NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	124.05
Volume:	130.743
LogP:	1.381
LogD:	1.694
LogS:	0.041
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	2.078
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.578
MDCK Permeability:	1.408203570463229e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.655
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	57.03965759277344%
Volume Distribution (VD):	0.775
Pgp-substrate:	38.85905838012695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.731
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.394
CYP2D6-substrate:	0.782
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	15.676
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.619
Maximum Recommended Daily Dose:	0.689
Skin Sensitization:	0.927
Carcinogencity:	0.057
Eye Corrosion:	0.978
Eye Irritation:	0.99
Respiratory Toxicity:	0.244

Download Data

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

Natural Product: NPC295295

Natural Product ID:	NPC295295
*Common Name:**	Orcinol
IUPAC Name:	5-methylbenzene-1,3-diol
Synonyms:	5-Methyl Resorcinol; 5-Methylresorcinol; Orcinol; Oricinol
Standard InCHIKey:	OIPPWFOQEKKFEE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H8O2/c1-5-2-6(8)4-7(9)3-5/h2-4,8-9H,1H3
SMILES:	Cc1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL110059
PubChem CID:	10436
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.lwt.2014.11.023]
NPO996	Acacia confusa	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[10843598]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO32513	Penicillium citrinum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18281952]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO996	Acacia confusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20047272]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20524638]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[22233034]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]
NPO33336	Penicillium sp. HN29-3B1	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26230970]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[27140807]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	n.a.	n.a.	PMID[33127538]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561895]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	fresh sarcotestas	Kwanak Campus of Seoul National University, Seoul, Korea	1996-Sep	PMID[9677265]
NPO18110	Lilium maximowiczii	Species	Liliaceae	Eukaryota	diseased bulbs	n.a.	n.a.	PMID[9677274]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	St. Louis	1996-SEP	PMID[9834151]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834158]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Wood	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21293	Parmelia tinctorum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6118	Erica umbellata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8365	Gymnadenia albida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5664	Davallia mariesii	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1919	Erica arborea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8365	Gymnadenia albida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1919	Erica arborea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6118	Erica umbellata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4725	Isodon lihsienensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21293	Parmelia tinctorum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5664	Davallia mariesii	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8365	Gymnadenia albida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6118	Erica umbellata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1919	Erica arborea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21293	Parmelia tinctorum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5786	Desmodium oxyphyllum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20304	Astragalus pectinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18110	Lilium maximowiczii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO66	Siphula decumbens	Species	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21293	Parmelia tinctorum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2851	Acanthella acuta	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4633	Calypogeia integristipula	Species	Calypogeiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1919	Erica arborea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8365	Gymnadenia albida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2258	Johnius belangerii	Species	Sciaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5664	Davallia mariesii	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19943	Fleischmannia hymenophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18807	Coffea pseudozanguebariae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO996	Acacia confusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6619	Phoebe clemensii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2777	Cirsium brevistylum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6513	Vernonia condensata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13015	Pilosella officinarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4725	Isodon lihsienensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17423	Solanum coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20689	Roystonea regia	Species	Arecaceae	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	2
IC50	8
Others	13

Activity Type	# Activity
Individual Protein	6
Organism	11
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT657	Individual Protein	1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1	Bos taurus	IC50	>	250.0	ug.mL-1	PMID[502514]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	>	100000.0	nM	PMID[502518]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	16800000.0	nM	PMID[502510]
NPT35	Others	n.a.		LogP	=	1.27	n.a.	PMID[502510]
NPT35	Others	n.a.		pKa	=	9.3	n.a.	PMID[502510]
NPT35	Others	n.a.		LogD	=	1.27	n.a.	PMID[502510]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Log 1/I50	=	1.77	1/M	PMID[502510]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	EC50	=	4030.0	nM	PMID[502511]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	EC50	=	4030.0	nM	PMID[502511]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	1000000.0	nM	PMID[502512]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	1100000.0	nM	PMID[502512]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	1700000.0	nM	PMID[502512]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	>	8100000.0	nM	PMID[502512]
NPT1	Others	Radical scavenging activity		IC50	=	800.0	nM	PMID[502513]
NPT5063	Organism	Bipolaris leersiae	Bipolaris leersiae	Inhibition	=	30.0	%	PMID[502515]
NPT5063	Organism	Bipolaris leersiae	Bipolaris leersiae	Inhibition	=	80.0	%	PMID[502515]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	31.0	%	PMID[502517]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	28.0	%	PMID[502517]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	46.0	%	PMID[502517]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	63.0	%	PMID[502517]
NPT35	Others	n.a.		Activity	<	50.0	%	PMID[502519]
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[502519]

☑ 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 NPC295295 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	374
0.1-0.2	2767
0.2-0.3	9633
0.3-0.4	10441
0.4-0.5	5713
0.5-0.6	9124
0.6-0.7	3703
0.7-0.8	749
0.8-0.85	115
0.85-0.9	43
0.9-0.95	34
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC166761
0.9348	High Similarity	NPC291789
0.9255	High Similarity	NPC147310
0.9255	High Similarity	NPC137415
0.9255	High Similarity	NPC294186
0.9255	High Similarity	NPC24407
0.9255	High Similarity	NPC192032
0.9255	High Similarity	NPC166313
0.9255	High Similarity	NPC11280
0.9158	High Similarity	NPC302219
0.9158	High Similarity	NPC168303
0.9158	High Similarity	NPC71002
0.9158	High Similarity	NPC249828
0.9158	High Similarity	NPC94351
0.9158	High Similarity	NPC146798
0.9158	High Similarity	NPC85479
0.9158	High Similarity	NPC53051
0.9158	High Similarity	NPC106396
0.9158	High Similarity	NPC222522
0.9158	High Similarity	NPC242342
0.9158	High Similarity	NPC313030
0.9158	High Similarity	NPC24404
0.9149	High Similarity	NPC10588
0.9149	High Similarity	NPC248573
0.9149	High Similarity	NPC275053
0.9149	High Similarity	NPC161571
0.9062	High Similarity	NPC227458
0.9062	High Similarity	NPC244513
0.9062	High Similarity	NPC218879
0.9053	High Similarity	NPC100340
0.9053	High Similarity	NPC143659
0.9053	High Similarity	NPC284011
0.9053	High Similarity	NPC72947
0.8977	High Similarity	NPC150837
0.8969	High Similarity	NPC37802
0.8878	High Similarity	NPC164576
0.8878	High Similarity	NPC99836
0.8878	High Similarity	NPC12640
0.8878	High Similarity	NPC201662
0.8866	High Similarity	NPC102216
0.8866	High Similarity	NPC241891
0.8866	High Similarity	NPC30506
0.8842	High Similarity	NPC80027
0.8788	High Similarity	NPC232523
0.8788	High Similarity	NPC204901
0.8788	High Similarity	NPC305603
0.8788	High Similarity	NPC61033
0.8788	High Similarity	NPC158253
0.8776	High Similarity	NPC246056
0.8776	High Similarity	NPC134829
0.8776	High Similarity	NPC292452
0.87	High Similarity	NPC174981
0.8687	High Similarity	NPC39097
0.8687	High Similarity	NPC39664
0.8687	High Similarity	NPC109691
0.8687	High Similarity	NPC470700
0.8687	High Similarity	NPC302681
0.8687	High Similarity	NPC118286
0.8681	High Similarity	NPC27974
0.8681	High Similarity	NPC19680
0.8621	High Similarity	NPC4154
0.8614	High Similarity	NPC33728
0.8614	High Similarity	NPC299568
0.8614	High Similarity	NPC186385
0.8614	High Similarity	NPC19808
0.86	High Similarity	NPC54844
0.86	High Similarity	NPC176527
0.8529	High Similarity	NPC94045
0.8529	High Similarity	NPC242178
0.8529	High Similarity	NPC168657
0.8529	High Similarity	NPC224870
0.8523	High Similarity	NPC270094
0.8515	High Similarity	NPC187958
0.8515	High Similarity	NPC58427
0.8515	High Similarity	NPC34864
0.8515	High Similarity	NPC105727
0.8515	High Similarity	NPC114392
0.8511	High Similarity	NPC29373
0.8495	Intermediate Similarity	NPC312304
0.8447	Intermediate Similarity	NPC296920
0.8447	Intermediate Similarity	NPC165770
0.8447	Intermediate Similarity	NPC4493
0.8447	Intermediate Similarity	NPC225679
0.8447	Intermediate Similarity	NPC224527
0.8447	Intermediate Similarity	NPC476632
0.8447	Intermediate Similarity	NPC90520
0.8447	Intermediate Similarity	NPC255068
0.8444	Intermediate Similarity	NPC124436
0.8431	Intermediate Similarity	NPC202647
0.8404	Intermediate Similarity	NPC231150
0.84	Intermediate Similarity	NPC471350
0.8365	Intermediate Similarity	NPC166995
0.8365	Intermediate Similarity	NPC473521
0.8365	Intermediate Similarity	NPC43525
0.8365	Intermediate Similarity	NPC280606
0.8352	Intermediate Similarity	NPC286904
0.8352	Intermediate Similarity	NPC248817
0.8351	Intermediate Similarity	NPC88420
0.835	Intermediate Similarity	NPC43411
0.8333	Intermediate Similarity	NPC107522
0.8317	Intermediate Similarity	NPC248904
0.8316	Intermediate Similarity	NPC306884
0.8316	Intermediate Similarity	NPC94139
0.8316	Intermediate Similarity	NPC147284
0.8316	Intermediate Similarity	NPC55903
0.8316	Intermediate Similarity	NPC162314
0.8316	Intermediate Similarity	NPC3358
0.8316	Intermediate Similarity	NPC210497
0.83	Intermediate Similarity	NPC119860
0.8298	Intermediate Similarity	NPC47950
0.8298	Intermediate Similarity	NPC192
0.8298	Intermediate Similarity	NPC300478
0.8286	Intermediate Similarity	NPC319803
0.8286	Intermediate Similarity	NPC117846
0.8286	Intermediate Similarity	NPC23804
0.8286	Intermediate Similarity	NPC263753
0.8286	Intermediate Similarity	NPC62546
0.8286	Intermediate Similarity	NPC162113
0.8269	Intermediate Similarity	NPC268032
0.8261	Intermediate Similarity	NPC197783
0.8242	Intermediate Similarity	NPC265146
0.8229	Intermediate Similarity	NPC245187
0.8218	Intermediate Similarity	NPC474839
0.8208	Intermediate Similarity	NPC107240
0.8208	Intermediate Similarity	NPC180508
0.8208	Intermediate Similarity	NPC228287
0.8208	Intermediate Similarity	NPC22610
0.8208	Intermediate Similarity	NPC276737
0.82	Intermediate Similarity	NPC168393
0.82	Intermediate Similarity	NPC315022
0.8182	Intermediate Similarity	NPC130103
0.8172	Intermediate Similarity	NPC23167
0.8172	Intermediate Similarity	NPC407
0.8172	Intermediate Similarity	NPC307235
0.8172	Intermediate Similarity	NPC184169
0.8163	Intermediate Similarity	NPC474073
0.8163	Intermediate Similarity	NPC152097
0.8163	Intermediate Similarity	NPC475078
0.8155	Intermediate Similarity	NPC61885
0.8155	Intermediate Similarity	NPC63698
0.8152	Intermediate Similarity	NPC175313
0.8144	Intermediate Similarity	NPC222146
0.8144	Intermediate Similarity	NPC257182
0.8144	Intermediate Similarity	NPC313650
0.8144	Intermediate Similarity	NPC274678
0.8131	Intermediate Similarity	NPC246760
0.8131	Intermediate Similarity	NPC84999
0.8131	Intermediate Similarity	NPC472893
0.8131	Intermediate Similarity	NPC167934
0.8131	Intermediate Similarity	NPC53906
0.8131	Intermediate Similarity	NPC808
0.8119	Intermediate Similarity	NPC130817
0.8119	Intermediate Similarity	NPC315936
0.8113	Intermediate Similarity	NPC261343
0.8085	Intermediate Similarity	NPC104216
0.8085	Intermediate Similarity	NPC25493
0.8085	Intermediate Similarity	NPC113460
0.8081	Intermediate Similarity	NPC260775
0.8065	Intermediate Similarity	NPC155393
0.8061	Intermediate Similarity	NPC312132
0.8061	Intermediate Similarity	NPC259512
0.8056	Intermediate Similarity	NPC114064
0.8056	Intermediate Similarity	NPC123559
0.8056	Intermediate Similarity	NPC141090
0.8056	Intermediate Similarity	NPC203113
0.8056	Intermediate Similarity	NPC193067
0.8056	Intermediate Similarity	NPC150624
0.8041	Intermediate Similarity	NPC76938
0.8021	Intermediate Similarity	NPC270547
0.8021	Intermediate Similarity	NPC155908
0.8021	Intermediate Similarity	NPC304541
0.8	Intermediate Similarity	NPC70677
0.8	Intermediate Similarity	NPC318325
0.8	Intermediate Similarity	NPC242240
0.8	Intermediate Similarity	NPC130756
0.8	Intermediate Similarity	NPC177420
0.8	Intermediate Similarity	NPC248396
0.8	Intermediate Similarity	NPC72729
0.8	Intermediate Similarity	NPC280347
0.8	Intermediate Similarity	NPC48730
0.8	Intermediate Similarity	NPC174911
0.8	Intermediate Similarity	NPC258219
0.8	Intermediate Similarity	NPC129373
0.8	Intermediate Similarity	NPC12931
0.8	Intermediate Similarity	NPC123273
0.8	Intermediate Similarity	NPC98772
0.7982	Intermediate Similarity	NPC219070
0.7982	Intermediate Similarity	NPC244816
0.7982	Intermediate Similarity	NPC69261
0.7982	Intermediate Similarity	NPC33270
0.7982	Intermediate Similarity	NPC277588
0.7982	Intermediate Similarity	NPC259638
0.7982	Intermediate Similarity	NPC50521
0.7982	Intermediate Similarity	NPC15860
0.7982	Intermediate Similarity	NPC474933
0.7982	Intermediate Similarity	NPC470759
0.7982	Intermediate Similarity	NPC127894
0.7982	Intermediate Similarity	NPC221549
0.7982	Intermediate Similarity	NPC195466
0.798	Intermediate Similarity	NPC109955

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 NPC295295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	1108
0.2-0.3	2056
0.3-0.4	2868
0.4-0.5	1652
0.5-0.6	823
0.6-0.7	216
0.7-0.8	35
0.8-0.85	2
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9149	High Similarity	NPD1242	Phase 1
0.866	High Similarity	NPD846	Approved
0.866	High Similarity	NPD940	Approved
0.8621	High Similarity	NPD9093	Approved
0.8614	High Similarity	NPD4750	Phase 3
0.8523	High Similarity	NPD9089	Approved
0.8444	Intermediate Similarity	NPD111	Approved
0.8144	Intermediate Similarity	NPD844	Approved
0.8061	Intermediate Similarity	NPD288	Approved
0.8	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD9094	Approved
0.7857	Intermediate Similarity	NPD2934	Approved
0.7857	Intermediate Similarity	NPD2933	Approved
0.7857	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2860	Approved
0.7778	Intermediate Similarity	NPD2859	Approved
0.7723	Intermediate Similarity	NPD3020	Approved
0.767	Intermediate Similarity	NPD9500	Approved
0.7624	Intermediate Similarity	NPD9273	Approved
0.7614	Intermediate Similarity	NPD9087	Approved
0.7576	Intermediate Similarity	NPD845	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.7473	Intermediate Similarity	NPD9088	Approved
0.7453	Intermediate Similarity	NPD1445	Approved
0.7453	Intermediate Similarity	NPD1444	Approved
0.7426	Intermediate Similarity	NPD1809	Phase 2
0.7407	Intermediate Similarity	NPD3021	Approved
0.7407	Intermediate Similarity	NPD3022	Approved
0.7339	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD602	Approved
0.7311	Intermediate Similarity	NPD858	Approved
0.7311	Intermediate Similarity	NPD599	Approved
0.7311	Intermediate Similarity	NPD859	Approved
0.7281	Intermediate Similarity	NPD1548	Phase 1
0.7273	Intermediate Similarity	NPD228	Approved
0.7265	Intermediate Similarity	NPD9269	Phase 2
0.7248	Intermediate Similarity	NPD1792	Phase 2
0.7217	Intermediate Similarity	NPD9268	Approved
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD422	Phase 1
0.7174	Intermediate Similarity	NPD9294	Approved
0.7167	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD3027	Phase 3
0.7131	Intermediate Similarity	NPD4625	Phase 3
0.7107	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9610	Approved
0.7103	Intermediate Similarity	NPD9244	Approved
0.7103	Intermediate Similarity	NPD9608	Approved
0.7091	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9618	Approved
0.708	Intermediate Similarity	NPD9614	Approved
0.7073	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD2342	Discontinued
0.7064	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9377	Approved
0.7054	Intermediate Similarity	NPD9379	Approved
0.7054	Intermediate Similarity	NPD7635	Approved
0.7049	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD74	Approved
0.7	Intermediate Similarity	NPD9295	Approved
0.7	Intermediate Similarity	NPD9266	Approved
0.6972	Remote Similarity	NPD968	Approved
0.693	Remote Similarity	NPD1791	Approved
0.693	Remote Similarity	NPD1793	Approved
0.6917	Remote Similarity	NPD2983	Phase 2
0.6917	Remote Similarity	NPD2982	Phase 2
0.6911	Remote Similarity	NPD4908	Phase 1
0.6909	Remote Similarity	NPD9267	Approved
0.6909	Remote Similarity	NPD9264	Approved
0.6909	Remote Similarity	NPD9263	Approved
0.6909	Remote Similarity	NPD290	Approved
0.6905	Remote Similarity	NPD230	Phase 1
0.6897	Remote Similarity	NPD9613	Approved
0.6897	Remote Similarity	NPD9615	Approved
0.6897	Remote Similarity	NPD9616	Approved
0.6864	Remote Similarity	NPD9381	Approved
0.6864	Remote Similarity	NPD9384	Approved
0.685	Remote Similarity	NPD2568	Approved
0.6842	Remote Similarity	NPD2228	Approved
0.6842	Remote Similarity	NPD2234	Approved
0.6842	Remote Similarity	NPD2229	Approved
0.6838	Remote Similarity	NPD316	Approved
0.6838	Remote Similarity	NPD3091	Approved
0.6833	Remote Similarity	NPD2981	Phase 2
0.6825	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1613	Approved
0.6825	Remote Similarity	NPD943	Approved
0.6822	Remote Similarity	NPD3028	Approved
0.681	Remote Similarity	NPD9493	Approved
0.68	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD9622	Approved
0.6768	Remote Similarity	NPD9073	Approved
0.6752	Remote Similarity	NPD317	Approved
0.6752	Remote Similarity	NPD856	Approved
0.6752	Remote Similarity	NPD318	Approved
0.6752	Remote Similarity	NPD16	Approved
0.675	Remote Similarity	NPD3092	Approved
0.675	Remote Similarity	NPD1201	Approved
0.6744	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3019	Approved
0.6723	Remote Similarity	NPD4059	Approved
0.6723	Remote Similarity	NPD2932	Approved
0.6695	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD9545	Approved
0.6694	Remote Similarity	NPD3018	Phase 2
0.6692	Remote Similarity	NPD6100	Approved
0.6692	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9296	Approved
0.6667	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4093	Discontinued
0.6639	Remote Similarity	NPD1357	Approved
0.6615	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD9619	Approved
0.6613	Remote Similarity	NPD9621	Approved
0.6613	Remote Similarity	NPD9620	Approved
0.6612	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6696	Suspended
0.6583	Remote Similarity	NPD2286	Discontinued
0.6583	Remote Similarity	NPD1751	Approved
0.6583	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1778	Approved
0.6581	Remote Similarity	NPD709	Approved
0.6581	Remote Similarity	NPD256	Approved
0.6581	Remote Similarity	NPD255	Approved
0.6562	Remote Similarity	NPD1240	Approved
0.6562	Remote Similarity	NPD1555	Discontinued
0.6562	Remote Similarity	NPD468	Phase 1
0.6557	Remote Similarity	NPD1608	Approved
0.6555	Remote Similarity	NPD1759	Phase 1
0.6552	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2684	Approved
0.6545	Remote Similarity	NPD9261	Approved
0.6532	Remote Similarity	NPD1133	Approved
0.6532	Remote Similarity	NPD1470	Approved
0.6532	Remote Similarity	NPD1129	Approved
0.6532	Remote Similarity	NPD1134	Approved
0.6532	Remote Similarity	NPD1135	Approved
0.6532	Remote Similarity	NPD1131	Approved
0.6504	Remote Similarity	NPD1755	Approved
0.6504	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD497	Approved
0.6496	Remote Similarity	NPD9281	Approved
0.6496	Remote Similarity	NPD475	Phase 2
0.6493	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1091	Approved
0.6471	Remote Similarity	NPD1758	Phase 1
0.6466	Remote Similarity	NPD821	Approved
0.6462	Remote Similarity	NPD1607	Approved
0.6452	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD3095	Discontinued
0.6446	Remote Similarity	NPD4626	Approved
0.6434	Remote Similarity	NPD2238	Phase 2
0.6429	Remote Similarity	NPD2861	Phase 2
0.6423	Remote Similarity	NPD2230	Approved
0.6423	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD2233	Approved
0.6423	Remote Similarity	NPD2561	Approved
0.6423	Remote Similarity	NPD2232	Approved
0.6423	Remote Similarity	NPD2562	Approved
0.641	Remote Similarity	NPD495	Approved
0.641	Remote Similarity	NPD5283	Phase 1
0.641	Remote Similarity	NPD498	Approved
0.641	Remote Similarity	NPD496	Approved
0.6406	Remote Similarity	NPD601	Approved
0.6406	Remote Similarity	NPD597	Approved
0.6406	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD598	Approved
0.64	Remote Similarity	NPD3053	Approved
0.64	Remote Similarity	NPD3055	Approved
0.6393	Remote Similarity	NPD3496	Discontinued
0.6393	Remote Similarity	NPD1980	Approved
0.6393	Remote Similarity	NPD1983	Approved
0.6393	Remote Similarity	NPD1981	Approved
0.6387	Remote Similarity	NPD9568	Approved
0.6378	Remote Similarity	NPD596	Approved
0.6378	Remote Similarity	NPD600	Approved
0.6372	Remote Similarity	NPD3134	Approved
0.6371	Remote Similarity	NPD4659	Approved
0.6364	Remote Similarity	NPD1510	Phase 2
0.6364	Remote Similarity	NPD9250	Approved
0.6357	Remote Similarity	NPD1136	Approved
0.6357	Remote Similarity	NPD1132	Approved
0.6357	Remote Similarity	NPD1130	Approved
0.635	Remote Similarity	NPD7390	Discontinued
0.6349	Remote Similarity	NPD6584	Phase 3
0.6349	Remote Similarity	NPD257	Approved
0.6349	Remote Similarity	NPD258	Approved
0.6325	Remote Similarity	NPD7843	Approved
0.6324	Remote Similarity	NPD302	Approved
0.6324	Remote Similarity	NPD2219	Phase 1
0.6321	Remote Similarity	NPD159	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5310	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