NPASS Compound

Structure

NPC17585 OpenBabel07101718192D 32 34 0 0 1 0 0 0 0 0999 V2000 -6.4187 -4.4396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3220 -1.7373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4722 -1.7624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9736 -0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0216 1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9327 -2.0210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7364 -2.9448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5486 -1.1582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0953 -3.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0345 -3.5768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9539 -2.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5287 0.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7307 -0.6860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2773 -3.2033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8932 -2.3405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7914 -0.7847 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0896 -1.4167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7576 -3.3630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9271 0.2378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 -0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8179 -0.4722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1446 1.1383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8948 -3.7471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2252 0.8698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 -1.8889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8253 0.5297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4073 0.0781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5755 -3.8352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4537 -0.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 15 2 0 0 0 0 10 11 2 0 0 0 0 12 20 1 0 0 0 0 13 23 1 6 0 0 0 13 32 1 0 0 0 0 14 24 2 0 0 0 0 14 29 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 10 1 6 0 0 0 16 17 1 0 0 0 0 16 30 1 0 0 0 0 17 12 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 6 0 0 0 19 31 1 1 0 0 0 20 25 2 0 0 0 0 20 30 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 27 2 0 0 0 0 22 31 1 0 0 0 0 23 5 1 1 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.17
Volume:	441.352
LogP:	2.185
LogD:	1.259
LogS:	-3.473
# Rotatable Bonds:	7
TPSA:	117.73
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	5.42
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.116
MDCK Permeability:	7.537019700976089e-05
Pgp-inhibitor:	0.69
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.495
20% Bioavailability (F20%):	0.772
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.837
Plasma Protein Binding (PPB):	64.36844635009766%
Volume Distribution (VD):	1.272
Pgp-substrate:	45.28813552856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.264
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	7.132
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.817
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.424
Maximum Recommended Daily Dose:	0.185
Skin Sensitization:	0.303
Carcinogencity:	0.038
Eye Corrosion:	0.018
Eye Irritation:	0.035
Respiratory Toxicity:	0.82

Download Data

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

Natural Product: NPC17585

Natural Product ID:	NPC17585
*Common Name:**	Uvedalin
IUPAC Name:	methyl (3aS,4S,5S,6E,10E,11aR)-5-acetyloxy-4-[(2R,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
Synonyms:
Standard InCHIKey:	JIEVJXRUYDZFTD-CVQTXJQTSA-N
Standard InCHI:	InChI=1S/C23H28O9/c1-11-8-7-9-15(21(26)28-6)18(29-14(4)24)19(31-22(27)23(5)13(3)32-23)17-12(2)20(25)30-16(17)10-11/h9-10,13,16-19H,2,7-8H2,1,3-6H3/b11-10+,15-9+/t13-,16-,17+,18+,19+,23-/m1/s1
SMILES:	COC(=O)/C/1=C/CC/C(=C/[C@@H]2[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)[C@]1(C)O[C@@H]1C)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380784
PubChem CID:	73353398
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides 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
NPO24243	Smallanthus sonchifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO24243	Smallanthus sonchifolius	Species	Asteraceae	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	3837.07	nM	PMID[515659]
NPT27	Others	Unspecified		IC50	=	11420.0	nM	PMID[515659]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	3830.0	nM	PMID[515659]

☑ 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 NPC17585 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	271
0.1-0.2	1857
0.2-0.3	6215
0.3-0.4	11445
0.4-0.5	13488
0.5-0.6	6028
0.6-0.7	2626
0.7-0.8	599
0.8-0.85	104
0.85-0.9	48
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC477512
0.957	High Similarity	NPC264477
0.957	High Similarity	NPC477511
0.9271	High Similarity	NPC477510
0.9271	High Similarity	NPC471143
0.9255	High Similarity	NPC475949
0.9247	High Similarity	NPC471140
0.9149	High Similarity	NPC471144
0.9101	High Similarity	NPC266957
0.9082	High Similarity	NPC477513
0.9022	High Similarity	NPC165383
0.8958	High Similarity	NPC474339
0.8958	High Similarity	NPC164598
0.8925	High Similarity	NPC473316
0.8925	High Similarity	NPC471147
0.8925	High Similarity	NPC140543
0.8925	High Similarity	NPC473330
0.8913	High Similarity	NPC20713
0.8901	High Similarity	NPC166919
0.8901	High Similarity	NPC151770
0.8866	High Similarity	NPC149371
0.8854	High Similarity	NPC288876
0.883	High Similarity	NPC475659
0.883	High Similarity	NPC471142
0.8804	High Similarity	NPC475748
0.8763	High Similarity	NPC201718
0.8763	High Similarity	NPC47880
0.875	High Similarity	NPC208233
0.8737	High Similarity	NPC473859
0.8737	High Similarity	NPC35498
0.8723	High Similarity	NPC476267
0.8681	High Similarity	NPC231889
0.8673	High Similarity	NPC471148
0.8587	High Similarity	NPC475902
0.8571	High Similarity	NPC50637
0.8542	High Similarity	NPC230800
0.8542	High Similarity	NPC279621
0.8542	High Similarity	NPC476275
0.85	High Similarity	NPC474741
0.8462	Intermediate Similarity	NPC319795
0.8462	Intermediate Similarity	NPC50362
0.8462	Intermediate Similarity	NPC38468
0.8438	Intermediate Similarity	NPC477922
0.8404	Intermediate Similarity	NPC312042
0.8404	Intermediate Similarity	NPC473619
0.8404	Intermediate Similarity	NPC329857
0.8404	Intermediate Similarity	NPC469718
0.8404	Intermediate Similarity	NPC251385
0.8404	Intermediate Similarity	NPC49342
0.84	Intermediate Similarity	NPC474166
0.84	Intermediate Similarity	NPC19239
0.8384	Intermediate Similarity	NPC476270
0.8367	Intermediate Similarity	NPC473326
0.8367	Intermediate Similarity	NPC279561
0.8351	Intermediate Similarity	NPC477921
0.8351	Intermediate Similarity	NPC476315
0.8333	Intermediate Similarity	NPC474247
0.8333	Intermediate Similarity	NPC57405
0.8333	Intermediate Similarity	NPC474716
0.8333	Intermediate Similarity	NPC303942
0.8316	Intermediate Similarity	NPC473321
0.8298	Intermediate Similarity	NPC475971
0.828	Intermediate Similarity	NPC475703
0.8247	Intermediate Similarity	NPC471141
0.8247	Intermediate Similarity	NPC270013
0.8247	Intermediate Similarity	NPC14961
0.8247	Intermediate Similarity	NPC474947
0.8242	Intermediate Similarity	NPC272814
0.8235	Intermediate Similarity	NPC9303
0.8235	Intermediate Similarity	NPC16313
0.8235	Intermediate Similarity	NPC475802
0.8229	Intermediate Similarity	NPC212486
0.8229	Intermediate Similarity	NPC476300
0.8229	Intermediate Similarity	NPC125674
0.8229	Intermediate Similarity	NPC228451
0.8229	Intermediate Similarity	NPC475838
0.8218	Intermediate Similarity	NPC472755
0.8218	Intermediate Similarity	NPC475945
0.8218	Intermediate Similarity	NPC475871
0.82	Intermediate Similarity	NPC15993
0.82	Intermediate Similarity	NPC474742
0.8191	Intermediate Similarity	NPC287089
0.819	Intermediate Similarity	NPC475495
0.8172	Intermediate Similarity	NPC204048
0.8155	Intermediate Similarity	NPC72813
0.8155	Intermediate Similarity	NPC194620
0.8155	Intermediate Similarity	NPC475587
0.8155	Intermediate Similarity	NPC324327
0.8155	Intermediate Similarity	NPC474421
0.8155	Intermediate Similarity	NPC326994
0.8155	Intermediate Similarity	NPC475510
0.8144	Intermediate Similarity	NPC81386
0.8144	Intermediate Similarity	NPC474035
0.8119	Intermediate Similarity	NPC472754
0.8119	Intermediate Similarity	NPC320019
0.8119	Intermediate Similarity	NPC474747
0.8119	Intermediate Similarity	NPC324017
0.8113	Intermediate Similarity	NPC475277
0.8113	Intermediate Similarity	NPC477093
0.8113	Intermediate Similarity	NPC473522
0.81	Intermediate Similarity	NPC469551
0.8085	Intermediate Similarity	NPC5130
0.8077	Intermediate Similarity	NPC14862
0.8077	Intermediate Similarity	NPC473939
0.8077	Intermediate Similarity	NPC55972
0.8077	Intermediate Similarity	NPC327286
0.8077	Intermediate Similarity	NPC169888
0.8077	Intermediate Similarity	NPC233379
0.8077	Intermediate Similarity	NPC474664
0.8077	Intermediate Similarity	NPC473595
0.8061	Intermediate Similarity	NPC36954
0.8041	Intermediate Similarity	NPC295204
0.8041	Intermediate Similarity	NPC288240
0.8041	Intermediate Similarity	NPC475912
0.8041	Intermediate Similarity	NPC162205
0.8041	Intermediate Similarity	NPC273579
0.8022	Intermediate Similarity	NPC141810
0.8021	Intermediate Similarity	NPC179394
0.8021	Intermediate Similarity	NPC62815
0.8021	Intermediate Similarity	NPC144133
0.8021	Intermediate Similarity	NPC474232
0.8021	Intermediate Similarity	NPC475855
0.8021	Intermediate Similarity	NPC51004
0.802	Intermediate Similarity	NPC185141
0.802	Intermediate Similarity	NPC133907
0.802	Intermediate Similarity	NPC472753
0.802	Intermediate Similarity	NPC110443
0.802	Intermediate Similarity	NPC128733
0.802	Intermediate Similarity	NPC46998
0.8	Intermediate Similarity	NPC15218
0.8	Intermediate Similarity	NPC469631
0.8	Intermediate Similarity	NPC475906
0.8	Intermediate Similarity	NPC473715
0.8	Intermediate Similarity	NPC474213
0.8	Intermediate Similarity	NPC475922
0.8	Intermediate Similarity	NPC38154
0.8	Intermediate Similarity	NPC471047
0.8	Intermediate Similarity	NPC475819
0.8	Intermediate Similarity	NPC469653
0.8	Intermediate Similarity	NPC469628
0.8	Intermediate Similarity	NPC270126
0.7982	Intermediate Similarity	NPC471146
0.7981	Intermediate Similarity	NPC469558
0.798	Intermediate Similarity	NPC76862
0.798	Intermediate Similarity	NPC470883
0.798	Intermediate Similarity	NPC158416
0.798	Intermediate Similarity	NPC39859
0.7978	Intermediate Similarity	NPC141789
0.7978	Intermediate Similarity	NPC476028
0.7978	Intermediate Similarity	NPC171204
0.7961	Intermediate Similarity	NPC472756
0.7959	Intermediate Similarity	NPC190294
0.7938	Intermediate Similarity	NPC30515
0.7938	Intermediate Similarity	NPC184463
0.7925	Intermediate Similarity	NPC161816
0.7925	Intermediate Similarity	NPC473975
0.7925	Intermediate Similarity	NPC473843
0.7925	Intermediate Similarity	NPC115257
0.7925	Intermediate Similarity	NPC474586
0.7925	Intermediate Similarity	NPC281624
0.7925	Intermediate Similarity	NPC473594
0.7917	Intermediate Similarity	NPC307411
0.7917	Intermediate Similarity	NPC474032
0.7912	Intermediate Similarity	NPC281132
0.7895	Intermediate Similarity	NPC471739
0.7885	Intermediate Similarity	NPC223450
0.7872	Intermediate Similarity	NPC474547
0.7872	Intermediate Similarity	NPC470755
0.7864	Intermediate Similarity	NPC4620
0.7864	Intermediate Similarity	NPC475873
0.7857	Intermediate Similarity	NPC179746
0.7857	Intermediate Similarity	NPC81419
0.7857	Intermediate Similarity	NPC475302
0.785	Intermediate Similarity	NPC194619
0.7849	Intermediate Similarity	NPC474703
0.7849	Intermediate Similarity	NPC128429
0.7835	Intermediate Similarity	NPC80875
0.783	Intermediate Similarity	NPC471934
0.7826	Intermediate Similarity	NPC207188
0.7818	Intermediate Similarity	NPC475305
0.7812	Intermediate Similarity	NPC202672
0.7812	Intermediate Similarity	NPC476805
0.781	Intermediate Similarity	NPC26617
0.7802	Intermediate Similarity	NPC617
0.78	Intermediate Similarity	NPC172998
0.78	Intermediate Similarity	NPC31645
0.78	Intermediate Similarity	NPC301596
0.78	Intermediate Similarity	NPC476009
0.78	Intermediate Similarity	NPC299396
0.7789	Intermediate Similarity	NPC279859
0.7789	Intermediate Similarity	NPC469910
0.7789	Intermediate Similarity	NPC475491
0.7789	Intermediate Similarity	NPC38576
0.7789	Intermediate Similarity	NPC469626
0.7789	Intermediate Similarity	NPC284902
0.7788	Intermediate Similarity	NPC220964
0.7788	Intermediate Similarity	NPC100487
0.7788	Intermediate Similarity	NPC475676
0.7778	Intermediate Similarity	NPC121825
0.7778	Intermediate Similarity	NPC473877

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 NPC17585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	2481
0.2-0.3	3858
0.3-0.4	1713
0.4-0.5	590
0.5-0.6	226
0.6-0.7	31
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6698	Approved
0.7475	Intermediate Similarity	NPD46	Approved
0.7374	Intermediate Similarity	NPD1695	Approved
0.7129	Intermediate Similarity	NPD7838	Discovery
0.7117	Intermediate Similarity	NPD6371	Approved
0.7059	Intermediate Similarity	NPD7983	Approved
0.7019	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5282	Discontinued
0.6754	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD5209	Approved
0.6491	Remote Similarity	NPD6686	Approved
0.6462	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6008	Approved
0.6455	Remote Similarity	NPD6648	Approved
0.6446	Remote Similarity	NPD6319	Approved
0.6423	Remote Similarity	NPD7642	Approved
0.6396	Remote Similarity	NPD5344	Discontinued
0.6393	Remote Similarity	NPD8517	Approved
0.6393	Remote Similarity	NPD8513	Phase 3
0.6393	Remote Similarity	NPD8515	Approved
0.6393	Remote Similarity	NPD8516	Approved
0.6379	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5778	Approved
0.6355	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7115	Discovery
0.6321	Remote Similarity	NPD5785	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.629	Remote Similarity	NPD7829	Approved
0.629	Remote Similarity	NPD7830	Approved
0.6271	Remote Similarity	NPD6053	Discontinued
0.624	Remote Similarity	NPD7492	Approved
0.619	Remote Similarity	NPD6616	Approved
0.6186	Remote Similarity	NPD2204	Approved
0.6182	Remote Similarity	NPD7839	Suspended
0.6179	Remote Similarity	NPD6054	Approved
0.6154	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7078	Approved
0.6142	Remote Similarity	NPD8074	Phase 3
0.6134	Remote Similarity	NPD8297	Approved
0.6129	Remote Similarity	NPD6015	Approved
0.6129	Remote Similarity	NPD6016	Approved
0.6117	Remote Similarity	NPD6110	Phase 1
0.6095	Remote Similarity	NPD5786	Approved
0.6095	Remote Similarity	NPD4249	Approved
0.6094	Remote Similarity	NPD7736	Approved
0.608	Remote Similarity	NPD5988	Approved
0.608	Remote Similarity	NPD6370	Approved
0.6077	Remote Similarity	NPD7260	Phase 2
0.6068	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6650	Approved
0.605	Remote Similarity	NPD6649	Approved
0.6048	Remote Similarity	NPD6059	Approved
0.6047	Remote Similarity	NPD7319	Approved
0.6038	Remote Similarity	NPD4250	Approved
0.6038	Remote Similarity	NPD4251	Approved
0.6032	Remote Similarity	NPD8328	Phase 3
0.6017	Remote Similarity	NPD6373	Approved
0.6017	Remote Similarity	NPD6372	Approved
0.6016	Remote Similarity	NPD8293	Discontinued
0.5983	Remote Similarity	NPD5697	Approved
0.5966	Remote Similarity	NPD2067	Discontinued
0.5963	Remote Similarity	NPD5693	Phase 1
0.5962	Remote Similarity	NPD7154	Phase 3
0.5952	Remote Similarity	NPD8080	Discontinued
0.595	Remote Similarity	NPD4632	Approved
0.5938	Remote Similarity	NPD8451	Approved
0.5938	Remote Similarity	NPD8273	Phase 1
0.5938	Remote Similarity	NPD7507	Approved
0.5935	Remote Similarity	NPD6009	Approved
0.5932	Remote Similarity	NPD6881	Approved
0.5932	Remote Similarity	NPD6899	Approved
0.5926	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6101	Approved
0.5922	Remote Similarity	NPD5369	Approved
0.5909	Remote Similarity	NPD6845	Suspended
0.5906	Remote Similarity	NPD7604	Phase 2
0.5897	Remote Similarity	NPD6675	Approved
0.5897	Remote Similarity	NPD5739	Approved
0.5897	Remote Similarity	NPD6402	Approved
0.5897	Remote Similarity	NPD7128	Approved
0.5891	Remote Similarity	NPD8448	Approved
0.5882	Remote Similarity	NPD6013	Approved
0.5882	Remote Similarity	NPD6012	Approved
0.5882	Remote Similarity	NPD6014	Approved
0.5873	Remote Similarity	NPD5983	Phase 2
0.5868	Remote Similarity	NPD6882	Approved
0.5865	Remote Similarity	NPD6435	Approved
0.5865	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4269	Approved
0.5865	Remote Similarity	NPD4270	Approved
0.5847	Remote Similarity	NPD5701	Approved
0.5842	Remote Similarity	NPD4756	Discovery
0.5833	Remote Similarity	NPD7290	Approved
0.5833	Remote Similarity	NPD7102	Approved
0.5833	Remote Similarity	NPD5737	Approved
0.5833	Remote Similarity	NPD6672	Approved
0.5833	Remote Similarity	NPD6883	Approved
0.5825	Remote Similarity	NPD4252	Approved
0.5825	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6411	Approved
0.5806	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5695	Phase 3
0.5798	Remote Similarity	NPD7320	Approved
0.5798	Remote Similarity	NPD6011	Approved
0.5789	Remote Similarity	NPD7638	Approved
0.5789	Remote Similarity	NPD5696	Approved
0.5785	Remote Similarity	NPD6847	Approved
0.5785	Remote Similarity	NPD8130	Phase 1
0.5785	Remote Similarity	NPD6617	Approved
0.5785	Remote Similarity	NPD6869	Approved
0.576	Remote Similarity	NPD7641	Discontinued
0.5758	Remote Similarity	NPD8391	Approved
0.5758	Remote Similarity	NPD8390	Approved
0.5758	Remote Similarity	NPD8392	Approved
0.5748	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD8444	Approved
0.5739	Remote Similarity	NPD7639	Approved
0.5739	Remote Similarity	NPD7640	Approved
0.5736	Remote Similarity	NPD8341	Approved
0.5736	Remote Similarity	NPD8299	Approved
0.5736	Remote Similarity	NPD8340	Approved
0.5736	Remote Similarity	NPD8342	Approved
0.5702	Remote Similarity	NPD6083	Phase 2
0.5702	Remote Similarity	NPD6084	Phase 2
0.5702	Remote Similarity	NPD4634	Approved
0.5701	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6336	Discontinued
0.568	Remote Similarity	NPD7500	Approved
0.5673	Remote Similarity	NPD5368	Approved
0.5673	Remote Similarity	NPD4822	Approved
0.5673	Remote Similarity	NPD4821	Approved
0.5673	Remote Similarity	NPD4820	Approved
0.5673	Remote Similarity	NPD4819	Approved
0.5662	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5362	Discontinued
0.5644	Remote Similarity	NPD8039	Approved
0.5636	Remote Similarity	NPD6080	Approved
0.5636	Remote Similarity	NPD6904	Approved
0.5636	Remote Similarity	NPD6673	Approved
0.5631	Remote Similarity	NPD4268	Approved
0.5631	Remote Similarity	NPD4271	Approved
0.5625	Remote Similarity	NPD6921	Approved
0.5606	Remote Similarity	NPD6033	Approved
0.56	Remote Similarity	NPD6274	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