NPASS Compound

Structure

NPC475172 OpenBabel07101718272D 42 45 0 0 1 0 0 0 0 0999 V2000 1.5000 -7.8790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.2810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7024 -5.2885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1398 -4.3615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -7.0130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -7.0130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -6.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8125 -1.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8614 -2.0451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0933 -3.5014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8364 -2.8322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1887 -4.6705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2377 -4.9795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5067 -2.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0908 -4.0525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -8.7451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -7.8790 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -5.2810 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.5556 -2.4052 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.6535 -3.0232 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -4.4149 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.7024 -3.3322 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.3966 -3.6924 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.2498 -2.7653 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0419 -3.7435 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.4945 -4.3104 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.3477 -3.3833 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5000 -8.6111 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.5000 -9.6111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -10.6111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4306 -1.2702 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 11.6167 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3869 -1.6861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0451 -5.0546 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 12.6872 -3.7946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4271 -3.1525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -9.6111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2009 -2.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7850 -4.4126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -9.6111 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 11.4088 -1.4781 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 11.7361 -4.1036 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 37 1 0 0 0 0 18 21 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 38 1 0 0 0 0 25 39 1 0 0 0 0 28 40 1 0 0 0 0 29 40 2 0 0 0 0 30 40 2 0 0 0 0 31 41 1 0 0 0 0 32 41 2 0 0 0 0 33 41 2 0 0 0 0 34 42 1 0 0 0 0 35 42 2 0 0 0 0 36 42 2 0 0 0 0 37 40 1 0 0 0 0 38 41 1 0 0 0 0 39 42 1 0 0 0 0 M CHG 3 28 -1 31 -1 34 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	657.21
Volume:	598.377
LogP:	3.249
LogD:	2.198
LogS:	-4.749
# Rotatable Bonds:	12
TPSA:	199.29
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	5.592
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985
MDCK Permeability:	3.5217395634390414e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.151

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	95.42264556884766%
Volume Distribution (VD):	1.352
Pgp-substrate:	2.1298434734344482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.792
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	1.613
Half-life (T1/2):	0.003

ADMET: Toxicity

hERG Blockers:	0.928
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.984
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.995
Carcinogencity:	0.889
Eye Corrosion:	0.997
Eye Irritation:	0.895
Respiratory Toxicity:	0.995

Download Data

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

Natural Product: NPC475172

Natural Product ID:	NPC475172
*Common Name:**	5Alpha-Cholestane-2Beta,3Alpha,26-Triyl Sulfate
IUPAC Name:	trisodium;[(6R)-6-[(2S,3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-2,3-disulfonatooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptyl] sulfate
Synonyms:
Standard InCHIKey:	KCVWSWMWWCSSME-HSLRMJKYSA-K
Standard InCHI:	InChI=1S/C27H48O12S3.3Na/c1-17(16-37-40(28,29)30)6-5-7-18(2)21-10-11-22-20-9-8-19-14-24(38-41(31,32)33)25(39-42(34,35)36)15-27(19,4)23(20)12-13-26(21,22)3;;;/h17-25H,5-16H2,1-4H3,(H,28,29,30)(H,31,32,33)(H,34,35,36);;;/q;3*+1/p-3/t17?,18-,19+,20+,21-,22+,23+,24+,25+,26-,27+;;;/m1.../s1
SMILES:	CC(CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CC(C(C4)OS(=O)(=O)[O-])OS(=O)(=O)[O-])C)C)COS(=O)(=O)[O-].[Na+].[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500050
PubChem CID:	44559769
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

*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
NPO458	Ophiarachna incrassata	Species	Ophiodermatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7853009]
NPO458	Ophiarachna incrassata	Species	Ophiodermatidae	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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	11000.0	nM	PMID[541873]

☑ 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 NPC475172 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	448
0.1-0.2	6281
0.2-0.3	18819
0.3-0.4	7459
0.4-0.5	5293
0.5-0.6	3498
0.6-0.7	731
0.7-0.8	146
0.8-0.85	8
0.85-0.9	5
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC477603
0.9394	High Similarity	NPC324984
0.9394	High Similarity	NPC477821
0.9394	High Similarity	NPC323900
0.9394	High Similarity	NPC477823
0.9394	High Similarity	NPC477822
0.9394	High Similarity	NPC473552
0.8857	High Similarity	NPC477601
0.8857	High Similarity	NPC473916
0.8857	High Similarity	NPC477602
0.8824	High Similarity	NPC478103
0.8571	High Similarity	NPC478130
0.8493	Intermediate Similarity	NPC474132
0.8451	Intermediate Similarity	NPC478105
0.8182	Intermediate Similarity	NPC114891
0.8158	Intermediate Similarity	NPC477599
0.8108	Intermediate Similarity	NPC478128
0.803	Intermediate Similarity	NPC218585
0.803	Intermediate Similarity	NPC71460
0.803	Intermediate Similarity	NPC148174
0.8026	Intermediate Similarity	NPC473534
0.8	Intermediate Similarity	NPC107919
0.7949	Intermediate Similarity	NPC469878
0.7887	Intermediate Similarity	NPC231945
0.7826	Intermediate Similarity	NPC142712
0.7821	Intermediate Similarity	NPC478054
0.7794	Intermediate Similarity	NPC69149
0.7794	Intermediate Similarity	NPC118937
0.7794	Intermediate Similarity	NPC159654
0.7794	Intermediate Similarity	NPC167995
0.7794	Intermediate Similarity	NPC281540
0.7778	Intermediate Similarity	NPC126642
0.7746	Intermediate Similarity	NPC241085
0.7746	Intermediate Similarity	NPC299948
0.7746	Intermediate Similarity	NPC66407
0.7746	Intermediate Similarity	NPC470830
0.7714	Intermediate Similarity	NPC475884
0.7714	Intermediate Similarity	NPC48079
0.7714	Intermediate Similarity	NPC473230
0.7703	Intermediate Similarity	NPC158208
0.7703	Intermediate Similarity	NPC196136
0.7703	Intermediate Similarity	NPC243027
0.7681	Intermediate Similarity	NPC474380
0.7681	Intermediate Similarity	NPC41577
0.7681	Intermediate Similarity	NPC473276
0.7671	Intermediate Similarity	NPC470610
0.7671	Intermediate Similarity	NPC153719
0.7654	Intermediate Similarity	NPC477600
0.7639	Intermediate Similarity	NPC63588
0.7639	Intermediate Similarity	NPC192192
0.7639	Intermediate Similarity	NPC251201
0.7639	Intermediate Similarity	NPC232925
0.7632	Intermediate Similarity	NPC329117
0.7632	Intermediate Similarity	NPC475337
0.7606	Intermediate Similarity	NPC472741
0.76	Intermediate Similarity	NPC163597
0.7576	Intermediate Similarity	NPC476735
0.7571	Intermediate Similarity	NPC44122
0.7568	Intermediate Similarity	NPC192501
0.7568	Intermediate Similarity	NPC48795
0.7568	Intermediate Similarity	NPC10476
0.7568	Intermediate Similarity	NPC228994
0.7534	Intermediate Similarity	NPC109457
0.7534	Intermediate Similarity	NPC470071
0.7534	Intermediate Similarity	NPC157777
0.7534	Intermediate Similarity	NPC131506
0.7534	Intermediate Similarity	NPC127094
0.7534	Intermediate Similarity	NPC187471
0.7534	Intermediate Similarity	NPC1340
0.7534	Intermediate Similarity	NPC252182
0.7534	Intermediate Similarity	NPC100586
0.7534	Intermediate Similarity	NPC157422
0.7531	Intermediate Similarity	NPC478094
0.7531	Intermediate Similarity	NPC477604
0.75	Intermediate Similarity	NPC320824
0.75	Intermediate Similarity	NPC105208
0.75	Intermediate Similarity	NPC302578
0.75	Intermediate Similarity	NPC477227
0.75	Intermediate Similarity	NPC192046
0.75	Intermediate Similarity	NPC477820
0.75	Intermediate Similarity	NPC99264
0.75	Intermediate Similarity	NPC128951
0.75	Intermediate Similarity	NPC254037
0.75	Intermediate Similarity	NPC129829
0.7467	Intermediate Similarity	NPC317242
0.7465	Intermediate Similarity	NPC63190
0.7432	Intermediate Similarity	NPC472341
0.7432	Intermediate Similarity	NPC473238
0.7429	Intermediate Similarity	NPC243469
0.7429	Intermediate Similarity	NPC475943
0.7429	Intermediate Similarity	NPC472946
0.7429	Intermediate Similarity	NPC190827
0.7403	Intermediate Similarity	NPC67657
0.7403	Intermediate Similarity	NPC18857
0.7403	Intermediate Similarity	NPC147993
0.7397	Intermediate Similarity	NPC282454
0.7333	Intermediate Similarity	NPC304499
0.7297	Intermediate Similarity	NPC127283
0.7297	Intermediate Similarity	NPC151018
0.7297	Intermediate Similarity	NPC195530
0.7297	Intermediate Similarity	NPC156277
0.7297	Intermediate Similarity	NPC58057
0.7297	Intermediate Similarity	NPC8004
0.7297	Intermediate Similarity	NPC473279
0.7297	Intermediate Similarity	NPC320549
0.7284	Intermediate Similarity	NPC478102
0.7273	Intermediate Similarity	NPC474574
0.7273	Intermediate Similarity	NPC185915
0.7273	Intermediate Similarity	NPC64081
0.7273	Intermediate Similarity	NPC133596
0.7273	Intermediate Similarity	NPC11907
0.7262	Intermediate Similarity	NPC477606
0.726	Intermediate Similarity	NPC470833
0.7237	Intermediate Similarity	NPC231680
0.7237	Intermediate Similarity	NPC91387
0.7237	Intermediate Similarity	NPC270306
0.7222	Intermediate Similarity	NPC204233
0.72	Intermediate Similarity	NPC232112
0.7183	Intermediate Similarity	NPC260116
0.7179	Intermediate Similarity	NPC102708
0.7143	Intermediate Similarity	NPC317363
0.7143	Intermediate Similarity	NPC4209
0.7143	Intermediate Similarity	NPC91573
0.7143	Intermediate Similarity	NPC470145
0.7123	Intermediate Similarity	NPC475893
0.7105	Intermediate Similarity	NPC280026
0.7105	Intermediate Similarity	NPC477508
0.7105	Intermediate Similarity	NPC272359
0.7105	Intermediate Similarity	NPC167702
0.7105	Intermediate Similarity	NPC254340
0.7089	Intermediate Similarity	NPC477287
0.7089	Intermediate Similarity	NPC477282
0.7089	Intermediate Similarity	NPC287452
0.7089	Intermediate Similarity	NPC81074
0.7067	Intermediate Similarity	NPC111234
0.7059	Intermediate Similarity	NPC162685
0.7051	Intermediate Similarity	NPC212453
0.7051	Intermediate Similarity	NPC207010
0.7051	Intermediate Similarity	NPC317913
0.7037	Intermediate Similarity	NPC477284
0.7037	Intermediate Similarity	NPC60018
0.7037	Intermediate Similarity	NPC121121
0.7037	Intermediate Similarity	NPC202688
0.7037	Intermediate Similarity	NPC154043
0.7027	Intermediate Similarity	NPC327728
0.7027	Intermediate Similarity	NPC6120
0.7027	Intermediate Similarity	NPC213178
0.7027	Intermediate Similarity	NPC131892
0.7024	Intermediate Similarity	NPC478104
0.7013	Intermediate Similarity	NPC185536
0.7013	Intermediate Similarity	NPC3403
0.7013	Intermediate Similarity	NPC231256
0.7013	Intermediate Similarity	NPC195155
0.7013	Intermediate Similarity	NPC212879
0.7013	Intermediate Similarity	NPC174964
0.7013	Intermediate Similarity	NPC240235
0.7013	Intermediate Similarity	NPC103822
0.7013	Intermediate Similarity	NPC97534
0.7013	Intermediate Similarity	NPC230704
0.7013	Intermediate Similarity	NPC70982
0.7013	Intermediate Similarity	NPC178383
0.7013	Intermediate Similarity	NPC273366
0.7013	Intermediate Similarity	NPC104387
0.7013	Intermediate Similarity	NPC212733
0.7011	Intermediate Similarity	NPC476669
0.7	Intermediate Similarity	NPC470609
0.7	Intermediate Similarity	NPC16449
0.6988	Remote Similarity	NPC478127
0.6974	Remote Similarity	NPC195489
0.6962	Remote Similarity	NPC171426
0.6962	Remote Similarity	NPC34046
0.6962	Remote Similarity	NPC324700
0.6962	Remote Similarity	NPC185465
0.6962	Remote Similarity	NPC80089
0.6962	Remote Similarity	NPC224802
0.6962	Remote Similarity	NPC301707
0.6957	Remote Similarity	NPC95958
0.6951	Remote Similarity	NPC216420
0.6951	Remote Similarity	NPC207013
0.6951	Remote Similarity	NPC211135
0.6951	Remote Similarity	NPC85095
0.6944	Remote Similarity	NPC80463
0.6933	Remote Similarity	NPC45296
0.6932	Remote Similarity	NPC475325
0.6932	Remote Similarity	NPC477605
0.6923	Remote Similarity	NPC278091
0.6923	Remote Similarity	NPC472486
0.6923	Remote Similarity	NPC5767
0.6923	Remote Similarity	NPC14112
0.6923	Remote Similarity	NPC472487
0.6923	Remote Similarity	NPC475742
0.6923	Remote Similarity	NPC86305
0.6923	Remote Similarity	NPC93662
0.6923	Remote Similarity	NPC78067
0.6914	Remote Similarity	NPC190940
0.6914	Remote Similarity	NPC109533
0.6914	Remote Similarity	NPC12933
0.6912	Remote Similarity	NPC135438
0.6905	Remote Similarity	NPC323958
0.6901	Remote Similarity	NPC249078

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 NPC475172 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	5033
0.2-0.3	2817
0.3-0.4	492
0.4-0.5	227
0.5-0.6	149
0.6-0.7	33
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4787	Phase 1
0.7297	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5364	Discontinued
0.7143	Intermediate Similarity	NPD6117	Approved
0.7105	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6116	Phase 1
0.7027	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6697	Approved
0.6962	Remote Similarity	NPD6114	Approved
0.6962	Remote Similarity	NPD6118	Approved
0.6962	Remote Similarity	NPD6115	Approved
0.6892	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5360	Phase 3
0.679	Remote Similarity	NPD7525	Registered
0.6711	Remote Similarity	NPD4789	Approved
0.6711	Remote Similarity	NPD4245	Approved
0.6711	Remote Similarity	NPD4244	Approved
0.6623	Remote Similarity	NPD5777	Approved
0.6591	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6700	Approved
0.6585	Remote Similarity	NPD6928	Phase 2
0.6582	Remote Similarity	NPD3703	Phase 2
0.6579	Remote Similarity	NPD3698	Phase 2
0.6517	Remote Similarity	NPD6702	Approved
0.6517	Remote Similarity	NPD6703	Approved
0.6486	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6081	Approved
0.641	Remote Similarity	NPD4758	Discontinued
0.6375	Remote Similarity	NPD6942	Approved
0.6375	Remote Similarity	NPD7339	Approved
0.6341	Remote Similarity	NPD3671	Phase 1
0.6279	Remote Similarity	NPD3668	Phase 3
0.6264	Remote Similarity	NPD8171	Discontinued
0.6234	Remote Similarity	NPD6705	Phase 1
0.6207	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4224	Phase 2
0.617	Remote Similarity	NPD7920	Phase 3
0.617	Remote Similarity	NPD7919	Phase 3
0.6136	Remote Similarity	NPD8308	Discontinued
0.6105	Remote Similarity	NPD8088	Phase 1
0.6098	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4748	Discontinued
0.5978	Remote Similarity	NPD8034	Phase 2
0.5978	Remote Similarity	NPD8035	Phase 2
0.5976	Remote Similarity	NPD3702	Approved
0.5968	Remote Similarity	NPD1460	Approved
0.5909	Remote Similarity	NPD4786	Approved
0.5904	Remote Similarity	NPD6933	Approved
0.5882	Remote Similarity	NPD7645	Phase 2
0.5854	Remote Similarity	NPD6926	Approved
0.5854	Remote Similarity	NPD6924	Approved
0.5833	Remote Similarity	NPD586	Phase 1
0.5802	Remote Similarity	NPD4243	Approved
0.5795	Remote Similarity	NPD4788	Approved
0.5789	Remote Similarity	NPD7991	Discontinued
0.5781	Remote Similarity	NPD1462	Approved
0.5761	Remote Similarity	NPD5328	Approved
0.5682	Remote Similarity	NPD3667	Approved
0.5672	Remote Similarity	NPD384	Approved
0.5672	Remote Similarity	NPD385	Approved
0.5663	Remote Similarity	NPD4784	Approved
0.5663	Remote Similarity	NPD4785	Approved
0.5644	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6079	Approved
0.561	Remote Similarity	NPD7151	Approved
0.561	Remote Similarity	NPD7152	Approved
0.561	Remote Similarity	NPD7150	Approved
0.5604	Remote Similarity	NPD3618	Phase 1

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