NPASS Compound

Structure

CID37870 OpenBabel06191715372D 34 37 0 0 0 0 0 0 0 0999 V2000 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 -0.5000 1.8660 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 -3.5000 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 -3.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.8660 -1.5000 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 2.5981 -1.5000 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 -0.0000 1.0000 0.0000 C 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 5.1962 1.0000 0.0000 O 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 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 28 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 17 21 2 0 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 26 2 0 0 0 0 19 29 1 0 0 0 0 20 22 2 0 0 0 0 20 33 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 30 1 0 0 0 0 24 27 2 0 0 0 0 24 31 1 0 0 0 0 25 32 2 0 0 0 0 26 33 1 0 0 0 0 27 34 1 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.2
Volume:	484.995
LogP:	7.398
LogD:	4.023
LogS:	-2.335
# Rotatable Bonds:	4
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	3.601
Fsp3:	0.321
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:	-4.835
MDCK Permeability:	1.6495907402713783e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.618
20% Bioavailability (F20%):	0.862
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	84.1668472290039%
Volume Distribution (VD):	0.895
Pgp-substrate:	15.95291519165039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.729
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.846
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.318
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.148
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	3.803
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.269
Rat Oral Acute Toxicity:	0.854
Maximum Recommended Daily Dose:	0.553
Skin Sensitization:	0.712
Carcinogencity:	0.612
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC37870

Natural Product ID:	NPC37870
*Common Name:**	Tovophylline A
IUPAC Name:	5,9,11-trihydroxy-3,3-dimethyl-6,10-bis(3-methylbut-2-enyl)pyrano[3,2-a]xanthen-12-one
Synonyms:
Standard InCHIKey:	ADFJMFQSYNRLEH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H30O6/c1-14(2)7-9-16-19(29)13-20-22(23(16)30)25(32)21-17-11-12-28(5,6)34-27(17)24(31)18(26(21)33-20)10-8-15(3)4/h7-8,11-13,29-31H,9-10H2,1-6H3
SMILES:	CC(=CCc1c(cc2c(c1O)c(=O)c1c3C=CC(C)(C)Oc3c(c(CC=C(C)C)c1o2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479795
PubChem CID:	42645954
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:0003518] 4-prenylated xanthones

*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
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]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296616]
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		n.a.	n.a.	Database[FooDB]
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]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	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]
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]
NPO22337	Garcinia dulcis	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[TM-MC]
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]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	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]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	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]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	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	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	74.7	%	PMID[523431]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.6	ug.mL-1	PMID[523432]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.6	ug.mL-1	PMID[523433]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	2.8	ug.mL-1	PMID[523432]
NPT2	Others	Unspecified		Ratio IC50	=	0.93	n.a.	PMID[523432]

☑ 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 NPC37870 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	474
0.1-0.2	1955
0.2-0.3	4492
0.3-0.4	11206
0.4-0.5	6687
0.5-0.6	3630
0.6-0.7	5156
0.7-0.8	5208
0.8-0.85	2318
0.85-0.9	1097
0.9-0.95	413
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC207690
0.9872	High Similarity	NPC23298
0.9872	High Similarity	NPC189473
0.9809	High Similarity	NPC275780
0.9809	High Similarity	NPC472450
0.9809	High Similarity	NPC239752
0.9747	High Similarity	NPC472449
0.9747	High Similarity	NPC39091
0.9682	High Similarity	NPC229632
0.9682	High Similarity	NPC25152
0.9682	High Similarity	NPC329760
0.9679	High Similarity	NPC204290
0.9679	High Similarity	NPC139036
0.9679	High Similarity	NPC471973
0.9625	High Similarity	NPC476637
0.9623	High Similarity	NPC43319
0.962	High Similarity	NPC248638
0.962	High Similarity	NPC270837
0.962	High Similarity	NPC152659
0.962	High Similarity	NPC236132
0.962	High Similarity	NPC236521
0.9618	High Similarity	NPC167678
0.9618	High Similarity	NPC61010
0.9618	High Similarity	NPC29876
0.9615	High Similarity	NPC474290
0.9615	High Similarity	NPC100123
0.9563	High Similarity	NPC218226
0.9557	High Similarity	NPC472448
0.9557	High Similarity	NPC83922
0.9557	High Similarity	NPC294965
0.9554	High Similarity	NPC119224
0.9554	High Similarity	NPC228785
0.9554	High Similarity	NPC320359
0.9554	High Similarity	NPC14353
0.9554	High Similarity	NPC56085
0.9554	High Similarity	NPC200746
0.9551	High Similarity	NPC136674
0.9497	High Similarity	NPC306321
0.9497	High Similarity	NPC186686
0.9497	High Similarity	NPC220313
0.9497	High Similarity	NPC146134
0.9497	High Similarity	NPC303460
0.9494	High Similarity	NPC278052
0.9494	High Similarity	NPC40491
0.9494	High Similarity	NPC259456
0.9494	High Similarity	NPC66288
0.949	High Similarity	NPC476242
0.9487	High Similarity	NPC191146
0.9487	High Similarity	NPC68093
0.9487	High Similarity	NPC142339
0.9487	High Similarity	NPC274730
0.9444	High Similarity	NPC101107
0.9441	High Similarity	NPC6588
0.9441	High Similarity	NPC117854
0.9441	High Similarity	NPC477154
0.9441	High Similarity	NPC126204
0.9437	High Similarity	NPC156432
0.9437	High Similarity	NPC303174
0.9434	High Similarity	NPC474162
0.9434	High Similarity	NPC474150
0.9434	High Similarity	NPC470694
0.943	High Similarity	NPC235018
0.943	High Similarity	NPC80375
0.943	High Similarity	NPC45146
0.943	High Similarity	NPC476980
0.9427	High Similarity	NPC218313
0.9427	High Similarity	NPC78225
0.9427	High Similarity	NPC236796
0.9427	High Similarity	NPC474681
0.9427	High Similarity	NPC165977
0.9427	High Similarity	NPC217677
0.9427	High Similarity	NPC300727
0.9427	High Similarity	NPC241904
0.939	High Similarity	NPC227906
0.9383	High Similarity	NPC475805
0.9379	High Similarity	NPC170245
0.9379	High Similarity	NPC272502
0.9375	High Similarity	NPC7483
0.9375	High Similarity	NPC197168
0.9371	High Similarity	NPC474187
0.9371	High Similarity	NPC278427
0.9371	High Similarity	NPC32694
0.9371	High Similarity	NPC234644
0.9367	High Similarity	NPC235448
0.9367	High Similarity	NPC204879
0.9363	High Similarity	NPC138243
0.9363	High Similarity	NPC133970
0.9363	High Similarity	NPC276444
0.9363	High Similarity	NPC5322
0.9363	High Similarity	NPC6633
0.9363	High Similarity	NPC471985
0.9359	High Similarity	NPC95842
0.9359	High Similarity	NPC280530
0.9359	High Similarity	NPC178964
0.9359	High Similarity	NPC89474
0.9321	High Similarity	NPC474024
0.9317	High Similarity	NPC25361
0.9317	High Similarity	NPC293319
0.9317	High Similarity	NPC326520
0.9313	High Similarity	NPC261470
0.9313	High Similarity	NPC52204
0.9308	High Similarity	NPC188433
0.9308	High Similarity	NPC192686
0.9308	High Similarity	NPC475886
0.9308	High Similarity	NPC119209
0.9308	High Similarity	NPC36217
0.9308	High Similarity	NPC474287
0.9308	High Similarity	NPC118256
0.9308	High Similarity	NPC474960
0.9304	High Similarity	NPC262286
0.9304	High Similarity	NPC476630
0.9304	High Similarity	NPC476981
0.9304	High Similarity	NPC218871
0.9304	High Similarity	NPC36852
0.9299	High Similarity	NPC200246
0.9299	High Similarity	NPC472280
0.9259	High Similarity	NPC120593
0.9255	High Similarity	NPC41301
0.9255	High Similarity	NPC475985
0.925	High Similarity	NPC474351
0.925	High Similarity	NPC475883
0.925	High Similarity	NPC266314
0.925	High Similarity	NPC258331
0.925	High Similarity	NPC311740
0.925	High Similarity	NPC474186
0.925	High Similarity	NPC57715
0.925	High Similarity	NPC474038
0.9245	High Similarity	NPC85121
0.9245	High Similarity	NPC185258
0.9245	High Similarity	NPC172770
0.9245	High Similarity	NPC280680
0.9245	High Similarity	NPC95936
0.9245	High Similarity	NPC250214
0.9241	High Similarity	NPC470600
0.9241	High Similarity	NPC472455
0.9241	High Similarity	NPC472907
0.9236	High Similarity	NPC170492
0.9236	High Similarity	NPC227337
0.9236	High Similarity	NPC274327
0.9236	High Similarity	NPC70433
0.9236	High Similarity	NPC183878
0.9236	High Similarity	NPC273462
0.9236	High Similarity	NPC160951
0.9236	High Similarity	NPC49402
0.9236	High Similarity	NPC472905
0.9236	High Similarity	NPC255350
0.9236	High Similarity	NPC231018
0.9236	High Similarity	NPC33051
0.9236	High Similarity	NPC176775
0.9236	High Similarity	NPC69394
0.9236	High Similarity	NPC47781
0.9236	High Similarity	NPC145379
0.9236	High Similarity	NPC22519
0.9231	High Similarity	NPC202157
0.9212	High Similarity	NPC310794
0.9207	High Similarity	NPC109827
0.9207	High Similarity	NPC124470
0.9207	High Similarity	NPC472276
0.9202	High Similarity	NPC476306
0.9198	High Similarity	NPC62261
0.9198	High Similarity	NPC50960
0.9198	High Similarity	NPC224280
0.9193	High Similarity	NPC472402
0.9193	High Similarity	NPC78332
0.9193	High Similarity	NPC201800
0.9193	High Similarity	NPC206605
0.9187	High Similarity	NPC84571
0.9187	High Similarity	NPC476280
0.9187	High Similarity	NPC475784
0.9187	High Similarity	NPC246478
0.9182	High Similarity	NPC161960
0.9182	High Similarity	NPC475267
0.9182	High Similarity	NPC304008
0.9182	High Similarity	NPC222814
0.9182	High Similarity	NPC472963
0.9182	High Similarity	NPC469584
0.9182	High Similarity	NPC472910
0.9182	High Similarity	NPC273843
0.9182	High Similarity	NPC474836
0.9182	High Similarity	NPC223787
0.9182	High Similarity	NPC473272
0.9182	High Similarity	NPC472914
0.9182	High Similarity	NPC156057
0.9182	High Similarity	NPC245758
0.9182	High Similarity	NPC472913
0.9182	High Similarity	NPC474208
0.9182	High Similarity	NPC48208
0.9182	High Similarity	NPC96167
0.9182	High Similarity	NPC187745
0.9182	High Similarity	NPC162869
0.9182	High Similarity	NPC284820
0.9182	High Similarity	NPC27337
0.9182	High Similarity	NPC79053
0.9182	High Similarity	NPC472911
0.9182	High Similarity	NPC52889
0.9177	High Similarity	NPC201136
0.9177	High Similarity	NPC57674
0.9177	High Similarity	NPC92659
0.9177	High Similarity	NPC256925
0.9177	High Similarity	NPC167815

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 NPC37870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	1020
0.2-0.3	1775
0.3-0.4	2708
0.4-0.5	1772
0.5-0.6	908
0.6-0.7	370
0.7-0.8	134
0.8-0.85	31
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD2801	Approved
0.8994	High Similarity	NPD2393	Clinical (unspecified phase)
0.8931	High Similarity	NPD1934	Approved
0.8782	High Similarity	NPD1511	Approved
0.8727	High Similarity	NPD6232	Discontinued
0.872	High Similarity	NPD5494	Approved
0.869	High Similarity	NPD5844	Phase 1
0.8683	High Similarity	NPD7473	Discontinued
0.8671	High Similarity	NPD1512	Approved
0.8623	High Similarity	NPD6167	Clinical (unspecified phase)
0.8623	High Similarity	NPD6168	Clinical (unspecified phase)
0.8623	High Similarity	NPD6166	Phase 2
0.8537	High Similarity	NPD3882	Suspended
0.8491	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7054	Approved
0.8457	Intermediate Similarity	NPD4380	Phase 2
0.8443	Intermediate Similarity	NPD6959	Discontinued
0.8421	Intermediate Similarity	NPD7074	Phase 3
0.8421	Intermediate Similarity	NPD7472	Approved
0.8415	Intermediate Similarity	NPD1465	Phase 2
0.8412	Intermediate Similarity	NPD3818	Discontinued
0.8375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD3817	Phase 2
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7819	Suspended
0.8266	Intermediate Similarity	NPD6797	Phase 2
0.8218	Intermediate Similarity	NPD7251	Discontinued
0.8171	Intermediate Similarity	NPD7808	Phase 3
0.8155	Intermediate Similarity	NPD7075	Discontinued
0.8155	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD3749	Approved
0.8046	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD2533	Approved
0.8037	Intermediate Similarity	NPD2534	Approved
0.8037	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD3750	Approved
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1549	Phase 2
0.7964	Intermediate Similarity	NPD7411	Suspended
0.7952	Intermediate Similarity	NPD3226	Approved
0.7937	Intermediate Similarity	NPD2346	Discontinued
0.7929	Intermediate Similarity	NPD5402	Approved
0.7925	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1510	Phase 2
0.7917	Intermediate Similarity	NPD6801	Discontinued
0.7911	Intermediate Similarity	NPD1607	Approved
0.791	Intermediate Similarity	NPD6559	Discontinued
0.7904	Intermediate Similarity	NPD6599	Discontinued
0.7898	Intermediate Similarity	NPD943	Approved
0.7888	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2796	Approved
0.7875	Intermediate Similarity	NPD6100	Approved
0.7875	Intermediate Similarity	NPD6099	Approved
0.7866	Intermediate Similarity	NPD7390	Discontinued
0.7853	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2800	Approved
0.7785	Intermediate Similarity	NPD1240	Approved
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2935	Discontinued
0.7758	Intermediate Similarity	NPD6799	Approved
0.7756	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3926	Phase 2
0.7713	Intermediate Similarity	NPD6779	Approved
0.7713	Intermediate Similarity	NPD6776	Approved
0.7713	Intermediate Similarity	NPD6780	Approved
0.7713	Intermediate Similarity	NPD6781	Approved
0.7713	Intermediate Similarity	NPD6782	Approved
0.7713	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6777	Approved
0.7713	Intermediate Similarity	NPD6778	Approved
0.7707	Intermediate Similarity	NPD4625	Phase 3
0.7702	Intermediate Similarity	NPD3748	Approved
0.7702	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD919	Approved
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7674	Intermediate Similarity	NPD7768	Phase 2
0.7657	Intermediate Similarity	NPD3787	Discontinued
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7605	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.7592	Intermediate Similarity	NPD7435	Discontinued
0.7584	Intermediate Similarity	NPD7228	Approved
0.7576	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1613	Approved
0.7557	Intermediate Similarity	NPD5711	Approved
0.7557	Intermediate Similarity	NPD5710	Approved
0.7516	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7783	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7696	Phase 3
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD4628	Phase 3
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7448	Intermediate Similarity	NPD6823	Phase 2
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.7438	Intermediate Similarity	NPD2313	Discontinued
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7416	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD920	Approved
0.7412	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD230	Phase 1
0.7398	Intermediate Similarity	NPD8151	Discontinued
0.7396	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD2344	Approved
0.7377	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3027	Phase 3
0.7368	Intermediate Similarity	NPD1653	Approved
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.7333	Intermediate Similarity	NPD5405	Approved
0.7333	Intermediate Similarity	NPD5406	Approved
0.7333	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD5404	Approved
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7801	Approved
0.7322	Intermediate Similarity	NPD7685	Pre-registration
0.7312	Intermediate Similarity	NPD8434	Phase 2
0.7294	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7263	Intermediate Similarity	NPD4360	Phase 2
0.7263	Intermediate Similarity	NPD4363	Phase 3
0.7256	Intermediate Similarity	NPD6651	Approved
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.7235	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2309	Approved
0.7219	Intermediate Similarity	NPD6190	Approved
0.7215	Intermediate Similarity	NPD4749	Approved
0.7205	Intermediate Similarity	NPD4908	Phase 1
0.7197	Intermediate Similarity	NPD1201	Approved
0.7195	Intermediate Similarity	NPD1933	Approved
0.7193	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3300	Phase 2
0.7169	Intermediate Similarity	NPD4308	Phase 3
0.7167	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD4287	Approved
0.7135	Intermediate Similarity	NPD7240	Approved
0.7128	Intermediate Similarity	NPD2493	Approved
0.7128	Intermediate Similarity	NPD2494	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7121	Intermediate Similarity	NPD7584	Approved
0.712	Intermediate Similarity	NPD6213	Phase 3
0.712	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6212	Phase 3
0.7119	Intermediate Similarity	NPD4288	Approved
0.7117	Intermediate Similarity	NPD3268	Approved
0.7107	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6844	Discontinued
0.7101	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7098	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7549	Discontinued
0.7087	Intermediate Similarity	NPD7907	Approved
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7081	Intermediate Similarity	NPD2798	Approved
0.7073	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD4665	Approved
0.7059	Intermediate Similarity	NPD7003	Approved
0.7041	Intermediate Similarity	NPD3450	Approved
0.7041	Intermediate Similarity	NPD3452	Approved
0.7033	Intermediate Similarity	NPD5242	Approved
0.703	Intermediate Similarity	NPD4060	Phase 1
0.7026	Intermediate Similarity	NPD8285	Discontinued
0.702	Intermediate Similarity	NPD8319	Approved
0.702	Intermediate Similarity	NPD4583	Approved
0.702	Intermediate Similarity	NPD8320	Phase 1
0.702	Intermediate Similarity	NPD4582	Approved
0.7019	Intermediate Similarity	NPD1203	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