NPASS Compound

Structure

CID139778 OpenBabel06191715502D 32 37 0 0 1 0 0 0 0 0999 V2000 0.8371 -1.4498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3689 -1.9327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0193 2.8652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1867 1.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9162 -1.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8371 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1185 0.5092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9091 0.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4953 2.3365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8401 0.9102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2029 -0.1171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4404 -0.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4314 2.0959 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0228 1.5205 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9213 1.6014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8245 0.9207 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5931 0.7757 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6988 0.0877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4919 1.1313 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1042 -0.1579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4057 0.2342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.2342 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4057 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2490 0.5427 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3211 0.8719 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1238 0.0951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1896 0.3201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4588 -1.4336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8351 1.9163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 1.8006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0229 -1.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 11 26 1 0 0 0 0 12 29 1 0 0 0 0 13 9 1 6 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 6 0 0 0 15 30 1 1 0 0 0 16 25 1 6 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 6 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 18 24 1 1 0 0 0 19 27 1 6 0 0 0 20 21 1 0 0 0 0 20 32 1 6 0 0 0 21 23 1 6 0 0 0 21 25 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 0 0 0 0 23 12 1 1 0 0 0 24 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	451.29
Volume:	453.355
LogP:	1.376
LogD:	2.088
LogS:	-3.717
# Rotatable Bonds:	6
TPSA:	80.62
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	7.093
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.387
MDCK Permeability:	5.4826654377393425e-05
Pgp-inhibitor:	0.137
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.406
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	20.80428695678711%
Volume Distribution (VD):	0.946
Pgp-substrate:	56.082035064697266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.987
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.302
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.496

ADMET: Excretion

Clearance (CL):	6.025
Half-life (T1/2):	0.455

ADMET: Toxicity

hERG Blockers:	0.238
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.471
Maximum Recommended Daily Dose:	0.162
Skin Sensitization:	0.729
Carcinogencity:	0.03
Eye Corrosion:	0.177
Eye Irritation:	0.01
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC139778

Natural Product ID:	NPC139778
*Common Name:**	Chasmanine
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DBODJJZRZFZBBD-RIVIBFSZSA-N
Standard InCHI:	InChI=1S/C25H41NO6/c1-6-26-11-23(12-29-2)8-7-16(31-4)25-14-9-13-15(30-3)10-24(28,17(14)19(13)27)18(22(25)26)20(32-5)21(23)25/h13-22,27-28H,6-12H2,1-5H3/t13-,14-,15+,16+,17-,18+,19+,20+,21-,22?,23+,24-,25+/m1/s1
SMILES:	CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]5C[C@@H]6[C@H](C[C@@]([C@H]5[C@H]6O)([C@@H]([C@@H]([C@H]23)OC)C14)O)OC)OC)COC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2227793
PubChem CID:	20055812
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid alkaloids

*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
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[10978212]
NPO9806	Aconitum hemsleyanum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[12736463]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	tuber	n.a.	PMID[12913245]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1293938]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16181762]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[18044843]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[21417277]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21466157]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22223386]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Lateral roots	n.a.	n.a.	PMID[22607495]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22628040]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22907155]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23225552]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23707213]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23707213]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24170571]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24190290]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24190290]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24793215]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[27761113]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[300080]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[300080]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30892884]
NPO31280	Aconitum tatsinenense	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[331924]
NPO5	Aconitum geniculatum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[337598]
NPO5	Aconitum geniculatum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[337610]
NPO5	Aconitum geniculatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[338609]
NPO9220	Aconitum kongboense	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[377474]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5	Aconitum geniculatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9806	Aconitum hemsleyanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9220	Aconitum kongboense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5	Aconitum geniculatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9806	Aconitum hemsleyanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4893	Aconitum ciliare	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14688	Aconitum triphyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9220	Aconitum kongboense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9806	Aconitum hemsleyanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	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
Others	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	69.59	%	PMID[513091]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	53.29	%	PMID[513091]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	90.55	%	PMID[513091]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	72.47	%	PMID[513091]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	61.64	%	PMID[513091]

☑ 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 NPC139778 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	268
0.1-0.2	4166
0.2-0.3	18741
0.3-0.4	10416
0.4-0.5	6002
0.5-0.6	2580
0.6-0.7	478
0.7-0.8	32
0.8-0.85	2
0.85-0.9	3
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC48127
0.9703	High Similarity	NPC8009
0.9703	High Similarity	NPC83047
0.9703	High Similarity	NPC267217
0.9182	High Similarity	NPC96080
0.9182	High Similarity	NPC99905
0.9182	High Similarity	NPC208118
0.9	High Similarity	NPC475887
0.8632	High Similarity	NPC476497
0.8559	High Similarity	NPC476967
0.8547	High Similarity	NPC476501
0.8158	Intermediate Similarity	NPC476502
0.8017	Intermediate Similarity	NPC212106
0.8	Intermediate Similarity	NPC474210
0.7719	Intermediate Similarity	NPC287764
0.7521	Intermediate Similarity	NPC476504
0.748	Intermediate Similarity	NPC476503
0.7458	Intermediate Similarity	NPC476499
0.7288	Intermediate Similarity	NPC476498
0.7244	Intermediate Similarity	NPC309249
0.7182	Intermediate Similarity	NPC155985
0.7154	Intermediate Similarity	NPC470593
0.7154	Intermediate Similarity	NPC470594
0.708	Intermediate Similarity	NPC201712
0.7009	Intermediate Similarity	NPC46981
0.6991	Remote Similarity	NPC475249
0.6967	Remote Similarity	NPC476955
0.6923	Remote Similarity	NPC109533
0.6903	Remote Similarity	NPC473537
0.687	Remote Similarity	NPC475518
0.6842	Remote Similarity	NPC252564
0.6825	Remote Similarity	NPC238323
0.6818	Remote Similarity	NPC312637
0.6814	Remote Similarity	NPC289140
0.6733	Remote Similarity	NPC304499
0.6697	Remote Similarity	NPC21035
0.6696	Remote Similarity	NPC220111
0.6695	Remote Similarity	NPC212874
0.6667	Remote Similarity	NPC28224
0.6569	Remote Similarity	NPC475458
0.6567	Remote Similarity	NPC262050
0.6542	Remote Similarity	NPC296734
0.6538	Remote Similarity	NPC476233
0.6538	Remote Similarity	NPC302578
0.6538	Remote Similarity	NPC185915
0.6538	Remote Similarity	NPC128951
0.6538	Remote Similarity	NPC192046
0.6538	Remote Similarity	NPC477227
0.6538	Remote Similarity	NPC105208
0.6535	Remote Similarity	NPC187471
0.6535	Remote Similarity	NPC470071
0.6535	Remote Similarity	NPC252182
0.6535	Remote Similarity	NPC1340
0.6505	Remote Similarity	NPC317242
0.6476	Remote Similarity	NPC18857
0.6476	Remote Similarity	NPC67657
0.6446	Remote Similarity	NPC317534
0.6442	Remote Similarity	NPC163597
0.6436	Remote Similarity	NPC251201
0.6436	Remote Similarity	NPC232925
0.6436	Remote Similarity	NPC63588
0.6435	Remote Similarity	NPC174117
0.6429	Remote Similarity	NPC165396
0.6415	Remote Similarity	NPC287452
0.6415	Remote Similarity	NPC269333
0.6415	Remote Similarity	NPC81074
0.6415	Remote Similarity	NPC477282
0.641	Remote Similarity	NPC91604
0.6404	Remote Similarity	NPC311246
0.6404	Remote Similarity	NPC167644
0.64	Remote Similarity	NPC478137
0.6389	Remote Similarity	NPC475388
0.6378	Remote Similarity	NPC221196
0.6378	Remote Similarity	NPC39485
0.6373	Remote Similarity	NPC157422
0.6373	Remote Similarity	NPC127094
0.6373	Remote Similarity	NPC100586
0.6373	Remote Similarity	NPC109457
0.6372	Remote Similarity	NPC279329
0.6364	Remote Similarity	NPC266651
0.6364	Remote Similarity	NPC232044
0.6364	Remote Similarity	NPC273290
0.6355	Remote Similarity	NPC248944
0.6355	Remote Similarity	NPC7479
0.6355	Remote Similarity	NPC257296
0.6348	Remote Similarity	NPC477224
0.6348	Remote Similarity	NPC3538
0.6348	Remote Similarity	NPC113500
0.6346	Remote Similarity	NPC243027
0.6346	Remote Similarity	NPC196136
0.6346	Remote Similarity	NPC158208
0.6341	Remote Similarity	NPC473994
0.6337	Remote Similarity	NPC66407
0.6337	Remote Similarity	NPC477820
0.6333	Remote Similarity	NPC241879
0.6325	Remote Similarity	NPC292819
0.6321	Remote Similarity	NPC471769
0.6316	Remote Similarity	NPC59006
0.6316	Remote Similarity	NPC36372
0.6316	Remote Similarity	NPC470537
0.6316	Remote Similarity	NPC293609
0.6311	Remote Similarity	NPC153719
0.6311	Remote Similarity	NPC470610
0.6306	Remote Similarity	NPC471240
0.6283	Remote Similarity	NPC228059
0.6275	Remote Similarity	NPC282454
0.6275	Remote Similarity	NPC192192
0.6273	Remote Similarity	NPC320824
0.6273	Remote Similarity	NPC227260
0.6262	Remote Similarity	NPC476176
0.6261	Remote Similarity	NPC277774
0.626	Remote Similarity	NPC470595
0.625	Remote Similarity	NPC48795
0.625	Remote Similarity	NPC5943
0.625	Remote Similarity	NPC161928
0.625	Remote Similarity	NPC192501
0.625	Remote Similarity	NPC477508
0.625	Remote Similarity	NPC210658
0.625	Remote Similarity	NPC228994
0.625	Remote Similarity	NPC472396
0.625	Remote Similarity	NPC10476
0.625	Remote Similarity	NPC176012
0.625	Remote Similarity	NPC470592
0.6241	Remote Similarity	NPC94881
0.6241	Remote Similarity	NPC265275
0.6241	Remote Similarity	NPC48886
0.624	Remote Similarity	NPC34977
0.624	Remote Similarity	NPC246399
0.6239	Remote Similarity	NPC470611
0.6238	Remote Similarity	NPC474756
0.6228	Remote Similarity	NPC473542
0.6226	Remote Similarity	NPC64081
0.6226	Remote Similarity	NPC11907
0.6226	Remote Similarity	NPC133596
0.6226	Remote Similarity	NPC474574
0.6216	Remote Similarity	NPC290612
0.6212	Remote Similarity	NPC473477
0.621	Remote Similarity	NPC253645
0.621	Remote Similarity	NPC85001
0.621	Remote Similarity	NPC95920
0.621	Remote Similarity	NPC147835
0.6207	Remote Similarity	NPC30687
0.6207	Remote Similarity	NPC473503
0.6207	Remote Similarity	NPC252253
0.6207	Remote Similarity	NPC309866
0.6207	Remote Similarity	NPC24960
0.6207	Remote Similarity	NPC175
0.6207	Remote Similarity	NPC473774
0.6207	Remote Similarity	NPC45959
0.6204	Remote Similarity	NPC16449
0.6204	Remote Similarity	NPC474714
0.6195	Remote Similarity	NPC281004
0.6195	Remote Similarity	NPC128475
0.6194	Remote Similarity	NPC280903
0.6186	Remote Similarity	NPC477222
0.6186	Remote Similarity	NPC477223
0.6182	Remote Similarity	NPC478054
0.6182	Remote Similarity	NPC232023
0.6179	Remote Similarity	NPC478053
0.6176	Remote Similarity	NPC129829
0.6176	Remote Similarity	NPC478139
0.6176	Remote Similarity	NPC254037
0.6174	Remote Similarity	NPC149966
0.6174	Remote Similarity	NPC5632
0.6174	Remote Similarity	NPC473830
0.6174	Remote Similarity	NPC204881
0.6168	Remote Similarity	NPC471045
0.6168	Remote Similarity	NPC147993
0.6165	Remote Similarity	NPC296686
0.6161	Remote Similarity	NPC155531
0.6161	Remote Similarity	NPC131365
0.6161	Remote Similarity	NPC215968
0.616	Remote Similarity	NPC472359
0.6154	Remote Similarity	NPC473064
0.6154	Remote Similarity	NPC92196
0.6154	Remote Similarity	NPC473067
0.6154	Remote Similarity	NPC469710
0.6154	Remote Similarity	NPC473065
0.6148	Remote Similarity	NPC475239
0.6147	Remote Similarity	NPC73515
0.6147	Remote Similarity	NPC192456
0.614	Remote Similarity	NPC102725
0.614	Remote Similarity	NPC82955
0.614	Remote Similarity	NPC323156
0.614	Remote Similarity	NPC473472
0.6134	Remote Similarity	NPC473638
0.6121	Remote Similarity	NPC88962
0.6121	Remote Similarity	NPC144790
0.6121	Remote Similarity	NPC149400
0.6106	Remote Similarity	NPC140446
0.6106	Remote Similarity	NPC43912
0.6102	Remote Similarity	NPC476510
0.6102	Remote Similarity	NPC139271
0.6102	Remote Similarity	NPC156377
0.6102	Remote Similarity	NPC473287
0.6102	Remote Similarity	NPC142264
0.6102	Remote Similarity	NPC304011
0.6091	Remote Similarity	NPC154043
0.6091	Remote Similarity	NPC60018
0.6091	Remote Similarity	NPC202688

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 NPC139778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	2235
0.2-0.3	4809
0.3-0.4	1348
0.4-0.5	481
0.5-0.6	103
0.6-0.7	25
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7182	Intermediate Similarity	NPD7991	Discontinued
0.7155	Intermediate Similarity	NPD7646	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7919	Phase 3
0.6903	Remote Similarity	NPD7920	Phase 3
0.6842	Remote Similarity	NPD8088	Phase 1
0.6829	Remote Similarity	NPD7754	Approved
0.6829	Remote Similarity	NPD7755	Approved
0.678	Remote Similarity	NPD6920	Discontinued
0.6752	Remote Similarity	NPD7911	Approved
0.6752	Remote Similarity	NPD7912	Approved
0.6752	Remote Similarity	NPD7987	Approved
0.6752	Remote Similarity	NPD7986	Approved
0.6667	Remote Similarity	NPD8174	Phase 2
0.6639	Remote Similarity	NPD8040	Discontinued
0.6583	Remote Similarity	NPD7989	Approved
0.6583	Remote Similarity	NPD7990	Approved
0.6496	Remote Similarity	NPD8418	Phase 2
0.6455	Remote Similarity	NPD8308	Discontinued
0.6393	Remote Similarity	NPD6415	Discontinued
0.6355	Remote Similarity	NPD6928	Phase 2
0.632	Remote Similarity	NPD8077	Approved
0.632	Remote Similarity	NPD8078	Approved
0.6299	Remote Similarity	NPD6940	Discontinued
0.6142	Remote Similarity	NPD8298	Phase 2
0.6019	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD8171	Discontinued
0.5971	Remote Similarity	NPD8449	Approved
0.5929	Remote Similarity	NPD8450	Suspended
0.5812	Remote Similarity	NPD6700	Approved
0.5812	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4787	Phase 1
0.5789	Remote Similarity	NPD394	Phase 3
0.5763	Remote Similarity	NPD6702	Approved
0.5763	Remote Similarity	NPD6703	Approved
0.5693	Remote Similarity	NPD591	Approved
0.5693	Remote Similarity	NPD577	Phase 3

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