NPASS Compound

Structure

NPC1827 OpenBabel07101718182D 28 30 0 0 0 0 0 0 0 0999 V2000 2.8399 0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0960 3.5275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9693 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1044 3.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5382 2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6677 4.5779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 3.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 0.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 3.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 1.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5984 -0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0988 3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.2470 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 26 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 9 1 0 0 0 0 5 20 2 0 0 0 0 6 10 1 0 0 0 0 6 21 2 0 0 0 0 7 12 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 28 1 0 0 0 0 16 27 1 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 24 2 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.06
Volume:	364.258
LogP:	4.1
LogD:	1.128
LogS:	-4.206
# Rotatable Bonds:	4
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	3.288
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.385
MDCK Permeability:	1.1781365174101666e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.485
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	91.52540588378906%
Volume Distribution (VD):	0.677
Pgp-substrate:	3.2466824054718018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.131
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	1.313
Half-life (T1/2):	0.515

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.857
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.176
Skin Sensitization:	0.721
Carcinogencity:	0.015
Eye Corrosion:	0.005
Eye Irritation:	0.906
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC1827

Natural Product ID:	NPC1827
*Common Name:**	1,10-Diformyl-3-Hydroxy-9-Methoxy-4,7-Dimethyl-6-Oxobenzo[B][1,4]Benzodioxepine-2-Carboxylic Acid
IUPAC Name:	1,10-diformyl-3-hydroxy-9-methoxy-4,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid
Synonyms:
Standard InCHIKey:	LRRJGRUEHSZJRI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H14O9/c1-7-4-11(26-3)9(5-20)16-12(7)19(25)28-15-8(2)14(22)13(18(23)24)10(6-21)17(15)27-16/h4-6,22H,1-3H3,(H,23,24)
SMILES:	COc1cc(C)c2c(c1C=O)Oc1c(OC2=O)c(C)c(c(c1C=O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL229087
PubChem CID:	16755902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO2574	Usnea articulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17629329]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24725159]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2574	Usnea articulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
Others	5

Activity Type	# Activity
Cell Line	6
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[469434]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[469434]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	150000.0	nM	PMID[469434]
NPT35	Others	n.a.		Activity	=	30.0	%	PMID[469433]
NPT35	Others	n.a.		Stability	=	94.1	%	PMID[469434]
NPT35	Others	n.a.		Stability	=	88.5	%	PMID[469434]
NPT35	Others	n.a.		Stability	=	89.6	%	PMID[469434]
NPT35	Others	n.a.		Stability	=	89.5	%	PMID[469434]

☑ 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 NPC1827 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	399
0.1-0.2	1908
0.2-0.3	4699
0.3-0.4	10282
0.4-0.5	7572
0.5-0.6	3736
0.6-0.7	5243
0.7-0.8	6551
0.8-0.85	1966
0.85-0.9	290
0.9-0.95	36
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC26568
0.9875	High Similarity	NPC246716
0.9875	High Similarity	NPC10576
0.9753	High Similarity	NPC181523
0.9752	High Similarity	NPC20543
0.9752	High Similarity	NPC239440
0.975	High Similarity	NPC272485
0.975	High Similarity	NPC292788
0.9693	High Similarity	NPC139350
0.9573	High Similarity	NPC289147
0.9565	High Similarity	NPC20216
0.9563	High Similarity	NPC156082
0.9518	High Similarity	NPC470091
0.9518	High Similarity	NPC329161
0.9518	High Similarity	NPC240887
0.9518	High Similarity	NPC113446
0.9509	High Similarity	NPC17219
0.9503	High Similarity	NPC112981
0.9375	High Similarity	NPC143050
0.9329	High Similarity	NPC49487
0.9329	High Similarity	NPC99613
0.9325	High Similarity	NPC29160
0.9321	High Similarity	NPC300984
0.9273	High Similarity	NPC109827
0.9273	High Similarity	NPC124470
0.9268	High Similarity	NPC234331
0.9264	High Similarity	NPC267153
0.9259	High Similarity	NPC93739
0.9217	High Similarity	NPC158226
0.9212	High Similarity	NPC163130
0.9212	High Similarity	NPC165979
0.9202	High Similarity	NPC474350
0.9202	High Similarity	NPC284007
0.9198	High Similarity	NPC303565
0.9146	High Similarity	NPC8070
0.9125	High Similarity	NPC89625
0.9125	High Similarity	NPC149618
0.9125	High Similarity	NPC471800
0.9074	High Similarity	NPC168616
0.9074	High Similarity	NPC83763
0.9074	High Similarity	NPC238381
0.9024	High Similarity	NPC108767
0.9018	High Similarity	NPC200594
0.897	High Similarity	NPC197168
0.8963	High Similarity	NPC66288
0.8951	High Similarity	NPC54928
0.8938	High Similarity	NPC133856
0.8916	High Similarity	NPC25361
0.8909	High Similarity	NPC294965
0.8902	High Similarity	NPC47623
0.8902	High Similarity	NPC475886
0.8902	High Similarity	NPC474287
0.8896	High Similarity	NPC217677
0.8896	High Similarity	NPC165977
0.8882	High Similarity	NPC273483
0.8855	High Similarity	NPC234004
0.8855	High Similarity	NPC236132
0.8855	High Similarity	NPC270837
0.8848	High Similarity	NPC474186
0.8848	High Similarity	NPC474351
0.8848	High Similarity	NPC474187
0.8848	High Similarity	NPC475883
0.8841	High Similarity	NPC45846
0.8834	High Similarity	NPC472456
0.8834	High Similarity	NPC146211
0.8814	High Similarity	NPC220369
0.8812	High Similarity	NPC291049
0.8812	High Similarity	NPC233267
0.8795	High Similarity	NPC8300
0.8795	High Similarity	NPC144843
0.8788	High Similarity	NPC84571
0.8788	High Similarity	NPC56085
0.8788	High Similarity	NPC14353
0.8788	High Similarity	NPC228785
0.8779	High Similarity	NPC207467
0.8772	High Similarity	NPC245975
0.8765	High Similarity	NPC289968
0.8765	High Similarity	NPC175978
0.8764	High Similarity	NPC214901
0.8758	High Similarity	NPC213382
0.8758	High Similarity	NPC164527
0.875	High Similarity	NPC105415
0.875	High Similarity	NPC472452
0.8743	High Similarity	NPC101769
0.8743	High Similarity	NPC7483
0.8735	High Similarity	NPC61010
0.8735	High Similarity	NPC278052
0.8735	High Similarity	NPC311740
0.8735	High Similarity	NPC40491
0.8728	High Similarity	NPC473785
0.8727	High Similarity	NPC100123
0.8712	High Similarity	NPC475895
0.8704	High Similarity	NPC204350
0.8696	High Similarity	NPC285527
0.8696	High Similarity	NPC106334
0.869	High Similarity	NPC326520
0.869	High Similarity	NPC85057
0.869	High Similarity	NPC130920
0.8683	High Similarity	NPC229632
0.8675	High Similarity	NPC320359
0.8675	High Similarity	NPC119224
0.8667	High Similarity	NPC241904
0.8667	High Similarity	NPC44199
0.8667	High Similarity	NPC300727
0.8667	High Similarity	NPC263483
0.8659	High Similarity	NPC20541
0.865	High Similarity	NPC199773
0.8642	High Similarity	NPC119929
0.8639	High Similarity	NPC170245
0.8639	High Similarity	NPC37870
0.8639	High Similarity	NPC30027
0.8634	High Similarity	NPC5537
0.8631	High Similarity	NPC477689
0.8631	High Similarity	NPC248638
0.8631	High Similarity	NPC41301
0.8631	High Similarity	NPC152659
0.8631	High Similarity	NPC236521
0.8631	High Similarity	NPC220313
0.8623	High Similarity	NPC266314
0.8614	High Similarity	NPC85121
0.8614	High Similarity	NPC476242
0.8606	High Similarity	NPC5379
0.8606	High Similarity	NPC14561
0.8606	High Similarity	NPC197751
0.8606	High Similarity	NPC77807
0.8606	High Similarity	NPC274730
0.8606	High Similarity	NPC227062
0.8606	High Similarity	NPC142339
0.8605	High Similarity	NPC277510
0.8605	High Similarity	NPC233956
0.8598	High Similarity	NPC280937
0.8596	High Similarity	NPC295436
0.8589	High Similarity	NPC117579
0.8588	High Similarity	NPC76647
0.8588	High Similarity	NPC6588
0.8588	High Similarity	NPC117854
0.8588	High Similarity	NPC477154
0.8588	High Similarity	NPC474024
0.858	High Similarity	NPC239752
0.858	High Similarity	NPC472450
0.858	High Similarity	NPC275780
0.8571	High Similarity	NPC154720
0.8571	High Similarity	NPC25152
0.8571	High Similarity	NPC265795
0.8571	High Similarity	NPC52204
0.8571	High Similarity	NPC470694
0.8564	High Similarity	NPC198163
0.8563	High Similarity	NPC243701
0.8563	High Similarity	NPC292415
0.8563	High Similarity	NPC36217
0.8563	High Similarity	NPC299436
0.8562	High Similarity	NPC134621
0.8555	High Similarity	NPC470454
0.8555	High Similarity	NPC199533
0.8554	High Similarity	NPC199463
0.8554	High Similarity	NPC476981
0.8554	High Similarity	NPC223787
0.8554	High Similarity	NPC262286
0.8554	High Similarity	NPC108456
0.8554	High Similarity	NPC236796
0.8554	High Similarity	NPC178976
0.8554	High Similarity	NPC36852
0.8554	High Similarity	NPC181960
0.8554	High Similarity	NPC78225
0.8554	High Similarity	NPC469584
0.8554	High Similarity	NPC37543
0.8547	High Similarity	NPC475669
0.8547	High Similarity	NPC260263
0.8545	High Similarity	NPC472048
0.8545	High Similarity	NPC82592
0.8545	High Similarity	NPC472909
0.8545	High Similarity	NPC16082
0.8545	High Similarity	NPC16286
0.8545	High Similarity	NPC38898
0.8545	High Similarity	NPC37392
0.8537	High Similarity	NPC154683
0.8537	High Similarity	NPC271681
0.8537	High Similarity	NPC475116
0.8537	High Similarity	NPC281272
0.8537	High Similarity	NPC40356
0.8537	High Similarity	NPC217447
0.8529	High Similarity	NPC43319
0.8529	High Similarity	NPC272502
0.8529	High Similarity	NPC39091
0.8528	High Similarity	NPC202595
0.8528	High Similarity	NPC294646
0.8528	High Similarity	NPC225129
0.8528	High Similarity	NPC306821
0.8528	High Similarity	NPC179183
0.8528	High Similarity	NPC60413
0.8521	High Similarity	NPC23298
0.8521	High Similarity	NPC470459
0.8521	High Similarity	NPC207690
0.8521	High Similarity	NPC273959
0.8521	High Similarity	NPC475985
0.8521	High Similarity	NPC189473
0.8519	High Similarity	NPC2569
0.8519	High Similarity	NPC172329
0.8514	High Similarity	NPC212290
0.8512	High Similarity	NPC473106

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 NPC1827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	1054
0.2-0.3	2024
0.3-0.4	2621
0.4-0.5	1669
0.5-0.6	886
0.6-0.7	348
0.7-0.8	145
0.8-0.85	22
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8909	High Similarity	NPD6232	Discontinued
0.875	High Similarity	NPD7473	Discontinued
0.8647	High Similarity	NPD5844	Phase 1
0.8373	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8313	Intermediate Similarity	NPD1934	Approved
0.8263	Intermediate Similarity	NPD1465	Phase 2
0.8263	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD3226	Approved
0.8214	Intermediate Similarity	NPD3817	Phase 2
0.8166	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD5494	Approved
0.8081	Intermediate Similarity	NPD1247	Approved
0.8081	Intermediate Similarity	NPD6959	Discontinued
0.8075	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD919	Approved
0.8059	Intermediate Similarity	NPD3882	Suspended
0.8034	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.7967	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD3818	Discontinued
0.795	Intermediate Similarity	NPD1551	Phase 2
0.7943	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD1511	Approved
0.7929	Intermediate Similarity	NPD7411	Suspended
0.7892	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6559	Discontinued
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7865	Intermediate Similarity	NPD7074	Phase 3
0.7844	Intermediate Similarity	NPD1512	Approved
0.784	Intermediate Similarity	NPD2935	Discontinued
0.7836	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7054	Approved
0.7798	Intermediate Similarity	NPD920	Approved
0.7791	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7765	Intermediate Similarity	NPD7472	Approved
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7746	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4967	Phase 2
0.7746	Intermediate Similarity	NPD4965	Approved
0.774	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5710	Approved
0.7727	Intermediate Similarity	NPD5711	Approved
0.7725	Intermediate Similarity	NPD6799	Approved
0.7722	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD447	Suspended
0.7701	Intermediate Similarity	NPD3749	Approved
0.7688	Intermediate Similarity	NPD5402	Approved
0.7683	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2346	Discontinued
0.7679	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1607	Approved
0.7651	Intermediate Similarity	NPD3750	Approved
0.7644	Intermediate Similarity	NPD7768	Phase 2
0.7637	Intermediate Similarity	NPD7808	Phase 3
0.7636	Intermediate Similarity	NPD1549	Phase 2
0.7624	Intermediate Similarity	NPD6797	Phase 2
0.76	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD230	Phase 1
0.759	Intermediate Similarity	NPD2800	Approved
0.7584	Intermediate Similarity	NPD3926	Phase 2
0.7582	Intermediate Similarity	NPD7251	Discontinued
0.7574	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7199	Phase 2
0.7568	Intermediate Similarity	NPD8434	Phase 2
0.7561	Intermediate Similarity	NPD1510	Phase 2
0.7561	Intermediate Similarity	NPD2799	Discontinued
0.756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD1240	Approved
0.7527	Intermediate Similarity	NPD5953	Discontinued
0.7514	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7228	Approved
0.744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7390	Discontinued
0.741	Intermediate Similarity	NPD2796	Approved
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD8313	Approved
0.7387	Intermediate Similarity	NPD7783	Phase 2
0.7387	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7435	Discontinued
0.7384	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8151	Discontinued
0.7349	Intermediate Similarity	NPD3748	Approved
0.7337	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD6778	Approved
0.732	Intermediate Similarity	NPD6776	Approved
0.732	Intermediate Similarity	NPD6779	Approved
0.732	Intermediate Similarity	NPD6780	Approved
0.732	Intermediate Similarity	NPD6781	Approved
0.732	Intermediate Similarity	NPD6777	Approved
0.732	Intermediate Similarity	NPD6782	Approved
0.7317	Intermediate Similarity	NPD943	Approved
0.7301	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7283	Intermediate Similarity	NPD5403	Approved
0.7268	Intermediate Similarity	NPD3751	Discontinued
0.7267	Intermediate Similarity	NPD5401	Approved
0.7246	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1653	Approved
0.7238	Intermediate Similarity	NPD7229	Phase 3
0.7209	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD7698	Approved
0.7208	Intermediate Similarity	NPD7696	Phase 3
0.7205	Intermediate Similarity	NPD1203	Approved
0.7202	Intermediate Similarity	NPD6100	Approved
0.7202	Intermediate Similarity	NPD6099	Approved
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5242	Approved
0.7195	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD6832	Phase 2
0.7172	Intermediate Similarity	NPD7871	Phase 2
0.7172	Intermediate Similarity	NPD7870	Phase 2
0.7169	Intermediate Similarity	NPD1933	Approved
0.7169	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7874	Approved
0.7164	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2344	Approved
0.7126	Intermediate Similarity	NPD6651	Approved
0.7126	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9494	Approved
0.7117	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7240	Approved
0.7108	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4060	Phase 1
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7093	Intermediate Similarity	NPD6190	Approved
0.7091	Intermediate Similarity	NPD411	Approved
0.7088	Intermediate Similarity	NPD8127	Discontinued
0.7073	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7701	Phase 2
0.7062	Intermediate Similarity	NPD6535	Approved
0.7062	Intermediate Similarity	NPD6534	Approved
0.7049	Intermediate Similarity	NPD3787	Discontinued
0.7041	Intermediate Similarity	NPD4308	Phase 3
0.7037	Intermediate Similarity	NPD1283	Approved
0.703	Intermediate Similarity	NPD4625	Phase 3
0.703	Intermediate Similarity	NPD3027	Phase 3
0.7019	Intermediate Similarity	NPD9717	Approved
0.7019	Intermediate Similarity	NPD1608	Approved
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7005	Intermediate Similarity	NPD8285	Discontinued
0.7	Intermediate Similarity	NPD4476	Approved
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD5353	Approved
0.6994	Remote Similarity	NPD2309	Approved
0.6989	Remote Similarity	NPD7177	Discontinued
0.6989	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3268	Approved
0.6985	Remote Similarity	NPD6823	Phase 2
0.6984	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7801	Approved
0.6959	Remote Similarity	NPD1471	Phase 3
0.6957	Remote Similarity	NPD1611	Approved
0.6957	Remote Similarity	NPD422	Phase 1
0.6954	Remote Similarity	NPD7699	Phase 2
0.6954	Remote Similarity	NPD7700	Phase 2
0.6936	Remote Similarity	NPD7003	Approved
0.6932	Remote Similarity	NPD6273	Approved
0.6931	Remote Similarity	NPD7685	Pre-registration
0.6927	Remote Similarity	NPD6386	Approved
0.6927	Remote Similarity	NPD6385	Approved
0.6927	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD9269	Phase 2
0.6911	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4288	Approved
0.6905	Remote Similarity	NPD2979	Phase 3
0.6904	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7549	Discontinued
0.689	Remote Similarity	NPD1470	Approved
0.689	Remote Similarity	NPD2797	Approved
0.6886	Remote Similarity	NPD3764	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