NPASS Compound

Structure

CID282987 OpenBabel06191716092D 34 37 0 0 1 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 1.7321 0.0000 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 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -3.4641 3.0000 0.0000 C 0 0 0 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 -4.3301 2.5000 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 -4.3301 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 -7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -3.4641 4.0000 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 -5.1962 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 0.0000 0.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 22 1 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 12 1 0 0 0 0 9 25 1 0 0 0 0 10 19 2 0 0 0 0 10 26 1 0 0 0 0 11 5 1 6 0 0 0 11 13 1 0 0 0 0 11 32 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 15 1 0 0 0 0 13 27 1 1 0 0 0 14 16 1 0 0 0 0 14 28 2 0 0 0 0 15 17 1 0 0 0 0 15 29 1 6 0 0 0 16 18 2 0 0 0 0 16 30 1 0 0 0 0 17 21 1 0 0 0 0 17 31 1 1 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 19 34 1 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 21 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.09
Volume:	430.728
LogP:	-0.027
LogD:	-0.107
LogS:	-3.942
# Rotatable Bonds:	4
TPSA:	230.74
# H-Bond Aceptor:	13
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	4.169
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.403
MDCK Permeability:	7.825270586181432e-06
Pgp-inhibitor:	0.034
Pgp-substrate:	0.194
Human Intestinal Absorption (HIA):	0.573
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	90.19216918945312%
Volume Distribution (VD):	0.759
Pgp-substrate:	15.691261291503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.158
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	4.821
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.229
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.868
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.887
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.791
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC282987

Natural Product ID:	NPC282987
*Common Name:**	Gossypetin-8-Glucoside
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Gossypetin-8-Glucoside
Standard InCHIKey:	SJRXVLUZMMDCNG-KKPQBLLMSA-N
Standard InCHI:	InChI=1S/C21H20O13/c22-5-11-13(27)15(29)17(31)21(32-11)34-19-10(26)4-9(25)12-14(28)16(30)18(33-20(12)19)6-1-2-7(23)8(24)3-6/h1-4,11,13,15,17,21-27,29-31H,5H2/t11-,13-,15+,17-,21+/m1/s1
SMILES:	c1cc(c(cc1c1c(c(=O)c2c(cc(c(c2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402915
PubChem CID:	5281621
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003540] Flavonoid-8-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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO29734	Fioria vitifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23738444]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	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
EC50	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2266	Individual Protein	Fructose-1,6-bisphosphatase	Homo sapiens	Inhibition	<	20.0	%	PMID[543270]
NPT1	Others	Radical scavenging activity		EC50	=	25.5	ug	PMID[543268]
NPT2	Others	Unspecified		Inhibition	=	99.06	%	PMID[543269]

☑ 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 NPC282987 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	480
0.1-0.2	1934
0.2-0.3	4573
0.3-0.4	10218
0.4-0.5	7698
0.5-0.6	4218
0.6-0.7	5367
0.7-0.8	5064
0.8-0.85	1443
0.85-0.9	1064
0.9-0.95	461
0.95-1	177

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC84265
1.0	High Similarity	NPC245014
0.9938	High Similarity	NPC117260
0.9938	High Similarity	NPC476405
0.9876	High Similarity	NPC24043
0.9876	High Similarity	NPC101026
0.9876	High Similarity	NPC169977
0.9876	High Similarity	NPC42773
0.9876	High Similarity	NPC45522
0.9876	High Similarity	NPC21666
0.9874	High Similarity	NPC58716
0.9874	High Similarity	NPC146792
0.9874	High Similarity	NPC45618
0.9815	High Similarity	NPC101191
0.9815	High Similarity	NPC477848
0.9815	High Similarity	NPC49344
0.9815	High Similarity	NPC135277
0.9815	High Similarity	NPC43211
0.9815	High Similarity	NPC115760
0.9815	High Similarity	NPC210094
0.9815	High Similarity	NPC237435
0.9812	High Similarity	NPC201292
0.9812	High Similarity	NPC469931
0.9812	High Similarity	NPC45638
0.9812	High Similarity	NPC58053
0.9812	High Similarity	NPC186807
0.9812	High Similarity	NPC475942
0.9812	High Similarity	NPC93337
0.9812	High Similarity	NPC105025
0.9812	High Similarity	NPC226294
0.9811	High Similarity	NPC197285
0.9811	High Similarity	NPC21100
0.9755	High Similarity	NPC211532
0.9755	High Similarity	NPC8573
0.9755	High Similarity	NPC169733
0.9755	High Similarity	NPC233994
0.9755	High Similarity	NPC472385
0.9755	High Similarity	NPC198324
0.9748	High Similarity	NPC277205
0.9695	High Similarity	NPC168584
0.9693	High Similarity	NPC264735
0.9691	High Similarity	NPC3583
0.9691	High Similarity	NPC205076
0.9691	High Similarity	NPC211594
0.9691	High Similarity	NPC172807
0.9691	High Similarity	NPC307518
0.9691	High Similarity	NPC48773
0.9691	High Similarity	NPC254540
0.9691	High Similarity	NPC259152
0.9689	High Similarity	NPC225434
0.9689	High Similarity	NPC471457
0.9689	High Similarity	NPC219904
0.9689	High Similarity	NPC112755
0.9689	High Similarity	NPC170675
0.9689	High Similarity	NPC120099
0.9689	High Similarity	NPC203050
0.9689	High Similarity	NPC223747
0.9688	High Similarity	NPC253662
0.9688	High Similarity	NPC145038
0.9688	High Similarity	NPC88789
0.9688	High Similarity	NPC56077
0.9688	High Similarity	NPC274618
0.9688	High Similarity	NPC118284
0.9688	High Similarity	NPC179950
0.9688	High Similarity	NPC281131
0.9688	High Similarity	NPC276222
0.9688	High Similarity	NPC308404
0.9686	High Similarity	NPC270335
0.9686	High Similarity	NPC191306
0.9636	High Similarity	NPC473682
0.9636	High Similarity	NPC241423
0.9636	High Similarity	NPC470444
0.9636	High Similarity	NPC110941
0.9636	High Similarity	NPC470443
0.9636	High Similarity	NPC126784
0.9636	High Similarity	NPC473571
0.9634	High Similarity	NPC268533
0.9634	High Similarity	NPC65563
0.9634	High Similarity	NPC470949
0.9632	High Similarity	NPC204693
0.9632	High Similarity	NPC4390
0.963	High Similarity	NPC285197
0.963	High Similarity	NPC22195
0.963	High Similarity	NPC206123
0.963	High Similarity	NPC21190
0.963	High Similarity	NPC224462
0.963	High Similarity	NPC34287
0.963	High Similarity	NPC20505
0.963	High Similarity	NPC155763
0.963	High Similarity	NPC105511
0.963	High Similarity	NPC471416
0.963	High Similarity	NPC183357
0.963	High Similarity	NPC235260
0.9627	High Similarity	NPC325555
0.9627	High Similarity	NPC127546
0.9627	High Similarity	NPC265530
0.9627	High Similarity	NPC226304
0.9627	High Similarity	NPC52550
0.9627	High Similarity	NPC84362
0.9627	High Similarity	NPC223424
0.9627	High Similarity	NPC317489
0.9627	High Similarity	NPC173637
0.9625	High Similarity	NPC55786
0.9625	High Similarity	NPC19388
0.9625	High Similarity	NPC240431
0.9625	High Similarity	NPC311830
0.9625	High Similarity	NPC22832
0.9623	High Similarity	NPC189142
0.9623	High Similarity	NPC77660
0.9578	High Similarity	NPC222674
0.9578	High Similarity	NPC473073
0.9578	High Similarity	NPC473071
0.9573	High Similarity	NPC472607
0.9571	High Similarity	NPC26230
0.9571	High Similarity	NPC60735
0.9571	High Similarity	NPC190003
0.9571	High Similarity	NPC153755
0.9571	High Similarity	NPC175107
0.9568	High Similarity	NPC95855
0.9568	High Similarity	NPC138927
0.9568	High Similarity	NPC472381
0.9568	High Similarity	NPC210042
0.9568	High Similarity	NPC472383
0.9565	High Similarity	NPC135599
0.9565	High Similarity	NPC254306
0.9565	High Similarity	NPC99957
0.9565	High Similarity	NPC328940
0.9565	High Similarity	NPC113968
0.9565	High Similarity	NPC181616
0.9565	High Similarity	NPC277174
0.9565	High Similarity	NPC73855
0.9563	High Similarity	NPC88023
0.9563	High Similarity	NPC88043
0.9563	High Similarity	NPC243930
0.9563	High Similarity	NPC222936
0.9563	High Similarity	NPC94777
0.9563	High Similarity	NPC284960
0.9563	High Similarity	NPC168822
0.9563	High Similarity	NPC309025
0.9563	High Similarity	NPC19709
0.9521	High Similarity	NPC107987
0.9521	High Similarity	NPC36138
0.9521	High Similarity	NPC470449
0.9521	High Similarity	NPC470446
0.9521	High Similarity	NPC470447
0.9521	High Similarity	NPC473072
0.9521	High Similarity	NPC470445
0.9515	High Similarity	NPC472382
0.9515	High Similarity	NPC472991
0.9515	High Similarity	NPC472992
0.9515	High Similarity	NPC472380
0.9515	High Similarity	NPC472384
0.9512	High Similarity	NPC51774
0.9512	High Similarity	NPC239549
0.9512	High Similarity	NPC236191
0.9509	High Similarity	NPC116864
0.9509	High Similarity	NPC255157
0.9509	High Similarity	NPC44558
0.9509	High Similarity	NPC95866
0.9509	High Similarity	NPC67105
0.9509	High Similarity	NPC474434
0.9509	High Similarity	NPC156869
0.9509	High Similarity	NPC254855
0.9509	High Similarity	NPC67326
0.9509	High Similarity	NPC29958
0.9509	High Similarity	NPC244776
0.9509	High Similarity	NPC259896
0.9509	High Similarity	NPC72249
0.9509	High Similarity	NPC136042
0.9506	High Similarity	NPC42892
0.9506	High Similarity	NPC135345
0.9506	High Similarity	NPC160156
0.9506	High Similarity	NPC92565
0.9506	High Similarity	NPC275454
0.9506	High Similarity	NPC229729
0.9506	High Similarity	NPC93099
0.9506	High Similarity	NPC45400
0.9503	High Similarity	NPC165720
0.95	High Similarity	NPC473043
0.9464	High Similarity	NPC148710
0.9464	High Similarity	NPC470416
0.9464	High Similarity	NPC470451
0.9464	High Similarity	NPC470455
0.9455	High Similarity	NPC294815
0.9455	High Similarity	NPC220173
0.9455	High Similarity	NPC16194
0.9455	High Similarity	NPC473327
0.9455	High Similarity	NPC19108
0.9455	High Similarity	NPC253685
0.9455	High Similarity	NPC476472
0.9451	High Similarity	NPC471725
0.9451	High Similarity	NPC155877
0.9451	High Similarity	NPC267254
0.9451	High Similarity	NPC134532
0.9451	High Similarity	NPC245452
0.9451	High Similarity	NPC472386
0.9451	High Similarity	NPC203259
0.9451	High Similarity	NPC33054
0.9451	High Similarity	NPC471748
0.9451	High Similarity	NPC301683

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 NPC282987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	432
0.1-0.2	960
0.2-0.3	2074
0.3-0.4	2679
0.4-0.5	1712
0.5-0.6	858
0.6-0.7	281
0.7-0.8	115
0.8-0.85	15
0.85-0.9	15
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9815	High Similarity	NPD4338	Clinical (unspecified phase)
0.9451	High Similarity	NPD6797	Phase 2
0.9448	High Similarity	NPD7054	Approved
0.9394	High Similarity	NPD7251	Discontinued
0.939	High Similarity	NPD7472	Approved
0.9387	High Similarity	NPD3818	Discontinued
0.9337	High Similarity	NPD7808	Phase 3
0.9273	High Similarity	NPD7074	Phase 3
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.9062	High Similarity	NPD2801	Approved
0.903	High Similarity	NPD6168	Clinical (unspecified phase)
0.903	High Similarity	NPD6167	Clinical (unspecified phase)
0.903	High Similarity	NPD6166	Phase 2
0.8882	High Similarity	NPD1934	Approved
0.8869	High Similarity	NPD7804	Clinical (unspecified phase)
0.8773	High Similarity	NPD3817	Phase 2
0.8742	High Similarity	NPD1512	Approved
0.872	High Similarity	NPD3882	Suspended
0.8712	High Similarity	NPD2393	Clinical (unspecified phase)
0.8659	High Similarity	NPD5402	Approved
0.8616	High Similarity	NPD1511	Approved
0.8606	High Similarity	NPD4868	Clinical (unspecified phase)
0.8528	High Similarity	NPD4380	Phase 2
0.8439	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD1653	Approved
0.8343	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8286	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD5403	Approved
0.8221	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6801	Discontinued
0.8177	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD3751	Discontinued
0.8155	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD3787	Discontinued
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD5401	Approved
0.8075	Intermediate Similarity	NPD1549	Phase 2
0.8049	Intermediate Similarity	NPD6799	Approved
0.8047	Intermediate Similarity	NPD1465	Phase 2
0.7978	Intermediate Similarity	NPD7685	Pre-registration
0.7931	Intermediate Similarity	NPD6232	Discontinued
0.7901	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.7874	Intermediate Similarity	NPD1247	Approved
0.7872	Intermediate Similarity	NPD6778	Approved
0.7872	Intermediate Similarity	NPD6779	Approved
0.7872	Intermediate Similarity	NPD6781	Approved
0.7872	Intermediate Similarity	NPD6776	Approved
0.7872	Intermediate Similarity	NPD6782	Approved
0.7872	Intermediate Similarity	NPD6780	Approved
0.7872	Intermediate Similarity	NPD6777	Approved
0.7869	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7228	Approved
0.784	Intermediate Similarity	NPD2796	Approved
0.7836	Intermediate Similarity	NPD7819	Suspended
0.7824	Intermediate Similarity	NPD7411	Suspended
0.7818	Intermediate Similarity	NPD6190	Approved
0.7798	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8313	Approved
0.779	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7765	Intermediate Similarity	NPD6599	Discontinued
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.775	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1613	Approved
0.7749	Intermediate Similarity	NPD7435	Discontinued
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.7674	Intermediate Similarity	NPD37	Approved
0.7657	Intermediate Similarity	NPD919	Approved
0.7656	Intermediate Similarity	NPD7698	Approved
0.7656	Intermediate Similarity	NPD7696	Phase 3
0.7656	Intermediate Similarity	NPD7697	Approved
0.7651	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4965	Approved
0.7644	Intermediate Similarity	NPD4966	Approved
0.7644	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD943	Approved
0.7617	Intermediate Similarity	NPD7871	Phase 2
0.7617	Intermediate Similarity	NPD7870	Phase 2
0.7606	Intermediate Similarity	NPD6534	Approved
0.7606	Intermediate Similarity	NPD6535	Approved
0.759	Intermediate Similarity	NPD7701	Phase 2
0.7576	Intermediate Similarity	NPD7266	Discontinued
0.7545	Intermediate Similarity	NPD3750	Approved
0.7542	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7584	Approved
0.7531	Intermediate Similarity	NPD1240	Approved
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3749	Approved
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7485	Intermediate Similarity	NPD1933	Approved
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7475	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7801	Approved
0.7475	Intermediate Similarity	NPD7783	Phase 2
0.7462	Intermediate Similarity	NPD8151	Discontinued
0.7455	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3027	Phase 3
0.7439	Intermediate Similarity	NPD1607	Approved
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8455	Phase 2
0.7423	Intermediate Similarity	NPD6823	Phase 2
0.741	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD7240	Approved
0.7378	Intermediate Similarity	NPD447	Suspended
0.7345	Intermediate Similarity	NPD7768	Phase 2
0.7344	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4628	Phase 3
0.7301	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7246	Intermediate Similarity	NPD3748	Approved
0.7231	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6213	Phase 3
0.7188	Intermediate Similarity	NPD6212	Phase 3
0.7184	Intermediate Similarity	NPD920	Approved
0.7176	Intermediate Similarity	NPD2800	Approved
0.7176	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8319	Approved
0.7172	Intermediate Similarity	NPD8320	Phase 1
0.717	Intermediate Similarity	NPD1091	Approved
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7585	Approved
0.7117	Intermediate Similarity	NPD9494	Approved
0.7102	Intermediate Similarity	NPD3226	Approved
0.71	Intermediate Similarity	NPD7583	Approved
0.7092	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7076	Intermediate Similarity	NPD6674	Discontinued
0.7074	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD4360	Phase 2
0.7052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7286	Phase 2
0.7041	Intermediate Similarity	NPD7033	Discontinued
0.7035	Intermediate Similarity	NPD7680	Approved
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD6798	Discontinued
0.6977	Remote Similarity	NPD1243	Approved
0.6977	Remote Similarity	NPD1652	Phase 2
0.6975	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4908	Phase 1
0.697	Remote Similarity	NPD6832	Phase 2
0.6959	Remote Similarity	NPD2346	Discontinued
0.6959	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2798	Approved
0.6941	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD6651	Approved
0.6919	Remote Similarity	NPD5242	Approved
0.6918	Remote Similarity	NPD1548	Phase 1
0.6914	Remote Similarity	NPD9269	Phase 2
0.6914	Remote Similarity	NPD7390	Discontinued
0.691	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2861	Phase 2
0.69	Remote Similarity	NPD5005	Approved
0.69	Remote Similarity	NPD5006	Approved
0.6895	Remote Similarity	NPD7549	Discontinued
0.689	Remote Similarity	NPD4111	Phase 1
0.689	Remote Similarity	NPD4665	Approved
0.6886	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5711	Approved
0.6865	Remote Similarity	NPD5710	Approved
0.6864	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6355	Discontinued
0.6864	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5124	Phase 1
0.6852	Remote Similarity	NPD1610	Phase 2
0.6842	Remote Similarity	NPD1509	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