NPASS Compound

Structure

NPC470981 OpenBabel07101718292D 30 31 0 0 0 0 0 0 0 0999 V2000 -1.6779 -0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3896 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2286 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8727 -3.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5507 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7117 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3896 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0338 -2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8727 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1948 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0338 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0338 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8727 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1948 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1948 -3.3906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0338 0.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7117 -1.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3558 -1.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 1.4531 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 7 1 0 0 0 0 2 11 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 29 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 24 2 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	406.475
LogP:	3.967
LogD:	2.028
LogS:	-3.27
# Rotatable Bonds:	4
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	3.305
Fsp3:	0.455
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:	-4.871
MDCK Permeability:	2.1110899979248643e-05
Pgp-inhibitor:	0.214
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.24808502197266%
Volume Distribution (VD):	0.349
Pgp-substrate:	1.361962914466858%

ADMET: Metabolism

CYP1A2-inhibitor:	0.228
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.216
CYP2C9-inhibitor:	0.747
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	1.778
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.908
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.155
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC470981

Natural Product ID:	NPC470981
*Common Name:**	Methylarzanol
IUPAC Name:	5-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-2-ethyl-6-methoxy-3-methylpyran-4-one
Synonyms:	Methylarzanol
Standard InCHIKey:	PBPNYHLWMORBRT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H28O7/c1-7-17-12(4)19(25)16(23(29-6)30-17)10-15-20(26)14(9-8-11(2)3)21(27)18(13(5)24)22(15)28/h8,26-28H,7,9-10H2,1-6H3
SMILES:	COc1oc(CC)c(c(=O)c1Cc1c(O)c(CC=C(C)C)c(c(c1O)C(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334813
PubChem CID:	16215412
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
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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[537651]

☑ 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 NPC470981 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	335
0.1-0.2	1525
0.2-0.3	4060
0.3-0.4	9171
0.4-0.5	9906
0.5-0.6	4231
0.6-0.7	6118
0.7-0.8	5036
0.8-0.85	1600
0.85-0.9	668
0.9-0.95	46
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC21378
0.9213	High Similarity	NPC470987
0.907	High Similarity	NPC185624
0.9032	High Similarity	NPC91105
0.9008	High Similarity	NPC470210
0.9	High Similarity	NPC470988
0.896	High Similarity	NPC65761
0.896	High Similarity	NPC472029
0.8952	High Similarity	NPC215392
0.8931	High Similarity	NPC470984
0.8898	High Similarity	NPC267846
0.8898	High Similarity	NPC328983
0.8871	High Similarity	NPC229649
0.8871	High Similarity	NPC149246
0.8855	High Similarity	NPC215875
0.8855	High Similarity	NPC15834
0.8828	High Similarity	NPC98254
0.8828	High Similarity	NPC72158
0.8828	High Similarity	NPC23126
0.8828	High Similarity	NPC162612
0.8828	High Similarity	NPC266689
0.8828	High Similarity	NPC190043
0.8828	High Similarity	NPC316625
0.8828	High Similarity	NPC116513
0.8828	High Similarity	NPC103356
0.8828	High Similarity	NPC169250
0.8828	High Similarity	NPC105157
0.8828	High Similarity	NPC30501
0.8828	High Similarity	NPC100067
0.8828	High Similarity	NPC329205
0.8819	High Similarity	NPC475733
0.88	High Similarity	NPC303737
0.8797	High Similarity	NPC101752
0.8788	High Similarity	NPC16197
0.876	High Similarity	NPC21305
0.876	High Similarity	NPC221777
0.876	High Similarity	NPC473017
0.875	High Similarity	NPC62952
0.8731	High Similarity	NPC470985
0.8731	High Similarity	NPC174999
0.8731	High Similarity	NPC470989
0.873	High Similarity	NPC232708
0.873	High Similarity	NPC309765
0.873	High Similarity	NPC66252
0.8722	High Similarity	NPC103842
0.8712	High Similarity	NPC285054
0.8702	High Similarity	NPC475042
0.8702	High Similarity	NPC275504
0.8702	High Similarity	NPC250057
0.8692	High Similarity	NPC476119
0.8692	High Similarity	NPC474998
0.8667	High Similarity	NPC474624
0.8667	High Similarity	NPC131782
0.8667	High Similarity	NPC138047
0.8657	High Similarity	NPC156092
0.8657	High Similarity	NPC13575
0.8657	High Similarity	NPC131039
0.8651	High Similarity	NPC226275
0.864	High Similarity	NPC294037
0.8629	High Similarity	NPC209486
0.8629	High Similarity	NPC40649
0.8626	High Similarity	NPC186628
0.8626	High Similarity	NPC84772
0.8623	High Similarity	NPC266725
0.8603	High Similarity	NPC470083
0.8603	High Similarity	NPC183639
0.8603	High Similarity	NPC199458
0.8603	High Similarity	NPC131130
0.8603	High Similarity	NPC219584
0.8593	High Similarity	NPC1486
0.8593	High Similarity	NPC41461
0.8593	High Similarity	NPC25287
0.8593	High Similarity	NPC150399
0.8593	High Similarity	NPC477243
0.8593	High Similarity	NPC249606
0.8593	High Similarity	NPC12165
0.8593	High Similarity	NPC98115
0.8593	High Similarity	NPC168105
0.8593	High Similarity	NPC186838
0.8593	High Similarity	NPC477242
0.8593	High Similarity	NPC477244
0.8593	High Similarity	NPC274109
0.8593	High Similarity	NPC66349
0.8582	High Similarity	NPC125920
0.8571	High Similarity	NPC40524
0.8571	High Similarity	NPC139074
0.8571	High Similarity	NPC146642
0.8571	High Similarity	NPC103105
0.8571	High Similarity	NPC213485
0.8561	High Similarity	NPC324482
0.8561	High Similarity	NPC279566
0.855	High Similarity	NPC230818
0.854	High Similarity	NPC241975
0.854	High Similarity	NPC470986
0.854	High Similarity	NPC217186
0.854	High Similarity	NPC23257
0.854	High Similarity	NPC53181
0.854	High Similarity	NPC139554
0.854	High Similarity	NPC283429
0.854	High Similarity	NPC19476
0.8529	High Similarity	NPC322301
0.8529	High Similarity	NPC153979
0.8529	High Similarity	NPC317119
0.8529	High Similarity	NPC255801
0.8529	High Similarity	NPC472419
0.8527	High Similarity	NPC290466
0.8519	High Similarity	NPC60667
0.8516	High Similarity	NPC306288
0.8507	High Similarity	NPC108113
0.8507	High Similarity	NPC93756
0.8507	High Similarity	NPC18877
0.8507	High Similarity	NPC82225
0.8507	High Similarity	NPC28753
0.8507	High Similarity	NPC294593
0.8507	High Similarity	NPC204960
0.8507	High Similarity	NPC159623
0.8507	High Similarity	NPC144051
0.8507	High Similarity	NPC20560
0.8504	High Similarity	NPC196976
0.8504	High Similarity	NPC242895
0.8496	Intermediate Similarity	NPC27490
0.8489	Intermediate Similarity	NPC112829
0.8489	Intermediate Similarity	NPC470556
0.8489	Intermediate Similarity	NPC294432
0.8478	Intermediate Similarity	NPC159275
0.8478	Intermediate Similarity	NPC471587
0.8478	Intermediate Similarity	NPC241100
0.8478	Intermediate Similarity	NPC213659
0.8478	Intermediate Similarity	NPC80962
0.8478	Intermediate Similarity	NPC144118
0.8478	Intermediate Similarity	NPC204985
0.8478	Intermediate Similarity	NPC172250
0.8478	Intermediate Similarity	NPC215311
0.8478	Intermediate Similarity	NPC326109
0.8478	Intermediate Similarity	NPC219917
0.8478	Intermediate Similarity	NPC253822
0.8478	Intermediate Similarity	NPC48624
0.8478	Intermediate Similarity	NPC259166
0.8478	Intermediate Similarity	NPC221173
0.8467	Intermediate Similarity	NPC243528
0.8467	Intermediate Similarity	NPC477055
0.8467	Intermediate Similarity	NPC470668
0.8467	Intermediate Similarity	NPC272844
0.8467	Intermediate Similarity	NPC19622
0.8467	Intermediate Similarity	NPC254168
0.8467	Intermediate Similarity	NPC248995
0.8467	Intermediate Similarity	NPC470669
0.8467	Intermediate Similarity	NPC251681
0.8467	Intermediate Similarity	NPC471620
0.8467	Intermediate Similarity	NPC112789
0.8467	Intermediate Similarity	NPC21350
0.8467	Intermediate Similarity	NPC477056
0.8462	Intermediate Similarity	NPC38775
0.8456	Intermediate Similarity	NPC156910
0.8444	Intermediate Similarity	NPC70859
0.8444	Intermediate Similarity	NPC130899
0.8444	Intermediate Similarity	NPC61153
0.8444	Intermediate Similarity	NPC164136
0.8444	Intermediate Similarity	NPC286336
0.8444	Intermediate Similarity	NPC283590
0.8438	Intermediate Similarity	NPC32032
0.8438	Intermediate Similarity	NPC218333
0.8438	Intermediate Similarity	NPC133909
0.8433	Intermediate Similarity	NPC10971
0.8429	Intermediate Similarity	NPC33653
0.8429	Intermediate Similarity	NPC470553
0.8429	Intermediate Similarity	NPC131043
0.8429	Intermediate Similarity	NPC474939
0.8429	Intermediate Similarity	NPC313039
0.8429	Intermediate Similarity	NPC473976
0.8429	Intermediate Similarity	NPC307895
0.8429	Intermediate Similarity	NPC470909
0.8429	Intermediate Similarity	NPC184738
0.8429	Intermediate Similarity	NPC96216
0.8429	Intermediate Similarity	NPC198459
0.8429	Intermediate Similarity	NPC109812
0.8417	Intermediate Similarity	NPC26051
0.8417	Intermediate Similarity	NPC268204
0.8417	Intermediate Similarity	NPC52789
0.8417	Intermediate Similarity	NPC469404
0.8417	Intermediate Similarity	NPC282300
0.8417	Intermediate Similarity	NPC55832
0.8417	Intermediate Similarity	NPC470555
0.8417	Intermediate Similarity	NPC110969
0.8413	Intermediate Similarity	NPC161617
0.8409	Intermediate Similarity	NPC69235
0.8409	Intermediate Similarity	NPC212379
0.8406	Intermediate Similarity	NPC301217
0.8406	Intermediate Similarity	NPC295384
0.8406	Intermediate Similarity	NPC18260
0.8406	Intermediate Similarity	NPC472343
0.8406	Intermediate Similarity	NPC240305
0.8406	Intermediate Similarity	NPC55018
0.8406	Intermediate Similarity	NPC303633
0.8406	Intermediate Similarity	NPC275903
0.8406	Intermediate Similarity	NPC78913
0.8406	Intermediate Similarity	NPC477956
0.8406	Intermediate Similarity	NPC216978
0.8406	Intermediate Similarity	NPC470211
0.8406	Intermediate Similarity	NPC220062

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 NPC470981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	977
0.2-0.3	1847
0.3-0.4	2679
0.4-0.5	1861
0.5-0.6	1027
0.6-0.7	312
0.7-0.8	112
0.8-0.85	27
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD6651	Approved
0.8239	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1240	Approved
0.8116	Intermediate Similarity	NPD1510	Phase 2
0.8112	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1607	Approved
0.8014	Intermediate Similarity	NPD2800	Approved
0.7986	Intermediate Similarity	NPD2533	Approved
0.7986	Intermediate Similarity	NPD2534	Approved
0.7986	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2532	Approved
0.7958	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4380	Phase 2
0.7826	Intermediate Similarity	NPD943	Approved
0.7817	Intermediate Similarity	NPD1549	Phase 2
0.7793	Intermediate Similarity	NPD7390	Discontinued
0.7785	Intermediate Similarity	NPD7411	Suspended
0.7763	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2796	Approved
0.7676	Intermediate Similarity	NPD2935	Discontinued
0.7658	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7075	Discontinued
0.7632	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6801	Discontinued
0.7566	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7819	Suspended
0.7551	Intermediate Similarity	NPD6799	Approved
0.7517	Intermediate Similarity	NPD1243	Approved
0.7481	Intermediate Similarity	NPD9493	Approved
0.7451	Intermediate Similarity	NPD2801	Approved
0.7445	Intermediate Similarity	NPD1164	Approved
0.7432	Intermediate Similarity	NPD1511	Approved
0.7431	Intermediate Similarity	NPD5406	Approved
0.7431	Intermediate Similarity	NPD5408	Approved
0.7431	Intermediate Similarity	NPD5404	Approved
0.7431	Intermediate Similarity	NPD5405	Approved
0.7397	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2798	Approved
0.7386	Intermediate Similarity	NPD1934	Approved
0.7375	Intermediate Similarity	NPD3818	Discontinued
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7361	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7768	Phase 2
0.7347	Intermediate Similarity	NPD3750	Approved
0.7342	Intermediate Similarity	NPD5710	Approved
0.7342	Intermediate Similarity	NPD5711	Approved
0.7342	Intermediate Similarity	NPD6232	Discontinued
0.7333	Intermediate Similarity	NPD1512	Approved
0.7329	Intermediate Similarity	NPD7054	Approved
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD920	Approved
0.7284	Intermediate Similarity	NPD7074	Phase 3
0.7284	Intermediate Similarity	NPD7472	Approved
0.7279	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD2654	Approved
0.7278	Intermediate Similarity	NPD6959	Discontinued
0.7266	Intermediate Similarity	NPD74	Approved
0.7266	Intermediate Similarity	NPD9266	Approved
0.7248	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3882	Suspended
0.7241	Intermediate Similarity	NPD2799	Discontinued
0.7239	Intermediate Similarity	NPD9545	Approved
0.7239	Intermediate Similarity	NPD6797	Phase 2
0.72	Intermediate Similarity	NPD940	Approved
0.72	Intermediate Similarity	NPD846	Approved
0.7195	Intermediate Similarity	NPD6559	Discontinued
0.7195	Intermediate Similarity	NPD7251	Discontinued
0.7194	Intermediate Similarity	NPD1470	Approved
0.7192	Intermediate Similarity	NPD1551	Phase 2
0.7188	Intermediate Similarity	NPD9267	Approved
0.7188	Intermediate Similarity	NPD9264	Approved
0.7188	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9263	Approved
0.7183	Intermediate Similarity	NPD2313	Discontinued
0.7179	Intermediate Similarity	NPD3817	Phase 2
0.7153	Intermediate Similarity	NPD5124	Phase 1
0.7153	Intermediate Similarity	NPD230	Phase 1
0.7153	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7808	Phase 3
0.7134	Intermediate Similarity	NPD5953	Discontinued
0.7117	Intermediate Similarity	NPD7286	Phase 2
0.7101	Intermediate Similarity	NPD9269	Phase 2
0.7101	Intermediate Similarity	NPD9717	Approved
0.7089	Intermediate Similarity	NPD3749	Approved
0.7078	Intermediate Similarity	NPD7458	Discontinued
0.7071	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD5403	Approved
0.7059	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9268	Approved
0.7048	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6166	Phase 2
0.7037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD422	Phase 1
0.7027	Intermediate Similarity	NPD2344	Approved
0.7007	Intermediate Similarity	NPD3748	Approved
0.6963	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3268	Approved
0.694	Remote Similarity	NPD9281	Approved
0.6937	Remote Similarity	NPD919	Approved
0.6928	Remote Similarity	NPD5401	Approved
0.6928	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6832	Phase 2
0.6918	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5494	Approved
0.6887	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9261	Approved
0.6857	Remote Similarity	NPD3972	Approved
0.6846	Remote Similarity	NPD6099	Approved
0.6846	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD2309	Approved
0.6831	Remote Similarity	NPD2797	Approved
0.6818	Remote Similarity	NPD4750	Phase 3
0.6803	Remote Similarity	NPD1933	Approved
0.68	Remote Similarity	NPD2346	Discontinued
0.6781	Remote Similarity	NPD520	Approved
0.6779	Remote Similarity	NPD7033	Discontinued
0.6776	Remote Similarity	NPD4628	Phase 3
0.6753	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3226	Approved
0.675	Remote Similarity	NPD5402	Approved
0.6748	Remote Similarity	NPD1247	Approved
0.6742	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1296	Phase 2
0.6712	Remote Similarity	NPD3764	Approved
0.6712	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1729	Discontinued
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1809	Phase 2
0.6648	Remote Similarity	NPD4363	Phase 3
0.6648	Remote Similarity	NPD4360	Phase 2
0.6625	Remote Similarity	NPD37	Approved
0.6619	Remote Similarity	NPD1548	Phase 1
0.6612	Remote Similarity	NPD7584	Approved
0.661	Remote Similarity	NPD4361	Phase 2
0.661	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6020	Phase 2
0.6599	Remote Similarity	NPD411	Approved
0.6597	Remote Similarity	NPD3267	Approved
0.6597	Remote Similarity	NPD3266	Approved
0.6581	Remote Similarity	NPD3300	Phase 2
0.6577	Remote Similarity	NPD447	Suspended
0.6575	Remote Similarity	NPD4908	Phase 1
0.6566	Remote Similarity	NPD3926	Phase 2
0.6562	Remote Similarity	NPD5889	Approved
0.6562	Remote Similarity	NPD5890	Approved
0.6562	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD3400	Discontinued
0.6554	Remote Similarity	NPD6534	Approved
0.6554	Remote Similarity	NPD6535	Approved
0.6552	Remote Similarity	NPD1019	Discontinued
0.6543	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2859	Approved
0.6535	Remote Similarity	NPD2860	Approved
0.6529	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3225	Approved
0.6525	Remote Similarity	NPD2932	Approved
0.6525	Remote Similarity	NPD4626	Approved
0.6525	Remote Similarity	NPD3019	Approved
0.6524	Remote Similarity	NPD6234	Discontinued
0.6515	Remote Similarity	NPD5048	Discontinued
0.6514	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD845	Approved
0.6503	Remote Similarity	NPD4965	Approved
0.6503	Remote Similarity	NPD4966	Approved
0.6503	Remote Similarity	NPD4967	Phase 2
0.65	Remote Similarity	NPD6585	Discontinued
0.6496	Remote Similarity	NPD1241	Discontinued
0.6491	Remote Similarity	NPD6104	Discontinued
0.6481	Remote Similarity	NPD1465	Phase 2
0.6471	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6777	Approved
0.6464	Remote Similarity	NPD6780	Approved
0.6464	Remote Similarity	NPD6778	Approved
0.6464	Remote Similarity	NPD6781	Approved
0.6464	Remote Similarity	NPD6776	Approved
0.6464	Remote Similarity	NPD6779	Approved
0.6464	Remote Similarity	NPD6782	Approved
0.6462	Remote Similarity	NPD1242	Phase 1
0.6457	Remote Similarity	NPD2934	Approved
0.6457	Remote Similarity	NPD2933	Approved
0.6456	Remote Similarity	NPD5049	Phase 3
0.6452	Remote Similarity	NPD8151	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