NPASS Compound

Structure

NPC473916 OpenBabel07101718202D 39 42 0 0 1 0 0 0 0 0999 V2000 0.5000 -6.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -7.2610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6398 -3.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2024 -4.6705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.5289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -5.5289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.6629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3614 -1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3125 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5933 -2.8833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3364 -2.2142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5419 -3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5908 -3.4344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7377 -4.3615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -5.5289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -6.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -4.6629 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.1535 -2.4052 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0000 -3.7969 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.2024 -2.7142 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.0556 -1.7872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.6887 -4.0525 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.7498 -2.1473 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.8966 -3.0743 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0067 -1.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.8477 -2.7653 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.9945 -3.6924 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.4319 -4.7216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2146 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -5.3950 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 2.5000 -6.3950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -7.3950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7749 -3.2505 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 13.1872 -3.1765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1131 -1.7642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -6.3950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7009 -1.8383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -6.3950 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 12.4440 -2.5074 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 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 16 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 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 22 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 36 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 20 27 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 25 1 0 0 0 0 23 37 1 0 0 0 0 24 26 1 0 0 0 0 25 29 1 0 0 0 0 30 38 1 0 0 0 0 31 38 2 0 0 0 0 32 38 2 0 0 0 0 33 39 1 0 0 0 0 34 39 2 0 0 0 0 35 39 2 0 0 0 0 36 38 1 0 0 0 0 37 39 1 0 0 0 0 M CHG 2 30 -1 33 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.25
Volume:	563.606
LogP:	3.338
LogD:	2.125
LogS:	-3.204
# Rotatable Bonds:	10
TPSA:	173.32
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	5.435
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
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:	-4.903
MDCK Permeability:	2.0782259525731206e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	97.3664321899414%
Volume Distribution (VD):	1.44
Pgp-substrate:	2.390056610107422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.442
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	1.35
Half-life (T1/2):	0.008

ADMET: Toxicity

hERG Blockers:	0.879
Human Hepatotoxicity (H-HT):	0.899
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.683
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.978
Carcinogencity:	0.842
Eye Corrosion:	0.983
Eye Irritation:	0.396
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC473916

Natural Product ID:	NPC473916
*Common Name:**	5Beta-Cholestane-3Alpha,4Alpha,11Beta,21-Tetraol 3,21-Di-Sulfate
IUPAC Name:	disodium;[(3R,4S,5S,8S,9S,10S,11S,13S,14S,17R)-4,11-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfonatooxyheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:
Standard InCHIKey:	GMTSFJVPCBXTQJ-MLJWSNOLSA-L
Standard InCHI:	InChI=1S/C27H48O10S2.2Na/c1-16(2)6-5-7-17(15-36-38(30,31)32)19-10-11-20-18-8-9-21-25(29)23(37-39(33,34)35)12-13-26(21,3)24(18)22(28)14-27(19,20)4;;/h16-25,28-29H,5-15H2,1-4H3,(H,30,31,32)(H,33,34,35);;/q;2*+1/p-2/t17-,18-,19+,20-,21+,22-,23+,24+,25-,26-,27+;;/m0../s1
SMILES:	CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H]([C@H]2O)OS(=O)(=O)[O-])COS(=O)(=O)[O-])C.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455235
PubChem CID:	14238131
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:0000516] Dihydroxy 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]
NPO40253	Ophioplocus januarii	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	PMID[8864241]
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
Others	17

Activity Type	# Activity
Cell Line	1
Organism	16
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	100.0	%	PMID[495471]
NPT2	Others	Unspecified		IC50	=	62000.0	nM	PMID[495470]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	Inhibition	=	0.0	%	PMID[495471]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	Inhibition	=	25.0	%	PMID[495471]
NPT6586	Organism	Human poliovirus 3	Human poliovirus 3	Activity	=	0.0	%	PMID[495471]
NPT6618	Organism	Junin virus	Junin virus	Activity	=	26.0	%	PMID[495471]
NPT6586	Organism	Human poliovirus 3	Human poliovirus 3	Activity	=	24.0	%	PMID[495471]
NPT6618	Organism	Junin virus	Junin virus	Activity	=	33.0	%	PMID[495471]
NPT6586	Organism	Human poliovirus 3	Human poliovirus 3	Activity	=	30.0	%	PMID[495471]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	8.0	%	PMID[495471]
NPT6618	Organism	Junin virus	Junin virus	Activity	=	28.0	%	PMID[495471]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	35.0	%	PMID[495471]
NPT6618	Organism	Junin virus	Junin virus	Activity	=	24.0	%	PMID[495471]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	7.0	%	PMID[495471]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	2.0	%	PMID[495471]

☑ 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 NPC473916 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	415
0.1-0.2	4722
0.2-0.3	16118
0.3-0.4	10041
0.4-0.5	4763
0.5-0.6	4512
0.6-0.7	1691
0.7-0.8	340
0.8-0.85	60
0.85-0.9	24
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477601
1.0	High Similarity	NPC477602
0.9155	High Similarity	NPC477821
0.9155	High Similarity	NPC478103
0.9155	High Similarity	NPC477822
0.9155	High Similarity	NPC324984
0.9155	High Similarity	NPC473552
0.9155	High Similarity	NPC323900
0.9155	High Similarity	NPC477823
0.8904	High Similarity	NPC478130
0.8857	High Similarity	NPC475172
0.8846	High Similarity	NPC478054
0.8784	High Similarity	NPC196136
0.8784	High Similarity	NPC243027
0.8784	High Similarity	NPC158208
0.8767	High Similarity	NPC470610
0.8767	High Similarity	NPC153719
0.8718	High Similarity	NPC477599
0.8667	High Similarity	NPC163597
0.8649	High Similarity	NPC48795
0.8649	High Similarity	NPC10476
0.8649	High Similarity	NPC228994
0.8649	High Similarity	NPC192501
0.8642	High Similarity	NPC477600
0.8611	High Similarity	NPC107919
0.8611	High Similarity	NPC66407
0.8571	High Similarity	NPC477603
0.8553	High Similarity	NPC477227
0.8553	High Similarity	NPC192046
0.8553	High Similarity	NPC128951
0.8553	High Similarity	NPC302578
0.8553	High Similarity	NPC105208
0.8533	High Similarity	NPC317242
0.85	High Similarity	NPC320824
0.8493	Intermediate Similarity	NPC231945
0.8493	Intermediate Similarity	NPC251201
0.8493	Intermediate Similarity	NPC192192
0.8493	Intermediate Similarity	NPC232925
0.8493	Intermediate Similarity	NPC63588
0.8442	Intermediate Similarity	NPC67657
0.8442	Intermediate Similarity	NPC18857
0.8442	Intermediate Similarity	NPC147993
0.8378	Intermediate Similarity	NPC127094
0.8378	Intermediate Similarity	NPC1340
0.8378	Intermediate Similarity	NPC187471
0.8378	Intermediate Similarity	NPC252182
0.8378	Intermediate Similarity	NPC470071
0.8356	Intermediate Similarity	NPC241085
0.8356	Intermediate Similarity	NPC299948
0.8356	Intermediate Similarity	NPC477820
0.8356	Intermediate Similarity	NPC129829
0.8356	Intermediate Similarity	NPC254037
0.8356	Intermediate Similarity	NPC470833
0.8356	Intermediate Similarity	NPC470830
0.8312	Intermediate Similarity	NPC185915
0.8312	Intermediate Similarity	NPC11907
0.8312	Intermediate Similarity	NPC133596
0.8312	Intermediate Similarity	NPC64081
0.8312	Intermediate Similarity	NPC474574
0.8289	Intermediate Similarity	NPC91387
0.8289	Intermediate Similarity	NPC270306
0.8289	Intermediate Similarity	NPC231680
0.8286	Intermediate Similarity	NPC114891
0.8194	Intermediate Similarity	NPC142712
0.8158	Intermediate Similarity	NPC304499
0.8143	Intermediate Similarity	NPC148174
0.8143	Intermediate Similarity	NPC71460
0.8143	Intermediate Similarity	NPC218585
0.8133	Intermediate Similarity	NPC131506
0.8133	Intermediate Similarity	NPC157777
0.8101	Intermediate Similarity	NPC477282
0.8101	Intermediate Similarity	NPC287452
0.8101	Intermediate Similarity	NPC81074
0.8082	Intermediate Similarity	NPC473230
0.8082	Intermediate Similarity	NPC475884
0.8082	Intermediate Similarity	NPC48079
0.8082	Intermediate Similarity	NPC63190
0.8056	Intermediate Similarity	NPC473276
0.8056	Intermediate Similarity	NPC474380
0.8056	Intermediate Similarity	NPC41577
0.8026	Intermediate Similarity	NPC473238
0.8026	Intermediate Similarity	NPC472341
0.8025	Intermediate Similarity	NPC121121
0.8025	Intermediate Similarity	NPC60018
0.8025	Intermediate Similarity	NPC202688
0.8025	Intermediate Similarity	NPC154043
0.8	Intermediate Similarity	NPC16449
0.7973	Intermediate Similarity	NPC472741
0.7945	Intermediate Similarity	NPC44122
0.7931	Intermediate Similarity	NPC476669
0.7927	Intermediate Similarity	NPC211135
0.7927	Intermediate Similarity	NPC216420
0.7927	Intermediate Similarity	NPC85095
0.7917	Intermediate Similarity	NPC69149
0.7917	Intermediate Similarity	NPC281540
0.7917	Intermediate Similarity	NPC118937
0.7917	Intermediate Similarity	NPC159654
0.7917	Intermediate Similarity	NPC167995
0.7895	Intermediate Similarity	NPC157422
0.7895	Intermediate Similarity	NPC109457
0.7895	Intermediate Similarity	NPC100586
0.7875	Intermediate Similarity	NPC474132
0.7875	Intermediate Similarity	NPC269333
0.7867	Intermediate Similarity	NPC99264
0.7857	Intermediate Similarity	NPC477604
0.7841	Intermediate Similarity	NPC475325
0.7838	Intermediate Similarity	NPC204233
0.7831	Intermediate Similarity	NPC255882
0.7831	Intermediate Similarity	NPC469878
0.7821	Intermediate Similarity	NPC478105
0.7816	Intermediate Similarity	NPC476668
0.7816	Intermediate Similarity	NPC473637
0.7808	Intermediate Similarity	NPC260116
0.7808	Intermediate Similarity	NPC190827
0.7808	Intermediate Similarity	NPC243469
0.7808	Intermediate Similarity	NPC472946
0.7808	Intermediate Similarity	NPC475943
0.7805	Intermediate Similarity	NPC475388
0.7778	Intermediate Similarity	NPC470609
0.7778	Intermediate Similarity	NPC249078
0.7778	Intermediate Similarity	NPC236099
0.7778	Intermediate Similarity	NPC209686
0.7763	Intermediate Similarity	NPC282454
0.775	Intermediate Similarity	NPC324700
0.775	Intermediate Similarity	NPC224802
0.775	Intermediate Similarity	NPC80089
0.775	Intermediate Similarity	NPC102708
0.775	Intermediate Similarity	NPC171426
0.775	Intermediate Similarity	NPC34046
0.7738	Intermediate Similarity	NPC232044
0.7738	Intermediate Similarity	NPC266651
0.7738	Intermediate Similarity	NPC273290
0.7733	Intermediate Similarity	NPC474756
0.7733	Intermediate Similarity	NPC475893
0.7722	Intermediate Similarity	NPC470145
0.7722	Intermediate Similarity	NPC91573
0.7714	Intermediate Similarity	NPC476735
0.7711	Intermediate Similarity	NPC470070
0.7711	Intermediate Similarity	NPC477285
0.7711	Intermediate Similarity	NPC111582
0.7692	Intermediate Similarity	NPC308440
0.7692	Intermediate Similarity	NPC472503
0.7683	Intermediate Similarity	NPC190940
0.7667	Intermediate Similarity	NPC473287
0.7662	Intermediate Similarity	NPC127283
0.7662	Intermediate Similarity	NPC195530
0.7662	Intermediate Similarity	NPC473279
0.7662	Intermediate Similarity	NPC8004
0.7654	Intermediate Similarity	NPC220379
0.7654	Intermediate Similarity	NPC201276
0.7654	Intermediate Similarity	NPC80891
0.7647	Intermediate Similarity	NPC121981
0.7647	Intermediate Similarity	NPC471240
0.764	Intermediate Similarity	NPC473503
0.764	Intermediate Similarity	NPC477605
0.7625	Intermediate Similarity	NPC212453
0.7625	Intermediate Similarity	NPC202540
0.7625	Intermediate Similarity	NPC476233
0.7619	Intermediate Similarity	NPC227260
0.7619	Intermediate Similarity	NPC478102
0.7595	Intermediate Similarity	NPC103822
0.759	Intermediate Similarity	NPC7988
0.759	Intermediate Similarity	NPC470611
0.759	Intermediate Similarity	NPC286719
0.759	Intermediate Similarity	NPC477286
0.7586	Intermediate Similarity	NPC473472
0.7586	Intermediate Similarity	NPC20822
0.7586	Intermediate Similarity	NPC477606
0.7582	Intermediate Similarity	NPC477226
0.7564	Intermediate Similarity	NPC232112
0.7561	Intermediate Similarity	NPC78545
0.7561	Intermediate Similarity	NPC71535
0.7558	Intermediate Similarity	NPC263802
0.7558	Intermediate Similarity	NPC474657
0.7558	Intermediate Similarity	NPC186145
0.7558	Intermediate Similarity	NPC140446
0.7558	Intermediate Similarity	NPC43912
0.7558	Intermediate Similarity	NPC475313
0.7556	Intermediate Similarity	NPC469710
0.7531	Intermediate Similarity	NPC471769
0.7531	Intermediate Similarity	NPC477817
0.7531	Intermediate Similarity	NPC31828
0.7531	Intermediate Similarity	NPC471045
0.7531	Intermediate Similarity	NPC477819
0.7531	Intermediate Similarity	NPC329117
0.7531	Intermediate Similarity	NPC478128
0.7529	Intermediate Similarity	NPC290612
0.75	Intermediate Similarity	NPC4209
0.75	Intermediate Similarity	NPC469987
0.75	Intermediate Similarity	NPC207013
0.75	Intermediate Similarity	NPC473638
0.75	Intermediate Similarity	NPC223143
0.7471	Intermediate Similarity	NPC281004
0.7471	Intermediate Similarity	NPC128475
0.7471	Intermediate Similarity	NPC475664
0.747	Intermediate Similarity	NPC12933
0.747	Intermediate Similarity	NPC469745
0.747	Intermediate Similarity	NPC73515
0.747	Intermediate Similarity	NPC109533
0.7468	Intermediate Similarity	NPC475458

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 NPC473916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	4493
0.2-0.3	3057
0.3-0.4	724
0.4-0.5	239
0.5-0.6	192
0.6-0.7	35
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8611	High Similarity	NPD4267	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6114	Approved
0.775	Intermediate Similarity	NPD6118	Approved
0.775	Intermediate Similarity	NPD6115	Approved
0.775	Intermediate Similarity	NPD6697	Approved
0.7532	Intermediate Similarity	NPD4787	Phase 1
0.75	Intermediate Similarity	NPD6117	Approved
0.7436	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6116	Phase 1
0.7375	Intermediate Similarity	NPD3703	Phase 2
0.7303	Intermediate Similarity	NPD6701	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6700	Approved
0.725	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6702	Approved
0.7222	Intermediate Similarity	NPD6703	Approved
0.7179	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD6928	Phase 2
0.7108	Intermediate Similarity	NPD5364	Discontinued
0.6957	Remote Similarity	NPD8171	Discontinued
0.6875	Remote Similarity	NPD4245	Approved
0.6875	Remote Similarity	NPD4244	Approved
0.6875	Remote Similarity	NPD4789	Approved
0.6835	Remote Similarity	NPD5360	Phase 3
0.6835	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6942	Approved
0.6548	Remote Similarity	NPD7339	Approved
0.6538	Remote Similarity	NPD371	Approved
0.6512	Remote Similarity	NPD3671	Phase 1
0.6495	Remote Similarity	NPD7920	Phase 3
0.6495	Remote Similarity	NPD7919	Phase 3
0.6429	Remote Similarity	NPD8088	Phase 1
0.642	Remote Similarity	NPD6705	Phase 1
0.6386	Remote Similarity	NPD6081	Approved
0.6386	Remote Similarity	NPD4758	Discontinued
0.6279	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6933	Approved
0.6275	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7645	Phase 2
0.6237	Remote Similarity	NPD7524	Approved
0.62	Remote Similarity	NPD8418	Phase 2
0.618	Remote Similarity	NPD4748	Discontinued
0.6173	Remote Similarity	NPD4224	Phase 2
0.6146	Remote Similarity	NPD8034	Phase 2
0.6146	Remote Similarity	NPD8035	Phase 2
0.6143	Remote Similarity	NPD385	Approved
0.6143	Remote Similarity	NPD384	Approved
0.6129	Remote Similarity	NPD8308	Discontinued
0.6122	Remote Similarity	NPD7991	Discontinued
0.6105	Remote Similarity	NPD5328	Approved
0.61	Remote Similarity	NPD7638	Approved
0.6087	Remote Similarity	NPD4786	Approved
0.6071	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6929	Approved
0.6064	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6926	Approved
0.6047	Remote Similarity	NPD6924	Approved
0.604	Remote Similarity	NPD7639	Approved
0.604	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD5777	Approved
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD6931	Approved
0.5979	Remote Similarity	NPD6079	Approved
0.5978	Remote Similarity	NPD6695	Phase 3
0.5978	Remote Similarity	NPD4788	Approved
0.5977	Remote Similarity	NPD3702	Approved
0.5957	Remote Similarity	NPD3618	Phase 1
0.5922	Remote Similarity	NPD7632	Discontinued
0.5914	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD3668	Phase 3
0.587	Remote Similarity	NPD3667	Approved
0.5862	Remote Similarity	NPD1811	Approved
0.5862	Remote Similarity	NPD1810	Approved
0.5843	Remote Similarity	NPD5776	Phase 2
0.5843	Remote Similarity	NPD6925	Approved
0.5843	Remote Similarity	NPD6932	Approved
0.5841	Remote Similarity	NPD7516	Approved
0.5814	Remote Similarity	NPD4243	Approved
0.5814	Remote Similarity	NPD7152	Approved
0.5814	Remote Similarity	NPD7150	Approved
0.5814	Remote Similarity	NPD7151	Approved
0.5778	Remote Similarity	NPD7145	Approved
0.5775	Remote Similarity	NPD386	Approved
0.5775	Remote Similarity	NPD388	Approved
0.5765	Remote Similarity	NPD6923	Approved
0.5765	Remote Similarity	NPD6922	Approved
0.5758	Remote Similarity	NPD4202	Approved
0.5752	Remote Similarity	NPD7327	Approved
0.5752	Remote Similarity	NPD7328	Approved
0.5743	Remote Similarity	NPD5222	Approved
0.5743	Remote Similarity	NPD4697	Phase 3
0.5743	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5221	Approved
0.5729	Remote Similarity	NPD7750	Discontinued
0.5714	Remote Similarity	NPD6683	Phase 2
0.5698	Remote Similarity	NPD7144	Approved
0.5698	Remote Similarity	NPD7143	Approved
0.5688	Remote Similarity	NPD4634	Approved
0.5686	Remote Similarity	NPD5173	Approved
0.5686	Remote Similarity	NPD4755	Approved
0.5684	Remote Similarity	NPD6893	Approved
0.5682	Remote Similarity	NPD4784	Approved
0.5682	Remote Similarity	NPD4785	Approved
0.5676	Remote Similarity	NPD8133	Approved
0.5673	Remote Similarity	NPD4159	Approved
0.5657	Remote Similarity	NPD7515	Phase 2
0.5652	Remote Similarity	NPD7514	Phase 3
0.5652	Remote Similarity	NPD8377	Approved
0.5652	Remote Similarity	NPD8294	Approved
0.5652	Remote Similarity	NPD7509	Discontinued
0.5648	Remote Similarity	NPD8174	Phase 2
0.5631	Remote Similarity	NPD5290	Discontinued
0.5603	Remote Similarity	NPD8378	Approved
0.5603	Remote Similarity	NPD8033	Approved
0.5603	Remote Similarity	NPD8380	Approved
0.5603	Remote Similarity	NPD8296	Approved
0.5603	Remote Similarity	NPD8379	Approved
0.5603	Remote Similarity	NPD8335	Approved
0.56	Remote Similarity	NPD6399	Phase 3

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