NPASS Compound

Structure

CID170503 OpenBabel06191715542D 21 24 0 0 1 0 0 0 0 0999 V2000 0.3216 2.1511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5753 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3717 -2.3243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -1.4044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5666 -2.7696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6004 -0.9298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3764 -1.3628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3803 -2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0064 -2.7474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5747 0.0094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7784 -2.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5814 -0.9038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7953 -1.3751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7964 -2.2859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7853 0.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7961 -1.3626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0053 -0.9136 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 1.5950 -2.7302 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7802 1.3671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7875 0.4550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 9 1 1 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	281.14
Volume:	298.417
LogP:	2.501
LogD:	2.828
LogS:	-2.1
# Rotatable Bonds:	2
TPSA:	30.49
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.917
Synthetic Accessibility Score:	2.868
Fsp3:	0.333
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:	-4.923
MDCK Permeability:	1.8711067241383716e-05
Pgp-inhibitor:	0.499
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	70.45613861083984%
Volume Distribution (VD):	2.279
Pgp-substrate:	10.288162231445312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.713
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.285
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.563
CYP2D6-inhibitor:	0.763
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.896

ADMET: Excretion

Clearance (CL):	4.667
Half-life (T1/2):	0.239

ADMET: Toxicity

hERG Blockers:	0.647
Human Hepatotoxicity (H-HT):	0.531
Drug-inuced Liver Injury (DILI):	0.4
AMES Toxicity:	0.414
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.269
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC170503

Natural Product ID:	NPC170503
*Common Name:**	(S)-1,2-Dimethoxy-5,6,6A,7-Tetrahydro-4H-Dibenzo[De,G]Quinoline
IUPAC Name:	(6aS)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms:
Standard InCHIKey:	QQKAHDMMPBQDAC-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C18H19NO2/c1-20-15-10-12-7-8-19-14-9-11-5-3-4-6-13(11)17(16(12)14)18(15)21-2/h3-6,10,14,19H,7-9H2,1-2H3/t14-/m0/s1
SMILES:	COc1cc2CCN[C@H]3Cc4ccccc4-c(c23)c1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL325416
PubChem CID:	41169
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
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	Stems	Tainan Hsien, Taiwan, Republic of China	2000-JAN	PMID[16038551]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[18175990]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19938815]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13118	Paeonia officinalis	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13118	Paeonia officinalis	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13097	Guatteria amplifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO474	Beilschmiedia kunstleri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11948	Ferulago sylvatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20070.1	Crinum stuhlmannii subsp. delagoense	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12080	Metrodorea flavida	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10161	Macaranga pleiostemona	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3390	Radermachia sinica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15978	Nalanthamala diospyri	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13118	Paeonia officinalis	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7346	Ligularia odontomanes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11817	Seiridium cardinale	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1187	Baccharis scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12316	Pterospermum lanceolatum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11706	Gordonia terrae	Species	Gordoniaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1863	Alpinia pricei	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12193	Metadina trichotoma	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8078	Palaquium leiocarpum	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13097	Guatteria amplifolia	Species	Annonaceae	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	1
Others	4

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Aggregation	=	77.1	%	PMID[524458]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Aggregation	=	0.0	%	PMID[524458]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Aggregation	=	30.6	%	PMID[524458]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	IC50	=	210600.0	nM	PMID[524458]

☑ 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 NPC170503 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	366
0.1-0.2	2038
0.2-0.3	11429
0.3-0.4	6258
0.4-0.5	8595
0.5-0.6	11004
0.6-0.7	2244
0.7-0.8	452
0.8-0.85	184
0.85-0.9	90
0.9-0.95	28
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126519
1.0	High Similarity	NPC203784
0.9592	High Similarity	NPC81733
0.9592	High Similarity	NPC326316
0.9542	High Similarity	NPC304659
0.9542	High Similarity	NPC86144
0.9542	High Similarity	NPC35627
0.9542	High Similarity	NPC81247
0.9542	High Similarity	NPC476573
0.9412	High Similarity	NPC189470
0.9355	High Similarity	NPC204947
0.9276	High Similarity	NPC476572
0.9272	High Similarity	NPC325871
0.9272	High Similarity	NPC99659
0.9241	High Similarity	NPC192135
0.9241	High Similarity	NPC477020
0.9241	High Similarity	NPC66341
0.9236	High Similarity	NPC69712
0.9236	High Similarity	NPC26240
0.9236	High Similarity	NPC477562
0.9236	High Similarity	NPC6152
0.9156	High Similarity	NPC477559
0.9156	High Similarity	NPC306902
0.9156	High Similarity	NPC27410
0.9156	High Similarity	NPC166014
0.9156	High Similarity	NPC266753
0.9156	High Similarity	NPC160298
0.9156	High Similarity	NPC232924
0.9114	High Similarity	NPC152212
0.9012	High Similarity	NPC474507
0.9012	High Similarity	NPC267408
0.9006	High Similarity	NPC148709
0.9006	High Similarity	NPC476577
0.9006	High Similarity	NPC112575
0.9006	High Similarity	NPC173416
0.8981	High Similarity	NPC225774
0.8957	High Similarity	NPC474506
0.8957	High Similarity	NPC32413
0.8951	High Similarity	NPC23219
0.8944	High Similarity	NPC477558
0.894	High Similarity	NPC207824
0.894	High Similarity	NPC60538
0.8924	High Similarity	NPC476432
0.8924	High Similarity	NPC24264
0.8924	High Similarity	NPC219341
0.8917	High Similarity	NPC324144
0.8912	High Similarity	NPC470925
0.8896	High Similarity	NPC258695
0.8896	High Similarity	NPC470879
0.8868	High Similarity	NPC306555
0.8868	High Similarity	NPC474931
0.8868	High Similarity	NPC158376
0.8868	High Similarity	NPC12053
0.8868	High Similarity	NPC145832
0.8868	High Similarity	NPC298979
0.8868	High Similarity	NPC81218
0.8868	High Similarity	NPC117188
0.8868	High Similarity	NPC205421
0.8868	High Similarity	NPC247389
0.8861	High Similarity	NPC13504
0.8861	High Similarity	NPC96603
0.8861	High Similarity	NPC212794
0.8861	High Similarity	NPC253043
0.8861	High Similarity	NPC196447
0.8861	High Similarity	NPC306843
0.8861	High Similarity	NPC78222
0.8861	High Similarity	NPC302527
0.8861	High Similarity	NPC136508
0.8861	High Similarity	NPC477563
0.8861	High Similarity	NPC16805
0.8861	High Similarity	NPC167546
0.8848	High Similarity	NPC135772
0.8844	High Similarity	NPC314682
0.8841	High Similarity	NPC155442
0.8841	High Similarity	NPC476574
0.8841	High Similarity	NPC312918
0.8841	High Similarity	NPC477561
0.8836	High Similarity	NPC253429
0.8831	High Similarity	NPC2295
0.8831	High Similarity	NPC477564
0.8824	High Similarity	NPC76213
0.8824	High Similarity	NPC277669
0.8816	High Similarity	NPC219162
0.8816	High Similarity	NPC92541
0.8812	High Similarity	NPC241055
0.8808	High Similarity	NPC476144
0.8808	High Similarity	NPC210437
0.8808	High Similarity	NPC16107
0.8808	High Similarity	NPC106295
0.8808	High Similarity	NPC51957
0.8797	High Similarity	NPC1229
0.8784	High Similarity	NPC188163
0.8784	High Similarity	NPC474915
0.8784	High Similarity	NPC213206
0.8784	High Similarity	NPC328750
0.8766	High Similarity	NPC470924
0.875	High Similarity	NPC210918
0.875	High Similarity	NPC7467
0.8742	High Similarity	NPC168409
0.8684	High Similarity	NPC90844
0.8684	High Similarity	NPC95075
0.8684	High Similarity	NPC253883
0.8684	High Similarity	NPC144863
0.8675	High Similarity	NPC476575
0.8667	High Similarity	NPC128019
0.8667	High Similarity	NPC136860
0.8667	High Similarity	NPC476567
0.8662	High Similarity	NPC79328
0.8654	High Similarity	NPC187022
0.8654	High Similarity	NPC80129
0.8654	High Similarity	NPC244112
0.8642	High Similarity	NPC168753
0.8642	High Similarity	NPC118274
0.8631	High Similarity	NPC57036
0.8627	High Similarity	NPC130941
0.8608	High Similarity	NPC7393
0.8589	High Similarity	NPC149090
0.8589	High Similarity	NPC19520
0.8589	High Similarity	NPC239775
0.8588	High Similarity	NPC475754
0.858	High Similarity	NPC476576
0.858	High Similarity	NPC186546
0.8562	High Similarity	NPC476151
0.8562	High Similarity	NPC475393
0.8562	High Similarity	NPC160692
0.8553	High Similarity	NPC185838
0.8537	High Similarity	NPC285941
0.8509	High Similarity	NPC39103
0.8509	High Similarity	NPC2770
0.8494	Intermediate Similarity	NPC320223
0.8494	Intermediate Similarity	NPC114364
0.8485	Intermediate Similarity	NPC128560
0.8485	Intermediate Similarity	NPC199465
0.8485	Intermediate Similarity	NPC229166
0.8481	Intermediate Similarity	NPC29647
0.8452	Intermediate Similarity	NPC103379
0.8452	Intermediate Similarity	NPC477565
0.8452	Intermediate Similarity	NPC275132
0.8443	Intermediate Similarity	NPC220961
0.8443	Intermediate Similarity	NPC126284
0.8442	Intermediate Similarity	NPC191376
0.8442	Intermediate Similarity	NPC179825
0.8442	Intermediate Similarity	NPC321505
0.843	Intermediate Similarity	NPC117717
0.8418	Intermediate Similarity	NPC278799
0.8418	Intermediate Similarity	NPC249797
0.8418	Intermediate Similarity	NPC295691
0.8418	Intermediate Similarity	NPC110416
0.8418	Intermediate Similarity	NPC39701
0.8418	Intermediate Similarity	NPC2413
0.8418	Intermediate Similarity	NPC193949
0.8418	Intermediate Similarity	NPC127674
0.8418	Intermediate Similarity	NPC469817
0.8418	Intermediate Similarity	NPC172765
0.8418	Intermediate Similarity	NPC216459
0.8418	Intermediate Similarity	NPC54379
0.8418	Intermediate Similarity	NPC41178
0.8418	Intermediate Similarity	NPC276588
0.8418	Intermediate Similarity	NPC5238
0.8418	Intermediate Similarity	NPC184026
0.8418	Intermediate Similarity	NPC204828
0.8418	Intermediate Similarity	NPC189266
0.8418	Intermediate Similarity	NPC207757
0.8418	Intermediate Similarity	NPC138487
0.8408	Intermediate Similarity	NPC114124
0.8408	Intermediate Similarity	NPC26601
0.8395	Intermediate Similarity	NPC209377
0.8387	Intermediate Similarity	NPC475959
0.8387	Intermediate Similarity	NPC246587
0.8387	Intermediate Similarity	NPC428
0.8387	Intermediate Similarity	NPC147390
0.8387	Intermediate Similarity	NPC476571
0.8387	Intermediate Similarity	NPC24233
0.8387	Intermediate Similarity	NPC135538
0.8385	Intermediate Similarity	NPC60186
0.8373	Intermediate Similarity	NPC329969
0.8366	Intermediate Similarity	NPC294249
0.8365	Intermediate Similarity	NPC146288
0.8344	Intermediate Similarity	NPC195392
0.8344	Intermediate Similarity	NPC223077
0.8344	Intermediate Similarity	NPC56887
0.8344	Intermediate Similarity	NPC193853
0.8343	Intermediate Similarity	NPC248642
0.8333	Intermediate Similarity	NPC233650
0.8302	Intermediate Similarity	NPC76079
0.8294	Intermediate Similarity	NPC302275
0.8294	Intermediate Similarity	NPC156576
0.8282	Intermediate Similarity	NPC4138
0.8282	Intermediate Similarity	NPC284183
0.8282	Intermediate Similarity	NPC121275
0.8282	Intermediate Similarity	NPC134858
0.828	Intermediate Similarity	NPC88249
0.828	Intermediate Similarity	NPC151895
0.828	Intermediate Similarity	NPC220858
0.828	Intermediate Similarity	NPC192768
0.828	Intermediate Similarity	NPC97221
0.8274	Intermediate Similarity	NPC190461
0.8261	Intermediate Similarity	NPC477080
0.8253	Intermediate Similarity	NPC475215
0.8253	Intermediate Similarity	NPC108434

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 NPC170503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	795
0.2-0.3	1089
0.3-0.4	1780
0.4-0.5	2766
0.5-0.6	1697
0.6-0.7	622
0.7-0.8	170
0.8-0.85	9
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8808	High Similarity	NPD4584	Approved
0.8784	High Similarity	NPD4664	Clinical (unspecified phase)
0.8654	High Similarity	NPD7298	Approved
0.8571	High Similarity	NPD6030	Approved
0.8571	High Similarity	NPD6031	Approved
0.8377	Intermediate Similarity	NPD2420	Approved
0.8377	Intermediate Similarity	NPD2421	Approved
0.8312	Intermediate Similarity	NPD3845	Phase 1
0.8312	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD4017	Approved
0.8148	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3051	Approved
0.811	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3109	Approved
0.8067	Intermediate Similarity	NPD3110	Approved
0.8038	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7598	Phase 2
0.8013	Intermediate Similarity	NPD5241	Discontinued
0.7987	Intermediate Similarity	NPD3641	Approved
0.7987	Intermediate Similarity	NPD3639	Approved
0.7987	Intermediate Similarity	NPD4727	Phase 1
0.7987	Intermediate Similarity	NPD3640	Phase 3
0.7974	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD2970	Approved
0.7964	Intermediate Similarity	NPD2969	Approved
0.7929	Intermediate Similarity	NPD8251	Approved
0.7929	Intermediate Similarity	NPD8099	Discontinued
0.7929	Intermediate Similarity	NPD8252	Approved
0.7927	Intermediate Similarity	NPD6788	Approved
0.7917	Intermediate Similarity	NPD27	Approved
0.7917	Intermediate Similarity	NPD2489	Approved
0.7917	Intermediate Similarity	NPD4481	Phase 3
0.7882	Intermediate Similarity	NPD8156	Discontinued
0.7862	Intermediate Similarity	NPD1424	Approved
0.7844	Intermediate Similarity	NPD6107	Approved
0.7834	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD5718	Phase 2
0.7811	Intermediate Similarity	NPD2898	Approved
0.7803	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4166	Phase 2
0.7791	Intermediate Similarity	NPD6297	Approved
0.7791	Intermediate Similarity	NPD4772	Phase 2
0.7791	Intermediate Similarity	NPD4773	Phase 2
0.7785	Intermediate Similarity	NPD5160	Discontinued
0.7785	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7833	Phase 2
0.7771	Intermediate Similarity	NPD7831	Phase 2
0.7764	Intermediate Similarity	NPD5976	Discontinued
0.7748	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD2968	Approved
0.7657	Intermediate Similarity	NPD2971	Approved
0.7647	Intermediate Similarity	NPD4474	Approved
0.7647	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4475	Approved
0.7633	Intermediate Similarity	NPD7802	Discontinued
0.7614	Intermediate Similarity	NPD8054	Approved
0.7614	Intermediate Similarity	NPD8053	Approved
0.7614	Intermediate Similarity	NPD6851	Approved
0.7614	Intermediate Similarity	NPD6853	Approved
0.7588	Intermediate Similarity	NPD4010	Discontinued
0.7584	Intermediate Similarity	NPD7906	Approved
0.7578	Intermediate Similarity	NPD3124	Discontinued
0.7566	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4577	Approved
0.7557	Intermediate Similarity	NPD4578	Approved
0.7547	Intermediate Similarity	NPD3060	Approved
0.7547	Intermediate Similarity	NPD4162	Approved
0.753	Intermediate Similarity	NPD5720	Discontinued
0.7516	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5754	Discontinued
0.7458	Intermediate Similarity	NPD7310	Approved
0.7458	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7312	Approved
0.7458	Intermediate Similarity	NPD7311	Approved
0.7458	Intermediate Similarity	NPD7313	Approved
0.7455	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6896	Approved
0.7452	Intermediate Similarity	NPD6895	Approved
0.743	Intermediate Similarity	NPD4663	Approved
0.7429	Intermediate Similarity	NPD7479	Phase 2
0.7423	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3532	Approved
0.7419	Intermediate Similarity	NPD3530	Approved
0.7419	Intermediate Similarity	NPD3531	Approved
0.7416	Intermediate Similarity	NPD7309	Approved
0.7416	Intermediate Similarity	NPD6618	Phase 2
0.7414	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2154	Approved
0.7405	Intermediate Similarity	NPD2156	Approved
0.7405	Intermediate Similarity	NPD2155	Approved
0.7403	Intermediate Similarity	NPD2490	Approved
0.7403	Intermediate Similarity	NPD2488	Approved
0.7391	Intermediate Similarity	NPD6748	Discontinued
0.7389	Intermediate Similarity	NPD2989	Phase 2
0.7389	Intermediate Similarity	NPD2986	Phase 2
0.7384	Intermediate Similarity	NPD6071	Discontinued
0.7381	Intermediate Similarity	NPD4585	Approved
0.7375	Intermediate Similarity	NPD4257	Approved
0.7375	Intermediate Similarity	NPD4256	Phase 2
0.7371	Intermediate Similarity	NPD42	Phase 2
0.7371	Intermediate Similarity	NPD6042	Phase 2
0.7368	Intermediate Similarity	NPD6037	Discontinued
0.7366	Intermediate Similarity	NPD6612	Phase 2
0.7355	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4055	Discovery
0.7337	Intermediate Similarity	NPD2560	Approved
0.7337	Intermediate Similarity	NPD5977	Approved
0.7337	Intermediate Similarity	NPD2563	Approved
0.7337	Intermediate Similarity	NPD5978	Approved
0.7329	Intermediate Similarity	NPD5177	Phase 3
0.731	Intermediate Similarity	NPD5709	Phase 3
0.731	Intermediate Similarity	NPD7400	Phase 3
0.729	Intermediate Similarity	NPD5155	Approved
0.729	Intermediate Similarity	NPD5156	Approved
0.7278	Intermediate Similarity	NPD2977	Approved
0.7278	Intermediate Similarity	NPD2653	Approved
0.7278	Intermediate Similarity	NPD2978	Approved
0.7277	Intermediate Similarity	NPD4859	Phase 1
0.7273	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4666	Phase 3
0.7267	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD595	Approved
0.726	Intermediate Similarity	NPD593	Approved
0.7255	Intermediate Similarity	NPD3055	Approved
0.7255	Intermediate Similarity	NPD3053	Approved
0.7243	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6687	Approved
0.7241	Intermediate Similarity	NPD4083	Discontinued
0.7241	Intermediate Similarity	NPD6688	Approved
0.7239	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1669	Approved
0.7226	Intermediate Similarity	NPD2606	Approved
0.7226	Intermediate Similarity	NPD2605	Approved
0.7226	Intermediate Similarity	NPD3594	Approved
0.7226	Intermediate Similarity	NPD3595	Approved
0.7204	Intermediate Similarity	NPD2974	Approved
0.7204	Intermediate Similarity	NPD2975	Approved
0.7204	Intermediate Similarity	NPD7034	Discontinued
0.7204	Intermediate Similarity	NPD2973	Approved
0.7198	Intermediate Similarity	NPD7291	Discontinued
0.7195	Intermediate Similarity	NPD2120	Phase 2
0.719	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1753	Discontinued
0.7178	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5313	Approved
0.7175	Intermediate Similarity	NPD4873	Discontinued
0.7175	Intermediate Similarity	NPD5312	Approved
0.717	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3637	Approved
0.7161	Intermediate Similarity	NPD3635	Approved
0.7161	Intermediate Similarity	NPD3636	Approved
0.716	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7153	Discontinued
0.716	Intermediate Similarity	NPD7110	Phase 1
0.7135	Intermediate Similarity	NPD7262	Phase 1
0.7135	Intermediate Similarity	NPD3920	Phase 2
0.7134	Intermediate Similarity	NPD1336	Approved
0.7134	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3049	Approved
0.7128	Intermediate Similarity	NPD8095	Phase 1
0.7126	Intermediate Similarity	NPD1914	Approved
0.712	Intermediate Similarity	NPD4040	Phase 1
0.7117	Intermediate Similarity	NPD2460	Phase 3
0.7117	Intermediate Similarity	NPD2459	Approved
0.7117	Intermediate Similarity	NPD2458	Approved
0.7108	Intermediate Similarity	NPD2874	Phase 2
0.7108	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7124	Phase 2
0.709	Intermediate Similarity	NPD4580	Approved
0.7089	Intermediate Similarity	NPD2674	Phase 3
0.7083	Intermediate Similarity	NPD2883	Discontinued
0.7079	Intermediate Similarity	NPD5096	Phase 3
0.7079	Intermediate Similarity	NPD5095	Phase 3
0.7073	Intermediate Similarity	NPD6331	Phase 2
0.7066	Intermediate Similarity	NPD6090	Discontinued
0.7062	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3452	Approved
0.7053	Intermediate Similarity	NPD3450	Approved
0.7053	Intermediate Similarity	NPD2494	Approved
0.7053	Intermediate Similarity	NPD2493	Approved
0.7044	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2677	Approved
0.7025	Intermediate Similarity	NPD7294	Phase 1
0.7024	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5722	Discontinued
0.7017	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3349	Phase 2
0.7006	Intermediate Similarity	NPD7020	Approved
0.7006	Intermediate Similarity	NPD7019	Approved
0.7006	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6996	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data