NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	266.942
LogP:	1.318
LogD:	1.266
LogS:	-2.241
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	4.687
Fsp3:	0.6
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:	-4.695
MDCK Permeability:	2.2817059289081953e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	68.2602310180664%
Volume Distribution (VD):	1.032
Pgp-substrate:	42.46881866455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.636
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.322
CYP3A4-substrate:	0.345

ADMET: Excretion

Clearance (CL):	8.361
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.098
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.596
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.073
Carcinogencity:	0.861
Eye Corrosion:	0.004
Eye Irritation:	0.036
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC91695

Natural Product ID:	NPC91695
*Common Name:**	4-Hydroxy-3,5A,9-Trimethyl-3A,4,5,9B-Tetrahydro-3H-Benzo[G][1]Benzofuran-2,8-Dione
IUPAC Name:	4-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
Synonyms:
Standard InCHIKey:	LUHMMHZLDLBAKX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-7-9(16)4-5-15(3)6-10(17)11-8(2)14(18)19-13(11)12(7)15/h4-5,8,10-11,13,17H,6H2,1-3H3
SMILES:	CC1=C2C3C(C(C)C(=O)O3)C(CC2(C)C=CC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1673435
PubChem CID:	621620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and 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
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO473	Artemisia maritima	Species	Asteraceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT98	Individual Protein	HERG	Homo sapiens	IC50	=	109647.82	nM	PMID[544207]

☑ 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 NPC91695 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	180
0.1-0.2	1028
0.2-0.3	3904
0.3-0.4	6838
0.4-0.5	14152
0.5-0.6	7237
0.6-0.7	6605
0.7-0.8	2649
0.8-0.85	89
0.85-0.9	11
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70145
0.9053	High Similarity	NPC216478
0.8842	High Similarity	NPC202833
0.8778	High Similarity	NPC177932
0.8763	High Similarity	NPC47024
0.8617	High Similarity	NPC252433
0.86	High Similarity	NPC296950
0.8586	High Similarity	NPC58329
0.8542	High Similarity	NPC183012
0.8476	Intermediate Similarity	NPC25909
0.8469	Intermediate Similarity	NPC23364
0.8454	Intermediate Similarity	NPC165528
0.8454	Intermediate Similarity	NPC284518
0.8454	Intermediate Similarity	NPC228766
0.8438	Intermediate Similarity	NPC148000
0.8438	Intermediate Similarity	NPC469596
0.8438	Intermediate Similarity	NPC225474
0.8421	Intermediate Similarity	NPC233345
0.8421	Intermediate Similarity	NPC473944
0.8421	Intermediate Similarity	NPC186363
0.8416	Intermediate Similarity	NPC146731
0.84	Intermediate Similarity	NPC273005
0.84	Intermediate Similarity	NPC469606
0.84	Intermediate Similarity	NPC31058
0.84	Intermediate Similarity	NPC476081
0.8365	Intermediate Similarity	NPC5103
0.8351	Intermediate Similarity	NPC259042
0.8351	Intermediate Similarity	NPC157686
0.835	Intermediate Similarity	NPC275539
0.835	Intermediate Similarity	NPC189075
0.8333	Intermediate Similarity	NPC469607
0.8316	Intermediate Similarity	NPC158488
0.8298	Intermediate Similarity	NPC277771
0.8298	Intermediate Similarity	NPC215831
0.828	Intermediate Similarity	NPC250981
0.8265	Intermediate Similarity	NPC134072
0.8265	Intermediate Similarity	NPC93245
0.8265	Intermediate Similarity	NPC234993
0.8252	Intermediate Similarity	NPC143609
0.8252	Intermediate Similarity	NPC110496
0.8247	Intermediate Similarity	NPC477129
0.8247	Intermediate Similarity	NPC250075
0.8247	Intermediate Similarity	NPC477130
0.8247	Intermediate Similarity	NPC24861
0.8218	Intermediate Similarity	NPC165250
0.8218	Intermediate Similarity	NPC164551
0.8211	Intermediate Similarity	NPC168131
0.8211	Intermediate Similarity	NPC5509
0.8211	Intermediate Similarity	NPC73995
0.82	Intermediate Similarity	NPC473219
0.82	Intermediate Similarity	NPC470761
0.819	Intermediate Similarity	NPC235014
0.8182	Intermediate Similarity	NPC473963
0.8182	Intermediate Similarity	NPC287668
0.8173	Intermediate Similarity	NPC476479
0.8163	Intermediate Similarity	NPC316215
0.8155	Intermediate Similarity	NPC477125
0.8155	Intermediate Similarity	NPC34768
0.8155	Intermediate Similarity	NPC111952
0.8144	Intermediate Similarity	NPC139692
0.8144	Intermediate Similarity	NPC475657
0.8137	Intermediate Similarity	NPC120321
0.8137	Intermediate Similarity	NPC478057
0.8137	Intermediate Similarity	NPC159533
0.8131	Intermediate Similarity	NPC469454
0.8131	Intermediate Similarity	NPC469463
0.8131	Intermediate Similarity	NPC469496
0.8125	Intermediate Similarity	NPC153853
0.8119	Intermediate Similarity	NPC242666
0.8119	Intermediate Similarity	NPC308824
0.8119	Intermediate Similarity	NPC471412
0.8113	Intermediate Similarity	NPC304180
0.8113	Intermediate Similarity	NPC469656
0.8113	Intermediate Similarity	NPC179798
0.8113	Intermediate Similarity	NPC474846
0.8113	Intermediate Similarity	NPC469655
0.8105	Intermediate Similarity	NPC136879
0.8105	Intermediate Similarity	NPC477128
0.8105	Intermediate Similarity	NPC477302
0.81	Intermediate Similarity	NPC316598
0.8095	Intermediate Similarity	NPC474243
0.8081	Intermediate Similarity	NPC473964
0.8081	Intermediate Similarity	NPC165632
0.8077	Intermediate Similarity	NPC302788
0.8077	Intermediate Similarity	NPC187435
0.8077	Intermediate Similarity	NPC67321
0.8073	Intermediate Similarity	NPC469684
0.8061	Intermediate Similarity	NPC474841
0.8061	Intermediate Similarity	NPC471446
0.8061	Intermediate Similarity	NPC473434
0.8061	Intermediate Similarity	NPC57117
0.8058	Intermediate Similarity	NPC258532
0.8041	Intermediate Similarity	NPC72845
0.8039	Intermediate Similarity	NPC162973
0.8039	Intermediate Similarity	NPC235369
0.8039	Intermediate Similarity	NPC295791
0.8039	Intermediate Similarity	NPC137430
0.8037	Intermediate Similarity	NPC472002
0.8037	Intermediate Similarity	NPC194951
0.8037	Intermediate Similarity	NPC269530
0.8037	Intermediate Similarity	NPC12046
0.8021	Intermediate Similarity	NPC116620
0.8021	Intermediate Similarity	NPC218927
0.8021	Intermediate Similarity	NPC206001
0.802	Intermediate Similarity	NPC54705
0.802	Intermediate Similarity	NPC476299
0.802	Intermediate Similarity	NPC471413
0.802	Intermediate Similarity	NPC474012
0.8019	Intermediate Similarity	NPC478209
0.8019	Intermediate Similarity	NPC253906
0.8	Intermediate Similarity	NPC136781
0.8	Intermediate Similarity	NPC284707
0.8	Intermediate Similarity	NPC474343
0.8	Intermediate Similarity	NPC322903
0.8	Intermediate Similarity	NPC476802
0.8	Intermediate Similarity	NPC89171
0.7982	Intermediate Similarity	NPC270478
0.7981	Intermediate Similarity	NPC478208
0.7981	Intermediate Similarity	NPC252296
0.798	Intermediate Similarity	NPC476245
0.798	Intermediate Similarity	NPC304886
0.7979	Intermediate Similarity	NPC52628
0.7963	Intermediate Similarity	NPC157441
0.7963	Intermediate Similarity	NPC474271
0.7963	Intermediate Similarity	NPC56448
0.7961	Intermediate Similarity	NPC110989
0.7961	Intermediate Similarity	NPC254202
0.7961	Intermediate Similarity	NPC99266
0.7961	Intermediate Similarity	NPC8196
0.7961	Intermediate Similarity	NPC156681
0.7959	Intermediate Similarity	NPC115021
0.7959	Intermediate Similarity	NPC166346
0.7941	Intermediate Similarity	NPC111292
0.7941	Intermediate Similarity	NPC224720
0.7941	Intermediate Similarity	NPC476240
0.7941	Intermediate Similarity	NPC476223
0.7941	Intermediate Similarity	NPC244456
0.7941	Intermediate Similarity	NPC469657
0.7941	Intermediate Similarity	NPC475958
0.7938	Intermediate Similarity	NPC475776
0.7938	Intermediate Similarity	NPC144133
0.7938	Intermediate Similarity	NPC475855
0.7938	Intermediate Similarity	NPC179394
0.7938	Intermediate Similarity	NPC152467
0.7925	Intermediate Similarity	NPC469370
0.7921	Intermediate Similarity	NPC476806
0.7921	Intermediate Similarity	NPC57079
0.7921	Intermediate Similarity	NPC476807
0.7921	Intermediate Similarity	NPC108368
0.7917	Intermediate Similarity	NPC226863
0.7909	Intermediate Similarity	NPC98249
0.7909	Intermediate Similarity	NPC53396
0.7905	Intermediate Similarity	NPC184512
0.7905	Intermediate Similarity	NPC179380
0.79	Intermediate Similarity	NPC242848
0.79	Intermediate Similarity	NPC29952
0.7895	Intermediate Similarity	NPC6979
0.7895	Intermediate Similarity	NPC85698
0.789	Intermediate Similarity	NPC238667
0.7885	Intermediate Similarity	NPC203659
0.7885	Intermediate Similarity	NPC118911
0.7879	Intermediate Similarity	NPC470697
0.787	Intermediate Similarity	NPC277769
0.787	Intermediate Similarity	NPC236217
0.787	Intermediate Similarity	NPC90952
0.7864	Intermediate Similarity	NPC238397
0.7864	Intermediate Similarity	NPC155332
0.7864	Intermediate Similarity	NPC32577
0.7864	Intermediate Similarity	NPC471363
0.7864	Intermediate Similarity	NPC225353
0.7864	Intermediate Similarity	NPC114540
0.7857	Intermediate Similarity	NPC477574
0.7857	Intermediate Similarity	NPC473675
0.785	Intermediate Similarity	NPC472666
0.785	Intermediate Similarity	NPC41551
0.785	Intermediate Similarity	NPC474567
0.7843	Intermediate Similarity	NPC476274
0.7838	Intermediate Similarity	NPC124676
0.7838	Intermediate Similarity	NPC146280
0.7835	Intermediate Similarity	NPC194642
0.7835	Intermediate Similarity	NPC174342
0.783	Intermediate Similarity	NPC469916
0.783	Intermediate Similarity	NPC325054
0.783	Intermediate Similarity	NPC306265
0.783	Intermediate Similarity	NPC472825
0.783	Intermediate Similarity	NPC472439
0.7822	Intermediate Similarity	NPC53844
0.7822	Intermediate Similarity	NPC84335
0.7822	Intermediate Similarity	NPC253826
0.7822	Intermediate Similarity	NPC151681
0.7822	Intermediate Similarity	NPC121402
0.7822	Intermediate Similarity	NPC175351
0.7822	Intermediate Similarity	NPC38530
0.7822	Intermediate Similarity	NPC224356
0.7822	Intermediate Similarity	NPC132753
0.7818	Intermediate Similarity	NPC471127
0.7818	Intermediate Similarity	NPC234858
0.7818	Intermediate Similarity	NPC154363
0.7812	Intermediate Similarity	NPC305029
0.781	Intermediate Similarity	NPC218158

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 NPC91695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1350
0.2-0.3	3584
0.3-0.4	2564
0.4-0.5	934
0.5-0.6	292
0.6-0.7	221
0.7-0.8	53
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8778	High Similarity	NPD1694	Approved
0.78	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD7638	Approved
0.7685	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7640	Approved
0.767	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.7434	Intermediate Similarity	NPD7115	Discovery
0.7407	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5697	Approved
0.7339	Intermediate Similarity	NPD6881	Approved
0.7339	Intermediate Similarity	NPD6899	Approved
0.7308	Intermediate Similarity	NPD7902	Approved
0.7297	Intermediate Similarity	NPD6649	Approved
0.7297	Intermediate Similarity	NPD6650	Approved
0.7292	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7228	Intermediate Similarity	NPD5785	Approved
0.7228	Intermediate Similarity	NPD6698	Approved
0.7228	Intermediate Similarity	NPD46	Approved
0.7207	Intermediate Similarity	NPD7290	Approved
0.7207	Intermediate Similarity	NPD6371	Approved
0.7207	Intermediate Similarity	NPD6883	Approved
0.7207	Intermediate Similarity	NPD7102	Approved
0.7196	Intermediate Similarity	NPD7632	Discontinued
0.7184	Intermediate Similarity	NPD5282	Discontinued
0.7184	Intermediate Similarity	NPD7748	Approved
0.7182	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6011	Approved
0.7172	Intermediate Similarity	NPD3618	Phase 1
0.7168	Intermediate Similarity	NPD4632	Approved
0.7157	Intermediate Similarity	NPD7515	Phase 2
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6008	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD6847	Approved
0.7117	Intermediate Similarity	NPD6373	Approved
0.7117	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD5344	Discontinued
0.7094	Intermediate Similarity	NPD6319	Approved
0.7091	Intermediate Similarity	NPD5701	Approved
0.7087	Intermediate Similarity	NPD5779	Approved
0.7087	Intermediate Similarity	NPD5778	Approved
0.7087	Intermediate Similarity	NPD6399	Phase 3
0.708	Intermediate Similarity	NPD8297	Approved
0.708	Intermediate Similarity	NPD6882	Approved
0.7037	Intermediate Similarity	NPD5211	Phase 2
0.7027	Intermediate Similarity	NPD7320	Approved
0.7019	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7900	Approved
0.7009	Intermediate Similarity	NPD5286	Approved
0.7009	Intermediate Similarity	NPD4696	Approved
0.7009	Intermediate Similarity	NPD5285	Approved
0.7	Intermediate Similarity	NPD7492	Approved
0.699	Remote Similarity	NPD6079	Approved
0.6983	Remote Similarity	NPD6009	Approved
0.6981	Remote Similarity	NPD6084	Phase 2
0.6981	Remote Similarity	NPD6083	Phase 2
0.6961	Remote Similarity	NPD1695	Approved
0.6952	Remote Similarity	NPD5695	Phase 3
0.6949	Remote Similarity	NPD6054	Approved
0.6942	Remote Similarity	NPD6616	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.6937	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6053	Discontinued
0.6916	Remote Similarity	NPD5696	Approved
0.6909	Remote Similarity	NPD5141	Approved
0.6893	Remote Similarity	NPD7838	Discovery
0.6891	Remote Similarity	NPD5983	Phase 2
0.6891	Remote Similarity	NPD6016	Approved
0.6891	Remote Similarity	NPD6015	Approved
0.6887	Remote Similarity	NPD5222	Approved
0.6887	Remote Similarity	NPD5221	Approved
0.6887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7078	Approved
0.6881	Remote Similarity	NPD5226	Approved
0.6881	Remote Similarity	NPD5225	Approved
0.6881	Remote Similarity	NPD5224	Approved
0.6881	Remote Similarity	NPD4633	Approved
0.6852	Remote Similarity	NPD6648	Approved
0.6833	Remote Similarity	NPD5988	Approved
0.6833	Remote Similarity	NPD6370	Approved
0.6832	Remote Similarity	NPD6684	Approved
0.6832	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7334	Approved
0.6832	Remote Similarity	NPD6409	Approved
0.6832	Remote Similarity	NPD7521	Approved
0.6832	Remote Similarity	NPD7146	Approved
0.6832	Remote Similarity	NPD5330	Approved
0.6829	Remote Similarity	NPD7736	Approved
0.6827	Remote Similarity	NPD6411	Approved
0.6827	Remote Similarity	NPD7637	Suspended
0.6827	Remote Similarity	NPD5281	Approved
0.6827	Remote Similarity	NPD5284	Approved
0.6822	Remote Similarity	NPD5173	Approved
0.6822	Remote Similarity	NPD4755	Approved
0.6818	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD5174	Approved
0.6814	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7507	Approved
0.68	Remote Similarity	NPD3666	Approved
0.68	Remote Similarity	NPD3133	Approved
0.68	Remote Similarity	NPD3665	Phase 1
0.6796	Remote Similarity	NPD5328	Approved
0.6792	Remote Similarity	NPD5210	Approved
0.6792	Remote Similarity	NPD4629	Approved
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5223	Approved
0.6777	Remote Similarity	NPD7604	Phase 2
0.6774	Remote Similarity	NPD7319	Approved
0.6765	Remote Similarity	NPD3573	Approved
0.6762	Remote Similarity	NPD4202	Approved
0.6759	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD6274	Approved
0.675	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7503	Approved
0.675	Remote Similarity	NPD8516	Approved
0.675	Remote Similarity	NPD8513	Phase 3
0.675	Remote Similarity	NPD8515	Approved
0.675	Remote Similarity	NPD8517	Approved
0.6733	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5363	Approved
0.6729	Remote Similarity	NPD4697	Phase 3
0.6723	Remote Similarity	NPD7100	Approved
0.6723	Remote Similarity	NPD7101	Approved
0.6701	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6903	Approved
0.6699	Remote Similarity	NPD5737	Approved
0.6699	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4700	Approved
0.6696	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD7328	Approved
0.6639	Remote Similarity	NPD6335	Approved
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD6313	Approved
0.6635	Remote Similarity	NPD4753	Phase 2
0.6635	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6101	Approved
0.6613	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD6868	Approved
0.6602	Remote Similarity	NPD4251	Approved
0.6602	Remote Similarity	NPD4250	Approved
0.66	Remote Similarity	NPD5209	Approved
0.66	Remote Similarity	NPD6435	Approved
0.66	Remote Similarity	NPD3667	Approved
0.6583	Remote Similarity	NPD7516	Approved
0.6579	Remote Similarity	NPD4730	Approved
0.6579	Remote Similarity	NPD4729	Approved
0.6571	Remote Similarity	NPD5207	Approved
0.6542	Remote Similarity	NPD6001	Approved
0.6535	Remote Similarity	NPD7154	Phase 3
0.6509	Remote Similarity	NPD8034	Phase 2
0.6509	Remote Similarity	NPD8035	Phase 2
0.6509	Remote Similarity	NPD7983	Approved
0.6505	Remote Similarity	NPD4623	Approved
0.6505	Remote Similarity	NPD4519	Discontinued
0.6505	Remote Similarity	NPD5279	Phase 3
0.6484	Remote Similarity	NPD6845	Suspended
0.648	Remote Similarity	NPD8074	Phase 3
0.6475	Remote Similarity	NPD8379	Approved
0.6475	Remote Similarity	NPD6921	Approved
0.6475	Remote Similarity	NPD8378	Approved
0.6475	Remote Similarity	NPD8296	Approved
0.6475	Remote Similarity	NPD8380	Approved
0.6475	Remote Similarity	NPD8335	Approved
0.6471	Remote Similarity	NPD4786	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5250	Approved
0.6466	Remote Similarity	NPD5249	Phase 3
0.6466	Remote Similarity	NPD5248	Approved
0.6466	Remote Similarity	NPD5251	Approved
0.6466	Remote Similarity	NPD5247	Approved
0.6436	Remote Similarity	NPD4269	Approved
0.6436	Remote Similarity	NPD4270	Approved
0.6435	Remote Similarity	NPD5128	Approved
0.641	Remote Similarity	NPD5215	Approved
0.641	Remote Similarity	NPD5217	Approved
0.641	Remote Similarity	NPD5216	Approved
0.6408	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4768	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