NPASS Compound

Structure

CID206028 OpenBabel06191715592D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 -2.2321 -0.8660 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 -3.5000 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 1.5000 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 2.5981 -0.5000 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 0.8660 -1.5000 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 1.7321 -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 1 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 0.8660 -0.5000 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 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 15 2 0 0 0 0 12 14 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 19 2 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 1 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 21 1 0 0 0 0 19 24 1 0 0 0 0 21 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.22
Volume:	361.928
LogP:	4.714
LogD:	3.91
LogS:	-4.19
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.852
Synthetic Accessibility Score:	3.658
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166
MDCK Permeability:	1.8743841792456806e-05
Pgp-inhibitor:	0.848
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.427
Plasma Protein Binding (PPB):	96.39085388183594%
Volume Distribution (VD):	1.777
Pgp-substrate:	3.7889022827148438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.77
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.503
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.387
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.461
CYP3A4-substrate:	0.675

ADMET: Excretion

Clearance (CL):	10.82
Half-life (T1/2):	0.473

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.563
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.16
Carcinogencity:	0.13
Eye Corrosion:	0.003
Eye Irritation:	0.486
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC206028

Natural Product ID:	NPC206028
*Common Name:**	Triptonoterpene Methyl Ether
IUPAC Name:	(4aS,10aR)-5-hydroxy-8-methoxy-1,1,4a-trimethyl-7-propan-2-yl-4,9,10,10a-tetrahydro-3H-phenanthren-2-one
Synonyms:
Standard InCHIKey:	SPNKZMRXBVCONG-KKSFZXQISA-N
Standard InCHI:	InChI=1S/C21H30O3/c1-12(2)14-11-15(22)18-13(19(14)24-6)7-8-16-20(3,4)17(23)9-10-21(16,18)5/h11-12,16,22H,7-10H2,1-6H3/t16-,21-/m0/s1
SMILES:	CC(C)c1cc(c2c(CC[C@H]3C(C)(C)C(=O)CC[C@]23C)c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3798093
PubChem CID:	15011611
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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(99)00339-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10746886]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[23252270]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[535601]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8328267]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2000, 53, 715-722.]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	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
IC50	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	>	100000.0	nM	PMID[477629]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	47810.0	nM	PMID[477629]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	29260.0	nM	PMID[477629]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[477629]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[477629]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39810.0	nM	PMID[477629]

☑ 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 NPC206028 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	306
0.1-0.2	1497
0.2-0.3	2884
0.3-0.4	7950
0.4-0.5	11211
0.5-0.6	5108
0.6-0.7	10724
0.7-0.8	2828
0.8-0.85	163
0.85-0.9	22
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.937	High Similarity	NPC258073
0.9302	High Similarity	NPC27394
0.8968	High Similarity	NPC75432
0.8889	High Similarity	NPC471187
0.8872	High Similarity	NPC474610
0.8846	High Similarity	NPC470725
0.8806	High Similarity	NPC98804
0.8722	High Similarity	NPC213122
0.8712	High Similarity	NPC251549
0.8676	High Similarity	NPC76312
0.8672	High Similarity	NPC181334
0.8661	High Similarity	NPC11250
0.8661	High Similarity	NPC49441
0.8651	High Similarity	NPC32322
0.8651	High Similarity	NPC259703
0.8651	High Similarity	NPC129176
0.8636	High Similarity	NPC164295
0.8605	High Similarity	NPC477213
0.8593	High Similarity	NPC471670
0.8583	High Similarity	NPC154696
0.8583	High Similarity	NPC249340
0.8583	High Similarity	NPC162935
0.8571	High Similarity	NPC85595
0.8571	High Similarity	NPC165612
0.8571	High Similarity	NPC312560
0.8551	High Similarity	NPC124365
0.855	High Similarity	NPC176590
0.854	High Similarity	NPC79372
0.8529	High Similarity	NPC156888
0.8529	High Similarity	NPC470721
0.8529	High Similarity	NPC6100
0.8529	High Similarity	NPC470722
0.8527	High Similarity	NPC248557
0.8525	High Similarity	NPC98372
0.8519	High Similarity	NPC252343
0.8516	High Similarity	NPC176208
0.8516	High Similarity	NPC121168
0.8496	Intermediate Similarity	NPC239134
0.8473	Intermediate Similarity	NPC319422
0.8473	Intermediate Similarity	NPC477214
0.8473	Intermediate Similarity	NPC477211
0.8473	Intermediate Similarity	NPC477212
0.8467	Intermediate Similarity	NPC265335
0.8462	Intermediate Similarity	NPC137750
0.845	Intermediate Similarity	NPC198014
0.8438	Intermediate Similarity	NPC48623
0.8438	Intermediate Similarity	NPC253627
0.8438	Intermediate Similarity	NPC168707
0.8429	Intermediate Similarity	NPC474599
0.8425	Intermediate Similarity	NPC478121
0.8385	Intermediate Similarity	NPC61685
0.8382	Intermediate Similarity	NPC281513
0.8382	Intermediate Similarity	NPC22222
0.8372	Intermediate Similarity	NPC152946
0.8369	Intermediate Similarity	NPC196941
0.8369	Intermediate Similarity	NPC309169
0.8359	Intermediate Similarity	NPC45663
0.8359	Intermediate Similarity	NPC241001
0.8359	Intermediate Similarity	NPC100108
0.8359	Intermediate Similarity	NPC277798
0.8358	Intermediate Similarity	NPC474246
0.8358	Intermediate Similarity	NPC474143
0.8358	Intermediate Similarity	NPC471851
0.8357	Intermediate Similarity	NPC201297
0.8346	Intermediate Similarity	NPC131684
0.8333	Intermediate Similarity	NPC69424
0.8333	Intermediate Similarity	NPC176130
0.8333	Intermediate Similarity	NPC78364
0.8333	Intermediate Similarity	NPC84672
0.8321	Intermediate Similarity	NPC76119
0.8321	Intermediate Similarity	NPC87985
0.8321	Intermediate Similarity	NPC194847
0.8321	Intermediate Similarity	NPC21797
0.8321	Intermediate Similarity	NPC4286
0.832	Intermediate Similarity	NPC283169
0.8298	Intermediate Similarity	NPC163948
0.8296	Intermediate Similarity	NPC289624
0.8296	Intermediate Similarity	NPC27578
0.8293	Intermediate Similarity	NPC77772
0.8293	Intermediate Similarity	NPC275627
0.8284	Intermediate Similarity	NPC108129
0.8284	Intermediate Similarity	NPC196621
0.8284	Intermediate Similarity	NPC196193
0.8284	Intermediate Similarity	NPC253488
0.8284	Intermediate Similarity	NPC249425
0.8281	Intermediate Similarity	NPC318552
0.8281	Intermediate Similarity	NPC103916
0.8281	Intermediate Similarity	NPC135467
0.8281	Intermediate Similarity	NPC260832
0.8281	Intermediate Similarity	NPC190501
0.8273	Intermediate Similarity	NPC1268
0.8271	Intermediate Similarity	NPC81261
0.8271	Intermediate Similarity	NPC201069
0.8271	Intermediate Similarity	NPC47288
0.8258	Intermediate Similarity	NPC474737
0.8254	Intermediate Similarity	NPC312105
0.8252	Intermediate Similarity	NPC300540
0.8252	Intermediate Similarity	NPC58752
0.8244	Intermediate Similarity	NPC111088
0.8222	Intermediate Similarity	NPC153019
0.8209	Intermediate Similarity	NPC276238
0.8203	Intermediate Similarity	NPC471449
0.8203	Intermediate Similarity	NPC42657
0.8201	Intermediate Similarity	NPC475104
0.8195	Intermediate Similarity	NPC72667
0.8195	Intermediate Similarity	NPC186889
0.8194	Intermediate Similarity	NPC470757
0.8194	Intermediate Similarity	NPC52692
0.8188	Intermediate Similarity	NPC472308
0.8182	Intermediate Similarity	NPC320847
0.8175	Intermediate Similarity	NPC35797
0.8175	Intermediate Similarity	NPC202225
0.8175	Intermediate Similarity	NPC192948
0.8162	Intermediate Similarity	NPC183103
0.8154	Intermediate Similarity	NPC475839
0.8148	Intermediate Similarity	NPC475880
0.8148	Intermediate Similarity	NPC475102
0.8145	Intermediate Similarity	NPC260323
0.8145	Intermediate Similarity	NPC176279
0.8145	Intermediate Similarity	NPC470770
0.8145	Intermediate Similarity	NPC266937
0.8125	Intermediate Similarity	NPC139047
0.8125	Intermediate Similarity	NPC63010
0.812	Intermediate Similarity	NPC254492
0.812	Intermediate Similarity	NPC71610
0.8116	Intermediate Similarity	NPC22644
0.8112	Intermediate Similarity	NPC471600
0.8112	Intermediate Similarity	NPC260152
0.811	Intermediate Similarity	NPC477137
0.811	Intermediate Similarity	NPC92
0.811	Intermediate Similarity	NPC308311
0.811	Intermediate Similarity	NPC469663
0.811	Intermediate Similarity	NPC38893
0.8106	Intermediate Similarity	NPC199273
0.8106	Intermediate Similarity	NPC474237
0.8102	Intermediate Similarity	NPC470406
0.8102	Intermediate Similarity	NPC49742
0.8102	Intermediate Similarity	NPC211352
0.8102	Intermediate Similarity	NPC78307
0.8102	Intermediate Similarity	NPC59459
0.8102	Intermediate Similarity	NPC477139
0.8099	Intermediate Similarity	NPC69755
0.8099	Intermediate Similarity	NPC329493
0.8095	Intermediate Similarity	NPC471534
0.8092	Intermediate Similarity	NPC476332
0.8092	Intermediate Similarity	NPC473464
0.8088	Intermediate Similarity	NPC476847
0.808	Intermediate Similarity	NPC62867
0.808	Intermediate Similarity	NPC177962
0.8077	Intermediate Similarity	NPC212559
0.8077	Intermediate Similarity	NPC474175
0.8074	Intermediate Similarity	NPC171460
0.8074	Intermediate Similarity	NPC303910
0.8074	Intermediate Similarity	NPC57552
0.8069	Intermediate Similarity	NPC478163
0.8067	Intermediate Similarity	NPC67197
0.8065	Intermediate Similarity	NPC132720
0.8062	Intermediate Similarity	NPC51341
0.8062	Intermediate Similarity	NPC469644
0.806	Intermediate Similarity	NPC471530
0.8058	Intermediate Similarity	NPC475549
0.8058	Intermediate Similarity	NPC141934
0.8047	Intermediate Similarity	NPC172219
0.8047	Intermediate Similarity	NPC304510
0.8047	Intermediate Similarity	NPC238176
0.8047	Intermediate Similarity	NPC25648
0.8047	Intermediate Similarity	NPC187993
0.8043	Intermediate Similarity	NPC274876
0.8042	Intermediate Similarity	NPC224884
0.8042	Intermediate Similarity	NPC316691
0.8042	Intermediate Similarity	NPC209085
0.8033	Intermediate Similarity	NPC30416
0.803	Intermediate Similarity	NPC275145
0.8029	Intermediate Similarity	NPC118253
0.8027	Intermediate Similarity	NPC294646
0.8014	Intermediate Similarity	NPC476191
0.8014	Intermediate Similarity	NPC470407
0.8	Intermediate Similarity	NPC470723
0.8	Intermediate Similarity	NPC290601
0.8	Intermediate Similarity	NPC469507
0.8	Intermediate Similarity	NPC223912
0.8	Intermediate Similarity	NPC201419
0.8	Intermediate Similarity	NPC474131
0.8	Intermediate Similarity	NPC60389
0.8	Intermediate Similarity	NPC211565
0.8	Intermediate Similarity	NPC3009
0.7986	Intermediate Similarity	NPC279463
0.7986	Intermediate Similarity	NPC152209
0.7985	Intermediate Similarity	NPC128321
0.7985	Intermediate Similarity	NPC470724
0.7984	Intermediate Similarity	NPC471671
0.7971	Intermediate Similarity	NPC227719
0.797	Intermediate Similarity	NPC147896
0.797	Intermediate Similarity	NPC276962
0.797	Intermediate Similarity	NPC190086
0.797	Intermediate Similarity	NPC15127
0.7969	Intermediate Similarity	NPC236070
0.7969	Intermediate Similarity	NPC308828
0.7969	Intermediate Similarity	NPC126759
0.7969	Intermediate Similarity	NPC69539

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 NPC206028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	962
0.2-0.3	1295
0.3-0.4	2468
0.4-0.5	2173
0.5-0.6	1244
0.6-0.7	609
0.7-0.8	98
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8346	Intermediate Similarity	NPD1651	Approved
0.8281	Intermediate Similarity	NPD3019	Approved
0.8261	Intermediate Similarity	NPD6099	Approved
0.8261	Intermediate Similarity	NPD6100	Approved
0.8244	Intermediate Similarity	NPD1283	Approved
0.8156	Intermediate Similarity	NPD7003	Approved
0.814	Intermediate Similarity	NPD2932	Approved
0.8106	Intermediate Similarity	NPD6696	Suspended
0.8015	Intermediate Similarity	NPD1281	Approved
0.8	Intermediate Similarity	NPD4626	Approved
0.7969	Intermediate Similarity	NPD7340	Approved
0.7956	Intermediate Similarity	NPD8032	Phase 2
0.7937	Intermediate Similarity	NPD7635	Approved
0.7914	Intermediate Similarity	NPD4097	Suspended
0.7895	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1398	Phase 1
0.7872	Intermediate Similarity	NPD2935	Discontinued
0.7817	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2979	Phase 3
0.7752	Intermediate Similarity	NPD6671	Approved
0.7744	Intermediate Similarity	NPD1611	Approved
0.7721	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD4624	Approved
0.7698	Intermediate Similarity	NPD6663	Approved
0.7681	Intermediate Similarity	NPD4625	Phase 3
0.7669	Intermediate Similarity	NPD3023	Approved
0.7669	Intermediate Similarity	NPD3026	Approved
0.7664	Intermediate Similarity	NPD5736	Approved
0.7652	Intermediate Similarity	NPD3024	Approved
0.7652	Intermediate Similarity	NPD3025	Approved
0.7652	Intermediate Similarity	NPD5691	Approved
0.7647	Intermediate Similarity	NPD2797	Approved
0.7643	Intermediate Similarity	NPD3620	Phase 2
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD4140	Approved
0.7643	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1201	Approved
0.76	Intermediate Similarity	NPD3226	Approved
0.76	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7458	Discontinued
0.7594	Intermediate Similarity	NPD1778	Approved
0.7591	Intermediate Similarity	NPD2798	Approved
0.7568	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3972	Approved
0.754	Intermediate Similarity	NPD2342	Discontinued
0.7536	Intermediate Similarity	NPD2861	Phase 2
0.7519	Intermediate Similarity	NPD5585	Approved
0.7517	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD5327	Phase 3
0.75	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7644	Approved
0.75	Intermediate Similarity	NPD3268	Approved
0.748	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3091	Approved
0.7426	Intermediate Similarity	NPD2233	Approved
0.7426	Intermediate Similarity	NPD1608	Approved
0.7426	Intermediate Similarity	NPD2232	Approved
0.7426	Intermediate Similarity	NPD2230	Approved
0.7415	Intermediate Similarity	NPD8166	Discontinued
0.7407	Intermediate Similarity	NPD3496	Discontinued
0.7391	Intermediate Similarity	NPD1470	Approved
0.7379	Intermediate Similarity	NPD2531	Phase 2
0.7379	Intermediate Similarity	NPD4476	Approved
0.7379	Intermediate Similarity	NPD2438	Suspended
0.7379	Intermediate Similarity	NPD4477	Approved
0.7376	Intermediate Similarity	NPD7985	Registered
0.7375	Intermediate Similarity	NPD7473	Discontinued
0.7343	Intermediate Similarity	NPD5735	Approved
0.7342	Intermediate Similarity	NPD6959	Discontinued
0.7338	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1876	Approved
0.731	Intermediate Similarity	NPD2799	Discontinued
0.7305	Intermediate Similarity	NPD7095	Approved
0.7296	Intermediate Similarity	NPD6232	Discontinued
0.7292	Intermediate Similarity	NPD6353	Approved
0.7285	Intermediate Similarity	NPD6090	Discontinued
0.7254	Intermediate Similarity	NPD6798	Discontinued
0.7254	Intermediate Similarity	NPD2313	Discontinued
0.7254	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4359	Approved
0.7236	Intermediate Similarity	NPD288	Approved
0.723	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1535	Discovery
0.7226	Intermediate Similarity	NPD3092	Approved
0.7222	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2533	Approved
0.7219	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD2534	Approved
0.7215	Intermediate Similarity	NPD6234	Discontinued
0.7211	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7028	Phase 2
0.7206	Intermediate Similarity	NPD4059	Approved
0.7206	Intermediate Similarity	NPD17	Approved
0.7203	Intermediate Similarity	NPD6233	Phase 2
0.7197	Intermediate Similarity	NPD4966	Approved
0.7197	Intermediate Similarity	NPD4967	Phase 2
0.7197	Intermediate Similarity	NPD4965	Approved
0.7192	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD968	Approved
0.7181	Intermediate Similarity	NPD4110	Phase 3
0.7181	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5844	Phase 1
0.7174	Intermediate Similarity	NPD1481	Phase 2
0.7172	Intermediate Similarity	NPD1607	Approved
0.7172	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2237	Approved
0.7162	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4750	Phase 3
0.7154	Intermediate Similarity	NPD844	Approved
0.7152	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD5951	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.7132	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7427	Discontinued
0.7122	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4908	Phase 1
0.7105	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5762	Approved
0.7095	Intermediate Similarity	NPD6004	Phase 3
0.7095	Intermediate Similarity	NPD5763	Approved
0.7095	Intermediate Similarity	NPD6002	Phase 3
0.7095	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6005	Phase 3
0.709	Intermediate Similarity	NPD709	Approved
0.708	Intermediate Similarity	NPD3095	Discontinued
0.7075	Intermediate Similarity	NPD4308	Phase 3
0.707	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7819	Suspended
0.707	Intermediate Similarity	NPD5929	Approved
0.7068	Intermediate Similarity	NPD5283	Phase 1
0.7067	Intermediate Similarity	NPD3750	Approved
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7063	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7008	Discontinued
0.7039	Intermediate Similarity	NPD7041	Phase 2
0.7039	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1240	Approved
0.7029	Intermediate Similarity	NPD3847	Discontinued
0.7027	Intermediate Similarity	NPD5406	Approved
0.7027	Intermediate Similarity	NPD5405	Approved
0.7027	Intermediate Similarity	NPD5408	Approved
0.7027	Intermediate Similarity	NPD5404	Approved
0.7025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8127	Discontinued
0.7016	Intermediate Similarity	NPD1809	Phase 2
0.7015	Intermediate Similarity	NPD497	Approved
0.7	Intermediate Similarity	NPD6674	Discontinued
0.7	Intermediate Similarity	NPD1669	Approved
0.6992	Remote Similarity	NPD845	Approved
0.6986	Remote Similarity	NPD3657	Discovery
0.6986	Remote Similarity	NPD4618	Approved
0.6986	Remote Similarity	NPD4622	Approved
0.6984	Remote Similarity	NPD3020	Approved
0.698	Remote Similarity	NPD2344	Approved
0.6978	Remote Similarity	NPD1610	Phase 2
0.6978	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD3300	Phase 2
0.6972	Remote Similarity	NPD6584	Phase 3
0.6966	Remote Similarity	NPD4870	Approved
0.6964	Remote Similarity	NPD8312	Approved
0.6964	Remote Similarity	NPD8313	Approved
0.6962	Remote Similarity	NPD2801	Approved
0.6959	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1510	Phase 2
0.6954	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.694	Remote Similarity	NPD495	Approved
0.694	Remote Similarity	NPD496	Approved
0.694	Remote Similarity	NPD498	Approved
0.694	Remote Similarity	NPD1241	Discontinued
0.6939	Remote Similarity	NPD6651	Approved
0.6934	Remote Similarity	NPD1894	Discontinued
0.6933	Remote Similarity	NPD7037	Approved
0.6933	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2238	Phase 2
0.6918	Remote Similarity	NPD3110	Approved
0.6918	Remote Similarity	NPD3109	Approved
0.6917	Remote Similarity	NPD228	Approved
0.6909	Remote Similarity	NPD7177	Discontinued
0.6909	Remote Similarity	NPD7228	Approved
0.6897	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3764	Approved
0.6894	Remote Similarity	NPD5451	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