NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	524.2
Volume:	516.822
LogP:	2.707
LogD:	1.01
LogS:	-3.951
# Rotatable Bonds:	6
TPSA:	129.34
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	6.11
Fsp3:	0.586
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:	-5.313
MDCK Permeability:	1.7540478438604623e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.928
Human Intestinal Absorption (HIA):	0.267
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.796

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.885
Plasma Protein Binding (PPB):	86.21964263916016%
Volume Distribution (VD):	1.071
Pgp-substrate:	16.30343246459961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.356
CYP2C19-inhibitor:	0.738
CYP2C19-substrate:	0.191
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	4.494
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.507
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.345
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.173
Carcinogencity:	0.398
Eye Corrosion:	0.004
Eye Irritation:	0.009
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC478179

Natural Product ID:	NPC478179
*Common Name:**	methyl 2-[(1S,5R,6R,12R,14S,15R,17S,18S)-14-acetyloxy-6-(furan-3-yl)-17-hydroxy-1,5,15-trimethyl-8,13-dioxo-7-oxapentacyclo[13.2.1.02,11.05,10.012,17]octadeca-2(11),9-dien-18-yl]acetate
IUPAC Name:	methyl 2-[(1S,5R,6R,12R,14S,15R,17S,18S)-14-acetyloxy-6-(furan-3-yl)-17-hydroxy-1,5,15-trimethyl-8,13-dioxo-7-oxapentacyclo[13.2.1.02,11.05,10.012,17]octadeca-2(11),9-dien-18-yl]acetate
Synonyms:
Standard InCHIKey:	XHFDKRUZXVKRBV-CNZSFKCRSA-N
Standard InCHI:	InChI=1S/C29H32O9/c1-14(30)37-25-23(33)22-21-16(28(4)18(11-19(31)35-5)27(25,3)13-29(22,28)34)6-8-26(2)17(21)10-20(32)38-24(26)15-7-9-36-12-15/h7,9-10,12,18,22,24-25,34H,6,8,11,13H2,1-5H3/t18-,22-,24-,25+,26+,27+,28+,29-/m0/s1
SMILES:	CC(=O)O[C@@H]1C(=O)[C@@H]2C3=C(CC[C@@]4(C3=CC(=O)O[C@H]4C5=COC=C5)C)[C@]6([C@@]2(C[C@@]1([C@@H]6CC(=O)OC)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181597
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	121500	nM	PMID[26114936]

☑ 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 NPC478179 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	355
0.1-0.2	1400
0.2-0.3	3108
0.3-0.4	5817
0.4-0.5	11063
0.5-0.6	10006
0.6-0.7	9284
0.7-0.8	1295
0.8-0.85	294
0.85-0.9	71
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9682	High Similarity	NPC478178
0.9308	High Similarity	NPC165218
0.9207	High Similarity	NPC236004
0.9207	High Similarity	NPC469576
0.9187	High Similarity	NPC663
0.9187	High Similarity	NPC224394
0.9152	High Similarity	NPC469633
0.9096	High Similarity	NPC478177
0.9091	High Similarity	NPC94763
0.9074	High Similarity	NPC214600
0.9006	High Similarity	NPC197596
0.9	High Similarity	NPC474932
0.8976	High Similarity	NPC471437
0.897	High Similarity	NPC285227
0.897	High Similarity	NPC159232
0.8963	High Similarity	NPC327922
0.8957	High Similarity	NPC149945
0.8924	High Similarity	NPC246164
0.8889	High Similarity	NPC472767
0.8889	High Similarity	NPC6326
0.8882	High Similarity	NPC477403
0.8854	High Similarity	NPC472654
0.8834	High Similarity	NPC51568
0.8834	High Similarity	NPC234660
0.883	High Similarity	NPC242068
0.883	High Similarity	NPC247563
0.882	High Similarity	NPC249021
0.882	High Similarity	NPC470118
0.8812	High Similarity	NPC214541
0.8812	High Similarity	NPC44675
0.8797	High Similarity	NPC156189
0.8788	High Similarity	NPC476861
0.8788	High Similarity	NPC476850
0.878	High Similarity	NPC476857
0.878	High Similarity	NPC476856
0.878	High Similarity	NPC476858
0.8773	High Similarity	NPC329938
0.8773	High Similarity	NPC5079
0.8765	High Similarity	NPC475295
0.8765	High Similarity	NPC473473
0.8765	High Similarity	NPC470938
0.8758	High Similarity	NPC204663
0.8758	High Similarity	NPC469485
0.875	High Similarity	NPC57998
0.875	High Similarity	NPC30222
0.8742	High Similarity	NPC272590
0.8726	High Similarity	NPC471174
0.8721	High Similarity	NPC105395
0.872	High Similarity	NPC469338
0.872	High Similarity	NPC292389
0.8712	High Similarity	NPC470789
0.8712	High Similarity	NPC472653
0.8712	High Similarity	NPC25255
0.8712	High Similarity	NPC477402
0.8704	High Similarity	NPC195131
0.8704	High Similarity	NPC472777
0.8704	High Similarity	NPC472776
0.8704	High Similarity	NPC472778
0.8704	High Similarity	NPC286722
0.8704	High Similarity	NPC261597
0.8704	High Similarity	NPC173544
0.8704	High Similarity	NPC36655
0.8696	High Similarity	NPC35000
0.8696	High Similarity	NPC264943
0.8696	High Similarity	NPC469336
0.869	High Similarity	NPC469848
0.8688	High Similarity	NPC469503
0.8683	High Similarity	NPC470995
0.8675	High Similarity	NPC476853
0.8675	High Similarity	NPC472764
0.8675	High Similarity	NPC476224
0.8667	High Similarity	NPC470940
0.8667	High Similarity	NPC469849
0.8667	High Similarity	NPC276551
0.8667	High Similarity	NPC123088
0.8667	High Similarity	NPC476860
0.8659	High Similarity	NPC96443
0.8659	High Similarity	NPC69028
0.8659	High Similarity	NPC290400
0.8659	High Similarity	NPC193798
0.8659	High Similarity	NPC82851
0.8659	High Similarity	NPC472668
0.865	High Similarity	NPC475226
0.8642	High Similarity	NPC209364
0.8639	High Similarity	NPC471632
0.8634	High Similarity	NPC178932
0.8634	High Similarity	NPC282445
0.8623	High Similarity	NPC472766
0.8623	High Similarity	NPC472765
0.8616	High Similarity	NPC195325
0.8616	High Similarity	NPC470791
0.8616	High Similarity	NPC470790
0.8614	High Similarity	NPC470875
0.8614	High Similarity	NPC23387
0.8614	High Similarity	NPC472141
0.8608	High Similarity	NPC216755
0.8606	High Similarity	NPC477405
0.8606	High Similarity	NPC471168
0.8606	High Similarity	NPC134254
0.8606	High Similarity	NPC472669
0.8606	High Similarity	NPC419
0.8606	High Similarity	NPC39986
0.8606	High Similarity	NPC302369
0.8598	High Similarity	NPC335761
0.8598	High Similarity	NPC191828
0.8589	High Similarity	NPC197137
0.8589	High Similarity	NPC187149
0.8589	High Similarity	NPC45101
0.8589	High Similarity	NPC472772
0.8589	High Similarity	NPC472283
0.8588	High Similarity	NPC167340
0.858	High Similarity	NPC141538
0.858	High Similarity	NPC92979
0.858	High Similarity	NPC296807
0.858	High Similarity	NPC155939
0.8571	High Similarity	NPC472659
0.8563	High Similarity	NPC472651
0.8563	High Similarity	NPC472774
0.8563	High Similarity	NPC472775
0.8563	High Similarity	NPC173516
0.8562	High Similarity	NPC476122
0.8562	High Similarity	NPC469335
0.8562	High Similarity	NPC159927
0.8562	High Similarity	NPC470997
0.8554	High Similarity	NPC261184
0.8545	High Similarity	NPC471166
0.8545	High Similarity	NPC471167
0.8545	High Similarity	NPC149896
0.8545	High Similarity	NPC117986
0.8544	High Similarity	NPC346
0.8537	High Similarity	NPC307383
0.8537	High Similarity	NPC475967
0.8535	High Similarity	NPC251865
0.8528	High Similarity	NPC126723
0.8528	High Similarity	NPC107646
0.8526	High Similarity	NPC121158
0.8521	High Similarity	NPC169299
0.8521	High Similarity	NPC160818
0.8512	High Similarity	NPC242334
0.8512	High Similarity	NPC471397
0.8512	High Similarity	NPC271235
0.8512	High Similarity	NPC472652
0.8509	High Similarity	NPC116717
0.85	High Similarity	NPC471001
0.8491	Intermediate Similarity	NPC250228
0.8491	Intermediate Similarity	NPC470941
0.8491	Intermediate Similarity	NPC221809
0.8485	Intermediate Similarity	NPC475381
0.8471	Intermediate Similarity	NPC223415
0.8466	Intermediate Similarity	NPC469850
0.8457	Intermediate Similarity	NPC33938
0.8457	Intermediate Similarity	NPC75906
0.8452	Intermediate Similarity	NPC472282
0.8452	Intermediate Similarity	NPC473753
0.8452	Intermediate Similarity	NPC473766
0.8447	Intermediate Similarity	NPC196864
0.8447	Intermediate Similarity	NPC477404
0.8443	Intermediate Similarity	NPC271657
0.8434	Intermediate Similarity	NPC188649
0.8434	Intermediate Similarity	NPC470792
0.8434	Intermediate Similarity	NPC5741
0.8434	Intermediate Similarity	NPC263432
0.8434	Intermediate Similarity	NPC200782
0.8434	Intermediate Similarity	NPC472771
0.8434	Intermediate Similarity	NPC18347
0.8434	Intermediate Similarity	NPC470939
0.843	Intermediate Similarity	NPC470181
0.8428	Intermediate Similarity	NPC262198
0.8424	Intermediate Similarity	NPC474611
0.8424	Intermediate Similarity	NPC237155
0.8424	Intermediate Similarity	NPC472779
0.8415	Intermediate Similarity	NPC41880
0.8415	Intermediate Similarity	NPC60973
0.8412	Intermediate Similarity	NPC475237
0.8412	Intermediate Similarity	NPC475641
0.8402	Intermediate Similarity	NPC160651
0.8397	Intermediate Similarity	NPC56197
0.8395	Intermediate Similarity	NPC18135
0.8393	Intermediate Similarity	NPC475779
0.8385	Intermediate Similarity	NPC329180
0.8385	Intermediate Similarity	NPC234494
0.8385	Intermediate Similarity	NPC470998
0.8385	Intermediate Similarity	NPC211625
0.8383	Intermediate Similarity	NPC469846
0.8383	Intermediate Similarity	NPC288602
0.8383	Intermediate Similarity	NPC472773
0.8383	Intermediate Similarity	NPC472139
0.8383	Intermediate Similarity	NPC88841
0.8375	Intermediate Similarity	NPC255414
0.8373	Intermediate Similarity	NPC305016
0.8364	Intermediate Similarity	NPC195954
0.8364	Intermediate Similarity	NPC299038
0.8364	Intermediate Similarity	NPC214495
0.8364	Intermediate Similarity	NPC475066
0.8364	Intermediate Similarity	NPC470119
0.8354	Intermediate Similarity	NPC476262
0.8354	Intermediate Similarity	NPC470741
0.8354	Intermediate Similarity	NPC471175
0.8354	Intermediate Similarity	NPC243577
0.8354	Intermediate Similarity	NPC472785

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 NPC478179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	995
0.2-0.3	2182
0.3-0.4	2664
0.4-0.5	1871
0.5-0.6	836
0.6-0.7	277
0.7-0.8	20
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8812	High Similarity	NPD5760	Phase 2
0.8812	High Similarity	NPD5761	Phase 2
0.8161	Intermediate Similarity	NPD6765	Approved
0.8161	Intermediate Similarity	NPD6764	Approved
0.8155	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD8434	Phase 2
0.7978	Intermediate Similarity	NPD6784	Approved
0.7978	Intermediate Similarity	NPD6785	Approved
0.753	Intermediate Similarity	NPD7236	Approved
0.743	Intermediate Similarity	NPD7799	Discontinued
0.7412	Intermediate Similarity	NPD7239	Suspended
0.7299	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7819	Suspended
0.7297	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7251	Intermediate Similarity	NPD920	Approved
0.7225	Intermediate Similarity	NPD6599	Discontinued
0.7193	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD6801	Discontinued
0.7135	Intermediate Similarity	NPD919	Approved
0.7135	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8404	Phase 2
0.7062	Intermediate Similarity	NPD5402	Approved
0.7062	Intermediate Similarity	NPD3817	Phase 2
0.7056	Intermediate Similarity	NPD1247	Approved
0.7035	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1471	Phase 3
0.7024	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7058	Phase 2
0.7022	Intermediate Similarity	NPD7057	Phase 3
0.7018	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4628	Phase 3
0.6989	Remote Similarity	NPD6559	Discontinued
0.6983	Remote Similarity	NPD3749	Approved
0.6977	Remote Similarity	NPD6799	Approved
0.6971	Remote Similarity	NPD3226	Approved
0.6961	Remote Similarity	NPD8127	Discontinued
0.6936	Remote Similarity	NPD2532	Approved
0.6936	Remote Similarity	NPD2534	Approved
0.6936	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5762	Approved
0.6923	Remote Similarity	NPD5763	Approved
0.6923	Remote Similarity	NPD6004	Phase 3
0.6906	Remote Similarity	NPD5494	Approved
0.6893	Remote Similarity	NPD7411	Suspended
0.6885	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2796	Approved
0.6857	Remote Similarity	NPD5403	Approved
0.6842	Remote Similarity	NPD1243	Approved
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2800	Approved
0.6839	Remote Similarity	NPD5401	Approved
0.6833	Remote Similarity	NPD3882	Suspended
0.6828	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2346	Discontinued
0.6811	Remote Similarity	NPD7473	Discontinued
0.6809	Remote Similarity	NPD7685	Pre-registration
0.6806	Remote Similarity	NPD8150	Discontinued
0.6805	Remote Similarity	NPD7033	Discontinued
0.6805	Remote Similarity	NPD2799	Discontinued
0.6802	Remote Similarity	NPD3750	Approved
0.6789	Remote Similarity	NPD8407	Phase 2
0.6784	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3818	Discontinued
0.6772	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7497	Discontinued
0.6747	Remote Similarity	NPD2313	Discontinued
0.6743	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4380	Phase 2
0.6738	Remote Similarity	NPD5844	Phase 1
0.6726	Remote Similarity	NPD6355	Discontinued
0.6722	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8368	Discontinued
0.6706	Remote Similarity	NPD3748	Approved
0.6703	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1549	Phase 2
0.6685	Remote Similarity	NPD7199	Phase 2
0.6685	Remote Similarity	NPD6959	Discontinued
0.6684	Remote Similarity	NPD3751	Discontinued
0.6684	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6649	Remote Similarity	NPD8313	Approved
0.6649	Remote Similarity	NPD6232	Discontinued
0.6649	Remote Similarity	NPD8312	Approved
0.6648	Remote Similarity	NPD7028	Phase 2
0.6648	Remote Similarity	NPD7768	Phase 2
0.6648	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7907	Approved
0.6632	Remote Similarity	NPD7251	Discontinued
0.663	Remote Similarity	NPD2801	Approved
0.6628	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2344	Approved
0.6627	Remote Similarity	NPD6832	Phase 2
0.6613	Remote Similarity	NPD3926	Phase 2
0.6608	Remote Similarity	NPD1510	Phase 2
0.6607	Remote Similarity	NPD8032	Phase 2
0.6606	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7808	Phase 3
0.6592	Remote Similarity	NPD7458	Discontinued
0.6592	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6797	Phase 2
0.6578	Remote Similarity	NPD6166	Phase 2
0.6578	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1934	Approved
0.6564	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3787	Discontinued
0.6559	Remote Similarity	NPD7229	Phase 3
0.6557	Remote Similarity	NPD4967	Phase 2
0.6557	Remote Similarity	NPD4966	Approved
0.6557	Remote Similarity	NPD4965	Approved
0.6548	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3268	Approved
0.6548	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4107	Approved
0.6517	Remote Similarity	NPD1512	Approved
0.6514	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4308	Phase 3
0.6509	Remote Similarity	NPD6663	Approved
0.6506	Remote Similarity	NPD5647	Approved
0.6495	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6353	Approved
0.6491	Remote Similarity	NPD6651	Approved
0.6486	Remote Similarity	NPD6234	Discontinued
0.6484	Remote Similarity	NPD37	Approved
0.648	Remote Similarity	NPD8435	Approved
0.6477	Remote Similarity	NPD2309	Approved
0.6474	Remote Similarity	NPD7054	Approved
0.6473	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7874	Approved
0.6471	Remote Similarity	NPD5711	Approved
0.6471	Remote Similarity	NPD5710	Approved
0.6463	Remote Similarity	NPD1608	Approved
0.6462	Remote Similarity	NPD4665	Approved
0.6462	Remote Similarity	NPD4111	Phase 1
0.645	Remote Similarity	NPD3764	Approved
0.6446	Remote Similarity	NPD2797	Approved
0.644	Remote Similarity	NPD7472	Approved
0.644	Remote Similarity	NPD7074	Phase 3
0.6436	Remote Similarity	NPD6782	Approved
0.6436	Remote Similarity	NPD6779	Approved
0.6436	Remote Similarity	NPD6780	Approved
0.6436	Remote Similarity	NPD6776	Approved
0.6436	Remote Similarity	NPD6777	Approved
0.6436	Remote Similarity	NPD6781	Approved
0.6436	Remote Similarity	NPD6778	Approved
0.6433	Remote Similarity	NPD5735	Approved
0.6422	Remote Similarity	NPD7697	Approved
0.6422	Remote Similarity	NPD7696	Phase 3
0.6422	Remote Similarity	NPD7698	Approved
0.642	Remote Similarity	NPD7003	Approved
0.6412	Remote Similarity	NPD6233	Phase 2
0.6412	Remote Similarity	NPD7961	Discontinued
0.6407	Remote Similarity	NPD2798	Approved
0.6406	Remote Similarity	NPD5953	Discontinued
0.6404	Remote Similarity	NPD1511	Approved
0.6404	Remote Similarity	NPD4482	Phase 3
0.6402	Remote Similarity	NPD2403	Approved
0.6396	Remote Similarity	NPD8360	Approved
0.6396	Remote Similarity	NPD8361	Approved
0.6395	Remote Similarity	NPD1607	Approved
0.6395	Remote Similarity	NPD6653	Approved
0.6391	Remote Similarity	NPD7095	Approved
0.639	Remote Similarity	NPD7871	Phase 2
0.639	Remote Similarity	NPD7870	Phase 2
0.6389	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7286	Phase 2
0.6384	Remote Similarity	NPD3887	Approved
0.6384	Remote Similarity	NPD6190	Approved
0.6383	Remote Similarity	NPD7315	Approved
0.6383	Remote Similarity	NPD6808	Phase 2
0.6374	Remote Similarity	NPD1240	Approved
0.6374	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4307	Phase 2
0.6373	Remote Similarity	NPD3057	Approved
0.6369	Remote Similarity	NPD5736	Approved
0.6368	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9717	Approved
0.6353	Remote Similarity	NPD6798	Discontinued
0.6347	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6362	Approved
0.6347	Remote Similarity	NPD3267	Approved
0.6347	Remote Similarity	NPD3266	Approved
0.6341	Remote Similarity	NPD7457	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