NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	424.25
Volume:	440.237
LogP:	4.433
LogD:	3.621
LogS:	-4.438
# Rotatable Bonds:	8
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	4.491
Fsp3:	0.739
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	4.1673105442896485e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.657
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.794

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	91.97643280029297%
Volume Distribution (VD):	2.143
Pgp-substrate:	7.146737575531006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.138
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.486
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	3.181
Half-life (T1/2):	0.506

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.397
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.82
Carcinogencity:	0.062
Eye Corrosion:	0.137
Eye Irritation:	0.314
Respiratory Toxicity:	0.152

Download Data

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

Natural Product: NPC477748

Natural Product ID:	NPC477748
*Common Name:**	[(2R,3S,4S,5R,6S)-5-acetyloxy-3-hydroxy-2-methyl-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-4-yl] 3-methylbut-2-enoate
IUPAC Name:	[(2R,3S,4S,5R,6S)-5-acetyloxy-3-hydroxy-2-methyl-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-4-yl] 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	OWFNCOMYPJMMPG-CIKNZCACSA-N
Standard InCHI:	InChI=1S/C23H36O7/c1-13(2)12-18(25)29-20-19(26)15(4)27-22(21(20)28-16(5)24)30-23(6,7)17-10-8-14(3)9-11-17/h8,12,15,17,19-22,26H,9-11H2,1-7H3/t15-,17+,19+,20+,21-,22+/m1/s1
SMILES:	C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC(C)(C)[C@@H]2CCC(=CC2)C)OC(=O)C)OC(=O)C=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122180069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO33680	Pittosporum venulosum	Species	Pittosporaceae	Eukaryota	n.a.	State Forest 144, Mt. Windsor Tableland, Queensland, Australia	1995-JUL	PMID[25984885]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	8120	nM	PMID[25984885]

☑ 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 NPC477748 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	186
0.1-0.2	1313
0.2-0.3	4969
0.3-0.4	11418
0.4-0.5	11916
0.5-0.6	7773
0.6-0.7	4383
0.7-0.8	674
0.8-0.85	48
0.85-0.9	11
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC202886
0.9765	High Similarity	NPC477749
0.9059	High Similarity	NPC477746
0.9059	High Similarity	NPC477747
0.8941	High Similarity	NPC266718
0.875	High Similarity	NPC248312
0.869	High Similarity	NPC100697
0.8602	High Similarity	NPC309503
0.8602	High Similarity	NPC96597
0.8602	High Similarity	NPC91197
0.8602	High Similarity	NPC239547
0.8602	High Similarity	NPC155319
0.8602	High Similarity	NPC125551
0.8571	High Similarity	NPC238090
0.8571	High Similarity	NPC472195
0.8571	High Similarity	NPC472196
0.8506	High Similarity	NPC475035
0.8488	Intermediate Similarity	NPC20072
0.8478	Intermediate Similarity	NPC159698
0.8409	Intermediate Similarity	NPC471494
0.8333	Intermediate Similarity	NPC280991
0.8315	Intermediate Similarity	NPC311163
0.828	Intermediate Similarity	NPC96736
0.828	Intermediate Similarity	NPC2003
0.828	Intermediate Similarity	NPC25701
0.828	Intermediate Similarity	NPC178949
0.8256	Intermediate Similarity	NPC127295
0.8256	Intermediate Similarity	NPC163362
0.8247	Intermediate Similarity	NPC201191
0.8229	Intermediate Similarity	NPC130792
0.8222	Intermediate Similarity	NPC475037
0.8182	Intermediate Similarity	NPC239961
0.8172	Intermediate Similarity	NPC67398
0.8172	Intermediate Similarity	NPC91654
0.8172	Intermediate Similarity	NPC320089
0.8172	Intermediate Similarity	NPC474792
0.8163	Intermediate Similarity	NPC151516
0.8161	Intermediate Similarity	NPC469469
0.8152	Intermediate Similarity	NPC118078
0.8144	Intermediate Similarity	NPC198992
0.8125	Intermediate Similarity	NPC198422
0.8125	Intermediate Similarity	NPC40182
0.8105	Intermediate Similarity	NPC54731
0.8085	Intermediate Similarity	NPC294293
0.8085	Intermediate Similarity	NPC256368
0.8065	Intermediate Similarity	NPC302584
0.8043	Intermediate Similarity	NPC309310
0.8	Intermediate Similarity	NPC470124
0.8	Intermediate Similarity	NPC82251
0.8	Intermediate Similarity	NPC229655
0.8	Intermediate Similarity	NPC475034
0.7979	Intermediate Similarity	NPC61201
0.7979	Intermediate Similarity	NPC474835
0.7959	Intermediate Similarity	NPC2313
0.7959	Intermediate Similarity	NPC475157
0.7959	Intermediate Similarity	NPC471637
0.7959	Intermediate Similarity	NPC154132
0.7959	Intermediate Similarity	NPC57586
0.7959	Intermediate Similarity	NPC475655
0.7957	Intermediate Similarity	NPC303451
0.7957	Intermediate Similarity	NPC327253
0.7957	Intermediate Similarity	NPC6414
0.7941	Intermediate Similarity	NPC206618
0.7938	Intermediate Similarity	NPC169468
0.7938	Intermediate Similarity	NPC61630
0.7938	Intermediate Similarity	NPC307517
0.7938	Intermediate Similarity	NPC81483
0.7917	Intermediate Similarity	NPC143446
0.7912	Intermediate Similarity	NPC470836
0.7889	Intermediate Similarity	NPC473308
0.7879	Intermediate Similarity	NPC121423
0.7872	Intermediate Similarity	NPC472197
0.7872	Intermediate Similarity	NPC472199
0.7865	Intermediate Similarity	NPC251026
0.7857	Intermediate Similarity	NPC477716
0.7857	Intermediate Similarity	NPC477721
0.7849	Intermediate Similarity	NPC133450
0.7843	Intermediate Similarity	NPC392
0.7843	Intermediate Similarity	NPC38948
0.7843	Intermediate Similarity	NPC177524
0.7843	Intermediate Similarity	NPC219900
0.7826	Intermediate Similarity	NPC475186
0.7826	Intermediate Similarity	NPC471055
0.7826	Intermediate Similarity	NPC471056
0.7826	Intermediate Similarity	NPC316138
0.7826	Intermediate Similarity	NPC313658
0.7826	Intermediate Similarity	NPC118077
0.7812	Intermediate Similarity	NPC469543
0.7812	Intermediate Similarity	NPC108141
0.781	Intermediate Similarity	NPC287075
0.781	Intermediate Similarity	NPC473159
0.7802	Intermediate Similarity	NPC470658
0.78	Intermediate Similarity	NPC197736
0.7791	Intermediate Similarity	NPC326661
0.7789	Intermediate Similarity	NPC320552
0.7778	Intermediate Similarity	NPC2379
0.7778	Intermediate Similarity	NPC231601
0.7778	Intermediate Similarity	NPC31019
0.7778	Intermediate Similarity	NPC477717
0.7778	Intermediate Similarity	NPC44261
0.7778	Intermediate Similarity	NPC473315
0.7778	Intermediate Similarity	NPC263087
0.7778	Intermediate Similarity	NPC142111
0.7778	Intermediate Similarity	NPC219038
0.7778	Intermediate Similarity	NPC27314
0.7778	Intermediate Similarity	NPC106912
0.7766	Intermediate Similarity	NPC3952
0.7766	Intermediate Similarity	NPC471569
0.7766	Intermediate Similarity	NPC177668
0.7757	Intermediate Similarity	NPC203862
0.7755	Intermediate Similarity	NPC472015
0.7755	Intermediate Similarity	NPC65700
0.7745	Intermediate Similarity	NPC472390
0.7736	Intermediate Similarity	NPC84949
0.7736	Intermediate Similarity	NPC31354
0.7736	Intermediate Similarity	NPC69576
0.7736	Intermediate Similarity	NPC471633
0.7732	Intermediate Similarity	NPC256230
0.7732	Intermediate Similarity	NPC306041
0.7727	Intermediate Similarity	NPC321728
0.7723	Intermediate Similarity	NPC470768
0.7723	Intermediate Similarity	NPC86095
0.7717	Intermediate Similarity	NPC208473
0.7714	Intermediate Similarity	NPC470025
0.7714	Intermediate Similarity	NPC328074
0.7714	Intermediate Similarity	NPC321272
0.7714	Intermediate Similarity	NPC317460
0.7708	Intermediate Similarity	NPC211238
0.7708	Intermediate Similarity	NPC472198
0.7701	Intermediate Similarity	NPC40049
0.77	Intermediate Similarity	NPC223834
0.77	Intermediate Similarity	NPC471599
0.77	Intermediate Similarity	NPC470571
0.77	Intermediate Similarity	NPC222062
0.77	Intermediate Similarity	NPC472815
0.77	Intermediate Similarity	NPC195510
0.77	Intermediate Similarity	NPC13171
0.7692	Intermediate Similarity	NPC166279
0.7692	Intermediate Similarity	NPC316708
0.7684	Intermediate Similarity	NPC9447
0.7677	Intermediate Similarity	NPC255677
0.7677	Intermediate Similarity	NPC79631
0.7677	Intermediate Similarity	NPC244878
0.7677	Intermediate Similarity	NPC306344
0.7677	Intermediate Similarity	NPC324841
0.7677	Intermediate Similarity	NPC22149
0.767	Intermediate Similarity	NPC48548
0.767	Intermediate Similarity	NPC128795
0.767	Intermediate Similarity	NPC135015
0.767	Intermediate Similarity	NPC217921
0.7664	Intermediate Similarity	NPC207637
0.7664	Intermediate Similarity	NPC199428
0.7664	Intermediate Similarity	NPC5311
0.7664	Intermediate Similarity	NPC193382
0.7664	Intermediate Similarity	NPC310341
0.7664	Intermediate Similarity	NPC99620
0.766	Intermediate Similarity	NPC470734
0.766	Intermediate Similarity	NPC249408
0.766	Intermediate Similarity	NPC285588
0.766	Intermediate Similarity	NPC104129
0.7653	Intermediate Similarity	NPC477719
0.7653	Intermediate Similarity	NPC477718
0.7653	Intermediate Similarity	NPC474182
0.7653	Intermediate Similarity	NPC98112
0.7653	Intermediate Similarity	NPC474194
0.7647	Intermediate Similarity	NPC470767
0.7647	Intermediate Similarity	NPC85670
0.7647	Intermediate Similarity	NPC470763
0.7647	Intermediate Similarity	NPC315070
0.7642	Intermediate Similarity	NPC470027
0.7629	Intermediate Similarity	NPC230347
0.7629	Intermediate Similarity	NPC275310
0.7629	Intermediate Similarity	NPC286612
0.7629	Intermediate Similarity	NPC240838
0.7624	Intermediate Similarity	NPC120009
0.7624	Intermediate Similarity	NPC267869
0.7624	Intermediate Similarity	NPC234304
0.7624	Intermediate Similarity	NPC281378
0.7624	Intermediate Similarity	NPC197541
0.7624	Intermediate Similarity	NPC284929
0.7624	Intermediate Similarity	NPC118761
0.7619	Intermediate Similarity	NPC470026
0.7619	Intermediate Similarity	NPC17791
0.7614	Intermediate Similarity	NPC477089
0.7609	Intermediate Similarity	NPC34581
0.7609	Intermediate Similarity	NPC163606
0.76	Intermediate Similarity	NPC28304
0.76	Intermediate Similarity	NPC154127
0.76	Intermediate Similarity	NPC11974
0.76	Intermediate Similarity	NPC285231
0.76	Intermediate Similarity	NPC20673
0.76	Intermediate Similarity	NPC298255
0.76	Intermediate Similarity	NPC21568
0.76	Intermediate Similarity	NPC472554
0.7596	Intermediate Similarity	NPC40728
0.7596	Intermediate Similarity	NPC316974
0.7596	Intermediate Similarity	NPC133625
0.7593	Intermediate Similarity	NPC471355
0.7593	Intermediate Similarity	NPC84987
0.7593	Intermediate Similarity	NPC243196

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 NPC477748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1652
0.2-0.3	4039
0.3-0.4	2235
0.4-0.5	675
0.5-0.6	314
0.6-0.7	64
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7843	Intermediate Similarity	NPD6686	Approved
0.7766	Intermediate Similarity	NPD6698	Approved
0.7766	Intermediate Similarity	NPD46	Approved
0.7755	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7328	Approved
0.7523	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7503	Approved
0.7455	Intermediate Similarity	NPD7516	Approved
0.7396	Intermediate Similarity	NPD7838	Discovery
0.7387	Intermediate Similarity	NPD8294	Approved
0.7387	Intermediate Similarity	NPD8377	Approved
0.7321	Intermediate Similarity	NPD8033	Approved
0.7321	Intermediate Similarity	NPD8378	Approved
0.7321	Intermediate Similarity	NPD8335	Approved
0.7321	Intermediate Similarity	NPD8296	Approved
0.7321	Intermediate Similarity	NPD8380	Approved
0.7321	Intermediate Similarity	NPD8379	Approved
0.7255	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD6412	Phase 2
0.7168	Intermediate Similarity	NPD8513	Phase 3
0.7168	Intermediate Similarity	NPD8515	Approved
0.7168	Intermediate Similarity	NPD8517	Approved
0.7168	Intermediate Similarity	NPD8516	Approved
0.7069	Intermediate Similarity	NPD7507	Approved
0.6972	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7319	Approved
0.6827	Remote Similarity	NPD6648	Approved
0.6731	Remote Similarity	NPD7638	Approved
0.6696	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7983	Approved
0.6628	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8328	Phase 3
0.661	Remote Similarity	NPD7830	Approved
0.661	Remote Similarity	NPD7829	Approved
0.6607	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8074	Phase 3
0.6577	Remote Similarity	NPD6371	Approved
0.6571	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD368	Approved
0.6471	Remote Similarity	NPD7642	Approved
0.6408	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8451	Approved
0.6325	Remote Similarity	NPD7641	Discontinued
0.6311	Remote Similarity	NPD8448	Approved
0.6311	Remote Similarity	NPD7637	Suspended
0.6311	Remote Similarity	NPD8293	Discontinued
0.6303	Remote Similarity	NPD8444	Approved
0.6283	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7115	Discovery
0.6238	Remote Similarity	NPD4251	Approved
0.6238	Remote Similarity	NPD4250	Approved
0.6238	Remote Similarity	NPD7524	Approved
0.6226	Remote Similarity	NPD7839	Suspended
0.6186	Remote Similarity	NPD4822	Approved
0.6186	Remote Similarity	NPD4819	Approved
0.6186	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4821	Approved
0.6186	Remote Similarity	NPD4820	Approved
0.616	Remote Similarity	NPD8390	Approved
0.616	Remote Similarity	NPD8392	Approved
0.616	Remote Similarity	NPD8391	Approved
0.6148	Remote Similarity	NPD8340	Approved
0.6148	Remote Similarity	NPD8342	Approved
0.6148	Remote Similarity	NPD8341	Approved
0.6148	Remote Similarity	NPD7492	Approved
0.6148	Remote Similarity	NPD8299	Approved
0.6139	Remote Similarity	NPD4249	Approved
0.6124	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6051	Approved
0.6117	Remote Similarity	NPD6101	Approved
0.6106	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6009	Approved
0.61	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6616	Approved
0.6091	Remote Similarity	NPD7632	Discontinued
0.6083	Remote Similarity	NPD6059	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6058	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7078	Approved
0.604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6882	Approved
0.6019	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6084	Phase 2
0.6018	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD7154	Phase 3
0.6	Remote Similarity	NPD6411	Approved
0.5984	Remote Similarity	NPD8080	Discontinued
0.5983	Remote Similarity	NPD4632	Approved
0.5979	Remote Similarity	NPD4268	Approved
0.5979	Remote Similarity	NPD4271	Approved
0.5966	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7625	Phase 1
0.595	Remote Similarity	NPD6319	Approved
0.5935	Remote Similarity	NPD6067	Discontinued
0.5929	Remote Similarity	NPD5739	Approved
0.5929	Remote Similarity	NPD6675	Approved
0.5929	Remote Similarity	NPD7128	Approved
0.5929	Remote Similarity	NPD4211	Phase 1
0.5929	Remote Similarity	NPD6402	Approved
0.5926	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD3168	Discontinued
0.5905	Remote Similarity	NPD5785	Approved
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD6016	Approved
0.59	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6435	Approved
0.5897	Remote Similarity	NPD8297	Approved
0.5888	Remote Similarity	NPD7748	Approved
0.5888	Remote Similarity	NPD5282	Discontinued
0.5882	Remote Similarity	NPD1694	Approved
0.5872	Remote Similarity	NPD7902	Approved
0.5859	Remote Similarity	NPD7332	Phase 2
0.5859	Remote Similarity	NPD7514	Phase 3
0.5854	Remote Similarity	NPD5988	Approved
0.5849	Remote Similarity	NPD7515	Phase 2
0.5842	Remote Similarity	NPD5362	Discontinued
0.5842	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3669	Approved
0.5833	Remote Similarity	NPD7505	Discontinued
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5695	Phase 3
0.5826	Remote Similarity	NPD6899	Approved
0.5826	Remote Similarity	NPD6881	Approved
0.5826	Remote Similarity	NPD7320	Approved
0.5816	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.581	Remote Similarity	NPD1695	Approved
0.5794	Remote Similarity	NPD6399	Phase 3
0.5778	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6372	Approved
0.5776	Remote Similarity	NPD6373	Approved
0.5772	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7750	Discontinued
0.5752	Remote Similarity	NPD1407	Approved
0.5748	Remote Similarity	NPD8337	Approved
0.5748	Remote Similarity	NPD8336	Approved
0.5745	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5209	Approved
0.5739	Remote Similarity	NPD5697	Approved
0.5739	Remote Similarity	NPD5701	Approved
0.5736	Remote Similarity	NPD7260	Phase 2
0.5729	Remote Similarity	NPD1811	Approved
0.5729	Remote Similarity	NPD1810	Approved
0.5728	Remote Similarity	NPD5363	Approved
0.5726	Remote Similarity	NPD7290	Approved
0.5726	Remote Similarity	NPD7102	Approved
0.5726	Remote Similarity	NPD5126	Approved
0.5726	Remote Similarity	NPD6883	Approved
0.5726	Remote Similarity	NPD5125	Phase 3
0.5714	Remote Similarity	NPD8273	Phase 1
0.5714	Remote Similarity	NPD5776	Phase 2
0.5714	Remote Similarity	NPD6932	Approved
0.5714	Remote Similarity	NPD6925	Approved
0.5702	Remote Similarity	NPD7500	Approved
0.57	Remote Similarity	NPD5368	Approved
0.57	Remote Similarity	NPD6930	Phase 2
0.57	Remote Similarity	NPD6931	Approved
0.5686	Remote Similarity	NPD5332	Approved
0.5686	Remote Similarity	NPD5331	Approved
0.568	Remote Similarity	NPD7604	Phase 2
0.5678	Remote Similarity	NPD6869	Approved
0.5678	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6847	Approved
0.5678	Remote Similarity	NPD6650	Approved
0.5678	Remote Similarity	NPD6617	Approved
0.5678	Remote Similarity	NPD6649	Approved
0.5678	Remote Similarity	NPD8130	Phase 1
0.5676	Remote Similarity	NPD5696	Approved
0.5673	Remote Similarity	NPD7521	Approved
0.5673	Remote Similarity	NPD6684	Approved
0.5673	Remote Similarity	NPD7334	Approved
0.5673	Remote Similarity	NPD6409	Approved
0.5673	Remote Similarity	NPD5330	Approved
0.5673	Remote Similarity	NPD7146	Approved
0.567	Remote Similarity	NPD8039	Approved
0.567	Remote Similarity	NPD8264	Approved
0.5657	Remote Similarity	NPD7145	Approved
0.5652	Remote Similarity	NPD6640	Phase 3
0.5645	Remote Similarity	NPD5983	Phase 2
0.5644	Remote Similarity	NPD6902	Approved
0.5644	Remote Similarity	NPD5369	Approved
0.5644	Remote Similarity	NPD4790	Discontinued
0.5644	Remote Similarity	NPD6898	Phase 1
0.5641	Remote Similarity	NPD6014	Approved
0.5641	Remote Similarity	NPD6012	Approved
0.5641	Remote Similarity	NPD6013	Approved
0.563	Remote Similarity	NPD6430	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