NPASS Compound

Structure

NPC471669 OpenBabel07101719252D 46 50 0 0 1 0 0 0 0 0999 V2000 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -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 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -5.1962 -3.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 16 2 0 0 0 0 8 41 1 0 0 0 0 9 1 1 6 0 0 0 9 25 1 0 0 0 0 9 42 1 0 0 0 0 10 30 2 0 0 0 0 10 41 1 0 0 0 0 11 26 1 0 0 0 0 12 31 1 0 0 0 0 13 14 2 0 0 0 0 13 32 1 0 0 0 0 14 33 1 0 0 0 0 15 18 2 0 0 0 0 15 34 1 0 0 0 0 16 18 1 0 0 0 0 16 43 1 0 0 0 0 17 8 1 1 0 0 0 17 19 1 0 0 0 0 17 44 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 35 1 1 0 0 0 20 27 1 0 0 0 0 20 36 2 0 0 0 0 21 23 1 0 0 0 0 21 37 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 22 38 1 6 0 0 0 23 29 1 0 0 0 0 23 39 1 6 0 0 0 24 28 1 0 0 0 0 24 40 1 6 0 0 0 25 45 1 1 0 0 0 26 27 2 0 0 0 0 26 43 1 0 0 0 0 27 46 1 0 0 0 0 28 42 1 0 0 0 0 28 46 1 1 0 0 0 29 44 1 0 0 0 0 29 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	652.16
Volume:	593.063
LogP:	0.815
LogD:	0.058
LogS:	-4.493
# Rotatable Bonds:	8
TPSA:	275.5
# H-Bond Aceptor:	17
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	4.853
Fsp3:	0.448
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.47
MDCK Permeability:	4.4134601921541616e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.829
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	84.93936920166016%
Volume Distribution (VD):	0.613
Pgp-substrate:	19.853084564208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.161
CYP2D6-inhibitor:	0.121
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	1.36
Half-life (T1/2):	0.798

ADMET: Toxicity

hERG Blockers:	0.247
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.847
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.892
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.346
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC471669

Natural Product ID:	NPC471669
*Common Name:**	[(2R,3R,4R,5R,6S)-6-[(2S,3R,4S,5R,6S)-6-[2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-4-Oxochromen-3-Yl]Oxy-4,5-Dihydroxy-2-Methyloxan-3-Yl]Oxy-3,4,5-Trihydroxyoxan-2-Yl]Methyl Acetate
IUPAC Name:	[(2R,3R,4R,5R,6S)-6-[(2S,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Synonyms:
Standard InCHIKey:	AATRYBSLZLJIJX-FNBLAZGBSA-N
Standard InCHI:	InChI=1S/C29H32O17/c1-9-25(45-29-23(39)21(37)19(35)17(44-29)8-41-10(2)30)22(38)24(40)28(42-9)46-27-20(36)18-15(34)6-12(31)7-16(18)43-26(27)11-3-4-13(32)14(33)5-11/h3-7,9,17,19,21-25,28-29,31-35,37-40H,8H2,1-2H3/t9-,17+,19-,21+,22-,23+,24+,25-,28-,29-/m0/s1
SMILES:	CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)OC5C(C(C(C(O5)COC(=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL309225
PubChem CID:	44460558
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
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11549443]
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9871657]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	65.4	ng ml-1	PMID[568670]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	52.1	ng ml-1	PMID[568670]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	40.3	ng ml-1	PMID[568670]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	27.4	ng ml-1	PMID[568670]

☑ 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 NPC471669 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	426
0.1-0.2	1844
0.2-0.3	4293
0.3-0.4	9407
0.4-0.5	8554
0.5-0.6	4803
0.6-0.7	5603
0.7-0.8	5258
0.8-0.85	1506
0.85-0.9	446
0.9-0.95	414
0.95-1	143

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC89127
0.9939	High Similarity	NPC173837
0.9878	High Similarity	NPC473862
0.9817	High Similarity	NPC16194
0.9817	High Similarity	NPC473327
0.9817	High Similarity	NPC19108
0.9817	High Similarity	NPC476472
0.9817	High Similarity	NPC253685
0.9817	High Similarity	NPC220173
0.9817	High Similarity	NPC294815
0.9816	High Similarity	NPC471725
0.9816	High Similarity	NPC203259
0.9816	High Similarity	NPC33054
0.9816	High Similarity	NPC134532
0.9816	High Similarity	NPC176740
0.9816	High Similarity	NPC155877
0.9816	High Similarity	NPC471748
0.976	High Similarity	NPC470446
0.976	High Similarity	NPC241781
0.976	High Similarity	NPC470449
0.976	High Similarity	NPC162394
0.976	High Similarity	NPC470445
0.976	High Similarity	NPC156785
0.976	High Similarity	NPC470447
0.9758	High Similarity	NPC122467
0.9758	High Similarity	NPC14187
0.9758	High Similarity	NPC202908
0.9758	High Similarity	NPC292019
0.9755	High Similarity	NPC29958
0.9755	High Similarity	NPC67105
0.9755	High Similarity	NPC156869
0.9755	High Similarity	NPC136042
0.9755	High Similarity	NPC116864
0.9755	High Similarity	NPC244776
0.9755	High Similarity	NPC67326
0.9755	High Similarity	NPC259896
0.9755	High Similarity	NPC254855
0.9755	High Similarity	NPC255157
0.9755	High Similarity	NPC95866
0.9702	High Similarity	NPC275977
0.9702	High Similarity	NPC470455
0.9702	High Similarity	NPC470451
0.9702	High Similarity	NPC470713
0.9702	High Similarity	NPC223860
0.9702	High Similarity	NPC249560
0.9702	High Similarity	NPC25946
0.9702	High Similarity	NPC470720
0.9702	High Similarity	NPC21359
0.9702	High Similarity	NPC470717
0.9702	High Similarity	NPC460984
0.9699	High Similarity	NPC89052
0.9699	High Similarity	NPC251417
0.9695	High Similarity	NPC175107
0.9695	High Similarity	NPC153755
0.9695	High Similarity	NPC26230
0.9695	High Similarity	NPC190003
0.9695	High Similarity	NPC60735
0.9693	High Similarity	NPC227508
0.9645	High Similarity	NPC295625
0.9645	High Similarity	NPC473554
0.9645	High Similarity	NPC470719
0.9645	High Similarity	NPC33083
0.9643	High Similarity	NPC470718
0.9641	High Similarity	NPC110941
0.9641	High Similarity	NPC470443
0.9641	High Similarity	NPC126784
0.9641	High Similarity	NPC473682
0.9641	High Similarity	NPC473571
0.9641	High Similarity	NPC241423
0.9641	High Similarity	NPC192539
0.9641	High Similarity	NPC470444
0.9639	High Similarity	NPC219043
0.9639	High Similarity	NPC65563
0.9639	High Similarity	NPC48984
0.9639	High Similarity	NPC470949
0.9636	High Similarity	NPC4390
0.9634	High Similarity	NPC285197
0.9634	High Similarity	NPC155763
0.9634	High Similarity	NPC235260
0.9634	High Similarity	NPC20505
0.9632	High Similarity	NPC275454
0.9632	High Similarity	NPC52550
0.9632	High Similarity	NPC84362
0.9632	High Similarity	NPC223424
0.9632	High Similarity	NPC317489
0.9632	High Similarity	NPC173637
0.9632	High Similarity	NPC127546
0.9588	High Similarity	NPC97817
0.9588	High Similarity	NPC72554
0.9588	High Similarity	NPC30011
0.9581	High Similarity	NPC120952
0.9581	High Similarity	NPC113836
0.9581	High Similarity	NPC139571
0.9581	High Similarity	NPC253521
0.9581	High Similarity	NPC293626
0.9581	High Similarity	NPC217520
0.9581	High Similarity	NPC196127
0.9581	High Similarity	NPC37668
0.9581	High Similarity	NPC258044
0.9581	High Similarity	NPC35167
0.9581	High Similarity	NPC217387
0.9581	High Similarity	NPC267680
0.9578	High Similarity	NPC294629
0.9578	High Similarity	NPC223426
0.9578	High Similarity	NPC81042
0.9578	High Similarity	NPC214621
0.9578	High Similarity	NPC34267
0.9573	High Similarity	NPC138927
0.9573	High Similarity	NPC120099
0.9573	High Similarity	NPC225434
0.9573	High Similarity	NPC270578
0.9573	High Similarity	NPC219904
0.9573	High Similarity	NPC195257
0.9573	High Similarity	NPC86008
0.9573	High Similarity	NPC209296
0.9573	High Similarity	NPC203050
0.9573	High Similarity	NPC52382
0.9573	High Similarity	NPC223747
0.9571	High Similarity	NPC308404
0.9571	High Similarity	NPC64425
0.9571	High Similarity	NPC113968
0.9571	High Similarity	NPC276222
0.9571	High Similarity	NPC210073
0.9571	High Similarity	NPC73855
0.9571	High Similarity	NPC274618
0.9571	High Similarity	NPC145038
0.9571	High Similarity	NPC88789
0.9571	High Similarity	NPC118284
0.9571	High Similarity	NPC281131
0.9571	High Similarity	NPC8856
0.9571	High Similarity	NPC135599
0.9571	High Similarity	NPC56077
0.9571	High Similarity	NPC115674
0.9571	High Similarity	NPC277174
0.9571	High Similarity	NPC179950
0.9571	High Similarity	NPC253662
0.9571	High Similarity	NPC328940
0.9529	High Similarity	NPC474093
0.9529	High Similarity	NPC104910
0.9527	High Similarity	NPC473072
0.9521	High Similarity	NPC8573
0.9521	High Similarity	NPC61904
0.9521	High Similarity	NPC472385
0.9521	High Similarity	NPC169733
0.9521	High Similarity	NPC198324
0.9521	High Similarity	NPC144097
0.9515	High Similarity	NPC206123
0.9512	High Similarity	NPC265530
0.9512	High Similarity	NPC325555
0.9512	High Similarity	NPC226304
0.9512	High Similarity	NPC160156
0.9512	High Similarity	NPC92565
0.9509	High Similarity	NPC277205
0.9509	High Similarity	NPC55786
0.9509	High Similarity	NPC19388
0.9509	High Similarity	NPC240431
0.9474	High Similarity	NPC475179
0.9471	High Similarity	NPC148710
0.9467	High Similarity	NPC473071
0.9467	High Similarity	NPC473073
0.9464	High Similarity	NPC477895
0.9461	High Similarity	NPC210094
0.9461	High Similarity	NPC101191
0.9461	High Similarity	NPC237435
0.9461	High Similarity	NPC198199
0.9461	High Similarity	NPC477848
0.9461	High Similarity	NPC115760
0.9461	High Similarity	NPC264735
0.9461	High Similarity	NPC49344
0.9461	High Similarity	NPC135277
0.9461	High Similarity	NPC43211
0.9458	High Similarity	NPC180918
0.9458	High Similarity	NPC245452
0.9455	High Similarity	NPC105283
0.9455	High Similarity	NPC43587
0.9451	High Similarity	NPC197285
0.9451	High Similarity	NPC21100
0.9448	High Similarity	NPC19709
0.9412	High Similarity	NPC135831
0.9412	High Similarity	NPC97119
0.9412	High Similarity	NPC36138
0.9412	High Similarity	NPC297503
0.9405	High Similarity	NPC472384
0.9405	High Similarity	NPC268533
0.9405	High Similarity	NPC472382
0.9405	High Similarity	NPC233994
0.9405	High Similarity	NPC211532
0.9405	High Similarity	NPC472380
0.9401	High Similarity	NPC21666
0.9401	High Similarity	NPC24043
0.9401	High Similarity	NPC208668
0.9401	High Similarity	NPC204693
0.9401	High Similarity	NPC169977
0.9401	High Similarity	NPC101026
0.9401	High Similarity	NPC472993
0.9401	High Similarity	NPC42773
0.9401	High Similarity	NPC45522
0.9401	High Similarity	NPC25724
0.9398	High Similarity	NPC218488
0.9398	High Similarity	NPC44328

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 NPC471669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	960
0.2-0.3	2043
0.3-0.4	2691
0.4-0.5	1830
0.5-0.6	842
0.6-0.7	261
0.7-0.8	98
0.8-0.85	24
0.85-0.9	7
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9877	High Similarity	NPD7251	Discontinued
0.9816	High Similarity	NPD6797	Phase 2
0.9697	High Similarity	NPD7808	Phase 3
0.9634	High Similarity	NPD7472	Approved
0.9573	High Similarity	NPD7054	Approved
0.9461	High Similarity	NPD4338	Clinical (unspecified phase)
0.9398	High Similarity	NPD7074	Phase 3
0.9222	High Similarity	NPD7804	Clinical (unspecified phase)
0.9042	High Similarity	NPD6166	Phase 2
0.9042	High Similarity	NPD6168	Clinical (unspecified phase)
0.9042	High Similarity	NPD6167	Clinical (unspecified phase)
0.8935	High Similarity	NPD3818	Discontinued
0.8909	High Similarity	NPD4381	Clinical (unspecified phase)
0.8902	High Similarity	NPD3817	Phase 2
0.8683	High Similarity	NPD7075	Discontinued
0.8671	High Similarity	NPD7993	Clinical (unspecified phase)
0.8667	High Similarity	NPD1934	Approved
0.8614	High Similarity	NPD2393	Clinical (unspecified phase)
0.8528	High Similarity	NPD1512	Approved
0.8512	High Similarity	NPD3882	Suspended
0.8512	High Similarity	NPD4868	Clinical (unspecified phase)
0.8503	High Similarity	NPD7096	Clinical (unspecified phase)
0.8503	High Similarity	NPD2801	Approved
0.8452	Intermediate Similarity	NPD5402	Approved
0.8443	Intermediate Similarity	NPD6801	Discontinued
0.8405	Intermediate Similarity	NPD1511	Approved
0.8364	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8305	Intermediate Similarity	NPD6559	Discontinued
0.8297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6799	Approved
0.8242	Intermediate Similarity	NPD5401	Approved
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD8313	Approved
0.8111	Intermediate Similarity	NPD8312	Approved
0.8095	Intermediate Similarity	NPD1653	Approved
0.8079	Intermediate Similarity	NPD7228	Approved
0.807	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.7978	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD1465	Phase 2
0.7955	Intermediate Similarity	NPD3787	Discontinued
0.7953	Intermediate Similarity	NPD7411	Suspended
0.7943	Intermediate Similarity	NPD5494	Approved
0.7933	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7266	Discontinued
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7473	Discontinued
0.7919	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7879	Intermediate Similarity	NPD1549	Phase 2
0.7865	Intermediate Similarity	NPD7435	Discontinued
0.7861	Intermediate Similarity	NPD8455	Phase 2
0.7853	Intermediate Similarity	NPD6232	Discontinued
0.7846	Intermediate Similarity	NPD8151	Discontinued
0.7826	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7199	Phase 2
0.7796	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD919	Approved
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2796	Approved
0.7738	Intermediate Similarity	NPD6190	Approved
0.7706	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7240	Approved
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7684	Intermediate Similarity	NPD6234	Discontinued
0.7679	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7874	Approved
0.7626	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD6776	Approved
0.7617	Intermediate Similarity	NPD6781	Approved
0.7617	Intermediate Similarity	NPD6780	Approved
0.7617	Intermediate Similarity	NPD6779	Approved
0.7617	Intermediate Similarity	NPD6782	Approved
0.7617	Intermediate Similarity	NPD6778	Approved
0.7617	Intermediate Similarity	NPD6777	Approved
0.76	Intermediate Similarity	NPD37	Approved
0.759	Intermediate Similarity	NPD7698	Approved
0.759	Intermediate Similarity	NPD7696	Phase 3
0.759	Intermediate Similarity	NPD7697	Approved
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3750	Approved
0.7571	Intermediate Similarity	NPD4966	Approved
0.7571	Intermediate Similarity	NPD4965	Approved
0.7571	Intermediate Similarity	NPD4967	Phase 2
0.7571	Intermediate Similarity	NPD7768	Phase 2
0.7563	Intermediate Similarity	NPD7584	Approved
0.7561	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1613	Approved
0.7551	Intermediate Similarity	NPD8320	Phase 1
0.7551	Intermediate Similarity	NPD8319	Approved
0.7546	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7701	Phase 2
0.7515	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD1247	Approved
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7462	Intermediate Similarity	NPD7870	Phase 2
0.7462	Intermediate Similarity	NPD7871	Phase 2
0.7455	Intermediate Similarity	NPD1240	Approved
0.744	Intermediate Similarity	NPD1551	Phase 2
0.743	Intermediate Similarity	NPD3749	Approved
0.7423	Intermediate Similarity	NPD7699	Phase 2
0.7423	Intermediate Similarity	NPD7700	Phase 2
0.7418	Intermediate Similarity	NPD3926	Phase 2
0.7407	Intermediate Similarity	NPD8150	Discontinued
0.7407	Intermediate Similarity	NPD8434	Phase 2
0.7377	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1607	Approved
0.7358	Intermediate Similarity	NPD6535	Approved
0.7358	Intermediate Similarity	NPD6534	Approved
0.735	Intermediate Similarity	NPD7585	Approved
0.7349	Intermediate Similarity	NPD943	Approved
0.7337	Intermediate Similarity	NPD2935	Discontinued
0.733	Intermediate Similarity	NPD7458	Discontinued
0.7327	Intermediate Similarity	NPD7801	Approved
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD447	Suspended
0.73	Intermediate Similarity	NPD7583	Approved
0.7299	Intermediate Similarity	NPD2533	Approved
0.7299	Intermediate Similarity	NPD2534	Approved
0.7299	Intermediate Similarity	NPD2532	Approved
0.7296	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.726	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7680	Approved
0.7229	Intermediate Similarity	NPD6798	Discontinued
0.7216	Intermediate Similarity	NPD920	Approved
0.7212	Intermediate Similarity	NPD6832	Phase 2
0.7202	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6233	Phase 2
0.7181	Intermediate Similarity	NPD5953	Discontinued
0.7176	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7033	Discontinued
0.7166	Intermediate Similarity	NPD7286	Phase 2
0.7135	Intermediate Similarity	NPD3226	Approved
0.711	Intermediate Similarity	NPD1243	Approved
0.711	Intermediate Similarity	NPD1652	Phase 2
0.7102	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6099	Approved
0.7035	Intermediate Similarity	NPD6100	Approved
0.7033	Intermediate Similarity	NPD5353	Approved
0.703	Intermediate Similarity	NPD1203	Approved
0.7024	Intermediate Similarity	NPD2313	Discontinued
0.7017	Intermediate Similarity	NPD6844	Discontinued
0.7016	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD6674	Discontinued
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.7	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2346	Discontinued
0.6994	Remote Similarity	NPD1091	Approved
0.6977	Remote Similarity	NPD2799	Discontinued
0.6971	Remote Similarity	NPD7930	Approved
0.6961	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6651	Approved
0.6954	Remote Similarity	NPD6212	Phase 3
0.6954	Remote Similarity	NPD6213	Phase 3
0.6954	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7390	Discontinued
0.6944	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4060	Phase 1
0.6935	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD3268	Approved
0.6919	Remote Similarity	NPD7097	Phase 1
0.6905	Remote Similarity	NPD4908	Phase 1
0.6898	Remote Similarity	NPD5711	Approved
0.6898	Remote Similarity	NPD5710	Approved
0.689	Remote Similarity	NPD422	Phase 1
0.6886	Remote Similarity	NPD2798	Approved
0.6882	Remote Similarity	NPD4062	Phase 3
0.6868	Remote Similarity	NPD6386	Approved
0.6868	Remote Similarity	NPD6385	Approved
0.6867	Remote Similarity	NPD3225	Approved
0.6864	Remote Similarity	NPD7095	Approved
0.6862	Remote Similarity	NPD5242	Approved
0.6856	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD9269	Phase 2
0.6848	Remote Similarity	NPD9717	Approved
0.6847	Remote Similarity	NPD5006	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