NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	424.25
Volume:	440.237
LogP:	4.087
LogD:	3.617
LogS:	-4.226
# 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:	4.523
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:	-4.679
MDCK Permeability:	2.6417033950565383e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	91.38390350341797%
Volume Distribution (VD):	2.46
Pgp-substrate:	6.16975212097168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.534
CYP2C9-inhibitor:	0.44
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.137
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	4.658
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.68
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.471
Carcinogencity:	0.086
Eye Corrosion:	0.017
Eye Irritation:	0.175
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC477749

Natural Product ID:	NPC477749
*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] (Z)-2-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] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	FEKXOQQBOGOFSV-SRQMRGMMSA-N
Standard InCHI:	InChI=1S/C23H36O7/c1-8-14(3)21(26)29-19-18(25)15(4)27-22(20(19)28-16(5)24)30-23(6,7)17-11-9-13(2)10-12-17/h8-9,15,17-20,22,25H,10-12H2,1-7H3/b14-8-/t15-,17+,18+,19+,20-,22+/m1/s1
SMILES:	C/C=C(/C)\C(=O)O[C@H]1[C@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC(C)(C)[C@@H]2CCC(=CC2)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122180070
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	=	29170	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 NPC477749 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	189
0.1-0.2	1240
0.2-0.3	4897
0.3-0.4	10700
0.4-0.5	12411
0.5-0.6	7670
0.6-0.7	4778
0.7-0.8	735
0.8-0.85	60
0.85-0.9	11
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC477748
0.9651	High Similarity	NPC202886
0.907	High Similarity	NPC477747
0.907	High Similarity	NPC477746
0.8953	High Similarity	NPC266718
0.8791	High Similarity	NPC472195
0.8791	High Similarity	NPC472196
0.8791	High Similarity	NPC238090
0.8736	High Similarity	NPC475035
0.8696	High Similarity	NPC159698
0.8556	High Similarity	NPC248312
0.8488	Intermediate Similarity	NPC100697
0.8454	Intermediate Similarity	NPC201191
0.8444	Intermediate Similarity	NPC475037
0.8421	Intermediate Similarity	NPC239547
0.8421	Intermediate Similarity	NPC155319
0.8421	Intermediate Similarity	NPC125551
0.8421	Intermediate Similarity	NPC96597
0.8421	Intermediate Similarity	NPC309503
0.8421	Intermediate Similarity	NPC91197
0.8298	Intermediate Similarity	NPC2003
0.8298	Intermediate Similarity	NPC25701
0.8295	Intermediate Similarity	NPC20072
0.8222	Intermediate Similarity	NPC470124
0.8222	Intermediate Similarity	NPC471494
0.8222	Intermediate Similarity	NPC475034
0.82	Intermediate Similarity	NPC239961
0.8191	Intermediate Similarity	NPC61201
0.8191	Intermediate Similarity	NPC320089
0.8182	Intermediate Similarity	NPC469469
0.8182	Intermediate Similarity	NPC151516
0.8172	Intermediate Similarity	NPC303451
0.8172	Intermediate Similarity	NPC6414
0.8172	Intermediate Similarity	NPC118078
0.8163	Intermediate Similarity	NPC198992
0.8163	Intermediate Similarity	NPC280991
0.8144	Intermediate Similarity	NPC198422
0.8144	Intermediate Similarity	NPC40182
0.8132	Intermediate Similarity	NPC311163
0.8125	Intermediate Similarity	NPC54731
0.8105	Intermediate Similarity	NPC178949
0.8105	Intermediate Similarity	NPC256368
0.8105	Intermediate Similarity	NPC96736
0.8105	Intermediate Similarity	NPC294293
0.8068	Intermediate Similarity	NPC163362
0.8068	Intermediate Similarity	NPC127295
0.8061	Intermediate Similarity	NPC130792
0.8043	Intermediate Similarity	NPC118077
0.8043	Intermediate Similarity	NPC475186
0.8039	Intermediate Similarity	NPC177524
0.8039	Intermediate Similarity	NPC219900
0.8039	Intermediate Similarity	NPC392
0.8021	Intermediate Similarity	NPC469543
0.802	Intermediate Similarity	NPC82251
0.8	Intermediate Similarity	NPC44261
0.8	Intermediate Similarity	NPC473159
0.8	Intermediate Similarity	NPC474792
0.8	Intermediate Similarity	NPC67398
0.8	Intermediate Similarity	NPC91654
0.798	Intermediate Similarity	NPC57586
0.798	Intermediate Similarity	NPC471637
0.798	Intermediate Similarity	NPC475157
0.798	Intermediate Similarity	NPC154132
0.798	Intermediate Similarity	NPC2313
0.798	Intermediate Similarity	NPC475655
0.7979	Intermediate Similarity	NPC327253
0.7959	Intermediate Similarity	NPC472015
0.7959	Intermediate Similarity	NPC81483
0.7959	Intermediate Similarity	NPC61630
0.7959	Intermediate Similarity	NPC307517
0.7959	Intermediate Similarity	NPC169468
0.7938	Intermediate Similarity	NPC306041
0.7938	Intermediate Similarity	NPC143446
0.7921	Intermediate Similarity	NPC86095
0.7912	Intermediate Similarity	NPC473308
0.79	Intermediate Similarity	NPC121423
0.79	Intermediate Similarity	NPC222062
0.79	Intermediate Similarity	NPC195510
0.79	Intermediate Similarity	NPC13171
0.7895	Intermediate Similarity	NPC472197
0.7895	Intermediate Similarity	NPC472199
0.7895	Intermediate Similarity	NPC302584
0.7889	Intermediate Similarity	NPC251026
0.7879	Intermediate Similarity	NPC306344
0.7879	Intermediate Similarity	NPC22149
0.7879	Intermediate Similarity	NPC255677
0.7872	Intermediate Similarity	NPC285588
0.7872	Intermediate Similarity	NPC309310
0.7872	Intermediate Similarity	NPC133450
0.7857	Intermediate Similarity	NPC474182
0.7849	Intermediate Similarity	NPC313658
0.7849	Intermediate Similarity	NPC316138
0.7835	Intermediate Similarity	NPC108141
0.783	Intermediate Similarity	NPC287075
0.7822	Intermediate Similarity	NPC234304
0.7822	Intermediate Similarity	NPC118761
0.7822	Intermediate Similarity	NPC267869
0.7822	Intermediate Similarity	NPC197541
0.7822	Intermediate Similarity	NPC197736
0.7822	Intermediate Similarity	NPC284929
0.7816	Intermediate Similarity	NPC326661
0.7816	Intermediate Similarity	NPC229655
0.7812	Intermediate Similarity	NPC320552
0.7812	Intermediate Similarity	NPC474835
0.7802	Intermediate Similarity	NPC2379
0.7802	Intermediate Similarity	NPC142111
0.7802	Intermediate Similarity	NPC263087
0.7802	Intermediate Similarity	NPC27314
0.7802	Intermediate Similarity	NPC473315
0.7802	Intermediate Similarity	NPC31019
0.7802	Intermediate Similarity	NPC106912
0.78	Intermediate Similarity	NPC219038
0.78	Intermediate Similarity	NPC28304
0.78	Intermediate Similarity	NPC298255
0.7789	Intermediate Similarity	NPC117596
0.7789	Intermediate Similarity	NPC177668
0.7789	Intermediate Similarity	NPC471569
0.7789	Intermediate Similarity	NPC3952
0.7788	Intermediate Similarity	NPC206618
0.7778	Intermediate Similarity	NPC65700
0.7778	Intermediate Similarity	NPC203627
0.7767	Intermediate Similarity	NPC474285
0.7767	Intermediate Similarity	NPC254538
0.7755	Intermediate Similarity	NPC256230
0.7755	Intermediate Similarity	NPC472995
0.7753	Intermediate Similarity	NPC321728
0.7742	Intermediate Similarity	NPC208473
0.7742	Intermediate Similarity	NPC470836
0.7736	Intermediate Similarity	NPC470025
0.7736	Intermediate Similarity	NPC321272
0.7736	Intermediate Similarity	NPC328074
0.7736	Intermediate Similarity	NPC317460
0.7732	Intermediate Similarity	NPC71589
0.7732	Intermediate Similarity	NPC472198
0.7723	Intermediate Similarity	NPC471599
0.7723	Intermediate Similarity	NPC261117
0.7723	Intermediate Similarity	NPC223834
0.7723	Intermediate Similarity	NPC310804
0.7714	Intermediate Similarity	NPC235014
0.7714	Intermediate Similarity	NPC472508
0.7714	Intermediate Similarity	NPC316708
0.7708	Intermediate Similarity	NPC9447
0.7708	Intermediate Similarity	NPC110072
0.7708	Intermediate Similarity	NPC472125
0.7708	Intermediate Similarity	NPC472126
0.7708	Intermediate Similarity	NPC472124
0.7706	Intermediate Similarity	NPC470515
0.77	Intermediate Similarity	NPC477716
0.77	Intermediate Similarity	NPC79631
0.77	Intermediate Similarity	NPC244878
0.77	Intermediate Similarity	NPC477721
0.7692	Intermediate Similarity	NPC217921
0.7692	Intermediate Similarity	NPC48548
0.7692	Intermediate Similarity	NPC135015
0.7692	Intermediate Similarity	NPC128795
0.7692	Intermediate Similarity	NPC38948
0.7685	Intermediate Similarity	NPC207637
0.7685	Intermediate Similarity	NPC471816
0.7677	Intermediate Similarity	NPC476613
0.7677	Intermediate Similarity	NPC278506
0.7677	Intermediate Similarity	NPC266842
0.7677	Intermediate Similarity	NPC476612
0.7677	Intermediate Similarity	NPC474194
0.767	Intermediate Similarity	NPC315070
0.767	Intermediate Similarity	NPC218158
0.767	Intermediate Similarity	NPC85670
0.7664	Intermediate Similarity	NPC470027
0.7664	Intermediate Similarity	NPC264153
0.766	Intermediate Similarity	NPC471055
0.766	Intermediate Similarity	NPC471056
0.7653	Intermediate Similarity	NPC170204
0.7642	Intermediate Similarity	NPC17791
0.7642	Intermediate Similarity	NPC470026
0.7636	Intermediate Similarity	NPC470914
0.7636	Intermediate Similarity	NPC470517
0.7636	Intermediate Similarity	NPC470911
0.7636	Intermediate Similarity	NPC470915
0.7634	Intermediate Similarity	NPC470658
0.7624	Intermediate Similarity	NPC154127
0.7624	Intermediate Similarity	NPC20673
0.7624	Intermediate Similarity	NPC477717
0.7624	Intermediate Similarity	NPC476611
0.7619	Intermediate Similarity	NPC133625
0.7619	Intermediate Similarity	NPC316974
0.7619	Intermediate Similarity	NPC40728
0.7615	Intermediate Similarity	NPC474483
0.7615	Intermediate Similarity	NPC203862
0.7609	Intermediate Similarity	NPC231601
0.7604	Intermediate Similarity	NPC470573
0.7604	Intermediate Similarity	NPC473448
0.7604	Intermediate Similarity	NPC65665
0.7604	Intermediate Similarity	NPC473311
0.7604	Intermediate Similarity	NPC216826
0.7604	Intermediate Similarity	NPC231710
0.7604	Intermediate Similarity	NPC120021
0.7604	Intermediate Similarity	NPC270908
0.7604	Intermediate Similarity	NPC307699
0.76	Intermediate Similarity	NPC70733
0.76	Intermediate Similarity	NPC187761
0.76	Intermediate Similarity	NPC151093

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 NPC477749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1581
0.2-0.3	4032
0.3-0.4	2276
0.4-0.5	686
0.5-0.6	337
0.6-0.7	67
0.7-0.8	7
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
0.8039	Intermediate Similarity	NPD6686	Approved
0.7959	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD46	Approved
0.7789	Intermediate Similarity	NPD6698	Approved
0.7604	Intermediate Similarity	NPD7838	Discovery
0.75	Intermediate Similarity	NPD7503	Approved
0.7387	Intermediate Similarity	NPD7327	Approved
0.7387	Intermediate Similarity	NPD7328	Approved
0.734	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7516	Approved
0.7282	Intermediate Similarity	NPD5344	Discontinued
0.7264	Intermediate Similarity	NPD6412	Phase 2
0.7257	Intermediate Similarity	NPD8294	Approved
0.7257	Intermediate Similarity	NPD8377	Approved
0.7193	Intermediate Similarity	NPD8033	Approved
0.7193	Intermediate Similarity	NPD8378	Approved
0.7193	Intermediate Similarity	NPD8513	Phase 3
0.7193	Intermediate Similarity	NPD8516	Approved
0.7193	Intermediate Similarity	NPD8296	Approved
0.7193	Intermediate Similarity	NPD8380	Approved
0.7193	Intermediate Similarity	NPD8517	Approved
0.7193	Intermediate Similarity	NPD8379	Approved
0.7193	Intermediate Similarity	NPD8335	Approved
0.7193	Intermediate Similarity	NPD8515	Approved
0.7094	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7319	Approved
0.6857	Remote Similarity	NPD6648	Approved
0.6789	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7830	Approved
0.678	Remote Similarity	NPD7829	Approved
0.6762	Remote Similarity	NPD7638	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD6371	Approved
0.6726	Remote Similarity	NPD8133	Approved
0.6701	Remote Similarity	NPD6110	Phase 1
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD7642	Approved
0.6637	Remote Similarity	NPD6053	Discontinued
0.6612	Remote Similarity	NPD8074	Phase 3
0.6496	Remote Similarity	NPD7641	Discontinued
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6423	Remote Similarity	NPD7736	Approved
0.6417	Remote Similarity	NPD6370	Approved
0.641	Remote Similarity	NPD7115	Discovery
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD8451	Approved
0.6346	Remote Similarity	NPD7637	Suspended
0.6341	Remote Similarity	NPD8293	Discontinued
0.6341	Remote Similarity	NPD8448	Approved
0.6333	Remote Similarity	NPD8444	Approved
0.6322	Remote Similarity	NPD368	Approved
0.6316	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7492	Approved
0.6279	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4250	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.6271	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6009	Approved
0.6262	Remote Similarity	NPD7839	Suspended
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.6238	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4822	Approved
0.6224	Remote Similarity	NPD4820	Approved
0.6224	Remote Similarity	NPD4821	Approved
0.6224	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4819	Approved
0.621	Remote Similarity	NPD7078	Approved
0.6207	Remote Similarity	NPD6882	Approved
0.619	Remote Similarity	NPD8390	Approved
0.619	Remote Similarity	NPD8392	Approved
0.619	Remote Similarity	NPD8391	Approved
0.6179	Remote Similarity	NPD8340	Approved
0.6179	Remote Similarity	NPD8341	Approved
0.6179	Remote Similarity	NPD8299	Approved
0.6179	Remote Similarity	NPD8342	Approved
0.6176	Remote Similarity	NPD4249	Approved
0.6154	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4632	Approved
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7632	Discontinued
0.6117	Remote Similarity	NPD7524	Approved
0.6116	Remote Similarity	NPD6059	Approved
0.6116	Remote Similarity	NPD6319	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5785	Approved
0.6078	Remote Similarity	NPD1694	Approved
0.6068	Remote Similarity	NPD8297	Approved
0.6066	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD6015	Approved
0.6055	Remote Similarity	NPD6083	Phase 2
0.6055	Remote Similarity	NPD6084	Phase 2
0.6053	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7154	Phase 3
0.6038	Remote Similarity	NPD6411	Approved
0.602	Remote Similarity	NPD4271	Approved
0.602	Remote Similarity	NPD4268	Approved
0.6019	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8080	Discontinued
0.6016	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6899	Approved
0.598	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6067	Discontinued
0.5965	Remote Similarity	NPD6402	Approved
0.5965	Remote Similarity	NPD7128	Approved
0.5965	Remote Similarity	NPD6675	Approved
0.5965	Remote Similarity	NPD5739	Approved
0.5943	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5209	Approved
0.5941	Remote Similarity	NPD6435	Approved
0.5926	Remote Similarity	NPD5282	Discontinued
0.5926	Remote Similarity	NPD7748	Approved
0.5922	Remote Similarity	NPD5363	Approved
0.5913	Remote Similarity	NPD5697	Approved
0.5909	Remote Similarity	NPD7902	Approved
0.5906	Remote Similarity	NPD8337	Approved
0.5906	Remote Similarity	NPD8336	Approved
0.5897	Remote Similarity	NPD7102	Approved
0.5897	Remote Similarity	NPD7290	Approved
0.5897	Remote Similarity	NPD6883	Approved
0.5891	Remote Similarity	NPD7260	Phase 2
0.5888	Remote Similarity	NPD7515	Phase 2
0.5882	Remote Similarity	NPD5362	Discontinued
0.5882	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6695	Phase 3
0.5882	Remote Similarity	NPD3669	Approved
0.5872	Remote Similarity	NPD5695	Phase 3
0.587	Remote Similarity	NPD7625	Phase 1
0.5868	Remote Similarity	NPD7500	Approved
0.5862	Remote Similarity	NPD7320	Approved
0.5859	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6847	Approved
0.5847	Remote Similarity	NPD6649	Approved
0.5847	Remote Similarity	NPD6650	Approved
0.5847	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6869	Approved
0.5847	Remote Similarity	NPD8130	Phase 1
0.5847	Remote Similarity	NPD6617	Approved
0.584	Remote Similarity	NPD7604	Phase 2
0.5833	Remote Similarity	NPD6399	Phase 3
0.5826	Remote Similarity	NPD4211	Phase 1
0.5818	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6013	Approved
0.5812	Remote Similarity	NPD6012	Approved
0.5812	Remote Similarity	NPD6373	Approved
0.5812	Remote Similarity	NPD6014	Approved
0.5812	Remote Similarity	NPD6372	Approved
0.5806	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5983	Phase 2
0.5794	Remote Similarity	NPD3168	Discontinued
0.5789	Remote Similarity	NPD1407	Approved
0.5776	Remote Similarity	NPD5701	Approved
0.5748	Remote Similarity	NPD8273	Phase 1
0.5748	Remote Similarity	NPD6336	Discontinued
0.5743	Remote Similarity	NPD5368	Approved
0.5743	Remote Similarity	NPD7332	Phase 2
0.5743	Remote Similarity	NPD7514	Phase 3
0.5738	Remote Similarity	NPD7505	Discontinued
0.5728	Remote Similarity	NPD5332	Approved
0.5728	Remote Similarity	NPD5331	Approved
0.5726	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD8039	Approved
0.5714	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.5692	Remote Similarity	NPD5956	Approved
0.5686	Remote Similarity	NPD5369	Approved
0.5686	Remote Similarity	NPD4790	Discontinued
0.566	Remote Similarity	NPD7750	Discontinued
0.5659	Remote Similarity	NPD6033	Approved
0.5652	Remote Similarity	NPD7266	Discontinued
0.5652	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7900	Approved
0.5635	Remote Similarity	NPD5125	Phase 3
0.5635	Remote Similarity	NPD5126	Approved
0.5631	Remote Similarity	NPD4269	Approved
0.5631	Remote Similarity	NPD4270	Approved
0.563	Remote Similarity	NPD4634	Approved
0.563	Remote Similarity	NPD6421	Discontinued
0.5625	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD1811	Approved
0.5612	Remote Similarity	NPD1810	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