NPASS Compound

Structure

NPC475208 OpenBabel07101719192D 57 63 0 0 1 0 0 0 0 0999 V2000 -7.2288 1.0196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1634 -3.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1941 -3.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5181 -0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8421 2.7778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 -0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 1.9385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 -2.4231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 -2.4231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3575 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7150 4.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8729 2.7778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2926 1.2705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 -1.4538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1969 0.4846 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8756 4.3615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5181 1.4538 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6788 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6788 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0417 2.2067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0363 4.8462 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1055 2.4575 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1969 4.3615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4202 1.7722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1969 3.3923 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1969 1.4538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6710 0.8360 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0363 2.9077 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0495 0.4015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6788 -2.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5181 0.4846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3575 1.9385 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8394 0.4846 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 -1.6788 -0.9692 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7150 5.8154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9037 2.7778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0363 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 0.4846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7271 2.8920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0363 5.8154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8546 3.3937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3575 4.8462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4840 2.0230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3575 2.9077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7986 1.3377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6072 0.5851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8756 3.3923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0363 1.9385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9857 0.1506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 37 1 0 0 0 0 3 37 1 0 0 0 0 6 40 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 40 1 0 0 0 0 12 13 1 0 0 0 0 12 37 1 0 0 0 0 13 42 1 0 0 0 0 14 21 1 0 0 0 0 14 37 1 0 0 0 0 15 22 1 0 0 0 0 15 38 1 0 0 0 0 16 26 1 0 0 0 0 16 41 1 0 0 0 0 17 43 1 0 0 0 0 18 39 1 0 0 0 0 18 44 1 0 0 0 0 19 1 1 1 0 0 0 19 27 1 0 0 0 0 19 54 1 0 0 0 0 20 21 1 0 0 0 0 20 41 1 0 0 0 0 21 42 1 6 0 0 0 22 33 1 0 0 0 0 22 45 1 1 0 0 0 23 17 1 1 0 0 0 23 28 1 0 0 0 0 23 55 1 0 0 0 0 24 38 1 1 0 0 0 24 39 1 0 0 0 0 25 38 1 1 0 0 0 25 40 1 0 0 0 0 26 42 1 6 0 0 0 26 46 1 0 0 0 0 27 29 1 0 0 0 0 27 47 1 6 0 0 0 28 30 1 0 0 0 0 28 48 1 6 0 0 0 29 31 1 0 0 0 0 29 49 1 1 0 0 0 30 32 1 0 0 0 0 30 50 1 1 0 0 0 31 34 1 0 0 0 0 31 51 1 1 0 0 0 32 35 1 0 0 0 0 32 52 1 6 0 0 0 33 39 1 1 0 0 0 33 56 1 0 0 0 0 34 54 1 0 0 0 0 34 57 1 6 0 0 0 35 55 1 0 0 0 0 35 56 1 1 0 0 0 36 53 2 0 0 0 0 36 57 1 0 0 0 0 38 4 1 1 0 0 0 39 5 1 1 0 0 0 40 41 1 6 0 0 0 41 7 1 6 0 0 0 42 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	812.46
Volume:	801.673
LogP:	2.323
LogD:	1.571
LogS:	-3.427
# Rotatable Bonds:	7
TPSA:	256.29
# H-Bond Aceptor:	15
# H-Bond Donor:	10
# Rings:	7
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.098
Synthetic Accessibility Score:	6.074
Fsp3:	0.929
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:	-5.774
MDCK Permeability:	5.60469925403595e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.762
20% Bioavailability (F20%):	0.302
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	72.33736419677734%
Volume Distribution (VD):	0.32
Pgp-substrate:	16.550579071044922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	0.891
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.184
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC475208

Natural Product ID:	NPC475208
*Common Name:**	3-O-Beta-D-Glucopyranosyl-28-O-Alpha-L-Rhamnopyranosyl-16Alpha-Hydrox Yprotobassic Acid
IUPAC Name:	[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:
Standard InCHIKey:	STQISEBYTPHEPL-YIGUUSMJSA-N
Standard InCHI:	InChI=1S/C42H68O15/c1-19-27(47)29(49)31(51)34(54-19)57-36(53)42-13-12-37(2,3)14-21(42)20-8-9-25-38(4)15-22(45)33(56-35-32(52)30(50)28(48)23(17-43)55-35)39(5,18-44)24(38)10-11-40(25,6)41(20,7)16-26(42)46/h8,19,21-35,43-52H,9-18H2,1-7H3/t19-,21-,22-,23+,24+,25+,26+,27-,28+,29+,30-,31+,32+,33-,34-,35-,38-,39-,40+,41+,42+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501038
PubChem CID:	44575353
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10543897]
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	78.0	ug.mL-1	PMID[453495]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	>	1250.0	ug.mL-1	PMID[453495]

☑ 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 NPC475208 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	268
0.1-0.2	1784
0.2-0.3	5066
0.3-0.4	10923
0.4-0.5	11134
0.5-0.6	6370
0.6-0.7	4033
0.7-0.8	1934
0.8-0.85	493
0.85-0.9	271
0.9-0.95	198
0.95-1	223

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC238935
0.9904	High Similarity	NPC48249
0.9904	High Similarity	NPC80843
0.9904	High Similarity	NPC1046
0.9808	High Similarity	NPC179434
0.9808	High Similarity	NPC31839
0.972	High Similarity	NPC300419
0.9717	High Similarity	NPC475486
0.9717	High Similarity	NPC164389
0.9714	High Similarity	NPC139894
0.9714	High Similarity	NPC473383
0.9712	High Similarity	NPC7870
0.9712	High Similarity	NPC474589
0.9712	High Similarity	NPC102914
0.9712	High Similarity	NPC164194
0.9712	High Similarity	NPC75747
0.9712	High Similarity	NPC90856
0.9712	High Similarity	NPC127056
0.9712	High Similarity	NPC270667
0.9712	High Similarity	NPC279554
0.9712	High Similarity	NPC242611
0.9712	High Similarity	NPC68419
0.9712	High Similarity	NPC29069
0.9712	High Similarity	NPC108709
0.9712	High Similarity	NPC174679
0.9712	High Similarity	NPC475296
0.9712	High Similarity	NPC59804
0.9712	High Similarity	NPC110139
0.9712	High Similarity	NPC136877
0.9712	High Similarity	NPC56713
0.9712	High Similarity	NPC199457
0.963	High Similarity	NPC237191
0.9626	High Similarity	NPC476992
0.9626	High Similarity	NPC26626
0.9626	High Similarity	NPC291903
0.9626	High Similarity	NPC51465
0.9626	High Similarity	NPC75287
0.9626	High Similarity	NPC37134
0.9626	High Similarity	NPC305267
0.9626	High Similarity	NPC288205
0.9623	High Similarity	NPC73318
0.9623	High Similarity	NPC150400
0.9623	High Similarity	NPC134835
0.9623	High Similarity	NPC163183
0.9623	High Similarity	NPC96641
0.9623	High Similarity	NPC473343
0.9619	High Similarity	NPC164419
0.9619	High Similarity	NPC108748
0.9619	High Similarity	NPC235841
0.9619	High Similarity	NPC211798
0.9619	High Similarity	NPC473481
0.9619	High Similarity	NPC297208
0.9619	High Similarity	NPC30397
0.9615	High Similarity	NPC57362
0.9615	High Similarity	NPC237503
0.9615	High Similarity	NPC167383
0.9615	High Similarity	NPC306746
0.9615	High Similarity	NPC204407
0.9615	High Similarity	NPC127853
0.9541	High Similarity	NPC471577
0.9537	High Similarity	NPC104137
0.9537	High Similarity	NPC85154
0.9537	High Similarity	NPC286457
0.9537	High Similarity	NPC473452
0.9537	High Similarity	NPC470876
0.9537	High Similarity	NPC8524
0.9537	High Similarity	NPC323359
0.9537	High Similarity	NPC123522
0.9537	High Similarity	NPC191827
0.9537	High Similarity	NPC309223
0.9537	High Similarity	NPC475119
0.9537	High Similarity	NPC475209
0.9537	High Similarity	NPC220160
0.9537	High Similarity	NPC475514
0.9537	High Similarity	NPC102505
0.9537	High Similarity	NPC33012
0.9537	High Similarity	NPC473824
0.9537	High Similarity	NPC69811
0.9528	High Similarity	NPC139044
0.9528	High Similarity	NPC324875
0.9528	High Similarity	NPC475516
0.9528	High Similarity	NPC104400
0.9528	High Similarity	NPC104071
0.9528	High Similarity	NPC276093
0.9528	High Similarity	NPC292677
0.9528	High Similarity	NPC257468
0.9528	High Similarity	NPC100383
0.9528	High Similarity	NPC469946
0.9528	High Similarity	NPC475504
0.9528	High Similarity	NPC101744
0.9528	High Similarity	NPC473373
0.9528	High Similarity	NPC471383
0.9528	High Similarity	NPC102439
0.9528	High Similarity	NPC128925
0.9528	High Similarity	NPC116794
0.9528	High Similarity	NPC109079
0.9528	High Similarity	NPC10320
0.9528	High Similarity	NPC256798
0.9528	High Similarity	NPC79718
0.9524	High Similarity	NPC476880
0.9524	High Similarity	NPC476883
0.9524	High Similarity	NPC476886
0.9524	High Similarity	NPC78046
0.9524	High Similarity	NPC220984
0.9524	High Similarity	NPC476881
0.9524	High Similarity	NPC269095
0.9524	High Similarity	NPC274507
0.9524	High Similarity	NPC476885
0.9524	High Similarity	NPC476887
0.9524	High Similarity	NPC476884
0.9524	High Similarity	NPC476882
0.9519	High Similarity	NPC177246
0.9519	High Similarity	NPC476123
0.9519	High Similarity	NPC284807
0.9519	High Similarity	NPC28198
0.9455	High Similarity	NPC153673
0.9455	High Similarity	NPC142151
0.9455	High Similarity	NPC267694
0.9455	High Similarity	NPC473645
0.9455	High Similarity	NPC110385
0.9455	High Similarity	NPC37860
0.9455	High Similarity	NPC144644
0.945	High Similarity	NPC473459
0.945	High Similarity	NPC105800
0.945	High Similarity	NPC232237
0.9439	High Similarity	NPC47063
0.9439	High Similarity	NPC133818
0.9439	High Similarity	NPC204458
0.9439	High Similarity	NPC258885
0.9439	High Similarity	NPC323341
0.9439	High Similarity	NPC192600
0.9439	High Similarity	NPC114304
0.9439	High Similarity	NPC475287
0.9439	High Similarity	NPC46665
0.9439	High Similarity	NPC475467
0.9439	High Similarity	NPC219180
0.9439	High Similarity	NPC124296
0.9439	High Similarity	NPC251263
0.9439	High Similarity	NPC166422
0.9439	High Similarity	NPC114287
0.9439	High Similarity	NPC151543
0.9439	High Similarity	NPC269315
0.9439	High Similarity	NPC473826
0.9439	High Similarity	NPC189884
0.9439	High Similarity	NPC174720
0.9439	High Similarity	NPC241909
0.9439	High Similarity	NPC155410
0.9439	High Similarity	NPC295823
0.9439	High Similarity	NPC271138
0.9439	High Similarity	NPC309714
0.9439	High Similarity	NPC138334
0.9434	High Similarity	NPC191763
0.9429	High Similarity	NPC137917
0.9423	High Similarity	NPC283849
0.9423	High Similarity	NPC473538
0.9369	High Similarity	NPC275225
0.9369	High Similarity	NPC51099
0.9369	High Similarity	NPC293031
0.9369	High Similarity	NPC68767
0.9364	High Similarity	NPC114441
0.9364	High Similarity	NPC25663
0.9364	High Similarity	NPC6377
0.9364	High Similarity	NPC214484
0.9364	High Similarity	NPC473884
0.9364	High Similarity	NPC208381
0.9364	High Similarity	NPC472949
0.9364	High Similarity	NPC469945
0.9364	High Similarity	NPC309780
0.9364	High Similarity	NPC180550
0.9364	High Similarity	NPC207738
0.9364	High Similarity	NPC157868
0.9364	High Similarity	NPC39211
0.9364	High Similarity	NPC135849
0.9364	High Similarity	NPC475171
0.9364	High Similarity	NPC473386
0.9364	High Similarity	NPC35405
0.9364	High Similarity	NPC51564
0.9364	High Similarity	NPC11551
0.9358	High Similarity	NPC471580
0.9358	High Similarity	NPC471547
0.9358	High Similarity	NPC473405
0.9352	High Similarity	NPC161717
0.9352	High Similarity	NPC79643
0.9352	High Similarity	NPC204414
0.9352	High Similarity	NPC250247
0.9352	High Similarity	NPC41061
0.9352	High Similarity	NPC469782
0.9352	High Similarity	NPC236638
0.9352	High Similarity	NPC123199
0.9352	High Similarity	NPC57484
0.9352	High Similarity	NPC475160
0.9352	High Similarity	NPC476068
0.9352	High Similarity	NPC43550
0.9352	High Similarity	NPC473714
0.9352	High Similarity	NPC60557
0.9352	High Similarity	NPC475140
0.9352	High Similarity	NPC261506
0.9352	High Similarity	NPC65105
0.9352	High Similarity	NPC76972
0.9352	High Similarity	NPC70809

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 NPC475208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	2106
0.2-0.3	3811
0.3-0.4	1929
0.4-0.5	619
0.5-0.6	278
0.6-0.7	125
0.7-0.8	31
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9035	High Similarity	NPD8328	Phase 3
0.9009	High Similarity	NPD8295	Clinical (unspecified phase)
0.8889	High Similarity	NPD8132	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD8133	Approved
0.8036	Intermediate Similarity	NPD6412	Phase 2
0.7965	Intermediate Similarity	NPD6686	Approved
0.7903	Intermediate Similarity	NPD7319	Approved
0.785	Intermediate Similarity	NPD7748	Approved
0.7833	Intermediate Similarity	NPD8377	Approved
0.7833	Intermediate Similarity	NPD8294	Approved
0.7823	Intermediate Similarity	NPD7736	Approved
0.7805	Intermediate Similarity	NPD7507	Approved
0.7798	Intermediate Similarity	NPD7902	Approved
0.7769	Intermediate Similarity	NPD8296	Approved
0.7769	Intermediate Similarity	NPD8516	Approved
0.7769	Intermediate Similarity	NPD8380	Approved
0.7769	Intermediate Similarity	NPD8513	Phase 3
0.7769	Intermediate Similarity	NPD8033	Approved
0.7769	Intermediate Similarity	NPD8335	Approved
0.7769	Intermediate Similarity	NPD8379	Approved
0.7769	Intermediate Similarity	NPD8515	Approved
0.7769	Intermediate Similarity	NPD8517	Approved
0.7769	Intermediate Similarity	NPD8378	Approved
0.7664	Intermediate Similarity	NPD7515	Phase 2
0.7603	Intermediate Similarity	NPD7516	Approved
0.76	Intermediate Similarity	NPD8293	Discontinued
0.7523	Intermediate Similarity	NPD7900	Approved
0.7523	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7328	Approved
0.7521	Intermediate Similarity	NPD7327	Approved
0.7419	Intermediate Similarity	NPD6370	Approved
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7503	Approved
0.7302	Intermediate Similarity	NPD7492	Approved
0.7258	Intermediate Similarity	NPD6054	Approved
0.7258	Intermediate Similarity	NPD6319	Approved
0.7258	Intermediate Similarity	NPD6059	Approved
0.7244	Intermediate Similarity	NPD6616	Approved
0.7241	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7078	Approved
0.7182	Intermediate Similarity	NPD8035	Phase 2
0.7182	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8297	Approved
0.7107	Intermediate Similarity	NPD6882	Approved
0.7105	Intermediate Similarity	NPD7638	Approved
0.7063	Intermediate Similarity	NPD6015	Approved
0.7063	Intermediate Similarity	NPD6016	Approved
0.7043	Intermediate Similarity	NPD7640	Approved
0.7043	Intermediate Similarity	NPD7639	Approved
0.7027	Intermediate Similarity	NPD6411	Approved
0.7025	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7645	Phase 2
0.7016	Intermediate Similarity	NPD6009	Approved
0.7016	Intermediate Similarity	NPD7115	Discovery
0.7008	Intermediate Similarity	NPD5988	Approved
0.6964	Remote Similarity	NPD6399	Phase 3
0.6953	Remote Similarity	NPD6067	Discontinued
0.6944	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8074	Phase 3
0.6911	Remote Similarity	NPD4632	Approved
0.6891	Remote Similarity	NPD6402	Approved
0.6891	Remote Similarity	NPD5739	Approved
0.6891	Remote Similarity	NPD6675	Approved
0.6891	Remote Similarity	NPD7128	Approved
0.686	Remote Similarity	NPD6373	Approved
0.686	Remote Similarity	NPD6372	Approved
0.6847	Remote Similarity	NPD6101	Approved
0.6847	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8171	Discontinued
0.681	Remote Similarity	NPD4225	Approved
0.6797	Remote Similarity	NPD6921	Approved
0.6777	Remote Similarity	NPD7320	Approved
0.6777	Remote Similarity	NPD6899	Approved
0.6777	Remote Similarity	NPD6881	Approved
0.6748	Remote Similarity	NPD6649	Approved
0.6748	Remote Similarity	NPD6650	Approved
0.6748	Remote Similarity	NPD8130	Phase 1
0.6742	Remote Similarity	NPD6033	Approved
0.6726	Remote Similarity	NPD7983	Approved
0.6694	Remote Similarity	NPD5697	Approved
0.6694	Remote Similarity	NPD5701	Approved
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6637	Remote Similarity	NPD6698	Approved
0.6637	Remote Similarity	NPD46	Approved
0.6613	Remote Similarity	NPD6847	Approved
0.6613	Remote Similarity	NPD6617	Approved
0.6613	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6013	Approved
0.6585	Remote Similarity	NPD6014	Approved
0.6585	Remote Similarity	NPD6012	Approved
0.6581	Remote Similarity	NPD6083	Phase 2
0.6581	Remote Similarity	NPD6084	Phase 2
0.6577	Remote Similarity	NPD3618	Phase 1
0.6565	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD5328	Approved
0.6545	Remote Similarity	NPD4786	Approved
0.6538	Remote Similarity	NPD5983	Phase 2
0.6518	Remote Similarity	NPD3573	Approved
0.6514	Remote Similarity	NPD3667	Approved
0.6504	Remote Similarity	NPD6011	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6493	Remote Similarity	NPD8337	Approved
0.6493	Remote Similarity	NPD8336	Approved
0.6484	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6008	Approved
0.6466	Remote Similarity	NPD6336	Discontinued
0.6455	Remote Similarity	NPD3669	Approved
0.6455	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4755	Approved
0.6435	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6423	Remote Similarity	NPD8449	Approved
0.6423	Remote Similarity	NPD8338	Approved
0.6414	Remote Similarity	NPD7625	Phase 1
0.6406	Remote Similarity	NPD6940	Discontinued
0.6404	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8342	Approved
0.6391	Remote Similarity	NPD8340	Approved
0.6391	Remote Similarity	NPD8341	Approved
0.6391	Remote Similarity	NPD8299	Approved
0.6387	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4202	Approved
0.6377	Remote Similarity	NPD8450	Suspended
0.6356	Remote Similarity	NPD7839	Suspended
0.6343	Remote Similarity	NPD8451	Approved
0.6333	Remote Similarity	NPD4696	Approved
0.6333	Remote Similarity	NPD5285	Approved
0.6333	Remote Similarity	NPD5286	Approved
0.6333	Remote Similarity	NPD4700	Approved
0.633	Remote Similarity	NPD7525	Registered
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD7829	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD7830	Approved
0.6316	Remote Similarity	NPD6672	Approved
0.6296	Remote Similarity	NPD6697	Approved
0.6296	Remote Similarity	NPD6115	Approved
0.6296	Remote Similarity	NPD8448	Approved
0.6296	Remote Similarity	NPD6118	Approved
0.6296	Remote Similarity	NPD6114	Approved
0.6293	Remote Similarity	NPD7637	Suspended
0.6288	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5344	Discontinued
0.6279	Remote Similarity	NPD6274	Approved
0.6277	Remote Similarity	NPD8391	Approved
0.6277	Remote Similarity	NPD8390	Approved
0.6277	Remote Similarity	NPD5956	Approved
0.6277	Remote Similarity	NPD8392	Approved
0.6273	Remote Similarity	NPD1780	Approved
0.6273	Remote Similarity	NPD1779	Approved
0.6271	Remote Similarity	NPD5695	Phase 3
0.626	Remote Similarity	NPD7100	Approved
0.626	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3666	Approved
0.6241	Remote Similarity	NPD8080	Discontinued
0.623	Remote Similarity	NPD5225	Approved
0.623	Remote Similarity	NPD5224	Approved
0.623	Remote Similarity	NPD5211	Phase 2
0.623	Remote Similarity	NPD4633	Approved
0.623	Remote Similarity	NPD5226	Approved
0.6218	Remote Similarity	NPD5221	Approved
0.6218	Remote Similarity	NPD4697	Phase 3
0.6218	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5222	Approved
0.6214	Remote Similarity	NPD8415	Approved
0.621	Remote Similarity	NPD4767	Approved
0.621	Remote Similarity	NPD4768	Approved
0.6204	Remote Similarity	NPD6116	Phase 1
0.6183	Remote Similarity	NPD6335	Approved
0.6179	Remote Similarity	NPD5175	Approved
0.6179	Remote Similarity	NPD5174	Approved
0.6167	Remote Similarity	NPD5173	Approved
0.6165	Remote Similarity	NPD6908	Approved
0.6165	Remote Similarity	NPD8444	Approved
0.6165	Remote Similarity	NPD6909	Approved
0.616	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6868	Approved
0.6148	Remote Similarity	NPD5223	Approved
0.6142	Remote Similarity	NPD6371	Approved
0.614	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6356	Clinical (unspecified phase)

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