NPASS Compound

Structure

NPC98750 OpenBabel07101718322D 21 22 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 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 2 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 -3.4641 1.0000 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 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 -1.7321 -0.0000 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 2 1 0 0 0 0 1 6 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 3 1 6 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 20 1 6 0 0 0 7 4 1 6 0 0 0 7 9 1 0 0 0 0 7 21 1 0 0 0 0 8 16 1 1 0 0 0 9 10 1 0 0 0 0 9 17 1 1 0 0 0 10 11 1 0 0 0 0 10 18 1 6 0 0 0 11 12 1 0 0 0 0 11 19 1 1 0 0 0 12 20 1 6 0 0 0 12 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.14
Volume:	280.314
LogP:	-2.557
LogD:	-2.697
LogS:	-0.275
# Rotatable Bonds:	4
TPSA:	151.87
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	4.411
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.899
MDCK Permeability:	0.00011594452371355146
Pgp-inhibitor:	0.001
Pgp-substrate:	0.525
Human Intestinal Absorption (HIA):	0.939
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.207
Plasma Protein Binding (PPB):	16.797029495239258%
Volume Distribution (VD):	0.31
Pgp-substrate:	78.2851791381836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	1.396
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.386
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC98750

Natural Product ID:	NPC98750
*Common Name:**	3-O-Beta-D-Glucopyranosylfagomine
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(2R,3R,4R)-3-hydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	ZFBSYXPXCAAPOU-FYKVHUBJSA-N
Standard InCHI:	InChI=1S/C12H23NO8/c14-3-5-8(16)6(1-2-13-5)20-12-11(19)10(18)9(17)7(4-15)21-12/h5-19H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-/m1/s1
SMILES:	C1CN[C@H](CO)[C@H]([C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464522
PubChem CID:	10852369
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
NPO33446	aglaonema treubii	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10560746]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[17396934]
NPO12473	Castanospermum australe	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2213032]
NPO21156	Xanthocercis zambesiaca	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9157194]
NPO21156	Xanthocercis zambesiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157194]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544568]
NPO33446	aglaonema treubii	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544568]
NPO12473	Castanospermum australe	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544568]
NPO21156	Xanthocercis zambesiaca	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[9544568]
NPO21156	Xanthocercis zambesiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544568]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21156	Xanthocercis zambesiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12473	Castanospermum australe	Species	Fabaceae	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	9

Activity Type	# Activity
Individual Protein	1
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	<	50.0	%	PMID[463062]
NPT2	Others	Unspecified		Inhibition	<	50.0	%	PMID[463062]

☑ 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 NPC98750 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	274
0.1-0.2	10819
0.2-0.3	21131
0.3-0.4	8394
0.4-0.5	1578
0.5-0.6	315
0.6-0.7	114
0.7-0.8	61
0.8-0.85	2
0.85-0.9	5
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC70574
0.96	High Similarity	NPC36927
0.96	High Similarity	NPC271772
0.8831	High Similarity	NPC100204
0.8831	High Similarity	NPC83248
0.8701	High Similarity	NPC150557
0.8537	High Similarity	NPC306838
0.85	High Similarity	NPC165119
0.8481	Intermediate Similarity	NPC471420
0.8125	Intermediate Similarity	NPC318258
0.7917	Intermediate Similarity	NPC69669
0.7917	Intermediate Similarity	NPC218150
0.7917	Intermediate Similarity	NPC2432
0.7917	Intermediate Similarity	NPC22774
0.7917	Intermediate Similarity	NPC306462
0.7917	Intermediate Similarity	NPC150680
0.7867	Intermediate Similarity	NPC471418
0.7763	Intermediate Similarity	NPC268922
0.7733	Intermediate Similarity	NPC291650
0.7733	Intermediate Similarity	NPC322801
0.7733	Intermediate Similarity	NPC129100
0.7703	Intermediate Similarity	NPC198341
0.7703	Intermediate Similarity	NPC471892
0.7703	Intermediate Similarity	NPC223386
0.7703	Intermediate Similarity	NPC75435
0.7703	Intermediate Similarity	NPC142290
0.7703	Intermediate Similarity	NPC471780
0.76	Intermediate Similarity	NPC286851
0.76	Intermediate Similarity	NPC303798
0.76	Intermediate Similarity	NPC315980
0.7564	Intermediate Similarity	NPC476696
0.7564	Intermediate Similarity	NPC476695
0.7564	Intermediate Similarity	NPC476694
0.7561	Intermediate Similarity	NPC316807
0.75	Intermediate Similarity	NPC315969
0.75	Intermediate Similarity	NPC143809
0.75	Intermediate Similarity	NPC76726
0.75	Intermediate Similarity	NPC290106
0.75	Intermediate Similarity	NPC193593
0.7447	Intermediate Similarity	NPC315036
0.7412	Intermediate Similarity	NPC263058
0.7386	Intermediate Similarity	NPC123746
0.7386	Intermediate Similarity	NPC43850
0.7386	Intermediate Similarity	NPC314408
0.7386	Intermediate Similarity	NPC477060
0.7386	Intermediate Similarity	NPC314007
0.7386	Intermediate Similarity	NPC470282
0.7273	Intermediate Similarity	NPC313552
0.7263	Intermediate Similarity	NPC471628
0.7263	Intermediate Similarity	NPC56298
0.7222	Intermediate Similarity	NPC195969
0.7222	Intermediate Similarity	NPC176381
0.7191	Intermediate Similarity	NPC214376
0.7125	Intermediate Similarity	NPC28959
0.7125	Intermediate Similarity	NPC137554
0.7125	Intermediate Similarity	NPC255535
0.7125	Intermediate Similarity	NPC285014
0.7125	Intermediate Similarity	NPC299603
0.7123	Intermediate Similarity	NPC204709
0.7105	Intermediate Similarity	NPC163134
0.7105	Intermediate Similarity	NPC471419
0.7041	Intermediate Similarity	NPC221148
0.7027	Intermediate Similarity	NPC170172
0.7021	Intermediate Similarity	NPC330590
0.7	Intermediate Similarity	NPC327753
0.7	Intermediate Similarity	NPC327486
0.7	Intermediate Similarity	NPC223174
0.6989	Remote Similarity	NPC315334
0.6882	Remote Similarity	NPC328646
0.6854	Remote Similarity	NPC253975
0.6854	Remote Similarity	NPC192025
0.6854	Remote Similarity	NPC125253
0.6829	Remote Similarity	NPC474468
0.6827	Remote Similarity	NPC314306
0.6806	Remote Similarity	NPC67660
0.6806	Remote Similarity	NPC165198
0.6806	Remote Similarity	NPC145112
0.6806	Remote Similarity	NPC58629
0.6806	Remote Similarity	NPC89145
0.6806	Remote Similarity	NPC107914
0.6806	Remote Similarity	NPC242073
0.6806	Remote Similarity	NPC157514
0.6806	Remote Similarity	NPC269166
0.6806	Remote Similarity	NPC246558
0.679	Remote Similarity	NPC475694
0.679	Remote Similarity	NPC473710
0.6778	Remote Similarity	NPC83839
0.6739	Remote Similarity	NPC470284
0.6712	Remote Similarity	NPC303727
0.6709	Remote Similarity	NPC69798
0.6709	Remote Similarity	NPC101746
0.6709	Remote Similarity	NPC116377
0.6709	Remote Similarity	NPC77191
0.6709	Remote Similarity	NPC473952
0.6635	Remote Similarity	NPC57436
0.6635	Remote Similarity	NPC121479
0.6628	Remote Similarity	NPC314968
0.6628	Remote Similarity	NPC314772
0.6623	Remote Similarity	NPC8087
0.6623	Remote Similarity	NPC62507
0.6593	Remote Similarity	NPC469363
0.6579	Remote Similarity	NPC233364
0.6579	Remote Similarity	NPC471421
0.6543	Remote Similarity	NPC34291
0.6543	Remote Similarity	NPC126664
0.6528	Remote Similarity	NPC326533
0.6484	Remote Similarity	NPC476523
0.6447	Remote Similarity	NPC472025
0.641	Remote Similarity	NPC57846
0.641	Remote Similarity	NPC474014
0.641	Remote Similarity	NPC30126
0.6404	Remote Similarity	NPC219340
0.6392	Remote Similarity	NPC470283
0.6375	Remote Similarity	NPC474928
0.6364	Remote Similarity	NPC290179
0.6364	Remote Similarity	NPC317023
0.6364	Remote Similarity	NPC34877
0.6351	Remote Similarity	NPC130683
0.6351	Remote Similarity	NPC323361
0.6341	Remote Similarity	NPC171850
0.633	Remote Similarity	NPC313813
0.6316	Remote Similarity	NPC10262
0.6316	Remote Similarity	NPC65832
0.6316	Remote Similarity	NPC311668
0.6301	Remote Similarity	NPC23134
0.6301	Remote Similarity	NPC124963
0.6301	Remote Similarity	NPC233726
0.63	Remote Similarity	NPC315170
0.6296	Remote Similarity	NPC241597
0.6282	Remote Similarity	NPC143326
0.6203	Remote Similarity	NPC477763
0.6203	Remote Similarity	NPC477757
0.6203	Remote Similarity	NPC477753
0.6203	Remote Similarity	NPC477750
0.6203	Remote Similarity	NPC477762
0.6203	Remote Similarity	NPC477755
0.6186	Remote Similarity	NPC208537
0.6186	Remote Similarity	NPC270005
0.6173	Remote Similarity	NPC233034
0.6145	Remote Similarity	NPC107224
0.614	Remote Similarity	NPC20035
0.6117	Remote Similarity	NPC227622
0.6058	Remote Similarity	NPC239705
0.6058	Remote Similarity	NPC314413
0.6058	Remote Similarity	NPC314398
0.6038	Remote Similarity	NPC317534
0.6027	Remote Similarity	NPC157193
0.6027	Remote Similarity	NPC42503
0.6027	Remote Similarity	NPC299781
0.6027	Remote Similarity	NPC282143
0.6026	Remote Similarity	NPC219040
0.602	Remote Similarity	NPC475603
0.602	Remote Similarity	NPC61894
0.6019	Remote Similarity	NPC188453
0.6019	Remote Similarity	NPC42320
0.6	Remote Similarity	NPC94319
0.6	Remote Similarity	NPC62845
0.6	Remote Similarity	NPC322449
0.6	Remote Similarity	NPC166242
0.6	Remote Similarity	NPC92874
0.6	Remote Similarity	NPC189854
0.5976	Remote Similarity	NPC6848
0.5946	Remote Similarity	NPC323574
0.5943	Remote Similarity	NPC325900
0.5943	Remote Similarity	NPC10897
0.593	Remote Similarity	NPC306973
0.5926	Remote Similarity	NPC17455
0.5921	Remote Similarity	NPC272396
0.5905	Remote Similarity	NPC55336
0.5904	Remote Similarity	NPC471760
0.5904	Remote Similarity	NPC12040
0.5904	Remote Similarity	NPC471761
0.5904	Remote Similarity	NPC190418
0.5904	Remote Similarity	NPC76881
0.5904	Remote Similarity	NPC147292
0.5897	Remote Similarity	NPC8979
0.5897	Remote Similarity	NPC148424
0.589	Remote Similarity	NPC14144
0.5888	Remote Similarity	NPC59589
0.5888	Remote Similarity	NPC137453
0.5862	Remote Similarity	NPC185084
0.5843	Remote Similarity	NPC477002
0.5833	Remote Similarity	NPC255377
0.5833	Remote Similarity	NPC477764
0.5833	Remote Similarity	NPC176017
0.5833	Remote Similarity	NPC477751
0.5833	Remote Similarity	NPC92246
0.5833	Remote Similarity	NPC289758
0.5833	Remote Similarity	NPC199857
0.5833	Remote Similarity	NPC477752
0.5833	Remote Similarity	NPC477756
0.5833	Remote Similarity	NPC285364
0.5833	Remote Similarity	NPC69445
0.5833	Remote Similarity	NPC21209
0.5833	Remote Similarity	NPC73906
0.5833	Remote Similarity	NPC165846
0.582	Remote Similarity	NPC262050
0.5814	Remote Similarity	NPC115800
0.5814	Remote Similarity	NPC163538
0.5802	Remote Similarity	NPC472026

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 NPC98750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	3108
0.2-0.3	4401
0.3-0.4	1192
0.4-0.5	187
0.5-0.6	73
0.6-0.7	65
0.7-0.8	36
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
0.7917	Intermediate Similarity	NPD9028	Phase 2
0.7917	Intermediate Similarity	NPD9029	Phase 3
0.7917	Intermediate Similarity	NPD9026	Phase 2
0.7917	Intermediate Similarity	NPD9027	Phase 3
0.7733	Intermediate Similarity	NPD9033	Approved
0.7733	Intermediate Similarity	NPD9032	Approved
0.7733	Intermediate Similarity	NPD9030	Approved
0.7733	Intermediate Similarity	NPD9031	Approved
0.7471	Intermediate Similarity	NPD3200	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4282	Approved
0.7397	Intermediate Similarity	NPD9455	Approved
0.7396	Intermediate Similarity	NPD8045	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3202	Approved
0.7386	Intermediate Similarity	NPD3209	Approved
0.7386	Intermediate Similarity	NPD3201	Approved
0.7386	Intermediate Similarity	NPD3208	Approved
0.7386	Intermediate Similarity	NPD3203	Approved
0.7386	Intermediate Similarity	NPD3207	Approved
0.7375	Intermediate Similarity	NPD9034	Approved
0.7375	Intermediate Similarity	NPD67	Phase 2
0.7297	Intermediate Similarity	NPD393	Approved
0.7263	Intermediate Similarity	NPD4837	Approved
0.7263	Intermediate Similarity	NPD4838	Approved
0.7263	Intermediate Similarity	NPD4835	Approved
0.7263	Intermediate Similarity	NPD4836	Approved
0.7222	Intermediate Similarity	NPD5797	Approved
0.7222	Intermediate Similarity	NPD5796	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5795	Approved
0.7222	Intermediate Similarity	NPD5798	Approved
0.7222	Intermediate Similarity	NPD5794	Approved
0.7191	Intermediate Similarity	NPD2698	Approved
0.7108	Intermediate Similarity	NPD372	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5376	Approved
0.7041	Intermediate Similarity	NPD1449	Approved
0.7041	Intermediate Similarity	NPD1450	Approved
0.7021	Intermediate Similarity	NPD5378	Approved
0.7021	Intermediate Similarity	NPD5377	Approved
0.7021	Intermediate Similarity	NPD5381	Approved
0.7	Intermediate Similarity	NPD9445	Approved
0.6947	Remote Similarity	NPD6428	Approved
0.6933	Remote Similarity	NPD9239	Approved
0.6933	Remote Similarity	NPD9240	Approved
0.6827	Remote Similarity	NPD6429	Approved
0.6827	Remote Similarity	NPD6430	Approved
0.6806	Remote Similarity	NPD893	Approved
0.6806	Remote Similarity	NPD888	Phase 3
0.6806	Remote Similarity	NPD891	Phase 3
0.6806	Remote Similarity	NPD892	Phase 3
0.6806	Remote Similarity	NPD890	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2700	Approved
0.6795	Remote Similarity	NPD1457	Discontinued
0.6701	Remote Similarity	NPD881	Approved
0.6635	Remote Similarity	NPD4833	Approved
0.6635	Remote Similarity	NPD8087	Discontinued
0.6635	Remote Similarity	NPD35	Approved
0.6629	Remote Similarity	NPD882	Phase 2
0.6629	Remote Similarity	NPD883	Phase 2
0.6628	Remote Similarity	NPD9434	Approved
0.6628	Remote Similarity	NPD9435	Approved
0.6627	Remote Similarity	NPD6704	Discontinued
0.6571	Remote Similarity	NPD2690	Discontinued
0.6545	Remote Similarity	NPD8346	Approved
0.6545	Remote Similarity	NPD8345	Approved
0.6545	Remote Similarity	NPD8347	Approved
0.6543	Remote Similarity	NPD9443	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD905	Approved
0.6528	Remote Similarity	NPD904	Phase 3
0.6484	Remote Similarity	NPD361	Discontinued
0.6458	Remote Similarity	NPD1447	Phase 3
0.6458	Remote Similarity	NPD1446	Phase 3
0.641	Remote Similarity	NPD9024	Phase 2
0.641	Remote Similarity	NPD9022	Phase 2
0.6389	Remote Similarity	NPD3204	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD889	Approved
0.6351	Remote Similarity	NPD894	Approved
0.6351	Remote Similarity	NPD895	Approved
0.6351	Remote Similarity	NPD887	Approved
0.6346	Remote Similarity	NPD8140	Approved
0.633	Remote Similarity	NPD4831	Approved
0.633	Remote Similarity	NPD4830	Approved
0.633	Remote Similarity	NPD4832	Approved
0.6316	Remote Similarity	NPD3716	Discontinued
0.6304	Remote Similarity	NPD9401	Discovery
0.6296	Remote Similarity	NPD3731	Phase 3
0.6226	Remote Similarity	NPD6941	Approved
0.6216	Remote Similarity	NPD2269	Approved
0.6203	Remote Similarity	NPD6123	Approved
0.619	Remote Similarity	NPD8307	Discontinued
0.6173	Remote Similarity	NPD9440	Discontinued
0.6163	Remote Similarity	NPD389	Phase 3
0.614	Remote Similarity	NPD6436	Phase 3
0.6139	Remote Similarity	NPD2255	Approved
0.6117	Remote Similarity	NPD8139	Approved
0.6117	Remote Similarity	NPD8085	Approved
0.6117	Remote Similarity	NPD8084	Approved
0.6117	Remote Similarity	NPD8138	Approved
0.6117	Remote Similarity	NPD8086	Approved
0.6117	Remote Similarity	NPD8082	Approved
0.6117	Remote Similarity	NPD8083	Approved
0.6105	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD394	Phase 3
0.6058	Remote Similarity	NPD8276	Approved
0.6058	Remote Similarity	NPD8275	Approved
0.6	Remote Similarity	NPD4826	Approved
0.6	Remote Similarity	NPD4828	Approved
0.6	Remote Similarity	NPD4827	Approved
0.6	Remote Similarity	NPD8081	Approved
0.5962	Remote Similarity	NPD7139	Approved
0.5962	Remote Similarity	NPD7140	Approved
0.5962	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD8393	Approved
0.5833	Remote Similarity	NPD8997	Approved
0.5833	Remote Similarity	NPD9000	Phase 3
0.5833	Remote Similarity	NPD8998	Phase 2
0.5833	Remote Similarity	NPD8999	Phase 3
0.5833	Remote Similarity	NPD8993	Phase 1
0.5823	Remote Similarity	NPD369	Approved
0.578	Remote Similarity	NPD8306	Approved
0.578	Remote Similarity	NPD8305	Approved
0.5765	Remote Similarity	NPD9444	Discontinued
0.5763	Remote Similarity	NPD577	Phase 3
0.5763	Remote Similarity	NPD591	Approved
0.5714	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8966	Approved
0.5676	Remote Similarity	NPD8965	Approved
0.5663	Remote Similarity	NPD847	Phase 1
0.5647	Remote Similarity	NPD374	Approved
0.5647	Remote Similarity	NPD373	Approved
0.5641	Remote Similarity	NPD7346	Approved
0.5625	Remote Similarity	NPD9657	Discontinued
0.5618	Remote Similarity	NPD9653	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD1407	Approved
0.56	Remote Similarity	NPD8522	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