NPASS Compound

Structure

CID206123 OpenBabel06191715592D 33 36 0 0 1 0 0 0 0 0999 V2000 3.4641 2.0000 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 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 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 0.8660 -1.5000 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 2.5981 -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 0.8660 0.5000 0.0000 C 0 0 1 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 0.8660 -5.5000 0.0000 O 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 0.0000 -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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 5 2 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 23 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 25 1 0 0 0 0 13 31 1 0 0 0 0 14 30 1 0 0 0 0 15 8 1 6 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 21 1 0 0 0 0 16 26 2 0 0 0 0 17 18 1 0 0 0 0 17 27 1 1 0 0 0 18 19 1 0 0 0 0 18 28 1 6 0 0 0 19 22 1 0 0 0 0 19 29 1 1 0 0 0 20 21 2 0 0 0 0 20 31 1 0 0 0 0 21 33 1 0 0 0 0 22 32 1 0 0 0 0 22 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.12
Volume:	430.443
LogP:	0.706
LogD:	0.681
LogS:	-4.122
# Rotatable Bonds:	5
TPSA:	179.28
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	3.816
Fsp3:	0.318
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.085
MDCK Permeability:	1.6667168893036433e-05
Pgp-inhibitor:	0.057
Pgp-substrate:	0.481
Human Intestinal Absorption (HIA):	0.354
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	84.74820709228516%
Volume Distribution (VD):	0.851
Pgp-substrate:	14.508692741394043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.212
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.459
CYP2D6-inhibitor:	0.153
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	5.361
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.134
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.253
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.056
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: NPC206123

Natural Product ID:	NPC206123
*Common Name:**	Isorhamnetin-3-Glucoside
IUPAC Name:	7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Isorhamnetin-3-Glucoside
Standard InCHIKey:	KIYXGLNKZKZJHP-LNBCOLIQSA-N
Standard InCHI:	InChI=1S/C22H22O11/c1-30-14-6-9(2-5-12(14)25)20-21(16(26)11-4-3-10(24)7-13(11)31-20)33-22-19(29)18(28)17(27)15(8-23)32-22/h2-7,15,17-19,22-25,27-29H,8H2,1H3/t15-,17-,18+,19-,22+/m1/s1
SMILES:	COc1cc(ccc1O)c1c(c(=O)c2ccc(cc2o1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520748
PubChem CID:	44575188
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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
NPO40994	Inula britannica	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[10650074]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31577434]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	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
IC50	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[564749]
NPT1	Others	Radical scavenging activity		IC50	>	100.0	ug.mL-1	PMID[564749]

☑ 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 NPC206123 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	440
0.1-0.2	1822
0.2-0.3	4199
0.3-0.4	9805
0.4-0.5	8237
0.5-0.6	4214
0.6-0.7	5210
0.7-0.8	5295
0.8-0.85	1669
0.85-0.9	1102
0.9-0.95	496
0.95-1	208

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC120099
0.9937	High Similarity	NPC225434
0.9937	High Similarity	NPC219904
0.9937	High Similarity	NPC203050
0.9937	High Similarity	NPC223747
0.9874	High Similarity	NPC226304
0.9874	High Similarity	NPC127546
0.9874	High Similarity	NPC265530
0.9874	High Similarity	NPC223424
0.9874	High Similarity	NPC52550
0.9874	High Similarity	NPC325555
0.9874	High Similarity	NPC317489
0.9874	High Similarity	NPC173637
0.9874	High Similarity	NPC84362
0.9814	High Similarity	NPC153755
0.9811	High Similarity	NPC88789
0.9811	High Similarity	NPC277174
0.9811	High Similarity	NPC73855
0.9811	High Similarity	NPC179950
0.9811	High Similarity	NPC145038
0.9811	High Similarity	NPC281131
0.9811	High Similarity	NPC56077
0.9811	High Similarity	NPC276222
0.9811	High Similarity	NPC253662
0.9811	High Similarity	NPC274618
0.9811	High Similarity	NPC118284
0.9811	High Similarity	NPC135599
0.9811	High Similarity	NPC308404
0.9811	High Similarity	NPC197285
0.9811	High Similarity	NPC113968
0.9811	High Similarity	NPC328940
0.9811	High Similarity	NPC21100
0.9753	High Similarity	NPC45522
0.9753	High Similarity	NPC169977
0.9753	High Similarity	NPC4390
0.9753	High Similarity	NPC21666
0.9753	High Similarity	NPC42773
0.9753	High Similarity	NPC24043
0.9753	High Similarity	NPC101026
0.9752	High Similarity	NPC116864
0.9752	High Similarity	NPC244776
0.9752	High Similarity	NPC95866
0.975	High Similarity	NPC229729
0.9748	High Similarity	NPC22832
0.9748	High Similarity	NPC311830
0.9748	High Similarity	NPC19388
0.9748	High Similarity	NPC277205
0.9748	High Similarity	NPC55786
0.9748	High Similarity	NPC240431
0.9695	High Similarity	NPC217520
0.9695	High Similarity	NPC139571
0.9693	High Similarity	NPC476472
0.9693	High Similarity	NPC294815
0.9693	High Similarity	NPC473327
0.9693	High Similarity	NPC16194
0.9693	High Similarity	NPC19108
0.9693	High Similarity	NPC220173
0.9691	High Similarity	NPC245452
0.9691	High Similarity	NPC476405
0.9691	High Similarity	NPC33054
0.9691	High Similarity	NPC176740
0.9691	High Similarity	NPC26230
0.9691	High Similarity	NPC203259
0.9691	High Similarity	NPC117260
0.9691	High Similarity	NPC471748
0.9691	High Similarity	NPC175107
0.9691	High Similarity	NPC190003
0.9691	High Similarity	NPC471725
0.9691	High Similarity	NPC155877
0.9691	High Similarity	NPC134532
0.9691	High Similarity	NPC60735
0.9689	High Similarity	NPC52382
0.9689	High Similarity	NPC270578
0.9686	High Similarity	NPC284960
0.9686	High Similarity	NPC309025
0.9686	High Similarity	NPC19709
0.9686	High Similarity	NPC270335
0.9686	High Similarity	NPC191306
0.9686	High Similarity	NPC222936
0.9686	High Similarity	NPC88023
0.9686	High Similarity	NPC243930
0.9686	High Similarity	NPC168822
0.9634	High Similarity	NPC472385
0.9634	High Similarity	NPC198324
0.963	High Similarity	NPC285197
0.963	High Similarity	NPC84265
0.963	High Similarity	NPC245014
0.963	High Similarity	NPC136042
0.963	High Similarity	NPC67326
0.963	High Similarity	NPC255157
0.963	High Similarity	NPC51326
0.963	High Similarity	NPC67105
0.963	High Similarity	NPC259896
0.963	High Similarity	NPC235260
0.963	High Similarity	NPC231194
0.963	High Similarity	NPC72249
0.963	High Similarity	NPC156869
0.963	High Similarity	NPC20505
0.963	High Similarity	NPC155763
0.963	High Similarity	NPC29958
0.963	High Similarity	NPC254855
0.963	High Similarity	NPC282987
0.9627	High Similarity	NPC48640
0.9627	High Similarity	NPC92565
0.9627	High Similarity	NPC149244
0.9627	High Similarity	NPC160156
0.9623	High Similarity	NPC77660
0.9623	High Similarity	NPC189142
0.9623	High Similarity	NPC473043
0.9576	High Similarity	NPC173837
0.9576	High Similarity	NPC251417
0.9576	High Similarity	NPC477895
0.9576	High Similarity	NPC168584
0.9576	High Similarity	NPC35167
0.9576	High Similarity	NPC89052
0.9573	High Similarity	NPC135277
0.9573	High Similarity	NPC237435
0.9573	High Similarity	NPC214621
0.9573	High Similarity	NPC264735
0.9573	High Similarity	NPC43211
0.9573	High Similarity	NPC115760
0.9573	High Similarity	NPC223426
0.9573	High Similarity	NPC81042
0.9573	High Similarity	NPC101191
0.9573	High Similarity	NPC49344
0.9573	High Similarity	NPC294629
0.9573	High Similarity	NPC210094
0.9573	High Similarity	NPC34267
0.9573	High Similarity	NPC477848
0.9571	High Similarity	NPC205076
0.9571	High Similarity	NPC307518
0.9571	High Similarity	NPC48773
0.9571	High Similarity	NPC235575
0.9568	High Similarity	NPC105025
0.9568	High Similarity	NPC201292
0.9568	High Similarity	NPC209296
0.9568	High Similarity	NPC58053
0.9568	High Similarity	NPC229687
0.9568	High Similarity	NPC475942
0.9568	High Similarity	NPC138927
0.9568	High Similarity	NPC186807
0.9568	High Similarity	NPC195257
0.9568	High Similarity	NPC93337
0.9568	High Similarity	NPC226294
0.9568	High Similarity	NPC227508
0.9568	High Similarity	NPC469931
0.9568	High Similarity	NPC45638
0.9565	High Similarity	NPC255615
0.9565	High Similarity	NPC115674
0.9565	High Similarity	NPC254306
0.9565	High Similarity	NPC236934
0.9565	High Similarity	NPC67037
0.9565	High Similarity	NPC5778
0.9565	High Similarity	NPC210073
0.9563	High Similarity	NPC88043
0.956	High Similarity	NPC182045
0.9521	High Similarity	NPC36138
0.9518	High Similarity	NPC126784
0.9518	High Similarity	NPC470444
0.9518	High Similarity	NPC470443
0.9518	High Similarity	NPC473571
0.9518	High Similarity	NPC192539
0.9518	High Similarity	NPC110941
0.9518	High Similarity	NPC241423
0.9518	High Similarity	NPC473682
0.9515	High Similarity	NPC202908
0.9515	High Similarity	NPC89127
0.9515	High Similarity	NPC122467
0.9515	High Similarity	NPC65563
0.9515	High Similarity	NPC48984
0.9515	High Similarity	NPC144097
0.9515	High Similarity	NPC233994
0.9515	High Similarity	NPC211532
0.9515	High Similarity	NPC8573
0.9515	High Similarity	NPC470949
0.9515	High Similarity	NPC219043
0.9515	High Similarity	NPC169733
0.9515	High Similarity	NPC61904
0.9515	High Similarity	NPC14187
0.9515	High Similarity	NPC292019
0.9515	High Similarity	NPC471669
0.9512	High Similarity	NPC472993
0.9509	High Similarity	NPC105511
0.9509	High Similarity	NPC224462
0.9506	High Similarity	NPC58716
0.9506	High Similarity	NPC275454
0.9506	High Similarity	NPC116745
0.9506	High Similarity	NPC146792
0.9506	High Similarity	NPC45618
0.9506	High Similarity	NPC45400
0.9503	High Similarity	NPC165720
0.9503	High Similarity	NPC34531
0.95	High Similarity	NPC127782
0.95	High Similarity	NPC300537
0.9497	High Similarity	NPC110349
0.9464	High Similarity	NPC470416
0.9464	High Similarity	NPC25946
0.9464	High Similarity	NPC460984
0.9464	High Similarity	NPC470720
0.9464	High Similarity	NPC21359

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 NPC206123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	944
0.2-0.3	1949
0.3-0.4	2684
0.4-0.5	1792
0.5-0.6	910
0.6-0.7	296
0.7-0.8	129
0.8-0.85	13
0.85-0.9	16
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9691	High Similarity	NPD6797	Phase 2
0.9632	High Similarity	NPD7251	Discontinued
0.9573	High Similarity	NPD4338	Clinical (unspecified phase)
0.9573	High Similarity	NPD7808	Phase 3
0.9568	High Similarity	NPD7054	Approved
0.9509	High Similarity	NPD7472	Approved
0.939	High Similarity	NPD7074	Phase 3
0.9387	High Similarity	NPD3818	Discontinued
0.925	High Similarity	NPD4381	Clinical (unspecified phase)
0.9146	High Similarity	NPD6168	Clinical (unspecified phase)
0.9146	High Similarity	NPD6166	Phase 2
0.9146	High Similarity	NPD6167	Clinical (unspecified phase)
0.9096	High Similarity	NPD7804	Clinical (unspecified phase)
0.9006	High Similarity	NPD3817	Phase 2
0.9	High Similarity	NPD1934	Approved
0.8951	High Similarity	NPD3882	Suspended
0.8827	High Similarity	NPD2801	Approved
0.8827	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD1512	Approved
0.8667	High Similarity	NPD7075	Discontinued
0.8642	High Similarity	NPD4380	Phase 2
0.8616	High Similarity	NPD1511	Approved
0.8606	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD5402	Approved
0.8537	High Similarity	NPD6801	Discontinued
0.8497	Intermediate Similarity	NPD6559	Discontinued
0.8485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD5403	Approved
0.8439	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD5401	Approved
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD1653	Approved
0.8235	Intermediate Similarity	NPD5494	Approved
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8177	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD3751	Discontinued
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD6599	Discontinued
0.8079	Intermediate Similarity	NPD7685	Pre-registration
0.8063	Intermediate Similarity	NPD2796	Approved
0.8047	Intermediate Similarity	NPD7819	Suspended
0.8047	Intermediate Similarity	NPD1465	Phase 2
0.8036	Intermediate Similarity	NPD7411	Suspended
0.8035	Intermediate Similarity	NPD3787	Discontinued
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7989	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD919	Approved
0.7931	Intermediate Similarity	NPD6232	Discontinued
0.7901	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7874	Intermediate Similarity	NPD7199	Phase 2
0.7874	Intermediate Similarity	NPD6959	Discontinued
0.7874	Intermediate Similarity	NPD1247	Approved
0.7853	Intermediate Similarity	NPD7228	Approved
0.7818	Intermediate Similarity	NPD6190	Approved
0.7791	Intermediate Similarity	NPD7266	Discontinued
0.779	Intermediate Similarity	NPD8313	Approved
0.779	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD3926	Phase 2
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD6780	Approved
0.7772	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7758	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1240	Approved
0.775	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1613	Approved
0.7749	Intermediate Similarity	NPD7435	Discontinued
0.774	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD7584	Approved
0.7702	Intermediate Similarity	NPD1933	Approved
0.7674	Intermediate Similarity	NPD37	Approved
0.7654	Intermediate Similarity	NPD1607	Approved
0.7651	Intermediate Similarity	NPD3750	Approved
0.7644	Intermediate Similarity	NPD4965	Approved
0.7644	Intermediate Similarity	NPD4967	Phase 2
0.7644	Intermediate Similarity	NPD4966	Approved
0.764	Intermediate Similarity	NPD943	Approved
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD230	Phase 1
0.7565	Intermediate Similarity	NPD7698	Approved
0.7565	Intermediate Similarity	NPD7696	Phase 3
0.7565	Intermediate Similarity	NPD7697	Approved
0.7562	Intermediate Similarity	NPD3027	Phase 3
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7543	Intermediate Similarity	NPD7768	Phase 2
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7515	Intermediate Similarity	NPD1551	Phase 2
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7701	Phase 2
0.75	Intermediate Similarity	NPD3749	Approved
0.7485	Intermediate Similarity	NPD447	Suspended
0.7455	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8455	Phase 2
0.741	Intermediate Similarity	NPD2935	Discontinued
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7700	Phase 2
0.7396	Intermediate Similarity	NPD7699	Phase 2
0.7391	Intermediate Similarity	NPD7240	Approved
0.7387	Intermediate Similarity	NPD7801	Approved
0.7381	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3748	Approved
0.7348	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7333	Intermediate Similarity	NPD6823	Phase 2
0.7323	Intermediate Similarity	NPD7585	Approved
0.732	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7783	Phase 2
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7283	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD7583	Approved
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7243	Intermediate Similarity	NPD5953	Discontinued
0.7222	Intermediate Similarity	NPD9494	Approved
0.72	Intermediate Similarity	NPD3226	Approved
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6832	Phase 2
0.7176	Intermediate Similarity	NPD2800	Approved
0.7176	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD6674	Discontinued
0.7175	Intermediate Similarity	NPD6844	Discontinued
0.717	Intermediate Similarity	NPD1091	Approved
0.7168	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7151	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4360	Phase 2
0.715	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7135	Intermediate Similarity	NPD7286	Phase 2
0.7101	Intermediate Similarity	NPD6100	Approved
0.7101	Intermediate Similarity	NPD6099	Approved
0.7099	Intermediate Similarity	NPD1203	Approved
0.7098	Intermediate Similarity	NPD6212	Phase 3
0.7098	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6213	Phase 3
0.7095	Intermediate Similarity	NPD5353	Approved
0.7092	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7081	Intermediate Similarity	NPD2163	Approved
0.7076	Intermediate Similarity	NPD1652	Phase 2
0.7073	Intermediate Similarity	NPD4908	Phase 1
0.7066	Intermediate Similarity	NPD6355	Discontinued
0.7066	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2344	Approved
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7041	Intermediate Similarity	NPD2799	Discontinued
0.7035	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7680	Approved
0.7024	Intermediate Similarity	NPD6651	Approved
0.7011	Intermediate Similarity	NPD5242	Approved
0.7011	Intermediate Similarity	NPD7390	Discontinued
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8127	Discontinued
0.6988	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6842	Approved
0.6979	Remote Similarity	NPD6841	Approved
0.6979	Remote Similarity	NPD6843	Phase 3
0.6965	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5124	Phase 1
0.6964	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7038	Approved
0.6931	Remote Similarity	NPD7039	Approved
0.6927	Remote Similarity	NPD6386	Approved
0.6927	Remote Similarity	NPD6385	Approved
0.6918	Remote Similarity	NPD1548	Phase 1
0.6914	Remote Similarity	NPD9269	Phase 2

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