NPASS Compound

Structure

NPC470211 OpenBabel07101718292D 31 32 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 -1.7321 3.0000 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 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 -4.3301 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 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 -3.4641 2.0000 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 -0.8660 1.5000 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 2.0000 0.0000 O 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 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 17 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 31 1 0 0 0 0 5 12 1 0 0 0 0 5 18 2 0 0 0 0 6 14 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 19 2 0 0 0 0 8 11 2 0 0 0 0 8 19 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 26 2 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 25 31 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.21
Volume:	458.726
LogP:	4.521
LogD:	3.534
LogS:	-4.306
# Rotatable Bonds:	10
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	3.266
Fsp3:	0.269
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:	-4.878
MDCK Permeability:	1.9383478502277285e-05
Pgp-inhibitor:	0.379
Pgp-substrate:	0.372
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	100.23887634277344%
Volume Distribution (VD):	0.305
Pgp-substrate:	0.4915429353713989%

ADMET: Metabolism

CYP1A2-inhibitor:	0.792
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.777
CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.806
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.525
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	8.575
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.259
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.937
Carcinogencity:	0.386
Eye Corrosion:	0.003
Eye Irritation:	0.15
Respiratory Toxicity:	0.761

Download Data

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

Natural Product: NPC470211

Natural Product ID:	NPC470211
*Common Name:**	Xanthoangelol G
IUPAC Name:	(E)-1-[2-hydroxy-3-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienyl]-4-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:	Xanthoangelol G
Standard InCHIKey:	NYGYGFOLOACYGB-NKUGMWFWSA-N
Standard InCHI:	InChI=1S/C26H30O5/c1-17(2)23(28)14-6-18(3)5-12-22-25(31-4)16-13-21(26(22)30)24(29)15-9-19-7-10-20(27)11-8-19/h5,7-11,13,15-16,23,27-28,30H,1,6,12,14H2,2-4H3/b15-9+,18-5+
SMILES:	CC(=C)C(CCC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823414
PubChem CID:	42607536
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	=	24200.0	nM	PMID[552654]
NPT2228	Individual Protein	Neuraminidase	Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1))	Ki	=	20000.0	nM	PMID[552654]

☑ 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 NPC470211 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	338
0.1-0.2	1389
0.2-0.3	3630
0.3-0.4	9352
0.4-0.5	9279
0.5-0.6	3590
0.6-0.7	5789
0.7-0.8	5882
0.8-0.85	1922
0.85-0.9	981
0.9-0.95	449
0.95-1	96

Similarity Score	Similarity Level	Natural Product ID
0.9852	High Similarity	NPC470087
0.9852	High Similarity	NPC321980
0.9774	High Similarity	NPC98115
0.9774	High Similarity	NPC150399
0.9774	High Similarity	NPC249606
0.9774	High Similarity	NPC186838
0.9774	High Similarity	NPC12165
0.9774	High Similarity	NPC1486
0.9774	High Similarity	NPC477243
0.9774	High Similarity	NPC477244
0.9774	High Similarity	NPC477242
0.9774	High Similarity	NPC41461
0.9774	High Similarity	NPC274109
0.9774	High Similarity	NPC25287
0.9774	High Similarity	NPC66349
0.9774	High Similarity	NPC168105
0.9708	High Similarity	NPC301751
0.9708	High Similarity	NPC476178
0.9708	High Similarity	NPC117836
0.9708	High Similarity	NPC51887
0.9708	High Similarity	NPC475705
0.9708	High Similarity	NPC245482
0.9706	High Similarity	NPC470089
0.9701	High Similarity	NPC472419
0.9701	High Similarity	NPC153979
0.9701	High Similarity	NPC317119
0.9699	High Similarity	NPC131039
0.9699	High Similarity	NPC13575
0.9699	High Similarity	NPC156092
0.9635	High Similarity	NPC148545
0.9632	High Similarity	NPC219917
0.9632	High Similarity	NPC48624
0.9632	High Similarity	NPC326109
0.9632	High Similarity	NPC259166
0.9632	High Similarity	NPC144118
0.9632	High Similarity	NPC215311
0.9632	High Similarity	NPC213659
0.9632	High Similarity	NPC204985
0.9632	High Similarity	NPC172250
0.9632	High Similarity	NPC80962
0.963	High Similarity	NPC21350
0.963	High Similarity	NPC471620
0.9624	High Similarity	NPC103842
0.9624	High Similarity	NPC164136
0.9624	High Similarity	NPC286336
0.9568	High Similarity	NPC316769
0.9565	High Similarity	NPC143896
0.9565	High Similarity	NPC91560
0.9565	High Similarity	NPC221432
0.9565	High Similarity	NPC310130
0.9565	High Similarity	NPC164980
0.9565	High Similarity	NPC75049
0.9565	High Similarity	NPC149026
0.9565	High Similarity	NPC169591
0.9565	High Similarity	NPC68104
0.9565	High Similarity	NPC39329
0.9565	High Similarity	NPC175504
0.9565	High Similarity	NPC257097
0.9565	High Similarity	NPC150408
0.9562	High Similarity	NPC55832
0.9562	High Similarity	NPC469404
0.9562	High Similarity	NPC268204
0.9562	High Similarity	NPC52789
0.9562	High Similarity	NPC26051
0.9559	High Similarity	NPC472366
0.9559	High Similarity	NPC295384
0.9559	High Similarity	NPC283429
0.9559	High Similarity	NPC477956
0.9549	High Similarity	NPC294593
0.9549	High Similarity	NPC82225
0.9549	High Similarity	NPC159623
0.9549	High Similarity	NPC337373
0.9549	High Similarity	NPC188646
0.9549	High Similarity	NPC27643
0.9549	High Similarity	NPC204960
0.9549	High Similarity	NPC312318
0.9549	High Similarity	NPC18877
0.9549	High Similarity	NPC20560
0.9549	High Similarity	NPC472365
0.9549	High Similarity	NPC263670
0.9549	High Similarity	NPC175098
0.9549	High Similarity	NPC56031
0.9549	High Similarity	NPC139813
0.9549	High Similarity	NPC242294
0.9549	High Similarity	NPC144051
0.9549	High Similarity	NPC192304
0.9549	High Similarity	NPC28753
0.95	High Similarity	NPC51070
0.95	High Similarity	NPC222298
0.9496	High Similarity	NPC236766
0.9496	High Similarity	NPC473015
0.9496	High Similarity	NPC209040
0.9496	High Similarity	NPC473013
0.9496	High Similarity	NPC197252
0.9493	High Similarity	NPC227579
0.9493	High Similarity	NPC78
0.9493	High Similarity	NPC194432
0.9493	High Similarity	NPC324436
0.9493	High Similarity	NPC328164
0.9493	High Similarity	NPC265040
0.9493	High Similarity	NPC177354
0.9493	High Similarity	NPC10937
0.9493	High Similarity	NPC228504
0.9493	High Similarity	NPC296917
0.9493	High Similarity	NPC66515
0.9493	High Similarity	NPC166482
0.9493	High Similarity	NPC148757
0.9493	High Similarity	NPC64915
0.9493	High Similarity	NPC40833
0.9493	High Similarity	NPC1089
0.9493	High Similarity	NPC125855
0.9493	High Similarity	NPC182852
0.9493	High Similarity	NPC324134
0.9493	High Similarity	NPC107572
0.9493	High Similarity	NPC223500
0.9493	High Similarity	NPC306829
0.9493	High Similarity	NPC76372
0.9493	High Similarity	NPC161506
0.9493	High Similarity	NPC32739
0.9493	High Similarity	NPC37496
0.9493	High Similarity	NPC166934
0.9493	High Similarity	NPC167624
0.9493	High Similarity	NPC76338
0.9493	High Similarity	NPC220998
0.9489	High Similarity	NPC101366
0.9489	High Similarity	NPC11056
0.9489	High Similarity	NPC253822
0.9485	High Similarity	NPC243528
0.9485	High Similarity	NPC251681
0.9485	High Similarity	NPC124269
0.9474	High Similarity	NPC129132
0.9474	High Similarity	NPC257756
0.9474	High Similarity	NPC87231
0.9474	High Similarity	NPC212631
0.9474	High Similarity	NPC205468
0.9429	High Similarity	NPC472629
0.9424	High Similarity	NPC214166
0.9424	High Similarity	NPC77794
0.9424	High Similarity	NPC223812
0.9424	High Similarity	NPC478086
0.9424	High Similarity	NPC185276
0.9424	High Similarity	NPC316816
0.9424	High Similarity	NPC107177
0.9424	High Similarity	NPC125894
0.9424	High Similarity	NPC81697
0.9424	High Similarity	NPC85162
0.9424	High Similarity	NPC278249
0.942	High Similarity	NPC213322
0.942	High Similarity	NPC166689
0.942	High Similarity	NPC4743
0.942	High Similarity	NPC96408
0.942	High Similarity	NPC156190
0.942	High Similarity	NPC110969
0.942	High Similarity	NPC312391
0.942	High Similarity	NPC17170
0.942	High Similarity	NPC258630
0.942	High Similarity	NPC110038
0.942	High Similarity	NPC279650
0.942	High Similarity	NPC248372
0.942	High Similarity	NPC3188
0.942	High Similarity	NPC324386
0.9416	High Similarity	NPC139554
0.9412	High Similarity	NPC162680
0.9412	High Similarity	NPC181124
0.9412	High Similarity	NPC209560
0.9412	High Similarity	NPC294409
0.9412	High Similarity	NPC7013
0.9412	High Similarity	NPC303644
0.9412	High Similarity	NPC188879
0.9412	High Similarity	NPC116632
0.9407	High Similarity	NPC84699
0.9398	High Similarity	NPC66384
0.9398	High Similarity	NPC164236
0.9398	High Similarity	NPC64359
0.9398	High Similarity	NPC475008
0.9398	High Similarity	NPC186097
0.9398	High Similarity	NPC475009
0.9398	High Similarity	NPC128348
0.9398	High Similarity	NPC189106
0.9398	High Similarity	NPC309717
0.9398	High Similarity	NPC112192
0.9398	High Similarity	NPC262359
0.9398	High Similarity	NPC313618
0.9398	High Similarity	NPC308037
0.9366	High Similarity	NPC89442
0.9362	High Similarity	NPC472627
0.9362	High Similarity	NPC110303
0.9362	High Similarity	NPC23728
0.9357	High Similarity	NPC224714
0.9357	High Similarity	NPC473014
0.9357	High Similarity	NPC87486
0.9357	High Similarity	NPC131579
0.9357	High Similarity	NPC235217
0.9357	High Similarity	NPC124780
0.9357	High Similarity	NPC131568
0.9357	High Similarity	NPC476055
0.9357	High Similarity	NPC319752
0.9357	High Similarity	NPC470890
0.9353	High Similarity	NPC11561
0.9353	High Similarity	NPC147145

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 NPC470211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	915
0.2-0.3	1497
0.3-0.4	2535
0.4-0.5	2022
0.5-0.6	1197
0.6-0.7	483
0.7-0.8	155
0.8-0.85	31
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9398	High Similarity	NPD1240	Approved
0.9265	High Similarity	NPD1510	Phase 2
0.9259	High Similarity	NPD1607	Approved
0.9203	High Similarity	NPD1549	Phase 2
0.9167	High Similarity	NPD4380	Phase 2
0.913	High Similarity	NPD1550	Clinical (unspecified phase)
0.913	High Similarity	NPD1552	Clinical (unspecified phase)
0.9085	High Similarity	NPD4378	Clinical (unspecified phase)
0.8951	High Similarity	NPD7410	Clinical (unspecified phase)
0.8921	High Similarity	NPD2796	Approved
0.8851	High Similarity	NPD2393	Clinical (unspecified phase)
0.8844	High Similarity	NPD7411	Suspended
0.88	High Similarity	NPD7075	Discontinued
0.8792	High Similarity	NPD8443	Clinical (unspecified phase)
0.8784	High Similarity	NPD6801	Discontinued
0.8725	High Similarity	NPD7096	Clinical (unspecified phase)
0.8621	High Similarity	NPD6799	Approved
0.86	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD6651	Approved
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8533	High Similarity	NPD1934	Approved
0.8521	High Similarity	NPD2935	Discontinued
0.8472	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6599	Discontinued
0.8366	Intermediate Similarity	NPD3882	Suspended
0.8366	Intermediate Similarity	NPD7768	Phase 2
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6959	Discontinued
0.8264	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD1511	Approved
0.8235	Intermediate Similarity	NPD2801	Approved
0.8228	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6166	Phase 2
0.8219	Intermediate Similarity	NPD2800	Approved
0.82	Intermediate Similarity	NPD5403	Approved
0.8188	Intermediate Similarity	NPD2533	Approved
0.8188	Intermediate Similarity	NPD2532	Approved
0.8188	Intermediate Similarity	NPD2534	Approved
0.8163	Intermediate Similarity	NPD3750	Approved
0.8133	Intermediate Similarity	NPD1512	Approved
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8101	Intermediate Similarity	NPD6232	Discontinued
0.8095	Intermediate Similarity	NPD1243	Approved
0.8089	Intermediate Similarity	NPD5494	Approved
0.8086	Intermediate Similarity	NPD5953	Discontinued
0.8079	Intermediate Similarity	NPD920	Approved
0.8075	Intermediate Similarity	NPD7286	Phase 2
0.8069	Intermediate Similarity	NPD2799	Discontinued
0.8069	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD5401	Approved
0.8063	Intermediate Similarity	NPD7473	Discontinued
0.8054	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD943	Approved
0.8041	Intermediate Similarity	NPD4628	Phase 3
0.8037	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7054	Approved
0.7962	Intermediate Similarity	NPD3749	Approved
0.7959	Intermediate Similarity	NPD2344	Approved
0.7949	Intermediate Similarity	NPD3817	Phase 2
0.7947	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1203	Approved
0.7914	Intermediate Similarity	NPD7472	Approved
0.7899	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6832	Phase 2
0.7872	Intermediate Similarity	NPD2798	Approved
0.7866	Intermediate Similarity	NPD6797	Phase 2
0.7853	Intermediate Similarity	NPD5844	Phase 1
0.7852	Intermediate Similarity	NPD2654	Approved
0.7842	Intermediate Similarity	NPD3972	Approved
0.7834	Intermediate Similarity	NPD5402	Approved
0.7823	Intermediate Similarity	NPD3748	Approved
0.7823	Intermediate Similarity	NPD7033	Discontinued
0.7818	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.7763	Intermediate Similarity	NPD7390	Discontinued
0.7748	Intermediate Similarity	NPD2309	Approved
0.7737	Intermediate Similarity	NPD9545	Approved
0.7721	Intermediate Similarity	NPD9493	Approved
0.7714	Intermediate Similarity	NPD9717	Approved
0.7688	Intermediate Similarity	NPD919	Approved
0.7665	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4908	Phase 1
0.763	Intermediate Similarity	NPD4363	Phase 3
0.763	Intermediate Similarity	NPD4360	Phase 2
0.7628	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD7458	Discontinued
0.7619	Intermediate Similarity	NPD5124	Phase 1
0.7619	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1548	Phase 1
0.7593	Intermediate Similarity	NPD1247	Approved
0.759	Intermediate Similarity	NPD1729	Discontinued
0.7586	Intermediate Similarity	NPD3027	Phase 3
0.7552	Intermediate Similarity	NPD1164	Approved
0.7546	Intermediate Similarity	NPD5710	Approved
0.7546	Intermediate Similarity	NPD5711	Approved
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3268	Approved
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD422	Phase 1
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD230	Phase 1
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7003	Approved
0.7431	Intermediate Similarity	NPD2797	Approved
0.7431	Intermediate Similarity	NPD1470	Approved
0.7429	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5406	Approved
0.7417	Intermediate Similarity	NPD5405	Approved
0.7417	Intermediate Similarity	NPD5408	Approved
0.7417	Intermediate Similarity	NPD5404	Approved
0.7405	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1201	Approved
0.7383	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4662	Approved
0.7372	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD4661	Approved
0.7361	Intermediate Similarity	NPD1876	Approved
0.7351	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4308	Phase 3
0.7315	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6798	Discontinued
0.7297	Intermediate Similarity	NPD3764	Approved
0.7294	Intermediate Similarity	NPD6104	Discontinued
0.7268	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD1933	Approved
0.7262	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1019	Discontinued
0.7255	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3225	Approved
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7222	Intermediate Similarity	NPD6777	Approved
0.7222	Intermediate Similarity	NPD6779	Approved
0.7222	Intermediate Similarity	NPD6781	Approved
0.7222	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6778	Approved
0.7222	Intermediate Similarity	NPD6776	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD1465	Phase 2
0.7222	Intermediate Similarity	NPD6780	Approved
0.7222	Intermediate Similarity	NPD6782	Approved
0.7211	Intermediate Similarity	NPD9494	Approved
0.7209	Intermediate Similarity	NPD8313	Approved
0.7209	Intermediate Similarity	NPD8312	Approved
0.7208	Intermediate Similarity	NPD2424	Discontinued
0.7205	Intermediate Similarity	NPD5890	Approved
0.7205	Intermediate Similarity	NPD5889	Approved
0.72	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3266	Approved
0.7192	Intermediate Similarity	NPD3267	Approved
0.7183	Intermediate Similarity	NPD1651	Approved
0.7181	Intermediate Similarity	NPD1296	Phase 2
0.7181	Intermediate Similarity	NPD411	Approved
0.7179	Intermediate Similarity	NPD3887	Approved
0.7178	Intermediate Similarity	NPD4288	Approved
0.7178	Intermediate Similarity	NPD2296	Approved
0.7172	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6844	Discontinued
0.716	Intermediate Similarity	NPD3751	Discontinued
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4966	Approved
0.7134	Intermediate Similarity	NPD4965	Approved
0.7134	Intermediate Similarity	NPD4967	Phase 2
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD9266	Approved
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7123	Intermediate Similarity	NPD1283	Approved
0.7117	Intermediate Similarity	NPD5761	Phase 2
0.7117	Intermediate Similarity	NPD5760	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