NPASS Compound

Structure

NPC473621 OpenBabel07101719512D 52 57 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 0.0000 4.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 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 0.8660 4.5000 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 5.1962 -0.0000 0.0000 C 0 0 0 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 4.3301 -0.5000 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 1.7321 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 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 1 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 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 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 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 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 -3.4641 1.0000 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 -1.7321 -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 2.5981 2.5000 0.0000 O 0 3 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 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 13 1 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 1 0 0 0 0 5 14 2 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 33 1 0 0 0 0 9 1 1 6 0 0 0 9 19 1 0 0 0 0 9 46 1 0 0 0 0 10 27 1 0 0 0 0 11 34 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 35 1 0 0 0 0 14 36 1 0 0 0 0 15 37 1 0 0 0 0 16 47 2 0 0 0 0 17 27 2 0 0 0 0 17 48 1 0 0 0 0 18 8 1 1 0 0 0 18 20 1 0 0 0 0 18 49 1 0 0 0 0 19 21 1 0 0 0 0 19 38 1 1 0 0 0 20 22 1 0 0 0 0 20 39 1 6 0 0 0 21 24 1 0 0 0 0 21 40 1 6 0 0 0 22 25 1 0 0 0 0 22 41 1 1 0 0 0 23 26 1 0 0 0 0 23 28 1 0 0 0 0 23 42 1 1 0 0 0 24 29 1 0 0 0 0 24 43 1 6 0 0 0 25 30 1 0 0 0 0 25 44 1 6 0 0 0 26 31 1 0 0 0 0 26 45 1 6 0 0 0 27 47 1 0 0 0 0 28 32 1 0 0 0 0 28 50 1 6 0 0 0 29 46 1 0 0 0 0 29 51 1 6 0 0 0 30 49 1 0 0 0 0 30 50 1 1 0 0 0 31 51 1 1 0 0 0 31 52 1 0 0 0 0 32 48 1 1 0 0 0 32 52 1 0 0 0 0 M CHG 1 47 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	743.2
Volume:	666.72
LogP:	-0.784
LogD:	-0.217
LogS:	-2.389
# Rotatable Bonds:	8
TPSA:	329.67
# H-Bond Aceptor:	20
# H-Bond Donor:	13
# Rings:	6
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	5.534
Fsp3:	0.531
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.714
MDCK Permeability:	2.884684181481134e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.979
20% Bioavailability (F20%):	0.171
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	84.5328140258789%
Volume Distribution (VD):	0.513
Pgp-substrate:	18.513383865356445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.369
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.418
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.338
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.508
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.19
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC473621

Natural Product ID:	NPC473621
*Common Name:**	E163
IUPAC Name:	(2S,3S,4S,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	SHNZRWDOZIKVHM-XHFJEOHCSA-O
Standard InCHI:	InChI=1S/C32H38O20/c1-9-19(38)21(40)24(43)29(46-9)51-31-26(45)23(42)28(50-30-25(44)22(41)20(39)18(8-33)49-30)32(52-31)48-17-7-12-14(36)5-11(34)6-16(12)47-27(17)10-2-3-13(35)15(37)4-10/h2-7,9,18-26,28-33,38-45H,8H2,1H3,(H3-,34,35,36,37)/p+1/t9-,18-,19-,20-,21+,22+,23+,24+,25-,26+,28-,29+,30+,31+,32-/m1/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(C(C(O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C=C5)O)O)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447326
PubChem CID:	44558982
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
NPO33237	tart cherries	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075763]

☑ 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	=	39.0	%	PMID[490478]

☑ 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 NPC473621 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	474
0.1-0.2	1793
0.2-0.3	4051
0.3-0.4	9434
0.4-0.5	8339
0.5-0.6	5243
0.6-0.7	5742
0.7-0.8	5202
0.8-0.85	1442
0.85-0.9	499
0.9-0.95	414
0.95-1	64

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC280945
0.972	High Similarity	NPC473480
0.972	High Similarity	NPC15538
0.9514	High Similarity	NPC125755
0.951	High Similarity	NPC469313
0.951	High Similarity	NPC76176
0.951	High Similarity	NPC138227
0.951	High Similarity	NPC168579
0.9444	High Similarity	NPC475096
0.9444	High Similarity	NPC277867
0.9444	High Similarity	NPC161700
0.9441	High Similarity	NPC37793
0.9404	High Similarity	NPC185231
0.9315	High Similarity	NPC227902
0.9301	High Similarity	NPC273932
0.9301	High Similarity	NPC89686
0.9301	High Similarity	NPC257095
0.9247	High Similarity	NPC190714
0.9247	High Similarity	NPC99515
0.9241	High Similarity	NPC225445
0.9236	High Similarity	NPC475084
0.9236	High Similarity	NPC189115
0.9236	High Similarity	NPC469559
0.9211	High Similarity	NPC147743
0.9211	High Similarity	NPC4809
0.9211	High Similarity	NPC73517
0.9172	High Similarity	NPC473044
0.9172	High Similarity	NPC116922
0.9167	High Similarity	NPC469661
0.915	High Similarity	NPC205613
0.915	High Similarity	NPC212614
0.915	High Similarity	NPC86630
0.915	High Similarity	NPC151474
0.915	High Similarity	NPC471404
0.915	High Similarity	NPC106601
0.915	High Similarity	NPC159526
0.9122	High Similarity	NPC175976
0.911	High Similarity	NPC25292
0.911	High Similarity	NPC473045
0.9097	High Similarity	NPC106944
0.9091	High Similarity	NPC1253
0.9091	High Similarity	NPC87777
0.9091	High Similarity	NPC262328
0.9091	High Similarity	NPC100936
0.9054	High Similarity	NPC39657
0.9041	High Similarity	NPC252169
0.9041	High Similarity	NPC113680
0.9041	High Similarity	NPC278961
0.9034	High Similarity	NPC210192
0.9028	High Similarity	NPC98777
0.9028	High Similarity	NPC212770
0.9021	High Similarity	NPC40664
0.9021	High Similarity	NPC165482
0.9021	High Similarity	NPC138350
0.9021	High Similarity	NPC203230
0.9021	High Similarity	NPC3293
0.9021	High Similarity	NPC197723
0.9021	High Similarity	NPC242028
0.9007	High Similarity	NPC169404
0.9007	High Similarity	NPC322899
0.9007	High Similarity	NPC469944
0.9007	High Similarity	NPC46283
0.9007	High Similarity	NPC21902
0.9007	High Similarity	NPC53587
0.9007	High Similarity	NPC176186
0.9007	High Similarity	NPC226108
0.9007	High Similarity	NPC272552
0.9007	High Similarity	NPC134911
0.9007	High Similarity	NPC44192
0.9	High Similarity	NPC472710
0.9	High Similarity	NPC472709
0.898	High Similarity	NPC177597
0.8973	High Similarity	NPC5262
0.8973	High Similarity	NPC472714
0.8958	High Similarity	NPC211549
0.8958	High Similarity	NPC470413
0.8958	High Similarity	NPC138738
0.8958	High Similarity	NPC59324
0.8958	High Similarity	NPC65530
0.8951	High Similarity	NPC238243
0.8947	High Similarity	NPC224161
0.8947	High Similarity	NPC150442
0.8947	High Similarity	NPC78809
0.894	High Similarity	NPC259707
0.8933	High Similarity	NPC51328
0.8933	High Similarity	NPC55158
0.8933	High Similarity	NPC35877
0.8933	High Similarity	NPC286235
0.8933	High Similarity	NPC55715
0.8933	High Similarity	NPC95392
0.8912	High Similarity	NPC81638
0.8889	High Similarity	NPC177035
0.8889	High Similarity	NPC306441
0.8889	High Similarity	NPC164857
0.8889	High Similarity	NPC52277
0.8889	High Similarity	NPC16435
0.8889	High Similarity	NPC199459
0.8889	High Similarity	NPC46335
0.8882	High Similarity	NPC226809
0.8882	High Similarity	NPC279406
0.8881	High Similarity	NPC188555
0.8881	High Similarity	NPC130496
0.8874	High Similarity	NPC470927
0.8874	High Similarity	NPC475224
0.8874	High Similarity	NPC225815
0.8874	High Similarity	NPC185955
0.8874	High Similarity	NPC469706
0.8874	High Similarity	NPC214326
0.8874	High Similarity	NPC9933
0.8874	High Similarity	NPC218041
0.8874	High Similarity	NPC260781
0.8874	High Similarity	NPC182368
0.8874	High Similarity	NPC145979
0.8874	High Similarity	NPC469707
0.8874	High Similarity	NPC257970
0.8867	High Similarity	NPC270751
0.8867	High Similarity	NPC248132
0.8867	High Similarity	NPC281549
0.8867	High Similarity	NPC130449
0.8851	High Similarity	NPC471063
0.8851	High Similarity	NPC171932
0.8851	High Similarity	NPC28440
0.8851	High Similarity	NPC472712
0.8851	High Similarity	NPC187774
0.8851	High Similarity	NPC472713
0.8851	High Similarity	NPC473046
0.8851	High Similarity	NPC118385
0.8844	High Similarity	NPC128337
0.8844	High Similarity	NPC230718
0.8844	High Similarity	NPC49542
0.8844	High Similarity	NPC5253
0.8844	High Similarity	NPC84207
0.8844	High Similarity	NPC472353
0.8844	High Similarity	NPC139976
0.8828	High Similarity	NPC134260
0.8824	High Similarity	NPC306267
0.8824	High Similarity	NPC20050
0.8819	High Similarity	NPC121812
0.8819	High Similarity	NPC470236
0.8819	High Similarity	NPC260898
0.8819	High Similarity	NPC470356
0.8819	High Similarity	NPC234333
0.8819	High Similarity	NPC61946
0.8819	High Similarity	NPC47398
0.8819	High Similarity	NPC112939
0.8819	High Similarity	NPC164787
0.8819	High Similarity	NPC112246
0.8819	High Similarity	NPC474206
0.8819	High Similarity	NPC151224
0.8819	High Similarity	NPC94750
0.8811	High Similarity	NPC11060
0.8811	High Similarity	NPC115022
0.8811	High Similarity	NPC294166
0.8808	High Similarity	NPC259347
0.8808	High Similarity	NPC94871
0.8808	High Similarity	NPC306890
0.8808	High Similarity	NPC476398
0.8808	High Similarity	NPC106138
0.8808	High Similarity	NPC473427
0.8808	High Similarity	NPC471062
0.8808	High Similarity	NPC470933
0.8808	High Similarity	NPC476386
0.88	High Similarity	NPC275284
0.88	High Similarity	NPC213074
0.88	High Similarity	NPC15956
0.88	High Similarity	NPC114505
0.88	High Similarity	NPC31325
0.88	High Similarity	NPC224674
0.88	High Similarity	NPC193473
0.8784	High Similarity	NPC470950
0.8784	High Similarity	NPC185307
0.8784	High Similarity	NPC46092
0.8776	High Similarity	NPC178054
0.8776	High Similarity	NPC108674
0.8767	High Similarity	NPC292487
0.8759	High Similarity	NPC230734
0.8759	High Similarity	NPC269091
0.8759	High Similarity	NPC470802
0.8759	High Similarity	NPC474639
0.8759	High Similarity	NPC227503
0.8759	High Similarity	NPC302701
0.8758	High Similarity	NPC215060
0.8758	High Similarity	NPC59692
0.8758	High Similarity	NPC233467
0.8758	High Similarity	NPC476352
0.875	High Similarity	NPC251981
0.875	High Similarity	NPC35731
0.875	High Similarity	NPC170694
0.875	High Similarity	NPC187194
0.875	High Similarity	NPC477612
0.875	High Similarity	NPC87696
0.875	High Similarity	NPC107478
0.875	High Similarity	NPC476411
0.875	High Similarity	NPC238140
0.875	High Similarity	NPC13745
0.875	High Similarity	NPC48863
0.8741	High Similarity	NPC61477
0.8741	High Similarity	NPC261619
0.8741	High Similarity	NPC78770
0.8741	High Similarity	NPC254275

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 NPC473621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	954
0.2-0.3	2055
0.3-0.4	2713
0.4-0.5	1802
0.5-0.6	821
0.6-0.7	264
0.7-0.8	94
0.8-0.85	21
0.85-0.9	6
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD1613	Approved
0.8741	High Similarity	NPD1612	Clinical (unspecified phase)
0.8642	High Similarity	NPD7074	Phase 3
0.8528	High Similarity	NPD7472	Approved
0.8466	Intermediate Similarity	NPD7054	Approved
0.8462	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7251	Discontinued
0.8403	Intermediate Similarity	NPD3027	Phase 3
0.8392	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7808	Phase 3
0.8364	Intermediate Similarity	NPD6797	Phase 2
0.8323	Intermediate Similarity	NPD1653	Approved
0.8267	Intermediate Similarity	NPD7266	Discontinued
0.8182	Intermediate Similarity	NPD7228	Approved
0.8039	Intermediate Similarity	NPD6674	Discontinued
0.8024	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1091	Approved
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7959	Intermediate Similarity	NPD4908	Phase 1
0.7952	Intermediate Similarity	NPD6166	Phase 2
0.7952	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD8455	Phase 2
0.7914	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD7240	Approved
0.7758	Intermediate Similarity	NPD6234	Discontinued
0.773	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1610	Phase 2
0.7669	Intermediate Similarity	NPD37	Approved
0.7665	Intermediate Similarity	NPD7199	Phase 2
0.7636	Intermediate Similarity	NPD4966	Approved
0.7636	Intermediate Similarity	NPD4967	Phase 2
0.7636	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD6559	Discontinued
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.7533	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7417	Intermediate Similarity	NPD3018	Phase 2
0.741	Intermediate Similarity	NPD2801	Approved
0.7386	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD4749	Approved
0.7366	Intermediate Similarity	NPD7680	Approved
0.7358	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7447	Phase 1
0.7337	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4380	Phase 2
0.7329	Intermediate Similarity	NPD5058	Phase 3
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7305	Intermediate Similarity	NPD1465	Phase 2
0.7299	Intermediate Similarity	NPD5844	Phase 1
0.7284	Intermediate Similarity	NPD1511	Approved
0.7284	Intermediate Similarity	NPD7212	Phase 2
0.7284	Intermediate Similarity	NPD7213	Phase 3
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD7843	Approved
0.7273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD2983	Phase 2
0.7267	Intermediate Similarity	NPD2982	Phase 2
0.7262	Intermediate Similarity	NPD3817	Phase 2
0.7261	Intermediate Similarity	NPD7097	Phase 1
0.725	Intermediate Similarity	NPD1652	Phase 2
0.7248	Intermediate Similarity	NPD3705	Approved
0.7247	Intermediate Similarity	NPD8054	Approved
0.7247	Intermediate Similarity	NPD8053	Approved
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD3882	Suspended
0.7219	Intermediate Similarity	NPD8651	Approved
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2981	Phase 2
0.7195	Intermediate Similarity	NPD1512	Approved
0.7179	Intermediate Similarity	NPD4060	Phase 1
0.7162	Intermediate Similarity	NPD1357	Approved
0.716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4536	Approved
0.7152	Intermediate Similarity	NPD4538	Approved
0.7152	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7127	Intermediate Similarity	NPD6843	Phase 3
0.7127	Intermediate Similarity	NPD6841	Approved
0.7127	Intermediate Similarity	NPD6842	Approved
0.7123	Intermediate Similarity	NPD7157	Approved
0.7123	Intermediate Similarity	NPD6671	Approved
0.7104	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7819	Suspended
0.7093	Intermediate Similarity	NPD5494	Approved
0.7083	Intermediate Similarity	NPD228	Approved
0.7073	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5402	Approved
0.7059	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6959	Discontinued
0.7048	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7549	Discontinued
0.702	Intermediate Similarity	NPD422	Phase 1
0.7019	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7783	Phase 2
0.701	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2978	Approved
0.7	Intermediate Similarity	NPD2977	Approved
0.7	Intermediate Similarity	NPD5588	Approved
0.7	Intermediate Similarity	NPD5960	Phase 3
0.6995	Remote Similarity	NPD8151	Discontinued
0.6995	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2684	Approved
0.6986	Remote Similarity	NPD5283	Phase 1
0.6982	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1549	Phase 2
0.6964	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1558	Phase 1
0.6962	Remote Similarity	NPD3620	Phase 2
0.6957	Remote Similarity	NPD6100	Approved
0.6957	Remote Similarity	NPD6099	Approved
0.6951	Remote Similarity	NPD6190	Approved
0.6946	Remote Similarity	NPD5403	Approved
0.6943	Remote Similarity	NPD6798	Discontinued
0.6941	Remote Similarity	NPD6801	Discontinued
0.694	Remote Similarity	NPD7906	Approved
0.6933	Remote Similarity	NPD5177	Phase 3
0.6928	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD4678	Approved
0.6923	Remote Similarity	NPD4675	Approved
0.6919	Remote Similarity	NPD7768	Phase 2
0.6918	Remote Similarity	NPD6355	Discontinued
0.6914	Remote Similarity	NPD6232	Discontinued
0.6914	Remote Similarity	NPD5762	Approved
0.6914	Remote Similarity	NPD3540	Phase 1
0.6914	Remote Similarity	NPD5763	Approved
0.691	Remote Similarity	NPD8156	Discontinued
0.6894	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7473	Discontinued
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3750	Approved
0.6882	Remote Similarity	NPD7411	Suspended
0.6879	Remote Similarity	NPD7095	Approved
0.6868	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8127	Discontinued
0.6854	Remote Similarity	NPD8252	Approved
0.6854	Remote Similarity	NPD8251	Approved
0.6854	Remote Similarity	NPD8099	Discontinued
0.6852	Remote Similarity	NPD3539	Phase 1
0.6848	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2677	Approved
0.6842	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3022	Approved
0.6828	Remote Similarity	NPD3021	Approved
0.6826	Remote Similarity	NPD5401	Approved
0.6826	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5735	Approved
0.6813	Remote Similarity	NPD7311	Approved
0.6813	Remote Similarity	NPD7312	Approved
0.6813	Remote Similarity	NPD7313	Approved
0.6813	Remote Similarity	NPD7310	Approved
0.681	Remote Similarity	NPD1375	Discontinued
0.6795	Remote Similarity	NPD6584	Phase 3
0.6792	Remote Similarity	NPD6233	Phase 2
0.679	Remote Similarity	NPD7033	Discontinued
0.679	Remote Similarity	NPD4108	Discontinued
0.6788	Remote Similarity	NPD7466	Approved
0.6788	Remote Similarity	NPD4628	Phase 3
0.6788	Remote Similarity	NPD3892	Phase 2
0.6786	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5126	Approved
0.6776	Remote Similarity	NPD7309	Approved
0.6776	Remote Similarity	NPD5846	Approved
0.6776	Remote Similarity	NPD6516	Phase 2
0.6776	Remote Similarity	NPD5125	Phase 3
0.6768	Remote Similarity	NPD2424	Discontinued
0.6766	Remote Similarity	NPD6799	Approved
0.6765	Remote Similarity	NPD4005	Discontinued
0.6748	Remote Similarity	NPD2796	Approved
0.6742	Remote Similarity	NPD27	Approved
0.6742	Remote Similarity	NPD2489	Approved
0.6736	Remote Similarity	NPD7698	Approved
0.6736	Remote Similarity	NPD7697	Approved
0.6736	Remote Similarity	NPD7696	Phase 3
0.6727	Remote Similarity	NPD3060	Approved
0.6726	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7584	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