NPASS Compound

Structure

CID39409 OpenBabel06191715372D 27 28 0 0 0 0 0 0 0 0999 V2000 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 12 2 0 0 0 0 10 24 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 27 1 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.01
Volume:	382.691
LogP:	5.371
LogD:	4.0
LogS:	-6.286
# Rotatable Bonds:	6
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	2.852
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.775
MDCK Permeability:	2.381314516242128e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	100.69501495361328%
Volume Distribution (VD):	0.628
Pgp-substrate:	2.2745211124420166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.375
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.68
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.715

ADMET: Excretion

Clearance (CL):	9.653
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.642
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.875
Maximum Recommended Daily Dose:	0.689
Skin Sensitization:	0.556
Carcinogencity:	0.073
Eye Corrosion:	0.004
Eye Irritation:	0.929
Respiratory Toxicity:	0.762

Download Data

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

Natural Product: NPC39409

Natural Product ID:	NPC39409
*Common Name:**	Buellin
IUPAC Name:	methyl 3-chloro-6-(3,5-dichloro-2-hydroxy-4-methoxy-6-methylphenoxy)-4-methoxy-2-methylbenzoate
Synonyms:	Buellin
Standard InCHIKey:	OYHGZQVOFWBBGE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H17Cl3O6/c1-7-11(18(23)26-5)9(6-10(24-3)12(7)19)27-16-8(2)13(20)17(25-4)14(21)15(16)22/h6,22H,1-5H3
SMILES:	COc1c(Cl)c(C)c(c(c1Cl)O)Oc1cc(OC)c(c(c1C(=O)OC)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079644
PubChem CID:	44614015
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
NPO13590	Diploicia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919064]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6208	Trichogoniopsis morii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13590	Diploicia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8523	Haematoxylon campechianum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5477	Mycosphaerella laricina	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25148	Helichrysum italicum	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	250.0	nM	PMID[525555]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	>	10000.0	nM	PMID[525555]

☑ 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 NPC39409 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	500
0.1-0.2	2616
0.2-0.3	7704
0.3-0.4	12101
0.4-0.5	4076
0.5-0.6	5963
0.6-0.7	7266
0.7-0.8	2404
0.8-0.85	36
0.85-0.9	10
0.9-0.95	11
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC471810
0.9714	High Similarity	NPC471806
0.9657	High Similarity	NPC121100
0.9657	High Similarity	NPC471805
0.9657	High Similarity	NPC471813
0.9602	High Similarity	NPC471807
0.9489	High Similarity	NPC471804
0.9489	High Similarity	NPC471803
0.9489	High Similarity	NPC471812
0.9375	High Similarity	NPC471811
0.9375	High Similarity	NPC471809
0.9318	High Similarity	NPC195675
0.9318	High Similarity	NPC471808
0.9318	High Similarity	NPC471814
0.9148	High Similarity	NPC471801
0.9143	High Similarity	NPC108278
0.9091	High Similarity	NPC471802
0.9034	High Similarity	NPC175804
0.8876	High Similarity	NPC28160
0.8757	High Similarity	NPC214901
0.8703	High Similarity	NPC220369
0.8652	High Similarity	NPC188618
0.8571	High Similarity	NPC154720
0.8564	High Similarity	NPC198163
0.85	High Similarity	NPC470422
0.8368	Intermediate Similarity	NPC193676
0.8306	Intermediate Similarity	NPC45072
0.8295	Intermediate Similarity	NPC238381
0.8218	Intermediate Similarity	NPC289968
0.8201	Intermediate Similarity	NPC470099
0.8191	Intermediate Similarity	NPC474499
0.8182	Intermediate Similarity	NPC54928
0.8177	Intermediate Similarity	NPC472032
0.8125	Intermediate Similarity	NPC471800
0.8105	Intermediate Similarity	NPC470100
0.8056	Intermediate Similarity	NPC474096
0.8054	Intermediate Similarity	NPC477568
0.8034	Intermediate Similarity	NPC300727
0.8034	Intermediate Similarity	NPC241904
0.8022	Intermediate Similarity	NPC472452
0.8	Intermediate Similarity	NPC298401
0.8	Intermediate Similarity	NPC472405
0.7989	Intermediate Similarity	NPC83763
0.7989	Intermediate Similarity	NPC476242
0.7989	Intermediate Similarity	NPC168616
0.7979	Intermediate Similarity	NPC247104
0.7978	Intermediate Similarity	NPC274730
0.7967	Intermediate Similarity	NPC173352
0.7967	Intermediate Similarity	NPC58653
0.7967	Intermediate Similarity	NPC8070
0.7956	Intermediate Similarity	NPC473696
0.7946	Intermediate Similarity	NPC474857
0.7944	Intermediate Similarity	NPC14353
0.7944	Intermediate Similarity	NPC200594
0.7944	Intermediate Similarity	NPC228785
0.7944	Intermediate Similarity	NPC56085
0.7938	Intermediate Similarity	NPC48822
0.7927	Intermediate Similarity	NPC221185
0.7923	Intermediate Similarity	NPC474061
0.7923	Intermediate Similarity	NPC28669
0.7921	Intermediate Similarity	NPC20541
0.7912	Intermediate Similarity	NPC156082
0.7912	Intermediate Similarity	NPC300984
0.7912	Intermediate Similarity	NPC470081
0.7912	Intermediate Similarity	NPC474350
0.7901	Intermediate Similarity	NPC40491
0.7901	Intermediate Similarity	NPC278052
0.7901	Intermediate Similarity	NPC61010
0.7901	Intermediate Similarity	NPC303565
0.7895	Intermediate Similarity	NPC99937
0.7892	Intermediate Similarity	NPC107283
0.7892	Intermediate Similarity	NPC109827
0.7892	Intermediate Similarity	NPC470562
0.7892	Intermediate Similarity	NPC124470
0.7892	Intermediate Similarity	NPC470565
0.7892	Intermediate Similarity	NPC277865
0.7889	Intermediate Similarity	NPC45846
0.7889	Intermediate Similarity	NPC100123
0.7877	Intermediate Similarity	NPC227062
0.7869	Intermediate Similarity	NPC112981
0.7869	Intermediate Similarity	NPC267153
0.7865	Intermediate Similarity	NPC255350
0.7865	Intermediate Similarity	NPC160951
0.7865	Intermediate Similarity	NPC145379
0.7865	Intermediate Similarity	NPC22519
0.7865	Intermediate Similarity	NPC176775
0.7865	Intermediate Similarity	NPC136411
0.7865	Intermediate Similarity	NPC231018
0.7865	Intermediate Similarity	NPC47781
0.7865	Intermediate Similarity	NPC183878
0.7865	Intermediate Similarity	NPC250822
0.7865	Intermediate Similarity	NPC75279
0.7865	Intermediate Similarity	NPC276409
0.7865	Intermediate Similarity	NPC89474
0.7865	Intermediate Similarity	NPC274327
0.7865	Intermediate Similarity	NPC69394
0.7861	Intermediate Similarity	NPC264922
0.7857	Intermediate Similarity	NPC93739
0.7849	Intermediate Similarity	NPC158226
0.7849	Intermediate Similarity	NPC470560
0.7845	Intermediate Similarity	NPC200746
0.7845	Intermediate Similarity	NPC320359
0.7841	Intermediate Similarity	NPC328119
0.7841	Intermediate Similarity	NPC48479
0.7841	Intermediate Similarity	NPC177298
0.7838	Intermediate Similarity	NPC165979
0.7838	Intermediate Similarity	NPC163130
0.7833	Intermediate Similarity	NPC165977
0.7833	Intermediate Similarity	NPC217677
0.7833	Intermediate Similarity	NPC469584
0.7833	Intermediate Similarity	NPC472404
0.7826	Intermediate Similarity	NPC20216
0.7821	Intermediate Similarity	NPC227325
0.7821	Intermediate Similarity	NPC16082
0.7821	Intermediate Similarity	NPC167815
0.7821	Intermediate Similarity	NPC280339
0.7821	Intermediate Similarity	NPC201136
0.7821	Intermediate Similarity	NPC146165
0.7821	Intermediate Similarity	NPC196439
0.7821	Intermediate Similarity	NPC20830
0.7821	Intermediate Similarity	NPC138360
0.7821	Intermediate Similarity	NPC4455
0.7821	Intermediate Similarity	NPC256612
0.7821	Intermediate Similarity	NPC128863
0.7821	Intermediate Similarity	NPC163780
0.7821	Intermediate Similarity	NPC2476
0.7821	Intermediate Similarity	NPC208197
0.7821	Intermediate Similarity	NPC50715
0.7821	Intermediate Similarity	NPC82592
0.7821	Intermediate Similarity	NPC213622
0.7821	Intermediate Similarity	NPC183597
0.7821	Intermediate Similarity	NPC92659
0.7814	Intermediate Similarity	NPC236132
0.7814	Intermediate Similarity	NPC7483
0.7814	Intermediate Similarity	NPC270837
0.7814	Intermediate Similarity	NPC234004
0.7814	Intermediate Similarity	NPC220313
0.7814	Intermediate Similarity	NPC133065
0.7814	Intermediate Similarity	NPC152659
0.7814	Intermediate Similarity	NPC284007
0.7814	Intermediate Similarity	NPC236521
0.7814	Intermediate Similarity	NPC248638
0.7814	Intermediate Similarity	NPC475985
0.7809	Intermediate Similarity	NPC199773
0.7809	Intermediate Similarity	NPC71334
0.7809	Intermediate Similarity	NPC256283
0.7809	Intermediate Similarity	NPC187498
0.7809	Intermediate Similarity	NPC100887
0.7809	Intermediate Similarity	NPC156222
0.7809	Intermediate Similarity	NPC142540
0.7809	Intermediate Similarity	NPC212678
0.7809	Intermediate Similarity	NPC57030
0.7809	Intermediate Similarity	NPC25270
0.7809	Intermediate Similarity	NPC241498
0.7809	Intermediate Similarity	NPC162313
0.7809	Intermediate Similarity	NPC83508
0.7809	Intermediate Similarity	NPC131624
0.7809	Intermediate Similarity	NPC275836
0.7809	Intermediate Similarity	NPC293183
0.7809	Intermediate Similarity	NPC198826
0.7809	Intermediate Similarity	NPC301323
0.7809	Intermediate Similarity	NPC120163
0.7809	Intermediate Similarity	NPC275722
0.7809	Intermediate Similarity	NPC239128
0.7809	Intermediate Similarity	NPC188203
0.7809	Intermediate Similarity	NPC222830
0.7806	Intermediate Similarity	NPC313541
0.7797	Intermediate Similarity	NPC225129
0.779	Intermediate Similarity	NPC329091
0.7789	Intermediate Similarity	NPC151292
0.7784	Intermediate Similarity	NPC272485
0.7784	Intermediate Similarity	NPC120464
0.7784	Intermediate Similarity	NPC292788
0.7778	Intermediate Similarity	NPC108744
0.7778	Intermediate Similarity	NPC268161
0.7778	Intermediate Similarity	NPC200388
0.7778	Intermediate Similarity	NPC472456
0.7778	Intermediate Similarity	NPC472916
0.7778	Intermediate Similarity	NPC474520
0.7778	Intermediate Similarity	NPC49824
0.7778	Intermediate Similarity	NPC142339
0.7778	Intermediate Similarity	NPC100916
0.7778	Intermediate Similarity	NPC55619
0.7778	Intermediate Similarity	NPC150227
0.7772	Intermediate Similarity	NPC68850
0.7772	Intermediate Similarity	NPC316091
0.7772	Intermediate Similarity	NPC326520
0.7772	Intermediate Similarity	NPC275780
0.7772	Intermediate Similarity	NPC39306
0.7772	Intermediate Similarity	NPC239752
0.7772	Intermediate Similarity	NPC472450
0.7771	Intermediate Similarity	NPC138978
0.7766	Intermediate Similarity	NPC139350
0.7765	Intermediate Similarity	NPC281477
0.776	Intermediate Similarity	NPC294965
0.776	Intermediate Similarity	NPC8300
0.776	Intermediate Similarity	NPC191606
0.776	Intermediate Similarity	NPC470103
0.776	Intermediate Similarity	NPC25152
0.7759	Intermediate Similarity	NPC95123

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 NPC39409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	1246
0.2-0.3	2444
0.3-0.4	2623
0.4-0.5	1500
0.5-0.6	680
0.6-0.7	188
0.7-0.8	29
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
0.7865	Intermediate Similarity	NPD2801	Approved
0.7684	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2403	Approved
0.7611	Intermediate Similarity	NPD1934	Approved
0.7571	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD3817	Phase 2
0.7486	Intermediate Similarity	NPD3882	Suspended
0.7473	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD1465	Phase 2
0.7473	Intermediate Similarity	NPD6232	Discontinued
0.7458	Intermediate Similarity	NPD1511	Approved
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD1512	Approved
0.7371	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7354	Intermediate Similarity	NPD7473	Discontinued
0.7302	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6166	Phase 2
0.7302	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7054	Approved
0.724	Intermediate Similarity	NPD7074	Phase 3
0.724	Intermediate Similarity	NPD7472	Approved
0.7225	Intermediate Similarity	NPD3818	Discontinued
0.7189	Intermediate Similarity	NPD7819	Suspended
0.7167	Intermediate Similarity	NPD6799	Approved
0.7113	Intermediate Similarity	NPD6797	Phase 2
0.709	Intermediate Similarity	NPD5494	Approved
0.7081	Intermediate Similarity	NPD958	Approved
0.7077	Intermediate Similarity	NPD7251	Discontinued
0.7074	Intermediate Similarity	NPD7075	Discontinued
0.7041	Intermediate Similarity	NPD7808	Phase 3
0.7033	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD2533	Approved
0.7033	Intermediate Similarity	NPD2534	Approved
0.7033	Intermediate Similarity	NPD2532	Approved
0.7027	Intermediate Similarity	NPD6599	Discontinued
0.7005	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5402	Approved
0.6966	Remote Similarity	NPD2935	Discontinued
0.6963	Remote Similarity	NPD6959	Discontinued
0.6952	Remote Similarity	NPD6801	Discontinued
0.6939	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1184	Approved
0.6932	Remote Similarity	NPD230	Phase 1
0.6919	Remote Similarity	NPD957	Approved
0.6906	Remote Similarity	NPD3750	Approved
0.6895	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7199	Phase 2
0.6868	Remote Similarity	NPD2354	Approved
0.6859	Remote Similarity	NPD6234	Discontinued
0.6845	Remote Similarity	NPD4380	Phase 2
0.6836	Remote Similarity	NPD447	Suspended
0.6833	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7411	Suspended
0.6806	Remote Similarity	NPD3749	Approved
0.6804	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1549	Phase 2
0.678	Remote Similarity	NPD1240	Approved
0.678	Remote Similarity	NPD4360	Phase 2
0.678	Remote Similarity	NPD4363	Phase 3
0.6778	Remote Similarity	NPD1551	Phase 2
0.6771	Remote Similarity	NPD919	Approved
0.6761	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7768	Phase 2
0.6722	Remote Similarity	NPD1510	Phase 2
0.6721	Remote Similarity	NPD4628	Phase 3
0.6718	Remote Similarity	NPD3926	Phase 2
0.6704	Remote Similarity	NPD1607	Approved
0.6702	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1247	Approved
0.6699	Remote Similarity	NPD6312	Discontinued
0.6685	Remote Similarity	NPD2796	Approved
0.6685	Remote Similarity	NPD3887	Approved
0.6685	Remote Similarity	NPD943	Approved
0.6684	Remote Similarity	NPD37	Approved
0.6684	Remote Similarity	NPD5403	Approved
0.6684	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD4361	Phase 2
0.6667	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2800	Approved
0.665	Remote Similarity	NPD6559	Discontinued
0.6649	Remote Similarity	NPD1653	Approved
0.6648	Remote Similarity	NPD2353	Approved
0.6648	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3748	Approved
0.663	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7228	Approved
0.6614	Remote Similarity	NPD3226	Approved
0.6613	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4534	Discontinued
0.6602	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD454	Approved
0.6591	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5711	Approved
0.6582	Remote Similarity	NPD5710	Approved
0.6579	Remote Similarity	NPD4972	Discontinued
0.6578	Remote Similarity	NPD1578	Phase 2
0.6578	Remote Similarity	NPD5401	Approved
0.6556	Remote Similarity	NPD1933	Approved
0.6554	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3751	Discontinued
0.6522	Remote Similarity	NPD5958	Discontinued
0.652	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3027	Phase 3
0.6508	Remote Similarity	NPD920	Approved
0.6505	Remote Similarity	NPD6190	Approved
0.65	Remote Similarity	NPD7286	Phase 2
0.65	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1613	Approved
0.6497	Remote Similarity	NPD3787	Discontinued
0.6486	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1243	Approved
0.6477	Remote Similarity	NPD1203	Approved
0.6467	Remote Similarity	NPD2346	Discontinued
0.6465	Remote Similarity	NPD5242	Approved
0.6462	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD2799	Discontinued
0.6443	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5953	Discontinued
0.6413	Remote Similarity	NPD6100	Approved
0.6413	Remote Similarity	NPD6099	Approved
0.6413	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7685	Pre-registration
0.64	Remote Similarity	NPD9269	Phase 2
0.6393	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4538	Approved
0.6393	Remote Similarity	NPD4536	Approved
0.6374	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6832	Phase 2
0.6359	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5353	Approved
0.6359	Remote Similarity	NPD1163	Approved
0.635	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7390	Discontinued
0.6341	Remote Similarity	NPD8312	Approved
0.6341	Remote Similarity	NPD8313	Approved
0.6339	Remote Similarity	NPD6651	Approved
0.6332	Remote Similarity	NPD7229	Phase 3
0.6329	Remote Similarity	NPD8434	Phase 2
0.6324	Remote Similarity	NPD3303	Discontinued
0.6319	Remote Similarity	NPD4060	Phase 1
0.6318	Remote Similarity	NPD7783	Phase 2
0.6318	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD9494	Approved
0.6307	Remote Similarity	NPD1608	Approved
0.6307	Remote Similarity	NPD9717	Approved
0.6301	Remote Similarity	NPD8151	Discontinued
0.6296	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5058	Phase 3
0.6296	Remote Similarity	NPD7435	Discontinued
0.629	Remote Similarity	NPD2344	Approved
0.6289	Remote Similarity	NPD6386	Approved
0.6289	Remote Similarity	NPD6385	Approved
0.6286	Remote Similarity	NPD915	Approved
0.628	Remote Similarity	NPD6784	Approved
0.628	Remote Similarity	NPD6785	Approved
0.6276	Remote Similarity	NPD4288	Approved
0.6271	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5960	Phase 3
0.627	Remote Similarity	NPD5588	Approved
0.6264	Remote Similarity	NPD6233	Phase 2
0.625	Remote Similarity	NPD8150	Discontinued
0.625	Remote Similarity	NPD422	Phase 1
0.6244	Remote Similarity	NPD7240	Approved
0.6233	Remote Similarity	NPD6781	Approved
0.6233	Remote Similarity	NPD6779	Approved
0.6233	Remote Similarity	NPD6780	Approved
0.6233	Remote Similarity	NPD6778	Approved
0.6233	Remote Similarity	NPD6782	Approved
0.6233	Remote Similarity	NPD6776	Approved
0.6233	Remote Similarity	NPD6777	Approved
0.6232	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7549	Discontinued
0.6209	Remote Similarity	NPD3268	Approved
0.6209	Remote Similarity	NPD2313	Discontinued
0.6209	Remote Similarity	NPD411	Approved
0.6209	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD2797	Approved
0.6196	Remote Similarity	NPD6355	Discontinued
0.6186	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7033	Discontinued
0.6171	Remote Similarity	NPD9268	Approved
0.6168	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD2309	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