NPASS Compound

Structure

NPC47286 OpenBabel07101719242D 29 31 0 0 1 0 0 0 0 0999 V2000 7.8988 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 -1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -1.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 0.0055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 0.5055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 0.0055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8366 -2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2007 -0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 0.5055 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 3.5686 -0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 26 1 0 0 0 0 8 20 1 0 0 0 0 9 19 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 10 27 1 0 0 0 0 12 8 1 6 0 0 0 12 15 1 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 6 0 0 0 14 17 1 0 0 0 0 14 23 1 1 0 0 0 15 29 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 16 24 1 0 0 0 0 17 26 1 6 0 0 0 17 28 1 0 0 0 0 18 27 1 0 0 0 0 18 29 1 1 0 0 0 19 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.17
Volume:	391.504
LogP:	-0.367
LogD:	-1.085
LogS:	-2.096
# Rotatable Bonds:	8
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	4.229
Fsp3:	0.684
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:	-5.904
MDCK Permeability:	3.4698132367338985e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.784
Human Intestinal Absorption (HIA):	0.969
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	39.04497528076172%
Volume Distribution (VD):	0.359
Pgp-substrate:	39.38594055175781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	1.26
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.319
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.182
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.849
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.061
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC47286

Natural Product ID:	NPC47286
*Common Name:**	Phenylethyl-1-O-Beta-D-Apiofuranosyl-(1->4)-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3R,4R,5S,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)-2-(2-phenylethoxy)oxane-3,4-diol
Synonyms:
Standard InCHIKey:	YSMFIJDRMWRYKD-DXGCKQMKSA-N
Standard InCHI:	InChI=1S/C19H28O10/c20-8-12-15(29-18-16(24)19(25,9-21)10-27-18)13(22)14(23)17(28-12)26-7-6-11-4-2-1-3-5-11/h1-5,12-18,20-25H,6-10H2/t12-,13-,14-,15-,16+,17-,18+,19-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OCCc2ccccc2)[C@@H]([C@H]([C@@H]1O[C@@H]1OC[C@]([C@H]1O)(O)CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087813
PubChem CID:	44178762
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:0002207] O-glycosyl compounds

*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
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	710000.0	nM	PMID[550798]

☑ 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 NPC47286 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	201
0.1-0.2	932
0.2-0.3	2504
0.3-0.4	8228
0.4-0.5	17303
0.5-0.6	11008
0.6-0.7	2284
0.7-0.8	210
0.8-0.85	19
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC262826
0.9223	High Similarity	NPC264784
0.8762	High Similarity	NPC474148
0.8762	High Similarity	NPC276061
0.8738	High Similarity	NPC152384
0.8738	High Similarity	NPC37714
0.8725	High Similarity	NPC469527
0.8679	High Similarity	NPC30563
0.8641	High Similarity	NPC148060
0.8505	High Similarity	NPC43584
0.8496	Intermediate Similarity	NPC476445
0.8496	Intermediate Similarity	NPC469548
0.8496	Intermediate Similarity	NPC476448
0.8407	Intermediate Similarity	NPC469702
0.8407	Intermediate Similarity	NPC282409
0.8333	Intermediate Similarity	NPC229600
0.8318	Intermediate Similarity	NPC184633
0.8304	Intermediate Similarity	NPC266389
0.8304	Intermediate Similarity	NPC216605
0.8304	Intermediate Similarity	NPC122245
0.8276	Intermediate Similarity	NPC178449
0.8276	Intermediate Similarity	NPC470907
0.8276	Intermediate Similarity	NPC232454
0.8273	Intermediate Similarity	NPC120217
0.8214	Intermediate Similarity	NPC148055
0.8198	Intermediate Similarity	NPC157338
0.819	Intermediate Similarity	NPC471067
0.8136	Intermediate Similarity	NPC90318
0.8108	Intermediate Similarity	NPC474641
0.8091	Intermediate Similarity	NPC470825
0.8051	Intermediate Similarity	NPC287429
0.8036	Intermediate Similarity	NPC29607
0.8017	Intermediate Similarity	NPC469703
0.8017	Intermediate Similarity	NPC469704
0.8017	Intermediate Similarity	NPC160854
0.8017	Intermediate Similarity	NPC201402
0.8	Intermediate Similarity	NPC469687
0.7983	Intermediate Similarity	NPC470510
0.7949	Intermediate Similarity	NPC469686
0.7949	Intermediate Similarity	NPC55608
0.7899	Intermediate Similarity	NPC244454
0.7895	Intermediate Similarity	NPC175771
0.7876	Intermediate Similarity	NPC313193
0.7797	Intermediate Similarity	NPC266045
0.775	Intermediate Similarity	NPC145287
0.775	Intermediate Similarity	NPC57607
0.775	Intermediate Similarity	NPC317163
0.7742	Intermediate Similarity	NPC478255
0.7731	Intermediate Similarity	NPC476142
0.7712	Intermediate Similarity	NPC469412
0.7712	Intermediate Similarity	NPC198734
0.7692	Intermediate Similarity	NPC14950
0.7627	Intermediate Similarity	NPC60589
0.7627	Intermediate Similarity	NPC469708
0.7623	Intermediate Similarity	NPC267733
0.7623	Intermediate Similarity	NPC276047
0.7619	Intermediate Similarity	NPC164172
0.7583	Intermediate Similarity	NPC141970
0.7583	Intermediate Similarity	NPC52097
0.7583	Intermediate Similarity	NPC140561
0.7581	Intermediate Similarity	NPC469549
0.7581	Intermediate Similarity	NPC11025
0.7563	Intermediate Similarity	NPC269242
0.7561	Intermediate Similarity	NPC79715
0.7561	Intermediate Similarity	NPC175333
0.7561	Intermediate Similarity	NPC264900
0.7561	Intermediate Similarity	NPC156692
0.7561	Intermediate Similarity	NPC108659
0.7561	Intermediate Similarity	NPC471882
0.7561	Intermediate Similarity	NPC471881
0.7561	Intermediate Similarity	NPC173150
0.7561	Intermediate Similarity	NPC45224
0.7561	Intermediate Similarity	NPC231607
0.7561	Intermediate Similarity	NPC35288
0.7561	Intermediate Similarity	NPC288416
0.7559	Intermediate Similarity	NPC470881
0.7541	Intermediate Similarity	NPC123704
0.754	Intermediate Similarity	NPC471066
0.754	Intermediate Similarity	NPC471095
0.7521	Intermediate Similarity	NPC212176
0.752	Intermediate Similarity	NPC17567
0.75	Intermediate Similarity	NPC301857
0.75	Intermediate Similarity	NPC225307
0.75	Intermediate Similarity	NPC266343
0.75	Intermediate Similarity	NPC148982
0.75	Intermediate Similarity	NPC226712
0.75	Intermediate Similarity	NPC11724
0.748	Intermediate Similarity	NPC25821
0.748	Intermediate Similarity	NPC252114
0.748	Intermediate Similarity	NPC114096
0.748	Intermediate Similarity	NPC6836
0.748	Intermediate Similarity	NPC94179
0.748	Intermediate Similarity	NPC61181
0.746	Intermediate Similarity	NPC475824
0.7459	Intermediate Similarity	NPC87153
0.7459	Intermediate Similarity	NPC162925
0.7456	Intermediate Similarity	NPC185840
0.744	Intermediate Similarity	NPC184092
0.7431	Intermediate Similarity	NPC154905
0.7431	Intermediate Similarity	NPC60373
0.7419	Intermediate Similarity	NPC106677
0.7419	Intermediate Similarity	NPC148026
0.7419	Intermediate Similarity	NPC103533
0.7417	Intermediate Similarity	NPC476872
0.7402	Intermediate Similarity	NPC252833
0.7402	Intermediate Similarity	NPC473924
0.7398	Intermediate Similarity	NPC77651
0.7398	Intermediate Similarity	NPC126991
0.7398	Intermediate Similarity	NPC83218
0.7398	Intermediate Similarity	NPC28069
0.7385	Intermediate Similarity	NPC469696
0.7381	Intermediate Similarity	NPC472024
0.7381	Intermediate Similarity	NPC80600
0.7381	Intermediate Similarity	NPC289415
0.7381	Intermediate Similarity	NPC474491
0.7381	Intermediate Similarity	NPC470122
0.7381	Intermediate Similarity	NPC469705
0.7381	Intermediate Similarity	NPC17968
0.7381	Intermediate Similarity	NPC319995
0.7377	Intermediate Similarity	NPC138798
0.7374	Intermediate Similarity	NPC121478
0.7374	Intermediate Similarity	NPC73637
0.736	Intermediate Similarity	NPC158673
0.7344	Intermediate Similarity	NPC254398
0.7339	Intermediate Similarity	NPC92283
0.7339	Intermediate Similarity	NPC10883
0.7339	Intermediate Similarity	NPC35338
0.7339	Intermediate Similarity	NPC198918
0.7339	Intermediate Similarity	NPC204214
0.7339	Intermediate Similarity	NPC10121
0.7339	Intermediate Similarity	NPC124878
0.7339	Intermediate Similarity	NPC471157
0.7339	Intermediate Similarity	NPC471026
0.7339	Intermediate Similarity	NPC63404
0.7339	Intermediate Similarity	NPC231888
0.7339	Intermediate Similarity	NPC290276
0.7333	Intermediate Similarity	NPC233923
0.7333	Intermediate Similarity	NPC146673
0.7328	Intermediate Similarity	NPC328273
0.7328	Intermediate Similarity	NPC321638
0.7328	Intermediate Similarity	NPC321184
0.7328	Intermediate Similarity	NPC171134
0.7323	Intermediate Similarity	NPC219677
0.7323	Intermediate Similarity	NPC475067
0.7323	Intermediate Similarity	NPC235294
0.7323	Intermediate Similarity	NPC281798
0.7323	Intermediate Similarity	NPC9912
0.7323	Intermediate Similarity	NPC65942
0.7323	Intermediate Similarity	NPC46137
0.7323	Intermediate Similarity	NPC248307
0.7308	Intermediate Similarity	NPC469383
0.7302	Intermediate Similarity	NPC97326
0.7302	Intermediate Similarity	NPC27712
0.7302	Intermediate Similarity	NPC270849
0.7302	Intermediate Similarity	NPC26653
0.7295	Intermediate Similarity	NPC108286
0.7288	Intermediate Similarity	NPC473556
0.7288	Intermediate Similarity	NPC301651
0.728	Intermediate Similarity	NPC231627
0.728	Intermediate Similarity	NPC471025
0.7266	Intermediate Similarity	NPC254275
0.7257	Intermediate Similarity	NPC277788
0.7222	Intermediate Similarity	NPC237182
0.7222	Intermediate Similarity	NPC226101
0.7222	Intermediate Similarity	NPC302378
0.7222	Intermediate Similarity	NPC40377
0.7222	Intermediate Similarity	NPC146540
0.7222	Intermediate Similarity	NPC471024
0.7209	Intermediate Similarity	NPC28637
0.7209	Intermediate Similarity	NPC470143
0.7209	Intermediate Similarity	NPC322503
0.7197	Intermediate Similarity	NPC156376
0.7188	Intermediate Similarity	NPC254819
0.7188	Intermediate Similarity	NPC476407
0.7188	Intermediate Similarity	NPC225384
0.7188	Intermediate Similarity	NPC246869
0.7188	Intermediate Similarity	NPC138777
0.7172	Intermediate Similarity	NPC184030
0.7172	Intermediate Similarity	NPC164449
0.7168	Intermediate Similarity	NPC474376
0.7168	Intermediate Similarity	NPC136962
0.7168	Intermediate Similarity	NPC472316
0.7168	Intermediate Similarity	NPC472315
0.7168	Intermediate Similarity	NPC37115
0.7168	Intermediate Similarity	NPC475203
0.7165	Intermediate Similarity	NPC166040
0.7165	Intermediate Similarity	NPC477293
0.7165	Intermediate Similarity	NPC253595
0.7165	Intermediate Similarity	NPC295970
0.7165	Intermediate Similarity	NPC229784
0.7165	Intermediate Similarity	NPC248355
0.7165	Intermediate Similarity	NPC477294
0.7165	Intermediate Similarity	NPC307110
0.7164	Intermediate Similarity	NPC472353
0.7157	Intermediate Similarity	NPC99482
0.7155	Intermediate Similarity	NPC234376
0.7154	Intermediate Similarity	NPC169398
0.7154	Intermediate Similarity	NPC35731
0.7154	Intermediate Similarity	NPC886
0.7154	Intermediate Similarity	NPC34293

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 NPC47286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	688
0.2-0.3	1451
0.3-0.4	3486
0.4-0.5	2340
0.5-0.6	896
0.6-0.7	109
0.7-0.8	5
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
0.7931	Intermediate Similarity	NPD5126	Approved
0.7931	Intermediate Similarity	NPD5125	Phase 3
0.75	Intermediate Similarity	NPD1091	Approved
0.7456	Intermediate Similarity	NPD969	Suspended
0.7132	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6685	Approved
0.6952	Remote Similarity	NPD531	Approved
0.694	Remote Similarity	NPD7266	Discontinued
0.6903	Remote Similarity	NPD5765	Approved
0.6864	Remote Similarity	NPD6912	Phase 3
0.6783	Remote Similarity	NPD5048	Discontinued
0.6754	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7741	Discontinued
0.6714	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD9532	Phase 3
0.6637	Remote Similarity	NPD7798	Approved
0.6609	Remote Similarity	NPD6647	Phase 2
0.6574	Remote Similarity	NPD689	Discontinued
0.6565	Remote Similarity	NPD2613	Approved
0.6557	Remote Similarity	NPD2629	Approved
0.6549	Remote Similarity	NPD9495	Approved
0.6541	Remote Similarity	NPD4404	Approved
0.6538	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3705	Approved
0.6535	Remote Similarity	NPD9294	Approved
0.6504	Remote Similarity	NPD4198	Discontinued
0.6452	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2575	Approved
0.6418	Remote Similarity	NPD2570	Approved
0.6418	Remote Similarity	NPD2574	Discontinued
0.6418	Remote Similarity	NPD4746	Phase 3
0.6418	Remote Similarity	NPD4745	Approved
0.6418	Remote Similarity	NPD2571	Approved
0.6418	Remote Similarity	NPD3614	Approved
0.6418	Remote Similarity	NPD3615	Approved
0.6418	Remote Similarity	NPD3090	Approved
0.6418	Remote Similarity	NPD3087	Approved
0.6418	Remote Similarity	NPD3616	Approved
0.6418	Remote Similarity	NPD3088	Approved
0.6418	Remote Similarity	NPD3089	Approved
0.6418	Remote Similarity	NPD2573	Approved
0.6418	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2566	Approved
0.6417	Remote Similarity	NPD2067	Discontinued
0.6393	Remote Similarity	NPD7843	Approved
0.6387	Remote Similarity	NPD6406	Approved
0.6387	Remote Similarity	NPD290	Approved
0.635	Remote Similarity	NPD5886	Approved
0.635	Remote Similarity	NPD41	Approved
0.635	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD2160	Approved
0.6336	Remote Similarity	NPD2626	Approved
0.6336	Remote Similarity	NPD2627	Approved
0.6336	Remote Similarity	NPD2625	Approved
0.6336	Remote Similarity	NPD2159	Approved
0.6336	Remote Similarity	NPD2628	Approved
0.6333	Remote Similarity	NPD2684	Approved
0.6324	Remote Similarity	NPD4686	Approved
0.6324	Remote Similarity	NPD4685	Phase 3
0.6324	Remote Similarity	NPD4684	Phase 3
0.6321	Remote Similarity	NPD9491	Approved
0.6308	Remote Similarity	NPD7876	Discontinued
0.6304	Remote Similarity	NPD5588	Approved
0.6299	Remote Similarity	NPD1357	Approved
0.6279	Remote Similarity	NPD4217	Approved
0.6279	Remote Similarity	NPD3131	Approved
0.6279	Remote Similarity	NPD2610	Approved
0.6279	Remote Similarity	NPD4215	Approved
0.6279	Remote Similarity	NPD2612	Approved
0.6279	Remote Similarity	NPD2609	Approved
0.6279	Remote Similarity	NPD3132	Approved
0.6279	Remote Similarity	NPD2611	Approved
0.6279	Remote Similarity	NPD4216	Approved
0.6279	Remote Similarity	NPD2608	Approved
0.6279	Remote Similarity	NPD4218	Approved
0.6269	Remote Similarity	NPD3027	Phase 3
0.6242	Remote Similarity	NPD8455	Phase 2
0.6241	Remote Similarity	NPD6674	Discontinued
0.624	Remote Similarity	NPD7157	Approved
0.624	Remote Similarity	NPD7508	Discontinued
0.6239	Remote Similarity	NPD4719	Phase 2
0.6233	Remote Similarity	NPD1653	Approved
0.623	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1989	Approved
0.621	Remote Similarity	NPD2650	Approved
0.621	Remote Similarity	NPD2652	Approved
0.621	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3719	Approved
0.6195	Remote Similarity	NPD3718	Approved
0.6195	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD9713	Approved
0.614	Remote Similarity	NPD2934	Approved
0.614	Remote Similarity	NPD2933	Approved
0.614	Remote Similarity	NPD1693	Approved
0.6132	Remote Similarity	NPD9250	Approved
0.6132	Remote Similarity	NPD226	Approved
0.6131	Remote Similarity	NPD1613	Approved
0.6131	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD800	Approved
0.6124	Remote Similarity	NPD5723	Approved
0.6124	Remote Similarity	NPD5305	Approved
0.6124	Remote Similarity	NPD5306	Approved
0.6119	Remote Similarity	NPD5204	Approved
0.6118	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD4538	Approved
0.6115	Remote Similarity	NPD7097	Phase 1
0.6115	Remote Similarity	NPD4536	Approved
0.6115	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD1282	Approved
0.6091	Remote Similarity	NPD4793	Discontinued
0.609	Remote Similarity	NPD3094	Phase 2
0.6087	Remote Similarity	NPD2860	Approved
0.6087	Remote Similarity	NPD2859	Approved
0.608	Remote Similarity	NPD6010	Discontinued
0.6077	Remote Similarity	NPD4106	Approved
0.6077	Remote Similarity	NPD4135	Approved
0.6077	Remote Similarity	NPD4136	Approved
0.6071	Remote Similarity	NPD1090	Approved
0.6071	Remote Similarity	NPD1086	Approved
0.6071	Remote Similarity	NPD3672	Approved
0.6071	Remote Similarity	NPD3673	Approved
0.6071	Remote Similarity	NPD1089	Approved
0.6071	Remote Similarity	NPD5960	Phase 3
0.6068	Remote Similarity	NPD2066	Phase 3
0.605	Remote Similarity	NPD3683	Approved
0.605	Remote Similarity	NPD3680	Approved
0.605	Remote Similarity	NPD3682	Approved
0.605	Remote Similarity	NPD3681	Approved
0.6042	Remote Similarity	NPD6190	Approved
0.6042	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD1101	Approved
0.6033	Remote Similarity	NPD5705	Approved
0.6033	Remote Similarity	NPD5706	Approved
0.6033	Remote Similarity	NPD5704	Approved
0.6031	Remote Similarity	NPD4807	Approved
0.6031	Remote Similarity	NPD4806	Approved
0.6029	Remote Similarity	NPD4738	Phase 2
0.6018	Remote Similarity	NPD1239	Approved
0.6017	Remote Similarity	NPD2558	Approved
0.6017	Remote Similarity	NPD2553	Approved
0.6017	Remote Similarity	NPD2549	Approved
0.6017	Remote Similarity	NPD2555	Approved
0.6017	Remote Similarity	NPD2550	Approved
0.6017	Remote Similarity	NPD2552	Approved
0.6014	Remote Similarity	NPD6310	Approved
0.6014	Remote Similarity	NPD6309	Approved
0.6014	Remote Similarity	NPD6311	Approved
0.6014	Remote Similarity	NPD1652	Phase 2
0.6	Remote Similarity	NPD1237	Approved
0.6	Remote Similarity	NPD3664	Approved
0.6	Remote Similarity	NPD3661	Approved
0.6	Remote Similarity	NPD4814	Discontinued
0.6	Remote Similarity	NPD3662	Phase 3
0.6	Remote Similarity	NPD2861	Phase 2
0.6	Remote Similarity	NPD3663	Approved
0.5983	Remote Similarity	NPD9612	Approved
0.5983	Remote Similarity	NPD9609	Approved
0.5983	Remote Similarity	NPD9611	Approved
0.5982	Remote Similarity	NPD5346	Phase 2
0.5982	Remote Similarity	NPD5347	Phase 2
0.5969	Remote Similarity	NPD4479	Discontinued
0.5968	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD855	Approved
0.5966	Remote Similarity	NPD846	Approved
0.5966	Remote Similarity	NPD940	Approved
0.5966	Remote Similarity	NPD854	Approved
0.5966	Remote Similarity	NPD4189	Approved
0.5966	Remote Similarity	NPD4188	Approved
0.5965	Remote Similarity	NPD1088	Approved
0.5965	Remote Similarity	NPD752	Approved
0.596	Remote Similarity	NPD37	Approved
0.5957	Remote Similarity	NPD7033	Discontinued
0.5956	Remote Similarity	NPD5203	Approved
0.5956	Remote Similarity	NPD4620	Approved
0.5956	Remote Similarity	NPD5201	Approved
0.5956	Remote Similarity	NPD4617	Approved
0.5948	Remote Similarity	NPD4966	Approved
0.5948	Remote Similarity	NPD4965	Approved
0.5948	Remote Similarity	NPD4967	Phase 2
0.5946	Remote Similarity	NPD9538	Approved
0.5944	Remote Similarity	NPD2424	Discontinued
0.5943	Remote Similarity	NPD9490	Approved
0.5942	Remote Similarity	NPD6233	Phase 2
0.594	Remote Similarity	NPD3685	Discontinued
0.5932	Remote Similarity	NPD3020	Approved
0.5929	Remote Similarity	NPD6653	Approved
0.5926	Remote Similarity	NPD7247	Discontinued
0.5923	Remote Similarity	NPD4105	Approved
0.5923	Remote Similarity	NPD4102	Approved
0.592	Remote Similarity	NPD4572	Approved
0.592	Remote Similarity	NPD4573	Approved
0.592	Remote Similarity	NPD4571	Approved
0.5917	Remote Similarity	NPD4231	Approved
0.5917	Remote Similarity	NPD4658	Approved
0.5917	Remote Similarity	NPD4229	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