NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	446.16
Volume:	432.795
LogP:	1.59
LogD:	1.184
LogS:	-3.534
# Rotatable Bonds:	7
TPSA:	117.73
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	5.231
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.005
MDCK Permeability:	5.023902849643491e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.858
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.529
Plasma Protein Binding (PPB):	31.36248207092285%
Volume Distribution (VD):	0.941
Pgp-substrate:	55.87040328979492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.416
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	8.39
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.719
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.334
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.592
Skin Sensitization:	0.848
Carcinogencity:	0.52
Eye Corrosion:	0.815
Eye Irritation:	0.079
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC477509

Natural Product ID:	NPC477509
*Common Name:**	methyl (3aS,4S,5S,5aR,9aS,9bR)-5-acetyloxy-4-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-9-methyl-3-methylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-benzo[g][1]benzofuran-5a-carboxylate
IUPAC Name:	methyl (3aS,4S,5S,5aR,9aS,9bR)-5-acetyloxy-4-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-9-methyl-3-methylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-benzo[g][1]benzofuran-5a-carboxylate
Synonyms:
Standard InCHIKey:	MJPMGKKVXFTUTF-PAJLOVDVSA-N
Standard InCHI:	InChI=1S/C23H26O9/c1-10-8-7-9-23(21(27)28-6)15(10)16-14(11(2)19(25)30-16)17(18(23)29-13(4)24)31-20(26)22(5)12(3)32-22/h7-9,12,14-18H,2H2,1,3-6H3/t12-,14-,15+,16-,17-,18+,22-,23+/m0/s1
SMILES:	C[C@H]1[C@@](O1)(C)C(=O)O[C@H]2[C@@H]3[C@@H]([C@H]4C(=CC=C[C@@]4([C@@H]2OC(=O)C)C(=O)OC)C)OC(=O)C3=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122178693
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
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO18602	Melampodium leucanthum	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	2
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	670	nM	PMID[25685941]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	180	nM	PMID[25685941]
NPT2	Others	Unspecified		Ratio IC50	=	3.7	n.a.	PMID[25685941]

☑ 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 NPC477509 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	276
0.1-0.2	1419
0.2-0.3	4493
0.3-0.4	7487
0.4-0.5	13687
0.5-0.6	8565
0.6-0.7	5210
0.7-0.8	1408
0.8-0.85	133
0.85-0.9	18
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC270478
0.8818	High Similarity	NPC281624
0.8727	High Similarity	NPC469370
0.8649	High Similarity	NPC253906
0.8609	High Similarity	NPC284707
0.8571	High Similarity	NPC194619
0.8545	High Similarity	NPC475587
0.8545	High Similarity	NPC475510
0.8545	High Similarity	NPC474716
0.8534	High Similarity	NPC470186
0.8532	High Similarity	NPC477127
0.8522	High Similarity	NPC53396
0.8522	High Similarity	NPC469684
0.8522	High Similarity	NPC98249
0.8482	Intermediate Similarity	NPC473843
0.8482	Intermediate Similarity	NPC473594
0.8482	Intermediate Similarity	NPC474586
0.8482	Intermediate Similarity	NPC473975
0.8468	Intermediate Similarity	NPC473595
0.8468	Intermediate Similarity	NPC473939
0.8421	Intermediate Similarity	NPC477126
0.8421	Intermediate Similarity	NPC33360
0.8407	Intermediate Similarity	NPC179798
0.8407	Intermediate Similarity	NPC304180
0.8378	Intermediate Similarity	NPC180744
0.8348	Intermediate Similarity	NPC73314
0.8333	Intermediate Similarity	NPC24651
0.8318	Intermediate Similarity	NPC474921
0.8305	Intermediate Similarity	NPC475003
0.8276	Intermediate Similarity	NPC476710
0.8276	Intermediate Similarity	NPC476711
0.8273	Intermediate Similarity	NPC474166
0.8273	Intermediate Similarity	NPC19239
0.8264	Intermediate Similarity	NPC471939
0.8264	Intermediate Similarity	NPC181999
0.8264	Intermediate Similarity	NPC225049
0.8261	Intermediate Similarity	NPC469463
0.8261	Intermediate Similarity	NPC469496
0.8261	Intermediate Similarity	NPC56448
0.8261	Intermediate Similarity	NPC469454
0.825	Intermediate Similarity	NPC67251
0.8241	Intermediate Similarity	NPC264378
0.8235	Intermediate Similarity	NPC310511
0.8235	Intermediate Similarity	NPC477046
0.8235	Intermediate Similarity	NPC102822
0.823	Intermediate Similarity	NPC474242
0.822	Intermediate Similarity	NPC475520
0.8214	Intermediate Similarity	NPC469558
0.8205	Intermediate Similarity	NPC97908
0.8205	Intermediate Similarity	NPC476712
0.8205	Intermediate Similarity	NPC122033
0.8205	Intermediate Similarity	NPC470854
0.8205	Intermediate Similarity	NPC474654
0.8205	Intermediate Similarity	NPC470775
0.8205	Intermediate Similarity	NPC473590
0.8205	Intermediate Similarity	NPC296822
0.8205	Intermediate Similarity	NPC287343
0.8205	Intermediate Similarity	NPC476713
0.8205	Intermediate Similarity	NPC176513
0.8197	Intermediate Similarity	NPC471940
0.8197	Intermediate Similarity	NPC476008
0.8174	Intermediate Similarity	NPC473877
0.8167	Intermediate Similarity	NPC312833
0.8165	Intermediate Similarity	NPC469551
0.8158	Intermediate Similarity	NPC5103
0.8151	Intermediate Similarity	NPC143755
0.8151	Intermediate Similarity	NPC4548
0.8136	Intermediate Similarity	NPC473720
0.8136	Intermediate Similarity	NPC17772
0.8136	Intermediate Similarity	NPC470776
0.8136	Intermediate Similarity	NPC240509
0.8131	Intermediate Similarity	NPC56369
0.813	Intermediate Similarity	NPC236999
0.8125	Intermediate Similarity	NPC477125
0.812	Intermediate Similarity	NPC474333
0.812	Intermediate Similarity	NPC179626
0.8115	Intermediate Similarity	NPC477745
0.8115	Intermediate Similarity	NPC473635
0.8103	Intermediate Similarity	NPC470120
0.8099	Intermediate Similarity	NPC265557
0.8099	Intermediate Similarity	NPC472399
0.8099	Intermediate Similarity	NPC91693
0.8099	Intermediate Similarity	NPC473802
0.8099	Intermediate Similarity	NPC18945
0.8099	Intermediate Similarity	NPC105926
0.8095	Intermediate Similarity	NPC473548
0.8095	Intermediate Similarity	NPC475500
0.8095	Intermediate Similarity	NPC471136
0.8095	Intermediate Similarity	NPC100017
0.8095	Intermediate Similarity	NPC475154
0.8095	Intermediate Similarity	NPC182266
0.8095	Intermediate Similarity	NPC471137
0.8095	Intermediate Similarity	NPC223356
0.8087	Intermediate Similarity	NPC469656
0.8087	Intermediate Similarity	NPC474846
0.8087	Intermediate Similarity	NPC469655
0.808	Intermediate Similarity	NPC470185
0.807	Intermediate Similarity	NPC471934
0.8067	Intermediate Similarity	NPC470777
0.8067	Intermediate Similarity	NPC469488
0.8067	Intermediate Similarity	NPC472667
0.8051	Intermediate Similarity	NPC58662
0.8051	Intermediate Similarity	NPC23046
0.8051	Intermediate Similarity	NPC478204
0.8037	Intermediate Similarity	NPC66581
0.8037	Intermediate Similarity	NPC471446
0.8037	Intermediate Similarity	NPC474841
0.8037	Intermediate Similarity	NPC473434
0.8036	Intermediate Similarity	NPC283850
0.8036	Intermediate Similarity	NPC470297
0.8036	Intermediate Similarity	NPC477510
0.8036	Intermediate Similarity	NPC471143
0.8034	Intermediate Similarity	NPC473798
0.8033	Intermediate Similarity	NPC145238
0.8033	Intermediate Similarity	NPC473709
0.8033	Intermediate Similarity	NPC476729
0.8033	Intermediate Similarity	NPC470922
0.8033	Intermediate Similarity	NPC473919
0.8017	Intermediate Similarity	NPC222834
0.8017	Intermediate Similarity	NPC269530
0.8017	Intermediate Similarity	NPC170538
0.8017	Intermediate Similarity	NPC471933
0.8017	Intermediate Similarity	NPC317687
0.8	Intermediate Similarity	NPC251564
0.8	Intermediate Similarity	NPC477189
0.8	Intermediate Similarity	NPC475314
0.8	Intermediate Similarity	NPC112038
0.8	Intermediate Similarity	NPC475606
0.7983	Intermediate Similarity	NPC478205
0.7983	Intermediate Similarity	NPC478206
0.7983	Intermediate Similarity	NPC21326
0.7983	Intermediate Similarity	NPC188667
0.7983	Intermediate Similarity	NPC470420
0.7983	Intermediate Similarity	NPC108581
0.7983	Intermediate Similarity	NPC251310
0.7983	Intermediate Similarity	NPC204552
0.7982	Intermediate Similarity	NPC94377
0.7969	Intermediate Similarity	NPC68282
0.7967	Intermediate Similarity	NPC293112
0.7966	Intermediate Similarity	NPC96312
0.7966	Intermediate Similarity	NPC40632
0.7966	Intermediate Similarity	NPC470793
0.7966	Intermediate Similarity	NPC251236
0.7966	Intermediate Similarity	NPC328374
0.7966	Intermediate Similarity	NPC207217
0.7966	Intermediate Similarity	NPC474734
0.7965	Intermediate Similarity	NPC470979
0.7965	Intermediate Similarity	NPC470975
0.7965	Intermediate Similarity	NPC103088
0.7951	Intermediate Similarity	NPC11895
0.7951	Intermediate Similarity	NPC120724
0.7949	Intermediate Similarity	NPC208998
0.7949	Intermediate Similarity	NPC471204
0.7949	Intermediate Similarity	NPC159333
0.7949	Intermediate Similarity	NPC49451
0.7949	Intermediate Similarity	NPC7921
0.7946	Intermediate Similarity	NPC99510
0.7946	Intermediate Similarity	NPC61442
0.7937	Intermediate Similarity	NPC473485
0.7937	Intermediate Similarity	NPC475139
0.7937	Intermediate Similarity	NPC180902
0.7937	Intermediate Similarity	NPC474508
0.7934	Intermediate Similarity	NPC472401
0.7934	Intermediate Similarity	NPC470779
0.7931	Intermediate Similarity	NPC317107
0.7928	Intermediate Similarity	NPC476478
0.7928	Intermediate Similarity	NPC475958
0.7917	Intermediate Similarity	NPC156745
0.7917	Intermediate Similarity	NPC236918
0.7913	Intermediate Similarity	NPC475922
0.7913	Intermediate Similarity	NPC42662
0.7909	Intermediate Similarity	NPC216478
0.7903	Intermediate Similarity	NPC470780
0.7899	Intermediate Similarity	NPC27999
0.7899	Intermediate Similarity	NPC477116
0.7899	Intermediate Similarity	NPC474518
0.7895	Intermediate Similarity	NPC133422
0.7886	Intermediate Similarity	NPC172154
0.7886	Intermediate Similarity	NPC81736
0.7876	Intermediate Similarity	NPC258532
0.7876	Intermediate Similarity	NPC146731
0.7874	Intermediate Similarity	NPC168879
0.787	Intermediate Similarity	NPC477130
0.787	Intermediate Similarity	NPC477129
0.7869	Intermediate Similarity	NPC19464
0.7869	Intermediate Similarity	NPC310035
0.7869	Intermediate Similarity	NPC162009
0.7869	Intermediate Similarity	NPC188222
0.7869	Intermediate Similarity	NPC282003
0.7869	Intermediate Similarity	NPC257017
0.7863	Intermediate Similarity	NPC265391
0.7863	Intermediate Similarity	NPC474516
0.7863	Intermediate Similarity	NPC476801
0.7857	Intermediate Similarity	NPC476863
0.7857	Intermediate Similarity	NPC164551
0.7857	Intermediate Similarity	NPC476852
0.7857	Intermediate Similarity	NPC476862
0.7851	Intermediate Similarity	NPC145182
0.7851	Intermediate Similarity	NPC472759
0.7851	Intermediate Similarity	NPC329080

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 NPC477509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	1653
0.2-0.3	3745
0.3-0.4	2259
0.4-0.5	794
0.5-0.6	272
0.6-0.7	166
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7895	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6008	Approved
0.7458	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6648	Approved
0.7323	Intermediate Similarity	NPD7492	Approved
0.7317	Intermediate Similarity	NPD7115	Discovery
0.728	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7266	Intermediate Similarity	NPD6616	Approved
0.7222	Intermediate Similarity	NPD6016	Approved
0.7222	Intermediate Similarity	NPD6015	Approved
0.7209	Intermediate Similarity	NPD7078	Approved
0.719	Intermediate Similarity	NPD6649	Approved
0.719	Intermediate Similarity	NPD6650	Approved
0.7165	Intermediate Similarity	NPD6370	Approved
0.7165	Intermediate Similarity	NPD5988	Approved
0.7154	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.713	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6921	Approved
0.7087	Intermediate Similarity	NPD8517	Approved
0.7087	Intermediate Similarity	NPD8515	Approved
0.7087	Intermediate Similarity	NPD8513	Phase 3
0.7087	Intermediate Similarity	NPD8516	Approved
0.7083	Intermediate Similarity	NPD6899	Approved
0.7083	Intermediate Similarity	NPD6881	Approved
0.7073	Intermediate Similarity	NPD4632	Approved
0.704	Intermediate Similarity	NPD6009	Approved
0.7025	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD6373	Approved
0.7025	Intermediate Similarity	NPD6014	Approved
0.7025	Intermediate Similarity	NPD6013	Approved
0.7025	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD5344	Discontinued
0.7008	Intermediate Similarity	NPD6059	Approved
0.6992	Remote Similarity	NPD6882	Approved
0.6977	Remote Similarity	NPD8328	Phase 3
0.6977	Remote Similarity	NPD7604	Phase 2
0.6972	Remote Similarity	NPD1694	Approved
0.6967	Remote Similarity	NPD7102	Approved
0.6967	Remote Similarity	NPD6883	Approved
0.6967	Remote Similarity	NPD7290	Approved
0.6953	Remote Similarity	NPD5983	Phase 2
0.6947	Remote Similarity	NPD8293	Discontinued
0.6942	Remote Similarity	NPD6011	Approved
0.6917	Remote Similarity	NPD6675	Approved
0.6917	Remote Similarity	NPD5739	Approved
0.6917	Remote Similarity	NPD7128	Approved
0.6917	Remote Similarity	NPD6402	Approved
0.6911	Remote Similarity	NPD6847	Approved
0.6911	Remote Similarity	NPD6617	Approved
0.6911	Remote Similarity	NPD6869	Approved
0.6911	Remote Similarity	NPD8130	Phase 1
0.6905	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7260	Phase 2
0.6864	Remote Similarity	NPD1700	Approved
0.686	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5701	Approved
0.6842	Remote Similarity	NPD7319	Approved
0.6842	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD5778	Approved
0.6829	Remote Similarity	NPD4634	Approved
0.6818	Remote Similarity	NPD8074	Phase 3
0.6803	Remote Similarity	NPD7320	Approved
0.6754	Remote Similarity	NPD6411	Approved
0.6742	Remote Similarity	NPD6336	Discontinued
0.6726	Remote Similarity	NPD1695	Approved
0.6724	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6639	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD5285	Approved
0.6639	Remote Similarity	NPD5286	Approved
0.6638	Remote Similarity	NPD5282	Discontinued
0.6617	Remote Similarity	NPD7507	Approved
0.6609	Remote Similarity	NPD5694	Approved
0.6609	Remote Similarity	NPD7983	Approved
0.6609	Remote Similarity	NPD5693	Phase 1
0.6579	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6101	Approved
0.6569	Remote Similarity	NPD6845	Suspended
0.6562	Remote Similarity	NPD6274	Approved
0.656	Remote Similarity	NPD6371	Approved
0.6557	Remote Similarity	NPD5141	Approved
0.6555	Remote Similarity	NPD7638	Approved
0.6545	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7101	Approved
0.6538	Remote Similarity	NPD7100	Approved
0.6529	Remote Similarity	NPD5224	Approved
0.6529	Remote Similarity	NPD5225	Approved
0.6529	Remote Similarity	NPD4633	Approved
0.6529	Remote Similarity	NPD5226	Approved
0.6522	Remote Similarity	NPD7838	Discovery
0.6522	Remote Similarity	NPD5692	Phase 3
0.6522	Remote Similarity	NPD46	Approved
0.6522	Remote Similarity	NPD6698	Approved
0.6519	Remote Similarity	NPD6033	Approved
0.6512	Remote Similarity	NPD6317	Approved
0.6508	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7640	Approved
0.65	Remote Similarity	NPD7639	Approved
0.6496	Remote Similarity	NPD7900	Approved
0.6496	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5737	Approved
0.6491	Remote Similarity	NPD6672	Approved
0.6475	Remote Similarity	NPD5175	Approved
0.6475	Remote Similarity	NPD5174	Approved
0.6471	Remote Similarity	NPD4755	Approved
0.6466	Remote Similarity	NPD6050	Approved
0.6462	Remote Similarity	NPD6314	Approved
0.6462	Remote Similarity	NPD6335	Approved
0.6462	Remote Similarity	NPD6313	Approved
0.6446	Remote Similarity	NPD5223	Approved
0.6441	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5695	Phase 3
0.6439	Remote Similarity	NPD7503	Approved
0.6439	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5696	Approved
0.6412	Remote Similarity	NPD7516	Approved
0.641	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD4729	Approved
0.64	Remote Similarity	NPD4730	Approved
0.6387	Remote Similarity	NPD5222	Approved
0.6387	Remote Similarity	NPD5221	Approved
0.6387	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5207	Approved
0.6378	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4700	Approved
0.6349	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7327	Approved
0.6336	Remote Similarity	NPD7328	Approved
0.6333	Remote Similarity	NPD7902	Approved
0.6333	Remote Similarity	NPD5173	Approved
0.6333	Remote Similarity	NPD6084	Phase 2
0.6333	Remote Similarity	NPD6083	Phase 2
0.6328	Remote Similarity	NPD6053	Discontinued
0.6325	Remote Similarity	NPD7637	Suspended
0.6308	Remote Similarity	NPD6868	Approved
0.6299	Remote Similarity	NPD5249	Phase 3
0.6299	Remote Similarity	NPD5247	Approved
0.6299	Remote Similarity	NPD5248	Approved
0.6299	Remote Similarity	NPD5251	Approved
0.6299	Remote Similarity	NPD5250	Approved
0.6293	Remote Similarity	NPD6673	Approved
0.6293	Remote Similarity	NPD6080	Approved
0.6293	Remote Similarity	NPD6904	Approved
0.6281	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD8407	Phase 2
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD5209	Approved
0.624	Remote Similarity	NPD4767	Approved
0.624	Remote Similarity	NPD4768	Approved
0.6218	Remote Similarity	NPD6001	Approved
0.6218	Remote Similarity	NPD7748	Approved
0.6198	Remote Similarity	NPD5959	Approved
0.6194	Remote Similarity	NPD6909	Approved
0.6194	Remote Similarity	NPD6908	Approved
0.6187	Remote Similarity	NPD5956	Approved
0.6186	Remote Similarity	NPD5281	Approved
0.6186	Remote Similarity	NPD6079	Approved
0.6186	Remote Similarity	NPD5284	Approved
0.6182	Remote Similarity	NPD8368	Discontinued
0.6174	Remote Similarity	NPD5330	Approved
0.6174	Remote Similarity	NPD6684	Approved
0.6174	Remote Similarity	NPD6409	Approved
0.6174	Remote Similarity	NPD7521	Approved
0.6174	Remote Similarity	NPD7334	Approved
0.6174	Remote Similarity	NPD6098	Approved
0.6174	Remote Similarity	NPD7146	Approved
0.6167	Remote Similarity	NPD5654	Approved
0.6154	Remote Similarity	NPD8133	Approved
0.6142	Remote Similarity	NPD5128	Approved
0.6135	Remote Similarity	NPD7799	Discontinued
0.6124	Remote Similarity	NPD5216	Approved
0.6124	Remote Similarity	NPD5217	Approved
0.6124	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD6334	Approved
0.6111	Remote Similarity	NPD6333	Approved
0.6103	Remote Similarity	NPD7830	Approved
0.6103	Remote Similarity	NPD7829	Approved
0.6102	Remote Similarity	NPD3168	Discontinued
0.6099	Remote Similarity	NPD8338	Approved
0.6095	Remote Similarity	NPD8434	Phase 2
0.608	Remote Similarity	NPD4754	Approved
0.6074	Remote Similarity	NPD8380	Approved
0.6074	Remote Similarity	NPD8335	Approved
0.6074	Remote Similarity	NPD8033	Approved
0.6074	Remote Similarity	NPD8379	Approved
0.6074	Remote Similarity	NPD8296	Approved
0.6074	Remote Similarity	NPD8378	Approved
0.6068	Remote Similarity	NPD6903	Approved
0.6068	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6412	Phase 2
0.6055	Remote Similarity	NPD8039	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