NPASS Compound

Structure

CID273837 OpenBabel06191716082D 24 26 0 0 0 0 0 0 0 0999 V2000 -1.7321 4.0000 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 2.5981 -0.5000 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 -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 -0.8660 -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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 1.7321 1.0000 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 -1.7321 1.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 12 19 2 0 0 0 0 14 20 2 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.14
Volume:	348.745
LogP:	4.908
LogD:	4.067
LogS:	-6.345
# Rotatable Bonds:	3
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	2.244
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.703
MDCK Permeability:	1.670452365942765e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.955
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	99.44470977783203%
Volume Distribution (VD):	0.375
Pgp-substrate:	0.7654920816421509%

ADMET: Metabolism

CYP1A2-inhibitor:	0.757
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.196
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.529

ADMET: Excretion

Clearance (CL):	3.687
Half-life (T1/2):	0.096

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.079
Skin Sensitization:	0.046
Carcinogencity:	0.068
Eye Corrosion:	0.004
Eye Irritation:	0.312
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC273837

Natural Product ID:	NPC273837
*Common Name:**	Nigerapyrone B
IUPAC Name:	6-(3,5-dimethyl-2-phenylphenyl)-4-methoxy-3-methylpyran-2-one
Synonyms:	Nigerapyrone B
Standard InCHIKey:	GORRUIALEVAHBX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O3/c1-13-10-14(2)20(16-8-6-5-7-9-16)17(11-13)19-12-18(23-4)15(3)21(22)24-19/h5-12H,1-4H3
SMILES:	Cc1cc(C)c(c2ccccc2)c(c1)c1cc(c(C)c(=O)o1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823130
PubChem CID:	53483952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)88611-1]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np058103o]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/JR9620000040]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1966.10858561]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1972.10860562]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1985.10867263]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10695672]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12458767]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542363]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	sponge-derived	n.a.	PMID[15387655]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387655]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15556711]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620260]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17653510]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827758]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014861]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20028011]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21176790]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21543515]
NPO33567	Aspergillus niger MA-132	Species	Aspergillaceae	Eukaryota	obtained from the fresh tissue of the marine mangrove plant Avicennia marina	n.a.	n.a.	PMID[21774474]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21774474]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921072]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24684908]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25044953]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25062661]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293978]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26040782]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26132344]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26414728]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27245874]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32159958]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6073032]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	Database[Article]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO14234	Aspergillus niger	Species	Aspergillaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	62000.0	nM	PMID[528486]

☑ 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 NPC273837 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	421
0.1-0.2	1764
0.2-0.3	4495
0.3-0.4	11030
0.4-0.5	7258
0.5-0.6	5492
0.6-0.7	6824
0.7-0.8	4892
0.8-0.85	461
0.85-0.9	57
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8319	Intermediate Similarity	NPC228936
0.8214	Intermediate Similarity	NPC79496
0.8205	Intermediate Similarity	NPC289432
0.8205	Intermediate Similarity	NPC988
0.8205	Intermediate Similarity	NPC232958
0.8173	Intermediate Similarity	NPC5472
0.8165	Intermediate Similarity	NPC209632
0.8158	Intermediate Similarity	NPC221275
0.8142	Intermediate Similarity	NPC13784
0.8136	Intermediate Similarity	NPC144547
0.8125	Intermediate Similarity	NPC474157
0.8103	Intermediate Similarity	NPC228318
0.8103	Intermediate Similarity	NPC45794
0.8077	Intermediate Similarity	NPC23453
0.8073	Intermediate Similarity	NPC114594
0.8058	Intermediate Similarity	NPC119631
0.8034	Intermediate Similarity	NPC254233
0.802	Intermediate Similarity	NPC96625
0.8	Intermediate Similarity	NPC210092
0.7965	Intermediate Similarity	NPC210089
0.7963	Intermediate Similarity	NPC469481
0.7961	Intermediate Similarity	NPC213156
0.7961	Intermediate Similarity	NPC240108
0.7946	Intermediate Similarity	NPC99846
0.7946	Intermediate Similarity	NPC269023
0.7931	Intermediate Similarity	NPC135730
0.7899	Intermediate Similarity	NPC238861
0.7899	Intermediate Similarity	NPC77000
0.7869	Intermediate Similarity	NPC295664
0.7864	Intermediate Similarity	NPC173443
0.7857	Intermediate Similarity	NPC191395
0.7845	Intermediate Similarity	NPC474408
0.7845	Intermediate Similarity	NPC474095
0.7826	Intermediate Similarity	NPC128368
0.7826	Intermediate Similarity	NPC272524
0.7822	Intermediate Similarity	NPC53299
0.7818	Intermediate Similarity	NPC60679
0.7807	Intermediate Similarity	NPC133308
0.7768	Intermediate Similarity	NPC37622
0.7768	Intermediate Similarity	NPC30594
0.7767	Intermediate Similarity	NPC304760
0.7759	Intermediate Similarity	NPC196075
0.7759	Intermediate Similarity	NPC308744
0.7748	Intermediate Similarity	NPC472222
0.7748	Intermediate Similarity	NPC472221
0.7739	Intermediate Similarity	NPC66208
0.7739	Intermediate Similarity	NPC212415
0.7712	Intermediate Similarity	NPC105141
0.7712	Intermediate Similarity	NPC242764
0.7706	Intermediate Similarity	NPC98911
0.7706	Intermediate Similarity	NPC472318
0.7692	Intermediate Similarity	NPC474685
0.7692	Intermediate Similarity	NPC220893
0.7686	Intermediate Similarity	NPC212559
0.7672	Intermediate Similarity	NPC265002
0.767	Intermediate Similarity	NPC89377
0.7658	Intermediate Similarity	NPC234305
0.7652	Intermediate Similarity	NPC475002
0.7652	Intermediate Similarity	NPC473809
0.7652	Intermediate Similarity	NPC95126
0.7652	Intermediate Similarity	NPC167504
0.7647	Intermediate Similarity	NPC58616
0.7642	Intermediate Similarity	NPC51079
0.7642	Intermediate Similarity	NPC307139
0.7636	Intermediate Similarity	NPC42211
0.7632	Intermediate Similarity	NPC318327
0.7632	Intermediate Similarity	NPC83628
0.7632	Intermediate Similarity	NPC265407
0.7632	Intermediate Similarity	NPC17417
0.7632	Intermediate Similarity	NPC10251
0.7627	Intermediate Similarity	NPC283169
0.7611	Intermediate Similarity	NPC475203
0.7611	Intermediate Similarity	NPC474376
0.7611	Intermediate Similarity	NPC472316
0.7611	Intermediate Similarity	NPC472315
0.7611	Intermediate Similarity	NPC477251
0.7607	Intermediate Similarity	NPC307651
0.7597	Intermediate Similarity	NPC472524
0.7594	Intermediate Similarity	NPC472523
0.7589	Intermediate Similarity	NPC85977
0.7586	Intermediate Similarity	NPC234376
0.7586	Intermediate Similarity	NPC82899
0.7586	Intermediate Similarity	NPC270699
0.7581	Intermediate Similarity	NPC111088
0.7565	Intermediate Similarity	NPC196246
0.7565	Intermediate Similarity	NPC93084
0.7565	Intermediate Similarity	NPC214067
0.7565	Intermediate Similarity	NPC251854
0.7559	Intermediate Similarity	NPC131684
0.7557	Intermediate Similarity	NPC115861
0.7545	Intermediate Similarity	NPC325497
0.7545	Intermediate Similarity	NPC118343
0.7545	Intermediate Similarity	NPC221825
0.7544	Intermediate Similarity	NPC56493
0.754	Intermediate Similarity	NPC428300
0.7525	Intermediate Similarity	NPC99240
0.7523	Intermediate Similarity	NPC270654
0.7523	Intermediate Similarity	NPC226041
0.7522	Intermediate Similarity	NPC269457
0.752	Intermediate Similarity	NPC232387
0.75	Intermediate Similarity	NPC263754
0.75	Intermediate Similarity	NPC305912
0.75	Intermediate Similarity	NPC243355
0.75	Intermediate Similarity	NPC169050
0.75	Intermediate Similarity	NPC286608
0.75	Intermediate Similarity	NPC25648
0.75	Intermediate Similarity	NPC1082
0.75	Intermediate Similarity	NPC301943
0.75	Intermediate Similarity	NPC183154
0.75	Intermediate Similarity	NPC474365
0.7479	Intermediate Similarity	NPC473507
0.7478	Intermediate Similarity	NPC469636
0.7478	Intermediate Similarity	NPC281604
0.7477	Intermediate Similarity	NPC245927
0.7477	Intermediate Similarity	NPC70624
0.7476	Intermediate Similarity	NPC475710
0.7462	Intermediate Similarity	NPC185777
0.746	Intermediate Similarity	NPC51292
0.746	Intermediate Similarity	NPC5486
0.7459	Intermediate Similarity	NPC103916
0.7458	Intermediate Similarity	NPC477411
0.7458	Intermediate Similarity	NPC67377
0.7456	Intermediate Similarity	NPC119271
0.7456	Intermediate Similarity	NPC136962
0.7455	Intermediate Similarity	NPC35448
0.7455	Intermediate Similarity	NPC78701
0.7453	Intermediate Similarity	NPC26224
0.7434	Intermediate Similarity	NPC109637
0.7434	Intermediate Similarity	NPC31786
0.7434	Intermediate Similarity	NPC269644
0.7417	Intermediate Similarity	NPC190298
0.7417	Intermediate Similarity	NPC212891
0.7414	Intermediate Similarity	NPC174099
0.7398	Intermediate Similarity	NPC322569
0.7395	Intermediate Similarity	NPC306740
0.7395	Intermediate Similarity	NPC186933
0.7391	Intermediate Similarity	NPC203732
0.7387	Intermediate Similarity	NPC203925
0.7387	Intermediate Similarity	NPC146351
0.7385	Intermediate Similarity	NPC183103
0.7381	Intermediate Similarity	NPC470765
0.7379	Intermediate Similarity	NPC95429
0.7377	Intermediate Similarity	NPC204784
0.7377	Intermediate Similarity	NPC98748
0.7373	Intermediate Similarity	NPC199462
0.7368	Intermediate Similarity	NPC105899
0.7364	Intermediate Similarity	NPC276775
0.7364	Intermediate Similarity	NPC92754
0.7364	Intermediate Similarity	NPC249912
0.7364	Intermediate Similarity	NPC315769
0.736	Intermediate Similarity	NPC85511
0.736	Intermediate Similarity	NPC318067
0.735	Intermediate Similarity	NPC291799
0.735	Intermediate Similarity	NPC183700
0.7348	Intermediate Similarity	NPC309056
0.7345	Intermediate Similarity	NPC19856
0.7345	Intermediate Similarity	NPC89886
0.7344	Intermediate Similarity	NPC181675
0.7344	Intermediate Similarity	NPC81261
0.7339	Intermediate Similarity	NPC130398
0.7333	Intermediate Similarity	NPC226093
0.7333	Intermediate Similarity	NPC149691
0.7333	Intermediate Similarity	NPC476476
0.7333	Intermediate Similarity	NPC296526
0.7333	Intermediate Similarity	NPC471616
0.7328	Intermediate Similarity	NPC474364
0.7328	Intermediate Similarity	NPC40178
0.7328	Intermediate Similarity	NPC470406
0.7328	Intermediate Similarity	NPC206341
0.7323	Intermediate Similarity	NPC253681
0.7323	Intermediate Similarity	NPC473220
0.7323	Intermediate Similarity	NPC470753
0.7317	Intermediate Similarity	NPC280827
0.7317	Intermediate Similarity	NPC473243
0.7317	Intermediate Similarity	NPC243059
0.7315	Intermediate Similarity	NPC128645
0.7311	Intermediate Similarity	NPC153053
0.7311	Intermediate Similarity	NPC326664
0.7304	Intermediate Similarity	NPC94751
0.7304	Intermediate Similarity	NPC142326
0.7304	Intermediate Similarity	NPC326447
0.7302	Intermediate Similarity	NPC474532
0.7302	Intermediate Similarity	NPC265413
0.7302	Intermediate Similarity	NPC10154
0.7302	Intermediate Similarity	NPC89630
0.7302	Intermediate Similarity	NPC107846
0.7302	Intermediate Similarity	NPC75432
0.7297	Intermediate Similarity	NPC225060
0.7297	Intermediate Similarity	NPC154517
0.7293	Intermediate Similarity	NPC265515
0.7288	Intermediate Similarity	NPC471188
0.7288	Intermediate Similarity	NPC321852
0.7288	Intermediate Similarity	NPC280789
0.7288	Intermediate Similarity	NPC474689
0.7287	Intermediate Similarity	NPC471832
0.7287	Intermediate Similarity	NPC57552
0.7282	Intermediate Similarity	NPC243289
0.7282	Intermediate Similarity	NPC208183
0.7281	Intermediate Similarity	NPC171831
0.7281	Intermediate Similarity	NPC242913

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 NPC273837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	969
0.2-0.3	1394
0.3-0.4	2613
0.4-0.5	2101
0.5-0.6	1158
0.6-0.7	388
0.7-0.8	115
0.8-0.85	21
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8073	Intermediate Similarity	NPD5909	Discontinued
0.7966	Intermediate Similarity	NPD5691	Approved
0.7899	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1281	Approved
0.7757	Intermediate Similarity	NPD1989	Approved
0.775	Intermediate Similarity	NPD4626	Approved
0.7739	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7008	Discontinued
0.7692	Intermediate Similarity	NPD5951	Approved
0.7667	Intermediate Similarity	NPD1651	Approved
0.7632	Intermediate Similarity	NPD2182	Approved
0.7627	Intermediate Similarity	NPD4198	Discontinued
0.7623	Intermediate Similarity	NPD1611	Approved
0.7581	Intermediate Similarity	NPD1283	Approved
0.7565	Intermediate Similarity	NPD5235	Approved
0.7565	Intermediate Similarity	NPD5237	Approved
0.7565	Intermediate Similarity	NPD5236	Approved
0.7565	Intermediate Similarity	NPD5240	Approved
0.7565	Intermediate Similarity	NPD5239	Approved
0.7545	Intermediate Similarity	NPD1238	Approved
0.7521	Intermediate Similarity	NPD5535	Approved
0.7519	Intermediate Similarity	NPD2979	Phase 3
0.75	Intermediate Similarity	NPD1282	Approved
0.7455	Intermediate Similarity	NPD5926	Approved
0.7434	Intermediate Similarity	NPD164	Approved
0.7381	Intermediate Similarity	NPD2797	Approved
0.7345	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6287	Discontinued
0.7317	Intermediate Similarity	NPD5126	Approved
0.7317	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5125	Phase 3
0.7304	Intermediate Similarity	NPD3134	Approved
0.7281	Intermediate Similarity	NPD3048	Approved
0.7281	Intermediate Similarity	NPD3046	Approved
0.7281	Intermediate Similarity	NPD3047	Approved
0.7279	Intermediate Similarity	NPD7003	Approved
0.7265	Intermediate Similarity	NPD2067	Discontinued
0.7244	Intermediate Similarity	NPD3267	Approved
0.7244	Intermediate Similarity	NPD3266	Approved
0.7239	Intermediate Similarity	NPD2438	Suspended
0.7239	Intermediate Similarity	NPD2531	Phase 2
0.7232	Intermediate Similarity	NPD2066	Phase 3
0.7203	Intermediate Similarity	NPD2201	Approved
0.7185	Intermediate Similarity	NPD2346	Discontinued
0.7182	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6049	Phase 2
0.7182	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2106	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3972	Approved
0.7115	Intermediate Similarity	NPD3971	Phase 1
0.7107	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3268	Approved
0.7097	Intermediate Similarity	NPD5585	Approved
0.7094	Intermediate Similarity	NPD1358	Approved
0.7091	Intermediate Similarity	NPD1563	Approved
0.7069	Intermediate Similarity	NPD9697	Approved
0.7064	Intermediate Similarity	NPD1239	Approved
0.7045	Intermediate Similarity	NPD8032	Phase 2
0.7043	Intermediate Similarity	NPD1930	Approved
0.7043	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1929	Approved
0.7034	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5454	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2558	Approved
0.7018	Intermediate Similarity	NPD2552	Approved
0.7018	Intermediate Similarity	NPD2553	Approved
0.7018	Intermediate Similarity	NPD2549	Approved
0.7018	Intermediate Similarity	NPD2550	Approved
0.7018	Intermediate Similarity	NPD2555	Approved
0.7009	Intermediate Similarity	NPD1087	Approved
0.7008	Intermediate Similarity	NPD1877	Discontinued
0.6992	Remote Similarity	NPD4060	Phase 1
0.6992	Remote Similarity	NPD4307	Phase 2
0.6992	Remote Similarity	NPD4140	Approved
0.6984	Remote Similarity	NPD3847	Discontinued
0.6975	Remote Similarity	NPD5451	Approved
0.697	Remote Similarity	NPD2313	Discontinued
0.6957	Remote Similarity	NPD4188	Approved
0.6957	Remote Similarity	NPD4189	Approved
0.6949	Remote Similarity	NPD2342	Discontinued
0.6942	Remote Similarity	NPD6858	Approved
0.6942	Remote Similarity	NPD7635	Approved
0.6942	Remote Similarity	NPD7094	Approved
0.6937	Remote Similarity	NPD1202	Approved
0.6935	Remote Similarity	NPD7644	Approved
0.6923	Remote Similarity	NPD2798	Approved
0.6911	Remote Similarity	NPD6387	Discontinued
0.6905	Remote Similarity	NPD17	Approved
0.6903	Remote Similarity	NPD1564	Approved
0.6903	Remote Similarity	NPD1565	Approved
0.6903	Remote Similarity	NPD1566	Phase 3
0.6899	Remote Similarity	NPD1876	Approved
0.6899	Remote Similarity	NPD5667	Approved
0.6894	Remote Similarity	NPD4625	Phase 3
0.6889	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6010	Discontinued
0.688	Remote Similarity	NPD1894	Discontinued
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5736	Approved
0.6864	Remote Similarity	NPD3524	Approved
0.6864	Remote Similarity	NPD3526	Approved
0.6861	Remote Similarity	NPD4477	Approved
0.6861	Remote Similarity	NPD4476	Approved
0.685	Remote Similarity	NPD3897	Approved
0.685	Remote Similarity	NPD3895	Approved
0.685	Remote Similarity	NPD3896	Approved
0.685	Remote Similarity	NPD3898	Approved
0.6842	Remote Similarity	NPD3764	Approved
0.6829	Remote Similarity	NPD2629	Approved
0.6822	Remote Similarity	NPD5327	Phase 3
0.6822	Remote Similarity	NPD4359	Approved
0.6822	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1086	Approved
0.6818	Remote Similarity	NPD1090	Approved
0.6818	Remote Similarity	NPD3672	Approved
0.6818	Remote Similarity	NPD3673	Approved
0.6818	Remote Similarity	NPD1089	Approved
0.6818	Remote Similarity	NPD6832	Phase 2
0.6812	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1932	Approved
0.6794	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4308	Phase 3
0.6788	Remote Similarity	NPD3748	Approved
0.6788	Remote Similarity	NPD2799	Discontinued
0.6786	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6273	Approved
0.6769	Remote Similarity	NPD3225	Approved
0.6767	Remote Similarity	NPD7095	Approved
0.6763	Remote Similarity	NPD2897	Discontinued
0.6754	Remote Similarity	NPD3495	Discontinued
0.6752	Remote Similarity	NPD6647	Phase 2
0.6748	Remote Similarity	NPD5283	Phase 1
0.6748	Remote Similarity	NPD1241	Discontinued
0.6746	Remote Similarity	NPD7741	Discontinued
0.6744	Remote Similarity	NPD1608	Approved
0.6727	Remote Similarity	NPD800	Approved
0.6726	Remote Similarity	NPD1693	Approved
0.6723	Remote Similarity	NPD2551	Approved
0.6723	Remote Similarity	NPD2559	Approved
0.6723	Remote Similarity	NPD5705	Approved
0.6723	Remote Similarity	NPD5706	Approved
0.6723	Remote Similarity	NPD5704	Approved
0.6721	Remote Similarity	NPD1137	Approved
0.6721	Remote Similarity	NPD1139	Approved
0.6719	Remote Similarity	NPD3496	Discontinued
0.6719	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7294	Phase 1
0.6716	Remote Similarity	NPD6798	Discontinued
0.6716	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1088	Approved
0.6693	Remote Similarity	NPD3445	Approved
0.6693	Remote Similarity	NPD3444	Approved
0.6693	Remote Similarity	NPD3443	Approved
0.6692	Remote Similarity	NPD1669	Approved
0.6692	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4618	Approved
0.6691	Remote Similarity	NPD4622	Approved
0.6691	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6065	Approved
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD1138	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD7713	Phase 3
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD5618	Discontinued
0.6644	Remote Similarity	NPD3226	Approved
0.6644	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1778	Approved
0.664	Remote Similarity	NPD709	Approved
0.6638	Remote Similarity	NPD7798	Approved
0.6638	Remote Similarity	NPD3020	Approved
0.6619	Remote Similarity	NPD5408	Approved
0.6619	Remote Similarity	NPD5404	Approved
0.6619	Remote Similarity	NPD5405	Approved
0.6619	Remote Similarity	NPD5406	Approved
0.6619	Remote Similarity	NPD2935	Discontinued
0.6618	Remote Similarity	NPD3373	Approved
0.6615	Remote Similarity	NPD6637	Approved
0.6613	Remote Similarity	NPD496	Approved
0.6613	Remote Similarity	NPD495	Approved
0.6613	Remote Similarity	NPD498	Approved
0.6612	Remote Similarity	NPD2684	Approved
0.6612	Remote Similarity	NPD2329	Discontinued
0.6606	Remote Similarity	NPD9257	Approved
0.6606	Remote Similarity	NPD9259	Approved
0.6594	Remote Similarity	NPD5689	Approved
0.6594	Remote Similarity	NPD5688	Approved
0.6589	Remote Similarity	NPD4106	Approved
0.6589	Remote Similarity	NPD4135	Approved
0.6589	Remote Similarity	NPD4136	Approved
0.6587	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4572	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