NPASS Compound

Structure

NPC89131 OpenBabel07101718222D 32 35 0 0 0 0 0 0 0 0999 V2000 3.9703 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 -0.3660 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 5.7709 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 1.3660 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 2.9921 -1.2601 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 4.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7709 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 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 3.2709 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 2.3230 -2.0032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2709 0.5000 0.0000 O 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 6.2709 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 2.6831 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 30 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 12 25 2 0 0 0 0 14 23 1 0 0 0 0 15 31 1 0 0 0 0 16 18 2 0 0 0 0 16 26 1 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 20 22 2 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 22 24 1 0 0 0 0 23 32 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.1
Volume:	428.119
LogP:	3.668
LogD:	2.641
LogS:	-4.032
# Rotatable Bonds:	5
TPSA:	130.34
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	2.9
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	1.3826394024363253e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.883
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.245
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	97.34541320800781%
Volume Distribution (VD):	0.409
Pgp-substrate:	4.774709701538086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.876
CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.481
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.635
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.202
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	6.666
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.758
Skin Sensitization:	0.458
Carcinogencity:	0.404
Eye Corrosion:	0.004
Eye Irritation:	0.814
Respiratory Toxicity:	0.156

Download Data

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

Natural Product: NPC89131

Natural Product ID:	NPC89131
*Common Name:**	Methylinoscavin C
IUPAC Name:	3-acetyl-2-(3,4-dihydroxyphenyl)-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]furo[3,2-c]pyran-4-one
Synonyms:	Methylinoscavin C
Standard InCHIKey:	LWDOBNFZTXHPQD-ZZXKWVIFSA-N
Standard InCHI:	InChI=1S/C24H18O8/c1-12(25)21-22-20(32-23(21)14-5-8-16(26)18(28)10-14)11-15(31-24(22)29)6-3-13-4-7-17(27)19(9-13)30-2/h3-11,26-28H,1-2H3/b6-3+
SMILES:	COc1cc(/C=C/c2oc(=O)c3c(c2)oc(c3C(=O)C)c2ccc(c(c2)O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL205444
PubChem CID:	44410486
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16488146]
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	chonan-si, Korea	2005-APR	PMID[16499338]

☑ 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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[481783]
NPT1	Others	Radical scavenging activity		IC50	=	12300.0	nM	PMID[481783]

☑ 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 NPC89131 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	384
0.1-0.2	1750
0.2-0.3	4159
0.3-0.4	9781
0.4-0.5	8390
0.5-0.6	3998
0.6-0.7	5600
0.7-0.8	5835
0.8-0.85	1967
0.85-0.9	789
0.9-0.95	42
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC300680
0.9264	High Similarity	NPC247964
0.9193	High Similarity	NPC29411
0.9146	High Similarity	NPC47386
0.9091	High Similarity	NPC261471
0.908	High Similarity	NPC86477
0.9068	High Similarity	NPC312056
0.9068	High Similarity	NPC84515
0.9006	High Similarity	NPC188486
0.8982	High Similarity	NPC164384
0.8976	High Similarity	NPC37606
0.897	High Similarity	NPC218533
0.897	High Similarity	NPC78830
0.8951	High Similarity	NPC272722
0.8929	High Similarity	NPC297807
0.8896	High Similarity	NPC133065
0.8882	High Similarity	NPC16935
0.8882	High Similarity	NPC196879
0.8862	High Similarity	NPC473834
0.8862	High Similarity	NPC310794
0.8861	High Similarity	NPC267091
0.8855	High Similarity	NPC131866
0.8848	High Similarity	NPC186392
0.8848	High Similarity	NPC50394
0.8848	High Similarity	NPC247973
0.8841	High Similarity	NPC39306
0.8841	High Similarity	NPC291110
0.8841	High Similarity	NPC36320
0.8841	High Similarity	NPC45449
0.8824	High Similarity	NPC47883
0.8824	High Similarity	NPC475996
0.8824	High Similarity	NPC97523
0.8817	High Similarity	NPC98546
0.8812	High Similarity	NPC80489
0.8805	High Similarity	NPC60972
0.8805	High Similarity	NPC39732
0.8802	High Similarity	NPC174700
0.8797	High Similarity	NPC243891
0.8788	High Similarity	NPC277480
0.878	High Similarity	NPC1755
0.878	High Similarity	NPC263092
0.878	High Similarity	NPC59295
0.878	High Similarity	NPC39305
0.878	High Similarity	NPC1706
0.8758	High Similarity	NPC472461
0.8758	High Similarity	NPC45131
0.875	High Similarity	NPC476640
0.875	High Similarity	NPC82217
0.875	High Similarity	NPC216842
0.8736	High Similarity	NPC295436
0.8727	High Similarity	NPC37183
0.8726	High Similarity	NPC472969
0.872	High Similarity	NPC144843
0.872	High Similarity	NPC238995
0.8712	High Similarity	NPC260296
0.8712	High Similarity	NPC115432
0.8712	High Similarity	NPC130955
0.8704	High Similarity	NPC299520
0.8704	High Similarity	NPC129684
0.8698	High Similarity	NPC287243
0.8696	High Similarity	NPC208197
0.8696	High Similarity	NPC167815
0.8696	High Similarity	NPC128863
0.8696	High Similarity	NPC4455
0.8696	High Similarity	NPC146165
0.8696	High Similarity	NPC92659
0.8696	High Similarity	NPC196439
0.8696	High Similarity	NPC227325
0.8696	High Similarity	NPC2476
0.8696	High Similarity	NPC280339
0.8696	High Similarity	NPC20830
0.8696	High Similarity	NPC183597
0.8696	High Similarity	NPC256612
0.8696	High Similarity	NPC163780
0.8696	High Similarity	NPC201136
0.8696	High Similarity	NPC138360
0.8696	High Similarity	NPC50715
0.8696	High Similarity	NPC268008
0.869	High Similarity	NPC54098
0.869	High Similarity	NPC230619
0.8683	High Similarity	NPC280493
0.8671	High Similarity	NPC98809
0.8671	High Similarity	NPC476394
0.8667	High Similarity	NPC173729
0.8667	High Similarity	NPC272750
0.8667	High Similarity	NPC223006
0.8667	High Similarity	NPC477689
0.8667	High Similarity	NPC134047
0.8659	High Similarity	NPC469889
0.865	High Similarity	NPC244750
0.8647	High Similarity	NPC8127
0.8647	High Similarity	NPC49667
0.8647	High Similarity	NPC24258
0.8642	High Similarity	NPC265511
0.8642	High Similarity	NPC54928
0.8642	High Similarity	NPC472455
0.8639	High Similarity	NPC233956
0.8636	High Similarity	NPC326065
0.8634	High Similarity	NPC287504
0.8634	High Similarity	NPC231018
0.8634	High Similarity	NPC274327
0.8634	High Similarity	NPC47781
0.8634	High Similarity	NPC75279
0.8634	High Similarity	NPC160951
0.8634	High Similarity	NPC69394
0.8634	High Similarity	NPC183878
0.8634	High Similarity	NPC255350
0.8634	High Similarity	NPC22519
0.8634	High Similarity	NPC25127
0.8634	High Similarity	NPC176775
0.8634	High Similarity	NPC145379
0.8634	High Similarity	NPC276409
0.8634	High Similarity	NPC250822
0.8631	High Similarity	NPC476641
0.8631	High Similarity	NPC120220
0.8625	High Similarity	NPC75695
0.8623	High Similarity	NPC470704
0.8621	High Similarity	NPC248315
0.8616	High Similarity	NPC183950
0.8616	High Similarity	NPC52005
0.8616	High Similarity	NPC287101
0.8616	High Similarity	NPC137062
0.8616	High Similarity	NPC223579
0.8616	High Similarity	NPC177298
0.8616	High Similarity	NPC48479
0.8614	High Similarity	NPC38914
0.8614	High Similarity	NPC88243
0.8614	High Similarity	NPC204088
0.8614	High Similarity	NPC472277
0.8614	High Similarity	NPC259007
0.8614	High Similarity	NPC329215
0.8613	High Similarity	NPC154527
0.8606	High Similarity	NPC81679
0.8606	High Similarity	NPC144557
0.8606	High Similarity	NPC76687
0.8598	High Similarity	NPC47623
0.8598	High Similarity	NPC328102
0.8598	High Similarity	NPC476980
0.8598	High Similarity	NPC472961
0.8598	High Similarity	NPC53889
0.8598	High Similarity	NPC472962
0.8589	High Similarity	NPC224137
0.8589	High Similarity	NPC75215
0.8589	High Similarity	NPC35598
0.8589	High Similarity	NPC189179
0.8589	High Similarity	NPC227192
0.8589	High Similarity	NPC93376
0.8589	High Similarity	NPC222689
0.8588	High Similarity	NPC290304
0.8588	High Similarity	NPC227906
0.8588	High Similarity	NPC236327
0.858	High Similarity	NPC255807
0.858	High Similarity	NPC57674
0.858	High Similarity	NPC213622
0.858	High Similarity	NPC230149
0.858	High Similarity	NPC99199
0.858	High Similarity	NPC168247
0.858	High Similarity	NPC117992
0.858	High Similarity	NPC31018
0.858	High Similarity	NPC152951
0.858	High Similarity	NPC158226
0.858	High Similarity	NPC472584
0.858	High Similarity	NPC472280
0.858	High Similarity	NPC234255
0.8571	High Similarity	NPC295646
0.8571	High Similarity	NPC25270
0.8571	High Similarity	NPC187498
0.8571	High Similarity	NPC156222
0.8571	High Similarity	NPC471982
0.8571	High Similarity	NPC257648
0.8571	High Similarity	NPC289968
0.8571	High Similarity	NPC212678
0.8571	High Similarity	NPC41326
0.8571	High Similarity	NPC120163
0.8571	High Similarity	NPC142540
0.8571	High Similarity	NPC83508
0.8571	High Similarity	NPC477231
0.8571	High Similarity	NPC100887
0.8571	High Similarity	NPC301323
0.8571	High Similarity	NPC293183
0.8571	High Similarity	NPC288813
0.8571	High Similarity	NPC275722
0.8571	High Similarity	NPC241498
0.8571	High Similarity	NPC275836
0.8571	High Similarity	NPC239128
0.8571	High Similarity	NPC125300
0.8571	High Similarity	NPC188203
0.8571	High Similarity	NPC198826
0.8571	High Similarity	NPC256283
0.8571	High Similarity	NPC222830
0.8571	High Similarity	NPC57030
0.8571	High Similarity	NPC162313
0.8571	High Similarity	NPC207624
0.8571	High Similarity	NPC71334
0.8571	High Similarity	NPC55205
0.8571	High Similarity	NPC131624
0.8571	High Similarity	NPC247136
0.8571	High Similarity	NPC202470
0.8563	High Similarity	NPC226725
0.8563	High Similarity	NPC235610

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 NPC89131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	930
0.2-0.3	1730
0.3-0.4	2641
0.4-0.5	1908
0.5-0.6	1069
0.6-0.7	362
0.7-0.8	118
0.8-0.85	29
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8634	High Similarity	NPD2801	Approved
0.8623	High Similarity	NPD3818	Discontinued
0.8528	High Similarity	NPD3882	Suspended
0.8494	Intermediate Similarity	NPD6232	Discontinued
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD7473	Discontinued
0.8443	Intermediate Similarity	NPD3926	Phase 2
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1511	Approved
0.8293	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6166	Phase 2
0.8284	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD2344	Approved
0.8199	Intermediate Similarity	NPD1512	Approved
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8161	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD3749	Approved
0.814	Intermediate Similarity	NPD7054	Approved
0.8103	Intermediate Similarity	NPD6559	Discontinued
0.8095	Intermediate Similarity	NPD919	Approved
0.8092	Intermediate Similarity	NPD7074	Phase 3
0.8092	Intermediate Similarity	NPD7472	Approved
0.8075	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2309	Approved
0.8047	Intermediate Similarity	NPD5494	Approved
0.8036	Intermediate Similarity	NPD7075	Discontinued
0.7964	Intermediate Similarity	NPD7819	Suspended
0.7943	Intermediate Similarity	NPD6797	Phase 2
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD5844	Phase 1
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6801	Discontinued
0.7898	Intermediate Similarity	NPD7251	Discontinued
0.7895	Intermediate Similarity	NPD1247	Approved
0.7892	Intermediate Similarity	NPD4380	Phase 2
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD4628	Phase 3
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7808	Phase 3
0.7853	Intermediate Similarity	NPD6799	Approved
0.7844	Intermediate Similarity	NPD7411	Suspended
0.7834	Intermediate Similarity	NPD447	Suspended
0.7831	Intermediate Similarity	NPD3226	Approved
0.7818	Intermediate Similarity	NPD920	Approved
0.7811	Intermediate Similarity	NPD5402	Approved
0.7805	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7685	Pre-registration
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD8434	Phase 2
0.7759	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2935	Discontinued
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7716	Intermediate Similarity	NPD1243	Approved
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.7674	Intermediate Similarity	NPD6234	Discontinued
0.7669	Intermediate Similarity	NPD3750	Approved
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1549	Phase 2
0.764	Intermediate Similarity	NPD2796	Approved
0.7622	Intermediate Similarity	NPD6190	Approved
0.7605	Intermediate Similarity	NPD5403	Approved
0.7602	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD2533	Approved
0.759	Intermediate Similarity	NPD2534	Approved
0.7586	Intermediate Similarity	NPD6959	Discontinued
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD943	Approved
0.7547	Intermediate Similarity	NPD1240	Approved
0.7532	Intermediate Similarity	NPD3764	Approved
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2800	Approved
0.75	Intermediate Similarity	NPD2296	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.7485	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.7472	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD4966	Approved
0.7457	Intermediate Similarity	NPD4965	Approved
0.7453	Intermediate Similarity	NPD1607	Approved
0.7452	Intermediate Similarity	NPD9494	Approved
0.7443	Intermediate Similarity	NPD6808	Phase 2
0.7419	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8313	Approved
0.7418	Intermediate Similarity	NPD8312	Approved
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1471	Phase 3
0.7374	Intermediate Similarity	NPD7228	Approved
0.7362	Intermediate Similarity	NPD3748	Approved
0.7355	Intermediate Similarity	NPD1608	Approved
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7326	Intermediate Similarity	NPD6386	Approved
0.7326	Intermediate Similarity	NPD6385	Approved
0.7325	Intermediate Similarity	NPD1203	Approved
0.7317	Intermediate Similarity	NPD1551	Phase 2
0.7312	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD5242	Approved
0.7296	Intermediate Similarity	NPD6832	Phase 2
0.7283	Intermediate Similarity	NPD6280	Approved
0.7283	Intermediate Similarity	NPD6279	Approved
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7033	Discontinued
0.7251	Intermediate Similarity	NPD1653	Approved
0.725	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD4287	Approved
0.7215	Intermediate Similarity	NPD2797	Approved
0.7205	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7188	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2798	Approved
0.7169	Intermediate Similarity	NPD7266	Discontinued
0.7161	Intermediate Similarity	NPD17	Approved
0.716	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7134	Intermediate Similarity	NPD9717	Approved
0.7125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8151	Discontinued
0.712	Intermediate Similarity	NPD7038	Approved
0.712	Intermediate Similarity	NPD7039	Approved
0.7117	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1613	Approved
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5408	Approved
0.7108	Intermediate Similarity	NPD5405	Approved
0.7108	Intermediate Similarity	NPD5404	Approved
0.7108	Intermediate Similarity	NPD5406	Approved
0.7101	Intermediate Similarity	NPD2354	Approved
0.7099	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5536	Phase 2
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7056	Intermediate Similarity	NPD5710	Approved
0.7056	Intermediate Similarity	NPD5711	Approved
0.7056	Intermediate Similarity	NPD3787	Discontinued
0.7048	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8455	Phase 2
0.7045	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5761	Phase 2
0.7045	Intermediate Similarity	NPD5760	Phase 2
0.7041	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8166	Discontinued
0.7041	Intermediate Similarity	NPD7435	Discontinued
0.7037	Intermediate Similarity	NPD7095	Approved
0.7035	Intermediate Similarity	NPD6273	Approved
0.7032	Intermediate Similarity	NPD9545	Approved
0.7025	Intermediate Similarity	NPD3972	Approved
0.7018	Intermediate Similarity	NPD7390	Discontinued
0.7011	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD3266	Approved
0.6995	Remote Similarity	NPD2163	Approved
0.6994	Remote Similarity	NPD411	Approved
0.6978	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6778	Approved
0.6974	Remote Similarity	NPD6776	Approved
0.6974	Remote Similarity	NPD6782	Approved
0.6974	Remote Similarity	NPD6780	Approved
0.6974	Remote Similarity	NPD6777	Approved
0.6974	Remote Similarity	NPD6779	Approved
0.6974	Remote Similarity	NPD6781	Approved
0.6965	Remote Similarity	NPD7783	Phase 2
0.6965	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7003	Approved
0.6937	Remote Similarity	NPD3225	Approved
0.6937	Remote Similarity	NPD1876	Approved
0.6935	Remote Similarity	NPD7240	Approved
0.6928	Remote Similarity	NPD6651	Approved
0.6927	Remote Similarity	NPD6971	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