NPASS Compound

Structure

CID38099 OpenBabel06191715372D 22 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -0.0000 -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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -2.5981 -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 -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 3 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 -1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 5 1 0 0 0 0 2 10 2 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.13
Volume:	313.608
LogP:	2.067
LogD:	2.325
LogS:	-3.164
# Rotatable Bonds:	6
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	3.62
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.723
MDCK Permeability:	1.8236360119772144e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	79.67566680908203%
Volume Distribution (VD):	1.325
Pgp-substrate:	18.886146545410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.35
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.714
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.601
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.631
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	10.349
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.81
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.592
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.063
Carcinogencity:	0.862
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.299

Download Data

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

Natural Product: NPC38099

Natural Product ID:	NPC38099
*Common Name:**	Murpanicin
IUPAC Name:	8-(1-ethoxy-2-hydroxy-3-methylbut-3-enyl)-7-methoxychromen-2-one
Synonyms:
Standard InCHIKey:	GDLSTIJVZWVVPB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O5/c1-5-21-17(15(19)10(2)3)14-12(20-4)8-6-11-7-9-13(18)22-16(11)14/h6-9,15,17,19H,2,5H2,1,3-4H3
SMILES:	CCOC(c1c(OC)ccc2c1oc(=O)cc2)C(C(=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426682
PubChem CID:	188750
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
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]
NPO2715	Murraya paniculata	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]
NPO2715.1	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]
NPO2715.2	Murraya paniculata (l.) jack var. exotica (l.) huang	Varieties	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]
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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	43300.0	nM	PMID[513247]

☑ 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 NPC38099 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	356
0.1-0.2	1441
0.2-0.3	3687
0.3-0.4	8092
0.4-0.5	10328
0.5-0.6	4104
0.6-0.7	5576
0.7-0.8	4656
0.8-0.85	3147
0.85-0.9	1088
0.9-0.95	182
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC26954
0.9847	High Similarity	NPC151946
0.9845	High Similarity	NPC50896
0.9845	High Similarity	NPC326600
0.9845	High Similarity	NPC204353
0.9771	High Similarity	NPC155963
0.9769	High Similarity	NPC472525
0.9767	High Similarity	NPC31849
0.9699	High Similarity	NPC152771
0.9699	High Similarity	NPC195357
0.9697	High Similarity	NPC279573
0.9692	High Similarity	NPC62366
0.9692	High Similarity	NPC224475
0.9692	High Similarity	NPC180716
0.9692	High Similarity	NPC213173
0.9624	High Similarity	NPC312881
0.9621	High Similarity	NPC225106
0.9621	High Similarity	NPC232246
0.9621	High Similarity	NPC294456
0.9621	High Similarity	NPC281014
0.9621	High Similarity	NPC212124
0.9621	High Similarity	NPC153818
0.9621	High Similarity	NPC184861
0.9552	High Similarity	NPC287286
0.9549	High Similarity	NPC211110
0.9545	High Similarity	NPC188380
0.9545	High Similarity	NPC224543
0.9545	High Similarity	NPC78746
0.9538	High Similarity	NPC194277
0.947	High Similarity	NPC33986
0.9462	High Similarity	NPC29734
0.9416	High Similarity	NPC469701
0.9394	High Similarity	NPC98179
0.9394	High Similarity	NPC253574
0.9385	High Similarity	NPC113098
0.9343	High Similarity	NPC471824
0.9318	High Similarity	NPC163557
0.9318	High Similarity	NPC296624
0.9318	High Similarity	NPC318400
0.9318	High Similarity	NPC167111
0.9318	High Similarity	NPC133956
0.9318	High Similarity	NPC471910
0.9318	High Similarity	NPC207002
0.9313	High Similarity	NPC267336
0.9313	High Similarity	NPC272650
0.9308	High Similarity	NPC168710
0.9302	High Similarity	NPC121740
0.9302	High Similarity	NPC258567
0.9302	High Similarity	NPC224774
0.9275	High Similarity	NPC85624
0.9248	High Similarity	NPC18804
0.9248	High Similarity	NPC84894
0.9248	High Similarity	NPC267412
0.9248	High Similarity	NPC260265
0.9248	High Similarity	NPC287182
0.9248	High Similarity	NPC74655
0.9248	High Similarity	NPC307412
0.9248	High Similarity	NPC198381
0.9248	High Similarity	NPC55149
0.9248	High Similarity	NPC195343
0.9248	High Similarity	NPC164269
0.9248	High Similarity	NPC166672
0.9248	High Similarity	NPC127888
0.9248	High Similarity	NPC319859
0.9248	High Similarity	NPC100986
0.9248	High Similarity	NPC47163
0.9242	High Similarity	NPC14248
0.9231	High Similarity	NPC469453
0.9231	High Similarity	NPC185066
0.9214	High Similarity	NPC169510
0.9203	High Similarity	NPC471763
0.9179	High Similarity	NPC472424
0.9179	High Similarity	NPC86892
0.9179	High Similarity	NPC471625
0.9179	High Similarity	NPC469675
0.9179	High Similarity	NPC471909
0.9179	High Similarity	NPC281241
0.9173	High Similarity	NPC7526
0.9173	High Similarity	NPC469449
0.9173	High Similarity	NPC222036
0.9154	High Similarity	NPC243688
0.9143	High Similarity	NPC87950
0.9143	High Similarity	NPC296377
0.9143	High Similarity	NPC471764
0.9111	High Similarity	NPC471630
0.9111	High Similarity	NPC55615
0.9111	High Similarity	NPC128529
0.9111	High Similarity	NPC476455
0.9111	High Similarity	NPC160727
0.9111	High Similarity	NPC283019
0.9111	High Similarity	NPC149320
0.9111	High Similarity	NPC177281
0.9091	High Similarity	NPC80170
0.9084	High Similarity	NPC199204
0.907	High Similarity	NPC73413
0.907	High Similarity	NPC201667
0.9044	High Similarity	NPC471068
0.9044	High Similarity	NPC471069
0.9008	High Similarity	NPC473993
0.9	High Similarity	NPC471827
0.9	High Similarity	NPC471828
0.9	High Similarity	NPC93219
0.9	High Similarity	NPC244495
0.8992	High Similarity	NPC273772
0.8992	High Similarity	NPC472518
0.8992	High Similarity	NPC109675
0.8986	High Similarity	NPC300611
0.8986	High Similarity	NPC279851
0.8986	High Similarity	NPC472520
0.8978	High Similarity	NPC471071
0.8978	High Similarity	NPC471072
0.8978	High Similarity	NPC164148
0.8978	High Similarity	NPC43500
0.8978	High Similarity	NPC471070
0.8971	High Similarity	NPC283331
0.8951	High Similarity	NPC103116
0.8947	High Similarity	NPC32463
0.8939	High Similarity	NPC472519
0.8936	High Similarity	NPC205361
0.8931	High Similarity	NPC188327
0.8931	High Similarity	NPC234109
0.8923	High Similarity	NPC27671
0.8915	High Similarity	NPC96286
0.8915	High Similarity	NPC248429
0.8905	High Similarity	NPC131198
0.8889	High Similarity	NPC2363
0.8889	High Similarity	NPC241165
0.8889	High Similarity	NPC205797
0.8889	High Similarity	NPC469965
0.8889	High Similarity	NPC142563
0.8889	High Similarity	NPC141822
0.8889	High Similarity	NPC291551
0.8889	High Similarity	NPC1220
0.8881	High Similarity	NPC103799
0.8881	High Similarity	NPC250727
0.8873	High Similarity	NPC476347
0.8865	High Similarity	NPC226722
0.8857	High Similarity	NPC229916
0.8857	High Similarity	NPC138212
0.8849	High Similarity	NPC138149
0.8841	High Similarity	NPC47040
0.8841	High Similarity	NPC278600
0.8841	High Similarity	NPC35501
0.8841	High Similarity	NPC144512
0.8841	High Similarity	NPC137262
0.8841	High Similarity	NPC37428
0.8832	High Similarity	NPC103409
0.8824	High Similarity	NPC131950
0.8811	High Similarity	NPC476348
0.8811	High Similarity	NPC187398
0.8788	High Similarity	NPC471826
0.8786	High Similarity	NPC20631
0.8786	High Similarity	NPC93640
0.876	High Similarity	NPC163200
0.876	High Similarity	NPC235190
0.876	High Similarity	NPC180006
0.8741	High Similarity	NPC15577
0.8732	High Similarity	NPC101255
0.8732	High Similarity	NPC475719
0.8732	High Similarity	NPC108994
0.8732	High Similarity	NPC106126
0.8732	High Similarity	NPC43716
0.8723	High Similarity	NPC119640
0.8723	High Similarity	NPC183646
0.8714	High Similarity	NPC215512
0.8714	High Similarity	NPC310370
0.8714	High Similarity	NPC476442
0.8714	High Similarity	NPC183642
0.8712	High Similarity	NPC202594
0.8712	High Similarity	NPC232692
0.8705	High Similarity	NPC13067
0.8699	High Similarity	NPC470264
0.8692	High Similarity	NPC144418
0.8692	High Similarity	NPC187868
0.8692	High Similarity	NPC52247
0.869	High Similarity	NPC21184
0.869	High Similarity	NPC294522
0.869	High Similarity	NPC205727
0.869	High Similarity	NPC120426
0.8686	High Similarity	NPC92830
0.8676	High Similarity	NPC19157
0.8667	High Similarity	NPC19242
0.8662	High Similarity	NPC476457
0.8657	High Similarity	NPC219923
0.8657	High Similarity	NPC274717
0.8652	High Similarity	NPC184053
0.8639	High Similarity	NPC256141
0.8636	High Similarity	NPC111347
0.8636	High Similarity	NPC291899
0.8633	High Similarity	NPC139548
0.8633	High Similarity	NPC20511
0.8633	High Similarity	NPC474886
0.8633	High Similarity	NPC76336
0.8633	High Similarity	NPC52086
0.8633	High Similarity	NPC95162
0.8633	High Similarity	NPC148835
0.8623	High Similarity	NPC61499
0.8623	High Similarity	NPC472521
0.8621	High Similarity	NPC176903
0.8621	High Similarity	NPC30688

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 NPC38099 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	871
0.2-0.3	1796
0.3-0.4	2542
0.4-0.5	1926
0.5-0.6	1111
0.6-0.7	389
0.7-0.8	130
0.8-0.85	53
0.85-0.9	18
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD5124	Phase 1
0.8889	High Similarity	NPD5123	Clinical (unspecified phase)
0.8714	High Similarity	NPD1652	Phase 2
0.8692	High Similarity	NPD422	Phase 1
0.8367	Intermediate Similarity	NPD1653	Approved
0.8267	Intermediate Similarity	NPD6801	Discontinued
0.8212	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD7075	Discontinued
0.8143	Intermediate Similarity	NPD1613	Approved
0.8143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4380	Phase 2
0.8129	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD3027	Phase 3
0.8014	Intermediate Similarity	NPD4060	Phase 1
0.8014	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD2424	Discontinued
0.8	Intermediate Similarity	NPD1091	Approved
0.7986	Intermediate Similarity	NPD4908	Phase 1
0.7973	Intermediate Similarity	NPD6799	Approved
0.797	Intermediate Similarity	NPD1548	Phase 1
0.7937	Intermediate Similarity	NPD5844	Phase 1
0.7935	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD5403	Approved
0.7919	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD3750	Approved
0.7871	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1610	Phase 2
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7411	Suspended
0.7826	Intermediate Similarity	NPD8651	Approved
0.7823	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5402	Approved
0.78	Intermediate Similarity	NPD5401	Approved
0.7794	Intermediate Similarity	NPD3496	Discontinued
0.7786	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.777	Intermediate Similarity	NPD2797	Approved
0.777	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7768	Phase 2
0.7752	Intermediate Similarity	NPD2684	Approved
0.7746	Intermediate Similarity	NPD6798	Discontinued
0.7746	Intermediate Similarity	NPD1296	Phase 2
0.7742	Intermediate Similarity	NPD7819	Suspended
0.774	Intermediate Similarity	NPD2796	Approved
0.7727	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD4626	Approved
0.7716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6355	Discontinued
0.7708	Intermediate Similarity	NPD4340	Discontinued
0.7698	Intermediate Similarity	NPD3225	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD3817	Phase 2
0.7687	Intermediate Similarity	NPD6002	Phase 3
0.7687	Intermediate Similarity	NPD6004	Phase 3
0.7687	Intermediate Similarity	NPD5762	Approved
0.7687	Intermediate Similarity	NPD6005	Phase 3
0.7687	Intermediate Similarity	NPD5763	Approved
0.7687	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6559	Discontinued
0.7677	Intermediate Similarity	NPD1934	Approved
0.7674	Intermediate Similarity	NPD290	Approved
0.7674	Intermediate Similarity	NPD1358	Approved
0.7671	Intermediate Similarity	NPD3748	Approved
0.7671	Intermediate Similarity	NPD7033	Discontinued
0.7652	Intermediate Similarity	NPD7843	Approved
0.7651	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5691	Approved
0.7635	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD1551	Phase 2
0.7612	Intermediate Similarity	NPD7157	Approved
0.7603	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4538	Approved
0.7603	Intermediate Similarity	NPD4536	Approved
0.7584	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1243	Approved
0.7569	Intermediate Similarity	NPD6233	Phase 2
0.7568	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4625	Phase 3
0.7551	Intermediate Similarity	NPD1510	Phase 2
0.755	Intermediate Similarity	NPD6667	Approved
0.755	Intermediate Similarity	NPD6666	Approved
0.755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3818	Discontinued
0.7519	Intermediate Similarity	NPD9697	Approved
0.7519	Intermediate Similarity	NPD5535	Approved
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD8455	Phase 2
0.7516	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD7097	Phase 1
0.7468	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2415	Discontinued
0.7465	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3134	Approved
0.7452	Intermediate Similarity	NPD37	Approved
0.7451	Intermediate Similarity	NPD2533	Approved
0.7451	Intermediate Similarity	NPD2534	Approved
0.7451	Intermediate Similarity	NPD2532	Approved
0.745	Intermediate Similarity	NPD7266	Discontinued
0.7438	Intermediate Similarity	NPD919	Approved
0.7434	Intermediate Similarity	NPD5058	Phase 3
0.7432	Intermediate Similarity	NPD5588	Approved
0.7432	Intermediate Similarity	NPD5960	Phase 3
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7432	Intermediate Similarity	NPD2799	Discontinued
0.7429	Intermediate Similarity	NPD9717	Approved
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7423	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6166	Phase 2
0.7423	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4965	Approved
0.7421	Intermediate Similarity	NPD4967	Phase 2
0.7421	Intermediate Similarity	NPD4966	Approved
0.7421	Intermediate Similarity	NPD3882	Suspended
0.7415	Intermediate Similarity	NPD6653	Approved
0.7413	Intermediate Similarity	NPD2861	Phase 2
0.741	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4140	Approved
0.7397	Intermediate Similarity	NPD1240	Approved
0.7394	Intermediate Similarity	NPD7054	Approved
0.7386	Intermediate Similarity	NPD1511	Approved
0.7379	Intermediate Similarity	NPD2313	Discontinued
0.7361	Intermediate Similarity	NPD6832	Phase 2
0.7349	Intermediate Similarity	NPD7472	Approved
0.7349	Intermediate Similarity	NPD7074	Phase 3
0.7347	Intermediate Similarity	NPD230	Phase 1
0.7347	Intermediate Similarity	NPD447	Suspended
0.7346	Intermediate Similarity	NPD7199	Phase 2
0.7338	Intermediate Similarity	NPD1778	Approved
0.7329	Intermediate Similarity	NPD4062	Phase 3
0.7329	Intermediate Similarity	NPD6234	Discontinued
0.7321	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD6797	Phase 2
0.7301	Intermediate Similarity	NPD6232	Discontinued
0.7297	Intermediate Similarity	NPD1607	Approved
0.7296	Intermediate Similarity	NPD1465	Phase 2
0.729	Intermediate Similarity	NPD1512	Approved
0.7284	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD3267	Approved
0.7273	Intermediate Similarity	NPD7213	Phase 3
0.7273	Intermediate Similarity	NPD3266	Approved
0.7273	Intermediate Similarity	NPD1203	Approved
0.7273	Intermediate Similarity	NPD7212	Phase 2
0.7267	Intermediate Similarity	NPD6032	Approved
0.7262	Intermediate Similarity	NPD7251	Discontinued
0.7261	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1048	Approved
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7237	Intermediate Similarity	NPD6674	Discontinued
0.7237	Intermediate Similarity	NPD2800	Approved
0.7234	Intermediate Similarity	NPD1611	Approved
0.7233	Intermediate Similarity	NPD4433	Discontinued
0.7226	Intermediate Similarity	NPD6671	Approved
0.7226	Intermediate Similarity	NPD7447	Phase 1
0.7226	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3691	Phase 2
0.7222	Intermediate Similarity	NPD3690	Phase 2
0.7219	Intermediate Similarity	NPD7808	Phase 3
0.7202	Intermediate Similarity	NPD5953	Discontinued
0.7197	Intermediate Similarity	NPD3687	Approved
0.7197	Intermediate Similarity	NPD3686	Approved
0.7195	Intermediate Similarity	NPD7229	Phase 3
0.7186	Intermediate Similarity	NPD7286	Phase 2
0.7179	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4666	Phase 3
0.7172	Intermediate Similarity	NPD3018	Phase 2
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7162	Intermediate Similarity	NPD4307	Phase 2
0.716	Intermediate Similarity	NPD3749	Approved
0.7154	Intermediate Similarity	NPD846	Approved
0.7154	Intermediate Similarity	NPD940	Approved
0.7152	Intermediate Similarity	NPD3226	Approved
0.7152	Intermediate Similarity	NPD4476	Approved
0.7152	Intermediate Similarity	NPD4477	Approved
0.7152	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD7985	Registered
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6959	Discontinued
0.7133	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7228	Approved
0.7119	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5709	Phase 3
0.7115	Intermediate Similarity	NPD3536	Discontinued
0.7114	Intermediate Similarity	NPD1899	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