NPASS Compound

Structure

NPC272528 OpenBabel07101718322D 29 32 0 0 1 0 0 0 0 0999 V2000 7.0132 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 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 6 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 27 1 0 0 0 0 11 2 1 6 0 0 0 12 3 1 6 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 4 1 1 0 0 0 13 28 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 18 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 1 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 29 1 0 0 0 0 21 23 1 0 0 0 0 21 25 2 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 5 1 6 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.14
Volume:	412.845
LogP:	5.163
LogD:	4.244
LogS:	-5.701
# Rotatable Bonds:	3
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	5.314
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.735
MDCK Permeability:	1.080827132682316e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	82.77605438232422%
Volume Distribution (VD):	2.722
Pgp-substrate:	11.72517204284668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.959
CYP2C19-substrate:	0.601
CYP2C9-inhibitor:	0.926
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.921
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.677

ADMET: Excretion

Clearance (CL):	3.855
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.208
Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.94
Carcinogencity:	0.849
Eye Corrosion:	0.013
Eye Irritation:	0.044
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC272528

Natural Product ID:	NPC272528
*Common Name:**	PQCNMEKFPHIIHE-QESWSWRDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PQCNMEKFPHIIHE-QESWSWRDSA-N
Standard InCHI:	InChI=1S/C23H25ClO5/c1-6-11(2)7-8-14-9-15-16(10-27-14)18-17-20(12(3)13(4)28-22(17)26)29-23(18,5)21(25)19(15)24/h7-13,18H,6H2,1-5H3/b8-7+/t11-,12+,13+,18+,23-/m0/s1
SMILES:	CC[C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]3([C@H](C2=CO1)C1=C(O3)[C@@H]([C@H](OC1=O)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3621758
PubChem CID:	25141203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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	3
Others	4

Activity Type	# Activity
Cell Line	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	82.8	%	PMID[528124]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	99.3	%	PMID[528124]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	28.5	%	PMID[528124]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1900.0	nM	PMID[528124]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	20700.0	nM	PMID[528124]
NPT2	Others	Unspecified		Inhibition	=	97.7	%	PMID[528124]
NPT2	Others	Unspecified		IC50	=	5100.0	nM	PMID[528124]

☑ 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 NPC272528 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	247
0.1-0.2	1452
0.2-0.3	6198
0.3-0.4	14589
0.4-0.5	13880
0.5-0.6	5572
0.6-0.7	695
0.7-0.8	52
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8624	High Similarity	NPC243298
0.8485	Intermediate Similarity	NPC143210
0.8468	Intermediate Similarity	NPC245320
0.84	Intermediate Similarity	NPC12727
0.8393	Intermediate Similarity	NPC473145
0.8393	Intermediate Similarity	NPC31641
0.8367	Intermediate Similarity	NPC224270
0.823	Intermediate Similarity	NPC476815
0.8131	Intermediate Similarity	NPC232969
0.8131	Intermediate Similarity	NPC199107
0.8077	Intermediate Similarity	NPC185253
0.8077	Intermediate Similarity	NPC215253
0.8058	Intermediate Similarity	NPC134083
0.8019	Intermediate Similarity	NPC271059
0.8019	Intermediate Similarity	NPC25666
0.7981	Intermediate Similarity	NPC166770
0.785	Intermediate Similarity	NPC297281
0.785	Intermediate Similarity	NPC473144
0.783	Intermediate Similarity	NPC224172
0.7788	Intermediate Similarity	NPC318082
0.7677	Intermediate Similarity	NPC281172
0.7664	Intermediate Similarity	NPC469851
0.76	Intermediate Similarity	NPC291712
0.7573	Intermediate Similarity	NPC32944
0.7573	Intermediate Similarity	NPC193396
0.7573	Intermediate Similarity	NPC166110
0.7549	Intermediate Similarity	NPC95364
0.7549	Intermediate Similarity	NPC142159
0.7524	Intermediate Similarity	NPC31021
0.75	Intermediate Similarity	NPC248193
0.7404	Intermediate Similarity	NPC32552
0.7387	Intermediate Similarity	NPC469852
0.7339	Intermediate Similarity	NPC471699
0.7321	Intermediate Similarity	NPC469853
0.7196	Intermediate Similarity	NPC471698
0.7143	Intermediate Similarity	NPC469372
0.7105	Intermediate Similarity	NPC327106
0.7094	Intermediate Similarity	NPC321496
0.7043	Intermediate Similarity	NPC137911
0.7043	Intermediate Similarity	NPC228477
0.7041	Intermediate Similarity	NPC471225
0.7037	Intermediate Similarity	NPC295347
0.7009	Intermediate Similarity	NPC66108
0.7009	Intermediate Similarity	NPC476598
0.7009	Intermediate Similarity	NPC1108
0.7009	Intermediate Similarity	NPC476597
0.6981	Remote Similarity	NPC471818
0.6981	Remote Similarity	NPC220454
0.6981	Remote Similarity	NPC212679
0.6981	Remote Similarity	NPC469595
0.6972	Remote Similarity	NPC301596
0.6972	Remote Similarity	NPC172998
0.6972	Remote Similarity	NPC299396
0.6949	Remote Similarity	NPC326264
0.6944	Remote Similarity	NPC476596
0.6923	Remote Similarity	NPC203795
0.6909	Remote Similarity	NPC208094
0.6909	Remote Similarity	NPC84335
0.6909	Remote Similarity	NPC38530
0.6897	Remote Similarity	NPC23497
0.6887	Remote Similarity	NPC284561
0.6881	Remote Similarity	NPC273197
0.6881	Remote Similarity	NPC234339
0.6875	Remote Similarity	NPC244456
0.6875	Remote Similarity	NPC469657
0.6852	Remote Similarity	NPC165383
0.6852	Remote Similarity	NPC282644
0.6852	Remote Similarity	NPC29798
0.6827	Remote Similarity	NPC471060
0.6814	Remote Similarity	NPC235369
0.6807	Remote Similarity	NPC474271
0.6796	Remote Similarity	NPC288281
0.6792	Remote Similarity	NPC471057
0.6792	Remote Similarity	NPC471058
0.6792	Remote Similarity	NPC475902
0.6792	Remote Similarity	NPC472302
0.6789	Remote Similarity	NPC477129
0.6789	Remote Similarity	NPC477130
0.6789	Remote Similarity	NPC38830
0.6783	Remote Similarity	NPC477125
0.6783	Remote Similarity	NPC472645
0.6765	Remote Similarity	NPC42470
0.6733	Remote Similarity	NPC178277
0.6729	Remote Similarity	NPC280833
0.6729	Remote Similarity	NPC471054
0.6726	Remote Similarity	NPC168319
0.6726	Remote Similarity	NPC194028
0.6726	Remote Similarity	NPC472643
0.6726	Remote Similarity	NPC473384
0.6724	Remote Similarity	NPC133422
0.67	Remote Similarity	NPC473825
0.6699	Remote Similarity	NPC268122
0.6699	Remote Similarity	NPC471326
0.6699	Remote Similarity	NPC173609
0.6699	Remote Similarity	NPC221231
0.6696	Remote Similarity	NPC54843
0.6696	Remote Similarity	NPC474898
0.6695	Remote Similarity	NPC206595
0.6667	Remote Similarity	NPC112654
0.6667	Remote Similarity	NPC264819
0.6667	Remote Similarity	NPC260796
0.6667	Remote Similarity	NPC273005
0.6667	Remote Similarity	NPC189609
0.6667	Remote Similarity	NPC140591
0.6667	Remote Similarity	NPC303653
0.6667	Remote Similarity	NPC130030
0.6667	Remote Similarity	NPC291500
0.6667	Remote Similarity	NPC469606
0.6667	Remote Similarity	NPC197835
0.6667	Remote Similarity	NPC31058
0.6639	Remote Similarity	NPC179798
0.6639	Remote Similarity	NPC304180
0.6638	Remote Similarity	NPC266570
0.6638	Remote Similarity	NPC478052
0.6638	Remote Similarity	NPC34768
0.6638	Remote Similarity	NPC469607
0.6637	Remote Similarity	NPC110897
0.6636	Remote Similarity	NPC473658
0.6636	Remote Similarity	NPC26078
0.6635	Remote Similarity	NPC474703
0.6635	Remote Similarity	NPC193198
0.6635	Remote Similarity	NPC118423
0.661	Remote Similarity	NPC469370
0.6609	Remote Similarity	NPC471364
0.6609	Remote Similarity	NPC320294
0.6609	Remote Similarity	NPC471365
0.6609	Remote Similarity	NPC132395
0.6607	Remote Similarity	NPC110937
0.6604	Remote Similarity	NPC220478
0.6604	Remote Similarity	NPC279859
0.6604	Remote Similarity	NPC168248
0.6604	Remote Similarity	NPC38576
0.6602	Remote Similarity	NPC471325
0.6602	Remote Similarity	NPC275507
0.6583	Remote Similarity	NPC147180
0.6583	Remote Similarity	NPC221144
0.6583	Remote Similarity	NPC264634
0.6581	Remote Similarity	NPC266514
0.6577	Remote Similarity	NPC470978
0.6577	Remote Similarity	NPC470974
0.6577	Remote Similarity	NPC474947
0.6574	Remote Similarity	NPC307092
0.6574	Remote Similarity	NPC474844
0.6574	Remote Similarity	NPC51358
0.6571	Remote Similarity	NPC474359
0.6571	Remote Similarity	NPC149869
0.6571	Remote Similarity	NPC30486
0.6571	Remote Similarity	NPC159635
0.6569	Remote Similarity	NPC270126
0.6566	Remote Similarity	NPC294434
0.6566	Remote Similarity	NPC259599
0.6566	Remote Similarity	NPC15499
0.6566	Remote Similarity	NPC474758
0.6566	Remote Similarity	NPC117746
0.6562	Remote Similarity	NPC476008
0.6557	Remote Similarity	NPC270478
0.6555	Remote Similarity	NPC89408
0.6552	Remote Similarity	NPC476001
0.6552	Remote Similarity	NPC189616
0.6549	Remote Similarity	NPC35717
0.6542	Remote Similarity	NPC241054
0.6538	Remote Similarity	NPC10080
0.6538	Remote Similarity	NPC123908
0.6535	Remote Similarity	NPC68156
0.6535	Remote Similarity	NPC57744
0.6532	Remote Similarity	NPC158963
0.6531	Remote Similarity	NPC133098
0.6529	Remote Similarity	NPC469454
0.6529	Remote Similarity	NPC469496
0.6529	Remote Similarity	NPC56448
0.6529	Remote Similarity	NPC469463
0.6529	Remote Similarity	NPC159333
0.6514	Remote Similarity	NPC213636
0.6514	Remote Similarity	NPC329857
0.6514	Remote Similarity	NPC253177
0.6514	Remote Similarity	NPC280592
0.6514	Remote Similarity	NPC469718
0.6509	Remote Similarity	NPC67081
0.6509	Remote Similarity	NPC189311
0.6509	Remote Similarity	NPC471223
0.65	Remote Similarity	NPC43775
0.65	Remote Similarity	NPC474315
0.6496	Remote Similarity	NPC85529
0.6496	Remote Similarity	NPC32006
0.6496	Remote Similarity	NPC478208
0.6495	Remote Similarity	NPC470693
0.6491	Remote Similarity	NPC474012
0.6491	Remote Similarity	NPC472644
0.6491	Remote Similarity	NPC54705
0.6491	Remote Similarity	NPC476299
0.6486	Remote Similarity	NPC56525
0.6486	Remote Similarity	NPC84893
0.6486	Remote Similarity	NPC470697
0.6484	Remote Similarity	NPC477745
0.6481	Remote Similarity	NPC469628
0.6481	Remote Similarity	NPC478261
0.6481	Remote Similarity	NPC471047
0.6481	Remote Similarity	NPC478259
0.6481	Remote Similarity	NPC226863
0.6481	Remote Similarity	NPC469653

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 NPC272528 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1574
0.2-0.3	4119
0.3-0.4	2378
0.4-0.5	665
0.5-0.6	198
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6581	Remote Similarity	NPD6614	Approved
0.6577	Remote Similarity	NPD5654	Approved
0.646	Remote Similarity	NPD5959	Approved
0.6452	Remote Similarity	NPD6335	Approved
0.6452	Remote Similarity	NPD6314	Approved
0.6452	Remote Similarity	NPD6313	Approved
0.6446	Remote Similarity	NPD6053	Discontinued
0.6404	Remote Similarity	NPD5696	Approved
0.64	Remote Similarity	NPD7101	Approved
0.64	Remote Similarity	NPD7100	Approved
0.6306	Remote Similarity	NPD5693	Phase 1
0.6306	Remote Similarity	NPD5694	Approved
0.6303	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6899	Approved
0.623	Remote Similarity	NPD6649	Approved
0.623	Remote Similarity	NPD6650	Approved
0.6226	Remote Similarity	NPD5209	Approved
0.6218	Remote Similarity	NPD6675	Approved
0.6218	Remote Similarity	NPD7128	Approved
0.6218	Remote Similarity	NPD5739	Approved
0.6218	Remote Similarity	NPD6402	Approved
0.6216	Remote Similarity	NPD5692	Phase 3
0.6204	Remote Similarity	NPD1694	Approved
0.6198	Remote Similarity	NPD6372	Approved
0.6198	Remote Similarity	NPD6013	Approved
0.6198	Remote Similarity	NPD6014	Approved
0.6198	Remote Similarity	NPD6373	Approved
0.6198	Remote Similarity	NPD6012	Approved
0.6182	Remote Similarity	NPD6672	Approved
0.6182	Remote Similarity	NPD5737	Approved
0.6167	Remote Similarity	NPD5701	Approved
0.6161	Remote Similarity	NPD6050	Approved
0.616	Remote Similarity	NPD6868	Approved
0.6148	Remote Similarity	NPD6883	Approved
0.6148	Remote Similarity	NPD7102	Approved
0.6148	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD5695	Phase 3
0.6119	Remote Similarity	NPD7260	Phase 2
0.6116	Remote Similarity	NPD6011	Approved
0.6116	Remote Similarity	NPD7320	Approved
0.6111	Remote Similarity	NPD7115	Discovery
0.6098	Remote Similarity	NPD6617	Approved
0.6098	Remote Similarity	NPD8130	Phase 1
0.6098	Remote Similarity	NPD6847	Approved
0.6098	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4756	Discovery
0.6048	Remote Similarity	NPD6882	Approved
0.6048	Remote Similarity	NPD8297	Approved
0.6047	Remote Similarity	NPD5983	Phase 2
0.6034	Remote Similarity	NPD6084	Phase 2
0.6034	Remote Similarity	NPD6083	Phase 2
0.6016	Remote Similarity	NPD2067	Discontinued
0.6016	Remote Similarity	NPD5169	Approved
0.5985	Remote Similarity	NPD6336	Discontinued
0.5984	Remote Similarity	NPD5128	Approved
0.5982	Remote Similarity	NPD6080	Approved
0.5982	Remote Similarity	NPD6904	Approved
0.5982	Remote Similarity	NPD6673	Approved
0.5968	Remote Similarity	NPD5216	Approved
0.5968	Remote Similarity	NPD5217	Approved
0.5968	Remote Similarity	NPD5215	Approved
0.5968	Remote Similarity	NPD5127	Approved
0.5966	Remote Similarity	NPD5091	Approved
0.5965	Remote Similarity	NPD6399	Phase 3
0.595	Remote Similarity	NPD6008	Approved
0.5929	Remote Similarity	NPD5207	Approved
0.5923	Remote Similarity	NPD8513	Phase 3
0.5913	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5282	Discontinued
0.5913	Remote Similarity	NPD7900	Approved
0.5902	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5284	Approved
0.5877	Remote Similarity	NPD5281	Approved
0.5873	Remote Similarity	NPD4632	Approved
0.5872	Remote Similarity	NPD6110	Phase 1
0.5862	Remote Similarity	NPD4629	Approved
0.5862	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5210	Approved
0.5859	Remote Similarity	NPD6009	Approved
0.5856	Remote Similarity	NPD5330	Approved
0.5856	Remote Similarity	NPD7146	Approved
0.5856	Remote Similarity	NPD7521	Approved
0.5856	Remote Similarity	NPD6409	Approved
0.5856	Remote Similarity	NPD7334	Approved
0.5856	Remote Similarity	NPD6684	Approved
0.5841	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6101	Approved
0.584	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5211	Phase 2
0.5827	Remote Similarity	NPD5167	Approved
0.5826	Remote Similarity	NPD5778	Approved
0.5826	Remote Similarity	NPD5779	Approved
0.5804	Remote Similarity	NPD3573	Approved
0.5802	Remote Similarity	NPD8517	Approved
0.5802	Remote Similarity	NPD8515	Approved
0.5802	Remote Similarity	NPD8516	Approved
0.5798	Remote Similarity	NPD5286	Approved
0.5798	Remote Similarity	NPD4696	Approved
0.5798	Remote Similarity	NPD5285	Approved
0.5781	Remote Similarity	NPD6274	Approved
0.5763	Remote Similarity	NPD7902	Approved
0.5763	Remote Similarity	NPD4755	Approved
0.576	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6903	Approved
0.5752	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6411	Approved
0.5738	Remote Similarity	NPD5141	Approved
0.5736	Remote Similarity	NPD6317	Approved
0.5727	Remote Similarity	NPD7154	Phase 3
0.5726	Remote Similarity	NPD5168	Approved
0.5725	Remote Similarity	NPD6319	Approved
0.5725	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6098	Approved
0.5714	Remote Similarity	NPD8039	Approved
0.5714	Remote Similarity	NPD4225	Approved
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4633	Approved
0.5702	Remote Similarity	NPD5224	Approved
0.5702	Remote Similarity	NPD5225	Approved
0.5702	Remote Similarity	NPD5226	Approved
0.5702	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.569	Remote Similarity	NPD5133	Approved
0.568	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7639	Approved
0.5667	Remote Similarity	NPD4700	Approved
0.5667	Remote Similarity	NPD7640	Approved
0.5662	Remote Similarity	NPD6033	Approved
0.5656	Remote Similarity	NPD5175	Approved
0.5656	Remote Similarity	NPD5174	Approved
0.5652	Remote Similarity	NPD46	Approved
0.5652	Remote Similarity	NPD5785	Approved
0.5652	Remote Similarity	NPD6698	Approved
0.5645	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7748	Approved
0.5625	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD1696	Phase 3
0.562	Remote Similarity	NPD5223	Approved
0.56	Remote Similarity	NPD6686	Approved
0.56	Remote Similarity	NPD2685	Clinical (unspecified phase)

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