NPASS Compound

Structure

NPC471727 OpenBabel07101718332D 25 28 0 0 1 0 0 0 0 0999 V2000 -3.3446 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8274 -0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3102 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 -1.4483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8362 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 -0.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3446 0.9655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8362 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3446 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8362 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6723 -2.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -0.0000 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 12 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 24 1 0 0 0 0 13 21 1 1 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 22 2 0 0 0 0 16 19 1 0 0 0 0 16 20 1 6 0 0 0 17 19 1 0 0 0 0 17 23 1 6 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 20 21 1 1 0 0 0 21 5 1 1 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	364.798
LogP:	4.396
LogD:	3.454
LogS:	-2.903
# Rotatable Bonds:	0
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.775
Synthetic Accessibility Score:	4.656
Fsp3:	0.762
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:	-4.634
MDCK Permeability:	2.4211609343183227e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.313
Plasma Protein Binding (PPB):	80.28336334228516%
Volume Distribution (VD):	0.989
Pgp-substrate:	18.801830291748047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.156
CYP1A2-substrate:	0.645
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.309
CYP3A4-substrate:	0.597

ADMET: Excretion

Clearance (CL):	12.426
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.584
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.751
Carcinogencity:	0.955
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471727

Natural Product ID:	NPC471727
*Common Name:**	RCJJNXSFMKDPPQ-BKRLDNPDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RCJJNXSFMKDPPQ-BKRLDNPDSA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-12-10-15(22)14-11-13-6-7-16-19(2,3)17(23)8-9-20(16,4)21(13,5)25-18(14)24-12/h10,13,16-17,23H,6-9,11H2,1-5H3/t13-,16-,17-,20-,21-/m0/s1
SMILES:	CC1=CC(=O)C2=C(O1)OC3(C(C2)CCC4C3(CCC(C4(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109293
PubChem CID:	76335680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
MIC	10
Others	2

Activity Type	# Activity
Cell Line	2
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	LC50	=	15000.0	nM	PMID[551736]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	28000.0	nM	PMID[551736]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[551736]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[551736]

☑ 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 NPC471727 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	347
0.1-0.2	1388
0.2-0.3	2699
0.3-0.4	5608
0.4-0.5	9823
0.5-0.6	8730
0.6-0.7	6949
0.7-0.8	6917
0.8-0.85	214
0.85-0.9	18
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8804	High Similarity	NPC471728
0.8333	Intermediate Similarity	NPC291154
0.8229	Intermediate Similarity	NPC50070
0.8218	Intermediate Similarity	NPC472972
0.8155	Intermediate Similarity	NPC275583
0.8155	Intermediate Similarity	NPC95585
0.8155	Intermediate Similarity	NPC282233
0.81	Intermediate Similarity	NPC5532
0.81	Intermediate Similarity	NPC469545
0.81	Intermediate Similarity	NPC61369
0.8081	Intermediate Similarity	NPC103527
0.8081	Intermediate Similarity	NPC471207
0.8019	Intermediate Similarity	NPC272576
0.8	Intermediate Similarity	NPC139570
0.7982	Intermediate Similarity	NPC62696
0.7982	Intermediate Similarity	NPC293038
0.7981	Intermediate Similarity	NPC478057
0.798	Intermediate Similarity	NPC214756
0.798	Intermediate Similarity	NPC295643
0.798	Intermediate Similarity	NPC272075
0.7979	Intermediate Similarity	NPC64600
0.7963	Intermediate Similarity	NPC201992
0.7961	Intermediate Similarity	NPC471412
0.7941	Intermediate Similarity	NPC114274
0.7938	Intermediate Similarity	NPC328539
0.7917	Intermediate Similarity	NPC73038
0.7917	Intermediate Similarity	NPC472985
0.7917	Intermediate Similarity	NPC472986
0.7909	Intermediate Similarity	NPC102088
0.789	Intermediate Similarity	NPC11252
0.789	Intermediate Similarity	NPC289312
0.7885	Intermediate Similarity	NPC476769
0.7879	Intermediate Similarity	NPC65120
0.7879	Intermediate Similarity	NPC158030
0.7879	Intermediate Similarity	NPC472975
0.7879	Intermediate Similarity	NPC185936
0.7879	Intermediate Similarity	NPC472978
0.7879	Intermediate Similarity	NPC233455
0.7879	Intermediate Similarity	NPC168027
0.7879	Intermediate Similarity	NPC145067
0.7879	Intermediate Similarity	NPC4036
0.7864	Intermediate Similarity	NPC471413
0.7864	Intermediate Similarity	NPC476767
0.7857	Intermediate Similarity	NPC472973
0.785	Intermediate Similarity	NPC293850
0.7843	Intermediate Similarity	NPC472851
0.7843	Intermediate Similarity	NPC473456
0.7838	Intermediate Similarity	NPC235539
0.7838	Intermediate Similarity	NPC152199
0.7838	Intermediate Similarity	NPC134869
0.7835	Intermediate Similarity	NPC298904
0.783	Intermediate Similarity	NPC478052
0.783	Intermediate Similarity	NPC102352
0.783	Intermediate Similarity	NPC478208
0.7822	Intermediate Similarity	NPC473170
0.7822	Intermediate Similarity	NPC474727
0.7822	Intermediate Similarity	NPC473240
0.7818	Intermediate Similarity	NPC51978
0.7818	Intermediate Similarity	NPC178981
0.7818	Intermediate Similarity	NPC157441
0.781	Intermediate Similarity	NPC95899
0.781	Intermediate Similarity	NPC179208
0.7798	Intermediate Similarity	NPC171888
0.7798	Intermediate Similarity	NPC146945
0.7798	Intermediate Similarity	NPC471243
0.7788	Intermediate Similarity	NPC279143
0.7788	Intermediate Similarity	NPC14634
0.7778	Intermediate Similarity	NPC310546
0.7778	Intermediate Similarity	NPC27814
0.7778	Intermediate Similarity	NPC223093
0.7768	Intermediate Similarity	NPC309433
0.7767	Intermediate Similarity	NPC475876
0.7767	Intermediate Similarity	NPC58942
0.7767	Intermediate Similarity	NPC260149
0.7757	Intermediate Similarity	NPC144854
0.7757	Intermediate Similarity	NPC3316
0.7757	Intermediate Similarity	NPC202524
0.7755	Intermediate Similarity	NPC474925
0.7755	Intermediate Similarity	NPC193360
0.7755	Intermediate Similarity	NPC472802
0.7755	Intermediate Similarity	NPC158778
0.7748	Intermediate Similarity	NPC247069
0.7748	Intermediate Similarity	NPC474906
0.7748	Intermediate Similarity	NPC477580
0.7748	Intermediate Similarity	NPC18547
0.7745	Intermediate Similarity	NPC476327
0.7745	Intermediate Similarity	NPC476318
0.7745	Intermediate Similarity	NPC98874
0.7736	Intermediate Similarity	NPC475036
0.7736	Intermediate Similarity	NPC222161
0.7732	Intermediate Similarity	NPC158393
0.7727	Intermediate Similarity	NPC12046
0.7727	Intermediate Similarity	NPC194951
0.7727	Intermediate Similarity	NPC471967
0.7727	Intermediate Similarity	NPC205534
0.7723	Intermediate Similarity	NPC472977
0.7723	Intermediate Similarity	NPC470385
0.7723	Intermediate Similarity	NPC74751
0.7723	Intermediate Similarity	NPC474529
0.7723	Intermediate Similarity	NPC470386
0.7723	Intermediate Similarity	NPC196227
0.7723	Intermediate Similarity	NPC196485
0.7723	Intermediate Similarity	NPC474963
0.7723	Intermediate Similarity	NPC245972
0.7723	Intermediate Similarity	NPC472976
0.7723	Intermediate Similarity	NPC111015
0.7723	Intermediate Similarity	NPC23170
0.7714	Intermediate Similarity	NPC162973
0.7714	Intermediate Similarity	NPC309388
0.7714	Intermediate Similarity	NPC22388
0.7714	Intermediate Similarity	NPC475803
0.7706	Intermediate Similarity	NPC163314
0.7706	Intermediate Similarity	NPC197428
0.7706	Intermediate Similarity	NPC470065
0.77	Intermediate Similarity	NPC116726
0.7699	Intermediate Similarity	NPC176005
0.7699	Intermediate Similarity	NPC204552
0.7699	Intermediate Similarity	NPC188667
0.7699	Intermediate Similarity	NPC297179
0.7692	Intermediate Similarity	NPC104861
0.7692	Intermediate Similarity	NPC83709
0.7692	Intermediate Similarity	NPC471041
0.7692	Intermediate Similarity	NPC117685
0.7685	Intermediate Similarity	NPC154608
0.7685	Intermediate Similarity	NPC192813
0.7685	Intermediate Similarity	NPC277017
0.7685	Intermediate Similarity	NPC473288
0.7685	Intermediate Similarity	NPC275539
0.7685	Intermediate Similarity	NPC189075
0.7679	Intermediate Similarity	NPC302471
0.7677	Intermediate Similarity	NPC86319
0.7677	Intermediate Similarity	NPC69627
0.7677	Intermediate Similarity	NPC275740
0.7677	Intermediate Similarity	NPC186688
0.767	Intermediate Similarity	NPC476878
0.767	Intermediate Similarity	NPC272451
0.767	Intermediate Similarity	NPC189880
0.767	Intermediate Similarity	NPC476879
0.767	Intermediate Similarity	NPC18509
0.767	Intermediate Similarity	NPC190554
0.767	Intermediate Similarity	NPC89225
0.767	Intermediate Similarity	NPC108078
0.7664	Intermediate Similarity	NPC4115
0.7664	Intermediate Similarity	NPC469607
0.7664	Intermediate Similarity	NPC12823
0.7664	Intermediate Similarity	NPC278628
0.7664	Intermediate Similarity	NPC231530
0.7664	Intermediate Similarity	NPC127609
0.7658	Intermediate Similarity	NPC208998
0.7658	Intermediate Similarity	NPC7921
0.7658	Intermediate Similarity	NPC49451
0.7658	Intermediate Similarity	NPC471627
0.7658	Intermediate Similarity	NPC471173
0.7658	Intermediate Similarity	NPC255017
0.7658	Intermediate Similarity	NPC25909
0.7658	Intermediate Similarity	NPC260665
0.7653	Intermediate Similarity	NPC153604
0.7652	Intermediate Similarity	NPC275675
0.7647	Intermediate Similarity	NPC317586
0.7647	Intermediate Similarity	NPC279974
0.7647	Intermediate Similarity	NPC470016
0.7647	Intermediate Similarity	NPC470232
0.7647	Intermediate Similarity	NPC272617
0.7647	Intermediate Similarity	NPC271195
0.7647	Intermediate Similarity	NPC266899
0.7647	Intermediate Similarity	NPC148523
0.7642	Intermediate Similarity	NPC320294
0.7642	Intermediate Similarity	NPC312900
0.7642	Intermediate Similarity	NPC139347
0.7632	Intermediate Similarity	NPC473401
0.7632	Intermediate Similarity	NPC127530
0.7632	Intermediate Similarity	NPC473920
0.7629	Intermediate Similarity	NPC133954
0.7629	Intermediate Similarity	NPC470574
0.7624	Intermediate Similarity	NPC477855
0.7619	Intermediate Similarity	NPC471790
0.7619	Intermediate Similarity	NPC472637
0.7615	Intermediate Similarity	NPC476759
0.7615	Intermediate Similarity	NPC472534
0.7615	Intermediate Similarity	NPC246205
0.7615	Intermediate Similarity	NPC478210
0.7615	Intermediate Similarity	NPC143706
0.76	Intermediate Similarity	NPC134321
0.76	Intermediate Similarity	NPC472325
0.76	Intermediate Similarity	NPC291028
0.76	Intermediate Similarity	NPC475823
0.76	Intermediate Similarity	NPC232202
0.76	Intermediate Similarity	NPC85173
0.76	Intermediate Similarity	NPC474209
0.76	Intermediate Similarity	NPC128672
0.7596	Intermediate Similarity	NPC478056
0.7596	Intermediate Similarity	NPC471966
0.7596	Intermediate Similarity	NPC477854
0.7596	Intermediate Similarity	NPC119036
0.7593	Intermediate Similarity	NPC110496
0.7589	Intermediate Similarity	NPC243354
0.7589	Intermediate Similarity	NPC473798
0.7586	Intermediate Similarity	NPC28532
0.7579	Intermediate Similarity	NPC473217
0.7576	Intermediate Similarity	NPC40552

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 NPC471727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	897
0.2-0.3	1556
0.3-0.4	2520
0.4-0.5	2145
0.5-0.6	1142
0.6-0.7	438
0.7-0.8	131
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7879	Intermediate Similarity	NPD7515	Phase 2
0.7857	Intermediate Similarity	NPD5328	Approved
0.7768	Intermediate Similarity	NPD6009	Approved
0.7732	Intermediate Similarity	NPD3618	Phase 1
0.7723	Intermediate Similarity	NPD7748	Approved
0.77	Intermediate Similarity	NPD6079	Approved
0.767	Intermediate Similarity	NPD4755	Approved
0.7593	Intermediate Similarity	NPD6412	Phase 2
0.7573	Intermediate Similarity	NPD5221	Approved
0.7573	Intermediate Similarity	NPD4697	Phase 3
0.7573	Intermediate Similarity	NPD5222	Approved
0.7573	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6882	Approved
0.7565	Intermediate Similarity	NPD6059	Approved
0.7565	Intermediate Similarity	NPD6054	Approved
0.7524	Intermediate Similarity	NPD5286	Approved
0.7524	Intermediate Similarity	NPD4700	Approved
0.7524	Intermediate Similarity	NPD4696	Approved
0.7524	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.7475	Intermediate Similarity	NPD3573	Approved
0.7453	Intermediate Similarity	NPD5223	Approved
0.7451	Intermediate Similarity	NPD4202	Approved
0.7436	Intermediate Similarity	NPD6370	Approved
0.7436	Intermediate Similarity	NPD5988	Approved
0.7431	Intermediate Similarity	NPD5701	Approved
0.7431	Intermediate Similarity	NPD5697	Approved
0.7429	Intermediate Similarity	NPD7638	Approved
0.7383	Intermediate Similarity	NPD5226	Approved
0.7383	Intermediate Similarity	NPD4633	Approved
0.7383	Intermediate Similarity	NPD5211	Phase 2
0.7383	Intermediate Similarity	NPD5225	Approved
0.7383	Intermediate Similarity	NPD5224	Approved
0.7373	Intermediate Similarity	NPD8328	Phase 3
0.7364	Intermediate Similarity	NPD7320	Approved
0.7364	Intermediate Similarity	NPD6899	Approved
0.7364	Intermediate Similarity	NPD6011	Approved
0.7364	Intermediate Similarity	NPD6881	Approved
0.7358	Intermediate Similarity	NPD7640	Approved
0.7358	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD3133	Approved
0.7347	Intermediate Similarity	NPD3665	Phase 1
0.7347	Intermediate Similarity	NPD3666	Approved
0.7339	Intermediate Similarity	NPD6008	Approved
0.732	Intermediate Similarity	NPD3667	Approved
0.7315	Intermediate Similarity	NPD5174	Approved
0.7315	Intermediate Similarity	NPD4754	Approved
0.7315	Intermediate Similarity	NPD5175	Approved
0.7311	Intermediate Similarity	NPD7492	Approved
0.7297	Intermediate Similarity	NPD6372	Approved
0.7297	Intermediate Similarity	NPD6373	Approved
0.7297	Intermediate Similarity	NPD6012	Approved
0.7297	Intermediate Similarity	NPD6013	Approved
0.7297	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD7736	Approved
0.725	Intermediate Similarity	NPD6616	Approved
0.725	Intermediate Similarity	NPD7507	Approved
0.7248	Intermediate Similarity	NPD5141	Approved
0.7232	Intermediate Similarity	NPD7102	Approved
0.7232	Intermediate Similarity	NPD4634	Approved
0.7232	Intermediate Similarity	NPD6883	Approved
0.7232	Intermediate Similarity	NPD7290	Approved
0.7212	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7900	Approved
0.719	Intermediate Similarity	NPD7078	Approved
0.719	Intermediate Similarity	NPD8293	Discontinued
0.7182	Intermediate Similarity	NPD4767	Approved
0.7182	Intermediate Similarity	NPD4768	Approved
0.7172	Intermediate Similarity	NPD4786	Approved
0.7168	Intermediate Similarity	NPD6847	Approved
0.7168	Intermediate Similarity	NPD6649	Approved
0.7168	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6650	Approved
0.7168	Intermediate Similarity	NPD8130	Phase 1
0.7168	Intermediate Similarity	NPD6869	Approved
0.7168	Intermediate Similarity	NPD6617	Approved
0.7157	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6033	Approved
0.7119	Intermediate Similarity	NPD6319	Approved
0.7113	Intermediate Similarity	NPD4695	Discontinued
0.7105	Intermediate Similarity	NPD8297	Approved
0.7073	Intermediate Similarity	NPD7319	Approved
0.7059	Intermediate Similarity	NPD5983	Phase 2
0.7054	Intermediate Similarity	NPD4729	Approved
0.7054	Intermediate Similarity	NPD4730	Approved
0.7054	Intermediate Similarity	NPD6686	Approved
0.7054	Intermediate Similarity	NPD5128	Approved
0.703	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.697	Remote Similarity	NPD4221	Approved
0.697	Remote Similarity	NPD4223	Phase 3
0.6957	Remote Similarity	NPD6053	Discontinued
0.6952	Remote Similarity	NPD6399	Phase 3
0.6942	Remote Similarity	NPD7604	Phase 2
0.6942	Remote Similarity	NPD6067	Discontinued
0.6931	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5169	Approved
0.693	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5249	Phase 3
0.693	Remote Similarity	NPD5247	Approved
0.693	Remote Similarity	NPD5250	Approved
0.693	Remote Similarity	NPD5135	Approved
0.693	Remote Similarity	NPD5251	Approved
0.693	Remote Similarity	NPD5248	Approved
0.6923	Remote Similarity	NPD6274	Approved
0.6903	Remote Similarity	NPD5168	Approved
0.6893	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5217	Approved
0.687	Remote Similarity	NPD5215	Approved
0.687	Remote Similarity	NPD5216	Approved
0.687	Remote Similarity	NPD5127	Approved
0.6864	Remote Similarity	NPD6317	Approved
0.6864	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7115	Discovery
0.6863	Remote Similarity	NPD5279	Phase 3
0.6863	Remote Similarity	NPD7146	Approved
0.6863	Remote Similarity	NPD6684	Approved
0.6863	Remote Similarity	NPD7334	Approved
0.6863	Remote Similarity	NPD6409	Approved
0.6863	Remote Similarity	NPD5330	Approved
0.6863	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7645	Phase 2
0.6832	Remote Similarity	NPD3668	Phase 3
0.6832	Remote Similarity	NPD4197	Approved
0.6829	Remote Similarity	NPD6336	Discontinued
0.6827	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5210	Approved
0.6822	Remote Similarity	NPD4629	Approved
0.6822	Remote Similarity	NPD5695	Phase 3
0.6807	Remote Similarity	NPD6313	Approved
0.6807	Remote Similarity	NPD6314	Approved
0.6807	Remote Similarity	NPD6335	Approved
0.6789	Remote Similarity	NPD5696	Approved
0.678	Remote Similarity	NPD6868	Approved
0.6777	Remote Similarity	NPD7503	Approved
0.6771	Remote Similarity	NPD3703	Phase 2
0.6768	Remote Similarity	NPD7525	Registered
0.6765	Remote Similarity	NPD5329	Approved
0.6757	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7101	Approved
0.675	Remote Similarity	NPD7100	Approved
0.6735	Remote Similarity	NPD3617	Approved
0.6733	Remote Similarity	NPD4788	Approved
0.6731	Remote Similarity	NPD5737	Approved
0.6731	Remote Similarity	NPD6903	Approved
0.6731	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD5282	Discontinued
0.6699	Remote Similarity	NPD4519	Discontinued
0.6699	Remote Similarity	NPD4689	Approved
0.6699	Remote Similarity	NPD4690	Approved
0.6699	Remote Similarity	NPD4693	Phase 3
0.6699	Remote Similarity	NPD5205	Approved
0.6699	Remote Similarity	NPD4688	Approved
0.6699	Remote Similarity	NPD4623	Approved
0.6699	Remote Similarity	NPD4138	Approved
0.6698	Remote Similarity	NPD8035	Phase 2
0.6698	Remote Similarity	NPD8034	Phase 2
0.6698	Remote Similarity	NPD6411	Approved
0.6695	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7328	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6909	Approved
0.6638	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7516	Approved
0.661	Remote Similarity	NPD8133	Approved
0.6557	Remote Similarity	NPD8377	Approved
0.6557	Remote Similarity	NPD8294	Approved
0.6542	Remote Similarity	NPD5284	Approved
0.6542	Remote Similarity	NPD5281	Approved
0.6538	Remote Similarity	NPD5690	Phase 2
0.6538	Remote Similarity	NPD5280	Approved
0.6538	Remote Similarity	NPD4694	Approved
0.6509	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6101	Approved
0.6509	Remote Similarity	NPD6673	Approved
0.6509	Remote Similarity	NPD6904	Approved
0.6509	Remote Similarity	NPD6080	Approved
0.6504	Remote Similarity	NPD8296	Approved
0.6504	Remote Similarity	NPD8033	Approved
0.6504	Remote Similarity	NPD8378	Approved
0.6504	Remote Similarity	NPD8380	Approved
0.6504	Remote Similarity	NPD8335	Approved
0.6504	Remote Similarity	NPD8379	Approved
0.6486	Remote Similarity	NPD4225	Approved
0.6481	Remote Similarity	NPD5778	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