NPASS Compound

Structure

CID283331 OpenBabel06191716092D 26 28 0 0 1 0 0 0 0 0999 V2000 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -3.5491 1.8090 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 -6.6369 1.8660 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 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 -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 -4.1369 1.0000 0.0000 C 0 0 1 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 1.0000 0.0000 O 0 0 0 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 -3.5491 0.1910 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 -5.6369 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 21 1 0 0 0 0 7 20 1 0 0 0 0 8 13 1 0 0 0 0 8 14 2 0 0 0 0 9 13 1 0 0 0 0 9 15 2 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 22 2 0 0 0 0 12 26 1 0 0 0 0 13 17 2 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 6 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	5.07
LogD:	3.359
LogS:	-4.498
# Rotatable Bonds:	5
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	3.7
Fsp3:	0.429
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:	-4.742
MDCK Permeability:	2.3149419575929642e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.496

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	90.48786926269531%
Volume Distribution (VD):	1.046
Pgp-substrate:	12.239107131958008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.789
CYP1A2-substrate:	0.249
CYP2C19-inhibitor:	0.862
CYP2C19-substrate:	0.344
CYP2C9-inhibitor:	0.73
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.808
CYP2D6-substrate:	0.705
CYP3A4-inhibitor:	0.796
CYP3A4-substrate:	0.438

ADMET: Excretion

Clearance (CL):	2.108
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.705
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.591
Carcinogencity:	0.715
Eye Corrosion:	0.026
Eye Irritation:	0.057
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC283331

Natural Product ID:	NPC283331
*Common Name:**	(+)-Rutamarin
IUPAC Name:	2-[(2S)-6-(2-methylbut-3-en-2-yl)-7-oxo-2,3-dihydrofuro[3,2-g]chromen-2-yl]propan-2-yl acetate
Synonyms:
Standard InCHIKey:	AWMHMGFGCLBSAY-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-7-20(3,4)15-9-13-8-14-10-18(21(5,6)26-12(2)22)24-16(14)11-17(13)25-19(15)23/h7-9,11,18H,1,10H2,2-6H3/t18-/m0/s1
SMILES:	C=CC(c1cc2cc3C[C@H](Oc3cc2oc1=O)C(OC(=O)C)(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577084
PubChem CID:	442148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO442	Boenninghausenia japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO442	Boenninghausenia japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO442	Boenninghausenia japonica	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]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO442	Boenninghausenia japonica	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
Others	4

Activity Type	# Activity
CELL-LINE	1
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	>	150000.0	nM	PMID[507226]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	5430.0	nM	PMID[507226]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	39.6	n.a.	PMID[507226]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	7000.0	nM	PMID[507227]
NPT26641	CELL-LINE	P3HR-1	Homo sapiens	CC50	>	150000.0	nM	PMID[507227]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	21.0	n.a.	PMID[507227]

☑ 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 NPC283331 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	415
0.1-0.2	1637
0.2-0.3	3797
0.3-0.4	8968
0.4-0.5	9824
0.5-0.6	4214
0.6-0.7	6187
0.7-0.8	5887
0.8-0.85	1296
0.85-0.9	323
0.9-0.95	118
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC222036
0.9767	High Similarity	NPC7526
0.9692	High Similarity	NPC307412
0.9692	High Similarity	NPC55149
0.969	High Similarity	NPC14248
0.9398	High Similarity	NPC476455
0.9398	High Similarity	NPC149320
0.9398	High Similarity	NPC283019
0.9398	High Similarity	NPC177281
0.9398	High Similarity	NPC160727
0.9398	High Similarity	NPC55615
0.9398	High Similarity	NPC471630
0.9398	High Similarity	NPC128529
0.9394	High Similarity	NPC267412
0.9394	High Similarity	NPC47163
0.9394	High Similarity	NPC198381
0.9394	High Similarity	NPC195343
0.9394	High Similarity	NPC74655
0.9394	High Similarity	NPC319859
0.9394	High Similarity	NPC164269
0.9394	High Similarity	NPC84894
0.9394	High Similarity	NPC127888
0.9394	High Similarity	NPC166672
0.9394	High Similarity	NPC18804
0.9394	High Similarity	NPC287182
0.9394	High Similarity	NPC100986
0.9394	High Similarity	NPC260265
0.9323	High Similarity	NPC471625
0.9323	High Similarity	NPC281241
0.9323	High Similarity	NPC472424
0.9323	High Similarity	NPC86892
0.9323	High Similarity	NPC471909
0.9318	High Similarity	NPC296624
0.9318	High Similarity	NPC318400
0.9318	High Similarity	NPC471910
0.9318	High Similarity	NPC133956
0.9318	High Similarity	NPC167111
0.9318	High Similarity	NPC207002
0.9248	High Similarity	NPC253574
0.9248	High Similarity	NPC98179
0.9225	High Similarity	NPC188327
0.9225	High Similarity	NPC234109
0.9185	High Similarity	NPC155963
0.9185	High Similarity	NPC14697
0.9179	High Similarity	NPC469675
0.9179	High Similarity	NPC33986
0.9118	High Similarity	NPC151946
0.9118	High Similarity	NPC211110
0.9091	High Similarity	NPC80170
0.9084	High Similarity	NPC157212
0.9084	High Similarity	NPC472519
0.907	High Similarity	NPC201667
0.907	High Similarity	NPC73413
0.9051	High Similarity	NPC312881
0.9037	High Similarity	NPC472525
0.9015	High Similarity	NPC168710
0.9	High Similarity	NPC471827
0.9	High Similarity	NPC471828
0.8993	High Similarity	NPC183646
0.8993	High Similarity	NPC119640
0.8992	High Similarity	NPC273772
0.8992	High Similarity	NPC472518
0.8992	High Similarity	NPC109675
0.8986	High Similarity	NPC287286
0.8986	High Similarity	NPC152771
0.8986	High Similarity	NPC195357
0.8978	High Similarity	NPC279573
0.8971	High Similarity	NPC26954
0.8971	High Similarity	NPC38099
0.8963	High Similarity	NPC180716
0.8963	High Similarity	NPC62366
0.8963	High Similarity	NPC213173
0.8963	High Similarity	NPC224475
0.8939	High Similarity	NPC199204
0.8939	High Similarity	NPC185066
0.8931	High Similarity	NPC471826
0.8929	High Similarity	NPC476457
0.8923	High Similarity	NPC27671
0.8915	High Similarity	NPC248429
0.8915	High Similarity	NPC96286
0.8905	High Similarity	NPC232246
0.8905	High Similarity	NPC471068
0.8905	High Similarity	NPC471069
0.8905	High Similarity	NPC153818
0.8897	High Similarity	NPC229128
0.8889	High Similarity	NPC31849
0.8889	High Similarity	NPC163557
0.8881	High Similarity	NPC29734
0.8865	High Similarity	NPC76657
0.8864	High Similarity	NPC289316
0.8841	High Similarity	NPC307883
0.8841	High Similarity	NPC471071
0.8841	High Similarity	NPC471070
0.8841	High Similarity	NPC471072
0.8832	High Similarity	NPC224543
0.8832	High Similarity	NPC188380
0.8832	High Similarity	NPC78746
0.8824	High Similarity	NPC326600
0.8824	High Similarity	NPC50896
0.8824	High Similarity	NPC204353
0.8806	High Similarity	NPC113098
0.8788	High Similarity	NPC163248
0.8779	High Similarity	NPC291899
0.8779	High Similarity	NPC111347
0.8768	High Similarity	NPC281014
0.8768	High Similarity	NPC212124
0.8768	High Similarity	NPC225106
0.8768	High Similarity	NPC306365
0.8768	High Similarity	NPC184861
0.8768	High Similarity	NPC294456
0.876	High Similarity	NPC180006
0.876	High Similarity	NPC163200
0.876	High Similarity	NPC235190
0.8759	High Similarity	NPC61499
0.875	High Similarity	NPC55147
0.875	High Similarity	NPC469449
0.875	High Similarity	NPC54503
0.8741	High Similarity	NPC296377
0.8741	High Similarity	NPC272650
0.8741	High Similarity	NPC267336
0.8714	High Similarity	NPC155552
0.8702	High Similarity	NPC173350
0.8702	High Similarity	NPC50720
0.8702	High Similarity	NPC154176
0.8702	High Similarity	NPC290605
0.8692	High Similarity	NPC144418
0.8681	High Similarity	NPC169510
0.8676	High Similarity	NPC194277
0.8676	High Similarity	NPC469956
0.8676	High Similarity	NPC175159
0.8667	High Similarity	NPC19242
0.8662	High Similarity	NPC471824
0.8657	High Similarity	NPC60704
0.8657	High Similarity	NPC293642
0.8657	High Similarity	NPC139595
0.8633	High Similarity	NPC131198
0.8626	High Similarity	NPC13007
0.8626	High Similarity	NPC150214
0.8626	High Similarity	NPC257188
0.8613	High Similarity	NPC83535
0.8613	High Similarity	NPC469955
0.8613	High Similarity	NPC469952
0.8605	High Similarity	NPC281356
0.8605	High Similarity	NPC298796
0.8603	High Similarity	NPC472517
0.8601	High Similarity	NPC469701
0.8601	High Similarity	NPC85624
0.8591	High Similarity	NPC470625
0.8582	High Similarity	NPC258567
0.8582	High Similarity	NPC243688
0.8582	High Similarity	NPC138149
0.8582	High Similarity	NPC121740
0.8582	High Similarity	NPC472523
0.8582	High Similarity	NPC224774
0.8571	High Similarity	NPC270256
0.8561	High Similarity	NPC315807
0.8542	High Similarity	NPC171656
0.854	High Similarity	NPC19157
0.854	High Similarity	NPC123954
0.8531	High Similarity	NPC251372
0.8527	High Similarity	NPC265547
0.8527	High Similarity	NPC96705
0.8527	High Similarity	NPC152306
0.8521	High Similarity	NPC20631
0.8521	High Similarity	NPC470856
0.8521	High Similarity	NPC93640
0.8519	High Similarity	NPC469453
0.8507	High Similarity	NPC101894
0.8483	Intermediate Similarity	NPC471764
0.8483	Intermediate Similarity	NPC87950
0.8478	Intermediate Similarity	NPC241341
0.8478	Intermediate Similarity	NPC233018
0.8478	Intermediate Similarity	NPC36437
0.8478	Intermediate Similarity	NPC472522
0.8472	Intermediate Similarity	NPC106126
0.8472	Intermediate Similarity	NPC71739
0.8472	Intermediate Similarity	NPC108994
0.8467	Intermediate Similarity	NPC66430
0.8467	Intermediate Similarity	NPC37009
0.8462	Intermediate Similarity	NPC229916
0.8456	Intermediate Similarity	NPC131725
0.844	Intermediate Similarity	NPC253616
0.8435	Intermediate Similarity	NPC103116
0.8433	Intermediate Similarity	NPC202594
0.8433	Intermediate Similarity	NPC232692
0.8433	Intermediate Similarity	NPC244495
0.8433	Intermediate Similarity	NPC93219
0.8429	Intermediate Similarity	NPC167517
0.8429	Intermediate Similarity	NPC104796
0.8421	Intermediate Similarity	NPC143725
0.8417	Intermediate Similarity	NPC131950
0.8414	Intermediate Similarity	NPC294365
0.8406	Intermediate Similarity	NPC137669
0.8406	Intermediate Similarity	NPC319969
0.8403	Intermediate Similarity	NPC471763
0.8394	Intermediate Similarity	NPC32463
0.838	Intermediate Similarity	NPC36414
0.838	Intermediate Similarity	NPC71903
0.8372	Intermediate Similarity	NPC128633
0.837	Intermediate Similarity	NPC127604

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 NPC283331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	963
0.2-0.3	1708
0.3-0.4	2642
0.4-0.5	1942
0.5-0.6	1028
0.6-0.7	367
0.7-0.8	118
0.8-0.85	22
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8345	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD5124	Phase 1
0.8134	Intermediate Similarity	NPD422	Phase 1
0.8069	Intermediate Similarity	NPD1243	Approved
0.8054	Intermediate Similarity	NPD920	Approved
0.8027	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1296	Phase 2
0.7986	Intermediate Similarity	NPD2796	Approved
0.7986	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1652	Phase 2
0.7919	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3748	Approved
0.7908	Intermediate Similarity	NPD6801	Discontinued
0.7895	Intermediate Similarity	NPD6599	Discontinued
0.7891	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD919	Approved
0.7852	Intermediate Similarity	NPD6799	Approved
0.7821	Intermediate Similarity	NPD7075	Discontinued
0.777	Intermediate Similarity	NPD4628	Phase 3
0.7755	Intermediate Similarity	NPD2424	Discontinued
0.7674	Intermediate Similarity	NPD1358	Approved
0.7651	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD5691	Approved
0.7628	Intermediate Similarity	NPD7819	Suspended
0.7622	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7411	Suspended
0.761	Intermediate Similarity	NPD5494	Approved
0.7606	Intermediate Similarity	NPD6832	Phase 2
0.7586	Intermediate Similarity	NPD6355	Discontinued
0.7584	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5403	Approved
0.7571	Intermediate Similarity	NPD8651	Approved
0.7566	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5401	Approved
0.7551	Intermediate Similarity	NPD7033	Discontinued
0.7548	Intermediate Similarity	NPD4380	Phase 2
0.7532	Intermediate Similarity	NPD7768	Phase 2
0.7532	Intermediate Similarity	NPD1653	Approved
0.7519	Intermediate Similarity	NPD5535	Approved
0.7519	Intermediate Similarity	NPD9697	Approved
0.7518	Intermediate Similarity	NPD3267	Approved
0.7518	Intermediate Similarity	NPD2797	Approved
0.7518	Intermediate Similarity	NPD3266	Approved
0.7517	Intermediate Similarity	NPD4307	Phase 2
0.7516	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7484	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7464	Intermediate Similarity	NPD1778	Approved
0.7462	Intermediate Similarity	NPD3134	Approved
0.7451	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6002	Phase 3
0.745	Intermediate Similarity	NPD6005	Phase 3
0.745	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6004	Phase 3
0.7447	Intermediate Similarity	NPD3225	Approved
0.7445	Intermediate Similarity	NPD1548	Phase 1
0.7431	Intermediate Similarity	NPD7095	Approved
0.7421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3496	Discontinued
0.7405	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1549	Phase 2
0.7397	Intermediate Similarity	NPD4060	Phase 1
0.7389	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1551	Phase 2
0.7379	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3268	Approved
0.7375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7365	Intermediate Similarity	NPD7097	Phase 1
0.7358	Intermediate Similarity	NPD5402	Approved
0.7357	Intermediate Similarity	NPD1610	Phase 2
0.7353	Intermediate Similarity	NPD7157	Approved
0.7351	Intermediate Similarity	NPD2800	Approved
0.7346	Intermediate Similarity	NPD1247	Approved
0.7338	Intermediate Similarity	NPD2532	Approved
0.7338	Intermediate Similarity	NPD2534	Approved
0.7338	Intermediate Similarity	NPD4626	Approved
0.7338	Intermediate Similarity	NPD2533	Approved
0.7333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1241	Discontinued
0.7315	Intermediate Similarity	NPD2799	Discontinued
0.7315	Intermediate Similarity	NPD4308	Phase 3
0.7315	Intermediate Similarity	NPD1510	Phase 2
0.7312	Intermediate Similarity	NPD3882	Suspended
0.7303	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7266	Intermediate Similarity	NPD5585	Approved
0.725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7199	Phase 2
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7233	Intermediate Similarity	NPD37	Approved
0.7233	Intermediate Similarity	NPD1934	Approved
0.723	Intermediate Similarity	NPD4340	Discontinued
0.723	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3818	Discontinued
0.7226	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1019	Discontinued
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD5763	Approved
0.7218	Intermediate Similarity	NPD2684	Approved
0.7212	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8032	Phase 2
0.7211	Intermediate Similarity	NPD6233	Phase 2
0.7205	Intermediate Similarity	NPD4966	Approved
0.7205	Intermediate Similarity	NPD4965	Approved
0.7205	Intermediate Similarity	NPD4967	Phase 2
0.7195	Intermediate Similarity	NPD7229	Phase 3
0.7192	Intermediate Similarity	NPD3027	Phase 3
0.7192	Intermediate Similarity	NPD4625	Phase 3
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4110	Phase 3
0.7186	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9717	Approved
0.7179	Intermediate Similarity	NPD6273	Approved
0.7162	Intermediate Similarity	NPD1240	Approved
0.7161	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD6099	Approved
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4749	Approved
0.7132	Intermediate Similarity	NPD7843	Approved
0.7123	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7117	Intermediate Similarity	NPD6234	Discontinued
0.7114	Intermediate Similarity	NPD1933	Approved
0.7113	Intermediate Similarity	NPD1611	Approved
0.7113	Intermediate Similarity	NPD1091	Approved
0.7105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5058	Phase 3
0.7097	Intermediate Similarity	NPD6667	Approved
0.7097	Intermediate Similarity	NPD6666	Approved
0.7095	Intermediate Similarity	NPD4062	Phase 3
0.7092	Intermediate Similarity	NPD17	Approved
0.7081	Intermediate Similarity	NPD2801	Approved
0.7081	Intermediate Similarity	NPD8455	Phase 2
0.7078	Intermediate Similarity	NPD7466	Approved
0.707	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1607	Approved
0.7059	Intermediate Similarity	NPD4534	Discontinued
0.7055	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3018	Phase 2
0.7051	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3926	Phase 2
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7039	Intermediate Similarity	NPD4477	Approved
0.7039	Intermediate Similarity	NPD4476	Approved
0.7039	Intermediate Similarity	NPD6032	Approved
0.7037	Intermediate Similarity	NPD4288	Approved
0.7034	Intermediate Similarity	NPD1203	Approved
0.7018	Intermediate Similarity	NPD7549	Discontinued
0.7015	Intermediate Similarity	NPD290	Approved
0.7014	Intermediate Similarity	NPD5327	Phase 3
0.7014	Intermediate Similarity	NPD4359	Approved
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3705	Approved
0.6988	Remote Similarity	NPD6232	Discontinued
0.6987	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5588	Approved
0.6968	Remote Similarity	NPD7003	Approved
0.6966	Remote Similarity	NPD6696	Suspended
0.6962	Remote Similarity	NPD5049	Phase 3
0.6954	Remote Similarity	NPD6651	Approved
0.6954	Remote Similarity	NPD6653	Approved
0.6951	Remote Similarity	NPD6971	Discontinued
0.695	Remote Similarity	NPD1894	Discontinued
0.6944	Remote Similarity	NPD1608	Approved
0.6944	Remote Similarity	NPD2981	Phase 2
0.6944	Remote Similarity	NPD3972	Approved
0.6943	Remote Similarity	NPD1511	Approved
0.6939	Remote Similarity	NPD2861	Phase 2
0.6937	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2415	Discontinued
0.6933	Remote Similarity	NPD2979	Phase 3
0.6933	Remote Similarity	NPD5353	Approved
0.6923	Remote Similarity	NPD3847	Discontinued
0.6923	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3764	Approved
0.6913	Remote Similarity	NPD7985	Registered
0.6908	Remote Similarity	NPD4538	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