NPASS Compound

Structure

CID263676 OpenBabel06191716062D 22 24 0 0 0 0 0 0 0 0999 V2000 3.3412 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 3.1691 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 21 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 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 18 2 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.09
Volume:	305.648
LogP:	3.294
LogD:	3.229
LogS:	-4.461
# Rotatable Bonds:	5
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	2.193
Fsp3:	0.111
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:	-4.648
MDCK Permeability:	2.884899549826514e-05
Pgp-inhibitor:	0.063
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.308
Plasma Protein Binding (PPB):	93.67261505126953%
Volume Distribution (VD):	0.476
Pgp-substrate:	2.9731497764587402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.243
CYP2D6-substrate:	0.391
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	10.471
Half-life (T1/2):	0.414

ADMET: Toxicity

hERG Blockers:	0.226
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.374
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.079
Carcinogencity:	0.567
Eye Corrosion:	0.008
Eye Irritation:	0.917
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC263676

Natural Product ID:	NPC263676
*Common Name:**	Pongamol
IUPAC Name:	(Z)-3-hydroxy-1-(4-methoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one
Synonyms:	Pongamol
Standard InCHIKey:	IHWPQGIYXJKCOV-PTNGSMBKSA-N
Standard InCHI:	InChI=1S/C18H14O4/c1-21-18-13(7-8-17-14(18)9-10-22-17)16(20)11-15(19)12-5-3-2-4-6-12/h2-11,19H,1H3/b15-11-
SMILES:	COc1c(ccc2c1cco2)C(=O)/C=C(/c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458131
PubChem CID:	5320675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003542] Furanochalcones

*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
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10814365]
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]
NPO31471	Poncirus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17666859]
NPO3037	Derris indica	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[19515570]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
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]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26476665]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322358]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31471	Poncirus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31471	Poncirus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
EC50	1
IC50	8
MIC	4
Others	14

Activity Type	# Activity
Cell Line	3
Individual Protein	13
NON-MOLECULAR	2
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	6.1	uM	PMID[468017]
NPT15	Cell Line	Jurkat	Homo sapiens	Activity	=	17.0	%	PMID[468019]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	23.0	%	PMID[468019]
NPT744	Cell Line	IMR-32	Homo sapiens	Activity	=	38.0	%	PMID[468019]
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	1.69	n.a.	PMID[468021]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[468022]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	FC	=	2.0	n.a.	PMID[468022]
NPT2795	Individual Protein	Fluoroquinolone resistance protein	Staphylococcus aureus	MIC	=	256.0	ug.mL-1	PMID[468022]
NPT2795	Individual Protein	Fluoroquinolone resistance protein	Staphylococcus aureus	FC	=	0.0	n.a.	PMID[468022]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Activity	=	73.0	%	PMID[468023]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	EC50	=	10200.0	nM	PMID[468023]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	4500.0	nM	PMID[468023]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	4400.0	nM	PMID[468023]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	3900.0	nM	PMID[468023]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	2400.0	nM	PMID[468023]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18700.0	nM	PMID[468017]
NPT2	Others	Unspecified		Ratio	=	3.1	n.a.	PMID[468017]
NPT1	Others	Radical scavenging activity		SC50	=	11.2	%	PMID[468018]
NPT2	Others	Unspecified		Activity	=	103.5	uM	PMID[468018]
NPT2	Others	Unspecified		IC50	=	58.2	%	PMID[468018]
NPT35	Others	n.a.		IC50	=	11640000.0	nM	PMID[468020]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	78.0	%	PMID[468021]
NPT2	Others	Unspecified		MIC	=	32.0	ug.mL-1	PMID[468022]
NPT2	Others	Unspecified		FC	=	0.0	n.a.	PMID[468022]
NPT2	Others	Unspecified		MIC	=	64.0	ug.mL-1	PMID[468022]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	IC50	=	88000.0	nM	PMID[468022]

☑ 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 NPC263676 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	385
0.1-0.2	1736
0.2-0.3	4168
0.3-0.4	10811
0.4-0.5	7616
0.5-0.6	4227
0.6-0.7	5904
0.7-0.8	4470
0.8-0.85	2155
0.85-0.9	1042
0.9-0.95	173
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC116604
0.9655	High Similarity	NPC198427
0.9595	High Similarity	NPC253872
0.9592	High Similarity	NPC148423
0.9592	High Similarity	NPC135303
0.9533	High Similarity	NPC160015
0.9533	High Similarity	NPC247677
0.9524	High Similarity	NPC226644
0.9524	High Similarity	NPC37226
0.9477	High Similarity	NPC193998
0.947	High Similarity	NPC296957
0.947	High Similarity	NPC260902
0.9463	High Similarity	NPC130015
0.9463	High Similarity	NPC67654
0.9463	High Similarity	NPC38361
0.9459	High Similarity	NPC472406
0.9456	High Similarity	NPC306788
0.9452	High Similarity	NPC190572
0.9412	High Similarity	NPC304387
0.9408	High Similarity	NPC476349
0.9408	High Similarity	NPC476350
0.94	High Similarity	NPC41719
0.94	High Similarity	NPC122365
0.94	High Similarity	NPC1477
0.94	High Similarity	NPC213608
0.9396	High Similarity	NPC156244
0.9396	High Similarity	NPC472407
0.9396	High Similarity	NPC170169
0.9392	High Similarity	NPC296030
0.9392	High Similarity	NPC39929
0.9388	High Similarity	NPC130581
0.9388	High Similarity	NPC12148
0.9338	High Similarity	NPC198490
0.9338	High Similarity	NPC233776
0.9333	High Similarity	NPC5871
0.9329	High Similarity	NPC230713
0.9329	High Similarity	NPC78335
0.9324	High Similarity	NPC135325
0.932	High Similarity	NPC210826
0.932	High Similarity	NPC51641
0.932	High Similarity	NPC300267
0.9315	High Similarity	NPC225884
0.9315	High Similarity	NPC302181
0.9272	High Similarity	NPC183874
0.9262	High Similarity	NPC178202
0.9257	High Similarity	NPC17816
0.9252	High Similarity	NPC230943
0.9247	High Similarity	NPC53192
0.9231	High Similarity	NPC38914
0.9226	High Similarity	NPC219861
0.9216	High Similarity	NPC65504
0.9216	High Similarity	NPC269495
0.9211	High Similarity	NPC148938
0.9167	High Similarity	NPC109180
0.9167	High Similarity	NPC472581
0.9156	High Similarity	NPC40583
0.9145	High Similarity	NPC235333
0.9145	High Similarity	NPC472462
0.9139	High Similarity	NPC115324
0.9133	High Similarity	NPC88445
0.9133	High Similarity	NPC37208
0.9133	High Similarity	NPC221868
0.9133	High Similarity	NPC317492
0.9122	High Similarity	NPC98926
0.9122	High Similarity	NPC155144
0.9114	High Similarity	NPC241820
0.911	High Similarity	NPC28337
0.9097	High Similarity	NPC169
0.9091	High Similarity	NPC212967
0.9091	High Similarity	NPC246647
0.9091	High Similarity	NPC96342
0.9091	High Similarity	NPC164110
0.9091	High Similarity	NPC270044
0.9085	High Similarity	NPC297531
0.9085	High Similarity	NPC213936
0.9079	High Similarity	NPC207624
0.9073	High Similarity	NPC167576
0.9073	High Similarity	NPC155882
0.9073	High Similarity	NPC191104
0.9067	High Similarity	NPC272194
0.9067	High Similarity	NPC168085
0.9062	High Similarity	NPC157522
0.9032	High Similarity	NPC472877
0.9026	High Similarity	NPC180924
0.9013	High Similarity	NPC193976
0.9013	High Similarity	NPC23668
0.9013	High Similarity	NPC106372
0.9013	High Similarity	NPC58668
0.9	High Similarity	NPC74539
0.9	High Similarity	NPC304443
0.8993	High Similarity	NPC110776
0.8993	High Similarity	NPC271590
0.8974	High Similarity	NPC49009
0.8974	High Similarity	NPC260296
0.8974	High Similarity	NPC304839
0.8974	High Similarity	NPC220582
0.8974	High Similarity	NPC115432
0.8968	High Similarity	NPC268360
0.8966	High Similarity	NPC29638
0.8954	High Similarity	NPC142308
0.8947	High Similarity	NPC472421
0.894	High Similarity	NPC39195
0.8933	High Similarity	NPC215885
0.8933	High Similarity	NPC2416
0.8933	High Similarity	NPC476153
0.8926	High Similarity	NPC262935
0.8926	High Similarity	NPC251182
0.8926	High Similarity	NPC17262
0.8926	High Similarity	NPC172182
0.8924	High Similarity	NPC65846
0.8919	High Similarity	NPC3188
0.8917	High Similarity	NPC14822
0.8917	High Similarity	NPC74854
0.8917	High Similarity	NPC30655
0.8917	High Similarity	NPC45124
0.8912	High Similarity	NPC137009
0.891	High Similarity	NPC244750
0.8903	High Similarity	NPC474386
0.8896	High Similarity	NPC72370
0.8889	High Similarity	NPC474744
0.8889	High Similarity	NPC318424
0.8889	High Similarity	NPC474772
0.8889	High Similarity	NPC472423
0.8882	High Similarity	NPC214493
0.8882	High Similarity	NPC131866
0.8874	High Similarity	NPC308200
0.8868	High Similarity	NPC136641
0.8867	High Similarity	NPC87486
0.8867	High Similarity	NPC234629
0.8867	High Similarity	NPC184649
0.8867	High Similarity	NPC303185
0.8867	High Similarity	NPC124780
0.8867	High Similarity	NPC246903
0.8867	High Similarity	NPC311741
0.8854	High Similarity	NPC239270
0.8854	High Similarity	NPC95472
0.8854	High Similarity	NPC303210
0.8851	High Similarity	NPC101366
0.8844	High Similarity	NPC124269
0.8844	High Similarity	NPC471620
0.8839	High Similarity	NPC473193
0.8839	High Similarity	NPC99199
0.8836	High Similarity	NPC222633
0.8831	High Similarity	NPC473996
0.8831	High Similarity	NPC31627
0.8831	High Similarity	NPC476238
0.8831	High Similarity	NPC327269
0.8824	High Similarity	NPC476185
0.8824	High Similarity	NPC321896
0.8816	High Similarity	NPC145467
0.8816	High Similarity	NPC266572
0.8816	High Similarity	NPC266743
0.8812	High Similarity	NPC277480
0.8812	High Similarity	NPC53640
0.8808	High Similarity	NPC472629
0.8808	High Similarity	NPC299011
0.8808	High Similarity	NPC73320
0.8805	High Similarity	NPC155640
0.8805	High Similarity	NPC38591
0.88	High Similarity	NPC149026
0.88	High Similarity	NPC221432
0.88	High Similarity	NPC68104
0.88	High Similarity	NPC310130
0.88	High Similarity	NPC39329
0.88	High Similarity	NPC91560
0.88	High Similarity	NPC143896
0.88	High Similarity	NPC175504
0.88	High Similarity	NPC169591
0.88	High Similarity	NPC18585
0.88	High Similarity	NPC150408
0.88	High Similarity	NPC166138
0.88	High Similarity	NPC106985
0.88	High Similarity	NPC113770
0.88	High Similarity	NPC75049
0.88	High Similarity	NPC257097
0.88	High Similarity	NPC164980
0.8797	High Similarity	NPC472346
0.8792	High Similarity	NPC268204
0.8792	High Similarity	NPC110969
0.8792	High Similarity	NPC469404
0.8792	High Similarity	NPC52789
0.8792	High Similarity	NPC470087
0.8792	High Similarity	NPC213322
0.8792	High Similarity	NPC324386
0.8792	High Similarity	NPC22467
0.8792	High Similarity	NPC321980
0.8792	High Similarity	NPC26051
0.8792	High Similarity	NPC103362
0.8792	High Similarity	NPC4743
0.8792	High Similarity	NPC55832
0.8792	High Similarity	NPC312391
0.8792	High Similarity	NPC470089
0.8784	High Similarity	NPC78913
0.8784	High Similarity	NPC295384
0.8784	High Similarity	NPC477956
0.8784	High Similarity	NPC18260
0.8784	High Similarity	NPC37206
0.8782	High Similarity	NPC45131
0.8776	High Similarity	NPC188879
0.8776	High Similarity	NPC472419

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 NPC263676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	1002
0.2-0.3	1534
0.3-0.4	2701
0.4-0.5	1917
0.5-0.6	1130
0.6-0.7	342
0.7-0.8	111
0.8-0.85	38
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD920	Approved
0.8867	High Similarity	NPD642	Clinical (unspecified phase)
0.8766	High Similarity	NPD7411	Suspended
0.8742	High Similarity	NPD4378	Clinical (unspecified phase)
0.8733	High Similarity	NPD643	Clinical (unspecified phase)
0.8679	High Similarity	NPD1247	Approved
0.8599	High Similarity	NPD8443	Clinical (unspecified phase)
0.8591	High Similarity	NPD1549	Phase 2
0.8533	High Similarity	NPD1243	Approved
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8523	High Similarity	NPD2344	Approved
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8514	High Similarity	NPD1510	Phase 2
0.8497	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1240	Approved
0.8491	Intermediate Similarity	NPD3749	Approved
0.8456	Intermediate Similarity	NPD2796	Approved
0.8434	Intermediate Similarity	NPD6559	Discontinued
0.8418	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD2800	Approved
0.8405	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1607	Approved
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD919	Approved
0.8313	Intermediate Similarity	NPD3882	Suspended
0.8302	Intermediate Similarity	NPD7819	Suspended
0.8302	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2309	Approved
0.8278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7075	Discontinued
0.8239	Intermediate Similarity	NPD1934	Approved
0.8212	Intermediate Similarity	NPD1551	Phase 2
0.8199	Intermediate Similarity	NPD7768	Phase 2
0.8194	Intermediate Similarity	NPD6799	Approved
0.816	Intermediate Similarity	NPD5494	Approved
0.8125	Intermediate Similarity	NPD6801	Discontinued
0.811	Intermediate Similarity	NPD6959	Discontinued
0.8077	Intermediate Similarity	NPD1511	Approved
0.8075	Intermediate Similarity	NPD2801	Approved
0.8037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7976	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD1512	Approved
0.7937	Intermediate Similarity	NPD3226	Approved
0.7908	Intermediate Similarity	NPD2799	Discontinued
0.7885	Intermediate Similarity	NPD3750	Approved
0.787	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6232	Discontinued
0.7836	Intermediate Similarity	NPD5953	Discontinued
0.7824	Intermediate Similarity	NPD7286	Phase 2
0.7824	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7473	Discontinued
0.7806	Intermediate Similarity	NPD1471	Phase 3
0.7805	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD2296	Approved
0.7677	Intermediate Similarity	NPD3748	Approved
0.7662	Intermediate Similarity	NPD6651	Approved
0.7633	Intermediate Similarity	NPD6808	Phase 2
0.7593	Intermediate Similarity	NPD5403	Approved
0.759	Intermediate Similarity	NPD5402	Approved
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD5401	Approved
0.7576	Intermediate Similarity	NPD6280	Approved
0.7576	Intermediate Similarity	NPD6279	Approved
0.7572	Intermediate Similarity	NPD7074	Phase 3
0.7571	Intermediate Similarity	NPD8434	Phase 2
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7533	Intermediate Similarity	NPD1203	Approved
0.7532	Intermediate Similarity	NPD943	Approved
0.753	Intermediate Similarity	NPD5761	Phase 2
0.753	Intermediate Similarity	NPD5760	Phase 2
0.7529	Intermediate Similarity	NPD7229	Phase 3
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4287	Approved
0.7471	Intermediate Similarity	NPD7472	Approved
0.7471	Intermediate Similarity	NPD1729	Discontinued
0.745	Intermediate Similarity	NPD9717	Approved
0.7429	Intermediate Similarity	NPD6797	Phase 2
0.7427	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5710	Approved
0.7407	Intermediate Similarity	NPD7390	Discontinued
0.7403	Intermediate Similarity	NPD3268	Approved
0.7386	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD7251	Discontinued
0.7378	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2654	Approved
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7808	Phase 3
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7341	Intermediate Similarity	NPD2403	Approved
0.733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1465	Phase 2
0.7305	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3764	Approved
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7261	Intermediate Similarity	NPD230	Phase 1
0.7261	Intermediate Similarity	NPD447	Suspended
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2798	Approved
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7228	Intermediate Similarity	NPD4360	Phase 2
0.7228	Intermediate Similarity	NPD4363	Phase 3
0.7219	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3267	Approved
0.719	Intermediate Similarity	NPD3266	Approved
0.7188	Intermediate Similarity	NPD6099	Approved
0.7188	Intermediate Similarity	NPD6100	Approved
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3751	Discontinued
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7151	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7124	Intermediate Similarity	NPD3225	Approved
0.7123	Intermediate Similarity	NPD1241	Discontinued
0.7117	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7003	Approved
0.7114	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD3972	Approved
0.7101	Intermediate Similarity	NPD5889	Approved
0.7101	Intermediate Similarity	NPD5890	Approved
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7091	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7458	Discontinued
0.7078	Intermediate Similarity	NPD1164	Approved
0.7078	Intermediate Similarity	NPD2797	Approved
0.7076	Intermediate Similarity	NPD4288	Approved
0.707	Intermediate Similarity	NPD411	Approved
0.7069	Intermediate Similarity	NPD7199	Phase 2
0.7044	Intermediate Similarity	NPD1933	Approved
0.7044	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6002	Phase 3
0.7037	Intermediate Similarity	NPD6004	Phase 3
0.7037	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6005	Phase 3
0.7027	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8313	Approved
0.7017	Intermediate Similarity	NPD8312	Approved
0.7013	Intermediate Similarity	NPD1876	Approved
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6104	Discontinued
0.6989	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD9494	Approved
0.6981	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4307	Phase 2
0.6981	Remote Similarity	NPD1613	Approved
0.698	Remote Similarity	NPD9493	Approved
0.6977	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5408	Approved
0.6975	Remote Similarity	NPD5404	Approved
0.6975	Remote Similarity	NPD5406	Approved
0.6975	Remote Similarity	NPD5405	Approved
0.6968	Remote Similarity	NPD1470	Approved
0.6966	Remote Similarity	NPD7177	Discontinued
0.6962	Remote Similarity	NPD6798	Discontinued
0.6962	Remote Similarity	NPD1296	Phase 2
0.6959	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD6844	Discontinued
0.6946	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6585	Discontinued
0.6937	Remote Similarity	NPD6355	Discontinued
0.6936	Remote Similarity	NPD4965	Approved
0.6936	Remote Similarity	NPD4967	Phase 2
0.6936	Remote Similarity	NPD4966	Approved
0.6932	Remote Similarity	NPD3787	Discontinued
0.6919	Remote Similarity	NPD8455	Phase 2
0.6908	Remote Similarity	NPD17	Approved
0.6907	Remote Similarity	NPD7584	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