NPASS Compound

Structure

CID41719 OpenBabel06191715372D 22 25 0 0 0 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 12 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.07
Volume:	297.091
LogP:	3.992
LogD:	3.293
LogS:	-5.007
# Rotatable Bonds:	2
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	2.271
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.73
MDCK Permeability:	2.632114410516806e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	93.18590545654297%
Volume Distribution (VD):	0.607
Pgp-substrate:	6.335160255432129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.72
CYP2C19-inhibitor:	0.882
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.332
CYP2D6-substrate:	0.64
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	3.623
Half-life (T1/2):	0.238

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.28
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.435
Rat Oral Acute Toxicity:	0.482
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.088
Carcinogencity:	0.835
Eye Corrosion:	0.003
Eye Irritation:	0.531
Respiratory Toxicity:	0.74

Download Data

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

Natural Product: NPC41719

Natural Product ID:	NPC41719
*Common Name:**	Karanjin
IUPAC Name:	3-methoxy-2-phenylfuro[2,3-h]chromen-4-one
Synonyms:	Karanjin
Standard InCHIKey:	LKPQNZRGGNOPPU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O4/c1-20-18-15(19)13-7-8-14-12(9-10-21-14)17(13)22-16(18)11-5-3-2-4-6-11/h2-10H,1H3
SMILES:	COc1c(oc2c(c1=O)ccc1c2cco1)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL208484
PubChem CID:	100633
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001759] Furanoflavones

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO3037	Derris indica	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[19515570]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25630222]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19856	Millettia pulchra	Species	Fabaceae	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	7
Others	10
Potency	28

Activity Type	# Activity
Cell Line	1
Individual Protein	33
NON-MOLECULAR	1
Organism	3
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	15.8	%	PMID[524936]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[524939]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[524939]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[524940]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	3981.1	nM	PMID[524940]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	8912.5	nM	PMID[524939]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PMID[524939]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	707.9	nM	PMID[524941]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	11220.2	nM	PMID[524939]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	10000.0	nM	PMID[524940]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3162.3	nM	PMID[524939]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	1000.0	nM	PMID[524940]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[524941]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20587.8	nM	PMID[524941]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[524941]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	316.2	nM	PMID[524942]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[524941]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[524941]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	15.8	%	PMID[524944]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	32642.7	nM	PMID[524941]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[524941]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[524941]
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	1.57	n.a.	PMID[524947]
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	100000.0	nM	PMID[524948]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	30.0	nM	PMID[524949]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	30.0	nM	PMID[524949]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	4100.0	nM	PMID[524949]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	2700.0	nM	PMID[524949]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	35.0	%	PMID[524936]
NPT2	Others	Unspecified		Activity	=	0.0	n.a.	PMID[524937]
NPT2	Others	Unspecified		IC50	=	26.3	%	PMID[524938]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	35481.3	nM	PMID[524939]
NPT2	Others	Unspecified		Potency	=	115.8	nM	PMID[524941]
NPT2	Others	Unspecified		Potency	=	398.1	nM	PMID[524939]
NPT2	Others	Unspecified		Potency	n.a.	12995.3	nM	PMID[524941]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[524941]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[524941]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-42.6	%	PMID[524943]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-30.8	%	PMID[524943]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	50.39	%	PMID[524945]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	124.74	%	PMID[524945]
NPT35	Others	n.a.		IC50	=	4232000.0	nM	PMID[524946]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[524947]

☑ 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 NPC41719 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	618
0.1-0.2	2257
0.2-0.3	5667
0.3-0.4	11995
0.4-0.5	5438
0.5-0.6	4955
0.6-0.7	5723
0.7-0.8	4364
0.8-0.85	1442
0.85-0.9	214
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC135303
0.9795	High Similarity	NPC148423
0.9662	High Similarity	NPC130015
0.9662	High Similarity	NPC38361
0.9658	High Similarity	NPC306788
0.9595	High Similarity	NPC472407
0.9589	High Similarity	NPC198427
0.9542	High Similarity	NPC193998
0.9533	High Similarity	NPC233776
0.9521	High Similarity	NPC190572
0.94	High Similarity	NPC263676
0.9396	High Similarity	NPC472406
0.9205	High Similarity	NPC116604
0.92	High Similarity	NPC88445
0.9167	High Similarity	NPC219861
0.9139	High Similarity	NPC191104
0.9122	High Similarity	NPC17262
0.9108	High Similarity	NPC65846
0.9108	High Similarity	NPC109180
0.9103	High Similarity	NPC264293
0.9068	High Similarity	NPC62640
0.9067	High Similarity	NPC74539
0.9067	High Similarity	NPC304443
0.9057	High Similarity	NPC241820
0.902	High Similarity	NPC253872
0.8987	High Similarity	NPC472581
0.8974	High Similarity	NPC250076
0.8968	High Similarity	NPC247677
0.8968	High Similarity	NPC160015
0.8961	High Similarity	NPC213608
0.8961	High Similarity	NPC1477
0.8961	High Similarity	NPC122365
0.8947	High Similarity	NPC226644
0.8947	High Similarity	NPC37226
0.894	High Similarity	NPC471285
0.8933	High Similarity	NPC246903
0.8931	High Similarity	NPC38914
0.891	High Similarity	NPC65504
0.891	High Similarity	NPC260902
0.891	High Similarity	NPC296957
0.8904	High Similarity	NPC29638
0.8896	High Similarity	NPC5871
0.8896	High Similarity	NPC67654
0.8882	High Similarity	NPC266743
0.8882	High Similarity	NPC41853
0.8861	High Similarity	NPC304387
0.8859	High Similarity	NPC22467
0.8854	High Similarity	NPC476349
0.8854	High Similarity	NPC476350
0.8839	High Similarity	NPC472462
0.8831	High Similarity	NPC170169
0.8831	High Similarity	NPC156244
0.8824	High Similarity	NPC317492
0.8824	High Similarity	NPC37208
0.8824	High Similarity	NPC39929
0.8824	High Similarity	NPC221868
0.8824	High Similarity	NPC296030
0.882	High Similarity	NPC167479
0.8816	High Similarity	NPC12148
0.8816	High Similarity	NPC130581
0.8808	High Similarity	NPC208584
0.88	High Similarity	NPC166858
0.88	High Similarity	NPC313036
0.88	High Similarity	NPC51146
0.8797	High Similarity	NPC243509
0.879	High Similarity	NPC269495
0.8782	High Similarity	NPC295608
0.8782	High Similarity	NPC250769
0.8782	High Similarity	NPC198490
0.8782	High Similarity	NPC278010
0.8776	High Similarity	NPC72452
0.8776	High Similarity	NPC61546
0.8776	High Similarity	NPC254741
0.8766	High Similarity	NPC78335
0.8766	High Similarity	NPC230713
0.8758	High Similarity	NPC168085
0.8758	High Similarity	NPC155264
0.8758	High Similarity	NPC210460
0.8758	High Similarity	NPC193881
0.8758	High Similarity	NPC272194
0.8758	High Similarity	NPC67450
0.8758	High Similarity	NPC323137
0.8758	High Similarity	NPC135325
0.875	High Similarity	NPC210826
0.875	High Similarity	NPC179464
0.875	High Similarity	NPC51641
0.875	High Similarity	NPC178343
0.875	High Similarity	NPC5820
0.875	High Similarity	NPC300267
0.875	High Similarity	NPC306488
0.8742	High Similarity	NPC216092
0.8742	High Similarity	NPC225884
0.8742	High Similarity	NPC302181
0.8734	High Similarity	NPC40583
0.8734	High Similarity	NPC33320
0.8718	High Similarity	NPC131725
0.8718	High Similarity	NPC183874
0.8712	High Similarity	NPC190351
0.871	High Similarity	NPC98028
0.8701	High Similarity	NPC178202
0.8701	High Similarity	NPC470461
0.8699	High Similarity	NPC292998
0.8693	High Similarity	NPC17816
0.8688	High Similarity	NPC234536
0.8688	High Similarity	NPC78612
0.8684	High Similarity	NPC216538
0.8684	High Similarity	NPC179970
0.8684	High Similarity	NPC273538
0.8684	High Similarity	NPC230943
0.8679	High Similarity	NPC49009
0.8679	High Similarity	NPC169
0.8675	High Similarity	NPC53192
0.8675	High Similarity	NPC473042
0.8671	High Similarity	NPC268360
0.8671	High Similarity	NPC270044
0.8662	High Similarity	NPC148938
0.8649	High Similarity	NPC161196
0.8645	High Similarity	NPC61258
0.8645	High Similarity	NPC155882
0.8636	High Similarity	NPC470460
0.863	High Similarity	NPC182428
0.8627	High Similarity	NPC470458
0.8627	High Similarity	NPC124729
0.8625	High Similarity	NPC14822
0.8618	High Similarity	NPC190637
0.8618	High Similarity	NPC293053
0.8618	High Similarity	NPC9117
0.8618	High Similarity	NPC158874
0.8618	High Similarity	NPC24821
0.8618	High Similarity	NPC212932
0.8616	High Similarity	NPC472877
0.8609	High Similarity	NPC254010
0.8609	High Similarity	NPC136840
0.86	High Similarity	NPC11566
0.86	High Similarity	NPC262635
0.86	High Similarity	NPC136095
0.8599	High Similarity	NPC235333
0.8599	High Similarity	NPC72370
0.8591	High Similarity	NPC259685
0.859	High Similarity	NPC115324
0.8589	High Similarity	NPC476459
0.858	High Similarity	NPC179015
0.858	High Similarity	NPC173149
0.858	High Similarity	NPC204088
0.858	High Similarity	NPC259007
0.858	High Similarity	NPC136641
0.858	High Similarity	NPC329215
0.8571	High Similarity	NPC223354
0.8562	High Similarity	NPC95472
0.8562	High Similarity	NPC110776
0.8562	High Similarity	NPC311741
0.8562	High Similarity	NPC260296
0.8562	High Similarity	NPC326500
0.8562	High Similarity	NPC271590
0.8562	High Similarity	NPC278556
0.8562	High Similarity	NPC284424
0.8562	High Similarity	NPC234629
0.8562	High Similarity	NPC115432
0.8562	High Similarity	NPC303210
0.8562	High Similarity	NPC239270
0.8562	High Similarity	NPC155144
0.8562	High Similarity	NPC98926
0.8554	High Similarity	NPC66804
0.8553	High Similarity	NPC246647
0.8553	High Similarity	NPC200694
0.8553	High Similarity	NPC96342
0.8553	High Similarity	NPC164110
0.8553	High Similarity	NPC212967
0.8545	High Similarity	NPC157522
0.8544	High Similarity	NPC297531
0.8544	High Similarity	NPC213936
0.8544	High Similarity	NPC99199
0.8543	High Similarity	NPC59951
0.8543	High Similarity	NPC230285
0.8543	High Similarity	NPC146679
0.8543	High Similarity	NPC269652
0.8543	High Similarity	NPC472409
0.8543	High Similarity	NPC103342
0.8543	High Similarity	NPC184536
0.8543	High Similarity	NPC28337
0.8543	High Similarity	NPC281207
0.8543	High Similarity	NPC103904
0.8543	High Similarity	NPC101366
0.8535	High Similarity	NPC476238
0.8535	High Similarity	NPC327269
0.8535	High Similarity	NPC207624
0.8535	High Similarity	NPC288534
0.8535	High Similarity	NPC31627
0.8533	High Similarity	NPC17848
0.8533	High Similarity	NPC276905
0.8526	High Similarity	NPC476185
0.8526	High Similarity	NPC321896
0.8526	High Similarity	NPC167576
0.8516	High Similarity	NPC39195
0.8516	High Similarity	NPC244407
0.8516	High Similarity	NPC296869
0.8516	High Similarity	NPC266572
0.8514	High Similarity	NPC125269
0.8512	High Similarity	NPC104682
0.8509	High Similarity	NPC45124

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 NPC41719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	522
0.1-0.2	1029
0.2-0.3	1908
0.3-0.4	2803
0.4-0.5	1720
0.5-0.6	823
0.6-0.7	232
0.7-0.8	88
0.8-0.85	17
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD1247	Approved
0.9067	High Similarity	NPD920	Approved
0.8933	High Similarity	NPD642	Clinical (unspecified phase)
0.88	High Similarity	NPD643	Clinical (unspecified phase)
0.8734	High Similarity	NPD919	Approved
0.8684	High Similarity	NPD4378	Clinical (unspecified phase)
0.8649	High Similarity	NPD2796	Approved
0.86	High Similarity	NPD1243	Approved
0.8365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7411	Suspended
0.8302	Intermediate Similarity	NPD6801	Discontinued
0.8258	Intermediate Similarity	NPD6799	Approved
0.8221	Intermediate Similarity	NPD5494	Approved
0.8212	Intermediate Similarity	NPD1510	Phase 2
0.821	Intermediate Similarity	NPD7075	Discontinued
0.8205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.817	Intermediate Similarity	NPD1549	Phase 2
0.8148	Intermediate Similarity	NPD3882	Suspended
0.8105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1471	Phase 3
0.8105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD3749	Approved
0.8086	Intermediate Similarity	NPD3817	Phase 2
0.8063	Intermediate Similarity	NPD4380	Phase 2
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8059	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2344	Approved
0.7947	Intermediate Similarity	NPD1240	Approved
0.7925	Intermediate Similarity	NPD1512	Approved
0.7885	Intermediate Similarity	NPD2800	Approved
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5401	Approved
0.7857	Intermediate Similarity	NPD3748	Approved
0.7853	Intermediate Similarity	NPD1934	Approved
0.7843	Intermediate Similarity	NPD1607	Approved
0.7824	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7805	Intermediate Similarity	NPD2801	Approved
0.7799	Intermediate Similarity	NPD1511	Approved
0.7785	Intermediate Similarity	NPD2309	Approved
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5403	Approved
0.7758	Intermediate Similarity	NPD5402	Approved
0.7738	Intermediate Similarity	NPD6959	Discontinued
0.7719	Intermediate Similarity	NPD3818	Discontinued
0.7706	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6166	Phase 2
0.7706	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.761	Intermediate Similarity	NPD3750	Approved
0.7602	Intermediate Similarity	NPD2403	Approved
0.7588	Intermediate Similarity	NPD6808	Phase 2
0.7568	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3226	Approved
0.7531	Intermediate Similarity	NPD2534	Approved
0.7531	Intermediate Similarity	NPD2533	Approved
0.7531	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD6280	Approved
0.753	Intermediate Similarity	NPD6279	Approved
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD6232	Discontinued
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7473	Discontinued
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7443	Intermediate Similarity	NPD7251	Discontinued
0.7439	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7401	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7808	Phase 3
0.7396	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5953	Discontinued
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5844	Phase 1
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7368	Intermediate Similarity	NPD3267	Approved
0.7368	Intermediate Similarity	NPD3266	Approved
0.7358	Intermediate Similarity	NPD2935	Discontinued
0.7329	Intermediate Similarity	NPD2654	Approved
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2346	Discontinued
0.7283	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD7054	Approved
0.7262	Intermediate Similarity	NPD5889	Approved
0.7262	Intermediate Similarity	NPD5890	Approved
0.7235	Intermediate Similarity	NPD2296	Approved
0.7232	Intermediate Similarity	NPD7074	Phase 3
0.7232	Intermediate Similarity	NPD7472	Approved
0.7208	Intermediate Similarity	NPD2798	Approved
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5761	Phase 2
0.7176	Intermediate Similarity	NPD5760	Phase 2
0.717	Intermediate Similarity	NPD6651	Approved
0.7158	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD4307	Phase 2
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3751	Discontinued
0.7107	Intermediate Similarity	NPD1933	Approved
0.7101	Intermediate Similarity	NPD6585	Discontinued
0.7097	Intermediate Similarity	NPD1019	Discontinued
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7075	Intermediate Similarity	NPD1241	Discontinued
0.7073	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4361	Phase 2
0.7059	Intermediate Similarity	NPD3972	Approved
0.7048	Intermediate Similarity	NPD7390	Discontinued
0.7045	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD943	Approved
0.7039	Intermediate Similarity	NPD1729	Discontinued
0.7035	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1203	Approved
0.703	Intermediate Similarity	NPD3887	Approved
0.7025	Intermediate Similarity	NPD1296	Phase 2
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.6994	Remote Similarity	NPD2353	Approved
0.6994	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5711	Approved
0.6989	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5710	Approved
0.6989	Remote Similarity	NPD3787	Discontinued
0.6977	Remote Similarity	NPD1465	Phase 2
0.6975	Remote Similarity	NPD4308	Phase 3
0.6968	Remote Similarity	NPD1876	Approved
0.6959	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1548	Phase 1
0.6948	Remote Similarity	NPD9717	Approved
0.6936	Remote Similarity	NPD4288	Approved
0.6927	Remote Similarity	NPD2163	Approved
0.6918	Remote Similarity	NPD3764	Approved
0.6911	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6355	Discontinued
0.6883	Remote Similarity	NPD1610	Phase 2
0.6875	Remote Similarity	NPD6233	Phase 2
0.6868	Remote Similarity	NPD6764	Approved
0.6868	Remote Similarity	NPD6765	Approved
0.6863	Remote Similarity	NPD17	Approved
0.6859	Remote Similarity	NPD3225	Approved
0.6842	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7199	Phase 2
0.6829	Remote Similarity	NPD6100	Approved
0.6829	Remote Similarity	NPD6099	Approved
0.6826	Remote Similarity	NPD2354	Approved
0.6826	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6844	Discontinued
0.6815	Remote Similarity	NPD2797	Approved
0.679	Remote Similarity	NPD447	Suspended
0.679	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.679	Remote Similarity	NPD230	Phase 1
0.679	Remote Similarity	NPD5124	Phase 1
0.6774	Remote Similarity	NPD422	Phase 1
0.6768	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7003	Approved
0.6766	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5049	Phase 3
0.676	Remote Similarity	NPD5242	Approved
0.6747	Remote Similarity	NPD2424	Discontinued
0.6746	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7458	Discontinued
0.6731	Remote Similarity	NPD1608	Approved
0.6728	Remote Similarity	NPD3140	Approved
0.6728	Remote Similarity	NPD3142	Approved
0.672	Remote Similarity	NPD6785	Approved
0.672	Remote Similarity	NPD6784	Approved
0.6705	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8313	Approved
0.6703	Remote Similarity	NPD8312	Approved
0.6702	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7584	Approved
0.6688	Remote Similarity	NPD1651	Approved
0.6687	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8455	Phase 2
0.6685	Remote Similarity	NPD6104	Discontinued
0.6684	Remote Similarity	NPD8285	Discontinued
0.6667	Remote Similarity	NPD6971	Discontinued
0.6649	Remote Similarity	NPD6782	Approved
0.6649	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD6777	Approved
0.6649	Remote Similarity	NPD6781	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