NPASS Compound

Structure

NPC471209 OpenBabel07101718182D 32 35 0 0 1 0 0 0 0 0999 V2000 2.7285 -2.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6945 -0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 -0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 0.0517 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2802 -0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 0.7588 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 0.5000 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 -1.7321 -0.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9873 -1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9533 -1.8801 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 25 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 15 20 1 0 0 0 0 15 23 2 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 22 1 0 0 0 0 18 28 2 0 0 0 0 19 14 1 6 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 22 2 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.2
Volume:	449.807
LogP:	3.933
LogD:	2.938
LogS:	-4.005
# Rotatable Bonds:	5
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	3.88
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	1.8994980564457364e-05
Pgp-inhibitor:	0.358
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.86337280273438%
Volume Distribution (VD):	0.554
Pgp-substrate:	3.8117971420288086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.344
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.627
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.474
CYP2D6-substrate:	0.418
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	14.254
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.761
AMES Toxicity:	0.263
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.14
Skin Sensitization:	0.858
Carcinogencity:	0.544
Eye Corrosion:	0.003
Eye Irritation:	0.448
Respiratory Toxicity:	0.701

Download Data

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

Natural Product: NPC471209

Natural Product ID:	NPC471209
*Common Name:**	(8S)-8-(3,4-Dihydroxyphenyl)-5-Hydroxy-2-(4-Hydroxy-4-Methylpentyl)-2-Methyl-3,4,7,8-Tetrahydropyrano[3,2-G]Chromen-6-One
IUPAC Name:	(8S)-8-(3,4-dihydroxyphenyl)-5-hydroxy-2-(4-hydroxy-4-methylpentyl)-2-methyl-3,4,7,8-tetrahydropyrano[3,2-g]chromen-6-one
Synonyms:
Standard InCHIKey:	CMJDNOOYGNOVCM-UBDBMELISA-N
Standard InCHI:	InChI=1S/C25H30O7/c1-24(2,30)8-4-9-25(3)10-7-15-20(32-25)13-21-22(23(15)29)18(28)12-19(31-21)14-5-6-16(26)17(27)11-14/h5-6,11,13,19,26-27,29-30H,4,7-10,12H2,1-3H3/t19-,25?/m0/s1
SMILES:	O=C1C[C@H](Oc2c1c(O)c1c(c2)OC(CC1)(C)CCCC(O)(C)C)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2387711
PubChem CID:	71659627
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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	2
Ki	2

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	=	8400.0	nM	PMID[476796]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Ki	=	12500.0	nM	PMID[476796]
NPT2	Others	Unspecified		Ki	=	4800.0	nM	PMID[476795]
NPT2	Others	Unspecified		IC50	=	6200.0	nM	PMID[476795]

☑ 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 NPC471209 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	402
0.1-0.2	1594
0.2-0.3	4022
0.3-0.4	9890
0.4-0.5	8334
0.5-0.6	3357
0.6-0.7	4820
0.7-0.8	5523
0.8-0.85	2827
0.85-0.9	1464
0.9-0.95	403
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
0.9803	High Similarity	NPC471210
0.9803	High Similarity	NPC472632
0.9799	High Similarity	NPC192083
0.9799	High Similarity	NPC213896
0.9799	High Similarity	NPC74924
0.9739	High Similarity	NPC474034
0.9739	High Similarity	NPC474033
0.9737	High Similarity	NPC118256
0.9737	High Similarity	NPC174953
0.9737	High Similarity	NPC119209
0.9737	High Similarity	NPC192686
0.9735	High Similarity	NPC27337
0.9733	High Similarity	NPC321779
0.9732	High Similarity	NPC106976
0.9673	High Similarity	NPC471212
0.9673	High Similarity	NPC134783
0.9673	High Similarity	NPC474038
0.9673	High Similarity	NPC471211
0.9671	High Similarity	NPC473990
0.9669	High Similarity	NPC195796
0.9669	High Similarity	NPC291878
0.9669	High Similarity	NPC278778
0.9669	High Similarity	NPC35038
0.9667	High Similarity	NPC298692
0.9613	High Similarity	NPC293319
0.9613	High Similarity	NPC62261
0.9608	High Similarity	NPC475784
0.9608	High Similarity	NPC472624
0.9605	High Similarity	NPC291508
0.9605	High Similarity	NPC472598
0.9605	High Similarity	NPC284820
0.9605	High Similarity	NPC474055
0.9605	High Similarity	NPC473272
0.9603	High Similarity	NPC470327
0.9603	High Similarity	NPC477503
0.9603	High Similarity	NPC45849
0.9603	High Similarity	NPC200761
0.9551	High Similarity	NPC471213
0.9548	High Similarity	NPC186686
0.9548	High Similarity	NPC472625
0.9545	High Similarity	NPC472634
0.9545	High Similarity	NPC142252
0.9545	High Similarity	NPC26326
0.9542	High Similarity	NPC210459
0.9542	High Similarity	NPC53545
0.9542	High Similarity	NPC117418
0.9542	High Similarity	NPC22192
0.9539	High Similarity	NPC24640
0.9539	High Similarity	NPC470328
0.9539	High Similarity	NPC472626
0.9539	High Similarity	NPC282307
0.9539	High Similarity	NPC209614
0.9539	High Similarity	NPC170026
0.9536	High Similarity	NPC18727
0.9536	High Similarity	NPC170492
0.9484	High Similarity	NPC472635
0.9484	High Similarity	NPC476247
0.9484	High Similarity	NPC194427
0.9484	High Similarity	NPC474150
0.9484	High Similarity	NPC474162
0.9481	High Similarity	NPC36217
0.9481	High Similarity	NPC472630
0.9481	High Similarity	NPC321399
0.9481	High Similarity	NPC472631
0.9481	High Similarity	NPC328102
0.9481	High Similarity	NPC282009
0.9481	High Similarity	NPC287328
0.9477	High Similarity	NPC52889
0.9477	High Similarity	NPC223787
0.9474	High Similarity	NPC226025
0.9474	High Similarity	NPC67396
0.947	High Similarity	NPC475790
0.947	High Similarity	NPC219582
0.947	High Similarity	NPC302950
0.947	High Similarity	NPC236637
0.9467	High Similarity	NPC472633
0.9467	High Similarity	NPC88804
0.9467	High Similarity	NPC3825
0.9463	High Similarity	NPC294852
0.9463	High Similarity	NPC321011
0.9463	High Similarity	NPC188679
0.9427	High Similarity	NPC43319
0.9423	High Similarity	NPC124038
0.9419	High Similarity	NPC471499
0.9419	High Similarity	NPC173137
0.9419	High Similarity	NPC289771
0.9419	High Similarity	NPC198829
0.9416	High Similarity	NPC204879
0.9416	High Similarity	NPC469658
0.9416	High Similarity	NPC95936
0.9416	High Similarity	NPC85121
0.9416	High Similarity	NPC184755
0.9416	High Similarity	NPC250214
0.9416	High Similarity	NPC74178
0.9412	High Similarity	NPC276444
0.9412	High Similarity	NPC470600
0.9412	High Similarity	NPC471500
0.9412	High Similarity	NPC471985
0.9404	High Similarity	NPC474021
0.9404	High Similarity	NPC474023
0.9404	High Similarity	NPC154345
0.94	High Similarity	NPC183959
0.94	High Similarity	NPC1612
0.9367	High Similarity	NPC477154
0.9367	High Similarity	NPC117854
0.9367	High Similarity	NPC6588
0.9367	High Similarity	NPC218226
0.9367	High Similarity	NPC474024
0.9363	High Similarity	NPC300053
0.9363	High Similarity	NPC108433
0.9363	High Similarity	NPC224280
0.9359	High Similarity	NPC472448
0.9359	High Similarity	NPC220912
0.9359	High Similarity	NPC83922
0.9359	High Similarity	NPC201800
0.9355	High Similarity	NPC471976
0.9355	High Similarity	NPC204290
0.9355	High Similarity	NPC470326
0.9355	High Similarity	NPC476283
0.9355	High Similarity	NPC470183
0.9355	High Similarity	NPC28241
0.9351	High Similarity	NPC475267
0.9351	High Similarity	NPC471479
0.9351	High Similarity	NPC474681
0.9351	High Similarity	NPC218313
0.9351	High Similarity	NPC474208
0.9351	High Similarity	NPC237418
0.9351	High Similarity	NPC471515
0.9351	High Similarity	NPC474836
0.9351	High Similarity	NPC162869
0.9351	High Similarity	NPC67876
0.9351	High Similarity	NPC156057
0.9351	High Similarity	NPC78225
0.9351	High Similarity	NPC476630
0.9351	High Similarity	NPC218871
0.9351	High Similarity	NPC48208
0.9346	High Similarity	NPC152951
0.9346	High Similarity	NPC57674
0.9346	High Similarity	NPC477958
0.9346	High Similarity	NPC230149
0.9346	High Similarity	NPC256925
0.9346	High Similarity	NPC234255
0.9346	High Similarity	NPC113906
0.9346	High Similarity	NPC133392
0.9346	High Similarity	NPC117992
0.9346	High Similarity	NPC168247
0.9342	High Similarity	NPC157784
0.9342	High Similarity	NPC323626
0.9342	High Similarity	NPC63187
0.9342	High Similarity	NPC471982
0.9342	High Similarity	NPC324233
0.9342	High Similarity	NPC37684
0.9342	High Similarity	NPC472912
0.9338	High Similarity	NPC338131
0.9333	High Similarity	NPC3036
0.9329	High Similarity	NPC187282
0.9329	High Similarity	NPC290133
0.9329	High Similarity	NPC24136
0.9308	High Similarity	NPC288813
0.9304	High Similarity	NPC224851
0.9304	High Similarity	NPC120593
0.9299	High Similarity	NPC12461
0.9299	High Similarity	NPC236521
0.9299	High Similarity	NPC248638
0.9299	High Similarity	NPC152659
0.9299	High Similarity	NPC476295
0.9295	High Similarity	NPC158188
0.9295	High Similarity	NPC3629
0.9295	High Similarity	NPC29876
0.9295	High Similarity	NPC228383
0.9295	High Similarity	NPC167678
0.9295	High Similarity	NPC266314
0.9286	High Similarity	NPC78492
0.9286	High Similarity	NPC326037
0.9286	High Similarity	NPC68093
0.9286	High Similarity	NPC208152
0.9286	High Similarity	NPC13858
0.9286	High Similarity	NPC133970
0.9286	High Similarity	NPC5322
0.9286	High Similarity	NPC6633
0.9286	High Similarity	NPC472455
0.9286	High Similarity	NPC320825
0.9286	High Similarity	NPC191146
0.9286	High Similarity	NPC255106
0.9286	High Similarity	NPC235165
0.9281	High Similarity	NPC33051
0.9281	High Similarity	NPC7989
0.9281	High Similarity	NPC227337
0.9281	High Similarity	NPC223701
0.9281	High Similarity	NPC472583
0.9281	High Similarity	NPC141212
0.9281	High Similarity	NPC49402
0.9281	High Similarity	NPC273462
0.9281	High Similarity	NPC70433
0.9276	High Similarity	NPC244577
0.9276	High Similarity	NPC205046
0.9276	High Similarity	NPC472636
0.9276	High Similarity	NPC59162
0.9276	High Similarity	NPC472420
0.9276	High Similarity	NPC471676

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 NPC471209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	932
0.2-0.3	1714
0.3-0.4	2630
0.4-0.5	1799
0.5-0.6	1048
0.6-0.7	478
0.7-0.8	138
0.8-0.85	33
0.85-0.9	17
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9799	High Similarity	NPD2393	Clinical (unspecified phase)
0.947	High Similarity	NPD1934	Approved
0.9241	High Similarity	NPD6166	Phase 2
0.9241	High Similarity	NPD6168	Clinical (unspecified phase)
0.9241	High Similarity	NPD6167	Clinical (unspecified phase)
0.9067	High Similarity	NPD1511	Approved
0.9032	High Similarity	NPD2801	Approved
0.9012	High Similarity	NPD7074	Phase 3
0.8961	High Similarity	NPD4380	Phase 2
0.8951	High Similarity	NPD7054	Approved
0.8947	High Similarity	NPD1512	Approved
0.8896	High Similarity	NPD7472	Approved
0.8882	High Similarity	NPD4378	Clinical (unspecified phase)
0.8868	High Similarity	NPD5494	Approved
0.8841	High Similarity	NPD6797	Phase 2
0.8797	High Similarity	NPD4868	Clinical (unspecified phase)
0.8797	High Similarity	NPD3882	Suspended
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.8788	High Similarity	NPD7251	Discontinued
0.8742	High Similarity	NPD7075	Discontinued
0.8734	High Similarity	NPD8443	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8696	High Similarity	NPD6959	Discontinued
0.8671	High Similarity	NPD7096	Clinical (unspecified phase)
0.8659	High Similarity	NPD3818	Discontinued
0.8636	High Similarity	NPD7410	Clinical (unspecified phase)
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8623	High Similarity	NPD7808	Phase 3
0.8616	High Similarity	NPD3817	Phase 2
0.8606	High Similarity	NPD7804	Clinical (unspecified phase)
0.8553	High Similarity	NPD7819	Suspended
0.8544	High Similarity	NPD7411	Suspended
0.8512	High Similarity	NPD4338	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD2796	Approved
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8393	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD5844	Phase 1
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8267	Intermediate Similarity	NPD1240	Approved
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.8217	Intermediate Similarity	NPD6799	Approved
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD1613	Approved
0.8146	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD943	Approved
0.811	Intermediate Similarity	NPD7768	Phase 2
0.8049	Intermediate Similarity	NPD5402	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2800	Approved
0.7952	Intermediate Similarity	NPD3749	Approved
0.795	Intermediate Similarity	NPD5403	Approved
0.7937	Intermediate Similarity	NPD2532	Approved
0.7937	Intermediate Similarity	NPD2533	Approved
0.7937	Intermediate Similarity	NPD2534	Approved
0.7933	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1247	Approved
0.7911	Intermediate Similarity	NPD3750	Approved
0.7904	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD230	Phase 1
0.7829	Intermediate Similarity	NPD3027	Phase 3
0.7826	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6099	Approved
0.7771	Intermediate Similarity	NPD6100	Approved
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.773	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3926	Phase 2
0.7709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7657	Intermediate Similarity	NPD5953	Discontinued
0.7654	Intermediate Similarity	NPD7390	Discontinued
0.7647	Intermediate Similarity	NPD4908	Phase 1
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4363	Phase 3
0.7637	Intermediate Similarity	NPD4360	Phase 2
0.7636	Intermediate Similarity	NPD3226	Approved
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.7625	Intermediate Similarity	NPD1243	Approved
0.7622	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2346	Discontinued
0.7607	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3748	Approved
0.7595	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7586	Intermediate Similarity	NPD7228	Approved
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2313	Discontinued
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4625	Phase 3
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7474	Intermediate Similarity	NPD7584	Approved
0.747	Intermediate Similarity	NPD1653	Approved
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5710	Approved
0.7457	Intermediate Similarity	NPD5711	Approved
0.744	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7425	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7416	Intermediate Similarity	NPD7685	Pre-registration
0.7414	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1933	Approved
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7396	Intermediate Similarity	NPD37	Approved
0.7396	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7355	Intermediate Similarity	NPD9494	Approved
0.7353	Intermediate Similarity	NPD8455	Phase 2
0.7346	Intermediate Similarity	NPD2424	Discontinued
0.7338	Intermediate Similarity	NPD1203	Approved
0.732	Intermediate Similarity	NPD7783	Phase 2
0.732	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2309	Approved
0.7316	Intermediate Similarity	NPD7697	Approved
0.7316	Intermediate Similarity	NPD7696	Phase 3
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7316	Intermediate Similarity	NPD7698	Approved
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6844	Discontinued
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7254	Intermediate Similarity	NPD7701	Phase 2
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD4749	Approved
0.7195	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7179	Intermediate Similarity	NPD2798	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7167	Intermediate Similarity	NPD3823	Discontinued
0.7166	Intermediate Similarity	NPD6535	Approved
0.7166	Intermediate Similarity	NPD6534	Approved
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7127	Intermediate Similarity	NPD7240	Approved
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.7119	Intermediate Similarity	NPD5242	Approved
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD5408	Approved
0.7115	Intermediate Similarity	NPD2797	Approved
0.7111	Intermediate Similarity	NPD1729	Discontinued
0.711	Intermediate Similarity	NPD5353	Approved
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1652	Phase 2

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