NPASS Compound

Structure

NPC21378 OpenBabel07101718302D 29 30 0 0 0 0 0 0 0 0999 V2000 -1.6762 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5428 -2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3809 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0285 1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7047 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8666 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5428 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0285 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3524 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0285 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3524 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3524 1.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 -2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8666 0.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5143 0.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 -0.0000 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 23 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 29 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	412.395
LogP:	4.241
LogD:	1.686
LogS:	-3.448
# Rotatable Bonds:	6
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	3.228
Fsp3:	0.364
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:	-5.033
MDCK Permeability:	1.1174087376275565e-05
Pgp-inhibitor:	0.767
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.12
20% Bioavailability (F20%):	0.857
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	97.56745910644531%
Volume Distribution (VD):	0.475
Pgp-substrate:	2.963283061981201%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.847
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	4.56
Half-life (T1/2):	0.549

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.927
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.265
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC21378

Natural Product ID:	NPC21378
*Common Name:**	Arzanol
IUPAC Name:	3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methylpyran-2-one
Synonyms:	Arzanol
Standard InCHIKey:	ZOIAPLVBZQQHCG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-6-16-11(4)18(24)15(22(28)29-16)9-14-19(25)13(8-7-10(2)3)20(26)17(12(5)23)21(14)27/h7,24-27H,6,8-9H2,1-5H3
SMILES:	CCc1oc(=O)c(c(c1C)O)Cc1c(O)c(CC=C(C)C)c(c(c1O)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225421
PubChem CID:	54682566
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO32653	helichrysum italicum ssp. microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315926]
NPO25148.1	Helichrysum italicum	Under-species	n.a.	n.a.	Flowered aerial parts	Arzana, Sardinia	2010-Jul	PMID[23265253]

☑ 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	10
MIC	6
Others	3

Activity Type	# Activity
Individual Protein	4
Organism	9
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>=	30000.0	nM	PMID[573271]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[573268]
NPT2	Others	Unspecified		IC50	=	5600.0	nM	PMID[573268]
NPT2	Others	Unspecified		IC50	=	9200.0	nM	PMID[573268]
NPT2	Others	Unspecified		IC50	=	13300.0	nM	PMID[573268]
NPT2	Others	Unspecified		IC50	=	21800.0	nM	PMID[573268]
NPT2	Others	Unspecified		IC50	=	18700.0	nM	PMID[573268]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[573269]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[573269]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[573269]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	400.0	nM	PMID[573270]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	400.0	nM	PMID[573271]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	400.0	nM	PMID[573272]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	59.0	%	PMID[573272]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	48.0	%	PMID[573272]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	47.0	%	PMID[573272]

☑ 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 NPC21378 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	340
0.1-0.2	1610
0.2-0.3	4391
0.3-0.4	10039
0.4-0.5	8900
0.5-0.6	4567
0.6-0.7	5877
0.7-0.8	4690
0.8-0.85	1402
0.85-0.9	771
0.9-0.95	94
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470987
0.984	High Similarity	NPC185624
0.9762	High Similarity	NPC470988
0.9685	High Similarity	NPC470984
0.9462	High Similarity	NPC470989
0.9462	High Similarity	NPC470985
0.9389	High Similarity	NPC474624
0.9389	High Similarity	NPC138047
0.9389	High Similarity	NPC131782
0.9318	High Similarity	NPC219584
0.9318	High Similarity	NPC183639
0.9318	High Similarity	NPC199458
0.9318	High Similarity	NPC470083
0.9248	High Similarity	NPC470986
0.9248	High Similarity	NPC19476
0.9248	High Similarity	NPC241975
0.9213	High Similarity	NPC470981
0.9179	High Similarity	NPC221173
0.9111	High Similarity	NPC470555
0.9104	High Similarity	NPC472343
0.9091	High Similarity	NPC101752
0.9044	High Similarity	NPC470556
0.9044	High Similarity	NPC36181
0.9044	High Similarity	NPC294432
0.9044	High Similarity	NPC112829
0.9023	High Similarity	NPC470982
0.9023	High Similarity	NPC470983
0.9023	High Similarity	NPC174999
0.9008	High Similarity	NPC215875
0.9008	High Similarity	NPC15834
0.8978	High Similarity	NPC184738
0.8978	High Similarity	NPC307895
0.8978	High Similarity	NPC474939
0.8978	High Similarity	NPC112791
0.8978	High Similarity	NPC94794
0.8978	High Similarity	NPC33653
0.8978	High Similarity	NPC196459
0.8978	High Similarity	NPC87609
0.8978	High Similarity	NPC470553
0.8978	High Similarity	NPC470296
0.8978	High Similarity	NPC188632
0.8978	High Similarity	NPC470909
0.8978	High Similarity	NPC96216
0.8947	High Similarity	NPC50455
0.8939	High Similarity	NPC93756
0.8939	High Similarity	NPC16197
0.8939	High Similarity	NPC108113
0.8913	High Similarity	NPC288910
0.8913	High Similarity	NPC178627
0.8913	High Similarity	NPC469935
0.8913	High Similarity	NPC118059
0.8913	High Similarity	NPC469953
0.8913	High Similarity	NPC1886
0.8913	High Similarity	NPC196137
0.8913	High Similarity	NPC470554
0.8913	High Similarity	NPC133060
0.8905	High Similarity	NPC472344
0.8897	High Similarity	NPC16455
0.8897	High Similarity	NPC307990
0.8889	High Similarity	NPC91105
0.8889	High Similarity	NPC112789
0.8889	High Similarity	NPC131130
0.8889	High Similarity	NPC470668
0.8889	High Similarity	NPC19622
0.8889	High Similarity	NPC470669
0.8872	High Similarity	NPC103842
0.8872	High Similarity	NPC125920
0.8864	High Similarity	NPC10971
0.8864	High Similarity	NPC285054
0.8855	High Similarity	NPC250057
0.8849	High Similarity	NPC470322
0.8849	High Similarity	NPC470910
0.8849	High Similarity	NPC154217
0.8849	High Similarity	NPC57470
0.8849	High Similarity	NPC181388
0.8824	High Similarity	NPC217186
0.8824	High Similarity	NPC301217
0.8824	High Similarity	NPC220062
0.8824	High Similarity	NPC55018
0.8824	High Similarity	NPC275903
0.8824	High Similarity	NPC53181
0.8824	High Similarity	NPC96565
0.8824	High Similarity	NPC216978
0.8824	High Similarity	NPC139554
0.8824	High Similarity	NPC303633
0.8824	High Similarity	NPC23257
0.8819	High Similarity	NPC472029
0.8819	High Similarity	NPC65761
0.8815	High Similarity	NPC332594
0.881	High Similarity	NPC215392
0.8806	High Similarity	NPC13575
0.8806	High Similarity	NPC156092
0.8806	High Similarity	NPC60667
0.8797	High Similarity	NPC175943
0.8786	High Similarity	NPC285748
0.8786	High Similarity	NPC140120
0.8786	High Similarity	NPC180477
0.8786	High Similarity	NPC249942
0.8786	High Similarity	NPC297886
0.8779	High Similarity	NPC84772
0.8779	High Similarity	NPC186628
0.8777	High Similarity	NPC71184
0.8777	High Similarity	NPC206212
0.876	High Similarity	NPC267846
0.876	High Similarity	NPC328983
0.8759	High Similarity	NPC270883
0.8759	High Similarity	NPC172986
0.8759	High Similarity	NPC241100
0.8759	High Similarity	NPC261227
0.8759	High Similarity	NPC472603
0.8759	High Similarity	NPC471587
0.8759	High Similarity	NPC159275
0.875	High Similarity	NPC268178
0.875	High Similarity	NPC201395
0.875	High Similarity	NPC180501
0.875	High Similarity	NPC54820
0.875	High Similarity	NPC470672
0.875	High Similarity	NPC254168
0.875	High Similarity	NPC474487
0.875	High Similarity	NPC474504
0.875	High Similarity	NPC272844
0.875	High Similarity	NPC470671
0.875	High Similarity	NPC248995
0.8741	High Similarity	NPC194579
0.8741	High Similarity	NPC41461
0.8741	High Similarity	NPC477243
0.8741	High Similarity	NPC66349
0.8741	High Similarity	NPC249606
0.8741	High Similarity	NPC274109
0.8741	High Similarity	NPC186838
0.8741	High Similarity	NPC12165
0.8741	High Similarity	NPC1486
0.8741	High Similarity	NPC268081
0.8741	High Similarity	NPC25287
0.8741	High Similarity	NPC477244
0.8741	High Similarity	NPC156910
0.8741	High Similarity	NPC98115
0.8741	High Similarity	NPC168105
0.8741	High Similarity	NPC150399
0.8741	High Similarity	NPC477242
0.873	High Similarity	NPC229649
0.873	High Similarity	NPC149246
0.8723	High Similarity	NPC208303
0.8723	High Similarity	NPC469933
0.8723	High Similarity	NPC161864
0.8722	High Similarity	NPC103105
0.8712	High Similarity	NPC5515
0.8712	High Similarity	NPC279566
0.8712	High Similarity	NPC324482
0.8712	High Similarity	NPC270369
0.8702	High Similarity	NPC230818
0.8696	High Similarity	NPC316911
0.8696	High Similarity	NPC156590
0.8696	High Similarity	NPC118840
0.8696	High Similarity	NPC110969
0.8696	High Similarity	NPC282300
0.8696	High Similarity	NPC64908
0.8696	High Similarity	NPC316560
0.8696	High Similarity	NPC147688
0.8696	High Similarity	NPC205006
0.8692	High Similarity	NPC23126
0.8692	High Similarity	NPC98254
0.8692	High Similarity	NPC72158
0.8692	High Similarity	NPC30501
0.8692	High Similarity	NPC190043
0.8692	High Similarity	NPC162612
0.8692	High Similarity	NPC105157
0.8692	High Similarity	NPC329205
0.8692	High Similarity	NPC103356
0.8692	High Similarity	NPC100067
0.8692	High Similarity	NPC266689
0.8692	High Similarity	NPC316625
0.8692	High Similarity	NPC169250
0.8692	High Similarity	NPC116513
0.8686	High Similarity	NPC18260
0.8686	High Similarity	NPC472600
0.8686	High Similarity	NPC78913
0.8686	High Similarity	NPC283429
0.8686	High Similarity	NPC240305
0.8686	High Similarity	NPC472601
0.8682	High Similarity	NPC475733
0.8676	High Similarity	NPC253616
0.8676	High Similarity	NPC255801
0.8676	High Similarity	NPC472419
0.8676	High Similarity	NPC191835
0.8676	High Similarity	NPC317119
0.8676	High Similarity	NPC322301
0.8676	High Similarity	NPC153979
0.8676	High Similarity	NPC38153
0.8667	High Similarity	NPC151113
0.8667	High Similarity	NPC131039
0.8662	High Similarity	NPC469932
0.8662	High Similarity	NPC19238
0.8662	High Similarity	NPC104236
0.8662	High Similarity	NPC164205
0.8661	High Similarity	NPC303737
0.8657	High Similarity	NPC294593
0.8657	High Similarity	NPC159623
0.8657	High Similarity	NPC20560
0.8657	High Similarity	NPC82225

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 NPC21378 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	1002
0.2-0.3	1821
0.3-0.4	2735
0.4-0.5	1829
0.5-0.6	1004
0.6-0.7	308
0.7-0.8	98
0.8-0.85	36
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD6651	Approved
0.8511	High Similarity	NPD2533	Approved
0.8511	High Similarity	NPD4378	Clinical (unspecified phase)
0.8511	High Similarity	NPD2532	Approved
0.8511	High Similarity	NPD7410	Clinical (unspecified phase)
0.8511	High Similarity	NPD2534	Approved
0.8478	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD2800	Approved
0.837	Intermediate Similarity	NPD1240	Approved
0.8288	Intermediate Similarity	NPD7411	Suspended
0.8261	Intermediate Similarity	NPD1510	Phase 2
0.8248	Intermediate Similarity	NPD1607	Approved
0.8156	Intermediate Similarity	NPD1243	Approved
0.8143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7075	Discontinued
0.8108	Intermediate Similarity	NPD6801	Discontinued
0.8095	Intermediate Similarity	NPD4380	Phase 2
0.8085	Intermediate Similarity	NPD1549	Phase 2
0.8056	Intermediate Similarity	NPD6799	Approved
0.8054	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD7819	Suspended
0.7972	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3750	Approved
0.7943	Intermediate Similarity	NPD2796	Approved
0.7943	Intermediate Similarity	NPD2935	Discontinued
0.7933	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6599	Discontinued
0.7829	Intermediate Similarity	NPD7768	Phase 2
0.7826	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1511	Approved
0.7806	Intermediate Similarity	NPD5711	Approved
0.7806	Intermediate Similarity	NPD5710	Approved
0.7786	Intermediate Similarity	NPD9545	Approved
0.777	Intermediate Similarity	NPD920	Approved
0.7769	Intermediate Similarity	NPD9493	Approved
0.7746	Intermediate Similarity	NPD2799	Discontinued
0.774	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD943	Approved
0.7703	Intermediate Similarity	NPD1512	Approved
0.7698	Intermediate Similarity	NPD2313	Discontinued
0.7697	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD6232	Discontinued
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.7687	Intermediate Similarity	NPD422	Phase 1
0.7687	Intermediate Similarity	NPD7390	Discontinued
0.7662	Intermediate Similarity	NPD3749	Approved
0.7662	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD230	Phase 1
0.766	Intermediate Similarity	NPD5124	Phase 1
0.766	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7473	Discontinued
0.7647	Intermediate Similarity	NPD3817	Phase 2
0.7635	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1934	Approved
0.763	Intermediate Similarity	NPD9717	Approved
0.7622	Intermediate Similarity	NPD3748	Approved
0.7594	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1164	Approved
0.7591	Intermediate Similarity	NPD1203	Approved
0.7578	Intermediate Similarity	NPD5953	Discontinued
0.7569	Intermediate Similarity	NPD5404	Approved
0.7569	Intermediate Similarity	NPD5408	Approved
0.7569	Intermediate Similarity	NPD5406	Approved
0.7569	Intermediate Similarity	NPD5405	Approved
0.7562	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7286	Phase 2
0.7533	Intermediate Similarity	NPD5403	Approved
0.7516	Intermediate Similarity	NPD6959	Discontinued
0.7484	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3268	Approved
0.7422	Intermediate Similarity	NPD74	Approved
0.7422	Intermediate Similarity	NPD9266	Approved
0.7415	Intermediate Similarity	NPD2654	Approved
0.74	Intermediate Similarity	NPD5401	Approved
0.7389	Intermediate Similarity	NPD919	Approved
0.7372	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9267	Approved
0.7344	Intermediate Similarity	NPD9263	Approved
0.7344	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9264	Approved
0.7338	Intermediate Similarity	NPD2797	Approved
0.7324	Intermediate Similarity	NPD1296	Phase 2
0.7324	Intermediate Similarity	NPD3764	Approved
0.732	Intermediate Similarity	NPD3226	Approved
0.7305	Intermediate Similarity	NPD6832	Phase 2
0.7286	Intermediate Similarity	NPD2798	Approved
0.7284	Intermediate Similarity	NPD3818	Discontinued
0.7279	Intermediate Similarity	NPD2344	Approved
0.7279	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6166	Phase 2
0.726	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7246	Intermediate Similarity	NPD9269	Phase 2
0.7239	Intermediate Similarity	NPD7054	Approved
0.7212	Intermediate Similarity	NPD6559	Discontinued
0.7211	Intermediate Similarity	NPD6099	Approved
0.7211	Intermediate Similarity	NPD6100	Approved
0.7206	Intermediate Similarity	NPD9268	Approved
0.7197	Intermediate Similarity	NPD5402	Approved
0.7195	Intermediate Similarity	NPD7472	Approved
0.7195	Intermediate Similarity	NPD7074	Phase 3
0.7174	Intermediate Similarity	NPD1201	Approved
0.7169	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD3225	Approved
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD5494	Approved
0.7108	Intermediate Similarity	NPD7251	Discontinued
0.7092	Intermediate Similarity	NPD3266	Approved
0.7092	Intermediate Similarity	NPD3267	Approved
0.7092	Intermediate Similarity	NPD1470	Approved
0.709	Intermediate Similarity	NPD9281	Approved
0.7087	Intermediate Similarity	NPD940	Approved
0.7087	Intermediate Similarity	NPD846	Approved
0.7086	Intermediate Similarity	NPD2309	Approved
0.7083	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7808	Phase 3
0.7055	Intermediate Similarity	NPD447	Suspended
0.7031	Intermediate Similarity	NPD9261	Approved
0.7025	Intermediate Similarity	NPD1465	Phase 2
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1608	Approved
0.6987	Remote Similarity	NPD7458	Discontinued
0.6981	Remote Similarity	NPD4288	Approved
0.6975	Remote Similarity	NPD1247	Approved
0.6966	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6585	Discontinued
0.6923	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1019	Discontinued
0.6918	Remote Similarity	NPD520	Approved
0.6908	Remote Similarity	NPD7003	Approved
0.6903	Remote Similarity	NPD5049	Phase 3
0.6899	Remote Similarity	NPD5889	Approved
0.6899	Remote Similarity	NPD5890	Approved
0.6894	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1729	Discontinued
0.6884	Remote Similarity	NPD1548	Phase 1
0.6883	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3972	Approved
0.6871	Remote Similarity	NPD4307	Phase 2
0.6861	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4360	Phase 2
0.6857	Remote Similarity	NPD4363	Phase 3
0.6849	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4908	Phase 1
0.6824	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1933	Approved
0.6821	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6005	Phase 3
0.6821	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4287	Approved
0.6821	Remote Similarity	NPD6002	Phase 3
0.6821	Remote Similarity	NPD6004	Phase 3
0.6818	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4361	Phase 2
0.6809	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3926	Phase 2
0.6786	Remote Similarity	NPD4626	Approved
0.6786	Remote Similarity	NPD17	Approved
0.6761	Remote Similarity	NPD1481	Phase 2
0.6753	Remote Similarity	NPD6190	Approved
0.6753	Remote Similarity	NPD2354	Approved
0.6735	Remote Similarity	NPD6798	Discontinued
0.6732	Remote Similarity	NPD1652	Phase 2
0.6731	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7229	Phase 3
0.6718	Remote Similarity	NPD5909	Discontinued
0.6716	Remote Similarity	NPD4750	Phase 3
0.6713	Remote Similarity	NPD4749	Approved
0.6706	Remote Similarity	NPD6104	Discontinued
0.6705	Remote Similarity	NPD8150	Discontinued
0.669	Remote Similarity	NPD1535	Discovery
0.669	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2403	Approved
0.6647	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6234	Discontinued

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