NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.08
Volume:	261.72
LogP:	2.297
LogD:	1.431
LogS:	-2.526
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	2.722
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.003
MDCK Permeability:	6.043607299943687e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.735
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.878
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.7361068725586%
Volume Distribution (VD):	0.407
Pgp-substrate:	4.483479022979736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.804
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.437
CYP2C9-substrate:	0.835
CYP2D6-inhibitor:	0.268
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	13.483
Half-life (T1/2):	0.93

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.831
AMES Toxicity:	0.721
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.928
Carcinogencity:	0.066
Eye Corrosion:	0.04
Eye Irritation:	0.924
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC472046

Natural Product ID:	NPC472046
*Common Name:**	Karuquinone A
IUPAC Name:	5,8-dihydroxy-6-methyl-7-(2-oxopropyl)-2,3-dihydronaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	ZQIYBGRIURFSLB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O5/c1-6(15)5-8-7(2)13(18)11-9(16)3-4-10(17)12(11)14(8)19/h18-19H,3-5H2,1-2H3
SMILES:	CC(=O)Cc1c(O)c2C(=O)CCC(=O)c2c(c1C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3334765
PubChem CID:	86275690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348469]
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25163667]
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28257197]
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7122	Fusarium solani	Species	Nectriaceae	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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4000.0	nM	PMID[522223]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	1800.0	nM	PMID[522223]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[522223]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1900.0	nM	PMID[522223]

☑ 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 NPC472046 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	307
0.1-0.2	1638
0.2-0.3	4319
0.3-0.4	12020
0.4-0.5	8769
0.5-0.6	7685
0.6-0.7	6355
0.7-0.8	1413
0.8-0.85	158
0.85-0.9	29
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC472047
0.8952	High Similarity	NPC278928
0.8889	High Similarity	NPC88864
0.881	High Similarity	NPC205992
0.876	High Similarity	NPC155211
0.871	High Similarity	NPC306765
0.871	High Similarity	NPC1991
0.871	High Similarity	NPC96915
0.8699	High Similarity	NPC68756
0.8699	High Similarity	NPC142956
0.8699	High Similarity	NPC152525
0.8689	High Similarity	NPC307174
0.8672	High Similarity	NPC193169
0.864	High Similarity	NPC471530
0.8583	High Similarity	NPC199253
0.8583	High Similarity	NPC198305
0.8583	High Similarity	NPC136588
0.8583	High Similarity	NPC55949
0.8571	High Similarity	NPC282923
0.8561	High Similarity	NPC143438
0.856	High Similarity	NPC160499
0.8548	High Similarity	NPC310540
0.8527	High Similarity	NPC225051
0.8527	High Similarity	NPC52407
0.8512	High Similarity	NPC232178
0.8504	High Similarity	NPC146647
0.8504	High Similarity	NPC34414
0.848	Intermediate Similarity	NPC131799
0.8473	Intermediate Similarity	NPC474311
0.8473	Intermediate Similarity	NPC474813
0.8473	Intermediate Similarity	NPC272268
0.8473	Intermediate Similarity	NPC472308
0.8468	Intermediate Similarity	NPC375356
0.8462	Intermediate Similarity	NPC50924
0.845	Intermediate Similarity	NPC70622
0.8443	Intermediate Similarity	NPC285829
0.8443	Intermediate Similarity	NPC206778
0.8438	Intermediate Similarity	NPC31799
0.8438	Intermediate Similarity	NPC31539
0.8425	Intermediate Similarity	NPC48248
0.8413	Intermediate Similarity	NPC227741
0.8413	Intermediate Similarity	NPC295202
0.8413	Intermediate Similarity	NPC3224
0.8413	Intermediate Similarity	NPC231774
0.8413	Intermediate Similarity	NPC136342
0.8413	Intermediate Similarity	NPC49647
0.8409	Intermediate Similarity	NPC305060
0.8409	Intermediate Similarity	NPC245923
0.84	Intermediate Similarity	NPC234890
0.84	Intermediate Similarity	NPC173978
0.84	Intermediate Similarity	NPC74507
0.8397	Intermediate Similarity	NPC14377
0.8397	Intermediate Similarity	NPC258502
0.8397	Intermediate Similarity	NPC80035
0.8387	Intermediate Similarity	NPC300274
0.8372	Intermediate Similarity	NPC17083
0.8372	Intermediate Similarity	NPC85342
0.8359	Intermediate Similarity	NPC99731
0.8333	Intermediate Similarity	NPC254847
0.8333	Intermediate Similarity	NPC103540
0.8321	Intermediate Similarity	NPC288089
0.8308	Intermediate Similarity	NPC58685
0.8308	Intermediate Similarity	NPC309430
0.8308	Intermediate Similarity	NPC242358
0.8308	Intermediate Similarity	NPC110609
0.8308	Intermediate Similarity	NPC246693
0.8296	Intermediate Similarity	NPC92079
0.8281	Intermediate Similarity	NPC237225
0.8271	Intermediate Similarity	NPC53414
0.8271	Intermediate Similarity	NPC471905
0.8271	Intermediate Similarity	NPC147418
0.8271	Intermediate Similarity	NPC53206
0.8258	Intermediate Similarity	NPC161632
0.8254	Intermediate Similarity	NPC199273
0.8244	Intermediate Similarity	NPC114183
0.8244	Intermediate Similarity	NPC267205
0.8244	Intermediate Similarity	NPC53896
0.8244	Intermediate Similarity	NPC115458
0.8244	Intermediate Similarity	NPC314048
0.8244	Intermediate Similarity	NPC254603
0.8244	Intermediate Similarity	NPC171968
0.824	Intermediate Similarity	NPC282577
0.8231	Intermediate Similarity	NPC244699
0.8209	Intermediate Similarity	NPC61398
0.8209	Intermediate Similarity	NPC4214
0.8209	Intermediate Similarity	NPC416
0.8209	Intermediate Similarity	NPC123714
0.8209	Intermediate Similarity	NPC13715
0.8195	Intermediate Similarity	NPC315275
0.8195	Intermediate Similarity	NPC86524
0.8188	Intermediate Similarity	NPC471683
0.8182	Intermediate Similarity	NPC161304
0.8182	Intermediate Similarity	NPC240163
0.8182	Intermediate Similarity	NPC12070
0.8182	Intermediate Similarity	NPC270899
0.8175	Intermediate Similarity	NPC143898
0.8175	Intermediate Similarity	NPC275145
0.8162	Intermediate Similarity	NPC283292
0.8162	Intermediate Similarity	NPC124365
0.8162	Intermediate Similarity	NPC187843
0.8154	Intermediate Similarity	NPC117609
0.8154	Intermediate Similarity	NPC475741
0.8154	Intermediate Similarity	NPC108129
0.8148	Intermediate Similarity	NPC242994
0.8148	Intermediate Similarity	NPC26924
0.8148	Intermediate Similarity	NPC138099
0.8148	Intermediate Similarity	NPC190457
0.8145	Intermediate Similarity	NPC216297
0.8145	Intermediate Similarity	NPC7151
0.8145	Intermediate Similarity	NPC473662
0.8134	Intermediate Similarity	NPC471452
0.8125	Intermediate Similarity	NPC254492
0.8125	Intermediate Similarity	NPC51037
0.812	Intermediate Similarity	NPC281513
0.812	Intermediate Similarity	NPC283088
0.812	Intermediate Similarity	NPC249272
0.812	Intermediate Similarity	NPC22222
0.8116	Intermediate Similarity	NPC475813
0.8115	Intermediate Similarity	NPC108288
0.8115	Intermediate Similarity	NPC477453
0.811	Intermediate Similarity	NPC12818
0.811	Intermediate Similarity	NPC236189
0.8106	Intermediate Similarity	NPC294226
0.8095	Intermediate Similarity	NPC91478
0.8092	Intermediate Similarity	NPC41847
0.8092	Intermediate Similarity	NPC93015
0.8088	Intermediate Similarity	NPC315578
0.8088	Intermediate Similarity	NPC181560
0.8088	Intermediate Similarity	NPC169452
0.808	Intermediate Similarity	NPC190971
0.8074	Intermediate Similarity	NPC206207
0.8062	Intermediate Similarity	NPC176130
0.8062	Intermediate Similarity	NPC84672
0.8062	Intermediate Similarity	NPC83572
0.8062	Intermediate Similarity	NPC72667
0.8062	Intermediate Similarity	NPC78364
0.8062	Intermediate Similarity	NPC69424
0.806	Intermediate Similarity	NPC191976
0.8049	Intermediate Similarity	NPC269414
0.8047	Intermediate Similarity	NPC123506
0.8045	Intermediate Similarity	NPC202225
0.8045	Intermediate Similarity	NPC166480
0.8045	Intermediate Similarity	NPC44437
0.8045	Intermediate Similarity	NPC282780
0.8043	Intermediate Similarity	NPC469885
0.8043	Intermediate Similarity	NPC471682
0.8031	Intermediate Similarity	NPC273683
0.8031	Intermediate Similarity	NPC477153
0.803	Intermediate Similarity	NPC477406
0.8029	Intermediate Similarity	NPC246638
0.8029	Intermediate Similarity	NPC290550
0.8029	Intermediate Similarity	NPC305845
0.8029	Intermediate Similarity	NPC204045
0.8016	Intermediate Similarity	NPC120545
0.8015	Intermediate Similarity	NPC114620
0.8015	Intermediate Similarity	NPC103337
0.8015	Intermediate Similarity	NPC296158
0.8014	Intermediate Similarity	NPC112816
0.8	Intermediate Similarity	NPC96024
0.8	Intermediate Similarity	NPC300540
0.8	Intermediate Similarity	NPC53001
0.8	Intermediate Similarity	NPC247250
0.8	Intermediate Similarity	NPC767
0.7986	Intermediate Similarity	NPC244691
0.7986	Intermediate Similarity	NPC471906
0.7984	Intermediate Similarity	NPC15837
0.7984	Intermediate Similarity	NPC41567
0.7971	Intermediate Similarity	NPC69755
0.7971	Intermediate Similarity	NPC193555
0.7971	Intermediate Similarity	NPC257644
0.7971	Intermediate Similarity	NPC135524
0.7971	Intermediate Similarity	NPC474961
0.7971	Intermediate Similarity	NPC19631
0.7971	Intermediate Similarity	NPC239136
0.797	Intermediate Similarity	NPC48036
0.797	Intermediate Similarity	NPC263817
0.797	Intermediate Similarity	NPC59459
0.7956	Intermediate Similarity	NPC96421
0.7956	Intermediate Similarity	NPC183345
0.7955	Intermediate Similarity	NPC474517
0.7955	Intermediate Similarity	NPC72669
0.7955	Intermediate Similarity	NPC471851
0.7941	Intermediate Similarity	NPC173980
0.7941	Intermediate Similarity	NPC87723
0.7939	Intermediate Similarity	NPC303910
0.7939	Intermediate Similarity	NPC276238
0.7939	Intermediate Similarity	NPC171460
0.7937	Intermediate Similarity	NPC229649
0.7926	Intermediate Similarity	NPC118919
0.7923	Intermediate Similarity	NPC19432
0.7914	Intermediate Similarity	NPC66593
0.7914	Intermediate Similarity	NPC238629
0.791	Intermediate Similarity	NPC287604
0.791	Intermediate Similarity	NPC472262
0.791	Intermediate Similarity	NPC474519
0.791	Intermediate Similarity	NPC475645
0.791	Intermediate Similarity	NPC161964
0.7902	Intermediate Similarity	NPC294646
0.7902	Intermediate Similarity	NPC315520
0.7899	Intermediate Similarity	NPC110810

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 NPC472046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	1069
0.2-0.3	1883
0.3-0.4	3029
0.4-0.5	1850
0.5-0.6	754
0.6-0.7	226
0.7-0.8	23
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
0.8333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1470	Approved
0.816	Intermediate Similarity	NPD1201	Approved
0.8115	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7390	Discontinued
0.7681	Intermediate Similarity	NPD2346	Discontinued
0.7482	Intermediate Similarity	NPD5404	Approved
0.7482	Intermediate Similarity	NPD5408	Approved
0.7482	Intermediate Similarity	NPD5406	Approved
0.7482	Intermediate Similarity	NPD5405	Approved
0.7466	Intermediate Similarity	NPD3226	Approved
0.7431	Intermediate Similarity	NPD2534	Approved
0.7431	Intermediate Similarity	NPD2533	Approved
0.7431	Intermediate Similarity	NPD2532	Approved
0.7431	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3300	Phase 2
0.7372	Intermediate Similarity	NPD943	Approved
0.7364	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7635	Approved
0.7357	Intermediate Similarity	NPD2935	Discontinued
0.7286	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1164	Approved
0.7203	Intermediate Similarity	NPD2800	Approved
0.7165	Intermediate Similarity	NPD1398	Phase 1
0.7101	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2313	Discontinued
0.7063	Intermediate Similarity	NPD2344	Approved
0.7051	Intermediate Similarity	NPD6232	Discontinued
0.7045	Intermediate Similarity	NPD2932	Approved
0.7045	Intermediate Similarity	NPD3019	Approved
0.7025	Intermediate Similarity	NPD7473	Discontinued
0.7021	Intermediate Similarity	NPD1607	Approved
0.7021	Intermediate Similarity	NPD6651	Approved
0.7014	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7340	Approved
0.6987	Remote Similarity	NPD6959	Discontinued
0.696	Remote Similarity	NPD2342	Discontinued
0.6944	Remote Similarity	NPD1471	Phase 3
0.6923	Remote Similarity	NPD2799	Discontinued
0.6905	Remote Similarity	NPD9266	Approved
0.6905	Remote Similarity	NPD74	Approved
0.6885	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1240	Approved
0.6871	Remote Similarity	NPD2309	Approved
0.687	Remote Similarity	NPD9493	Approved
0.6846	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD497	Approved
0.6846	Remote Similarity	NPD5951	Approved
0.6835	Remote Similarity	NPD5710	Approved
0.6835	Remote Similarity	NPD5711	Approved
0.6825	Remote Similarity	NPD9264	Approved
0.6825	Remote Similarity	NPD9263	Approved
0.6825	Remote Similarity	NPD9267	Approved
0.6812	Remote Similarity	NPD2798	Approved
0.6806	Remote Similarity	NPD1510	Phase 2
0.6806	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1283	Approved
0.6777	Remote Similarity	NPD288	Approved
0.6769	Remote Similarity	NPD496	Approved
0.6769	Remote Similarity	NPD495	Approved
0.6769	Remote Similarity	NPD498	Approved
0.6738	Remote Similarity	NPD7985	Registered
0.6716	Remote Similarity	NPD1651	Approved
0.671	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2801	Approved
0.671	Remote Similarity	NPD7819	Suspended
0.6694	Remote Similarity	NPD844	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1511	Approved
0.6647	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.662	Remote Similarity	NPD411	Approved
0.662	Remote Similarity	NPD3764	Approved
0.6619	Remote Similarity	NPD1203	Approved
0.6618	Remote Similarity	NPD3023	Approved
0.6618	Remote Similarity	NPD3026	Approved
0.6615	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6212	Phase 3
0.6608	Remote Similarity	NPD6213	Phase 3
0.6608	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8150	Discontinued
0.6599	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD447	Suspended
0.6594	Remote Similarity	NPD1755	Approved
0.6593	Remote Similarity	NPD3025	Approved
0.6593	Remote Similarity	NPD3024	Approved
0.6591	Remote Similarity	NPD9281	Approved
0.6579	Remote Similarity	NPD1512	Approved
0.6577	Remote Similarity	NPD7003	Approved
0.657	Remote Similarity	NPD6535	Approved
0.657	Remote Similarity	NPD6534	Approved
0.6569	Remote Similarity	NPD1281	Approved
0.6569	Remote Similarity	NPD1611	Approved
0.6567	Remote Similarity	NPD7644	Approved
0.6562	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1549	Phase 2
0.6544	Remote Similarity	NPD4626	Approved
0.6544	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1934	Approved
0.6531	Remote Similarity	NPD6099	Approved
0.6531	Remote Similarity	NPD6100	Approved
0.6529	Remote Similarity	NPD845	Approved
0.6529	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3972	Approved
0.6522	Remote Similarity	NPD9269	Phase 2
0.6522	Remote Similarity	NPD9717	Approved
0.6516	Remote Similarity	NPD4380	Phase 2
0.6512	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1929	Approved
0.6508	Remote Similarity	NPD9261	Approved
0.6508	Remote Similarity	NPD1930	Approved
0.6508	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5031	Approved
0.6506	Remote Similarity	NPD5027	Approved
0.6506	Remote Similarity	NPD5029	Approved
0.6471	Remote Similarity	NPD9268	Approved
0.6467	Remote Similarity	NPD4955	Approved
0.6467	Remote Similarity	NPD5034	Approved
0.6467	Remote Similarity	NPD5028	Approved
0.6467	Remote Similarity	NPD4954	Approved
0.6467	Remote Similarity	NPD5026	Approved
0.6467	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD36	Approved
0.6462	Remote Similarity	NPD4750	Phase 3
0.6457	Remote Similarity	NPD7699	Phase 2
0.6457	Remote Similarity	NPD7700	Phase 2
0.6457	Remote Similarity	NPD1237	Approved
0.6456	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7458	Discontinued
0.6449	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1876	Approved
0.6429	Remote Similarity	NPD6696	Suspended
0.6429	Remote Similarity	NPD1932	Approved
0.6424	Remote Similarity	NPD5844	Phase 1
0.6423	Remote Similarity	NPD1809	Phase 2
0.6419	Remote Similarity	NPD1551	Phase 2
0.6418	Remote Similarity	NPD3317	Approved
0.6412	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5030	Phase 2
0.6403	Remote Similarity	NPD1608	Approved
0.6403	Remote Similarity	NPD4878	Approved
0.64	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5494	Approved
0.6397	Remote Similarity	NPD9545	Approved
0.6384	Remote Similarity	NPD6778	Approved
0.6384	Remote Similarity	NPD6776	Approved
0.6384	Remote Similarity	NPD6779	Approved
0.6384	Remote Similarity	NPD6777	Approved
0.6384	Remote Similarity	NPD6780	Approved
0.6384	Remote Similarity	NPD6782	Approved
0.6384	Remote Similarity	NPD6781	Approved
0.6375	Remote Similarity	NPD3749	Approved
0.637	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.637	Remote Similarity	NPD230	Phase 1
0.6358	Remote Similarity	NPD3750	Approved
0.6352	Remote Similarity	NPD2296	Approved
0.6351	Remote Similarity	NPD4308	Phase 3
0.6345	Remote Similarity	NPD6663	Approved
0.6331	Remote Similarity	NPD8312	Approved
0.6331	Remote Similarity	NPD8313	Approved
0.6329	Remote Similarity	NPD6844	Discontinued
0.6328	Remote Similarity	NPD164	Approved
0.6319	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5038	Approved
0.6316	Remote Similarity	NPD5037	Approved
0.6312	Remote Similarity	NPD3882	Suspended
0.6301	Remote Similarity	NPD2979	Phase 3
0.6294	Remote Similarity	NPD5736	Approved
0.6294	Remote Similarity	NPD9494	Approved
0.6289	Remote Similarity	NPD1465	Phase 2
0.6278	Remote Similarity	NPD7696	Phase 3
0.6278	Remote Similarity	NPD7698	Approved
0.6278	Remote Similarity	NPD7435	Discontinued
0.6278	Remote Similarity	NPD7697	Approved
0.6276	Remote Similarity	NPD3268	Approved
0.6273	Remote Similarity	NPD7075	Discontinued
0.627	Remote Similarity	NPD3020	Approved
0.627	Remote Similarity	NPD2066	Phase 3
0.6266	Remote Similarity	NPD7411	Suspended
0.626	Remote Similarity	NPD2329	Discontinued
0.6259	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5036	Approved
0.625	Remote Similarity	NPD4628	Phase 3
0.625	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8166	Discontinued
0.625	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7871	Phase 2
0.6243	Remote Similarity	NPD7870	Phase 2
0.6243	Remote Similarity	NPD6836	Approved
0.6241	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD520	Approved
0.6232	Remote Similarity	NPD5691	Approved
0.6228	Remote Similarity	NPD6020	Phase 2
0.6218	Remote Similarity	NPD920	Approved
0.6212	Remote Similarity	NPD3022	Approved
0.6212	Remote Similarity	NPD3021	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