NPASS Compound

Structure

CID234335 OpenBabel06191716032D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.1428 -2.0886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6107 -2.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 -4.6306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2079 -3.7843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9833 2.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8483 -2.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1648 -3.7837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6753 -2.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5436 -1.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5436 -0.4897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8482 -1.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5442 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5442 1.4691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8483 1.4692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6965 -0.9790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6323 -2.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1433 -3.7833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6969 -2.9368 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0518 2.4273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6966 0.9794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.9794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6966 -1.9583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8483 -0.4897 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8483 -0.4897 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9795 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 -0.8483 -1.4686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6965 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4240 -1.6341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3239 3.0826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2603 1.4804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8482 1.4692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 5 21 1 0 0 0 0 6 29 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 6 0 0 0 20 24 1 0 0 0 0 21 32 2 0 0 0 0 21 34 1 0 0 0 0 22 30 1 0 0 0 0 23 33 1 1 0 0 0 24 29 1 1 0 0 0 25 28 1 0 0 0 0 25 29 1 1 0 0 0 26 28 1 0 0 0 0 26 30 1 1 0 0 0 27 28 1 0 0 0 0 27 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	5.637
LogD:	4.988
LogS:	-4.887
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	4.868
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.72
MDCK Permeability:	1.2929672266182024e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.83
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.637
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	94.5134048461914%
Volume Distribution (VD):	1.115
Pgp-substrate:	2.3637442588806152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.177
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.286
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.662
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	4.602
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.362
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.456
Maximum Recommended Daily Dose:	0.53
Skin Sensitization:	0.092
Carcinogencity:	0.174
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC234335

Natural Product ID:	NPC234335
*Common Name:**	24-Methylcholesta-5,24(28)-Diene-3Beta,19-Diol-7Beta-Mono Aetate
IUPAC Name:	[(3S,7R,8S,9S,10S,13R,14S,17R)-3-hydroxy-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-7-yl] acetate
Synonyms:
Standard InCHIKey:	DXVRFEYOLWHNIF-VGBUTIAVSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18(2)19(3)7-8-20(4)24-9-10-25-28-26(12-13-29(24,25)6)30(17-31)14-11-23(33)15-22(30)16-27(28)34-21(5)32/h16,18,20,23-28,31,33H,3,7-15,17H2,1-2,4-6H3/t20-,23+,24-,25+,26+,27+,28+,29-,30-/m1/s1
SMILES:	OC[C@]12CC[C@@H](CC1=C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=C)C(C)C)C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471810
PubChem CID:	12069909
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO14781	Anthocleista vogelii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)97499-5]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO9675	Aphanoascus fulvescens	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10908107]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[17845002]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[24370010]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722490]
NPO9675	Aphanoascus fulvescens	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24165	Litophyton arboreum	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6694	Picconia excelsa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14781	Anthocleista vogelii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6931	Senna multiglandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	4
Others	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.81	ug ml-1	PMID[568249]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.87	ug ml-1	PMID[568249]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.38	ug ml-1	PMID[568249]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.42	ug ml-1	PMID[568249]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC50	=	1000000.0	nM	PMID[568250]

☑ 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 NPC234335 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	164
0.1-0.2	1118
0.2-0.3	4155
0.3-0.4	11126
0.4-0.5	10794
0.5-0.6	5978
0.6-0.7	6093
0.7-0.8	2909
0.8-0.85	294
0.85-0.9	61
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.914	High Similarity	NPC475617
0.9121	High Similarity	NPC54248
0.9121	High Similarity	NPC276103
0.9111	High Similarity	NPC474922
0.9043	High Similarity	NPC475344
0.9043	High Similarity	NPC476471
0.8966	High Similarity	NPC474970
0.8947	High Similarity	NPC474124
0.8889	High Similarity	NPC177641
0.8854	High Similarity	NPC473543
0.8824	High Similarity	NPC474752
0.8824	High Similarity	NPC474759
0.8824	High Similarity	NPC474731
0.8824	High Similarity	NPC82986
0.8824	High Similarity	NPC474683
0.8824	High Similarity	NPC7505
0.8778	High Similarity	NPC295668
0.875	High Similarity	NPC36688
0.875	High Similarity	NPC473523
0.8737	High Similarity	NPC222875
0.8737	High Similarity	NPC295110
0.8737	High Similarity	NPC247701
0.8737	High Similarity	NPC268829
0.8737	High Similarity	NPC25177
0.871	High Similarity	NPC304899
0.871	High Similarity	NPC88009
0.871	High Similarity	NPC253115
0.8681	High Similarity	NPC477574
0.8667	High Similarity	NPC473647
0.8667	High Similarity	NPC246028
0.8667	High Similarity	NPC261320
0.8636	High Similarity	NPC266511
0.8632	High Similarity	NPC251680
0.8632	High Similarity	NPC473510
0.8632	High Similarity	NPC477971
0.8632	High Similarity	NPC228251
0.8632	High Similarity	NPC477972
0.8632	High Similarity	NPC219285
0.8632	High Similarity	NPC20113
0.8632	High Similarity	NPC477968
0.8632	High Similarity	NPC161527
0.8617	High Similarity	NPC210337
0.8617	High Similarity	NPC475032
0.8617	High Similarity	NPC475033
0.8605	High Similarity	NPC209620
0.8605	High Similarity	NPC23852
0.8602	High Similarity	NPC281134
0.8588	High Similarity	NPC153987
0.8588	High Similarity	NPC44083
0.8571	High Similarity	NPC220216
0.8571	High Similarity	NPC119855
0.8571	High Similarity	NPC220217
0.8557	High Similarity	NPC97487
0.8557	High Similarity	NPC10232
0.8557	High Similarity	NPC189588
0.8557	High Similarity	NPC187302
0.8557	High Similarity	NPC196471
0.8557	High Similarity	NPC160583
0.8556	High Similarity	NPC470613
0.8556	High Similarity	NPC470612
0.8526	High Similarity	NPC218107
0.8523	High Similarity	NPC102048
0.8506	High Similarity	NPC470049
0.8506	High Similarity	NPC50964
0.8495	Intermediate Similarity	NPC279410
0.8495	Intermediate Similarity	NPC119562
0.8495	Intermediate Similarity	NPC105490
0.8488	Intermediate Similarity	NPC469802
0.8485	Intermediate Similarity	NPC475781
0.8478	Intermediate Similarity	NPC124374
0.8471	Intermediate Similarity	NPC87604
0.8462	Intermediate Similarity	NPC146554
0.8462	Intermediate Similarity	NPC177141
0.8444	Intermediate Similarity	NPC149224
0.8444	Intermediate Similarity	NPC471779
0.8438	Intermediate Similarity	NPC208358
0.8438	Intermediate Similarity	NPC230546
0.8427	Intermediate Similarity	NPC274448
0.8427	Intermediate Similarity	NPC157257
0.8421	Intermediate Similarity	NPC51499
0.8404	Intermediate Similarity	NPC276110
0.8387	Intermediate Similarity	NPC38232
0.8387	Intermediate Similarity	NPC7349
0.8387	Intermediate Similarity	NPC99653
0.8384	Intermediate Similarity	NPC186668
0.8372	Intermediate Similarity	NPC242767
0.8372	Intermediate Similarity	NPC28862
0.8372	Intermediate Similarity	NPC109546
0.8372	Intermediate Similarity	NPC143182
0.8372	Intermediate Similarity	NPC47982
0.8372	Intermediate Similarity	NPC81306
0.8372	Intermediate Similarity	NPC84694
0.837	Intermediate Similarity	NPC78973
0.8367	Intermediate Similarity	NPC472821
0.8351	Intermediate Similarity	NPC155974
0.8333	Intermediate Similarity	NPC471219
0.8333	Intermediate Similarity	NPC275086
0.8333	Intermediate Similarity	NPC261266
0.8333	Intermediate Similarity	NPC325229
0.8333	Intermediate Similarity	NPC152808
0.8333	Intermediate Similarity	NPC155011
0.8333	Intermediate Similarity	NPC6391
0.8333	Intermediate Similarity	NPC293287
0.8333	Intermediate Similarity	NPC477668
0.8333	Intermediate Similarity	NPC286153
0.8317	Intermediate Similarity	NPC472216
0.8317	Intermediate Similarity	NPC284828
0.8317	Intermediate Similarity	NPC5475
0.8317	Intermediate Similarity	NPC173905
0.8316	Intermediate Similarity	NPC72204
0.8315	Intermediate Similarity	NPC299963
0.8315	Intermediate Similarity	NPC470077
0.8298	Intermediate Similarity	NPC472360
0.8298	Intermediate Similarity	NPC472416
0.8298	Intermediate Similarity	NPC144202
0.8298	Intermediate Similarity	NPC3359
0.8295	Intermediate Similarity	NPC470614
0.8295	Intermediate Similarity	NPC1272
0.8295	Intermediate Similarity	NPC101462
0.8295	Intermediate Similarity	NPC472504
0.8283	Intermediate Similarity	NPC200861
0.828	Intermediate Similarity	NPC41239
0.828	Intermediate Similarity	NPC130840
0.8276	Intermediate Similarity	NPC234193
0.8276	Intermediate Similarity	NPC26117
0.8265	Intermediate Similarity	NPC154452
0.8261	Intermediate Similarity	NPC472240
0.8261	Intermediate Similarity	NPC262858
0.8261	Intermediate Similarity	NPC16265
0.8256	Intermediate Similarity	NPC473943
0.8256	Intermediate Similarity	NPC474216
0.8242	Intermediate Similarity	NPC166857
0.8235	Intermediate Similarity	NPC321016
0.8235	Intermediate Similarity	NPC321381
0.8235	Intermediate Similarity	NPC107059
0.8229	Intermediate Similarity	NPC99726
0.8229	Intermediate Similarity	NPC98112
0.8229	Intermediate Similarity	NPC141401
0.8229	Intermediate Similarity	NPC231751
0.8222	Intermediate Similarity	NPC35933
0.8218	Intermediate Similarity	NPC472218
0.8218	Intermediate Similarity	NPC472219
0.8218	Intermediate Similarity	NPC472217
0.8211	Intermediate Similarity	NPC37603
0.8211	Intermediate Similarity	NPC8774
0.8211	Intermediate Similarity	NPC469599
0.8211	Intermediate Similarity	NPC471786
0.8211	Intermediate Similarity	NPC477969
0.8211	Intermediate Similarity	NPC279974
0.8211	Intermediate Similarity	NPC135224
0.8202	Intermediate Similarity	NPC474634
0.8202	Intermediate Similarity	NPC477667
0.8202	Intermediate Similarity	NPC475789
0.8202	Intermediate Similarity	NPC23748
0.8191	Intermediate Similarity	NPC473678
0.8191	Intermediate Similarity	NPC27531
0.8182	Intermediate Similarity	NPC264245
0.8182	Intermediate Similarity	NPC85742
0.8182	Intermediate Similarity	NPC142163
0.8182	Intermediate Similarity	NPC47761
0.8182	Intermediate Similarity	NPC45897
0.8182	Intermediate Similarity	NPC470383
0.8182	Intermediate Similarity	NPC222153
0.8182	Intermediate Similarity	NPC297617
0.8172	Intermediate Similarity	NPC221111
0.8172	Intermediate Similarity	NPC280149
0.8172	Intermediate Similarity	NPC471896
0.8172	Intermediate Similarity	NPC273199
0.8172	Intermediate Similarity	NPC48732
0.8163	Intermediate Similarity	NPC176406
0.8163	Intermediate Similarity	NPC21064
0.8163	Intermediate Similarity	NPC11974
0.8163	Intermediate Similarity	NPC121072
0.8161	Intermediate Similarity	NPC100906
0.8161	Intermediate Similarity	NPC30986
0.8161	Intermediate Similarity	NPC209430
0.8155	Intermediate Similarity	NPC470076
0.8152	Intermediate Similarity	NPC471952
0.8152	Intermediate Similarity	NPC473879
0.8152	Intermediate Similarity	NPC474668
0.8144	Intermediate Similarity	NPC300179
0.8144	Intermediate Similarity	NPC247233
0.8144	Intermediate Similarity	NPC92275
0.8144	Intermediate Similarity	NPC102426
0.8144	Intermediate Similarity	NPC119036
0.8144	Intermediate Similarity	NPC98868
0.814	Intermediate Similarity	NPC198968
0.814	Intermediate Similarity	NPC318495
0.814	Intermediate Similarity	NPC155986
0.8137	Intermediate Similarity	NPC475030
0.8132	Intermediate Similarity	NPC329692
0.8132	Intermediate Similarity	NPC131813
0.8132	Intermediate Similarity	NPC102996
0.8125	Intermediate Similarity	NPC190713
0.8125	Intermediate Similarity	NPC94905
0.8125	Intermediate Similarity	NPC471903
0.8125	Intermediate Similarity	NPC12103
0.8125	Intermediate Similarity	NPC288970
0.8125	Intermediate Similarity	NPC211810
0.8125	Intermediate Similarity	NPC284194

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 NPC234335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1277
0.2-0.3	3853
0.3-0.4	2596
0.4-0.5	757
0.5-0.6	205
0.6-0.7	204
0.7-0.8	111
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8723	High Similarity	NPD7638	Approved
0.8632	High Similarity	NPD7640	Approved
0.8632	High Similarity	NPD7639	Approved
0.8261	Intermediate Similarity	NPD6051	Approved
0.8191	Intermediate Similarity	NPD6399	Phase 3
0.8118	Intermediate Similarity	NPD6942	Approved
0.8118	Intermediate Similarity	NPD7339	Approved
0.7912	Intermediate Similarity	NPD4786	Approved
0.79	Intermediate Similarity	NPD7632	Discontinued
0.7895	Intermediate Similarity	NPD7637	Suspended
0.7849	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6695	Phase 3
0.7717	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3667	Approved
0.7667	Intermediate Similarity	NPD7525	Registered
0.7556	Intermediate Similarity	NPD6929	Approved
0.7545	Intermediate Similarity	NPD7327	Approved
0.7545	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.7477	Intermediate Similarity	NPD7516	Approved
0.7474	Intermediate Similarity	NPD7524	Approved
0.7474	Intermediate Similarity	NPD7750	Discontinued
0.7473	Intermediate Similarity	NPD6931	Approved
0.7473	Intermediate Similarity	NPD6930	Phase 2
0.7455	Intermediate Similarity	NPD7115	Discovery
0.7426	Intermediate Similarity	NPD4225	Approved
0.7411	Intermediate Similarity	NPD8294	Approved
0.7411	Intermediate Similarity	NPD8377	Approved
0.7407	Intermediate Similarity	NPD6053	Discontinued
0.7396	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7386	Intermediate Similarity	NPD6924	Approved
0.7386	Intermediate Similarity	NPD6926	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD6686	Approved
0.7345	Intermediate Similarity	NPD8378	Approved
0.7345	Intermediate Similarity	NPD8296	Approved
0.7345	Intermediate Similarity	NPD8380	Approved
0.7345	Intermediate Similarity	NPD8335	Approved
0.7345	Intermediate Similarity	NPD7503	Approved
0.7345	Intermediate Similarity	NPD8379	Approved
0.7333	Intermediate Similarity	NPD7128	Approved
0.7333	Intermediate Similarity	NPD6925	Approved
0.7333	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD5776	Phase 2
0.7333	Intermediate Similarity	NPD6675	Approved
0.7333	Intermediate Similarity	NPD6402	Approved
0.732	Intermediate Similarity	NPD5328	Approved
0.7283	Intermediate Similarity	NPD7514	Phase 3
0.7263	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7145	Approved
0.7222	Intermediate Similarity	NPD6933	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6902	Approved
0.72	Intermediate Similarity	NPD7748	Approved
0.7196	Intermediate Similarity	NPD6899	Approved
0.7196	Intermediate Similarity	NPD6881	Approved
0.7196	Intermediate Similarity	NPD7320	Approved
0.7191	Intermediate Similarity	NPD4784	Approved
0.7191	Intermediate Similarity	NPD4785	Approved
0.7188	Intermediate Similarity	NPD3618	Phase 1
0.7174	Intermediate Similarity	NPD7645	Phase 2
0.7172	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD8034	Phase 2
0.7172	Intermediate Similarity	NPD7087	Discontinued
0.7172	Intermediate Similarity	NPD7515	Phase 2
0.7172	Intermediate Similarity	NPD6079	Approved
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.717	Intermediate Similarity	NPD6008	Approved
0.7159	Intermediate Similarity	NPD7150	Approved
0.7159	Intermediate Similarity	NPD7152	Approved
0.7159	Intermediate Similarity	NPD7151	Approved
0.7159	Intermediate Similarity	NPD4243	Approved
0.7158	Intermediate Similarity	NPD3666	Approved
0.7158	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3133	Approved
0.7158	Intermediate Similarity	NPD3668	Phase 3
0.7158	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD6932	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.7129	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6923	Approved
0.7126	Intermediate Similarity	NPD6922	Approved
0.7103	Intermediate Similarity	NPD5697	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.7103	Intermediate Similarity	NPD5701	Approved
0.7097	Intermediate Similarity	NPD7332	Phase 2
0.7094	Intermediate Similarity	NPD7507	Approved
0.7087	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6893	Approved
0.7064	Intermediate Similarity	NPD7102	Approved
0.7064	Intermediate Similarity	NPD7290	Approved
0.7064	Intermediate Similarity	NPD6883	Approved
0.7045	Intermediate Similarity	NPD7144	Approved
0.7045	Intermediate Similarity	NPD7143	Approved
0.7037	Intermediate Similarity	NPD6011	Approved
0.7027	Intermediate Similarity	NPD4632	Approved
0.701	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD8130	Phase 1
0.7	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6847	Approved
0.699	Remote Similarity	NPD7902	Approved
0.6989	Remote Similarity	NPD4195	Approved
0.6989	Remote Similarity	NPD6683	Phase 2
0.6972	Remote Similarity	NPD6012	Approved
0.6972	Remote Similarity	NPD6013	Approved
0.6972	Remote Similarity	NPD6014	Approved
0.697	Remote Similarity	NPD4753	Phase 2
0.697	Remote Similarity	NPD6673	Approved
0.697	Remote Similarity	NPD6080	Approved
0.697	Remote Similarity	NPD6904	Approved
0.6952	Remote Similarity	NPD5344	Discontinued
0.6937	Remote Similarity	NPD8297	Approved
0.6937	Remote Similarity	NPD6882	Approved
0.6931	Remote Similarity	NPD4202	Approved
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6917	Remote Similarity	NPD7319	Approved
0.6915	Remote Similarity	NPD4748	Discontinued
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5221	Approved
0.6893	Remote Similarity	NPD4697	Phase 3
0.6893	Remote Similarity	NPD5222	Approved
0.6882	Remote Similarity	NPD6118	Approved
0.6882	Remote Similarity	NPD6115	Approved
0.6882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6114	Approved
0.6882	Remote Similarity	NPD6697	Approved
0.6882	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8133	Approved
0.6875	Remote Similarity	NPD5362	Discontinued
0.6842	Remote Similarity	NPD6898	Phase 1
0.6842	Remote Similarity	NPD6009	Approved
0.6837	Remote Similarity	NPD5279	Phase 3
0.6832	Remote Similarity	NPD6411	Approved
0.6827	Remote Similarity	NPD5173	Approved
0.6827	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD6319	Approved
0.6796	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7604	Phase 2
0.6771	Remote Similarity	NPD4221	Approved
0.6771	Remote Similarity	NPD4223	Phase 3
0.6768	Remote Similarity	NPD4251	Approved
0.6768	Remote Similarity	NPD4250	Approved
0.6754	Remote Similarity	NPD6868	Approved
0.6752	Remote Similarity	NPD5983	Phase 2
0.6739	Remote Similarity	NPD4190	Phase 3
0.6739	Remote Similarity	NPD8264	Approved
0.6739	Remote Similarity	NPD5275	Approved
0.6737	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7509	Discontinued
0.6735	Remote Similarity	NPD5329	Approved
0.6733	Remote Similarity	NPD6698	Approved
0.6733	Remote Similarity	NPD5785	Approved
0.6733	Remote Similarity	NPD7838	Discovery
0.6733	Remote Similarity	NPD46	Approved
0.6729	Remote Similarity	NPD5211	Phase 2
0.6723	Remote Similarity	NPD7492	Approved
0.6701	Remote Similarity	NPD5331	Approved
0.6701	Remote Similarity	NPD5332	Approved
0.67	Remote Similarity	NPD5208	Approved
0.6699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7900	Approved
0.6698	Remote Similarity	NPD5286	Approved
0.6698	Remote Similarity	NPD6648	Approved
0.6698	Remote Similarity	NPD5285	Approved
0.6698	Remote Similarity	NPD4700	Approved
0.6698	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6638	Remote Similarity	NPD6335	Approved
0.6636	Remote Similarity	NPD4159	Approved
0.6636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5223	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