NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	3.515
LogD:	3.066
LogS:	-3.782
# 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:	2.315
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:	-5.016
MDCK Permeability:	1.1700512004608754e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.421
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	96.81810760498047%
Volume Distribution (VD):	0.554
Pgp-substrate:	5.627641201019287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.298
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.639
CYP2D6-substrate:	0.835
CYP3A4-inhibitor:	0.207
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	11.614
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.88
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.588
Skin Sensitization:	0.948
Carcinogencity:	0.853
Eye Corrosion:	0.092
Eye Irritation:	0.971
Respiratory Toxicity:	0.676

Download Data

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

Natural Product: NPC135062

Natural Product ID:	NPC135062
*Common Name:**	Ephemeranthoquinone B
IUPAC Name:	5-hydroxy-2-methoxy-9,10-dihydrophenanthrene-1,4-dione
Synonyms:	Ephemeranthoquinone B
Standard InCHIKey:	MSPMPZYZAACVTB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-19-12-7-11(17)14-9(15(12)18)6-5-8-3-2-4-10(16)13(8)14/h2-4,7,16H,5-6H2,1H3
SMILES:	COC1=CC(=O)C2=C(C1=O)CCc1c2c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2042413
PubChem CID:	56597129
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
NPO33438	cymbidium great flower marie laurencin	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537363]

☑ 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
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2800.0	nM	PMID[570834]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4880.0	nM	PMID[570834]

☑ 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 NPC135062 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	254
0.1-0.2	1390
0.2-0.3	3224
0.3-0.4	8546
0.4-0.5	10399
0.5-0.6	5910
0.6-0.7	10298
0.7-0.8	2470
0.8-0.85	169
0.85-0.9	31
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC164947
0.9256	High Similarity	NPC474766
0.9113	High Similarity	NPC237225
0.8968	High Similarity	NPC198305
0.8952	High Similarity	NPC51037
0.8906	High Similarity	NPC171968
0.8828	High Similarity	NPC309430
0.8819	High Similarity	NPC27659
0.881	High Similarity	NPC165257
0.88	High Similarity	NPC231774
0.879	High Similarity	NPC310540
0.8712	High Similarity	NPC173980
0.8689	High Similarity	NPC206778
0.8689	High Similarity	NPC285829
0.8667	High Similarity	NPC28951
0.8667	High Similarity	NPC325646
0.8651	High Similarity	NPC3224
0.8629	High Similarity	NPC307174
0.8615	High Similarity	NPC254603
0.8594	High Similarity	NPC146647
0.8594	High Similarity	NPC34414
0.856	High Similarity	NPC375356
0.8504	High Similarity	NPC306765
0.8485	Intermediate Similarity	NPC22644
0.848	Intermediate Similarity	NPC300274
0.8462	Intermediate Similarity	NPC205360
0.8462	Intermediate Similarity	NPC244699
0.8425	Intermediate Similarity	NPC123506
0.8425	Intermediate Similarity	NPC103540
0.8421	Intermediate Similarity	NPC38158
0.8413	Intermediate Similarity	NPC273683
0.8385	Intermediate Similarity	NPC55949
0.8385	Intermediate Similarity	NPC475741
0.8385	Intermediate Similarity	NPC253488
0.8372	Intermediate Similarity	NPC282923
0.8372	Intermediate Similarity	NPC48248
0.837	Intermediate Similarity	NPC477408
0.8361	Intermediate Similarity	NPC108288
0.8359	Intermediate Similarity	NPC15837
0.8359	Intermediate Similarity	NPC1991
0.8359	Intermediate Similarity	NPC96915
0.8358	Intermediate Similarity	NPC264022
0.8346	Intermediate Similarity	NPC281513
0.8346	Intermediate Similarity	NPC234890
0.8346	Intermediate Similarity	NPC74507
0.8346	Intermediate Similarity	NPC22222
0.8346	Intermediate Similarity	NPC474803
0.8346	Intermediate Similarity	NPC142956
0.8333	Intermediate Similarity	NPC59459
0.8333	Intermediate Similarity	NPC282577
0.8333	Intermediate Similarity	NPC217756
0.8333	Intermediate Similarity	NPC53896
0.8333	Intermediate Similarity	NPC91478
0.8308	Intermediate Similarity	NPC171460
0.8308	Intermediate Similarity	NPC278928
0.8308	Intermediate Similarity	NPC99731
0.8295	Intermediate Similarity	NPC471530
0.8284	Intermediate Similarity	NPC141934
0.8281	Intermediate Similarity	NPC287473
0.8279	Intermediate Similarity	NPC161304
0.8271	Intermediate Similarity	NPC50924
0.8261	Intermediate Similarity	NPC478164
0.8258	Intermediate Similarity	NPC110609
0.8258	Intermediate Similarity	NPC246693
0.8258	Intermediate Similarity	NPC88864
0.8258	Intermediate Similarity	NPC477406
0.8258	Intermediate Similarity	NPC58685
0.8258	Intermediate Similarity	NPC242358
0.8254	Intermediate Similarity	NPC154696
0.8254	Intermediate Similarity	NPC120545
0.8244	Intermediate Similarity	NPC199253
0.8244	Intermediate Similarity	NPC136588
0.8235	Intermediate Similarity	NPC114620
0.8235	Intermediate Similarity	NPC103337
0.8231	Intermediate Similarity	NPC96024
0.8231	Intermediate Similarity	NPC24869
0.822	Intermediate Similarity	NPC34715
0.8217	Intermediate Similarity	NPC71610
0.8217	Intermediate Similarity	NPC254492
0.8211	Intermediate Similarity	NPC477453
0.8203	Intermediate Similarity	NPC152525
0.8203	Intermediate Similarity	NPC68756
0.8203	Intermediate Similarity	NPC199273
0.8203	Intermediate Similarity	NPC173978
0.8195	Intermediate Similarity	NPC193169
0.8189	Intermediate Similarity	NPC46634
0.8188	Intermediate Similarity	NPC201297
0.8182	Intermediate Similarity	NPC93015
0.8182	Intermediate Similarity	NPC205992
0.8175	Intermediate Similarity	NPC259703
0.8175	Intermediate Similarity	NPC32322
0.8175	Intermediate Similarity	NPC190971
0.8162	Intermediate Similarity	NPC61590
0.816	Intermediate Similarity	NPC232178
0.8154	Intermediate Similarity	NPC72667
0.8148	Intermediate Similarity	NPC475549
0.8148	Intermediate Similarity	NPC315275
0.8143	Intermediate Similarity	NPC478160
0.8125	Intermediate Similarity	NPC275145
0.8125	Intermediate Similarity	NPC182646
0.812	Intermediate Similarity	NPC70622
0.812	Intermediate Similarity	NPC477407
0.812	Intermediate Similarity	NPC312560
0.8116	Intermediate Similarity	NPC110810
0.8106	Intermediate Similarity	NPC31799
0.8106	Intermediate Similarity	NPC117609
0.8102	Intermediate Similarity	NPC470407
0.8102	Intermediate Similarity	NPC1268
0.8102	Intermediate Similarity	NPC295339
0.8095	Intermediate Similarity	NPC216297
0.8095	Intermediate Similarity	NPC473662
0.8095	Intermediate Similarity	NPC7151
0.8092	Intermediate Similarity	NPC201419
0.8088	Intermediate Similarity	NPC284184
0.8088	Intermediate Similarity	NPC475957
0.8088	Intermediate Similarity	NPC305060
0.8088	Intermediate Similarity	NPC301341
0.808	Intermediate Similarity	NPC41567
0.8074	Intermediate Similarity	NPC283088
0.8071	Intermediate Similarity	NPC29932
0.8071	Intermediate Similarity	NPC477409
0.8062	Intermediate Similarity	NPC164014
0.806	Intermediate Similarity	NPC115458
0.806	Intermediate Similarity	NPC52407
0.806	Intermediate Similarity	NPC78307
0.806	Intermediate Similarity	NPC225051
0.806	Intermediate Similarity	NPC263817
0.8047	Intermediate Similarity	NPC176208
0.8045	Intermediate Similarity	NPC17083
0.8042	Intermediate Similarity	NPC80370
0.8033	Intermediate Similarity	NPC231717
0.8031	Intermediate Similarity	NPC165197
0.803	Intermediate Similarity	NPC25736
0.8017	Intermediate Similarity	NPC21162
0.8015	Intermediate Similarity	NPC193358
0.8015	Intermediate Similarity	NPC78364
0.8015	Intermediate Similarity	NPC69424
0.8015	Intermediate Similarity	NPC232996
0.8015	Intermediate Similarity	NPC45537
0.8015	Intermediate Similarity	NPC176130
0.8015	Intermediate Similarity	NPC324209
0.8015	Intermediate Similarity	NPC86524
0.8015	Intermediate Similarity	NPC84672
0.8015	Intermediate Similarity	NPC471670
0.8014	Intermediate Similarity	NPC474630
0.8	Intermediate Similarity	NPC160199
0.8	Intermediate Similarity	NPC274876
0.8	Intermediate Similarity	NPC202225
0.7986	Intermediate Similarity	NPC124365
0.7986	Intermediate Similarity	NPC283292
0.7984	Intermediate Similarity	NPC240163
0.7972	Intermediate Similarity	NPC474556
0.7971	Intermediate Similarity	NPC29771
0.7971	Intermediate Similarity	NPC299405
0.7971	Intermediate Similarity	NPC26924
0.7971	Intermediate Similarity	NPC216312
0.7971	Intermediate Similarity	NPC306835
0.7971	Intermediate Similarity	NPC476477
0.7971	Intermediate Similarity	NPC471602
0.7971	Intermediate Similarity	NPC256463
0.7971	Intermediate Similarity	NPC111422
0.797	Intermediate Similarity	NPC108129
0.7969	Intermediate Similarity	NPC25168
0.7967	Intermediate Similarity	NPC11824
0.7958	Intermediate Similarity	NPC136878
0.7955	Intermediate Similarity	NPC234175
0.7953	Intermediate Similarity	NPC478121
0.7941	Intermediate Similarity	NPC80035
0.7939	Intermediate Similarity	NPC227741
0.7939	Intermediate Similarity	NPC49647
0.7939	Intermediate Similarity	NPC136342
0.7939	Intermediate Similarity	NPC295202
0.7939	Intermediate Similarity	NPC160499
0.7931	Intermediate Similarity	NPC230848
0.7929	Intermediate Similarity	NPC474300
0.7929	Intermediate Similarity	NPC69755
0.7926	Intermediate Similarity	NPC294226
0.7926	Intermediate Similarity	NPC4170
0.7926	Intermediate Similarity	NPC314048
0.7923	Intermediate Similarity	NPC181334
0.7923	Intermediate Similarity	NPC117794
0.7917	Intermediate Similarity	NPC141523
0.7914	Intermediate Similarity	NPC42262
0.7914	Intermediate Similarity	NPC147542
0.7914	Intermediate Similarity	NPC37992
0.7914	Intermediate Similarity	NPC220496
0.7914	Intermediate Similarity	NPC32749
0.7914	Intermediate Similarity	NPC241349
0.7914	Intermediate Similarity	NPC327916
0.7914	Intermediate Similarity	NPC156872
0.7914	Intermediate Similarity	NPC315578
0.791	Intermediate Similarity	NPC471851
0.7907	Intermediate Similarity	NPC121168
0.7907	Intermediate Similarity	NPC139171
0.7907	Intermediate Similarity	NPC297193
0.7902	Intermediate Similarity	NPC476821
0.7902	Intermediate Similarity	NPC58373
0.7902	Intermediate Similarity	NPC77598
0.7899	Intermediate Similarity	NPC475104
0.7899	Intermediate Similarity	NPC230811

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 NPC135062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	950
0.2-0.3	1248
0.3-0.4	2469
0.4-0.5	2304
0.5-0.6	1282
0.6-0.7	568
0.7-0.8	64
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD1470	Approved
0.8361	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD1201	Approved
0.7953	Intermediate Similarity	NPD2932	Approved
0.7883	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3019	Approved
0.7754	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD3300	Phase 2
0.7519	Intermediate Similarity	NPD1283	Approved
0.7462	Intermediate Similarity	NPD1651	Approved
0.7458	Intermediate Similarity	NPD288	Approved
0.7405	Intermediate Similarity	NPD4626	Approved
0.7381	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD844	Approved
0.7364	Intermediate Similarity	NPD9493	Approved
0.7361	Intermediate Similarity	NPD8166	Discontinued
0.7348	Intermediate Similarity	NPD3023	Approved
0.7348	Intermediate Similarity	NPD3026	Approved
0.7339	Intermediate Similarity	NPD2342	Discontinued
0.7328	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3024	Approved
0.7328	Intermediate Similarity	NPD3025	Approved
0.7324	Intermediate Similarity	NPD5406	Approved
0.7324	Intermediate Similarity	NPD5408	Approved
0.7324	Intermediate Similarity	NPD5405	Approved
0.7324	Intermediate Similarity	NPD5404	Approved
0.7324	Intermediate Similarity	NPD2935	Discontinued
0.7319	Intermediate Similarity	NPD3764	Approved
0.7315	Intermediate Similarity	NPD3226	Approved
0.7293	Intermediate Similarity	NPD1281	Approved
0.7279	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1471	Phase 3
0.7266	Intermediate Similarity	NPD1241	Discontinued
0.7266	Intermediate Similarity	NPD6663	Approved
0.7241	Intermediate Similarity	NPD7003	Approved
0.7241	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3750	Approved
0.7236	Intermediate Similarity	NPD1237	Approved
0.7226	Intermediate Similarity	NPD5736	Approved
0.7214	Intermediate Similarity	NPD4060	Phase 1
0.7214	Intermediate Similarity	NPD943	Approved
0.7209	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1164	Approved
0.7194	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD7635	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7133	Intermediate Similarity	NPD1510	Phase 2
0.7132	Intermediate Similarity	NPD1876	Approved
0.7113	Intermediate Similarity	NPD1607	Approved
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7390	Discontinued
0.7092	Intermediate Similarity	NPD1240	Approved
0.7087	Intermediate Similarity	NPD4750	Phase 3
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2797	Approved
0.7077	Intermediate Similarity	NPD5951	Approved
0.7071	Intermediate Similarity	NPD3268	Approved
0.7068	Intermediate Similarity	NPD5691	Approved
0.7063	Intermediate Similarity	NPD9264	Approved
0.7063	Intermediate Similarity	NPD9267	Approved
0.7063	Intermediate Similarity	NPD9263	Approved
0.7059	Intermediate Similarity	NPD1755	Approved
0.7059	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD845	Approved
0.7047	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2344	Approved
0.7015	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4308	Phase 3
0.7008	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9545	Approved
0.6992	Remote Similarity	NPD3091	Approved
0.6985	Remote Similarity	NPD3972	Approved
0.6985	Remote Similarity	NPD9717	Approved
0.6985	Remote Similarity	NPD1608	Approved
0.6978	Remote Similarity	NPD9494	Approved
0.6966	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD6100	Approved
0.6957	Remote Similarity	NPD1203	Approved
0.695	Remote Similarity	NPD411	Approved
0.695	Remote Similarity	NPD6798	Discontinued
0.6939	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD447	Suspended
0.6918	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3020	Approved
0.6903	Remote Similarity	NPD7819	Suspended
0.6899	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3748	Approved
0.6892	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6273	Approved
0.6871	Remote Similarity	NPD1549	Phase 2
0.6863	Remote Similarity	NPD7458	Discontinued
0.6861	Remote Similarity	NPD4878	Approved
0.686	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2979	Phase 3
0.6846	Remote Similarity	NPD2309	Approved
0.6835	Remote Similarity	NPD3266	Approved
0.6835	Remote Similarity	NPD3267	Approved
0.6825	Remote Similarity	NPD164	Approved
0.6822	Remote Similarity	NPD3022	Approved
0.6822	Remote Similarity	NPD3021	Approved
0.6821	Remote Similarity	NPD2533	Approved
0.6821	Remote Similarity	NPD2534	Approved
0.6821	Remote Similarity	NPD2532	Approved
0.6818	Remote Similarity	NPD497	Approved
0.6818	Remote Similarity	NPD2629	Approved
0.6818	Remote Similarity	NPD7028	Phase 2
0.6818	Remote Similarity	NPD9281	Approved
0.6815	Remote Similarity	NPD3882	Suspended
0.6813	Remote Similarity	NPD6232	Discontinued
0.6807	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2859	Approved
0.6803	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2860	Approved
0.6803	Remote Similarity	NPD5763	Approved
0.6803	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1809	Phase 2
0.6803	Remote Similarity	NPD5762	Approved
0.679	Remote Similarity	NPD7473	Discontinued
0.6788	Remote Similarity	NPD3092	Approved
0.6788	Remote Similarity	NPD1611	Approved
0.6786	Remote Similarity	NPD8150	Discontinued
0.6783	Remote Similarity	NPD8032	Phase 2
0.6776	Remote Similarity	NPD1512	Approved
0.6774	Remote Similarity	NPD2066	Phase 3
0.6772	Remote Similarity	NPD7075	Discontinued
0.6767	Remote Similarity	NPD6671	Approved
0.6765	Remote Similarity	NPD4059	Approved
0.6765	Remote Similarity	NPD1778	Approved
0.6765	Remote Similarity	NPD3095	Discontinued
0.6765	Remote Similarity	NPD17	Approved
0.6761	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4625	Phase 3
0.6761	Remote Similarity	NPD7095	Approved
0.6747	Remote Similarity	NPD4954	Approved
0.6747	Remote Similarity	NPD5028	Approved
0.6747	Remote Similarity	NPD5026	Approved
0.6747	Remote Similarity	NPD4955	Approved
0.6747	Remote Similarity	NPD5034	Approved
0.6747	Remote Similarity	NPD36	Approved
0.6746	Remote Similarity	NPD1930	Approved
0.6746	Remote Similarity	NPD9261	Approved
0.6746	Remote Similarity	NPD1929	Approved
0.6746	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD498	Approved
0.6742	Remote Similarity	NPD496	Approved
0.6742	Remote Similarity	NPD495	Approved
0.6736	Remote Similarity	NPD4307	Phase 2
0.6735	Remote Similarity	NPD4477	Approved
0.6735	Remote Similarity	NPD1551	Phase 2
0.6735	Remote Similarity	NPD4476	Approved
0.6733	Remote Similarity	NPD6190	Approved
0.6721	Remote Similarity	NPD2933	Approved
0.6721	Remote Similarity	NPD2934	Approved
0.6715	Remote Similarity	NPD3496	Discontinued
0.6714	Remote Similarity	NPD3094	Phase 2
0.6694	Remote Similarity	NPD9495	Approved
0.6692	Remote Similarity	NPD1792	Phase 2
0.6691	Remote Similarity	NPD4749	Approved
0.669	Remote Similarity	NPD230	Phase 1
0.6689	Remote Similarity	NPD7236	Approved
0.6688	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5029	Approved
0.6687	Remote Similarity	NPD5027	Approved
0.6687	Remote Similarity	NPD5033	Approved
0.6687	Remote Similarity	NPD5031	Approved
0.6687	Remote Similarity	NPD5030	Phase 2
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD520	Approved
0.6667	Remote Similarity	NPD4956	Approved
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD940	Approved
0.6667	Remote Similarity	NPD5536	Phase 2
0.6646	Remote Similarity	NPD5402	Approved
0.6646	Remote Similarity	NPD6959	Discontinued
0.6646	Remote Similarity	NPD3751	Discontinued
0.6645	Remote Similarity	NPD1511	Approved
0.6645	Remote Similarity	NPD2649	Approved
0.6645	Remote Similarity	NPD2651	Approved
0.6644	Remote Similarity	NPD2897	Discontinued
0.6643	Remote Similarity	NPD7008	Discontinued
0.6642	Remote Similarity	NPD709	Approved
0.6642	Remote Similarity	NPD255	Approved
0.6642	Remote Similarity	NPD256	Approved
0.6642	Remote Similarity	NPD2286	Discontinued
0.6641	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7879	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data