NPASS Compound

Structure

CID215098 OpenBabel06191716002D 28 32 0 0 1 0 0 0 0 0999 V2000 0.1045 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4126 -1.2818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8164 0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -2.3523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0962 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9050 1.5882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7653 -1.8171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4563 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7435 -2.0250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1254 -0.1229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3118 0.6746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9105 1.4836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 22 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 26 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 12 17 2 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 13 1 6 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 12 1 1 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 21 23 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.14
Volume:	374.273
LogP:	2.564
LogD:	2.631
LogS:	-4.415
# Rotatable Bonds:	3
TPSA:	66.46
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	3.416
Fsp3:	0.381
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:	-4.89
MDCK Permeability:	5.139606582815759e-05
Pgp-inhibitor:	0.696
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	86.0892562866211%
Volume Distribution (VD):	1.833
Pgp-substrate:	7.338064193725586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.667
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.93
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	11.727
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.459
AMES Toxicity:	0.238
Rat Oral Acute Toxicity:	0.66
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.056
Carcinogencity:	0.799
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.842

Download Data

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

Natural Product: NPC215098

Natural Product ID:	NPC215098
*Common Name:**	(3R)-6,7-Dimethoxy-3-[(5S)-6-Methyl-7,8-Dihydro-5H-[1,3]Dioxolo[4,5-G]Isoquinolin-5-Yl]-3H-2-Benzofuran-1-One
IUPAC Name:	(3R)-6,7-dimethoxy-3-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Synonyms:	D-Beta-Hydrastine
Standard InCHIKey:	JZUTXVTYJDCMDU-RBUKOAKNSA-N
Standard InCHI:	InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m0/s1
SMILES:	COc1c(OC)ccc2c1C(=O)O[C@H]2[C@H]1N(C)CCc2c1cc1OCOc1c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1441048
PubChem CID:	656743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002188] Phthalide isoquinolines

*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
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20339	Corydalis stricta	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20339	Corydalis stricta	Species	Papaveraceae	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
AC50	2
IC50	1
Others	4
Potency	5

Activity Type	# Activity
Individual Protein	3
Organism	1
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	2818.4	nM	PMID[512997]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	9.75	%	PMID[512999]
NPT2	Others	Unspecified		Potency	=	3662.6	nM	PMID[512997]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	15101.4	nM	PMID[512998]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-1.4	%	PMID[512999]
NPT2	Others	Unspecified		Ac50	n.a.	0.631	uM	PMID[513000]
NPT2	Others	Unspecified		AC50	n.a.	631.0	nM	PMID[513000]
NPT2	Others	Unspecified		IC50	n.a.	33330.0	nM	PMID[513000]
NPT2	Others	Unspecified		Potency	n.a.	26603.2	nM	PubChem BioAssay data set

☑ 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 NPC215098 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	316
0.1-0.2	1458
0.2-0.3	4776
0.3-0.4	11493
0.4-0.5	5686
0.5-0.6	8560
0.6-0.7	9403
0.7-0.8	924
0.8-0.85	45
0.85-0.9	19
0.9-0.95	1
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46744
1.0	High Similarity	NPC73020
1.0	High Similarity	NPC70290
1.0	High Similarity	NPC124302
1.0	High Similarity	NPC14622
0.9887	High Similarity	NPC314100
0.9887	High Similarity	NPC120671
0.9887	High Similarity	NPC72788
0.9887	High Similarity	NPC226652
0.9777	High Similarity	NPC2173
0.9777	High Similarity	NPC328700
0.9777	High Similarity	NPC202771
0.9777	High Similarity	NPC119818
0.9274	High Similarity	NPC226708
0.904	High Similarity	NPC27887
0.8913	High Similarity	NPC125924
0.8859	High Similarity	NPC469816
0.8859	High Similarity	NPC469815
0.8743	High Similarity	NPC141440
0.871	High Similarity	NPC477258
0.8689	High Similarity	NPC477259
0.8689	High Similarity	NPC169387
0.8594	High Similarity	NPC80472
0.8541	High Similarity	NPC166979
0.8441	Intermediate Similarity	NPC208890
0.8438	Intermediate Similarity	NPC286135
0.8368	Intermediate Similarity	NPC24228
0.8316	Intermediate Similarity	NPC33256
0.8306	Intermediate Similarity	NPC222524
0.8287	Intermediate Similarity	NPC474708
0.8281	Intermediate Similarity	NPC207239
0.828	Intermediate Similarity	NPC83511
0.828	Intermediate Similarity	NPC116007
0.8254	Intermediate Similarity	NPC63152
0.8251	Intermediate Similarity	NPC308267
0.8232	Intermediate Similarity	NPC475845
0.8211	Intermediate Similarity	NPC94499
0.8207	Intermediate Similarity	NPC35680
0.8207	Intermediate Similarity	NPC474470
0.8182	Intermediate Similarity	NPC46990
0.8182	Intermediate Similarity	NPC474746
0.8182	Intermediate Similarity	NPC475981
0.8177	Intermediate Similarity	NPC474324
0.8177	Intermediate Similarity	NPC57812
0.8148	Intermediate Similarity	NPC237579
0.8142	Intermediate Similarity	NPC67978
0.8142	Intermediate Similarity	NPC303581
0.8138	Intermediate Similarity	NPC18306
0.8132	Intermediate Similarity	NPC86469
0.8098	Intermediate Similarity	NPC2314
0.8095	Intermediate Similarity	NPC230098
0.8087	Intermediate Similarity	NPC75958
0.8031	Intermediate Similarity	NPC470646
0.8022	Intermediate Similarity	NPC474858
0.8021	Intermediate Similarity	NPC244554
0.8021	Intermediate Similarity	NPC474745
0.8	Intermediate Similarity	NPC329992
0.7968	Intermediate Similarity	NPC474325
0.7967	Intermediate Similarity	NPC247972
0.7957	Intermediate Similarity	NPC304675
0.7949	Intermediate Similarity	NPC83019
0.7946	Intermediate Similarity	NPC225597
0.7946	Intermediate Similarity	NPC65403
0.7946	Intermediate Similarity	NPC477640
0.7946	Intermediate Similarity	NPC470739
0.7944	Intermediate Similarity	NPC301897
0.7943	Intermediate Similarity	NPC475959
0.7935	Intermediate Similarity	NPC290759
0.7935	Intermediate Similarity	NPC158148
0.7935	Intermediate Similarity	NPC266176
0.7935	Intermediate Similarity	NPC82533
0.7933	Intermediate Similarity	NPC31311
0.7933	Intermediate Similarity	NPC234392
0.7929	Intermediate Similarity	NPC207971
0.7914	Intermediate Similarity	NPC237044
0.7912	Intermediate Similarity	NPC78944
0.7906	Intermediate Similarity	NPC162694
0.7897	Intermediate Similarity	NPC204580
0.7895	Intermediate Similarity	NPC156576
0.7892	Intermediate Similarity	NPC474475
0.7889	Intermediate Similarity	NPC268077
0.788	Intermediate Similarity	NPC210918
0.788	Intermediate Similarity	NPC247389
0.7877	Intermediate Similarity	NPC41178
0.7877	Intermediate Similarity	NPC216459
0.7877	Intermediate Similarity	NPC138487
0.7872	Intermediate Similarity	NPC118633
0.7872	Intermediate Similarity	NPC121400
0.7872	Intermediate Similarity	NPC294790
0.7872	Intermediate Similarity	NPC148693
0.7865	Intermediate Similarity	NPC233029
0.7865	Intermediate Similarity	NPC210148
0.7849	Intermediate Similarity	NPC227683
0.7842	Intermediate Similarity	NPC248642
0.7838	Intermediate Similarity	NPC58766
0.7838	Intermediate Similarity	NPC475686
0.7833	Intermediate Similarity	NPC146288
0.7831	Intermediate Similarity	NPC220961
0.7826	Intermediate Similarity	NPC219341
0.7826	Intermediate Similarity	NPC476432
0.7826	Intermediate Similarity	NPC24264
0.7819	Intermediate Similarity	NPC241704
0.7816	Intermediate Similarity	NPC314914
0.7816	Intermediate Similarity	NPC478047
0.7816	Intermediate Similarity	NPC478046
0.7816	Intermediate Similarity	NPC321226
0.7816	Intermediate Similarity	NPC328856
0.7816	Intermediate Similarity	NPC180210
0.7814	Intermediate Similarity	NPC218614
0.7789	Intermediate Similarity	NPC473562
0.7784	Intermediate Similarity	NPC284842
0.7778	Intermediate Similarity	NPC284236
0.7778	Intermediate Similarity	NPC316368
0.7778	Intermediate Similarity	NPC78733
0.7778	Intermediate Similarity	NPC474427
0.7772	Intermediate Similarity	NPC167546
0.7772	Intermediate Similarity	NPC225774
0.7772	Intermediate Similarity	NPC231198
0.7772	Intermediate Similarity	NPC16805
0.7772	Intermediate Similarity	NPC302527
0.7772	Intermediate Similarity	NPC15212
0.7767	Intermediate Similarity	NPC478048
0.776	Intermediate Similarity	NPC9867
0.776	Intermediate Similarity	NPC153631
0.7754	Intermediate Similarity	NPC149090
0.7754	Intermediate Similarity	NPC19520
0.7753	Intermediate Similarity	NPC223125
0.7749	Intermediate Similarity	NPC102760
0.7747	Intermediate Similarity	NPC239113
0.7747	Intermediate Similarity	NPC477080
0.7747	Intermediate Similarity	NPC115123
0.7737	Intermediate Similarity	NPC126284
0.7737	Intermediate Similarity	NPC267408
0.7737	Intermediate Similarity	NPC32154
0.7727	Intermediate Similarity	NPC267414
0.772	Intermediate Similarity	NPC214116
0.7716	Intermediate Similarity	NPC474432
0.7716	Intermediate Similarity	NPC475713
0.7705	Intermediate Similarity	NPC26353
0.7703	Intermediate Similarity	NPC170101
0.7701	Intermediate Similarity	NPC311991
0.7692	Intermediate Similarity	NPC319549
0.7688	Intermediate Similarity	NPC100566
0.7688	Intermediate Similarity	NPC252960
0.7685	Intermediate Similarity	NPC476220
0.7685	Intermediate Similarity	NPC160113
0.7684	Intermediate Similarity	NPC15919
0.7684	Intermediate Similarity	NPC329816
0.7677	Intermediate Similarity	NPC71124
0.7676	Intermediate Similarity	NPC180306
0.7672	Intermediate Similarity	NPC187678
0.7667	Intermediate Similarity	NPC148898
0.7667	Intermediate Similarity	NPC223124
0.7656	Intermediate Similarity	NPC73492
0.7656	Intermediate Similarity	NPC299990
0.765	Intermediate Similarity	NPC154922
0.7626	Intermediate Similarity	NPC476258
0.7626	Intermediate Similarity	NPC304837
0.7626	Intermediate Similarity	NPC66909
0.7622	Intermediate Similarity	NPC320104
0.7617	Intermediate Similarity	NPC315914
0.7609	Intermediate Similarity	NPC232924
0.7609	Intermediate Similarity	NPC306902
0.7609	Intermediate Similarity	NPC160298
0.7609	Intermediate Similarity	NPC477559
0.7609	Intermediate Similarity	NPC266753
0.7609	Intermediate Similarity	NPC19600
0.7608	Intermediate Similarity	NPC195120
0.7608	Intermediate Similarity	NPC87560
0.7606	Intermediate Similarity	NPC471923
0.7604	Intermediate Similarity	NPC474506
0.7604	Intermediate Similarity	NPC32413
0.7602	Intermediate Similarity	NPC473716
0.7602	Intermediate Similarity	NPC475597
0.7594	Intermediate Similarity	NPC181653
0.7594	Intermediate Similarity	NPC190332
0.7592	Intermediate Similarity	NPC320223
0.7592	Intermediate Similarity	NPC114364
0.7582	Intermediate Similarity	NPC93593
0.7582	Intermediate Similarity	NPC308555
0.7581	Intermediate Similarity	NPC238530
0.7581	Intermediate Similarity	NPC232514
0.7581	Intermediate Similarity	NPC258322
0.7581	Intermediate Similarity	NPC276944
0.7581	Intermediate Similarity	NPC191352
0.7577	Intermediate Similarity	NPC214629
0.7566	Intermediate Similarity	NPC475453
0.7566	Intermediate Similarity	NPC473531
0.7565	Intermediate Similarity	NPC275132
0.7563	Intermediate Similarity	NPC254957
0.7557	Intermediate Similarity	NPC113455
0.7554	Intermediate Similarity	NPC329640
0.7554	Intermediate Similarity	NPC106786
0.7553	Intermediate Similarity	NPC241055
0.7552	Intermediate Similarity	NPC149285
0.7552	Intermediate Similarity	NPC470879
0.7552	Intermediate Similarity	NPC258695
0.755	Intermediate Similarity	NPC5374
0.7543	Intermediate Similarity	NPC188163
0.7543	Intermediate Similarity	NPC213206

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 NPC215098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	648
0.2-0.3	1120
0.3-0.4	2146
0.4-0.5	2475
0.5-0.6	1737
0.6-0.7	697
0.7-0.8	113
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4420	Approved
0.9777	High Similarity	NPD5006	Approved
0.9777	High Similarity	NPD5005	Approved
0.8143	Intermediate Similarity	NPD6625	Approved
0.8077	Intermediate Similarity	NPD5242	Approved
0.7821	Intermediate Similarity	NPD6386	Approved
0.7821	Intermediate Similarity	NPD6385	Approved
0.7807	Intermediate Similarity	NPD5313	Approved
0.7807	Intermediate Similarity	NPD5312	Approved
0.7778	Intermediate Similarity	NPD5457	Discontinued
0.7772	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7296	Approved
0.7626	Intermediate Similarity	NPD2973	Approved
0.7626	Intermediate Similarity	NPD2974	Approved
0.7626	Intermediate Similarity	NPD2975	Approved
0.76	Intermediate Similarity	NPD4107	Approved
0.76	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5978	Approved
0.7596	Intermediate Similarity	NPD5977	Approved
0.7581	Intermediate Similarity	NPD6107	Approved
0.7565	Intermediate Similarity	NPD6851	Approved
0.7565	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD6853	Approved
0.7553	Intermediate Similarity	NPD4481	Phase 3
0.7547	Intermediate Similarity	NPD6997	Phase 2
0.7543	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD2971	Approved
0.7513	Intermediate Similarity	NPD7280	Phase 3
0.7513	Intermediate Similarity	NPD2968	Approved
0.7513	Intermediate Similarity	NPD7281	Phase 3
0.7512	Intermediate Similarity	NPD4580	Approved
0.7512	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3641	Approved
0.75	Intermediate Similarity	NPD3639	Approved
0.75	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD3640	Phase 3
0.7486	Intermediate Similarity	NPD4584	Approved
0.7475	Intermediate Similarity	NPD2494	Approved
0.7475	Intermediate Similarity	NPD3452	Approved
0.7475	Intermediate Similarity	NPD4482	Phase 3
0.7475	Intermediate Similarity	NPD3450	Approved
0.7475	Intermediate Similarity	NPD2493	Approved
0.7472	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7930	Approved
0.7463	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6297	Approved
0.7418	Intermediate Similarity	NPD7907	Approved
0.7376	Intermediate Similarity	NPD7048	Phase 3
0.7374	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7827	Phase 1
0.7366	Intermediate Similarity	NPD4582	Approved
0.7366	Intermediate Similarity	NPD4583	Approved
0.7354	Intermediate Similarity	NPD5710	Approved
0.7354	Intermediate Similarity	NPD5711	Approved
0.7346	Intermediate Similarity	NPD7047	Phase 3
0.7344	Intermediate Similarity	NPD8156	Discontinued
0.7343	Intermediate Similarity	NPD7701	Phase 2
0.734	Intermediate Similarity	NPD5677	Discontinued
0.7336	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4665	Approved
0.7324	Intermediate Similarity	NPD4111	Phase 1
0.732	Intermediate Similarity	NPD7039	Approved
0.732	Intermediate Similarity	NPD7038	Approved
0.7318	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4002	Approved
0.7317	Intermediate Similarity	NPD4004	Approved
0.7297	Intermediate Similarity	NPD4846	Phase 2
0.7292	Intermediate Similarity	NPD8251	Approved
0.7292	Intermediate Similarity	NPD8252	Approved
0.7292	Intermediate Similarity	NPD8099	Discontinued
0.7291	Intermediate Similarity	NPD8285	Discontinued
0.7273	Intermediate Similarity	NPD7291	Discontinued
0.7246	Intermediate Similarity	NPD7999	Approved
0.7228	Intermediate Similarity	NPD5582	Discontinued
0.72	Intermediate Similarity	NPD2488	Approved
0.72	Intermediate Similarity	NPD2490	Approved
0.7192	Intermediate Similarity	NPD5564	Approved
0.7189	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3057	Approved
0.7181	Intermediate Similarity	NPD4966	Approved
0.7181	Intermediate Similarity	NPD4967	Phase 2
0.7181	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4965	Approved
0.7173	Intermediate Similarity	NPD6071	Discontinued
0.7166	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5676	Approved
0.7151	Intermediate Similarity	NPD5889	Approved
0.7151	Intermediate Similarity	NPD5890	Approved
0.7129	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2560	Approved
0.7128	Intermediate Similarity	NPD2563	Approved
0.7121	Intermediate Similarity	NPD6618	Phase 2
0.7115	Intermediate Similarity	NPD8319	Approved
0.7115	Intermediate Similarity	NPD8320	Phase 1
0.7105	Intermediate Similarity	NPD6234	Discontinued
0.7101	Intermediate Similarity	NPD2972	Approved
0.7101	Intermediate Similarity	NPD3533	Approved
0.71	Intermediate Similarity	NPD7906	Approved
0.7095	Intermediate Similarity	NPD4859	Phase 1
0.709	Intermediate Similarity	NPD6788	Approved
0.7083	Intermediate Similarity	NPD2899	Discontinued
0.7083	Intermediate Similarity	NPD3051	Approved
0.7081	Intermediate Similarity	NPD4210	Discontinued
0.7075	Intermediate Similarity	NPD7783	Phase 2
0.7075	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2977	Approved
0.7074	Intermediate Similarity	NPD2978	Approved
0.707	Intermediate Similarity	NPD5980	Discovery
0.7068	Intermediate Similarity	NPD5494	Approved
0.7059	Intermediate Similarity	NPD6873	Phase 2
0.7048	Intermediate Similarity	NPD7583	Approved
0.7047	Intermediate Similarity	NPD2970	Approved
0.7047	Intermediate Similarity	NPD2969	Approved
0.7043	Intermediate Similarity	NPD4017	Approved
0.7035	Intermediate Similarity	NPD8054	Approved
0.7035	Intermediate Similarity	NPD8053	Approved
0.7027	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6031	Approved
0.7027	Intermediate Similarity	NPD6030	Approved
0.7026	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3818	Discontinued
0.7024	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5689	Approved
0.7022	Intermediate Similarity	NPD5688	Approved
0.7021	Intermediate Similarity	NPD37	Approved
0.7019	Intermediate Similarity	NPD3448	Approved
0.7019	Intermediate Similarity	NPD2491	Approved
0.7014	Intermediate Similarity	NPD7585	Approved
0.701	Intermediate Similarity	NPD2898	Approved
0.7005	Intermediate Similarity	NPD6585	Discontinued
0.6995	Remote Similarity	NPD6808	Phase 2
0.6991	Remote Similarity	NPD8404	Phase 2
0.6986	Remote Similarity	NPD7497	Discontinued
0.6985	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4577	Approved
0.6985	Remote Similarity	NPD4578	Approved
0.6976	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4361	Phase 2
0.6968	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4773	Phase 2
0.6968	Remote Similarity	NPD4772	Phase 2
0.6968	Remote Similarity	NPD7110	Phase 1
0.6967	Remote Similarity	NPD7584	Approved
0.6965	Remote Similarity	NPD4663	Approved
0.6963	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2897	Discontinued
0.6957	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6874	Approved
0.6954	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5241	Discontinued
0.6939	Remote Similarity	NPD7228	Approved
0.6935	Remote Similarity	NPD5976	Discontinued
0.6931	Remote Similarity	NPD7298	Approved
0.6931	Remote Similarity	NPD6844	Discontinued
0.6927	Remote Similarity	NPD4360	Phase 2
0.6927	Remote Similarity	NPD4363	Phase 3
0.6923	Remote Similarity	NPD6779	Approved
0.6923	Remote Similarity	NPD6781	Approved
0.6923	Remote Similarity	NPD6782	Approved
0.6923	Remote Similarity	NPD6778	Approved
0.6923	Remote Similarity	NPD4236	Phase 3
0.6923	Remote Similarity	NPD27	Approved
0.6923	Remote Similarity	NPD6777	Approved
0.6923	Remote Similarity	NPD6780	Approved
0.6923	Remote Similarity	NPD4237	Approved
0.6923	Remote Similarity	NPD6776	Approved
0.6923	Remote Similarity	NPD2489	Approved
0.691	Remote Similarity	NPD4618	Approved
0.691	Remote Similarity	NPD1933	Approved
0.691	Remote Similarity	NPD8152	Approved
0.691	Remote Similarity	NPD4622	Approved
0.691	Remote Similarity	NPD8153	Approved
0.6907	Remote Similarity	NPD6232	Discontinued
0.6907	Remote Similarity	NPD7315	Approved
0.6907	Remote Similarity	NPD4166	Phase 2
0.6905	Remote Similarity	NPD7697	Approved
0.6905	Remote Similarity	NPD7696	Phase 3
0.6905	Remote Similarity	NPD7698	Approved
0.6901	Remote Similarity	NPD8151	Discontinued
0.69	Remote Similarity	NPD7313	Approved
0.69	Remote Similarity	NPD7312	Approved
0.69	Remote Similarity	NPD7311	Approved
0.69	Remote Similarity	NPD7310	Approved
0.69	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7223	Discontinued
0.6892	Remote Similarity	NPD7224	Discontinued
0.6891	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7811	Phase 3
0.6875	Remote Similarity	NPD7565	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data