NPASS Compound

Structure

CID119818 OpenBabel06191715472D 30 34 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 0.9706 1.5055 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 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 -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 1.8366 -0.9945 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 2 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 2.7026 0.5055 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 -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 0.9706 0.5055 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 23 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 23 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 28 1 0 0 0 0 10 29 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 19 2 0 0 0 0 13 25 1 0 0 0 0 14 20 2 0 0 0 0 14 28 1 0 0 0 0 15 21 2 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 15 1 1 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 12 1 1 0 0 0 18 30 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 27 1 0 0 0 0 22 24 2 0 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	413.15
Volume:	400.359
LogP:	1.937
LogD:	2.557
LogS:	-3.822
# Rotatable Bonds:	4
TPSA:	75.69
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	3.553
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	4.2441472032805905e-05
Pgp-inhibitor:	0.951
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.104

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	86.17273712158203%
Volume Distribution (VD):	1.578
Pgp-substrate:	9.035752296447754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.249
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.904
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.661
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.796
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	4.671
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.382
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.239
AMES Toxicity:	0.168
Rat Oral Acute Toxicity:	0.607
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.039
Carcinogencity:	0.65
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.838

Download Data

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

Natural Product: NPC119818

Natural Product ID:	NPC119818
*Common Name:**	(3R)-6,7-Dimethoxy-3-[(5R)-4-Methoxy-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-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	AKNNEGZIBPJZJG-QZTJIDSGSA-N
Standard InCHI:	InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18-/m1/s1
SMILES:	CN1CCc2cc3c(c(c2[C@@H]1[C@H]1c2ccc(c(c2C(=O)O1)OC)OC)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1403892
PubChem CID:	31411
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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
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]
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]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	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	8
Potency	22

Activity Type	# Activity
Individual Protein	28
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	1258.9	nM	PMID[534438]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	398.1	nM	PMID[534439]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	316.2	nM	PMID[534440]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	2511.9	nM	PMID[534441]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	2511.9	nM	PMID[534438]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	2511.9	nM	PMID[534441]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	10000.0	nM	PMID[534438]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	10000.0	nM	PMID[534439]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	15848.9	nM	PMID[534440]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	25118.9	nM	PMID[534441]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	1258.9	nM	PMID[534440]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	5011.9	nM	PMID[534441]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	2511.9	nM	PMID[534438]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	1584.9	nM	PMID[534439]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	354.8	nM	PMID[534438]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	25118.86	nM	PMID[534441]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	AC50	=	2511.89	nM	PMID[534438]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	2511.89	nM	PMID[534441]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	2511.89	nM	PMID[534441]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	AC50	=	5011.87	nM	PMID[534441]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	1258.93	nM	PMID[534438]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	2511.89	nM	PMID[534438]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	10000.0	nM	PMID[534438]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	26608.6	nM	PMID[534442]
NPT95	Individual Protein	Muscarinic acetylcholine receptor M1	Rattus norvegicus	Potency	=	125.9	nM	PMID[534441]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8492.1	nM	PMID[534438]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11995.5	nM	PMID[534438]

☑ 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 NPC119818 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	331
0.1-0.2	1536
0.2-0.3	5110
0.3-0.4	11629
0.4-0.5	5481
0.5-0.6	8074
0.6-0.7	9377
0.7-0.8	1078
0.8-0.85	50
0.85-0.9	14
0.9-0.95	1
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202771
1.0	High Similarity	NPC2173
1.0	High Similarity	NPC328700
0.9777	High Similarity	NPC70290
0.9777	High Similarity	NPC14622
0.9777	High Similarity	NPC46744
0.9777	High Similarity	NPC124302
0.9777	High Similarity	NPC215098
0.9777	High Similarity	NPC73020
0.9669	High Similarity	NPC120671
0.9669	High Similarity	NPC314100
0.9669	High Similarity	NPC226652
0.9669	High Similarity	NPC72788
0.9071	High Similarity	NPC226708
0.884	High Similarity	NPC27887
0.8802	High Similarity	NPC80472
0.8723	High Similarity	NPC125924
0.867	High Similarity	NPC469816
0.867	High Similarity	NPC469815
0.8656	High Similarity	NPC141440
0.8656	High Similarity	NPC208890
0.8646	High Similarity	NPC286135
0.8624	High Similarity	NPC477258
0.8602	High Similarity	NPC477259
0.8602	High Similarity	NPC169387
0.8466	Intermediate Similarity	NPC63152
0.8457	Intermediate Similarity	NPC166979
0.8306	Intermediate Similarity	NPC75958
0.8291	Intermediate Similarity	NPC46990
0.829	Intermediate Similarity	NPC24228
0.8254	Intermediate Similarity	NPC18306
0.8242	Intermediate Similarity	NPC474858
0.8238	Intermediate Similarity	NPC33256
0.8235	Intermediate Similarity	NPC244554
0.8226	Intermediate Similarity	NPC222524
0.8216	Intermediate Similarity	NPC329992
0.8207	Intermediate Similarity	NPC474708
0.8201	Intermediate Similarity	NPC83511
0.8201	Intermediate Similarity	NPC116007
0.8172	Intermediate Similarity	NPC308267
0.8152	Intermediate Similarity	NPC475845
0.8144	Intermediate Similarity	NPC470646
0.8135	Intermediate Similarity	NPC94499
0.8128	Intermediate Similarity	NPC35680
0.8128	Intermediate Similarity	NPC474470
0.8112	Intermediate Similarity	NPC207239
0.8105	Intermediate Similarity	NPC474746
0.8105	Intermediate Similarity	NPC475981
0.8098	Intermediate Similarity	NPC474324
0.8098	Intermediate Similarity	NPC57812
0.8066	Intermediate Similarity	NPC301897
0.8065	Intermediate Similarity	NPC303581
0.8065	Intermediate Similarity	NPC67978
0.8061	Intermediate Similarity	NPC83019
0.8021	Intermediate Similarity	NPC230098
0.8021	Intermediate Similarity	NPC2314
0.801	Intermediate Similarity	NPC204580
0.8	Intermediate Similarity	NPC473562
0.7979	Intermediate Similarity	NPC237579
0.7969	Intermediate Similarity	NPC9867
0.7968	Intermediate Similarity	NPC65403
0.7957	Intermediate Similarity	NPC86469
0.7947	Intermediate Similarity	NPC474745
0.7923	Intermediate Similarity	NPC26353
0.7895	Intermediate Similarity	NPC329816
0.7895	Intermediate Similarity	NPC474325
0.7892	Intermediate Similarity	NPC180306
0.7892	Intermediate Similarity	NPC247972
0.7884	Intermediate Similarity	NPC304675
0.7872	Intermediate Similarity	NPC470739
0.7872	Intermediate Similarity	NPC19520
0.7872	Intermediate Similarity	NPC149090
0.7872	Intermediate Similarity	NPC477640
0.7872	Intermediate Similarity	NPC225597
0.7865	Intermediate Similarity	NPC73492
0.7865	Intermediate Similarity	NPC299990
0.7861	Intermediate Similarity	NPC82533
0.7861	Intermediate Similarity	NPC158148
0.7861	Intermediate Similarity	NPC290759
0.7861	Intermediate Similarity	NPC266176
0.7857	Intermediate Similarity	NPC234392
0.7857	Intermediate Similarity	NPC31311
0.7842	Intermediate Similarity	NPC237044
0.7835	Intermediate Similarity	NPC214116
0.7835	Intermediate Similarity	NPC162694
0.7822	Intermediate Similarity	NPC268077
0.7819	Intermediate Similarity	NPC474475
0.7806	Intermediate Similarity	NPC475597
0.7806	Intermediate Similarity	NPC473716
0.7804	Intermediate Similarity	NPC315914
0.7802	Intermediate Similarity	NPC41178
0.7802	Intermediate Similarity	NPC138487
0.7802	Intermediate Similarity	NPC216459
0.7801	Intermediate Similarity	NPC148693
0.7801	Intermediate Similarity	NPC121400
0.7801	Intermediate Similarity	NPC118633
0.7801	Intermediate Similarity	NPC294790
0.7799	Intermediate Similarity	NPC195120
0.7799	Intermediate Similarity	NPC87560
0.7772	Intermediate Similarity	NPC329640
0.7772	Intermediate Similarity	NPC207971
0.7766	Intermediate Similarity	NPC58766
0.7766	Intermediate Similarity	NPC475686
0.7765	Intermediate Similarity	NPC37144
0.7765	Intermediate Similarity	NPC59907
0.7765	Intermediate Similarity	NPC475959
0.776	Intermediate Similarity	NPC146288
0.7749	Intermediate Similarity	NPC241704
0.7742	Intermediate Similarity	NPC78944
0.7742	Intermediate Similarity	NPC218614
0.7732	Intermediate Similarity	NPC156576
0.7727	Intermediate Similarity	NPC304837
0.7727	Intermediate Similarity	NPC476258
0.7725	Intermediate Similarity	NPC157983
0.7725	Intermediate Similarity	NPC118154
0.772	Intermediate Similarity	NPC32413
0.772	Intermediate Similarity	NPC474506
0.7713	Intermediate Similarity	NPC210918
0.7713	Intermediate Similarity	NPC247389
0.7711	Intermediate Similarity	NPC474427
0.7708	Intermediate Similarity	NPC15919
0.7705	Intermediate Similarity	NPC78733
0.7701	Intermediate Similarity	NPC231198
0.7701	Intermediate Similarity	NPC191352
0.7701	Intermediate Similarity	NPC258322
0.7696	Intermediate Similarity	NPC475768
0.7696	Intermediate Similarity	NPC187678
0.7692	Intermediate Similarity	NPC233029
0.7692	Intermediate Similarity	NPC210148
0.7688	Intermediate Similarity	NPC153631
0.7684	Intermediate Similarity	NPC227683
0.768	Intermediate Similarity	NPC248642
0.768	Intermediate Similarity	NPC102760
0.7668	Intermediate Similarity	NPC220961
0.7668	Intermediate Similarity	NPC258695
0.7668	Intermediate Similarity	NPC470879
0.7668	Intermediate Similarity	NPC32154
0.7667	Intermediate Similarity	NPC321226
0.7667	Intermediate Similarity	NPC478046
0.7667	Intermediate Similarity	NPC180210
0.7667	Intermediate Similarity	NPC328856
0.7667	Intermediate Similarity	NPC314914
0.7667	Intermediate Similarity	NPC478047
0.7665	Intermediate Similarity	NPC281581
0.766	Intermediate Similarity	NPC476432
0.766	Intermediate Similarity	NPC24264
0.766	Intermediate Similarity	NPC219341
0.7658	Intermediate Similarity	NPC113455
0.765	Intermediate Similarity	NPC475713
0.765	Intermediate Similarity	NPC474432
0.7632	Intermediate Similarity	NPC311991
0.763	Intermediate Similarity	NPC284236
0.763	Intermediate Similarity	NPC316368
0.7626	Intermediate Similarity	NPC319549
0.7619	Intermediate Similarity	NPC38964
0.7619	Intermediate Similarity	NPC252960
0.7619	Intermediate Similarity	NPC478048
0.7619	Intermediate Similarity	NPC284842
0.7619	Intermediate Similarity	NPC100566
0.7617	Intermediate Similarity	NPC327005
0.7617	Intermediate Similarity	NPC23219
0.7615	Intermediate Similarity	NPC476429
0.7606	Intermediate Similarity	NPC15212
0.7606	Intermediate Similarity	NPC302527
0.7606	Intermediate Similarity	NPC16805
0.7606	Intermediate Similarity	NPC167546
0.7606	Intermediate Similarity	NPC225774
0.7596	Intermediate Similarity	NPC148898
0.7594	Intermediate Similarity	NPC474043
0.7588	Intermediate Similarity	NPC24260
0.7588	Intermediate Similarity	NPC117717
0.7582	Intermediate Similarity	NPC223125
0.7581	Intermediate Similarity	NPC239113
0.7581	Intermediate Similarity	NPC155063
0.7581	Intermediate Similarity	NPC477080
0.7581	Intermediate Similarity	NPC115123
0.7579	Intermediate Similarity	NPC204908
0.7579	Intermediate Similarity	NPC83198
0.7577	Intermediate Similarity	NPC126284
0.7577	Intermediate Similarity	NPC267408
0.7576	Intermediate Similarity	NPC470642
0.7576	Intermediate Similarity	NPC82763
0.7574	Intermediate Similarity	NPC267414
0.7568	Intermediate Similarity	NPC348849
0.7568	Intermediate Similarity	NPC178195
0.7566	Intermediate Similarity	NPC61141
0.7566	Intermediate Similarity	NPC13916
0.7566	Intermediate Similarity	NPC264850
0.7566	Intermediate Similarity	NPC329717
0.7565	Intermediate Similarity	NPC112575
0.7563	Intermediate Similarity	NPC474009
0.7562	Intermediate Similarity	NPC66909
0.7559	Intermediate Similarity	NPC170101
0.7556	Intermediate Similarity	NPC120239
0.7554	Intermediate Similarity	NPC473732
0.7554	Intermediate Similarity	NPC104353
0.7553	Intermediate Similarity	NPC320104
0.7552	Intermediate Similarity	NPC232386
0.7552	Intermediate Similarity	NPC152680
0.7552	Intermediate Similarity	NPC190783

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 NPC119818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	671
0.2-0.3	1158
0.3-0.4	2224
0.4-0.5	2446
0.5-0.6	1702
0.6-0.7	629
0.7-0.8	104
0.8-0.85	2
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	NPD5006	Approved
1.0	High Similarity	NPD5005	Approved
0.9777	High Similarity	NPD4420	Approved
0.8333	Intermediate Similarity	NPD6625	Approved
0.8197	Intermediate Similarity	NPD5242	Approved
0.7737	Intermediate Similarity	NPD5313	Approved
0.7737	Intermediate Similarity	NPD5312	Approved
0.7717	Intermediate Similarity	NPD5353	Approved
0.7711	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD6385	Approved
0.765	Intermediate Similarity	NPD6386	Approved
0.7626	Intermediate Similarity	NPD7296	Approved
0.7624	Intermediate Similarity	NPD5457	Discontinued
0.7614	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2975	Approved
0.7562	Intermediate Similarity	NPD2973	Approved
0.7562	Intermediate Similarity	NPD2974	Approved
0.756	Intermediate Similarity	NPD7827	Phase 1
0.7552	Intermediate Similarity	NPD8156	Discontinued
0.7513	Intermediate Similarity	NPD6107	Approved
0.75	Intermediate Similarity	NPD8252	Approved
0.75	Intermediate Similarity	NPD8251	Approved
0.75	Intermediate Similarity	NPD8099	Discontinued
0.7488	Intermediate Similarity	NPD6997	Phase 2
0.7487	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD4846	Phase 2
0.7474	Intermediate Similarity	NPD5711	Approved
0.7474	Intermediate Similarity	NPD5710	Approved
0.7461	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD5677	Discontinued
0.7451	Intermediate Similarity	NPD4580	Approved
0.7451	Intermediate Similarity	NPD4107	Approved
0.7449	Intermediate Similarity	NPD7280	Phase 3
0.7449	Intermediate Similarity	NPD7281	Phase 3
0.7444	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD5978	Approved
0.7433	Intermediate Similarity	NPD5977	Approved
0.7418	Intermediate Similarity	NPD4584	Approved
0.7415	Intermediate Similarity	NPD2494	Approved
0.7415	Intermediate Similarity	NPD3452	Approved
0.7415	Intermediate Similarity	NPD3450	Approved
0.7415	Intermediate Similarity	NPD2493	Approved
0.7411	Intermediate Similarity	NPD6851	Approved
0.7411	Intermediate Similarity	NPD6853	Approved
0.7406	Intermediate Similarity	NPD7930	Approved
0.74	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4481	Phase 3
0.7374	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.7361	Intermediate Similarity	NPD7907	Approved
0.7361	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2971	Approved
0.736	Intermediate Similarity	NPD2968	Approved
0.7337	Intermediate Similarity	NPD3639	Approved
0.7337	Intermediate Similarity	NPD3641	Approved
0.7337	Intermediate Similarity	NPD3640	Phase 3
0.733	Intermediate Similarity	NPD4482	Phase 3
0.7321	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7048	Phase 3
0.7313	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4583	Approved
0.7308	Intermediate Similarity	NPD4582	Approved
0.7302	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6788	Approved
0.7302	Intermediate Similarity	NPD4967	Phase 2
0.7302	Intermediate Similarity	NPD4965	Approved
0.7302	Intermediate Similarity	NPD4966	Approved
0.7296	Intermediate Similarity	NPD6297	Approved
0.729	Intermediate Similarity	NPD7047	Phase 3
0.7273	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD4665	Approved
0.7269	Intermediate Similarity	NPD4111	Phase 1
0.7269	Intermediate Similarity	NPD2899	Discontinued
0.726	Intermediate Similarity	NPD4002	Approved
0.726	Intermediate Similarity	NPD4004	Approved
0.7236	Intermediate Similarity	NPD8053	Approved
0.7236	Intermediate Similarity	NPD8054	Approved
0.7233	Intermediate Similarity	NPD8285	Discontinued
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.722	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7999	Approved
0.7188	Intermediate Similarity	NPD5494	Approved
0.7172	Intermediate Similarity	NPD7038	Approved
0.7172	Intermediate Similarity	NPD7039	Approved
0.7171	Intermediate Similarity	NPD5582	Discontinued
0.7158	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7583	Approved
0.7151	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD8319	Approved
0.7129	Intermediate Similarity	NPD7291	Discontinued
0.7123	Intermediate Similarity	NPD7585	Approved
0.7103	Intermediate Similarity	NPD7783	Phase 2
0.7103	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4361	Phase 2
0.7087	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD8153	Approved
0.7082	Intermediate Similarity	NPD8152	Approved
0.7075	Intermediate Similarity	NPD7584	Approved
0.7072	Intermediate Similarity	NPD7223	Discontinued
0.7072	Intermediate Similarity	NPD7224	Discontinued
0.7059	Intermediate Similarity	NPD2488	Approved
0.7059	Intermediate Similarity	NPD2490	Approved
0.7056	Intermediate Similarity	NPD7228	Approved
0.7053	Intermediate Similarity	NPD5564	Approved
0.705	Intermediate Similarity	NPD7549	Discontinued
0.7048	Intermediate Similarity	NPD3057	Approved
0.7044	Intermediate Similarity	NPD7906	Approved
0.7039	Intermediate Similarity	NPD4363	Phase 3
0.7039	Intermediate Similarity	NPD4360	Phase 2
0.7037	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6723	Discontinued
0.7026	Intermediate Similarity	NPD6232	Discontinued
0.7026	Intermediate Similarity	NPD6071	Discontinued
0.7023	Intermediate Similarity	NPD5676	Approved
0.7021	Intermediate Similarity	NPD4210	Discontinued
0.7018	Intermediate Similarity	NPD8404	Phase 2
0.7016	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7497	Discontinued
0.7009	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD5890	Approved
0.7	Intermediate Similarity	NPD5889	Approved
0.6985	Remote Similarity	NPD7074	Phase 3
0.698	Remote Similarity	NPD6618	Phase 2
0.6979	Remote Similarity	NPD3817	Phase 2
0.6979	Remote Similarity	NPD2563	Approved
0.6979	Remote Similarity	NPD2560	Approved
0.6974	Remote Similarity	NPD7199	Phase 2
0.6967	Remote Similarity	NPD2972	Approved
0.6967	Remote Similarity	NPD3533	Approved
0.6965	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4859	Phase 1
0.6963	Remote Similarity	NPD1934	Approved
0.696	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2654	Approved
0.6952	Remote Similarity	NPD6777	Approved
0.6952	Remote Similarity	NPD6781	Approved
0.6952	Remote Similarity	NPD6780	Approved
0.6952	Remote Similarity	NPD6779	Approved
0.6952	Remote Similarity	NPD6776	Approved
0.6952	Remote Similarity	NPD1424	Approved
0.6952	Remote Similarity	NPD6782	Approved
0.6952	Remote Similarity	NPD6778	Approved
0.6941	Remote Similarity	NPD5980	Discovery
0.6939	Remote Similarity	NPD3051	Approved
0.6935	Remote Similarity	NPD7054	Approved
0.6934	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7698	Approved
0.6934	Remote Similarity	NPD7696	Phase 3
0.6934	Remote Similarity	NPD7697	Approved
0.6931	Remote Similarity	NPD4577	Approved
0.6931	Remote Similarity	NPD4578	Approved
0.6927	Remote Similarity	NPD2977	Approved
0.6927	Remote Similarity	NPD2978	Approved
0.6919	Remote Similarity	NPD7473	Discontinued
0.6917	Remote Similarity	NPD7708	Approved
0.6915	Remote Similarity	NPD7240	Approved
0.6912	Remote Similarity	NPD4663	Approved
0.6911	Remote Similarity	NPD4772	Phase 2
0.6911	Remote Similarity	NPD6873	Phase 2
0.6911	Remote Similarity	NPD4773	Phase 2
0.6907	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD2970	Approved
0.6904	Remote Similarity	NPD2969	Approved
0.6901	Remote Similarity	NPD7871	Phase 2
0.6901	Remote Similarity	NPD7870	Phase 2
0.69	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7472	Approved
0.6898	Remote Similarity	NPD7874	Approved
0.6898	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4017	Approved
0.6895	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2491	Approved
0.6887	Remote Similarity	NPD3448	Approved
0.6887	Remote Similarity	NPD6823	Phase 2
0.6884	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6030	Approved
0.6878	Remote Similarity	NPD6031	Approved
0.6875	Remote Similarity	NPD3382	Approved
0.6875	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3384	Approved
0.6875	Remote Similarity	NPD3383	Approved
0.6875	Remote Similarity	NPD6844	Discontinued
0.6872	Remote Similarity	NPD7803	Approved
0.6869	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD2898	Approved
0.6869	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5689	Approved
0.6868	Remote Similarity	NPD5688	Approved
0.6865	Remote Similarity	NPD4237	Approved
0.6865	Remote Similarity	NPD4236	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data