NPASS Compound

Structure

CID224774 OpenBabel06191716022D 23 24 0 0 1 0 0 0 0 0999 V2000 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -6.0622 2.5000 0.0000 C 0 0 3 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -3.4641 -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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 6 2 0 0 0 0 4 15 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 22 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 15 18 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.15
Volume:	336.773
LogP:	3.702
LogD:	3.461
LogS:	-3.756
# Rotatable Bonds:	6
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	3.185
Fsp3:	0.316
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:	-4.781
MDCK Permeability:	2.003411646001041e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.592
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.22
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	95.00054931640625%
Volume Distribution (VD):	0.86
Pgp-substrate:	4.712262153625488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.845
CYP2C19-substrate:	0.213
CYP2C9-inhibitor:	0.621
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.451
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.202
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	11.705
Half-life (T1/2):	0.387

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.68
Drug-inuced Liver Injury (DILI):	0.717
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.472
Skin Sensitization:	0.442
Carcinogencity:	0.315
Eye Corrosion:	0.003
Eye Irritation:	0.239
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC224774

Natural Product ID:	NPC224774
*Common Name:**	Anisocoumarin H
IUPAC Name:	7-[(2E)-5-hydroxy-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
Synonyms:	anisocoumarin H
Standard InCHIKey:	VNADFOGBKXRWGC-RIYZIHGNSA-N
Standard InCHI:	InChI=1S/C19H22O4/c1-13(2)10-16(20)11-14(3)8-9-22-17-6-4-15-5-7-19(21)23-18(15)12-17/h4-8,10,12,16,20H,9,11H2,1-3H3/b14-8+
SMILES:	C/C(=CCOc1ccc2c(c1)oc(=O)cc2)/CC(C=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL408980
PubChem CID:	14376449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
AC50	1
Ki	4
Others	3
Potency	23

Activity Type	# Activity
Individual Protein	23
Others	7
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1069	Individual Protein	Mu opioid receptor	Rattus norvegicus	Activity	>	50.0	%	PMID[526078]
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	Activity	>	50.0	%	PMID[526078]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	>	50.0	%	PMID[526078]
NPT1069	Individual Protein	Mu opioid receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[526078]
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	Ki	>	10000.0	nM	PMID[526078]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Ki	=	2600.0	nM	PMID[526078]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[526078]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[526079]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	19952.6	nM	PMID[526079]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	10322.5	nM	PMID[526079]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[526079]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[526079]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	37933.0	nM	PMID[526079]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[526079]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[526079]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[526079]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	9200.0	nM	PMID[526079]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[526079]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[526079]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[526079]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[526079]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	AC50	=	4645.0	nM	PMID[526079]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[526079]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	28183.8	nM	PMID[526079]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[526079]
NPT2	Others	Unspecified		Potency	n.a.	3548.1	nM	PMID[526079]
NPT2	Others	Unspecified		Potency	n.a.	18356.4	nM	PMID[526079]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[526079]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[526079]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[526079]

☑ 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 NPC224774 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	323
0.1-0.2	1494
0.2-0.3	4040
0.3-0.4	9683
0.4-0.5	9037
0.5-0.6	3949
0.6-0.7	6315
0.7-0.8	5221
0.8-0.85	1637
0.85-0.9	842
0.9-0.95	141
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258567
1.0	High Similarity	NPC121740
0.9917	High Similarity	NPC469453
0.9597	High Similarity	NPC113098
0.9524	High Similarity	NPC31849
0.952	High Similarity	NPC272650
0.952	High Similarity	NPC267336
0.952	High Similarity	NPC29734
0.9417	High Similarity	NPC180006
0.9417	High Similarity	NPC235190
0.9417	High Similarity	NPC163200
0.937	High Similarity	NPC2363
0.9302	High Similarity	NPC26954
0.9302	High Similarity	NPC38099
0.9297	High Similarity	NPC204353
0.9297	High Similarity	NPC50896
0.9297	High Similarity	NPC326600
0.9291	High Similarity	NPC194277
0.9256	High Similarity	NPC302107
0.925	High Similarity	NPC281356
0.925	High Similarity	NPC298796
0.9219	High Similarity	NPC469449
0.9206	High Similarity	NPC474289
0.92	High Similarity	NPC243688
0.9187	High Similarity	NPC109675
0.9187	High Similarity	NPC273772
0.918	High Similarity	NPC52247
0.918	High Similarity	NPC187868
0.9174	High Similarity	NPC247553
0.9167	High Similarity	NPC152306
0.9167	High Similarity	NPC265547
0.916	High Similarity	NPC151946
0.916	High Similarity	NPC279573
0.9147	High Similarity	NPC213173
0.9147	High Similarity	NPC224475
0.9147	High Similarity	NPC180716
0.9147	High Similarity	NPC62366
0.9127	High Similarity	NPC185066
0.9113	High Similarity	NPC201667
0.9113	High Similarity	NPC27671
0.9113	High Similarity	NPC73413
0.9084	High Similarity	NPC155963
0.9084	High Similarity	NPC131198
0.9077	High Similarity	NPC472525
0.907	High Similarity	NPC163557
0.9062	High Similarity	NPC250727
0.9055	High Similarity	NPC168710
0.904	High Similarity	NPC244495
0.904	High Similarity	NPC93219
0.9032	High Similarity	NPC472518
0.9023	High Similarity	NPC195357
0.9023	High Similarity	NPC152771
0.9016	High Similarity	NPC193193
0.9015	High Similarity	NPC43500
0.9015	High Similarity	NPC164148
0.9015	High Similarity	NPC211110
0.9008	High Similarity	NPC96705
0.9	High Similarity	NPC128633
0.8984	High Similarity	NPC32463
0.8976	High Similarity	NPC472519
0.8952	High Similarity	NPC96286
0.8952	High Similarity	NPC248429
0.8947	High Similarity	NPC312881
0.8939	High Similarity	NPC225106
0.8939	High Similarity	NPC232246
0.8939	High Similarity	NPC153818
0.8939	High Similarity	NPC471068
0.8939	High Similarity	NPC281014
0.8939	High Similarity	NPC294456
0.8939	High Similarity	NPC212124
0.8939	High Similarity	NPC184861
0.8939	High Similarity	NPC471069
0.8923	High Similarity	NPC291551
0.8923	High Similarity	NPC205797
0.8923	High Similarity	NPC142563
0.8923	High Similarity	NPC241165
0.8923	High Similarity	NPC1220
0.8923	High Similarity	NPC141822
0.8889	High Similarity	NPC232692
0.8889	High Similarity	NPC471827
0.8889	High Similarity	NPC202594
0.8889	High Similarity	NPC168259
0.8889	High Similarity	NPC471828
0.8881	High Similarity	NPC138149
0.8881	High Similarity	NPC287286
0.8881	High Similarity	NPC300611
0.888	High Similarity	NPC315807
0.8872	High Similarity	NPC471072
0.8872	High Similarity	NPC471071
0.8872	High Similarity	NPC144512
0.8872	High Similarity	NPC137262
0.8872	High Similarity	NPC37428
0.8872	High Similarity	NPC35501
0.8872	High Similarity	NPC471070
0.8872	High Similarity	NPC47040
0.8872	High Similarity	NPC278600
0.8871	High Similarity	NPC144418
0.8864	High Similarity	NPC188380
0.8864	High Similarity	NPC103409
0.8864	High Similarity	NPC78746
0.8864	High Similarity	NPC224543
0.8862	High Similarity	NPC31314
0.8855	High Similarity	NPC98179
0.8855	High Similarity	NPC253574
0.8846	High Similarity	NPC14248
0.8837	High Similarity	NPC80170
0.8837	High Similarity	NPC19242
0.8828	High Similarity	NPC219923
0.8828	High Similarity	NPC199204
0.8819	High Similarity	NPC101894
0.8819	High Similarity	NPC234109
0.8819	High Similarity	NPC188327
0.8815	High Similarity	NPC20631
0.8815	High Similarity	NPC93640
0.879	High Similarity	NPC319378
0.8788	High Similarity	NPC33986
0.8779	High Similarity	NPC167111
0.8779	High Similarity	NPC318400
0.8779	High Similarity	NPC222036
0.8779	High Similarity	NPC469965
0.8779	High Similarity	NPC133956
0.8779	High Similarity	NPC296624
0.8779	High Similarity	NPC471910
0.8779	High Similarity	NPC7526
0.8779	High Similarity	NPC207002
0.8759	High Similarity	NPC469701
0.875	High Similarity	NPC229916
0.875	High Similarity	NPC138212
0.8741	High Similarity	NPC476442
0.8741	High Similarity	NPC215512
0.873	High Similarity	NPC154176
0.873	High Similarity	NPC50720
0.873	High Similarity	NPC290605
0.873	High Similarity	NPC173350
0.8712	High Similarity	NPC18804
0.8712	High Similarity	NPC84894
0.8712	High Similarity	NPC198381
0.8712	High Similarity	NPC166672
0.8712	High Similarity	NPC287182
0.8712	High Similarity	NPC260265
0.8712	High Similarity	NPC127888
0.8712	High Similarity	NPC74655
0.8712	High Similarity	NPC307412
0.8712	High Similarity	NPC100986
0.8712	High Similarity	NPC319859
0.8712	High Similarity	NPC92830
0.8712	High Similarity	NPC55149
0.8712	High Similarity	NPC131950
0.8712	High Similarity	NPC267412
0.8712	High Similarity	NPC164269
0.8712	High Similarity	NPC195343
0.8712	High Similarity	NPC47163
0.8702	High Similarity	NPC281558
0.8702	High Similarity	NPC5423
0.8689	High Similarity	NPC33717
0.8686	High Similarity	NPC471824
0.8678	High Similarity	NPC235250
0.8672	High Similarity	NPC471826
0.8661	High Similarity	NPC291899
0.8651	High Similarity	NPC13007
0.8651	High Similarity	NPC257188
0.8651	High Similarity	NPC150214
0.8647	High Similarity	NPC61499
0.8647	High Similarity	NPC281241
0.8647	High Similarity	NPC472424
0.8647	High Similarity	NPC471625
0.8647	High Similarity	NPC471909
0.8647	High Similarity	NPC86892
0.8647	High Similarity	NPC469675
0.8636	High Similarity	NPC36437
0.8636	High Similarity	NPC241341
0.8636	High Similarity	NPC233018
0.8633	High Similarity	NPC476347
0.8623	High Similarity	NPC226722
0.8623	High Similarity	NPC475719
0.8623	High Similarity	NPC101255
0.8623	High Similarity	NPC85624
0.8623	High Similarity	NPC43716
0.8603	High Similarity	NPC183642
0.8603	High Similarity	NPC155552
0.8603	High Similarity	NPC310370
0.8593	High Similarity	NPC13067
0.8583	High Similarity	NPC76465
0.8583	High Similarity	NPC38761
0.8582	High Similarity	NPC160727
0.8582	High Similarity	NPC246177
0.8582	High Similarity	NPC476455
0.8582	High Similarity	NPC177281
0.8582	High Similarity	NPC223616
0.8582	High Similarity	NPC471630
0.8582	High Similarity	NPC283331
0.8582	High Similarity	NPC149320
0.8582	High Similarity	NPC128529
0.8582	High Similarity	NPC55615
0.8582	High Similarity	NPC317045
0.8582	High Similarity	NPC283019
0.8571	High Similarity	NPC187398
0.8571	High Similarity	NPC169510
0.8571	High Similarity	NPC476348
0.8561	High Similarity	NPC245120

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 NPC224774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	908
0.2-0.3	1698
0.3-0.4	2580
0.4-0.5	1930
0.5-0.6	1171
0.6-0.7	387
0.7-0.8	117
0.8-0.85	39
0.85-0.9	18
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.918	High Similarity	NPD422	Phase 1
0.8923	High Similarity	NPD5123	Clinical (unspecified phase)
0.8923	High Similarity	NPD5124	Phase 1
0.8603	High Similarity	NPD1652	Phase 2
0.855	High Similarity	NPD6859	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1548	Phase 1
0.8258	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1653	Approved
0.8231	Intermediate Similarity	NPD3225	Approved
0.812	Intermediate Similarity	NPD4908	Phase 1
0.8083	Intermediate Similarity	NPD9697	Approved
0.803	Intermediate Similarity	NPD2797	Approved
0.8017	Intermediate Similarity	NPD3134	Approved
0.8014	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD1296	Phase 2
0.8	Intermediate Similarity	NPD1091	Approved
0.8	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1551	Phase 2
0.7972	Intermediate Similarity	NPD6799	Approved
0.7951	Intermediate Similarity	NPD1358	Approved
0.7939	Intermediate Similarity	NPD9717	Approved
0.7931	Intermediate Similarity	NPD5403	Approved
0.7923	Intermediate Similarity	NPD3496	Discontinued
0.7914	Intermediate Similarity	NPD7033	Discontinued
0.7905	Intermediate Similarity	NPD6801	Discontinued
0.7887	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1549	Phase 2
0.7868	Intermediate Similarity	NPD3268	Approved
0.7857	Intermediate Similarity	NPD2796	Approved
0.7838	Intermediate Similarity	NPD7411	Suspended
0.7817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD290	Approved
0.7801	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD5401	Approved
0.7786	Intermediate Similarity	NPD3748	Approved
0.7778	Intermediate Similarity	NPD5535	Approved
0.7762	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1203	Approved
0.7754	Intermediate Similarity	NPD1613	Approved
0.7754	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD6832	Phase 2
0.771	Intermediate Similarity	NPD1778	Approved
0.7698	Intermediate Similarity	NPD4340	Discontinued
0.7697	Intermediate Similarity	NPD7075	Discontinued
0.7671	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3027	Phase 3
0.766	Intermediate Similarity	NPD1510	Phase 2
0.7651	Intermediate Similarity	NPD6599	Discontinued
0.7632	Intermediate Similarity	NPD7768	Phase 2
0.7626	Intermediate Similarity	NPD1240	Approved
0.7616	Intermediate Similarity	NPD7819	Suspended
0.7612	Intermediate Similarity	NPD4749	Approved
0.7609	Intermediate Similarity	NPD6798	Discontinued
0.7609	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2684	Approved
0.7582	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4626	Approved
0.7566	Intermediate Similarity	NPD5402	Approved
0.7557	Intermediate Similarity	NPD9545	Approved
0.7551	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4308	Phase 3
0.7533	Intermediate Similarity	NPD4380	Phase 2
0.7518	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.7484	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD7212	Phase 2
0.7483	Intermediate Similarity	NPD7213	Phase 3
0.7482	Intermediate Similarity	NPD1048	Approved
0.7467	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3817	Phase 2
0.745	Intermediate Similarity	NPD920	Approved
0.7448	Intermediate Similarity	NPD1243	Approved
0.7447	Intermediate Similarity	NPD6355	Discontinued
0.7445	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1019	Discontinued
0.7442	Intermediate Similarity	NPD1241	Discontinued
0.7431	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6002	Phase 3
0.7431	Intermediate Similarity	NPD6005	Phase 3
0.7431	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6004	Phase 3
0.7429	Intermediate Similarity	NPD6233	Phase 2
0.7424	Intermediate Similarity	NPD1894	Discontinued
0.7415	Intermediate Similarity	NPD6667	Approved
0.7415	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6666	Approved
0.741	Intermediate Similarity	NPD4625	Phase 3
0.7398	Intermediate Similarity	NPD940	Approved
0.7398	Intermediate Similarity	NPD846	Approved
0.7391	Intermediate Similarity	NPD2861	Phase 2
0.7391	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2424	Discontinued
0.7376	Intermediate Similarity	NPD4140	Approved
0.7361	Intermediate Similarity	NPD2935	Discontinued
0.7357	Intermediate Similarity	NPD411	Approved
0.7338	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7157	Approved
0.7324	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD230	Phase 1
0.7324	Intermediate Similarity	NPD447	Suspended
0.732	Intermediate Similarity	NPD1934	Approved
0.7315	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7447	Phase 1
0.7315	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5763	Approved
0.731	Intermediate Similarity	NPD5762	Approved
0.7305	Intermediate Similarity	NPD4062	Phase 3
0.7302	Intermediate Similarity	NPD968	Approved
0.7299	Intermediate Similarity	NPD8651	Approved
0.7296	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2799	Discontinued
0.729	Intermediate Similarity	NPD3882	Suspended
0.7273	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD2801	Approved
0.7267	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3018	Phase 2
0.7259	Intermediate Similarity	NPD3847	Discontinued
0.7254	Intermediate Similarity	NPD4307	Phase 2
0.7248	Intermediate Similarity	NPD1511	Approved
0.7246	Intermediate Similarity	NPD6362	Approved
0.7244	Intermediate Similarity	NPD3749	Approved
0.7231	Intermediate Similarity	NPD821	Approved
0.7226	Intermediate Similarity	NPD4288	Approved
0.7226	Intermediate Similarity	NPD3685	Discontinued
0.7222	Intermediate Similarity	NPD7097	Phase 1
0.7206	Intermediate Similarity	NPD1535	Discovery
0.7205	Intermediate Similarity	NPD3818	Discontinued
0.72	Intermediate Similarity	NPD2532	Approved
0.72	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD2533	Approved
0.7197	Intermediate Similarity	NPD6671	Approved
0.7195	Intermediate Similarity	NPD7549	Discontinued
0.7192	Intermediate Similarity	NPD7266	Discontinued
0.7163	Intermediate Similarity	NPD5163	Phase 2
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7054	Approved
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7153	Intermediate Similarity	NPD1608	Approved
0.7153	Intermediate Similarity	NPD6653	Approved
0.7152	Intermediate Similarity	NPD1512	Approved
0.7134	Intermediate Similarity	NPD6971	Discontinued
0.7134	Intermediate Similarity	NPD6559	Discontinued
0.7124	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6100	Approved
0.7123	Intermediate Similarity	NPD6099	Approved
0.7117	Intermediate Similarity	NPD7472	Approved
0.7113	Intermediate Similarity	NPD2313	Discontinued
0.7111	Intermediate Similarity	NPD5585	Approved
0.7107	Intermediate Similarity	NPD7199	Phase 2
0.7101	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2982	Phase 2
0.7101	Intermediate Similarity	NPD2983	Phase 2
0.7097	Intermediate Similarity	NPD37	Approved
0.7095	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2614	Approved
0.7091	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD919	Approved
0.7086	Intermediate Similarity	NPD3536	Discontinued
0.7083	Intermediate Similarity	NPD1933	Approved
0.7081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6166	Phase 2
0.7073	Intermediate Similarity	NPD6797	Phase 2
0.7073	Intermediate Similarity	NPD5953	Discontinued
0.7073	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5647	Approved
0.7071	Intermediate Similarity	NPD3691	Phase 2
0.7071	Intermediate Similarity	NPD3690	Phase 2
0.707	Intermediate Similarity	NPD4965	Approved
0.707	Intermediate Similarity	NPD4966	Approved
0.707	Intermediate Similarity	NPD4967	Phase 2
0.7059	Intermediate Similarity	NPD3686	Approved
0.7059	Intermediate Similarity	NPD3687	Approved
0.7055	Intermediate Similarity	NPD7286	Phase 2
0.7047	Intermediate Similarity	NPD3892	Phase 2
0.7042	Intermediate Similarity	NPD7095	Approved
0.7042	Intermediate Similarity	NPD3179	Approved
0.7042	Intermediate Similarity	NPD3180	Approved
0.7039	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6273	Approved
0.703	Intermediate Similarity	NPD7251	Discontinued
0.7029	Intermediate Similarity	NPD2981	Phase 2
0.702	Intermediate Similarity	NPD4357	Discontinued
0.7012	Intermediate Similarity	NPD7074	Phase 3
0.7007	Intermediate Similarity	NPD6032	Approved
0.7007	Intermediate Similarity	NPD4476	Approved
0.7007	Intermediate Similarity	NPD4477	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