NPASS Compound

Structure

NPC24258 OpenBabel07101718302D 30 33 0 0 0 0 0 0 0 0999 V2000 -2.2861 4.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -2.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1226 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8546 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1226 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9886 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8546 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9886 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7861 1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2861 2.7965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9886 -2.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7206 -1.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2861 2.7965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7861 3.6625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -1.8366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7807 1.8259 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 27 1 0 0 0 0 2 28 1 0 0 0 0 3 7 1 0 0 0 0 3 9 2 0 0 0 0 4 8 1 0 0 0 0 4 10 2 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 17 19 1 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.06
Volume:	381.788
LogP:	3.164
LogD:	2.207
LogS:	-4.782
# Rotatable Bonds:	5
TPSA:	159.8
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	2.934
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.376
MDCK Permeability:	3.515230127959512e-05
Pgp-inhibitor:	0.219
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.836
20% Bioavailability (F20%):	0.177
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	85.91333770751953%
Volume Distribution (VD):	0.659
Pgp-substrate:	23.442989349365234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.636
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.606
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.228
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	11.956
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.755
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.455
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.584
Carcinogencity:	0.011
Eye Corrosion:	0.004
Eye Irritation:	0.876
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC24258

Natural Product ID:	NPC24258
*Common Name:**	5,6,5',6'-Tetrahydroxy[3,3']Bibenzofuranyl-2,2'-Dicarboxylic Acid Dimethyl Ester
IUPAC Name:	methyl 3-(5,6-dihydroxy-2-methoxycarbonyl-1-benzofuran-3-yl)-5,6-dihydroxy-1-benzofuran-2-carboxylate
Synonyms:	kynapcin-24
Standard InCHIKey:	IVZFDKACPFMQDJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14O10/c1-27-19(25)17-15(7-3-9(21)11(23)5-13(7)29-17)16-8-4-10(22)12(24)6-14(8)30-18(16)20(26)28-2/h3-6,21-24H,1-2H3
SMILES:	COC(=O)c1c(c2cc(c(cc2o1)O)O)c1c2cc(c(cc2oc1C(=O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465606
PubChem CID:	10093198
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO32869	polyozellus multiflex	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809072]

☑ 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	1
Ki	1
Others	12

Activity Type	# Activity
Individual Protein	5
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6363	Individual Protein	Elastase 1	Homo sapiens	Activity	=	67.5	%	PMID[489955]
NPT6363	Individual Protein	Elastase 1	Homo sapiens	Activity	=	97.5	%	PMID[489955]
NPT6363	Individual Protein	Elastase 1	Homo sapiens	Activity	=	98.0	%	PMID[489955]
NPT6363	Individual Protein	Elastase 1	Homo sapiens	IC50	=	1140.0	nM	PMID[489955]
NPT6363	Individual Protein	Elastase 1	Homo sapiens	Ki	=	290.0	nM	PMID[489955]
NPT2	Others	Unspecified		Activity	=	3.1	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	5.6	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	5.9	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	22.0	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	27.6	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	29.0	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	3.7	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	6.6	%	PMID[489955]
NPT2	Others	Unspecified		Activity	=	4.0	%	PMID[489955]

☑ 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 NPC24258 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	410
0.1-0.2	2035
0.2-0.3	5039
0.3-0.4	10567
0.4-0.5	7208
0.5-0.6	4085
0.6-0.7	5655
0.7-0.8	5371
0.8-0.85	1772
0.85-0.9	518
0.9-0.95	35
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC71260
0.9405	High Similarity	NPC471841
0.9401	High Similarity	NPC117450
0.9298	High Similarity	NPC471842
0.9157	High Similarity	NPC45449
0.9152	High Similarity	NPC238995
0.9123	High Similarity	NPC98546
0.9096	High Similarity	NPC39305
0.9096	High Similarity	NPC1706
0.9096	High Similarity	NPC59295
0.9096	High Similarity	NPC263092
0.9096	High Similarity	NPC1755
0.9048	High Similarity	NPC86477
0.9042	High Similarity	NPC36320
0.9017	High Similarity	NPC47883
0.9012	High Similarity	NPC297807
0.9	High Similarity	NPC54098
0.9	High Similarity	NPC230619
0.8994	High Similarity	NPC202470
0.8976	High Similarity	NPC188486
0.897	High Similarity	NPC196879
0.8947	High Similarity	NPC277510
0.8947	High Similarity	NPC82217
0.8947	High Similarity	NPC216842
0.8947	High Similarity	NPC37606
0.8947	High Similarity	NPC476640
0.8941	High Similarity	NPC28042
0.8929	High Similarity	NPC29411
0.8927	High Similarity	NPC295436
0.8922	High Similarity	NPC272722
0.8922	High Similarity	NPC312056
0.8922	High Similarity	NPC84515
0.8895	High Similarity	NPC287243
0.8895	High Similarity	NPC289244
0.8882	High Similarity	NPC247136
0.8876	High Similarity	NPC60848
0.8869	High Similarity	NPC133065
0.8855	High Similarity	NPC16935
0.8848	High Similarity	NPC45131
0.8844	High Similarity	NPC8127
0.8844	High Similarity	NPC49667
0.8837	High Similarity	NPC30550
0.8837	High Similarity	NPC261471
0.883	High Similarity	NPC218533
0.883	High Similarity	NPC78830
0.883	High Similarity	NPC476641
0.8824	High Similarity	NPC470704
0.8817	High Similarity	NPC291110
0.8817	High Similarity	NPC39306
0.8814	High Similarity	NPC248315
0.88	High Similarity	NPC475996
0.878	High Similarity	NPC125300
0.8757	High Similarity	NPC226725
0.8743	High Similarity	NPC195832
0.8736	High Similarity	NPC164384
0.8735	High Similarity	NPC472461
0.8728	High Similarity	NPC149846
0.8728	High Similarity	NPC233956
0.8728	High Similarity	NPC473834
0.8728	High Similarity	NPC65885
0.8721	High Similarity	NPC281835
0.8713	High Similarity	NPC247973
0.8713	High Similarity	NPC50394
0.8713	High Similarity	NPC95715
0.8706	High Similarity	NPC37183
0.8706	High Similarity	NPC187923
0.8701	High Similarity	NPC154527
0.8678	High Similarity	NPC290304
0.8678	High Similarity	NPC236327
0.8671	High Similarity	NPC28589
0.8671	High Similarity	NPC248593
0.8671	High Similarity	NPC174700
0.8663	High Similarity	NPC211309
0.8663	High Similarity	NPC280493
0.8655	High Similarity	NPC277480
0.8647	High Similarity	NPC89131
0.8647	High Similarity	NPC110257
0.8636	High Similarity	NPC476273
0.8631	High Similarity	NPC193842
0.8623	High Similarity	NPC268161
0.8605	High Similarity	NPC241820
0.8596	High Similarity	NPC8070
0.8588	High Similarity	NPC97523
0.858	High Similarity	NPC471744
0.858	High Similarity	NPC23553
0.858	High Similarity	NPC300680
0.858	High Similarity	NPC77179
0.8571	High Similarity	NPC53917
0.8571	High Similarity	NPC305663
0.8571	High Similarity	NPC472438
0.8571	High Similarity	NPC235215
0.8571	High Similarity	NPC78302
0.8571	High Similarity	NPC176665
0.8571	High Similarity	NPC163524
0.8571	High Similarity	NPC29841
0.8571	High Similarity	NPC7973
0.8571	High Similarity	NPC287979
0.8571	High Similarity	NPC245975
0.8563	High Similarity	NPC214138
0.8563	High Similarity	NPC247964
0.8554	High Similarity	NPC289968
0.8554	High Similarity	NPC304954
0.8547	High Similarity	NPC304322
0.8539	High Similarity	NPC228209
0.8538	High Similarity	NPC472582
0.8538	High Similarity	NPC300984
0.8529	High Similarity	NPC231758
0.8529	High Similarity	NPC112418
0.8523	High Similarity	NPC107244
0.8521	High Similarity	NPC7846
0.8521	High Similarity	NPC115798
0.8521	High Similarity	NPC143828
0.8521	High Similarity	NPC18772
0.8521	High Similarity	NPC288669
0.8521	High Similarity	NPC18607
0.8521	High Similarity	NPC25495
0.8521	High Similarity	NPC130894
0.8521	High Similarity	NPC4481
0.8521	High Similarity	NPC300943
0.8521	High Similarity	NPC176300
0.8521	High Similarity	NPC253634
0.8521	High Similarity	NPC191459
0.8521	High Similarity	NPC22472
0.8521	High Similarity	NPC204854
0.8521	High Similarity	NPC105242
0.8521	High Similarity	NPC9609
0.8521	High Similarity	NPC19687
0.8521	High Similarity	NPC152166
0.8521	High Similarity	NPC261004
0.8514	High Similarity	NPC310794
0.8512	High Similarity	NPC100916
0.8512	High Similarity	NPC200388
0.8512	High Similarity	NPC55619
0.8512	High Similarity	NPC247017
0.8512	High Similarity	NPC98661
0.8512	High Similarity	NPC474520
0.8512	High Similarity	NPC43243
0.8512	High Similarity	NPC266960
0.8512	High Similarity	NPC245546
0.85	High Similarity	NPC47905
0.85	High Similarity	NPC139683
0.85	High Similarity	NPC73929
0.8497	Intermediate Similarity	NPC76482
0.8494	Intermediate Similarity	NPC171010
0.8492	Intermediate Similarity	NPC476170
0.8488	Intermediate Similarity	NPC88243
0.8488	Intermediate Similarity	NPC38914
0.8488	Intermediate Similarity	NPC267153
0.848	Intermediate Similarity	NPC93739
0.848	Intermediate Similarity	NPC471745
0.848	Intermediate Similarity	NPC164937
0.8476	Intermediate Similarity	NPC17816
0.8475	Intermediate Similarity	NPC221820
0.8475	Intermediate Similarity	NPC207467
0.8471	Intermediate Similarity	NPC304839
0.8471	Intermediate Similarity	NPC220582
0.8471	Intermediate Similarity	NPC130955
0.8471	Intermediate Similarity	NPC246478
0.8466	Intermediate Similarity	NPC224165
0.8462	Intermediate Similarity	NPC227192
0.8462	Intermediate Similarity	NPC203891
0.8462	Intermediate Similarity	NPC75215
0.8462	Intermediate Similarity	NPC101830
0.8462	Intermediate Similarity	NPC189179
0.8462	Intermediate Similarity	NPC224137
0.8462	Intermediate Similarity	NPC93376
0.8462	Intermediate Similarity	NPC110070
0.8457	Intermediate Similarity	NPC158226
0.8457	Intermediate Similarity	NPC475964
0.8457	Intermediate Similarity	NPC157522
0.8457	Intermediate Similarity	NPC476370
0.8452	Intermediate Similarity	NPC201451
0.8452	Intermediate Similarity	NPC44079
0.8452	Intermediate Similarity	NPC38898
0.8452	Intermediate Similarity	NPC80489
0.8452	Intermediate Similarity	NPC208197
0.8452	Intermediate Similarity	NPC26227
0.8448	Intermediate Similarity	NPC163130
0.8448	Intermediate Similarity	NPC165979
0.8443	Intermediate Similarity	NPC101996
0.8443	Intermediate Similarity	NPC161277
0.8443	Intermediate Similarity	NPC142540
0.8443	Intermediate Similarity	NPC39007
0.8443	Intermediate Similarity	NPC123886
0.8436	Intermediate Similarity	NPC246153
0.8436	Intermediate Similarity	NPC182693
0.8436	Intermediate Similarity	NPC8927
0.8436	Intermediate Similarity	NPC240508
0.8434	Intermediate Similarity	NPC260582
0.843	Intermediate Similarity	NPC41301
0.843	Intermediate Similarity	NPC109180
0.843	Intermediate Similarity	NPC284007
0.843	Intermediate Similarity	NPC470459
0.8427	Intermediate Similarity	NPC183843
0.8427	Intermediate Similarity	NPC473785
0.8424	Intermediate Similarity	NPC19545
0.8421	Intermediate Similarity	NPC303565
0.8421	Intermediate Similarity	NPC258331
0.8421	Intermediate Similarity	NPC308992
0.8421	Intermediate Similarity	NPC304387

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 NPC24258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	1039
0.2-0.3	2103
0.3-0.4	2712
0.4-0.5	1671
0.5-0.6	843
0.6-0.7	282
0.7-0.8	100
0.8-0.85	26
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8512	High Similarity	NPD3882	Suspended
0.8314	Intermediate Similarity	NPD1247	Approved
0.8284	Intermediate Similarity	NPD2801	Approved
0.8235	Intermediate Similarity	NPD3817	Phase 2
0.8218	Intermediate Similarity	NPD3926	Phase 2
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD1934	Approved
0.8092	Intermediate Similarity	NPD919	Approved
0.8084	Intermediate Similarity	NPD1512	Approved
0.8079	Intermediate Similarity	NPD3818	Discontinued
0.807	Intermediate Similarity	NPD1465	Phase 2
0.8068	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6166	Phase 2
0.8068	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD3749	Approved
0.8035	Intermediate Similarity	NPD7075	Discontinued
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.7965	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD1511	Approved
0.7964	Intermediate Similarity	NPD6799	Approved
0.7919	Intermediate Similarity	NPD5402	Approved
0.7907	Intermediate Similarity	NPD6801	Discontinued
0.7895	Intermediate Similarity	NPD6599	Discontinued
0.7861	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6797	Phase 2
0.7841	Intermediate Similarity	NPD5494	Approved
0.7802	Intermediate Similarity	NPD7251	Discontinued
0.7802	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7411	Suspended
0.7735	Intermediate Similarity	NPD5844	Phase 1
0.7719	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD2344	Approved
0.7706	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7074	Phase 3
0.7663	Intermediate Similarity	NPD7808	Phase 3
0.7657	Intermediate Similarity	NPD7819	Suspended
0.7637	Intermediate Similarity	NPD7054	Approved
0.7619	Intermediate Similarity	NPD1243	Approved
0.7611	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6959	Discontinued
0.7596	Intermediate Similarity	NPD7472	Approved
0.7594	Intermediate Similarity	NPD8434	Phase 2
0.756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3226	Approved
0.7529	Intermediate Similarity	NPD2309	Approved
0.7528	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD230	Phase 1
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5403	Approved
0.7514	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2533	Approved
0.7486	Intermediate Similarity	NPD4380	Phase 2
0.7486	Intermediate Similarity	NPD6234	Discontinued
0.7472	Intermediate Similarity	NPD7768	Phase 2
0.7456	Intermediate Similarity	NPD1549	Phase 2
0.7455	Intermediate Similarity	NPD943	Approved
0.7455	Intermediate Similarity	NPD1240	Approved
0.7447	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2935	Discontinued
0.7435	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7199	Phase 2
0.7399	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1510	Phase 2
0.7368	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD1607	Approved
0.7326	Intermediate Similarity	NPD6190	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD447	Suspended
0.7294	Intermediate Similarity	NPD1471	Phase 3
0.7293	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2403	Approved
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2796	Approved
0.7235	Intermediate Similarity	NPD1551	Phase 2
0.7204	Intermediate Similarity	NPD7228	Approved
0.7193	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5953	Discontinued
0.7168	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4628	Phase 3
0.715	Intermediate Similarity	NPD4287	Approved
0.7112	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD37	Approved
0.7081	Intermediate Similarity	NPD6808	Phase 2
0.7081	Intermediate Similarity	NPD3787	Discontinued
0.7076	Intermediate Similarity	NPD3748	Approved
0.7076	Intermediate Similarity	NPD2799	Discontinued
0.7074	Intermediate Similarity	NPD7286	Phase 2
0.7065	Intermediate Similarity	NPD7435	Discontinued
0.7048	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD2296	Approved
0.7024	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2346	Discontinued
0.6989	Remote Similarity	NPD5711	Approved
0.6989	Remote Similarity	NPD5710	Approved
0.6983	Remote Similarity	NPD1653	Approved
0.6979	Remote Similarity	NPD8313	Approved
0.6979	Remote Similarity	NPD8312	Approved
0.6977	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8151	Discontinued
0.6951	Remote Similarity	NPD9269	Phase 2
0.6949	Remote Similarity	NPD7390	Discontinued
0.6941	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1613	Approved
0.6931	Remote Similarity	NPD2163	Approved
0.6928	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD2313	Discontinued
0.6915	Remote Similarity	NPD6776	Approved
0.6915	Remote Similarity	NPD6782	Approved
0.6915	Remote Similarity	NPD6780	Approved
0.6915	Remote Similarity	NPD6777	Approved
0.6915	Remote Similarity	NPD6781	Approved
0.6915	Remote Similarity	NPD6779	Approved
0.6915	Remote Similarity	NPD6778	Approved
0.6901	Remote Similarity	NPD1933	Approved
0.6901	Remote Similarity	NPD6355	Discontinued
0.6898	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD7685	Pre-registration
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8150	Discontinued
0.6862	Remote Similarity	NPD5242	Approved
0.686	Remote Similarity	NPD6651	Approved
0.686	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7874	Approved
0.6836	Remote Similarity	NPD2354	Approved
0.6824	Remote Similarity	NPD3268	Approved
0.6824	Remote Similarity	NPD6798	Discontinued
0.6824	Remote Similarity	NPD3764	Approved
0.6816	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6832	Phase 2
0.6802	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7240	Approved
0.678	Remote Similarity	NPD7871	Phase 2
0.678	Remote Similarity	NPD7870	Phase 2
0.6765	Remote Similarity	NPD3027	Phase 3
0.6753	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1608	Approved
0.6747	Remote Similarity	NPD9717	Approved
0.6746	Remote Similarity	NPD7783	Phase 2
0.6746	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD9494	Approved
0.6744	Remote Similarity	NPD4060	Phase 1
0.6743	Remote Similarity	NPD6100	Approved
0.6743	Remote Similarity	NPD6099	Approved
0.6739	Remote Similarity	NPD6279	Approved
0.6739	Remote Similarity	NPD6280	Approved
0.6737	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7698	Approved
0.6732	Remote Similarity	NPD7697	Approved
0.6732	Remote Similarity	NPD7696	Phase 3
0.6707	Remote Similarity	NPD9268	Approved
0.6698	Remote Similarity	NPD7907	Approved
0.6684	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD5353	Approved
0.6649	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5404	Approved
0.6648	Remote Similarity	NPD5405	Approved
0.6648	Remote Similarity	NPD5406	Approved
0.6648	Remote Similarity	NPD5408	Approved
0.6628	Remote Similarity	NPD411	Approved
0.6627	Remote Similarity	NPD3266	Approved
0.6627	Remote Similarity	NPD3267	Approved
0.662	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6764	Approved
0.6615	Remote Similarity	NPD6765	Approved
0.6613	Remote Similarity	NPD8455	Phase 2
0.661	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2353	Approved
0.6607	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD6386	Approved
0.6595	Remote Similarity	NPD6385	Approved
0.6593	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5049	Phase 3
0.6591	Remote Similarity	NPD7033	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