NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	576.26
Volume:	565.527
LogP:	2.35
LogD:	1.534
LogS:	-4.159
# Rotatable Bonds:	9
TPSA:	162.1
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	5.921
Fsp3:	0.733
Lipinski Rule-of-5:	Rejected
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:	-5.369
MDCK Permeability:	6.377287354553118e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.466
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.444
Plasma Protein Binding (PPB):	65.46773529052734%
Volume Distribution (VD):	0.616
Pgp-substrate:	26.247655868530273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.394
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.658
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	5.945
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.592
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.918
Maximum Recommended Daily Dose:	0.377
Skin Sensitization:	0.13
Carcinogencity:	0.184
Eye Corrosion:	0.017
Eye Irritation:	0.179
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC476858

Natural Product ID:	NPC476858
*Common Name:**	ethyl (3S)-3-acetyloxy-3-[(1R,2R,5R,6R,7R,8S,10S,11S,14S)-11-(furan-3-yl)-8-hydroxy-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.01,14.02,7]pentadecan-6-yl]propanoate
IUPAC Name:	ethyl (3S)-3-acetyloxy-3-[(1R,2R,5R,6R,7R,8S,10S,11S,14S)-11-(furan-3-yl)-8-hydroxy-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.01,14.02,7]pentadecan-6-yl]propanoate
Synonyms:
Standard InCHIKey:	WOIPTRVZUMZNCI-ANNBEMHLSA-N
Standard InCHI:	InChI=1S/C30H40O11/c1-8-38-21(34)12-20(39-15(2)31)28(6)18(26(3,4)36)11-19(33)29(7)22(28)17(32)13-27(5)23(16-9-10-37-14-16)40-25(35)24-30(27,29)41-24/h9-10,14,17-18,20,22-24,32,36H,8,11-13H2,1-7H3/t17-,18-,20-,22+,23-,24+,27-,28+,29+,30+/m0/s1
SMILES:	CCOC(=O)C[C@@H]([C@]1([C@@H](CC(=O)[C@@]2([C@@H]1[C@H](C[C@@]3([C@]24[C@H](O4)C(=O)O[C@H]3C5=COC=C5)C)O)C)C(C)(C)O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	86302658
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	=	5100	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 NPC476858 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	362
0.1-0.2	1439
0.2-0.3	3276
0.3-0.4	5650
0.4-0.5	10243
0.5-0.6	10203
0.6-0.7	9080
0.7-0.8	1982
0.8-0.85	276
0.85-0.9	114
0.9-0.95	52
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476857
1.0	High Similarity	NPC476856
0.9871	High Similarity	NPC476853
0.9871	High Similarity	NPC476861
0.9871	High Similarity	NPC476850
0.9806	High Similarity	NPC23387
0.9804	High Similarity	NPC25255
0.9742	High Similarity	NPC123088
0.9742	High Similarity	NPC476860
0.974	High Similarity	NPC193798
0.9677	High Similarity	NPC234660
0.9677	High Similarity	NPC51568
0.9618	High Similarity	NPC472282
0.9613	High Similarity	NPC5079
0.9557	High Similarity	NPC471397
0.9551	High Similarity	NPC477405
0.9551	High Similarity	NPC134254
0.9551	High Similarity	NPC39986
0.9551	High Similarity	NPC302369
0.9548	High Similarity	NPC472653
0.9548	High Similarity	NPC335761
0.9494	High Similarity	NPC472774
0.9494	High Similarity	NPC173516
0.9494	High Similarity	NPC472775
0.949	High Similarity	NPC276551
0.9487	High Similarity	NPC69028
0.9487	High Similarity	NPC290400
0.9487	High Similarity	NPC96443
0.9487	High Similarity	NPC470939
0.9484	High Similarity	NPC477403
0.9484	High Similarity	NPC473473
0.9484	High Similarity	NPC475295
0.9484	High Similarity	NPC237155
0.9434	High Similarity	NPC160651
0.943	High Similarity	NPC470875
0.9427	High Similarity	NPC292389
0.9427	High Similarity	NPC469338
0.9423	High Similarity	NPC477402
0.9419	High Similarity	NPC286722
0.9371	High Similarity	NPC472651
0.9367	High Similarity	NPC469849
0.9367	High Similarity	NPC470940
0.9363	High Similarity	NPC263432
0.9363	High Similarity	NPC329938
0.9363	High Similarity	NPC117986
0.9363	High Similarity	NPC472771
0.9355	High Similarity	NPC107646
0.9355	High Similarity	NPC60973
0.9355	High Similarity	NPC263265
0.9355	High Similarity	NPC126723
0.9355	High Similarity	NPC209364
0.9313	High Similarity	NPC472652
0.9313	High Similarity	NPC271235
0.9304	High Similarity	NPC472773
0.9299	High Similarity	NPC475381
0.9299	High Similarity	NPC305016
0.9295	High Similarity	NPC472772
0.9295	High Similarity	NPC472283
0.929	High Similarity	NPC469336
0.925	High Similarity	NPC473766
0.925	High Similarity	NPC473753
0.9245	High Similarity	NPC271657
0.9241	High Similarity	NPC82851
0.9226	High Similarity	NPC178932
0.9172	High Similarity	NPC249021
0.9172	High Similarity	NPC45101
0.9167	High Similarity	NPC469850
0.9167	High Similarity	NPC264943
0.9161	High Similarity	NPC75906
0.9119	High Similarity	NPC200782
0.9119	High Similarity	NPC18347
0.9119	High Similarity	NPC149896
0.9114	High Similarity	NPC475967
0.9108	High Similarity	NPC469485
0.9103	High Similarity	NPC57998
0.9068	High Similarity	NPC475779
0.9062	High Similarity	NPC469846
0.9062	High Similarity	NPC476197
0.9057	High Similarity	NPC191828
0.9051	High Similarity	NPC187149
0.9051	High Similarity	NPC173544
0.9051	High Similarity	NPC299038
0.9051	High Similarity	NPC167142
0.9045	High Similarity	NPC44675
0.9045	High Similarity	NPC214541
0.9045	High Similarity	NPC281258
0.9038	High Similarity	NPC469503
0.9032	High Similarity	NPC196864
0.9032	High Similarity	NPC469335
0.9032	High Similarity	NPC477404
0.9032	High Similarity	NPC159927
0.902	High Similarity	NPC262198
0.9018	High Similarity	NPC470995
0.8981	High Similarity	NPC282445
0.8974	High Similarity	NPC18135
0.8951	High Similarity	NPC478178
0.8944	High Similarity	NPC419
0.8944	High Similarity	NPC224394
0.8944	High Similarity	NPC663
0.8935	High Similarity	NPC105395
0.8935	High Similarity	NPC242068
0.8935	High Similarity	NPC247563
0.8931	High Similarity	NPC36655
0.8931	High Similarity	NPC261597
0.8924	High Similarity	NPC476262
0.8917	High Similarity	NPC476201
0.8916	High Similarity	NPC262386
0.891	High Similarity	NPC46551
0.891	High Similarity	NPC476122
0.8902	High Similarity	NPC82602
0.8882	High Similarity	NPC207978
0.8882	High Similarity	NPC197596
0.8875	High Similarity	NPC473368
0.8875	High Similarity	NPC307383
0.8862	High Similarity	NPC478177
0.8855	High Similarity	NPC471437
0.8848	High Similarity	NPC160818
0.8848	High Similarity	NPC159232
0.8848	High Similarity	NPC169299
0.8848	High Similarity	NPC285227
0.8846	High Similarity	NPC125182
0.8846	High Similarity	NPC69647
0.8839	High Similarity	NPC221809
0.8839	High Similarity	NPC255414
0.8834	High Similarity	NPC93172
0.8834	High Similarity	NPC121995
0.8834	High Similarity	NPC97574
0.882	High Similarity	NPC470789
0.8805	High Similarity	NPC75310
0.8805	High Similarity	NPC35000
0.8797	High Similarity	NPC268905
0.8795	High Similarity	NPC469848
0.8788	High Similarity	NPC302392
0.878	High Similarity	NPC270312
0.878	High Similarity	NPC472764
0.878	High Similarity	NPC478179
0.8773	High Similarity	NPC470182
0.8766	High Similarity	NPC476944
0.8766	High Similarity	NPC86935
0.8765	High Similarity	NPC472767
0.8765	High Similarity	NPC188649
0.8765	High Similarity	NPC471167
0.8765	High Similarity	NPC211777
0.8765	High Similarity	NPC18986
0.8765	High Similarity	NPC471166
0.8758	High Similarity	NPC121158
0.8743	High Similarity	NPC236004
0.8742	High Similarity	NPC30222
0.8727	High Similarity	NPC472765
0.8727	High Similarity	NPC472766
0.8726	High Similarity	NPC195325
0.8726	High Similarity	NPC472654
0.872	High Similarity	NPC472141
0.872	High Similarity	NPC149945
0.8718	High Similarity	NPC470941
0.8712	High Similarity	NPC472139
0.8712	High Similarity	NPC471168
0.8712	High Similarity	NPC288602
0.8712	High Similarity	NPC88841
0.8712	High Similarity	NPC198047
0.8704	High Similarity	NPC287559
0.8701	High Similarity	NPC243577
0.8696	High Similarity	NPC472776
0.8696	High Similarity	NPC472778
0.8696	High Similarity	NPC472777
0.8696	High Similarity	NPC195954
0.8688	High Similarity	NPC92979
0.8679	High Similarity	NPC475777
0.8679	High Similarity	NPC44577
0.8667	High Similarity	NPC476224
0.8659	High Similarity	NPC56358
0.865	High Similarity	NPC6326
0.865	High Similarity	NPC68848
0.865	High Similarity	NPC472668
0.8647	High Similarity	NPC470938
0.8645	High Similarity	NPC251865
0.8642	High Similarity	NPC262872
0.8642	High Similarity	NPC475226
0.8642	High Similarity	NPC474611
0.8634	High Similarity	NPC41880
0.8631	High Similarity	NPC471632
0.8631	High Similarity	NPC94763
0.8627	High Similarity	NPC67003
0.8625	High Similarity	NPC114880
0.8616	High Similarity	NPC272590
0.8606	High Similarity	NPC214600
0.8599	High Similarity	NPC250228
0.8598	High Similarity	NPC472669
0.8598	High Similarity	NPC165218
0.859	High Similarity	NPC5676
0.859	High Similarity	NPC41182
0.858	High Similarity	NPC197137
0.858	High Similarity	NPC194499
0.858	High Similarity	NPC88007
0.8563	High Similarity	NPC472659
0.8562	High Similarity	NPC147168
0.8554	High Similarity	NPC100333
0.8553	High Similarity	NPC156189
0.8545	High Similarity	NPC261184
0.8545	High Similarity	NPC146991

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 NPC476858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	1039
0.2-0.3	2210
0.3-0.4	2615
0.4-0.5	1844
0.5-0.6	841
0.6-0.7	264
0.7-0.8	30
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
0.8547	High Similarity	NPD8434	Phase 2
0.8457	Intermediate Similarity	NPD5760	Phase 2
0.8457	Intermediate Similarity	NPD5761	Phase 2
0.8253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6765	Approved
0.7943	Intermediate Similarity	NPD6764	Approved
0.7765	Intermediate Similarity	NPD6785	Approved
0.7765	Intermediate Similarity	NPD6784	Approved
0.7692	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6559	Discontinued
0.7427	Intermediate Similarity	NPD6801	Discontinued
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7341	Intermediate Similarity	NPD5402	Approved
0.7337	Intermediate Similarity	NPD8404	Phase 2
0.733	Intermediate Similarity	NPD1247	Approved
0.7317	Intermediate Similarity	NPD1471	Phase 3
0.7283	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7262	Intermediate Similarity	NPD6799	Approved
0.7251	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD3817	Phase 2
0.7241	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3751	Discontinued
0.7216	Intermediate Similarity	NPD919	Approved
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.7182	Intermediate Similarity	NPD5844	Phase 1
0.7182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3749	Approved
0.7151	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD920	Approved
0.7135	Intermediate Similarity	NPD5403	Approved
0.7127	Intermediate Similarity	NPD7799	Discontinued
0.7126	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5401	Approved
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4380	Phase 2
0.7108	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3882	Suspended
0.7101	Intermediate Similarity	NPD7236	Approved
0.7081	Intermediate Similarity	NPD8312	Approved
0.7081	Intermediate Similarity	NPD8313	Approved
0.7077	Intermediate Similarity	NPD7435	Discontinued
0.7072	Intermediate Similarity	NPD7473	Discontinued
0.7062	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8407	Phase 2
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7033	Intermediate Similarity	NPD3818	Discontinued
0.7018	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.6994	Remote Similarity	NPD7239	Suspended
0.6989	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6273	Approved
0.6973	Remote Similarity	NPD8368	Discontinued
0.6973	Remote Similarity	NPD7251	Discontinued
0.694	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7808	Phase 3
0.6932	Remote Similarity	NPD1934	Approved
0.6919	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2533	Approved
0.6919	Remote Similarity	NPD6797	Phase 2
0.6919	Remote Similarity	NPD2532	Approved
0.6919	Remote Similarity	NPD2534	Approved
0.6909	Remote Similarity	NPD6355	Discontinued
0.6906	Remote Similarity	NPD6232	Discontinued
0.6901	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2799	Discontinued
0.6882	Remote Similarity	NPD7685	Pre-registration
0.6872	Remote Similarity	NPD8285	Discontinued
0.6868	Remote Similarity	NPD3926	Phase 2
0.6866	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7874	Approved
0.6865	Remote Similarity	NPD7074	Phase 3
0.6864	Remote Similarity	NPD1549	Phase 2
0.6857	Remote Similarity	NPD7458	Discontinued
0.6857	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6959	Discontinued
0.6848	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2796	Approved
0.6845	Remote Similarity	NPD6100	Approved
0.6845	Remote Similarity	NPD6099	Approved
0.6837	Remote Similarity	NPD6781	Approved
0.6837	Remote Similarity	NPD6778	Approved
0.6837	Remote Similarity	NPD6782	Approved
0.6837	Remote Similarity	NPD6777	Approved
0.6837	Remote Similarity	NPD6776	Approved
0.6837	Remote Similarity	NPD6780	Approved
0.6837	Remote Similarity	NPD6779	Approved
0.6836	Remote Similarity	NPD37	Approved
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7698	Approved
0.6818	Remote Similarity	NPD7697	Approved
0.6816	Remote Similarity	NPD4966	Approved
0.6816	Remote Similarity	NPD4965	Approved
0.6816	Remote Similarity	NPD4967	Phase 2
0.6811	Remote Similarity	NPD7054	Approved
0.6805	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5763	Approved
0.6805	Remote Similarity	NPD5762	Approved
0.6798	Remote Similarity	NPD2801	Approved
0.6786	Remote Similarity	NPD7033	Discontinued
0.6784	Remote Similarity	NPD7871	Phase 2
0.6784	Remote Similarity	NPD7870	Phase 2
0.6779	Remote Similarity	NPD7907	Approved
0.6776	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7472	Approved
0.6763	Remote Similarity	NPD4111	Phase 1
0.6746	Remote Similarity	NPD2935	Discontinued
0.6746	Remote Similarity	NPD1551	Phase 2
0.6744	Remote Similarity	NPD6190	Approved
0.6727	Remote Similarity	NPD2313	Discontinued
0.6727	Remote Similarity	NPD3268	Approved
0.6725	Remote Similarity	NPD2800	Approved
0.6725	Remote Similarity	NPD1243	Approved
0.6724	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7768	Phase 2
0.6719	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8435	Approved
0.6714	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6832	Phase 2
0.6706	Remote Similarity	NPD2344	Approved
0.67	Remote Similarity	NPD8319	Approved
0.67	Remote Similarity	NPD8320	Phase 1
0.6687	Remote Similarity	NPD6233	Phase 2
0.6686	Remote Similarity	NPD3750	Approved
0.6683	Remote Similarity	NPD4665	Approved
0.6683	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7199	Phase 2
0.6649	Remote Similarity	NPD2403	Approved
0.6648	Remote Similarity	NPD6234	Discontinued
0.6648	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3887	Approved
0.6632	Remote Similarity	NPD8360	Approved
0.6632	Remote Similarity	NPD8361	Approved
0.663	Remote Similarity	NPD7229	Phase 3
0.663	Remote Similarity	NPD7058	Phase 2
0.663	Remote Similarity	NPD7057	Phase 3
0.663	Remote Similarity	NPD6808	Phase 2
0.6627	Remote Similarity	NPD7097	Phase 1
0.6627	Remote Similarity	NPD6798	Discontinued
0.6627	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD8455	Phase 2
0.6611	Remote Similarity	NPD1465	Phase 2
0.66	Remote Similarity	NPD3057	Approved
0.6599	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1512	Approved
0.6591	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3748	Approved
0.6588	Remote Similarity	NPD1510	Phase 2
0.6585	Remote Similarity	NPD7783	Phase 2
0.6585	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6534	Approved
0.6582	Remote Similarity	NPD6535	Approved
0.6567	Remote Similarity	NPD7497	Discontinued
0.6566	Remote Similarity	NPD7700	Phase 2
0.6566	Remote Similarity	NPD7699	Phase 2
0.6552	Remote Similarity	NPD2354	Approved
0.6552	Remote Similarity	NPD2309	Approved
0.655	Remote Similarity	NPD4482	Phase 3
0.6543	Remote Similarity	NPD1608	Approved
0.6543	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5711	Approved
0.6541	Remote Similarity	NPD5710	Approved
0.654	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3764	Approved
0.6526	Remote Similarity	NPD7240	Approved
0.6524	Remote Similarity	NPD3266	Approved
0.6524	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3267	Approved
0.6517	Remote Similarity	NPD6823	Phase 2
0.6517	Remote Similarity	NPD3533	Approved
0.6517	Remote Similarity	NPD2972	Approved
0.6515	Remote Similarity	NPD8485	Approved
0.6512	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6005	Phase 3
0.6512	Remote Similarity	NPD6002	Phase 3
0.6512	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6004	Phase 3
0.6509	Remote Similarity	NPD447	Suspended
0.65	Remote Similarity	NPD4580	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