NPASS Compound

Structure

CID170779 OpenBabel06191715542D 24 27 0 0 1 0 0 0 0 0999 V2000 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6705 -0.3934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 0.6011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -0.8002 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 4 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 11 23 1 0 0 0 0 12 2 1 1 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 15 20 2 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 14 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.14
Volume:	336.956
LogP:	4.442
LogD:	3.73
LogS:	-6.227
# Rotatable Bonds:	3
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	3.335
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.892
MDCK Permeability:	2.997116644110065e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	95.88196563720703%
Volume Distribution (VD):	2.572
Pgp-substrate:	2.8316633701324463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.902
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.682
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.907
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.765

ADMET: Excretion

Clearance (CL):	14.977
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.217
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.259
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.809
Skin Sensitization:	0.462
Carcinogencity:	0.736
Eye Corrosion:	0.004
Eye Irritation:	0.116
Respiratory Toxicity:	0.616

Download Data

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

Natural Product: NPC170779

Natural Product ID:	NPC170779
*Common Name:**	(-)-Licarin B
IUPAC Name:	5-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]-1,3-benzodioxole
Synonyms:
Standard InCHIKey:	DMMQXURQRMNSBM-NSWCWGQASA-N
Standard InCHI:	InChI=1S/C20H20O4/c1-4-5-13-8-15-12(2)19(24-20(15)18(9-13)21-3)14-6-7-16-17(10-14)23-11-22-16/h4-10,12,19H,11H2,1-3H3/b5-4+/t12-,19-/m0/s1
SMILES:	C/C=C/c1cc2[C@H](C)[C@@H](c3ccc4c(c3)OCO4)Oc2c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL578403
PubChem CID:	10860310
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO490	Lophozonia menziesii	Species	0thofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	Species	Lauraceae	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	10
Ki	3
Others	4

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	7
Others	6
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	366000.0	nM	PMID[556185]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	25600.0	nM	PMID[556185]
NPT2	Others	Unspecified		IC50	=	14300.0	nM	PMID[556185]
NPT2	Others	Unspecified		Ratio IC50	=	426.0	n.a.	PMID[556185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	488000.0	nM	PMID[556185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	290000.0	nM	PMID[556185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	54600.0	nM	PMID[556185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	50600.0	nM	PMID[556186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	86.7	%	PMID[556186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	42.5	%	PMID[556186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	5.3	%	PMID[556186]
NPT23157	SINGLE PROTEIN	Sialidase A	Streptococcus pneumoniae	IC50	=	1500.0	nM	PMID[556187]
NPT2	Others	Unspecified		IC50	=	14000.0	nM	PMID[556187]
NPT23157	SINGLE PROTEIN	Sialidase A	Streptococcus pneumoniae	Ki	=	1300.0	nM	PMID[556187]
NPT2	Others	Unspecified		Ki	=	13500.0	nM	PMID[556187]
NPT2	Others	Unspecified		IC50	=	30700.0	nM	PMID[556187]
NPT2	Others	Unspecified		Ki	=	12100.0	nM	PMID[556187]

☑ 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 NPC170779 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	493
0.1-0.2	1624
0.2-0.3	4346
0.3-0.4	11870
0.4-0.5	6592
0.5-0.6	5055
0.6-0.7	9206
0.7-0.8	2852
0.8-0.85	505
0.85-0.9	128
0.9-0.95	22
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC90083
0.9535	High Similarity	NPC7744
0.9528	High Similarity	NPC158471
0.9528	High Similarity	NPC226862
0.9528	High Similarity	NPC165128
0.9528	High Similarity	NPC57119
0.9478	High Similarity	NPC472562
0.9449	High Similarity	NPC98745
0.938	High Similarity	NPC233224
0.938	High Similarity	NPC271208
0.9318	High Similarity	NPC474139
0.9308	High Similarity	NPC82111
0.9308	High Similarity	NPC227160
0.927	High Similarity	NPC180953
0.9191	High Similarity	NPC80326
0.9167	High Similarity	NPC266848
0.9167	High Similarity	NPC136750
0.913	High Similarity	NPC205316
0.9118	High Similarity	NPC58137
0.9118	High Similarity	NPC300798
0.9104	High Similarity	NPC78047
0.9091	High Similarity	NPC65183
0.9091	High Similarity	NPC158526
0.9091	High Similarity	NPC72046
0.9091	High Similarity	NPC129687
0.9091	High Similarity	NPC261812
0.9091	High Similarity	NPC219671
0.9091	High Similarity	NPC33611
0.9091	High Similarity	NPC147616
0.9091	High Similarity	NPC259742
0.9091	High Similarity	NPC100223
0.9091	High Similarity	NPC171928
0.9091	High Similarity	NPC230219
0.9091	High Similarity	NPC16830
0.9091	High Similarity	NPC104077
0.9062	High Similarity	NPC121783
0.9062	High Similarity	NPC34902
0.9062	High Similarity	NPC18449
0.9058	High Similarity	NPC471667
0.9058	High Similarity	NPC217635
0.9058	High Similarity	NPC79429
0.9051	High Similarity	NPC253878
0.9051	High Similarity	NPC174522
0.903	High Similarity	NPC189474
0.903	High Similarity	NPC135777
0.903	High Similarity	NPC142547
0.9023	High Similarity	NPC26394
0.9015	High Similarity	NPC192255
0.9	High Similarity	NPC158737
0.8993	High Similarity	NPC43508
0.8993	High Similarity	NPC476301
0.8978	High Similarity	NPC312199
0.8978	High Similarity	NPC471414
0.8976	High Similarity	NPC172676
0.8976	High Similarity	NPC57268
0.8976	High Similarity	NPC65933
0.8976	High Similarity	NPC216929
0.8976	High Similarity	NPC126935
0.8976	High Similarity	NPC312713
0.8976	High Similarity	NPC80241
0.8976	High Similarity	NPC301641
0.8955	High Similarity	NPC193026
0.8955	High Similarity	NPC47181
0.8955	High Similarity	NPC49603
0.8955	High Similarity	NPC187616
0.8955	High Similarity	NPC31530
0.8944	High Similarity	NPC98624
0.8936	High Similarity	NPC71726
0.8913	High Similarity	NPC246947
0.8913	High Similarity	NPC302506
0.8905	High Similarity	NPC216434
0.8905	High Similarity	NPC103448
0.8889	High Similarity	NPC25333
0.8889	High Similarity	NPC18576
0.8889	High Similarity	NPC49235
0.8889	High Similarity	NPC148893
0.8889	High Similarity	NPC174191
0.8865	High Similarity	NPC213074
0.8865	High Similarity	NPC15956
0.8865	High Similarity	NPC193473
0.8865	High Similarity	NPC224674
0.8865	High Similarity	NPC31325
0.8865	High Similarity	NPC114505
0.8865	High Similarity	NPC275284
0.8864	High Similarity	NPC476748
0.8849	High Similarity	NPC265154
0.8832	High Similarity	NPC123526
0.8832	High Similarity	NPC193666
0.8832	High Similarity	NPC88640
0.8824	High Similarity	NPC121651
0.8824	High Similarity	NPC54743
0.8824	High Similarity	NPC29799
0.8824	High Similarity	NPC156502
0.8824	High Similarity	NPC263367
0.8824	High Similarity	NPC177160
0.8824	High Similarity	NPC209985
0.8824	High Similarity	NPC10737
0.8824	High Similarity	NPC477939
0.8819	High Similarity	NPC344161
0.8806	High Similarity	NPC471505
0.8803	High Similarity	NPC270751
0.8788	High Similarity	NPC222127
0.8788	High Similarity	NPC82862
0.8786	High Similarity	NPC179521
0.8779	High Similarity	NPC40352
0.8779	High Similarity	NPC213711
0.8777	High Similarity	NPC311057
0.8777	High Similarity	NPC474295
0.8768	High Similarity	NPC226547
0.8759	High Similarity	NPC196420
0.8759	High Similarity	NPC185908
0.8759	High Similarity	NPC477938
0.8759	High Similarity	NPC101807
0.8759	High Similarity	NPC469981
0.8741	High Similarity	NPC240521
0.8723	High Similarity	NPC42716
0.8723	High Similarity	NPC11422
0.8723	High Similarity	NPC38041
0.8723	High Similarity	NPC279298
0.8723	High Similarity	NPC178014
0.8723	High Similarity	NPC474749
0.8723	High Similarity	NPC22150
0.8714	High Similarity	NPC474808
0.8712	High Similarity	NPC473092
0.8712	High Similarity	NPC177167
0.8712	High Similarity	NPC473093
0.8712	High Similarity	NPC8050
0.8699	High Similarity	NPC159922
0.8696	High Similarity	NPC156376
0.8696	High Similarity	NPC113550
0.8686	High Similarity	NPC11453
0.8686	High Similarity	NPC32189
0.8676	High Similarity	NPC16485
0.8676	High Similarity	NPC474478
0.8671	High Similarity	NPC301961
0.8671	High Similarity	NPC166584
0.8667	High Similarity	NPC18842
0.8667	High Similarity	NPC106739
0.8662	High Similarity	NPC205796
0.8662	High Similarity	NPC241846
0.8662	High Similarity	NPC112861
0.8662	High Similarity	NPC162193
0.8662	High Similarity	NPC276753
0.8662	High Similarity	NPC93610
0.8657	High Similarity	NPC171550
0.8657	High Similarity	NPC134764
0.8647	High Similarity	NPC281864
0.8647	High Similarity	NPC54321
0.8647	High Similarity	NPC328682
0.8643	High Similarity	NPC41782
0.8643	High Similarity	NPC131971
0.8636	High Similarity	NPC206882
0.8636	High Similarity	NPC112571
0.8636	High Similarity	NPC50683
0.8636	High Similarity	NPC285725
0.8633	High Similarity	NPC46591
0.8633	High Similarity	NPC177868
0.8623	High Similarity	NPC166184
0.8623	High Similarity	NPC283949
0.8613	High Similarity	NPC150534
0.8613	High Similarity	NPC184938
0.8613	High Similarity	NPC101624
0.8603	High Similarity	NPC196937
0.8603	High Similarity	NPC169973
0.8603	High Similarity	NPC1474
0.8601	High Similarity	NPC116019
0.8593	High Similarity	NPC228346
0.8593	High Similarity	NPC158079
0.8593	High Similarity	NPC40432
0.8593	High Similarity	NPC27843
0.8593	High Similarity	NPC115207
0.8593	High Similarity	NPC7171
0.8593	High Similarity	NPC161557
0.8592	High Similarity	NPC18979
0.8582	High Similarity	NPC298317
0.8582	High Similarity	NPC185307
0.8582	High Similarity	NPC470950
0.8582	High Similarity	NPC477898
0.8582	High Similarity	NPC255566
0.8571	High Similarity	NPC471908
0.8571	High Similarity	NPC87725
0.8571	High Similarity	NPC263261
0.8562	High Similarity	NPC302610
0.8561	High Similarity	NPC292487
0.8561	High Similarity	NPC9068
0.8561	High Similarity	NPC17348
0.8552	High Similarity	NPC472710
0.8552	High Similarity	NPC238140
0.8552	High Similarity	NPC472709
0.8551	High Similarity	NPC143895
0.8551	High Similarity	NPC25695
0.8551	High Similarity	NPC172818
0.855	High Similarity	NPC279379
0.8542	High Similarity	NPC226153
0.8542	High Similarity	NPC304048
0.854	High Similarity	NPC185680
0.854	High Similarity	NPC145722
0.854	High Similarity	NPC256776
0.8531	High Similarity	NPC226540
0.8529	High Similarity	NPC207400

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 NPC170779 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	925
0.2-0.3	1792
0.3-0.4	2767
0.4-0.5	1675
0.5-0.6	935
0.6-0.7	578
0.7-0.8	95
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8682	High Similarity	NPD3705	Approved
0.8268	Intermediate Similarity	NPD5283	Phase 1
0.8182	Intermediate Similarity	NPD6674	Discontinued
0.7974	Intermediate Similarity	NPD4965	Approved
0.7974	Intermediate Similarity	NPD4967	Phase 2
0.7974	Intermediate Similarity	NPD4966	Approved
0.7899	Intermediate Similarity	NPD2861	Phase 2
0.7871	Intermediate Similarity	NPD6234	Discontinued
0.7823	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3027	Phase 3
0.7778	Intermediate Similarity	NPD37	Approved
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7761	Intermediate Similarity	NPD1357	Approved
0.7746	Intermediate Similarity	NPD4060	Phase 1
0.7746	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1613	Approved
0.7718	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1375	Discontinued
0.7651	Intermediate Similarity	NPD5058	Phase 3
0.7606	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5494	Approved
0.7591	Intermediate Similarity	NPD1091	Approved
0.7589	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8651	Approved
0.7534	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7228	Approved
0.7518	Intermediate Similarity	NPD3018	Phase 2
0.7518	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6331	Phase 2
0.7482	Intermediate Similarity	NPD5327	Phase 3
0.7465	Intermediate Similarity	NPD4908	Phase 1
0.7451	Intermediate Similarity	NPD5976	Discontinued
0.7448	Intermediate Similarity	NPD6355	Discontinued
0.7432	Intermediate Similarity	NPD5763	Approved
0.7432	Intermediate Similarity	NPD5762	Approved
0.741	Intermediate Similarity	NPD2981	Phase 2
0.7403	Intermediate Similarity	NPD4210	Discontinued
0.74	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4110	Phase 3
0.7372	Intermediate Similarity	NPD5691	Approved
0.7357	Intermediate Similarity	NPD2982	Phase 2
0.7357	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2983	Phase 2
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7349	Intermediate Similarity	NPD7240	Approved
0.7343	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1610	Phase 2
0.7338	Intermediate Similarity	NPD1611	Approved
0.7333	Intermediate Similarity	NPD6387	Discontinued
0.7333	Intermediate Similarity	NPD7157	Approved
0.7329	Intermediate Similarity	NPD3657	Discovery
0.7329	Intermediate Similarity	NPD5735	Approved
0.7328	Intermediate Similarity	NPD2684	Approved
0.7317	Intermediate Similarity	NPD3818	Discontinued
0.7303	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5588	Approved
0.7297	Intermediate Similarity	NPD4108	Discontinued
0.7293	Intermediate Similarity	NPD1137	Approved
0.7293	Intermediate Similarity	NPD1139	Approved
0.729	Intermediate Similarity	NPD1653	Approved
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3620	Phase 2
0.7248	Intermediate Similarity	NPD2161	Phase 2
0.7246	Intermediate Similarity	NPD5585	Approved
0.7244	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5111	Phase 2
0.7241	Intermediate Similarity	NPD5109	Approved
0.7241	Intermediate Similarity	NPD5110	Phase 2
0.7239	Intermediate Similarity	NPD1138	Approved
0.7239	Intermediate Similarity	NPD5535	Approved
0.7239	Intermediate Similarity	NPD7843	Approved
0.7237	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4536	Approved
0.723	Intermediate Similarity	NPD4538	Approved
0.723	Intermediate Similarity	NPD7097	Phase 1
0.7219	Intermediate Similarity	NPD4236	Phase 3
0.7219	Intermediate Similarity	NPD4237	Approved
0.72	Intermediate Similarity	NPD7266	Discontinued
0.72	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6002	Phase 3
0.72	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6005	Phase 3
0.72	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD7028	Phase 2
0.7195	Intermediate Similarity	NPD4481	Phase 3
0.7194	Intermediate Similarity	NPD17	Approved
0.7194	Intermediate Similarity	NPD5126	Approved
0.7194	Intermediate Similarity	NPD5125	Phase 3
0.7192	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6696	Suspended
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7171	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2978	Approved
0.717	Intermediate Similarity	NPD2977	Approved
0.717	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD228	Approved
0.7162	Intermediate Similarity	NPD2157	Approved
0.7161	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2438	Suspended
0.7126	Intermediate Similarity	NPD7074	Phase 3
0.7124	Intermediate Similarity	NPD2677	Approved
0.7123	Intermediate Similarity	NPD6798	Discontinued
0.7117	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD7119	Phase 2
0.7107	Intermediate Similarity	NPD1934	Approved
0.7107	Intermediate Similarity	NPD3382	Approved
0.7107	Intermediate Similarity	NPD3383	Approved
0.7107	Intermediate Similarity	NPD3384	Approved
0.7093	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6671	Approved
0.7076	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3051	Approved
0.7071	Intermediate Similarity	NPD4626	Approved
0.7067	Intermediate Similarity	NPD5960	Phase 3
0.7066	Intermediate Similarity	NPD7054	Approved
0.7066	Intermediate Similarity	NPD5844	Phase 1
0.7063	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2922	Phase 1
0.7055	Intermediate Similarity	NPD7095	Approved
0.705	Intermediate Similarity	NPD1548	Phase 1
0.705	Intermediate Similarity	NPD1182	Approved
0.7047	Intermediate Similarity	NPD6353	Approved
0.7042	Intermediate Similarity	NPD1608	Approved
0.7042	Intermediate Similarity	NPD1840	Phase 2
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.703	Intermediate Similarity	NPD2969	Approved
0.703	Intermediate Similarity	NPD2970	Approved
0.7027	Intermediate Similarity	NPD1558	Phase 1
0.7024	Intermediate Similarity	NPD7472	Approved
0.7021	Intermediate Similarity	NPD3496	Discontinued
0.702	Intermediate Similarity	NPD3539	Phase 1
0.702	Intermediate Similarity	NPD6032	Approved
0.7019	Intermediate Similarity	NPD2560	Approved
0.7019	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2563	Approved
0.7019	Intermediate Similarity	NPD3817	Phase 2
0.7015	Intermediate Similarity	NPD3021	Approved
0.7015	Intermediate Similarity	NPD3022	Approved
0.7007	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD6896	Approved
0.7	Intermediate Similarity	NPD3445	Approved
0.7	Intermediate Similarity	NPD3444	Approved
0.7	Intermediate Similarity	NPD3443	Approved
0.7	Intermediate Similarity	NPD6895	Approved
0.6994	Remote Similarity	NPD919	Approved
0.6993	Remote Similarity	NPD4749	Approved
0.6993	Remote Similarity	NPD4162	Approved
0.6993	Remote Similarity	NPD3685	Discontinued
0.6993	Remote Similarity	NPD4359	Approved
0.6993	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD290	Approved
0.6987	Remote Similarity	NPD4123	Phase 3
0.698	Remote Similarity	NPD1933	Approved
0.6975	Remote Similarity	NPD3882	Suspended
0.6974	Remote Similarity	NPD3540	Phase 1
0.6972	Remote Similarity	NPD1281	Approved
0.6972	Remote Similarity	NPD776	Approved
0.6968	Remote Similarity	NPD6666	Approved
0.6968	Remote Similarity	NPD6667	Approved
0.6968	Remote Similarity	NPD7124	Phase 2
0.6959	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD709	Approved
0.6957	Remote Similarity	NPD2557	Approved
0.695	Remote Similarity	NPD6516	Phase 2
0.695	Remote Similarity	NPD5846	Approved
0.6948	Remote Similarity	NPD4628	Phase 3
0.6948	Remote Similarity	NPD7466	Approved
0.6928	Remote Similarity	NPD2424	Discontinued
0.6923	Remote Similarity	NPD1774	Approved
0.6919	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1247	Approved
0.6906	Remote Similarity	NPD3596	Phase 2
0.6901	Remote Similarity	NPD7808	Phase 3
0.6892	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5451	Approved
0.6886	Remote Similarity	NPD27	Approved
0.6886	Remote Similarity	NPD2489	Approved
0.6883	Remote Similarity	NPD3060	Approved
0.6883	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5177	Phase 3
0.6882	Remote Similarity	NPD6797	Phase 2
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7229	Phase 3
0.6867	Remote Similarity	NPD5123	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