NPASS Compound

Structure

CID17521 OpenBabel06191715342D 33 36 0 0 1 0 0 0 0 0999 V2000 -10.3331 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4670 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4670 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4670 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9670 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 29 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 10 1 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 23 1 0 0 0 0 8 9 1 0 0 0 0 8 30 1 0 0 0 0 9 31 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 11 16 1 0 0 0 0 11 24 2 0 0 0 0 12 32 1 0 0 0 0 13 16 2 0 0 0 0 13 31 1 0 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 14 33 1 0 0 0 0 15 22 1 6 0 0 0 15 32 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 21 1 0 0 0 0 19 27 1 1 0 0 0 20 29 1 0 0 0 0 21 30 1 6 0 0 0 21 33 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.16
Volume:	438.352
LogP:	0.22
LogD:	-0.132
LogS:	-2.274
# Rotatable Bonds:	6
TPSA:	168.28
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	4.505
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.771
MDCK Permeability:	4.723147867480293e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.143
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.468

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	47.33634948730469%
Volume Distribution (VD):	0.824
Pgp-substrate:	29.064687728881836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.343
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.553
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	2.259
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.761
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.247
Carcinogencity:	0.348
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC17521

Natural Product ID:	NPC17521
*Common Name:**	(2S)-2-(2-Hydroxypropan-2-Yl)-4-Methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxymethyl]-2,3-Dihydrofuro[3,2-G]Chromen-5-One
IUPAC Name:	(2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrofuro[3,2-g]chromen-5-one
Synonyms:	Prim-O-Glucosylcimifugin
Standard InCHIKey:	XIUVHOSBSDYXRG-UVTAEQIVSA-N
Standard InCHI:	InChI=1S/C22H28O11/c1-22(2,28)15-5-10-12(32-15)6-13-16(20(10)29-3)11(24)4-9(31-13)8-30-21-19(27)18(26)17(25)14(7-23)33-21/h4,6,14-15,17-19,21,23,25-28H,5,7-8H2,1-3H3/t14-,15+,17-,18+,19-,21-/m1/s1
SMILES:	CC(C)([C@@H]1Cc2c(cc3c(c(=O)cc(CO[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)o3)c2OC)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1734606
PubChem CID:	14034912
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones [CHEMONTID:0001735] Furanochromones

*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
NPO24623	Xestospongia muta	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1431940]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17703773]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19355	Natrii sulfas	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11856	Natrii sulfas exsiccatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO19355	Natrii sulfas	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16676	Folium aconiti kusnezoffii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24541	Trivalvaria macrophylla	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1727	Clusia nemorosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29364	Diplolophium buchananii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24187	Cardiopetalum calophyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23810	Streptomyces alboflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24623	Xestospongia muta	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23976	Ceanothus intergerrimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24664	Lecanora hybocarpa	Species	Lecanoraceae	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
Others	2
Potency	3

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	10318.3	nM	PMID[480202]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[480202]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	44668.4	nM	PMID[480202]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	111.8	%	PMID[480204]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	96.8	%	PMID[480204]

☑ 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 NPC17521 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	393
0.1-0.2	1576
0.2-0.3	3463
0.3-0.4	8319
0.4-0.5	10085
0.5-0.6	4966
0.6-0.7	5803
0.7-0.8	5128
0.8-0.85	2166
0.85-0.9	740
0.9-0.95	49
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC470607
0.98	High Similarity	NPC470606
0.9667	High Similarity	NPC470603
0.9667	High Similarity	NPC470604
0.9667	High Similarity	NPC470605
0.96	High Similarity	NPC78021
0.96	High Similarity	NPC87304
0.96	High Similarity	NPC108706
0.96	High Similarity	NPC211158
0.96	High Similarity	NPC268950
0.9467	High Similarity	NPC23253
0.94	High Similarity	NPC191154
0.94	High Similarity	NPC38775
0.9392	High Similarity	NPC474302
0.9359	High Similarity	NPC183672
0.9346	High Similarity	NPC45165
0.9338	High Similarity	NPC190217
0.9338	High Similarity	NPC134819
0.9295	High Similarity	NPC44947
0.9295	High Similarity	NPC93215
0.9295	High Similarity	NPC131745
0.9286	High Similarity	NPC122809
0.9286	High Similarity	NPC23817
0.9272	High Similarity	NPC106025
0.9272	High Similarity	NPC213723
0.9272	High Similarity	NPC214454
0.9272	High Similarity	NPC477240
0.9267	High Similarity	NPC10097
0.9267	High Similarity	NPC199335
0.9245	High Similarity	NPC473202
0.9236	High Similarity	NPC278419
0.9236	High Similarity	NPC124155
0.9236	High Similarity	NPC66087
0.9236	High Similarity	NPC179198
0.9236	High Similarity	NPC257566
0.9231	High Similarity	NPC47923
0.9226	High Similarity	NPC73511
0.9226	High Similarity	NPC43761
0.9221	High Similarity	NPC149368
0.9221	High Similarity	NPC265480
0.9216	High Similarity	NPC106625
0.9205	High Similarity	NPC88886
0.9205	High Similarity	NPC307052
0.9205	High Similarity	NPC139966
0.9205	High Similarity	NPC104172
0.92	High Similarity	NPC218685
0.92	High Similarity	NPC23084
0.92	High Similarity	NPC202494
0.92	High Similarity	NPC85773
0.9172	High Similarity	NPC150164
0.9172	High Similarity	NPC259834
0.9167	High Similarity	NPC472320
0.9167	High Similarity	NPC200708
0.9161	High Similarity	NPC156457
0.9161	High Similarity	NPC313163
0.9161	High Similarity	NPC258035
0.9161	High Similarity	NPC161749
0.9161	High Similarity	NPC197896
0.9156	High Similarity	NPC27408
0.9156	High Similarity	NPC99233
0.9156	High Similarity	NPC95090
0.915	High Similarity	NPC259182
0.915	High Similarity	NPC256141
0.915	High Similarity	NPC121001
0.9133	High Similarity	NPC469700
0.9114	High Similarity	NPC471286
0.9108	High Similarity	NPC303913
0.9097	High Similarity	NPC206378
0.9097	High Similarity	NPC261866
0.9097	High Similarity	NPC473657
0.9097	High Similarity	NPC295613
0.9097	High Similarity	NPC127406
0.9091	High Similarity	NPC143851
0.9091	High Similarity	NPC29763
0.9091	High Similarity	NPC83283
0.9091	High Similarity	NPC210003
0.9091	High Similarity	NPC39360
0.9085	High Similarity	NPC250488
0.9085	High Similarity	NPC472636
0.9085	High Similarity	NPC471675
0.908	High Similarity	NPC325176
0.9073	High Similarity	NPC91902
0.9073	High Similarity	NPC47388
0.9073	High Similarity	NPC473133
0.9073	High Similarity	NPC470670
0.9067	High Similarity	NPC474044
0.9067	High Similarity	NPC297788
0.9057	High Similarity	NPC294722
0.9057	High Similarity	NPC72016
0.9051	High Similarity	NPC190450
0.9051	High Similarity	NPC125991
0.9045	High Similarity	NPC110349
0.9045	High Similarity	NPC306978
0.9038	High Similarity	NPC60966
0.9038	High Similarity	NPC6985
0.9038	High Similarity	NPC473512
0.9038	High Similarity	NPC43638
0.9038	High Similarity	NPC182634
0.9038	High Similarity	NPC129827
0.9038	High Similarity	NPC65003
0.9038	High Similarity	NPC288084
0.9038	High Similarity	NPC108831
0.9038	High Similarity	NPC44931
0.9032	High Similarity	NPC72649
0.9032	High Similarity	NPC97052
0.9032	High Similarity	NPC39351
0.9032	High Similarity	NPC169248
0.9032	High Similarity	NPC26195
0.9026	High Similarity	NPC285623
0.9026	High Similarity	NPC327269
0.9026	High Similarity	NPC259767
0.9026	High Similarity	NPC10807
0.9026	High Similarity	NPC161881
0.9026	High Similarity	NPC56232
0.9026	High Similarity	NPC150123
0.9026	High Similarity	NPC244583
0.9026	High Similarity	NPC31627
0.9026	High Similarity	NPC473996
0.9026	High Similarity	NPC88484
0.9026	High Similarity	NPC476238
0.902	High Similarity	NPC180351
0.9012	High Similarity	NPC235575
0.9006	High Similarity	NPC259905
0.9006	High Similarity	NPC5319
0.9	High Similarity	NPC178851
0.8987	High Similarity	NPC182045
0.8981	High Similarity	NPC138811
0.8981	High Similarity	NPC41121
0.8981	High Similarity	NPC111929
0.8981	High Similarity	NPC473634
0.8981	High Similarity	NPC22062
0.8981	High Similarity	NPC279732
0.8981	High Similarity	NPC320283
0.8981	High Similarity	NPC50430
0.8981	High Similarity	NPC308265
0.8981	High Similarity	NPC472459
0.8974	High Similarity	NPC203500
0.8974	High Similarity	NPC170475
0.8974	High Similarity	NPC323593
0.8974	High Similarity	NPC307938
0.8968	High Similarity	NPC472583
0.8968	High Similarity	NPC223701
0.8968	High Similarity	NPC7989
0.8968	High Similarity	NPC469405
0.8963	High Similarity	NPC475233
0.8961	High Similarity	NPC472580
0.8961	High Similarity	NPC244577
0.8961	High Similarity	NPC474744
0.8961	High Similarity	NPC209846
0.8961	High Similarity	NPC477897
0.8961	High Similarity	NPC263384
0.8961	High Similarity	NPC289774
0.8961	High Similarity	NPC471677
0.8961	High Similarity	NPC474021
0.8961	High Similarity	NPC474023
0.8961	High Similarity	NPC318424
0.8961	High Similarity	NPC474772
0.8961	High Similarity	NPC472423
0.8961	High Similarity	NPC472422
0.8961	High Similarity	NPC471676
0.8961	High Similarity	NPC472420
0.8961	High Similarity	NPC328740
0.8957	High Similarity	NPC98776
0.8951	High Similarity	NPC78734
0.8951	High Similarity	NPC76047
0.8951	High Similarity	NPC212748
0.8951	High Similarity	NPC150767
0.8944	High Similarity	NPC477502
0.894	High Similarity	NPC294365
0.894	High Similarity	NPC171656
0.8938	High Similarity	NPC475979
0.8931	High Similarity	NPC300537
0.8931	High Similarity	NPC473043
0.8931	High Similarity	NPC127782
0.8924	High Similarity	NPC19554
0.8924	High Similarity	NPC43971
0.8924	High Similarity	NPC153342
0.8924	High Similarity	NPC142860
0.8924	High Similarity	NPC473623
0.8924	High Similarity	NPC246469
0.8924	High Similarity	NPC271479
0.8924	High Similarity	NPC271270
0.8924	High Similarity	NPC74749
0.8924	High Similarity	NPC97285
0.8924	High Similarity	NPC187379
0.8917	High Similarity	NPC78263
0.8917	High Similarity	NPC197304
0.8917	High Similarity	NPC77672
0.8917	High Similarity	NPC135391
0.8917	High Similarity	NPC133671
0.8917	High Similarity	NPC54802
0.8917	High Similarity	NPC210048
0.891	High Similarity	NPC304207
0.891	High Similarity	NPC207809
0.891	High Similarity	NPC111341
0.891	High Similarity	NPC217706
0.891	High Similarity	NPC87404
0.891	High Similarity	NPC470681
0.891	High Similarity	NPC259710
0.891	High Similarity	NPC279218

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 NPC17521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	915
0.2-0.3	1799
0.3-0.4	2703
0.4-0.5	1948
0.5-0.6	985
0.6-0.7	293
0.7-0.8	141
0.8-0.85	21
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9161	High Similarity	NPD4381	Clinical (unspecified phase)
0.9006	High Similarity	NPD7804	Clinical (unspecified phase)
0.8827	High Similarity	NPD3818	Discontinued
0.8774	High Similarity	NPD4380	Phase 2
0.8727	High Similarity	NPD6559	Discontinued
0.8659	High Similarity	NPD7054	Approved
0.8608	High Similarity	NPD7096	Clinical (unspecified phase)
0.8606	High Similarity	NPD7472	Approved
0.8606	High Similarity	NPD7074	Phase 3
0.8562	High Similarity	NPD7075	Discontinued
0.8554	High Similarity	NPD6797	Phase 2
0.8544	High Similarity	NPD6801	Discontinued
0.8503	High Similarity	NPD7251	Discontinued
0.8491	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7808	Phase 3
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD1934	Approved
0.8289	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD7819	Suspended
0.825	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD1549	Phase 2
0.8153	Intermediate Similarity	NPD6799	Approved
0.8144	Intermediate Similarity	NPD6166	Phase 2
0.8144	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD2801	Approved
0.8013	Intermediate Similarity	NPD2800	Approved
0.8013	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD920	Approved
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7987	Intermediate Similarity	NPD5401	Approved
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7939	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3882	Suspended
0.7925	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD7584	Approved
0.7879	Intermediate Similarity	NPD5402	Approved
0.7875	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.7865	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1512	Approved
0.7824	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8455	Phase 2
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7199	Phase 2
0.7738	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD1240	Approved
0.7722	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7679	Intermediate Similarity	NPD3749	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD8312	Approved
0.7651	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD1247	Approved
0.7628	Intermediate Similarity	NPD1607	Approved
0.7628	Intermediate Similarity	NPD6651	Approved
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD1653	Approved
0.7619	Intermediate Similarity	NPD4965	Approved
0.7619	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7614	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2424	Discontinued
0.7602	Intermediate Similarity	NPD3787	Discontinued
0.7602	Intermediate Similarity	NPD6232	Discontinued
0.76	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7568	Intermediate Similarity	NPD6776	Approved
0.7568	Intermediate Similarity	NPD6778	Approved
0.7568	Intermediate Similarity	NPD6782	Approved
0.7568	Intermediate Similarity	NPD6781	Approved
0.7568	Intermediate Similarity	NPD6780	Approved
0.7568	Intermediate Similarity	NPD6779	Approved
0.7568	Intermediate Similarity	NPD6777	Approved
0.7564	Intermediate Similarity	NPD5124	Phase 1
0.7564	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7529	Intermediate Similarity	NPD7228	Approved
0.7516	Intermediate Similarity	NPD3750	Approved
0.7513	Intermediate Similarity	NPD7583	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7474	Intermediate Similarity	NPD7585	Approved
0.7467	Intermediate Similarity	NPD1091	Approved
0.7453	Intermediate Similarity	NPD1652	Phase 2
0.7447	Intermediate Similarity	NPD7435	Discontinued
0.7435	Intermediate Similarity	NPD8151	Discontinued
0.7421	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7399	Intermediate Similarity	NPD5711	Approved
0.7399	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1551	Phase 2
0.7375	Intermediate Similarity	NPD2935	Discontinued
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.736	Intermediate Similarity	NPD7240	Approved
0.736	Intermediate Similarity	NPD7685	Pre-registration
0.7358	Intermediate Similarity	NPD7783	Phase 2
0.7358	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3926	Phase 2
0.7354	Intermediate Similarity	NPD7698	Approved
0.7354	Intermediate Similarity	NPD7697	Approved
0.7354	Intermediate Similarity	NPD7696	Phase 3
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7346	Intermediate Similarity	NPD2654	Approved
0.7342	Intermediate Similarity	NPD1933	Approved
0.7338	Intermediate Similarity	NPD2798	Approved
0.7317	Intermediate Similarity	NPD5058	Phase 3
0.7316	Intermediate Similarity	NPD7870	Phase 2
0.7316	Intermediate Similarity	NPD7871	Phase 2
0.7314	Intermediate Similarity	NPD2403	Approved
0.7302	Intermediate Similarity	NPD6823	Phase 2
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6535	Approved
0.7297	Intermediate Similarity	NPD4363	Phase 3
0.7297	Intermediate Similarity	NPD4360	Phase 2
0.7297	Intermediate Similarity	NPD6534	Approved
0.7294	Intermediate Similarity	NPD1465	Phase 2
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7701	Phase 2
0.7288	Intermediate Similarity	NPD7286	Phase 2
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD6099	Approved
0.7262	Intermediate Similarity	NPD3226	Approved
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7237	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2346	Discontinued
0.7222	Intermediate Similarity	NPD2344	Approved
0.7216	Intermediate Similarity	NPD7874	Approved
0.7216	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7700	Phase 2
0.7181	Intermediate Similarity	NPD7699	Phase 2
0.7179	Intermediate Similarity	NPD7801	Approved
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1613	Approved
0.7166	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4361	Phase 2
0.7157	Intermediate Similarity	NPD7930	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7134	Intermediate Similarity	NPD6674	Discontinued
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD230	Phase 1
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7117	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6004	Phase 3
0.7117	Intermediate Similarity	NPD6005	Phase 3
0.7117	Intermediate Similarity	NPD6002	Phase 3
0.7117	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.7078	Intermediate Similarity	NPD9717	Approved
0.7066	Intermediate Similarity	NPD7390	Discontinued
0.7048	Intermediate Similarity	NPD2309	Approved
0.7047	Intermediate Similarity	NPD8319	Approved
0.7047	Intermediate Similarity	NPD8320	Phase 1
0.7044	Intermediate Similarity	NPD3268	Approved
0.7029	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4908	Phase 1
0.7022	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD447	Suspended
0.7017	Intermediate Similarity	NPD3823	Discontinued
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6994	Remote Similarity	NPD5761	Phase 2
0.6994	Remote Similarity	NPD4308	Phase 3
0.6994	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5760	Phase 2
0.6973	Remote Similarity	NPD8150	Discontinued
0.6968	Remote Similarity	NPD6212	Phase 3
0.6968	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6213	Phase 3
0.6962	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1729	Discontinued
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD943	Approved
0.6944	Remote Similarity	NPD7893	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