NPASS Compound

Structure

CID305542 OpenBabel06191716112D 24 27 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 -3.4641 1.0000 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 -5.1962 -2.0000 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 -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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -0.5000 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 -4.3301 -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 -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 -5.1962 1.0000 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 -3.4641 -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 20 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.12
Volume:	328.02
LogP:	3.875
LogD:	3.214
LogS:	-3.967
# Rotatable Bonds:	0
TPSA:	71.69
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.623
Synthetic Accessibility Score:	3.019
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.745
MDCK Permeability:	2.1923598978901282e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	98.52806091308594%
Volume Distribution (VD):	0.462
Pgp-substrate:	1.3410176038742065%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.714
CYP2C19-inhibitor:	0.573
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.835
CYP2D6-substrate:	0.537
CYP3A4-inhibitor:	0.559
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	2.402
Half-life (T1/2):	0.255

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.372
Drug-inuced Liver Injury (DILI):	0.783
AMES Toxicity:	0.85
Rat Oral Acute Toxicity:	0.771
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.565
Carcinogencity:	0.924
Eye Corrosion:	0.006
Eye Irritation:	0.929
Respiratory Toxicity:	0.786

Download Data

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

Natural Product: NPC305542

Natural Product ID:	NPC305542
*Common Name:**	5-Hydroxynoracronycine
IUPAC Name:	6,11-dihydroxy-3,3,12-trimethylpyrano[2,3-c]acridin-7-one
Synonyms:	5-Hydroxynoracronycine
Standard InCHIKey:	JZQDCDLYNFZBIG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO4/c1-19(2)8-7-10-14(24-19)9-13(22)15-17(10)20(3)16-11(18(15)23)5-4-6-12(16)21/h4-9,21-22H,1-3H3
SMILES:	CC1(C)C=Cc2c(cc(c3c2n(C)c2c(cccc2O)c3=O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447169
PubChem CID:	5378702
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
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575960]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[21985060]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5476	Hortia arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7221	Korolkowia sewerzowi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2786	Clematis flammula	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5476	Hortia arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	2
ED50	2
IC50	11
Others	3

Activity Type	# Activity
Cell Line	7
Individual Protein	1
Organism	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	85.5	uM	PMID[555304]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	78.0	uM	PMID[555304]
NPT1353	Cell Line	CCRF-HSB-2	Homo sapiens	IC50	=	23600.0	nM	PMID[555305]
NPT1354	Cell Line	TGBC11TKB	Homo sapiens	IC50	=	16200.0	nM	PMID[555305]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[555305]
NPT319	Cell Line	B16	Mus musculus	IC50	>	40000.0	nM	PMID[555305]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	48000.0	nM	PMID[555306]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	9.3	ug.mL-1	PMID[555307]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	11100.0	nM	PMID[555304]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8700.0	nM	PMID[555304]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10200.0	nM	PMID[555304]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6800.0	nM	PMID[555304]
NPT2	Others	Unspecified		Ratio	=	7.7	n.a.	PMID[555304]
NPT2	Others	Unspecified		Ratio	=	9.0	n.a.	PMID[555304]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	0.9	ug.mL-1	PMID[555307]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	=	11.2	ug.mL-1	PMID[555307]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	125.0	ug.mL-1	PMID[555307]
NPT2	Others	Unspecified		Ratio IC50	=	10.0	n.a.	PMID[555307]

☑ 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 NPC305542 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	549
0.1-0.2	3150
0.2-0.3	11526
0.3-0.4	5398
0.4-0.5	8950
0.5-0.6	10107
0.6-0.7	2707
0.7-0.8	260
0.8-0.85	10
0.85-0.9	24
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9842	High Similarity	NPC30749
0.9634	High Similarity	NPC218303
0.963	High Similarity	NPC212123
0.9585	High Similarity	NPC176113
0.9353	High Similarity	NPC13249
0.9316	High Similarity	NPC15987
0.9202	High Similarity	NPC170333
0.9179	High Similarity	NPC474366
0.9005	High Similarity	NPC234933
0.8995	High Similarity	NPC148391
0.8929	High Similarity	NPC198160
0.8918	High Similarity	NPC288759
0.8916	High Similarity	NPC7560
0.8894	High Similarity	NPC116178
0.8861	High Similarity	NPC182853
0.885	High Similarity	NPC321166
0.885	High Similarity	NPC217903
0.8827	High Similarity	NPC301292
0.8827	High Similarity	NPC313112
0.8824	High Similarity	NPC76478
0.8806	High Similarity	NPC2905
0.8768	High Similarity	NPC134702
0.8756	High Similarity	NPC114468
0.8743	High Similarity	NPC206109
0.8743	High Similarity	NPC114039
0.8731	High Similarity	NPC133156
0.8667	High Similarity	NPC241263
0.8654	High Similarity	NPC285254
0.8641	High Similarity	NPC118189
0.8564	High Similarity	NPC295479
0.8564	High Similarity	NPC220241
0.8551	High Similarity	NPC329830
0.848	Intermediate Similarity	NPC268223
0.8402	Intermediate Similarity	NPC1820
0.8317	Intermediate Similarity	NPC87560
0.8317	Intermediate Similarity	NPC195120
0.8316	Intermediate Similarity	NPC298320
0.8177	Intermediate Similarity	NPC327005
0.8152	Intermediate Similarity	NPC157983
0.8152	Intermediate Similarity	NPC118154
0.7742	Intermediate Similarity	NPC251071
0.7737	Intermediate Similarity	NPC204867
0.765	Intermediate Similarity	NPC469439
0.7604	Intermediate Similarity	NPC299582
0.7537	Intermediate Similarity	NPC469437
0.7536	Intermediate Similarity	NPC83019
0.7513	Intermediate Similarity	NPC129578
0.7488	Intermediate Similarity	NPC204580
0.7475	Intermediate Similarity	NPC127082
0.745	Intermediate Similarity	NPC309692
0.7441	Intermediate Similarity	NPC41216
0.7427	Intermediate Similarity	NPC471825
0.7395	Intermediate Similarity	NPC25961
0.7368	Intermediate Similarity	NPC112937
0.733	Intermediate Similarity	NPC101957
0.733	Intermediate Similarity	NPC120105
0.7308	Intermediate Similarity	NPC264938
0.7304	Intermediate Similarity	NPC262725
0.7302	Intermediate Similarity	NPC330683
0.7302	Intermediate Similarity	NPC329567
0.73	Intermediate Similarity	NPC9475
0.7287	Intermediate Similarity	NPC38219
0.7287	Intermediate Similarity	NPC219915
0.7286	Intermediate Similarity	NPC17677
0.7277	Intermediate Similarity	NPC10027
0.7277	Intermediate Similarity	NPC65775
0.7269	Intermediate Similarity	NPC477825
0.7249	Intermediate Similarity	NPC311741
0.7249	Intermediate Similarity	NPC234629
0.7248	Intermediate Similarity	NPC477826
0.7248	Intermediate Similarity	NPC477827
0.724	Intermediate Similarity	NPC472633
0.7234	Intermediate Similarity	NPC144499
0.7225	Intermediate Similarity	NPC266572
0.7225	Intermediate Similarity	NPC37135
0.7225	Intermediate Similarity	NPC186397
0.7216	Intermediate Similarity	NPC280530
0.7216	Intermediate Similarity	NPC95842
0.7216	Intermediate Similarity	NPC178964
0.7196	Intermediate Similarity	NPC166138
0.7196	Intermediate Similarity	NPC18585
0.7196	Intermediate Similarity	NPC106985
0.7194	Intermediate Similarity	NPC218313
0.7194	Intermediate Similarity	NPC474681
0.7193	Intermediate Similarity	NPC227033
0.7188	Intermediate Similarity	NPC223988
0.7188	Intermediate Similarity	NPC266499
0.7181	Intermediate Similarity	NPC147688
0.7181	Intermediate Similarity	NPC205006
0.7181	Intermediate Similarity	NPC156590
0.7181	Intermediate Similarity	NPC64908
0.7181	Intermediate Similarity	NPC118840
0.7179	Intermediate Similarity	NPC93653
0.7173	Intermediate Similarity	NPC24673
0.7173	Intermediate Similarity	NPC110303
0.7173	Intermediate Similarity	NPC104406
0.7173	Intermediate Similarity	NPC201731
0.7173	Intermediate Similarity	NPC237635
0.7173	Intermediate Similarity	NPC317567
0.7173	Intermediate Similarity	NPC97716
0.7173	Intermediate Similarity	NPC473077
0.7173	Intermediate Similarity	NPC296998
0.7173	Intermediate Similarity	NPC23728
0.7173	Intermediate Similarity	NPC79469
0.7169	Intermediate Similarity	NPC470482
0.7169	Intermediate Similarity	NPC470481
0.7165	Intermediate Similarity	NPC142527
0.7157	Intermediate Similarity	NPC204879
0.715	Intermediate Similarity	NPC29777
0.715	Intermediate Similarity	NPC471115
0.7143	Intermediate Similarity	NPC214236
0.7143	Intermediate Similarity	NPC293852
0.7143	Intermediate Similarity	NPC78803
0.7143	Intermediate Similarity	NPC11561
0.7143	Intermediate Similarity	NPC62840
0.7143	Intermediate Similarity	NPC5322
0.7143	Intermediate Similarity	NPC217083
0.7143	Intermediate Similarity	NPC226636
0.7143	Intermediate Similarity	NPC59739
0.7143	Intermediate Similarity	NPC299080
0.7143	Intermediate Similarity	NPC133970
0.7143	Intermediate Similarity	NPC98416
0.7143	Intermediate Similarity	NPC6633
0.7135	Intermediate Similarity	NPC296869
0.7135	Intermediate Similarity	NPC132592
0.7135	Intermediate Similarity	NPC160821
0.7135	Intermediate Similarity	NPC6511
0.7128	Intermediate Similarity	NPC69769
0.7128	Intermediate Similarity	NPC235239
0.7128	Intermediate Similarity	NPC472462
0.7128	Intermediate Similarity	NPC172986
0.7128	Intermediate Similarity	NPC270883
0.7128	Intermediate Similarity	NPC261227
0.7128	Intermediate Similarity	NPC305355
0.7128	Intermediate Similarity	NPC475680
0.712	Intermediate Similarity	NPC144691
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	NPC142405
0.712	Intermediate Similarity	NPC195621
0.712	Intermediate Similarity	NPC301276
0.712	Intermediate Similarity	NPC83357
0.712	Intermediate Similarity	NPC88964
0.712	Intermediate Similarity	NPC196114
0.712	Intermediate Similarity	NPC67805
0.712	Intermediate Similarity	NPC176229
0.712	Intermediate Similarity	NPC267375
0.712	Intermediate Similarity	NPC477955
0.712	Intermediate Similarity	NPC312973
0.712	Intermediate Similarity	NPC475052
0.712	Intermediate Similarity	NPC214774
0.7117	Intermediate Similarity	NPC477828
0.7113	Intermediate Similarity	NPC305965
0.7113	Intermediate Similarity	NPC154345
0.7108	Intermediate Similarity	NPC472163
0.7103	Intermediate Similarity	NPC316164
0.7103	Intermediate Similarity	NPC471489
0.7098	Intermediate Similarity	NPC474052
0.7097	Intermediate Similarity	NPC478075
0.7095	Intermediate Similarity	NPC78284
0.7094	Intermediate Similarity	NPC474815
0.7092	Intermediate Similarity	NPC200246
0.7092	Intermediate Similarity	NPC275575
0.7092	Intermediate Similarity	NPC472280
0.7092	Intermediate Similarity	NPC55662
0.7092	Intermediate Similarity	NPC166054
0.709	Intermediate Similarity	NPC103362
0.709	Intermediate Similarity	NPC110969
0.7085	Intermediate Similarity	NPC234644
0.7085	Intermediate Similarity	NPC29876
0.7085	Intermediate Similarity	NPC167678
0.7083	Intermediate Similarity	NPC283234
0.7083	Intermediate Similarity	NPC140120
0.7083	Intermediate Similarity	NPC14001
0.7083	Intermediate Similarity	NPC166757
0.7077	Intermediate Similarity	NPC45934
0.7074	Intermediate Similarity	NPC301217
0.7074	Intermediate Similarity	NPC220062
0.7074	Intermediate Similarity	NPC303633
0.7074	Intermediate Similarity	NPC55018
0.7074	Intermediate Similarity	NPC96565
0.7074	Intermediate Similarity	NPC216978
0.7073	Intermediate Similarity	NPC99723
0.7072	Intermediate Similarity	NPC38964
0.7068	Intermediate Similarity	NPC209040
0.7068	Intermediate Similarity	NPC257236
0.7068	Intermediate Similarity	NPC278175
0.7064	Intermediate Similarity	NPC257728
0.7062	Intermediate Similarity	NPC227122
0.7062	Intermediate Similarity	NPC188403
0.7056	Intermediate Similarity	NPC472455
0.7056	Intermediate Similarity	NPC470600
0.7056	Intermediate Similarity	NPC282307
0.7056	Intermediate Similarity	NPC170026
0.705	Intermediate Similarity	NPC83922
0.705	Intermediate Similarity	NPC329760
0.705	Intermediate Similarity	NPC472448

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 NPC305542 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	708
0.2-0.3	1090
0.3-0.4	1766
0.4-0.5	2684
0.5-0.6	1972
0.6-0.7	531
0.7-0.8	63
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD2899	Discontinued
0.7681	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3298	Approved
0.7588	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD8461	Discontinued
0.7524	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3297	Approved
0.75	Intermediate Similarity	NPD6874	Approved
0.7468	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5860	Discontinued
0.7364	Intermediate Similarity	NPD5496	Approved
0.7363	Intermediate Similarity	NPD6104	Discontinued
0.7361	Intermediate Similarity	NPD1945	Phase 1
0.7357	Intermediate Similarity	NPD6625	Approved
0.733	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4360	Phase 2
0.7308	Intermediate Similarity	NPD4363	Phase 3
0.7302	Intermediate Similarity	NPD2907	Approved
0.7302	Intermediate Similarity	NPD2906	Approved
0.7299	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7584	Approved
0.724	Intermediate Similarity	NPD6198	Phase 1
0.7196	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8067	Phase 3
0.719	Intermediate Similarity	NPD4361	Phase 2
0.719	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD8367	Approved
0.7164	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4465	Phase 2
0.7163	Intermediate Similarity	NPD4467	Phase 2
0.7156	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6199	Discontinued
0.7129	Intermediate Similarity	NPD5937	Approved
0.7125	Intermediate Similarity	NPD8492	Approved
0.7114	Intermediate Similarity	NPD3446	Phase 1
0.7105	Intermediate Similarity	NPD7654	Discontinued
0.7083	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4082	Approved
0.7064	Intermediate Similarity	NPD1483	Discontinued
0.7064	Intermediate Similarity	NPD7585	Approved
0.7018	Intermediate Similarity	NPD7583	Approved
0.7018	Intermediate Similarity	NPD4596	Phase 1
0.7	Intermediate Similarity	NPD4981	Phase 2
0.6995	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3472	Approved
0.6986	Remote Similarity	NPD4022	Approved
0.6979	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6585	Discontinued
0.6965	Remote Similarity	NPD5183	Approved
0.6965	Remote Similarity	NPD5186	Approved
0.6964	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3372	Discontinued
0.6916	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7922	Phase 1
0.6905	Remote Similarity	NPD1898	Discontinued
0.6904	Remote Similarity	NPD6844	Discontinued
0.69	Remote Similarity	NPD3925	Approved
0.6893	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3793	Phase 3
0.6878	Remote Similarity	NPD6020	Phase 2
0.6869	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7043	Discontinued
0.6861	Remote Similarity	NPD4494	Approved
0.6861	Remote Similarity	NPD4492	Approved
0.6857	Remote Similarity	NPD4515	Suspended
0.6853	Remote Similarity	NPD5889	Approved
0.6853	Remote Similarity	NPD5890	Approved
0.6849	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5242	Approved
0.684	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5006	Approved
0.6835	Remote Similarity	NPD5005	Approved
0.6827	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4846	Phase 2
0.682	Remote Similarity	NPD2339	Phase 3
0.6807	Remote Similarity	NPD7417	Discontinued
0.6802	Remote Similarity	NPD4380	Phase 2
0.6798	Remote Similarity	NPD5711	Approved
0.6798	Remote Similarity	NPD5710	Approved
0.6792	Remote Similarity	NPD5928	Phase 1
0.6784	Remote Similarity	NPD1926	Approved
0.6784	Remote Similarity	NPD7819	Suspended
0.6774	Remote Similarity	NPD8285	Discontinued
0.6771	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7907	Approved
0.6768	Remote Similarity	NPD7411	Suspended
0.6766	Remote Similarity	NPD955	Approved
0.6757	Remote Similarity	NPD7701	Phase 2
0.6754	Remote Similarity	NPD1549	Phase 2
0.6751	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4493	Discontinued
0.6732	Remote Similarity	NPD2248	Approved
0.6732	Remote Similarity	NPD2246	Approved
0.6731	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4668	Phase 2
0.6728	Remote Similarity	NPD5196	Approved
0.6728	Remote Similarity	NPD5197	Approved
0.6728	Remote Similarity	NPD5194	Approved
0.6726	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7186	Phase 3
0.6712	Remote Similarity	NPD2494	Approved
0.6712	Remote Similarity	NPD7263	Phase 2
0.6712	Remote Similarity	NPD2493	Approved
0.6712	Remote Similarity	NPD3452	Approved
0.6712	Remote Similarity	NPD3450	Approved
0.6712	Remote Similarity	NPD6321	Discontinued
0.671	Remote Similarity	NPD7278	Phase 2
0.671	Remote Similarity	NPD7279	Phase 2
0.6702	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.67	Remote Similarity	NPD2801	Approved
0.6698	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7810	Phase 3
0.6697	Remote Similarity	NPD6644	Discontinued
0.6697	Remote Similarity	NPD7811	Phase 3
0.6696	Remote Similarity	NPD3893	Discontinued
0.6696	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD1510	Phase 2
0.6683	Remote Similarity	NPD7075	Discontinued
0.6683	Remote Similarity	NPD7479	Phase 2
0.6682	Remote Similarity	NPD2974	Approved
0.6682	Remote Similarity	NPD2975	Approved
0.6682	Remote Similarity	NPD2973	Approved
0.6682	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4665	Approved
0.6681	Remote Similarity	NPD4111	Phase 1
0.6681	Remote Similarity	NPD1505	Phase 2
0.6667	Remote Similarity	NPD683	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6652	Remote Similarity	NPD3263	Phase 3
0.6651	Remote Similarity	NPD5071	Phase 2
0.6651	Remote Similarity	NPD4420	Approved
0.665	Remote Similarity	NPD1934	Approved
0.6649	Remote Similarity	NPD2796	Approved
0.6638	Remote Similarity	NPD3912	Discontinued
0.6637	Remote Similarity	NPD3888	Discontinued
0.6637	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7546	Discontinued
0.6633	Remote Similarity	NPD7447	Phase 1
0.6626	Remote Similarity	NPD5488	Discontinued
0.6622	Remote Similarity	NPD4582	Approved
0.6622	Remote Similarity	NPD4583	Approved
0.6621	Remote Similarity	NPD5609	Approved
0.6621	Remote Similarity	NPD5608	Approved
0.662	Remote Similarity	NPD5610	Approved
0.662	Remote Similarity	NPD4539	Phase 1
0.6617	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7048	Phase 3
0.6608	Remote Similarity	NPD4455	Discontinued
0.6606	Remote Similarity	NPD4604	Approved
0.6606	Remote Similarity	NPD4605	Approved
0.6601	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3749	Approved
0.6599	Remote Similarity	NPD1512	Approved
0.6595	Remote Similarity	NPD6997	Phase 2
0.6591	Remote Similarity	NPD4580	Approved
0.6587	Remote Similarity	NPD7177	Discontinued
0.6585	Remote Similarity	NPD6959	Discontinued
0.6585	Remote Similarity	NPD2249	Approved
0.6585	Remote Similarity	NPD2247	Approved
0.6585	Remote Similarity	NPD2821	Approved
0.6582	Remote Similarity	NPD7213	Phase 3
0.6582	Remote Similarity	NPD7212	Phase 2
0.6582	Remote Similarity	NPD7031	Phase 1
0.658	Remote Similarity	NPD3437	Discontinued
0.6577	Remote Similarity	NPD4002	Approved
0.6577	Remote Similarity	NPD4004	Approved
0.6571	Remote Similarity	NPD3823	Discontinued
0.657	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7577	Discontinued
0.6565	Remote Similarity	NPD7395	Discontinued
0.6564	Remote Similarity	NPD7301	Phase 3
0.6564	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2434	Approved
0.6561	Remote Similarity	NPD1240	Approved
0.6561	Remote Similarity	NPD7803	Approved
0.656	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3882	Suspended
0.655	Remote Similarity	NPD8149	Discontinued
0.6549	Remote Similarity	NPD5914	Approved
0.6546	Remote Similarity	NPD2654	Approved
0.6545	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.654	Remote Similarity	NPD6962	Phase 2
0.654	Remote Similarity	NPD5637	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