NPASS Compound

Structure

CID40524 OpenBabel06191715372D 30 31 0 0 1 0 0 0 0 0999 V2000 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 -3.4641 -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 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 -4.3301 0.5000 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 -4.3301 -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 2.5981 -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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -5.1962 -1.0000 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 0.0000 -1.0000 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 2.5981 -2.5000 0.0000 C 0 0 3 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 2.5981 0.5000 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 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 15 2 0 0 0 0 6 9 2 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 14 25 1 0 0 0 0 16 23 1 0 0 0 0 18 21 2 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.19
Volume:	441.43
LogP:	4.874
LogD:	3.572
LogS:	-3.694
# Rotatable Bonds:	8
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	3.431
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.964
MDCK Permeability:	1.606843579793349e-05
Pgp-inhibitor:	0.447
Pgp-substrate:	0.427
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.778
30% Bioavailability (F30%):	0.493

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	100.0184555053711%
Volume Distribution (VD):	0.454
Pgp-substrate:	0.705449104309082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.848
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.465
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.707
CYP2C9-substrate:	0.73
CYP2D6-inhibitor:	0.867
CYP2D6-substrate:	0.758
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	13.519
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.556
Drug-inuced Liver Injury (DILI):	0.282
AMES Toxicity:	0.518
Rat Oral Acute Toxicity:	0.318
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.946
Carcinogencity:	0.465
Eye Corrosion:	0.003
Eye Irritation:	0.899
Respiratory Toxicity:	0.605

Download Data

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

Natural Product: NPC40524

Natural Product ID:	NPC40524
*Common Name:**	Bartericin A
IUPAC Name:	(E)-1-[2,4-dihydroxy-5-(2-hydroxy-3-methylbut-3-enyl)phenyl]-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
Synonyms:
Standard InCHIKey:	HJJNGNVCQLTMCE-JXMROGBWSA-N
Standard InCHI:	InChI=1S/C25H28O5/c1-15(2)5-8-18-11-17(6-9-21(18)26)7-10-22(27)20-12-19(13-23(28)16(3)4)24(29)14-25(20)30/h5-7,9-12,14,23,26,28-30H,3,8,13H2,1-2,4H3/b10-7+
SMILES:	CC(=CCc1cc(/C=C/C(=O)c2cc(CC(C(=C)C)O)c(cc2O)O)ccc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1169613
PubChem CID:	12136209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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
NPO12044.1	Dorstenia barteri var. subtriangularis	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO12044.1	Dorstenia barteri var. subtriangularis	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12044.1	Dorstenia barteri var. subtriangularis	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2150.0	nM	PMID[523551]

☑ 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 NPC40524 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	310
0.1-0.2	1254
0.2-0.3	3268
0.3-0.4	8714
0.4-0.5	10737
0.5-0.6	4206
0.6-0.7	6810
0.7-0.8	5590
0.8-0.85	1260
0.85-0.9	455
0.9-0.95	65
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213485
1.0	High Similarity	NPC139074
0.9844	High Similarity	NPC61153
0.9844	High Similarity	NPC130899
0.9844	High Similarity	NPC283590
0.9844	High Similarity	NPC70859
0.9841	High Similarity	NPC475042
0.9528	High Similarity	NPC474998
0.9524	High Similarity	NPC30501
0.9524	High Similarity	NPC162612
0.9524	High Similarity	NPC266689
0.9524	High Similarity	NPC169250
0.9524	High Similarity	NPC23126
0.9524	High Similarity	NPC190043
0.9524	High Similarity	NPC105157
0.9524	High Similarity	NPC103356
0.9524	High Similarity	NPC100067
0.9524	High Similarity	NPC98254
0.9524	High Similarity	NPC72158
0.9449	High Similarity	NPC473017
0.9449	High Similarity	NPC21305
0.9449	High Similarity	NPC221777
0.9444	High Similarity	NPC62952
0.9444	High Similarity	NPC267846
0.9375	High Similarity	NPC476119
0.9375	High Similarity	NPC120488
0.9375	High Similarity	NPC102829
0.937	High Similarity	NPC116513
0.9333	High Similarity	NPC321980
0.9333	High Similarity	NPC470087
0.9265	High Similarity	NPC148545
0.9242	High Similarity	NPC470210
0.9231	High Similarity	NPC275504
0.9197	High Similarity	NPC475705
0.9197	High Similarity	NPC476178
0.9197	High Similarity	NPC245482
0.9197	High Similarity	NPC51887
0.9197	High Similarity	NPC301751
0.9197	High Similarity	NPC117836
0.9191	High Similarity	NPC470089
0.9185	High Similarity	NPC470211
0.9167	High Similarity	NPC282780
0.9167	High Similarity	NPC166480
0.9127	High Similarity	NPC91105
0.9127	High Similarity	NPC309765
0.9127	High Similarity	NPC32032
0.9127	High Similarity	NPC133909
0.9065	High Similarity	NPC316769
0.9062	High Similarity	NPC475733
0.9055	High Similarity	NPC472029
0.9055	High Similarity	NPC65761
0.9051	High Similarity	NPC469404
0.9051	High Similarity	NPC135524
0.9051	High Similarity	NPC474961
0.9048	High Similarity	NPC45438
0.9048	High Similarity	NPC303737
0.9048	High Similarity	NPC19174
0.9048	High Similarity	NPC143427
0.9048	High Similarity	NPC267552
0.9048	High Similarity	NPC224273
0.9048	High Similarity	NPC156139
0.9048	High Similarity	NPC215392
0.9048	High Similarity	NPC242895
0.9048	High Similarity	NPC73532
0.9048	High Similarity	NPC196976
0.9048	High Similarity	NPC115159
0.903	High Similarity	NPC264112
0.903	High Similarity	NPC194764
0.903	High Similarity	NPC65005
0.903	High Similarity	NPC131039
0.9015	High Similarity	NPC175738
0.9	High Similarity	NPC51070
0.9	High Similarity	NPC222298
0.8992	High Similarity	NPC8745
0.8984	High Similarity	NPC13238
0.8978	High Similarity	NPC204985
0.8978	High Similarity	NPC172250
0.8978	High Similarity	NPC215311
0.8978	High Similarity	NPC213659
0.8978	High Similarity	NPC48624
0.8978	High Similarity	NPC259166
0.8978	High Similarity	NPC144118
0.8978	High Similarity	NPC80962
0.8978	High Similarity	NPC326109
0.8978	High Similarity	NPC219917
0.8978	High Similarity	NPC204045
0.8978	High Similarity	NPC305845
0.8971	High Similarity	NPC21350
0.8971	High Similarity	NPC112789
0.8971	High Similarity	NPC19622
0.8968	High Similarity	NPC297186
0.8968	High Similarity	NPC149246
0.8963	High Similarity	NPC41461
0.8963	High Similarity	NPC44960
0.8963	High Similarity	NPC477243
0.8963	High Similarity	NPC477244
0.8963	High Similarity	NPC25287
0.8963	High Similarity	NPC12165
0.8963	High Similarity	NPC98115
0.8963	High Similarity	NPC168105
0.8963	High Similarity	NPC249606
0.8963	High Similarity	NPC66349
0.8963	High Similarity	NPC186838
0.8963	High Similarity	NPC1486
0.8963	High Similarity	NPC474110
0.8963	High Similarity	NPC150399
0.8963	High Similarity	NPC274109
0.8963	High Similarity	NPC477242
0.8931	High Similarity	NPC92624
0.8931	High Similarity	NPC109123
0.8929	High Similarity	NPC472629
0.8921	High Similarity	NPC244691
0.8921	High Similarity	NPC471906
0.8915	High Similarity	NPC10926
0.8913	High Similarity	NPC268204
0.8913	High Similarity	NPC55832
0.8913	High Similarity	NPC52789
0.8913	High Similarity	NPC137649
0.8913	High Similarity	NPC26051
0.8905	High Similarity	NPC477956
0.8905	High Similarity	NPC283429
0.8905	High Similarity	NPC295384
0.8905	High Similarity	NPC275903
0.8897	High Similarity	NPC153979
0.8897	High Similarity	NPC317119
0.8897	High Similarity	NPC472419
0.8897	High Similarity	NPC175552
0.8889	High Similarity	NPC84699
0.8889	High Similarity	NPC13575
0.8889	High Similarity	NPC159525
0.8889	High Similarity	NPC156092
0.8881	High Similarity	NPC475088
0.8873	High Similarity	NPC89442
0.8864	High Similarity	NPC259942
0.8864	High Similarity	NPC147757
0.8857	High Similarity	NPC470890
0.8857	High Similarity	NPC124780
0.8857	High Similarity	NPC87486
0.8857	High Similarity	NPC224714
0.8841	High Similarity	NPC101366
0.8841	High Similarity	NPC253822
0.8841	High Similarity	NPC11056
0.8832	High Similarity	NPC471620
0.8832	High Similarity	NPC190457
0.8832	High Similarity	NPC242994
0.8832	High Similarity	NPC138099
0.8824	High Similarity	NPC213603
0.8819	High Similarity	NPC229649
0.8819	High Similarity	NPC146642
0.8815	High Similarity	NPC164136
0.8815	High Similarity	NPC103842
0.8815	High Similarity	NPC286336
0.8811	High Similarity	NPC61258
0.881	High Similarity	NPC188814
0.881	High Similarity	NPC158222
0.881	High Similarity	NPC195262
0.881	High Similarity	NPC161617
0.881	High Similarity	NPC473767
0.8803	High Similarity	NPC168085
0.8786	High Similarity	NPC175504
0.8786	High Similarity	NPC149026
0.8786	High Similarity	NPC150408
0.8786	High Similarity	NPC257097
0.8786	High Similarity	NPC39329
0.8786	High Similarity	NPC91560
0.8786	High Similarity	NPC68104
0.8786	High Similarity	NPC75049
0.8786	High Similarity	NPC221432
0.8786	High Similarity	NPC164980
0.8786	High Similarity	NPC169591
0.8786	High Similarity	NPC143896
0.8786	High Similarity	NPC310130
0.8768	High Similarity	NPC169452
0.8768	High Similarity	NPC181560
0.8768	High Similarity	NPC472366
0.8759	High Similarity	NPC303644
0.8759	High Similarity	NPC162680
0.8759	High Similarity	NPC209560
0.8759	High Similarity	NPC294409
0.8759	High Similarity	NPC7013
0.8759	High Similarity	NPC116632
0.8759	High Similarity	NPC181124
0.875	High Similarity	NPC474744
0.875	High Similarity	NPC263384
0.875	High Similarity	NPC471676
0.875	High Similarity	NPC474772
0.875	High Similarity	NPC472422
0.875	High Similarity	NPC191976
0.875	High Similarity	NPC472423
0.875	High Similarity	NPC244577
0.875	High Similarity	NPC118919
0.875	High Similarity	NPC472420
0.875	High Similarity	NPC226275
0.8741	High Similarity	NPC144051
0.8741	High Similarity	NPC159623
0.8741	High Similarity	NPC28753
0.8741	High Similarity	NPC242294
0.8741	High Similarity	NPC139813
0.8741	High Similarity	NPC294593
0.8741	High Similarity	NPC337373

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 NPC40524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	875
0.2-0.3	1471
0.3-0.4	2667
0.4-0.5	2175
0.5-0.6	1160
0.6-0.7	396
0.7-0.8	119
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD4380	Phase 2
0.8613	High Similarity	NPD1509	Clinical (unspecified phase)
0.8613	High Similarity	NPD1510	Phase 2
0.8593	High Similarity	NPD943	Approved
0.8593	High Similarity	NPD1240	Approved
0.8592	High Similarity	NPD4378	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1607	Approved
0.8429	Intermediate Similarity	NPD1549	Phase 2
0.8392	Intermediate Similarity	NPD7390	Discontinued
0.8378	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD2796	Approved
0.8212	Intermediate Similarity	NPD7075	Discontinued
0.8207	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD2935	Discontinued
0.8133	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8092	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD1164	Approved
0.8067	Intermediate Similarity	NPD6801	Discontinued
0.8067	Intermediate Similarity	NPD1934	Approved
0.8013	Intermediate Similarity	NPD7819	Suspended
0.7958	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1470	Approved
0.791	Intermediate Similarity	NPD1201	Approved
0.7902	Intermediate Similarity	NPD5404	Approved
0.7902	Intermediate Similarity	NPD5406	Approved
0.7902	Intermediate Similarity	NPD5408	Approved
0.7902	Intermediate Similarity	NPD5405	Approved
0.7891	Intermediate Similarity	NPD6799	Approved
0.7862	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6959	Discontinued
0.782	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6651	Approved
0.7808	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3882	Suspended
0.7792	Intermediate Similarity	NPD7768	Phase 2
0.7785	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6166	Phase 2
0.7785	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2801	Approved
0.777	Intermediate Similarity	NPD1511	Approved
0.774	Intermediate Similarity	NPD2800	Approved
0.774	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2534	Approved
0.7718	Intermediate Similarity	NPD2533	Approved
0.7718	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD6599	Discontinued
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7671	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1512	Approved
0.7658	Intermediate Similarity	NPD6232	Discontinued
0.7655	Intermediate Similarity	NPD1551	Phase 2
0.7643	Intermediate Similarity	NPD5494	Approved
0.7625	Intermediate Similarity	NPD7473	Discontinued
0.7616	Intermediate Similarity	NPD920	Approved
0.7607	Intermediate Similarity	NPD6559	Discontinued
0.7594	Intermediate Similarity	NPD9493	Approved
0.7593	Intermediate Similarity	NPD7074	Phase 3
0.7586	Intermediate Similarity	NPD2799	Discontinued
0.7568	Intermediate Similarity	NPD3750	Approved
0.7546	Intermediate Similarity	NPD5953	Discontinued
0.7535	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7286	Phase 2
0.7531	Intermediate Similarity	NPD7054	Approved
0.7519	Intermediate Similarity	NPD9266	Approved
0.7519	Intermediate Similarity	NPD74	Approved
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9545	Approved
0.7467	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD9269	Phase 2
0.7463	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD940	Approved
0.746	Intermediate Similarity	NPD846	Approved
0.7455	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD3400	Discontinued
0.7442	Intermediate Similarity	NPD9267	Approved
0.7442	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD9263	Approved
0.7442	Intermediate Similarity	NPD9264	Approved
0.7439	Intermediate Similarity	NPD6797	Phase 2
0.7426	Intermediate Similarity	NPD9268	Approved
0.7423	Intermediate Similarity	NPD5844	Phase 1
0.7413	Intermediate Similarity	NPD2313	Discontinued
0.7405	Intermediate Similarity	NPD3749	Approved
0.7394	Intermediate Similarity	NPD7251	Discontinued
0.7389	Intermediate Similarity	NPD5402	Approved
0.7376	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD5401	Approved
0.7349	Intermediate Similarity	NPD7808	Phase 3
0.7344	Intermediate Similarity	NPD1237	Approved
0.7305	Intermediate Similarity	NPD1203	Approved
0.7285	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7266	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3748	Approved
0.7225	Intermediate Similarity	NPD4363	Phase 3
0.7225	Intermediate Similarity	NPD4360	Phase 2
0.7214	Intermediate Similarity	NPD3972	Approved
0.7212	Intermediate Similarity	NPD6020	Phase 2
0.7185	Intermediate Similarity	NPD9281	Approved
0.7179	Intermediate Similarity	NPD3226	Approved
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7172	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3764	Approved
0.7171	Intermediate Similarity	NPD6190	Approved
0.716	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD919	Approved
0.7133	Intermediate Similarity	NPD2346	Discontinued
0.7133	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9261	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3300	Phase 2
0.7117	Intermediate Similarity	NPD5710	Approved
0.7117	Intermediate Similarity	NPD5711	Approved
0.7114	Intermediate Similarity	NPD7033	Discontinued
0.711	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1242	Phase 1
0.7103	Intermediate Similarity	NPD3027	Phase 3
0.7092	Intermediate Similarity	NPD9717	Approved
0.7076	Intermediate Similarity	NPD8150	Discontinued
0.7068	Intermediate Similarity	NPD4750	Phase 3
0.7063	Intermediate Similarity	NPD2859	Approved
0.7063	Intermediate Similarity	NPD2860	Approved
0.7051	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4908	Phase 1
0.7031	Intermediate Similarity	NPD3020	Approved
0.7027	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5048	Discontinued
0.7007	Intermediate Similarity	NPD520	Approved
0.7	Intermediate Similarity	NPD2932	Approved
0.7	Intermediate Similarity	NPD3019	Approved
0.6993	Remote Similarity	NPD7003	Approved
0.6989	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4361	Phase 2
0.6984	Remote Similarity	NPD2934	Approved
0.6984	Remote Similarity	NPD2933	Approved
0.6981	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3926	Phase 2
0.6964	Remote Similarity	NPD1729	Discontinued
0.6962	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6099	Approved
0.6954	Remote Similarity	NPD6100	Approved
0.6939	Remote Similarity	NPD3268	Approved
0.6932	Remote Similarity	NPD6535	Approved
0.6932	Remote Similarity	NPD6534	Approved
0.6913	Remote Similarity	NPD5124	Phase 1
0.6913	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1610	Phase 2
0.6892	Remote Similarity	NPD6407	Approved
0.6892	Remote Similarity	NPD6405	Approved
0.6887	Remote Similarity	NPD4308	Phase 3
0.6885	Remote Similarity	NPD7584	Approved
0.6883	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1876	Approved
0.687	Remote Similarity	NPD1930	Approved
0.687	Remote Similarity	NPD1929	Approved
0.687	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2424	Discontinued
0.6857	Remote Similarity	NPD1548	Phase 1
0.6846	Remote Similarity	NPD1613	Approved
0.6846	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6777	Approved
0.6833	Remote Similarity	NPD6781	Approved
0.6833	Remote Similarity	NPD6778	Approved
0.6833	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6782	Approved
0.6833	Remote Similarity	NPD6776	Approved
0.6833	Remote Similarity	NPD6780	Approved
0.6833	Remote Similarity	NPD6779	Approved
0.6832	Remote Similarity	NPD37	Approved
0.6832	Remote Similarity	NPD6844	Discontinued
0.6828	Remote Similarity	NPD2797	Approved
0.6816	Remote Similarity	NPD7700	Phase 2
0.6816	Remote Similarity	NPD7699	Phase 2
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4662	Approved
0.6815	Remote Similarity	NPD4661	Approved
0.6812	Remote Similarity	NPD5951	Approved
0.6802	Remote Similarity	NPD8312	Approved
0.6802	Remote Similarity	NPD8313	Approved
0.68	Remote Similarity	NPD447	Suspended
0.68	Remote Similarity	NPD8397	Clinical (unspecified phase)

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