NPASS Compound

Structure

CID147030 OpenBabel06191715522D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 3.4641 -2.0000 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 0.0000 -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 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 4.3301 -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 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 -0.5000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 14 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	287.755
LogP:	3.226
LogD:	3.144
LogS:	-3.834
# Rotatable Bonds:	2
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	2.929
Fsp3:	0.312
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:	-4.545
MDCK Permeability:	1.733820499794092e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	83.4808349609375%
Volume Distribution (VD):	0.972
Pgp-substrate:	12.44372844696045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.918
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.596
CYP2C19-substrate:	0.769
CYP2C9-inhibitor:	0.384
CYP2C9-substrate:	0.725
CYP2D6-inhibitor:	0.781
CYP2D6-substrate:	0.577
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.609

ADMET: Excretion

Clearance (CL):	6.296
Half-life (T1/2):	0.279

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.89
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.307
Carcinogencity:	0.854
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC147030

Natural Product ID:	NPC147030
*Common Name:**	5,10-Dimethoxy-2,2-Dimethylpyrano[3,2-G]Chromen-8-One
IUPAC Name:	5,10-dimethoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
Synonyms:
Standard InCHIKey:	QZUNAFWZEXJWGD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-16(2)8-7-10-12(18-3)9-5-6-11(17)20-13(9)15(19-4)14(10)21-16/h5-8H,1-4H3
SMILES:	COc1c2C=CC(Oc2c(c2c1ccc(=O)o2)OC)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334350
PubChem CID:	155148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003486] Linear 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
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730241]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9439	Ulmus pumila	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9439	Ulmus pumila	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9439	Ulmus pumila	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11217	Lupinus argenteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10840	Cestrum laevigatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9439	Ulmus pumila	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14155	Solanum pennellii	Species	Solanaceae	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
Ki	6

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	49300.0	nM	PMID[534116]
NPT3101	Individual Protein	Carbonic anhydrase XIII	Homo sapiens	Ki	>	100000.0	nM	PMID[534116]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	9310.0	nM	PMID[534116]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	9210.0	nM	PMID[534116]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	8350.0	nM	PMID[534116]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	860.0	nM	PMID[534116]

☑ 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 NPC147030 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	494
0.1-0.2	2211
0.2-0.3	5784
0.3-0.4	11453
0.4-0.5	5604
0.5-0.6	4399
0.6-0.7	5758
0.7-0.8	5092
0.8-0.85	1469
0.85-0.9	391
0.9-0.95	38
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC472521
0.9612	High Similarity	NPC472522
0.9542	High Similarity	NPC167517
0.9398	High Similarity	NPC270256
0.9385	High Similarity	NPC123954
0.9259	High Similarity	NPC472520
0.9259	High Similarity	NPC279851
0.9167	High Similarity	NPC233018
0.9167	High Similarity	NPC36437
0.9167	High Similarity	NPC241341
0.9154	High Similarity	NPC123127
0.9154	High Similarity	NPC27239
0.9104	High Similarity	NPC286843
0.9091	High Similarity	NPC137669
0.9084	High Similarity	NPC244799
0.9084	High Similarity	NPC240722
0.9055	High Similarity	NPC150214
0.903	High Similarity	NPC234865
0.8986	High Similarity	NPC236419
0.8984	High Similarity	NPC50720
0.8955	High Similarity	NPC309953
0.8947	High Similarity	NPC319969
0.8939	High Similarity	NPC19242
0.8881	High Similarity	NPC26673
0.8855	High Similarity	NPC289316
0.8846	High Similarity	NPC232692
0.8846	High Similarity	NPC202594
0.8841	High Similarity	NPC300611
0.8837	High Similarity	NPC143725
0.8832	High Similarity	NPC43500
0.8832	High Similarity	NPC164148
0.8815	High Similarity	NPC474600
0.8788	High Similarity	NPC474616
0.8779	High Similarity	NPC163248
0.8759	High Similarity	NPC474540
0.8759	High Similarity	NPC474530
0.8759	High Similarity	NPC474521
0.875	High Similarity	NPC240915
0.8741	High Similarity	NPC133956
0.8741	High Similarity	NPC207002
0.8741	High Similarity	NPC167111
0.8741	High Similarity	NPC296624
0.8741	High Similarity	NPC318400
0.8741	High Similarity	NPC471910
0.8692	High Similarity	NPC173350
0.8692	High Similarity	NPC290605
0.8692	High Similarity	NPC154176
0.8686	High Similarity	NPC126682
0.8686	High Similarity	NPC82271
0.8676	High Similarity	NPC260265
0.8676	High Similarity	NPC74655
0.8676	High Similarity	NPC100986
0.8676	High Similarity	NPC198381
0.8676	High Similarity	NPC166672
0.8676	High Similarity	NPC287182
0.8676	High Similarity	NPC47163
0.8676	High Similarity	NPC195343
0.8676	High Similarity	NPC319859
0.8676	High Similarity	NPC164269
0.8676	High Similarity	NPC127888
0.8676	High Similarity	NPC18804
0.8676	High Similarity	NPC84894
0.8676	High Similarity	NPC267412
0.8662	High Similarity	NPC205361
0.8657	High Similarity	NPC474617
0.8652	High Similarity	NPC471763
0.8636	High Similarity	NPC471826
0.8626	High Similarity	NPC291899
0.8623	High Similarity	NPC95162
0.8623	High Similarity	NPC52086
0.8623	High Similarity	NPC148835
0.8623	High Similarity	NPC20511
0.8623	High Similarity	NPC139548
0.8623	High Similarity	NPC20796
0.8623	High Similarity	NPC76336
0.8613	High Similarity	NPC471909
0.8613	High Similarity	NPC86892
0.8613	High Similarity	NPC472424
0.8613	High Similarity	NPC281241
0.8613	High Similarity	NPC471625
0.8582	High Similarity	NPC256555
0.8582	High Similarity	NPC34245
0.8582	High Similarity	NPC110067
0.8582	High Similarity	NPC7439
0.8582	High Similarity	NPC230157
0.8582	High Similarity	NPC138212
0.8582	High Similarity	NPC91492
0.8571	High Similarity	NPC474670
0.8571	High Similarity	NPC194841
0.8561	High Similarity	NPC13067
0.8561	High Similarity	NPC471828
0.8561	High Similarity	NPC471827
0.8551	High Similarity	NPC476455
0.8551	High Similarity	NPC55615
0.8551	High Similarity	NPC283019
0.8551	High Similarity	NPC128529
0.8551	High Similarity	NPC160727
0.8551	High Similarity	NPC149320
0.8551	High Similarity	NPC471630
0.8551	High Similarity	NPC177281
0.855	High Similarity	NPC109675
0.855	High Similarity	NPC273772
0.854	High Similarity	NPC307412
0.854	High Similarity	NPC7163
0.854	High Similarity	NPC55149
0.8529	High Similarity	NPC14248
0.8507	High Similarity	NPC474623
0.8507	High Similarity	NPC139595
0.8507	High Similarity	NPC474651
0.8507	High Similarity	NPC474636
0.8507	High Similarity	NPC293642
0.8507	High Similarity	NPC60704
0.8496	Intermediate Similarity	NPC127604
0.8485	Intermediate Similarity	NPC27671
0.8485	Intermediate Similarity	NPC201667
0.8485	Intermediate Similarity	NPC73413
0.8478	Intermediate Similarity	NPC224941
0.8478	Intermediate Similarity	NPC469675
0.8478	Intermediate Similarity	NPC472525
0.8478	Intermediate Similarity	NPC311430
0.8478	Intermediate Similarity	NPC73071
0.8473	Intermediate Similarity	NPC13007
0.8473	Intermediate Similarity	NPC257188
0.8473	Intermediate Similarity	NPC194626
0.8472	Intermediate Similarity	NPC15577
0.8472	Intermediate Similarity	NPC231149
0.8467	Intermediate Similarity	NPC222036
0.8467	Intermediate Similarity	NPC7526
0.8462	Intermediate Similarity	NPC476450
0.8456	Intermediate Similarity	NPC37009
0.8456	Intermediate Similarity	NPC66430
0.8435	Intermediate Similarity	NPC470264
0.8433	Intermediate Similarity	NPC474821
0.8429	Intermediate Similarity	NPC211110
0.8429	Intermediate Similarity	NPC279573
0.8414	Intermediate Similarity	NPC96294
0.8409	Intermediate Similarity	NPC472518
0.8406	Intermediate Similarity	NPC92830
0.8406	Intermediate Similarity	NPC224475
0.8406	Intermediate Similarity	NPC213173
0.8406	Intermediate Similarity	NPC180716
0.8397	Intermediate Similarity	NPC144418
0.8394	Intermediate Similarity	NPC19157
0.8382	Intermediate Similarity	NPC476399
0.8382	Intermediate Similarity	NPC80170
0.837	Intermediate Similarity	NPC157212
0.837	Intermediate Similarity	NPC185066
0.8369	Intermediate Similarity	NPC312881
0.8358	Intermediate Similarity	NPC474632
0.8357	Intermediate Similarity	NPC155963
0.8357	Intermediate Similarity	NPC153818
0.8357	Intermediate Similarity	NPC232246
0.8357	Intermediate Similarity	NPC476171
0.8356	Intermediate Similarity	NPC176903
0.8356	Intermediate Similarity	NPC30688
0.8346	Intermediate Similarity	NPC111347
0.8333	Intermediate Similarity	NPC83535
0.8333	Intermediate Similarity	NPC248429
0.8333	Intermediate Similarity	NPC96286
0.8333	Intermediate Similarity	NPC288238
0.831	Intermediate Similarity	NPC287286
0.831	Intermediate Similarity	NPC152771
0.831	Intermediate Similarity	NPC195357
0.8309	Intermediate Similarity	NPC168710
0.8299	Intermediate Similarity	NPC294522
0.8299	Intermediate Similarity	NPC114740
0.8299	Intermediate Similarity	NPC21184
0.8299	Intermediate Similarity	NPC120426
0.8299	Intermediate Similarity	NPC205727
0.8298	Intermediate Similarity	NPC151946
0.8288	Intermediate Similarity	NPC48366
0.8288	Intermediate Similarity	NPC139839
0.8286	Intermediate Similarity	NPC224543
0.8286	Intermediate Similarity	NPC38099
0.8286	Intermediate Similarity	NPC26954
0.8286	Intermediate Similarity	NPC283331
0.8286	Intermediate Similarity	NPC78746
0.8286	Intermediate Similarity	NPC188380
0.8276	Intermediate Similarity	NPC475872
0.8273	Intermediate Similarity	NPC62366
0.8264	Intermediate Similarity	NPC185127
0.8261	Intermediate Similarity	NPC469956
0.8261	Intermediate Similarity	NPC245120
0.8261	Intermediate Similarity	NPC137949
0.8261	Intermediate Similarity	NPC5423
0.8255	Intermediate Similarity	NPC144162
0.8244	Intermediate Similarity	NPC222175
0.8243	Intermediate Similarity	NPC213197
0.8235	Intermediate Similarity	NPC472519
0.8235	Intermediate Similarity	NPC210674
0.8235	Intermediate Similarity	NPC199204
0.8227	Intermediate Similarity	NPC225106
0.8227	Intermediate Similarity	NPC294456
0.8227	Intermediate Similarity	NPC474886
0.8227	Intermediate Similarity	NPC212124
0.8227	Intermediate Similarity	NPC184861
0.8227	Intermediate Similarity	NPC38874
0.8227	Intermediate Similarity	NPC281014
0.8222	Intermediate Similarity	NPC244364
0.8219	Intermediate Similarity	NPC476347

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 NPC147030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	1069
0.2-0.3	2091
0.3-0.4	2670
0.4-0.5	1651
0.5-0.6	824
0.6-0.7	295
0.7-0.8	92
0.8-0.85	26
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8201	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD5124	Phase 1
0.8108	Intermediate Similarity	NPD1653	Approved
0.7733	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5844	Phase 1
0.7595	Intermediate Similarity	NPD5494	Approved
0.7591	Intermediate Similarity	NPD422	Phase 1
0.7564	Intermediate Similarity	NPD3817	Phase 2
0.7532	Intermediate Similarity	NPD919	Approved
0.7515	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD2801	Approved
0.7465	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1652	Phase 2
0.7394	Intermediate Similarity	NPD3018	Phase 2
0.7394	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1613	Approved
0.7353	Intermediate Similarity	NPD7644	Approved
0.7343	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1247	Approved
0.7297	Intermediate Similarity	NPD3748	Approved
0.7296	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3027	Phase 3
0.7286	Intermediate Similarity	NPD2981	Phase 2
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3496	Discontinued
0.7246	Intermediate Similarity	NPD5691	Approved
0.7241	Intermediate Similarity	NPD1296	Phase 2
0.7234	Intermediate Similarity	NPD2983	Phase 2
0.7234	Intermediate Similarity	NPD2982	Phase 2
0.7233	Intermediate Similarity	NPD5402	Approved
0.7226	Intermediate Similarity	NPD920	Approved
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7215	Intermediate Similarity	NPD1934	Approved
0.7215	Intermediate Similarity	NPD6801	Discontinued
0.7214	Intermediate Similarity	NPD1611	Approved
0.7211	Intermediate Similarity	NPD447	Suspended
0.7178	Intermediate Similarity	NPD6232	Discontinued
0.717	Intermediate Similarity	NPD1465	Phase 2
0.717	Intermediate Similarity	NPD7819	Suspended
0.717	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2935	Discontinued
0.7133	Intermediate Similarity	NPD2796	Approved
0.7123	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7985	Registered
0.7121	Intermediate Similarity	NPD1358	Approved
0.7111	Intermediate Similarity	NPD5535	Approved
0.7105	Intermediate Similarity	NPD6674	Discontinued
0.7105	Intermediate Similarity	NPD1243	Approved
0.7099	Intermediate Similarity	NPD9697	Approved
0.7097	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1933	Approved
0.7071	Intermediate Similarity	NPD4626	Approved
0.7063	Intermediate Similarity	NPD3225	Approved
0.7059	Intermediate Similarity	NPD3750	Approved
0.7059	Intermediate Similarity	NPD5283	Phase 1
0.7055	Intermediate Similarity	NPD5677	Discontinued
0.7055	Intermediate Similarity	NPD4625	Phase 3
0.7048	Intermediate Similarity	NPD7473	Discontinued
0.7037	Intermediate Similarity	NPD7075	Discontinued
0.7032	Intermediate Similarity	NPD1511	Approved
0.7032	Intermediate Similarity	NPD6799	Approved
0.7027	Intermediate Similarity	NPD4060	Phase 1
0.7012	Intermediate Similarity	NPD7199	Phase 2
0.7007	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4749	Approved
0.6987	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2532	Approved
0.6987	Remote Similarity	NPD2533	Approved
0.6987	Remote Similarity	NPD2534	Approved
0.6987	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4908	Phase 1
0.6975	Remote Similarity	NPD3882	Suspended
0.6975	Remote Similarity	NPD4965	Approved
0.6975	Remote Similarity	NPD4966	Approved
0.6975	Remote Similarity	NPD4967	Phase 2
0.6972	Remote Similarity	NPD3705	Approved
0.6968	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1512	Approved
0.6937	Remote Similarity	NPD7411	Suspended
0.6929	Remote Similarity	NPD1548	Phase 1
0.6928	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3134	Approved
0.6914	Remote Similarity	NPD5353	Approved
0.6913	Remote Similarity	NPD4307	Phase 2
0.6909	Remote Similarity	NPD8127	Discontinued
0.6908	Remote Similarity	NPD3539	Phase 1
0.6899	Remote Similarity	NPD5403	Approved
0.6897	Remote Similarity	NPD2797	Approved
0.6897	Remote Similarity	NPD3266	Approved
0.6897	Remote Similarity	NPD3267	Approved
0.6892	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6234	Discontinued
0.6886	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6166	Phase 2
0.6886	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5401	Approved
0.6875	Remote Similarity	NPD4380	Phase 2
0.6875	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6599	Discontinued
0.6871	Remote Similarity	NPD7768	Phase 2
0.6867	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD230	Phase 1
0.6864	Remote Similarity	NPD7054	Approved
0.6863	Remote Similarity	NPD3540	Phase 1
0.6853	Remote Similarity	NPD1610	Phase 2
0.6839	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6671	Approved
0.6828	Remote Similarity	NPD8651	Approved
0.6826	Remote Similarity	NPD5242	Approved
0.6826	Remote Similarity	NPD3926	Phase 2
0.6824	Remote Similarity	NPD7472	Approved
0.6824	Remote Similarity	NPD7074	Phase 3
0.6824	Remote Similarity	NPD7095	Approved
0.6818	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2424	Discontinued
0.6815	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4357	Discontinued
0.6815	Remote Similarity	NPD5297	Approved
0.6803	Remote Similarity	NPD2861	Phase 2
0.6795	Remote Similarity	NPD6190	Approved
0.6795	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2313	Discontinued
0.6779	Remote Similarity	NPD3268	Approved
0.6774	Remote Similarity	NPD2800	Approved
0.6757	Remote Similarity	NPD6832	Phase 2
0.6755	Remote Similarity	NPD4340	Discontinued
0.6753	Remote Similarity	NPD7266	Discontinued
0.6744	Remote Similarity	NPD6559	Discontinued
0.6733	Remote Similarity	NPD6233	Phase 2
0.6732	Remote Similarity	NPD4308	Phase 3
0.6728	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5089	Approved
0.6728	Remote Similarity	NPD5090	Approved
0.6727	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1778	Approved
0.6712	Remote Similarity	NPD6696	Suspended
0.6711	Remote Similarity	NPD2653	Approved
0.6708	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7808	Phase 3
0.6691	Remote Similarity	NPD1398	Phase 1
0.6689	Remote Similarity	NPD2237	Approved
0.6688	Remote Similarity	NPD1551	Phase 2
0.6686	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7340	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD6798	Discontinued
0.6647	Remote Similarity	NPD7251	Discontinued
0.6646	Remote Similarity	NPD4585	Approved
0.6646	Remote Similarity	NPD3687	Approved
0.6646	Remote Similarity	NPD3686	Approved
0.6645	Remote Similarity	NPD5763	Approved
0.6645	Remote Similarity	NPD5762	Approved
0.6645	Remote Similarity	NPD1375	Discontinued
0.6645	Remote Similarity	NPD2346	Discontinued
0.6643	Remote Similarity	NPD5585	Approved
0.6626	Remote Similarity	NPD6385	Approved
0.6626	Remote Similarity	NPD6386	Approved
0.6624	Remote Similarity	NPD4628	Phase 3
0.6624	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4110	Phase 3
0.6623	Remote Similarity	NPD7033	Discontinued
0.6623	Remote Similarity	NPD1510	Phase 2
0.6623	Remote Similarity	NPD2799	Discontinued
0.6622	Remote Similarity	NPD1019	Discontinued
0.6621	Remote Similarity	NPD1091	Approved
0.6608	Remote Similarity	NPD7228	Approved
0.6605	Remote Similarity	NPD3226	Approved
0.6605	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD1549	Phase 2
0.6597	Remote Similarity	NPD17	Approved
0.6591	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4481	Phase 3
0.6582	Remote Similarity	NPD2219	Phase 1
0.6581	Remote Similarity	NPD6099	Approved
0.6581	Remote Similarity	NPD6100	Approved
0.6579	Remote Similarity	NPD4140	Approved
0.6575	Remote Similarity	NPD9717	Approved
0.6573	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2684	Approved
0.6564	Remote Similarity	NPD4675	Approved
0.6564	Remote Similarity	NPD4678	Approved
0.6562	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3146	Approved
0.6558	Remote Similarity	NPD6111	Discontinued

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