NPASS Compound

Structure

NPC338131 OpenBabel07101718232D 25 27 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -2.5981 -2.5000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 1 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 -0.0000 -1.0000 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 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 0.8660 -1.5000 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 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 21 2 0 0 0 0 13 9 1 6 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.11
Volume:	337.291
LogP:	2.573
LogD:	2.75
LogS:	-3.903
# Rotatable Bonds:	4
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.879
Synthetic Accessibility Score:	2.883
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.709
MDCK Permeability:	2.8230953830643557e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	83.42456817626953%
Volume Distribution (VD):	0.829
Pgp-substrate:	19.55341148376465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.548
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.633
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.389
CYP2D6-substrate:	0.745
CYP3A4-inhibitor:	0.782
CYP3A4-substrate:	0.497

ADMET: Excretion

Clearance (CL):	13.142
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.819
Skin Sensitization:	0.875
Carcinogencity:	0.149
Eye Corrosion:	0.006
Eye Irritation:	0.608
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC338131

Natural Product ID:	NPC338131
*Common Name:**	3',4',5'-Trimethoxyflavanone
IUPAC Name:	(2S)-5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	CTALFFOVOLJORS-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C18H18O7/c1-22-15-4-9(5-16(23-2)18(15)24-3)13-8-12(21)17-11(20)6-10(19)7-14(17)25-13/h4-7,13,19-20H,8H2,1-3H3/t13-/m0/s1
SMILES:	COc1c(OC)cc(cc1OC)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581354
PubChem CID:	40484424
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-O-methylated flavonoids

*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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[455213]

☑ 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 NPC338131 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	389
0.1-0.2	1609
0.2-0.3	4256
0.3-0.4	10144
0.4-0.5	7852
0.5-0.6	3317
0.6-0.7	4708
0.7-0.8	5434
0.8-0.85	2651
0.85-0.9	1821
0.9-0.95	444
0.95-1	72

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC18727
0.9728	High Similarity	NPC226025
0.9728	High Similarity	NPC477503
0.9728	High Similarity	NPC45849
0.9728	High Similarity	NPC200761
0.9728	High Similarity	NPC470327
0.9728	High Similarity	NPC37392
0.9726	High Similarity	NPC302950
0.9726	High Similarity	NPC219582
0.9726	High Similarity	NPC236637
0.9662	High Similarity	NPC195796
0.9662	High Similarity	NPC470328
0.9662	High Similarity	NPC209614
0.9662	High Similarity	NPC291878
0.9662	High Similarity	NPC472626
0.9662	High Similarity	NPC278778
0.9662	High Similarity	NPC35038
0.9653	High Similarity	NPC33265
0.9653	High Similarity	NPC62536
0.9597	High Similarity	NPC471515
0.9597	High Similarity	NPC472598
0.9597	High Similarity	NPC473272
0.9597	High Similarity	NPC474836
0.9597	High Similarity	NPC475267
0.9597	High Similarity	NPC162869
0.9597	High Similarity	NPC474208
0.9597	High Similarity	NPC223787
0.9597	High Similarity	NPC284820
0.9597	High Similarity	NPC48208
0.9597	High Similarity	NPC474055
0.9597	High Similarity	NPC471479
0.9597	High Similarity	NPC108456
0.9597	High Similarity	NPC156057
0.9597	High Similarity	NPC291508
0.9597	High Similarity	NPC27337
0.9595	High Similarity	NPC472909
0.9595	High Similarity	NPC255807
0.9595	High Similarity	NPC31018
0.9592	High Similarity	NPC106976
0.9592	High Similarity	NPC472912
0.9586	High Similarity	NPC195202
0.9533	High Similarity	NPC473990
0.953	High Similarity	NPC255106
0.953	High Similarity	NPC471500
0.953	High Similarity	NPC250922
0.953	High Similarity	NPC13858
0.953	High Similarity	NPC320825
0.953	High Similarity	NPC326037
0.953	High Similarity	NPC235165
0.9527	High Similarity	NPC298692
0.9527	High Similarity	NPC213896
0.9527	High Similarity	NPC192083
0.9527	High Similarity	NPC472915
0.9527	High Similarity	NPC280937
0.9527	High Similarity	NPC74924
0.9524	High Similarity	NPC117579
0.9521	High Similarity	NPC328119
0.9521	High Similarity	NPC48479
0.9521	High Similarity	NPC177298
0.9517	High Similarity	NPC12200
0.951	High Similarity	NPC73028
0.947	High Similarity	NPC470326
0.947	High Similarity	NPC119209
0.947	High Similarity	NPC36217
0.947	High Similarity	NPC287328
0.947	High Similarity	NPC472624
0.947	High Similarity	NPC174953
0.947	High Similarity	NPC472631
0.947	High Similarity	NPC299436
0.947	High Similarity	NPC475784
0.947	High Similarity	NPC472630
0.947	High Similarity	NPC192686
0.947	High Similarity	NPC118256
0.947	High Similarity	NPC282009
0.9467	High Similarity	NPC99597
0.9467	High Similarity	NPC245758
0.9467	High Similarity	NPC222814
0.9467	High Similarity	NPC472911
0.9467	High Similarity	NPC67876
0.9467	High Similarity	NPC472910
0.9467	High Similarity	NPC181960
0.9467	High Similarity	NPC210084
0.9467	High Similarity	NPC52530
0.9467	High Similarity	NPC469584
0.9467	High Similarity	NPC129684
0.9467	High Similarity	NPC472913
0.9467	High Similarity	NPC96167
0.9467	High Similarity	NPC472914
0.9467	High Similarity	NPC299520
0.9463	High Similarity	NPC67396
0.9463	High Similarity	NPC321779
0.9459	High Similarity	NPC471982
0.9459	High Similarity	NPC477231
0.9459	High Similarity	NPC260979
0.9459	High Similarity	NPC257648
0.9456	High Similarity	NPC179183
0.9456	High Similarity	NPC50728
0.9456	High Similarity	NPC219330
0.9456	High Similarity	NPC166753
0.9452	High Similarity	NPC321011
0.9452	High Similarity	NPC120464
0.9452	High Similarity	NPC476342
0.9452	High Similarity	NPC188679
0.9452	High Similarity	NPC294852
0.9448	High Similarity	NPC187282
0.9448	High Similarity	NPC24136
0.9448	High Similarity	NPC290133
0.9408	High Similarity	NPC472634
0.9408	High Similarity	NPC471499
0.9408	High Similarity	NPC471210
0.9408	High Similarity	NPC26326
0.9408	High Similarity	NPC471211
0.9408	High Similarity	NPC134783
0.9408	High Similarity	NPC158188
0.9408	High Similarity	NPC472632
0.9408	High Similarity	NPC474038
0.9408	High Similarity	NPC471212
0.9408	High Similarity	NPC474186
0.9404	High Similarity	NPC250214
0.9404	High Similarity	NPC152904
0.9404	High Similarity	NPC95936
0.9404	High Similarity	NPC22192
0.94	High Similarity	NPC24640
0.94	High Similarity	NPC472916
0.9396	High Similarity	NPC469550
0.9392	High Similarity	NPC31363
0.9392	High Similarity	NPC208043
0.9392	High Similarity	NPC308451
0.9392	High Similarity	NPC236769
0.9392	High Similarity	NPC226973
0.9392	High Similarity	NPC76376
0.9392	High Similarity	NPC149614
0.9388	High Similarity	NPC287101
0.9388	High Similarity	NPC52005
0.9388	High Similarity	NPC1612
0.9388	High Similarity	NPC223579
0.9388	High Similarity	NPC159103
0.9388	High Similarity	NPC137062
0.9388	High Similarity	NPC183959
0.9388	High Similarity	NPC183950
0.9371	High Similarity	NPC182421
0.9346	High Similarity	NPC474034
0.9346	High Similarity	NPC474033
0.9346	High Similarity	NPC201800
0.9346	High Similarity	NPC472635
0.9346	High Similarity	NPC476247
0.9346	High Similarity	NPC472964
0.9342	High Similarity	NPC472902
0.9342	High Similarity	NPC470183
0.9342	High Similarity	NPC101731
0.9342	High Similarity	NPC475886
0.9342	High Similarity	NPC263449
0.9342	High Similarity	NPC474287
0.9338	High Similarity	NPC78225
0.9338	High Similarity	NPC217677
0.9338	High Similarity	NPC300727
0.9338	High Similarity	NPC36852
0.9338	High Similarity	NPC262286
0.9338	High Similarity	NPC471209
0.9338	High Similarity	NPC52889
0.9338	High Similarity	NPC165977
0.9338	High Similarity	NPC183851
0.9338	High Similarity	NPC63454
0.9338	High Similarity	NPC470402
0.9338	High Similarity	NPC241904
0.9333	High Similarity	NPC2928
0.9333	High Similarity	NPC168247
0.9333	High Similarity	NPC152951
0.9333	High Similarity	NPC230149
0.9333	High Similarity	NPC57674
0.9333	High Similarity	NPC117992
0.9333	High Similarity	NPC213622
0.9329	High Similarity	NPC120537
0.9329	High Similarity	NPC39732
0.9329	High Similarity	NPC260491
0.9329	High Similarity	NPC19721
0.9329	High Similarity	NPC199100
0.9329	High Similarity	NPC60972
0.9329	High Similarity	NPC240476
0.9329	High Similarity	NPC101996
0.9329	High Similarity	NPC61506
0.9329	High Similarity	NPC246162
0.9329	High Similarity	NPC180234
0.9329	High Similarity	NPC9743
0.9329	High Similarity	NPC36835
0.9324	High Similarity	NPC306821
0.9324	High Similarity	NPC29231
0.9324	High Similarity	NPC239363
0.932	High Similarity	NPC261548
0.932	High Similarity	NPC3036
0.9315	High Similarity	NPC12377
0.931	High Similarity	NPC293201
0.9306	High Similarity	NPC29536
0.9301	High Similarity	NPC140890
0.9286	High Similarity	NPC474240
0.9286	High Similarity	NPC475985
0.9286	High Similarity	NPC197168
0.9286	High Similarity	NPC124038
0.9286	High Similarity	NPC186686
0.9286	High Similarity	NPC273959

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 NPC338131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	942
0.2-0.3	1792
0.3-0.4	2597
0.4-0.5	1729
0.5-0.6	1023
0.6-0.7	522
0.7-0.8	130
0.8-0.85	43
0.85-0.9	15
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9726	High Similarity	NPD1934	Approved
0.9527	High Similarity	NPD2393	Clinical (unspecified phase)
0.9267	High Similarity	NPD2801	Approved
0.9226	High Similarity	NPD6168	Clinical (unspecified phase)
0.9226	High Similarity	NPD6167	Clinical (unspecified phase)
0.9226	High Similarity	NPD6166	Phase 2
0.9048	High Similarity	NPD1511	Approved
0.9028	High Similarity	NPD1552	Clinical (unspecified phase)
0.9028	High Similarity	NPD1550	Clinical (unspecified phase)
0.902	High Similarity	NPD3882	Suspended
0.8994	High Similarity	NPD7074	Phase 3
0.8966	High Similarity	NPD1549	Phase 2
0.8954	High Similarity	NPD3817	Phase 2
0.8931	High Similarity	NPD7054	Approved
0.8926	High Similarity	NPD1512	Approved
0.8896	High Similarity	NPD4868	Clinical (unspecified phase)
0.8875	High Similarity	NPD7472	Approved
0.8868	High Similarity	NPD3818	Discontinued
0.8859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8846	High Similarity	NPD5494	Approved
0.8816	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD7075	Discontinued
0.8718	High Similarity	NPD4381	Clinical (unspecified phase)
0.8712	High Similarity	NPD7808	Phase 3
0.8704	High Similarity	NPD6797	Phase 2
0.8699	High Similarity	NPD2796	Approved
0.865	High Similarity	NPD7251	Discontinued
0.8645	High Similarity	NPD7096	Clinical (unspecified phase)
0.863	High Similarity	NPD1510	Phase 2
0.8598	High Similarity	NPD4338	Clinical (unspecified phase)
0.859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8553	High Similarity	NPD6959	Discontinued
0.8526	High Similarity	NPD7819	Suspended
0.85	High Similarity	NPD6232	Discontinued
0.8483	Intermediate Similarity	NPD1240	Approved
0.8466	Intermediate Similarity	NPD5844	Phase 1
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8421	Intermediate Similarity	NPD6799	Approved
0.8397	Intermediate Similarity	NPD7411	Suspended
0.8367	Intermediate Similarity	NPD1607	Approved
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8291	Intermediate Similarity	NPD1465	Phase 2
0.8231	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1613	Approved
0.8217	Intermediate Similarity	NPD6599	Discontinued
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6559	Discontinued
0.8138	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5402	Approved
0.811	Intermediate Similarity	NPD3926	Phase 2
0.8108	Intermediate Similarity	NPD943	Approved
0.8098	Intermediate Similarity	NPD1247	Approved
0.8086	Intermediate Similarity	NPD919	Approved
0.8082	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2800	Approved
0.8027	Intermediate Similarity	NPD3027	Phase 3
0.8025	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7973	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD6100	Approved
0.7961	Intermediate Similarity	NPD6099	Approved
0.7961	Intermediate Similarity	NPD2935	Discontinued
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7933	Intermediate Similarity	NPD447	Suspended
0.7922	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3749	Approved
0.7898	Intermediate Similarity	NPD5401	Approved
0.7871	Intermediate Similarity	NPD4628	Phase 3
0.7834	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1933	Approved
0.7778	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7763	Intermediate Similarity	NPD6651	Approved
0.7758	Intermediate Similarity	NPD6234	Discontinued
0.7744	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD4967	Phase 2
0.7744	Intermediate Similarity	NPD4965	Approved
0.7724	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD1243	Approved
0.7688	Intermediate Similarity	NPD920	Approved
0.7679	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2344	Approved
0.7662	Intermediate Similarity	NPD3748	Approved
0.7662	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1653	Approved
0.763	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3787	Discontinued
0.7616	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5953	Discontinued
0.761	Intermediate Similarity	NPD7390	Discontinued
0.7603	Intermediate Similarity	NPD1610	Phase 2
0.7602	Intermediate Similarity	NPD7286	Phase 2
0.7593	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD5353	Approved
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2346	Discontinued
0.7562	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7548	Intermediate Similarity	NPD7033	Discontinued
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7228	Approved
0.7533	Intermediate Similarity	NPD9494	Approved
0.7517	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD5711	Approved
0.7515	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6190	Approved
0.7484	Intermediate Similarity	NPD2309	Approved
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7471	Intermediate Similarity	NPD5242	Approved
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.7417	Intermediate Similarity	NPD2861	Phase 2
0.7394	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD6798	Discontinued
0.7386	Intermediate Similarity	NPD3268	Approved
0.7386	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD4749	Approved
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7358	Intermediate Similarity	NPD2654	Approved
0.7351	Intermediate Similarity	NPD2798	Approved
0.7349	Intermediate Similarity	NPD6844	Discontinued
0.7326	Intermediate Similarity	NPD2403	Approved
0.7322	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4625	Phase 3
0.7315	Intermediate Similarity	NPD1608	Approved
0.7315	Intermediate Similarity	NPD9717	Approved
0.7303	Intermediate Similarity	NPD3018	Phase 2
0.7289	Intermediate Similarity	NPD6386	Approved
0.7289	Intermediate Similarity	NPD6385	Approved
0.7285	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8151	Discontinued
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.726	Intermediate Similarity	NPD5536	Phase 2
0.725	Intermediate Similarity	NPD1652	Phase 2
0.7249	Intermediate Similarity	NPD7584	Approved
0.7248	Intermediate Similarity	NPD422	Phase 1
0.7244	Intermediate Similarity	NPD6355	Discontinued
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7209	Intermediate Similarity	NPD7229	Phase 3
0.7205	Intermediate Similarity	NPD4110	Phase 3
0.7205	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6776	Approved
0.7204	Intermediate Similarity	NPD6781	Approved
0.7204	Intermediate Similarity	NPD6782	Approved
0.7204	Intermediate Similarity	NPD6778	Approved
0.7204	Intermediate Similarity	NPD6780	Approved
0.7204	Intermediate Similarity	NPD6777	Approved
0.7204	Intermediate Similarity	NPD6779	Approved
0.72	Intermediate Similarity	NPD9269	Phase 2
0.7188	Intermediate Similarity	NPD2424	Discontinued
0.7178	Intermediate Similarity	NPD4357	Discontinued
0.7175	Intermediate Similarity	NPD7038	Approved
0.7175	Intermediate Similarity	NPD7039	Approved
0.7175	Intermediate Similarity	NPD7240	Approved
0.7174	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4361	Phase 2
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7167	Intermediate Similarity	NPD8150	Discontinued
0.7162	Intermediate Similarity	NPD9268	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD2983	Phase 2
0.7152	Intermediate Similarity	NPD2982	Phase 2
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD4661	Approved
0.7134	Intermediate Similarity	NPD4662	Approved
0.7133	Intermediate Similarity	NPD1201	Approved
0.7126	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7266	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