NPASS Compound

Structure

NPC473549 OpenBabel07101718182D 49 53 0 0 1 0 0 0 0 0999 V2000 4.0000 -7.2372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -8.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -8.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1398 -6.3178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7024 -7.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -8.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -7.2372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0419 -5.6998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1887 -6.6268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0908 -6.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2377 -6.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -10.7013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -11.5674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5067 -4.0525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0933 -5.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8614 -4.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5677 -2.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -8.1033 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0000 -7.2372 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -8.9693 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.2498 -4.7216 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.5000 -6.3712 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.5556 -4.3615 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.8364 -4.7885 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.8125 -3.6924 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.8246 -1.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.3966 -5.6487 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.8735 -1.7872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.6656 -2.7653 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.7024 -5.2885 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -9.8353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4088 -3.4344 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.3477 -5.3396 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.4945 -6.2667 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.6535 -4.9795 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -10.7013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7319 -3.7940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0204 -2.7142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.0325 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1304 -1.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7146 -3.0743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -9.8353 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 8.9103 -4.3104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -10.5674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -11.5674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -12.5674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.3598 -3.1254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2009 -4.4126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -11.5674 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 7 2 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 33 1 0 0 0 0 11 34 1 0 0 0 0 12 13 1 0 0 0 0 12 36 1 0 0 0 0 13 49 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 35 1 0 0 0 0 17 26 1 0 0 0 0 17 47 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 20 31 1 0 0 0 0 21 48 1 0 0 0 0 22 34 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 30 1 0 0 0 0 24 37 1 0 0 0 0 25 38 1 0 0 0 0 26 28 1 0 0 0 0 26 39 1 0 0 0 0 27 33 1 0 0 0 0 27 35 1 0 0 0 0 28 29 1 0 0 0 0 28 40 1 0 0 0 0 29 32 1 0 0 0 0 29 41 1 0 0 0 0 30 34 1 0 0 0 0 30 35 1 0 0 0 0 31 36 2 0 0 0 0 31 42 1 0 0 0 0 32 47 1 0 0 0 0 32 48 1 0 0 0 0 35 43 1 0 0 0 0 44 49 1 0 0 0 0 45 49 2 0 0 0 0 46 49 2 0 0 0 0 M CHG 1 42 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	716.37
Volume:	699.531
LogP:	-0.36
LogD:	0.476
LogS:	-1.853
# Rotatable Bonds:	10
TPSA:	229.63
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.054
Synthetic Accessibility Score:	6.091
Fsp3:	0.914
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.124
MDCK Permeability:	0.00010393966658739373
Pgp-inhibitor:	0.019
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.977
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	74.25965118408203%
Volume Distribution (VD):	0.644
Pgp-substrate:	5.410453796386719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.742
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.283
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	1.083
Half-life (T1/2):	0.29

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.867
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.231
Maximum Recommended Daily Dose:	0.566
Skin Sensitization:	0.689
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC473549

Natural Product ID:	NPC473549
*Common Name:**	Minutoside B
IUPAC Name:	sodium;2-[[(E,2S,3R,6R)-2,3-dimethyl-6-[(3S,5S,6S,8S,9R,10S,13R,14S,15R,17R)-6,8,15-trihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]hept-4-enoyl]amino]ethanesulfonate
Synonyms:
Standard InCHIKey:	QOUPUAWRCKUXRT-SDDQLLNASA-M
Standard InCHI:	InChI=1S/C35H59NO12S.Na/c1-18(20(3)31(42)36-12-13-49(44,45)46)6-7-19(2)22-15-24(37)30-34(22,5)11-9-27-33(4)10-8-21(14-23(33)25(38)16-35(27,30)43)48-32-29(41)28(40)26(39)17-47-32;/h6-7,18-30,32,37-41,43H,8-17H2,1-5H3,(H,36,42)(H,44,45,46);/q;+1/p-1/b7-6+;/t18-,19-,20+,21+,22-,23-,24-,25+,26-,27-,28+,29-,30-,32+,33+,34-,35+;/m1./s1
SMILES:	CC(C=CC(C)C(C)C(=O)NCCS(=O)(=O)[O-])C1CC(C2C1(CCC3C2(CC(C4C3(CCC(C4)OC5C(C(C(CO5)O)O)O)C)O)O)C)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445261
PubChem CID:	23679804
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:0001159] Taurinated bile acids 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
NPO7694	Anasterias minuta	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11858747]
NPO7694	Anasterias minuta	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16124779]
NPO7694	Anasterias minuta	Species	n.a.	n.a.	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	3.0	mm	PMID[515211]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IZ	=	5.0	mm	PMID[515211]

☑ 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 NPC473549 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	140
0.1-0.2	1479
0.2-0.3	9133
0.3-0.4	16828
0.4-0.5	8056
0.5-0.6	4643
0.6-0.7	1988
0.7-0.8	424
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8115	Intermediate Similarity	NPC475312
0.8115	Intermediate Similarity	NPC475354
0.7833	Intermediate Similarity	NPC475365
0.7833	Intermediate Similarity	NPC312774
0.7731	Intermediate Similarity	NPC4831
0.7731	Intermediate Similarity	NPC88000
0.7731	Intermediate Similarity	NPC472023
0.7731	Intermediate Similarity	NPC160734
0.7731	Intermediate Similarity	NPC309425
0.7731	Intermediate Similarity	NPC129372
0.7731	Intermediate Similarity	NPC47566
0.7705	Intermediate Similarity	NPC473469
0.768	Intermediate Similarity	NPC477050
0.7667	Intermediate Similarity	NPC136816
0.7656	Intermediate Similarity	NPC476692
0.7656	Intermediate Similarity	NPC476691
0.7647	Intermediate Similarity	NPC473200
0.7647	Intermediate Similarity	NPC7341
0.7642	Intermediate Similarity	NPC475634
0.7603	Intermediate Similarity	NPC114874
0.7603	Intermediate Similarity	NPC31907
0.7603	Intermediate Similarity	NPC120123
0.7603	Intermediate Similarity	NPC286969
0.7603	Intermediate Similarity	NPC472252
0.7603	Intermediate Similarity	NPC213190
0.7603	Intermediate Similarity	NPC8039
0.7603	Intermediate Similarity	NPC211879
0.7603	Intermediate Similarity	NPC189852
0.7603	Intermediate Similarity	NPC155010
0.7603	Intermediate Similarity	NPC16520
0.7603	Intermediate Similarity	NPC157659
0.7603	Intermediate Similarity	NPC131479
0.7603	Intermediate Similarity	NPC473020
0.7603	Intermediate Similarity	NPC245280
0.7581	Intermediate Similarity	NPC474573
0.7563	Intermediate Similarity	NPC234287
0.7563	Intermediate Similarity	NPC280825
0.7561	Intermediate Similarity	NPC478053
0.7561	Intermediate Similarity	NPC226642
0.7541	Intermediate Similarity	NPC165033
0.7541	Intermediate Similarity	NPC273879
0.754	Intermediate Similarity	NPC216595
0.754	Intermediate Similarity	NPC473567
0.7521	Intermediate Similarity	NPC159036
0.7521	Intermediate Similarity	NPC288694
0.7521	Intermediate Similarity	NPC312553
0.75	Intermediate Similarity	NPC235824
0.75	Intermediate Similarity	NPC472897
0.75	Intermediate Similarity	NPC472896
0.75	Intermediate Similarity	NPC7213
0.748	Intermediate Similarity	NPC269627
0.748	Intermediate Similarity	NPC473476
0.748	Intermediate Similarity	NPC160816
0.748	Intermediate Similarity	NPC473923
0.748	Intermediate Similarity	NPC242748
0.748	Intermediate Similarity	NPC69737
0.748	Intermediate Similarity	NPC472898
0.748	Intermediate Similarity	NPC473199
0.748	Intermediate Similarity	NPC26798
0.748	Intermediate Similarity	NPC127801
0.748	Intermediate Similarity	NPC152584
0.748	Intermediate Similarity	NPC472899
0.748	Intermediate Similarity	NPC208477
0.748	Intermediate Similarity	NPC208594
0.748	Intermediate Similarity	NPC472900
0.748	Intermediate Similarity	NPC194842
0.7459	Intermediate Similarity	NPC16573
0.7459	Intermediate Similarity	NPC473198
0.7458	Intermediate Similarity	NPC469710
0.744	Intermediate Similarity	NPC473328
0.744	Intermediate Similarity	NPC28844
0.744	Intermediate Similarity	NPC473318
0.7419	Intermediate Similarity	NPC63368
0.7419	Intermediate Similarity	NPC208650
0.7419	Intermediate Similarity	NPC231340
0.7419	Intermediate Similarity	NPC14946
0.7419	Intermediate Similarity	NPC181467
0.7398	Intermediate Similarity	NPC187400
0.7398	Intermediate Similarity	NPC221562
0.7398	Intermediate Similarity	NPC470885
0.7398	Intermediate Similarity	NPC475521
0.7395	Intermediate Similarity	NPC472989
0.7381	Intermediate Similarity	NPC472717
0.7381	Intermediate Similarity	NPC191439
0.7381	Intermediate Similarity	NPC65155
0.7381	Intermediate Similarity	NPC103627
0.7381	Intermediate Similarity	NPC170974
0.7373	Intermediate Similarity	NPC473503
0.736	Intermediate Similarity	NPC476540
0.736	Intermediate Similarity	NPC476541
0.736	Intermediate Similarity	NPC159005
0.736	Intermediate Similarity	NPC472988
0.736	Intermediate Similarity	NPC476539
0.736	Intermediate Similarity	NPC246124
0.736	Intermediate Similarity	NPC476538
0.736	Intermediate Similarity	NPC220427
0.736	Intermediate Similarity	NPC6931
0.736	Intermediate Similarity	NPC180183
0.736	Intermediate Similarity	NPC38217
0.7344	Intermediate Similarity	NPC476671
0.7344	Intermediate Similarity	NPC476693
0.7339	Intermediate Similarity	NPC474569
0.7323	Intermediate Similarity	NPC472715
0.7323	Intermediate Similarity	NPC197231
0.7323	Intermediate Similarity	NPC114188
0.7302	Intermediate Similarity	NPC306131
0.7302	Intermediate Similarity	NPC296761
0.7302	Intermediate Similarity	NPC125361
0.7302	Intermediate Similarity	NPC477027
0.7302	Intermediate Similarity	NPC472901
0.7302	Intermediate Similarity	NPC154085
0.7302	Intermediate Similarity	NPC51925
0.7302	Intermediate Similarity	NPC476835
0.7302	Intermediate Similarity	NPC43976
0.7302	Intermediate Similarity	NPC477026
0.7302	Intermediate Similarity	NPC475670
0.7302	Intermediate Similarity	NPC70204
0.7295	Intermediate Similarity	NPC31346
0.728	Intermediate Similarity	NPC234160
0.728	Intermediate Similarity	NPC33053
0.728	Intermediate Similarity	NPC190395
0.7273	Intermediate Similarity	NPC158088
0.7266	Intermediate Similarity	NPC231797
0.7266	Intermediate Similarity	NPC472716
0.7266	Intermediate Similarity	NPC19888
0.7258	Intermediate Similarity	NPC75608
0.725	Intermediate Similarity	NPC473287
0.7236	Intermediate Similarity	NPC272015
0.7213	Intermediate Similarity	NPC282669
0.7209	Intermediate Similarity	NPC144068
0.7203	Intermediate Similarity	NPC476668
0.7203	Intermediate Similarity	NPC473637
0.7203	Intermediate Similarity	NPC48463
0.72	Intermediate Similarity	NPC181845
0.72	Intermediate Similarity	NPC474015
0.72	Intermediate Similarity	NPC309448
0.719	Intermediate Similarity	NPC473890
0.719	Intermediate Similarity	NPC243728
0.719	Intermediate Similarity	NPC76486
0.7188	Intermediate Similarity	NPC475247
0.7188	Intermediate Similarity	NPC269466
0.7188	Intermediate Similarity	NPC13190
0.7188	Intermediate Similarity	NPC65167
0.7188	Intermediate Similarity	NPC294129
0.7188	Intermediate Similarity	NPC65034
0.7188	Intermediate Similarity	NPC208189
0.7188	Intermediate Similarity	NPC473021
0.7188	Intermediate Similarity	NPC472987
0.7177	Intermediate Similarity	NPC475701
0.7176	Intermediate Similarity	NPC157376
0.7176	Intermediate Similarity	NPC77319
0.7176	Intermediate Similarity	NPC244402
0.7176	Intermediate Similarity	NPC158344
0.7176	Intermediate Similarity	NPC471354
0.7176	Intermediate Similarity	NPC471353
0.7176	Intermediate Similarity	NPC93883
0.7176	Intermediate Similarity	NPC243196
0.7176	Intermediate Similarity	NPC142066
0.7176	Intermediate Similarity	NPC87250
0.7176	Intermediate Similarity	NPC20979
0.7176	Intermediate Similarity	NPC473852
0.7176	Intermediate Similarity	NPC34390
0.7176	Intermediate Similarity	NPC100048
0.7176	Intermediate Similarity	NPC474418
0.7176	Intermediate Similarity	NPC471355
0.7176	Intermediate Similarity	NPC99728
0.7176	Intermediate Similarity	NPC471351
0.7176	Intermediate Similarity	NPC50305
0.7176	Intermediate Similarity	NPC84987
0.7176	Intermediate Similarity	NPC476690
0.7176	Intermediate Similarity	NPC196429
0.7176	Intermediate Similarity	NPC27507
0.7176	Intermediate Similarity	NPC309034
0.7165	Intermediate Similarity	NPC42482
0.7165	Intermediate Similarity	NPC40440
0.7165	Intermediate Similarity	NPC302057
0.7164	Intermediate Similarity	NPC469943
0.7154	Intermediate Similarity	NPC477810
0.7154	Intermediate Similarity	NPC267510
0.7143	Intermediate Similarity	NPC476669
0.7143	Intermediate Similarity	NPC305423
0.7143	Intermediate Similarity	NPC283829
0.7143	Intermediate Similarity	NPC113044
0.7143	Intermediate Similarity	NPC230507
0.7143	Intermediate Similarity	NPC94272
0.7143	Intermediate Similarity	NPC475556
0.7143	Intermediate Similarity	NPC475629
0.7143	Intermediate Similarity	NPC14704
0.7143	Intermediate Similarity	NPC161676
0.7143	Intermediate Similarity	NPC470432
0.7132	Intermediate Similarity	NPC112274
0.7131	Intermediate Similarity	NPC157739
0.7131	Intermediate Similarity	NPC473638
0.7131	Intermediate Similarity	NPC216260
0.7131	Intermediate Similarity	NPC5358
0.7131	Intermediate Similarity	NPC473616
0.7121	Intermediate Similarity	NPC472080
0.7121	Intermediate Similarity	NPC10366
0.7121	Intermediate Similarity	NPC83287
0.712	Intermediate Similarity	NPC93352

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 NPC473549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	109
0.1-0.2	955
0.2-0.3	4846
0.3-0.4	2411
0.4-0.5	555
0.5-0.6	243
0.6-0.7	18
0.7-0.8	13
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
0.7143	Intermediate Similarity	NPD7625	Phase 1
0.7121	Intermediate Similarity	NPD7328	Approved
0.7121	Intermediate Similarity	NPD7327	Approved
0.7119	Intermediate Similarity	NPD6701	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6700	Approved
0.709	Intermediate Similarity	NPD8378	Approved
0.709	Intermediate Similarity	NPD8296	Approved
0.709	Intermediate Similarity	NPD8380	Approved
0.709	Intermediate Similarity	NPD8335	Approved
0.709	Intermediate Similarity	NPD8379	Approved
0.7068	Intermediate Similarity	NPD7516	Approved
0.7015	Intermediate Similarity	NPD8294	Approved
0.7015	Intermediate Similarity	NPD8377	Approved
0.6963	Remote Similarity	NPD8033	Approved
0.6917	Remote Similarity	NPD6703	Approved
0.6917	Remote Similarity	NPD6702	Approved
0.6715	Remote Similarity	NPD7503	Approved
0.6713	Remote Similarity	NPD8449	Approved
0.6667	Remote Similarity	NPD8450	Suspended
0.6643	Remote Similarity	NPD7507	Approved
0.662	Remote Similarity	NPD7319	Approved
0.6615	Remote Similarity	NPD6412	Phase 2
0.6585	Remote Similarity	NPD8171	Discontinued
0.6444	Remote Similarity	NPD8133	Approved
0.6439	Remote Similarity	NPD8174	Phase 2
0.6434	Remote Similarity	NPD7736	Approved
0.6312	Remote Similarity	NPD6370	Approved
0.6288	Remote Similarity	NPD5357	Phase 1
0.6268	Remote Similarity	NPD6067	Discontinued
0.622	Remote Similarity	NPD7991	Discontinued
0.617	Remote Similarity	NPD6054	Approved
0.616	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD8293	Discontinued
0.6134	Remote Similarity	NPD7525	Registered
0.609	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6059	Approved
0.6045	Remote Similarity	NPD6640	Phase 3
0.6042	Remote Similarity	NPD8328	Phase 3
0.6032	Remote Similarity	NPD3168	Discontinued
0.6014	Remote Similarity	NPD8297	Approved
0.6014	Remote Similarity	NPD6016	Approved
0.6014	Remote Similarity	NPD6015	Approved
0.6014	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD6928	Phase 2
0.5972	Remote Similarity	NPD5988	Approved
0.5959	Remote Similarity	NPD6616	Approved
0.5957	Remote Similarity	NPD6009	Approved
0.5957	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD6686	Approved
0.5944	Remote Similarity	NPD6319	Approved
0.5942	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD7604	Phase 2
0.592	Remote Similarity	NPD7524	Approved
0.5918	Remote Similarity	NPD7078	Approved
0.5906	Remote Similarity	NPD7136	Phase 2
0.5857	Remote Similarity	NPD4632	Approved
0.5833	Remote Similarity	NPD7638	Approved
0.5811	Remote Similarity	NPD8074	Phase 3
0.5806	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD6921	Approved
0.5793	Remote Similarity	NPD6908	Approved
0.5793	Remote Similarity	NPD6909	Approved
0.5789	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD7640	Approved
0.5778	Remote Similarity	NPD4754	Approved
0.5746	Remote Similarity	NPD4159	Approved
0.5726	Remote Similarity	NPD6695	Phase 3
0.5725	Remote Similarity	NPD6899	Approved
0.5725	Remote Similarity	NPD6881	Approved
0.5724	Remote Similarity	NPD8338	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD6650	Approved
0.5693	Remote Similarity	NPD5739	Approved
0.5693	Remote Similarity	NPD6402	Approved
0.5693	Remote Similarity	NPD6675	Approved
0.5693	Remote Similarity	NPD7128	Approved
0.5683	Remote Similarity	NPD6373	Approved
0.5683	Remote Similarity	NPD6372	Approved
0.5669	Remote Similarity	NPD7750	Discontinued
0.5667	Remote Similarity	NPD6033	Approved
0.5656	Remote Similarity	NPD7645	Phase 2
0.5652	Remote Similarity	NPD5697	Approved
0.5643	Remote Similarity	NPD7290	Approved
0.5643	Remote Similarity	NPD6883	Approved
0.5643	Remote Similarity	NPD7102	Approved
0.5643	Remote Similarity	NPD4634	Approved
0.5625	Remote Similarity	NPD6317	Approved
0.562	Remote Similarity	NPD3710	Phase 2
0.5612	Remote Similarity	NPD7320	Approved
0.5603	Remote Similarity	NPD6617	Approved
0.5603	Remote Similarity	NPD6869	Approved
0.5603	Remote Similarity	NPD6847	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