NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.05
Volume:	241.787
LogP:	2.401
LogD:	2.335
LogS:	-2.926
# 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:	0.605
Synthetic Accessibility Score:	2.192
Fsp3:	0.0
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:	-5.086
MDCK Permeability:	8.982323379314039e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	96.6189956665039%
Volume Distribution (VD):	0.534
Pgp-substrate:	3.337980031967163%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.157
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.558
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.69
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	13.424
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.748
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.924
Carcinogencity:	0.122
Eye Corrosion:	0.009
Eye Irritation:	0.955
Respiratory Toxicity:	0.111

Download Data

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

Natural Product: NPC8745

Natural Product ID:	NPC8745
*Common Name:**	2,4,6,3'-Tetrahydroxybenzophenone
IUPAC Name:	(3-hydroxyphenyl)-(2,4,6-trihydroxyphenyl)methanone
Synonyms:	2,4,6,3'-Tetrahydroxybenzophenone
Standard InCHIKey:	QWRYPHZJTWQLFX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10O5/c14-8-3-1-2-7(4-8)13(18)12-10(16)5-9(15)6-11(12)17/h1-6,14-17H
SMILES:	Oc1cccc(c1)C(=O)c1c(O)cc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445711
PubChem CID:	440991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	stems	n.a.	n.a.	PMID[12932126]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20681570]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	Twigs and leaves	Taichung, Taiwan	1993-Aug	PMID[9322359]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5049	Garcinia multiflora	Species	Clusiaceae	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
LD50	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	66300.0	nM	PMID[494768]
NPT140	Organism	Artemia	Artemia	LD50	>	100.0	uM	PMID[494768]

☑ 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 NPC8745 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	450
0.1-0.2	1924
0.2-0.3	5026
0.3-0.4	12157
0.4-0.5	5790
0.5-0.6	5275
0.6-0.7	6093
0.7-0.8	4984
0.8-0.85	749
0.85-0.9	187
0.9-0.95	56
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC10926
0.9832	High Similarity	NPC13238
0.9664	High Similarity	NPC32032
0.9664	High Similarity	NPC133909
0.958	High Similarity	NPC45438
0.958	High Similarity	NPC115159
0.958	High Similarity	NPC156139
0.958	High Similarity	NPC143427
0.958	High Similarity	NPC242895
0.958	High Similarity	NPC73532
0.958	High Similarity	NPC224273
0.958	High Similarity	NPC19174
0.958	High Similarity	NPC267552
0.952	High Similarity	NPC135801
0.9496	High Similarity	NPC297186
0.9496	High Similarity	NPC248363
0.944	High Similarity	NPC34070
0.944	High Similarity	NPC469526
0.9412	High Similarity	NPC159525
0.937	High Similarity	NPC282780
0.937	High Similarity	NPC44437
0.937	High Similarity	NPC166480
0.936	High Similarity	NPC26697
0.936	High Similarity	NPC233056
0.9328	High Similarity	NPC158222
0.928	High Similarity	NPC474998
0.928	High Similarity	NPC92624
0.928	High Similarity	NPC109123
0.9274	High Similarity	NPC105157
0.9274	High Similarity	NPC190043
0.9274	High Similarity	NPC30501
0.9274	High Similarity	NPC23126
0.9274	High Similarity	NPC98254
0.9274	High Similarity	NPC169250
0.9274	High Similarity	NPC103356
0.9274	High Similarity	NPC162612
0.9274	High Similarity	NPC266689
0.9274	High Similarity	NPC72158
0.9274	High Similarity	NPC100067
0.9256	High Similarity	NPC196976
0.9206	High Similarity	NPC259942
0.92	High Similarity	NPC473017
0.92	High Similarity	NPC21305
0.92	High Similarity	NPC221777
0.9194	High Similarity	NPC62952
0.9194	High Similarity	NPC267846
0.9174	High Similarity	NPC146642
0.9167	High Similarity	NPC161617
0.9154	High Similarity	NPC53206
0.9154	High Similarity	NPC53414
0.9127	High Similarity	NPC120488
0.9127	High Similarity	NPC102829
0.912	High Similarity	NPC107672
0.912	High Similarity	NPC116513
0.9091	High Similarity	NPC294037
0.9083	High Similarity	NPC40649
0.9083	High Similarity	NPC209486
0.9077	High Similarity	NPC264112
0.9077	High Similarity	NPC254847
0.9077	High Similarity	NPC65005
0.9077	High Similarity	NPC194764
0.9055	High Similarity	NPC147757
0.9055	High Similarity	NPC244441
0.9048	High Similarity	NPC179898
0.9024	High Similarity	NPC309765
0.9016	High Similarity	NPC149246
0.9015	High Similarity	NPC242994
0.9015	High Similarity	NPC138099
0.9008	High Similarity	NPC195262
0.9008	High Similarity	NPC290030
0.9008	High Similarity	NPC471905
0.9008	High Similarity	NPC188814
0.8992	High Similarity	NPC213485
0.8992	High Similarity	NPC139074
0.8992	High Similarity	NPC40524
0.8992	High Similarity	NPC267205
0.8984	High Similarity	NPC475042
0.8976	High Similarity	NPC476119
0.896	High Similarity	NPC477454
0.8947	High Similarity	NPC181560
0.8947	High Similarity	NPC169452
0.8947	High Similarity	NPC203063
0.8943	High Similarity	NPC303737
0.8943	High Similarity	NPC215392
0.8939	High Similarity	NPC212767
0.8939	High Similarity	NPC175552
0.8915	High Similarity	NPC175738
0.8915	High Similarity	NPC478190
0.8898	High Similarity	NPC95537
0.8889	High Similarity	NPC473691
0.8872	High Similarity	NPC143438
0.8872	High Similarity	NPC472903
0.8872	High Similarity	NPC190457
0.8871	High Similarity	NPC91105
0.8864	High Similarity	NPC193792
0.8864	High Similarity	NPC87545
0.8864	High Similarity	NPC235428
0.8864	High Similarity	NPC473391
0.8864	High Similarity	NPC472364
0.8855	High Similarity	NPC283590
0.8855	High Similarity	NPC70859
0.8855	High Similarity	NPC61153
0.8855	High Similarity	NPC130899
0.8815	High Similarity	NPC137649
0.8815	High Similarity	NPC49108
0.8815	High Similarity	NPC193555
0.8815	High Similarity	NPC73061
0.881	High Similarity	NPC475733
0.881	High Similarity	NPC262671
0.881	High Similarity	NPC201728
0.8806	High Similarity	NPC109232
0.88	High Similarity	NPC65761
0.88	High Similarity	NPC472029
0.879	High Similarity	NPC226275
0.8788	High Similarity	NPC39426
0.8788	High Similarity	NPC234560
0.8788	High Similarity	NPC118919
0.8788	High Similarity	NPC191976
0.877	High Similarity	NPC241089
0.8769	High Similarity	NPC262359
0.8769	High Similarity	NPC313618
0.876	High Similarity	NPC247477
0.876	High Similarity	NPC17840
0.875	High Similarity	NPC159855
0.875	High Similarity	NPC238629
0.875	High Similarity	NPC118288
0.875	High Similarity	NPC276111
0.875	High Similarity	NPC169479
0.875	High Similarity	NPC287722
0.875	High Similarity	NPC41263
0.8741	High Similarity	NPC472904
0.8741	High Similarity	NPC246638
0.8741	High Similarity	NPC290550
0.8741	High Similarity	NPC204045
0.8741	High Similarity	NPC305845
0.8731	High Similarity	NPC90665
0.8731	High Similarity	NPC12175
0.8731	High Similarity	NPC309154
0.8731	High Similarity	NPC55162
0.8731	High Similarity	NPC278323
0.8731	High Similarity	NPC279668
0.8722	High Similarity	NPC170742
0.8722	High Similarity	NPC44960
0.8722	High Similarity	NPC474110
0.8722	High Similarity	NPC213603
0.872	High Similarity	NPC283514
0.8712	High Similarity	NPC286336
0.8712	High Similarity	NPC161632
0.8712	High Similarity	NPC470210
0.8702	High Similarity	NPC87231
0.8702	High Similarity	NPC129132
0.8702	High Similarity	NPC212631
0.8702	High Similarity	NPC205468
0.8702	High Similarity	NPC257756
0.8692	High Similarity	NPC275504
0.8689	High Similarity	NPC121259
0.8686	High Similarity	NPC21599
0.8686	High Similarity	NPC193703
0.8682	High Similarity	NPC99731
0.8676	High Similarity	NPC135524
0.8667	High Similarity	NPC477956
0.8661	High Similarity	NPC103540
0.8657	High Similarity	NPC7013
0.8657	High Similarity	NPC162680
0.8657	High Similarity	NPC303644
0.8657	High Similarity	NPC116632
0.8657	High Similarity	NPC294409
0.8657	High Similarity	NPC209560
0.8657	High Similarity	NPC472419
0.8657	High Similarity	NPC181124
0.8647	High Similarity	NPC223836
0.8647	High Similarity	NPC239495
0.8647	High Similarity	NPC9985
0.8647	High Similarity	NPC131039
0.864	High Similarity	NPC198336
0.8636	High Similarity	NPC312318
0.8636	High Similarity	NPC159623
0.8636	High Similarity	NPC175098
0.8636	High Similarity	NPC82225
0.8636	High Similarity	NPC144051
0.8636	High Similarity	NPC192304
0.8636	High Similarity	NPC20560
0.8636	High Similarity	NPC18877
0.8636	High Similarity	NPC188646
0.8636	High Similarity	NPC263670
0.8636	High Similarity	NPC242294
0.8636	High Similarity	NPC475088
0.8636	High Similarity	NPC139813
0.8636	High Similarity	NPC204960
0.8636	High Similarity	NPC472365
0.8636	High Similarity	NPC56031
0.8636	High Similarity	NPC28753
0.8636	High Similarity	NPC337373
0.8636	High Similarity	NPC294593
0.8626	High Similarity	NPC64359
0.8626	High Similarity	NPC308037
0.8623	High Similarity	NPC155144
0.8618	High Similarity	NPC283844
0.8603	High Similarity	NPC101366
0.8594	High Similarity	NPC160499

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 NPC8745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	442
0.1-0.2	964
0.2-0.3	1599
0.3-0.4	2931
0.4-0.5	1850
0.5-0.6	952
0.6-0.7	295
0.7-0.8	96
0.8-0.85	15
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.952	High Similarity	NPD943	Approved
0.9077	High Similarity	NPD1509	Clinical (unspecified phase)
0.8788	High Similarity	NPD1510	Phase 2
0.8769	High Similarity	NPD1240	Approved
0.8661	High Similarity	NPD1470	Approved
0.8647	High Similarity	NPD651	Clinical (unspecified phase)
0.8636	High Similarity	NPD1607	Approved
0.8492	Intermediate Similarity	NPD1201	Approved
0.8456	Intermediate Similarity	NPD1549	Phase 2
0.8382	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8306	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD7390	Discontinued
0.8286	Intermediate Similarity	NPD1511	Approved
0.8231	Intermediate Similarity	NPD1164	Approved
0.8169	Intermediate Similarity	NPD1512	Approved
0.814	Intermediate Similarity	NPD9269	Phase 2
0.811	Intermediate Similarity	NPD9268	Approved
0.8099	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD5404	Approved
0.8043	Intermediate Similarity	NPD5408	Approved
0.8043	Intermediate Similarity	NPD5405	Approved
0.8043	Intermediate Similarity	NPD5406	Approved
0.7972	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1934	Approved
0.7951	Intermediate Similarity	NPD74	Approved
0.7951	Intermediate Similarity	NPD9266	Approved
0.7945	Intermediate Similarity	NPD4380	Phase 2
0.7919	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD2796	Approved
0.7914	Intermediate Similarity	NPD2935	Discontinued
0.7905	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2801	Approved
0.7869	Intermediate Similarity	NPD9267	Approved
0.7869	Intermediate Similarity	NPD9263	Approved
0.7869	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD9264	Approved
0.7817	Intermediate Similarity	NPD3750	Approved
0.7815	Intermediate Similarity	NPD1242	Phase 1
0.7786	Intermediate Similarity	NPD1551	Phase 2
0.7785	Intermediate Similarity	NPD7819	Suspended
0.7754	Intermediate Similarity	NPD230	Phase 1
0.7748	Intermediate Similarity	NPD3749	Approved
0.7734	Intermediate Similarity	NPD9493	Approved
0.773	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1203	Approved
0.7655	Intermediate Similarity	NPD6799	Approved
0.7651	Intermediate Similarity	NPD7411	Suspended
0.7632	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7075	Discontinued
0.7622	Intermediate Similarity	NPD2800	Approved
0.7616	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD940	Approved
0.7603	Intermediate Similarity	NPD846	Approved
0.758	Intermediate Similarity	NPD3818	Discontinued
0.7578	Intermediate Similarity	NPD9281	Approved
0.7557	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6232	Discontinued
0.7541	Intermediate Similarity	NPD9261	Approved
0.7536	Intermediate Similarity	NPD3764	Approved
0.7517	Intermediate Similarity	NPD2309	Approved
0.7516	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1243	Approved
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7481	Intermediate Similarity	NPD9545	Approved
0.7467	Intermediate Similarity	NPD6599	Discontinued
0.7465	Intermediate Similarity	NPD2799	Discontinued
0.7465	Intermediate Similarity	NPD3748	Approved
0.7452	Intermediate Similarity	NPD6166	Phase 2
0.7452	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6651	Approved
0.741	Intermediate Similarity	NPD2313	Discontinued
0.7386	Intermediate Similarity	NPD3817	Phase 2
0.7383	Intermediate Similarity	NPD920	Approved
0.7372	Intermediate Similarity	NPD6959	Discontinued
0.7372	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD6801	Discontinued
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7768	Phase 2
0.7333	Intermediate Similarity	NPD9717	Approved
0.7323	Intermediate Similarity	NPD4750	Phase 3
0.732	Intermediate Similarity	NPD1465	Phase 2
0.7308	Intermediate Similarity	NPD5494	Approved
0.7286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD7074	Phase 3
0.726	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD447	Suspended
0.7248	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2346	Discontinued
0.723	Intermediate Similarity	NPD3300	Phase 2
0.7222	Intermediate Similarity	NPD5953	Discontinued
0.7205	Intermediate Similarity	NPD7054	Approved
0.72	Intermediate Similarity	NPD1237	Approved
0.7172	Intermediate Similarity	NPD6100	Approved
0.7172	Intermediate Similarity	NPD6099	Approved
0.717	Intermediate Similarity	NPD3926	Phase 2
0.7163	Intermediate Similarity	NPD411	Approved
0.716	Intermediate Similarity	NPD7472	Approved
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5403	Approved
0.7152	Intermediate Similarity	NPD1247	Approved
0.7134	Intermediate Similarity	NPD919	Approved
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5401	Approved
0.7117	Intermediate Similarity	NPD6797	Phase 2
0.7113	Intermediate Similarity	NPD520	Approved
0.7111	Intermediate Similarity	NPD2932	Approved
0.7111	Intermediate Similarity	NPD3019	Approved
0.7103	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7286	Phase 2
0.708	Intermediate Similarity	NPD1608	Approved
0.708	Intermediate Similarity	NPD3972	Approved
0.7073	Intermediate Similarity	NPD6559	Discontinued
0.7073	Intermediate Similarity	NPD7251	Discontinued
0.7071	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD2859	Approved
0.7049	Intermediate Similarity	NPD2860	Approved
0.7047	Intermediate Similarity	NPD6190	Approved
0.703	Intermediate Similarity	NPD7808	Phase 3
0.7027	Intermediate Similarity	NPD2654	Approved
0.7021	Intermediate Similarity	NPD6832	Phase 2
0.7021	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3020	Approved
0.7014	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7007	Intermediate Similarity	NPD422	Phase 1
0.7007	Intermediate Similarity	NPD1471	Phase 3
0.6994	Remote Similarity	NPD6020	Phase 2
0.6986	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD4628	Phase 3
0.698	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2933	Approved
0.6967	Remote Similarity	NPD2934	Approved
0.6963	Remote Similarity	NPD1548	Phase 1
0.695	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2296	Approved
0.6928	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD3021	Approved
0.6923	Remote Similarity	NPD3022	Approved
0.6911	Remote Similarity	NPD844	Approved
0.6906	Remote Similarity	NPD1755	Approved
0.6894	Remote Similarity	NPD5711	Approved
0.6894	Remote Similarity	NPD5710	Approved
0.689	Remote Similarity	NPD5844	Phase 1
0.6867	Remote Similarity	NPD1196	Approved
0.6861	Remote Similarity	NPD17	Approved
0.6857	Remote Similarity	NPD1876	Approved
0.6855	Remote Similarity	NPD288	Approved
0.6842	Remote Similarity	NPD1543	Discontinued
0.6835	Remote Similarity	NPD4288	Approved
0.6828	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1613	Approved
0.6825	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2797	Approved
0.6806	Remote Similarity	NPD1296	Phase 2
0.68	Remote Similarity	NPD1195	Approved
0.6786	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4287	Approved
0.6783	Remote Similarity	NPD4908	Phase 1
0.6755	Remote Similarity	NPD3400	Discontinued
0.6748	Remote Similarity	NPD1202	Approved
0.6738	Remote Similarity	NPD1283	Approved
0.6738	Remote Similarity	NPD3225	Approved
0.6736	Remote Similarity	NPD3027	Phase 3
0.6732	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7458	Discontinued
0.6727	Remote Similarity	NPD3751	Discontinued
0.6723	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1930	Approved
0.6719	Remote Similarity	NPD1929	Approved
0.6716	Remote Similarity	NPD1241	Discontinued
0.6715	Remote Similarity	NPD1759	Phase 1
0.6714	Remote Similarity	NPD1481	Phase 2
0.6712	Remote Similarity	NPD4307	Phase 2
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3026	Approved
0.6691	Remote Similarity	NPD3023	Approved
0.669	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3267	Approved
0.669	Remote Similarity	NPD3266	Approved
0.6688	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD1651	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