NPASS Compound

Structure

CID143438 OpenBabel06191715502D 21 23 0 0 0 0 0 0 0 0999 V2000 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 -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 -2.5981 0.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 0.8660 1.5000 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 1.7321 0.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 5 2 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	3.333
LogD:	2.151
LogS:	-4.104
# Rotatable Bonds:	0
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	2.799
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.244
MDCK Permeability:	9.060494448931422e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.174
20% Bioavailability (F20%):	0.476
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.6645736694336%
Volume Distribution (VD):	0.37
Pgp-substrate:	4.402225017547607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.643
CYP2C9-substrate:	0.481
CYP2D6-inhibitor:	0.391
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	8.585
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.483
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.775
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.94
Carcinogencity:	0.499
Eye Corrosion:	0.013
Eye Irritation:	0.941
Respiratory Toxicity:	0.158

Download Data

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

Natural Product: NPC143438

Natural Product ID:	NPC143438
*Common Name:**	Catenarin
IUPAC Name:	1,4,5,7-tetrahydroxy-2-methylanthracene-9,10-dione
Synonyms:	Catenarin
Standard InCHIKey:	VWDXGKUTGQJJHJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c1-5-2-8(17)11-12(13(5)19)14(20)7-3-6(16)4-9(18)10(7)15(11)21/h2-4,16-19H,1H3
SMILES:	Oc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL29860
PubChem CID:	10150
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)90945-1]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374975]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24704449]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26967731]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22796	Cyperus rotundus	Species	Cyperaceae	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	8
MIC	1
Others	2

Activity Type	# Activity
Cell Line	9
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1306	Cell Line	WISH	Homo sapiens	IC50	>	100000.0	nM	PMID[471458]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	100000.0	nM	PMID[471458]
NPT80	Cell Line	Raji	Homo sapiens	IC50	>	100000.0	nM	PMID[471458]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[471458]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[471458]
NPT1307	Cell Line	Calu-1	Homo sapiens	IC50	>	100000.0	nM	PMID[471458]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	>	80.0	%	PMID[471459]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	41320.0	nM	PMID[471459]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	>=	80.0	%	PMID[471459]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	150000.0	nM	PMID[471457]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	100.0	ug.mL-1	PMID[471460]

☑ 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 NPC143438 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	434
0.1-0.2	1863
0.2-0.3	4307
0.3-0.4	11376
0.4-0.5	7412
0.5-0.6	5189
0.6-0.7	6025
0.7-0.8	5168
0.8-0.85	651
0.85-0.9	224
0.9-0.95	38
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC254847
0.9699	High Similarity	NPC471905
0.9699	High Similarity	NPC53414
0.9699	High Similarity	NPC53206
0.9556	High Similarity	NPC138099
0.9556	High Similarity	NPC190457
0.9556	High Similarity	NPC242994
0.9545	High Similarity	NPC267205
0.9485	High Similarity	NPC169452
0.9485	High Similarity	NPC181560
0.9474	High Similarity	NPC44437
0.9416	High Similarity	NPC290550
0.9416	High Similarity	NPC246638
0.9416	High Similarity	NPC204045
0.9416	High Similarity	NPC305845
0.9353	High Similarity	NPC471906
0.9353	High Similarity	NPC244691
0.9348	High Similarity	NPC135524
0.9348	High Similarity	NPC193555
0.9333	High Similarity	NPC191976
0.9281	High Similarity	NPC238629
0.9248	High Similarity	NPC205992
0.9231	High Similarity	NPC294646
0.9214	High Similarity	NPC21599
0.9214	High Similarity	NPC193703
0.9214	High Similarity	NPC48762
0.9209	High Similarity	NPC73061
0.9209	High Similarity	NPC474961
0.9185	High Similarity	NPC282780
0.9185	High Similarity	NPC166480
0.9155	High Similarity	NPC37709
0.9149	High Similarity	NPC34482
0.9137	High Similarity	NPC187843
0.9118	High Similarity	NPC161632
0.9098	High Similarity	NPC99731
0.9085	High Similarity	NPC470570
0.9078	High Similarity	NPC10764
0.9065	High Similarity	NPC203063
0.9023	High Similarity	NPC282923
0.9021	High Similarity	NPC118027
0.9021	High Similarity	NPC126767
0.9021	High Similarity	NPC56433
0.9021	High Similarity	NPC289042
0.9021	High Similarity	NPC190648
0.9021	High Similarity	NPC245584
0.9021	High Similarity	NPC312929
0.9	High Similarity	NPC110810
0.8971	High Similarity	NPC52407
0.8966	High Similarity	NPC147735
0.8958	High Similarity	NPC471907
0.8944	High Similarity	NPC19896
0.8944	High Similarity	NPC227841
0.8939	High Similarity	NPC10926
0.8921	High Similarity	NPC13715
0.8921	High Similarity	NPC61398
0.8921	High Similarity	NPC416
0.8921	High Similarity	NPC4214
0.8913	High Similarity	NPC474813
0.8913	High Similarity	NPC272268
0.8913	High Similarity	NPC118919
0.8913	High Similarity	NPC155211
0.8897	High Similarity	NPC70622
0.8881	High Similarity	NPC471683
0.8873	High Similarity	NPC293545
0.8873	High Similarity	NPC313047
0.8873	High Similarity	NPC451542
0.8873	High Similarity	NPC295712
0.8873	High Similarity	NPC474203
0.8873	High Similarity	NPC174905
0.8872	High Similarity	NPC8745
0.8872	High Similarity	NPC96915
0.8849	High Similarity	NPC147418
0.8849	High Similarity	NPC245923
0.8849	High Similarity	NPC53001
0.8841	High Similarity	NPC283088
0.8836	High Similarity	NPC255641
0.8836	High Similarity	NPC290954
0.8836	High Similarity	NPC470568
0.8832	High Similarity	NPC48036
0.8832	High Similarity	NPC314048
0.8824	High Similarity	NPC93015
0.8815	High Similarity	NPC92624
0.8815	High Similarity	NPC278928
0.8797	High Similarity	NPC103540
0.8794	High Similarity	NPC183345
0.8786	High Similarity	NPC123714
0.8786	High Similarity	NPC87723
0.8776	High Similarity	NPC470569
0.8768	High Similarity	NPC12070
0.8768	High Similarity	NPC288089
0.8768	High Similarity	NPC474519
0.8768	High Similarity	NPC50924
0.8759	High Similarity	NPC175738
0.8759	High Similarity	NPC290194
0.875	High Similarity	NPC259942
0.875	High Similarity	NPC147757
0.875	High Similarity	NPC136588
0.875	High Similarity	NPC12402
0.875	High Similarity	NPC199253
0.875	High Similarity	NPC31799
0.875	High Similarity	NPC62219
0.8742	High Similarity	NPC84571
0.8741	High Similarity	NPC471682
0.8741	High Similarity	NPC179898
0.8731	High Similarity	NPC160499
0.8725	High Similarity	NPC66029
0.8722	High Similarity	NPC13238
0.8722	High Similarity	NPC142956
0.8722	High Similarity	NPC173978
0.8716	High Similarity	NPC40356
0.8716	High Similarity	NPC154683
0.8707	High Similarity	NPC280295
0.8705	High Similarity	NPC249272
0.8705	High Similarity	NPC290803
0.8705	High Similarity	NPC258502
0.8705	High Similarity	NPC80035
0.8696	High Similarity	NPC115458
0.8696	High Similarity	NPC114183
0.8696	High Similarity	NPC37299
0.8696	High Similarity	NPC225051
0.8696	High Similarity	NPC180261
0.869	High Similarity	NPC271944
0.869	High Similarity	NPC110882
0.869	High Similarity	NPC85393
0.869	High Similarity	NPC300540
0.8684	High Similarity	NPC311740
0.8676	High Similarity	NPC109123
0.8676	High Similarity	NPC474998
0.8671	High Similarity	NPC257644
0.8671	High Similarity	NPC94076
0.8671	High Similarity	NPC182255
0.8671	High Similarity	NPC19631
0.8671	High Similarity	NPC137649
0.8671	High Similarity	NPC239136
0.8667	High Similarity	NPC105157
0.8667	High Similarity	NPC190043
0.8667	High Similarity	NPC266689
0.8667	High Similarity	NPC162612
0.8667	High Similarity	NPC100067
0.8667	High Similarity	NPC98254
0.8667	High Similarity	NPC30501
0.8667	High Similarity	NPC103356
0.8667	High Similarity	NPC72158
0.8667	High Similarity	NPC23126
0.8667	High Similarity	NPC169250
0.8662	High Similarity	NPC156872
0.8658	High Similarity	NPC470408
0.8658	High Similarity	NPC182921
0.8658	High Similarity	NPC218870
0.8658	High Similarity	NPC208806
0.8658	High Similarity	NPC214632
0.8658	High Similarity	NPC474824
0.8658	High Similarity	NPC107109
0.8657	High Similarity	NPC477454
0.8647	High Similarity	NPC375356
0.8643	High Similarity	NPC315275
0.8639	High Similarity	NPC477221
0.8633	High Similarity	NPC270899
0.863	High Similarity	NPC34802
0.8623	High Similarity	NPC478190
0.8613	High Similarity	NPC31539
0.8611	High Similarity	NPC167663
0.8611	High Similarity	NPC296752
0.8611	High Similarity	NPC66593
0.8611	High Similarity	NPC84266
0.8603	High Similarity	NPC221777
0.8603	High Similarity	NPC473017
0.8603	High Similarity	NPC48248
0.8603	High Similarity	NPC21305
0.8601	High Similarity	NPC92079
0.8601	High Similarity	NPC124365
0.86	High Similarity	NPC66508
0.86	High Similarity	NPC226656
0.8593	High Similarity	NPC3224
0.8593	High Similarity	NPC267846
0.8593	High Similarity	NPC473691
0.8593	High Similarity	NPC62952
0.8592	High Similarity	NPC26924
0.8592	High Similarity	NPC162939
0.8591	High Similarity	NPC175978
0.8582	High Similarity	NPC290030
0.8582	High Similarity	NPC44960
0.8582	High Similarity	NPC474110
0.8582	High Similarity	NPC471452
0.8582	High Similarity	NPC305060
0.8581	High Similarity	NPC315520
0.8581	High Similarity	NPC227122
0.8581	High Similarity	NPC205766
0.8581	High Similarity	NPC202595
0.8571	High Similarity	NPC133909
0.8571	High Similarity	NPC91478
0.8571	High Similarity	NPC32032
0.8571	High Similarity	NPC278375
0.8571	High Similarity	NPC2569
0.8571	High Similarity	NPC172329
0.8571	High Similarity	NPC300274
0.8561	High Similarity	NPC294226
0.8561	High Similarity	NPC53896
0.8561	High Similarity	NPC139074
0.8561	High Similarity	NPC213485

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 NPC143438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	989
0.2-0.3	1646
0.3-0.4	2957
0.4-0.5	1894
0.5-0.6	873
0.6-0.7	268
0.7-0.8	97
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9773	High Similarity	NPD1509	Clinical (unspecified phase)
0.8944	High Similarity	NPD7390	Discontinued
0.8797	High Similarity	NPD1470	Approved
0.8496	Intermediate Similarity	NPD1201	Approved
0.8489	Intermediate Similarity	NPD943	Approved
0.8322	Intermediate Similarity	NPD5405	Approved
0.8322	Intermediate Similarity	NPD5404	Approved
0.8322	Intermediate Similarity	NPD5408	Approved
0.8322	Intermediate Similarity	NPD5406	Approved
0.8252	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6232	Discontinued
0.8113	Intermediate Similarity	NPD7473	Discontinued
0.8112	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7972	Intermediate Similarity	NPD1240	Approved
0.791	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD3226	Approved
0.7881	Intermediate Similarity	NPD2532	Approved
0.7881	Intermediate Similarity	NPD2534	Approved
0.7881	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2533	Approved
0.7838	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7821	Intermediate Similarity	NPD7819	Suspended
0.7763	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1164	Approved
0.7718	Intermediate Similarity	NPD1549	Phase 2
0.7707	Intermediate Similarity	NPD2801	Approved
0.7707	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1511	Approved
0.7651	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2346	Discontinued
0.7651	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4380	Phase 2
0.7597	Intermediate Similarity	NPD1512	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7562	Intermediate Similarity	NPD3749	Approved
0.755	Intermediate Similarity	NPD2800	Approved
0.7547	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1934	Approved
0.7518	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD3750	Approved
0.7482	Intermediate Similarity	NPD9268	Approved
0.7469	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD7411	Suspended
0.7457	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3300	Phase 2
0.7357	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2796	Approved
0.7347	Intermediate Similarity	NPD3764	Approved
0.7346	Intermediate Similarity	NPD7075	Discontinued
0.7315	Intermediate Similarity	NPD230	Phase 1
0.7305	Intermediate Similarity	NPD3019	Approved
0.7303	Intermediate Similarity	NPD2344	Approved
0.7289	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3882	Suspended
0.7284	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD5710	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6020	Phase 2
0.7237	Intermediate Similarity	NPD6099	Approved
0.7237	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD1551	Phase 2
0.7225	Intermediate Similarity	NPD8150	Discontinued
0.7208	Intermediate Similarity	NPD1243	Approved
0.7188	Intermediate Similarity	NPD6599	Discontinued
0.7186	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6166	Phase 2
0.7186	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2932	Approved
0.7178	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3748	Approved
0.7171	Intermediate Similarity	NPD2799	Discontinued
0.7171	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6777	Approved
0.7167	Intermediate Similarity	NPD6778	Approved
0.7167	Intermediate Similarity	NPD6780	Approved
0.7167	Intermediate Similarity	NPD6782	Approved
0.7167	Intermediate Similarity	NPD6776	Approved
0.7167	Intermediate Similarity	NPD6779	Approved
0.7167	Intermediate Similarity	NPD6781	Approved
0.7161	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6651	Approved
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7115	Intermediate Similarity	NPD2309	Approved
0.7114	Intermediate Similarity	NPD2313	Discontinued
0.7108	Intermediate Similarity	NPD1247	Approved
0.7107	Intermediate Similarity	NPD920	Approved
0.7101	Intermediate Similarity	NPD7635	Approved
0.7101	Intermediate Similarity	NPD3818	Discontinued
0.7099	Intermediate Similarity	NPD6801	Discontinued
0.7097	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD9266	Approved
0.7059	Intermediate Similarity	NPD74	Approved
0.7051	Intermediate Similarity	NPD7003	Approved
0.7051	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7697	Approved
0.7049	Intermediate Similarity	NPD7696	Phase 3
0.7049	Intermediate Similarity	NPD7435	Discontinued
0.7025	Intermediate Similarity	NPD6799	Approved
0.7022	Intermediate Similarity	NPD6212	Phase 3
0.7022	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6213	Phase 3
0.7021	Intermediate Similarity	NPD9493	Approved
0.7012	Intermediate Similarity	NPD5402	Approved
0.7012	Intermediate Similarity	NPD3817	Phase 2
0.7011	Intermediate Similarity	NPD7870	Phase 2
0.7011	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD5951	Approved
0.6985	Remote Similarity	NPD9264	Approved
0.6985	Remote Similarity	NPD9267	Approved
0.6985	Remote Similarity	NPD2342	Discontinued
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9263	Approved
0.6981	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5953	Discontinued
0.6959	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2798	Approved
0.6952	Remote Similarity	NPD8151	Discontinued
0.6939	Remote Similarity	NPD1283	Approved
0.6933	Remote Similarity	NPD4625	Phase 3
0.6919	Remote Similarity	NPD7074	Phase 3
0.6917	Remote Similarity	NPD1242	Phase 1
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD3751	Discontinued
0.6898	Remote Similarity	NPD7701	Phase 2
0.6897	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3026	Approved
0.6897	Remote Similarity	NPD3023	Approved
0.6892	Remote Similarity	NPD1203	Approved
0.689	Remote Similarity	NPD37	Approved
0.6882	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3025	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD3024	Approved
0.6866	Remote Similarity	NPD940	Approved
0.6866	Remote Similarity	NPD846	Approved
0.686	Remote Similarity	NPD7054	Approved
0.686	Remote Similarity	NPD7286	Phase 2
0.6857	Remote Similarity	NPD8312	Approved
0.6857	Remote Similarity	NPD8313	Approved
0.6855	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8320	Phase 1
0.6828	Remote Similarity	NPD8319	Approved
0.6825	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7874	Approved
0.6824	Remote Similarity	NPD3926	Phase 2
0.6821	Remote Similarity	NPD7472	Approved
0.6811	Remote Similarity	NPD6823	Phase 2
0.6807	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD9545	Approved
0.6803	Remote Similarity	NPD3972	Approved
0.68	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6190	Approved
0.679	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7801	Approved
0.6786	Remote Similarity	NPD919	Approved
0.6786	Remote Similarity	NPD6234	Discontinued
0.6782	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6797	Phase 2
0.6776	Remote Similarity	NPD411	Approved
0.6766	Remote Similarity	NPD4965	Approved
0.6766	Remote Similarity	NPD4966	Approved
0.6766	Remote Similarity	NPD4967	Phase 2
0.6765	Remote Similarity	NPD7229	Phase 3
0.6761	Remote Similarity	NPD497	Approved
0.6761	Remote Similarity	NPD9281	Approved
0.6755	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD447	Suspended
0.6743	Remote Similarity	NPD7251	Discontinued
0.6735	Remote Similarity	NPD1281	Approved
0.6731	Remote Similarity	NPD4308	Phase 3
0.673	Remote Similarity	NPD4628	Phase 3
0.6712	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1876	Approved
0.6705	Remote Similarity	NPD7808	Phase 3
0.6691	Remote Similarity	NPD9261	Approved
0.669	Remote Similarity	NPD498	Approved
0.669	Remote Similarity	NPD496	Approved
0.669	Remote Similarity	NPD495	Approved
0.6689	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4287	Approved
0.6667	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6859	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