NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	267.823
LogP:	2.201
LogD:	2.289
LogS:	-3.914
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	2.835
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.719
MDCK Permeability:	1.1525222362251952e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	88.4786605834961%
Volume Distribution (VD):	0.5
Pgp-substrate:	11.18659782409668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.808
CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.656
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.602
CYP2D6-substrate:	0.789
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	20.476
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.282
Rat Oral Acute Toxicity:	0.747
Maximum Recommended Daily Dose:	0.274
Skin Sensitization:	0.926
Carcinogencity:	0.751
Eye Corrosion:	0.036
Eye Irritation:	0.942
Respiratory Toxicity:	0.612

Download Data

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

Natural Product: NPC1612

Natural Product ID:	NPC1612
*Common Name:**	Butin
IUPAC Name:	(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrochromen-4-one
Synonyms:	Butin
Standard InCHIKey:	MJBPUQUGJNAPAZ-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C15H12O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-6,14,16-17,19H,7H2/t14-/m0/s1
SMILES:	Oc1ccc2c(c1)O[C@@H](CC2=O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451168
PubChem CID:	92775
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104489]
NPO6062	Acacia mearnsii	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[21192716]
NPO26559	Glycine soja	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21545185]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22466953]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24450804]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9357	Mitragyna inermis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14975	Adenanthera pavonina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27620.1	Pteris cretica var. nervosa	Varieties	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25181	Cyperus papyrus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6062	Acacia mearnsii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9357	Mitragyna inermis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4916	Toxicodendron vernicifluum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25479	Sabal blackburniana	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27620.1	Pteris cretica var. nervosa	Varieties	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22798	Pseudofumaria lutea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6062	Acacia mearnsii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25181	Cyperus papyrus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14975	Adenanthera pavonina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4916	Toxicodendron vernicifluum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9620	Rhodococcus fascians	Species	0cardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13790	Abedus herberti	Species	Belostomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4916	Toxicodendron vernicifluum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14078	Paramecium tetraurelia	Species	Parameciidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6062	Acacia mearnsii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26723	Lachnophyllum gossypinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13685	Scrophularia umbrosa	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10917	Junceella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12213	Perriera orientalis	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9017	Fagus grandifolia	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12716	Stocksia brahuica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14975	Adenanthera pavonina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27620.1	Pteris cretica var. nervosa	Varieties	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26531	Aeschrion excelsa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13987	Solanum sublobatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8181	Hypoxylon tinctor	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26559	Glycine soja	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26403	Brachymeris montana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22798	Pseudofumaria lutea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26881	Croton zehntneri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8628	Strychnos erichsonii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5383	Othonna dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12021	Artemisia incanescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12564	Sinularia facile	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10325	Boletus pini	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25181	Cyperus papyrus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13600	Ichthyothere latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6599	Neorautanenia ficifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9357	Mitragyna inermis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26722	Dorstenia dinklagei	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8842	Neurymenia fraxinifolia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25479	Sabal blackburniana	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8308	Bryocaulon pseudosatoanum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3075	Dimorphotheca aurantiaca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29152	Caloboletus calopus	Species	Boletaceae	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
IC50	2
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	10.0	ug ml-1	PMID[488185]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	50.0	%	PMID[488186]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	9600.0	nM	PMID[488186]
NPT848	Cell Line	N9	Homo sapiens	IC50	=	28320.0	nM	PMID[488187]
NPT804	Cell Line	HT-22	Mus musculus	EC50	=	1700.0	nM	PMID[488188]

☑ 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 NPC1612 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	451
0.1-0.2	1790
0.2-0.3	4608
0.3-0.4	10825
0.4-0.5	6711
0.5-0.6	3463
0.6-0.7	4784
0.7-0.8	5436
0.8-0.85	2482
0.85-0.9	1649
0.9-0.95	454
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC183959
0.993	High Similarity	NPC294852
0.993	High Similarity	NPC321011
0.993	High Similarity	NPC188679
0.9726	High Similarity	NPC246328
0.9726	High Similarity	NPC325028
0.9726	High Similarity	NPC256346
0.9726	High Similarity	NPC27532
0.9724	High Similarity	NPC204515
0.9722	High Similarity	NPC105512
0.972	High Similarity	NPC95864
0.9658	High Similarity	NPC61506
0.9658	High Similarity	NPC260491
0.9658	High Similarity	NPC302950
0.9658	High Similarity	NPC236637
0.9658	High Similarity	NPC9743
0.9658	High Similarity	NPC219582
0.9658	High Similarity	NPC36835
0.9658	High Similarity	NPC240476
0.9658	High Similarity	NPC246162
0.9653	High Similarity	NPC3036
0.9592	High Similarity	NPC18727
0.9592	High Similarity	NPC141212
0.9592	High Similarity	NPC192083
0.9592	High Similarity	NPC213896
0.958	High Similarity	NPC70136
0.953	High Similarity	NPC99597
0.953	High Similarity	NPC291508
0.953	High Similarity	NPC52530
0.953	High Similarity	NPC210084
0.9527	High Similarity	NPC67396
0.9527	High Similarity	NPC321779
0.9524	High Similarity	NPC19721
0.9524	High Similarity	NPC106976
0.9521	High Similarity	NPC29231
0.9521	High Similarity	NPC62042
0.9517	High Similarity	NPC276930
0.9517	High Similarity	NPC196277
0.9517	High Similarity	NPC272721
0.9517	High Similarity	NPC119059
0.9517	High Similarity	NPC194856
0.9517	High Similarity	NPC43669
0.951	High Similarity	NPC38065
0.951	High Similarity	NPC279121
0.951	High Similarity	NPC242893
0.9463	High Similarity	NPC474638
0.9463	High Similarity	NPC195796
0.9463	High Similarity	NPC255106
0.9463	High Similarity	NPC471500
0.9463	High Similarity	NPC13858
0.9463	High Similarity	NPC291878
0.9463	High Similarity	NPC35038
0.9463	High Similarity	NPC24640
0.9463	High Similarity	NPC278778
0.9463	High Similarity	NPC235165
0.9463	High Similarity	NPC326037
0.9463	High Similarity	NPC320825
0.9463	High Similarity	NPC201837
0.9459	High Similarity	NPC167091
0.9459	High Similarity	NPC271779
0.9459	High Similarity	NPC292214
0.9459	High Similarity	NPC74924
0.9459	High Similarity	NPC469550
0.9459	High Similarity	NPC88645
0.9459	High Similarity	NPC298692
0.9459	High Similarity	NPC206238
0.9456	High Similarity	NPC251110
0.9456	High Similarity	NPC31363
0.9448	High Similarity	NPC207729
0.9448	High Similarity	NPC74881
0.9448	High Similarity	NPC51443
0.9448	High Similarity	NPC77378
0.9448	High Similarity	NPC108406
0.9441	High Similarity	NPC175013
0.9437	High Similarity	NPC182421
0.94	High Similarity	NPC48208
0.94	High Similarity	NPC474055
0.94	High Similarity	NPC156057
0.94	High Similarity	NPC471209
0.94	High Similarity	NPC472598
0.94	High Similarity	NPC299520
0.94	High Similarity	NPC129684
0.94	High Similarity	NPC471515
0.94	High Similarity	NPC475267
0.94	High Similarity	NPC67876
0.94	High Similarity	NPC27337
0.94	High Similarity	NPC162869
0.94	High Similarity	NPC471479
0.94	High Similarity	NPC474208
0.94	High Similarity	NPC474836
0.9396	High Similarity	NPC45849
0.9396	High Similarity	NPC470327
0.9396	High Similarity	NPC200761
0.9396	High Similarity	NPC2928
0.9396	High Similarity	NPC477503
0.9392	High Similarity	NPC101996
0.9392	High Similarity	NPC257648
0.9392	High Similarity	NPC199100
0.9392	High Similarity	NPC472912
0.9392	High Similarity	NPC120537
0.9392	High Similarity	NPC180234
0.9392	High Similarity	NPC39007
0.9392	High Similarity	NPC477231
0.9392	High Similarity	NPC260979
0.9392	High Similarity	NPC161277
0.9388	High Similarity	NPC61620
0.9388	High Similarity	NPC338131
0.9388	High Similarity	NPC248102
0.9384	High Similarity	NPC118726
0.9384	High Similarity	NPC218569
0.9384	High Similarity	NPC218490
0.9384	High Similarity	NPC12367
0.9379	High Similarity	NPC179271
0.9379	High Similarity	NPC20791
0.9342	High Similarity	NPC308992
0.9338	High Similarity	NPC210459
0.9338	High Similarity	NPC53545
0.9338	High Similarity	NPC117418
0.9338	High Similarity	NPC55738
0.9338	High Similarity	NPC22192
0.9333	High Similarity	NPC472916
0.9333	High Similarity	NPC209614
0.9333	High Similarity	NPC470328
0.9333	High Similarity	NPC472626
0.9333	High Similarity	NPC250922
0.9324	High Similarity	NPC260895
0.9324	High Similarity	NPC171010
0.9324	High Similarity	NPC149614
0.932	High Similarity	NPC52005
0.932	High Similarity	NPC137062
0.932	High Similarity	NPC87125
0.932	High Similarity	NPC223579
0.932	High Similarity	NPC270465
0.932	High Similarity	NPC287101
0.932	High Similarity	NPC183950
0.9315	High Similarity	NPC21835
0.9315	High Similarity	NPC188074
0.9315	High Similarity	NPC125449
0.9315	High Similarity	NPC168803
0.9315	High Similarity	NPC239312
0.9315	High Similarity	NPC275772
0.9315	High Similarity	NPC130230
0.9306	High Similarity	NPC287722
0.9306	High Similarity	NPC73028
0.9296	High Similarity	NPC147686
0.9296	High Similarity	NPC329225
0.9296	High Similarity	NPC472460
0.9281	High Similarity	NPC474033
0.9281	High Similarity	NPC472964
0.9281	High Similarity	NPC476247
0.9281	High Similarity	NPC474034
0.9276	High Similarity	NPC282009
0.9276	High Similarity	NPC328102
0.9276	High Similarity	NPC472624
0.9276	High Similarity	NPC118256
0.9276	High Similarity	NPC470183
0.9276	High Similarity	NPC471744
0.9276	High Similarity	NPC287328
0.9276	High Similarity	NPC36217
0.9276	High Similarity	NPC192686
0.9276	High Similarity	NPC472902
0.9276	High Similarity	NPC321399
0.9276	High Similarity	NPC263449
0.9276	High Similarity	NPC119209
0.9272	High Similarity	NPC222814
0.9272	High Similarity	NPC472910
0.9272	High Similarity	NPC245758
0.9272	High Similarity	NPC472911
0.9272	High Similarity	NPC472913
0.9272	High Similarity	NPC96167
0.9272	High Similarity	NPC472914
0.9272	High Similarity	NPC223787
0.9267	High Similarity	NPC255807
0.9267	High Similarity	NPC226025
0.9267	High Similarity	NPC113906
0.9267	High Similarity	NPC152951
0.9267	High Similarity	NPC37392
0.9267	High Similarity	NPC230149
0.9267	High Similarity	NPC57674
0.9267	High Similarity	NPC168247
0.9267	High Similarity	NPC31018
0.9267	High Similarity	NPC117992
0.9262	High Similarity	NPC323626
0.9262	High Similarity	NPC60972
0.9262	High Similarity	NPC324233
0.9262	High Similarity	NPC55205
0.9262	High Similarity	NPC39732
0.9257	High Similarity	NPC149127
0.9257	High Similarity	NPC45873
0.9257	High Similarity	NPC188871
0.9257	High Similarity	NPC10467
0.9257	High Similarity	NPC184136
0.9257	High Similarity	NPC3825
0.9257	High Similarity	NPC286342
0.9257	High Similarity	NPC179183
0.9257	High Similarity	NPC88804
0.9252	High Similarity	NPC19545
0.9252	High Similarity	NPC194653
0.9252	High Similarity	NPC139364
0.9252	High Similarity	NPC120464

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 NPC1612 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	928
0.2-0.3	1813
0.3-0.4	2601
0.4-0.5	1713
0.5-0.6	1022
0.6-0.7	455
0.7-0.8	122
0.8-0.85	37
0.85-0.9	11
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9658	High Similarity	NPD1934	Approved
0.9592	High Similarity	NPD2393	Clinical (unspecified phase)
0.951	High Similarity	NPD1511	Approved
0.9379	High Similarity	NPD1512	Approved
0.9296	High Similarity	NPD1549	Phase 2
0.9225	High Similarity	NPD1552	Clinical (unspecified phase)
0.9225	High Similarity	NPD1550	Clinical (unspecified phase)
0.9073	High Similarity	NPD2801	Approved
0.9038	High Similarity	NPD6167	Clinical (unspecified phase)
0.9038	High Similarity	NPD6168	Clinical (unspecified phase)
0.9038	High Similarity	NPD6166	Phase 2
0.8954	High Similarity	NPD4868	Clinical (unspecified phase)
0.8954	High Similarity	NPD3882	Suspended
0.8951	High Similarity	NPD1510	Phase 2
0.8924	High Similarity	NPD3818	Discontinued
0.8874	High Similarity	NPD4380	Phase 2
0.8812	High Similarity	NPD7074	Phase 3
0.8774	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD7054	Approved
0.8696	High Similarity	NPD7472	Approved
0.8671	High Similarity	NPD943	Approved
0.8671	High Similarity	NPD1240	Approved
0.8667	High Similarity	NPD4378	Clinical (unspecified phase)
0.8654	High Similarity	NPD7075	Discontinued
0.8645	High Similarity	NPD3817	Phase 2
0.8642	High Similarity	NPD6797	Phase 2
0.863	High Similarity	NPD2796	Approved
0.8589	High Similarity	NPD7251	Discontinued
0.8581	High Similarity	NPD7096	Clinical (unspecified phase)
0.8552	High Similarity	NPD1607	Approved
0.8544	High Similarity	NPD5494	Approved
0.8542	High Similarity	NPD1612	Clinical (unspecified phase)
0.8542	High Similarity	NPD1613	Approved
0.8537	High Similarity	NPD4338	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1465	Phase 2
0.8462	Intermediate Similarity	NPD7819	Suspended
0.8424	Intermediate Similarity	NPD7808	Phase 3
0.8415	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8261	Intermediate Similarity	NPD6959	Discontinued
0.8255	Intermediate Similarity	NPD1551	Phase 2
0.8231	Intermediate Similarity	NPD230	Phase 1
0.8182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD5402	Approved
0.8158	Intermediate Similarity	NPD3750	Approved
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6559	Discontinued
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8077	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD3749	Approved
0.8067	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5401	Approved
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8037	Intermediate Similarity	NPD1247	Approved
0.8028	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7768	Phase 2
0.7895	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD447	Suspended
0.7857	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2800	Approved
0.7848	Intermediate Similarity	NPD920	Approved
0.7838	Intermediate Similarity	NPD3027	Phase 3
0.7834	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3926	Phase 2
0.7829	Intermediate Similarity	NPD3748	Approved
0.7821	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1203	Approved
0.7806	Intermediate Similarity	NPD4628	Phase 3
0.7799	Intermediate Similarity	NPD1653	Approved
0.7798	Intermediate Similarity	NPD3751	Discontinued
0.7785	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7742	Intermediate Similarity	NPD1243	Approved
0.7736	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD2534	Approved
0.7722	Intermediate Similarity	NPD2532	Approved
0.7722	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD9494	Approved
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2313	Discontinued
0.7662	Intermediate Similarity	NPD6100	Approved
0.7662	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD6190	Approved
0.764	Intermediate Similarity	NPD3226	Approved
0.7632	Intermediate Similarity	NPD1933	Approved
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.7603	Intermediate Similarity	NPD9269	Phase 2
0.756	Intermediate Similarity	NPD3787	Discontinued
0.7558	Intermediate Similarity	NPD5953	Discontinued
0.7544	Intermediate Similarity	NPD7286	Phase 2
0.7533	Intermediate Similarity	NPD4908	Phase 1
0.7532	Intermediate Similarity	NPD2309	Approved
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD9717	Approved
0.7471	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6651	Approved
0.7443	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD1608	Approved
0.7351	Intermediate Similarity	NPD2861	Phase 2
0.7348	Intermediate Similarity	NPD4363	Phase 3
0.7348	Intermediate Similarity	NPD4360	Phase 2
0.7333	Intermediate Similarity	NPD1470	Approved
0.7329	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD9268	Approved
0.732	Intermediate Similarity	NPD411	Approved
0.7317	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7685	Pre-registration
0.7297	Intermediate Similarity	NPD422	Phase 1
0.7297	Intermediate Similarity	NPD1201	Approved
0.7289	Intermediate Similarity	NPD6844	Discontinued
0.7289	Intermediate Similarity	NPD37	Approved
0.7285	Intermediate Similarity	NPD2798	Approved
0.7283	Intermediate Similarity	NPD7228	Approved
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4966	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.726	Intermediate Similarity	NPD9545	Approved
0.7251	Intermediate Similarity	NPD5710	Approved
0.7251	Intermediate Similarity	NPD5711	Approved
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5242	Approved
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7208	Intermediate Similarity	NPD3268	Approved
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7202	Intermediate Similarity	NPD4288	Approved
0.7202	Intermediate Similarity	NPD5353	Approved
0.7196	Intermediate Similarity	NPD7584	Approved
0.7188	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1019	Discontinued
0.717	Intermediate Similarity	NPD7266	Discontinued
0.7162	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD1241	Discontinued
0.7152	Intermediate Similarity	NPD3225	Approved
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6779	Approved
0.7151	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7127	Intermediate Similarity	NPD4287	Approved
0.7123	Intermediate Similarity	NPD9493	Approved
0.712	Intermediate Similarity	NPD8151	Discontinued
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.7105	Intermediate Similarity	NPD2797	Approved
0.7102	Intermediate Similarity	NPD1729	Discontinued
0.7097	Intermediate Similarity	NPD3764	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7086	Intermediate Similarity	NPD4749	Approved
0.7081	Intermediate Similarity	NPD2654	Approved
0.7073	Intermediate Similarity	NPD4661	Approved
0.7073	Intermediate Similarity	NPD4662	Approved
0.707	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5124	Phase 1
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7051	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD8455	Phase 2
0.7037	Intermediate Similarity	NPD7435	Discontinued
0.7027	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4361	Phase 2
0.7024	Intermediate Similarity	NPD6385	Approved
0.7024	Intermediate Similarity	NPD6386	Approved
0.7022	Intermediate Similarity	NPD6104	Discontinued
0.702	Intermediate Similarity	NPD1481	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