NPASS Compound

Structure

NPC475233 OpenBabel07101718312D 41 45 0 0 1 0 0 0 0 0999 V2000 -8.7078 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -3.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1097 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -2.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2437 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6456 -1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6456 -4.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8736 3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 2.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -4.0933 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 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 37 1 0 0 0 0 3 10 2 0 0 0 0 3 12 1 0 0 0 0 4 10 1 0 0 0 0 4 14 2 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 15 2 0 0 0 0 7 28 1 0 0 0 0 8 27 1 0 0 0 0 8 29 1 0 0 0 0 9 27 1 0 0 0 0 9 38 1 0 0 0 0 11 37 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 30 1 0 0 0 0 15 18 1 0 0 0 0 15 39 1 0 0 0 0 16 7 1 1 0 0 0 16 20 1 0 0 0 0 16 40 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 19 31 2 0 0 0 0 20 22 1 0 0 0 0 20 32 1 6 0 0 0 21 33 2 0 0 0 0 22 23 1 0 0 0 0 22 34 1 1 0 0 0 23 25 1 0 0 0 0 23 41 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 6 0 0 0 24 35 1 0 0 0 0 25 39 1 1 0 0 0 25 40 1 0 0 0 0 26 38 1 0 0 0 0 26 41 1 1 0 0 0 27 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.16
Volume:	534.737
LogP:	1.305
LogD:	0.277
LogS:	-4.19
# Rotatable Bonds:	7
TPSA:	221.9
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	4.672
Fsp3:	0.481
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.364
MDCK Permeability:	1.2487530511862133e-05
Pgp-inhibitor:	0.571
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	76.2105941772461%
Volume Distribution (VD):	0.651
Pgp-substrate:	8.068002700805664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	2.544
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.314
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.867
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.098
Carcinogencity:	0.483
Eye Corrosion:	0.003
Eye Irritation:	0.118
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC475233

Natural Product ID:	NPC475233
*Common Name:**	Physcion 8-O-Rhamnosyl-(1->2)-Glucoside
IUPAC Name:	1-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8-hydroxy-3-methoxy-6-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	IODWPQMAPBGFAM-ZETRQFANSA-N
Standard InCHI:	InChI=1S/C27H30O14/c1-10-3-12-17(14(30)4-10)21(33)18-13(19(12)31)5-11(37-2)6-15(18)39-25-23(22(34)20(32)16(7-28)40-25)41-26-24(35)27(36,8-29)9-38-26/h3-6,16,20,22-26,28-30,32,34-36H,7-9H2,1-2H3/t16-,20-,22+,23-,24+,25-,26+,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1OC[C@]([C@H]1O)(O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501523
PubChem CID:	44584613
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO33118	Rhamnus	Genus	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350094]

☑ 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
ED50	2
Others	4

Activity Type	# Activity
Cell Line	1
CELL-LINE	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.58	ug ml-1	PMID[564092]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.5	ug ml-1	PMID[564092]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	78.2	%	PMID[564093]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	75.9	%	PMID[564093]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	76.7	%	PMID[564093]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	86.6	%	PMID[564093]

☑ 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 NPC475233 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	421
0.1-0.2	1642
0.2-0.3	3190
0.3-0.4	7641
0.4-0.5	10144
0.5-0.6	5198
0.6-0.7	5353
0.7-0.8	6577
0.8-0.85	2176
0.85-0.9	306
0.9-0.95	40
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC98776
0.9816	High Similarity	NPC30432
0.9816	High Similarity	NPC111536
0.9816	High Similarity	NPC271385
0.9816	High Similarity	NPC76128
0.9816	High Similarity	NPC5029
0.9697	High Similarity	NPC68381
0.9639	High Similarity	NPC46958
0.9639	High Similarity	NPC475246
0.9578	High Similarity	NPC3718
0.9573	High Similarity	NPC222455
0.9524	High Similarity	NPC153578
0.9524	High Similarity	NPC114257
0.9524	High Similarity	NPC277710
0.9524	High Similarity	NPC299149
0.9524	High Similarity	NPC212290
0.9515	High Similarity	NPC298778
0.9467	High Similarity	NPC475161
0.9467	High Similarity	NPC477860
0.9461	High Similarity	NPC146803
0.9455	High Similarity	NPC473202
0.9455	High Similarity	NPC259905
0.9451	High Similarity	NPC178851
0.9401	High Similarity	NPC472054
0.9353	High Similarity	NPC315221
0.9345	High Similarity	NPC474345
0.9302	High Similarity	NPC87583
0.9298	High Similarity	NPC313452
0.9286	High Similarity	NPC85368
0.9286	High Similarity	NPC213052
0.9286	High Similarity	NPC199357
0.9268	High Similarity	NPC212099
0.9268	High Similarity	NPC146837
0.9268	High Similarity	NPC278329
0.9268	High Similarity	NPC101116
0.9264	High Similarity	NPC470810
0.9249	High Similarity	NPC105591
0.9231	High Similarity	NPC470454
0.9231	High Similarity	NPC199533
0.9157	High Similarity	NPC478020
0.9157	High Similarity	NPC478022
0.9157	High Similarity	NPC178281
0.9152	High Similarity	NPC216752
0.9118	High Similarity	NPC63105
0.9107	High Similarity	NPC191653
0.9085	High Similarity	NPC470607
0.9075	High Similarity	NPC473631
0.9075	High Similarity	NPC475662
0.9075	High Similarity	NPC293227
0.9075	High Similarity	NPC473717
0.907	High Similarity	NPC245059
0.907	High Similarity	NPC84494
0.9064	High Similarity	NPC324220
0.9064	High Similarity	NPC312630
0.9059	High Similarity	NPC203751
0.9053	High Similarity	NPC212748
0.9036	High Similarity	NPC93215
0.9034	High Similarity	NPC314672
0.903	High Similarity	NPC200708
0.903	High Similarity	NPC472320
0.903	High Similarity	NPC470358
0.9024	High Similarity	NPC23817
0.9024	High Similarity	NPC470606
0.9017	High Similarity	NPC470453
0.9017	High Similarity	NPC208069
0.9017	High Similarity	NPC164047
0.9017	High Similarity	NPC470452
0.9017	High Similarity	NPC470448
0.9	High Similarity	NPC235575
0.8982	High Similarity	NPC471286
0.8982	High Similarity	NPC183672
0.8971	High Similarity	NPC221140
0.8971	High Similarity	NPC229817
0.8971	High Similarity	NPC475220
0.8971	High Similarity	NPC473686
0.8971	High Similarity	NPC475352
0.897	High Similarity	NPC73511
0.8963	High Similarity	NPC261866
0.8963	High Similarity	NPC265480
0.8963	High Similarity	NPC17521
0.8963	High Similarity	NPC149368
0.8953	High Similarity	NPC289876
0.8953	High Similarity	NPC102053
0.8941	High Similarity	NPC241874
0.8941	High Similarity	NPC478021
0.8941	High Similarity	NPC477573
0.8941	High Similarity	NPC477571
0.8941	High Similarity	NPC477572
0.8935	High Similarity	NPC249977
0.8935	High Similarity	NPC474024
0.8935	High Similarity	NPC477502
0.8935	High Similarity	NPC63470
0.8933	High Similarity	NPC314459
0.8933	High Similarity	NPC470199
0.8929	High Similarity	NPC7752
0.8922	High Similarity	NPC44947
0.8922	High Similarity	NPC259834
0.8922	High Similarity	NPC472402
0.8922	High Similarity	NPC131745
0.8916	High Similarity	NPC271479
0.8909	High Similarity	NPC161749
0.8909	High Similarity	NPC197896
0.8909	High Similarity	NPC258035
0.8909	High Similarity	NPC122809
0.8909	High Similarity	NPC156457
0.8909	High Similarity	NPC313163
0.8902	High Similarity	NPC470604
0.8902	High Similarity	NPC470603
0.8902	High Similarity	NPC99233
0.8902	High Similarity	NPC470605
0.8896	High Similarity	NPC40356
0.8896	High Similarity	NPC154683
0.8895	High Similarity	NPC108202
0.8895	High Similarity	NPC472607
0.8889	High Similarity	NPC261254
0.8889	High Similarity	NPC294501
0.8882	High Similarity	NPC229687
0.8876	High Similarity	NPC178173
0.8869	High Similarity	NPC66087
0.8869	High Similarity	NPC124155
0.8869	High Similarity	NPC257566
0.8869	High Similarity	NPC100849
0.8869	High Similarity	NPC179198
0.8869	High Similarity	NPC278419
0.8862	High Similarity	NPC30655
0.8862	High Similarity	NPC74854
0.8862	High Similarity	NPC47923
0.8862	High Similarity	NPC303913
0.8862	High Similarity	NPC45124
0.8857	High Similarity	NPC473883
0.8857	High Similarity	NPC478001
0.8855	High Similarity	NPC308265
0.8855	High Similarity	NPC279732
0.8851	High Similarity	NPC58538
0.8848	High Similarity	NPC45165
0.8848	High Similarity	NPC208152
0.8848	High Similarity	NPC78492
0.8848	High Similarity	NPC170475
0.8848	High Similarity	NPC206378
0.8844	High Similarity	NPC257714
0.8844	High Similarity	NPC156635
0.8841	High Similarity	NPC268950
0.8841	High Similarity	NPC78021
0.8841	High Similarity	NPC211158
0.8841	High Similarity	NPC108706
0.8841	High Similarity	NPC469405
0.8841	High Similarity	NPC106625
0.8841	High Similarity	NPC87304
0.8837	High Similarity	NPC154986
0.8834	High Similarity	NPC470569
0.8833	High Similarity	NPC470198
0.8833	High Similarity	NPC470193
0.8833	High Similarity	NPC470196
0.8833	High Similarity	NPC470195
0.8833	High Similarity	NPC470194
0.8833	High Similarity	NPC282474
0.8833	High Similarity	NPC470200
0.8833	High Similarity	NPC470197
0.8833	High Similarity	NPC316274
0.883	High Similarity	NPC287884
0.883	High Similarity	NPC8704
0.883	High Similarity	NPC44558
0.883	High Similarity	NPC315306
0.883	High Similarity	NPC76047
0.883	High Similarity	NPC313717
0.883	High Similarity	NPC150767
0.883	High Similarity	NPC105511
0.883	High Similarity	NPC224462
0.883	High Similarity	NPC78734
0.8824	High Similarity	NPC150131
0.8824	High Similarity	NPC225419
0.8824	High Similarity	NPC234497
0.8824	High Similarity	NPC229729
0.8824	High Similarity	NPC45400
0.8824	High Similarity	NPC324522
0.8824	High Similarity	NPC470341
0.8824	High Similarity	NPC472058
0.8824	High Similarity	NPC105414
0.8817	High Similarity	NPC475979
0.8817	High Similarity	NPC165720
0.8817	High Similarity	NPC294722
0.881	High Similarity	NPC473043
0.881	High Similarity	NPC150164
0.881	High Similarity	NPC127782
0.881	High Similarity	NPC310603
0.881	High Similarity	NPC300537
0.881	High Similarity	NPC190450
0.881	High Similarity	NPC125991
0.881	High Similarity	NPC473961
0.8802	High Similarity	NPC306978
0.8802	High Similarity	NPC472055
0.8802	High Similarity	NPC471976
0.8802	High Similarity	NPC328093
0.88	High Similarity	NPC53680
0.88	High Similarity	NPC170203
0.88	High Similarity	NPC85316
0.88	High Similarity	NPC208797
0.88	High Similarity	NPC197357
0.8795	High Similarity	NPC208651
0.8795	High Similarity	NPC206641

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 NPC475233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	895
0.2-0.3	1770
0.3-0.4	2702
0.4-0.5	1946
0.5-0.6	979
0.6-0.7	340
0.7-0.8	122
0.8-0.85	43
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD6559	Discontinued
0.8909	High Similarity	NPD4381	Clinical (unspecified phase)
0.8824	High Similarity	NPD3818	Discontinued
0.8814	High Similarity	NPD7879	Clinical (unspecified phase)
0.8663	High Similarity	NPD7804	Clinical (unspecified phase)
0.8639	High Similarity	NPD6959	Discontinued
0.8613	High Similarity	NPD7074	Phase 3
0.8555	High Similarity	NPD7054	Approved
0.8545	High Similarity	NPD4380	Phase 2
0.8523	High Similarity	NPD8313	Approved
0.8523	High Similarity	NPD8312	Approved
0.8506	High Similarity	NPD7472	Approved
0.8478	Intermediate Similarity	NPD6777	Approved
0.8478	Intermediate Similarity	NPD6781	Approved
0.8478	Intermediate Similarity	NPD6776	Approved
0.8478	Intermediate Similarity	NPD6780	Approved
0.8478	Intermediate Similarity	NPD6782	Approved
0.8478	Intermediate Similarity	NPD6778	Approved
0.8478	Intermediate Similarity	NPD6779	Approved
0.8457	Intermediate Similarity	NPD6797	Phase 2
0.8409	Intermediate Similarity	NPD7251	Discontinued
0.8393	Intermediate Similarity	NPD7819	Suspended
0.8393	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD6232	Discontinued
0.8362	Intermediate Similarity	NPD7808	Phase 3
0.8362	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7075	Discontinued
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8342	Intermediate Similarity	NPD7435	Discontinued
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8316	Intermediate Similarity	NPD8151	Discontinued
0.8294	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6166	Phase 2
0.8256	Intermediate Similarity	NPD5494	Approved
0.8245	Intermediate Similarity	NPD7697	Approved
0.8245	Intermediate Similarity	NPD7696	Phase 3
0.8245	Intermediate Similarity	NPD7698	Approved
0.8242	Intermediate Similarity	NPD2532	Approved
0.8242	Intermediate Similarity	NPD2534	Approved
0.8242	Intermediate Similarity	NPD2533	Approved
0.8235	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD1934	Approved
0.8207	Intermediate Similarity	NPD6534	Approved
0.8207	Intermediate Similarity	NPD6535	Approved
0.8201	Intermediate Similarity	NPD7871	Phase 2
0.8201	Intermediate Similarity	NPD7870	Phase 2
0.8182	Intermediate Similarity	NPD7228	Approved
0.8182	Intermediate Similarity	NPD3751	Discontinued
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD7701	Phase 2
0.8166	Intermediate Similarity	NPD7411	Suspended
0.814	Intermediate Similarity	NPD3749	Approved
0.8133	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6801	Discontinued
0.8118	Intermediate Similarity	NPD37	Approved
0.8095	Intermediate Similarity	NPD6823	Phase 2
0.8092	Intermediate Similarity	NPD6234	Discontinued
0.8083	Intermediate Similarity	NPD7874	Approved
0.8083	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD4966	Approved
0.8081	Intermediate Similarity	NPD4967	Phase 2
0.8081	Intermediate Similarity	NPD4965	Approved
0.8081	Intermediate Similarity	NPD3882	Suspended
0.8075	Intermediate Similarity	NPD7699	Phase 2
0.8075	Intermediate Similarity	NPD7700	Phase 2
0.8047	Intermediate Similarity	NPD3226	Approved
0.8041	Intermediate Similarity	NPD7783	Phase 2
0.8041	Intermediate Similarity	NPD7801	Approved
0.8041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1549	Phase 2
0.7966	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD2801	Approved
0.7955	Intermediate Similarity	NPD3787	Discontinued
0.7944	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5402	Approved
0.7917	Intermediate Similarity	NPD8320	Phase 1
0.7917	Intermediate Similarity	NPD8319	Approved
0.7914	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7199	Phase 2
0.7895	Intermediate Similarity	NPD6599	Discontinued
0.7861	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6213	Phase 3
0.7861	Intermediate Similarity	NPD6212	Phase 3
0.7861	Intermediate Similarity	NPD1465	Phase 2
0.7816	Intermediate Similarity	NPD3817	Phase 2
0.7802	Intermediate Similarity	NPD7240	Approved
0.7784	Intermediate Similarity	NPD8150	Discontinued
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7758	Intermediate Similarity	NPD2796	Approved
0.7753	Intermediate Similarity	NPD5710	Approved
0.7753	Intermediate Similarity	NPD5711	Approved
0.7751	Intermediate Similarity	NPD1511	Approved
0.7751	Intermediate Similarity	NPD6799	Approved
0.7751	Intermediate Similarity	NPD7390	Discontinued
0.7744	Intermediate Similarity	NPD7584	Approved
0.7725	Intermediate Similarity	NPD2800	Approved
0.7719	Intermediate Similarity	NPD5403	Approved
0.7719	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD2346	Discontinued
0.7709	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD8434	Phase 2
0.7685	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1607	Approved
0.7679	Intermediate Similarity	NPD4628	Phase 3
0.7679	Intermediate Similarity	NPD3750	Approved
0.7665	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1512	Approved
0.7657	Intermediate Similarity	NPD8455	Phase 2
0.763	Intermediate Similarity	NPD7458	Discontinued
0.763	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7685	Pre-registration
0.7602	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5401	Approved
0.7585	Intermediate Similarity	NPD8059	Phase 3
0.7585	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1240	Approved
0.7545	Intermediate Similarity	NPD6099	Approved
0.7545	Intermediate Similarity	NPD6100	Approved
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6674	Discontinued
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.7514	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5953	Discontinued
0.744	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD1551	Phase 2
0.7412	Intermediate Similarity	NPD1243	Approved
0.7403	Intermediate Similarity	NPD1247	Approved
0.7399	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2344	Approved
0.7389	Intermediate Similarity	NPD7930	Approved
0.7389	Intermediate Similarity	NPD919	Approved
0.7385	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3748	Approved
0.738	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1653	Approved
0.7371	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7229	Phase 3
0.735	Intermediate Similarity	NPD7585	Approved
0.7347	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7583	Approved
0.7299	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8285	Discontinued
0.7283	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7263	Intermediate Similarity	NPD5761	Phase 2
0.7263	Intermediate Similarity	NPD5760	Phase 2
0.7258	Intermediate Similarity	NPD7286	Phase 2
0.7257	Intermediate Similarity	NPD6273	Approved
0.724	Intermediate Similarity	NPD4287	Approved
0.7236	Intermediate Similarity	NPD7680	Approved
0.7235	Intermediate Similarity	NPD5404	Approved
0.7235	Intermediate Similarity	NPD5405	Approved
0.7235	Intermediate Similarity	NPD5406	Approved
0.7235	Intermediate Similarity	NPD5408	Approved
0.7229	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2309	Approved
0.7179	Intermediate Similarity	NPD4363	Phase 3
0.7179	Intermediate Similarity	NPD4360	Phase 2
0.7177	Intermediate Similarity	NPD8366	Approved
0.7164	Intermediate Similarity	NPD7999	Approved
0.716	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1470	Approved
0.7126	Intermediate Similarity	NPD6190	Approved
0.7126	Intermediate Similarity	NPD3764	Approved
0.7126	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2313	Discontinued
0.712	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7177	Discontinued
0.7112	Intermediate Similarity	NPD7799	Discontinued
0.7112	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4908	Phase 1
0.7104	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD230	Phase 1
0.7093	Intermediate Similarity	NPD7266	Discontinued
0.7093	Intermediate Similarity	NPD1471	Phase 3
0.7076	Intermediate Similarity	NPD7033	Discontinued
0.7069	Intermediate Similarity	NPD7003	Approved
0.7052	Intermediate Similarity	NPD2424	Discontinued
0.7042	Intermediate Similarity	NPD8491	Approved
0.7028	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7024	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6410	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data