NPASS Compound

Structure

CID158376 OpenBabel06191715532D 24 27 0 0 1 0 0 0 0 0999 V2000 1.6954 -3.8510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3857 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0165 1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6552 -2.9261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5057 -2.4556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5107 -1.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5148 -2.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0068 -2.9026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6636 0.0100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8224 -2.4247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6707 -0.9549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8414 -2.4150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5236 -1.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8297 0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8411 -1.4396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 -1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -0.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9823 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 1.6852 -2.8844 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7085 -0.0174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8365 0.4833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3680 -1.0166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8196 1.4443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 16 2 0 0 0 0 11 15 1 0 0 0 0 12 8 1 1 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 19 2 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	327.15
Volume:	333.293
LogP:	2.388
LogD:	2.496
LogS:	-2.32
# Rotatable Bonds:	2
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.888
Synthetic Accessibility Score:	3.137
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.85
MDCK Permeability:	1.5425493984366767e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	0.792
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.944
Plasma Protein Binding (PPB):	91.13134765625%
Volume Distribution (VD):	1.566
Pgp-substrate:	10.323784828186035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.367
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.698
CYP2D6-inhibitor:	0.143
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.899

ADMET: Excretion

Clearance (CL):	14.374
Half-life (T1/2):	0.541

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.705
AMES Toxicity:	0.528
Rat Oral Acute Toxicity:	0.619
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.845
Carcinogencity:	0.082
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC158376

Natural Product ID:	NPC158376
*Common Name:**	Corytuberine
IUPAC Name:	(6aS)-2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,11-diol
Synonyms:	Corytuberine
Standard InCHIKey:	WHFUDAOCYRYAKQ-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C19H21NO4/c1-20-7-6-11-9-14(24-3)19(22)17-15(11)12(20)8-10-4-5-13(23-2)18(21)16(10)17/h4-5,9,12,21-22H,6-8H2,1-3H3/t12-/m0/s1
SMILES:	COc1ccc2c(c1O)c1c(O)c(OC)cc3c1[C@H](C2)N(C)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227965
PubChem CID:	160500
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
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10785434]
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]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
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]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
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]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	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]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO9498	Papaver somniferum	Species	Papaveraceae	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]
NPO9498	Papaver somniferum	Species	Papaveraceae	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]
NPO29347	Hydnum aurantiacum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29086	Dovyalis hebecarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29246	Ixeris repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3020	Brickellia paniculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5075	Balaenoptera borealis	Species	Balaenopteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17311	Penicillium vulpinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29206	Lycopodium chinense	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29441	Eremophila oppositifolia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1518	Pedicularis chinensis	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1005	Pycnarrhena novoguineensis	Species	Menispermaceae	Eukaryota	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]
NPO15671	Iris decora	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29490	Taxillus yadoriki	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11791	Magnolia obovata	Species	Magnoliaceae	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
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells		IC50	=	21300.0	nM	PMID[535807]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	50000.0	nM	PMID[535808]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	200000.0	nM	PMID[535809]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	200000.0	nM	PMID[535809]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	>	200000.0	nM	PMID[535809]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[535807]
NPT2	Others	Unspecified		IC50	=	23200.0	nM	PMID[535807]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	4.0	n.a.	PMID[535807]

☑ 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 NPC158376 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	337
0.1-0.2	1634
0.2-0.3	7501
0.3-0.4	10582
0.4-0.5	5231
0.5-0.6	10624
0.6-0.7	5281
0.7-0.8	1057
0.8-0.85	232
0.85-0.9	136
0.9-0.95	58
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC145832
1.0	High Similarity	NPC205421
1.0	High Similarity	NPC81218
1.0	High Similarity	NPC474931
1.0	High Similarity	NPC12053
1.0	High Similarity	NPC117188
1.0	High Similarity	NPC306555
0.987	High Similarity	NPC212794
0.987	High Similarity	NPC13504
0.987	High Similarity	NPC306843
0.987	High Similarity	NPC78222
0.987	High Similarity	NPC96603
0.987	High Similarity	NPC253043
0.987	High Similarity	NPC196447
0.987	High Similarity	NPC136508
0.987	High Similarity	NPC477563
0.9805	High Similarity	NPC324144
0.9805	High Similarity	NPC1229
0.9675	High Similarity	NPC166014
0.9675	High Similarity	NPC27410
0.9623	High Similarity	NPC192135
0.9623	High Similarity	NPC477020
0.9623	High Similarity	NPC66341
0.9565	High Similarity	NPC320223
0.9565	High Similarity	NPC114364
0.956	High Similarity	NPC239775
0.9545	High Similarity	NPC476572
0.9497	High Similarity	NPC26240
0.9497	High Similarity	NPC477562
0.9497	High Similarity	NPC69712
0.9497	High Similarity	NPC168753
0.9497	High Similarity	NPC118274
0.9441	High Similarity	NPC128560
0.9441	High Similarity	NPC199465
0.9441	High Similarity	NPC229166
0.9416	High Similarity	NPC325871
0.9416	High Similarity	NPC99659
0.9363	High Similarity	NPC60186
0.9308	High Similarity	NPC81247
0.9308	High Similarity	NPC35627
0.9308	High Similarity	NPC476573
0.9268	High Similarity	NPC474507
0.9221	High Similarity	NPC326316
0.9221	High Similarity	NPC81733
0.9217	High Similarity	NPC135772
0.9157	High Similarity	NPC116284
0.9146	High Similarity	NPC476577
0.9146	High Similarity	NPC148709
0.9146	High Similarity	NPC173416
0.913	High Similarity	NPC247389
0.913	High Similarity	NPC298979
0.9096	High Similarity	NPC476574
0.9096	High Similarity	NPC155442
0.9096	High Similarity	NPC312918
0.9096	High Similarity	NPC477561
0.9068	High Similarity	NPC24264
0.9068	High Similarity	NPC219341
0.9068	High Similarity	NPC476432
0.9045	High Similarity	NPC189266
0.9045	High Similarity	NPC2413
0.9045	High Similarity	NPC184026
0.9045	High Similarity	NPC207757
0.9045	High Similarity	NPC5238
0.9045	High Similarity	NPC469817
0.9045	High Similarity	NPC193949
0.9045	High Similarity	NPC276588
0.9045	High Similarity	NPC110416
0.9045	High Similarity	NPC204828
0.9045	High Similarity	NPC249797
0.9045	High Similarity	NPC295691
0.9045	High Similarity	NPC39701
0.9045	High Similarity	NPC127674
0.9045	High Similarity	NPC172765
0.9045	High Similarity	NPC278799
0.9045	High Similarity	NPC54379
0.9042	High Similarity	NPC248642
0.9026	High Similarity	NPC147390
0.9026	High Similarity	NPC246587
0.9026	High Similarity	NPC428
0.9026	High Similarity	NPC476571
0.9026	High Similarity	NPC24233
0.9026	High Similarity	NPC135538
0.9006	High Similarity	NPC302527
0.9006	High Similarity	NPC16805
0.9006	High Similarity	NPC167546
0.9006	High Similarity	NPC225774
0.8988	High Similarity	NPC156576
0.8968	High Similarity	NPC477565
0.8968	High Similarity	NPC103379
0.8961	High Similarity	NPC321505
0.8961	High Similarity	NPC179825
0.8961	High Similarity	NPC191376
0.8951	High Similarity	NPC13916
0.8951	High Similarity	NPC264850
0.8922	High Similarity	NPC126284
0.891	High Similarity	NPC220858
0.891	High Similarity	NPC97221
0.891	High Similarity	NPC88249
0.891	High Similarity	NPC151895
0.891	High Similarity	NPC192768
0.8896	High Similarity	NPC210918
0.8895	High Similarity	NPC478093
0.8889	High Similarity	NPC82763
0.8889	High Similarity	NPC24465
0.8868	High Similarity	NPC203784
0.8868	High Similarity	NPC186063
0.8868	High Similarity	NPC170503
0.8868	High Similarity	NPC126519
0.8855	High Similarity	NPC477558
0.8844	High Similarity	NPC478092
0.8844	High Similarity	NPC478091
0.8844	High Similarity	NPC473589
0.8844	High Similarity	NPC30182
0.8839	High Similarity	NPC476151
0.8831	High Similarity	NPC185838
0.883	High Similarity	NPC186546
0.883	High Similarity	NPC476576
0.882	High Similarity	NPC160298
0.882	High Similarity	NPC306902
0.882	High Similarity	NPC232924
0.882	High Similarity	NPC266753
0.882	High Similarity	NPC477559
0.881	High Similarity	NPC32154
0.8805	High Similarity	NPC244112
0.878	High Similarity	NPC204947
0.878	High Similarity	NPC210140
0.878	High Similarity	NPC150879
0.8772	High Similarity	NPC320088
0.8772	High Similarity	NPC57036
0.8765	High Similarity	NPC80759
0.8765	High Similarity	NPC79402
0.8735	High Similarity	NPC149090
0.8735	High Similarity	NPC19520
0.8735	High Similarity	NPC231371
0.8727	High Similarity	NPC204908
0.8727	High Similarity	NPC83198
0.8721	High Similarity	NPC275680
0.8721	High Similarity	NPC22115
0.872	High Similarity	NPC124657
0.8704	High Similarity	NPC119649
0.8704	High Similarity	NPC271388
0.8704	High Similarity	NPC235143
0.8704	High Similarity	NPC230956
0.8704	High Similarity	NPC205255
0.869	High Similarity	NPC241704
0.8683	High Similarity	NPC152680
0.8683	High Similarity	NPC190783
0.8683	High Similarity	NPC232386
0.8679	High Similarity	NPC26601
0.8675	High Similarity	NPC6152
0.8675	High Similarity	NPC152212
0.8663	High Similarity	NPC214116
0.8659	High Similarity	NPC276944
0.8659	High Similarity	NPC134858
0.8659	High Similarity	NPC169743
0.8659	High Similarity	NPC238530
0.8659	High Similarity	NPC232514
0.8655	High Similarity	NPC33902
0.8655	High Similarity	NPC276674
0.8642	High Similarity	NPC221864
0.8639	High Similarity	NPC118633
0.8639	High Similarity	NPC148693
0.8639	High Similarity	NPC294790
0.8631	High Similarity	NPC329969
0.8625	High Similarity	NPC477564
0.8625	High Similarity	NPC2295
0.8621	High Similarity	NPC475754
0.8616	High Similarity	NPC277669
0.8616	High Similarity	NPC76213
0.8605	High Similarity	NPC16357
0.8605	High Similarity	NPC95426
0.8605	High Similarity	NPC302245
0.8599	High Similarity	NPC210437
0.8599	High Similarity	NPC106295
0.8599	High Similarity	NPC476144
0.8599	High Similarity	NPC16107
0.8599	High Similarity	NPC51957
0.8598	High Similarity	NPC233650
0.8589	High Similarity	NPC205167
0.8589	High Similarity	NPC249274
0.8588	High Similarity	NPC220961
0.8571	High Similarity	NPC470925
0.8571	High Similarity	NPC328750
0.8571	High Similarity	NPC474915
0.8571	High Similarity	NPC213206
0.8571	High Similarity	NPC78284
0.8571	High Similarity	NPC188163
0.8555	High Similarity	NPC65312
0.8555	High Similarity	NPC139783
0.8544	High Similarity	NPC7467
0.8538	High Similarity	NPC286119
0.8538	High Similarity	NPC474506
0.8538	High Similarity	NPC32413
0.8528	High Similarity	NPC111485
0.8506	High Similarity	NPC314682
0.8503	High Similarity	NPC241055
0.8494	Intermediate Similarity	NPC268503
0.8494	Intermediate Similarity	NPC256012
0.8494	Intermediate Similarity	NPC304659
0.8494	Intermediate Similarity	NPC86144

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 NPC158376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	799
0.2-0.3	1029
0.3-0.4	2025
0.4-0.5	2590
0.5-0.6	1643
0.6-0.7	662
0.7-0.8	170
0.8-0.85	21
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8896	High Similarity	NPD2420	Approved
0.8896	High Similarity	NPD2421	Approved
0.8614	High Similarity	NPD27	Approved
0.8614	High Similarity	NPD2489	Approved
0.8606	High Similarity	NPD3051	Approved
0.8599	High Similarity	NPD4584	Approved
0.8571	High Similarity	NPD4664	Clinical (unspecified phase)
0.8555	High Similarity	NPD7906	Approved
0.8554	High Similarity	NPD2969	Approved
0.8554	High Similarity	NPD2970	Approved
0.8488	Intermediate Similarity	NPD8053	Approved
0.8488	Intermediate Similarity	NPD8054	Approved
0.843	Intermediate Similarity	NPD4577	Approved
0.843	Intermediate Similarity	NPD4578	Approved
0.843	Intermediate Similarity	NPD7313	Approved
0.843	Intermediate Similarity	NPD7312	Approved
0.843	Intermediate Similarity	NPD7311	Approved
0.843	Intermediate Similarity	NPD7310	Approved
0.8391	Intermediate Similarity	NPD4663	Approved
0.8382	Intermediate Similarity	NPD7309	Approved
0.8293	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD2898	Approved
0.8176	Intermediate Similarity	NPD5241	Discontinued
0.8166	Intermediate Similarity	NPD4010	Discontinued
0.8155	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3845	Phase 1
0.8081	Intermediate Similarity	NPD8099	Discontinued
0.8081	Intermediate Similarity	NPD8252	Approved
0.8081	Intermediate Similarity	NPD8251	Approved
0.807	Intermediate Similarity	NPD4481	Phase 3
0.8045	Intermediate Similarity	NPD2488	Approved
0.8045	Intermediate Similarity	NPD2490	Approved
0.8036	Intermediate Similarity	NPD7831	Phase 2
0.8036	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7833	Phase 2
0.8035	Intermediate Similarity	NPD8156	Discontinued
0.8011	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6788	Approved
0.7946	Intermediate Similarity	NPD3450	Approved
0.7946	Intermediate Similarity	NPD2493	Approved
0.7946	Intermediate Similarity	NPD2494	Approved
0.7946	Intermediate Similarity	NPD3452	Approved
0.7939	Intermediate Similarity	NPD4017	Approved
0.7914	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7298	Approved
0.7853	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6071	Discontinued
0.7844	Intermediate Similarity	NPD4773	Phase 2
0.7844	Intermediate Similarity	NPD4772	Phase 2
0.7819	Intermediate Similarity	NPD4583	Approved
0.7819	Intermediate Similarity	NPD4582	Approved
0.7811	Intermediate Similarity	NPD2560	Approved
0.7811	Intermediate Similarity	NPD2563	Approved
0.7771	Intermediate Similarity	NPD3110	Approved
0.7771	Intermediate Similarity	NPD3109	Approved
0.7766	Intermediate Similarity	NPD4002	Approved
0.7766	Intermediate Similarity	NPD4004	Approved
0.7765	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2975	Approved
0.773	Intermediate Similarity	NPD2974	Approved
0.773	Intermediate Similarity	NPD2973	Approved
0.7711	Intermediate Similarity	NPD3639	Approved
0.7711	Intermediate Similarity	NPD6031	Approved
0.7711	Intermediate Similarity	NPD6030	Approved
0.7711	Intermediate Similarity	NPD3641	Approved
0.7711	Intermediate Similarity	NPD3640	Phase 3
0.7709	Intermediate Similarity	NPD2968	Approved
0.7709	Intermediate Similarity	NPD2971	Approved
0.7688	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4055	Discovery
0.7607	Intermediate Similarity	NPD5177	Phase 3
0.7606	Intermediate Similarity	NPD4580	Approved
0.7602	Intermediate Similarity	NPD7047	Phase 3
0.758	Intermediate Similarity	NPD5156	Approved
0.758	Intermediate Similarity	NPD5155	Approved
0.7578	Intermediate Similarity	NPD1753	Discontinued
0.755	Intermediate Similarity	NPD6997	Phase 2
0.7545	Intermediate Similarity	NPD6090	Discontinued
0.7544	Intermediate Similarity	NPD2978	Approved
0.7544	Intermediate Similarity	NPD2977	Approved
0.7532	Intermediate Similarity	NPD5718	Phase 2
0.7528	Intermediate Similarity	NPD6042	Phase 2
0.7528	Intermediate Similarity	NPD42	Phase 2
0.7516	Intermediate Similarity	NPD2606	Approved
0.7516	Intermediate Similarity	NPD2605	Approved
0.7516	Intermediate Similarity	NPD3595	Approved
0.7516	Intermediate Similarity	NPD3594	Approved
0.7515	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3060	Approved
0.7486	Intermediate Similarity	NPD7802	Discontinued
0.7485	Intermediate Similarity	NPD4726	Approved
0.7485	Intermediate Similarity	NPD4721	Approved
0.7485	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4725	Approved
0.7484	Intermediate Similarity	NPD2674	Phase 3
0.7468	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3636	Approved
0.7452	Intermediate Similarity	NPD3637	Approved
0.7452	Intermediate Similarity	NPD3635	Approved
0.7448	Intermediate Similarity	NPD4040	Phase 1
0.7444	Intermediate Similarity	NPD6297	Approved
0.7381	Intermediate Similarity	NPD4123	Phase 3
0.7381	Intermediate Similarity	NPD1424	Approved
0.7381	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4475	Approved
0.7375	Intermediate Similarity	NPD4474	Approved
0.7344	Intermediate Similarity	NPD3448	Approved
0.7344	Intermediate Similarity	NPD2491	Approved
0.7344	Intermediate Similarity	NPD3057	Approved
0.733	Intermediate Similarity	NPD4666	Phase 3
0.7321	Intermediate Similarity	NPD3124	Discontinued
0.7312	Intermediate Similarity	NPD3145	Approved
0.7312	Intermediate Similarity	NPD3144	Approved
0.731	Intermediate Similarity	NPD4005	Discontinued
0.7301	Intermediate Similarity	NPD6895	Approved
0.7301	Intermediate Similarity	NPD6896	Approved
0.7296	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4237	Approved
0.7289	Intermediate Similarity	NPD4236	Phase 3
0.7288	Intermediate Similarity	NPD6107	Approved
0.7283	Intermediate Similarity	NPD6853	Approved
0.7283	Intermediate Similarity	NPD6851	Approved
0.7277	Intermediate Similarity	NPD8095	Phase 1
0.7273	Intermediate Similarity	NPD5709	Phase 3
0.7262	Intermediate Similarity	NPD7124	Phase 2
0.7262	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6666	Approved
0.7262	Intermediate Similarity	NPD6667	Approved
0.7254	Intermediate Similarity	NPD3533	Approved
0.7254	Intermediate Similarity	NPD2972	Approved
0.7246	Intermediate Similarity	NPD5754	Discontinued
0.7241	Intermediate Similarity	NPD5772	Approved
0.7241	Intermediate Similarity	NPD5773	Approved
0.7235	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4257	Approved
0.7229	Intermediate Similarity	NPD4256	Phase 2
0.7228	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4420	Approved
0.7225	Intermediate Similarity	NPD6072	Discontinued
0.7222	Intermediate Similarity	NPD2238	Phase 2
0.7219	Intermediate Similarity	NPD7598	Phase 2
0.7216	Intermediate Similarity	NPD5604	Discontinued
0.7209	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5160	Discontinued
0.7202	Intermediate Similarity	NPD3692	Discontinued
0.7198	Intermediate Similarity	NPD7479	Phase 2
0.7195	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2122	Discontinued
0.7193	Intermediate Similarity	NPD5976	Discontinued
0.7193	Intermediate Similarity	NPD4727	Phase 1
0.7189	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7447	Phase 1
0.7174	Intermediate Similarity	NPD7549	Discontinued
0.7168	Intermediate Similarity	NPD4678	Approved
0.7168	Intermediate Similarity	NPD4675	Approved
0.7157	Intermediate Similarity	NPD7907	Approved
0.7151	Intermediate Similarity	NPD6747	Phase 1
0.7151	Intermediate Similarity	NPD4166	Phase 2
0.7143	Intermediate Similarity	NPD4873	Discontinued
0.7143	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6748	Discontinued
0.7135	Intermediate Similarity	NPD5677	Discontinued
0.7135	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2230	Approved
0.7134	Intermediate Similarity	NPD823	Approved
0.7134	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2232	Approved
0.7134	Intermediate Similarity	NPD2233	Approved
0.7134	Intermediate Similarity	NPD817	Approved
0.7126	Intermediate Similarity	NPD7037	Approved
0.7118	Intermediate Similarity	NPD7213	Phase 3
0.7118	Intermediate Similarity	NPD7212	Phase 2
0.7111	Intermediate Similarity	NPD6687	Approved
0.7111	Intermediate Similarity	NPD6688	Approved
0.7107	Intermediate Similarity	NPD3053	Approved
0.7107	Intermediate Similarity	NPD3055	Approved
0.7102	Intermediate Similarity	NPD5978	Approved
0.7102	Intermediate Similarity	NPD5977	Approved
0.7101	Intermediate Similarity	NPD2677	Approved
0.71	Intermediate Similarity	NPD7827	Phase 1
0.7099	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4093	Discontinued
0.7093	Intermediate Similarity	NPD1914	Approved
0.709	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1669	Approved
0.7083	Intermediate Similarity	NPD4162	Approved
0.7079	Intermediate Similarity	NPD7400	Phase 3
0.7077	Intermediate Similarity	NPD5005	Approved
0.7077	Intermediate Similarity	NPD5006	Approved
0.7065	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4107	Approved
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD5087	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