NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1874.19
Volume:	1658.67
LogP:	3.132
LogD:	1.543
LogS:	-2.351
# Rotatable Bonds:	20
TPSA:	877.36
# H-Bond Aceptor:	52
# H-Bond Donor:	29
# Rings:	14
# Heavy Atoms:	52

MedChem Properties

QED Drug-Likeness Score:	0.042
Synthetic Accessibility Score:	6.788
Fsp3:	0.146
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-8.05
MDCK Permeability:	3.906315669155447e-06
Pgp-inhibitor:	0.017
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	98.6275405883789%
Volume Distribution (VD):	-0.518
Pgp-substrate:	570.4795532226562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.462
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.0
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	15.242
Half-life (T1/2):	0.992

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.999
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.989
Carcinogencity:	0.001
Eye Corrosion:	0.003
Eye Irritation:	0.98
Respiratory Toxicity:	0.0

Download Data

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

Natural Product: NPC223468

Natural Product ID:	NPC223468
*Common Name:**	Menthol
IUPAC Name:	5-methyl-2-propan-2-ylcyclohexan-1-ol
Synonyms:	Aqua-Cool; Aquasoothe; Arjun; Catarrh; Dermacool; DL-Menthol; Fisherman's Friend Lozenges; Halls; Karvol; Lockets; Meggezones; Menthol; Muirs; Therapeutic Mineral Ice; Tixylix Decongestant Inh; Vocalzone
Standard InCHIKey:	NOOLISFMXDJSKH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3
SMILES:	CC(C)C1CCC(C)CC1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256087
PubChem CID:	1254
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane monoterpenoids

*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

☑ 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	18
IC50	5
Kd	2
LD50	2
MIC	1
Others	70
Potency	10

Activity Type	# Activity
Individual Protein	34
Organism	59
Others	14
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	EC50	=	28400.0	nM	PMID[502525]
NPT467	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Mus musculus	EC50	=	56000.0	nM	PMID[502525]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	Activity	=	10.0	uM	PMID[502526]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	IC50	=	92000.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	IC50	=	19000.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	IC50	=	520000.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	Kd	=	14400.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	29000.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	818000.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	34100.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	38400.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	11700.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	38800.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	93000.0	nM	PMID[502527]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	35300.0	nM	PMID[502527]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[502531]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	2.2	nM	PMID[502532]
NPT5259	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	=	3000.0	nM	PMID[502542]
NPT1841	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Rattus norvegicus	Activity	=	140.0	pA/pF	PMID[502543]
NPT1841	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Rattus norvegicus	EC50	=	75000.0	nM	PMID[502543]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	EC50	=	31622.78	nM	PMID[502545]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	EC50	=	30000.0	nM	PMID[502545]
NPT467	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Mus musculus	EC50	=	95000.0	nM	PMID[502545]
NPT4107	Organism	Culex pipiens	Culex pipiens	Ratio	=	53.0	n.a.	PMID[502522]
NPT1348	Organism	Psoroptes cuniculi	Psoroptes cuniculi	Activity	=	100.0	%	PMID[502523]
NPT167	Organism	Propionibacterium acnes	Propionibacterium acnes	MIC	=	400.0	ug.mL-1	PMID[502524]
NPT2	Others	Unspecified		EC50	=	477000.0	nM	PMID[502527]
NPT2	Others	Unspecified		Kd	=	220000.0	nM	PMID[502527]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	32.2	%	PMID[502529]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	119.5	%	PMID[502529]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	1.8	%	PMID[502529]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	24.4	%	PMID[502529]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[502531]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1901.2	nM	PMID[502531]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502533]
NPT694	Individual Protein	UDP-glucuronosyltransferase 1-3	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502533]
NPT702	Individual Protein	UDP-glucuronosyltransferase 1-6	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502533]
NPT697	Individual Protein	UDP-glucuronosyltransferase 2B7	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502533]
NPT697	Individual Protein	UDP-glucuronosyltransferase 2B7	Homo sapiens	Activity	=	4.0	pm/min/mg	PMID[502533]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502534]
NPT702	Individual Protein	UDP-glucuronosyltransferase 1-6	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502534]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502534]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502534]
NPT704	Individual Protein	UDP-glucuronosyltransferase 2B15	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[502534]
NPT1327	Organism	Lipaphis erysimi	Lipaphis erysimi	Ratio	=	0.584	n.a.	PMID[502535]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	3.3	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	0.0	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	30.0	%	PMID[502537]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	EC50	=	452.0	ug.mL-1	PMID[502538]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	EC50	=	2884031.5	nM	PMID[502538]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	26.7	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	40.0	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	23.3	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	20.0	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	36.7	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	33.0	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	16.7	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	46.7	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	33.3	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	13.3	%	PMID[502537]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	6.7	%	PMID[502537]
NPT734	Organism	Musca domestica	Musca domestica	LD50	=	128.9	ug	PMID[502539]
NPT735	Individual Protein	GABA receptor subunit	Musca domestica	Activity	=	80.0	%	PMID[502539]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	LC50	=	13.7	microg/cm3	PMID[502540]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	LC50	=	12.9	microg/cm3	PMID[502540]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	LC50	=	12.8	microg/cm3	PMID[502540]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	LC50	=	13.0	microg/cm3	PMID[502540]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LC50	=	9.36	ug.mL-1	PMID[502541]
NPT3472	Organism	Theba pisana	Theba pisana	LD50	=	99.44	ug	PMID[502541]
NPT3472	Organism	Theba pisana	Theba pisana	LC50	>	100.0	ug.mL-1	PMID[502541]
NPT35	Others	n.a.		Activity	=	0.31	equiv	PMID[502544]
NPT35	Others	n.a.		Activity	=	0.0	equiv	PMID[502544]
NPT35	Others	n.a.		Activity	=	0.49	equiv	PMID[502544]
NPT35	Others	n.a.		Activity	=	0.39	equiv	PMID[502544]
NPT35	Others	n.a.		Activity	=	0.22	equiv	PMID[502544]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[502547]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[502547]
NPT2	Others	Unspecified		Potency	n.a.	27056.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13685.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61094.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54947.7	nM	PubChem BioAssay data set

☑ 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 NPC223468 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	375
0.1-0.2	5826
0.2-0.3	19094
0.3-0.4	9758
0.4-0.5	5870
0.5-0.6	1503
0.6-0.7	226
0.7-0.8	31
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC84030
1.0	High Similarity	NPC198540
1.0	High Similarity	NPC287550
1.0	High Similarity	NPC147343
1.0	High Similarity	NPC176309
0.8864	High Similarity	NPC144891
0.86	High Similarity	NPC53209
0.8367	Intermediate Similarity	NPC307022
0.8077	Intermediate Similarity	NPC471269
0.8077	Intermediate Similarity	NPC67508
0.8077	Intermediate Similarity	NPC84824
0.7963	Intermediate Similarity	NPC47663
0.7907	Intermediate Similarity	NPC177022
0.7818	Intermediate Similarity	NPC185116
0.7778	Intermediate Similarity	NPC236588
0.7778	Intermediate Similarity	NPC135438
0.7778	Intermediate Similarity	NPC160261
0.7778	Intermediate Similarity	NPC469759
0.7755	Intermediate Similarity	NPC314087
0.7736	Intermediate Similarity	NPC89069
0.7736	Intermediate Similarity	NPC277917
0.7736	Intermediate Similarity	NPC166894
0.7736	Intermediate Similarity	NPC283655
0.7736	Intermediate Similarity	NPC178223
0.7708	Intermediate Similarity	NPC77550
0.7708	Intermediate Similarity	NPC108441
0.7647	Intermediate Similarity	NPC274261
0.7647	Intermediate Similarity	NPC291724
0.7636	Intermediate Similarity	NPC475515
0.7636	Intermediate Similarity	NPC215671
0.7636	Intermediate Similarity	NPC87296
0.7556	Intermediate Similarity	NPC221022
0.7544	Intermediate Similarity	NPC95804
0.7544	Intermediate Similarity	NPC185547
0.7455	Intermediate Similarity	NPC29976
0.7455	Intermediate Similarity	NPC150713
0.7414	Intermediate Similarity	NPC292419
0.7414	Intermediate Similarity	NPC290791
0.7358	Intermediate Similarity	NPC102336
0.7358	Intermediate Similarity	NPC36002
0.7347	Intermediate Similarity	NPC473914
0.7288	Intermediate Similarity	NPC101128
0.7288	Intermediate Similarity	NPC94897
0.7273	Intermediate Similarity	NPC328441
0.7255	Intermediate Similarity	NPC316035
0.7255	Intermediate Similarity	NPC294858
0.7241	Intermediate Similarity	NPC148174
0.7241	Intermediate Similarity	NPC218585
0.7241	Intermediate Similarity	NPC71460
0.7209	Intermediate Similarity	NPC283682
0.72	Intermediate Similarity	NPC14552
0.7167	Intermediate Similarity	NPC41577
0.7167	Intermediate Similarity	NPC2728
0.7167	Intermediate Similarity	NPC282619
0.7167	Intermediate Similarity	NPC473276
0.7167	Intermediate Similarity	NPC80463
0.7167	Intermediate Similarity	NPC11555
0.7167	Intermediate Similarity	NPC260116
0.7167	Intermediate Similarity	NPC172613
0.7167	Intermediate Similarity	NPC60837
0.7167	Intermediate Similarity	NPC474380
0.7167	Intermediate Similarity	NPC208198
0.7143	Intermediate Similarity	NPC240994
0.7143	Intermediate Similarity	NPC313795
0.7143	Intermediate Similarity	NPC215358
0.7119	Intermediate Similarity	NPC209686
0.7119	Intermediate Similarity	NPC236099
0.7119	Intermediate Similarity	NPC249078
0.7119	Intermediate Similarity	NPC114891
0.7091	Intermediate Similarity	NPC300189
0.7049	Intermediate Similarity	NPC142712
0.7049	Intermediate Similarity	NPC44122
0.7049	Intermediate Similarity	NPC473929
0.7037	Intermediate Similarity	NPC161473
0.7	Intermediate Similarity	NPC159654
0.7	Intermediate Similarity	NPC281540
0.7	Intermediate Similarity	NPC69149
0.7	Intermediate Similarity	NPC68656
0.7	Intermediate Similarity	NPC225415
0.7	Intermediate Similarity	NPC118937
0.7	Intermediate Similarity	NPC219940
0.7	Intermediate Similarity	NPC167995
0.7	Intermediate Similarity	NPC144650
0.6977	Remote Similarity	NPC1748
0.6977	Remote Similarity	NPC66124
0.6977	Remote Similarity	NPC193062
0.6977	Remote Similarity	NPC319034
0.6977	Remote Similarity	NPC72324
0.6964	Remote Similarity	NPC170780
0.6964	Remote Similarity	NPC3025
0.6935	Remote Similarity	NPC185874
0.6935	Remote Similarity	NPC48079
0.6935	Remote Similarity	NPC473230
0.6935	Remote Similarity	NPC475884
0.6935	Remote Similarity	NPC269077
0.6935	Remote Similarity	NPC139207
0.6935	Remote Similarity	NPC204233
0.6935	Remote Similarity	NPC253303
0.6909	Remote Similarity	NPC32222
0.6909	Remote Similarity	NPC202146
0.6889	Remote Similarity	NPC61665
0.6885	Remote Similarity	NPC300442
0.6885	Remote Similarity	NPC258595
0.6852	Remote Similarity	NPC476149
0.6852	Remote Similarity	NPC300235
0.6852	Remote Similarity	NPC244869
0.6852	Remote Similarity	NPC476136
0.6825	Remote Similarity	NPC474756
0.6825	Remote Similarity	NPC244790
0.6825	Remote Similarity	NPC469987
0.6825	Remote Similarity	NPC475893
0.6825	Remote Similarity	NPC472741
0.6825	Remote Similarity	NPC266578
0.6774	Remote Similarity	NPC475897
0.6744	Remote Similarity	NPC267243
0.6744	Remote Similarity	NPC122962
0.6724	Remote Similarity	NPC476735
0.6724	Remote Similarity	NPC474769
0.6724	Remote Similarity	NPC189290
0.6719	Remote Similarity	NPC210323
0.6719	Remote Similarity	NPC470833
0.6719	Remote Similarity	NPC299948
0.6719	Remote Similarity	NPC66407
0.6719	Remote Similarity	NPC107919
0.6719	Remote Similarity	NPC254037
0.6719	Remote Similarity	NPC470830
0.6719	Remote Similarity	NPC129829
0.6719	Remote Similarity	NPC241085
0.6719	Remote Similarity	NPC234511
0.6719	Remote Similarity	NPC477820
0.6667	Remote Similarity	NPC472984
0.6667	Remote Similarity	NPC476928
0.6667	Remote Similarity	NPC210316
0.6667	Remote Similarity	NPC251335
0.6667	Remote Similarity	NPC87439
0.6667	Remote Similarity	NPC97967
0.6667	Remote Similarity	NPC63190
0.6615	Remote Similarity	NPC63588
0.6615	Remote Similarity	NPC232925
0.6615	Remote Similarity	NPC283316
0.6615	Remote Similarity	NPC45296
0.6615	Remote Similarity	NPC231945
0.6615	Remote Similarity	NPC251201
0.6615	Remote Similarity	NPC92801
0.6615	Remote Similarity	NPC192192
0.6615	Remote Similarity	NPC282454
0.6613	Remote Similarity	NPC472946
0.661	Remote Similarity	NPC95958
0.66	Remote Similarity	NPC302939
0.66	Remote Similarity	NPC287331
0.6562	Remote Similarity	NPC276616
0.6562	Remote Similarity	NPC2648
0.6562	Remote Similarity	NPC96484
0.6562	Remote Similarity	NPC245795
0.6552	Remote Similarity	NPC291147
0.6552	Remote Similarity	NPC119425
0.6522	Remote Similarity	NPC474392
0.6522	Remote Similarity	NPC474914
0.6515	Remote Similarity	NPC110799
0.6515	Remote Similarity	NPC131506
0.6515	Remote Similarity	NPC89310
0.6515	Remote Similarity	NPC478103
0.6515	Remote Similarity	NPC242992
0.6515	Remote Similarity	NPC127094
0.6515	Remote Similarity	NPC100586
0.6515	Remote Similarity	NPC470071
0.6515	Remote Similarity	NPC301226
0.6515	Remote Similarity	NPC252182
0.6515	Remote Similarity	NPC167706
0.6515	Remote Similarity	NPC195530
0.6515	Remote Similarity	NPC1340
0.6515	Remote Similarity	NPC157422
0.6515	Remote Similarity	NPC473279
0.6515	Remote Similarity	NPC23954
0.6515	Remote Similarity	NPC111234
0.6515	Remote Similarity	NPC157777
0.6515	Remote Similarity	NPC187471
0.6515	Remote Similarity	NPC164022
0.6515	Remote Similarity	NPC109457
0.6512	Remote Similarity	NPC112242
0.6512	Remote Similarity	NPC24506
0.6512	Remote Similarity	NPC225783
0.6512	Remote Similarity	NPC147096
0.6512	Remote Similarity	NPC236797
0.6512	Remote Similarity	NPC163556
0.6512	Remote Similarity	NPC185041
0.6508	Remote Similarity	NPC202017
0.6508	Remote Similarity	NPC326310
0.65	Remote Similarity	NPC475412
0.6462	Remote Similarity	NPC213178
0.6462	Remote Similarity	NPC6120
0.6462	Remote Similarity	NPC327728
0.6462	Remote Similarity	NPC131892
0.6452	Remote Similarity	NPC96793
0.6452	Remote Similarity	NPC323424
0.6441	Remote Similarity	NPC240206
0.6418	Remote Similarity	NPC470610
0.6418	Remote Similarity	NPC68426
0.6418	Remote Similarity	NPC211009
0.6418	Remote Similarity	NPC201373

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 NPC223468 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	517
0.1-0.2	4800
0.2-0.3	2724
0.3-0.4	725
0.4-0.5	312
0.5-0.6	60
0.6-0.7	8
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD385	Approved
1.0	High Similarity	NPD384	Approved
0.7708	Intermediate Similarity	NPD388	Approved
0.7708	Intermediate Similarity	NPD386	Approved
0.7288	Intermediate Similarity	NPD371	Approved
0.6735	Remote Similarity	NPD1462	Approved
0.6719	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1460	Approved
0.66	Remote Similarity	NPD367	Approved
0.6462	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4787	Phase 1
0.6349	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD3703	Phase 2
0.6222	Remote Similarity	NPD5383	Approved
0.6222	Remote Similarity	NPD2272	Approved
0.6212	Remote Similarity	NPD3698	Phase 2
0.6143	Remote Similarity	NPD6117	Approved
0.6129	Remote Similarity	NPD368	Approved
0.6119	Remote Similarity	NPD4244	Approved
0.6119	Remote Similarity	NPD4245	Approved
0.6087	Remote Similarity	NPD1811	Approved
0.6087	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1810	Approved
0.6066	Remote Similarity	NPD3198	Approved
0.6056	Remote Similarity	NPD6116	Phase 1
0.6047	Remote Similarity	NPD8988	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6697	Approved
0.5972	Remote Similarity	NPD6115	Approved
0.5972	Remote Similarity	NPD6118	Approved
0.5972	Remote Similarity	NPD6114	Approved
0.5932	Remote Similarity	NPD342	Phase 1
0.589	Remote Similarity	NPD7645	Phase 2
0.5882	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD9426	Discontinued
0.5882	Remote Similarity	NPD4789	Approved
0.5821	Remote Similarity	NPD6705	Phase 1
0.5811	Remote Similarity	NPD7525	Registered
0.5775	Remote Similarity	NPD7339	Approved
0.5775	Remote Similarity	NPD6942	Approved
0.5763	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD3671	Phase 1
0.5741	Remote Similarity	NPD634	Phase 3
0.5694	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD7909	Approved
0.5634	Remote Similarity	NPD6926	Approved
0.5634	Remote Similarity	NPD6924	Approved
0.56	Remote Similarity	NPD6928	Phase 2
0.56	Remote Similarity	NPD4748	Discontinued

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