NPASS Compound

Structure

NPC281241 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 2.5981 -1.5000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -0.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 6 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	322.347
LogP:	3.766
LogD:	3.301
LogS:	-3.691
# Rotatable Bonds:	3
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	3.302
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.654
MDCK Permeability:	2.520888483559247e-05
Pgp-inhibitor:	0.802
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	94.07695770263672%
Volume Distribution (VD):	0.879
Pgp-substrate:	9.139395713806152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.82
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.667
CYP2C19-substrate:	0.301
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.78
CYP2D6-inhibitor:	0.256
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.21
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	6.93
Half-life (T1/2):	0.306

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.229
Skin Sensitization:	0.141
Carcinogencity:	0.894
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.628

Download Data

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

Natural Product: NPC281241

Natural Product ID:	NPC281241
*Common Name:**	[(9R)-8,8-Dimethyl-2-Oxo-9,10-Dihydropyrano[2,3-H]Chromen-9-Yl] 2-Methylpropanoate
IUPAC Name:	[(9R)-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-h]chromen-9-yl] 2-methylpropanoate
Synonyms:
Standard InCHIKey:	PKHNHXIOSSYBJU-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C18H20O5/c1-10(2)17(20)21-14-9-12-13(23-18(14,3)4)7-5-11-6-8-15(19)22-16(11)12/h5-8,10,14H,9H2,1-4H3/t14-/m1/s1
SMILES:	O=C(C(C)C)O[C@@H]1Cc2c(OC1(C)C)ccc1c2oc(=O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449490
PubChem CID:	11823236
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO32915	prionosciadium watsoni	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088423]

☑ 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	2
Others	28

Activity Type	# Activity
Cell Line	8
CELL-LINE	12
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	Survival	=	45.72	%	PMID[540216]
NPT886	Cell Line	NIH3T3	Mus musculus	Survival	=	55.6	%	PMID[540216]
NPT886	Cell Line	NIH3T3	Mus musculus	Survival	=	67.43	%	PMID[540216]
NPT886	Cell Line	NIH3T3	Mus musculus	Survival	=	83.14	%	PMID[540216]
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	31.31	%	PMID[540216]
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	25.89	%	PMID[540216]
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	19.53	%	PMID[540216]
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	8.13	%	PMID[540216]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	23.52	%	PMID[540215]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	237000.0	nM	PMID[540215]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	169000.0	nM	PMID[540215]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	19.59	%	PMID[540215]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	58.81	%	PMID[540215]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	100.0	%	PMID[540215]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	20.0	%	PMID[540215]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	54.3	%	PMID[540215]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	84.92	%	PMID[540215]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	GI	=	87.38	%	PMID[540215]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	100.08	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	101.3	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	110.34	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	147.43	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Survival	=	44.77	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Survival	=	56.11	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Survival	=	66.48	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Survival	=	82.32	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	28.99	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	23.78	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	18.04	%	PMID[540216]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	7.64	%	PMID[540216]

☑ 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 NPC281241 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	416
0.1-0.2	1646
0.2-0.3	4074
0.3-0.4	9180
0.4-0.5	9424
0.5-0.6	4062
0.6-0.7	5920
0.7-0.8	5532
0.8-0.85	1848
0.85-0.9	392
0.9-0.95	154
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471625
1.0	High Similarity	NPC86892
1.0	High Similarity	NPC472424
1.0	High Similarity	NPC471909
0.9922	High Similarity	NPC128529
0.9922	High Similarity	NPC55615
0.9922	High Similarity	NPC283019
0.9922	High Similarity	NPC166672
0.9922	High Similarity	NPC471630
0.9922	High Similarity	NPC160727
0.9922	High Similarity	NPC74655
0.9922	High Similarity	NPC476455
0.9922	High Similarity	NPC195343
0.9922	High Similarity	NPC177281
0.9922	High Similarity	NPC198381
0.9922	High Similarity	NPC149320
0.9922	High Similarity	NPC287182
0.9922	High Similarity	NPC164269
0.9922	High Similarity	NPC127888
0.9922	High Similarity	NPC100986
0.9922	High Similarity	NPC47163
0.9922	High Similarity	NPC84894
0.9922	High Similarity	NPC267412
0.9922	High Similarity	NPC319859
0.9922	High Similarity	NPC18804
0.9922	High Similarity	NPC260265
0.9844	High Similarity	NPC133956
0.9844	High Similarity	NPC167111
0.9844	High Similarity	NPC207002
0.9844	High Similarity	NPC318400
0.9844	High Similarity	NPC471910
0.9844	High Similarity	NPC296624
0.9624	High Similarity	NPC287286
0.9621	High Similarity	NPC211110
0.9615	High Similarity	NPC307412
0.9615	High Similarity	NPC55149
0.9549	High Similarity	NPC312881
0.9538	High Similarity	NPC222036
0.9538	High Similarity	NPC7526
0.9478	High Similarity	NPC152771
0.9478	High Similarity	NPC195357
0.9474	High Similarity	NPC279573
0.9462	High Similarity	NPC14248
0.9398	High Similarity	NPC155963
0.9398	High Similarity	NPC153818
0.9398	High Similarity	NPC232246
0.9394	High Similarity	NPC469675
0.9338	High Similarity	NPC183646
0.9338	High Similarity	NPC119640
0.9328	High Similarity	NPC151946
0.9323	High Similarity	NPC78746
0.9323	High Similarity	NPC224543
0.9323	High Similarity	NPC188380
0.9323	High Similarity	NPC283331
0.9308	High Similarity	NPC80170
0.9297	High Similarity	NPC471826
0.927	High Similarity	NPC476457
0.9254	High Similarity	NPC281014
0.9254	High Similarity	NPC225106
0.9254	High Similarity	NPC294456
0.9254	High Similarity	NPC212124
0.9254	High Similarity	NPC184861
0.9248	High Similarity	NPC472525
0.9231	High Similarity	NPC168710
0.9219	High Similarity	NPC471828
0.9219	High Similarity	NPC471827
0.9203	High Similarity	NPC469701
0.9179	High Similarity	NPC38099
0.9179	High Similarity	NPC26954
0.9173	High Similarity	NPC180716
0.9173	High Similarity	NPC62366
0.9173	High Similarity	NPC213173
0.9173	High Similarity	NPC224475
0.9154	High Similarity	NPC199204
0.9154	High Similarity	NPC139595
0.9154	High Similarity	NPC293642
0.9154	High Similarity	NPC60704
0.9154	High Similarity	NPC472519
0.9141	High Similarity	NPC201667
0.9141	High Similarity	NPC27671
0.9141	High Similarity	NPC111347
0.9141	High Similarity	NPC73413
0.9104	High Similarity	NPC33986
0.9098	High Similarity	NPC31849
0.9098	High Similarity	NPC469955
0.9098	High Similarity	NPC469952
0.9065	High Similarity	NPC85624
0.9062	High Similarity	NPC472518
0.9062	High Similarity	NPC109675
0.9062	High Similarity	NPC273772
0.9044	High Similarity	NPC270256
0.903	High Similarity	NPC98179
0.903	High Similarity	NPC326600
0.903	High Similarity	NPC253574
0.903	High Similarity	NPC204353
0.903	High Similarity	NPC50896
0.9008	High Similarity	NPC185066
0.9	High Similarity	NPC234109
0.9	High Similarity	NPC188327
0.8993	High Similarity	NPC471824
0.8992	High Similarity	NPC291899
0.8984	High Similarity	NPC248429
0.8984	High Similarity	NPC96286
0.8947	High Similarity	NPC29734
0.8936	High Similarity	NPC296377
0.8936	High Similarity	NPC87950
0.8936	High Similarity	NPC471764
0.8915	High Similarity	NPC154176
0.8915	High Similarity	NPC50720
0.8915	High Similarity	NPC290605
0.8915	High Similarity	NPC173350
0.8881	High Similarity	NPC469956
0.8881	High Similarity	NPC194277
0.8881	High Similarity	NPC19157
0.8873	High Similarity	NPC169510
0.8872	High Similarity	NPC113098
0.8865	High Similarity	NPC171656
0.8865	High Similarity	NPC294365
0.8864	High Similarity	NPC157212
0.8837	High Similarity	NPC150214
0.8837	High Similarity	NPC257188
0.8837	High Similarity	NPC13007
0.8832	High Similarity	NPC471068
0.8832	High Similarity	NPC306365
0.8832	High Similarity	NPC14697
0.8832	High Similarity	NPC471069
0.8828	High Similarity	NPC235190
0.8828	High Similarity	NPC180006
0.8828	High Similarity	NPC163200
0.8815	High Similarity	NPC241165
0.8815	High Similarity	NPC142563
0.8815	High Similarity	NPC1220
0.8815	High Similarity	NPC163557
0.8815	High Similarity	NPC291551
0.8815	High Similarity	NPC469449
0.8815	High Similarity	NPC54503
0.8815	High Similarity	NPC141822
0.8815	High Similarity	NPC469965
0.8815	High Similarity	NPC55147
0.8815	High Similarity	NPC205797
0.8806	High Similarity	NPC272650
0.8806	High Similarity	NPC267336
0.8788	High Similarity	NPC289316
0.8777	High Similarity	NPC472523
0.8769	High Similarity	NPC315807
0.8768	High Similarity	NPC144512
0.8768	High Similarity	NPC37428
0.8768	High Similarity	NPC137262
0.8768	High Similarity	NPC47040
0.8768	High Similarity	NPC471070
0.8768	High Similarity	NPC35501
0.8768	High Similarity	NPC471072
0.8768	High Similarity	NPC278600
0.8768	High Similarity	NPC307883
0.8768	High Similarity	NPC471071
0.876	High Similarity	NPC144418
0.8759	High Similarity	NPC167517
0.875	High Similarity	NPC309953
0.875	High Similarity	NPC131950
0.875	High Similarity	NPC103116
0.8741	High Similarity	NPC123954
0.8731	High Similarity	NPC19242
0.8712	High Similarity	NPC163248
0.8696	High Similarity	NPC131198
0.8686	High Similarity	NPC311430
0.8686	High Similarity	NPC224941
0.8676	High Similarity	NPC472522
0.8676	High Similarity	NPC241341
0.8676	High Similarity	NPC233018
0.8676	High Similarity	NPC36437
0.8672	High Similarity	NPC298796
0.8672	High Similarity	NPC281356
0.8662	High Similarity	NPC43716
0.8662	High Similarity	NPC295696
0.8662	High Similarity	NPC76657
0.8662	High Similarity	NPC475719
0.8662	High Similarity	NPC101255
0.8647	High Similarity	NPC258567
0.8647	High Similarity	NPC121740
0.8647	High Similarity	NPC243688
0.8647	High Similarity	NPC224774
0.8643	High Similarity	NPC138149
0.8643	High Similarity	NPC155552
0.8636	High Similarity	NPC202594
0.8636	High Similarity	NPC232692
0.8626	High Similarity	NPC143725
0.8623	High Similarity	NPC104796
0.8623	High Similarity	NPC286843
0.8621	High Similarity	NPC164299
0.8613	High Similarity	NPC147030
0.8603	High Similarity	NPC319969
0.8603	High Similarity	NPC175159
0.8603	High Similarity	NPC137669
0.8594	High Similarity	NPC152306
0.8594	High Similarity	NPC265547
0.8594	High Similarity	NPC96705
0.8593	High Similarity	NPC32463
0.8592	High Similarity	NPC471763
0.8582	High Similarity	NPC469453
0.8582	High Similarity	NPC20631

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 NPC281241 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	951
0.2-0.3	1755
0.3-0.4	2640
0.4-0.5	1889
0.5-0.6	1034
0.6-0.7	361
0.7-0.8	116
0.8-0.85	34
0.85-0.9	8
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD5124	Phase 1
0.8815	High Similarity	NPD5123	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1652	Phase 2
0.8195	Intermediate Similarity	NPD422	Phase 1
0.8146	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7972	Intermediate Similarity	NPD3748	Approved
0.7961	Intermediate Similarity	NPD6801	Discontinued
0.7945	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1653	Approved
0.7929	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1296	Phase 2
0.7914	Intermediate Similarity	NPD4908	Phase 1
0.7867	Intermediate Similarity	NPD920	Approved
0.7829	Intermediate Similarity	NPD4380	Phase 2
0.7808	Intermediate Similarity	NPD2424	Discontinued
0.78	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1610	Phase 2
0.7792	Intermediate Similarity	NPD7819	Suspended
0.7785	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD7097	Phase 1
0.7778	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5494	Approved
0.7764	Intermediate Similarity	NPD5844	Phase 1
0.7755	Intermediate Similarity	NPD1243	Approved
0.7734	Intermediate Similarity	NPD1358	Approved
0.7733	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD5535	Approved
0.7704	Intermediate Similarity	NPD5691	Approved
0.7703	Intermediate Similarity	NPD3750	Approved
0.7698	Intermediate Similarity	NPD3266	Approved
0.7698	Intermediate Similarity	NPD2797	Approved
0.7698	Intermediate Similarity	NPD3267	Approved
0.7692	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3134	Approved
0.7647	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5403	Approved
0.763	Intermediate Similarity	NPD1548	Phase 1
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7616	Intermediate Similarity	NPD5401	Approved
0.7597	Intermediate Similarity	NPD6599	Discontinued
0.7595	Intermediate Similarity	NPD919	Approved
0.758	Intermediate Similarity	NPD7768	Phase 2
0.7578	Intermediate Similarity	NPD9697	Approved
0.7569	Intermediate Similarity	NPD4307	Phase 2
0.7569	Intermediate Similarity	NPD4060	Phase 1
0.7568	Intermediate Similarity	NPD1549	Phase 2
0.7554	Intermediate Similarity	NPD4749	Approved
0.7552	Intermediate Similarity	NPD6798	Discontinued
0.7552	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3268	Approved
0.7535	Intermediate Similarity	NPD6832	Phase 2
0.7535	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6355	Discontinued
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD3225	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.747	Intermediate Similarity	NPD7549	Discontinued
0.7467	Intermediate Similarity	NPD4628	Phase 3
0.7465	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3496	Discontinued
0.7439	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1091	Approved
0.741	Intermediate Similarity	NPD6559	Discontinued
0.7397	Intermediate Similarity	NPD4340	Discontinued
0.7391	Intermediate Similarity	NPD4626	Approved
0.7383	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6004	Phase 3
0.7383	Intermediate Similarity	NPD6005	Phase 3
0.7383	Intermediate Similarity	NPD6002	Phase 3
0.7383	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD2799	Discontinued
0.7365	Intermediate Similarity	NPD4308	Phase 3
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7362	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3027	Phase 3
0.7343	Intermediate Similarity	NPD2861	Phase 2
0.7342	Intermediate Similarity	NPD8455	Phase 2
0.7333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1551	Phase 2
0.7315	Intermediate Similarity	NPD2935	Discontinued
0.731	Intermediate Similarity	NPD2313	Discontinued
0.7297	Intermediate Similarity	NPD4536	Approved
0.7297	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4538	Approved
0.7296	Intermediate Similarity	NPD2415	Discontinued
0.729	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1611	Approved
0.7285	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1933	Approved
0.7279	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD2684	Approved
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD5763	Approved
0.7267	Intermediate Similarity	NPD5762	Approved
0.7259	Intermediate Similarity	NPD1241	Discontinued
0.7255	Intermediate Similarity	NPD5058	Phase 3
0.7255	Intermediate Similarity	NPD6667	Approved
0.7255	Intermediate Similarity	NPD6666	Approved
0.725	Intermediate Similarity	NPD4966	Approved
0.725	Intermediate Similarity	NPD4967	Phase 2
0.725	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD7095	Approved
0.7239	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD7466	Approved
0.7237	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2801	Approved
0.7226	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4140	Approved
0.7205	Intermediate Similarity	NPD3749	Approved
0.72	Intermediate Similarity	NPD6100	Approved
0.72	Intermediate Similarity	NPD2438	Suspended
0.72	Intermediate Similarity	NPD6099	Approved
0.7197	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5585	Approved
0.7192	Intermediate Similarity	NPD7985	Registered
0.7188	Intermediate Similarity	NPD5353	Approved
0.7185	Intermediate Similarity	NPD7843	Approved
0.7178	Intermediate Similarity	NPD1247	Approved
0.7178	Intermediate Similarity	NPD7199	Phase 2
0.7178	Intermediate Similarity	NPD8127	Discontinued
0.7174	Intermediate Similarity	NPD7644	Approved
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7163	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.7161	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2533	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7153	Intermediate Similarity	NPD7157	Approved
0.7152	Intermediate Similarity	NPD6166	Phase 2
0.7152	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1778	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7133	Intermediate Similarity	NPD5588	Approved
0.7133	Intermediate Similarity	NPD5960	Phase 3
0.7126	Intermediate Similarity	NPD7054	Approved
0.7125	Intermediate Similarity	NPD1465	Phase 2
0.7113	Intermediate Similarity	NPD9717	Approved
0.7108	Intermediate Similarity	NPD7473	Discontinued
0.7103	Intermediate Similarity	NPD3018	Phase 2
0.7097	Intermediate Similarity	NPD7212	Phase 2
0.7097	Intermediate Similarity	NPD7213	Phase 3
0.7097	Intermediate Similarity	NPD1511	Approved
0.7095	Intermediate Similarity	NPD1240	Approved
0.7095	Intermediate Similarity	NPD2979	Phase 3
0.7091	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6032	Approved
0.7083	Intermediate Similarity	NPD7472	Approved
0.7083	Intermediate Similarity	NPD7074	Phase 3
0.7081	Intermediate Similarity	NPD4288	Approved
0.7078	Intermediate Similarity	NPD3887	Approved
0.7073	Intermediate Similarity	NPD6959	Discontinued
0.7068	Intermediate Similarity	NPD290	Approved
0.7067	Intermediate Similarity	NPD2200	Suspended
0.7063	Intermediate Similarity	NPD4433	Discontinued
0.7059	Intermediate Similarity	NPD6674	Discontinued
0.7059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7447	Phase 1
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7048	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD447	Suspended
0.7047	Intermediate Similarity	NPD4618	Approved
0.7047	Intermediate Similarity	NPD4622	Approved
0.7041	Intermediate Similarity	NPD6797	Phase 2
0.7039	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7266	Discontinued
0.7039	Intermediate Similarity	NPD2346	Discontinued
0.7037	Intermediate Similarity	NPD3882	Suspended
0.7034	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6671	Approved
0.7027	Intermediate Similarity	NPD8032	Phase 2
0.7027	Intermediate Similarity	NPD4062	Phase 3
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7006	Intermediate Similarity	NPD6273	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