NPASS Compound

Structure

NPC470446 OpenBabel07101719252D 48 52 0 0 1 0 0 0 0 0999 V2000 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 -4.3301 1.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 0.8660 -0.5000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 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 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 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 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 1 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 -0.0000 4.0000 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 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 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 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 0.8660 2.5000 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 1 0 0 0 0 3 42 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 43 1 0 0 0 0 9 1 1 1 0 0 0 9 25 1 0 0 0 0 9 44 1 0 0 0 0 10 31 2 0 0 0 0 10 45 1 0 0 0 0 11 26 1 0 0 0 0 12 13 2 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 27 1 0 0 0 0 14 34 1 0 0 0 0 15 17 2 0 0 0 0 15 46 1 0 0 0 0 16 8 1 6 0 0 0 16 18 1 0 0 0 0 16 47 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 35 1 1 0 0 0 19 27 2 0 0 0 0 19 36 1 0 0 0 0 20 28 1 0 0 0 0 20 37 2 0 0 0 0 21 23 1 0 0 0 0 21 38 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 22 39 1 1 0 0 0 23 30 1 0 0 0 0 23 40 1 1 0 0 0 24 29 1 0 0 0 0 24 41 1 1 0 0 0 25 45 1 6 0 0 0 26 28 2 0 0 0 0 26 46 1 0 0 0 0 27 42 1 0 0 0 0 28 48 1 0 0 0 0 29 43 1 6 0 0 0 29 44 1 0 0 0 0 30 47 1 0 0 0 0 30 48 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	682.17
Volume:	619.15
LogP:	0.298
LogD:	0.006
LogS:	-3.787
# Rotatable Bonds:	9
TPSA:	284.73
# H-Bond Aceptor:	18
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.101
Synthetic Accessibility Score:	4.974
Fsp3:	0.467
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.503
MDCK Permeability:	3.930670936824754e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.833
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	82.99195098876953%
Volume Distribution (VD):	0.592
Pgp-substrate:	22.654865264892578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.317
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.333
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.795
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.616
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.3
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC470446

Natural Product ID:	NPC470446
*Common Name:**	6-Methoxyquercetin-3-O-(4-O-Acetyl)-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	[(2S,3R,4S,5R,6R)-6-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	NMYATQQEONGBHA-ASCKONKUSA-N
Standard InCHI:	InChI=1S/C30H34O18/c1-9-25(45-10(2)31)22(39)24(41)29(44-9)43-8-16-18(35)21(38)23(40)30(47-16)48-28-20(37)17-15(7-14(34)27(42-3)19(17)36)46-26(28)11-4-5-12(32)13(33)6-11/h4-7,9,16,18,21-25,29-30,32-36,38-41H,8H2,1-3H3/t9-,16+,18+,21-,22-,23+,24+,25-,29+,30-/m0/s1
SMILES:	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)OC)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037048
PubChem CID:	57409957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.16	mM	PMID[529334]

☑ 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 NPC470446 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	434
0.1-0.2	1896
0.2-0.3	4407
0.3-0.4	9683
0.4-0.5	8361
0.5-0.6	4730
0.6-0.7	5750
0.7-0.8	4962
0.8-0.85	1436
0.85-0.9	533
0.9-0.95	388
0.95-1	117

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470449
1.0	High Similarity	NPC470445
1.0	High Similarity	NPC470447
0.994	High Similarity	NPC470455
0.994	High Similarity	NPC470451
0.988	High Similarity	NPC473571
0.988	High Similarity	NPC126784
0.988	High Similarity	NPC241423
0.988	High Similarity	NPC470443
0.988	High Similarity	NPC473682
0.988	High Similarity	NPC470444
0.988	High Similarity	NPC110941
0.982	High Similarity	NPC173837
0.9763	High Similarity	NPC473072
0.976	High Similarity	NPC198324
0.976	High Similarity	NPC89127
0.976	High Similarity	NPC472385
0.976	High Similarity	NPC65563
0.976	High Similarity	NPC8573
0.976	High Similarity	NPC169733
0.976	High Similarity	NPC471669
0.976	High Similarity	NPC470949
0.9706	High Similarity	NPC148710
0.9704	High Similarity	NPC473073
0.9704	High Similarity	NPC473071
0.9701	High Similarity	NPC477848
0.9701	High Similarity	NPC19108
0.9701	High Similarity	NPC49344
0.9701	High Similarity	NPC220173
0.9701	High Similarity	NPC237435
0.9701	High Similarity	NPC294815
0.9701	High Similarity	NPC43211
0.9701	High Similarity	NPC473327
0.9701	High Similarity	NPC264735
0.9701	High Similarity	NPC135277
0.9701	High Similarity	NPC16194
0.9701	High Similarity	NPC101191
0.9701	High Similarity	NPC476472
0.9701	High Similarity	NPC210094
0.9701	High Similarity	NPC253685
0.9701	High Similarity	NPC115760
0.9647	High Similarity	NPC36138
0.9643	High Similarity	NPC473862
0.9643	High Similarity	NPC211532
0.9643	High Similarity	NPC472380
0.9643	High Similarity	NPC472382
0.9643	High Similarity	NPC268533
0.9643	High Similarity	NPC472384
0.9643	High Similarity	NPC233994
0.9641	High Similarity	NPC21666
0.9641	High Similarity	NPC45522
0.9641	High Similarity	NPC4390
0.9641	High Similarity	NPC24043
0.9641	High Similarity	NPC101026
0.9641	High Similarity	NPC169977
0.9641	High Similarity	NPC42773
0.9641	High Similarity	NPC204693
0.9591	High Similarity	NPC470717
0.9591	High Similarity	NPC21359
0.9591	High Similarity	NPC470416
0.9591	High Similarity	NPC470713
0.9591	High Similarity	NPC460984
0.9591	High Similarity	NPC25946
0.9591	High Similarity	NPC470720
0.9586	High Similarity	NPC89052
0.9586	High Similarity	NPC251417
0.9581	High Similarity	NPC60735
0.9581	High Similarity	NPC471748
0.9581	High Similarity	NPC176740
0.9581	High Similarity	NPC476405
0.9581	High Similarity	NPC134532
0.9581	High Similarity	NPC33054
0.9581	High Similarity	NPC153755
0.9581	High Similarity	NPC117260
0.9581	High Similarity	NPC254540
0.9581	High Similarity	NPC155877
0.9581	High Similarity	NPC211594
0.9581	High Similarity	NPC172807
0.9581	High Similarity	NPC471725
0.9581	High Similarity	NPC3583
0.9581	High Similarity	NPC175107
0.9581	High Similarity	NPC26230
0.9581	High Similarity	NPC259152
0.9581	High Similarity	NPC190003
0.9581	High Similarity	NPC203259
0.9535	High Similarity	NPC295625
0.9535	High Similarity	NPC470719
0.9535	High Similarity	NPC473554
0.9532	High Similarity	NPC470718
0.9532	High Similarity	NPC156785
0.9532	High Similarity	NPC241781
0.9532	High Similarity	NPC107987
0.9532	High Similarity	NPC162394
0.9529	High Similarity	NPC192539
0.9527	High Similarity	NPC202908
0.9527	High Similarity	NPC14187
0.9527	High Similarity	NPC219043
0.9527	High Similarity	NPC292019
0.9527	High Similarity	NPC122467
0.9527	High Similarity	NPC48984
0.9521	High Similarity	NPC116864
0.9521	High Similarity	NPC285197
0.9521	High Similarity	NPC136042
0.9521	High Similarity	NPC95866
0.9521	High Similarity	NPC255157
0.9521	High Similarity	NPC235260
0.9521	High Similarity	NPC67105
0.9521	High Similarity	NPC155763
0.9521	High Similarity	NPC245014
0.9521	High Similarity	NPC84265
0.9521	High Similarity	NPC254855
0.9521	High Similarity	NPC67326
0.9521	High Similarity	NPC29958
0.9521	High Similarity	NPC244776
0.9521	High Similarity	NPC282987
0.9521	High Similarity	NPC156869
0.9521	High Similarity	NPC259896
0.9521	High Similarity	NPC20505
0.9477	High Similarity	NPC275977
0.9477	High Similarity	NPC249560
0.9477	High Similarity	NPC223860
0.9474	High Similarity	NPC222674
0.9471	High Similarity	NPC258044
0.9471	High Similarity	NPC139571
0.9471	High Similarity	NPC217520
0.9471	High Similarity	NPC113836
0.9471	High Similarity	NPC35167
0.9471	High Similarity	NPC267680
0.9471	High Similarity	NPC196127
0.9471	High Similarity	NPC293626
0.9471	High Similarity	NPC168584
0.9471	High Similarity	NPC253521
0.9471	High Similarity	NPC120952
0.9471	High Similarity	NPC217387
0.9471	High Similarity	NPC37668
0.9467	High Similarity	NPC142996
0.9467	High Similarity	NPC102028
0.9464	High Similarity	NPC472386
0.9461	High Similarity	NPC201292
0.9461	High Similarity	NPC86008
0.9461	High Similarity	NPC209296
0.9461	High Similarity	NPC45638
0.9461	High Similarity	NPC226294
0.9461	High Similarity	NPC186807
0.9461	High Similarity	NPC203050
0.9461	High Similarity	NPC219904
0.9461	High Similarity	NPC58053
0.9461	High Similarity	NPC138927
0.9461	High Similarity	NPC475942
0.9461	High Similarity	NPC105025
0.9461	High Similarity	NPC227508
0.9461	High Similarity	NPC469931
0.9461	High Similarity	NPC195257
0.9461	High Similarity	NPC223747
0.9461	High Similarity	NPC93337
0.9461	High Similarity	NPC120099
0.9461	High Similarity	NPC225434
0.9422	High Similarity	NPC33083
0.9422	High Similarity	NPC474093
0.9422	High Similarity	NPC104910
0.9412	High Similarity	NPC472991
0.9412	High Similarity	NPC144097
0.9412	High Similarity	NPC472992
0.9412	High Similarity	NPC61904
0.9408	High Similarity	NPC239549
0.9408	High Similarity	NPC236191
0.9408	High Similarity	NPC51774
0.9408	High Similarity	NPC163165
0.9405	High Similarity	NPC22195
0.9405	High Similarity	NPC206123
0.9405	High Similarity	NPC183357
0.9405	High Similarity	NPC21190
0.9401	High Similarity	NPC325555
0.9401	High Similarity	NPC84362
0.9401	High Similarity	NPC52550
0.9401	High Similarity	NPC223424
0.9401	High Similarity	NPC317489
0.9401	High Similarity	NPC265530
0.9401	High Similarity	NPC226304
0.9401	High Similarity	NPC45618
0.9401	High Similarity	NPC58716
0.9401	High Similarity	NPC275454
0.9401	High Similarity	NPC127546
0.9401	High Similarity	NPC173637
0.9401	High Similarity	NPC146792
0.9368	High Similarity	NPC97817
0.9368	High Similarity	NPC30011
0.9368	High Similarity	NPC72554
0.9368	High Similarity	NPC475179
0.9357	High Similarity	NPC472387
0.9357	High Similarity	NPC477895
0.9357	High Similarity	NPC476621
0.9357	High Similarity	NPC476622
0.9357	High Similarity	NPC476619
0.9357	High Similarity	NPC476618
0.9357	High Similarity	NPC476623
0.9357	High Similarity	NPC476620
0.9353	High Similarity	NPC34267
0.9353	High Similarity	NPC214621
0.9353	High Similarity	NPC198199

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 NPC470446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	979
0.2-0.3	2105
0.3-0.4	2693
0.4-0.5	1792
0.5-0.6	810
0.6-0.7	251
0.7-0.8	96
0.8-0.85	24
0.85-0.9	3
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9701	High Similarity	NPD4338	Clinical (unspecified phase)
0.9641	High Similarity	NPD7251	Discontinued
0.9583	High Similarity	NPD7808	Phase 3
0.9581	High Similarity	NPD6797	Phase 2
0.9521	High Similarity	NPD7472	Approved
0.9461	High Similarity	NPD7054	Approved
0.929	High Similarity	NPD7074	Phase 3
0.9006	High Similarity	NPD7804	Clinical (unspecified phase)
0.8947	High Similarity	NPD3818	Discontinued
0.8941	High Similarity	NPD6166	Phase 2
0.8941	High Similarity	NPD6168	Clinical (unspecified phase)
0.8941	High Similarity	NPD6167	Clinical (unspecified phase)
0.8802	High Similarity	NPD3817	Phase 2
0.8743	High Similarity	NPD2801	Approved
0.8698	High Similarity	NPD4381	Clinical (unspecified phase)
0.858	High Similarity	NPD7993	Clinical (unspecified phase)
0.858	High Similarity	NPD5402	Approved
0.8571	High Similarity	NPD1934	Approved
0.8529	High Similarity	NPD3882	Suspended
0.848	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1512	Approved
0.8304	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD6801	Discontinued
0.8225	Intermediate Similarity	NPD1653	Approved
0.8204	Intermediate Similarity	NPD1511	Approved
0.8171	Intermediate Similarity	NPD5494	Approved
0.8166	Intermediate Similarity	NPD5403	Approved
0.8129	Intermediate Similarity	NPD4380	Phase 2
0.8122	Intermediate Similarity	NPD6559	Discontinued
0.8101	Intermediate Similarity	NPD7228	Approved
0.8095	Intermediate Similarity	NPD6799	Approved
0.8056	Intermediate Similarity	NPD5844	Phase 1
0.8047	Intermediate Similarity	NPD5401	Approved
0.8033	Intermediate Similarity	NPD8312	Approved
0.8033	Intermediate Similarity	NPD8313	Approved
0.8022	Intermediate Similarity	NPD7685	Pre-registration
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3751	Discontinued
0.7989	Intermediate Similarity	NPD1465	Phase 2
0.7979	Intermediate Similarity	NPD7435	Discontinued
0.7978	Intermediate Similarity	NPD3787	Discontinued
0.7946	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7473	Discontinued
0.7941	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7819	Suspended
0.7877	Intermediate Similarity	NPD6232	Discontinued
0.7833	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD8151	Discontinued
0.7771	Intermediate Similarity	NPD7411	Suspended
0.7765	Intermediate Similarity	NPD6190	Approved
0.7746	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD7874	Approved
0.7739	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7266	Discontinued
0.7738	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD6777	Approved
0.7732	Intermediate Similarity	NPD6776	Approved
0.7732	Intermediate Similarity	NPD6778	Approved
0.7732	Intermediate Similarity	NPD6781	Approved
0.7732	Intermediate Similarity	NPD6779	Approved
0.7732	Intermediate Similarity	NPD6782	Approved
0.7732	Intermediate Similarity	NPD6780	Approved
0.773	Intermediate Similarity	NPD7240	Approved
0.7722	Intermediate Similarity	NPD1247	Approved
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7722	Intermediate Similarity	NPD6959	Discontinued
0.7709	Intermediate Similarity	NPD6234	Discontinued
0.7709	Intermediate Similarity	NPD919	Approved
0.7704	Intermediate Similarity	NPD7698	Approved
0.7704	Intermediate Similarity	NPD7696	Phase 3
0.7704	Intermediate Similarity	NPD7697	Approved
0.77	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7783	Phase 2
0.7692	Intermediate Similarity	NPD1549	Phase 2
0.7684	Intermediate Similarity	NPD8455	Phase 2
0.7638	Intermediate Similarity	NPD7701	Phase 2
0.7627	Intermediate Similarity	NPD37	Approved
0.7602	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD4967	Phase 2
0.7598	Intermediate Similarity	NPD4966	Approved
0.7598	Intermediate Similarity	NPD4965	Approved
0.7596	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7871	Phase 2
0.7576	Intermediate Similarity	NPD7870	Phase 2
0.7574	Intermediate Similarity	NPD2796	Approved
0.7538	Intermediate Similarity	NPD7700	Phase 2
0.7538	Intermediate Similarity	NPD7699	Phase 2
0.7529	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1510	Phase 2
0.7487	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8320	Phase 1
0.7487	Intermediate Similarity	NPD8319	Approved
0.7485	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6535	Approved
0.7474	Intermediate Similarity	NPD6534	Approved
0.7471	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3926	Phase 2
0.744	Intermediate Similarity	NPD1933	Approved
0.744	Intermediate Similarity	NPD230	Phase 1
0.7438	Intermediate Similarity	NPD7801	Approved
0.7435	Intermediate Similarity	NPD8434	Phase 2
0.7435	Intermediate Similarity	NPD8150	Discontinued
0.7413	Intermediate Similarity	NPD7584	Approved
0.7403	Intermediate Similarity	NPD7768	Phase 2
0.7399	Intermediate Similarity	NPD3750	Approved
0.7387	Intermediate Similarity	NPD6823	Phase 2
0.7381	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1613	Approved
0.7368	Intermediate Similarity	NPD2935	Discontinued
0.7368	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3749	Approved
0.7337	Intermediate Similarity	NPD447	Suspended
0.7323	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD943	Approved
0.7278	Intermediate Similarity	NPD1240	Approved
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7264	Intermediate Similarity	NPD7680	Approved
0.7232	Intermediate Similarity	NPD2532	Approved
0.7232	Intermediate Similarity	NPD2534	Approved
0.7232	Intermediate Similarity	NPD2533	Approved
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7585	Approved
0.7202	Intermediate Similarity	NPD3027	Phase 3
0.7193	Intermediate Similarity	NPD1607	Approved
0.7167	Intermediate Similarity	NPD7458	Discontinued
0.7157	Intermediate Similarity	NPD7583	Approved
0.7151	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5953	Discontinued
0.7114	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3748	Approved
0.7105	Intermediate Similarity	NPD7286	Phase 2
0.7083	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3226	Approved
0.7071	Intermediate Similarity	NPD6212	Phase 3
0.7071	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6213	Phase 3
0.7065	Intermediate Similarity	NPD5353	Approved
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7041	Intermediate Similarity	NPD6832	Phase 2
0.7039	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6355	Discontinued
0.7011	Intermediate Similarity	NPD7033	Discontinued
0.6959	Remote Similarity	NPD2313	Discontinued
0.6959	Remote Similarity	NPD7549	Discontinued
0.6949	Remote Similarity	NPD6674	Discontinued
0.6949	Remote Similarity	NPD2800	Approved
0.6949	Remote Similarity	NPD1243	Approved
0.6949	Remote Similarity	NPD1652	Phase 2
0.6942	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2346	Discontinued
0.6927	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2799	Discontinued
0.691	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6385	Approved
0.6902	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6386	Approved
0.6895	Remote Similarity	NPD5242	Approved
0.6888	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD9494	Approved
0.6878	Remote Similarity	NPD8127	Discontinued
0.6878	Remote Similarity	NPD5006	Approved
0.6878	Remote Similarity	NPD5005	Approved
0.6875	Remote Similarity	NPD6100	Approved
0.6875	Remote Similarity	NPD6099	Approved
0.6872	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4360	Phase 2
0.6866	Remote Similarity	NPD4363	Phase 3
0.6864	Remote Similarity	NPD1203	Approved
0.6857	Remote Similarity	NPD7097	Phase 1
0.6842	Remote Similarity	NPD5710	Approved
0.6842	Remote Similarity	NPD5711	Approved
0.684	Remote Similarity	NPD7930	Approved
0.6839	Remote Similarity	NPD5124	Phase 1
0.6839	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1091	Approved
0.6806	Remote Similarity	NPD7907	Approved
0.6804	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD8059	Phase 3
0.68	Remote Similarity	NPD6651	Approved
0.6796	Remote Similarity	NPD7390	Discontinued
0.6793	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD8067	Phase 3
0.6786	Remote Similarity	NPD9269	Phase 2
0.6782	Remote Similarity	NPD4060	Phase 1

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