NPASS Compound

Structure

CID63020 OpenBabel06191715402D 34 38 0 0 1 0 0 0 0 0999 V2000 -5.7291 -0.3470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1917 -0.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4563 -1.4251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9629 -0.5717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0244 -1.9169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8724 1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9815 3.9421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6474 -0.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 -1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1184 1.4251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6465 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -2.8523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8242 -2.3774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8231 0.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2959 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8242 1.4261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6482 1.9014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7902 -0.1980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1182 0.4744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6477 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6468 -0.9508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4710 -2.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4716 0.4749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4722 2.3763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4705 -1.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8237 -1.4266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8240 0.4754 0.0000 C 0 0 1 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 -2.4719 1.4256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3250 -2.8689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5681 2.6703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1789 3.0122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 34 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 31 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 27 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 31 1 1 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 31 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.36
Volume:	520.411
LogP:	5.775
LogD:	5.475
LogS:	-6.023
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	4.691
Fsp3:	0.871
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.205
MDCK Permeability:	3.306446524220519e-05
Pgp-inhibitor:	0.564
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.646
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	87.83771514892578%
Volume Distribution (VD):	1.051
Pgp-substrate:	2.76825213432312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.773
CYP2C19-inhibitor:	0.17
CYP2C19-substrate:	0.968
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	4.978
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.407
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.108
Carcinogencity:	0.014
Eye Corrosion:	0.025
Eye Irritation:	0.134
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC63020

Natural Product ID:	NPC63020
*Common Name:**	Methyl Betulonate
IUPAC Name:	methyl (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
Synonyms:	Methyl Betulonate
Standard InCHIKey:	XXCPTCZYFSRIGU-DSBZJMBESA-N
Standard InCHI:	InChI=1S/C31H48O3/c1-19(2)20-11-16-31(26(33)34-8)18-17-29(6)21(25(20)31)9-10-23-28(5)14-13-24(32)27(3,4)22(28)12-15-30(23,29)7/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,28-,29+,30+,31-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376266
PubChem CID:	10766700
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[10661881]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387673]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[28294414]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	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
ED50	1
GI50	6
IC50	12
Others	4

Activity Type	# Activity
Cell Line	17
NON-MOLECULAR	3
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	250000.0	nM	PMID[525572]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	250000.0	nM	PMID[525573]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	250000.0	nM	PMID[525573]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	239000.0	nM	PMID[525573]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	250000.0	nM	PMID[525573]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	250000.0	nM	PMID[525573]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	36250.0	nM	PMID[525576]
NPT1215	Cell Line	8505C	Homo sapiens	IC50	>	100000.0	nM	PMID[525576]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	98100.0	nM	PMID[525576]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[525576]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	2.3	ug.mL-1	PMID[525577]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	2.3	ug.mL-1	PMID[525577]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	2.7	ug.mL-1	PMID[525577]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	2.7	ug.mL-1	PMID[525577]
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[525577]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	400000.0	nM	PMID[525578]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	400000.0	nM	PMID[525578]
NPT856	Organism	Semliki forest virus	Semliki forest virus	Activity	=	71.0	%	PMID[525574]
NPT27	Others	Unspecified		Activity	=	83.0	%	PMID[525574]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	68050.0	nM	PMID[525576]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2.2	ug.mL-1	PMID[525577]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2.4	ug.mL-1	PMID[525577]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	100000.0	nM	PMID[525578]

☑ 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 NPC63020 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	192
0.1-0.2	1897
0.2-0.3	10455
0.3-0.4	13573
0.4-0.5	6187
0.5-0.6	5607
0.6-0.7	3653
0.7-0.8	1015
0.8-0.85	78
0.85-0.9	35
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC192744
0.9306	High Similarity	NPC279241
0.9079	High Similarity	NPC471475
0.9067	High Similarity	NPC68828
0.8987	High Similarity	NPC475509
0.8875	High Similarity	NPC98270
0.8875	High Similarity	NPC201655
0.8861	High Similarity	NPC472740
0.8831	High Similarity	NPC201459
0.8816	High Similarity	NPC66105
0.8765	High Similarity	NPC12774
0.8718	High Similarity	NPC267517
0.8684	High Similarity	NPC246445
0.8659	High Similarity	NPC33768
0.8642	High Similarity	NPC294438
0.8642	High Similarity	NPC264317
0.8608	High Similarity	NPC103754
0.8608	High Similarity	NPC474484
0.859	High Similarity	NPC118987
0.8571	High Similarity	NPC212661
0.8571	High Similarity	NPC471035
0.8554	High Similarity	NPC4309
0.8554	High Similarity	NPC474719
0.8537	High Similarity	NPC2783
0.8533	High Similarity	NPC330659
0.8533	High Similarity	NPC244708
0.8533	High Similarity	NPC161187
0.8533	High Similarity	NPC36310
0.8481	Intermediate Similarity	NPC170038
0.8472	Intermediate Similarity	NPC43300
0.8442	Intermediate Similarity	NPC20466
0.8434	Intermediate Similarity	NPC269360
0.8434	Intermediate Similarity	NPC264005
0.8415	Intermediate Similarity	NPC470223
0.8395	Intermediate Similarity	NPC170862
0.8395	Intermediate Similarity	NPC472743
0.8395	Intermediate Similarity	NPC245866
0.8395	Intermediate Similarity	NPC475726
0.8395	Intermediate Similarity	NPC471037
0.8395	Intermediate Similarity	NPC175410
0.8375	Intermediate Similarity	NPC147066
0.8372	Intermediate Similarity	NPC475700
0.8354	Intermediate Similarity	NPC305835
0.8333	Intermediate Similarity	NPC16377
0.8333	Intermediate Similarity	NPC471900
0.8313	Intermediate Similarity	NPC70661
0.8313	Intermediate Similarity	NPC471042
0.8293	Intermediate Similarity	NPC474233
0.8293	Intermediate Similarity	NPC475745
0.8293	Intermediate Similarity	NPC263974
0.8293	Intermediate Similarity	NPC474482
0.8293	Intermediate Similarity	NPC312660
0.8272	Intermediate Similarity	NPC100297
0.8272	Intermediate Similarity	NPC240302
0.8272	Intermediate Similarity	NPC476458
0.8272	Intermediate Similarity	NPC327969
0.8272	Intermediate Similarity	NPC321289
0.8272	Intermediate Similarity	NPC258153
0.8267	Intermediate Similarity	NPC108131
0.8256	Intermediate Similarity	NPC471901
0.8256	Intermediate Similarity	NPC160506
0.8256	Intermediate Similarity	NPC475416
0.825	Intermediate Similarity	NPC304194
0.8235	Intermediate Similarity	NPC213832
0.8235	Intermediate Similarity	NPC271974
0.8235	Intermediate Similarity	NPC220498
0.8235	Intermediate Similarity	NPC247312
0.8235	Intermediate Similarity	NPC57954
0.8228	Intermediate Similarity	NPC321690
0.8214	Intermediate Similarity	NPC134197
0.8193	Intermediate Similarity	NPC292553
0.8193	Intermediate Similarity	NPC474971
0.8182	Intermediate Similarity	NPC159497
0.8182	Intermediate Similarity	NPC255168
0.8182	Intermediate Similarity	NPC280877
0.8161	Intermediate Similarity	NPC287118
0.8161	Intermediate Similarity	NPC473690
0.8161	Intermediate Similarity	NPC244356
0.8161	Intermediate Similarity	NPC475061
0.8161	Intermediate Similarity	NPC471902
0.8161	Intermediate Similarity	NPC224060
0.8148	Intermediate Similarity	NPC162632
0.8148	Intermediate Similarity	NPC201912
0.8148	Intermediate Similarity	NPC232625
0.8148	Intermediate Similarity	NPC263272
0.8148	Intermediate Similarity	NPC38350
0.8148	Intermediate Similarity	NPC267691
0.8148	Intermediate Similarity	NPC274050
0.814	Intermediate Similarity	NPC169933
0.8125	Intermediate Similarity	NPC477371
0.8125	Intermediate Similarity	NPC215843
0.8118	Intermediate Similarity	NPC28227
0.8118	Intermediate Similarity	NPC474845
0.8101	Intermediate Similarity	NPC106078
0.8101	Intermediate Similarity	NPC472300
0.8101	Intermediate Similarity	NPC475932
0.8101	Intermediate Similarity	NPC238227
0.8095	Intermediate Similarity	NPC80590
0.8095	Intermediate Similarity	NPC472738
0.8095	Intermediate Similarity	NPC195640
0.8095	Intermediate Similarity	NPC472505
0.8095	Intermediate Similarity	NPC264127
0.8072	Intermediate Similarity	NPC264665
0.8072	Intermediate Similarity	NPC109512
0.8072	Intermediate Similarity	NPC74595
0.8072	Intermediate Similarity	NPC320801
0.8068	Intermediate Similarity	NPC303863
0.8049	Intermediate Similarity	NPC251779
0.8049	Intermediate Similarity	NPC260956
0.8049	Intermediate Similarity	NPC170985
0.8049	Intermediate Similarity	NPC320514
0.8049	Intermediate Similarity	NPC145143
0.8049	Intermediate Similarity	NPC477858
0.8049	Intermediate Similarity	NPC69101
0.8046	Intermediate Similarity	NPC218301
0.8025	Intermediate Similarity	NPC104545
0.8023	Intermediate Similarity	NPC471043
0.8023	Intermediate Similarity	NPC474570
0.8	Intermediate Similarity	NPC4643
0.8	Intermediate Similarity	NPC96496
0.8	Intermediate Similarity	NPC469996
0.8	Intermediate Similarity	NPC57469
0.7976	Intermediate Similarity	NPC29447
0.7976	Intermediate Similarity	NPC323765
0.7975	Intermediate Similarity	NPC89294
0.7973	Intermediate Similarity	NPC96812
0.7973	Intermediate Similarity	NPC189917
0.7973	Intermediate Similarity	NPC168824
0.7973	Intermediate Similarity	NPC39462
0.7973	Intermediate Similarity	NPC107704
0.7955	Intermediate Similarity	NPC291373
0.7952	Intermediate Similarity	NPC271784
0.7952	Intermediate Similarity	NPC5280
0.7952	Intermediate Similarity	NPC470046
0.7952	Intermediate Similarity	NPC83569
0.7952	Intermediate Similarity	NPC200752
0.7952	Intermediate Similarity	NPC70834
0.7952	Intermediate Similarity	NPC473742
0.7952	Intermediate Similarity	NPC470047
0.7952	Intermediate Similarity	NPC167103
0.7952	Intermediate Similarity	NPC69279
0.7949	Intermediate Similarity	NPC166797
0.7927	Intermediate Similarity	NPC471898
0.7927	Intermediate Similarity	NPC477372
0.7922	Intermediate Similarity	NPC197701
0.7907	Intermediate Similarity	NPC255176
0.7907	Intermediate Similarity	NPC183374
0.7907	Intermediate Similarity	NPC472220
0.7907	Intermediate Similarity	NPC211162
0.7907	Intermediate Similarity	NPC146937
0.7907	Intermediate Similarity	NPC97884
0.7907	Intermediate Similarity	NPC472739
0.7901	Intermediate Similarity	NPC231431
0.7901	Intermediate Similarity	NPC16394
0.7901	Intermediate Similarity	NPC47808
0.7901	Intermediate Similarity	NPC158846
0.7895	Intermediate Similarity	NPC477857
0.7882	Intermediate Similarity	NPC10005
0.7882	Intermediate Similarity	NPC155011
0.7882	Intermediate Similarity	NPC329943
0.7882	Intermediate Similarity	NPC9892
0.7882	Intermediate Similarity	NPC98236
0.7882	Intermediate Similarity	NPC269396
0.7882	Intermediate Similarity	NPC91525
0.7875	Intermediate Similarity	NPC471899
0.7875	Intermediate Similarity	NPC107039
0.7875	Intermediate Similarity	NPC471897
0.7865	Intermediate Similarity	NPC277399
0.7857	Intermediate Similarity	NPC239362
0.7857	Intermediate Similarity	NPC100391
0.7857	Intermediate Similarity	NPC96095
0.7841	Intermediate Similarity	NPC470230
0.7841	Intermediate Similarity	NPC154101
0.7831	Intermediate Similarity	NPC163236
0.7831	Intermediate Similarity	NPC476935
0.7831	Intermediate Similarity	NPC142683
0.7831	Intermediate Similarity	NPC133391
0.7816	Intermediate Similarity	NPC24772
0.7816	Intermediate Similarity	NPC305039
0.7816	Intermediate Similarity	NPC474700
0.7816	Intermediate Similarity	NPC116146
0.7816	Intermediate Similarity	NPC11611
0.7805	Intermediate Similarity	NPC164999
0.7805	Intermediate Similarity	NPC476265
0.7805	Intermediate Similarity	NPC477057
0.7805	Intermediate Similarity	NPC37038
0.7805	Intermediate Similarity	NPC206735
0.7805	Intermediate Similarity	NPC274522
0.7792	Intermediate Similarity	NPC91369
0.7792	Intermediate Similarity	NPC477929
0.7791	Intermediate Similarity	NPC142361
0.7791	Intermediate Similarity	NPC136948
0.7791	Intermediate Similarity	NPC162107
0.7791	Intermediate Similarity	NPC46912
0.7791	Intermediate Similarity	NPC173089
0.7791	Intermediate Similarity	NPC128644
0.7791	Intermediate Similarity	NPC93778
0.7791	Intermediate Similarity	NPC474684
0.7791	Intermediate Similarity	NPC288952
0.7791	Intermediate Similarity	NPC158141

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 NPC63020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2275
0.2-0.3	4415
0.3-0.4	1499
0.4-0.5	387
0.5-0.6	185
0.6-0.7	144
0.7-0.8	61
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD7520	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD8035	Phase 2
0.8256	Intermediate Similarity	NPD8034	Phase 2
0.8118	Intermediate Similarity	NPD6672	Approved
0.8118	Intermediate Similarity	NPD5737	Approved
0.8095	Intermediate Similarity	NPD6409	Approved
0.8095	Intermediate Similarity	NPD5330	Approved
0.8095	Intermediate Similarity	NPD7521	Approved
0.8095	Intermediate Similarity	NPD7334	Approved
0.8095	Intermediate Similarity	NPD7146	Approved
0.8095	Intermediate Similarity	NPD6098	Approved
0.8095	Intermediate Similarity	NPD6684	Approved
0.7952	Intermediate Similarity	NPD4788	Approved
0.7922	Intermediate Similarity	NPD5777	Approved
0.7907	Intermediate Similarity	NPD6903	Approved
0.7816	Intermediate Similarity	NPD6904	Approved
0.7816	Intermediate Similarity	NPD6080	Approved
0.7816	Intermediate Similarity	NPD6673	Approved
0.7753	Intermediate Similarity	NPD6399	Phase 3
0.7733	Intermediate Similarity	NPD4224	Phase 2
0.7701	Intermediate Similarity	NPD5208	Approved
0.7692	Intermediate Similarity	NPD6081	Approved
0.7647	Intermediate Similarity	NPD4786	Approved
0.7582	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7748	Approved
0.7473	Intermediate Similarity	NPD7900	Approved
0.7444	Intermediate Similarity	NPD5693	Phase 1
0.7444	Intermediate Similarity	NPD6050	Approved
0.7444	Intermediate Similarity	NPD7515	Phase 2
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7412	Intermediate Similarity	NPD4221	Approved
0.7412	Intermediate Similarity	NPD3667	Approved
0.7412	Intermediate Similarity	NPD4223	Phase 3
0.7356	Intermediate Similarity	NPD5329	Approved
0.7342	Intermediate Similarity	NPD4747	Approved
0.7342	Intermediate Similarity	NPD4789	Approved
0.7333	Intermediate Similarity	NPD5207	Approved
0.7333	Intermediate Similarity	NPD5692	Phase 3
0.7317	Intermediate Similarity	NPD6117	Approved
0.7308	Intermediate Similarity	NPD5360	Phase 3
0.7308	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6001	Approved
0.7253	Intermediate Similarity	NPD5694	Approved
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4197	Approved
0.7241	Intermediate Similarity	NPD3133	Approved
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD7902	Approved
0.7229	Intermediate Similarity	NPD6116	Phase 1
0.7222	Intermediate Similarity	NPD5328	Approved
0.7215	Intermediate Similarity	NPD4137	Phase 3
0.7204	Intermediate Similarity	NPD5695	Phase 3
0.7195	Intermediate Similarity	NPD3702	Approved
0.7191	Intermediate Similarity	NPD3573	Approved
0.7158	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD6697	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7125	Intermediate Similarity	NPD4691	Approved
0.7125	Intermediate Similarity	NPD4245	Approved
0.7125	Intermediate Similarity	NPD4244	Approved
0.7089	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4688	Approved
0.7079	Intermediate Similarity	NPD4690	Approved
0.7079	Intermediate Similarity	NPD5205	Approved
0.7079	Intermediate Similarity	NPD4138	Approved
0.7079	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD4693	Phase 3
0.7079	Intermediate Similarity	NPD4689	Approved
0.7073	Intermediate Similarity	NPD5733	Approved
0.7065	Intermediate Similarity	NPD5284	Approved
0.7065	Intermediate Similarity	NPD5281	Approved
0.7065	Intermediate Similarity	NPD6079	Approved
0.7033	Intermediate Similarity	NPD4753	Phase 2
0.7033	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3698	Phase 2
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7732	Phase 3
0.69	Remote Similarity	NPD6675	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.6897	Remote Similarity	NPD4692	Approved
0.6897	Remote Similarity	NPD4139	Approved
0.6889	Remote Similarity	NPD5280	Approved
0.6889	Remote Similarity	NPD5279	Phase 3
0.6889	Remote Similarity	NPD4694	Approved
0.6889	Remote Similarity	NPD5690	Phase 2
0.6869	Remote Similarity	NPD6052	Approved
0.6867	Remote Similarity	NPD4687	Approved
0.6867	Remote Similarity	NPD4058	Approved
0.6848	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD5654	Approved
0.6829	Remote Similarity	NPD4758	Discontinued
0.6829	Remote Similarity	NPD5276	Approved
0.6809	Remote Similarity	NPD4202	Approved
0.6804	Remote Similarity	NPD7638	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6735	Remote Similarity	NPD7640	Approved
0.6735	Remote Similarity	NPD7639	Approved
0.6733	Remote Similarity	NPD6008	Approved
0.6703	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5959	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6627	Remote Similarity	NPD4243	Approved
0.6604	Remote Similarity	NPD7094	Approved
0.6604	Remote Similarity	NPD6858	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6598	Remote Similarity	NPD5221	Approved
0.6598	Remote Similarity	NPD7614	Phase 1
0.6598	Remote Similarity	NPD4697	Phase 3
0.6598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5222	Approved
0.6591	Remote Similarity	NPD4695	Discontinued
0.6591	Remote Similarity	NPD7525	Registered
0.6588	Remote Similarity	NPD3703	Phase 2
0.6588	Remote Similarity	NPD6942	Approved
0.6588	Remote Similarity	NPD7339	Approved
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD5364	Discontinued
0.6552	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6531	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD4623	Approved
0.6522	Remote Similarity	NPD4519	Discontinued
0.6509	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6505	Remote Similarity	NPD6412	Phase 2
0.6477	Remote Similarity	NPD7645	Phase 2
0.6471	Remote Similarity	NPD4785	Approved
0.6471	Remote Similarity	NPD4784	Approved
0.6449	Remote Similarity	NPD8133	Approved
0.6422	Remote Similarity	NPD7115	Discovery
0.6421	Remote Similarity	NPD4096	Approved
0.6413	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD5286	Approved
0.64	Remote Similarity	NPD4700	Approved
0.64	Remote Similarity	NPD5285	Approved
0.64	Remote Similarity	NPD4696	Approved
0.64	Remote Similarity	NPD6404	Discontinued
0.6364	Remote Similarity	NPD3671	Phase 1
0.6337	Remote Similarity	NPD5223	Approved
0.633	Remote Similarity	NPD6868	Approved
0.6322	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4632	Approved
0.6289	Remote Similarity	NPD5133	Approved
0.6279	Remote Similarity	NPD6926	Approved
0.6279	Remote Similarity	NPD6924	Approved
0.6275	Remote Similarity	NPD5211	Phase 2
0.6275	Remote Similarity	NPD5224	Approved
0.6275	Remote Similarity	NPD5225	Approved
0.6275	Remote Similarity	NPD4633	Approved
0.6275	Remote Similarity	NPD5226	Approved
0.6275	Remote Similarity	NPD7632	Discontinued
0.6263	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5707	Approved
0.6216	Remote Similarity	NPD6335	Approved
0.6214	Remote Similarity	NPD4754	Approved
0.6214	Remote Similarity	NPD5175	Approved
0.6214	Remote Similarity	NPD5174	Approved
0.6211	Remote Similarity	NPD4518	Approved
0.6207	Remote Similarity	NPD5275	Approved
0.6207	Remote Similarity	NPD8039	Approved
0.6207	Remote Similarity	NPD4190	Phase 3
0.6196	Remote Similarity	NPD5362	Discontinued
0.6186	Remote Similarity	NPD7637	Suspended
0.6186	Remote Similarity	NPD6411	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