NPASS Compound

Structure

CID99659 OpenBabel06191715442D 26 29 0 0 1 0 0 0 0 0999 V2000 1.7002 -3.8618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1888 -2.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3953 -0.0518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0165 1.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4354 -0.2711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5178 -1.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5220 -2.4065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0068 -2.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6683 0.0100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6598 -2.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 -0.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6755 -0.9576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8247 -2.4316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5128 -2.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5307 -1.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8320 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8434 -1.4437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -0.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 -2.8926 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -2.9617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 -1.0195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8219 1.4484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8343 0.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 14 20 1 0 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 20 21 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.18
Volume:	367.885
LogP:	2.733
LogD:	3.035
LogS:	-3.1
# Rotatable Bonds:	4
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.84
Synthetic Accessibility Score:	2.929
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.905
MDCK Permeability:	3.0847648304188624e-05
Pgp-inhibitor:	0.886
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.341
30% Bioavailability (F30%):	0.705

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	63.276206970214844%
Volume Distribution (VD):	1.752
Pgp-substrate:	25.53768539428711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.165
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.941
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.93

ADMET: Excretion

Clearance (CL):	10.268
Half-life (T1/2):	0.471

ADMET: Toxicity

hERG Blockers:	0.388
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.739
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.857
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.164
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC99659

Natural Product ID:	NPC99659
*Common Name:**	Glaucine
IUPAC Name:	(6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms:	Glaucine
Standard InCHIKey:	RUZIUYOSRDWYQF-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1
SMILES:	COc1cc2c(cc1OC)C[C@H]1c3c2c(OC)c(OC)cc3CCN1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228082
PubChem CID:	16754
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	root	n.a.	PMID[24317429]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24897106]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO31526	Xylopia laevigata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[27399666]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15671	Iris decora	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28458	Coccoloba dugandiana	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5075	Balaenoptera borealis	Species	Balaenopteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1005	Pycnarrhena novoguineensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28873	Epinetrum mangenotii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29235	Musca autumnalis	Species	Muscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1518	Pedicularis chinensis	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29272	Paronychia argentea	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29520	Curculigo breviscapa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2556	Platytaenia dasycarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3020	Brickellia paniculata	Species	Asteraceae	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	8
Ki	5
Others	22

Activity Type	# Activity
Cell Line	1
Individual Protein	7
Organism	8
Others	19

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4163	Individual Protein	Protein tyrosine phosphatase receptor type C-associated protein	Homo sapiens	IC50	=	88000.0	nM	PMID[449573]
NPT1076	Cell Line	B-cells		IC50	>	100000.0	nM	PMID[449574]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Ki	=	2900.0	nM	PMID[449575]
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	Ki	=	2800.0	nM	PMID[449575]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Ki	=	966.0	nM	PMID[449579]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Ki	=	43.0	nM	PMID[449579]
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	FC	=	22.0	n.a.	PMID[449580]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[449574]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[449574]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	50.0	%	PMID[449575]
NPT1	Others	Radical scavenging activity		Activity	=	0.8	%	PMID[449577]
NPT1	Others	Radical scavenging activity		Activity	=	1.2	%	PMID[449577]
NPT1	Others	Radical scavenging activity		Activity	=	1.1	%	PMID[449577]
NPT1	Others	Radical scavenging activity		Activity	=	1.3	%	PMID[449577]
NPT1	Others	Radical scavenging activity		Activity	=	1.4	%	PMID[449577]
NPT1	Others	Radical scavenging activity		Activity	=	1.6	%	PMID[449577]
NPT27	Others	Unspecified		CC50	=	115000.0	nM	PMID[449577]
NPT1831	Organism	Human echovirus 13	Human echovirus 13	IC50	=	60000.0	nM	PMID[449577]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.9	n.a.	PMID[449577]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	IC50	=	60000.0	nM	PMID[449577]
NPT1832	Organism	Human rhinovirus 14	Human rhinovirus 14	CC50	=	182000.0	nM	PMID[449577]
NPT27	Others	Unspecified		IC50	=	22000.0	nM	PMID[449577]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	8.3	n.a.	PMID[449577]
NPT1833	Organism	Human coxsackievirus B1	Human coxsackievirus B1	IC50	=	21000.0	nM	PMID[449577]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	5.5	n.a.	PMID[449577]
NPT2	Others	Unspecified		IC50	=	96900.0	nM	PMID[449578]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	=	171.0	nM	PMID[449579]
NPT2	Others	Unspecified		Ratio Ki	=	4.0	n.a.	PMID[449579]
NPT2	Others	Unspecified		Ratio Ki	=	22.0	n.a.	PMID[449579]
NPT2	Others	Unspecified		FC	=	7.0	n.a.	PMID[449580]

☑ 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 NPC99659 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	374
0.1-0.2	1751
0.2-0.3	8321
0.3-0.4	9744
0.4-0.5	6165
0.5-0.6	11841
0.6-0.7	3559
0.7-0.8	536
0.8-0.85	209
0.85-0.9	127
0.9-0.95	59
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC325871
0.9864	High Similarity	NPC476572
0.9658	High Similarity	NPC326316
0.9658	High Similarity	NPC81733
0.9539	High Similarity	NPC13504
0.9539	High Similarity	NPC96603
0.9539	High Similarity	NPC253043
0.9539	High Similarity	NPC477563
0.9539	High Similarity	NPC136508
0.9539	High Similarity	NPC196447
0.9539	High Similarity	NPC78222
0.9539	High Similarity	NPC306843
0.9539	High Similarity	NPC212794
0.9539	High Similarity	NPC302527
0.9539	High Similarity	NPC16805
0.9539	High Similarity	NPC167546
0.9477	High Similarity	NPC476432
0.9477	High Similarity	NPC24264
0.9474	High Similarity	NPC324144
0.9416	High Similarity	NPC117188
0.9416	High Similarity	NPC12053
0.9416	High Similarity	NPC247389
0.9416	High Similarity	NPC210918
0.9416	High Similarity	NPC474931
0.9416	High Similarity	NPC158376
0.9416	High Similarity	NPC205421
0.9416	High Similarity	NPC81218
0.9416	High Similarity	NPC306555
0.9416	High Similarity	NPC145832
0.9412	High Similarity	NPC225774
0.9351	High Similarity	NPC219341
0.929	High Similarity	NPC204947
0.9272	High Similarity	NPC203784
0.9272	High Similarity	NPC126519
0.9272	High Similarity	NPC170503
0.9236	High Similarity	NPC19520
0.9236	High Similarity	NPC149090
0.9236	High Similarity	NPC239775
0.9221	High Similarity	NPC1229
0.9216	High Similarity	NPC477559
0.9216	High Similarity	NPC266753
0.9216	High Similarity	NPC166014
0.9216	High Similarity	NPC160298
0.9216	High Similarity	NPC306902
0.9216	High Similarity	NPC232924
0.9216	High Similarity	NPC27410
0.9205	High Similarity	NPC244112
0.9172	High Similarity	NPC477562
0.9172	High Similarity	NPC26240
0.9172	High Similarity	NPC69712
0.9172	High Similarity	NPC6152
0.9119	High Similarity	NPC229166
0.9119	High Similarity	NPC199465
0.9119	High Similarity	NPC128560
0.9057	High Similarity	NPC66341
0.9057	High Similarity	NPC477020
0.9057	High Similarity	NPC192135
0.9051	High Similarity	NPC168753
0.9051	High Similarity	NPC118274
0.9006	High Similarity	NPC114364
0.9006	High Similarity	NPC320223
0.8993	High Similarity	NPC210437
0.8993	High Similarity	NPC106295
0.8993	High Similarity	NPC51957
0.8993	High Similarity	NPC476144
0.8993	High Similarity	NPC16107
0.898	High Similarity	NPC128019
0.898	High Similarity	NPC136860
0.898	High Similarity	NPC476567
0.8973	High Similarity	NPC213206
0.8973	High Similarity	NPC188163
0.8973	High Similarity	NPC474915
0.8973	High Similarity	NPC470925
0.8973	High Similarity	NPC328750
0.8951	High Similarity	NPC220961
0.8933	High Similarity	NPC7467
0.8933	High Similarity	NPC130941
0.8924	High Similarity	NPC298979
0.891	High Similarity	NPC60186
0.8904	High Similarity	NPC314682
0.8889	High Similarity	NPC190461
0.8874	High Similarity	NPC219162
0.8874	High Similarity	NPC92541
0.8868	High Similarity	NPC241055
0.8861	High Similarity	NPC86144
0.8861	High Similarity	NPC476573
0.8861	High Similarity	NPC304659
0.8861	High Similarity	NPC35627
0.8861	High Similarity	NPC81247
0.8841	High Similarity	NPC116284
0.8841	High Similarity	NPC248642
0.8834	High Similarity	NPC126284
0.8834	High Similarity	NPC258695
0.8834	High Similarity	NPC470879
0.8834	High Similarity	NPC474507
0.8824	High Similarity	NPC470924
0.8797	High Similarity	NPC168409
0.8788	High Similarity	NPC156576
0.8788	High Similarity	NPC302275
0.878	High Similarity	NPC312918
0.878	High Similarity	NPC476574
0.878	High Similarity	NPC32413
0.878	High Similarity	NPC155442
0.878	High Similarity	NPC477561
0.878	High Similarity	NPC474506
0.8773	High Similarity	NPC23219
0.8742	High Similarity	NPC144863
0.8742	High Similarity	NPC253883
0.8742	High Similarity	NPC95075
0.8742	High Similarity	NPC90844
0.8734	High Similarity	NPC189470
0.872	High Similarity	NPC267408
0.8712	High Similarity	NPC173416
0.8712	High Similarity	NPC476577
0.8712	High Similarity	NPC148709
0.8712	High Similarity	NPC112575
0.871	High Similarity	NPC123323
0.8688	High Similarity	NPC150879
0.8683	High Similarity	NPC47077
0.8683	High Similarity	NPC14507
0.8675	High Similarity	NPC135772
0.8659	High Similarity	NPC118633
0.8659	High Similarity	NPC148693
0.8659	High Similarity	NPC294790
0.8654	High Similarity	NPC323443
0.8654	High Similarity	NPC180756
0.865	High Similarity	NPC477558
0.8631	High Similarity	NPC237579
0.8618	High Similarity	NPC476151
0.8609	High Similarity	NPC185838
0.859	High Similarity	NPC469817
0.859	High Similarity	NPC39701
0.859	High Similarity	NPC172765
0.859	High Similarity	NPC295691
0.859	High Similarity	NPC276588
0.859	High Similarity	NPC2413
0.859	High Similarity	NPC193949
0.859	High Similarity	NPC249797
0.859	High Similarity	NPC127674
0.859	High Similarity	NPC110416
0.859	High Similarity	NPC138487
0.859	High Similarity	NPC184026
0.859	High Similarity	NPC54379
0.859	High Similarity	NPC189266
0.859	High Similarity	NPC204828
0.859	High Similarity	NPC5238
0.859	High Similarity	NPC207757
0.859	High Similarity	NPC216459
0.859	High Similarity	NPC41178
0.859	High Similarity	NPC278799
0.8589	High Similarity	NPC285941
0.858	High Similarity	NPC82763
0.8571	High Similarity	NPC192768
0.8571	High Similarity	NPC88249
0.8571	High Similarity	NPC57036
0.8571	High Similarity	NPC214116
0.8571	High Similarity	NPC97221
0.8571	High Similarity	NPC220858
0.8571	High Similarity	NPC151895
0.8562	High Similarity	NPC147390
0.8562	High Similarity	NPC246587
0.8562	High Similarity	NPC135538
0.8562	High Similarity	NPC428
0.8562	High Similarity	NPC476571
0.8562	High Similarity	NPC475959
0.8562	High Similarity	NPC24465
0.8562	High Similarity	NPC169743
0.8562	High Similarity	NPC24233
0.8535	High Similarity	NPC186063
0.8535	High Similarity	NPC146288
0.8521	High Similarity	NPC476576
0.8521	High Similarity	NPC312531
0.8521	High Similarity	NPC186546
0.8516	High Similarity	NPC476568
0.8509	High Similarity	NPC13916
0.8509	High Similarity	NPC264850
0.8506	High Similarity	NPC477565
0.8506	High Similarity	NPC103379
0.85	High Similarity	NPC233650
0.8497	Intermediate Similarity	NPC179825
0.8497	Intermediate Similarity	NPC321505
0.8497	Intermediate Similarity	NPC191376
0.8491	Intermediate Similarity	NPC119649
0.8491	Intermediate Similarity	NPC230956
0.8491	Intermediate Similarity	NPC271388
0.8491	Intermediate Similarity	NPC205255
0.8491	Intermediate Similarity	NPC235143
0.8485	Intermediate Similarity	NPC241704
0.848	Intermediate Similarity	NPC478093
0.8466	Intermediate Similarity	NPC152212
0.8462	Intermediate Similarity	NPC320088
0.8462	Intermediate Similarity	NPC233029
0.8462	Intermediate Similarity	NPC26601
0.8462	Intermediate Similarity	NPC210148
0.8447	Intermediate Similarity	NPC134858
0.8438	Intermediate Similarity	NPC79402
0.8438	Intermediate Similarity	NPC80759
0.843	Intermediate Similarity	NPC30182
0.843	Intermediate Similarity	NPC478091
0.843	Intermediate Similarity	NPC478092

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 NPC99659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	815
0.2-0.3	1043
0.3-0.4	2024
0.4-0.5	2587
0.5-0.6	1685
0.6-0.7	583
0.7-0.8	155
0.8-0.85	30
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD4584	Approved
0.8973	High Similarity	NPD4664	Clinical (unspecified phase)
0.8509	High Similarity	NPD3051	Approved
0.8431	Intermediate Similarity	NPD2420	Approved
0.8431	Intermediate Similarity	NPD2421	Approved
0.8415	Intermediate Similarity	NPD8252	Approved
0.8415	Intermediate Similarity	NPD8251	Approved
0.8415	Intermediate Similarity	NPD8099	Discontinued
0.8405	Intermediate Similarity	NPD4481	Phase 3
0.8364	Intermediate Similarity	NPD8156	Discontinued
0.8354	Intermediate Similarity	NPD7298	Approved
0.8344	Intermediate Similarity	NPD2970	Approved
0.8344	Intermediate Similarity	NPD2969	Approved
0.8313	Intermediate Similarity	NPD6788	Approved
0.828	Intermediate Similarity	NPD4017	Approved
0.8182	Intermediate Similarity	NPD2489	Approved
0.8182	Intermediate Similarity	NPD27	Approved
0.816	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3641	Approved
0.8153	Intermediate Similarity	NPD3639	Approved
0.8153	Intermediate Similarity	NPD3640	Phase 3
0.8121	Intermediate Similarity	NPD3110	Approved
0.8121	Intermediate Similarity	NPD3109	Approved
0.8075	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD8054	Approved
0.807	Intermediate Similarity	NPD8053	Approved
0.8065	Intermediate Similarity	NPD5241	Discontinued
0.8038	Intermediate Similarity	NPD6031	Approved
0.8038	Intermediate Similarity	NPD6030	Approved
0.8035	Intermediate Similarity	NPD7906	Approved
0.8026	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2971	Approved
0.8012	Intermediate Similarity	NPD2968	Approved
0.795	Intermediate Similarity	NPD4773	Phase 2
0.795	Intermediate Similarity	NPD4772	Phase 2
0.7919	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4577	Approved
0.7907	Intermediate Similarity	NPD7313	Approved
0.7907	Intermediate Similarity	NPD4578	Approved
0.7907	Intermediate Similarity	NPD7312	Approved
0.7907	Intermediate Similarity	NPD7310	Approved
0.7907	Intermediate Similarity	NPD7311	Approved
0.7874	Intermediate Similarity	NPD4663	Approved
0.7867	Intermediate Similarity	NPD5718	Phase 2
0.7861	Intermediate Similarity	NPD7309	Approved
0.7857	Intermediate Similarity	NPD2898	Approved
0.7844	Intermediate Similarity	NPD4010	Discontinued
0.7834	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7831	Phase 2
0.7818	Intermediate Similarity	NPD7833	Phase 2
0.7784	Intermediate Similarity	NPD7802	Discontinued
0.7738	Intermediate Similarity	NPD6071	Discontinued
0.7722	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4055	Discovery
0.7697	Intermediate Similarity	NPD2563	Approved
0.7697	Intermediate Similarity	NPD4475	Approved
0.7697	Intermediate Similarity	NPD4474	Approved
0.7697	Intermediate Similarity	NPD2560	Approved
0.7688	Intermediate Similarity	NPD1424	Approved
0.7679	Intermediate Similarity	NPD6107	Approved
0.7673	Intermediate Similarity	NPD3845	Phase 1
0.7673	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2488	Approved
0.764	Intermediate Similarity	NPD2490	Approved
0.7625	Intermediate Similarity	NPD3124	Discontinued
0.7624	Intermediate Similarity	NPD2973	Approved
0.7624	Intermediate Similarity	NPD2974	Approved
0.7624	Intermediate Similarity	NPD2975	Approved
0.7616	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6896	Approved
0.7613	Intermediate Similarity	NPD6895	Approved
0.7602	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7124	Phase 2
0.7547	Intermediate Similarity	NPD5754	Discontinued
0.7541	Intermediate Similarity	NPD8095	Phase 1
0.7531	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4166	Phase 2
0.7516	Intermediate Similarity	NPD7598	Phase 2
0.75	Intermediate Similarity	NPD4580	Approved
0.7485	Intermediate Similarity	NPD4727	Phase 1
0.7485	Intermediate Similarity	NPD6687	Approved
0.7485	Intermediate Similarity	NPD5976	Discontinued
0.7485	Intermediate Similarity	NPD6688	Approved
0.7469	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3452	Approved
0.7459	Intermediate Similarity	NPD2494	Approved
0.7459	Intermediate Similarity	NPD2493	Approved
0.7459	Intermediate Similarity	NPD3450	Approved
0.7438	Intermediate Similarity	NPD6748	Discontinued
0.7429	Intermediate Similarity	NPD6297	Approved
0.7416	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5312	Approved
0.7414	Intermediate Similarity	NPD5313	Approved
0.7403	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4005	Discontinued
0.7391	Intermediate Similarity	NPD4420	Approved
0.7381	Intermediate Similarity	NPD5978	Approved
0.7381	Intermediate Similarity	NPD5977	Approved
0.7375	Intermediate Similarity	NPD5177	Phase 3
0.7353	Intermediate Similarity	NPD7400	Phase 3
0.734	Intermediate Similarity	NPD4583	Approved
0.734	Intermediate Similarity	NPD4582	Approved
0.7338	Intermediate Similarity	NPD5156	Approved
0.7338	Intermediate Similarity	NPD5155	Approved
0.733	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4585	Approved
0.7317	Intermediate Similarity	NPD6090	Discontinued
0.7312	Intermediate Similarity	NPD4107	Approved
0.731	Intermediate Similarity	NPD5677	Discontinued
0.7305	Intermediate Similarity	NPD7110	Phase 1
0.7305	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4004	Approved
0.7287	Intermediate Similarity	NPD4002	Approved
0.7273	Intermediate Similarity	NPD2606	Approved
0.7273	Intermediate Similarity	NPD3594	Approved
0.7273	Intermediate Similarity	NPD3595	Approved
0.7273	Intermediate Similarity	NPD2605	Approved
0.7267	Intermediate Similarity	NPD4237	Approved
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7267	Intermediate Similarity	NPD3060	Approved
0.7263	Intermediate Similarity	NPD6853	Approved
0.7263	Intermediate Similarity	NPD6851	Approved
0.725	Intermediate Similarity	NPD4726	Approved
0.725	Intermediate Similarity	NPD4721	Approved
0.725	Intermediate Similarity	NPD4725	Approved
0.7238	Intermediate Similarity	NPD7291	Discontinued
0.7237	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5005	Approved
0.7234	Intermediate Similarity	NPD5006	Approved
0.7233	Intermediate Similarity	NPD1753	Discontinued
0.7222	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD42	Phase 2
0.7216	Intermediate Similarity	NPD6042	Phase 2
0.7215	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6037	Discontinued
0.7208	Intermediate Similarity	NPD3637	Approved
0.7208	Intermediate Similarity	NPD3635	Approved
0.7208	Intermediate Similarity	NPD3636	Approved
0.7205	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4482	Phase 3
0.7178	Intermediate Similarity	NPD5160	Discontinued
0.7171	Intermediate Similarity	NPD1669	Approved
0.717	Intermediate Similarity	NPD6111	Discontinued
0.7169	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1914	Approved
0.7152	Intermediate Similarity	NPD4123	Phase 3
0.7143	Intermediate Similarity	NPD6875	Approved
0.7143	Intermediate Similarity	NPD3057	Approved
0.7143	Intermediate Similarity	NPD7047	Phase 3
0.7143	Intermediate Similarity	NPD6876	Approved
0.7134	Intermediate Similarity	NPD6666	Approved
0.7134	Intermediate Similarity	NPD6667	Approved
0.7128	Intermediate Similarity	NPD6612	Phase 2
0.7126	Intermediate Similarity	NPD6747	Phase 1
0.7108	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD5089	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7101	Intermediate Similarity	NPD5090	Approved
0.71	Intermediate Similarity	NPD6997	Phase 2
0.7083	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3920	Phase 2
0.7072	Intermediate Similarity	NPD6618	Phase 2
0.707	Intermediate Similarity	NPD7294	Phase 1
0.7068	Intermediate Similarity	NPD4040	Phase 1
0.7063	Intermediate Similarity	NPD2200	Suspended
0.7059	Intermediate Similarity	NPD5720	Discontinued
0.7059	Intermediate Similarity	NPD7034	Discontinued
0.7055	Intermediate Similarity	NPD4162	Approved
0.7053	Intermediate Similarity	NPD3533	Approved
0.7053	Intermediate Similarity	NPD2972	Approved
0.7052	Intermediate Similarity	NPD5709	Phase 3
0.7032	Intermediate Similarity	NPD7905	Discontinued
0.7027	Intermediate Similarity	NPD3921	Approved
0.7027	Intermediate Similarity	NPD3922	Approved
0.7027	Intermediate Similarity	NPD3924	Approved
0.7027	Intermediate Similarity	NPD3923	Approved
0.7025	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2674	Phase 3
0.7024	Intermediate Similarity	NPD4210	Discontinued
0.7018	Intermediate Similarity	NPD5773	Approved
0.7018	Intermediate Similarity	NPD5772	Approved
0.7018	Intermediate Similarity	NPD2978	Approved
0.7018	Intermediate Similarity	NPD2977	Approved
0.7012	Intermediate Similarity	NPD6331	Phase 2
0.7011	Intermediate Similarity	NPD4666	Phase 3
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD6072	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data