NPASS Compound

Structure

CID171460 OpenBabel06191715542D 23 25 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	4.693
LogD:	4.05
LogS:	-5.767
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	3.737
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.945
MDCK Permeability:	1.781398350431118e-05
Pgp-inhibitor:	0.913
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.897
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	98.63964080810547%
Volume Distribution (VD):	0.316
Pgp-substrate:	1.855483889579773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.523
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.826
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.703
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.656
CYP2D6-substrate:	0.364
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	3.45
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.268
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.276
Carcinogencity:	0.071
Eye Corrosion:	0.006
Eye Irritation:	0.895
Respiratory Toxicity:	0.808

Download Data

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

Natural Product: NPC171460

Natural Product ID:	NPC171460
*Common Name:**	Montbretol
IUPAC Name:	(4aR)-6,10-dihydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4-dihydro-2H-phenanthren-9-one
Synonyms:
Standard InCHIKey:	XLUHSPYVUOVWRM-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-11(2)12-9-13-14(10-15(12)21)20(5)8-6-7-19(3,4)18(20)17(23)16(13)22/h9-11,21,23H,6-8H2,1-5H3/t20-/m1/s1
SMILES:	OC1=C2C(C)(C)CCC[C@@]2(c2c(C1=O)cc(C(C)C)c(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469670
PubChem CID:	3009284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17869103]
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	bark	n.a.	n.a.	PMID[18549276]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	whole plants	east Texas, USA	2009-2011	PMID[24210499]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24210499]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26905523]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	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
GI50	6
IC50	2
Others	5

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	8.3	%	PMID[522921]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	11.9	%	PMID[522921]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	54.4	%	PMID[522921]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	55.4	%	PMID[522921]
NPT171	Cell Line	MRC5	Homo sapiens	GI50	=	20010.0	nM	PMID[522922]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	11450.0	nM	PMID[522922]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	13170.0	nM	PMID[522922]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	11070.0	nM	PMID[522922]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	25000.0	nM	PMID[522922]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	23080.0	nM	PMID[522922]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	10.0	ug.mL-1	PMID[522923]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	>	10.0	ug.mL-1	PMID[522923]

☑ 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 NPC171460 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	336
0.1-0.2	1574
0.2-0.3	3186
0.3-0.4	8227
0.4-0.5	10629
0.5-0.6	6845
0.6-0.7	9011
0.7-0.8	2494
0.8-0.85	309
0.85-0.9	52
0.9-0.95	22
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC72667
0.9754	High Similarity	NPC254492
0.9675	High Similarity	NPC84672
0.9675	High Similarity	NPC78364
0.9675	High Similarity	NPC176130
0.9675	High Similarity	NPC69424
0.959	High Similarity	NPC199273
0.9528	High Similarity	NPC78307
0.9512	High Similarity	NPC123506
0.9444	High Similarity	NPC108129
0.944	High Similarity	NPC96024
0.9426	High Similarity	NPC282577
0.937	High Similarity	NPC471851
0.9365	High Similarity	NPC276238
0.9365	High Similarity	NPC303910
0.9344	High Similarity	NPC154696
0.9286	High Similarity	NPC3009
0.9237	High Similarity	NPC475957
0.9225	High Similarity	NPC477139
0.9225	High Similarity	NPC138472
0.9194	High Similarity	NPC273683
0.9167	High Similarity	NPC230811
0.916	High Similarity	NPC471670
0.9154	High Similarity	NPC202225
0.9106	High Similarity	NPC259703
0.9106	High Similarity	NPC32322
0.9077	High Similarity	NPC111845
0.8976	High Similarity	NPC15837
0.8947	High Similarity	NPC36868
0.8915	High Similarity	NPC117899
0.8898	High Similarity	NPC137750
0.8872	High Similarity	NPC474311
0.8846	High Similarity	NPC253488
0.8837	High Similarity	NPC193203
0.8828	High Similarity	NPC71610
0.881	High Similarity	NPC176208
0.8806	High Similarity	NPC53001
0.8797	High Similarity	NPC153088
0.8788	High Similarity	NPC4170
0.8779	High Similarity	NPC239134
0.8779	High Similarity	NPC18798
0.8759	High Similarity	NPC308572
0.8759	High Similarity	NPC248068
0.8741	High Similarity	NPC87723
0.874	High Similarity	NPC471187
0.874	High Similarity	NPC275145
0.873	High Similarity	NPC162935
0.873	High Similarity	NPC249340
0.8722	High Similarity	NPC12070
0.8722	High Similarity	NPC50924
0.8705	High Similarity	NPC478160
0.8702	High Similarity	NPC27659
0.8692	High Similarity	NPC229894
0.8672	High Similarity	NPC164014
0.8672	High Similarity	NPC181334
0.8667	High Similarity	NPC277559
0.8661	High Similarity	NPC11250
0.8657	High Similarity	NPC249272
0.8657	High Similarity	NPC22644
0.8651	High Similarity	NPC241001
0.8647	High Similarity	NPC114183
0.8636	High Similarity	NPC164295
0.8623	High Similarity	NPC201297
0.8613	High Similarity	NPC471853
0.8583	High Similarity	NPC120545
0.8582	High Similarity	NPC5568
0.8582	High Similarity	NPC270899
0.8571	High Similarity	NPC165612
0.8571	High Similarity	NPC312560
0.8561	High Similarity	NPC478164
0.8561	High Similarity	NPC100242
0.855	High Similarity	NPC48248
0.8529	High Similarity	NPC49911
0.8519	High Similarity	NPC477596
0.8519	High Similarity	NPC283088
0.8516	High Similarity	NPC307174
0.8516	High Similarity	NPC91478
0.8516	High Similarity	NPC121168
0.8507	High Similarity	NPC59459
0.8507	High Similarity	NPC53896
0.8504	High Similarity	NPC190971
0.8496	Intermediate Similarity	NPC17083
0.8496	Intermediate Similarity	NPC41847
0.8496	Intermediate Similarity	NPC93015
0.8496	Intermediate Similarity	NPC476847
0.8496	Intermediate Similarity	NPC244699
0.8489	Intermediate Similarity	NPC477209
0.8485	Intermediate Similarity	NPC146647
0.8485	Intermediate Similarity	NPC25736
0.8485	Intermediate Similarity	NPC34414
0.8478	Intermediate Similarity	NPC181560
0.8478	Intermediate Similarity	NPC169452
0.8473	Intermediate Similarity	NPC19432
0.8473	Intermediate Similarity	NPC471530
0.8468	Intermediate Similarity	NPC322197
0.8456	Intermediate Similarity	NPC191976
0.8456	Intermediate Similarity	NPC86524
0.8456	Intermediate Similarity	NPC7464
0.8456	Intermediate Similarity	NPC472308
0.8455	Intermediate Similarity	NPC242136
0.845	Intermediate Similarity	NPC198014
0.845	Intermediate Similarity	NPC174991
0.8444	Intermediate Similarity	NPC477594
0.8438	Intermediate Similarity	NPC253627
0.8433	Intermediate Similarity	NPC183103
0.8433	Intermediate Similarity	NPC58685
0.8425	Intermediate Similarity	NPC190501
0.8425	Intermediate Similarity	NPC478121
0.8425	Intermediate Similarity	NPC318552
0.8421	Intermediate Similarity	NPC198305
0.8421	Intermediate Similarity	NPC470725
0.8406	Intermediate Similarity	NPC242994
0.8406	Intermediate Similarity	NPC138099
0.8397	Intermediate Similarity	NPC474737
0.8397	Intermediate Similarity	NPC231774
0.8397	Intermediate Similarity	NPC160499
0.8397	Intermediate Similarity	NPC3224
0.8394	Intermediate Similarity	NPC471905
0.8394	Intermediate Similarity	NPC471452
0.8394	Intermediate Similarity	NPC264022
0.8385	Intermediate Similarity	NPC173978
0.8385	Intermediate Similarity	NPC310540
0.8385	Intermediate Similarity	NPC474766
0.8385	Intermediate Similarity	NPC142956
0.8382	Intermediate Similarity	NPC80035
0.8382	Intermediate Similarity	NPC290803
0.8374	Intermediate Similarity	NPC231717
0.8374	Intermediate Similarity	NPC250323
0.8372	Intermediate Similarity	NPC164947
0.837	Intermediate Similarity	NPC52407
0.837	Intermediate Similarity	NPC225051
0.837	Intermediate Similarity	NPC115458
0.837	Intermediate Similarity	NPC49742
0.837	Intermediate Similarity	NPC267205
0.8369	Intermediate Similarity	NPC196941
0.8369	Intermediate Similarity	NPC309169
0.8359	Intermediate Similarity	NPC472981
0.8358	Intermediate Similarity	NPC474517
0.8358	Intermediate Similarity	NPC72669
0.8358	Intermediate Similarity	NPC291001
0.8357	Intermediate Similarity	NPC184935
0.8357	Intermediate Similarity	NPC193555
0.8346	Intermediate Similarity	NPC42657
0.8346	Intermediate Similarity	NPC278928
0.8346	Intermediate Similarity	NPC99731
0.8345	Intermediate Similarity	NPC476534
0.8333	Intermediate Similarity	NPC149773
0.8333	Intermediate Similarity	NPC262936
0.8333	Intermediate Similarity	NPC23667
0.8333	Intermediate Similarity	NPC473779
0.8333	Intermediate Similarity	NPC91887
0.8333	Intermediate Similarity	NPC46242
0.8333	Intermediate Similarity	NPC50615
0.8333	Intermediate Similarity	NPC469857
0.8333	Intermediate Similarity	NPC30491
0.8333	Intermediate Similarity	NPC114333
0.8333	Intermediate Similarity	NPC13715
0.8333	Intermediate Similarity	NPC157284
0.8333	Intermediate Similarity	NPC28592
0.8333	Intermediate Similarity	NPC245760
0.8333	Intermediate Similarity	NPC473479
0.8333	Intermediate Similarity	NPC5014
0.8333	Intermediate Similarity	NPC165191
0.8333	Intermediate Similarity	NPC289358
0.8333	Intermediate Similarity	NPC297797
0.8333	Intermediate Similarity	NPC174087
0.8333	Intermediate Similarity	NPC477849
0.8333	Intermediate Similarity	NPC51531
0.8333	Intermediate Similarity	NPC42384
0.8333	Intermediate Similarity	NPC4214
0.8321	Intermediate Similarity	NPC87985
0.8321	Intermediate Similarity	NPC254847
0.8309	Intermediate Similarity	NPC282780
0.8309	Intermediate Similarity	NPC218854
0.8309	Intermediate Similarity	NPC52368
0.8309	Intermediate Similarity	NPC166480
0.8308	Intermediate Similarity	NPC135062
0.8296	Intermediate Similarity	NPC309430
0.8296	Intermediate Similarity	NPC175738
0.8293	Intermediate Similarity	NPC260323
0.8293	Intermediate Similarity	NPC176279
0.8286	Intermediate Similarity	NPC110810
0.8284	Intermediate Similarity	NPC55949
0.8281	Intermediate Similarity	NPC285829
0.8281	Intermediate Similarity	NPC206778
0.8273	Intermediate Similarity	NPC294330
0.8271	Intermediate Similarity	NPC282923
0.8271	Intermediate Similarity	NPC24869
0.8261	Intermediate Similarity	NPC119542
0.8261	Intermediate Similarity	NPC477592
0.8261	Intermediate Similarity	NPC53206
0.8261	Intermediate Similarity	NPC53414
0.8261	Intermediate Similarity	NPC186647
0.8261	Intermediate Similarity	NPC290601
0.8258	Intermediate Similarity	NPC306765
0.8254	Intermediate Similarity	NPC477453
0.8254	Intermediate Similarity	NPC471668
0.8252	Intermediate Similarity	NPC143685
0.8248	Intermediate Similarity	NPC258502
0.8244	Intermediate Similarity	NPC152525

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 NPC171460 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	947
0.2-0.3	1325
0.3-0.4	2609
0.4-0.5	2236
0.5-0.6	1175
0.6-0.7	454
0.7-0.8	64
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD2932	Approved
0.8492	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3019	Approved
0.8321	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1201	Approved
0.8045	Intermediate Similarity	NPD1470	Approved
0.7986	Intermediate Similarity	NPD7390	Discontinued
0.7969	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD7003	Approved
0.7872	Intermediate Similarity	NPD5404	Approved
0.7872	Intermediate Similarity	NPD5406	Approved
0.7872	Intermediate Similarity	NPD5408	Approved
0.7872	Intermediate Similarity	NPD5405	Approved
0.7812	Intermediate Similarity	NPD5951	Approved
0.7803	Intermediate Similarity	NPD3023	Approved
0.7803	Intermediate Similarity	NPD3026	Approved
0.7801	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD3300	Phase 2
0.7786	Intermediate Similarity	NPD3025	Approved
0.7786	Intermediate Similarity	NPD3024	Approved
0.7687	Intermediate Similarity	NPD3972	Approved
0.76	Intermediate Similarity	NPD7458	Discontinued
0.7594	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6663	Approved
0.7568	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5736	Approved
0.7534	Intermediate Similarity	NPD8166	Discontinued
0.7519	Intermediate Similarity	NPD7635	Approved
0.7518	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7463	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2346	Discontinued
0.7445	Intermediate Similarity	NPD1283	Approved
0.7444	Intermediate Similarity	NPD3091	Approved
0.7431	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD2342	Discontinued
0.7394	Intermediate Similarity	NPD943	Approved
0.7388	Intermediate Similarity	NPD1651	Approved
0.7379	Intermediate Similarity	NPD2935	Discontinued
0.7344	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD4059	Approved
0.7333	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2799	Discontinued
0.7297	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1809	Phase 2
0.7292	Intermediate Similarity	NPD1607	Approved
0.7287	Intermediate Similarity	NPD4750	Phase 3
0.7285	Intermediate Similarity	NPD6273	Approved
0.7266	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3020	Approved
0.7255	Intermediate Similarity	NPD3226	Approved
0.7254	Intermediate Similarity	NPD3764	Approved
0.7246	Intermediate Similarity	NPD1755	Approved
0.7236	Intermediate Similarity	NPD288	Approved
0.7236	Intermediate Similarity	NPD3495	Discontinued
0.723	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3092	Approved
0.7226	Intermediate Similarity	NPD1281	Approved
0.7211	Intermediate Similarity	NPD2344	Approved
0.7194	Intermediate Similarity	NPD1876	Approved
0.7181	Intermediate Similarity	NPD4628	Phase 3
0.7181	Intermediate Similarity	NPD3750	Approved
0.7179	Intermediate Similarity	NPD7819	Suspended
0.7174	Intermediate Similarity	NPD4878	Approved
0.7162	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7473	Discontinued
0.7154	Intermediate Similarity	NPD844	Approved
0.7153	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6959	Discontinued
0.7111	Intermediate Similarity	NPD7610	Discontinued
0.7105	Intermediate Similarity	NPD2533	Approved
0.7105	Intermediate Similarity	NPD2532	Approved
0.7105	Intermediate Similarity	NPD2534	Approved
0.7099	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1930	Approved
0.7087	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1929	Approved
0.7086	Intermediate Similarity	NPD7236	Approved
0.7083	Intermediate Similarity	NPD8032	Phase 2
0.7081	Intermediate Similarity	NPD6232	Discontinued
0.708	Intermediate Similarity	NPD3095	Discontinued
0.7075	Intermediate Similarity	NPD1510	Phase 2
0.7073	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7008	Discontinued
0.7059	Intermediate Similarity	NPD9545	Approved
0.7055	Intermediate Similarity	NPD6651	Approved
0.7045	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4060	Phase 1
0.7031	Intermediate Similarity	NPD1237	Approved
0.7029	Intermediate Similarity	NPD4879	Approved
0.7023	Intermediate Similarity	NPD3022	Approved
0.7023	Intermediate Similarity	NPD3021	Approved
0.7021	Intermediate Similarity	NPD3094	Phase 2
0.702	Intermediate Similarity	NPD2309	Approved
0.702	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2859	Approved
0.7016	Intermediate Similarity	NPD2860	Approved
0.7007	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD2800	Approved
0.7	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD845	Approved
0.6987	Remote Similarity	NPD6599	Discontinued
0.6984	Remote Similarity	NPD2066	Phase 3
0.698	Remote Similarity	NPD1471	Phase 3
0.6968	Remote Similarity	NPD7239	Suspended
0.6964	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1751	Approved
0.6957	Remote Similarity	NPD2286	Discontinued
0.6947	Remote Similarity	NPD74	Approved
0.6947	Remote Similarity	NPD9266	Approved
0.6941	Remote Similarity	NPD8150	Discontinued
0.6939	Remote Similarity	NPD4097	Suspended
0.6937	Remote Similarity	NPD7075	Discontinued
0.6935	Remote Similarity	NPD2933	Approved
0.6935	Remote Similarity	NPD2934	Approved
0.6934	Remote Similarity	NPD7009	Phase 2
0.6923	Remote Similarity	NPD4208	Discontinued
0.6918	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2979	Phase 3
0.6918	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9493	Approved
0.6901	Remote Similarity	NPD2797	Approved
0.6897	Remote Similarity	NPD3268	Approved
0.6897	Remote Similarity	NPD2313	Discontinued
0.6889	Remote Similarity	NPD2629	Approved
0.6884	Remote Similarity	NPD4093	Discontinued
0.6879	Remote Similarity	NPD4380	Phase 2
0.687	Remote Similarity	NPD9264	Approved
0.687	Remote Similarity	NPD9263	Approved
0.687	Remote Similarity	NPD9267	Approved
0.6867	Remote Similarity	NPD6020	Phase 2
0.6867	Remote Similarity	NPD5844	Phase 1
0.6855	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3748	Approved
0.6846	Remote Similarity	NPD4308	Phase 3
0.6839	Remote Similarity	NPD1512	Approved
0.6821	Remote Similarity	NPD1549	Phase 2
0.6809	Remote Similarity	NPD1608	Approved
0.6809	Remote Similarity	NPD9269	Phase 2
0.6806	Remote Similarity	NPD3635	Approved
0.6806	Remote Similarity	NPD3637	Approved
0.6806	Remote Similarity	NPD3636	Approved
0.6806	Remote Similarity	NPD9494	Approved
0.68	Remote Similarity	NPD2796	Approved
0.6791	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7028	Phase 2
0.677	Remote Similarity	NPD3882	Suspended
0.6763	Remote Similarity	NPD9268	Approved
0.6759	Remote Similarity	NPD2606	Approved
0.6759	Remote Similarity	NPD4207	Discontinued
0.6759	Remote Similarity	NPD2605	Approved
0.6755	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5029	Approved
0.6746	Remote Similarity	NPD5031	Approved
0.6746	Remote Similarity	NPD5027	Approved
0.6736	Remote Similarity	NPD2195	Approved
0.6736	Remote Similarity	NPD2194	Approved
0.6736	Remote Similarity	NPD4624	Approved
0.6736	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7411	Suspended
0.6714	Remote Similarity	NPD4589	Approved
0.6713	Remote Similarity	NPD6696	Suspended
0.6712	Remote Similarity	NPD5156	Approved
0.6712	Remote Similarity	NPD5155	Approved
0.6712	Remote Similarity	NPD7095	Approved
0.6712	Remote Similarity	NPD4625	Phase 3
0.671	Remote Similarity	NPD1511	Approved
0.6707	Remote Similarity	NPD7177	Discontinued
0.6706	Remote Similarity	NPD5026	Approved
0.6706	Remote Similarity	NPD5034	Approved
0.6706	Remote Similarity	NPD36	Approved
0.6706	Remote Similarity	NPD5028	Approved
0.6706	Remote Similarity	NPD4955	Approved
0.6706	Remote Similarity	NPD4954	Approved
0.6691	Remote Similarity	NPD1241	Discontinued
0.6691	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2438	Suspended
0.6689	Remote Similarity	NPD4140	Approved
0.6689	Remote Similarity	NPD2531	Phase 2
0.6689	Remote Similarity	NPD3620	Phase 2
0.6689	Remote Similarity	NPD4476	Approved
0.6689	Remote Similarity	NPD4477	Approved
0.6687	Remote Similarity	NPD1934	Approved
0.6687	Remote Similarity	NPD6801	Discontinued
0.6686	Remote Similarity	NPD5968	Phase 3
0.6686	Remote Similarity	NPD7879	Clinical (unspecified phase)

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