NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	364.849
LogP:	2.665
LogD:	3.05
LogS:	-3.351
# Rotatable Bonds:	3
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	4.901
Fsp3:	0.75
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:	-4.858
MDCK Permeability:	1.7897224097396247e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.533
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.728
30% Bioavailability (F30%):	0.255

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.555
Plasma Protein Binding (PPB):	93.77781677246094%
Volume Distribution (VD):	1.315
Pgp-substrate:	8.363941192626953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.438
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.436
CYP2C9-inhibitor:	0.323
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	11.033
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.224
Carcinogencity:	0.552
Eye Corrosion:	0.009
Eye Irritation:	0.05
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC477949

Natural Product ID:	NPC477949
*Common Name:**	3-[2-[(1R,2R,3aR,6S,8aR)-6,8a-dihydroxy-1,2,5,5-tetramethyl-4-oxo-2,3,3a,6,7,8-hexahydroazulen-1-yl]ethyl]-2H-furan-5-one
IUPAC Name:	3-[2-[(1R,2R,3aR,6S,8aR)-6,8a-dihydroxy-1,2,5,5-tetramethyl-4-oxo-2,3,3a,6,7,8-hexahydroazulen-1-yl]ethyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	LEZWSCIWQQGIDL-DMIHOJOZSA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-12-9-14-17(23)18(2,3)15(21)6-8-20(14,24)19(12,4)7-5-13-10-16(22)25-11-13/h10,12,14-15,21,24H,5-9,11H2,1-4H3/t12-,14+,15+,19-,20-/m1/s1
SMILES:	C[C@@H]1C[C@H]2C(=O)C([C@H](CC[C@@]2([C@]1(C)CCC3=CC(=O)OC3)O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90682203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO23559	Solidago shortii	Species	Asteraceae	Eukaryota	above-ground portion	Shaw Nature Reserve (Missouri Botanical Garden) (N 38 28.579, W 90 49.500)	2008-SEP	PMID[24922615]
NPO23559	Solidago shortii	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	=	66	%	PMID[24922615]

☑ 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 NPC477949 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	223
0.1-0.2	1333
0.2-0.3	5414
0.3-0.4	12379
0.4-0.5	10457
0.5-0.6	6830
0.6-0.7	4913
0.7-0.8	1064
0.8-0.85	75
0.85-0.9	3
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9263	High Similarity	NPC477950
0.8936	High Similarity	NPC469873
0.8673	High Similarity	NPC171759
0.8673	High Similarity	NPC475099
0.8557	High Similarity	NPC108475
0.8557	High Similarity	NPC170143
0.8557	High Similarity	NPC213947
0.8542	High Similarity	NPC476488
0.8542	High Similarity	NPC476487
0.8542	High Similarity	NPC37408
0.8454	Intermediate Similarity	NPC126156
0.8454	Intermediate Similarity	NPC24956
0.8454	Intermediate Similarity	NPC18019
0.8387	Intermediate Similarity	NPC45957
0.8387	Intermediate Similarity	NPC471657
0.8367	Intermediate Similarity	NPC161493
0.8351	Intermediate Similarity	NPC52044
0.8351	Intermediate Similarity	NPC67584
0.8265	Intermediate Similarity	NPC91771
0.8265	Intermediate Similarity	NPC142529
0.8265	Intermediate Similarity	NPC213078
0.8261	Intermediate Similarity	NPC154893
0.8261	Intermediate Similarity	NPC37005
0.8261	Intermediate Similarity	NPC53011
0.8261	Intermediate Similarity	NPC16887
0.8247	Intermediate Similarity	NPC477131
0.8229	Intermediate Similarity	NPC221282
0.8229	Intermediate Similarity	NPC475925
0.8211	Intermediate Similarity	NPC170775
0.8211	Intermediate Similarity	NPC212664
0.82	Intermediate Similarity	NPC469872
0.82	Intermediate Similarity	NPC469864
0.82	Intermediate Similarity	NPC280963
0.819	Intermediate Similarity	NPC257240
0.819	Intermediate Similarity	NPC179642
0.8182	Intermediate Similarity	NPC311904
0.8172	Intermediate Similarity	NPC245434
0.8163	Intermediate Similarity	NPC213698
0.8155	Intermediate Similarity	NPC179891
0.8144	Intermediate Similarity	NPC153590
0.8144	Intermediate Similarity	NPC308656
0.8144	Intermediate Similarity	NPC200237
0.8144	Intermediate Similarity	NPC473273
0.8144	Intermediate Similarity	NPC60386
0.8144	Intermediate Similarity	NPC473234
0.8144	Intermediate Similarity	NPC473263
0.8137	Intermediate Similarity	NPC110989
0.8125	Intermediate Similarity	NPC37607
0.8125	Intermediate Similarity	NPC301969
0.8125	Intermediate Similarity	NPC54065
0.8125	Intermediate Similarity	NPC297474
0.8119	Intermediate Similarity	NPC150923
0.81	Intermediate Similarity	NPC141191
0.8095	Intermediate Similarity	NPC477102
0.8085	Intermediate Similarity	NPC474045
0.8085	Intermediate Similarity	NPC261253
0.8081	Intermediate Similarity	NPC185553
0.8061	Intermediate Similarity	NPC323008
0.8061	Intermediate Similarity	NPC53685
0.8061	Intermediate Similarity	NPC262133
0.8061	Intermediate Similarity	NPC198853
0.8061	Intermediate Similarity	NPC90453
0.8061	Intermediate Similarity	NPC470013
0.8061	Intermediate Similarity	NPC127019
0.8061	Intermediate Similarity	NPC473331
0.8061	Intermediate Similarity	NPC470010
0.8061	Intermediate Similarity	NPC167219
0.8058	Intermediate Similarity	NPC203659
0.8058	Intermediate Similarity	NPC309190
0.8041	Intermediate Similarity	NPC35959
0.8041	Intermediate Similarity	NPC293001
0.8041	Intermediate Similarity	NPC131209
0.8041	Intermediate Similarity	NPC133888
0.8041	Intermediate Similarity	NPC290651
0.8041	Intermediate Similarity	NPC29821
0.8041	Intermediate Similarity	NPC171360
0.8041	Intermediate Similarity	NPC57304
0.8041	Intermediate Similarity	NPC63193
0.8041	Intermediate Similarity	NPC184063
0.8041	Intermediate Similarity	NPC133698
0.8039	Intermediate Similarity	NPC225353
0.8037	Intermediate Similarity	NPC76550
0.8037	Intermediate Similarity	NPC138757
0.8037	Intermediate Similarity	NPC123855
0.8021	Intermediate Similarity	NPC215556
0.8021	Intermediate Similarity	NPC155935
0.8019	Intermediate Similarity	NPC477103
0.8	Intermediate Similarity	NPC69385
0.8	Intermediate Similarity	NPC169205
0.8	Intermediate Similarity	NPC201658
0.8	Intermediate Similarity	NPC308191
0.798	Intermediate Similarity	NPC170120
0.798	Intermediate Similarity	NPC48803
0.798	Intermediate Similarity	NPC90121
0.798	Intermediate Similarity	NPC193645
0.798	Intermediate Similarity	NPC304886
0.798	Intermediate Similarity	NPC275960
0.7963	Intermediate Similarity	NPC106395
0.7963	Intermediate Similarity	NPC46269
0.7959	Intermediate Similarity	NPC37816
0.7959	Intermediate Similarity	NPC135776
0.7941	Intermediate Similarity	NPC116139
0.7938	Intermediate Similarity	NPC51486
0.7938	Intermediate Similarity	NPC19087
0.7938	Intermediate Similarity	NPC35809
0.7938	Intermediate Similarity	NPC216284
0.7938	Intermediate Similarity	NPC473448
0.7921	Intermediate Similarity	NPC244411
0.7921	Intermediate Similarity	NPC222011
0.7921	Intermediate Similarity	NPC221615
0.7917	Intermediate Similarity	NPC91248
0.7917	Intermediate Similarity	NPC79549
0.7905	Intermediate Similarity	NPC26617
0.7895	Intermediate Similarity	NPC144625
0.7895	Intermediate Similarity	NPC56593
0.7895	Intermediate Similarity	NPC261721
0.7895	Intermediate Similarity	NPC64153
0.789	Intermediate Similarity	NPC133677
0.789	Intermediate Similarity	NPC67290
0.789	Intermediate Similarity	NPC138303
0.7885	Intermediate Similarity	NPC100487
0.7879	Intermediate Similarity	NPC96541
0.7864	Intermediate Similarity	NPC86077
0.7864	Intermediate Similarity	NPC66110
0.7857	Intermediate Similarity	NPC286341
0.7857	Intermediate Similarity	NPC472705
0.7857	Intermediate Similarity	NPC191339
0.7857	Intermediate Similarity	NPC284185
0.785	Intermediate Similarity	NPC206595
0.7843	Intermediate Similarity	NPC54705
0.7838	Intermediate Similarity	NPC475372
0.7835	Intermediate Similarity	NPC38392
0.7835	Intermediate Similarity	NPC168679
0.7835	Intermediate Similarity	NPC232747
0.7835	Intermediate Similarity	NPC32922
0.7835	Intermediate Similarity	NPC12872
0.7818	Intermediate Similarity	NPC469794
0.7818	Intermediate Similarity	NPC72772
0.781	Intermediate Similarity	NPC243998
0.781	Intermediate Similarity	NPC54737
0.7807	Intermediate Similarity	NPC129992
0.78	Intermediate Similarity	NPC220221
0.78	Intermediate Similarity	NPC472873
0.78	Intermediate Similarity	NPC163228
0.7789	Intermediate Similarity	NPC476628
0.7789	Intermediate Similarity	NPC204105
0.7789	Intermediate Similarity	NPC261380
0.7789	Intermediate Similarity	NPC146850
0.7789	Intermediate Similarity	NPC287015
0.7789	Intermediate Similarity	NPC300082
0.7789	Intermediate Similarity	NPC284534
0.7788	Intermediate Similarity	NPC475945
0.7788	Intermediate Similarity	NPC475871
0.7788	Intermediate Similarity	NPC474775
0.7778	Intermediate Similarity	NPC287311
0.7768	Intermediate Similarity	NPC312536
0.7767	Intermediate Similarity	NPC195192
0.7767	Intermediate Similarity	NPC304738
0.7767	Intermediate Similarity	NPC472753
0.7767	Intermediate Similarity	NPC62670
0.7757	Intermediate Similarity	NPC47951
0.7755	Intermediate Similarity	NPC77337
0.7755	Intermediate Similarity	NPC253144
0.7755	Intermediate Similarity	NPC145666
0.7748	Intermediate Similarity	NPC475323
0.7748	Intermediate Similarity	NPC475305
0.7748	Intermediate Similarity	NPC473656
0.7745	Intermediate Similarity	NPC470188
0.7745	Intermediate Similarity	NPC64742
0.7736	Intermediate Similarity	NPC204884
0.7732	Intermediate Similarity	NPC217983
0.7732	Intermediate Similarity	NPC207114
0.7732	Intermediate Similarity	NPC178875
0.7723	Intermediate Similarity	NPC9812
0.7714	Intermediate Similarity	NPC121099
0.7708	Intermediate Similarity	NPC469676
0.7708	Intermediate Similarity	NPC67493
0.77	Intermediate Similarity	NPC65829
0.77	Intermediate Similarity	NPC469632
0.77	Intermediate Similarity	NPC298919
0.7699	Intermediate Similarity	NPC472004
0.7692	Intermediate Similarity	NPC25639
0.7692	Intermediate Similarity	NPC472754
0.7692	Intermediate Similarity	NPC118405
0.7692	Intermediate Similarity	NPC474747
0.7684	Intermediate Similarity	NPC290052
0.7684	Intermediate Similarity	NPC82297
0.7679	Intermediate Similarity	NPC288679
0.7679	Intermediate Similarity	NPC475401
0.7677	Intermediate Similarity	NPC123177
0.7677	Intermediate Similarity	NPC70595
0.7677	Intermediate Similarity	NPC177037
0.7677	Intermediate Similarity	NPC155215
0.7677	Intermediate Similarity	NPC74103
0.7677	Intermediate Similarity	NPC150978
0.7677	Intermediate Similarity	NPC472814
0.767	Intermediate Similarity	NPC474718
0.7664	Intermediate Similarity	NPC472825
0.766	Intermediate Similarity	NPC133844
0.7653	Intermediate Similarity	NPC295312

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 NPC477949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	2008
0.2-0.3	3846
0.3-0.4	2149
0.4-0.5	512
0.5-0.6	224
0.6-0.7	186
0.7-0.8	16
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD6371	Approved
0.8125	Intermediate Similarity	NPD5785	Approved
0.798	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5363	Approved
0.7579	Intermediate Similarity	NPD5362	Discontinued
0.7553	Intermediate Similarity	NPD5369	Approved
0.7545	Intermediate Similarity	NPD6053	Discontinued
0.7475	Intermediate Similarity	NPD1695	Approved
0.7474	Intermediate Similarity	NPD4269	Approved
0.7474	Intermediate Similarity	NPD4270	Approved
0.7419	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7638	Approved
0.7347	Intermediate Similarity	NPD5786	Approved
0.7333	Intermediate Similarity	NPD7640	Approved
0.7333	Intermediate Similarity	NPD7639	Approved
0.7308	Intermediate Similarity	NPD6084	Phase 2
0.7308	Intermediate Similarity	NPD6083	Phase 2
0.7292	Intermediate Similarity	NPD6435	Approved
0.7282	Intermediate Similarity	NPD5695	Phase 3
0.7263	Intermediate Similarity	NPD4252	Approved
0.719	Intermediate Similarity	NPD7319	Approved
0.7184	Intermediate Similarity	NPD5282	Discontinued
0.7182	Intermediate Similarity	NPD7320	Approved
0.7172	Intermediate Similarity	NPD4249	Approved
0.7157	Intermediate Similarity	NPD5693	Phase 1
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.7113	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5209	Approved
0.71	Intermediate Similarity	NPD4250	Approved
0.71	Intermediate Similarity	NPD4251	Approved
0.7091	Intermediate Similarity	NPD5697	Approved
0.7091	Intermediate Similarity	NPD5701	Approved
0.7083	Intermediate Similarity	NPD4822	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.7083	Intermediate Similarity	NPD4821	Approved
0.7083	Intermediate Similarity	NPD4819	Approved
0.7083	Intermediate Similarity	NPD5368	Approved
0.7083	Intermediate Similarity	NPD4820	Approved
0.7083	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5696	Approved
0.7059	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7041	Intermediate Similarity	NPD5331	Approved
0.7041	Intermediate Similarity	NPD5332	Approved
0.703	Intermediate Similarity	NPD6903	Approved
0.7027	Intermediate Similarity	NPD6881	Approved
0.7027	Intermediate Similarity	NPD6899	Approved
0.7027	Intermediate Similarity	NPD6686	Approved
0.7027	Intermediate Similarity	NPD6011	Approved
0.701	Intermediate Similarity	NPD4790	Discontinued
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.699	Remote Similarity	NPD5281	Approved
0.699	Remote Similarity	NPD7637	Suspended
0.699	Remote Similarity	NPD5284	Approved
0.6983	Remote Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD3133	Approved
0.697	Remote Similarity	NPD3666	Approved
0.697	Remote Similarity	NPD3665	Phase 1
0.6964	Remote Similarity	NPD6372	Approved
0.6964	Remote Similarity	NPD6014	Approved
0.6964	Remote Similarity	NPD6013	Approved
0.6964	Remote Similarity	NPD6012	Approved
0.6964	Remote Similarity	NPD6373	Approved
0.6961	Remote Similarity	NPD4753	Phase 2
0.6949	Remote Similarity	NPD6319	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD4202	Approved
0.6903	Remote Similarity	NPD7290	Approved
0.6903	Remote Similarity	NPD7102	Approved
0.6903	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD4271	Approved
0.6875	Remote Similarity	NPD4268	Approved
0.687	Remote Similarity	NPD4632	Approved
0.6869	Remote Similarity	NPD7154	Phase 3
0.6863	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7492	Approved
0.6842	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6650	Approved
0.6842	Remote Similarity	NPD6869	Approved
0.6842	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD8130	Phase 1
0.6842	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD4755	Approved
0.6807	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6803	Remote Similarity	NPD6616	Approved
0.6796	Remote Similarity	NPD6080	Approved
0.6796	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD6904	Approved
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6412	Phase 2
0.6783	Remote Similarity	NPD6882	Approved
0.6783	Remote Similarity	NPD8297	Approved
0.678	Remote Similarity	NPD7328	Approved
0.678	Remote Similarity	NPD7327	Approved
0.6768	Remote Similarity	NPD4223	Phase 3
0.6768	Remote Similarity	NPD4221	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6759	Remote Similarity	NPD4225	Approved
0.6754	Remote Similarity	NPD4634	Approved
0.675	Remote Similarity	NPD6015	Approved
0.675	Remote Similarity	NPD6016	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6748	Remote Similarity	NPD7078	Approved
0.6733	Remote Similarity	NPD1694	Approved
0.6731	Remote Similarity	NPD5692	Phase 3
0.6731	Remote Similarity	NPD5207	Approved
0.6727	Remote Similarity	NPD7632	Discontinued
0.6727	Remote Similarity	NPD5211	Phase 2
0.6723	Remote Similarity	NPD7516	Approved
0.6699	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD5737	Approved
0.6699	Remote Similarity	NPD5208	Approved
0.6697	Remote Similarity	NPD5286	Approved
0.6697	Remote Similarity	NPD5285	Approved
0.6697	Remote Similarity	NPD4700	Approved
0.6697	Remote Similarity	NPD4696	Approved
0.6695	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4629	Approved
0.6636	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD5223	Approved
0.6635	Remote Similarity	NPD6051	Approved
0.6634	Remote Similarity	NPD4197	Approved
0.6612	Remote Similarity	NPD8033	Approved
0.6612	Remote Similarity	NPD8296	Approved
0.6612	Remote Similarity	NPD8379	Approved
0.6612	Remote Similarity	NPD8378	Approved
0.6612	Remote Similarity	NPD5983	Phase 2
0.6612	Remote Similarity	NPD8380	Approved
0.6612	Remote Similarity	NPD8335	Approved
0.661	Remote Similarity	NPD6274	Approved
0.6607	Remote Similarity	NPD5141	Approved
0.6577	Remote Similarity	NPD5226	Approved
0.6577	Remote Similarity	NPD5225	Approved
0.6577	Remote Similarity	NPD4633	Approved
0.6577	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD7838	Discovery
0.6569	Remote Similarity	NPD5329	Approved
0.6555	Remote Similarity	NPD6317	Approved
0.6542	Remote Similarity	NPD6001	Approved
0.6518	Remote Similarity	NPD5174	Approved
0.6518	Remote Similarity	NPD5175	Approved
0.6518	Remote Similarity	NPD4754	Approved
0.6509	Remote Similarity	NPD6411	Approved
0.6505	Remote Similarity	NPD4690	Approved
0.6505	Remote Similarity	NPD5280	Approved
0.6505	Remote Similarity	NPD3618	Phase 1
0.6505	Remote Similarity	NPD4688	Approved
0.6505	Remote Similarity	NPD5690	Phase 2
0.6505	Remote Similarity	NPD4689	Approved
0.6505	Remote Similarity	NPD5205	Approved
0.6505	Remote Similarity	NPD4694	Approved
0.6505	Remote Similarity	NPD4138	Approved
0.6505	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6098	Approved
0.6505	Remote Similarity	NPD4693	Phase 3
0.6504	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD6335	Approved
0.65	Remote Similarity	NPD6314	Approved
0.6476	Remote Similarity	NPD5328	Approved
0.6475	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4786	Approved
0.6471	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7101	Approved
0.6446	Remote Similarity	NPD7100	Approved
0.6436	Remote Similarity	NPD3667	Approved
0.6429	Remote Similarity	NPD6033	Approved
0.6404	Remote Similarity	NPD4768	Approved
0.6404	Remote Similarity	NPD4767	Approved
0.64	Remote Similarity	NPD6336	Discontinued
0.6389	Remote Similarity	NPD7748	Approved
0.6381	Remote Similarity	NPD4518	Approved
0.6373	Remote Similarity	NPD4788	Approved
0.6373	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD7902	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