NPASS Compound

Structure

CID146134 OpenBabel06191715502D 29 33 0 0 0 0 0 0 0 0999 V2000 8.7602 -1.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6637 -2.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 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 -2.0000 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 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 6.0622 -1.5000 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 -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 4.3301 -0.5000 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 3.4641 0.0000 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 7.7942 -1.5000 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 0.0000 -2.0000 0.0000 O 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 13 1 0 0 0 0 9 15 2 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 19 2 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 21 2 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 21 29 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	397.868
LogP:	5.879
LogD:	3.503
LogS:	-3.736
# Rotatable Bonds:	0
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	3.322
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.86
MDCK Permeability:	1.6803767721285112e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.99382781982422%
Volume Distribution (VD):	0.553
Pgp-substrate:	3.6372597217559814%

ADMET: Metabolism

CYP1A2-inhibitor:	0.393
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.35
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.608
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.241
CYP2D6-substrate:	0.324
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	1.872
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.67
AMES Toxicity:	0.337
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.601
Skin Sensitization:	0.669
Carcinogencity:	0.179
Eye Corrosion:	0.003
Eye Irritation:	0.117
Respiratory Toxicity:	0.174

Download Data

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

Natural Product: NPC146134

Natural Product ID:	NPC146134
*Common Name:**	Br-Xanthone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QFURCBFEIGTKCW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-22(2)7-5-11-14(28-22)10-16-18(19(11)25)20(26)17-12-6-8-23(3,4)29-21(12)13(24)9-15(17)27-16/h9-10,24-25H,5-8H2,1-4H3
SMILES:	Oc1cc2oc3cc4OC(C)(C)CCc4c(c3c(=O)c2c2c1OC(C)(C)CC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517938
PubChem CID:	13964005
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	14.0	%	PMID[549614]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	18.0	%	PMID[549614]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	15.0	%	PMID[549614]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	27.0	%	PMID[549614]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	28.0	%	PMID[549614]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	31.0	%	PMID[549614]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	36.0	%	PMID[549614]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	3.0	%	PMID[549614]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	0.0	%	PMID[549614]

☑ 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 NPC146134 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	476
0.1-0.2	2135
0.2-0.3	4980
0.3-0.4	11861
0.4-0.5	5782
0.5-0.6	4039
0.6-0.7	5226
0.7-0.8	5037
0.8-0.85	2040
0.85-0.9	923
0.9-0.95	176
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC25152
0.9806	High Similarity	NPC52204
0.9745	High Similarity	NPC472449
0.9744	High Similarity	NPC236521
0.9744	High Similarity	NPC152659
0.9744	High Similarity	NPC248638
0.9677	High Similarity	NPC200746
0.9618	High Similarity	NPC23298
0.9618	High Similarity	NPC189473
0.9615	High Similarity	NPC61010
0.9613	High Similarity	NPC100123
0.956	High Similarity	NPC477154
0.956	High Similarity	NPC117854
0.956	High Similarity	NPC6588
0.9557	High Similarity	NPC275780
0.9557	High Similarity	NPC472450
0.9557	High Similarity	NPC239752
0.9551	High Similarity	NPC320359
0.9551	High Similarity	NPC228785
0.9551	High Similarity	NPC14353
0.9551	High Similarity	NPC56085
0.9497	High Similarity	NPC39091
0.9497	High Similarity	NPC37870
0.949	High Similarity	NPC40491
0.949	High Similarity	NPC278052
0.9487	High Similarity	NPC476242
0.9484	High Similarity	NPC142339
0.9484	High Similarity	NPC274730
0.943	High Similarity	NPC229632
0.943	High Similarity	NPC329760
0.9427	High Similarity	NPC471973
0.9427	High Similarity	NPC139036
0.9427	High Similarity	NPC80375
0.9427	High Similarity	NPC204290
0.9423	High Similarity	NPC236796
0.9423	High Similarity	NPC300727
0.9423	High Similarity	NPC165977
0.9423	High Similarity	NPC217677
0.9423	High Similarity	NPC136674
0.9423	High Similarity	NPC241904
0.9379	High Similarity	NPC326877
0.9375	High Similarity	NPC170245
0.9371	High Similarity	NPC306321
0.9371	High Similarity	NPC207690
0.9371	High Similarity	NPC220313
0.9371	High Similarity	NPC7483
0.9371	High Similarity	NPC303460
0.9371	High Similarity	NPC236132
0.9367	High Similarity	NPC29876
0.9367	High Similarity	NPC167678
0.9363	High Similarity	NPC474290
0.9359	High Similarity	NPC191146
0.9359	High Similarity	NPC138243
0.9359	High Similarity	NPC68093
0.9359	High Similarity	NPC470600
0.9355	High Similarity	NPC89474
0.9313	High Similarity	NPC326520
0.9313	High Similarity	NPC293319
0.9308	High Similarity	NPC472448
0.9308	High Similarity	NPC83922
0.9304	High Similarity	NPC235018
0.9304	High Similarity	NPC475886
0.9304	High Similarity	NPC45146
0.9304	High Similarity	NPC119224
0.9304	High Similarity	NPC474287
0.9299	High Similarity	NPC36852
0.9299	High Similarity	NPC262286
0.9299	High Similarity	NPC78225
0.9259	High Similarity	NPC475805
0.9259	High Similarity	NPC476637
0.9259	High Similarity	NPC177480
0.9255	High Similarity	NPC120593
0.925	High Similarity	NPC475985
0.925	High Similarity	NPC186686
0.925	High Similarity	NPC41301
0.925	High Similarity	NPC270837
0.9245	High Similarity	NPC475883
0.9245	High Similarity	NPC259456
0.9245	High Similarity	NPC134783
0.9245	High Similarity	NPC32694
0.9245	High Similarity	NPC474186
0.9245	High Similarity	NPC474351
0.9245	High Similarity	NPC474187
0.9241	High Similarity	NPC235448
0.9226	High Similarity	NPC202157
0.9202	High Similarity	NPC101107
0.9202	High Similarity	NPC103307
0.9202	High Similarity	NPC74559
0.9198	High Similarity	NPC8965
0.9198	High Similarity	NPC126204
0.9198	High Similarity	NPC474024
0.9193	High Similarity	NPC62261
0.9193	High Similarity	NPC156432
0.9193	High Similarity	NPC224280
0.9187	High Similarity	NPC474150
0.9187	High Similarity	NPC470694
0.9187	High Similarity	NPC474162
0.9187	High Similarity	NPC261470
0.9187	High Similarity	NPC220912
0.9187	High Similarity	NPC294965
0.9182	High Similarity	NPC188433
0.9182	High Similarity	NPC36217
0.9182	High Similarity	NPC174953
0.9182	High Similarity	NPC476980
0.9177	High Similarity	NPC223787
0.9177	High Similarity	NPC79053
0.9177	High Similarity	NPC469584
0.9177	High Similarity	NPC474681
0.9177	High Similarity	NPC218313
0.9172	High Similarity	NPC256925
0.9172	High Similarity	NPC166054
0.9172	High Similarity	NPC113906
0.9172	High Similarity	NPC55662
0.9172	High Similarity	NPC200246
0.9161	High Similarity	NPC151473
0.9136	High Similarity	NPC272560
0.9136	High Similarity	NPC43319
0.913	High Similarity	NPC197168
0.913	High Similarity	NPC474350
0.913	High Similarity	NPC273959
0.9125	High Similarity	NPC471212
0.9125	High Similarity	NPC266314
0.9125	High Similarity	NPC40037
0.9125	High Similarity	NPC472632
0.9125	High Similarity	NPC278427
0.9125	High Similarity	NPC471210
0.9125	High Similarity	NPC228383
0.9125	High Similarity	NPC471211
0.9125	High Similarity	NPC66288
0.9125	High Similarity	NPC57715
0.9125	High Similarity	NPC234644
0.9119	High Similarity	NPC95936
0.9119	High Similarity	NPC185258
0.9119	High Similarity	NPC329091
0.9119	High Similarity	NPC204879
0.9119	High Similarity	NPC473990
0.9119	High Similarity	NPC172770
0.9119	High Similarity	NPC250214
0.9114	High Similarity	NPC115853
0.9114	High Similarity	NPC5322
0.9114	High Similarity	NPC471985
0.9114	High Similarity	NPC276444
0.9114	High Similarity	NPC472907
0.9114	High Similarity	NPC6633
0.9114	High Similarity	NPC133970
0.9108	High Similarity	NPC280530
0.9108	High Similarity	NPC472905
0.9108	High Similarity	NPC227337
0.9108	High Similarity	NPC273462
0.9108	High Similarity	NPC49402
0.9108	High Similarity	NPC95842
0.9108	High Similarity	NPC70433
0.9108	High Similarity	NPC178964
0.9108	High Similarity	NPC33051
0.9107	High Similarity	NPC150977
0.9103	High Similarity	NPC171010
0.9085	High Similarity	NPC472276
0.908	High Similarity	NPC218226
0.908	High Similarity	NPC476306
0.9074	High Similarity	NPC473286
0.9074	High Similarity	NPC25361
0.9074	High Similarity	NPC234052
0.9074	High Similarity	NPC50960
0.9068	High Similarity	NPC474033
0.9068	High Similarity	NPC206605
0.9068	High Similarity	NPC201800
0.9068	High Similarity	NPC474034
0.9068	High Similarity	NPC472402
0.9062	High Similarity	NPC474960
0.9062	High Similarity	NPC119209
0.9062	High Similarity	NPC246478
0.9062	High Similarity	NPC192686
0.9062	High Similarity	NPC118256
0.9057	High Similarity	NPC472911
0.9057	High Similarity	NPC218871
0.9057	High Similarity	NPC474208
0.9057	High Similarity	NPC48208
0.9057	High Similarity	NPC27337
0.9057	High Similarity	NPC52889
0.9057	High Similarity	NPC472914
0.9057	High Similarity	NPC476981
0.9057	High Similarity	NPC476630
0.9057	High Similarity	NPC471209
0.9057	High Similarity	NPC245758
0.9057	High Similarity	NPC219867
0.9057	High Similarity	NPC222814
0.9057	High Similarity	NPC472963
0.9057	High Similarity	NPC474836
0.9057	High Similarity	NPC96167
0.9057	High Similarity	NPC472913
0.9057	High Similarity	NPC161960
0.9057	High Similarity	NPC475267
0.9057	High Similarity	NPC304008
0.9057	High Similarity	NPC472910
0.9057	High Similarity	NPC180011
0.9057	High Similarity	NPC156057
0.9057	High Similarity	NPC162869
0.9057	High Similarity	NPC187745
0.9051	High Similarity	NPC230149
0.9051	High Similarity	NPC168247

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 NPC146134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	1067
0.2-0.3	1947
0.3-0.4	2785
0.4-0.5	1635
0.5-0.6	875
0.6-0.7	278
0.7-0.8	115
0.8-0.85	26
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8987	High Similarity	NPD2801	Approved
0.8868	High Similarity	NPD2393	Clinical (unspecified phase)
0.8805	High Similarity	NPD1934	Approved
0.8727	High Similarity	NPD6166	Phase 2
0.8727	High Similarity	NPD6168	Clinical (unspecified phase)
0.8727	High Similarity	NPD6167	Clinical (unspecified phase)
0.8712	High Similarity	NPD5494	Approved
0.8634	High Similarity	NPD1465	Phase 2
0.8631	High Similarity	NPD7074	Phase 3
0.8545	High Similarity	NPD6959	Discontinued
0.8535	High Similarity	NPD1511	Approved
0.8462	Intermediate Similarity	NPD7054	Approved
0.8428	Intermediate Similarity	NPD1512	Approved
0.8415	Intermediate Similarity	NPD3882	Suspended
0.8412	Intermediate Similarity	NPD7472	Approved
0.8383	Intermediate Similarity	NPD6232	Discontinued
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8303	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6797	Phase 2
0.825	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4380	Phase 2
0.8208	Intermediate Similarity	NPD7251	Discontinued
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD7808	Phase 3
0.8137	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3817	Phase 2
0.8046	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7075	Discontinued
0.8035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2800	Approved
0.7929	Intermediate Similarity	NPD3749	Approved
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1549	Phase 2
0.7844	Intermediate Similarity	NPD7411	Suspended
0.7805	Intermediate Similarity	NPD2533	Approved
0.7805	Intermediate Similarity	NPD2532	Approved
0.7805	Intermediate Similarity	NPD2534	Approved
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6801	Discontinued
0.7791	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD943	Approved
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7390	Discontinued
0.7706	Intermediate Similarity	NPD5402	Approved
0.7688	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7228	Approved
0.767	Intermediate Similarity	NPD3751	Discontinued
0.7658	Intermediate Similarity	NPD1240	Approved
0.7644	Intermediate Similarity	NPD3787	Discontinued
0.764	Intermediate Similarity	NPD6100	Approved
0.764	Intermediate Similarity	NPD6099	Approved
0.764	Intermediate Similarity	NPD2796	Approved
0.764	Intermediate Similarity	NPD2935	Discontinued
0.7636	Intermediate Similarity	NPD6799	Approved
0.7628	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3226	Approved
0.7606	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD6559	Discontinued
0.7593	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6599	Discontinued
0.7572	Intermediate Similarity	NPD6234	Discontinued
0.7562	Intermediate Similarity	NPD1607	Approved
0.7558	Intermediate Similarity	NPD7768	Phase 2
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7471	Intermediate Similarity	NPD919	Approved
0.7469	Intermediate Similarity	NPD3748	Approved
0.7438	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7435	Discontinued
0.7396	Intermediate Similarity	NPD7697	Approved
0.7391	Intermediate Similarity	NPD230	Phase 1
0.7391	Intermediate Similarity	NPD8150	Discontinued
0.7391	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD7199	Phase 2
0.7385	Intermediate Similarity	NPD8151	Discontinued
0.7384	Intermediate Similarity	NPD37	Approved
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2799	Discontinued
0.7358	Intermediate Similarity	NPD4625	Phase 3
0.7356	Intermediate Similarity	NPD4966	Approved
0.7356	Intermediate Similarity	NPD4967	Phase 2
0.7356	Intermediate Similarity	NPD4965	Approved
0.7349	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6651	Approved
0.7345	Intermediate Similarity	NPD5711	Approved
0.7345	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD7701	Phase 2
0.7303	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5403	Approved
0.7294	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD920	Approved
0.7289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1243	Approved
0.7273	Intermediate Similarity	NPD2344	Approved
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7254	Intermediate Similarity	NPD6823	Phase 2
0.725	Intermediate Similarity	NPD3027	Phase 3
0.7249	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD6535	Approved
0.7238	Intermediate Similarity	NPD7286	Phase 2
0.7225	Intermediate Similarity	NPD7700	Phase 2
0.7225	Intermediate Similarity	NPD7699	Phase 2
0.7213	Intermediate Similarity	NPD7240	Approved
0.7205	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2313	Discontinued
0.7176	Intermediate Similarity	NPD5401	Approved
0.7174	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5953	Discontinued
0.7151	Intermediate Similarity	NPD1653	Approved
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7136	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.7118	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD8434	Phase 2
0.7108	Intermediate Similarity	NPD1551	Phase 2
0.7101	Intermediate Similarity	NPD2309	Approved
0.7101	Intermediate Similarity	NPD6190	Approved
0.7099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4908	Phase 1
0.7076	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1933	Approved
0.7072	Intermediate Similarity	NPD2403	Approved
0.7068	Intermediate Similarity	NPD4363	Phase 3
0.7068	Intermediate Similarity	NPD4360	Phase 2
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.7037	Intermediate Similarity	NPD4287	Approved
0.7019	Intermediate Similarity	NPD9494	Approved
0.7011	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD1470	Approved
0.6989	Remote Similarity	NPD7549	Discontinued
0.6981	Remote Similarity	NPD4749	Approved
0.6981	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1201	Approved
0.6959	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3300	Phase 2
0.6949	Remote Similarity	NPD8455	Phase 2
0.6941	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2493	Approved
0.6939	Remote Similarity	NPD2494	Approved
0.6935	Remote Similarity	NPD7584	Approved
0.6927	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6213	Phase 3
0.6927	Remote Similarity	NPD6212	Phase 3
0.6923	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5242	Approved
0.6918	Remote Similarity	NPD9269	Phase 2
0.6914	Remote Similarity	NPD7458	Discontinued
0.691	Remote Similarity	NPD4288	Approved
0.6909	Remote Similarity	NPD4060	Phase 1
0.6908	Remote Similarity	NPD7907	Approved
0.6907	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1203	Approved
0.6893	Remote Similarity	NPD4665	Approved
0.6893	Remote Similarity	NPD4111	Phase 1
0.6893	Remote Similarity	NPD6844	Discontinued
0.689	Remote Similarity	NPD3268	Approved
0.689	Remote Similarity	NPD3764	Approved
0.6882	Remote Similarity	NPD6674	Discontinued
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1471	Phase 3
0.6855	Remote Similarity	NPD1610	Phase 2
0.6853	Remote Similarity	NPD3452	Approved
0.6853	Remote Similarity	NPD3450	Approved
0.6852	Remote Similarity	NPD2798	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