NPASS Compound

Structure

CID111485 OpenBabel06191715462D 24 28 0 0 1 0 0 0 0 0999 V2000 4.8918 -0.1765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2989 -1.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0895 -0.6395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2875 1.6763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6942 -0.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6828 1.6760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6941 1.2134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 -0.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5446 0.7493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8918 -0.1765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 1.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8917 0.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4853 0.2867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0898 1.2131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2875 -0.1764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4965 0.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4966 -0.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8807 1.2127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8809 0.2864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0896 0.2867 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2987 1.2133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2988 -0.6395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.4988 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 20 1 0 0 0 0 2 22 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 17 1 0 0 0 0 6 11 2 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 4 1 1 0 0 0 14 20 1 0 0 0 0 15 3 1 1 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	324.737
LogP:	2.464
LogD:	2.905
LogS:	-2.416
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.873
Synthetic Accessibility Score:	4.116
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.824
MDCK Permeability:	3.0910880013834685e-05
Pgp-inhibitor:	0.227
Pgp-substrate:	0.946
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.931
Plasma Protein Binding (PPB):	71.88538360595703%
Volume Distribution (VD):	1.981
Pgp-substrate:	14.247708320617676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.765
CYP2C19-substrate:	0.875
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.67
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	18.593
Half-life (T1/2):	0.269

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.772
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.519
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.416
Carcinogencity:	0.865
Eye Corrosion:	0.008
Eye Irritation:	0.13
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC111485

Natural Product ID:	NPC111485
*Common Name:**	Caryachine
IUPAC Name:	n.a.
Synonyms:	Caryachine
Standard InCHIKey:	TZJNFQHUSMXCIT-GJZGRUSLSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-20-14-4-11-6-18-19(24-9-23-18)8-13(11)15(20)3-10-5-17(22-2)16(21)7-12(10)14/h5-8,14-15,21H,3-4,9H2,1-2H3/t14-,15-/m0/s1
SMILES:	CN1[C@H]2Cc3cc4c(cc3[C@@H]1Cc1cc(c(cc21)O)OC)OCO4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480663
PubChem CID:	44575219
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002793] Pavine alkaloids

*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
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	twig	n.a.	PMID[16204994]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	Oakham, MA, US	n.a.	PMID[16562853]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17250743]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	leaves	Lai-I, Pingtung County, Taiwan	2005-May	PMID[20704331]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6229	Chenopodiastrum murale	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6615	Aplidium solidum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13040	Veretillum cynomorium	Species	Veretillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11833	Dyssodia anthemidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14223	Harpullia cupanioides	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5040	Polygonatum polyanthemum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12064	Lychnophora pinaster	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14366	Youngia japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14086	Parthenium confertum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13241	Coprosma foetidissima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2770	Pyropolyporus fomentarius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14639	Balanophora polyandra	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20068	Fusarium striatum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2075	Zanthoxylum ocumarense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15911	Streptomyces graminofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12296	Sphaerechinus granularis	Species	Toxopneustidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13755	Gonotheca helianthoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1946	Veronica stricta	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16090	Panicum crus-galli	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8632	Aralia hispida	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13631	Microglossa pyrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11607	Marrubium parviflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14344	Trifolium diffusum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15098	Cyttaria johowii	Species	Cyttariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6241	Girgensohnia oppositiflora	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7878	Lysastrosoma anthosticta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1202	Psathyrotes ramosissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14485	Eriocephalus kingesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14996	Lobelia syphilitica	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14885	Lilium rubrum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10936	Andira retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26228	Phymatopteris hastata	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7036	Davidsonia pruriens	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3521	Geranium collinum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12818	Lespedeza maximowiczi	Species	Fabaceae	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
EC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	EC50	=	9000.0	nM	PMID[529653]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Activity	=	5.0	uM	PMID[529653]

☑ 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 NPC111485 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	262
0.1-0.2	1466
0.2-0.3	7336
0.3-0.4	10851
0.4-0.5	6338
0.5-0.6	11230
0.6-0.7	4033
0.7-0.8	768
0.8-0.85	225
0.85-0.9	129
0.9-0.95	53
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC232514
0.9737	High Similarity	NPC276944
0.9737	High Similarity	NPC238530
0.9527	High Similarity	NPC151895
0.9527	High Similarity	NPC192768
0.9527	High Similarity	NPC88249
0.9527	High Similarity	NPC97221
0.9527	High Similarity	NPC220858
0.94	High Similarity	NPC210148
0.94	High Similarity	NPC233029
0.9276	High Similarity	NPC138487
0.9276	High Similarity	NPC276588
0.9276	High Similarity	NPC216459
0.9276	High Similarity	NPC278799
0.9276	High Similarity	NPC207757
0.9276	High Similarity	NPC110416
0.9276	High Similarity	NPC184026
0.9276	High Similarity	NPC249797
0.9276	High Similarity	NPC127674
0.9276	High Similarity	NPC5238
0.9276	High Similarity	NPC39701
0.9276	High Similarity	NPC172765
0.9276	High Similarity	NPC54379
0.9276	High Similarity	NPC41178
0.9276	High Similarity	NPC469817
0.9276	High Similarity	NPC295691
0.9276	High Similarity	NPC193949
0.9276	High Similarity	NPC189266
0.9276	High Similarity	NPC2413
0.9276	High Similarity	NPC204828
0.9262	High Similarity	NPC476571
0.9262	High Similarity	NPC147390
0.9262	High Similarity	NPC246587
0.9262	High Similarity	NPC135538
0.9262	High Similarity	NPC475959
0.9262	High Similarity	NPC24233
0.9262	High Similarity	NPC428
0.9216	High Similarity	NPC146288
0.9195	High Similarity	NPC191376
0.9195	High Similarity	NPC321505
0.9195	High Similarity	NPC179825
0.9091	High Similarity	NPC31311
0.9091	High Similarity	NPC234392
0.9068	High Similarity	NPC128560
0.9068	High Similarity	NPC229166
0.9068	High Similarity	NPC199465
0.906	High Similarity	NPC185838
0.9054	High Similarity	NPC128019
0.9054	High Similarity	NPC136860
0.9054	High Similarity	NPC476567
0.9006	High Similarity	NPC2314
0.8994	High Similarity	NPC298979
0.8974	High Similarity	NPC477080
0.8957	High Similarity	NPC320223
0.8957	High Similarity	NPC114364
0.8947	High Similarity	NPC477565
0.8947	High Similarity	NPC103379
0.8896	High Similarity	NPC37272
0.8868	High Similarity	NPC24465
0.8868	High Similarity	NPC121275
0.8868	High Similarity	NPC4138
0.8868	High Similarity	NPC284183
0.8846	High Similarity	NPC186063
0.8831	High Similarity	NPC76213
0.8831	High Similarity	NPC277669
0.8816	High Similarity	NPC210437
0.8816	High Similarity	NPC16107
0.8816	High Similarity	NPC476144
0.8816	High Similarity	NPC106295
0.8816	High Similarity	NPC476151
0.8816	High Similarity	NPC51957
0.8812	High Similarity	NPC250846
0.8812	High Similarity	NPC240841
0.8812	High Similarity	NPC42549
0.8812	High Similarity	NPC264850
0.8812	High Similarity	NPC256012
0.8812	High Similarity	NPC317272
0.8812	High Similarity	NPC13916
0.8812	High Similarity	NPC268503
0.8805	High Similarity	NPC59567
0.8795	High Similarity	NPC116284
0.8792	High Similarity	NPC213206
0.8792	High Similarity	NPC328750
0.8792	High Similarity	NPC188163
0.8792	High Similarity	NPC474915
0.8758	High Similarity	NPC7467
0.8758	High Similarity	NPC100566
0.8735	High Similarity	NPC155442
0.8735	High Similarity	NPC476574
0.8735	High Similarity	NPC312918
0.8735	High Similarity	NPC477561
0.8726	High Similarity	NPC147091
0.8725	High Similarity	NPC314682
0.8704	High Similarity	NPC66573
0.8701	High Similarity	NPC207824
0.8701	High Similarity	NPC60538
0.8688	High Similarity	NPC324144
0.8679	High Similarity	NPC306902
0.8679	High Similarity	NPC205167
0.8679	High Similarity	NPC232924
0.8679	High Similarity	NPC215829
0.8679	High Similarity	NPC27410
0.8679	High Similarity	NPC97072
0.8679	High Similarity	NPC166014
0.8679	High Similarity	NPC160298
0.8679	High Similarity	NPC477559
0.8679	High Similarity	NPC266753
0.8662	High Similarity	NPC93593
0.8655	High Similarity	NPC24260
0.8654	High Similarity	NPC82285
0.8654	High Similarity	NPC133011
0.865	High Similarity	NPC109925
0.8649	High Similarity	NPC7018
0.8649	High Similarity	NPC131204
0.8649	High Similarity	NPC301050
0.8642	High Similarity	NPC181653
0.8642	High Similarity	NPC210140
0.8642	High Similarity	NPC190332
0.8634	High Similarity	NPC96603
0.8634	High Similarity	NPC167546
0.8634	High Similarity	NPC136508
0.8634	High Similarity	NPC16805
0.8634	High Similarity	NPC212794
0.8634	High Similarity	NPC196447
0.8634	High Similarity	NPC302527
0.8634	High Similarity	NPC13504
0.8634	High Similarity	NPC306843
0.8634	High Similarity	NPC477563
0.8634	High Similarity	NPC78222
0.8634	High Similarity	NPC253043
0.8631	High Similarity	NPC135772
0.8616	High Similarity	NPC106786
0.8606	High Similarity	NPC187678
0.8599	High Similarity	NPC477564
0.8599	High Similarity	NPC2295
0.858	High Similarity	NPC24264
0.858	High Similarity	NPC476432
0.8562	High Similarity	NPC249274
0.8544	High Similarity	NPC78733
0.8538	High Similarity	NPC82763
0.8537	High Similarity	NPC152212
0.8537	High Similarity	NPC311991
0.8535	High Similarity	NPC148898
0.8535	High Similarity	NPC26601
0.8535	High Similarity	NPC223124
0.8528	High Similarity	NPC145832
0.8528	High Similarity	NPC247389
0.8528	High Similarity	NPC210918
0.8528	High Similarity	NPC12053
0.8528	High Similarity	NPC117188
0.8528	High Similarity	NPC205421
0.8528	High Similarity	NPC474931
0.8528	High Similarity	NPC306555
0.8528	High Similarity	NPC158376
0.8528	High Similarity	NPC81218
0.8519	High Similarity	NPC134858
0.8519	High Similarity	NPC225774
0.8506	High Similarity	NPC24228
0.8503	High Similarity	NPC294790
0.8503	High Similarity	NPC148693
0.8503	High Similarity	NPC118633
0.8497	Intermediate Similarity	NPC294249
0.8485	Intermediate Similarity	NPC225597
0.8485	Intermediate Similarity	NPC477640
0.8485	Intermediate Similarity	NPC475215
0.8485	Intermediate Similarity	NPC470739
0.8485	Intermediate Similarity	NPC108434
0.848	Intermediate Similarity	NPC186546
0.848	Intermediate Similarity	NPC476576
0.8476	Intermediate Similarity	NPC290759
0.8476	Intermediate Similarity	NPC158148
0.8476	Intermediate Similarity	NPC266176
0.8476	Intermediate Similarity	NPC475686
0.8476	Intermediate Similarity	NPC58766
0.8476	Intermediate Similarity	NPC82533
0.8466	Intermediate Similarity	NPC219341
0.8462	Intermediate Similarity	NPC248642
0.8457	Intermediate Similarity	NPC233650
0.8457	Intermediate Similarity	NPC320104
0.8452	Intermediate Similarity	NPC126284
0.8452	Intermediate Similarity	NPC32154
0.8443	Intermediate Similarity	NPC237044
0.8428	Intermediate Similarity	NPC76079
0.8428	Intermediate Similarity	NPC80129
0.8428	Intermediate Similarity	NPC187022
0.8424	Intermediate Similarity	NPC474475
0.8412	Intermediate Similarity	NPC156576
0.8408	Intermediate Similarity	NPC223125
0.8408	Intermediate Similarity	NPC274026
0.8397	Intermediate Similarity	NPC130941
0.8395	Intermediate Similarity	NPC60186
0.8393	Intermediate Similarity	NPC474325
0.8383	Intermediate Similarity	NPC477558
0.8383	Intermediate Similarity	NPC304675
0.8383	Intermediate Similarity	NPC49353
0.8375	Intermediate Similarity	NPC247639
0.8375	Intermediate Similarity	NPC25084
0.8373	Intermediate Similarity	NPC149090
0.8373	Intermediate Similarity	NPC239775
0.8373	Intermediate Similarity	NPC19520

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 NPC111485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	709
0.2-0.3	1091
0.3-0.4	1925
0.4-0.5	2667
0.5-0.6	1783
0.6-0.7	637
0.7-0.8	142
0.8-0.85	20
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8816	High Similarity	NPD4584	Approved
0.8792	High Similarity	NPD4664	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD4010	Discontinued
0.8428	Intermediate Similarity	NPD7298	Approved
0.8365	Intermediate Similarity	NPD4772	Phase 2
0.8365	Intermediate Similarity	NPD4773	Phase 2
0.8246	Intermediate Similarity	NPD8053	Approved
0.8246	Intermediate Similarity	NPD8054	Approved
0.8228	Intermediate Similarity	NPD3639	Approved
0.8228	Intermediate Similarity	NPD3640	Phase 3
0.8228	Intermediate Similarity	NPD3641	Approved
0.8148	Intermediate Similarity	NPD2978	Approved
0.8148	Intermediate Similarity	NPD2977	Approved
0.8144	Intermediate Similarity	NPD2898	Approved
0.8125	Intermediate Similarity	NPD4017	Approved
0.8121	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD2489	Approved
0.8036	Intermediate Similarity	NPD27	Approved
0.8025	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5241	Discontinued
0.8	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7833	Phase 2
0.8	Intermediate Similarity	NPD7831	Phase 2
0.7987	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2421	Approved
0.7925	Intermediate Similarity	NPD2420	Approved
0.7888	Intermediate Similarity	NPD6031	Approved
0.7888	Intermediate Similarity	NPD6030	Approved
0.7881	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD2970	Approved
0.787	Intermediate Similarity	NPD2969	Approved
0.7862	Intermediate Similarity	NPD3845	Phase 1
0.7857	Intermediate Similarity	NPD6107	Approved
0.7836	Intermediate Similarity	NPD8252	Approved
0.7836	Intermediate Similarity	NPD8251	Approved
0.7836	Intermediate Similarity	NPD8099	Discontinued
0.7811	Intermediate Similarity	NPD3051	Approved
0.7811	Intermediate Similarity	NPD4166	Phase 2
0.7791	Intermediate Similarity	NPD8156	Discontinued
0.7771	Intermediate Similarity	NPD7280	Phase 3
0.7771	Intermediate Similarity	NPD7281	Phase 3
0.7756	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD5718	Phase 2
0.7706	Intermediate Similarity	NPD6071	Discontinued
0.7702	Intermediate Similarity	NPD3124	Discontinued
0.7701	Intermediate Similarity	NPD6297	Approved
0.7697	Intermediate Similarity	NPD7906	Approved
0.7679	Intermediate Similarity	NPD5604	Discontinued
0.767	Intermediate Similarity	NPD7311	Approved
0.767	Intermediate Similarity	NPD7312	Approved
0.767	Intermediate Similarity	NPD7310	Approved
0.767	Intermediate Similarity	NPD7313	Approved
0.7665	Intermediate Similarity	NPD2563	Approved
0.7665	Intermediate Similarity	NPD2560	Approved
0.7662	Intermediate Similarity	NPD2674	Phase 3
0.7662	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7309	Approved
0.7595	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5313	Approved
0.7586	Intermediate Similarity	NPD5312	Approved
0.7572	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4577	Approved
0.7571	Intermediate Similarity	NPD4578	Approved
0.7544	Intermediate Similarity	NPD7802	Discontinued
0.7542	Intermediate Similarity	NPD4663	Approved
0.7528	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6853	Approved
0.7528	Intermediate Similarity	NPD6851	Approved
0.7515	Intermediate Similarity	NPD6788	Approved
0.7514	Intermediate Similarity	NPD4481	Phase 3
0.7484	Intermediate Similarity	NPD3145	Approved
0.7484	Intermediate Similarity	NPD3144	Approved
0.7472	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6896	Approved
0.7468	Intermediate Similarity	NPD6895	Approved
0.7468	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4420	Approved
0.7453	Intermediate Similarity	NPD5177	Phase 3
0.7453	Intermediate Similarity	NPD3060	Approved
0.744	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD2490	Approved
0.7418	Intermediate Similarity	NPD2488	Approved
0.7405	Intermediate Similarity	NPD2492	Phase 1
0.7353	Intermediate Similarity	NPD5977	Approved
0.7353	Intermediate Similarity	NPD5978	Approved
0.7351	Intermediate Similarity	NPD5582	Discontinued
0.7351	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4237	Approved
0.7346	Intermediate Similarity	NPD4236	Phase 3
0.7318	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1753	Discontinued
0.7302	Intermediate Similarity	NPD5006	Approved
0.7302	Intermediate Similarity	NPD5005	Approved
0.7278	Intermediate Similarity	NPD3109	Approved
0.7278	Intermediate Similarity	NPD3110	Approved
0.7273	Intermediate Similarity	NPD3053	Approved
0.7273	Intermediate Similarity	NPD3055	Approved
0.7262	Intermediate Similarity	NPD4005	Discontinued
0.7262	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4727	Phase 1
0.7239	Intermediate Similarity	NPD4162	Approved
0.7209	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4108	Discontinued
0.7198	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5773	Approved
0.7193	Intermediate Similarity	NPD5772	Approved
0.7186	Intermediate Similarity	NPD6090	Discontinued
0.7178	Intermediate Similarity	NPD7037	Approved
0.7176	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7110	Phase 1
0.7174	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4055	Discovery
0.716	Intermediate Similarity	NPD824	Approved
0.7159	Intermediate Similarity	NPD6688	Approved
0.7159	Intermediate Similarity	NPD6687	Approved
0.7158	Intermediate Similarity	NPD3452	Approved
0.7158	Intermediate Similarity	NPD3450	Approved
0.7158	Intermediate Similarity	NPD2494	Approved
0.7158	Intermediate Similarity	NPD2493	Approved
0.7152	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3885	Approved
0.7143	Intermediate Similarity	NPD2122	Discontinued
0.7143	Intermediate Similarity	NPD3815	Phase 1
0.7143	Intermediate Similarity	NPD3816	Phase 1
0.7143	Intermediate Similarity	NPD6618	Phase 2
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7827	Phase 1
0.7135	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4123	Phase 3
0.712	Intermediate Similarity	NPD3349	Phase 2
0.7108	Intermediate Similarity	NPD7124	Phase 2
0.7107	Intermediate Similarity	NPD4474	Approved
0.7107	Intermediate Similarity	NPD4475	Approved
0.7105	Intermediate Similarity	NPD2668	Approved
0.7105	Intermediate Similarity	NPD2667	Approved
0.7097	Intermediate Similarity	NPD7296	Approved
0.7091	Intermediate Similarity	NPD6331	Phase 2
0.7091	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5156	Approved
0.7089	Intermediate Similarity	NPD5155	Approved
0.7088	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2232	Approved
0.7078	Intermediate Similarity	NPD2230	Approved
0.7078	Intermediate Similarity	NPD2233	Approved
0.707	Intermediate Similarity	NPD3636	Approved
0.707	Intermediate Similarity	NPD3635	Approved
0.707	Intermediate Similarity	NPD3637	Approved
0.7066	Intermediate Similarity	NPD7598	Phase 2
0.7053	Intermediate Similarity	NPD8095	Phase 1
0.7048	Intermediate Similarity	NPD3692	Discontinued
0.7047	Intermediate Similarity	NPD4583	Approved
0.7047	Intermediate Similarity	NPD4582	Approved
0.7041	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4093	Discontinued
0.7027	Intermediate Similarity	NPD7291	Discontinued
0.7027	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3594	Approved
0.7025	Intermediate Similarity	NPD2605	Approved
0.7025	Intermediate Similarity	NPD3595	Approved
0.7025	Intermediate Similarity	NPD2606	Approved
0.7024	Intermediate Similarity	NPD1424	Approved
0.7018	Intermediate Similarity	NPD6875	Approved
0.7018	Intermediate Similarity	NPD6876	Approved
0.7015	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3705	Approved
0.7012	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3656	Approved
0.7012	Intermediate Similarity	NPD1375	Discontinued
0.701	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7247	Discontinued
0.7	Intermediate Similarity	NPD4873	Discontinued
0.6995	Remote Similarity	NPD2971	Approved
0.6995	Remote Similarity	NPD2968	Approved
0.6995	Remote Similarity	NPD4002	Approved
0.6995	Remote Similarity	NPD4004	Approved
0.6989	Remote Similarity	NPD5677	Discontinued
0.6988	Remote Similarity	NPD6748	Discontinued
0.6988	Remote Similarity	NPD5754	Discontinued
0.6987	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5310	Approved
0.6987	Remote Similarity	NPD5311	Approved
0.6975	Remote Similarity	NPD817	Approved
0.6975	Remote Similarity	NPD823	Approved
0.6973	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4083	Discontinued
0.6961	Remote Similarity	NPD7479	Phase 2
0.6959	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3620	Phase 2
0.6957	Remote Similarity	NPD2238	Phase 2
0.6957	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2161	Phase 2

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