NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.04
Volume:	239.1
LogP:	3.315
LogD:	2.753
LogS:	-4.931
# Rotatable Bonds:	0
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	2.042
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.907
MDCK Permeability:	1.3889446563553065e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238
Plasma Protein Binding (PPB):	98.35930633544922%
Volume Distribution (VD):	0.569
Pgp-substrate:	1.5671775341033936%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.233
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.607
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	8.015
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.876
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.598
Skin Sensitization:	0.372
Carcinogencity:	0.84
Eye Corrosion:	0.004
Eye Irritation:	0.974
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC44437

Natural Product ID:	NPC44437
*Common Name:**	Xanthopurpurin
IUPAC Name:	1,3-dihydroxyanthracene-9,10-dione
Synonyms:	1,3-Dihydroxy-Anthraquinone; Xanthopurpurin
Standard InCHIKey:	WPWWKBNOXTZDQJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H
SMILES:	c1ccc2c(c1)C(=O)c1cc(cc(c1C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL372711
PubChem CID:	196978
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
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350148]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762798]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21044847]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	root	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[21973054]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22860454]
NPO20880	Conocybe siliginea	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32816486]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30535	Morinda umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20572	Vepris louisii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4192	Gynochthodes umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2784	Radix rubiae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30535	Morinda umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8020	Lychnophora columnaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20064	Litsea konishii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20364	Ophelia bicornis	Species	Opheliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4192	Gynochthodes umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10014	Rubia tinctorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20822	Asperula odora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15980	Croton penduliflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17395	Asperula odorata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19956	Pulveroboletus retipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20572	Vepris louisii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20880	Conocybe siliginea	Species	Bolbitiaceae	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	5
Ki	2
Others	4

Activity Type	# Activity
Cell Line	3
CELL-LINE	4
Individual Protein	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	Ki	=	2270.0	nM	PMID[489859]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	29000.0	nM	PMID[489860]
NPT2844	Cell Line	MES-SA	Homo sapiens	IC50	=	30000.0	nM	PMID[489860]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	55000.0	nM	PMID[489860]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	86.9	%	PMID[489858]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	85.0	%	PMID[489858]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	3.8	%	PMID[489858]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	82.6	%	PMID[489858]
NPT980	Individual Protein	Apoptosis regulator Bcl-2	Homo sapiens	Ki	=	1700.0	nM	PMID[489859]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23000.0	nM	PMID[489860]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21000.0	nM	PMID[489860]

☑ 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 NPC44437 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	440
0.1-0.2	1819
0.2-0.3	4203
0.3-0.4	11175
0.4-0.5	7436
0.5-0.6	5055
0.6-0.7	6295
0.7-0.8	5229
0.8-0.85	726
0.85-0.9	248
0.9-0.95	58
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9769	High Similarity	NPC53414
0.9769	High Similarity	NPC53206
0.9692	High Similarity	NPC254847
0.9621	High Similarity	NPC242994
0.9621	High Similarity	NPC138099
0.9618	High Similarity	NPC471905
0.9549	High Similarity	NPC203063
0.9549	High Similarity	NPC169452
0.9549	High Similarity	NPC181560
0.9474	High Similarity	NPC143438
0.9474	High Similarity	NPC190457
0.9462	High Similarity	NPC267205
0.9407	High Similarity	NPC193555
0.9407	High Similarity	NPC73061
0.9389	High Similarity	NPC282780
0.9389	High Similarity	NPC166480
0.937	High Similarity	NPC8745
0.9338	High Similarity	NPC238629
0.9333	High Similarity	NPC204045
0.9333	High Similarity	NPC246638
0.9333	High Similarity	NPC305845
0.9333	High Similarity	NPC290550
0.9302	High Similarity	NPC99731
0.9291	High Similarity	NPC10926
0.9291	High Similarity	NPC103540
0.927	High Similarity	NPC193703
0.927	High Similarity	NPC21599
0.9265	High Similarity	NPC135524
0.9248	High Similarity	NPC191976
0.9213	High Similarity	NPC13238
0.9154	High Similarity	NPC92624
0.9134	High Similarity	NPC375356
0.913	High Similarity	NPC244691
0.913	High Similarity	NPC19896
0.913	High Similarity	NPC48762
0.913	High Similarity	NPC471906
0.9091	High Similarity	NPC175738
0.9084	High Similarity	NPC259942
0.9077	High Similarity	NPC179898
0.9077	High Similarity	NPC282923
0.9065	High Similarity	NPC34482
0.9055	High Similarity	NPC91478
0.9055	High Similarity	NPC133909
0.9055	High Similarity	NPC300274
0.9055	High Similarity	NPC32032
0.903	High Similarity	NPC161632
0.9023	High Similarity	NPC52407
0.9023	High Similarity	NPC294226
0.9015	High Similarity	NPC93015
0.9	High Similarity	NPC470570
0.8986	High Similarity	NPC474961
0.8986	High Similarity	NPC137649
0.8976	High Similarity	NPC73532
0.8976	High Similarity	NPC242895
0.8976	High Similarity	NPC156139
0.8976	High Similarity	NPC224273
0.8976	High Similarity	NPC19174
0.8976	High Similarity	NPC115159
0.8976	High Similarity	NPC45438
0.8976	High Similarity	NPC267552
0.8976	High Similarity	NPC120545
0.8976	High Similarity	NPC143427
0.8971	High Similarity	NPC416
0.8971	High Similarity	NPC4214
0.8971	High Similarity	NPC61398
0.8971	High Similarity	NPC13715
0.8963	High Similarity	NPC118919
0.8947	High Similarity	NPC135801
0.8947	High Similarity	NPC70622
0.8939	High Similarity	NPC147757
0.8939	High Similarity	NPC31799
0.8936	High Similarity	NPC190648
0.8936	High Similarity	NPC312929
0.8936	High Similarity	NPC126767
0.8936	High Similarity	NPC37709
0.8936	High Similarity	NPC245584
0.8936	High Similarity	NPC118027
0.8936	High Similarity	NPC56433
0.8936	High Similarity	NPC289042
0.8923	High Similarity	NPC3224
0.8923	High Similarity	NPC96915
0.8921	High Similarity	NPC474203
0.8921	High Similarity	NPC451542
0.8921	High Similarity	NPC313047
0.8921	High Similarity	NPC295712
0.8898	High Similarity	NPC248363
0.8898	High Similarity	NPC297186
0.8897	High Similarity	NPC290030
0.8897	High Similarity	NPC147418
0.8889	High Similarity	NPC283088
0.8881	High Similarity	NPC255641
0.8881	High Similarity	NPC290954
0.8873	High Similarity	NPC471907
0.8872	High Similarity	NPC34070
0.8872	High Similarity	NPC469526
0.8872	High Similarity	NPC205992
0.8864	High Similarity	NPC474998
0.8864	High Similarity	NPC109123
0.8855	High Similarity	NPC103356
0.8855	High Similarity	NPC190043
0.8855	High Similarity	NPC100067
0.8855	High Similarity	NPC30501
0.8855	High Similarity	NPC105157
0.8855	High Similarity	NPC98254
0.8855	High Similarity	NPC23126
0.8855	High Similarity	NPC162612
0.8855	High Similarity	NPC72158
0.8855	High Similarity	NPC169250
0.8855	High Similarity	NPC266689
0.8846	High Similarity	NPC477454
0.8841	High Similarity	NPC183345
0.8841	High Similarity	NPC156872
0.8819	High Similarity	NPC159525
0.8815	High Similarity	NPC50924
0.8815	High Similarity	NPC288089
0.8806	High Similarity	NPC478190
0.8797	High Similarity	NPC199253
0.8797	High Similarity	NPC26697
0.8797	High Similarity	NPC136588
0.8797	High Similarity	NPC233056
0.8788	High Similarity	NPC21305
0.8788	High Similarity	NPC95537
0.8788	High Similarity	NPC473017
0.8788	High Similarity	NPC221777
0.8786	High Similarity	NPC174905
0.8786	High Similarity	NPC293545
0.8779	High Similarity	NPC473691
0.8779	High Similarity	NPC62952
0.8779	High Similarity	NPC231774
0.8779	High Similarity	NPC160499
0.8779	High Similarity	NPC267846
0.8777	High Similarity	NPC187843
0.8777	High Similarity	NPC110810
0.8769	High Similarity	NPC142956
0.8769	High Similarity	NPC173978
0.8768	High Similarity	NPC472903
0.8759	High Similarity	NPC53001
0.8759	High Similarity	NPC44960
0.8759	High Similarity	NPC474110
0.8759	High Similarity	NPC149889
0.8759	High Similarity	NPC312338
0.875	High Similarity	NPC80035
0.875	High Similarity	NPC258502
0.875	High Similarity	NPC147735
0.875	High Similarity	NPC294646
0.875	High Similarity	NPC470568
0.8741	High Similarity	NPC115458
0.8741	High Similarity	NPC225051
0.8741	High Similarity	NPC48036
0.874	High Similarity	NPC158222
0.8732	High Similarity	NPC110882
0.8732	High Similarity	NPC271944
0.8732	High Similarity	NPC85393
0.8731	High Similarity	NPC244699
0.8723	High Similarity	NPC475201
0.8723	High Similarity	NPC10764
0.8723	High Similarity	NPC227841
0.8714	High Similarity	NPC19631
0.8714	High Similarity	NPC49108
0.8714	High Similarity	NPC239136
0.8714	High Similarity	NPC257644
0.8712	High Similarity	NPC116513
0.8702	High Similarity	NPC262671
0.8702	High Similarity	NPC201728
0.8699	High Similarity	NPC208806
0.8696	High Similarity	NPC20210
0.8696	High Similarity	NPC87723
0.869	High Similarity	NPC470569
0.8686	High Similarity	NPC194764
0.8686	High Similarity	NPC264112
0.8686	High Similarity	NPC65005
0.8682	High Similarity	NPC196976
0.8676	High Similarity	NPC12070
0.8676	High Similarity	NPC474519
0.8662	High Similarity	NPC12402
0.8657	High Similarity	NPC62219
0.8657	High Similarity	NPC17840
0.8657	High Similarity	NPC247477
0.8652	High Similarity	NPC296752
0.8652	High Similarity	NPC66593
0.8652	High Similarity	NPC471682
0.8647	High Similarity	NPC48248
0.8647	High Similarity	NPC41263
0.8647	High Similarity	NPC234175
0.8643	High Similarity	NPC472904
0.8639	High Similarity	NPC226656
0.8639	High Similarity	NPC66508
0.8633	High Similarity	NPC26924
0.8633	High Similarity	NPC162939
0.863	High Similarity	NPC40356
0.863	High Similarity	NPC154683
0.8621	High Similarity	NPC280295
0.8621	High Similarity	NPC205766
0.8615	High Similarity	NPC283514
0.8615	High Similarity	NPC309765
0.8613	High Similarity	NPC249272
0.8613	High Similarity	NPC290803
0.8605	High Similarity	NPC146642
0.8603	High Similarity	NPC139074
0.8603	High Similarity	NPC314048

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 NPC44437 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	966
0.2-0.3	1516
0.3-0.4	2899
0.4-0.5	1955
0.5-0.6	969
0.6-0.7	312
0.7-0.8	102
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9692	High Similarity	NPD1509	Clinical (unspecified phase)
0.9291	High Similarity	NPD1470	Approved
0.8976	High Similarity	NPD1201	Approved
0.8947	High Similarity	NPD943	Approved
0.8723	High Similarity	NPD7390	Discontinued
0.8551	High Similarity	NPD651	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD5406	Approved
0.8489	Intermediate Similarity	NPD5404	Approved
0.8489	Intermediate Similarity	NPD5405	Approved
0.8489	Intermediate Similarity	NPD5408	Approved
0.8417	Intermediate Similarity	NPD1510	Phase 2
0.8359	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1607	Approved
0.8261	Intermediate Similarity	NPD1240	Approved
0.8112	Intermediate Similarity	NPD1549	Phase 2
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.8042	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8015	Intermediate Similarity	NPD1164	Approved
0.7986	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7819	Suspended
0.7959	Intermediate Similarity	NPD1511	Approved
0.7922	Intermediate Similarity	NPD3749	Approved
0.7905	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD3750	Approved
0.7852	Intermediate Similarity	NPD1512	Approved
0.7815	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7763	Intermediate Similarity	NPD4380	Phase 2
0.773	Intermediate Similarity	NPD3764	Approved
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD2532	Approved
0.7667	Intermediate Similarity	NPD2533	Approved
0.7664	Intermediate Similarity	NPD9269	Phase 2
0.7662	Intermediate Similarity	NPD1934	Approved
0.763	Intermediate Similarity	NPD9268	Approved
0.7613	Intermediate Similarity	NPD2801	Approved
0.7603	Intermediate Similarity	NPD2796	Approved
0.7603	Intermediate Similarity	NPD2935	Discontinued
0.7597	Intermediate Similarity	NPD7411	Suspended
0.7574	Intermediate Similarity	NPD3019	Approved
0.7551	Intermediate Similarity	NPD2344	Approved
0.7551	Intermediate Similarity	NPD2346	Discontinued
0.7534	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3748	Approved
0.7533	Intermediate Similarity	NPD3300	Phase 2
0.7516	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD1551	Phase 2
0.7468	Intermediate Similarity	NPD7075	Discontinued
0.7462	Intermediate Similarity	NPD74	Approved
0.7462	Intermediate Similarity	NPD9266	Approved
0.745	Intermediate Similarity	NPD2800	Approved
0.7445	Intermediate Similarity	NPD2932	Approved
0.7407	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7768	Phase 2
0.74	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1465	Phase 2
0.7385	Intermediate Similarity	NPD9264	Approved
0.7385	Intermediate Similarity	NPD9267	Approved
0.7385	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD9263	Approved
0.7372	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2309	Approved
0.7329	Intermediate Similarity	NPD230	Phase 1
0.7323	Intermediate Similarity	NPD1242	Phase 1
0.7317	Intermediate Similarity	NPD3818	Discontinued
0.7315	Intermediate Similarity	NPD1471	Phase 3
0.7308	Intermediate Similarity	NPD6599	Discontinued
0.7301	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6166	Phase 2
0.7301	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD6020	Phase 2
0.7267	Intermediate Similarity	NPD5494	Approved
0.7255	Intermediate Similarity	NPD6799	Approved
0.7254	Intermediate Similarity	NPD1203	Approved
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7241	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1243	Approved
0.7215	Intermediate Similarity	NPD6801	Discontinued
0.7203	Intermediate Similarity	NPD2798	Approved
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD3023	Approved
0.7143	Intermediate Similarity	NPD3026	Approved
0.7143	Intermediate Similarity	NPD4750	Phase 3
0.7132	Intermediate Similarity	NPD846	Approved
0.7132	Intermediate Similarity	NPD940	Approved
0.7132	Intermediate Similarity	NPD9281	Approved
0.7125	Intermediate Similarity	NPD3817	Phase 2
0.7122	Intermediate Similarity	NPD3025	Approved
0.7122	Intermediate Similarity	NPD3024	Approved
0.7121	Intermediate Similarity	NPD2342	Discontinued
0.7115	Intermediate Similarity	NPD920	Approved
0.7097	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5953	Discontinued
0.7078	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD9261	Approved
0.7073	Intermediate Similarity	NPD5711	Approved
0.7073	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD9545	Approved
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7035	Intermediate Similarity	NPD8150	Discontinued
0.703	Intermediate Similarity	NPD3926	Phase 2
0.7025	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7074	Phase 3
0.7019	Intermediate Similarity	NPD5402	Approved
0.7007	Intermediate Similarity	NPD5951	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6535	Approved
0.6989	Remote Similarity	NPD6534	Approved
0.6972	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7054	Approved
0.6964	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4287	Approved
0.6944	Remote Similarity	NPD1283	Approved
0.6944	Remote Similarity	NPD1876	Approved
0.6939	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD7472	Approved
0.6923	Remote Similarity	NPD4878	Approved
0.6923	Remote Similarity	NPD9717	Approved
0.6918	Remote Similarity	NPD7458	Discontinued
0.6914	Remote Similarity	NPD4288	Approved
0.6909	Remote Similarity	NPD1247	Approved
0.6903	Remote Similarity	NPD6190	Approved
0.6901	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5403	Approved
0.6894	Remote Similarity	NPD37	Approved
0.6892	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD411	Approved
0.689	Remote Similarity	NPD919	Approved
0.6889	Remote Similarity	NPD6777	Approved
0.6889	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6781	Approved
0.6889	Remote Similarity	NPD6776	Approved
0.6889	Remote Similarity	NPD6780	Approved
0.6889	Remote Similarity	NPD6778	Approved
0.6889	Remote Similarity	NPD6779	Approved
0.6889	Remote Similarity	NPD6782	Approved
0.6882	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6797	Phase 2
0.6879	Remote Similarity	NPD1651	Approved
0.6879	Remote Similarity	NPD5401	Approved
0.6872	Remote Similarity	NPD7700	Phase 2
0.6872	Remote Similarity	NPD7699	Phase 2
0.6867	Remote Similarity	NPD447	Suspended
0.6864	Remote Similarity	NPD7286	Phase 2
0.686	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD8313	Approved
0.6857	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1610	Phase 2
0.6848	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6663	Approved
0.6842	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD7251	Discontinued
0.6839	Remote Similarity	NPD8166	Discontinued
0.6839	Remote Similarity	NPD4628	Phase 3
0.681	Remote Similarity	NPD2296	Approved
0.681	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1608	Approved
0.6803	Remote Similarity	NPD5736	Approved
0.6802	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6234	Discontinued
0.6779	Remote Similarity	NPD3268	Approved
0.6779	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7435	Discontinued
0.6776	Remote Similarity	NPD7698	Approved
0.6776	Remote Similarity	NPD7697	Approved
0.6776	Remote Similarity	NPD7696	Phase 3
0.6774	Remote Similarity	NPD8151	Discontinued
0.6772	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4965	Approved
0.6768	Remote Similarity	NPD4966	Approved
0.6768	Remote Similarity	NPD4967	Phase 2
0.6767	Remote Similarity	NPD1237	Approved
0.6766	Remote Similarity	NPD7229	Phase 3
0.6757	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4908	Phase 1
0.6742	Remote Similarity	NPD6213	Phase 3
0.6742	Remote Similarity	NPD6212	Phase 3
0.6742	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7871	Phase 2

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