NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	259.907
LogP:	3.059
LogD:	3.091
LogS:	-3.413
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	5.127
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.665
MDCK Permeability:	1.8757553334580734e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.764
30% Bioavailability (F30%):	0.55

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.248
Plasma Protein Binding (PPB):	82.54301452636719%
Volume Distribution (VD):	0.997
Pgp-substrate:	23.53436279296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.359
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.506
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.434
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	9.906
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.455
Skin Sensitization:	0.849
Carcinogencity:	0.535
Eye Corrosion:	0.513
Eye Irritation:	0.309
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC215671

Natural Product ID:	NPC215671
*Common Name:**	SFJOMLIUSIKKRA-FUQNVFFISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SFJOMLIUSIKKRA-FUQNVFFISA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-13(2)8-11-10(13)4-6-14(3)9-15(11,17)7-5-12(14)16/h10-12,16-17H,4-9H2,1-3H3/t10-,11+,12+,14+,15-/m1/s1
SMILES:	O[C@H]1CC[C@]2(C[C@]1(C)CC[C@@H]1[C@@H]2CC1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3315225
PubChem CID:	21726648
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO19965	Helenium alternifolium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1021/jo01271a036]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[10945272]
NPO23006	Moringa stenopetala	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12709911]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332846]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	Amami Oshima, Kagoshima Prefecture, Japan	n.a.	PMID[16933862]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331379]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21563811]
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[21615146]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21928797]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO40536	Streptomyces albolongus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26933756]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29578342]
NPO14240	Justicia ghiesbreghtiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748395]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15763	Huperzia lucidula	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22438	Asclepias speciosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19965	Helenium alternifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20771	Thalictrum fortunei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22113	Anthocercis genistoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14240	Justicia ghiesbreghtiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22756	Epimedium versicolor	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22953	Eupatorium pauciflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21032	Manilkara hexandra	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22438	Asclepias speciosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21158	Viburnum fur	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8115	Polyopes affinis	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13409	Crocus asturicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20967	Doriopsilla albopunctata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22698	Achillea pannonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27929	Aphanamixis polystachya	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20203	Syringa komarowi	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21654	Cyerce cristallina	Species	Caliphyllidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22308	Stevia satureiaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20896	Mimosa tenuiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27489	Alloascoidea hylecoeti	Species	Alloascoideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20522	Pyura sacciformis	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22887	Scutellaria violacea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21725	Uncaria glabrata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15763	Huperzia lucidula	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20583	Phaulopsis imbricata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20261	Teucrium trifidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20088	Piper sintenense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26325	Annulusmagnus triseptatus	Species	Annulatascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20707	Stillingia sanguinolenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4478	Parmelia pseudoreticulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22499	Corydalis flabellata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20457	Spirastrella inconstans	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20021	Physcia aegialita	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28103	Erica carnea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19891	Diospyros crassiflora	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21089	Mourera fluviatilis	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20381	Echites hirsuta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22048	Pteris palmiformis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21599	Ricciocarpos natans	Species	Ricciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23006	Moringa stenopetala	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18123	Dichapetalum madagascariense	Species	Dichapetalaceae	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	3

Activity Type	# Activity
Others	4
PROTEIN-PROTEIN INTERACTION	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	10.22	%	PMID[515249]
NPT2	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[515249]
NPT2	Others	Unspecified		Inhibition	=	5.93	%	PMID[515249]
NPT25209	PROTEIN-PROTEIN INTERACTION	Transforming growth factor beta-1 proprotein/Mothers against decapentaplegic homolog 3	Mus musculus	Inhibition	=	67.92	%	PMID[515250]
NPT25209	PROTEIN-PROTEIN INTERACTION	Transforming growth factor beta-1 proprotein/Mothers against decapentaplegic homolog 3	Mus musculus	IC50	=	3670.0	nM	PMID[515250]

☑ 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 NPC215671 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	470
0.1-0.2	5887
0.2-0.3	19329
0.3-0.4	9137
0.4-0.5	6299
0.5-0.6	1393
0.6-0.7	157
0.7-0.8	18
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475515
1.0	High Similarity	NPC87296
0.9091	High Similarity	NPC471269
0.8571	High Similarity	NPC53209
0.8333	Intermediate Similarity	NPC294858
0.8136	Intermediate Similarity	NPC236588
0.7833	Intermediate Similarity	NPC135438
0.7812	Intermediate Similarity	NPC80463
0.7759	Intermediate Similarity	NPC161473
0.7719	Intermediate Similarity	NPC307022
0.7636	Intermediate Similarity	NPC223468
0.7636	Intermediate Similarity	NPC287550
0.7636	Intermediate Similarity	NPC176309
0.7636	Intermediate Similarity	NPC84030
0.7636	Intermediate Similarity	NPC147343
0.7636	Intermediate Similarity	NPC198540
0.7619	Intermediate Similarity	NPC185547
0.7619	Intermediate Similarity	NPC95804
0.7576	Intermediate Similarity	NPC139207
0.7576	Intermediate Similarity	NPC185874
0.75	Intermediate Similarity	NPC300189
0.746	Intermediate Similarity	NPC475412
0.7419	Intermediate Similarity	NPC47663
0.7407	Intermediate Similarity	NPC144891
0.7385	Intermediate Similarity	NPC94897
0.7302	Intermediate Similarity	NPC185116
0.7273	Intermediate Similarity	NPC260116
0.7273	Intermediate Similarity	NPC240994
0.7206	Intermediate Similarity	NPC472741
0.7167	Intermediate Similarity	NPC102336
0.7167	Intermediate Similarity	NPC36002
0.7164	Intermediate Similarity	NPC44122
0.7164	Intermediate Similarity	NPC473929
0.7143	Intermediate Similarity	NPC164022
0.7143	Intermediate Similarity	NPC471272
0.7121	Intermediate Similarity	NPC144650
0.7121	Intermediate Similarity	NPC101128
0.7101	Intermediate Similarity	NPC66407
0.7101	Intermediate Similarity	NPC470833
0.7077	Intermediate Similarity	NPC475807
0.7059	Intermediate Similarity	NPC476928
0.7059	Intermediate Similarity	NPC48079
0.7059	Intermediate Similarity	NPC269077
0.7059	Intermediate Similarity	NPC253303
0.7042	Intermediate Similarity	NPC253805
0.7018	Intermediate Similarity	NPC14552
0.7015	Intermediate Similarity	NPC2728
0.7015	Intermediate Similarity	NPC208198
0.7015	Intermediate Similarity	NPC282619
0.7015	Intermediate Similarity	NPC11555
0.7015	Intermediate Similarity	NPC60837
0.7015	Intermediate Similarity	NPC172613
0.7	Intermediate Similarity	NPC282454
0.6984	Remote Similarity	NPC291147
0.697	Remote Similarity	NPC114891
0.697	Remote Similarity	NPC236099
0.697	Remote Similarity	NPC292419
0.697	Remote Similarity	NPC209686
0.697	Remote Similarity	NPC290791
0.697	Remote Similarity	NPC249078
0.6957	Remote Similarity	NPC474756
0.6957	Remote Similarity	NPC244790
0.6957	Remote Similarity	NPC475893
0.6944	Remote Similarity	NPC470151
0.6912	Remote Similarity	NPC142712
0.6912	Remote Similarity	NPC475897
0.6901	Remote Similarity	NPC1340
0.6901	Remote Similarity	NPC127094
0.6901	Remote Similarity	NPC470071
0.6901	Remote Similarity	NPC157422
0.6901	Remote Similarity	NPC187471
0.6901	Remote Similarity	NPC252182
0.6901	Remote Similarity	NPC109457
0.6901	Remote Similarity	NPC100586
0.6897	Remote Similarity	NPC314087
0.6866	Remote Similarity	NPC219940
0.6866	Remote Similarity	NPC167995
0.6866	Remote Similarity	NPC281540
0.6866	Remote Similarity	NPC118937
0.6866	Remote Similarity	NPC159654
0.6857	Remote Similarity	NPC299948
0.6857	Remote Similarity	NPC477820
0.6857	Remote Similarity	NPC254037
0.6857	Remote Similarity	NPC241085
0.6857	Remote Similarity	NPC210323
0.6857	Remote Similarity	NPC470830
0.6857	Remote Similarity	NPC107919
0.6857	Remote Similarity	NPC129829
0.6849	Remote Similarity	NPC131584
0.6849	Remote Similarity	NPC139765
0.6842	Remote Similarity	NPC108441
0.6842	Remote Similarity	NPC77550
0.6818	Remote Similarity	NPC218585
0.6818	Remote Similarity	NPC148174
0.6818	Remote Similarity	NPC71460
0.6812	Remote Similarity	NPC475884
0.6812	Remote Similarity	NPC204233
0.6812	Remote Similarity	NPC472984
0.6812	Remote Similarity	NPC473230
0.6806	Remote Similarity	NPC95165
0.6806	Remote Similarity	NPC476422
0.6774	Remote Similarity	NPC32222
0.6774	Remote Similarity	NPC202146
0.6769	Remote Similarity	NPC475968
0.6765	Remote Similarity	NPC473276
0.6765	Remote Similarity	NPC258595
0.6765	Remote Similarity	NPC474380
0.6765	Remote Similarity	NPC472946
0.6765	Remote Similarity	NPC41577
0.6761	Remote Similarity	NPC63588
0.6761	Remote Similarity	NPC92801
0.6761	Remote Similarity	NPC231945
0.6761	Remote Similarity	NPC232925
0.6761	Remote Similarity	NPC192192
0.6761	Remote Similarity	NPC251201
0.6757	Remote Similarity	NPC1973
0.6757	Remote Similarity	NPC167873
0.6753	Remote Similarity	NPC473257
0.6721	Remote Similarity	NPC300235
0.6721	Remote Similarity	NPC476136
0.6721	Remote Similarity	NPC476149
0.6721	Remote Similarity	NPC244869
0.6719	Remote Similarity	NPC150713
0.6719	Remote Similarity	NPC119425
0.6719	Remote Similarity	NPC29976
0.6714	Remote Similarity	NPC276616
0.6714	Remote Similarity	NPC245795
0.6714	Remote Similarity	NPC471238
0.6714	Remote Similarity	NPC469987
0.6714	Remote Similarity	NPC2648
0.6712	Remote Similarity	NPC10476
0.6712	Remote Similarity	NPC237510
0.6712	Remote Similarity	NPC304499
0.6712	Remote Similarity	NPC228994
0.6712	Remote Similarity	NPC192501
0.6712	Remote Similarity	NPC475793
0.6712	Remote Similarity	NPC74639
0.6712	Remote Similarity	NPC475458
0.6667	Remote Similarity	NPC167706
0.6667	Remote Similarity	NPC157777
0.6667	Remote Similarity	NPC307865
0.6667	Remote Similarity	NPC283655
0.6667	Remote Similarity	NPC473279
0.6667	Remote Similarity	NPC178223
0.6667	Remote Similarity	NPC477792
0.6667	Remote Similarity	NPC89069
0.6667	Remote Similarity	NPC85105
0.6667	Remote Similarity	NPC131506
0.6667	Remote Similarity	NPC478103
0.6667	Remote Similarity	NPC277917
0.6667	Remote Similarity	NPC166894
0.6667	Remote Similarity	NPC195530
0.6667	Remote Similarity	NPC149550
0.6622	Remote Similarity	NPC472950
0.6622	Remote Similarity	NPC317242
0.6622	Remote Similarity	NPC158208
0.6622	Remote Similarity	NPC243027
0.6622	Remote Similarity	NPC3403
0.6622	Remote Similarity	NPC196136
0.6622	Remote Similarity	NPC472952
0.662	Remote Similarity	NPC9942
0.6618	Remote Similarity	NPC199937
0.6618	Remote Similarity	NPC69149
0.6618	Remote Similarity	NPC68656
0.6579	Remote Similarity	NPC475725
0.6579	Remote Similarity	NPC272841
0.6579	Remote Similarity	NPC147993
0.6575	Remote Similarity	NPC472341
0.6575	Remote Similarity	NPC470610
0.6575	Remote Similarity	NPC473238
0.6575	Remote Similarity	NPC153719
0.6571	Remote Similarity	NPC63190
0.6562	Remote Similarity	NPC170780
0.6562	Remote Similarity	NPC3025
0.6533	Remote Similarity	NPC163597
0.6533	Remote Similarity	NPC63958
0.6528	Remote Similarity	NPC283316
0.6522	Remote Similarity	NPC300442
0.6515	Remote Similarity	NPC95958
0.65	Remote Similarity	NPC127997
0.65	Remote Similarity	NPC316035
0.65	Remote Similarity	NPC95969
0.6486	Remote Similarity	NPC477508
0.6486	Remote Similarity	NPC48795
0.6479	Remote Similarity	NPC478228
0.6447	Remote Similarity	NPC302578
0.6447	Remote Similarity	NPC185915
0.6447	Remote Similarity	NPC64081
0.6447	Remote Similarity	NPC472805
0.6447	Remote Similarity	NPC128951
0.6447	Remote Similarity	NPC169994
0.6447	Remote Similarity	NPC475031
0.6447	Remote Similarity	NPC476233
0.6447	Remote Similarity	NPC90979
0.6447	Remote Similarity	NPC474574
0.6447	Remote Similarity	NPC105208
0.6447	Remote Similarity	NPC477227
0.6447	Remote Similarity	NPC192046
0.6438	Remote Similarity	NPC471271
0.6438	Remote Similarity	NPC471268

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 NPC215671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	603
0.1-0.2	4959
0.2-0.3	2669
0.3-0.4	622
0.4-0.5	251
0.5-0.6	41
0.6-0.7	3
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7636	Intermediate Similarity	NPD385	Approved
0.7636	Intermediate Similarity	NPD384	Approved
0.6866	Remote Similarity	NPD371	Approved
0.6857	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD388	Approved
0.6842	Remote Similarity	NPD386	Approved
0.6528	Remote Similarity	NPD4787	Phase 1
0.6389	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6116	Phase 1
0.6216	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7525	Registered
0.6184	Remote Similarity	NPD3703	Phase 2
0.6104	Remote Similarity	NPD6117	Approved
0.6056	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1810	Approved
0.6053	Remote Similarity	NPD1811	Approved
0.5949	Remote Similarity	NPD6115	Approved
0.5949	Remote Similarity	NPD6114	Approved
0.5949	Remote Similarity	NPD6118	Approved
0.5949	Remote Similarity	NPD6697	Approved
0.5946	Remote Similarity	NPD3698	Phase 2
0.5875	Remote Similarity	NPD7645	Phase 2
0.5867	Remote Similarity	NPD4245	Approved
0.5867	Remote Similarity	NPD4244	Approved
0.5867	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD5360	Phase 3
0.5811	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4748	Discontinued
0.5802	Remote Similarity	NPD6928	Phase 2
0.5763	Remote Similarity	NPD1462	Approved
0.575	Remote Similarity	NPD3671	Phase 1
0.5696	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.569	Remote Similarity	NPD1460	Approved
0.5667	Remote Similarity	NPD367	Approved
0.5658	Remote Similarity	NPD4789	Approved
0.5641	Remote Similarity	NPD6926	Approved
0.5641	Remote Similarity	NPD6924	Approved
0.5634	Remote Similarity	NPD368	Approved
0.561	Remote Similarity	NPD7509	Discontinued
0.56	Remote Similarity	NPD6705	Phase 1

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