NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	267.589
LogP:	2.136
LogD:	2.351
LogS:	-3.676
# Rotatable Bonds:	3
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	2.811
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	1.8382002963335253e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.122

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	81.22718048095703%
Volume Distribution (VD):	1.092
Pgp-substrate:	12.87404727935791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.637
CYP2C19-substrate:	0.524
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.812
CYP2D6-inhibitor:	0.66
CYP2D6-substrate:	0.819
CYP3A4-inhibitor:	0.637
CYP3A4-substrate:	0.408

ADMET: Excretion

Clearance (CL):	9.012
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.842
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.696
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.62
Skin Sensitization:	0.392
Carcinogencity:	0.894
Eye Corrosion:	0.016
Eye Irritation:	0.211
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC175159

Natural Product ID:	NPC175159
*Common Name:**	Murralongin
IUPAC Name:	2-(7-methoxy-2-oxochromen-8-yl)-3-methylbut-2-enal
Synonyms:	Murralongin
Standard InCHIKey:	PBAZKMWQUBDDLZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-9(2)11(8-16)14-12(18-3)6-4-10-5-7-13(17)19-15(10)14/h4-8H,1-3H3
SMILES:	O=CC(=C(C)C)c1c(OC)ccc2c1oc(=O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098016
PubChem CID:	179620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO5744	Galipea panamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20423106]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO33003	murraya alata	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25621853]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715.1	Murraya paniculata var. exotica	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715.1	Murraya paniculata var. exotica	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5744	Galipea panamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2715	Murraya paniculata	Species	Rutaceae	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	1
Ki	6
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	CC50	=	121.4	ug.mL-1	PMID[471429]
NPT3101	Individual Protein	Carbonic anhydrase XIII	Homo sapiens	Ki	=	8890.0	nM	PMID[471430]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	100000.0	nM	PMID[471430]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	12400.0	nM	PMID[471431]
NPT3632	Organism	Leishmania panamensis	Leishmania panamensis	EC50	>	100.0	ug.mL-1	PMID[471429]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	9110.0	nM	PMID[471430]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	8850.0	nM	PMID[471430]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	8120.0	nM	PMID[471430]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	7440.0	nM	PMID[471430]

☑ 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 NPC175159 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	414
0.1-0.2	1941
0.2-0.3	5354
0.3-0.4	11397
0.4-0.5	6311
0.5-0.6	5032
0.6-0.7	5581
0.7-0.8	4890
0.8-0.85	1207
0.85-0.9	445
0.9-0.95	107
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.992	High Similarity	NPC472517
0.9457	High Similarity	NPC55147
0.937	High Similarity	NPC472519
0.9313	High Similarity	NPC229128
0.9308	High Similarity	NPC54503
0.9173	High Similarity	NPC472516
0.9127	High Similarity	NPC472518
0.9098	High Similarity	NPC104796
0.9058	High Similarity	NPC208584
0.9055	High Similarity	NPC201667
0.9055	High Similarity	NPC73413
0.9048	High Similarity	NPC96286
0.9048	High Similarity	NPC248429
0.8978	High Similarity	NPC229916
0.8976	High Similarity	NPC109675
0.8976	High Similarity	NPC273772
0.8971	High Similarity	NPC310370
0.8971	High Similarity	NPC183642
0.8968	High Similarity	NPC144418
0.8963	High Similarity	NPC253616
0.8963	High Similarity	NPC221046
0.8923	High Similarity	NPC199204
0.8915	High Similarity	NPC188327
0.8915	High Similarity	NPC234109
0.8906	High Similarity	NPC27671
0.8897	High Similarity	NPC36414
0.8889	High Similarity	NPC163200
0.8889	High Similarity	NPC268081
0.8881	High Similarity	NPC61499
0.888	High Similarity	NPC281356
0.888	High Similarity	NPC298796
0.8855	High Similarity	NPC168710
0.8837	High Similarity	NPC471828
0.8837	High Similarity	NPC471827
0.8832	High Similarity	NPC472515
0.8828	High Similarity	NPC173350
0.8828	High Similarity	NPC290605
0.8828	High Similarity	NPC154176
0.8824	High Similarity	NPC332594
0.8824	High Similarity	NPC307883
0.8803	High Similarity	NPC88445
0.88	High Similarity	NPC152306
0.88	High Similarity	NPC96705
0.88	High Similarity	NPC265547
0.8794	High Similarity	NPC74539
0.8794	High Similarity	NPC304443
0.8788	High Similarity	NPC80170
0.8779	High Similarity	NPC185066
0.8769	High Similarity	NPC471826
0.876	High Similarity	NPC111347
0.8759	High Similarity	NPC71903
0.875	High Similarity	NPC471068
0.875	High Similarity	NPC13007
0.875	High Similarity	NPC257188
0.875	High Similarity	NPC471069
0.8741	High Similarity	NPC191104
0.8741	High Similarity	NPC66705
0.874	High Similarity	NPC180006
0.874	High Similarity	NPC235190
0.8731	High Similarity	NPC222036
0.8731	High Similarity	NPC7526
0.8714	High Similarity	NPC71739
0.8714	High Similarity	NPC76657
0.8714	High Similarity	NPC295696
0.8696	High Similarity	NPC155552
0.8696	High Similarity	NPC136095
0.8696	High Similarity	NPC170812
0.8692	High Similarity	NPC93219
0.8692	High Similarity	NPC165556
0.8692	High Similarity	NPC244495
0.8686	High Similarity	NPC471070
0.8686	High Similarity	NPC471071
0.8686	High Similarity	NPC471072
0.8682	High Similarity	NPC315807
0.8676	High Similarity	NPC283331
0.8676	High Similarity	NPC476455
0.8676	High Similarity	NPC128529
0.8676	High Similarity	NPC471630
0.8676	High Similarity	NPC283019
0.8676	High Similarity	NPC55615
0.8676	High Similarity	NPC160727
0.8676	High Similarity	NPC223616
0.8676	High Similarity	NPC177281
0.8676	High Similarity	NPC149320
0.8667	High Similarity	NPC287182
0.8667	High Similarity	NPC195343
0.8667	High Similarity	NPC319859
0.8667	High Similarity	NPC55149
0.8667	High Similarity	NPC267412
0.8667	High Similarity	NPC18804
0.8667	High Similarity	NPC84894
0.8667	High Similarity	NPC74655
0.8667	High Similarity	NPC260265
0.8667	High Similarity	NPC307412
0.8667	High Similarity	NPC100986
0.8667	High Similarity	NPC166672
0.8667	High Similarity	NPC198381
0.8667	High Similarity	NPC47163
0.8667	High Similarity	NPC164269
0.8667	High Similarity	NPC127888
0.8657	High Similarity	NPC194277
0.8657	High Similarity	NPC307289
0.8657	High Similarity	NPC14248
0.8652	High Similarity	NPC246903
0.8643	High Similarity	NPC51146
0.8643	High Similarity	NPC166858
0.864	High Similarity	NPC128633
0.8636	High Similarity	NPC157212
0.8633	High Similarity	NPC470856
0.8615	High Similarity	NPC291899
0.8603	High Similarity	NPC472424
0.8603	High Similarity	NPC471625
0.8603	High Similarity	NPC281241
0.8603	High Similarity	NPC471909
0.8603	High Similarity	NPC86892
0.8601	High Similarity	NPC266743
0.8593	High Similarity	NPC296624
0.8593	High Similarity	NPC207002
0.8593	High Similarity	NPC31849
0.8593	High Similarity	NPC229646
0.8593	High Similarity	NPC471910
0.8593	High Similarity	NPC133956
0.8593	High Similarity	NPC167111
0.8593	High Similarity	NPC163557
0.8593	High Similarity	NPC318400
0.8561	High Similarity	NPC243688
0.8561	High Similarity	NPC37512
0.8551	High Similarity	NPC38153
0.8551	High Similarity	NPC103001
0.8542	High Similarity	NPC103116
0.8538	High Similarity	NPC50720
0.8529	High Similarity	NPC253574
0.8529	High Similarity	NPC326600
0.8529	High Similarity	NPC204353
0.8529	High Similarity	NPC50896
0.8529	High Similarity	NPC62366
0.8529	High Similarity	NPC98179
0.8519	High Similarity	NPC119985
0.8519	High Similarity	NPC19157
0.8519	High Similarity	NPC280476
0.8511	High Similarity	NPC313036
0.8511	High Similarity	NPC251372
0.8507	High Similarity	NPC469929
0.8478	Intermediate Similarity	NPC155963
0.8467	Intermediate Similarity	NPC33986
0.8467	Intermediate Similarity	NPC469675
0.8462	Intermediate Similarity	NPC150214
0.8462	Intermediate Similarity	NPC190572
0.844	Intermediate Similarity	NPC254010
0.8435	Intermediate Similarity	NPC131725
0.8433	Intermediate Similarity	NPC474289
0.8429	Intermediate Similarity	NPC472523
0.8429	Intermediate Similarity	NPC473209
0.8429	Intermediate Similarity	NPC262635
0.8421	Intermediate Similarity	NPC224774
0.8421	Intermediate Similarity	NPC258567
0.8421	Intermediate Similarity	NPC49852
0.8421	Intermediate Similarity	NPC121740
0.8421	Intermediate Similarity	NPC475496
0.8417	Intermediate Similarity	NPC148738
0.8417	Intermediate Similarity	NPC327612
0.8417	Intermediate Similarity	NPC151946
0.8417	Intermediate Similarity	NPC211110
0.8417	Intermediate Similarity	NPC319870
0.8417	Intermediate Similarity	NPC73078
0.8406	Intermediate Similarity	NPC188380
0.8406	Intermediate Similarity	NPC60667
0.8406	Intermediate Similarity	NPC224543
0.8406	Intermediate Similarity	NPC78746
0.8406	Intermediate Similarity	NPC38099
0.8406	Intermediate Similarity	NPC46869
0.8406	Intermediate Similarity	NPC26954
0.8394	Intermediate Similarity	NPC180716
0.8394	Intermediate Similarity	NPC224475
0.8394	Intermediate Similarity	NPC213173
0.8392	Intermediate Similarity	NPC171656
0.8389	Intermediate Similarity	NPC269495
0.8385	Intermediate Similarity	NPC187868
0.8385	Intermediate Similarity	NPC52247
0.8382	Intermediate Similarity	NPC469956
0.8378	Intermediate Similarity	NPC250769
0.8378	Intermediate Similarity	NPC295608
0.8378	Intermediate Similarity	NPC278010
0.837	Intermediate Similarity	NPC113098
0.837	Intermediate Similarity	NPC32463
0.8358	Intermediate Similarity	NPC2401
0.8358	Intermediate Similarity	NPC139595
0.8358	Intermediate Similarity	NPC473907
0.8358	Intermediate Similarity	NPC469453
0.8358	Intermediate Similarity	NPC60704
0.8358	Intermediate Similarity	NPC293642
0.8357	Intermediate Similarity	NPC312881
0.8356	Intermediate Similarity	NPC155882
0.8346	Intermediate Similarity	NPC101894
0.8345	Intermediate Similarity	NPC225106
0.8345	Intermediate Similarity	NPC232246
0.8345	Intermediate Similarity	NPC294456
0.8345	Intermediate Similarity	NPC184861
0.8345	Intermediate Similarity	NPC309452
0.8345	Intermediate Similarity	NPC281014

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 NPC175159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	1002
0.2-0.3	1775
0.3-0.4	2735
0.4-0.5	1803
0.5-0.6	982
0.6-0.7	316
0.7-0.8	96
0.8-0.85	33
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8794	High Similarity	NPD920	Approved
0.8652	High Similarity	NPD642	Clinical (unspecified phase)
0.8647	High Similarity	NPD1296	Phase 2
0.8643	High Similarity	NPD643	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD1243	Approved
0.8406	Intermediate Similarity	NPD3748	Approved
0.8385	Intermediate Similarity	NPD422	Phase 1
0.837	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD2796	Approved
0.8214	Intermediate Similarity	NPD1551	Phase 2
0.8212	Intermediate Similarity	NPD919	Approved
0.8112	Intermediate Similarity	NPD3750	Approved
0.811	Intermediate Similarity	NPD1241	Discontinued
0.8088	Intermediate Similarity	NPD6832	Phase 2
0.8069	Intermediate Similarity	NPD6799	Approved
0.8058	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD5124	Phase 1
0.8054	Intermediate Similarity	NPD7411	Suspended
0.8042	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD3267	Approved
0.8	Intermediate Similarity	NPD3266	Approved
0.7972	Intermediate Similarity	NPD1549	Phase 2
0.7947	Intermediate Similarity	NPD7819	Suspended
0.7947	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1019	Discontinued
0.791	Intermediate Similarity	NPD9717	Approved
0.7902	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1510	Phase 2
0.7868	Intermediate Similarity	NPD2797	Approved
0.7867	Intermediate Similarity	NPD6599	Discontinued
0.7862	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4307	Phase 2
0.7857	Intermediate Similarity	NPD1240	Approved
0.7847	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7768	Phase 2
0.7792	Intermediate Similarity	NPD7075	Discontinued
0.777	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD5401	Approved
0.7762	Intermediate Similarity	NPD2799	Discontinued
0.776	Intermediate Similarity	NPD9697	Approved
0.7756	Intermediate Similarity	NPD1247	Approved
0.7746	Intermediate Similarity	NPD1607	Approved
0.774	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1203	Approved
0.7714	Intermediate Similarity	NPD2313	Discontinued
0.7714	Intermediate Similarity	NPD3268	Approved
0.7697	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD17	Approved
0.7676	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1652	Phase 2
0.7669	Intermediate Similarity	NPD1548	Phase 1
0.7667	Intermediate Similarity	NPD5403	Approved
0.7664	Intermediate Similarity	NPD3225	Approved
0.7655	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4308	Phase 3
0.7586	Intermediate Similarity	NPD2935	Discontinued
0.7574	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3817	Phase 2
0.7537	Intermediate Similarity	NPD9545	Approved
0.7533	Intermediate Similarity	NPD2534	Approved
0.7533	Intermediate Similarity	NPD2533	Approved
0.7533	Intermediate Similarity	NPD2532	Approved
0.7518	Intermediate Similarity	NPD1608	Approved
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1358	Approved
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5535	Approved
0.7481	Intermediate Similarity	NPD5691	Approved
0.7469	Intermediate Similarity	NPD5844	Phase 1
0.7468	Intermediate Similarity	NPD5494	Approved
0.7465	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6798	Discontinued
0.7452	Intermediate Similarity	NPD3749	Approved
0.7445	Intermediate Similarity	NPD1281	Approved
0.7445	Intermediate Similarity	NPD1610	Phase 2
0.7436	Intermediate Similarity	NPD4288	Approved
0.7436	Intermediate Similarity	NPD5402	Approved
0.7436	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2800	Approved
0.7431	Intermediate Similarity	NPD230	Phase 1
0.7431	Intermediate Similarity	NPD1933	Approved
0.7431	Intermediate Similarity	NPD447	Suspended
0.7422	Intermediate Similarity	NPD3134	Approved
0.7407	Intermediate Similarity	NPD1894	Discontinued
0.7397	Intermediate Similarity	NPD7033	Discontinued
0.7378	Intermediate Similarity	NPD5953	Discontinued
0.7362	Intermediate Similarity	NPD7286	Phase 2
0.7351	Intermediate Similarity	NPD1511	Approved
0.7347	Intermediate Similarity	NPD4476	Approved
0.7347	Intermediate Similarity	NPD4477	Approved
0.7343	Intermediate Similarity	NPD411	Approved
0.7342	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3226	Approved
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7324	Intermediate Similarity	NPD4908	Phase 1
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6355	Discontinued
0.7308	Intermediate Similarity	NPD1934	Approved
0.7299	Intermediate Similarity	NPD1778	Approved
0.7297	Intermediate Similarity	NPD6004	Phase 3
0.7297	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6002	Phase 3
0.7297	Intermediate Similarity	NPD2346	Discontinued
0.7297	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6005	Phase 3
0.7286	Intermediate Similarity	NPD1283	Approved
0.7278	Intermediate Similarity	NPD3882	Suspended
0.7267	Intermediate Similarity	NPD7229	Phase 3
0.7266	Intermediate Similarity	NPD1481	Phase 2
0.7261	Intermediate Similarity	NPD1465	Phase 2
0.7261	Intermediate Similarity	NPD2801	Approved
0.7259	Intermediate Similarity	NPD9493	Approved
0.7255	Intermediate Similarity	NPD1512	Approved
0.7241	Intermediate Similarity	NPD2979	Phase 3
0.7226	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1535	Discovery
0.7194	Intermediate Similarity	NPD1611	Approved
0.7192	Intermediate Similarity	NPD4622	Approved
0.7192	Intermediate Similarity	NPD4618	Approved
0.7174	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD6233	Phase 2
0.7161	Intermediate Similarity	NPD1653	Approved
0.716	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD6651	Approved
0.7134	Intermediate Similarity	NPD5889	Approved
0.7134	Intermediate Similarity	NPD5890	Approved
0.7133	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD6971	Discontinued
0.7122	Intermediate Similarity	NPD3496	Discontinued
0.7115	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2438	Suspended
0.7105	Intermediate Similarity	NPD3887	Approved
0.7103	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3764	Approved
0.7101	Intermediate Similarity	NPD1651	Approved
0.7095	Intermediate Similarity	NPD5689	Approved
0.7095	Intermediate Similarity	NPD5688	Approved
0.7091	Intermediate Similarity	NPD3818	Discontinued
0.7086	Intermediate Similarity	NPD2654	Approved
0.7078	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2353	Approved
0.7067	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2798	Approved
0.7059	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8032	Phase 2
0.7055	Intermediate Similarity	NPD4062	Phase 3
0.7044	Intermediate Similarity	NPD8455	Phase 2
0.7042	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD7003	Approved
0.7032	Intermediate Similarity	NPD5049	Phase 3
0.7032	Intermediate Similarity	NPD2186	Approved
0.7032	Intermediate Similarity	NPD6273	Approved
0.703	Intermediate Similarity	NPD7473	Discontinued
0.7014	Intermediate Similarity	NPD454	Approved
0.7013	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3926	Phase 2
0.7012	Intermediate Similarity	NPD5242	Approved
0.7007	Intermediate Similarity	NPD4060	Phase 1
0.7007	Intermediate Similarity	NPD3142	Approved
0.7007	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3140	Approved
0.7007	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD2531	Phase 2
0.7	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD3847	Discontinued
0.6994	Remote Similarity	NPD7199	Phase 2
0.6994	Remote Similarity	NPD6959	Discontinued
0.6988	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD37	Approved
0.698	Remote Similarity	NPD7097	Phase 1
0.6978	Remote Similarity	NPD5585	Approved
0.6966	Remote Similarity	NPD2614	Approved
0.6966	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6585	Discontinued
0.6959	Remote Similarity	NPD4340	Discontinued
0.6957	Remote Similarity	NPD4967	Phase 2
0.6957	Remote Similarity	NPD4966	Approved
0.6957	Remote Similarity	NPD4965	Approved
0.6954	Remote Similarity	NPD2344	Approved
0.6951	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD5710	Approved
0.6948	Remote Similarity	NPD6667	Approved
0.6948	Remote Similarity	NPD6666	Approved
0.6923	Remote Similarity	NPD9261	Approved
0.6923	Remote Similarity	NPD8651	Approved
0.6923	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4625	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data