NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.04
Volume:	262.55
LogP:	3.743
LogD:	2.386
LogS:	-4.762
# Rotatable Bonds:	1
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	2.438
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.952
MDCK Permeability:	1.0133071555173956e-05
Pgp-inhibitor:	0.412
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.08
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	99.06681060791016%
Volume Distribution (VD):	0.487
Pgp-substrate:	0.9490590691566467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.542
CYP2C9-substrate:	0.221
CYP2D6-inhibitor:	0.334
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.457
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	1.993
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.807
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.485
Skin Sensitization:	0.535
Carcinogencity:	0.824
Eye Corrosion:	0.005
Eye Irritation:	0.961
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC73061

Natural Product ID:	NPC73061
*Common Name:**	1,3-Dihydroxy-2-Formylanthraquinone
IUPAC Name:	1,3-dihydroxy-9,10-dioxoanthracene-2-carbaldehyde
Synonyms:
Standard InCHIKey:	NSGZEHPFOUCUHD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H8O5/c16-6-10-11(17)5-9-12(15(10)20)14(19)8-4-2-1-3-7(8)13(9)18/h1-6,17,20H
SMILES:	c1ccc2c(c1)C(=O)c1cc(c(C=O)c(c1C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2297225
PubChem CID:	160712
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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520235]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1254564]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855442]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192236]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26048790]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26195800]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8626242]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28134	Coprosma lineariifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21767	Rubia iberica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26764	Morinda tinctoria	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]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21767	Rubia iberica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28134	Coprosma lineariifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6050	Hymenodictyon excelsum	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]
NPO16765	Knoxia valerianoides	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]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11827	Zerynthia polyxena	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21767	Rubia iberica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13446	Stachys recta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10807	Melanothamnus somalensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10967	Parmelia gigas	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15917	Monilinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2868	Perna viridis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6430	Cercosporina kikuchii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3376	Eriostemon brucei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26859	Solanum curtipes	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7106	Talaromyces helicus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11734	Chara corallina	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11305	Garcinia cantleyana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18675	Pteris aquilina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO861	Siphonaria funiculata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	42000.0	nM	PMID[508077]
NPT2844	Cell Line	MES-SA	Homo sapiens	IC50	=	18000.0	nM	PMID[508077]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	36000.0	nM	PMID[508077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40000.0	nM	PMID[508077]

☑ 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 NPC73061 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	425
0.1-0.2	1900
0.2-0.3	4260
0.3-0.4	11429
0.4-0.5	7306
0.5-0.6	5233
0.6-0.7	6110
0.7-0.8	5248
0.8-0.85	604
0.85-0.9	138
0.9-0.95	43
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9489	High Similarity	NPC190457
0.9485	High Similarity	NPC53414
0.9485	High Similarity	NPC53206
0.9424	High Similarity	NPC193555
0.9412	High Similarity	NPC254847
0.9407	High Similarity	NPC44437
0.9353	High Similarity	NPC305845
0.9353	High Similarity	NPC290550
0.9353	High Similarity	NPC204045
0.9348	High Similarity	NPC138099
0.9348	High Similarity	NPC242994
0.9343	High Similarity	NPC471905
0.9291	High Similarity	NPC21599
0.9291	High Similarity	NPC193703
0.9286	High Similarity	NPC135524
0.9281	High Similarity	NPC169452
0.9281	High Similarity	NPC183345
0.9281	High Similarity	NPC181560
0.9265	High Similarity	NPC474519
0.9247	High Similarity	NPC208806
0.9209	High Similarity	NPC162939
0.9209	High Similarity	NPC143438
0.9191	High Similarity	NPC267205
0.9155	High Similarity	NPC471906
0.9155	High Similarity	NPC48762
0.9155	High Similarity	NPC244691
0.9091	High Similarity	NPC34482
0.9078	High Similarity	NPC187843
0.9078	High Similarity	NPC246638
0.9051	High Similarity	NPC52407
0.9044	High Similarity	NPC93015
0.9028	High Similarity	NPC470570
0.9014	High Similarity	NPC474961
0.9007	High Similarity	NPC203063
0.9	High Similarity	NPC13715
0.9	High Similarity	NPC4214
0.8993	High Similarity	NPC191976
0.8986	High Similarity	NPC282780
0.8986	High Similarity	NPC166480
0.8978	High Similarity	NPC70622
0.8971	High Similarity	NPC31799
0.8971	High Similarity	NPC62219
0.8921	High Similarity	NPC278375
0.8912	High Similarity	NPC290954
0.8912	High Similarity	NPC255641
0.8904	High Similarity	NPC471907
0.8897	High Similarity	NPC99731
0.8857	High Similarity	NPC86524
0.8849	High Similarity	NPC288089
0.8836	High Similarity	NPC126767
0.8836	High Similarity	NPC56433
0.8836	High Similarity	NPC190648
0.8836	High Similarity	NPC312929
0.8836	High Similarity	NPC289042
0.8836	High Similarity	NPC118027
0.8836	High Similarity	NPC245584
0.8832	High Similarity	NPC199253
0.8832	High Similarity	NPC136588
0.8824	High Similarity	NPC282923
0.8819	High Similarity	NPC238629
0.8819	High Similarity	NPC66593
0.8815	High Similarity	NPC8745
0.8803	High Similarity	NPC26924
0.8786	High Similarity	NPC161632
0.8786	High Similarity	NPC80035
0.8784	High Similarity	NPC147735
0.8784	High Similarity	NPC470568
0.8777	High Similarity	NPC48036
0.8777	High Similarity	NPC115458
0.8768	High Similarity	NPC275504
0.8767	High Similarity	NPC314437
0.8759	High Similarity	NPC19896
0.8759	High Similarity	NPC476119
0.875	High Similarity	NPC137649
0.8741	High Similarity	NPC10926
0.8741	High Similarity	NPC315578
0.8741	High Similarity	NPC103540
0.8732	High Similarity	NPC61398
0.8732	High Similarity	NPC416
0.8725	High Similarity	NPC470569
0.8723	High Similarity	NPC118919
0.8707	High Similarity	NPC37709
0.8699	High Similarity	NPC12402
0.8696	High Similarity	NPC147757
0.869	High Similarity	NPC295712
0.869	High Similarity	NPC474203
0.869	High Similarity	NPC313047
0.869	High Similarity	NPC451542
0.8681	High Similarity	NPC110810
0.8667	High Similarity	NPC40356
0.8667	High Similarity	NPC13238
0.8667	High Similarity	NPC154683
0.8658	High Similarity	NPC280295
0.8658	High Similarity	NPC294646
0.8652	High Similarity	NPC283088
0.8645	High Similarity	NPC101769
0.8643	High Similarity	NPC314048
0.8643	High Similarity	NPC53896
0.8633	High Similarity	NPC205992
0.8633	High Similarity	NPC41847
0.8623	High Similarity	NPC92624
0.8611	High Similarity	NPC96421
0.8611	High Similarity	NPC156872
0.8611	High Similarity	NPC99441
0.8609	High Similarity	NPC214632
0.8593	High Similarity	NPC375356
0.8592	High Similarity	NPC315275
0.8592	High Similarity	NPC272268
0.8582	High Similarity	NPC50924
0.8581	High Similarity	NPC290194
0.8571	High Similarity	NPC175738
0.8571	High Similarity	NPC478190
0.8571	High Similarity	NPC49282
0.8562	High Similarity	NPC293545
0.8562	High Similarity	NPC174905
0.8561	High Similarity	NPC259942
0.8553	High Similarity	NPC226656
0.8553	High Similarity	NPC66508
0.8552	High Similarity	NPC37530
0.8551	High Similarity	NPC95537
0.8551	High Similarity	NPC179898
0.854	High Similarity	NPC160499
0.8533	High Similarity	NPC205766
0.8531	High Similarity	NPC53001
0.8531	High Similarity	NPC471452
0.8529	High Similarity	NPC142956
0.8529	High Similarity	NPC173978
0.8521	High Similarity	NPC258502
0.8519	High Similarity	NPC133909
0.8519	High Similarity	NPC91478
0.8519	High Similarity	NPC32032
0.8519	High Similarity	NPC300274
0.8514	High Similarity	NPC110882
0.8514	High Similarity	NPC85393
0.8514	High Similarity	NPC271944
0.8514	High Similarity	NPC143685
0.8511	High Similarity	NPC213485
0.8511	High Similarity	NPC294226
0.8511	High Similarity	NPC40524
0.8511	High Similarity	NPC225051
0.8511	High Similarity	NPC139074
0.8511	High Similarity	NPC477139
0.8506	High Similarity	NPC324736
0.8503	High Similarity	NPC10764
0.8503	High Similarity	NPC227841
0.8503	High Similarity	NPC475201
0.8503	High Similarity	NPC79627
0.85	High Similarity	NPC475042
0.8497	Intermediate Similarity	NPC474861
0.8493	Intermediate Similarity	NPC469520
0.8493	Intermediate Similarity	NPC19631
0.8493	Intermediate Similarity	NPC182255
0.8493	Intermediate Similarity	NPC94076
0.8493	Intermediate Similarity	NPC257644
0.8493	Intermediate Similarity	NPC239136
0.8489	Intermediate Similarity	NPC474998
0.8489	Intermediate Similarity	NPC109123
0.8487	Intermediate Similarity	NPC107109
0.8487	Intermediate Similarity	NPC472211
0.8478	Intermediate Similarity	NPC162612
0.8478	Intermediate Similarity	NPC169250
0.8478	Intermediate Similarity	NPC23126
0.8478	Intermediate Similarity	NPC72158
0.8478	Intermediate Similarity	NPC98254
0.8478	Intermediate Similarity	NPC105157
0.8478	Intermediate Similarity	NPC103356
0.8478	Intermediate Similarity	NPC100067
0.8478	Intermediate Similarity	NPC190043
0.8478	Intermediate Similarity	NPC30501
0.8478	Intermediate Similarity	NPC266689
0.8472	Intermediate Similarity	NPC87723
0.8467	Intermediate Similarity	NPC477221
0.8467	Intermediate Similarity	NPC329933
0.8456	Intermediate Similarity	NPC119767
0.8456	Intermediate Similarity	NPC34802
0.8451	Intermediate Similarity	NPC12070
0.8446	Intermediate Similarity	NPC478019
0.8444	Intermediate Similarity	NPC156139
0.8444	Intermediate Similarity	NPC242895
0.8444	Intermediate Similarity	NPC45438
0.8444	Intermediate Similarity	NPC224273
0.8444	Intermediate Similarity	NPC120545
0.8444	Intermediate Similarity	NPC115159
0.8444	Intermediate Similarity	NPC19174
0.8444	Intermediate Similarity	NPC73532
0.8444	Intermediate Similarity	NPC267552
0.8444	Intermediate Similarity	NPC143427
0.8442	Intermediate Similarity	NPC178976
0.8442	Intermediate Similarity	NPC263483
0.844	Intermediate Similarity	NPC135801
0.8435	Intermediate Similarity	NPC84266
0.8435	Intermediate Similarity	NPC167663
0.8435	Intermediate Similarity	NPC471682
0.8435	Intermediate Similarity	NPC296752
0.8425	Intermediate Similarity	NPC91019
0.8425	Intermediate Similarity	NPC106519
0.8421	Intermediate Similarity	NPC312338
0.8421	Intermediate Similarity	NPC149889
0.8417	Intermediate Similarity	NPC48248
0.8417	Intermediate Similarity	NPC21305

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 NPC73061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	993
0.2-0.3	1600
0.3-0.4	2953
0.4-0.5	1887
0.5-0.6	921
0.6-0.7	269
0.7-0.8	93
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD1509	Clinical (unspecified phase)
0.8741	High Similarity	NPD1470	Approved
0.8503	High Similarity	NPD7390	Discontinued
0.8444	Intermediate Similarity	NPD1201	Approved
0.844	Intermediate Similarity	NPD943	Approved
0.8276	Intermediate Similarity	NPD5406	Approved
0.8276	Intermediate Similarity	NPD5405	Approved
0.8276	Intermediate Similarity	NPD5408	Approved
0.8276	Intermediate Similarity	NPD5404	Approved
0.8207	Intermediate Similarity	NPD1510	Phase 2
0.8082	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7963	Intermediate Similarity	NPD7473	Discontinued
0.7961	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1240	Approved
0.7919	Intermediate Similarity	NPD1549	Phase 2
0.7898	Intermediate Similarity	NPD7819	Suspended
0.7871	Intermediate Similarity	NPD3226	Approved
0.7868	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6959	Discontinued
0.7771	Intermediate Similarity	NPD7411	Suspended
0.7727	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD2532	Approved
0.7727	Intermediate Similarity	NPD2533	Approved
0.7727	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4380	Phase 2
0.7692	Intermediate Similarity	NPD1164	Approved
0.7682	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1551	Phase 2
0.7613	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1511	Approved
0.7531	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7468	Intermediate Similarity	NPD3750	Approved
0.7452	Intermediate Similarity	NPD1512	Approved
0.7434	Intermediate Similarity	NPD2796	Approved
0.7434	Intermediate Similarity	NPD2935	Discontinued
0.7423	Intermediate Similarity	NPD7075	Discontinued
0.7403	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7768	Phase 2
0.7362	Intermediate Similarity	NPD3882	Suspended
0.7346	Intermediate Similarity	NPD2801	Approved
0.7346	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5844	Phase 1
0.7315	Intermediate Similarity	NPD3764	Approved
0.731	Intermediate Similarity	NPD6559	Discontinued
0.7296	Intermediate Similarity	NPD920	Approved
0.7289	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7261	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9269	Phase 2
0.7232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5494	Approved
0.7212	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9268	Approved
0.7179	Intermediate Similarity	NPD2800	Approved
0.7178	Intermediate Similarity	NPD6801	Discontinued
0.7176	Intermediate Similarity	NPD3818	Discontinued
0.7171	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD2344	Approved
0.7161	Intermediate Similarity	NPD1471	Phase 3
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3019	Approved
0.7152	Intermediate Similarity	NPD3300	Phase 2
0.7152	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7143	Intermediate Similarity	NPD3748	Approved
0.7135	Intermediate Similarity	NPD6020	Phase 2
0.7107	Intermediate Similarity	NPD6799	Approved
0.7102	Intermediate Similarity	NPD8150	Discontinued
0.7099	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD919	Approved
0.7056	Intermediate Similarity	NPD6535	Approved
0.7056	Intermediate Similarity	NPD6534	Approved
0.7052	Intermediate Similarity	NPD5953	Discontinued
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2932	Approved
0.7032	Intermediate Similarity	NPD2799	Discontinued
0.703	Intermediate Similarity	NPD1465	Phase 2
0.7029	Intermediate Similarity	NPD9266	Approved
0.7029	Intermediate Similarity	NPD74	Approved
0.7025	Intermediate Similarity	NPD7003	Approved
0.7013	Intermediate Similarity	NPD6651	Approved
0.6994	Remote Similarity	NPD7458	Discontinued
0.6993	Remote Similarity	NPD9493	Approved
0.6988	Remote Similarity	NPD3817	Phase 2
0.6987	Remote Similarity	NPD6099	Approved
0.6987	Remote Similarity	NPD6100	Approved
0.6981	Remote Similarity	NPD2309	Approved
0.6974	Remote Similarity	NPD2313	Discontinued
0.6962	Remote Similarity	NPD1243	Approved
0.6957	Remote Similarity	NPD6782	Approved
0.6957	Remote Similarity	NPD6780	Approved
0.6957	Remote Similarity	NPD6777	Approved
0.6957	Remote Similarity	NPD6781	Approved
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2342	Discontinued
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD6778	Approved
0.6957	Remote Similarity	NPD6779	Approved
0.6957	Remote Similarity	NPD6776	Approved
0.6957	Remote Similarity	NPD9267	Approved
0.694	Remote Similarity	NPD7699	Phase 2
0.694	Remote Similarity	NPD7700	Phase 2
0.6936	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1283	Approved
0.6897	Remote Similarity	NPD9545	Approved
0.6897	Remote Similarity	NPD7074	Phase 3
0.6889	Remote Similarity	NPD1242	Phase 1
0.6886	Remote Similarity	NPD5402	Approved
0.6879	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1203	Approved
0.6857	Remote Similarity	NPD4750	Phase 3
0.6853	Remote Similarity	NPD5951	Approved
0.6849	Remote Similarity	NPD1651	Approved
0.6845	Remote Similarity	NPD7697	Approved
0.6845	Remote Similarity	NPD7696	Phase 3
0.6845	Remote Similarity	NPD7698	Approved
0.6845	Remote Similarity	NPD7435	Discontinued
0.6842	Remote Similarity	NPD8151	Discontinued
0.6839	Remote Similarity	NPD7286	Phase 2
0.6839	Remote Similarity	NPD7054	Approved
0.6825	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2798	Approved
0.6813	Remote Similarity	NPD6213	Phase 3
0.6813	Remote Similarity	NPD4628	Phase 3
0.6813	Remote Similarity	NPD6212	Phase 3
0.6813	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7871	Phase 2
0.6809	Remote Similarity	NPD7870	Phase 2
0.6809	Remote Similarity	NPD8320	Phase 1
0.6809	Remote Similarity	NPD8319	Approved
0.6802	Remote Similarity	NPD3926	Phase 2
0.68	Remote Similarity	NPD7472	Approved
0.6797	Remote Similarity	NPD4625	Phase 3
0.678	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3972	Approved
0.6776	Remote Similarity	NPD9494	Approved
0.677	Remote Similarity	NPD6190	Approved
0.6768	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5403	Approved
0.6766	Remote Similarity	NPD37	Approved
0.6761	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6797	Phase 2
0.6757	Remote Similarity	NPD3026	Approved
0.6757	Remote Similarity	NPD3023	Approved
0.6753	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5401	Approved
0.6748	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7229	Phase 3
0.6736	Remote Similarity	NPD9281	Approved
0.6735	Remote Similarity	NPD3025	Approved
0.6735	Remote Similarity	NPD3024	Approved
0.673	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7251	Discontinued
0.6722	Remote Similarity	NPD8434	Phase 2
0.6715	Remote Similarity	NPD940	Approved
0.6715	Remote Similarity	NPD846	Approved
0.6711	Remote Similarity	NPD1610	Phase 2
0.6711	Remote Similarity	NPD1281	Approved
0.671	Remote Similarity	NPD6663	Approved
0.6708	Remote Similarity	NPD8166	Discontinued
0.6702	Remote Similarity	NPD7701	Phase 2
0.6689	Remote Similarity	NPD1876	Approved
0.6686	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7177	Discontinued
0.6685	Remote Similarity	NPD7808	Phase 3
0.6684	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6648	Remote Similarity	NPD4287	Approved
0.6648	Remote Similarity	NPD5035	Approved
0.6647	Remote Similarity	NPD4965	Approved
0.6647	Remote Similarity	NPD4966	Approved
0.6647	Remote Similarity	NPD4967	Phase 2
0.6645	Remote Similarity	NPD3268	Approved
0.6645	Remote Similarity	NPD411	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