NPASS Compound

Structure

CID134819 OpenBabel06191715492D 27 29 0 0 1 0 0 0 0 0999 V2000 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 1.5000 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 -1.5000 0.0000 C 0 0 0 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 1.7321 1.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 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 3.4641 1.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -0.0000 1.0000 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 7 1 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 12 2 0 0 0 0 5 10 1 0 0 0 0 5 11 2 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 8 25 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 21 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 25 1 6 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.13
Volume:	360.145
LogP:	0.82
LogD:	0.724
LogS:	-2.935
# Rotatable Bonds:	4
TPSA:	149.82
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	3.937
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.873
MDCK Permeability:	2.4308834326802753e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.847
Human Intestinal Absorption (HIA):	0.218
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.79

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	85.4137954711914%
Volume Distribution (VD):	1.0
Pgp-substrate:	12.07064437866211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.226
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.401
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.446
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	1.776
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.627
AMES Toxicity:	0.686
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.451
Carcinogencity:	0.266
Eye Corrosion:	0.003
Eye Irritation:	0.128
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC134819

Natural Product ID:	NPC134819
*Common Name:**	Urachromone A
IUPAC Name:	5-hydroxy-2-propan-2-yl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Urachromone A
Standard InCHIKey:	SSCRSMIEYROIGW-SOVHRIKKSA-N
Standard InCHI:	InChI=1S/C18H22O9/c1-7(2)11-5-10(21)14-9(20)3-8(4-12(14)26-11)25-18-17(24)16(23)15(22)13(6-19)27-18/h3-5,7,13,15-20,22-24H,6H2,1-2H3/t13-,15-,16+,17-,18-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)C(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2164955
PubChem CID:	25243498
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757709]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO3784	Saccharopolyspora spinosa	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18345667]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23078294]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23513740]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5633	Osyris abyssinica	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO40	Ostryopsis davidiana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1889	Panorpa japonica	Species	Panorpidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6594	Hypericum sikokumontanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3784	Saccharopolyspora spinosa	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4698	Polymnia uvedalia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO969	Streptomyces setonensis	Species	Streptomycetaceae	Bacteria	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
EC50	1
IC50	1
Others	9

Activity Type	# Activity
Cell Line	1
Organism	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	69.5	ug.mL-1	PMID[568550]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	31.03	n.a.	PMID[568550]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2.24	ug.mL-1	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	13.7	%	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	156400.0	nM	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	50.9	%	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.7	%	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	22.4	%	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	8.11	%	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	4.76	%	PMID[568550]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	11.5	%	PMID[568550]

☑ 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 NPC134819 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	373
0.1-0.2	1489
0.2-0.3	3557
0.3-0.4	8750
0.4-0.5	10041
0.5-0.6	4370
0.6-0.7	5623
0.7-0.8	5257
0.8-0.85	2390
0.85-0.9	672
0.9-0.95	160
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC191154
0.9793	High Similarity	NPC106025
0.9793	High Similarity	NPC477240
0.9793	High Similarity	NPC214454
0.9792	High Similarity	NPC199335
0.9728	High Similarity	NPC78021
0.9728	High Similarity	NPC268950
0.9728	High Similarity	NPC108706
0.9728	High Similarity	NPC87304
0.9728	High Similarity	NPC211158
0.9726	High Similarity	NPC190217
0.9722	High Similarity	NPC23084
0.9662	High Similarity	NPC470603
0.9662	High Similarity	NPC95090
0.9662	High Similarity	NPC470604
0.9662	High Similarity	NPC27408
0.9662	High Similarity	NPC470605
0.9595	High Similarity	NPC39360
0.9595	High Similarity	NPC106625
0.9595	High Similarity	NPC29763
0.9595	High Similarity	NPC143851
0.9595	High Similarity	NPC83283
0.9595	High Similarity	NPC210003
0.9536	High Similarity	NPC473623
0.9533	High Similarity	NPC470606
0.9533	High Similarity	NPC108831
0.9533	High Similarity	NPC129827
0.9533	High Similarity	NPC60966
0.9533	High Similarity	NPC182634
0.9533	High Similarity	NPC44931
0.9533	High Similarity	NPC65003
0.9533	High Similarity	NPC473512
0.953	High Similarity	NPC99233
0.9527	High Similarity	NPC259182
0.9527	High Similarity	NPC88484
0.9527	High Similarity	NPC259767
0.9527	High Similarity	NPC121001
0.9524	High Similarity	NPC213723
0.9524	High Similarity	NPC38775
0.947	High Similarity	NPC41121
0.947	High Similarity	NPC473634
0.947	High Similarity	NPC470607
0.947	High Similarity	NPC472459
0.947	High Similarity	NPC73511
0.947	High Similarity	NPC320283
0.947	High Similarity	NPC22062
0.947	High Similarity	NPC138811
0.947	High Similarity	NPC111929
0.9467	High Similarity	NPC127406
0.9467	High Similarity	NPC307938
0.9467	High Similarity	NPC203500
0.9467	High Similarity	NPC323593
0.9467	High Similarity	NPC261866
0.9467	High Similarity	NPC206378
0.9452	High Similarity	NPC218685
0.9408	High Similarity	NPC187379
0.9404	High Similarity	NPC133671
0.9404	High Similarity	NPC54802
0.9404	High Similarity	NPC161749
0.9404	High Similarity	NPC197896
0.9404	High Similarity	NPC313163
0.9404	High Similarity	NPC258035
0.9404	High Similarity	NPC77672
0.9404	High Similarity	NPC78263
0.9404	High Similarity	NPC156457
0.9404	High Similarity	NPC23817
0.9404	High Similarity	NPC135391
0.9404	High Similarity	NPC197304
0.9404	High Similarity	NPC6985
0.9404	High Similarity	NPC43638
0.9404	High Similarity	NPC122809
0.94	High Similarity	NPC97052
0.94	High Similarity	NPC39351
0.94	High Similarity	NPC26195
0.94	High Similarity	NPC72649
0.94	High Similarity	NPC169248
0.9351	High Similarity	NPC473644
0.9346	High Similarity	NPC163242
0.9346	High Similarity	NPC215710
0.9346	High Similarity	NPC224530
0.9346	High Similarity	NPC216496
0.9346	High Similarity	NPC116458
0.9346	High Similarity	NPC173582
0.9346	High Similarity	NPC101636
0.9346	High Similarity	NPC276377
0.9346	High Similarity	NPC85707
0.9346	High Similarity	NPC303913
0.9346	High Similarity	NPC259957
0.9346	High Similarity	NPC473438
0.9346	High Similarity	NPC249281
0.9346	High Similarity	NPC129217
0.9346	High Similarity	NPC246943
0.9346	High Similarity	NPC265885
0.9346	High Similarity	NPC159579
0.9346	High Similarity	NPC48093
0.9346	High Similarity	NPC253788
0.9346	High Similarity	NPC139320
0.9346	High Similarity	NPC181465
0.9346	High Similarity	NPC476215
0.9342	High Similarity	NPC308265
0.9338	High Similarity	NPC149368
0.9338	High Similarity	NPC295613
0.9338	High Similarity	NPC473657
0.9338	High Similarity	NPC170475
0.9338	High Similarity	NPC45165
0.9338	High Similarity	NPC17521
0.9338	High Similarity	NPC265480
0.9329	High Similarity	NPC23253
0.9324	High Similarity	NPC139966
0.9324	High Similarity	NPC307052
0.929	High Similarity	NPC294722
0.9286	High Similarity	NPC150164
0.9286	High Similarity	NPC131745
0.9286	High Similarity	NPC473043
0.9286	High Similarity	NPC298171
0.9286	High Similarity	NPC27942
0.9286	High Similarity	NPC44947
0.9286	High Similarity	NPC475382
0.9286	High Similarity	NPC240306
0.9281	High Similarity	NPC97285
0.9281	High Similarity	NPC271270
0.9281	High Similarity	NPC142860
0.9281	High Similarity	NPC136761
0.9281	High Similarity	NPC470405
0.9281	High Similarity	NPC471079
0.9281	High Similarity	NPC304741
0.9281	High Similarity	NPC153342
0.9281	High Similarity	NPC246469
0.9281	High Similarity	NPC271479
0.9276	High Similarity	NPC288084
0.9257	High Similarity	NPC10097
0.9226	High Similarity	NPC94777
0.9226	High Similarity	NPC19709
0.9226	High Similarity	NPC278419
0.9226	High Similarity	NPC179198
0.9226	High Similarity	NPC183672
0.9226	High Similarity	NPC222936
0.9226	High Similarity	NPC284960
0.9226	High Similarity	NPC309025
0.9226	High Similarity	NPC257566
0.9226	High Similarity	NPC121703
0.9226	High Similarity	NPC124155
0.9226	High Similarity	NPC311850
0.9226	High Similarity	NPC243930
0.9226	High Similarity	NPC66087
0.9226	High Similarity	NPC88023
0.9221	High Similarity	NPC64305
0.9221	High Similarity	NPC195685
0.9221	High Similarity	NPC135846
0.9221	High Similarity	NPC477629
0.9221	High Similarity	NPC210961
0.9221	High Similarity	NPC472994
0.9221	High Similarity	NPC477628
0.9221	High Similarity	NPC47923
0.9221	High Similarity	NPC297987
0.9221	High Similarity	NPC282169
0.9221	High Similarity	NPC270675
0.9221	High Similarity	NPC470125
0.9221	High Similarity	NPC170052
0.9216	High Similarity	NPC43761
0.9216	High Similarity	NPC104677
0.9167	High Similarity	NPC135358
0.9167	High Similarity	NPC475979
0.9167	High Similarity	NPC22832
0.9167	High Similarity	NPC311830
0.9167	High Similarity	NPC287889
0.9167	High Similarity	NPC139060
0.9167	High Similarity	NPC72016
0.9161	High Similarity	NPC189142
0.9161	High Similarity	NPC77660
0.9161	High Similarity	NPC300537
0.9161	High Similarity	NPC190450
0.9161	High Similarity	NPC259834
0.9161	High Similarity	NPC127782
0.9156	High Similarity	NPC200708
0.9156	High Similarity	NPC110349
0.9156	High Similarity	NPC472320
0.9108	High Similarity	NPC203145
0.9108	High Similarity	NPC189564
0.9108	High Similarity	NPC11432
0.9108	High Similarity	NPC32641
0.9108	High Similarity	NPC68592
0.9108	High Similarity	NPC115674
0.9108	High Similarity	NPC64425
0.9108	High Similarity	NPC135599
0.9108	High Similarity	NPC186816
0.9108	High Similarity	NPC99957
0.9108	High Similarity	NPC181616
0.9108	High Similarity	NPC262222
0.9108	High Similarity	NPC113968
0.9108	High Similarity	NPC277174
0.9108	High Similarity	NPC73855
0.9108	High Similarity	NPC221342
0.9108	High Similarity	NPC477613
0.9108	High Similarity	NPC142142
0.9108	High Similarity	NPC12013
0.9108	High Similarity	NPC476470
0.9108	High Similarity	NPC298666
0.9108	High Similarity	NPC256188
0.9108	High Similarity	NPC210073

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 NPC134819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	869
0.2-0.3	1781
0.3-0.4	2680
0.4-0.5	1975
0.5-0.6	1039
0.6-0.7	311
0.7-0.8	130
0.8-0.85	27
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9404	High Similarity	NPD4381	Clinical (unspecified phase)
0.8994	High Similarity	NPD7804	Clinical (unspecified phase)
0.8994	High Similarity	NPD7054	Approved
0.8938	High Similarity	NPD7472	Approved
0.8882	High Similarity	NPD6797	Phase 2
0.8827	High Similarity	NPD7251	Discontinued
0.882	High Similarity	NPD7074	Phase 3
0.8812	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD7808	Phase 3
0.8758	High Similarity	NPD4380	Phase 2
0.8659	High Similarity	NPD4338	Clinical (unspecified phase)
0.8581	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD1552	Clinical (unspecified phase)
0.8544	High Similarity	NPD7075	Discontinued
0.8526	High Similarity	NPD1934	Approved
0.8526	High Similarity	NPD6801	Discontinued
0.8523	High Similarity	NPD1549	Phase 2
0.8485	Intermediate Similarity	NPD6559	Discontinued
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6799	Approved
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD2801	Approved
0.8344	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD5403	Approved
0.8302	Intermediate Similarity	NPD3817	Phase 2
0.8302	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD1511	Approved
0.8228	Intermediate Similarity	NPD7411	Suspended
0.82	Intermediate Similarity	NPD1510	Phase 2
0.8194	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD5401	Approved
0.817	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1512	Approved
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD5402	Approved
0.8054	Intermediate Similarity	NPD1240	Approved
0.805	Intermediate Similarity	NPD6599	Discontinued
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7947	Intermediate Similarity	NPD1607	Approved
0.7939	Intermediate Similarity	NPD6959	Discontinued
0.7925	Intermediate Similarity	NPD1653	Approved
0.7829	Intermediate Similarity	NPD6651	Approved
0.78	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1091	Approved
0.7778	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7584	Approved
0.7771	Intermediate Similarity	NPD5494	Approved
0.7756	Intermediate Similarity	NPD2800	Approved
0.7746	Intermediate Similarity	NPD8312	Approved
0.7746	Intermediate Similarity	NPD8313	Approved
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7707	Intermediate Similarity	NPD3750	Approved
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7647	Intermediate Similarity	NPD7473	Discontinued
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1652	Phase 2
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7602	Intermediate Similarity	NPD3751	Discontinued
0.759	Intermediate Similarity	NPD7768	Phase 2
0.7576	Intermediate Similarity	NPD8455	Phase 2
0.7574	Intermediate Similarity	NPD6232	Discontinued
0.7574	Intermediate Similarity	NPD3787	Discontinued
0.7558	Intermediate Similarity	NPD5844	Phase 1
0.7545	Intermediate Similarity	NPD3749	Approved
0.7532	Intermediate Similarity	NPD5124	Phase 1
0.7532	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1243	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7531	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD7685	Pre-registration
0.7515	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD7228	Approved
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7473	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1465	Phase 2
0.7452	Intermediate Similarity	NPD6099	Approved
0.7452	Intermediate Similarity	NPD6100	Approved
0.7446	Intermediate Similarity	NPD6776	Approved
0.7446	Intermediate Similarity	NPD6780	Approved
0.7446	Intermediate Similarity	NPD6778	Approved
0.7446	Intermediate Similarity	NPD6782	Approved
0.7446	Intermediate Similarity	NPD6777	Approved
0.7446	Intermediate Similarity	NPD6781	Approved
0.7446	Intermediate Similarity	NPD6779	Approved
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7432	Intermediate Similarity	NPD422	Phase 1
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD2798	Approved
0.7407	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8151	Discontinued
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3748	Approved
0.7383	Intermediate Similarity	NPD9717	Approved
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7363	Intermediate Similarity	NPD4363	Phase 3
0.7363	Intermediate Similarity	NPD4360	Phase 2
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7355	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7585	Approved
0.7351	Intermediate Similarity	NPD1203	Approved
0.7342	Intermediate Similarity	NPD2935	Discontinued
0.7338	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.7326	Intermediate Similarity	NPD7435	Discontinued
0.732	Intermediate Similarity	NPD4908	Phase 1
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2654	Approved
0.7302	Intermediate Similarity	NPD7583	Approved
0.7294	Intermediate Similarity	NPD919	Approved
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7246	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7783	Phase 2
0.7239	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2797	Approved
0.7234	Intermediate Similarity	NPD7697	Approved
0.7234	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7226	Intermediate Similarity	NPD2313	Discontinued
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7209	Intermediate Similarity	NPD1247	Approved
0.72	Intermediate Similarity	NPD1610	Phase 2
0.7197	Intermediate Similarity	NPD447	Suspended
0.7196	Intermediate Similarity	NPD7871	Phase 2
0.7196	Intermediate Similarity	NPD7870	Phase 2
0.7195	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7266	Discontinued
0.7188	Intermediate Similarity	NPD2344	Approved
0.7184	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6823	Phase 2
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.7174	Intermediate Similarity	NPD6534	Approved
0.7174	Intermediate Similarity	NPD6535	Approved
0.7173	Intermediate Similarity	NPD7701	Phase 2
0.7168	Intermediate Similarity	NPD5711	Approved
0.7168	Intermediate Similarity	NPD5710	Approved
0.7167	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD9545	Approved
0.715	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7135	Intermediate Similarity	NPD7240	Approved
0.7134	Intermediate Similarity	NPD943	Approved
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7126	Intermediate Similarity	NPD3926	Phase 2
0.7126	Intermediate Similarity	NPD3226	Approved
0.7107	Intermediate Similarity	NPD7097	Phase 1
0.7098	Intermediate Similarity	NPD7874	Approved
0.7098	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD2403	Approved
0.7078	Intermediate Similarity	NPD5647	Approved
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.7059	Intermediate Similarity	NPD7700	Phase 2
0.7059	Intermediate Similarity	NPD7699	Phase 2
0.7059	Intermediate Similarity	NPD3225	Approved
0.7051	Intermediate Similarity	NPD3027	Phase 3
0.7043	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4361	Phase 2
0.703	Intermediate Similarity	NPD7390	Discontinued
0.7027	Intermediate Similarity	NPD9493	Approved
0.7018	Intermediate Similarity	NPD5353	Approved
0.7016	Intermediate Similarity	NPD8319	Approved
0.7016	Intermediate Similarity	NPD8320	Phase 1
0.7013	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD3267	Approved
0.7012	Intermediate Similarity	NPD6190	Approved
0.7012	Intermediate Similarity	NPD2309	Approved
0.7006	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6844	Discontinued
0.6994	Remote Similarity	NPD6674	Discontinued
0.6993	Remote Similarity	NPD4749	Approved
0.6988	Remote Similarity	NPD4661	Approved
0.6988	Remote Similarity	NPD4662	Approved
0.6981	Remote Similarity	NPD1899	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