NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	1.519
LogD:	1.535
LogS:	-2.466
# 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:	0.676
Synthetic Accessibility Score:	4.568
Fsp3:	0.867
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:	-4.613
MDCK Permeability:	9.470662189414725e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.863
Plasma Protein Binding (PPB):	47.0208625793457%
Volume Distribution (VD):	0.57
Pgp-substrate:	38.73611831665039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.581
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.155
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	10.163
Half-life (T1/2):	0.783

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.607
Drug-inuced Liver Injury (DILI):	0.461
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.762
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.168
Carcinogencity:	0.329
Eye Corrosion:	0.355
Eye Irritation:	0.288
Respiratory Toxicity:	0.493

Download Data

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

Natural Product: NPC215030

Natural Product ID:	NPC215030
*Common Name:**	(11S)-10Alpha-Hydroxy-3-Oxo-4Betah-Guaiano-12,6Alpha-Lactone
IUPAC Name:	(3S,3aS,6R,6aR,9S,9aR,9bS)-6-hydroxy-3,6,9-trimethyl-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
Synonyms:
Standard InCHIKey:	HWMHVPGJPQEKFZ-IGRWEYARSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-7-9-4-5-15(3,18)10-6-11(16)8(2)12(10)13(9)19-14(7)17/h7-10,12-13,18H,4-6H2,1-3H3/t7-,8+,9-,10+,12-,13-,15+/m0/s1
SMILES:	C[C@H]1[C@@H]2CC[C@](C)([C@@H]3CC(=O)[C@@H](C)[C@@H]3[C@H]2OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465422
PubChem CID:	11311642
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:0001770] Guaianolides 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
NPO21931	Quercus phillyraeoides	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15635221]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067155]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21931	Quercus phillyraeoides	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28437	Hypomyces aurantius	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22206	Browallia speciosa	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23089	Reseda duriaeana	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21931	Quercus phillyraeoides	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6546	Maytenus rigida	Species	Celastraceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	32000.0	nM	PMID[502207]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	160000.0	nM	PMID[502207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	230000.0	nM	PMID[502207]

☑ 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 NPC215030 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	484
0.1-0.2	4223
0.2-0.3	13425
0.3-0.4	11764
0.4-0.5	8168
0.5-0.6	3838
0.6-0.7	642
0.7-0.8	144
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC179922
0.8293	Intermediate Similarity	NPC178875
0.8286	Intermediate Similarity	NPC157518
0.8171	Intermediate Similarity	NPC118601
0.8133	Intermediate Similarity	NPC477867
0.8108	Intermediate Similarity	NPC470243
0.8082	Intermediate Similarity	NPC98711
0.8082	Intermediate Similarity	NPC475062
0.8052	Intermediate Similarity	NPC83108
0.8052	Intermediate Similarity	NPC214030
0.7975	Intermediate Similarity	NPC156658
0.7975	Intermediate Similarity	NPC258965
0.7975	Intermediate Similarity	NPC51507
0.7901	Intermediate Similarity	NPC111409
0.7901	Intermediate Similarity	NPC157328
0.7821	Intermediate Similarity	NPC70996
0.7816	Intermediate Similarity	NPC470424
0.7778	Intermediate Similarity	NPC212340
0.7765	Intermediate Similarity	NPC32922
0.7727	Intermediate Similarity	NPC163228
0.7722	Intermediate Similarity	NPC470014
0.7701	Intermediate Similarity	NPC153590
0.7683	Intermediate Similarity	NPC128246
0.7654	Intermediate Similarity	NPC126248
0.7647	Intermediate Similarity	NPC79549
0.7619	Intermediate Similarity	NPC309757
0.7619	Intermediate Similarity	NPC236692
0.7558	Intermediate Similarity	NPC200580
0.7558	Intermediate Similarity	NPC215556
0.7532	Intermediate Similarity	NPC51249
0.7532	Intermediate Similarity	NPC473699
0.7532	Intermediate Similarity	NPC475232
0.7532	Intermediate Similarity	NPC474100
0.7532	Intermediate Similarity	NPC475260
0.7532	Intermediate Similarity	NPC473775
0.75	Intermediate Similarity	NPC300082
0.75	Intermediate Similarity	NPC135776
0.75	Intermediate Similarity	NPC284534
0.75	Intermediate Similarity	NPC475616
0.75	Intermediate Similarity	NPC204105
0.7471	Intermediate Similarity	NPC216284
0.7467	Intermediate Similarity	NPC319007
0.7412	Intermediate Similarity	NPC470242
0.7412	Intermediate Similarity	NPC476717
0.7386	Intermediate Similarity	NPC474065
0.7386	Intermediate Similarity	NPC155215
0.7381	Intermediate Similarity	NPC291310
0.7368	Intermediate Similarity	NPC28526
0.7349	Intermediate Similarity	NPC102156
0.7349	Intermediate Similarity	NPC148740
0.7342	Intermediate Similarity	NPC471491
0.7333	Intermediate Similarity	NPC286842
0.7333	Intermediate Similarity	NPC476053
0.7326	Intermediate Similarity	NPC239938
0.7326	Intermediate Similarity	NPC270270
0.7303	Intermediate Similarity	NPC200237
0.7303	Intermediate Similarity	NPC473273
0.7303	Intermediate Similarity	NPC473263
0.7303	Intermediate Similarity	NPC258216
0.7303	Intermediate Similarity	NPC473234
0.7303	Intermediate Similarity	NPC308656
0.7303	Intermediate Similarity	NPC60386
0.7294	Intermediate Similarity	NPC473350
0.7253	Intermediate Similarity	NPC142529
0.7253	Intermediate Similarity	NPC91771
0.7253	Intermediate Similarity	NPC126156
0.7241	Intermediate Similarity	NPC53158
0.7241	Intermediate Similarity	NPC207114
0.7241	Intermediate Similarity	NPC217983
0.7241	Intermediate Similarity	NPC470009
0.7222	Intermediate Similarity	NPC473331
0.7209	Intermediate Similarity	NPC470657
0.7209	Intermediate Similarity	NPC187661
0.7204	Intermediate Similarity	NPC471381
0.7204	Intermediate Similarity	NPC186861
0.7191	Intermediate Similarity	NPC184063
0.7191	Intermediate Similarity	NPC133698
0.7191	Intermediate Similarity	NPC131209
0.7176	Intermediate Similarity	NPC194859
0.7176	Intermediate Similarity	NPC473791
0.7176	Intermediate Similarity	NPC224386
0.7174	Intermediate Similarity	NPC471150
0.716	Intermediate Similarity	NPC474003
0.716	Intermediate Similarity	NPC169389
0.7159	Intermediate Similarity	NPC168679
0.7159	Intermediate Similarity	NPC12872
0.7159	Intermediate Similarity	NPC155935
0.7143	Intermediate Similarity	NPC311642
0.7143	Intermediate Similarity	NPC100366
0.7143	Intermediate Similarity	NPC164289
0.7143	Intermediate Similarity	NPC246076
0.7143	Intermediate Similarity	NPC472873
0.7143	Intermediate Similarity	NPC5714
0.7143	Intermediate Similarity	NPC242771
0.7126	Intermediate Similarity	NPC190753
0.7126	Intermediate Similarity	NPC31349
0.7126	Intermediate Similarity	NPC475773
0.7125	Intermediate Similarity	NPC155441
0.7123	Intermediate Similarity	NPC469923
0.7111	Intermediate Similarity	NPC475788
0.7108	Intermediate Similarity	NPC1882
0.7108	Intermediate Similarity	NPC134227
0.7097	Intermediate Similarity	NPC211087
0.7093	Intermediate Similarity	NPC476715
0.7079	Intermediate Similarity	NPC35809
0.7079	Intermediate Similarity	NPC297474
0.7079	Intermediate Similarity	NPC54065
0.7079	Intermediate Similarity	NPC19087
0.7065	Intermediate Similarity	NPC193785
0.7059	Intermediate Similarity	NPC15091
0.7059	Intermediate Similarity	NPC54468
0.7059	Intermediate Similarity	NPC245665
0.7045	Intermediate Similarity	NPC191221
0.7045	Intermediate Similarity	NPC203170
0.7045	Intermediate Similarity	NPC91248
0.7033	Intermediate Similarity	NPC323008
0.7033	Intermediate Similarity	NPC198853
0.7033	Intermediate Similarity	NPC470010
0.7033	Intermediate Similarity	NPC470013
0.7033	Intermediate Similarity	NPC262133
0.7033	Intermediate Similarity	NPC470423
0.7033	Intermediate Similarity	NPC477131
0.7013	Intermediate Similarity	NPC82315
0.7011	Intermediate Similarity	NPC67493
0.7011	Intermediate Similarity	NPC56593
0.701	Intermediate Similarity	NPC168890
0.701	Intermediate Similarity	NPC469441
0.701	Intermediate Similarity	NPC41674
0.701	Intermediate Similarity	NPC228311
0.701	Intermediate Similarity	NPC252234
0.7	Intermediate Similarity	NPC133888
0.7	Intermediate Similarity	NPC52756
0.7	Intermediate Similarity	NPC286341
0.7	Intermediate Similarity	NPC29821
0.7	Intermediate Similarity	NPC191339
0.7	Intermediate Similarity	NPC293001
0.7	Intermediate Similarity	NPC35959
0.7	Intermediate Similarity	NPC475925
0.7	Intermediate Similarity	NPC57304
0.7	Intermediate Similarity	NPC125164
0.7	Intermediate Similarity	NPC171360
0.7	Intermediate Similarity	NPC63193
0.6989	Remote Similarity	NPC213947
0.6989	Remote Similarity	NPC311904
0.6989	Remote Similarity	NPC108475
0.6989	Remote Similarity	NPC170143
0.6986	Remote Similarity	NPC469921
0.6977	Remote Similarity	NPC477434
0.6966	Remote Similarity	NPC472872
0.6966	Remote Similarity	NPC38392
0.6966	Remote Similarity	NPC61688
0.6957	Remote Similarity	NPC52044
0.6957	Remote Similarity	NPC37408
0.6957	Remote Similarity	NPC67584
0.6957	Remote Similarity	NPC475900
0.6957	Remote Similarity	NPC470191
0.6951	Remote Similarity	NPC208223
0.6947	Remote Similarity	NPC171759
0.6939	Remote Similarity	NPC290247
0.6939	Remote Similarity	NPC469788
0.6939	Remote Similarity	NPC469787
0.6939	Remote Similarity	NPC176756
0.6933	Remote Similarity	NPC314103
0.6932	Remote Similarity	NPC186148
0.6932	Remote Similarity	NPC201658
0.6923	Remote Similarity	NPC161035
0.6923	Remote Similarity	NPC472238
0.6923	Remote Similarity	NPC476189
0.6923	Remote Similarity	NPC472237
0.6915	Remote Similarity	NPC253995
0.6915	Remote Similarity	NPC274695
0.6915	Remote Similarity	NPC45125
0.6914	Remote Similarity	NPC217725
0.6914	Remote Similarity	NPC132064
0.6914	Remote Similarity	NPC228411
0.6907	Remote Similarity	NPC473701
0.6907	Remote Similarity	NPC473526
0.6905	Remote Similarity	NPC73052
0.6905	Remote Similarity	NPC293418
0.6905	Remote Similarity	NPC125366
0.6905	Remote Similarity	NPC290508
0.6892	Remote Similarity	NPC469922
0.6889	Remote Similarity	NPC246173
0.6889	Remote Similarity	NPC37607
0.6889	Remote Similarity	NPC301969
0.6883	Remote Similarity	NPC469925
0.6882	Remote Similarity	NPC476009
0.6882	Remote Similarity	NPC213078
0.6869	Remote Similarity	NPC329876
0.6869	Remote Similarity	NPC220773
0.6869	Remote Similarity	NPC278693
0.6869	Remote Similarity	NPC167044
0.686	Remote Similarity	NPC474266
0.686	Remote Similarity	NPC476721
0.686	Remote Similarity	NPC472847
0.6857	Remote Similarity	NPC319589
0.6854	Remote Similarity	NPC226491
0.6854	Remote Similarity	NPC177629
0.6854	Remote Similarity	NPC58219
0.6854	Remote Similarity	NPC477614

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 NPC215030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	674
0.1-0.2	4165
0.2-0.3	2929
0.3-0.4	805
0.4-0.5	416
0.5-0.6	144
0.6-0.7	17
0.7-0.8	0
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
0.7073	Intermediate Similarity	NPD4802	Phase 2
0.7073	Intermediate Similarity	NPD4238	Approved
0.6849	Remote Similarity	NPD3198	Approved
0.6771	Remote Similarity	NPD1700	Approved
0.6707	Remote Similarity	NPD3702	Approved
0.6593	Remote Similarity	NPD1695	Approved
0.6566	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6435	Approved
0.6494	Remote Similarity	NPD7909	Approved
0.6471	Remote Similarity	NPD6114	Approved
0.6471	Remote Similarity	NPD6118	Approved
0.6471	Remote Similarity	NPD6697	Approved
0.6471	Remote Similarity	NPD6115	Approved
0.6421	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.641	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD229	Approved
0.6353	Remote Similarity	NPD6116	Phase 1
0.6322	Remote Similarity	NPD5368	Approved
0.631	Remote Similarity	NPD3703	Phase 2
0.625	Remote Similarity	NPD1780	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD1779	Approved
0.6235	Remote Similarity	NPD6117	Approved
0.6203	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6008	Approved
0.6176	Remote Similarity	NPD634	Phase 3
0.6164	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5777	Approved
0.6145	Remote Similarity	NPD6081	Approved
0.6125	Remote Similarity	NPD4224	Phase 2
0.6117	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4249	Approved
0.6087	Remote Similarity	NPD5786	Approved
0.6078	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6399	Phase 3
0.6022	Remote Similarity	NPD4251	Approved
0.6022	Remote Similarity	NPD4250	Approved
0.5981	Remote Similarity	NPD6053	Discontinued
0.5979	Remote Similarity	NPD5282	Discontinued
0.5952	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD8034	Phase 2
0.5938	Remote Similarity	NPD8035	Phase 2
0.5934	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5362	Discontinued
0.5934	Remote Similarity	NPD3669	Approved
0.5909	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3698	Phase 2
0.5833	Remote Similarity	NPD4245	Approved
0.5833	Remote Similarity	NPD4789	Approved
0.5833	Remote Similarity	NPD4244	Approved
0.5824	Remote Similarity	NPD4270	Approved
0.5824	Remote Similarity	NPD7345	Approved
0.5824	Remote Similarity	NPD4269	Approved
0.5806	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6371	Approved
0.5783	Remote Similarity	NPD5360	Phase 3
0.5783	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD2266	Phase 2
0.5755	Remote Similarity	NPD7320	Approved
0.5733	Remote Similarity	NPD3728	Approved
0.5733	Remote Similarity	NPD3730	Approved
0.5732	Remote Similarity	NPD375	Phase 2
0.5728	Remote Similarity	NPD8085	Approved
0.5728	Remote Similarity	NPD8083	Approved
0.5728	Remote Similarity	NPD8138	Approved
0.5728	Remote Similarity	NPD8086	Approved
0.5728	Remote Similarity	NPD8139	Approved
0.5728	Remote Similarity	NPD8084	Approved
0.5728	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD6372	Approved
0.5701	Remote Similarity	NPD6373	Approved
0.5676	Remote Similarity	NPD3186	Phase 1
0.5673	Remote Similarity	NPD8276	Approved
0.5673	Remote Similarity	NPD8275	Approved
0.566	Remote Similarity	NPD5697	Approved
0.566	Remote Similarity	NPD5701	Approved
0.5638	Remote Similarity	NPD5363	Approved
0.5636	Remote Similarity	NPD4632	Approved
0.5619	Remote Similarity	NPD8081	Approved
0.5612	Remote Similarity	NPD7983	Approved
0.5607	Remote Similarity	NPD6881	Approved
0.5607	Remote Similarity	NPD6899	Approved
0.5607	Remote Similarity	NPD6011	Approved
0.5607	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4820	Approved
0.5604	Remote Similarity	NPD4821	Approved
0.5604	Remote Similarity	NPD4819	Approved
0.5604	Remote Similarity	NPD6928	Phase 2
0.5604	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4822	Approved
0.5604	Remote Similarity	NPD4252	Approved
0.56	Remote Similarity	NPD5695	Phase 3

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