NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	3.344
LogD:	2.692
LogS:	-4.671
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	1.913
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	2.0030400264658965e-05
Pgp-inhibitor:	0.784
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.212
Plasma Protein Binding (PPB):	98.85205841064453%
Volume Distribution (VD):	0.448
Pgp-substrate:	1.0866224765777588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.506
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.677
CYP2C9-substrate:	0.606
CYP2D6-inhibitor:	0.211
CYP2D6-substrate:	0.323
CYP3A4-inhibitor:	0.561
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	5.883
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.864
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.356
Skin Sensitization:	0.099
Carcinogencity:	0.954
Eye Corrosion:	0.004
Eye Irritation:	0.961
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC73416

Natural Product ID:	NPC73416
*Common Name:**	1-Hydroxy-2-Methoxyanthracene-9,10-Dione
IUPAC Name:	1-hydroxy-2-methoxyanthracene-9,10-dione
Synonyms:	Alizarin-2-Methyl Ether
Standard InCHIKey:	BYQWRZGQEZAOPQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c1-19-11-7-6-10-12(15(11)18)14(17)9-5-3-2-4-8(9)13(10)16/h2-7,18H,1H3
SMILES:	COc1ccc2c(C(=O)c3ccccc3C2=O)c1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451977
PubChem CID:	80103
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22860454]
NPO20880	Conocybe siliginea	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32816486]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7097296]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30535	Morinda umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20572	Vepris louisii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30535	Morinda umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19956	Pulveroboletus retipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20572	Vepris louisii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20822	Asperula odora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8020	Lychnophora columnaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20880	Conocybe siliginea	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20064	Litsea konishii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20364	Ophelia bicornis	Species	Opheliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15980	Croton penduliflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19792	Populus tomentosa	Species	Salicaceae	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	5
Others	1
Potency	8

Activity Type	# Activity
Cell Line	6
Individual Protein	5
Organism	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	126.0	%	PMID[454179]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	2238.7	nM	PMID[454180]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[454180]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	3162.3	nM	PMID[454180]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	9528.3	nM	PMID[454180]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[454181]
NPT1505	Cell Line	J82	Homo sapiens	IC50	>	100000.0	nM	PMID[454181]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC50	>	100000.0	nM	PMID[454181]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	100000.0	nM	PMID[454181]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	100000.0	nM	PMID[454181]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	1584.9	nM	PMID[454180]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	2238.7	nM	PMID[454180]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	6573.3	nM	PMID[454180]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	16511.3	nM	PMID[454180]

☑ 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 NPC73416 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	414
0.1-0.2	1841
0.2-0.3	4185
0.3-0.4	10982
0.4-0.5	6907
0.5-0.6	3527
0.6-0.7	6528
0.7-0.8	6698
0.8-0.85	1424
0.85-0.9	156
0.9-0.95	26
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC160777
0.9583	High Similarity	NPC473201
0.9583	High Similarity	NPC118427
0.9583	High Similarity	NPC302783
0.9568	High Similarity	NPC84273
0.9517	High Similarity	NPC312338
0.9517	High Similarity	NPC149889
0.9517	High Similarity	NPC164912
0.9448	High Similarity	NPC144283
0.9424	High Similarity	NPC223336
0.9362	High Similarity	NPC141817
0.9362	High Similarity	NPC176030
0.9362	High Similarity	NPC169214
0.9362	High Similarity	NPC192597
0.9362	High Similarity	NPC229218
0.931	High Similarity	NPC37220
0.9262	High Similarity	NPC178976
0.9195	High Similarity	NPC77807
0.9195	High Similarity	NPC14561
0.9195	High Similarity	NPC5379
0.9133	High Similarity	NPC37543
0.9133	High Similarity	NPC199463
0.913	High Similarity	NPC294226
0.9091	High Similarity	NPC11314
0.9079	High Similarity	NPC311740
0.9071	High Similarity	NPC324929
0.9067	High Similarity	NPC279605
0.906	High Similarity	NPC107109
0.9054	High Similarity	NPC78505
0.9048	High Similarity	NPC134293
0.9041	High Similarity	NPC58373
0.9013	High Similarity	NPC84571
0.9	High Similarity	NPC258502
0.8966	High Similarity	NPC309169
0.8966	High Similarity	NPC229787
0.8966	High Similarity	NPC196941
0.8944	High Similarity	NPC61398
0.8944	High Similarity	NPC416
0.894	High Similarity	NPC213401
0.8936	High Similarity	NPC141934
0.8926	High Similarity	NPC306011
0.8926	High Similarity	NPC472838
0.8912	High Similarity	NPC52692
0.8904	High Similarity	NPC478019
0.8903	High Similarity	NPC26386
0.8867	High Similarity	NPC137125
0.8867	High Similarity	NPC3744
0.8865	High Similarity	NPC89504
0.8865	High Similarity	NPC95485
0.8865	High Similarity	NPC88065
0.8859	High Similarity	NPC58310
0.8859	High Similarity	NPC295977
0.8844	High Similarity	NPC39361
0.8836	High Similarity	NPC142165
0.8836	High Similarity	NPC19896
0.8828	High Similarity	NPC69755
0.8808	High Similarity	NPC475770
0.8808	High Similarity	NPC474000
0.88	High Similarity	NPC70320
0.88	High Similarity	NPC75377
0.8792	High Similarity	NPC200060
0.8792	High Similarity	NPC237441
0.8792	High Similarity	NPC40290
0.8792	High Similarity	NPC69430
0.8792	High Similarity	NPC139293
0.8792	High Similarity	NPC142876
0.8792	High Similarity	NPC195763
0.8792	High Similarity	NPC264289
0.8792	High Similarity	NPC333691
0.8792	High Similarity	NPC264550
0.8786	High Similarity	NPC50763
0.8784	High Similarity	NPC125449
0.8784	High Similarity	NPC188074
0.8777	High Similarity	NPC66905
0.8777	High Similarity	NPC117609
0.8768	High Similarity	NPC234175
0.8767	High Similarity	NPC239608
0.8767	High Similarity	NPC46161
0.8767	High Similarity	NPC50954
0.8767	High Similarity	NPC287722
0.8767	High Similarity	NPC254659
0.875	High Similarity	NPC38898
0.875	High Similarity	NPC1268
0.8741	High Similarity	NPC147418
0.8733	High Similarity	NPC472279
0.8733	High Similarity	NPC29231
0.8733	High Similarity	NPC85131
0.8733	High Similarity	NPC151473
0.8725	High Similarity	NPC287395
0.8725	High Similarity	NPC183655
0.8725	High Similarity	NPC194653
0.8725	High Similarity	NPC203747
0.8725	High Similarity	NPC139364
0.8725	High Similarity	NPC80710
0.8725	High Similarity	NPC254702
0.8707	High Similarity	NPC91694
0.8707	High Similarity	NPC300603
0.8701	High Similarity	NPC245891
0.8701	High Similarity	NPC104876
0.8696	High Similarity	NPC32163
0.8696	High Similarity	NPC16651
0.8693	High Similarity	NPC288353
0.869	High Similarity	NPC203063
0.8684	High Similarity	NPC472905
0.8684	High Similarity	NPC127172
0.8684	High Similarity	NPC93552
0.8675	High Similarity	NPC256406
0.8667	High Similarity	NPC472837
0.8658	High Similarity	NPC245584
0.8658	High Similarity	NPC118027
0.8658	High Similarity	NPC312929
0.8658	High Similarity	NPC56433
0.8658	High Similarity	NPC126767
0.8658	High Similarity	NPC190648
0.8658	High Similarity	NPC77598
0.8658	High Similarity	NPC289042
0.8649	High Similarity	NPC225351
0.8645	High Similarity	NPC185617
0.8639	High Similarity	NPC53016
0.8636	High Similarity	NPC296044
0.8636	High Similarity	NPC167098
0.8636	High Similarity	NPC136674
0.8636	High Similarity	NPC472963
0.863	High Similarity	NPC124365
0.8627	High Similarity	NPC472048
0.8627	High Similarity	NPC152951
0.8627	High Similarity	NPC117992
0.8627	High Similarity	NPC234485
0.8627	High Similarity	NPC57674
0.8627	High Similarity	NPC168247
0.8627	High Similarity	NPC39184
0.8627	High Similarity	NPC230149
0.8623	High Similarity	NPC177925
0.8618	High Similarity	NPC100971
0.8618	High Similarity	NPC245382
0.8618	High Similarity	NPC269451
0.8618	High Similarity	NPC121522
0.8618	High Similarity	NPC209487
0.8618	High Similarity	NPC295646
0.8618	High Similarity	NPC216769
0.8618	High Similarity	NPC131266
0.8618	High Similarity	NPC100263
0.8618	High Similarity	NPC474993
0.8618	High Similarity	NPC291802
0.8618	High Similarity	NPC181209
0.8618	High Similarity	NPC35763
0.8616	High Similarity	NPC163130
0.8616	High Similarity	NPC165979
0.8609	High Similarity	NPC280295
0.8609	High Similarity	NPC290954
0.8609	High Similarity	NPC255641
0.86	High Similarity	NPC272721
0.86	High Similarity	NPC43669
0.86	High Similarity	NPC196277
0.86	High Similarity	NPC55327
0.8599	High Similarity	NPC101769
0.8591	High Similarity	NPC12377
0.859	High Similarity	NPC472906
0.8581	High Similarity	NPC477410
0.8581	High Similarity	NPC235448
0.8581	High Similarity	NPC242893
0.8581	High Similarity	NPC38065
0.8581	High Similarity	NPC207732
0.8581	High Similarity	NPC275278
0.8571	High Similarity	NPC470762
0.8571	High Similarity	NPC301178
0.8571	High Similarity	NPC472455
0.8571	High Similarity	NPC472907
0.8571	High Similarity	NPC478223
0.8571	High Similarity	NPC284556
0.8571	High Similarity	NPC474167
0.8571	High Similarity	NPC312256
0.8562	High Similarity	NPC271779
0.8562	High Similarity	NPC167091
0.8562	High Similarity	NPC124714
0.8562	High Similarity	NPC50823
0.8562	High Similarity	NPC88645
0.8562	High Similarity	NPC292214
0.8562	High Similarity	NPC70433
0.8562	High Similarity	NPC49402
0.8562	High Similarity	NPC305710
0.8562	High Similarity	NPC206238
0.8562	High Similarity	NPC469550
0.8562	High Similarity	NPC33051
0.8562	High Similarity	NPC78987
0.8562	High Similarity	NPC82336
0.8562	High Similarity	NPC227337
0.8562	High Similarity	NPC273462
0.8553	High Similarity	NPC124842
0.8553	High Similarity	NPC45291
0.8553	High Similarity	NPC234331
0.8553	High Similarity	NPC19980
0.8553	High Similarity	NPC31363
0.8544	High Similarity	NPC303174
0.8543	High Similarity	NPC102003
0.8543	High Similarity	NPC261322
0.8543	High Similarity	NPC171916
0.8543	High Similarity	NPC38545
0.8543	High Similarity	NPC92722
0.8535	High Similarity	NPC294965

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 NPC73416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1005
0.2-0.3	1515
0.3-0.4	2636
0.4-0.5	1868
0.5-0.6	1048
0.6-0.7	514
0.7-0.8	140
0.8-0.85	25
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8535	High Similarity	NPD6232	Discontinued
0.8491	Intermediate Similarity	NPD7473	Discontinued
0.8377	Intermediate Similarity	NPD1934	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8298	Intermediate Similarity	NPD9494	Approved
0.8286	Intermediate Similarity	NPD1470	Approved
0.8217	Intermediate Similarity	NPD3882	Suspended
0.8212	Intermediate Similarity	NPD1511	Approved
0.8205	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD943	Approved
0.8105	Intermediate Similarity	NPD1512	Approved
0.8065	Intermediate Similarity	NPD3226	Approved
0.8054	Intermediate Similarity	NPD2346	Discontinued
0.8054	Intermediate Similarity	NPD2344	Approved
0.8041	Intermediate Similarity	NPD1510	Phase 2
0.8027	Intermediate Similarity	NPD1607	Approved
0.8014	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD1201	Approved
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7862	Intermediate Similarity	NPD1465	Phase 2
0.7843	Intermediate Similarity	NPD2309	Approved
0.7838	Intermediate Similarity	NPD447	Suspended
0.7815	Intermediate Similarity	NPD1471	Phase 3
0.7806	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD4380	Phase 2
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1549	Phase 2
0.775	Intermediate Similarity	NPD7819	Suspended
0.773	Intermediate Similarity	NPD5494	Approved
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7724	Intermediate Similarity	NPD2798	Approved
0.7722	Intermediate Similarity	NPD7458	Discontinued
0.7702	Intermediate Similarity	NPD3817	Phase 2
0.7698	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7074	Phase 3
0.7662	Intermediate Similarity	NPD7003	Approved
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7628	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7054	Approved
0.7607	Intermediate Similarity	NPD7075	Discontinued
0.7597	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1283	Approved
0.7586	Intermediate Similarity	NPD1876	Approved
0.758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6959	Discontinued
0.7574	Intermediate Similarity	NPD7472	Approved
0.7569	Intermediate Similarity	NPD3972	Approved
0.7548	Intermediate Similarity	NPD8166	Discontinued
0.7548	Intermediate Similarity	NPD4628	Phase 3
0.7535	Intermediate Similarity	NPD1651	Approved
0.7531	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5536	Phase 2
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1933	Approved
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7464	Intermediate Similarity	NPD228	Approved
0.7455	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD6599	Discontinued
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3750	Approved
0.7427	Intermediate Similarity	NPD6797	Phase 2
0.7417	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3620	Phase 2
0.7415	Intermediate Similarity	NPD1203	Approved
0.7407	Intermediate Similarity	NPD7411	Suspended
0.7405	Intermediate Similarity	NPD7390	Discontinued
0.7405	Intermediate Similarity	NPD6799	Approved
0.7403	Intermediate Similarity	NPD2796	Approved
0.7403	Intermediate Similarity	NPD5404	Approved
0.7403	Intermediate Similarity	NPD5408	Approved
0.7403	Intermediate Similarity	NPD5406	Approved
0.7403	Intermediate Similarity	NPD5405	Approved
0.74	Intermediate Similarity	NPD3764	Approved
0.7399	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7251	Discontinued
0.7379	Intermediate Similarity	NPD1281	Approved
0.7378	Intermediate Similarity	NPD5977	Approved
0.7378	Intermediate Similarity	NPD5978	Approved
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD1247	Approved
0.7362	Intermediate Similarity	NPD6801	Discontinued
0.7362	Intermediate Similarity	NPD37	Approved
0.7349	Intermediate Similarity	NPD919	Approved
0.7341	Intermediate Similarity	NPD7808	Phase 3
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6273	Approved
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2296	Approved
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7241	Intermediate Similarity	NPD4626	Approved
0.7239	Intermediate Similarity	NPD7028	Phase 2
0.7235	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5283	Phase 1
0.7233	Intermediate Similarity	NPD3300	Phase 2
0.7229	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD4965	Approved
0.7229	Intermediate Similarity	NPD4967	Phase 2
0.7229	Intermediate Similarity	NPD7768	Phase 2
0.7215	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD6780	Approved
0.7213	Intermediate Similarity	NPD6777	Approved
0.7213	Intermediate Similarity	NPD6781	Approved
0.7213	Intermediate Similarity	NPD6778	Approved
0.7213	Intermediate Similarity	NPD6776	Approved
0.7213	Intermediate Similarity	NPD6782	Approved
0.7211	Intermediate Similarity	NPD9717	Approved
0.7203	Intermediate Similarity	NPD9493	Approved
0.7184	Intermediate Similarity	NPD6559	Discontinued
0.7181	Intermediate Similarity	NPD1164	Approved
0.7179	Intermediate Similarity	NPD1551	Phase 2
0.7178	Intermediate Similarity	NPD824	Approved
0.7175	Intermediate Similarity	NPD8150	Discontinued
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.7171	Intermediate Similarity	NPD411	Approved
0.717	Intermediate Similarity	NPD6190	Approved
0.7162	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2800	Approved
0.7151	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3019	Approved
0.7115	Intermediate Similarity	NPD4308	Phase 3
0.7115	Intermediate Similarity	NPD3748	Approved
0.711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3027	Phase 3
0.7097	Intermediate Similarity	NPD7435	Discontinued
0.7095	Intermediate Similarity	NPD1608	Approved
0.7086	Intermediate Similarity	NPD7685	Pre-registration
0.7086	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1613	Approved
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5402	Approved
0.7063	Intermediate Similarity	NPD2354	Approved
0.7059	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD6832	Phase 2
0.7032	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2932	Approved
0.7005	Intermediate Similarity	NPD7698	Approved
0.7005	Intermediate Similarity	NPD7696	Phase 3
0.7005	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4110	Phase 3
0.7	Intermediate Similarity	NPD8151	Discontinued
0.6993	Remote Similarity	NPD1241	Discontinued
0.6993	Remote Similarity	NPD7095	Approved
0.6988	Remote Similarity	NPD6385	Approved
0.6988	Remote Similarity	NPD6873	Phase 2
0.6988	Remote Similarity	NPD6386	Approved
0.6987	Remote Similarity	NPD6651	Approved
0.6986	Remote Similarity	NPD9545	Approved
0.698	Remote Similarity	NPD9269	Phase 2
0.6972	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2651	Approved
0.697	Remote Similarity	NPD2649	Approved
0.697	Remote Similarity	NPD3455	Phase 2
0.6968	Remote Similarity	NPD7870	Phase 2
0.6968	Remote Similarity	NPD7871	Phase 2
0.6968	Remote Similarity	NPD2979	Phase 3
0.6962	Remote Similarity	NPD6100	Approved
0.6962	Remote Similarity	NPD2438	Suspended
0.6962	Remote Similarity	NPD6099	Approved
0.6954	Remote Similarity	NPD7177	Discontinued
0.6954	Remote Similarity	NPD2797	Approved
0.6951	Remote Similarity	NPD920	Approved
0.6951	Remote Similarity	NPD5403	Approved
0.695	Remote Similarity	NPD3022	Approved
0.695	Remote Similarity	NPD3021	Approved
0.6947	Remote Similarity	NPD7701	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