NPASS Compound

Structure

NPC58164 OpenBabel07101718182D 21 22 0 0 0 0 0 0 0 0999 V2000 -0.0000 -3.0000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 2.5981 -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 4.3301 0.5000 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 0.8660 0.5000 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 0.8660 -1.5000 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 0.8660 1.5000 0.0000 O 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 0.8660 -2.5000 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	302.181
LogP:	2.847
LogD:	3.057
LogS:	-3.312
# Rotatable Bonds:	5
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.884
Synthetic Accessibility Score:	2.389
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	1.92112238437403e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	97.82001495361328%
Volume Distribution (VD):	0.561
Pgp-substrate:	2.0553836822509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.786
CYP2C19-substrate:	0.421
CYP2C9-inhibitor:	0.658
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.682
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	6.674
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.947
Carcinogencity:	0.45
Eye Corrosion:	0.009
Eye Irritation:	0.92
Respiratory Toxicity:	0.37

Download Data

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

Natural Product: NPC58164

Natural Product ID:	NPC58164
*Common Name:**	Macharistol
IUPAC Name:	2,4-dimethoxy-5-[(E)-3-phenylprop-2-enyl]benzene-1,3-diol
Synonyms:	macharistol
Standard InCHIKey:	UNXRJDKKDAMIOH-RMKNXTFCSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-20-16-13(11-14(18)17(21-2)15(16)19)10-6-9-12-7-4-3-5-8-12/h3-9,11,18-19H,10H2,1-2H3/b9-6+
SMILES:	COc1c(C/C=C/c2ccccc2)cc(c(c1O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523511
PubChem CID:	10085384
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO27571	Machaerium aristulatum	Species	Dolichopodidae	Eukaryota	stems	n.a.	n.a.	PMID[11720542]
NPO27571	Machaerium aristulatum	Species	Dolichopodidae	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
EC50	5
Others	6

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	1.7	ug.mL-1	PMID[464571]
NPT1851	Cell Line	Col2	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[464571]
NPT858	Cell Line	LNCaP	Homo sapiens	EC50	=	2.4	ug.mL-1	PMID[464571]
NPT737	Cell Line	HUVEC	Homo sapiens	EC50	=	1.3	ug.mL-1	PMID[464571]
NPT91	Cell Line	KB	Homo sapiens	GI	=	23.0	%	PMID[464571]
NPT91	Cell Line	KB	Homo sapiens	GI	=	0.0	%	PMID[464571]
NPT1851	Cell Line	Col2	Homo sapiens	GI	=	35.0	%	PMID[464571]
NPT27	Others	Unspecified		EC50	=	3.0	ug.mL-1	PMID[464571]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	31.0	%	PMID[464571]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	45.0	%	PMID[464571]

☑ 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 NPC58164 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	423
0.1-0.2	1842
0.2-0.3	6205
0.3-0.4	13056
0.4-0.5	3722
0.5-0.6	4217
0.6-0.7	7011
0.7-0.8	4725
0.8-0.85	766
0.85-0.9	448
0.9-0.95	240
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC10225
0.9919	High Similarity	NPC51840
0.9919	High Similarity	NPC299221
0.9919	High Similarity	NPC311680
0.9919	High Similarity	NPC234488
0.976	High Similarity	NPC6451
0.9756	High Similarity	NPC266691
0.9754	High Similarity	NPC18924
0.9754	High Similarity	NPC28730
0.9754	High Similarity	NPC78974
0.9754	High Similarity	NPC223136
0.9754	High Similarity	NPC103823
0.9754	High Similarity	NPC214406
0.9754	High Similarity	NPC44748
0.968	High Similarity	NPC474356
0.968	High Similarity	NPC232275
0.968	High Similarity	NPC45715
0.968	High Similarity	NPC12275
0.9675	High Similarity	NPC169474
0.9675	High Similarity	NPC159968
0.9675	High Similarity	NPC236791
0.9675	High Similarity	NPC246620
0.9675	High Similarity	NPC282000
0.9675	High Similarity	NPC124452
0.9675	High Similarity	NPC293054
0.9675	High Similarity	NPC324112
0.9675	High Similarity	NPC74817
0.9675	High Similarity	NPC82679
0.9672	High Similarity	NPC234400
0.9672	High Similarity	NPC299584
0.9672	High Similarity	NPC60885
0.9672	High Similarity	NPC82483
0.9672	High Similarity	NPC265483
0.96	High Similarity	NPC214860
0.96	High Similarity	NPC192687
0.96	High Similarity	NPC224157
0.959	High Similarity	NPC183446
0.9531	High Similarity	NPC472337
0.952	High Similarity	NPC190144
0.952	High Similarity	NPC45824
0.9512	High Similarity	NPC193544
0.9512	High Similarity	NPC475169
0.9512	High Similarity	NPC105925
0.9512	High Similarity	NPC233410
0.9512	High Similarity	NPC221077
0.9512	High Similarity	NPC17943
0.9512	High Similarity	NPC251855
0.9512	High Similarity	NPC208950
0.9512	High Similarity	NPC116907
0.9512	High Similarity	NPC472093
0.9512	High Similarity	NPC57490
0.9512	High Similarity	NPC203133
0.9512	High Similarity	NPC117214
0.9512	High Similarity	NPC298757
0.9508	High Similarity	NPC95168
0.9457	High Similarity	NPC472336
0.9457	High Similarity	NPC472334
0.9444	High Similarity	NPC126836
0.944	High Similarity	NPC28765
0.944	High Similarity	NPC154866
0.9435	High Similarity	NPC112596
0.9426	High Similarity	NPC262253
0.9426	High Similarity	NPC473411
0.9426	High Similarity	NPC71579
0.9385	High Similarity	NPC90615
0.9385	High Similarity	NPC103976
0.9385	High Similarity	NPC6262
0.9385	High Similarity	NPC326797
0.9385	High Similarity	NPC276490
0.9385	High Similarity	NPC474282
0.9385	High Similarity	NPC107551
0.9385	High Similarity	NPC201145
0.9385	High Similarity	NPC73535
0.9385	High Similarity	NPC272157
0.9385	High Similarity	NPC102904
0.9385	High Similarity	NPC176051
0.9385	High Similarity	NPC25111
0.9375	High Similarity	NPC229442
0.9375	High Similarity	NPC168059
0.9365	High Similarity	NPC170844
0.9365	High Similarity	NPC212015
0.9365	High Similarity	NPC476968
0.936	High Similarity	NPC216836
0.936	High Similarity	NPC252131
0.936	High Similarity	NPC236760
0.936	High Similarity	NPC210355
0.936	High Similarity	NPC127587
0.936	High Similarity	NPC266555
0.935	High Similarity	NPC228922
0.935	High Similarity	NPC282496
0.935	High Similarity	NPC136319
0.935	High Similarity	NPC233526
0.935	High Similarity	NPC121115
0.935	High Similarity	NPC197757
0.9344	High Similarity	NPC75713
0.9344	High Similarity	NPC285289
0.9313	High Similarity	NPC79622
0.9313	High Similarity	NPC245207
0.9313	High Similarity	NPC212942
0.9313	High Similarity	NPC29868
0.9313	High Similarity	NPC319647
0.9313	High Similarity	NPC127218
0.9313	High Similarity	NPC25966
0.9308	High Similarity	NPC300846
0.9308	High Similarity	NPC476639
0.9308	High Similarity	NPC114155
0.9302	High Similarity	NPC310854
0.9302	High Similarity	NPC106215
0.9297	High Similarity	NPC127624
0.9297	High Similarity	NPC86655
0.9297	High Similarity	NPC202762
0.9286	High Similarity	NPC470213
0.9286	High Similarity	NPC186843
0.9286	High Similarity	NPC98631
0.9286	High Similarity	NPC206615
0.928	High Similarity	NPC76451
0.928	High Similarity	NPC223953
0.9268	High Similarity	NPC41562
0.9268	High Similarity	NPC246967
0.9268	High Similarity	NPC135414
0.9268	High Similarity	NPC474864
0.9262	High Similarity	NPC166759
0.9242	High Similarity	NPC160283
0.9242	High Similarity	NPC254759
0.9242	High Similarity	NPC73505
0.9242	High Similarity	NPC284464
0.9242	High Similarity	NPC165026
0.9242	High Similarity	NPC295719
0.9242	High Similarity	NPC34431
0.9231	High Similarity	NPC283009
0.9231	High Similarity	NPC474206
0.9231	High Similarity	NPC121812
0.9231	High Similarity	NPC201357
0.9231	High Similarity	NPC256262
0.9231	High Similarity	NPC195022
0.9231	High Similarity	NPC134968
0.9231	High Similarity	NPC94750
0.9231	High Similarity	NPC112246
0.9231	High Similarity	NPC261873
0.9231	High Similarity	NPC255147
0.9231	High Similarity	NPC281521
0.9231	High Similarity	NPC111655
0.9231	High Similarity	NPC112939
0.9231	High Similarity	NPC470356
0.9225	High Similarity	NPC475840
0.9225	High Similarity	NPC471391
0.9225	High Similarity	NPC32778
0.9225	High Similarity	NPC37196
0.9225	High Similarity	NPC94236
0.9225	High Similarity	NPC471390
0.9219	High Similarity	NPC474017
0.9219	High Similarity	NPC470095
0.9219	High Similarity	NPC472597
0.9219	High Similarity	NPC470096
0.9206	High Similarity	NPC242032
0.918	High Similarity	NPC247364
0.918	High Similarity	NPC61516
0.918	High Similarity	NPC10932
0.918	High Similarity	NPC232084
0.918	High Similarity	NPC474565
0.9173	High Similarity	NPC471389
0.9167	High Similarity	NPC30951
0.9167	High Similarity	NPC6369
0.9167	High Similarity	NPC292882
0.916	High Similarity	NPC143139
0.916	High Similarity	NPC205442
0.916	High Similarity	NPC474639
0.916	High Similarity	NPC270456
0.916	High Similarity	NPC162659
0.916	High Similarity	NPC202846
0.916	High Similarity	NPC248727
0.916	High Similarity	NPC306441
0.916	High Similarity	NPC230734
0.916	High Similarity	NPC173660
0.916	High Similarity	NPC16435
0.916	High Similarity	NPC227503
0.916	High Similarity	NPC265433
0.9154	High Similarity	NPC276026
0.9154	High Similarity	NPC7515
0.9154	High Similarity	NPC206737
0.9154	High Similarity	NPC56764
0.9154	High Similarity	NPC469659
0.9154	High Similarity	NPC555
0.9154	High Similarity	NPC188378
0.9154	High Similarity	NPC289258
0.9154	High Similarity	NPC317380
0.9154	High Similarity	NPC103967
0.9147	High Similarity	NPC253105
0.9147	High Similarity	NPC7903
0.9147	High Similarity	NPC35932
0.9147	High Similarity	NPC161203
0.9147	High Similarity	NPC160991
0.9147	High Similarity	NPC16208
0.9147	High Similarity	NPC184447
0.9147	High Similarity	NPC201587
0.9141	High Similarity	NPC472338
0.9141	High Similarity	NPC91291
0.9141	High Similarity	NPC220935
0.912	High Similarity	NPC206487
0.912	High Similarity	NPC5796

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 NPC58164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	957
0.2-0.3	1962
0.3-0.4	2768
0.4-0.5	1543
0.5-0.6	836
0.6-0.7	586
0.7-0.8	113
0.8-0.85	9
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9365	High Similarity	NPD3027	Phase 3
0.8984	High Similarity	NPD1529	Clinical (unspecified phase)
0.8906	High Similarity	NPD1530	Clinical (unspecified phase)
0.8855	High Similarity	NPD1612	Clinical (unspecified phase)
0.8855	High Similarity	NPD1613	Approved
0.8615	High Similarity	NPD3018	Phase 2
0.845	Intermediate Similarity	NPD2982	Phase 2
0.845	Intermediate Similarity	NPD2983	Phase 2
0.8443	Intermediate Similarity	NPD228	Approved
0.8372	Intermediate Similarity	NPD2981	Phase 2
0.8356	Intermediate Similarity	NPD2801	Approved
0.8168	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD5283	Phase 1
0.8134	Intermediate Similarity	NPD4908	Phase 1
0.8125	Intermediate Similarity	NPD1548	Phase 1
0.8041	Intermediate Similarity	NPD1934	Approved
0.8015	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1610	Phase 2
0.8014	Intermediate Similarity	NPD1653	Approved
0.7943	Intermediate Similarity	NPD3540	Phase 1
0.7926	Intermediate Similarity	NPD2861	Phase 2
0.7881	Intermediate Similarity	NPD3882	Suspended
0.7872	Intermediate Similarity	NPD3539	Phase 1
0.7867	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1511	Approved
0.784	Intermediate Similarity	NPD3021	Approved
0.784	Intermediate Similarity	NPD3022	Approved
0.781	Intermediate Similarity	NPD4625	Phase 3
0.777	Intermediate Similarity	NPD1558	Phase 1
0.7761	Intermediate Similarity	NPD4749	Approved
0.7755	Intermediate Similarity	NPD1512	Approved
0.7752	Intermediate Similarity	NPD6671	Approved
0.7662	Intermediate Similarity	NPD6234	Discontinued
0.7647	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6166	Phase 2
0.7635	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5536	Phase 2
0.763	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD1242	Phase 1
0.7619	Intermediate Similarity	NPD4357	Discontinued
0.7612	Intermediate Similarity	NPD3705	Approved
0.7612	Intermediate Similarity	NPD422	Phase 1
0.7603	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3817	Phase 2
0.7566	Intermediate Similarity	NPD37	Approved
0.7561	Intermediate Similarity	NPD940	Approved
0.7561	Intermediate Similarity	NPD846	Approved
0.755	Intermediate Similarity	NPD4678	Approved
0.755	Intermediate Similarity	NPD4675	Approved
0.7518	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4060	Phase 1
0.7518	Intermediate Similarity	NPD3620	Phase 2
0.7516	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2219	Phase 1
0.7481	Intermediate Similarity	NPD1091	Approved
0.7466	Intermediate Similarity	NPD3060	Approved
0.746	Intermediate Similarity	NPD968	Approved
0.7453	Intermediate Similarity	NPD7472	Approved
0.7453	Intermediate Similarity	NPD7074	Phase 3
0.7448	Intermediate Similarity	NPD7266	Discontinued
0.7447	Intermediate Similarity	NPD2674	Phase 3
0.7438	Intermediate Similarity	NPD3818	Discontinued
0.7432	Intermediate Similarity	NPD7124	Phase 2
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD4750	Phase 3
0.7419	Intermediate Similarity	NPD4967	Phase 2
0.7419	Intermediate Similarity	NPD4965	Approved
0.7419	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD1240	Approved
0.7391	Intermediate Similarity	NPD5844	Phase 1
0.7388	Intermediate Similarity	NPD1357	Approved
0.7375	Intermediate Similarity	NPD7473	Discontinued
0.7368	Intermediate Similarity	NPD4005	Discontinued
0.7347	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5177	Phase 3
0.7344	Intermediate Similarity	NPD2684	Approved
0.7343	Intermediate Similarity	NPD230	Phase 1
0.7342	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7228	Approved
0.732	Intermediate Similarity	NPD4380	Phase 2
0.7319	Intermediate Similarity	NPD2922	Phase 1
0.731	Intermediate Similarity	NPD1510	Phase 2
0.7301	Intermediate Similarity	NPD6797	Phase 2
0.7292	Intermediate Similarity	NPD1607	Approved
0.729	Intermediate Similarity	NPD1465	Phase 2
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7278	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD943	Approved
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD290	Approved
0.7261	Intermediate Similarity	NPD4055	Discovery
0.7256	Intermediate Similarity	NPD7251	Discontinued
0.7254	Intermediate Similarity	NPD3145	Approved
0.7254	Intermediate Similarity	NPD3144	Approved
0.7252	Intermediate Similarity	NPD7843	Approved
0.725	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6190	Approved
0.7241	Intermediate Similarity	NPD6111	Discontinued
0.7237	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6674	Discontinued
0.723	Intermediate Similarity	NPD4236	Phase 3
0.723	Intermediate Similarity	NPD4237	Approved
0.723	Intermediate Similarity	NPD1652	Phase 2
0.7219	Intermediate Similarity	NPD4123	Phase 3
0.7219	Intermediate Similarity	NPD7447	Phase 1
0.7218	Intermediate Similarity	NPD7157	Approved
0.7213	Intermediate Similarity	NPD9296	Approved
0.7213	Intermediate Similarity	NPD2933	Approved
0.7213	Intermediate Similarity	NPD2934	Approved
0.7212	Intermediate Similarity	NPD7549	Discontinued
0.7212	Intermediate Similarity	NPD7808	Phase 3
0.7203	Intermediate Similarity	NPD6233	Phase 2
0.7194	Intermediate Similarity	NPD8651	Approved
0.7194	Intermediate Similarity	NPD6696	Suspended
0.7179	Intermediate Similarity	NPD2977	Approved
0.7179	Intermediate Similarity	NPD2978	Approved
0.7163	Intermediate Similarity	NPD9494	Approved
0.7162	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2859	Approved
0.7154	Intermediate Similarity	NPD2860	Approved
0.7153	Intermediate Similarity	NPD2238	Phase 2
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6100	Approved
0.7134	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD5110	Phase 2
0.7133	Intermediate Similarity	NPD5111	Phase 2
0.7133	Intermediate Similarity	NPD5109	Approved
0.7133	Intermediate Similarity	NPD2677	Approved
0.7126	Intermediate Similarity	NPD8053	Approved
0.7126	Intermediate Similarity	NPD8054	Approved
0.7123	Intermediate Similarity	NPD4538	Approved
0.7123	Intermediate Similarity	NPD4536	Approved
0.7123	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3020	Approved
0.7113	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6584	Phase 3
0.7091	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4626	Approved
0.7067	Intermediate Similarity	NPD3892	Phase 2
0.7067	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7095	Approved
0.7051	Intermediate Similarity	NPD5090	Approved
0.7051	Intermediate Similarity	NPD5089	Approved
0.705	Intermediate Similarity	NPD2232	Approved
0.705	Intermediate Similarity	NPD2233	Approved
0.705	Intermediate Similarity	NPD2230	Approved
0.7047	Intermediate Similarity	NPD1549	Phase 2
0.7044	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7075	Discontinued
0.7023	Intermediate Similarity	NPD5451	Approved
0.7014	Intermediate Similarity	NPD5718	Phase 2
0.7014	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD4162	Approved
0.6993	Remote Similarity	NPD1424	Approved
0.6993	Remote Similarity	NPD600	Approved
0.6993	Remote Similarity	NPD596	Approved
0.6992	Remote Similarity	NPD7635	Approved
0.6986	Remote Similarity	NPD447	Suspended
0.6986	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6355	Discontinued
0.6986	Remote Similarity	NPD5124	Phase 1
0.6981	Remote Similarity	NPD6788	Approved
0.698	Remote Similarity	NPD1375	Discontinued
0.6978	Remote Similarity	NPD1535	Discovery
0.697	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD839	Approved
0.6966	Remote Similarity	NPD840	Approved
0.6963	Remote Similarity	NPD709	Approved
0.6962	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5960	Phase 3
0.6959	Remote Similarity	NPD5588	Approved
0.6959	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6516	Phase 2
0.6957	Remote Similarity	NPD5846	Approved
0.6954	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4097	Suspended
0.6929	Remote Similarity	NPD1481	Phase 2
0.6928	Remote Similarity	NPD5297	Approved
0.6928	Remote Similarity	NPD1774	Approved
0.6923	Remote Similarity	NPD7261	Clinical (unspecified phase)

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