NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	440.18
Volume:	459.01
LogP:	5.38
LogD:	3.302
LogS:	-3.934
# Rotatable Bonds:	8
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	3.293
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.039
MDCK Permeability:	1.0648277566360775e-05
Pgp-inhibitor:	0.392
Pgp-substrate:	0.709
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.853

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.53253936767578%
Volume Distribution (VD):	0.429
Pgp-substrate:	1.198305368423462%

ADMET: Metabolism

CYP1A2-inhibitor:	0.761
CYP1A2-substrate:	0.401
CYP2C19-inhibitor:	0.886
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.915
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.89
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.455
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	13.602
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.277
Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.476
Skin Sensitization:	0.601
Carcinogencity:	0.112
Eye Corrosion:	0.003
Eye Irritation:	0.877
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC477956

Natural Product ID:	NPC477956
*Common Name:**	Sophoradione
IUPAC Name:	1-[2,4-dihydroxy-6-methoxy-3-(5-methyl-2-prop-1-en-2-ylhex-4-enyl)phenyl]-2-(2,4-dihydroxyphenyl)ethane-1,2-dione
Synonyms:	sophoradione
Standard InCHIKey:	NYHVTLRKAYFBIT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H28O7/c1-13(2)6-7-15(14(3)4)10-18-20(28)12-21(32-5)22(23(18)29)25(31)24(30)17-9-8-16(26)11-19(17)27/h6,8-9,11-12,15,26-29H,3,7,10H2,1-2,4-5H3
SMILES:	CC(=CCC(CC1=C(C(=C(C=C1O)OC)C(=O)C(=O)C2=C(C=C(C=C2)O)O)O)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16083185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19231	Sophora flavescens	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	29.4	ug/ml	PMID[16933887]

☑ 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 NPC477956 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	366
0.1-0.2	1503
0.2-0.3	3713
0.3-0.4	9655
0.4-0.5	8819
0.5-0.6	3478
0.6-0.7	5868
0.7-0.8	5488
0.8-0.85	2158
0.85-0.9	1173
0.9-0.95	434
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC153979
0.985	High Similarity	NPC472419
0.9776	High Similarity	NPC21350
0.9774	High Similarity	NPC150399
0.9774	High Similarity	NPC186838
0.9774	High Similarity	NPC41461
0.9774	High Similarity	NPC25287
0.9774	High Similarity	NPC12165
0.9774	High Similarity	NPC249606
0.9774	High Similarity	NPC477243
0.9774	High Similarity	NPC1486
0.9774	High Similarity	NPC274109
0.9774	High Similarity	NPC477242
0.9774	High Similarity	NPC477244
0.9774	High Similarity	NPC168105
0.9774	High Similarity	NPC66349
0.9774	High Similarity	NPC98115
0.9706	High Similarity	NPC26051
0.9706	High Similarity	NPC55832
0.9706	High Similarity	NPC268204
0.9706	High Similarity	NPC52789
0.9701	High Similarity	NPC317119
0.9699	High Similarity	NPC131039
0.9699	High Similarity	NPC13575
0.9699	High Similarity	NPC156092
0.9632	High Similarity	NPC259166
0.9632	High Similarity	NPC144118
0.9632	High Similarity	NPC219917
0.9632	High Similarity	NPC253822
0.9632	High Similarity	NPC326109
0.9632	High Similarity	NPC215311
0.9632	High Similarity	NPC48624
0.9632	High Similarity	NPC204985
0.9632	High Similarity	NPC101366
0.9632	High Similarity	NPC11056
0.9632	High Similarity	NPC213659
0.9632	High Similarity	NPC80962
0.9632	High Similarity	NPC172250
0.9627	High Similarity	NPC24394
0.9627	High Similarity	NPC213603
0.9624	High Similarity	NPC103842
0.9624	High Similarity	NPC286336
0.9562	High Similarity	NPC470087
0.9562	High Similarity	NPC470089
0.9562	High Similarity	NPC321980
0.9562	High Similarity	NPC469404
0.9559	High Similarity	NPC470211
0.9559	High Similarity	NPC472366
0.9559	High Similarity	NPC295384
0.9559	High Similarity	NPC283429
0.9549	High Similarity	NPC294593
0.9549	High Similarity	NPC139813
0.9549	High Similarity	NPC82225
0.9549	High Similarity	NPC159623
0.9549	High Similarity	NPC337373
0.9549	High Similarity	NPC188646
0.9549	High Similarity	NPC27643
0.9549	High Similarity	NPC204960
0.9549	High Similarity	NPC312318
0.9549	High Similarity	NPC18877
0.9549	High Similarity	NPC20560
0.9549	High Similarity	NPC472365
0.9549	High Similarity	NPC263670
0.9549	High Similarity	NPC175098
0.9549	High Similarity	NPC56031
0.9549	High Similarity	NPC242294
0.9549	High Similarity	NPC144051
0.9549	High Similarity	NPC192304
0.9549	High Similarity	NPC28753
0.9496	High Similarity	NPC476055
0.9496	High Similarity	NPC234629
0.9496	High Similarity	NPC328623
0.9496	High Similarity	NPC311741
0.9493	High Similarity	NPC297600
0.9489	High Similarity	NPC265178
0.9485	High Similarity	NPC243528
0.9485	High Similarity	NPC309154
0.9485	High Similarity	NPC472368
0.9485	High Similarity	NPC90665
0.9485	High Similarity	NPC12175
0.9485	High Similarity	NPC55162
0.9485	High Similarity	NPC279668
0.9485	High Similarity	NPC278323
0.9485	High Similarity	NPC471620
0.9485	High Similarity	NPC251681
0.9481	High Similarity	NPC472364
0.9481	High Similarity	NPC473391
0.9474	High Similarity	NPC129132
0.9474	High Similarity	NPC257756
0.9474	High Similarity	NPC87231
0.9474	High Similarity	NPC212631
0.9474	High Similarity	NPC205468
0.9433	High Similarity	NPC39195
0.9429	High Similarity	NPC477955
0.9429	High Similarity	NPC25844
0.9424	High Similarity	NPC301751
0.9424	High Similarity	NPC476178
0.9424	High Similarity	NPC245482
0.9424	High Similarity	NPC166138
0.9424	High Similarity	NPC18585
0.9424	High Similarity	NPC117836
0.9424	High Similarity	NPC106985
0.9424	High Similarity	NPC51887
0.9424	High Similarity	NPC475705
0.942	High Similarity	NPC110969
0.942	High Similarity	NPC126534
0.942	High Similarity	NPC282300
0.942	High Similarity	NPC40118
0.942	High Similarity	NPC232021
0.942	High Similarity	NPC49108
0.9416	High Similarity	NPC109232
0.9412	High Similarity	NPC181124
0.9412	High Similarity	NPC162680
0.9412	High Similarity	NPC294409
0.9412	High Similarity	NPC209560
0.9412	High Similarity	NPC7013
0.9412	High Similarity	NPC303644
0.9412	High Similarity	NPC23870
0.9412	High Similarity	NPC116632
0.9398	High Similarity	NPC164236
0.9398	High Similarity	NPC262359
0.9398	High Similarity	NPC27490
0.9398	High Similarity	NPC64359
0.9398	High Similarity	NPC475008
0.9398	High Similarity	NPC186097
0.9398	High Similarity	NPC475009
0.9398	High Similarity	NPC66384
0.9398	High Similarity	NPC128348
0.9398	High Similarity	NPC189106
0.9398	High Similarity	NPC309717
0.9398	High Similarity	NPC112192
0.9398	High Similarity	NPC313618
0.9398	High Similarity	NPC308037
0.9362	High Similarity	NPC308200
0.9357	High Similarity	NPC473013
0.9357	High Similarity	NPC473015
0.9357	High Similarity	NPC271288
0.9353	High Similarity	NPC11561
0.9353	High Similarity	NPC148545
0.9353	High Similarity	NPC144499
0.9353	High Similarity	NPC226636
0.9348	High Similarity	NPC69769
0.9348	High Similarity	NPC241100
0.9348	High Similarity	NPC270883
0.9348	High Similarity	NPC172986
0.9348	High Similarity	NPC261227
0.9348	High Similarity	NPC159275
0.9343	High Similarity	NPC124269
0.9338	High Similarity	NPC235428
0.9338	High Similarity	NPC472367
0.9338	High Similarity	NPC476333
0.9338	High Similarity	NPC87545
0.9333	High Similarity	NPC164136
0.9328	High Similarity	NPC215875
0.9328	High Similarity	NPC15834
0.9323	High Similarity	NPC324482
0.9301	High Similarity	NPC472279
0.9296	High Similarity	NPC266572
0.9296	High Similarity	NPC152233
0.9296	High Similarity	NPC145467
0.9291	High Similarity	NPC299011
0.9291	High Similarity	NPC316769
0.9286	High Similarity	NPC68104
0.9286	High Similarity	NPC91560
0.9286	High Similarity	NPC164980
0.9286	High Similarity	NPC75049
0.9286	High Similarity	NPC149026
0.9286	High Similarity	NPC81697
0.9286	High Similarity	NPC143896
0.9286	High Similarity	NPC107177
0.9286	High Similarity	NPC257097
0.9286	High Similarity	NPC169591
0.9286	High Similarity	NPC125894
0.9286	High Similarity	NPC223812
0.9286	High Similarity	NPC77794
0.9286	High Similarity	NPC85162
0.9286	High Similarity	NPC39329
0.9286	High Similarity	NPC175504
0.9286	High Similarity	NPC278249
0.9286	High Similarity	NPC150408
0.9286	High Similarity	NPC310130
0.9286	High Similarity	NPC221432
0.9281	High Similarity	NPC147688
0.9281	High Similarity	NPC64908
0.9281	High Similarity	NPC3188
0.9281	High Similarity	NPC118840
0.9281	High Similarity	NPC103362
0.9281	High Similarity	NPC205006
0.9281	High Similarity	NPC156590
0.9281	High Similarity	NPC26238
0.9275	High Similarity	NPC53181
0.9275	High Similarity	NPC217186
0.9275	High Similarity	NPC96565
0.9275	High Similarity	NPC220062
0.9275	High Similarity	NPC216978
0.9275	High Similarity	NPC78913
0.9275	High Similarity	NPC55018
0.9275	High Similarity	NPC18260
0.9275	High Similarity	NPC301217
0.9275	High Similarity	NPC303633

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 NPC477956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	952
0.2-0.3	1455
0.3-0.4	2583
0.4-0.5	1980
0.5-0.6	1199
0.6-0.7	447
0.7-0.8	151
0.8-0.85	38
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9398	High Similarity	NPD1240	Approved
0.9265	High Similarity	NPD1510	Phase 2
0.9259	High Similarity	NPD1607	Approved
0.922	High Similarity	NPD4378	Clinical (unspecified phase)
0.8951	High Similarity	NPD7410	Clinical (unspecified phase)
0.8929	High Similarity	NPD1549	Phase 2
0.8904	High Similarity	NPD4380	Phase 2
0.8857	High Similarity	NPD1550	Clinical (unspecified phase)
0.8857	High Similarity	NPD1552	Clinical (unspecified phase)
0.8792	High Similarity	NPD8443	Clinical (unspecified phase)
0.8786	High Similarity	NPD2796	Approved
0.8725	High Similarity	NPD2393	Clinical (unspecified phase)
0.8716	High Similarity	NPD7411	Suspended
0.8705	High Similarity	NPD6651	Approved
0.8675	High Similarity	NPD7075	Discontinued
0.8652	High Similarity	NPD2935	Discontinued
0.86	High Similarity	NPD7819	Suspended
0.86	High Similarity	NPD7096	Clinical (unspecified phase)
0.8531	High Similarity	NPD970	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD6799	Approved
0.8487	Intermediate Similarity	NPD3882	Suspended
0.8477	Intermediate Similarity	NPD2801	Approved
0.8472	Intermediate Similarity	NPD2800	Approved
0.8451	Intermediate Similarity	NPD2799	Discontinued
0.8414	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1934	Approved
0.8411	Intermediate Similarity	NPD6801	Discontinued
0.8408	Intermediate Similarity	NPD7473	Discontinued
0.8367	Intermediate Similarity	NPD1511	Approved
0.8366	Intermediate Similarity	NPD7768	Phase 2
0.8345	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8322	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD2534	Approved
0.8311	Intermediate Similarity	NPD2533	Approved
0.8311	Intermediate Similarity	NPD2532	Approved
0.8298	Intermediate Similarity	NPD943	Approved
0.8288	Intermediate Similarity	NPD3750	Approved
0.8278	Intermediate Similarity	NPD6599	Discontinued
0.8264	Intermediate Similarity	NPD1551	Phase 2
0.8255	Intermediate Similarity	NPD1512	Approved
0.8219	Intermediate Similarity	NPD1243	Approved
0.8207	Intermediate Similarity	NPD2344	Approved
0.8205	Intermediate Similarity	NPD5494	Approved
0.82	Intermediate Similarity	NPD920	Approved
0.8199	Intermediate Similarity	NPD5953	Discontinued
0.8194	Intermediate Similarity	NPD3749	Approved
0.8156	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD2798	Approved
0.8075	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7286	Phase 2
0.8067	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2313	Discontinued
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2309	Approved
0.7949	Intermediate Similarity	NPD3817	Phase 2
0.7945	Intermediate Similarity	NPD3748	Approved
0.7929	Intermediate Similarity	NPD1203	Approved
0.7902	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7390	Discontinued
0.7857	Intermediate Similarity	NPD3226	Approved
0.7852	Intermediate Similarity	NPD2654	Approved
0.7843	Intermediate Similarity	NPD5403	Approved
0.7842	Intermediate Similarity	NPD3972	Approved
0.7818	Intermediate Similarity	NPD6559	Discontinued
0.7805	Intermediate Similarity	NPD7074	Phase 3
0.78	Intermediate Similarity	NPD4628	Phase 3
0.777	Intermediate Similarity	NPD6099	Approved
0.777	Intermediate Similarity	NPD6100	Approved
0.7762	Intermediate Similarity	NPD6832	Phase 2
0.7762	Intermediate Similarity	NPD4908	Phase 1
0.7744	Intermediate Similarity	NPD7054	Approved
0.7742	Intermediate Similarity	NPD7458	Discontinued
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5402	Approved
0.7721	Intermediate Similarity	NPD9493	Approved
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7716	Intermediate Similarity	NPD3926	Phase 2
0.7714	Intermediate Similarity	NPD9717	Approved
0.7712	Intermediate Similarity	NPD5401	Approved
0.7702	Intermediate Similarity	NPD1247	Approved
0.7697	Intermediate Similarity	NPD7472	Approved
0.7688	Intermediate Similarity	NPD919	Approved
0.7682	Intermediate Similarity	NPD7003	Approved
0.7682	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1164	Approved
0.7676	Intermediate Similarity	NPD1470	Approved
0.7655	Intermediate Similarity	NPD3268	Approved
0.7654	Intermediate Similarity	NPD5710	Approved
0.7654	Intermediate Similarity	NPD5711	Approved
0.7651	Intermediate Similarity	NPD6797	Phase 2
0.7643	Intermediate Similarity	NPD1610	Phase 2
0.7643	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5844	Phase 1
0.7619	Intermediate Similarity	NPD230	Phase 1
0.7609	Intermediate Similarity	NPD9545	Approved
0.7606	Intermediate Similarity	NPD1876	Approved
0.7605	Intermediate Similarity	NPD7251	Discontinued
0.7584	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7808	Phase 3
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD2797	Approved
0.7534	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD5408	Approved
0.7533	Intermediate Similarity	NPD5404	Approved
0.7533	Intermediate Similarity	NPD5405	Approved
0.7533	Intermediate Similarity	NPD5406	Approved
0.7532	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4360	Phase 2
0.7529	Intermediate Similarity	NPD4363	Phase 3
0.7518	Intermediate Similarity	NPD422	Phase 1
0.7518	Intermediate Similarity	NPD1201	Approved
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7485	Intermediate Similarity	NPD1729	Discontinued
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1548	Phase 1
0.7467	Intermediate Similarity	NPD7033	Discontinued
0.7467	Intermediate Similarity	NPD4308	Phase 3
0.7465	Intermediate Similarity	NPD1608	Approved
0.744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7429	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2296	Approved
0.7383	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5124	Phase 1
0.7383	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD1471	Phase 3
0.7361	Intermediate Similarity	NPD1283	Approved
0.7347	Intermediate Similarity	NPD3027	Phase 3
0.7347	Intermediate Similarity	NPD4625	Phase 3
0.7345	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.7329	Intermediate Similarity	NPD9494	Approved
0.7318	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3267	Approved
0.731	Intermediate Similarity	NPD3266	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1651	Approved
0.7297	Intermediate Similarity	NPD411	Approved
0.7296	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4288	Approved
0.7267	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD37	Approved
0.7262	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD17	Approved
0.7246	Intermediate Similarity	NPD2403	Approved
0.7246	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD3225	Approved
0.7214	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8313	Approved
0.7209	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4287	Approved
0.72	Intermediate Similarity	NPD4307	Phase 2
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7181	Intermediate Similarity	NPD1296	Phase 2
0.7172	Intermediate Similarity	NPD4749	Approved
0.7162	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6279	Approved
0.716	Intermediate Similarity	NPD6280	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4966	Approved
0.7134	Intermediate Similarity	NPD4965	Approved
0.7134	Intermediate Similarity	NPD4967	Phase 2
0.7133	Intermediate Similarity	NPD4626	Approved
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD9266	Approved
0.7127	Intermediate Similarity	NPD6778	Approved
0.7127	Intermediate Similarity	NPD6777	Approved
0.7127	Intermediate Similarity	NPD6780	Approved
0.7127	Intermediate Similarity	NPD6776	Approved
0.7127	Intermediate Similarity	NPD6781	Approved
0.7127	Intermediate Similarity	NPD6782	Approved
0.7127	Intermediate Similarity	NPD6779	Approved
0.7117	Intermediate Similarity	NPD5761	Phase 2
0.7117	Intermediate Similarity	NPD5760	Phase 2
0.7107	Intermediate Similarity	NPD5049	Phase 3
0.7103	Intermediate Similarity	NPD9269	Phase 2
0.7099	Intermediate Similarity	NPD5890	Approved
0.7099	Intermediate Similarity	NPD5889	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