NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	3.244
LogD:	3.044
LogS:	-3.724
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	2.286
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.992
MDCK Permeability:	1.228034307132475e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.342
20% Bioavailability (F20%):	0.609
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	96.43102264404297%
Volume Distribution (VD):	0.546
Pgp-substrate:	5.6997904777526855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.217
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.57
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.651
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	13.023
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.417
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.951
Carcinogencity:	0.761
Eye Corrosion:	0.055
Eye Irritation:	0.966
Respiratory Toxicity:	0.746

Download Data

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

Natural Product: NPC164947

Natural Product ID:	NPC164947
*Common Name:**	Ephemeranthoquinone
IUPAC Name:	7-hydroxy-2-methoxy-9,10-dihydrophenanthrene-1,4-dione
Synonyms:	Ephemeranthoquinone
Standard InCHIKey:	SBMILRCXQPFDME-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-19-13-7-12(17)14-10-5-3-9(16)6-8(10)2-4-11(14)15(13)18/h3,5-7,16H,2,4H2,1H3
SMILES:	COC1=CC(=O)C2=C(C1=O)CCc1c2ccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472431
PubChem CID:	10038025
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO15918	Nidema boothii	Species	Orchidaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[14987052]
NPO8084	Axinyssa tethyoides	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15918	Nidema boothii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26581	Cyperus pilosus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5052	Physocarpus intermedius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3197	Polyporus confluens	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7189	Saraca asoca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2128	Lebeckia plukenetiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3906	Securigera securidaca	Species	Fabaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	10900.0	nM	PMID[449404]

☑ 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 NPC164947 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	250
0.1-0.2	1392
0.2-0.3	3239
0.3-0.4	8567
0.4-0.5	10227
0.5-0.6	5704
0.6-0.7	10462
0.7-0.8	2700
0.8-0.85	132
0.85-0.9	17
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC474766
0.9576	High Similarity	NPC135062
0.9194	High Similarity	NPC27659
0.906	High Similarity	NPC325646
0.906	High Similarity	NPC28951
0.873	High Similarity	NPC237225
0.8702	High Similarity	NPC264022
0.8626	High Similarity	NPC38158
0.8594	High Similarity	NPC198305
0.8571	High Similarity	NPC51037
0.8571	High Similarity	NPC15837
0.855	High Similarity	NPC22644
0.8548	High Similarity	NPC91478
0.8538	High Similarity	NPC171968
0.8492	Intermediate Similarity	NPC123506
0.8485	Intermediate Similarity	NPC475549
0.848	Intermediate Similarity	NPC273683
0.8468	Intermediate Similarity	NPC120545
0.8462	Intermediate Similarity	NPC309430
0.845	Intermediate Similarity	NPC253488
0.8438	Intermediate Similarity	NPC165257
0.8425	Intermediate Similarity	NPC231774
0.8413	Intermediate Similarity	NPC164014
0.8413	Intermediate Similarity	NPC310540
0.8403	Intermediate Similarity	NPC231717
0.84	Intermediate Similarity	NPC282577
0.839	Intermediate Similarity	NPC21162
0.8385	Intermediate Similarity	NPC244699
0.8372	Intermediate Similarity	NPC171460
0.8358	Intermediate Similarity	NPC173980
0.8333	Intermediate Similarity	NPC11824
0.8321	Intermediate Similarity	NPC477407
0.832	Intermediate Similarity	NPC154696
0.8306	Intermediate Similarity	NPC285829
0.8306	Intermediate Similarity	NPC206778
0.8295	Intermediate Similarity	NPC96024
0.8281	Intermediate Similarity	NPC71610
0.8281	Intermediate Similarity	NPC254492
0.8281	Intermediate Similarity	NPC3224
0.8268	Intermediate Similarity	NPC199273
0.8268	Intermediate Similarity	NPC474803
0.8258	Intermediate Similarity	NPC254603
0.8258	Intermediate Similarity	NPC59459
0.8258	Intermediate Similarity	NPC53896
0.8254	Intermediate Similarity	NPC307174
0.8248	Intermediate Similarity	NPC201297
0.824	Intermediate Similarity	NPC259703
0.824	Intermediate Similarity	NPC32322
0.8231	Intermediate Similarity	NPC34414
0.8231	Intermediate Similarity	NPC146647
0.8231	Intermediate Similarity	NPC99731
0.8222	Intermediate Similarity	NPC475104
0.8217	Intermediate Similarity	NPC72667
0.8217	Intermediate Similarity	NPC324209
0.8195	Intermediate Similarity	NPC50924
0.8189	Intermediate Similarity	NPC375356
0.8188	Intermediate Similarity	NPC478164
0.8182	Intermediate Similarity	NPC239302
0.8182	Intermediate Similarity	NPC312560
0.8175	Intermediate Similarity	NPC110810
0.8168	Intermediate Similarity	NPC172673
0.816	Intermediate Similarity	NPC318552
0.816	Intermediate Similarity	NPC190501
0.8154	Intermediate Similarity	NPC24869
0.8154	Intermediate Similarity	NPC234175
0.8145	Intermediate Similarity	NPC328694
0.814	Intermediate Similarity	NPC306765
0.8136	Intermediate Similarity	NPC34715
0.812	Intermediate Similarity	NPC4170
0.812	Intermediate Similarity	NPC78307
0.811	Intermediate Similarity	NPC139171
0.811	Intermediate Similarity	NPC300274
0.811	Intermediate Similarity	NPC176208
0.8106	Intermediate Similarity	NPC205360
0.8106	Intermediate Similarity	NPC93015
0.8095	Intermediate Similarity	NPC294361
0.8095	Intermediate Similarity	NPC236520
0.8095	Intermediate Similarity	NPC190971
0.808	Intermediate Similarity	NPC42657
0.8077	Intermediate Similarity	NPC84672
0.8077	Intermediate Similarity	NPC78364
0.8077	Intermediate Similarity	NPC69424
0.8077	Intermediate Similarity	NPC176130
0.8077	Intermediate Similarity	NPC262936
0.8077	Intermediate Similarity	NPC30491
0.8074	Intermediate Similarity	NPC471670
0.8071	Intermediate Similarity	NPC478160
0.8062	Intermediate Similarity	NPC287473
0.8062	Intermediate Similarity	NPC103540
0.8049	Intermediate Similarity	NPC23402
0.803	Intermediate Similarity	NPC55949
0.803	Intermediate Similarity	NPC475741
0.803	Intermediate Similarity	NPC117609
0.8029	Intermediate Similarity	NPC114620
0.8029	Intermediate Similarity	NPC477408
0.8029	Intermediate Similarity	NPC103337
0.8028	Intermediate Similarity	NPC474556
0.8017	Intermediate Similarity	NPC212718
0.8017	Intermediate Similarity	NPC470355
0.8016	Intermediate Similarity	NPC478121
0.8015	Intermediate Similarity	NPC282923
0.8015	Intermediate Similarity	NPC475957
0.8015	Intermediate Similarity	NPC119542
0.8015	Intermediate Similarity	NPC48248
0.8	Intermediate Similarity	NPC177925
0.8	Intermediate Similarity	NPC1991
0.8	Intermediate Similarity	NPC95172
0.8	Intermediate Similarity	NPC22222
0.8	Intermediate Similarity	NPC280869
0.8	Intermediate Similarity	NPC88141
0.8	Intermediate Similarity	NPC281513
0.8	Intermediate Similarity	NPC96915
0.8	Intermediate Similarity	NPC471935
0.8	Intermediate Similarity	NPC471930
0.8	Intermediate Similarity	NPC283088
0.8	Intermediate Similarity	NPC471929
0.7985	Intermediate Similarity	NPC52407
0.7985	Intermediate Similarity	NPC263817
0.7984	Intermediate Similarity	NPC477453
0.7984	Intermediate Similarity	NPC74507
0.7984	Intermediate Similarity	NPC108288
0.7984	Intermediate Similarity	NPC234890
0.7984	Intermediate Similarity	NPC142956
0.7984	Intermediate Similarity	NPC173978
0.7983	Intermediate Similarity	NPC226699
0.7972	Intermediate Similarity	NPC80370
0.797	Intermediate Similarity	NPC471851
0.7969	Intermediate Similarity	NPC217756
0.7969	Intermediate Similarity	NPC121168
0.7966	Intermediate Similarity	NPC13495
0.7958	Intermediate Similarity	NPC58373
0.7955	Intermediate Similarity	NPC25736
0.7955	Intermediate Similarity	NPC276238
0.7955	Intermediate Similarity	NPC278928
0.7941	Intermediate Similarity	NPC141934
0.7941	Intermediate Similarity	NPC315275
0.7941	Intermediate Similarity	NPC86524
0.7939	Intermediate Similarity	NPC471530
0.7937	Intermediate Similarity	NPC473974
0.7937	Intermediate Similarity	NPC258366
0.7937	Intermediate Similarity	NPC31296
0.7937	Intermediate Similarity	NPC79933
0.7934	Intermediate Similarity	NPC222905
0.7926	Intermediate Similarity	NPC202225
0.7923	Intermediate Similarity	NPC137416
0.7917	Intermediate Similarity	NPC58310
0.7917	Intermediate Similarity	NPC475718
0.7917	Intermediate Similarity	NPC295977
0.7913	Intermediate Similarity	NPC260000
0.791	Intermediate Similarity	NPC242358
0.791	Intermediate Similarity	NPC88864
0.791	Intermediate Similarity	NPC110609
0.791	Intermediate Similarity	NPC246693
0.791	Intermediate Similarity	NPC165612
0.791	Intermediate Similarity	NPC58685
0.791	Intermediate Similarity	NPC477406
0.7907	Intermediate Similarity	NPC471187
0.7907	Intermediate Similarity	NPC198014
0.7903	Intermediate Similarity	NPC161304
0.7903	Intermediate Similarity	NPC322197
0.7899	Intermediate Similarity	NPC70843
0.7899	Intermediate Similarity	NPC470407
0.7899	Intermediate Similarity	NPC6984
0.7899	Intermediate Similarity	NPC29989
0.7899	Intermediate Similarity	NPC95178
0.7899	Intermediate Similarity	NPC69332
0.7895	Intermediate Similarity	NPC199253
0.7895	Intermediate Similarity	NPC136588
0.7895	Intermediate Similarity	NPC108129
0.7895	Intermediate Similarity	NPC470725
0.7891	Intermediate Similarity	NPC253627
0.7886	Intermediate Similarity	NPC242136
0.7883	Intermediate Similarity	NPC186647
0.7883	Intermediate Similarity	NPC471152
0.7883	Intermediate Similarity	NPC36868
0.7883	Intermediate Similarity	NPC290601
0.7879	Intermediate Similarity	NPC201419
0.7879	Intermediate Similarity	NPC3009
0.7879	Intermediate Similarity	NPC469930
0.7872	Intermediate Similarity	NPC29932
0.7862	Intermediate Similarity	NPC306011
0.7862	Intermediate Similarity	NPC472838
0.7862	Intermediate Similarity	NPC230848
0.7857	Intermediate Similarity	NPC308572
0.7857	Intermediate Similarity	NPC141817
0.7857	Intermediate Similarity	NPC229218
0.7857	Intermediate Similarity	NPC192597
0.7857	Intermediate Similarity	NPC41567
0.7857	Intermediate Similarity	NPC176030
0.7857	Intermediate Similarity	NPC169214
0.7852	Intermediate Similarity	NPC294226
0.7852	Intermediate Similarity	NPC475457
0.7852	Intermediate Similarity	NPC477139
0.7852	Intermediate Similarity	NPC18982
0.7852	Intermediate Similarity	NPC193169
0.7852	Intermediate Similarity	NPC475627
0.7852	Intermediate Similarity	NPC475346
0.7852	Intermediate Similarity	NPC314048
0.7846	Intermediate Similarity	NPC68756
0.7846	Intermediate Similarity	NPC111088

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 NPC164947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	953
0.2-0.3	1221
0.3-0.4	2444
0.4-0.5	2292
0.5-0.6	1321
0.6-0.7	591
0.7-0.8	71
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8306	Intermediate Similarity	NPD2932	Approved
0.816	Intermediate Similarity	NPD3019	Approved
0.8062	Intermediate Similarity	NPD1470	Approved
0.8031	Intermediate Similarity	NPD1201	Approved
0.7984	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD1283	Approved
0.7795	Intermediate Similarity	NPD1651	Approved
0.7681	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3026	Approved
0.7674	Intermediate Similarity	NPD3023	Approved
0.766	Intermediate Similarity	NPD8166	Discontinued
0.7656	Intermediate Similarity	NPD3024	Approved
0.7656	Intermediate Similarity	NPD3025	Approved
0.7615	Intermediate Similarity	NPD1281	Approved
0.76	Intermediate Similarity	NPD1241	Discontinued
0.7574	Intermediate Similarity	NPD6663	Approved
0.7537	Intermediate Similarity	NPD5736	Approved
0.75	Intermediate Similarity	NPD3764	Approved
0.7462	Intermediate Similarity	NPD4626	Approved
0.7444	Intermediate Similarity	NPD1876	Approved
0.7431	Intermediate Similarity	NPD3300	Phase 2
0.7385	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5406	Approved
0.7376	Intermediate Similarity	NPD5405	Approved
0.7376	Intermediate Similarity	NPD5408	Approved
0.7376	Intermediate Similarity	NPD5404	Approved
0.7376	Intermediate Similarity	NPD2935	Discontinued
0.7324	Intermediate Similarity	NPD2346	Discontinued
0.7308	Intermediate Similarity	NPD9545	Approved
0.7308	Intermediate Similarity	NPD3091	Approved
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1237	Approved
0.7293	Intermediate Similarity	NPD3972	Approved
0.7292	Intermediate Similarity	NPD7003	Approved
0.7292	Intermediate Similarity	NPD3750	Approved
0.7266	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4060	Phase 1
0.7259	Intermediate Similarity	NPD1164	Approved
0.7258	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3020	Approved
0.7239	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD288	Approved
0.7203	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1471	Phase 3
0.7183	Intermediate Similarity	NPD1510	Phase 2
0.7163	Intermediate Similarity	NPD1607	Approved
0.7162	Intermediate Similarity	NPD6273	Approved
0.7154	Intermediate Similarity	NPD9493	Approved
0.7153	Intermediate Similarity	NPD9494	Approved
0.7153	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2859	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD2860	Approved
0.7143	Intermediate Similarity	NPD844	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7132	Intermediate Similarity	NPD5951	Approved
0.7121	Intermediate Similarity	NPD5691	Approved
0.712	Intermediate Similarity	NPD2342	Discontinued
0.7111	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1755	Approved
0.7095	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3092	Approved
0.7086	Intermediate Similarity	NPD7028	Phase 2
0.708	Intermediate Similarity	NPD2798	Approved
0.7071	Intermediate Similarity	NPD8032	Phase 2
0.7068	Intermediate Similarity	NPD4059	Approved
0.7068	Intermediate Similarity	NPD3095	Discontinued
0.7063	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD2933	Approved
0.7059	Intermediate Similarity	NPD2934	Approved
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7095	Approved
0.7049	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1608	Approved
0.702	Intermediate Similarity	NPD3226	Approved
0.7007	Intermediate Similarity	NPD3094	Phase 2
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6986	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7635	Approved
0.6972	Remote Similarity	NPD6355	Discontinued
0.697	Remote Similarity	NPD5536	Phase 2
0.6966	Remote Similarity	NPD2344	Approved
0.6953	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7819	Suspended
0.6947	Remote Similarity	NPD255	Approved
0.6947	Remote Similarity	NPD256	Approved
0.6944	Remote Similarity	NPD3748	Approved
0.694	Remote Similarity	NPD2286	Discontinued
0.694	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4628	Phase 3
0.6929	Remote Similarity	NPD74	Approved
0.6929	Remote Similarity	NPD9266	Approved
0.6918	Remote Similarity	NPD1549	Phase 2
0.6912	Remote Similarity	NPD1481	Phase 2
0.6908	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7458	Discontinued
0.6899	Remote Similarity	NPD228	Approved
0.6897	Remote Similarity	NPD2531	Phase 2
0.6897	Remote Similarity	NPD2438	Suspended
0.6892	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6190	Approved
0.6884	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD2313	Discontinued
0.6879	Remote Similarity	NPD3268	Approved
0.6875	Remote Similarity	NPD4750	Phase 3
0.687	Remote Similarity	NPD111	Approved
0.687	Remote Similarity	NPD2629	Approved
0.6866	Remote Similarity	NPD4093	Discontinued
0.686	Remote Similarity	NPD1809	Phase 2
0.6853	Remote Similarity	NPD230	Phase 1
0.685	Remote Similarity	NPD9263	Approved
0.685	Remote Similarity	NPD9264	Approved
0.685	Remote Similarity	NPD9267	Approved
0.6849	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1535	Discovery
0.6838	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD257	Approved
0.6835	Remote Similarity	NPD4624	Approved
0.6835	Remote Similarity	NPD258	Approved
0.6833	Remote Similarity	NPD845	Approved
0.6831	Remote Similarity	NPD6233	Phase 2
0.6829	Remote Similarity	NPD2066	Phase 3
0.6828	Remote Similarity	NPD4308	Phase 3
0.6821	Remote Similarity	NPD1512	Approved
0.6815	Remote Similarity	NPD17	Approved
0.6815	Remote Similarity	NPD1751	Approved
0.6815	Remote Similarity	NPD7075	Discontinued
0.6809	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1929	Approved
0.68	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1930	Approved
0.68	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4878	Approved
0.6788	Remote Similarity	NPD9717	Approved
0.6788	Remote Similarity	NPD9269	Phase 2
0.6783	Remote Similarity	NPD825	Approved
0.6783	Remote Similarity	NPD826	Approved
0.6783	Remote Similarity	NPD4140	Approved
0.6781	Remote Similarity	NPD6099	Approved
0.6781	Remote Similarity	NPD4477	Approved
0.6781	Remote Similarity	NPD4476	Approved
0.6781	Remote Similarity	NPD6100	Approved
0.6779	Remote Similarity	NPD2354	Approved
0.6779	Remote Similarity	NPD2309	Approved
0.6774	Remote Similarity	NPD1242	Phase 1
0.6765	Remote Similarity	NPD3847	Discontinued
0.6763	Remote Similarity	NPD1203	Approved
0.6761	Remote Similarity	NPD411	Approved
0.6755	Remote Similarity	NPD2532	Approved
0.6755	Remote Similarity	NPD2533	Approved
0.6755	Remote Similarity	NPD2534	Approved
0.6752	Remote Similarity	NPD3882	Suspended
0.675	Remote Similarity	NPD6232	Discontinued
0.6748	Remote Similarity	NPD9495	Approved
0.6746	Remote Similarity	NPD164	Approved
0.6744	Remote Similarity	NPD1792	Phase 2
0.6741	Remote Similarity	NPD9268	Approved
0.6733	Remote Similarity	NPD7236	Approved
0.6731	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7473	Discontinued
0.672	Remote Similarity	NPD940	Approved
0.672	Remote Similarity	NPD846	Approved
0.6713	Remote Similarity	NPD4062	Phase 3
0.6713	Remote Similarity	NPD259	Phase 1
0.6694	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7008	Discontinued
0.6689	Remote Similarity	NPD1511	Approved
0.6687	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5283	Phase 1
0.6645	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6599	Discontinued
0.6645	Remote Similarity	NPD4380	Phase 2
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6643	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4879	Approved
0.6642	Remote Similarity	NPD9568	Approved
0.6641	Remote Similarity	NPD1445	Approved
0.6641	Remote Similarity	NPD1444	Approved
0.6639	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2353	Approved
0.6622	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5762	Approved
0.6622	Remote Similarity	NPD5763	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