0.8415	Intermediate Similarity	NPC49599
0.8415	Intermediate Similarity	NPC49627
0.8395	Intermediate Similarity	NPC185915
0.8391	Intermediate Similarity	NPC474668
0.8391	Intermediate Similarity	NPC470542
0.8391	Intermediate Similarity	NPC67872
0.8391	Intermediate Similarity	NPC160304
0.8375	Intermediate Similarity	NPC158208
0.8375	Intermediate Similarity	NPC231256
0.8375	Intermediate Similarity	NPC185536
0.8375	Intermediate Similarity	NPC230704
0.8375	Intermediate Similarity	NPC104387
0.8375	Intermediate Similarity	NPC103822
0.8375	Intermediate Similarity	NPC240235
0.8375	Intermediate Similarity	NPC196136
0.8375	Intermediate Similarity	NPC178383
0.8375	Intermediate Similarity	NPC243027
0.8375	Intermediate Similarity	NPC212879
0.8375	Intermediate Similarity	NPC70982
0.8372	Intermediate Similarity	NPC94462
0.8372	Intermediate Similarity	NPC237344
0.8372	Intermediate Similarity	NPC139724
0.8354	Intermediate Similarity	NPC95165
0.8354	Intermediate Similarity	NPC153719
0.8353	Intermediate Similarity	NPC86238
0.8352	Intermediate Similarity	NPC292718
0.8352	Intermediate Similarity	NPC111834
0.8352	Intermediate Similarity	NPC306797
0.8352	Intermediate Similarity	NPC169270
0.8333	Intermediate Similarity	NPC63588
0.8333	Intermediate Similarity	NPC45296
0.8333	Intermediate Similarity	NPC30166
0.8333	Intermediate Similarity	NPC232925
0.8333	Intermediate Similarity	NPC277399
0.8333	Intermediate Similarity	NPC7988
0.8333	Intermediate Similarity	NPC251201
0.8315	Intermediate Similarity	NPC41554
0.8315	Intermediate Similarity	NPC97404
0.8313	Intermediate Similarity	NPC236237
0.8313	Intermediate Similarity	NPC102253
0.8313	Intermediate Similarity	NPC13554
0.8313	Intermediate Similarity	NPC236112
0.8313	Intermediate Similarity	NPC26117
0.8313	Intermediate Similarity	NPC322313
0.8295	Intermediate Similarity	NPC470361
0.8293	Intermediate Similarity	NPC167037
0.8293	Intermediate Similarity	NPC244385
0.8293	Intermediate Similarity	NPC6978
0.8293	Intermediate Similarity	NPC138621
0.828	Intermediate Similarity	NPC208358
0.828	Intermediate Similarity	NPC471247
0.8276	Intermediate Similarity	NPC470620
0.8261	Intermediate Similarity	NPC477226
0.8261	Intermediate Similarity	NPC274793
0.8261	Intermediate Similarity	NPC475032
0.8261	Intermediate Similarity	NPC170978
0.8261	Intermediate Similarity	NPC475033
0.8261	Intermediate Similarity	NPC76486
0.825	Intermediate Similarity	NPC196358
0.825	Intermediate Similarity	NPC254509
0.825	Intermediate Similarity	NPC5046
0.825	Intermediate Similarity	NPC49168
0.825	Intermediate Similarity	NPC192638
0.825	Intermediate Similarity	NPC228994
0.825	Intermediate Similarity	NPC10476
0.825	Intermediate Similarity	NPC145552
0.825	Intermediate Similarity	NPC192501
0.825	Intermediate Similarity	NPC25511
0.825	Intermediate Similarity	NPC304499
0.825	Intermediate Similarity	NPC62657
0.8242	Intermediate Similarity	NPC473348
0.8242	Intermediate Similarity	NPC241047
0.8235	Intermediate Similarity	NPC113978
0.8222	Intermediate Similarity	NPC296620
0.8222	Intermediate Similarity	NPC26046
0.8222	Intermediate Similarity	NPC291373
0.8222	Intermediate Similarity	NPC98193
0.8214	Intermediate Similarity	NPC470383
0.8205	Intermediate Similarity	NPC477820
0.8202	Intermediate Similarity	NPC219937
0.8202	Intermediate Similarity	NPC291484
0.8202	Intermediate Similarity	NPC11216
0.8202	Intermediate Similarity	NPC194485
0.8202	Intermediate Similarity	NPC80561
0.8202	Intermediate Similarity	NPC107189
0.8202	Intermediate Similarity	NPC53890
0.8202	Intermediate Similarity	NPC204188
0.8202	Intermediate Similarity	NPC329596
0.8202	Intermediate Similarity	NPC3345
0.8202	Intermediate Similarity	NPC123252
0.8193	Intermediate Similarity	NPC80530
0.8193	Intermediate Similarity	NPC287452
0.8193	Intermediate Similarity	NPC273410
0.8193	Intermediate Similarity	NPC472463
0.8193	Intermediate Similarity	NPC1319
0.8191	Intermediate Similarity	NPC155974
0.8191	Intermediate Similarity	NPC31346
0.8182	Intermediate Similarity	NPC133588
0.8182	Intermediate Similarity	NPC22376
0.8182	Intermediate Similarity	NPC2158
0.8171	Intermediate Similarity	NPC119355
0.8171	Intermediate Similarity	NPC331618
0.8171	Intermediate Similarity	NPC257191
0.8171	Intermediate Similarity	NPC212241
0.8171	Intermediate Similarity	NPC248830
0.8161	Intermediate Similarity	NPC293287
0.8161	Intermediate Similarity	NPC152808
0.8161	Intermediate Similarity	NPC6391
0.8152	Intermediate Similarity	NPC471903
0.8148	Intermediate Similarity	NPC200243
0.814	Intermediate Similarity	NPC299963
0.814	Intermediate Similarity	NPC185568
0.814	Intermediate Similarity	NPC238992

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 NPC255882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	2468
0.2-0.3	4241
0.3-0.4	1550
0.4-0.5	319
0.5-0.6	158
0.6-0.7	197
0.7-0.8	40
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD7525	Registered
0.7975	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6942	Approved
0.7711	Intermediate Similarity	NPD7339	Approved
0.7473	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7524	Approved
0.7444	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6933	Approved
0.7356	Intermediate Similarity	NPD6929	Approved
0.7356	Intermediate Similarity	NPD7645	Phase 2
0.7333	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4748	Discontinued
0.7273	Intermediate Similarity	NPD6931	Approved
0.7273	Intermediate Similarity	NPD6930	Phase 2
0.7229	Intermediate Similarity	NPD4787	Phase 1
0.7222	Intermediate Similarity	NPD6695	Phase 3
0.7222	Intermediate Similarity	NPD4788	Approved
0.7176	Intermediate Similarity	NPD6924	Approved
0.7176	Intermediate Similarity	NPD4785	Approved
0.7176	Intermediate Similarity	NPD6926	Approved
0.7176	Intermediate Similarity	NPD4784	Approved
0.7158	Intermediate Similarity	NPD8034	Phase 2
0.7158	Intermediate Similarity	NPD8035	Phase 2
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD4243	Approved
0.7126	Intermediate Similarity	NPD6932	Approved
0.7126	Intermediate Similarity	NPD6925	Approved
0.7126	Intermediate Similarity	NPD5776	Phase 2
0.7083	Intermediate Similarity	NPD4202	Approved
0.7079	Intermediate Similarity	NPD6928	Phase 2
0.7071	Intermediate Similarity	NPD7638	Approved
0.7048	Intermediate Similarity	NPD4634	Approved
0.7045	Intermediate Similarity	NPD6697	Approved
0.7045	Intermediate Similarity	NPD7145	Approved
0.7045	Intermediate Similarity	NPD6115	Approved
0.7045	Intermediate Similarity	NPD6118	Approved
0.7045	Intermediate Similarity	NPD6114	Approved
0.7	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD4700	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.6966	Remote Similarity	NPD6683	Phase 2
0.6947	Remote Similarity	NPD5328	Approved
0.6941	Remote Similarity	NPD7151	Approved
0.6941	Remote Similarity	NPD7150	Approved
0.6941	Remote Similarity	NPD7152	Approved
0.6932	Remote Similarity	NPD6116	Phase 1
0.6923	Remote Similarity	NPD3667	Approved
0.6915	Remote Similarity	NPD7750	Discontinued
0.6909	Remote Similarity	NPD7327	Approved
0.6909	Remote Similarity	NPD7328	Approved
0.6907	Remote Similarity	NPD8171	Discontinued
0.6905	Remote Similarity	NPD6922	Approved
0.6905	Remote Similarity	NPD6923	Approved
0.6889	Remote Similarity	NPD7514	Phase 3
0.6889	Remote Similarity	NPD7509	Discontinued
0.6882	Remote Similarity	NPD6893	Approved
0.6875	Remote Similarity	NPD8033	Approved
0.6863	Remote Similarity	NPD5211	Phase 2
0.6863	Remote Similarity	NPD4633	Approved
0.6863	Remote Similarity	NPD5224	Approved
0.6863	Remote Similarity	NPD5225	Approved
0.6863	Remote Similarity	NPD5226	Approved
0.6827	Remote Similarity	NPD7128	Approved
0.6827	Remote Similarity	NPD6675	Approved
0.6827	Remote Similarity	NPD5739	Approved
0.6827	Remote Similarity	NPD6402	Approved
0.6824	Remote Similarity	NPD7144	Approved
0.6824	Remote Similarity	NPD7143	Approved
0.6818	Remote Similarity	NPD6117	Approved
0.6813	Remote Similarity	NPD6902	Approved
0.6809	Remote Similarity	NPD3618	Phase 1
0.6804	Remote Similarity	NPD6079	Approved
0.6796	Remote Similarity	NPD5174	Approved
0.6796	Remote Similarity	NPD5175	Approved
0.6786	Remote Similarity	NPD8294	Approved
0.6786	Remote Similarity	NPD8377	Approved
0.6774	Remote Similarity	NPD3133	Approved
0.6774	Remote Similarity	NPD3665	Phase 1
0.6774	Remote Similarity	NPD3666	Approved
0.6771	Remote Similarity	NPD4753	Phase 2
0.6765	Remote Similarity	NPD5223	Approved
0.6765	Remote Similarity	NPD4159	Approved
0.6762	Remote Similarity	NPD6412	Phase 2
0.6744	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6399	Phase 3
0.6731	Remote Similarity	NPD5141	Approved
0.6726	Remote Similarity	NPD8379	Approved
0.6726	Remote Similarity	NPD8378	Approved
0.6726	Remote Similarity	NPD8335	Approved
0.6726	Remote Similarity	NPD8296	Approved
0.6726	Remote Similarity	NPD8380	Approved
0.6705	Remote Similarity	NPD3703	Phase 2
0.6705	Remote Similarity	NPD5275	Approved
0.6705	Remote Similarity	NPD4190	Phase 3
0.6703	Remote Similarity	NPD7332	Phase 2
0.6698	Remote Similarity	NPD7320	Approved
0.6698	Remote Similarity	NPD6899	Approved
0.6698	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6697	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD4754	Approved
0.6633	Remote Similarity	NPD7087	Discontinued
0.663	Remote Similarity	NPD6898	Phase 1
0.6628	Remote Similarity	NPD4244	Approved
0.6628	Remote Similarity	NPD4245	Approved
0.6606	Remote Similarity	NPD8297	Approved
0.6604	Remote Similarity	NPD5701	Approved
0.6604	Remote Similarity	NPD5697	Approved
0.6593	Remote Similarity	NPD4195	Approved
0.6591	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7290	Approved
0.6574	Remote Similarity	NPD7102	Approved
0.6574	Remote Similarity	NPD6883	Approved
0.6542	Remote Similarity	NPD5128	Approved
0.6542	Remote Similarity	NPD4730	Approved
0.6542	Remote Similarity	NPD4729	Approved
0.6538	Remote Similarity	NPD7632	Discontinued
0.6535	Remote Similarity	NPD4697	Phase 3
0.6535	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5222	Approved
0.6535	Remote Similarity	NPD5221	Approved
0.6514	Remote Similarity	NPD6649	Approved
0.6514	Remote Similarity	NPD6869	Approved
0.6514	Remote Similarity	NPD6847	Approved
0.6514	Remote Similarity	NPD6617	Approved
0.6514	Remote Similarity	NPD6650	Approved
0.6514	Remote Similarity	NPD8130	Phase 1
0.6512	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3698	Phase 2
0.6496	Remote Similarity	NPD7507	Approved
0.6491	Remote Similarity	NPD6054	Approved
0.6491	Remote Similarity	NPD6319	Approved
0.6491	Remote Similarity	NPD6059	Approved
0.6481	Remote Similarity	NPD6012	Approved
0.6481	Remote Similarity	NPD6014	Approved
0.6481	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD5173	Approved
0.6465	Remote Similarity	NPD7515	Phase 2
0.6455	Remote Similarity	NPD6882	Approved
0.6436	Remote Similarity	NPD4629	Approved
0.6436	Remote Similarity	NPD5210	Approved
0.6435	Remote Similarity	NPD7503	Approved
0.6422	Remote Similarity	NPD5249	Phase 3
0.6422	Remote Similarity	NPD5247	Approved
0.6422	Remote Similarity	NPD5248	Approved
0.6422	Remote Similarity	NPD5250	Approved
0.6422	Remote Similarity	NPD5251	Approved
0.6421	Remote Similarity	NPD3668	Phase 3
0.6389	Remote Similarity	NPD6011	Approved
0.6383	Remote Similarity	NPD4223	Phase 3
0.6383	Remote Similarity	NPD4221	Approved
0.6379	Remote Similarity	NPD6370	Approved
0.6372	Remote Similarity	NPD6009	Approved
0.6364	Remote Similarity	NPD5215	Approved
0.6364	Remote Similarity	NPD5216	Approved
0.6364	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5217	Approved
0.6355	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD5329	Approved
0.6333	Remote Similarity	NPD7319	Approved
0.631	Remote Similarity	NPD371	Approved
0.6304	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7637	Suspended
0.6293	Remote Similarity	NPD6016	Approved
0.6293	Remote Similarity	NPD6015	Approved
0.6273	Remote Similarity	NPD5169	Approved
0.6273	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5135	Approved
0.6271	Remote Similarity	NPD7492	Approved
0.6263	Remote Similarity	NPD6051	Approved
0.6262	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD4789	Approved
0.625	Remote Similarity	NPD4197	Approved
0.6239	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5988	Approved
0.6228	Remote Similarity	NPD7115	Discovery
0.6218	Remote Similarity	NPD6616	Approved
0.6216	Remote Similarity	NPD5127	Approved
0.6207	Remote Similarity	NPD5360	Phase 3
0.6207	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6700	Approved
0.62	Remote Similarity	NPD7136	Phase 2
0.6186	Remote Similarity	NPD7604	Phase 2

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