NPASS Compound

Structure

NPC470210 OpenBabel07101718292D 30 31 0 0 0 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 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 2.5981 2.5000 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 -4.3301 -1.5000 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 -6.0622 -0.5000 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 1.7321 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 -0.5000 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 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 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 -6.0622 -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 -0.8660 -0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 -6.9282 -2.0000 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 1.7321 -2.0000 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 2.5981 4.5000 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 16 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 11 1 0 0 0 0 4 16 2 0 0 0 0 5 15 1 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 6 17 2 0 0 0 0 7 10 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 24 2 0 0 0 0 21 26 2 0 0 0 0 22 27 1 0 0 0 0 23 29 1 0 0 0 0 23 30 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.19
Volume:	435.56
LogP:	3.899
LogD:	3.008
LogS:	-4.149
# Rotatable Bonds:	10
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	2.848
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.833
MDCK Permeability:	2.189237784477882e-05
Pgp-inhibitor:	0.063
Pgp-substrate:	0.074
Human Intestinal Absorption (HIA):	0.157
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.506

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	100.45389556884766%
Volume Distribution (VD):	0.445
Pgp-substrate:	0.6730543375015259%

ADMET: Metabolism

CYP1A2-inhibitor:	0.679
CYP1A2-substrate:	0.652
CYP2C19-inhibitor:	0.587
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.832
CYP2D6-substrate:	0.774
CYP3A4-inhibitor:	0.452
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	8.229
Half-life (T1/2):	0.752

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.597
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.664
Skin Sensitization:	0.953
Carcinogencity:	0.606
Eye Corrosion:	0.003
Eye Irritation:	0.442
Respiratory Toxicity:	0.842

Download Data

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

Natural Product: NPC470210

Natural Product ID:	NPC470210
*Common Name:**	Xanthokeistal A
IUPAC Name:	(E)-1-[3-[(E)-6,6-dimethoxy-3-methylhex-2-enyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:	Xanthokeistal A
Standard InCHIKey:	ADTPLEJVNULKHA-BJRVJWNUSA-N
Standard InCHI:	InChI=1S/C24H28O6/c1-16(5-15-23(29-2)30-3)4-11-19-22(27)14-12-20(24(19)28)21(26)13-8-17-6-9-18(25)10-7-17/h4,6-10,12-14,23,25,27-28H,5,11,15H2,1-3H3/b13-8+,16-4+
SMILES:	CC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)O)CCC(OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823413
PubChem CID:	56666829
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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	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
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2228	Individual Protein	Neuraminidase	Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1))	IC50	=	30900.0	nM	PMID[449330]
NPT2228	Individual Protein	Neuraminidase	Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1))	Ki	=	33500.0	nM	PMID[449330]

☑ 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 NPC470210 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	300
0.1-0.2	1377
0.2-0.3	3379
0.3-0.4	9457
0.4-0.5	10055
0.5-0.6	4367
0.6-0.7	6973
0.7-0.8	5553
0.8-0.85	902
0.85-0.9	287
0.9-0.95	46
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9385	High Similarity	NPC475042
0.9375	High Similarity	NPC100067
0.9375	High Similarity	NPC103356
0.9375	High Similarity	NPC98254
0.9375	High Similarity	NPC23126
0.9375	High Similarity	NPC169250
0.9375	High Similarity	NPC190043
0.9375	High Similarity	NPC162612
0.9375	High Similarity	NPC266689
0.9375	High Similarity	NPC105157
0.9375	High Similarity	NPC72158
0.9375	High Similarity	NPC30501
0.9302	High Similarity	NPC473017
0.9302	High Similarity	NPC21305
0.9302	High Similarity	NPC221777
0.9297	High Similarity	NPC62952
0.9297	High Similarity	NPC267846
0.9242	High Similarity	NPC213485
0.9242	High Similarity	NPC40524
0.9242	High Similarity	NPC139074
0.9231	High Similarity	NPC474998
0.9231	High Similarity	NPC476119
0.9225	High Similarity	NPC116513
0.9118	High Similarity	NPC112789
0.9118	High Similarity	NPC19622
0.9104	High Similarity	NPC283590
0.9104	High Similarity	NPC130899
0.9104	High Similarity	NPC61153
0.9104	High Similarity	NPC70859
0.9091	High Similarity	NPC275504
0.9051	High Similarity	NPC275903
0.9037	High Similarity	NPC131039
0.9008	High Similarity	NPC470981
0.8984	High Similarity	NPC91105
0.8984	High Similarity	NPC133909
0.8984	High Similarity	NPC32032
0.8984	High Similarity	NPC309765
0.8971	High Similarity	NPC168105
0.8971	High Similarity	NPC98115
0.8971	High Similarity	NPC477244
0.8971	High Similarity	NPC1486
0.8971	High Similarity	NPC249606
0.8971	High Similarity	NPC66349
0.8971	High Similarity	NPC186838
0.8971	High Similarity	NPC150399
0.8971	High Similarity	NPC274109
0.8971	High Similarity	NPC477242
0.8971	High Similarity	NPC41461
0.8971	High Similarity	NPC477243
0.8971	High Similarity	NPC25287
0.8971	High Similarity	NPC12165
0.8915	High Similarity	NPC65761
0.8915	High Similarity	NPC472029
0.8913	High Similarity	NPC470211
0.8906	High Similarity	NPC73532
0.8906	High Similarity	NPC156139
0.8906	High Similarity	NPC19174
0.8906	High Similarity	NPC215392
0.8906	High Similarity	NPC267552
0.8906	High Similarity	NPC303737
0.8906	High Similarity	NPC115159
0.8906	High Similarity	NPC143427
0.8906	High Similarity	NPC242895
0.8906	High Similarity	NPC196976
0.8906	High Similarity	NPC45438
0.8906	High Similarity	NPC224273
0.8905	High Similarity	NPC317119
0.8905	High Similarity	NPC472419
0.8905	High Similarity	NPC153979
0.8897	High Similarity	NPC156092
0.8897	High Similarity	NPC13575
0.8889	High Similarity	NPC282780
0.8889	High Similarity	NPC166480
0.8889	High Similarity	NPC318424
0.8849	High Similarity	NPC213659
0.8849	High Similarity	NPC326109
0.8849	High Similarity	NPC144118
0.8849	High Similarity	NPC48624
0.8849	High Similarity	NPC259166
0.8849	High Similarity	NPC219917
0.8849	High Similarity	NPC204985
0.8849	High Similarity	NPC172250
0.8849	High Similarity	NPC80962
0.8849	High Similarity	NPC215311
0.8841	High Similarity	NPC21350
0.8841	High Similarity	NPC471620
0.8828	High Similarity	NPC149246
0.8828	High Similarity	NPC297186
0.8824	High Similarity	NPC103842
0.8824	High Similarity	NPC286336
0.8797	High Similarity	NPC102829
0.8797	High Similarity	NPC120488
0.8786	High Similarity	NPC26051
0.8786	High Similarity	NPC55832
0.8786	High Similarity	NPC470089
0.8786	High Similarity	NPC268204
0.8786	High Similarity	NPC469404
0.8786	High Similarity	NPC52789
0.8786	High Similarity	NPC470087
0.8786	High Similarity	NPC321980
0.8779	High Similarity	NPC475733
0.8777	High Similarity	NPC283429
0.8777	High Similarity	NPC295384
0.8777	High Similarity	NPC472366
0.8777	High Similarity	NPC477956
0.8759	High Similarity	NPC65005
0.8759	High Similarity	NPC194764
0.8759	High Similarity	NPC264112
0.875	High Similarity	NPC56031
0.875	High Similarity	NPC28753
0.875	High Similarity	NPC337373
0.875	High Similarity	NPC159623
0.875	High Similarity	NPC144051
0.875	High Similarity	NPC472365
0.875	High Similarity	NPC204960
0.875	High Similarity	NPC82225
0.875	High Similarity	NPC312318
0.875	High Similarity	NPC159525
0.875	High Similarity	NPC263670
0.875	High Similarity	NPC27643
0.875	High Similarity	NPC20560
0.875	High Similarity	NPC188646
0.875	High Similarity	NPC139813
0.875	High Similarity	NPC242294
0.875	High Similarity	NPC192304
0.875	High Similarity	NPC294593
0.875	High Similarity	NPC18877
0.875	High Similarity	NPC175098
0.8741	High Similarity	NPC175738
0.8741	High Similarity	NPC262359
0.8723	High Similarity	NPC148545
0.8714	High Similarity	NPC101366
0.8714	High Similarity	NPC11056
0.8714	High Similarity	NPC253822
0.8712	High Similarity	NPC8745
0.8705	High Similarity	NPC243528
0.8705	High Similarity	NPC251681
0.8705	High Similarity	NPC124269
0.8702	High Similarity	NPC13238
0.8696	High Similarity	NPC213603
0.8686	High Similarity	NPC164136
0.8682	High Similarity	NPC229649
0.8676	High Similarity	NPC129132
0.8676	High Similarity	NPC205468
0.8676	High Similarity	NPC257756
0.8676	High Similarity	NPC87231
0.8676	High Similarity	NPC212631
0.8672	High Similarity	NPC158222
0.8672	High Similarity	NPC188814
0.8672	High Similarity	NPC195262
0.8672	High Similarity	NPC161617
0.8662	High Similarity	NPC164980
0.8662	High Similarity	NPC68104
0.8662	High Similarity	NPC310130
0.8662	High Similarity	NPC175504
0.8662	High Similarity	NPC91560
0.8662	High Similarity	NPC257097
0.8662	High Similarity	NPC150408
0.8662	High Similarity	NPC117836
0.8662	High Similarity	NPC476178
0.8662	High Similarity	NPC301751
0.8662	High Similarity	NPC475705
0.8662	High Similarity	NPC39329
0.8662	High Similarity	NPC169591
0.8662	High Similarity	NPC245482
0.8662	High Similarity	NPC221432
0.8662	High Similarity	NPC143896
0.8662	High Similarity	NPC75049
0.8662	High Similarity	NPC149026
0.8662	High Similarity	NPC51887
0.8657	High Similarity	NPC92624
0.8657	High Similarity	NPC109123
0.8652	High Similarity	NPC110969
0.8652	High Similarity	NPC3188
0.8636	High Similarity	NPC10926
0.8633	High Similarity	NPC181124
0.8633	High Similarity	NPC188879
0.8633	High Similarity	NPC162680
0.8633	High Similarity	NPC303644
0.8633	High Similarity	NPC7013
0.8633	High Similarity	NPC116632
0.8633	High Similarity	NPC209560
0.8633	High Similarity	NPC294409
0.8623	High Similarity	NPC118919
0.8615	High Similarity	NPC226275
0.8613	High Similarity	NPC475088
0.8605	High Similarity	NPC294037
0.8603	High Similarity	NPC64359
0.8603	High Similarity	NPC313618
0.8603	High Similarity	NPC309717
0.8603	High Similarity	NPC475008
0.8603	High Similarity	NPC112192
0.8603	High Similarity	NPC189106
0.8603	High Similarity	NPC66384
0.8603	High Similarity	NPC186097
0.8603	High Similarity	NPC475009
0.8603	High Similarity	NPC308037
0.8603	High Similarity	NPC164236
0.8603	High Similarity	NPC128348
0.8601	High Similarity	NPC473013

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 NPC470210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	883
0.2-0.3	1485
0.3-0.4	2743
0.4-0.5	2133
0.5-0.6	1153
0.6-0.7	347
0.7-0.8	115
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8603	High Similarity	NPD1240	Approved
0.8489	Intermediate Similarity	NPD1510	Phase 2
0.8478	Intermediate Similarity	NPD1607	Approved
0.8357	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD943	Approved
0.831	Intermediate Similarity	NPD1549	Phase 2
0.8255	Intermediate Similarity	NPD7411	Suspended
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD4380	Phase 2
0.8105	Intermediate Similarity	NPD7075	Discontinued
0.8042	Intermediate Similarity	NPD2935	Discontinued
0.8042	Intermediate Similarity	NPD2796	Approved
0.8027	Intermediate Similarity	NPD6799	Approved
0.8027	Intermediate Similarity	NPD7390	Discontinued
0.8026	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD7819	Suspended
0.8026	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6801	Discontinued
0.7956	Intermediate Similarity	NPD1164	Approved
0.7945	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6651	Approved
0.7829	Intermediate Similarity	NPD6599	Discontinued
0.7812	Intermediate Similarity	NPD3818	Discontinued
0.7806	Intermediate Similarity	NPD7768	Phase 2
0.7799	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD5406	Approved
0.7793	Intermediate Similarity	NPD5405	Approved
0.7793	Intermediate Similarity	NPD5408	Approved
0.7793	Intermediate Similarity	NPD5404	Approved
0.7744	Intermediate Similarity	NPD9493	Approved
0.773	Intermediate Similarity	NPD6559	Discontinued
0.7727	Intermediate Similarity	NPD1934	Approved
0.7716	Intermediate Similarity	NPD7074	Phase 3
0.7704	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1470	Approved
0.7692	Intermediate Similarity	NPD3882	Suspended
0.7687	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1551	Phase 2
0.7664	Intermediate Similarity	NPD1201	Approved
0.7654	Intermediate Similarity	NPD7054	Approved
0.763	Intermediate Similarity	NPD9545	Approved
0.7616	Intermediate Similarity	NPD2534	Approved
0.7616	Intermediate Similarity	NPD2532	Approved
0.7616	Intermediate Similarity	NPD2533	Approved
0.7607	Intermediate Similarity	NPD7472	Approved
0.7603	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD3750	Approved
0.7564	Intermediate Similarity	NPD2801	Approved
0.7562	Intermediate Similarity	NPD6232	Discontinued
0.7561	Intermediate Similarity	NPD6797	Phase 2
0.7561	Intermediate Similarity	NPD5953	Discontinued
0.755	Intermediate Similarity	NPD1511	Approved
0.7546	Intermediate Similarity	NPD7286	Phase 2
0.7538	Intermediate Similarity	NPD74	Approved
0.7538	Intermediate Similarity	NPD9266	Approved
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7531	Intermediate Similarity	NPD7473	Discontinued
0.7518	Intermediate Similarity	NPD2798	Approved
0.7517	Intermediate Similarity	NPD1243	Approved
0.7517	Intermediate Similarity	NPD2800	Approved
0.7516	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD6959	Discontinued
0.7483	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7808	Phase 3
0.7462	Intermediate Similarity	NPD9264	Approved
0.7462	Intermediate Similarity	NPD9263	Approved
0.7462	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD9267	Approved
0.7451	Intermediate Similarity	NPD1512	Approved
0.7447	Intermediate Similarity	NPD1203	Approved
0.7421	Intermediate Similarity	NPD3749	Approved
0.7413	Intermediate Similarity	NPD6832	Phase 2
0.7405	Intermediate Similarity	NPD3817	Phase 2
0.7403	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5403	Approved
0.7397	Intermediate Similarity	NPD230	Phase 1
0.7386	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6166	Phase 2
0.7362	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD846	Approved
0.7344	Intermediate Similarity	NPD940	Approved
0.7329	Intermediate Similarity	NPD5494	Approved
0.731	Intermediate Similarity	NPD2313	Discontinued
0.7273	Intermediate Similarity	NPD5401	Approved
0.7262	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3748	Approved
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7234	Intermediate Similarity	NPD9717	Approved
0.7234	Intermediate Similarity	NPD9269	Phase 2
0.7234	Intermediate Similarity	NPD3972	Approved
0.7226	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9281	Approved
0.7194	Intermediate Similarity	NPD9268	Approved
0.7192	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD2309	Approved
0.7171	Intermediate Similarity	NPD2654	Approved
0.7163	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD919	Approved
0.7154	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD520	Approved
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7089	Intermediate Similarity	NPD3226	Approved
0.7081	Intermediate Similarity	NPD5402	Approved
0.7075	Intermediate Similarity	NPD3268	Approved
0.7075	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1933	Approved
0.7045	Intermediate Similarity	NPD6535	Approved
0.7045	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD2346	Discontinued
0.703	Intermediate Similarity	NPD5710	Approved
0.703	Intermediate Similarity	NPD5711	Approved
0.7024	Intermediate Similarity	NPD6020	Phase 2
0.702	Intermediate Similarity	NPD7033	Discontinued
0.7013	Intermediate Similarity	NPD3400	Discontinued
0.7013	Intermediate Similarity	NPD7003	Approved
0.6995	Remote Similarity	NPD7584	Approved
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1729	Discontinued
0.697	Remote Similarity	NPD1247	Approved
0.697	Remote Similarity	NPD1237	Approved
0.6966	Remote Similarity	NPD2797	Approved
0.6966	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2859	Approved
0.6953	Remote Similarity	NPD2860	Approved
0.6944	Remote Similarity	NPD6782	Approved
0.6944	Remote Similarity	NPD6780	Approved
0.6944	Remote Similarity	NPD6777	Approved
0.6944	Remote Similarity	NPD6779	Approved
0.6944	Remote Similarity	NPD6776	Approved
0.6944	Remote Similarity	NPD6778	Approved
0.6944	Remote Similarity	NPD6781	Approved
0.6939	Remote Similarity	NPD4908	Phase 1
0.6933	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7700	Phase 2
0.6927	Remote Similarity	NPD7699	Phase 2
0.6923	Remote Similarity	NPD422	Phase 1
0.6919	Remote Similarity	NPD8313	Approved
0.6919	Remote Similarity	NPD8312	Approved
0.6918	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5048	Discontinued
0.6908	Remote Similarity	NPD4308	Phase 3
0.6903	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3926	Phase 2
0.6879	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD2934	Approved
0.6875	Remote Similarity	NPD2933	Approved
0.687	Remote Similarity	NPD1242	Phase 1
0.6863	Remote Similarity	NPD6099	Approved
0.6863	Remote Similarity	NPD6100	Approved
0.6859	Remote Similarity	NPD6190	Approved
0.6854	Remote Similarity	NPD4363	Phase 3
0.6854	Remote Similarity	NPD4360	Phase 2
0.6852	Remote Similarity	NPD37	Approved
0.6842	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4750	Phase 3
0.6831	Remote Similarity	NPD7696	Phase 3
0.6831	Remote Similarity	NPD7697	Approved
0.6831	Remote Similarity	NPD7435	Discontinued
0.6831	Remote Similarity	NPD7698	Approved
0.6828	Remote Similarity	NPD8151	Discontinued
0.6821	Remote Similarity	NPD5124	Phase 1
0.6821	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7266	Discontinued
0.6818	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4361	Phase 2
0.6815	Remote Similarity	NPD3300	Phase 2
0.6806	Remote Similarity	NPD1610	Phase 2
0.6803	Remote Similarity	NPD1019	Discontinued
0.68	Remote Similarity	NPD8150	Discontinued
0.6798	Remote Similarity	NPD6212	Phase 3
0.6798	Remote Similarity	NPD6213	Phase 3
0.6798	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3020	Approved
0.6793	Remote Similarity	NPD7870	Phase 2
0.6793	Remote Similarity	NPD8320	Phase 1
0.6793	Remote Similarity	NPD8319	Approved
0.6793	Remote Similarity	NPD7871	Phase 2
0.679	Remote Similarity	NPD5890	Approved
0.679	Remote Similarity	NPD5889	Approved

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