NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.197
LogD:	1.702
LogS:	-1.89
# 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:	0.531
Synthetic Accessibility Score:	4.678
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.796
MDCK Permeability:	4.3532345443964005e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	64.76067352294922%
Volume Distribution (VD):	0.64
Pgp-substrate:	49.864219665527344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.387
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	14.312
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.195
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.806
Maximum Recommended Daily Dose:	0.795
Skin Sensitization:	0.683
Carcinogencity:	0.878
Eye Corrosion:	0.847
Eye Irritation:	0.862
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC200237

Natural Product ID:	NPC200237
*Common Name:**	Burrodin
IUPAC Name:	(3aR,5S,5aS,6S,8aS,9aR)-6-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
Synonyms:	Burrodin
Standard InCHIKey:	HSNYUOAAQCCKRP-UGKIOTTESA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7,9-11,13,16H,2,4-6H2,1,3H3/t7-,9+,10-,11+,13+,15+/m0/s1
SMILES:	C[C@H]1C[C@H]2OC(=O)C(=C)[C@H]2C[C@]2([C@H]1[C@@H](O)CC2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509159
PubChem CID:	177140
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:0002046] Ambrosanolides and secoambrosanolides

*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
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	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	3

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	3800.0	nM	PMID[522342]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9500.0	nM	PMID[522343]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	251400.0	nM	PMID[522341]

☑ 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 NPC200237 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	255
0.1-0.2	1885
0.2-0.3	6857
0.3-0.4	13967
0.4-0.5	9940
0.5-0.6	6546
0.6-0.7	2776
0.7-0.8	360
0.8-0.85	41
0.85-0.9	36
0.9-0.95	30
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC91771
0.9663	High Similarity	NPC142529
0.9545	High Similarity	NPC153590
0.9438	High Similarity	NPC473331
0.9326	High Similarity	NPC473263
0.9326	High Similarity	NPC473234
0.9326	High Similarity	NPC60386
0.9326	High Similarity	NPC473273
0.9326	High Similarity	NPC308656
0.9302	High Similarity	NPC56593
0.9247	High Similarity	NPC171759
0.9213	High Similarity	NPC286341
0.9213	High Similarity	NPC191339
0.9205	High Similarity	NPC155935
0.9205	High Similarity	NPC12872
0.9205	High Similarity	NPC168679
0.913	High Similarity	NPC311904
0.9101	High Similarity	NPC54065
0.9101	High Similarity	NPC35809
0.9101	High Similarity	NPC297474
0.9	High Similarity	NPC171360
0.9	High Similarity	NPC35959
0.9	High Similarity	NPC57304
0.9	High Similarity	NPC133888
0.9	High Similarity	NPC29821
0.9	High Similarity	NPC293001
0.9	High Similarity	NPC63193
0.8977	High Similarity	NPC201658
0.8977	High Similarity	NPC118601
0.8925	High Similarity	NPC170143
0.8925	High Similarity	NPC108475
0.8925	High Similarity	NPC213947
0.8889	High Similarity	NPC19087
0.8876	High Similarity	NPC178875
0.8817	High Similarity	NPC126156
0.8791	High Similarity	NPC184063
0.8778	High Similarity	NPC38392
0.8778	High Similarity	NPC215556
0.875	High Similarity	NPC204105
0.875	High Similarity	NPC284534
0.875	High Similarity	NPC300082
0.871	High Similarity	NPC163228
0.8681	High Similarity	NPC216284
0.8667	High Similarity	NPC207114
0.8667	High Similarity	NPC79549
0.8667	High Similarity	NPC217983
0.8652	High Similarity	NPC236692
0.8652	High Similarity	NPC238593
0.8652	High Similarity	NPC187661
0.8652	High Similarity	NPC309757
0.8636	High Similarity	NPC194859
0.8636	High Similarity	NPC224386
0.8617	High Similarity	NPC18019
0.8617	High Similarity	NPC24956
0.8605	High Similarity	NPC290508
0.8605	High Similarity	NPC73052
0.8605	High Similarity	NPC293418
0.8605	High Similarity	NPC6823
0.8556	High Similarity	NPC24728
0.8526	High Similarity	NPC471150
0.8523	High Similarity	NPC54468
0.8511	High Similarity	NPC476053
0.8462	Intermediate Similarity	NPC471149
0.8444	Intermediate Similarity	NPC304558
0.8444	Intermediate Similarity	NPC470242
0.8409	Intermediate Similarity	NPC246076
0.8387	Intermediate Similarity	NPC155215
0.837	Intermediate Similarity	NPC283409
0.8352	Intermediate Similarity	NPC270270
0.8351	Intermediate Similarity	NPC471381
0.8333	Intermediate Similarity	NPC474313
0.8316	Intermediate Similarity	NPC472873
0.8316	Intermediate Similarity	NPC48803
0.8316	Intermediate Similarity	NPC90121
0.8316	Intermediate Similarity	NPC275960
0.8316	Intermediate Similarity	NPC193645
0.8315	Intermediate Similarity	NPC245665
0.8315	Intermediate Similarity	NPC111409
0.8315	Intermediate Similarity	NPC128246
0.8298	Intermediate Similarity	NPC258216
0.8298	Intermediate Similarity	NPC135776
0.8295	Intermediate Similarity	NPC47635
0.8295	Intermediate Similarity	NPC126248
0.828	Intermediate Similarity	NPC106510
0.828	Intermediate Similarity	NPC71533
0.8256	Intermediate Similarity	NPC208223
0.8242	Intermediate Similarity	NPC67493
0.8229	Intermediate Similarity	NPC476009
0.82	Intermediate Similarity	NPC203659
0.8191	Intermediate Similarity	NPC475925
0.8182	Intermediate Similarity	NPC156658
0.8182	Intermediate Similarity	NPC258965
0.8182	Intermediate Similarity	NPC51507
0.8182	Intermediate Similarity	NPC225353
0.8163	Intermediate Similarity	NPC186861
0.8152	Intermediate Similarity	NPC190753
0.8144	Intermediate Similarity	NPC169205
0.8144	Intermediate Similarity	NPC477949
0.8125	Intermediate Similarity	NPC170120
0.8125	Intermediate Similarity	NPC475900
0.8125	Intermediate Similarity	NPC52044
0.8125	Intermediate Similarity	NPC213698
0.81	Intermediate Similarity	NPC110989
0.8085	Intermediate Similarity	NPC301969
0.8085	Intermediate Similarity	NPC37607
0.8081	Intermediate Similarity	NPC477950
0.8065	Intermediate Similarity	NPC91248
0.8061	Intermediate Similarity	NPC141191
0.8043	Intermediate Similarity	NPC64153
0.8041	Intermediate Similarity	NPC185553
0.8021	Intermediate Similarity	NPC127019
0.8	Intermediate Similarity	NPC131209
0.7979	Intermediate Similarity	NPC472872
0.7979	Intermediate Similarity	NPC32922
0.7959	Intermediate Similarity	NPC161493
0.7957	Intermediate Similarity	NPC186148
0.7941	Intermediate Similarity	NPC44004
0.7941	Intermediate Similarity	NPC54737
0.7938	Intermediate Similarity	NPC67584
0.7935	Intermediate Similarity	NPC235792
0.7921	Intermediate Similarity	NPC221421
0.7917	Intermediate Similarity	NPC475788
0.7912	Intermediate Similarity	NPC215294
0.7907	Intermediate Similarity	NPC320537
0.7907	Intermediate Similarity	NPC143979
0.79	Intermediate Similarity	NPC475099
0.7895	Intermediate Similarity	NPC246173
0.7879	Intermediate Similarity	NPC45125
0.7872	Intermediate Similarity	NPC58219
0.7872	Intermediate Similarity	NPC177629
0.7857	Intermediate Similarity	NPC213078
0.7843	Intermediate Similarity	NPC100487
0.7835	Intermediate Similarity	NPC470013
0.7835	Intermediate Similarity	NPC470010
0.7835	Intermediate Similarity	NPC323008
0.7835	Intermediate Similarity	NPC198853
0.7835	Intermediate Similarity	NPC167219
0.7835	Intermediate Similarity	NPC262133
0.7826	Intermediate Similarity	NPC156485
0.7822	Intermediate Similarity	NPC80144
0.7822	Intermediate Similarity	NPC474747
0.7812	Intermediate Similarity	NPC74103
0.7812	Intermediate Similarity	NPC123177
0.7812	Intermediate Similarity	NPC150978
0.7812	Intermediate Similarity	NPC133698
0.7812	Intermediate Similarity	NPC70595
0.7812	Intermediate Similarity	NPC221282
0.7789	Intermediate Similarity	NPC295312
0.7789	Intermediate Similarity	NPC92974
0.7789	Intermediate Similarity	NPC173926
0.7789	Intermediate Similarity	NPC117405
0.7789	Intermediate Similarity	NPC52198
0.7778	Intermediate Similarity	NPC181151
0.7755	Intermediate Similarity	NPC37408
0.7755	Intermediate Similarity	NPC469873
0.7745	Intermediate Similarity	NPC475945
0.7745	Intermediate Similarity	NPC475871
0.7745	Intermediate Similarity	NPC474775
0.7742	Intermediate Similarity	NPC21471
0.7742	Intermediate Similarity	NPC33570
0.7742	Intermediate Similarity	NPC161957
0.7742	Intermediate Similarity	NPC329749
0.7732	Intermediate Similarity	NPC475488
0.7723	Intermediate Similarity	NPC150923
0.7723	Intermediate Similarity	NPC67296
0.7723	Intermediate Similarity	NPC474742
0.7714	Intermediate Similarity	NPC139838
0.7714	Intermediate Similarity	NPC59489
0.7708	Intermediate Similarity	NPC253144
0.77	Intermediate Similarity	NPC249171
0.77	Intermediate Similarity	NPC49833
0.77	Intermediate Similarity	NPC221615
0.7685	Intermediate Similarity	NPC471380
0.7685	Intermediate Similarity	NPC123117
0.7685	Intermediate Similarity	NPC471382
0.7684	Intermediate Similarity	NPC224652
0.7684	Intermediate Similarity	NPC53158
0.7684	Intermediate Similarity	NPC202672
0.7677	Intermediate Similarity	NPC76862
0.7677	Intermediate Similarity	NPC158416
0.7677	Intermediate Similarity	NPC39859
0.7677	Intermediate Similarity	NPC470883
0.766	Intermediate Similarity	NPC475019
0.766	Intermediate Similarity	NPC474949
0.7653	Intermediate Similarity	NPC90453
0.7653	Intermediate Similarity	NPC477131
0.7634	Intermediate Similarity	NPC474780
0.7629	Intermediate Similarity	NPC261607
0.7629	Intermediate Similarity	NPC284185
0.7629	Intermediate Similarity	NPC12172
0.7629	Intermediate Similarity	NPC111114
0.7629	Intermediate Similarity	NPC290651
0.7629	Intermediate Similarity	NPC300312
0.7629	Intermediate Similarity	NPC208886
0.7624	Intermediate Similarity	NPC267921
0.7624	Intermediate Similarity	NPC70865
0.7624	Intermediate Similarity	NPC280963
0.7614	Intermediate Similarity	NPC179922
0.7604	Intermediate Similarity	NPC116620
0.7604	Intermediate Similarity	NPC268298

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 NPC200237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	2607
0.2-0.3	3903
0.3-0.4	1592
0.4-0.5	419
0.5-0.6	264
0.6-0.7	47
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5785	Approved
0.7524	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6371	Approved
0.7423	Intermediate Similarity	NPD1695	Approved
0.7292	Intermediate Similarity	NPD5786	Approved
0.7188	Intermediate Similarity	NPD5363	Approved
0.7128	Intermediate Similarity	NPD5369	Approved
0.7053	Intermediate Similarity	NPD4269	Approved
0.7053	Intermediate Similarity	NPD4270	Approved
0.6875	Remote Similarity	NPD6435	Approved
0.6875	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD4252	Approved
0.6837	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5362	Discontinued
0.6796	Remote Similarity	NPD5282	Discontinued
0.6789	Remote Similarity	NPD6008	Approved
0.6768	Remote Similarity	NPD4249	Approved
0.67	Remote Similarity	NPD4251	Approved
0.67	Remote Similarity	NPD4250	Approved
0.6698	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5368	Approved
0.6636	Remote Similarity	NPD7640	Approved
0.6636	Remote Similarity	NPD7639	Approved
0.6542	Remote Similarity	NPD4225	Approved
0.6538	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD5779	Approved
0.6529	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD1694	Approved
0.6475	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD6319	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6458	Remote Similarity	NPD4802	Phase 2
0.6458	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4238	Approved
0.6442	Remote Similarity	NPD6411	Approved
0.6442	Remote Similarity	NPD7983	Approved
0.6429	Remote Similarity	NPD5697	Approved
0.6423	Remote Similarity	NPD7078	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6381	Remote Similarity	NPD6399	Phase 3
0.6379	Remote Similarity	NPD4632	Approved
0.6372	Remote Similarity	NPD6899	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD6011	Approved
0.6372	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6881	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD5209	Approved
0.6356	Remote Similarity	NPD7115	Discovery
0.6348	Remote Similarity	NPD6649	Approved
0.6348	Remote Similarity	NPD6650	Approved
0.6346	Remote Similarity	NPD46	Approved
0.6346	Remote Similarity	NPD6698	Approved
0.6339	Remote Similarity	NPD6675	Approved
0.6339	Remote Similarity	NPD5739	Approved
0.6339	Remote Similarity	NPD7128	Approved
0.6339	Remote Similarity	NPD6402	Approved
0.6333	Remote Similarity	NPD6059	Approved
0.6327	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7319	Approved
0.6316	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD6372	Approved
0.6316	Remote Similarity	NPD6014	Approved
0.6311	Remote Similarity	NPD6903	Approved
0.63	Remote Similarity	NPD4788	Approved
0.63	Remote Similarity	NPD7154	Phase 3
0.63	Remote Similarity	NPD5331	Approved
0.63	Remote Similarity	NPD5332	Approved
0.6296	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD6084	Phase 2
0.629	Remote Similarity	NPD8293	Discontinued
0.6286	Remote Similarity	NPD7637	Suspended
0.6283	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD7146	Approved
0.6275	Remote Similarity	NPD6409	Approved
0.6275	Remote Similarity	NPD5330	Approved
0.6275	Remote Similarity	NPD7521	Approved
0.6275	Remote Similarity	NPD6684	Approved
0.6275	Remote Similarity	NPD7334	Approved
0.6263	Remote Similarity	NPD4790	Discontinued
0.6262	Remote Similarity	NPD5695	Phase 3
0.6261	Remote Similarity	NPD7102	Approved
0.6261	Remote Similarity	NPD6883	Approved
0.6261	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5696	Approved
0.6238	Remote Similarity	NPD3665	Phase 1
0.6238	Remote Similarity	NPD3666	Approved
0.6238	Remote Similarity	NPD3133	Approved
0.6228	Remote Similarity	NPD6686	Approved
0.6218	Remote Similarity	NPD6009	Approved
0.6216	Remote Similarity	NPD7632	Discontinued
0.621	Remote Similarity	NPD7507	Approved
0.6207	Remote Similarity	NPD6869	Approved
0.6207	Remote Similarity	NPD6847	Approved
0.6207	Remote Similarity	NPD8130	Phase 1
0.6207	Remote Similarity	NPD6617	Approved
0.62	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4821	Approved
0.6162	Remote Similarity	NPD4822	Approved
0.6162	Remote Similarity	NPD4820	Approved
0.6162	Remote Similarity	NPD4819	Approved
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6882	Approved
0.6148	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5983	Phase 2
0.614	Remote Similarity	NPD6412	Phase 2
0.6132	Remote Similarity	NPD8035	Phase 2
0.6132	Remote Similarity	NPD5693	Phase 1
0.6132	Remote Similarity	NPD8034	Phase 2
0.6126	Remote Similarity	NPD1700	Approved
0.6122	Remote Similarity	NPD4271	Approved
0.6122	Remote Similarity	NPD4268	Approved
0.6121	Remote Similarity	NPD4634	Approved
0.6111	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5211	Phase 2
0.6068	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7839	Suspended
0.6048	Remote Similarity	NPD7604	Phase 2
0.6047	Remote Similarity	NPD6845	Suspended
0.604	Remote Similarity	NPD3667	Approved
0.6038	Remote Similarity	NPD5207	Approved
0.6038	Remote Similarity	NPD7838	Discovery
0.6036	Remote Similarity	NPD4696	Approved
0.6036	Remote Similarity	NPD5285	Approved
0.6036	Remote Similarity	NPD5286	Approved
0.6023	Remote Similarity	NPD3198	Approved
0.6019	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8266	Approved
0.6016	Remote Similarity	NPD8267	Approved
0.6016	Remote Similarity	NPD8268	Approved
0.6016	Remote Similarity	NPD8269	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5984	Remote Similarity	NPD6033	Approved
0.5982	Remote Similarity	NPD5223	Approved
0.5981	Remote Similarity	NPD5284	Approved
0.5981	Remote Similarity	NPD6079	Approved
0.5981	Remote Similarity	NPD5281	Approved
0.5969	Remote Similarity	NPD7260	Phase 2
0.5966	Remote Similarity	NPD8133	Approved
0.5965	Remote Similarity	NPD5141	Approved
0.5963	Remote Similarity	NPD5210	Approved
0.5963	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD3618	Phase 1
0.5952	Remote Similarity	NPD6336	Discontinued
0.595	Remote Similarity	NPD6317	Approved
0.5943	Remote Similarity	NPD4753	Phase 2
0.5943	Remote Similarity	NPD5328	Approved
0.5943	Remote Similarity	NPD5370	Suspended
0.5929	Remote Similarity	NPD5226	Approved
0.5929	Remote Similarity	NPD5224	Approved
0.5929	Remote Similarity	NPD5225	Approved
0.5929	Remote Similarity	NPD4633	Approved
0.5922	Remote Similarity	NPD4786	Approved
0.5909	Remote Similarity	NPD5221	Approved
0.5909	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4697	Phase 3
0.5909	Remote Similarity	NPD5222	Approved
0.5902	Remote Similarity	NPD6314	Approved
0.5902	Remote Similarity	NPD6335	Approved
0.5902	Remote Similarity	NPD6313	Approved
0.5893	Remote Similarity	NPD4700	Approved
0.5887	Remote Similarity	NPD8515	Approved
0.5887	Remote Similarity	NPD8517	Approved
0.5887	Remote Similarity	NPD8516	Approved
0.5887	Remote Similarity	NPD8513	Phase 3
0.5877	Remote Similarity	NPD5175	Approved
0.5877	Remote Similarity	NPD5174	Approved
0.5872	Remote Similarity	NPD6001	Approved
0.5856	Remote Similarity	NPD5173	Approved
0.5854	Remote Similarity	NPD7100	Approved
0.5854	Remote Similarity	NPD7101	Approved
0.5849	Remote Similarity	NPD5737	Approved
0.5849	Remote Similarity	NPD6672	Approved
0.5833	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD6334	Approved
0.5821	Remote Similarity	NPD6333	Approved
0.5816	Remote Similarity	NPD3702	Approved
0.581	Remote Similarity	NPD5279	Phase 3
0.5804	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6673	Approved
0.5794	Remote Similarity	NPD6080	Approved
0.5794	Remote Similarity	NPD6904	Approved
0.578	Remote Similarity	NPD4202	Approved
0.5769	Remote Similarity	NPD5956	Approved
0.5763	Remote Similarity	NPD4061	Clinical (unspecified phase)

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