NPASS Compound

Structure

CID241263 OpenBabel06191716042D 23 26 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 4.3301 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 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.12
Volume:	319.23
LogP:	3.941
LogD:	3.312
LogS:	-4.16
# Rotatable Bonds:	1
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	2.703
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.918
MDCK Permeability:	1.5799374523339793e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355
Plasma Protein Binding (PPB):	93.17726135253906%
Volume Distribution (VD):	0.608
Pgp-substrate:	3.1609535217285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.367
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.892
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	2.236
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.93
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.817
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.912
Carcinogencity:	0.919
Eye Corrosion:	0.013
Eye Irritation:	0.817
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC241263

Natural Product ID:	NPC241263
*Common Name:**	Des-N-Methylacronycine
IUPAC Name:	6-methoxy-3,3-dimethyl-12H-pyrano[2,3-c]acridin-7-one
Synonyms:	Des-N-Methylacronycine
Standard InCHIKey:	NEYQKEUFRBPEJP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO3/c1-19(2)9-8-12-14(23-19)10-15(22-3)16-17(12)20-13-7-5-4-6-11(13)18(16)21/h4-10H,1-3H3,(H,20,21)
SMILES:	CC1(C)C=Cc2c(cc(c3c2[nH]c2ccccc2c3=O)OC)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454827
PubChem CID:	6325047
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29975532]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27785	Atalantia buxifolia	Species	Rutaceae	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	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[550245]
NPT319	Cell Line	B16	Mus musculus	IC50	>	40000.0	nM	PMID[550245]
NPT1353	Cell Line	CCRF-HSB-2	Homo sapiens	IC50	>	40000.0	nM	PMID[550245]
NPT1354	Cell Line	TGBC11TKB	Homo sapiens	IC50	>	40000.0	nM	PMID[550245]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[550246]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[550246]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[550246]

☑ 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 NPC241263 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	561
0.1-0.2	3553
0.2-0.3	12531
0.3-0.4	4303
0.4-0.5	9976
0.5-0.6	9485
0.6-0.7	1884
0.7-0.8	354
0.8-0.85	31
0.85-0.9	13
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9613	High Similarity	NPC288759
0.9609	High Similarity	NPC234933
0.9508	High Similarity	NPC301292
0.9508	High Similarity	NPC313112
0.9293	High Similarity	NPC15987
0.8906	High Similarity	NPC218303
0.8895	High Similarity	NPC198160
0.8866	High Similarity	NPC176113
0.8852	High Similarity	NPC1820
0.8804	High Similarity	NPC114039
0.8804	High Similarity	NPC206109
0.8763	High Similarity	NPC116178
0.8718	High Similarity	NPC321166
0.8718	High Similarity	NPC217903
0.8718	High Similarity	NPC30749
0.8667	High Similarity	NPC305542
0.8564	High Similarity	NPC474366
0.8416	Intermediate Similarity	NPC329830
0.841	Intermediate Similarity	NPC212123
0.8261	Intermediate Similarity	NPC298320
0.8213	Intermediate Similarity	NPC13249
0.815	Intermediate Similarity	NPC295479
0.815	Intermediate Similarity	NPC220241
0.8111	Intermediate Similarity	NPC299582
0.8069	Intermediate Similarity	NPC268223
0.7913	Intermediate Similarity	NPC134702
0.7913	Intermediate Similarity	NPC182853
0.7913	Intermediate Similarity	NPC87560
0.7913	Intermediate Similarity	NPC195120
0.7897	Intermediate Similarity	NPC170333
0.7854	Intermediate Similarity	NPC148391
0.7833	Intermediate Similarity	NPC25961
0.7831	Intermediate Similarity	NPC327005
0.7799	Intermediate Similarity	NPC118189
0.7799	Intermediate Similarity	NPC7560
0.7795	Intermediate Similarity	NPC471825
0.7751	Intermediate Similarity	NPC118154
0.7751	Intermediate Similarity	NPC157983
0.7718	Intermediate Similarity	NPC114468
0.7714	Intermediate Similarity	NPC76478
0.7711	Intermediate Similarity	NPC41216
0.7681	Intermediate Similarity	NPC2905
0.7673	Intermediate Similarity	NPC133156
0.7663	Intermediate Similarity	NPC204867
0.757	Intermediate Similarity	NPC285254
0.7526	Intermediate Similarity	NPC49184
0.7513	Intermediate Similarity	NPC73280
0.75	Intermediate Similarity	NPC469439
0.7487	Intermediate Similarity	NPC9475
0.7465	Intermediate Similarity	NPC198503
0.7416	Intermediate Similarity	NPC472409
0.7409	Intermediate Similarity	NPC283810
0.7345	Intermediate Similarity	NPC157855
0.7309	Intermediate Similarity	NPC151171
0.7303	Intermediate Similarity	NPC17848
0.7293	Intermediate Similarity	NPC59522
0.7288	Intermediate Similarity	NPC161196
0.7281	Intermediate Similarity	NPC115588
0.7273	Intermediate Similarity	NPC93653
0.7269	Intermediate Similarity	NPC251071
0.7263	Intermediate Similarity	NPC11566
0.726	Intermediate Similarity	NPC222561
0.7216	Intermediate Similarity	NPC127082
0.7206	Intermediate Similarity	NPC100863
0.72	Intermediate Similarity	NPC45389
0.7198	Intermediate Similarity	NPC38219
0.7196	Intermediate Similarity	NPC169402
0.7194	Intermediate Similarity	NPC472163
0.7183	Intermediate Similarity	NPC116238
0.7182	Intermediate Similarity	NPC103362
0.7182	Intermediate Similarity	NPC52576
0.7174	Intermediate Similarity	NPC110303
0.7174	Intermediate Similarity	NPC23728
0.7159	Intermediate Similarity	NPC229646
0.7158	Intermediate Similarity	NPC179970
0.7151	Intermediate Similarity	NPC259685
0.7143	Intermediate Similarity	NPC85613
0.7143	Intermediate Similarity	NPC11561
0.7143	Intermediate Similarity	NPC226636
0.7143	Intermediate Similarity	NPC147145
0.7135	Intermediate Similarity	NPC46869
0.7135	Intermediate Similarity	NPC160821
0.7135	Intermediate Similarity	NPC132592
0.7129	Intermediate Similarity	NPC477161
0.7127	Intermediate Similarity	NPC150522
0.7127	Intermediate Similarity	NPC305355
0.7127	Intermediate Similarity	NPC475680
0.712	Intermediate Similarity	NPC54577
0.712	Intermediate Similarity	NPC246948
0.712	Intermediate Similarity	NPC470647
0.712	Intermediate Similarity	NPC20488
0.712	Intermediate Similarity	NPC111786
0.712	Intermediate Similarity	NPC195621
0.712	Intermediate Similarity	NPC83357
0.712	Intermediate Similarity	NPC88964
0.712	Intermediate Similarity	NPC67805
0.712	Intermediate Similarity	NPC176229
0.712	Intermediate Similarity	NPC267375
0.712	Intermediate Similarity	NPC142405
0.712	Intermediate Similarity	NPC301276
0.712	Intermediate Similarity	NPC312973
0.712	Intermediate Similarity	NPC475052
0.712	Intermediate Similarity	NPC214774
0.7119	Intermediate Similarity	NPC292998
0.7114	Intermediate Similarity	NPC474059
0.7104	Intermediate Similarity	NPC17262
0.7104	Intermediate Similarity	NPC219915
0.7104	Intermediate Similarity	NPC106985
0.7104	Intermediate Similarity	NPC166138
0.7104	Intermediate Similarity	NPC18585
0.7102	Intermediate Similarity	NPC284424
0.7095	Intermediate Similarity	NPC478075
0.7095	Intermediate Similarity	NPC257266
0.7095	Intermediate Similarity	NPC254741
0.7089	Intermediate Similarity	NPC310211
0.7089	Intermediate Similarity	NPC308137
0.7088	Intermediate Similarity	NPC156590
0.7088	Intermediate Similarity	NPC205006
0.7088	Intermediate Similarity	NPC118840
0.7088	Intermediate Similarity	NPC64908
0.7088	Intermediate Similarity	NPC147688
0.7088	Intermediate Similarity	NPC110969
0.7081	Intermediate Similarity	NPC97716
0.7081	Intermediate Similarity	NPC283234
0.7081	Intermediate Similarity	NPC201731
0.7081	Intermediate Similarity	NPC473077
0.7081	Intermediate Similarity	NPC24673
0.7081	Intermediate Similarity	NPC296998
0.7081	Intermediate Similarity	NPC79469
0.7081	Intermediate Similarity	NPC87714
0.7081	Intermediate Similarity	NPC104406
0.7081	Intermediate Similarity	NPC237635
0.7079	Intermediate Similarity	NPC22476
0.7079	Intermediate Similarity	NPC125269
0.7079	Intermediate Similarity	NPC475411
0.7065	Intermediate Similarity	NPC311741
0.7065	Intermediate Similarity	NPC234629
0.7065	Intermediate Similarity	NPC209040
0.7062	Intermediate Similarity	NPC473655
0.7062	Intermediate Similarity	NPC257728
0.7062	Intermediate Similarity	NPC101294
0.7059	Intermediate Similarity	NPC230313
0.7056	Intermediate Similarity	NPC5167
0.7051	Intermediate Similarity	NPC298436
0.7049	Intermediate Similarity	NPC62840
0.7049	Intermediate Similarity	NPC293852
0.7049	Intermediate Similarity	NPC299080
0.7049	Intermediate Similarity	NPC144499
0.7049	Intermediate Similarity	NPC214236
0.7049	Intermediate Similarity	NPC217083
0.7049	Intermediate Similarity	NPC59739
0.7049	Intermediate Similarity	NPC78803
0.7043	Intermediate Similarity	NPC161191
0.7043	Intermediate Similarity	NPC6511
0.7043	Intermediate Similarity	NPC266572
0.7043	Intermediate Similarity	NPC296869
0.7039	Intermediate Similarity	NPC99854
0.7033	Intermediate Similarity	NPC172986
0.7033	Intermediate Similarity	NPC235239
0.7033	Intermediate Similarity	NPC270883
0.7033	Intermediate Similarity	NPC69769
0.7033	Intermediate Similarity	NPC171094
0.7033	Intermediate Similarity	NPC261227
0.7033	Intermediate Similarity	NPC241100
0.7033	Intermediate Similarity	NPC159275
0.703	Intermediate Similarity	NPC469437
0.7028	Intermediate Similarity	NPC153365
0.7027	Intermediate Similarity	NPC144691
0.7027	Intermediate Similarity	NPC477955
0.7023	Intermediate Similarity	NPC298449
0.702	Intermediate Similarity	NPC28368
0.7018	Intermediate Similarity	NPC174760
0.7018	Intermediate Similarity	NPC150239
0.7011	Intermediate Similarity	NPC143896
0.7011	Intermediate Similarity	NPC91560
0.7011	Intermediate Similarity	NPC316816
0.7011	Intermediate Similarity	NPC478086
0.7011	Intermediate Similarity	NPC75049
0.7011	Intermediate Similarity	NPC310130
0.7011	Intermediate Similarity	NPC257097
0.7011	Intermediate Similarity	NPC68104
0.7011	Intermediate Similarity	NPC169591
0.7011	Intermediate Similarity	NPC149026
0.7011	Intermediate Similarity	NPC39329
0.7011	Intermediate Similarity	NPC214166
0.7011	Intermediate Similarity	NPC221432
0.7011	Intermediate Similarity	NPC164980
0.7011	Intermediate Similarity	NPC150408
0.7011	Intermediate Similarity	NPC175504
0.7006	Intermediate Similarity	NPC278556
0.7005	Intermediate Similarity	NPC164299
0.7005	Intermediate Similarity	NPC77777
0.6996	Remote Similarity	NPC67401
0.6995	Remote Similarity	NPC3188
0.6995	Remote Similarity	NPC22467
0.6995	Remote Similarity	NPC282300
0.699	Remote Similarity	NPC129578
0.6989	Remote Similarity	NPC218300
0.6989	Remote Similarity	NPC282335
0.6989	Remote Similarity	NPC471285

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 NPC241263 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	729
0.2-0.3	1046
0.3-0.4	1597
0.4-0.5	2689
0.5-0.6	2068
0.6-0.7	595
0.7-0.8	67
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8308	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5186	Approved
0.7784	Intermediate Similarity	NPD5183	Approved
0.7703	Intermediate Similarity	NPD2899	Discontinued
0.7512	Intermediate Similarity	NPD3297	Approved
0.7427	Intermediate Similarity	NPD7584	Approved
0.7415	Intermediate Similarity	NPD3298	Approved
0.7387	Intermediate Similarity	NPD5937	Approved
0.7268	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6874	Approved
0.7254	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD2246	Approved
0.724	Intermediate Similarity	NPD2248	Approved
0.7236	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5496	Approved
0.7196	Intermediate Similarity	NPD955	Approved
0.7194	Intermediate Similarity	NPD6104	Discontinued
0.7174	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4979	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4981	Phase 2
0.7115	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7583	Approved
0.7095	Intermediate Similarity	NPD2796	Approved
0.7085	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6198	Phase 1
0.7071	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7585	Approved
0.7041	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4539	Phase 1
0.7005	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6625	Approved
0.6973	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5071	Phase 2
0.6946	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5637	Discontinued
0.6935	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.692	Remote Similarity	NPD8461	Discontinued
0.6906	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7627	Approved
0.6905	Remote Similarity	NPD7626	Approved
0.6897	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6719	Approved
0.6878	Remote Similarity	NPD6585	Discontinued
0.6875	Remote Similarity	NPD7654	Discontinued
0.6869	Remote Similarity	NPD3793	Phase 3
0.6864	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1926	Approved
0.6842	Remote Similarity	NPD5890	Approved
0.6842	Remote Similarity	NPD2366	Approved
0.6842	Remote Similarity	NPD7411	Suspended
0.6842	Remote Similarity	NPD5889	Approved
0.684	Remote Similarity	NPD6250	Discontinued
0.684	Remote Similarity	NPD4467	Phase 2
0.684	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4465	Phase 2
0.6827	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4613	Phase 2
0.6821	Remote Similarity	NPD2247	Approved
0.6821	Remote Similarity	NPD2249	Approved
0.6818	Remote Similarity	NPD7803	Approved
0.6816	Remote Similarity	NPD3925	Approved
0.6816	Remote Similarity	NPD7545	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD1898	Discontinued
0.6812	Remote Similarity	NPD4360	Phase 2
0.6812	Remote Similarity	NPD4363	Phase 3
0.6794	Remote Similarity	NPD4668	Phase 2
0.6787	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5928	Phase 1
0.6779	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7922	Phase 1
0.6753	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1309	Phase 2
0.6753	Remote Similarity	NPD1307	Phase 2
0.675	Remote Similarity	NPD7479	Phase 2
0.6745	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1549	Phase 2
0.6735	Remote Similarity	NPD6457	Approved
0.673	Remote Similarity	NPD3289	Phase 3
0.673	Remote Similarity	NPD2339	Phase 3
0.673	Remote Similarity	NPD3290	Approved
0.6728	Remote Similarity	NPD5416	Discontinued
0.6728	Remote Similarity	NPD1945	Phase 1
0.6724	Remote Similarity	NPD6790	Phase 1
0.6716	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2654	Approved
0.6702	Remote Similarity	NPD4380	Phase 2
0.6701	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3964	Approved
0.6699	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4361	Phase 2
0.6698	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6321	Discontinued
0.6697	Remote Similarity	NPD5632	Approved
0.6696	Remote Similarity	NPD4952	Phase 3
0.6695	Remote Similarity	NPD1483	Discontinued
0.6685	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7819	Suspended
0.6684	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4515	Suspended
0.6683	Remote Similarity	NPD3446	Phase 1
0.6683	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6644	Discontinued
0.6682	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5860	Discontinued
0.6667	Remote Similarity	NPD8067	Phase 3
0.6667	Remote Similarity	NPD4846	Phase 2
0.6667	Remote Similarity	NPD3515	Approved
0.6667	Remote Similarity	NPD7316	Discontinued
0.6667	Remote Similarity	NPD6962	Phase 2
0.6667	Remote Similarity	NPD3516	Approved
0.6653	Remote Similarity	NPD7708	Approved
0.665	Remote Similarity	NPD4354	Approved
0.665	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6357	Discontinued
0.6637	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4302	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3154	Approved
0.6634	Remote Similarity	NPD3153	Approved
0.6633	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6801	Discontinued
0.6631	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1240	Approved
0.663	Remote Similarity	NPD3142	Approved
0.663	Remote Similarity	NPD3140	Approved
0.6623	Remote Similarity	NPD6199	Discontinued
0.6618	Remote Similarity	NPD7546	Discontinued
0.6617	Remote Similarity	NPD3965	Phase 1
0.6613	Remote Similarity	NPD1243	Approved
0.6612	Remote Similarity	NPD7955	Approved
0.6612	Remote Similarity	NPD7956	Approved
0.6609	Remote Similarity	NPD4373	Phase 2
0.6606	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5494	Approved
0.6598	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4082	Approved
0.659	Remote Similarity	NPD4859	Phase 1
0.6589	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2216	Approved
0.6583	Remote Similarity	NPD2215	Approved
0.6582	Remote Similarity	NPD7075	Discontinued
0.6581	Remote Similarity	NPD7417	Discontinued
0.658	Remote Similarity	NPD2836	Approved
0.6578	Remote Similarity	NPD5410	Discontinued
0.6576	Remote Similarity	NPD1626	Approved
0.6576	Remote Similarity	NPD1510	Phase 2
0.6573	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2821	Approved
0.6564	Remote Similarity	NPD7186	Phase 3
0.6561	Remote Similarity	NPD6799	Approved
0.6561	Remote Similarity	NPD5293	Phase 2
0.6559	Remote Similarity	NPD4598	Approved
0.6559	Remote Similarity	NPD4597	Approved
0.6557	Remote Similarity	NPD5194	Approved
0.6557	Remote Similarity	NPD5197	Approved
0.6557	Remote Similarity	NPD1607	Approved
0.6557	Remote Similarity	NPD5196	Approved
0.6552	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7279	Phase 2
0.6549	Remote Similarity	NPD7278	Phase 2
0.6548	Remote Similarity	NPD3252	Approved
0.6544	Remote Similarity	NPD6296	Discontinued
0.6542	Remote Similarity	NPD7476	Discontinued
0.6538	Remote Similarity	NPD4259	Approved
0.6538	Remote Similarity	NPD4258	Approved
0.6535	Remote Similarity	NPD6020	Phase 2
0.6532	Remote Similarity	NPD8149	Discontinued
0.6526	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4888	Discontinued
0.6526	Remote Similarity	NPD4662	Approved
0.6526	Remote Similarity	NPD4661	Approved
0.6512	Remote Similarity	NPD5005	Approved
0.6512	Remote Similarity	NPD5006	Approved
0.6509	Remote Similarity	NPD5515	Phase 2
0.6508	Remote Similarity	NPD643	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1913	Phase 1
0.65	Remote Similarity	NPD5242	Approved
0.65	Remote Similarity	NPD683	Approved
0.65	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD2672	Discontinued
0.6495	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3748	Approved
0.6485	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3912	Discontinued

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