NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.04
Volume:	171.722
LogP:	1.961
LogD:	2.229
LogS:	-2.645
# Rotatable Bonds:	0
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	3.18
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.922
MDCK Permeability:	6.930598374310648e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.195
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	96.40174102783203%
Volume Distribution (VD):	0.469
Pgp-substrate:	6.079950332641602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.881
CYP1A2-substrate:	0.624
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.537
CYP2D6-inhibitor:	0.326
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	15.475
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.63
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.242
Skin Sensitization:	0.776
Carcinogencity:	0.819
Eye Corrosion:	0.895
Eye Irritation:	0.936
Respiratory Toxicity:	0.478

Download Data

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

Natural Product: NPC275356

Natural Product ID:	NPC275356
*Common Name:**	5,7-Dihydroxy-4-Methylphthalide
IUPAC Name:	5,7-dihydroxy-4-methyl-3H-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	GXYQICKPCCBIIX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8O4/c1-4-5-3-13-9(12)8(5)7(11)2-6(4)10/h2,10-11H,3H2,1H3
SMILES:	Cc1c2COC(=O)c2c(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575424
PubChem CID:	14503052
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO33263	eupenicillium parvum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18991460]
NPO30824	Eurotium repens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667972]
NPO10055	Stichoneuron caudatum	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24606395]
NPO6417	Lecanora grumosa	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4946	Antidesma venosum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7499	Mammillaria krameri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11458	Hymenoxys subintegra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6874	Desmodium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6189	Rhamnus nipalensis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10055	Stichoneuron caudatum	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8748	Dacrydium nidulum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1387	Lactarius violascens	Species	Russulaceae	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
Others	5

Activity Type	# Activity
Individual Protein	5
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[548791]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[548791]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[548791]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	<	40.0	%	PMID[548791]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	<	40.0	%	PMID[548791]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	18.08	ug.mL-1	PMID[548792]

☑ 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 NPC275356 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	343
0.1-0.2	1649
0.2-0.3	3831
0.3-0.4	8672
0.4-0.5	9954
0.5-0.6	4067
0.6-0.7	6835
0.7-0.8	6263
0.8-0.85	840
0.85-0.9	191
0.9-0.95	51
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC166583
0.9429	High Similarity	NPC53362
0.9416	High Similarity	NPC90411
0.9412	High Similarity	NPC88269
0.9398	High Similarity	NPC153783
0.9343	High Similarity	NPC472601
0.9343	High Similarity	NPC472600
0.9333	High Similarity	NPC158481
0.9333	High Similarity	NPC50455
0.9275	High Similarity	NPC472605
0.9275	High Similarity	NPC37530
0.9275	High Similarity	NPC472604
0.9275	High Similarity	NPC472603
0.9265	High Similarity	NPC70380
0.9265	High Similarity	NPC194579
0.9248	High Similarity	NPC219892
0.9248	High Similarity	NPC189823
0.9231	High Similarity	NPC119929
0.9231	High Similarity	NPC179178
0.9209	High Similarity	NPC82913
0.9209	High Similarity	NPC322112
0.9203	High Similarity	NPC99441
0.9203	High Similarity	NPC187690
0.9197	High Similarity	NPC191835
0.9197	High Similarity	NPC94248
0.9197	High Similarity	NPC212693
0.9191	High Similarity	NPC235115
0.9161	High Similarity	NPC198927
0.9149	High Similarity	NPC75694
0.9143	High Similarity	NPC472610
0.9143	High Similarity	NPC159721
0.913	High Similarity	NPC105456
0.913	High Similarity	NPC139634
0.9124	High Similarity	NPC135837
0.9103	High Similarity	NPC271681
0.9085	High Similarity	NPC260946
0.9078	High Similarity	NPC42540
0.9078	High Similarity	NPC151607
0.9065	High Similarity	NPC165172
0.9058	High Similarity	NPC33144
0.9058	High Similarity	NPC221104
0.9058	High Similarity	NPC472602
0.9058	High Similarity	NPC478200
0.9051	High Similarity	NPC291454
0.9044	High Similarity	NPC175943
0.903	High Similarity	NPC296158
0.9021	High Similarity	NPC8817
0.9021	High Similarity	NPC137296
0.9014	High Similarity	NPC473692
0.9014	High Similarity	NPC83272
0.9007	High Similarity	NPC471731
0.9007	High Similarity	NPC472006
0.9007	High Similarity	NPC51106
0.9	High Similarity	NPC478217
0.9	High Similarity	NPC313123
0.9	High Similarity	NPC1704
0.9	High Similarity	NPC244923
0.9	High Similarity	NPC67650
0.9	High Similarity	NPC53649
0.8993	High Similarity	NPC52358
0.8993	High Similarity	NPC32360
0.8993	High Similarity	NPC471819
0.8993	High Similarity	NPC268052
0.8986	High Similarity	NPC71256
0.8978	High Similarity	NPC182496
0.8978	High Similarity	NPC180905
0.8951	High Similarity	NPC470357
0.8951	High Similarity	NPC107625
0.8951	High Similarity	NPC473023
0.8936	High Similarity	NPC471733
0.8929	High Similarity	NPC155205
0.8929	High Similarity	NPC158472
0.8904	High Similarity	NPC240768
0.8904	High Similarity	NPC200773
0.8881	High Similarity	NPC471689
0.8873	High Similarity	NPC469542
0.8873	High Similarity	NPC478202
0.8865	High Similarity	NPC158634
0.8865	High Similarity	NPC149533
0.8865	High Similarity	NPC478201
0.8865	High Similarity	NPC472035
0.8865	High Similarity	NPC470842
0.8857	High Similarity	NPC247409
0.8857	High Similarity	NPC92655
0.8849	High Similarity	NPC245058
0.8849	High Similarity	NPC65837
0.8849	High Similarity	NPC474849
0.8849	High Similarity	NPC149372
0.8849	High Similarity	NPC178467
0.8849	High Similarity	NPC474771
0.8841	High Similarity	NPC278375
0.8836	High Similarity	NPC96501
0.8811	High Similarity	NPC478203
0.8811	High Similarity	NPC210966
0.8811	High Similarity	NPC126882
0.8803	High Similarity	NPC474385
0.8797	High Similarity	NPC201728
0.8797	High Similarity	NPC262671
0.8794	High Similarity	NPC64664
0.8786	High Similarity	NPC475974
0.8784	High Similarity	NPC192189
0.8777	High Similarity	NPC326847
0.8777	High Similarity	NPC156967
0.8777	High Similarity	NPC472599
0.8768	High Similarity	NPC475645
0.8759	High Similarity	NPC471734
0.875	High Similarity	NPC257558
0.8732	High Similarity	NPC475730
0.8725	High Similarity	NPC79998
0.8725	High Similarity	NPC199926
0.8723	High Similarity	NPC474655
0.8716	High Similarity	NPC175978
0.8716	High Similarity	NPC273483
0.8714	High Similarity	NPC261292
0.8714	High Similarity	NPC301915
0.8707	High Similarity	NPC56204
0.8707	High Similarity	NPC469619
0.8707	High Similarity	NPC469670
0.8705	High Similarity	NPC142027
0.8705	High Similarity	NPC27407
0.8699	High Similarity	NPC153417
0.8699	High Similarity	NPC470359
0.8696	High Similarity	NPC48036
0.8696	High Similarity	NPC37299
0.8696	High Similarity	NPC180261
0.869	High Similarity	NPC225173
0.869	High Similarity	NPC472033
0.869	High Similarity	NPC471735
0.869	High Similarity	NPC163846
0.8686	High Similarity	NPC7012
0.8686	High Similarity	NPC214702
0.8686	High Similarity	NPC470831
0.8684	High Similarity	NPC117985
0.8681	High Similarity	NPC470932
0.8681	High Similarity	NPC210425
0.8681	High Similarity	NPC280404
0.8681	High Similarity	NPC86373
0.8681	High Similarity	NPC277426
0.8671	High Similarity	NPC250755
0.8671	High Similarity	NPC297985
0.8671	High Similarity	NPC469579
0.8667	High Similarity	NPC150227
0.8662	High Similarity	NPC327187
0.8662	High Similarity	NPC168471
0.8662	High Similarity	NPC156872
0.8652	High Similarity	NPC197666
0.8652	High Similarity	NPC126739
0.8652	High Similarity	NPC472403
0.8652	High Similarity	NPC9121
0.8652	High Similarity	NPC177307
0.8649	High Similarity	NPC70016
0.8649	High Similarity	NPC215921
0.8643	High Similarity	NPC471690
0.8639	High Similarity	NPC4423
0.8639	High Similarity	NPC270160
0.8639	High Similarity	NPC233267
0.8639	High Similarity	NPC77325
0.8639	High Similarity	NPC237440
0.8639	High Similarity	NPC291049
0.8633	High Similarity	NPC474394
0.863	High Similarity	NPC125801
0.863	High Similarity	NPC14098
0.863	High Similarity	NPC476463
0.863	High Similarity	NPC472036
0.8623	High Similarity	NPC476389
0.8621	High Similarity	NPC472034
0.8621	High Similarity	NPC134621
0.8613	High Similarity	NPC17840
0.8613	High Similarity	NPC247477
0.8613	High Similarity	NPC62219
0.8611	High Similarity	NPC354984
0.8609	High Similarity	NPC190020
0.8609	High Similarity	NPC473395
0.8609	High Similarity	NPC84935
0.8609	High Similarity	NPC77679
0.8603	High Similarity	NPC41263
0.8601	High Similarity	NPC220106
0.8593	High Similarity	NPC95309
0.8581	High Similarity	NPC470107
0.8581	High Similarity	NPC202595
0.8571	High Similarity	NPC221352
0.8571	High Similarity	NPC290803
0.8571	High Similarity	NPC2569
0.8571	High Similarity	NPC172329
0.8571	High Similarity	NPC37139
0.8571	High Similarity	NPC105415
0.8562	High Similarity	NPC470570
0.8562	High Similarity	NPC267509
0.8562	High Similarity	NPC237208
0.8552	High Similarity	NPC48762
0.8552	High Similarity	NPC27106
0.8552	High Similarity	NPC21599
0.8552	High Similarity	NPC95123
0.8552	High Similarity	NPC66404
0.8552	High Similarity	NPC193703
0.8552	High Similarity	NPC184702
0.8543	High Similarity	NPC146211
0.8542	High Similarity	NPC94076
0.8542	High Similarity	NPC105648
0.8542	High Similarity	NPC182255

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 NPC275356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	977
0.2-0.3	1910
0.3-0.4	2660
0.4-0.5	1793
0.5-0.6	1058
0.6-0.7	311
0.7-0.8	120
0.8-0.85	10
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9149	High Similarity	NPD2532	Approved
0.9149	High Similarity	NPD2534	Approved
0.9149	High Similarity	NPD2533	Approved
0.8857	High Similarity	NPD970	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD230	Phase 1
0.8289	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD2800	Approved
0.8269	Intermediate Similarity	NPD5710	Approved
0.8269	Intermediate Similarity	NPD5711	Approved
0.8252	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6232	Discontinued
0.8133	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7972	Intermediate Similarity	NPD1240	Approved
0.7945	Intermediate Similarity	NPD2935	Discontinued
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD9545	Approved
0.7905	Intermediate Similarity	NPD1243	Approved
0.7898	Intermediate Similarity	NPD3749	Approved
0.7891	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1607	Approved
0.7838	Intermediate Similarity	NPD1549	Phase 2
0.7832	Intermediate Similarity	NPD3764	Approved
0.7815	Intermediate Similarity	NPD7390	Discontinued
0.7806	Intermediate Similarity	NPD7411	Suspended
0.7785	Intermediate Similarity	NPD7075	Discontinued
0.7778	Intermediate Similarity	NPD9493	Approved
0.7756	Intermediate Similarity	NPD1934	Approved
0.7748	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4380	Phase 2
0.7733	Intermediate Similarity	NPD3750	Approved
0.7733	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD943	Approved
0.7722	Intermediate Similarity	NPD3882	Suspended
0.7722	Intermediate Similarity	NPD7768	Phase 2
0.7707	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1465	Phase 2
0.7703	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD1511	Approved
0.7677	Intermediate Similarity	NPD3226	Approved
0.7658	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD9269	Phase 2
0.7643	Intermediate Similarity	NPD6801	Discontinued
0.7625	Intermediate Similarity	NPD919	Approved
0.7619	Intermediate Similarity	NPD6651	Approved
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD9268	Approved
0.7607	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1512	Approved
0.7595	Intermediate Similarity	NPD2801	Approved
0.7586	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5404	Approved
0.7584	Intermediate Similarity	NPD5406	Approved
0.7584	Intermediate Similarity	NPD5405	Approved
0.7584	Intermediate Similarity	NPD5408	Approved
0.7582	Intermediate Similarity	NPD6799	Approved
0.7578	Intermediate Similarity	NPD5494	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7547	Intermediate Similarity	NPD3817	Phase 2
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.7532	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7483	Intermediate Similarity	NPD1470	Approved
0.7483	Intermediate Similarity	NPD1164	Approved
0.747	Intermediate Similarity	NPD7286	Phase 2
0.7467	Intermediate Similarity	NPD2796	Approved
0.7466	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1201	Approved
0.744	Intermediate Similarity	NPD6559	Discontinued
0.7434	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD447	Suspended
0.7423	Intermediate Similarity	NPD1247	Approved
0.7421	Intermediate Similarity	NPD37	Approved
0.7407	Intermediate Similarity	NPD6234	Discontinued
0.74	Intermediate Similarity	NPD2799	Discontinued
0.74	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD4966	Approved
0.7391	Intermediate Similarity	NPD4965	Approved
0.7391	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5953	Discontinued
0.7346	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2344	Approved
0.7289	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6166	Phase 2
0.7289	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1203	Approved
0.723	Intermediate Similarity	NPD411	Approved
0.723	Intermediate Similarity	NPD2313	Discontinued
0.7225	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD7074	Phase 3
0.7208	Intermediate Similarity	NPD2654	Approved
0.7203	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9266	Approved
0.7185	Intermediate Similarity	NPD74	Approved
0.7183	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD1283	Approved
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD7054	Approved
0.7153	Intermediate Similarity	NPD1608	Approved
0.7124	Intermediate Similarity	NPD6099	Approved
0.7124	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD7472	Approved
0.7115	Intermediate Similarity	NPD2309	Approved
0.7113	Intermediate Similarity	NPD5691	Approved
0.7111	Intermediate Similarity	NPD9264	Approved
0.7111	Intermediate Similarity	NPD9263	Approved
0.7111	Intermediate Similarity	NPD9267	Approved
0.7111	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7228	Approved
0.7086	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6002	Phase 3
0.7078	Intermediate Similarity	NPD6005	Phase 3
0.7078	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6004	Phase 3
0.7076	Intermediate Similarity	NPD6797	Phase 2
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1019	Discontinued
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7251	Discontinued
0.7025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3926	Phase 2
0.7019	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1729	Discontinued
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD5403	Approved
0.6994	Remote Similarity	NPD7808	Phase 3
0.6993	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5401	Approved
0.6981	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6832	Phase 2
0.6968	Remote Similarity	NPD1471	Phase 3
0.6966	Remote Similarity	NPD1281	Approved
0.6957	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8312	Approved
0.6954	Remote Similarity	NPD8313	Approved
0.6952	Remote Similarity	NPD8151	Discontinued
0.6949	Remote Similarity	NPD4287	Approved
0.6948	Remote Similarity	NPD7033	Discontinued
0.6944	Remote Similarity	NPD17	Approved
0.6943	Remote Similarity	NPD7003	Approved
0.6936	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD9494	Approved
0.6909	Remote Similarity	NPD4288	Approved
0.6908	Remote Similarity	NPD2979	Phase 3
0.6908	Remote Similarity	NPD4060	Phase 1
0.6889	Remote Similarity	NPD6535	Approved
0.6889	Remote Similarity	NPD6534	Approved
0.6887	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1296	Phase 2
0.6882	Remote Similarity	NPD2403	Approved
0.6879	Remote Similarity	NPD9281	Approved
0.6875	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7435	Discontinued
0.6863	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5124	Phase 1
0.6849	Remote Similarity	NPD1610	Phase 2
0.6846	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD520	Approved
0.6842	Remote Similarity	NPD6663	Approved
0.6836	Remote Similarity	NPD8434	Phase 2
0.6832	Remote Similarity	NPD6273	Approved
0.6828	Remote Similarity	NPD8320	Phase 1
0.6828	Remote Similarity	NPD8319	Approved
0.6828	Remote Similarity	NPD1778	Approved
0.6824	Remote Similarity	NPD5242	Approved
0.6824	Remote Similarity	NPD6696	Suspended
0.6821	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4625	Phase 3
0.6815	Remote Similarity	NPD9261	Approved
0.6812	Remote Similarity	NPD2182	Approved
0.681	Remote Similarity	NPD7458	Discontinued
0.6807	Remote Similarity	NPD5353	Approved
0.6802	Remote Similarity	NPD7177	Discontinued
0.6802	Remote Similarity	NPD3751	Discontinued
0.6802	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5736	Approved
0.6795	Remote Similarity	NPD4476	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