NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.04
Volume:	253.76
LogP:	3.233
LogD:	2.318
LogS:	-3.607
# Rotatable Bonds:	1
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	1.76
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.572
MDCK Permeability:	1.5600109691149555e-05
Pgp-inhibitor:	0.624
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	95.86417388916016%
Volume Distribution (VD):	0.266
Pgp-substrate:	1.2969377040863037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.377
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.306
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	0.728
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.802
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.311
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.112
Carcinogencity:	0.798
Eye Corrosion:	0.003
Eye Irritation:	0.868
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC158157

Natural Product ID:	NPC158157
*Common Name:**	Anthraquinone-2-Carboxylic Acid
IUPAC Name:	9,10-dioxoanthracene-2-carboxylic acid
Synonyms:	Anthraquinone-2-Carboxylic Acid
Standard InCHIKey:	ASDLSKCKYGVMAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H8O4/c16-13-9-3-1-2-4-10(9)14(17)12-7-8(15(18)19)5-6-11(12)13/h1-7H,(H,18,19)
SMILES:	O=C1c2cc(ccc2C(=O)c2c1cccc2)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455581
PubChem CID:	67030
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0001911] Anthracenecarboxylic acids and derivatives [CHEMONTID:0002424] Anthracenecarboxylic acids

*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
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1338	Individual Protein	Sialidase 2	Homo sapiens	IC50	=	800000.0	nM	PMID[545969]
NPT2	Others	Unspecified		Activity	<	50.0	%	PMID[545968]
NPT2	Others	Unspecified		Ratio IC50	=	1.9	n.a.	PMID[545969]
NPT2	Others	Unspecified		IC50	=	430000.0	nM	PMID[545969]

☑ 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 NPC158157 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	323
0.1-0.2	1488
0.2-0.3	3242
0.3-0.4	9727
0.4-0.5	11756
0.5-0.6	10252
0.6-0.7	5166
0.7-0.8	683
0.8-0.85	46
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC196673
0.9138	High Similarity	NPC167323
0.9138	High Similarity	NPC269923
0.9083	High Similarity	NPC318327
0.8983	High Similarity	NPC85511
0.8839	High Similarity	NPC66208
0.8796	High Similarity	NPC255676
0.8772	High Similarity	NPC476357
0.8684	High Similarity	NPC471721
0.8636	High Similarity	NPC105899
0.8609	High Similarity	NPC186933
0.8596	High Similarity	NPC93287
0.8537	High Similarity	NPC115797
0.8537	High Similarity	NPC51448
0.8532	High Similarity	NPC25458
0.8532	High Similarity	NPC284477
0.8504	High Similarity	NPC288089
0.8421	Intermediate Similarity	NPC474057
0.839	Intermediate Similarity	NPC228318
0.8364	Intermediate Similarity	NPC304873
0.8349	Intermediate Similarity	NPC228435
0.8349	Intermediate Similarity	NPC217621
0.8288	Intermediate Similarity	NPC329556
0.8279	Intermediate Similarity	NPC91478
0.8273	Intermediate Similarity	NPC282895
0.8261	Intermediate Similarity	NPC95126
0.8261	Intermediate Similarity	NPC475002
0.8257	Intermediate Similarity	NPC229242
0.8244	Intermediate Similarity	NPC4214
0.8241	Intermediate Similarity	NPC61944
0.8211	Intermediate Similarity	NPC228739
0.8197	Intermediate Similarity	NPC120545
0.819	Intermediate Similarity	NPC280789
0.819	Intermediate Similarity	NPC186128
0.8182	Intermediate Similarity	NPC26924
0.8165	Intermediate Similarity	NPC253423
0.816	Intermediate Similarity	NPC474106
0.8145	Intermediate Similarity	NPC295664
0.8145	Intermediate Similarity	NPC142956
0.8142	Intermediate Similarity	NPC134120
0.8142	Intermediate Similarity	NPC172483
0.812	Intermediate Similarity	NPC315578
0.8115	Intermediate Similarity	NPC472981
0.8099	Intermediate Similarity	NPC202015
0.8065	Intermediate Similarity	NPC375356
0.8065	Intermediate Similarity	NPC318067
0.8053	Intermediate Similarity	NPC329282
0.8047	Intermediate Similarity	NPC199253
0.8047	Intermediate Similarity	NPC136588
0.8047	Intermediate Similarity	NPC31799
0.8034	Intermediate Similarity	NPC292834
0.8034	Intermediate Similarity	NPC79496
0.8031	Intermediate Similarity	NPC282923
0.8017	Intermediate Similarity	NPC318173
0.8015	Intermediate Similarity	NPC80035
0.8	Intermediate Similarity	NPC211439
0.8	Intermediate Similarity	NPC469843
0.8	Intermediate Similarity	NPC164014
0.8	Intermediate Similarity	NPC236189
0.8	Intermediate Similarity	NPC115458
0.8	Intermediate Similarity	NPC212891
0.8	Intermediate Similarity	NPC249811
0.7984	Intermediate Similarity	NPC300274
0.7984	Intermediate Similarity	NPC93015
0.7983	Intermediate Similarity	NPC274839
0.7983	Intermediate Similarity	NPC306740
0.7983	Intermediate Similarity	NPC215419
0.7982	Intermediate Similarity	NPC172925
0.7966	Intermediate Similarity	NPC143768
0.7965	Intermediate Similarity	NPC274443
0.7949	Intermediate Similarity	NPC265513
0.7949	Intermediate Similarity	NPC210089
0.7941	Intermediate Similarity	NPC66593
0.7937	Intermediate Similarity	NPC103540
0.7931	Intermediate Similarity	NPC85493
0.7926	Intermediate Similarity	NPC290550
0.7923	Intermediate Similarity	NPC70622
0.792	Intermediate Similarity	NPC328107
0.7913	Intermediate Similarity	NPC37914
0.7907	Intermediate Similarity	NPC27659
0.7895	Intermediate Similarity	NPC249067
0.7891	Intermediate Similarity	NPC95537
0.7891	Intermediate Similarity	NPC48248
0.7891	Intermediate Similarity	NPC234175
0.789	Intermediate Similarity	NPC261181
0.789	Intermediate Similarity	NPC289883
0.7881	Intermediate Similarity	NPC471188
0.7876	Intermediate Similarity	NPC222390
0.7876	Intermediate Similarity	NPC244427
0.7874	Intermediate Similarity	NPC96915
0.7863	Intermediate Similarity	NPC225051
0.7863	Intermediate Similarity	NPC52407
0.7863	Intermediate Similarity	NPC53896
0.7857	Intermediate Similarity	NPC173978
0.7846	Intermediate Similarity	NPC205992
0.784	Intermediate Similarity	NPC223351
0.7836	Intermediate Similarity	NPC13715
0.7833	Intermediate Similarity	NPC221275
0.7829	Intermediate Similarity	NPC146647
0.7829	Intermediate Similarity	NPC99731
0.7829	Intermediate Similarity	NPC34414
0.782	Intermediate Similarity	NPC272268
0.782	Intermediate Similarity	NPC472308
0.7807	Intermediate Similarity	NPC247976
0.7805	Intermediate Similarity	NPC472708
0.7805	Intermediate Similarity	NPC204784
0.7797	Intermediate Similarity	NPC133308
0.7797	Intermediate Similarity	NPC167504
0.7797	Intermediate Similarity	NPC260818
0.7787	Intermediate Similarity	NPC323440
0.7787	Intermediate Similarity	NPC222968
0.7787	Intermediate Similarity	NPC80605
0.7778	Intermediate Similarity	NPC19256
0.7778	Intermediate Similarity	NPC62765
0.7778	Intermediate Similarity	NPC275145
0.777	Intermediate Similarity	NPC314437
0.7769	Intermediate Similarity	NPC55949
0.7769	Intermediate Similarity	NPC31539
0.776	Intermediate Similarity	NPC369
0.776	Intermediate Similarity	NPC293831
0.7759	Intermediate Similarity	NPC100767
0.7752	Intermediate Similarity	NPC96024
0.7744	Intermediate Similarity	NPC161632
0.7744	Intermediate Similarity	NPC258502
0.7742	Intermediate Similarity	NPC232958
0.7742	Intermediate Similarity	NPC183339
0.7742	Intermediate Similarity	NPC133389
0.7742	Intermediate Similarity	NPC234337
0.7739	Intermediate Similarity	NPC472221
0.7739	Intermediate Similarity	NPC472222
0.7731	Intermediate Similarity	NPC321852
0.7724	Intermediate Similarity	NPC328694
0.7721	Intermediate Similarity	NPC183345
0.7721	Intermediate Similarity	NPC96421
0.7705	Intermediate Similarity	NPC242764
0.7705	Intermediate Similarity	NPC105141
0.7698	Intermediate Similarity	NPC307174
0.7698	Intermediate Similarity	NPC68167
0.7692	Intermediate Similarity	NPC276238
0.7687	Intermediate Similarity	NPC155211
0.7686	Intermediate Similarity	NPC93181
0.768	Intermediate Similarity	NPC144547
0.7679	Intermediate Similarity	NPC156021
0.7674	Intermediate Similarity	NPC84672
0.7674	Intermediate Similarity	NPC176130
0.7674	Intermediate Similarity	NPC78364
0.7674	Intermediate Similarity	NPC69424
0.7669	Intermediate Similarity	NPC50924
0.7667	Intermediate Similarity	NPC470253
0.7667	Intermediate Similarity	NPC13784
0.7656	Intermediate Similarity	NPC275576
0.7652	Intermediate Similarity	NPC58685
0.7642	Intermediate Similarity	NPC45794
0.7638	Intermediate Similarity	NPC51079
0.7632	Intermediate Similarity	NPC136810
0.7632	Intermediate Similarity	NPC133809
0.7632	Intermediate Similarity	NPC128248
0.763	Intermediate Similarity	NPC53414
0.763	Intermediate Similarity	NPC53206
0.763	Intermediate Similarity	NPC62272
0.7623	Intermediate Similarity	NPC322197
0.7623	Intermediate Similarity	NPC135730
0.7615	Intermediate Similarity	NPC229894
0.7612	Intermediate Similarity	NPC283088
0.7612	Intermediate Similarity	NPC477596
0.7609	Intermediate Similarity	NPC193555
0.7609	Intermediate Similarity	NPC73061
0.7607	Intermediate Similarity	NPC142326
0.7607	Intermediate Similarity	NPC94751
0.7603	Intermediate Similarity	NPC130591
0.7603	Intermediate Similarity	NPC67377
0.7603	Intermediate Similarity	NPC153053
0.7603	Intermediate Similarity	NPC234637
0.76	Intermediate Similarity	NPC988
0.76	Intermediate Similarity	NPC289432
0.7597	Intermediate Similarity	NPC254492
0.7597	Intermediate Similarity	NPC3224
0.7597	Intermediate Similarity	NPC169913
0.7597	Intermediate Similarity	NPC160499
0.7594	Intermediate Similarity	NPC477139
0.7594	Intermediate Similarity	NPC294226
0.7593	Intermediate Similarity	NPC267262
0.7591	Intermediate Similarity	NPC225243
0.7586	Intermediate Similarity	NPC31786
0.7586	Intermediate Similarity	NPC114594
0.7583	Intermediate Similarity	NPC158282
0.7578	Intermediate Similarity	NPC199273
0.7576	Intermediate Similarity	NPC244699
0.7576	Intermediate Similarity	NPC17083
0.7576	Intermediate Similarity	NPC18798
0.7574	Intermediate Similarity	NPC61398
0.7574	Intermediate Similarity	NPC416
0.7565	Intermediate Similarity	NPC320891
0.7559	Intermediate Similarity	NPC65627
0.7559	Intermediate Similarity	NPC282577
0.7559	Intermediate Similarity	NPC283514
0.7557	Intermediate Similarity	NPC117899
0.7557	Intermediate Similarity	NPC25736
0.7557	Intermediate Similarity	NPC471832
0.7556	Intermediate Similarity	NPC474813

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 NPC158157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	916
0.2-0.3	1316
0.3-0.4	2659
0.4-0.5	2487
0.5-0.6	1118
0.6-0.7	288
0.7-0.8	58
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8938	High Similarity	NPD5951	Approved
0.8487	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1929	Approved
0.8288	Intermediate Similarity	NPD1930	Approved
0.8198	Intermediate Similarity	NPD1932	Approved
0.811	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD7008	Discontinued
0.7937	Intermediate Similarity	NPD1470	Approved
0.7895	Intermediate Similarity	NPD1237	Approved
0.789	Intermediate Similarity	NPD1202	Approved
0.7857	Intermediate Similarity	NPD2066	Phase 3
0.7778	Intermediate Similarity	NPD9258	Approved
0.7778	Intermediate Similarity	NPD2329	Discontinued
0.7778	Intermediate Similarity	NPD9256	Approved
0.776	Intermediate Similarity	NPD1201	Approved
0.7706	Intermediate Similarity	NPD1239	Approved
0.7698	Intermediate Similarity	NPD4878	Approved
0.7638	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5406	Approved
0.763	Intermediate Similarity	NPD5408	Approved
0.763	Intermediate Similarity	NPD5405	Approved
0.763	Intermediate Similarity	NPD5404	Approved
0.7606	Intermediate Similarity	NPD3226	Approved
0.7586	Intermediate Similarity	NPD164	Approved
0.7556	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2346	Discontinued
0.7438	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6966	Discovery
0.7407	Intermediate Similarity	NPD9259	Approved
0.7407	Intermediate Similarity	NPD9257	Approved
0.7402	Intermediate Similarity	NPD4879	Approved
0.7391	Intermediate Similarity	NPD1238	Approved
0.7385	Intermediate Similarity	NPD1164	Approved
0.7368	Intermediate Similarity	NPD1566	Phase 3
0.7368	Intermediate Similarity	NPD1564	Approved
0.7368	Intermediate Similarity	NPD1565	Approved
0.7345	Intermediate Similarity	NPD1693	Approved
0.7333	Intermediate Similarity	NPD2182	Approved
0.7323	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1086	Approved
0.7297	Intermediate Similarity	NPD1090	Approved
0.7297	Intermediate Similarity	NPD1089	Approved
0.7295	Intermediate Similarity	NPD9508	Approved
0.7286	Intermediate Similarity	NPD7003	Approved
0.728	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1317	Discontinued
0.7257	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7217	Intermediate Similarity	NPD3495	Discontinued
0.7214	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6287	Discontinued
0.7207	Intermediate Similarity	NPD800	Approved
0.7197	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2345	Approved
0.7182	Intermediate Similarity	NPD650	Approved
0.7176	Intermediate Similarity	NPD1283	Approved
0.7168	Intermediate Similarity	NPD1088	Approved
0.7155	Intermediate Similarity	NPD9495	Approved
0.7143	Intermediate Similarity	NPD5909	Discontinued
0.713	Intermediate Similarity	NPD9491	Approved
0.712	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1563	Approved
0.7087	Intermediate Similarity	NPD7610	Discontinued
0.708	Intermediate Similarity	NPD7609	Phase 3
0.7068	Intermediate Similarity	NPD4980	Approved
0.7054	Intermediate Similarity	NPD3019	Approved
0.7045	Intermediate Similarity	NPD1888	Phase 1
0.7027	Intermediate Similarity	NPD1087	Approved
0.7018	Intermediate Similarity	NPD1508	Approved
0.7018	Intermediate Similarity	NPD7631	Approved
0.7007	Intermediate Similarity	NPD7458	Discontinued
0.7007	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3268	Approved
0.6984	Remote Similarity	NPD2629	Approved
0.6983	Remote Similarity	NPD1989	Approved
0.6977	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD9264	Approved
0.6967	Remote Similarity	NPD9267	Approved
0.6967	Remote Similarity	NPD2342	Discontinued
0.6967	Remote Similarity	NPD9263	Approved
0.695	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1281	Approved
0.6944	Remote Similarity	NPD226	Approved
0.6944	Remote Similarity	NPD942	Approved
0.6944	Remote Similarity	NPD7236	Approved
0.6934	Remote Similarity	NPD7961	Discontinued
0.6929	Remote Similarity	NPD2799	Discontinued
0.6929	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD2932	Approved
0.6923	Remote Similarity	NPD3750	Approved
0.6917	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD9266	Approved
0.6911	Remote Similarity	NPD74	Approved
0.6905	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7009	Phase 2
0.6897	Remote Similarity	NPD9260	Approved
0.6897	Remote Similarity	NPD7390	Discontinued
0.6892	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1245	Approved
0.6842	Remote Similarity	NPD5157	Phase 1
0.6842	Remote Similarity	NPD5159	Phase 2
0.6842	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1843	Approved
0.6831	Remote Similarity	NPD1471	Phase 3
0.6831	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5277	Phase 2
0.6824	Remote Similarity	NPD7239	Suspended
0.6815	Remote Similarity	NPD2798	Approved
0.6812	Remote Similarity	NPD7714	Approved
0.6812	Remote Similarity	NPD7715	Approved
0.6809	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4628	Phase 3
0.6797	Remote Similarity	NPD4198	Discontinued
0.6794	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1876	Approved
0.6791	Remote Similarity	NPD1574	Approved
0.6786	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6647	Phase 2
0.6769	Remote Similarity	NPD9545	Approved
0.6767	Remote Similarity	NPD3972	Approved
0.6761	Remote Similarity	NPD2935	Discontinued
0.6759	Remote Similarity	NPD9490	Approved
0.6752	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6049	Phase 2
0.6744	Remote Similarity	NPD9493	Approved
0.6742	Remote Similarity	NPD3023	Approved
0.6742	Remote Similarity	NPD1889	Phase 1
0.6742	Remote Similarity	NPD3026	Approved
0.6741	Remote Similarity	NPD3266	Approved
0.6741	Remote Similarity	NPD1203	Approved
0.6741	Remote Similarity	NPD3267	Approved
0.6739	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD9281	Approved
0.6719	Remote Similarity	NPD1246	Approved
0.6718	Remote Similarity	NPD1651	Approved
0.6718	Remote Similarity	NPD3024	Approved
0.6718	Remote Similarity	NPD4102	Approved
0.6718	Remote Similarity	NPD4105	Approved
0.6718	Remote Similarity	NPD3025	Approved
0.6693	Remote Similarity	NPD6858	Approved
0.6693	Remote Similarity	NPD7094	Approved
0.6691	Remote Similarity	NPD6663	Approved
0.669	Remote Similarity	NPD8166	Discontinued
0.669	Remote Similarity	NPD3748	Approved
0.6689	Remote Similarity	NPD6273	Approved
0.6689	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD3971	Phase 1
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD5086	Approved
0.6643	Remote Similarity	NPD4307	Phase 2
0.6643	Remote Similarity	NPD943	Approved
0.6642	Remote Similarity	NPD1608	Approved
0.6642	Remote Similarity	NPD5736	Approved
0.6639	Remote Similarity	NPD9261	Approved
0.6624	Remote Similarity	NPD6232	Discontinued
0.6622	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2797	Approved
0.6617	Remote Similarity	NPD4136	Approved
0.6617	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4106	Approved
0.6617	Remote Similarity	NPD4135	Approved
0.6604	Remote Similarity	NPD7473	Discontinued
0.6601	Remote Similarity	NPD7819	Suspended
0.6599	Remote Similarity	NPD3300	Phase 2
0.6579	Remote Similarity	NPD4793	Discontinued
0.6573	Remote Similarity	NPD1510	Phase 2
0.6562	Remote Similarity	NPD7635	Approved
0.6549	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1607	Approved
0.6545	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5306	Approved
0.6541	Remote Similarity	NPD4199	Phase 3
0.6541	Remote Similarity	NPD1104	Approved
0.6541	Remote Similarity	NPD4626	Approved
0.6541	Remote Similarity	NPD5305	Approved
0.6538	Remote Similarity	NPD3317	Approved
0.6529	Remote Similarity	NPD7798	Approved
0.6528	Remote Similarity	NPD1551	Phase 2
0.6525	Remote Similarity	NPD4453	Approved
0.6525	Remote Similarity	NPD4445	Approved
0.6525	Remote Similarity	NPD4452	Approved
0.6525	Remote Similarity	NPD2979	Phase 3
0.6519	Remote Similarity	NPD9717	Approved
0.6519	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2344	Approved
0.6475	Remote Similarity	NPD1616	Discontinued
0.6474	Remote Similarity	NPD3749	Approved
0.6466	Remote Similarity	NPD9268	Approved
0.6466	Remote Similarity	NPD5346	Phase 2
0.6466	Remote Similarity	NPD5347	Phase 2
0.646	Remote Similarity	NPD7177	Discontinued

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