NPASS Compound

Structure

NPC232023 OpenBabel07101719252D 33 36 0 0 1 0 0 0 0 0999 V2000 -1.7660 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3840 6.3564 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 -0.4593 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 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 -4.0313 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7441 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0531 5.6132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 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 2 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 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 2 0 0 0 0 0 0 0 0 0 -4.3403 6.7722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 17 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 24 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 17 2 1 1 0 0 0 17 20 1 0 0 0 0 18 3 1 1 0 0 0 19 30 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 25 1 0 0 0 0 22 31 1 6 0 0 0 23 32 1 1 0 0 0 24 26 1 6 0 0 0 24 28 1 0 0 0 0 25 27 1 6 0 0 0 25 28 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 28 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.35
Volume:	499.933
LogP:	3.52
LogD:	3.654
LogS:	-3.985
# 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:	0.386
Synthetic Accessibility Score:	5.173
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:	-4.901
MDCK Permeability:	1.683880327618681e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.335
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	81.39434051513672%
Volume Distribution (VD):	0.706
Pgp-substrate:	14.092357635498047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.531
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	6.581
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.233
Maximum Recommended Daily Dose:	0.843
Skin Sensitization:	0.727
Carcinogencity:	0.323
Eye Corrosion:	0.016
Eye Irritation:	0.065
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC232023

Natural Product ID:	NPC232023
*Common Name:**	Certonardosterol C
IUPAC Name:	(3S,5S,6S,8S,9R,10S,13R,14S,15R,17R)-17-[(2R,6S)-7-hydroxy-6-methyl-5-methylideneheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15-tetrol
Synonyms:	Certonardosterol C
Standard InCHIKey:	AHDGWLLYXUUQCO-BOCJNLEFSA-N
Standard InCHI:	InChI=1S/C28H48O5/c1-16(18(3)15-29)6-7-17(2)20-13-22(31)25-27(20,5)11-9-24-26(4)10-8-19(30)12-21(26)23(32)14-28(24,25)33/h17-25,29-33H,1,6-15H2,2-5H3/t17-,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@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](C[C@@H]3[C@H](C[C@@]21O)O)O)O)[C@H](C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476696
PubChem CID:	21629546
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	=	14.1	ug ml-1	PMID[475341]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	20.2	ug ml-1	PMID[475341]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	15.1	ug ml-1	PMID[475341]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	13.3	ug ml-1	PMID[475341]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	23.9	ug ml-1	PMID[475341]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	25.0	ug.mL-1	PMID[475341]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[475341]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	25.0	ug.mL-1	PMID[475341]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25.0	ug.mL-1	PMID[475341]

☑ 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 NPC232023 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	202
0.1-0.2	2196
0.2-0.3	7732
0.3-0.4	15477
0.4-0.5	6465
0.5-0.6	4787
0.6-0.7	4207
0.7-0.8	1368
0.8-0.85	163
0.85-0.9	77
0.9-0.95	19
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC121981
0.961	High Similarity	NPC78545
0.961	High Similarity	NPC71535
0.9383	High Similarity	NPC201273
0.9375	High Similarity	NPC256567
0.9375	High Similarity	NPC255882
0.9351	High Similarity	NPC477819
0.9351	High Similarity	NPC31828
0.9351	High Similarity	NPC477817
0.925	High Similarity	NPC216420
0.925	High Similarity	NPC85095
0.925	High Similarity	NPC211135
0.9146	High Similarity	NPC6605
0.9114	High Similarity	NPC475679
0.9114	High Similarity	NPC47149
0.9012	High Similarity	NPC470929
0.9012	High Similarity	NPC110778
0.9	High Similarity	NPC157655
0.8987	High Similarity	NPC475727
0.8987	High Similarity	NPC116119
0.8987	High Similarity	NPC472742
0.8987	High Similarity	NPC80297
0.8987	High Similarity	NPC24504
0.8987	High Similarity	NPC476316
0.8961	High Similarity	NPC3403
0.8941	High Similarity	NPC475751
0.8941	High Similarity	NPC473956
0.8916	High Similarity	NPC24277
0.8902	High Similarity	NPC475798
0.8902	High Similarity	NPC86238
0.8902	High Similarity	NPC124172
0.8902	High Similarity	NPC127606
0.8861	High Similarity	NPC301707
0.8861	High Similarity	NPC472500
0.8861	High Similarity	NPC472501
0.8861	High Similarity	NPC42853
0.8861	High Similarity	NPC472499
0.8861	High Similarity	NPC472502
0.8861	High Similarity	NPC475
0.8831	High Similarity	NPC472503
0.8831	High Similarity	NPC304499
0.8831	High Similarity	NPC308440
0.8824	High Similarity	NPC109744
0.878	High Similarity	NPC141941
0.878	High Similarity	NPC477818
0.878	High Similarity	NPC193870
0.875	High Similarity	NPC5604
0.875	High Similarity	NPC49627
0.875	High Similarity	NPC49599
0.8734	High Similarity	NPC260301
0.8734	High Similarity	NPC307336
0.8734	High Similarity	NPC138502
0.8734	High Similarity	NPC202540
0.8706	High Similarity	NPC475664
0.8675	High Similarity	NPC209802
0.8659	High Similarity	NPC470614
0.8659	High Similarity	NPC1272
0.8642	High Similarity	NPC236237
0.8642	High Similarity	NPC322313
0.8642	High Similarity	NPC102253
0.8608	High Similarity	NPC91573
0.8608	High Similarity	NPC78067
0.8608	High Similarity	NPC14112
0.8608	High Similarity	NPC278091
0.8608	High Similarity	NPC38141
0.8608	High Similarity	NPC86305
0.8608	High Similarity	NPC93662
0.8605	High Similarity	NPC74258
0.8605	High Similarity	NPC105495
0.8588	High Similarity	NPC186145
0.8588	High Similarity	NPC474657
0.8588	High Similarity	NPC477600
0.8571	High Similarity	NPC111234
0.8554	High Similarity	NPC113978
0.8537	High Similarity	NPC470383
0.8523	High Similarity	NPC26046
0.8519	High Similarity	NPC80530
0.8519	High Similarity	NPC273410
0.8506	High Similarity	NPC10274
0.8506	High Similarity	NPC219937
0.8506	High Similarity	NPC123252
0.8506	High Similarity	NPC194485
0.8506	High Similarity	NPC53890
0.85	High Similarity	NPC302578
0.85	High Similarity	NPC477227
0.85	High Similarity	NPC105208
0.85	High Similarity	NPC192046
0.85	High Similarity	NPC128951
0.85	High Similarity	NPC185915
0.8488	Intermediate Similarity	NPC470542
0.8488	Intermediate Similarity	NPC160304
0.8488	Intermediate Similarity	NPC473436
0.8481	Intermediate Similarity	NPC104387
0.8481	Intermediate Similarity	NPC240235
0.8481	Intermediate Similarity	NPC317242
0.8481	Intermediate Similarity	NPC178383
0.8481	Intermediate Similarity	NPC70982
0.8481	Intermediate Similarity	NPC230704
0.8481	Intermediate Similarity	NPC103822
0.8481	Intermediate Similarity	NPC212879
0.8481	Intermediate Similarity	NPC185536
0.8481	Intermediate Similarity	NPC231256
0.8471	Intermediate Similarity	NPC139724
0.8471	Intermediate Similarity	NPC6391
0.8471	Intermediate Similarity	NPC152808
0.8471	Intermediate Similarity	NPC293287
0.8452	Intermediate Similarity	NPC242016
0.8442	Intermediate Similarity	NPC63588
0.8442	Intermediate Similarity	NPC45296
0.8442	Intermediate Similarity	NPC251201
0.8442	Intermediate Similarity	NPC232925
0.8427	Intermediate Similarity	NPC3359
0.8415	Intermediate Similarity	NPC26117
0.8409	Intermediate Similarity	NPC97404
0.8409	Intermediate Similarity	NPC219516
0.8409	Intermediate Similarity	NPC130840
0.8409	Intermediate Similarity	NPC41554
0.8395	Intermediate Similarity	NPC244385
0.8395	Intermediate Similarity	NPC138621
0.8395	Intermediate Similarity	NPC472342
0.8395	Intermediate Similarity	NPC18857
0.8395	Intermediate Similarity	NPC6978
0.8395	Intermediate Similarity	NPC67657
0.8395	Intermediate Similarity	NPC285761
0.8395	Intermediate Similarity	NPC167037
0.8391	Intermediate Similarity	NPC470361
0.8375	Intermediate Similarity	NPC63958
0.8375	Intermediate Similarity	NPC163597
0.8354	Intermediate Similarity	NPC25511
0.8354	Intermediate Similarity	NPC196358
0.8354	Intermediate Similarity	NPC145552
0.8354	Intermediate Similarity	NPC62657
0.8354	Intermediate Similarity	NPC476736
0.8354	Intermediate Similarity	NPC192638
0.8354	Intermediate Similarity	NPC5046
0.8354	Intermediate Similarity	NPC49168
0.8354	Intermediate Similarity	NPC254509
0.8333	Intermediate Similarity	NPC207013
0.8312	Intermediate Similarity	NPC66407
0.8312	Intermediate Similarity	NPC477820
0.8295	Intermediate Similarity	NPC46758
0.8295	Intermediate Similarity	NPC3345
0.8295	Intermediate Similarity	NPC291484
0.8295	Intermediate Similarity	NPC329596
0.8295	Intermediate Similarity	NPC11216
0.8295	Intermediate Similarity	NPC80561
0.8295	Intermediate Similarity	NPC204188
0.8293	Intermediate Similarity	NPC472463
0.8293	Intermediate Similarity	NPC287452
0.8293	Intermediate Similarity	NPC1319
0.8276	Intermediate Similarity	NPC2158
0.8272	Intermediate Similarity	NPC212241
0.8272	Intermediate Similarity	NPC331618
0.8272	Intermediate Similarity	NPC248830
0.8272	Intermediate Similarity	NPC257191
0.8272	Intermediate Similarity	NPC119355
0.8256	Intermediate Similarity	NPC269058
0.8256	Intermediate Similarity	NPC261266
0.8256	Intermediate Similarity	NPC299068
0.8256	Intermediate Similarity	NPC145245
0.8256	Intermediate Similarity	NPC71520
0.825	Intermediate Similarity	NPC243027
0.825	Intermediate Similarity	NPC158208
0.825	Intermediate Similarity	NPC196136
0.825	Intermediate Similarity	NPC200243
0.8235	Intermediate Similarity	NPC299963
0.8235	Intermediate Similarity	NPC474493
0.8228	Intermediate Similarity	NPC153719
0.8228	Intermediate Similarity	NPC472506
0.8228	Intermediate Similarity	NPC470610
0.8228	Intermediate Similarity	NPC195489
0.8214	Intermediate Similarity	NPC248886
0.8214	Intermediate Similarity	NPC30166
0.8193	Intermediate Similarity	NPC13554
0.8182	Intermediate Similarity	NPC474756
0.8182	Intermediate Similarity	NPC101886
0.8171	Intermediate Similarity	NPC102708
0.8171	Intermediate Similarity	NPC477522
0.8171	Intermediate Similarity	NPC87604
0.8161	Intermediate Similarity	NPC475313
0.8161	Intermediate Similarity	NPC271967
0.8152	Intermediate Similarity	NPC170978
0.8152	Intermediate Similarity	NPC477226
0.8148	Intermediate Similarity	NPC237460
0.814	Intermediate Similarity	NPC318390
0.814	Intermediate Similarity	NPC470360
0.814	Intermediate Similarity	NPC474349
0.814	Intermediate Similarity	NPC474189
0.8132	Intermediate Similarity	NPC241047
0.8125	Intermediate Similarity	NPC475458
0.8125	Intermediate Similarity	NPC192501
0.8125	Intermediate Similarity	NPC10476
0.8125	Intermediate Similarity	NPC48795
0.8125	Intermediate Similarity	NPC228994
0.8111	Intermediate Similarity	NPC98193
0.8101	Intermediate Similarity	NPC470071
0.8101	Intermediate Similarity	NPC252182
0.8101	Intermediate Similarity	NPC187471
0.8101	Intermediate Similarity	NPC1340
0.8101	Intermediate Similarity	NPC127094

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 NPC232023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2512
0.2-0.3	4277
0.3-0.4	1506
0.4-0.5	282
0.5-0.6	153
0.6-0.7	191
0.7-0.8	60
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD7525	Registered
0.7927	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7339	Approved
0.7805	Intermediate Similarity	NPD6942	Approved
0.7765	Intermediate Similarity	NPD6930	Phase 2
0.7765	Intermediate Similarity	NPD6931	Approved
0.7753	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6695	Phase 3
0.7647	Intermediate Similarity	NPD6929	Approved
0.7619	Intermediate Similarity	NPD6932	Approved
0.7558	Intermediate Similarity	NPD4748	Discontinued
0.7531	Intermediate Similarity	NPD4787	Phase 1
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4788	Approved
0.747	Intermediate Similarity	NPD6926	Approved
0.747	Intermediate Similarity	NPD6924	Approved
0.747	Intermediate Similarity	NPD4784	Approved
0.747	Intermediate Similarity	NPD4785	Approved
0.7442	Intermediate Similarity	NPD7645	Phase 2
0.7442	Intermediate Similarity	NPD6683	Phase 2
0.7439	Intermediate Similarity	NPD4243	Approved
0.7412	Intermediate Similarity	NPD5776	Phase 2
0.7412	Intermediate Similarity	NPD6925	Approved
0.7396	Intermediate Similarity	NPD4755	Approved
0.7363	Intermediate Similarity	NPD7524	Approved
0.7363	Intermediate Similarity	NPD7750	Discontinued
0.7356	Intermediate Similarity	NPD7514	Phase 3
0.734	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD6893	Approved
0.7326	Intermediate Similarity	NPD7145	Approved
0.7294	Intermediate Similarity	NPD6933	Approved
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7245	Intermediate Similarity	NPD4700	Approved
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7222	Intermediate Similarity	NPD4786	Approved
0.7159	Intermediate Similarity	NPD7332	Phase 2
0.7159	Intermediate Similarity	NPD7509	Discontinued
0.7159	Intermediate Similarity	NPD6928	Phase 2
0.7143	Intermediate Similarity	NPD7638	Approved
0.7126	Intermediate Similarity	NPD6697	Approved
0.7126	Intermediate Similarity	NPD6115	Approved
0.7126	Intermediate Similarity	NPD6118	Approved
0.7126	Intermediate Similarity	NPD6114	Approved
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD5224	Approved
0.7079	Intermediate Similarity	NPD6902	Approved
0.7079	Intermediate Similarity	NPD6898	Phase 1
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7053	Intermediate Similarity	NPD7087	Discontinued
0.703	Intermediate Similarity	NPD5175	Approved
0.703	Intermediate Similarity	NPD5174	Approved
0.7024	Intermediate Similarity	NPD7151	Approved
0.7024	Intermediate Similarity	NPD7152	Approved
0.7024	Intermediate Similarity	NPD7150	Approved
0.7021	Intermediate Similarity	NPD5328	Approved
0.7021	Intermediate Similarity	NPD4753	Phase 2
0.7011	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD3667	Approved
0.6988	Remote Similarity	NPD6922	Approved
0.6988	Remote Similarity	NPD6923	Approved
0.6977	Remote Similarity	NPD4190	Phase 3
0.6977	Remote Similarity	NPD5275	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.6961	Remote Similarity	NPD5141	Approved
0.6952	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6909	Remote Similarity	NPD7516	Approved
0.6905	Remote Similarity	NPD7144	Approved
0.6905	Remote Similarity	NPD7143	Approved
0.6897	Remote Similarity	NPD6117	Approved
0.6893	Remote Similarity	NPD4768	Approved
0.6893	Remote Similarity	NPD4767	Approved
0.6882	Remote Similarity	NPD3618	Phase 1
0.6875	Remote Similarity	NPD6079	Approved
0.6863	Remote Similarity	NPD4754	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6854	Remote Similarity	NPD4195	Approved
0.6848	Remote Similarity	NPD3133	Approved
0.6848	Remote Similarity	NPD3665	Phase 1
0.6848	Remote Similarity	NPD3666	Approved
0.6827	Remote Similarity	NPD5701	Approved
0.6827	Remote Similarity	NPD5697	Approved
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6399	Phase 3
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD7290	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6786	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD8296	Approved
0.6786	Remote Similarity	NPD8379	Approved
0.6786	Remote Similarity	NPD8033	Approved
0.6786	Remote Similarity	NPD8378	Approved
0.6782	Remote Similarity	NPD3703	Phase 2
0.6762	Remote Similarity	NPD5128	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD8130	Phase 1
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6649	Approved
0.6729	Remote Similarity	NPD6650	Approved
0.6706	Remote Similarity	NPD4244	Approved
0.6706	Remote Similarity	NPD4245	Approved
0.67	Remote Similarity	NPD6083	Phase 2
0.67	Remote Similarity	NPD6084	Phase 2
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6696	Remote Similarity	NPD8377	Approved
0.6696	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6633	Remote Similarity	NPD8171	Discontinued
0.663	Remote Similarity	NPD4221	Approved
0.663	Remote Similarity	NPD4223	Phase 3
0.6606	Remote Similarity	NPD4632	Approved
0.6606	Remote Similarity	NPD8133	Approved
0.6604	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.66	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5222	Approved
0.66	Remote Similarity	NPD5221	Approved
0.66	Remote Similarity	NPD4697	Phase 3
0.6596	Remote Similarity	NPD5329	Approved
0.6588	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3698	Phase 2
0.6588	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5215	Approved
0.6574	Remote Similarity	NPD5217	Approved
0.6574	Remote Similarity	NPD5216	Approved
0.6571	Remote Similarity	NPD6008	Approved
0.6556	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6054	Approved
0.6549	Remote Similarity	NPD6059	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD7515	Phase 2
0.6531	Remote Similarity	NPD7637	Suspended
0.6509	Remote Similarity	NPD6412	Phase 2
0.6495	Remote Similarity	NPD6051	Approved
0.6489	Remote Similarity	NPD3668	Phase 3
0.6489	Remote Similarity	NPD4197	Approved
0.6481	Remote Similarity	NPD5169	Approved
0.6481	Remote Similarity	NPD5135	Approved
0.6481	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5360	Phase 3
0.6471	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6370	Approved
0.6429	Remote Similarity	NPD7136	Phase 2
0.6429	Remote Similarity	NPD6009	Approved
0.6422	Remote Similarity	NPD5127	Approved
0.641	Remote Similarity	NPD7507	Approved
0.6404	Remote Similarity	NPD6319	Approved
0.6387	Remote Similarity	NPD7319	Approved
0.6354	Remote Similarity	NPD4688	Approved
0.6354	Remote Similarity	NPD4689	Approved
0.6354	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5205	Approved
0.6354	Remote Similarity	NPD4138	Approved
0.6354	Remote Similarity	NPD4693	Phase 3
0.6354	Remote Similarity	NPD4690	Approved
0.6348	Remote Similarity	NPD7503	Approved
0.6348	Remote Similarity	NPD6015	Approved
0.6348	Remote Similarity	NPD6016	Approved
0.6339	Remote Similarity	NPD6274	Approved
0.6337	Remote Similarity	NPD5695	Phase 3
0.6325	Remote Similarity	NPD7492	Approved
0.6322	Remote Similarity	NPD4789	Approved
0.6316	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD7100	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