NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	502.22
Volume:	490.139
LogP:	2.462
LogD:	1.932
LogS:	-4.566
# Rotatable Bonds:	4
TPSA:	124.8
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	5.871
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.364
MDCK Permeability:	2.099066841765307e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.773
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.387
Plasma Protein Binding (PPB):	65.7166976928711%
Volume Distribution (VD):	1.149
Pgp-substrate:	31.776254653930664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.341
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.707
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.797
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	9.414
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.431
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.83
Skin Sensitization:	0.164
Carcinogencity:	0.121
Eye Corrosion:	0.029
Eye Irritation:	0.044
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC476850

Natural Product ID:	NPC476850
*Common Name:**	methyl 2-[(1R,2R,4S,7S,8S,10S,11R,12R,13R,16R)-7-(furan-3-yl)-10-hydroxy-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.02,4.02,8.012,16]octadecan-13-yl]acetate
IUPAC Name:	methyl 2-[(1R,2R,4S,7S,8S,10S,11R,12R,13R,16R)-7-(furan-3-yl)-10-hydroxy-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.02,4.02,8.012,16]octadecan-13-yl]acetate
Synonyms:
Standard InCHIKey:	SQTDQWTYVSNTOG-WJQCSXITSA-N
Standard InCHI:	InChI=1S/C27H34O9/c1-23(2)15-9-16(29)26(5)19(25(15,4)17(35-23)10-18(30)32-6)14(28)11-24(3)20(13-7-8-33-12-13)34-22(31)21-27(24,26)36-21/h7-8,12,14-15,17,19-21,28H,9-11H2,1-6H3/t14-,15-,17+,19+,20-,21+,24-,25+,26+,27+/m0/s1
SMILES:	C[C@@]12C[C@@H]([C@@H]3[C@@]4([C@@H](CC(=O)[C@]3([C@@]15[C@H](O5)C(=O)O[C@H]2C6=COC=C6)C)C(O[C@@H]4CC(=O)OC)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	86302631
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid 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
NPO33678	Clausena emarginata	Species	Rutaceae	Eukaryota	stems	Xishuangbanna, Yunnan Province, China	2010-AUG	PMID[24593150]

☑ 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	6

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT1820	Cell Line	NCI-H1650	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT2	Others	Unspecified		IC50	=	10000	nM	PMID[24593150]
NPT2	Others	Unspecified		IC50	>	10000	nM	PMID[24593150]

☑ 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 NPC476850 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	370
0.1-0.2	1428
0.2-0.3	3259
0.3-0.4	5501
0.4-0.5	10477
0.5-0.6	10525
0.6-0.7	9286
0.7-0.8	1378
0.8-0.85	262
0.85-0.9	143
0.9-0.95	57
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476861
0.9871	High Similarity	NPC476858
0.9871	High Similarity	NPC476857
0.9871	High Similarity	NPC476856
0.9871	High Similarity	NPC123088
0.9745	High Similarity	NPC476853
0.9682	High Similarity	NPC23387
0.9677	High Similarity	NPC25255
0.9618	High Similarity	NPC476860
0.9615	High Similarity	NPC193798
0.9554	High Similarity	NPC51568
0.9554	High Similarity	NPC234660
0.9497	High Similarity	NPC472282
0.9497	High Similarity	NPC472651
0.949	High Similarity	NPC5079
0.9437	High Similarity	NPC271235
0.9437	High Similarity	NPC471397
0.9437	High Similarity	NPC472652
0.943	High Similarity	NPC477405
0.943	High Similarity	NPC39986
0.943	High Similarity	NPC134254
0.943	High Similarity	NPC302369
0.9427	High Similarity	NPC335761
0.9427	High Similarity	NPC472653
0.9427	High Similarity	NPC305016
0.9375	High Similarity	NPC472775
0.9375	High Similarity	NPC173516
0.9375	High Similarity	NPC472774
0.9371	High Similarity	NPC276551
0.9367	High Similarity	NPC470939
0.9367	High Similarity	NPC290400
0.9367	High Similarity	NPC69028
0.9367	High Similarity	NPC117986
0.9367	High Similarity	NPC96443
0.9363	High Similarity	NPC473473
0.9363	High Similarity	NPC237155
0.9363	High Similarity	NPC477403
0.9363	High Similarity	NPC475295
0.9317	High Similarity	NPC160651
0.9313	High Similarity	NPC470875
0.9308	High Similarity	NPC469338
0.9308	High Similarity	NPC292389
0.9304	High Similarity	NPC477402
0.9299	High Similarity	NPC286722
0.929	High Similarity	NPC75906
0.925	High Similarity	NPC469849
0.925	High Similarity	NPC470940
0.9245	High Similarity	NPC472771
0.9245	High Similarity	NPC263432
0.9245	High Similarity	NPC329938
0.9241	High Similarity	NPC475967
0.9236	High Similarity	NPC60973
0.9236	High Similarity	NPC107646
0.9236	High Similarity	NPC209364
0.9236	High Similarity	NPC263265
0.9236	High Similarity	NPC126723
0.9231	High Similarity	NPC57998
0.9187	High Similarity	NPC469846
0.9187	High Similarity	NPC472773
0.9182	High Similarity	NPC475381
0.9182	High Similarity	NPC191828
0.9177	High Similarity	NPC472283
0.9177	High Similarity	NPC187149
0.9177	High Similarity	NPC299038
0.9177	High Similarity	NPC472772
0.9172	High Similarity	NPC214541
0.9172	High Similarity	NPC469336
0.9172	High Similarity	NPC44675
0.9136	High Similarity	NPC473766
0.9136	High Similarity	NPC473753
0.913	High Similarity	NPC271657
0.9125	High Similarity	NPC82851
0.9108	High Similarity	NPC178932
0.9103	High Similarity	NPC18135
0.9068	High Similarity	NPC419
0.9057	High Similarity	NPC261597
0.9057	High Similarity	NPC45101
0.9057	High Similarity	NPC36655
0.9057	High Similarity	NPC249021
0.9053	High Similarity	NPC242068
0.9053	High Similarity	NPC105395
0.9053	High Similarity	NPC247563
0.9051	High Similarity	NPC469850
0.9051	High Similarity	NPC264943
0.9024	High Similarity	NPC470995
0.9024	High Similarity	NPC82602
0.9006	High Similarity	NPC200782
0.9006	High Similarity	NPC18347
0.9006	High Similarity	NPC149896
0.8994	High Similarity	NPC469485
0.897	High Similarity	NPC285227
0.897	High Similarity	NPC159232
0.897	High Similarity	NPC169299
0.897	High Similarity	NPC160818
0.8968	High Similarity	NPC221809
0.8957	High Similarity	NPC475779
0.8957	High Similarity	NPC478178
0.8951	High Similarity	NPC224394
0.8951	High Similarity	NPC663
0.8951	High Similarity	NPC476197
0.8938	High Similarity	NPC167142
0.8938	High Similarity	NPC173544
0.8931	High Similarity	NPC281258
0.8924	High Similarity	NPC469503
0.8924	High Similarity	NPC268905
0.8917	High Similarity	NPC469335
0.8917	High Similarity	NPC477404
0.8917	High Similarity	NPC196864
0.8917	High Similarity	NPC159927
0.8916	High Similarity	NPC469848
0.8903	High Similarity	NPC262198
0.8889	High Similarity	NPC197596
0.8869	High Similarity	NPC478177
0.8868	High Similarity	NPC282445
0.8862	High Similarity	NPC471437
0.8854	High Similarity	NPC195325
0.8841	High Similarity	NPC472141
0.8834	High Similarity	NPC472139
0.8834	High Similarity	NPC471168
0.8827	High Similarity	NPC470789
0.882	High Similarity	NPC472776
0.882	High Similarity	NPC472777
0.882	High Similarity	NPC472778
0.8812	High Similarity	NPC476262
0.881	High Similarity	NPC262386
0.8805	High Similarity	NPC476201
0.8797	High Similarity	NPC476122
0.8797	High Similarity	NPC46551
0.8788	High Similarity	NPC478179
0.8788	High Similarity	NPC472764
0.8774	High Similarity	NPC251865
0.8773	High Similarity	NPC207978
0.8773	High Similarity	NPC471166
0.8773	High Similarity	NPC472767
0.8773	High Similarity	NPC471167
0.8765	High Similarity	NPC473368
0.8765	High Similarity	NPC475226
0.8765	High Similarity	NPC307383
0.8765	High Similarity	NPC470938
0.875	High Similarity	NPC236004
0.8735	High Similarity	NPC472766
0.8735	High Similarity	NPC472765
0.8734	High Similarity	NPC472654
0.8734	High Similarity	NPC69647
0.8734	High Similarity	NPC125182
0.8727	High Similarity	NPC214600
0.8727	High Similarity	NPC97574
0.8727	High Similarity	NPC93172
0.8727	High Similarity	NPC149945
0.8727	High Similarity	NPC121995
0.8726	High Similarity	NPC250228
0.8726	High Similarity	NPC255414
0.8704	High Similarity	NPC197137
0.8696	High Similarity	NPC35000
0.8696	High Similarity	NPC75310
0.8696	High Similarity	NPC92979
0.8683	High Similarity	NPC302392
0.8675	High Similarity	NPC270312
0.8675	High Similarity	NPC476224
0.8675	High Similarity	NPC100333
0.8667	High Similarity	NPC470182
0.8662	High Similarity	NPC346
0.8659	High Similarity	NPC188649
0.8659	High Similarity	NPC6326
0.8659	High Similarity	NPC211777
0.8659	High Similarity	NPC18986
0.8659	High Similarity	NPC472668
0.8654	High Similarity	NPC86935
0.8654	High Similarity	NPC476944
0.8645	High Similarity	NPC121158
0.8639	High Similarity	NPC471632
0.8639	High Similarity	NPC94763
0.8634	High Similarity	NPC30222
0.8625	High Similarity	NPC272590
0.8608	High Similarity	NPC470941
0.8606	High Similarity	NPC288602
0.8606	High Similarity	NPC472669
0.8606	High Similarity	NPC198047
0.8606	High Similarity	NPC285567
0.8606	High Similarity	NPC165218
0.8606	High Similarity	NPC14499
0.8606	High Similarity	NPC283209
0.8606	High Similarity	NPC475039
0.8606	High Similarity	NPC476035
0.8606	High Similarity	NPC88841
0.8598	High Similarity	NPC287559
0.859	High Similarity	NPC267632
0.859	High Similarity	NPC243577
0.8589	High Similarity	NPC470118
0.8589	High Similarity	NPC195954
0.8589	High Similarity	NPC304692
0.858	High Similarity	NPC141538
0.858	High Similarity	NPC296807
0.858	High Similarity	NPC155939
0.8571	High Similarity	NPC476940
0.8571	High Similarity	NPC472659
0.8571	High Similarity	NPC475777
0.8571	High Similarity	NPC44577
0.8571	High Similarity	NPC476939
0.8562	High Similarity	NPC156189

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 NPC476850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	1004
0.2-0.3	2242
0.3-0.4	2688
0.4-0.5	1832
0.5-0.6	794
0.6-0.7	255
0.7-0.8	19
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8466	Intermediate Similarity	NPD5761	Phase 2
0.8466	Intermediate Similarity	NPD5760	Phase 2
0.8448	Intermediate Similarity	NPD8434	Phase 2
0.8263	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6765	Approved
0.7955	Intermediate Similarity	NPD6764	Approved
0.7778	Intermediate Similarity	NPD6784	Approved
0.7778	Intermediate Similarity	NPD6785	Approved
0.7602	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7075	Discontinued
0.7427	Intermediate Similarity	NPD6599	Discontinued
0.7399	Intermediate Similarity	NPD7819	Suspended
0.738	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6559	Discontinued
0.7341	Intermediate Similarity	NPD6801	Discontinued
0.7305	Intermediate Similarity	NPD4628	Phase 3
0.7297	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8404	Phase 2
0.7257	Intermediate Similarity	NPD5402	Approved
0.7247	Intermediate Similarity	NPD1247	Approved
0.7229	Intermediate Similarity	NPD1471	Phase 3
0.7191	Intermediate Similarity	NPD5494	Approved
0.7184	Intermediate Similarity	NPD7411	Suspended
0.7176	Intermediate Similarity	NPD6799	Approved
0.7168	Intermediate Similarity	NPD3226	Approved
0.7159	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD7799	Discontinued
0.7135	Intermediate Similarity	NPD919	Approved
0.7111	Intermediate Similarity	NPD3787	Discontinued
0.7104	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5844	Phase 1
0.7079	Intermediate Similarity	NPD3749	Approved
0.7074	Intermediate Similarity	NPD8150	Discontinued
0.7052	Intermediate Similarity	NPD5403	Approved
0.7052	Intermediate Similarity	NPD920	Approved
0.7043	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5401	Approved
0.7029	Intermediate Similarity	NPD4380	Phase 2
0.7024	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD3882	Suspended
0.7018	Intermediate Similarity	NPD7236	Approved
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.7005	Intermediate Similarity	NPD8312	Approved
0.7005	Intermediate Similarity	NPD8313	Approved
0.6995	Remote Similarity	NPD7473	Discontinued
0.6983	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8407	Phase 2
0.6961	Remote Similarity	NPD8127	Discontinued
0.6957	Remote Similarity	NPD3818	Discontinued
0.694	Remote Similarity	NPD6166	Phase 2
0.694	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4966	Approved
0.6927	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4965	Approved
0.6927	Remote Similarity	NPD4967	Phase 2
0.6923	Remote Similarity	NPD2346	Discontinued
0.6914	Remote Similarity	NPD7239	Suspended
0.691	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7251	Discontinued
0.6898	Remote Similarity	NPD8368	Discontinued
0.6897	Remote Similarity	NPD6273	Approved
0.6865	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7808	Phase 3
0.6854	Remote Similarity	NPD1934	Approved
0.6845	Remote Similarity	NPD6797	Phase 2
0.6845	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2534	Approved
0.6839	Remote Similarity	NPD2532	Approved
0.6839	Remote Similarity	NPD2533	Approved
0.6831	Remote Similarity	NPD6232	Discontinued
0.6826	Remote Similarity	NPD6355	Discontinued
0.6821	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7685	Pre-registration
0.6805	Remote Similarity	NPD2799	Discontinued
0.6802	Remote Similarity	NPD8285	Discontinued
0.6798	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7874	Approved
0.6793	Remote Similarity	NPD3926	Phase 2
0.6793	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7074	Phase 3
0.6784	Remote Similarity	NPD1549	Phase 2
0.678	Remote Similarity	NPD7458	Discontinued
0.678	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6959	Discontinued
0.6774	Remote Similarity	NPD7228	Approved
0.6768	Remote Similarity	NPD6776	Approved
0.6768	Remote Similarity	NPD6780	Approved
0.6768	Remote Similarity	NPD6778	Approved
0.6768	Remote Similarity	NPD6782	Approved
0.6768	Remote Similarity	NPD6781	Approved
0.6768	Remote Similarity	NPD6777	Approved
0.6768	Remote Similarity	NPD6779	Approved
0.6766	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6100	Approved
0.6765	Remote Similarity	NPD2796	Approved
0.6765	Remote Similarity	NPD6099	Approved
0.676	Remote Similarity	NPD37	Approved
0.6758	Remote Similarity	NPD6234	Discontinued
0.675	Remote Similarity	NPD7697	Approved
0.675	Remote Similarity	NPD7696	Phase 3
0.675	Remote Similarity	NPD7698	Approved
0.6738	Remote Similarity	NPD7054	Approved
0.6725	Remote Similarity	NPD5762	Approved
0.6725	Remote Similarity	NPD5763	Approved
0.6725	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2801	Approved
0.6716	Remote Similarity	NPD7871	Phase 2
0.6716	Remote Similarity	NPD7870	Phase 2
0.6714	Remote Similarity	NPD7907	Approved
0.6706	Remote Similarity	NPD7033	Discontinued
0.6702	Remote Similarity	NPD7472	Approved
0.6699	Remote Similarity	NPD4111	Phase 1
0.6685	Remote Similarity	NPD7199	Phase 2
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6651	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8435	Approved
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7768	Phase 2
0.6647	Remote Similarity	NPD3268	Approved
0.6647	Remote Similarity	NPD2800	Approved
0.6647	Remote Similarity	NPD1243	Approved
0.6647	Remote Similarity	NPD2313	Discontinued
0.6634	Remote Similarity	NPD8320	Phase 1
0.6634	Remote Similarity	NPD8319	Approved
0.6632	Remote Similarity	NPD7240	Approved
0.6628	Remote Similarity	NPD2344	Approved
0.6627	Remote Similarity	NPD6832	Phase 2
0.6619	Remote Similarity	NPD4665	Approved
0.6618	Remote Similarity	NPD7701	Phase 2
0.6609	Remote Similarity	NPD3750	Approved
0.6607	Remote Similarity	NPD6233	Phase 2
0.6602	Remote Similarity	NPD7801	Approved
0.66	Remote Similarity	NPD4107	Approved
0.659	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7095	Approved
0.6584	Remote Similarity	NPD7497	Discontinued
0.6578	Remote Similarity	NPD2403	Approved
0.6573	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3887	Approved
0.6564	Remote Similarity	NPD8360	Approved
0.6564	Remote Similarity	NPD8361	Approved
0.6559	Remote Similarity	NPD7229	Phase 3
0.6559	Remote Similarity	NPD6808	Phase 2
0.6557	Remote Similarity	NPD7058	Phase 2
0.6557	Remote Similarity	NPD7057	Phase 3
0.655	Remote Similarity	NPD7097	Phase 1
0.6548	Remote Similarity	NPD6798	Discontinued
0.6548	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1465	Phase 2
0.6538	Remote Similarity	NPD8455	Phase 2
0.6535	Remote Similarity	NPD3057	Approved
0.6533	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6002	Phase 3
0.6532	Remote Similarity	NPD6005	Phase 3
0.6532	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6004	Phase 3
0.6522	Remote Similarity	NPD7783	Phase 2
0.6522	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1512	Approved
0.6515	Remote Similarity	NPD6534	Approved
0.6515	Remote Similarity	NPD6535	Approved
0.6512	Remote Similarity	NPD1510	Phase 2
0.6512	Remote Similarity	NPD3748	Approved
0.6507	Remote Similarity	NPD7930	Approved
0.65	Remote Similarity	NPD7700	Phase 2
0.65	Remote Similarity	NPD7699	Phase 2
0.6497	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4482	Phase 3
0.6479	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD2309	Approved
0.6477	Remote Similarity	NPD2354	Approved
0.6474	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5711	Approved
0.6471	Remote Similarity	NPD5710	Approved
0.6463	Remote Similarity	NPD1608	Approved
0.6453	Remote Similarity	NPD6823	Phase 2
0.6453	Remote Similarity	NPD2972	Approved
0.6453	Remote Similarity	NPD3533	Approved
0.645	Remote Similarity	NPD8485	Approved
0.645	Remote Similarity	NPD3764	Approved
0.645	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD3266	Approved
0.6446	Remote Similarity	NPD3267	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