NPASS Compound

Structure

CID321779 OpenBabel06191716162D 32 34 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 0.0000 2.0000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 3 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 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 2.5981 1.5000 0.0000 C 0 0 1 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 0.5000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 7 1 0 0 0 0 4 14 2 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 19 2 0 0 0 0 11 23 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 16 19 1 0 0 0 0 16 25 2 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 15 1 6 0 0 0 22 32 1 0 0 0 0 23 24 2 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.18
Volume:	453.09
LogP:	3.706
LogD:	2.979
LogS:	-3.819
# Rotatable Bonds:	7
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	3.906
Fsp3:	0.32
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:	-5.216
MDCK Permeability:	9.33355295273941e-06
Pgp-inhibitor:	0.118
Pgp-substrate:	0.833
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.737
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	93.98384857177734%
Volume Distribution (VD):	0.361
Pgp-substrate:	3.256441354751587%

ADMET: Metabolism

CYP1A2-inhibitor:	0.223
CYP1A2-substrate:	0.736
CYP2C19-inhibitor:	0.308
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.8
CYP2C9-substrate:	0.783
CYP2D6-inhibitor:	0.676
CYP2D6-substrate:	0.516
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	11.21
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.494
Drug-inuced Liver Injury (DILI):	0.768
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.948
Carcinogencity:	0.247
Eye Corrosion:	0.003
Eye Irritation:	0.871
Respiratory Toxicity:	0.853

Download Data

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

Natural Product: NPC321779

Natural Product ID:	NPC321779
*Common Name:**	Tanariflavanone D
IUPAC Name:	(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienyl]-2,3-dihydrochromen-4-one
Synonyms:	tanariflavanone D
Standard InCHIKey:	VALTWXVTFHGVHS-ILVSVAAVSA-N
Standard InCHI:	InChI=1S/C25H28O7/c1-13(2)17(26)8-5-14(3)4-7-16-19(28)11-23-24(25(16)31)21(30)12-22(32-23)15-6-9-18(27)20(29)10-15/h4,6,9-11,17,22,26-29,31H,1,5,7-8,12H2,2-3H3/b14-4+/t17?,22-/m0/s1
SMILES:	C=C(C)C(CC/C(=C/Cc1c(cc2c(C(=O)C[C@@H](c3ccc(c(c3)O)O)O2)c1O)O)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499116
PubChem CID:	11247668
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
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11421757]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
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]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18844422]
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]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28972755]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	4
Ki	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	19.5	ug.mL-1	PMID[478601]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	=	15400.0	nM	PMID[478602]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Ki	=	11700.0	nM	PMID[478602]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.5	ug.mL-1	PMID[478601]
NPT1	Others	Radical scavenging activity		IC50	=	20000.0	nM	PMID[478601]

☑ 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 NPC321779 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	394
0.1-0.2	1501
0.2-0.3	3803
0.3-0.4	9350
0.4-0.5	9026
0.5-0.6	3297
0.6-0.7	4640
0.7-0.8	5398
0.8-0.85	2839
0.85-0.9	1831
0.9-0.95	527
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC192083
0.9932	High Similarity	NPC213896
0.9866	High Similarity	NPC472598
0.9866	High Similarity	NPC474055
0.9864	High Similarity	NPC106976
0.98	High Similarity	NPC22192
0.9799	High Similarity	NPC35038
0.9799	High Similarity	NPC195796
0.9799	High Similarity	NPC278778
0.9799	High Similarity	NPC291878
0.9797	High Similarity	NPC298692
0.9797	High Similarity	NPC74924
0.9735	High Similarity	NPC282009
0.9735	High Similarity	NPC287328
0.9735	High Similarity	NPC321399
0.9733	High Similarity	NPC291508
0.9733	High Similarity	NPC27337
0.9733	High Similarity	NPC471209
0.9732	High Similarity	NPC45849
0.9732	High Similarity	NPC200761
0.9732	High Similarity	NPC477503
0.9732	High Similarity	NPC470327
0.9671	High Similarity	NPC471499
0.9671	High Similarity	NPC474038
0.9671	High Similarity	NPC472634
0.9671	High Similarity	NPC26326
0.9671	High Similarity	NPC142252
0.9671	High Similarity	NPC472632
0.9669	High Similarity	NPC210459
0.9669	High Similarity	NPC117418
0.9669	High Similarity	NPC53545
0.9667	High Similarity	NPC470328
0.9667	High Similarity	NPC209614
0.9667	High Similarity	NPC472626
0.9664	High Similarity	NPC18727
0.9608	High Similarity	NPC474034
0.9608	High Similarity	NPC476247
0.9608	High Similarity	NPC474033
0.9608	High Similarity	NPC472635
0.9605	High Similarity	NPC472630
0.9605	High Similarity	NPC475784
0.9605	High Similarity	NPC118256
0.9605	High Similarity	NPC192686
0.9605	High Similarity	NPC174953
0.9605	High Similarity	NPC119209
0.9605	High Similarity	NPC470326
0.9605	High Similarity	NPC472631
0.9605	High Similarity	NPC472624
0.9605	High Similarity	NPC36217
0.9603	High Similarity	NPC223787
0.96	High Similarity	NPC226025
0.96	High Similarity	NPC67396
0.9597	High Similarity	NPC323626
0.9597	High Similarity	NPC236637
0.9597	High Similarity	NPC219582
0.9597	High Similarity	NPC324233
0.9597	High Similarity	NPC302950
0.9595	High Similarity	NPC88804
0.9595	High Similarity	NPC3825
0.9592	High Similarity	NPC321011
0.9592	High Similarity	NPC294852
0.9592	High Similarity	NPC188679
0.9545	High Similarity	NPC124038
0.9545	High Similarity	NPC472625
0.9542	High Similarity	NPC289771
0.9542	High Similarity	NPC471210
0.9539	High Similarity	NPC95936
0.9539	High Similarity	NPC85121
0.9539	High Similarity	NPC473990
0.9539	High Similarity	NPC250214
0.9536	High Similarity	NPC24640
0.9536	High Similarity	NPC326037
0.9536	High Similarity	NPC13858
0.9536	High Similarity	NPC471500
0.9536	High Similarity	NPC320825
0.9527	High Similarity	NPC183959
0.9527	High Similarity	NPC1612
0.9481	High Similarity	NPC211107
0.9481	High Similarity	NPC201800
0.9477	High Similarity	NPC328102
0.9477	High Similarity	NPC476283
0.9477	High Similarity	NPC470183
0.9474	High Similarity	NPC474836
0.9474	High Similarity	NPC78225
0.9474	High Similarity	NPC52530
0.9474	High Similarity	NPC471515
0.9474	High Similarity	NPC473272
0.9474	High Similarity	NPC162869
0.9474	High Similarity	NPC156057
0.9474	High Similarity	NPC284820
0.9474	High Similarity	NPC474208
0.9474	High Similarity	NPC475267
0.9474	High Similarity	NPC471479
0.9474	High Similarity	NPC48208
0.947	High Similarity	NPC117992
0.947	High Similarity	NPC152951
0.947	High Similarity	NPC113906
0.947	High Similarity	NPC133392
0.947	High Similarity	NPC168247
0.947	High Similarity	NPC57674
0.947	High Similarity	NPC230149
0.9467	High Similarity	NPC37684
0.9467	High Similarity	NPC472912
0.9467	High Similarity	NPC36835
0.9467	High Similarity	NPC246162
0.9467	High Similarity	NPC63187
0.9467	High Similarity	NPC260491
0.9467	High Similarity	NPC471982
0.9467	High Similarity	NPC61506
0.9467	High Similarity	NPC240476
0.9467	High Similarity	NPC9743
0.9467	High Similarity	NPC157784
0.9463	High Similarity	NPC338131
0.9459	High Similarity	NPC3036
0.9459	High Similarity	NPC119059
0.9456	High Similarity	NPC472629
0.9456	High Similarity	NPC187282
0.9456	High Similarity	NPC24136
0.9456	High Similarity	NPC290133
0.9423	High Similarity	NPC471213
0.9419	High Similarity	NPC186686
0.9419	High Similarity	NPC476295
0.9416	High Similarity	NPC471212
0.9416	High Similarity	NPC266314
0.9416	High Similarity	NPC471211
0.9416	High Similarity	NPC134783
0.9416	High Similarity	NPC158188
0.9416	High Similarity	NPC198829
0.9412	High Similarity	NPC469658
0.9412	High Similarity	NPC329091
0.9408	High Similarity	NPC170026
0.9408	High Similarity	NPC68093
0.9408	High Similarity	NPC78492
0.9408	High Similarity	NPC255106
0.9408	High Similarity	NPC191146
0.9408	High Similarity	NPC250922
0.9408	High Similarity	NPC282307
0.9408	High Similarity	NPC235165
0.9408	High Similarity	NPC208152
0.9404	High Similarity	NPC49402
0.9404	High Similarity	NPC70433
0.9404	High Similarity	NPC33051
0.9404	High Similarity	NPC325028
0.9404	High Similarity	NPC227337
0.9404	High Similarity	NPC27532
0.9404	High Similarity	NPC170492
0.9404	High Similarity	NPC273462
0.9404	High Similarity	NPC256346
0.9404	High Similarity	NPC246328
0.94	High Similarity	NPC244577
0.94	High Similarity	NPC263384
0.94	High Similarity	NPC278476
0.94	High Similarity	NPC254412
0.94	High Similarity	NPC262039
0.94	High Similarity	NPC472420
0.94	High Similarity	NPC262038
0.94	High Similarity	NPC319910
0.94	High Similarity	NPC205046
0.94	High Similarity	NPC472422
0.94	High Similarity	NPC204515
0.94	High Similarity	NPC154345
0.94	High Similarity	NPC471677
0.94	High Similarity	NPC304295
0.94	High Similarity	NPC59162
0.94	High Similarity	NPC471676
0.9396	High Similarity	NPC105512
0.9396	High Similarity	NPC38545
0.9396	High Similarity	NPC171916
0.9392	High Similarity	NPC108406
0.9392	High Similarity	NPC95864
0.9392	High Similarity	NPC472627
0.9388	High Similarity	NPC124780
0.9388	High Similarity	NPC470890
0.9388	High Similarity	NPC87486
0.9359	High Similarity	NPC62261
0.9359	High Similarity	NPC108433
0.9359	High Similarity	NPC293319
0.9359	High Similarity	NPC300053
0.9359	High Similarity	NPC472277
0.9359	High Similarity	NPC475888
0.9355	High Similarity	NPC474162
0.9355	High Similarity	NPC194427
0.9355	High Similarity	NPC472964
0.9355	High Similarity	NPC220912
0.9355	High Similarity	NPC127782
0.9355	High Similarity	NPC474150
0.9355	High Similarity	NPC300537
0.9351	High Similarity	NPC472902
0.9351	High Similarity	NPC263449
0.9351	High Similarity	NPC299436
0.9346	High Similarity	NPC96167
0.9346	High Similarity	NPC472914
0.9346	High Similarity	NPC52889
0.9346	High Similarity	NPC245758
0.9346	High Similarity	NPC99597
0.9346	High Similarity	NPC472911
0.9346	High Similarity	NPC67876
0.9346	High Similarity	NPC472913
0.9346	High Similarity	NPC222814
0.9346	High Similarity	NPC210084

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 NPC321779 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	910
0.2-0.3	1719
0.3-0.4	2579
0.4-0.5	1826
0.5-0.6	1031
0.6-0.7	539
0.7-0.8	142
0.8-0.85	37
0.85-0.9	18
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9932	High Similarity	NPD2393	Clinical (unspecified phase)
0.9597	High Similarity	NPD1934	Approved
0.9236	High Similarity	NPD6167	Clinical (unspecified phase)
0.9236	High Similarity	NPD6168	Clinical (unspecified phase)
0.9236	High Similarity	NPD6166	Phase 2
0.9189	High Similarity	NPD1511	Approved
0.915	High Similarity	NPD2801	Approved
0.9079	High Similarity	NPD4380	Phase 2
0.9067	High Similarity	NPD1512	Approved
0.9006	High Similarity	NPD7074	Phase 3
0.9	High Similarity	NPD4378	Clinical (unspecified phase)
0.8944	High Similarity	NPD7054	Approved
0.8912	High Similarity	NPD1552	Clinical (unspecified phase)
0.8912	High Similarity	NPD1550	Clinical (unspecified phase)
0.891	High Similarity	NPD3882	Suspended
0.8889	High Similarity	NPD7472	Approved
0.8882	High Similarity	NPD3818	Discontinued
0.8854	High Similarity	NPD7075	Discontinued
0.8851	High Similarity	NPD1549	Phase 2
0.8834	High Similarity	NPD6797	Phase 2
0.879	High Similarity	NPD4868	Clinical (unspecified phase)
0.8782	High Similarity	NPD7096	Clinical (unspecified phase)
0.878	High Similarity	NPD7251	Discontinued
0.8742	High Similarity	NPD5494	Approved
0.8734	High Similarity	NPD4381	Clinical (unspecified phase)
0.8726	High Similarity	NPD3817	Phase 2
0.8726	High Similarity	NPD8443	Clinical (unspecified phase)
0.8662	High Similarity	NPD7819	Suspended
0.8614	High Similarity	NPD7808	Phase 3
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8599	High Similarity	NPD6801	Discontinued
0.8598	High Similarity	NPD7804	Clinical (unspecified phase)
0.8591	High Similarity	NPD2796	Approved
0.8571	High Similarity	NPD6959	Discontinued
0.8535	High Similarity	NPD7411	Suspended
0.8523	High Similarity	NPD1510	Phase 2
0.8506	High Similarity	NPD7410	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD5844	Phase 1
0.8443	Intermediate Similarity	NPD6559	Discontinued
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.8383	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1240	Approved
0.8378	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1613	Approved
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD6799	Approved
0.8267	Intermediate Similarity	NPD1607	Approved
0.8255	Intermediate Similarity	NPD943	Approved
0.8193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5402	Approved
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8108	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.8098	Intermediate Similarity	NPD7768	Phase 2
0.8086	Intermediate Similarity	NPD1465	Phase 2
0.8065	Intermediate Similarity	NPD2800	Approved
0.8065	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD3027	Phase 3
0.805	Intermediate Similarity	NPD5403	Approved
0.8041	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7925	Intermediate Similarity	NPD5401	Approved
0.7898	Intermediate Similarity	NPD3750	Approved
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7861	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3749	Approved
0.7826	Intermediate Similarity	NPD920	Approved
0.7811	Intermediate Similarity	NPD3926	Phase 2
0.7792	Intermediate Similarity	NPD6651	Approved
0.7763	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6099	Approved
0.7756	Intermediate Similarity	NPD6100	Approved
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.773	Intermediate Similarity	NPD3226	Approved
0.7722	Intermediate Similarity	NPD4363	Phase 3
0.7722	Intermediate Similarity	NPD4360	Phase 2
0.7722	Intermediate Similarity	NPD1243	Approved
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7688	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6234	Discontinued
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7635	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4908	Phase 1
0.7625	Intermediate Similarity	NPD6190	Approved
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7613	Intermediate Similarity	NPD447	Suspended
0.7595	Intermediate Similarity	NPD2344	Approved
0.7593	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD37	Approved
0.758	Intermediate Similarity	NPD3748	Approved
0.758	Intermediate Similarity	NPD7033	Discontinued
0.7572	Intermediate Similarity	NPD7228	Approved
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4967	Phase 2
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7541	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1933	Approved
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4625	Phase 3
0.746	Intermediate Similarity	NPD7584	Approved
0.7451	Intermediate Similarity	NPD9494	Approved
0.7438	Intermediate Similarity	NPD2424	Discontinued
0.7434	Intermediate Similarity	NPD1203	Approved
0.7419	Intermediate Similarity	NPD6782	Approved
0.7419	Intermediate Similarity	NPD6778	Approved
0.7419	Intermediate Similarity	NPD6776	Approved
0.7419	Intermediate Similarity	NPD6777	Approved
0.7419	Intermediate Similarity	NPD6779	Approved
0.7419	Intermediate Similarity	NPD6780	Approved
0.7419	Intermediate Similarity	NPD6781	Approved
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7391	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4361	Phase 2
0.7389	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8150	Discontinued
0.7389	Intermediate Similarity	NPD8434	Phase 2
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7341	Intermediate Similarity	NPD7229	Phase 3
0.7338	Intermediate Similarity	NPD2861	Phase 2
0.7337	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD6798	Discontinued
0.7308	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7284	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD7266	Discontinued
0.7247	Intermediate Similarity	NPD3823	Discontinued
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.7237	Intermediate Similarity	NPD1608	Approved
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD2797	Approved
0.7202	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD5242	Approved
0.7193	Intermediate Similarity	NPD5353	Approved
0.7191	Intermediate Similarity	NPD1729	Discontinued
0.719	Intermediate Similarity	NPD4749	Approved
0.7178	Intermediate Similarity	NPD2654	Approved
0.7173	Intermediate Similarity	NPD7870	Phase 2
0.7173	Intermediate Similarity	NPD7871	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7171	Intermediate Similarity	NPD1201	Approved
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7169	Intermediate Similarity	NPD4662	Approved
0.7169	Intermediate Similarity	NPD4661	Approved
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7151	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD6534	Approved
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7135	Intermediate Similarity	NPD5760	Phase 2
0.7135	Intermediate Similarity	NPD5761	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