NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.06
Volume:	271.005
LogP:	4.368
LogD:	3.167
LogS:	-6.172
# Rotatable Bonds:	1
TPSA:	43.35
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	2.195
Fsp3:	0.0
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:	-4.709
MDCK Permeability:	2.0325716832303442e-05
Pgp-inhibitor:	0.904
Pgp-substrate:	0.591
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.886
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	95.83763122558594%
Volume Distribution (VD):	1.163
Pgp-substrate:	4.452617168426514%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.759
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.573
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.438
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	4.584
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.327
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.204
Skin Sensitization:	0.104
Carcinogencity:	0.836
Eye Corrosion:	0.004
Eye Irritation:	0.849
Respiratory Toxicity:	0.807

Download Data

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

Natural Product: NPC306788

Natural Product ID:	NPC306788
*Common Name:**	Lanceolatin B
IUPAC Name:	2-phenylfuro[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	NQNOTBRHBRJKKH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H10O3/c18-14-10-16(11-4-2-1-3-5-11)20-17-12(14)6-7-15-13(17)8-9-19-15/h1-10H
SMILES:	O=c1cc(oc2c1ccc1c2cco1)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224157
PubChem CID:	10978265
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
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]
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]
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]
NPO21911	Tephrosia purpurea	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]
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21911	Tephrosia purpurea	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	2
IC50	16
MIC	1
Others	11

Activity Type	# Activity
Cell Line	6
Individual Protein	18
NON-MOLECULAR	2
Organism	1
Others	2
SINGLE PROTEIN	1

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	=	21.0	%	PMID[487612]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	22.9	uM	PMID[487613]
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	1.64	n.a.	PMID[487615]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	20590.0	nM	PMID[487616]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Activity	=	100.0	%	PMID[487617]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	60.0	%	PMID[487617]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	9.2	%	PMID[487617]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	7.1	%	PMID[487617]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	81.0	%	PMID[487617]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	700.0	nM	PMID[487617]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	EC50	=	14400.0	nM	PMID[487617]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT241	Individual Protein	Cytochrome P450 2E1	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT628	Individual Protein	Cytochrome P450 2C8	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT627	Individual Protein	Cytochrome P450 2B6	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	187.0	nM	PMID[487617]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	390.0	nM	PMID[487617]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	20.0	nM	PMID[487617]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	290.0	nM	PMID[487617]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	76.0	nM	PMID[487617]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	76300.0	nM	PMID[487613]
NPT2	Others	Unspecified		Ratio	>	3.3	n.a.	PMID[487613]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	50.0	ug.mL-1	PMID[487614]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[487615]
NPT2	Others	Unspecified		Ratio IC50	=	19.5	n.a.	PMID[487617]
NPT24960	SINGLE PROTEIN	Cytochrome P450 2C18	Homo sapiens	IC50	>	20000.0	nM	PMID[487617]

☑ 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 NPC306788 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	687
0.1-0.2	2336
0.2-0.3	5940
0.3-0.4	12428
0.4-0.5	4813
0.5-0.6	5416
0.6-0.7	5389
0.7-0.8	4278
0.8-0.85	1160
0.85-0.9	221
0.9-0.95	21
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC148423
0.986	High Similarity	NPC135303
0.9792	High Similarity	NPC472407
0.9789	High Similarity	NPC198427
0.9724	High Similarity	NPC38361
0.9724	High Similarity	NPC130015
0.9658	High Similarity	NPC41719
0.9592	High Similarity	NPC233776
0.9586	High Similarity	NPC472406
0.958	High Similarity	NPC190572
0.9521	High Similarity	NPC116604
0.9456	High Similarity	NPC263676
0.9306	High Similarity	NPC17262
0.9252	High Similarity	NPC88445
0.9241	High Similarity	NPC246903
0.9216	High Similarity	NPC193998
0.9195	High Similarity	NPC253872
0.9189	High Similarity	NPC191104
0.9156	High Similarity	NPC65846
0.9116	High Similarity	NPC74539
0.9116	High Similarity	NPC304443
0.9103	High Similarity	NPC166858
0.9103	High Similarity	NPC51146
0.9097	High Similarity	NPC38914
0.9085	High Similarity	NPC29638
0.9054	High Similarity	NPC266743
0.9026	High Similarity	NPC304387
0.9013	High Similarity	NPC247677
0.9013	High Similarity	NPC160015
0.9007	High Similarity	NPC1477
0.9007	High Similarity	NPC122365
0.9007	High Similarity	NPC213608
0.8993	High Similarity	NPC37226
0.8993	High Similarity	NPC226644
0.8981	High Similarity	NPC167479
0.8981	High Similarity	NPC241820
0.8973	High Similarity	NPC313036
0.8968	High Similarity	NPC219861
0.8954	High Similarity	NPC296957
0.8954	High Similarity	NPC65504
0.8954	High Similarity	NPC260902
0.894	High Similarity	NPC67654
0.894	High Similarity	NPC5871
0.8926	High Similarity	NPC272194
0.8924	High Similarity	NPC41853
0.8919	High Similarity	NPC300267
0.8919	High Similarity	NPC51641
0.8912	High Similarity	NPC225884
0.8904	High Similarity	NPC22467
0.8896	High Similarity	NPC476350
0.8896	High Similarity	NPC476349
0.8882	High Similarity	NPC472462
0.8874	High Similarity	NPC156244
0.8874	High Similarity	NPC170169
0.8873	High Similarity	NPC292998
0.8867	High Similarity	NPC317492
0.8867	High Similarity	NPC39929
0.8867	High Similarity	NPC221868
0.8867	High Similarity	NPC37208
0.8867	High Similarity	NPC296030
0.8859	High Similarity	NPC130581
0.8859	High Similarity	NPC12148
0.8851	High Similarity	NPC208584
0.8831	High Similarity	NPC269495
0.8824	High Similarity	NPC278010
0.8824	High Similarity	NPC250769
0.8824	High Similarity	NPC198490
0.8824	High Similarity	NPC295608
0.8819	High Similarity	NPC254741
0.8808	High Similarity	NPC78335
0.8808	High Similarity	NPC230713
0.8808	High Similarity	NPC155882
0.88	High Similarity	NPC168085
0.88	High Similarity	NPC135325
0.8792	High Similarity	NPC210826
0.879	High Similarity	NPC109180
0.879	High Similarity	NPC472581
0.8784	High Similarity	NPC302181
0.8782	High Similarity	NPC264293
0.8776	High Similarity	NPC254010
0.8774	High Similarity	NPC472877
0.8774	High Similarity	NPC40583
0.8767	High Similarity	NPC262635
0.8758	High Similarity	NPC131725
0.8758	High Similarity	NPC62640
0.8758	High Similarity	NPC183874
0.875	High Similarity	NPC190351
0.8742	High Similarity	NPC178202
0.8733	High Similarity	NPC17816
0.8732	High Similarity	NPC284424
0.8725	High Similarity	NPC179970
0.8725	High Similarity	NPC155144
0.8725	High Similarity	NPC230943
0.8718	High Similarity	NPC49009
0.8718	High Similarity	NPC169
0.8716	High Similarity	NPC53192
0.871	High Similarity	NPC268360
0.871	High Similarity	NPC270044
0.8707	High Similarity	NPC28337
0.8707	High Similarity	NPC472409
0.8701	High Similarity	NPC148938
0.869	High Similarity	NPC161196
0.8671	High Similarity	NPC182428
0.8662	High Similarity	NPC14822
0.8654	High Similarity	NPC250076
0.8639	High Similarity	NPC11566
0.8639	High Similarity	NPC136095
0.8636	High Similarity	NPC72370
0.8636	High Similarity	NPC235333
0.863	High Similarity	NPC157855
0.863	High Similarity	NPC259685
0.8627	High Similarity	NPC115324
0.8616	High Similarity	NPC136641
0.8611	High Similarity	NPC223354
0.8611	High Similarity	NPC247743
0.8609	High Similarity	NPC471285
0.8601	High Similarity	NPC278556
0.86	High Similarity	NPC110776
0.86	High Similarity	NPC271590
0.86	High Similarity	NPC98926
0.86	High Similarity	NPC311741
0.86	High Similarity	NPC234629
0.8599	High Similarity	NPC95472
0.8599	High Similarity	NPC115432
0.8599	High Similarity	NPC239270
0.8599	High Similarity	NPC303210
0.8599	High Similarity	NPC260296
0.859	High Similarity	NPC164110
0.859	High Similarity	NPC212967
0.859	High Similarity	NPC246647
0.859	High Similarity	NPC96342
0.8589	High Similarity	NPC66804
0.8582	High Similarity	NPC50583
0.8581	High Similarity	NPC297531
0.8581	High Similarity	NPC99199
0.8581	High Similarity	NPC213936
0.8581	High Similarity	NPC101366
0.858	High Similarity	NPC157522
0.8571	High Similarity	NPC31627
0.8571	High Similarity	NPC17848
0.8571	High Similarity	NPC476238
0.8571	High Similarity	NPC327269
0.8571	High Similarity	NPC207624
0.8562	High Similarity	NPC476185
0.8562	High Similarity	NPC321896
0.8562	High Similarity	NPC167576
0.8553	High Similarity	NPC39195
0.8553	High Similarity	NPC266572
0.8553	High Similarity	NPC38591
0.8552	High Similarity	NPC125269
0.8544	High Similarity	NPC45124
0.8544	High Similarity	NPC472346
0.8544	High Similarity	NPC30655
0.8544	High Similarity	NPC74854
0.8543	High Similarity	NPC2416
0.8543	High Similarity	NPC476153
0.8543	High Similarity	NPC73320
0.8543	High Similarity	NPC215885
0.8542	High Similarity	NPC473655
0.8542	High Similarity	NPC229646
0.8542	High Similarity	NPC101294
0.8535	High Similarity	NPC244750
0.8533	High Similarity	NPC59522
0.8528	High Similarity	NPC72455
0.8526	High Similarity	NPC180924
0.8526	High Similarity	NPC470625
0.8523	High Similarity	NPC52789
0.8523	High Similarity	NPC268204
0.8523	High Similarity	NPC26051
0.8523	High Similarity	NPC103362
0.8523	High Similarity	NPC3188
0.8523	High Similarity	NPC55832
0.8523	High Similarity	NPC469404
0.8523	High Similarity	NPC110969
0.8519	High Similarity	NPC131866
0.8514	High Similarity	NPC18260
0.8514	High Similarity	NPC137009
0.8514	High Similarity	NPC78913
0.8514	High Similarity	NPC295384
0.8506	High Similarity	NPC58668
0.8506	High Similarity	NPC106372
0.8506	High Similarity	NPC23668
0.8506	High Similarity	NPC193976
0.8506	High Similarity	NPC471675
0.8503	High Similarity	NPC228661
0.8503	High Similarity	NPC103001
0.8497	Intermediate Similarity	NPC214493
0.8493	Intermediate Similarity	NPC99854
0.8493	Intermediate Similarity	NPC46869
0.8487	Intermediate Similarity	NPC104406
0.8487	Intermediate Similarity	NPC24673
0.8487	Intermediate Similarity	NPC308200
0.8487	Intermediate Similarity	NPC97716
0.8487	Intermediate Similarity	NPC237635
0.8487	Intermediate Similarity	NPC201731
0.8487	Intermediate Similarity	NPC79469
0.8485	Intermediate Similarity	NPC472606
0.8481	Intermediate Similarity	NPC220582
0.8481	Intermediate Similarity	NPC304839
0.8481	Intermediate Similarity	NPC243509

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 NPC306788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	575
0.1-0.2	1020
0.2-0.3	1814
0.3-0.4	2820
0.4-0.5	1785
0.5-0.6	792
0.6-0.7	230
0.7-0.8	92
0.8-0.85	15
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD642	Clinical (unspecified phase)
0.9116	High Similarity	NPD920	Approved
0.9103	High Similarity	NPD643	Clinical (unspecified phase)
0.8819	High Similarity	NPD2796	Approved
0.8782	High Similarity	NPD1247	Approved
0.8767	High Similarity	NPD1243	Approved
0.8477	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD919	Approved
0.8387	Intermediate Similarity	NPD7411	Suspended
0.8367	Intermediate Similarity	NPD1510	Phase 2
0.8322	Intermediate Similarity	NPD1549	Phase 2
0.8255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5494	Approved
0.8239	Intermediate Similarity	NPD3749	Approved
0.8235	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4380	Phase 2
0.8133	Intermediate Similarity	NPD2344	Approved
0.8095	Intermediate Similarity	NPD1240	Approved
0.8084	Intermediate Similarity	NPD6559	Discontinued
0.805	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7819	Suspended
0.8049	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3748	Approved
0.7988	Intermediate Similarity	NPD3926	Phase 2
0.7987	Intermediate Similarity	NPD1607	Approved
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7935	Intermediate Similarity	NPD6799	Approved
0.7935	Intermediate Similarity	NPD1511	Approved
0.7922	Intermediate Similarity	NPD2309	Approved
0.7908	Intermediate Similarity	NPD2800	Approved
0.7901	Intermediate Similarity	NPD7075	Discontinued
0.7901	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1934	Approved
0.7844	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD3818	Discontinued
0.784	Intermediate Similarity	NPD7768	Phase 2
0.784	Intermediate Similarity	NPD3882	Suspended
0.7838	Intermediate Similarity	NPD2313	Discontinued
0.7834	Intermediate Similarity	NPD1512	Approved
0.7832	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1551	Phase 2
0.7826	Intermediate Similarity	NPD2801	Approved
0.7778	Intermediate Similarity	NPD1471	Phase 3
0.7778	Intermediate Similarity	NPD3817	Phase 2
0.7758	Intermediate Similarity	NPD6959	Discontinued
0.775	Intermediate Similarity	NPD6599	Discontinued
0.7742	Intermediate Similarity	NPD3750	Approved
0.7658	Intermediate Similarity	NPD5401	Approved
0.7654	Intermediate Similarity	NPD6279	Approved
0.7654	Intermediate Similarity	NPD6280	Approved
0.7605	Intermediate Similarity	NPD6808	Phase 2
0.7588	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD5403	Approved
0.7561	Intermediate Similarity	NPD5402	Approved
0.7547	Intermediate Similarity	NPD2534	Approved
0.7547	Intermediate Similarity	NPD2532	Approved
0.7547	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6232	Discontinued
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7473	Discontinued
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7453	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5953	Discontinued
0.7389	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7383	Intermediate Similarity	NPD3267	Approved
0.7383	Intermediate Similarity	NPD3266	Approved
0.7372	Intermediate Similarity	NPD2935	Discontinued
0.7349	Intermediate Similarity	NPD2296	Approved
0.7342	Intermediate Similarity	NPD2654	Approved
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2798	Approved
0.7325	Intermediate Similarity	NPD2346	Discontinued
0.731	Intermediate Similarity	NPD2403	Approved
0.7294	Intermediate Similarity	NPD7229	Phase 3
0.7283	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD5890	Approved
0.7273	Intermediate Similarity	NPD5889	Approved
0.7263	Intermediate Similarity	NPD4287	Approved
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.7241	Intermediate Similarity	NPD7074	Phase 3
0.7241	Intermediate Similarity	NPD7472	Approved
0.7219	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1241	Discontinued
0.72	Intermediate Similarity	NPD6797	Phase 2
0.7197	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1548	Phase 1
0.7186	Intermediate Similarity	NPD5761	Phase 2
0.7186	Intermediate Similarity	NPD5760	Phase 2
0.7181	Intermediate Similarity	NPD3972	Approved
0.7179	Intermediate Similarity	NPD6651	Approved
0.7161	Intermediate Similarity	NPD4307	Phase 2
0.7161	Intermediate Similarity	NPD943	Approved
0.7159	Intermediate Similarity	NPD7251	Discontinued
0.7152	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7808	Phase 3
0.7115	Intermediate Similarity	NPD1933	Approved
0.7114	Intermediate Similarity	NPD1610	Phase 2
0.7108	Intermediate Similarity	NPD6585	Discontinued
0.7105	Intermediate Similarity	NPD1019	Discontinued
0.7102	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7033	Discontinued
0.7086	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD1465	Phase 2
0.7081	Intermediate Similarity	NPD4628	Phase 3
0.7065	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4361	Phase 2
0.7055	Intermediate Similarity	NPD7390	Discontinued
0.7041	Intermediate Similarity	NPD4288	Approved
0.7037	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3764	Approved
0.7013	Intermediate Similarity	NPD4908	Phase 1
0.7012	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4360	Phase 2
0.7011	Intermediate Similarity	NPD4363	Phase 3
0.6994	Remote Similarity	NPD5710	Approved
0.6994	Remote Similarity	NPD5711	Approved
0.6981	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD17	Approved
0.6974	Remote Similarity	NPD3225	Approved
0.6964	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD9717	Approved
0.6946	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6099	Approved
0.6937	Remote Similarity	NPD6100	Approved
0.6935	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3751	Discontinued
0.6928	Remote Similarity	NPD2797	Approved
0.6915	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD422	Phase 1
0.6871	Remote Similarity	NPD7003	Approved
0.6842	Remote Similarity	NPD1608	Approved
0.6839	Remote Similarity	NPD7199	Phase 2
0.6835	Remote Similarity	NPD3140	Approved
0.6835	Remote Similarity	NPD3142	Approved
0.6824	Remote Similarity	NPD6844	Discontinued
0.6818	Remote Similarity	NPD1164	Approved
0.6818	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1651	Approved
0.68	Remote Similarity	NPD3787	Discontinued
0.6796	Remote Similarity	NPD8313	Approved
0.6796	Remote Similarity	NPD8312	Approved
0.6792	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD230	Phase 1
0.6792	Remote Similarity	NPD447	Suspended
0.6792	Remote Similarity	NPD5124	Phase 1
0.6784	Remote Similarity	NPD8455	Phase 2
0.6768	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5242	Approved
0.6752	Remote Similarity	NPD4625	Phase 3
0.6748	Remote Similarity	NPD2424	Discontinued
0.6747	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7458	Discontinued
0.6733	Remote Similarity	NPD9545	Approved
0.673	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1613	Approved
0.6728	Remote Similarity	NPD5404	Approved
0.6728	Remote Similarity	NPD5408	Approved
0.6728	Remote Similarity	NPD5405	Approved
0.6728	Remote Similarity	NPD5406	Approved
0.6727	Remote Similarity	NPD3887	Approved
0.6726	Remote Similarity	NPD3873	Phase 3
0.6726	Remote Similarity	NPD3869	Phase 3
0.672	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1470	Approved
0.6709	Remote Similarity	NPD6798	Discontinued
0.6707	Remote Similarity	NPD4661	Approved
0.6707	Remote Similarity	NPD4662	Approved
0.6705	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7584	Approved
0.6688	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2353	Approved
0.6687	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3658	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