NPASS Compound

Structure

NPC63105 OpenBabel07101718292D 42 46 0 0 1 0 0 0 0 0999 V2000 -6.9282 -3.0000 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 -5.1962 -3.0000 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 -1.7321 -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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 2 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 -2.5981 -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 5.1962 -1.0000 0.0000 C 0 0 2 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 0 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 0.0000 2.0000 0.0000 C 0 0 1 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 -0.8660 1.5000 0.0000 C 0 0 2 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 2 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 6.9282 -0.0000 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 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 4.3301 -2.5000 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 2.5981 -1.5000 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 -5.1962 0.0000 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 2.5981 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 9 1 0 0 0 0 2 37 1 0 0 0 0 3 9 2 0 0 0 0 3 10 1 0 0 0 0 4 10 2 0 0 0 0 4 11 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 28 1 0 0 0 0 8 38 1 0 0 0 0 9 39 1 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 12 37 1 0 0 0 0 13 16 2 0 0 0 0 13 40 1 0 0 0 0 14 7 1 6 0 0 0 14 18 1 0 0 0 0 14 41 1 0 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 15 42 1 0 0 0 0 16 20 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 29 1 1 0 0 0 19 22 1 0 0 0 0 19 30 1 6 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 21 32 1 6 0 0 0 22 24 1 0 0 0 0 22 33 1 1 0 0 0 23 26 1 0 0 0 0 23 34 1 1 0 0 0 24 27 1 0 0 0 0 24 35 1 6 0 0 0 25 36 2 0 0 0 0 25 39 1 0 0 0 0 26 38 1 6 0 0 0 26 41 1 0 0 0 0 27 40 1 1 0 0 0 27 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.17
Volume:	546.164
LogP:	-0.207
LogD:	-0.406
LogS:	-2.348
# Rotatable Bonds:	7
TPSA:	238.2
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	4.796
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.411
MDCK Permeability:	4.443840589374304e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.882
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	65.48199462890625%
Volume Distribution (VD):	0.62
Pgp-substrate:	19.4132137298584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	1.111
Half-life (T1/2):	0.626

ADMET: Toxicity

hERG Blockers:	0.444
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.678
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC63105

Natural Product ID:	NPC63105
*Common Name:**	Toralactone-9-O-Gentiobioside
IUPAC Name:	10-hydroxy-7-methoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one
Synonyms:
Standard InCHIKey:	GBGJNKYTLIUCMX-YUMVGKRXSA-N
Standard InCHI:	InChI=1S/C27H32O15/c1-9-3-10-4-11-5-12(37-2)6-13(16(11)20(31)17(10)25(36)39-9)40-27-24(35)22(33)19(30)15(42-27)8-38-26-23(34)21(32)18(29)14(7-28)41-26/h3-6,14-15,18-19,21-24,26-35H,7-8H2,1-2H3/t14-,15-,18-,19-,21+,22+,23-,24-,26-,27-/m1/s1
SMILES:	Cc1cc2cc3cc(cc(c3c(c2c(=O)o1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3634701
PubChem CID:	5317701
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones [CHEMONTID:0001646] Naphthopyranone 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
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26483136]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	Inhibition	=	67.6	%	PMID[475335]
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	IC50	=	20000.0	nM	PMID[475335]

☑ 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 NPC63105 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	1831
0.2-0.3	3729
0.3-0.4	8893
0.4-0.5	9060
0.5-0.6	5332
0.6-0.7	5568
0.7-0.8	5999
0.8-0.85	1384
0.85-0.9	420
0.9-0.95	39
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC84494
0.9818	High Similarity	NPC245059
0.9816	High Similarity	NPC213052
0.9759	High Similarity	NPC470448
0.9759	High Similarity	NPC470452
0.9759	High Similarity	NPC470453
0.9759	High Similarity	NPC164047
0.9636	High Similarity	NPC199533
0.9636	High Similarity	NPC470454
0.9632	High Similarity	NPC259905
0.9573	High Similarity	NPC298778
0.9524	High Similarity	NPC475161
0.9524	High Similarity	NPC477860
0.9509	High Similarity	NPC178851
0.9461	High Similarity	NPC46958
0.9451	High Similarity	NPC249977
0.9401	High Similarity	NPC68381
0.9401	High Similarity	NPC474345
0.9357	High Similarity	NPC473686
0.9357	High Similarity	NPC475220
0.9357	High Similarity	NPC221140
0.9357	High Similarity	NPC475352
0.9357	High Similarity	NPC229817
0.9353	High Similarity	NPC475662
0.9353	High Similarity	NPC293227
0.9353	High Similarity	NPC473717
0.9353	High Similarity	NPC473631
0.9345	High Similarity	NPC475246
0.9329	High Similarity	NPC7752
0.9329	High Similarity	NPC99216
0.9286	High Similarity	NPC3718
0.9281	High Similarity	NPC76128
0.9281	High Similarity	NPC111536
0.9281	High Similarity	NPC271385
0.9281	High Similarity	NPC30432
0.9281	High Similarity	NPC5029
0.9277	High Similarity	NPC473202
0.9268	High Similarity	NPC124155
0.9268	High Similarity	NPC257566
0.9244	High Similarity	NPC87583
0.9244	High Similarity	NPC241847
0.9235	High Similarity	NPC277710
0.9235	High Similarity	NPC153578
0.9235	High Similarity	NPC114257
0.9235	High Similarity	NPC299149
0.9207	High Similarity	NPC216752
0.9207	High Similarity	NPC44947
0.9202	High Similarity	NPC328093
0.9146	High Similarity	NPC101636
0.9146	High Similarity	NPC47923
0.9118	High Similarity	NPC475233
0.9112	High Similarity	NPC208668
0.9112	High Similarity	NPC25724
0.9112	High Similarity	NPC472054
0.9107	High Similarity	NPC76047
0.9107	High Similarity	NPC150767
0.9107	High Similarity	NPC477572
0.9107	High Similarity	NPC477571
0.9107	High Similarity	NPC199079
0.9107	High Similarity	NPC78734
0.9107	High Similarity	NPC477573
0.9107	High Similarity	NPC210808
0.9096	High Similarity	NPC470200
0.9096	High Similarity	NPC470194
0.9096	High Similarity	NPC470193
0.9096	High Similarity	NPC316274
0.9096	High Similarity	NPC470196
0.9096	High Similarity	NPC470198
0.9096	High Similarity	NPC282474
0.9096	High Similarity	NPC470195
0.9096	High Similarity	NPC470197
0.9091	High Similarity	NPC298171
0.9091	High Similarity	NPC190450
0.908	High Similarity	NPC257309
0.908	High Similarity	NPC105591
0.9053	High Similarity	NPC288152
0.9053	High Similarity	NPC256760
0.9053	High Similarity	NPC257011
0.9053	High Similarity	NPC137871
0.9053	High Similarity	NPC9002
0.9048	High Similarity	NPC222455
0.9048	High Similarity	NPC5319
0.9042	High Similarity	NPC70441
0.9036	High Similarity	NPC17432
0.9034	High Similarity	NPC264302
0.9034	High Similarity	NPC48474
0.903	High Similarity	NPC303913
0.9024	High Similarity	NPC138811
0.9024	High Similarity	NPC473634
0.9024	High Similarity	NPC22062
0.9018	High Similarity	NPC261866
0.9012	High Similarity	NPC212290
0.9006	High Similarity	NPC324220
0.9006	High Similarity	NPC255799
0.9006	High Similarity	NPC312630
0.9	High Similarity	NPC203751
0.9	High Similarity	NPC85368
0.9	High Similarity	NPC98776
0.8994	High Similarity	NPC218488
0.8988	High Similarity	NPC298847
0.8988	High Similarity	NPC477502
0.8983	High Similarity	NPC314459
0.8983	High Similarity	NPC470199
0.8982	High Similarity	NPC475979
0.8982	High Similarity	NPC294722
0.8977	High Similarity	NPC314672
0.8976	High Similarity	NPC131745
0.8976	High Similarity	NPC259834
0.897	High Similarity	NPC246469
0.897	High Similarity	NPC470358
0.897	High Similarity	NPC473623
0.897	High Similarity	NPC472320
0.897	High Similarity	NPC97285
0.897	High Similarity	NPC271270
0.897	High Similarity	NPC142860
0.8966	High Similarity	NPC75574
0.8963	High Similarity	NPC44931
0.8963	High Similarity	NPC129827
0.8963	High Similarity	NPC65003
0.8963	High Similarity	NPC473512
0.8957	High Similarity	NPC470603
0.8957	High Similarity	NPC470604
0.8957	High Similarity	NPC470605
0.8947	High Similarity	NPC146803
0.8947	High Similarity	NPC294629
0.8935	High Similarity	NPC195257
0.8935	High Similarity	NPC209296
0.8935	High Similarity	NPC470206
0.8935	High Similarity	NPC470207
0.8935	High Similarity	NPC43587
0.8935	High Similarity	NPC293629
0.8929	High Similarity	NPC64425
0.8929	High Similarity	NPC178173
0.8929	High Similarity	NPC472621
0.8929	High Similarity	NPC210073
0.8929	High Similarity	NPC115674
0.8929	High Similarity	NPC68592
0.8929	High Similarity	NPC262222
0.8929	High Similarity	NPC298666
0.8927	High Similarity	NPC321046
0.8922	High Similarity	NPC278419
0.8922	High Similarity	NPC179198
0.8922	High Similarity	NPC66087
0.8922	High Similarity	NPC183672
0.8909	High Similarity	NPC73511
0.8909	High Similarity	NPC308265
0.8909	High Similarity	NPC43761
0.8908	High Similarity	NPC313452
0.8902	High Similarity	NPC473657
0.8902	High Similarity	NPC127406
0.8902	High Similarity	NPC295613
0.8902	High Similarity	NPC206378
0.8896	High Similarity	NPC211158
0.8896	High Similarity	NPC78021
0.8896	High Similarity	NPC87304
0.8896	High Similarity	NPC185103
0.8896	High Similarity	NPC268950
0.8896	High Similarity	NPC108706
0.8895	High Similarity	NPC289876
0.8895	High Similarity	NPC89127
0.8895	High Similarity	NPC102053
0.8895	High Similarity	NPC471669
0.8889	High Similarity	NPC34436
0.8889	High Similarity	NPC166674
0.8889	High Similarity	NPC46640
0.8889	High Similarity	NPC263119
0.8889	High Similarity	NPC219600
0.8882	High Similarity	NPC241874
0.8882	High Similarity	NPC105095
0.8882	High Similarity	NPC79056
0.8882	High Similarity	NPC177731
0.8882	High Similarity	NPC231194
0.8882	High Similarity	NPC51326
0.8882	High Similarity	NPC52598
0.8882	High Similarity	NPC44328
0.8876	High Similarity	NPC63470
0.8876	High Similarity	NPC474024
0.8876	High Similarity	NPC472622
0.8869	High Similarity	NPC15358
0.8869	High Similarity	NPC475497
0.8869	High Similarity	NPC178281
0.8869	High Similarity	NPC475366
0.8869	High Similarity	NPC284277
0.8862	High Similarity	NPC472876
0.8862	High Similarity	NPC475382
0.8862	High Similarity	NPC240306
0.8862	High Similarity	NPC473043
0.8857	High Similarity	NPC106700
0.8855	High Similarity	NPC271479
0.8855	High Similarity	NPC187379
0.8851	High Similarity	NPC53680
0.8851	High Similarity	NPC208797
0.8851	High Similarity	NPC315221
0.8848	High Similarity	NPC161749
0.8848	High Similarity	NPC197896
0.8848	High Similarity	NPC313163
0.8848	High Similarity	NPC258035
0.8848	High Similarity	NPC23817
0.8848	High Similarity	NPC470606
0.8848	High Similarity	NPC156457

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 NPC63105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	967
0.2-0.3	1911
0.3-0.4	2704
0.4-0.5	1901
0.5-0.6	863
0.6-0.7	256
0.7-0.8	136
0.8-0.85	19
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD7804	Clinical (unspecified phase)
0.8935	High Similarity	NPD7054	Approved
0.8882	High Similarity	NPD7472	Approved
0.8882	High Similarity	NPD7074	Phase 3
0.8848	High Similarity	NPD4381	Clinical (unspecified phase)
0.8802	High Similarity	NPD6959	Discontinued
0.8779	High Similarity	NPD7251	Discontinued
0.8779	High Similarity	NPD6559	Discontinued
0.8728	High Similarity	NPD7808	Phase 3
0.8721	High Similarity	NPD6797	Phase 2
0.8678	High Similarity	NPD8312	Approved
0.8678	High Similarity	NPD8313	Approved
0.8652	High Similarity	NPD7879	Clinical (unspecified phase)
0.8554	High Similarity	NPD7819	Suspended
0.8514	High Similarity	NPD4338	Clinical (unspecified phase)
0.8512	High Similarity	NPD7075	Discontinued
0.8497	Intermediate Similarity	NPD5844	Phase 1
0.8485	Intermediate Similarity	NPD4380	Phase 2
0.8457	Intermediate Similarity	NPD8151	Discontinued
0.8439	Intermediate Similarity	NPD3818	Discontinued
0.8421	Intermediate Similarity	NPD6232	Discontinued
0.8382	Intermediate Similarity	NPD7473	Discontinued
0.8368	Intermediate Similarity	NPD7783	Phase 2
0.8368	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7228	Approved
0.8324	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6166	Phase 2
0.8324	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6801	Discontinued
0.8235	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD8455	Phase 2
0.8191	Intermediate Similarity	NPD7435	Discontinued
0.8182	Intermediate Similarity	NPD2532	Approved
0.8182	Intermediate Similarity	NPD2534	Approved
0.8182	Intermediate Similarity	NPD2533	Approved
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD1934	Approved
0.8132	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD1465	Phase 2
0.8114	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7411	Suspended
0.8072	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3817	Phase 2
0.8037	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8032	Intermediate Similarity	NPD6777	Approved
0.8032	Intermediate Similarity	NPD6776	Approved
0.8032	Intermediate Similarity	NPD6779	Approved
0.8032	Intermediate Similarity	NPD6781	Approved
0.8032	Intermediate Similarity	NPD6778	Approved
0.8032	Intermediate Similarity	NPD6780	Approved
0.8032	Intermediate Similarity	NPD6782	Approved
0.8023	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD7697	Approved
0.8	Intermediate Similarity	NPD7698	Approved
0.8	Intermediate Similarity	NPD7696	Phase 3
0.7989	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD5402	Approved
0.7953	Intermediate Similarity	NPD37	Approved
0.7944	Intermediate Similarity	NPD7240	Approved
0.7941	Intermediate Similarity	NPD6599	Discontinued
0.7938	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7874	Approved
0.7931	Intermediate Similarity	NPD6234	Discontinued
0.7927	Intermediate Similarity	NPD7701	Phase 2
0.7919	Intermediate Similarity	NPD4967	Phase 2
0.7919	Intermediate Similarity	NPD4966	Approved
0.7919	Intermediate Similarity	NPD4965	Approved
0.7907	Intermediate Similarity	NPD2801	Approved
0.7886	Intermediate Similarity	NPD5494	Approved
0.787	Intermediate Similarity	NPD5403	Approved
0.7866	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8320	Phase 1
0.7865	Intermediate Similarity	NPD8319	Approved
0.7865	Intermediate Similarity	NPD7870	Phase 2
0.7865	Intermediate Similarity	NPD7871	Phase 2
0.7857	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6823	Phase 2
0.7841	Intermediate Similarity	NPD7199	Phase 2
0.7831	Intermediate Similarity	NPD3750	Approved
0.7831	Intermediate Similarity	NPD7699	Phase 2
0.7831	Intermediate Similarity	NPD4628	Phase 3
0.7831	Intermediate Similarity	NPD7700	Phase 2
0.7821	Intermediate Similarity	NPD3751	Discontinued
0.7818	Intermediate Similarity	NPD1549	Phase 2
0.7798	Intermediate Similarity	NPD6799	Approved
0.7798	Intermediate Similarity	NPD7390	Discontinued
0.7798	Intermediate Similarity	NPD1511	Approved
0.7797	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7458	Discontinued
0.7778	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD3749	Approved
0.7766	Intermediate Similarity	NPD6534	Approved
0.7766	Intermediate Similarity	NPD6535	Approved
0.7751	Intermediate Similarity	NPD5401	Approved
0.773	Intermediate Similarity	NPD8150	Discontinued
0.7716	Intermediate Similarity	NPD7801	Approved
0.7706	Intermediate Similarity	NPD1512	Approved
0.7697	Intermediate Similarity	NPD2796	Approved
0.7697	Intermediate Similarity	NPD5710	Approved
0.7697	Intermediate Similarity	NPD5711	Approved
0.7692	Intermediate Similarity	NPD7584	Approved
0.7654	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2346	Discontinued
0.765	Intermediate Similarity	NPD7685	Pre-registration
0.7647	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1510	Phase 2
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1653	Approved
0.7614	Intermediate Similarity	NPD3882	Suspended
0.759	Intermediate Similarity	NPD2935	Discontinued
0.759	Intermediate Similarity	NPD1551	Phase 2
0.7581	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7585	Approved
0.756	Intermediate Similarity	NPD6674	Discontinued
0.7549	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3748	Approved
0.7526	Intermediate Similarity	NPD6213	Phase 3
0.7526	Intermediate Similarity	NPD6212	Phase 3
0.7526	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1607	Approved
0.7515	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7583	Approved
0.7513	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7930	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6100	Approved
0.7485	Intermediate Similarity	NPD6099	Approved
0.7485	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD920	Approved
0.7457	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1243	Approved
0.7456	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7266	Discontinued
0.743	Intermediate Similarity	NPD919	Approved
0.7425	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7229	Phase 3
0.7394	Intermediate Similarity	NPD1240	Approved
0.7381	Intermediate Similarity	NPD5405	Approved
0.7381	Intermediate Similarity	NPD5406	Approved
0.7381	Intermediate Similarity	NPD5404	Approved
0.7381	Intermediate Similarity	NPD5408	Approved
0.736	Intermediate Similarity	NPD7680	Approved
0.7354	Intermediate Similarity	NPD8434	Phase 2
0.7353	Intermediate Similarity	NPD2800	Approved
0.7341	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4625	Phase 3
0.7312	Intermediate Similarity	NPD5953	Discontinued
0.731	Intermediate Similarity	NPD7003	Approved
0.7297	Intermediate Similarity	NPD7286	Phase 2
0.7286	Intermediate Similarity	NPD7999	Approved
0.7283	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5124	Phase 1
0.7245	Intermediate Similarity	NPD8285	Discontinued
0.7243	Intermediate Similarity	NPD7177	Discontinued
0.7241	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2799	Discontinued
0.7219	Intermediate Similarity	NPD7033	Discontinued
0.7216	Intermediate Similarity	NPD4360	Phase 2
0.7216	Intermediate Similarity	NPD4363	Phase 3
0.7208	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8059	Phase 3
0.7204	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6651	Approved
0.72	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6273	Approved
0.7191	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1613	Approved
0.7186	Intermediate Similarity	NPD4060	Phase 1
0.7186	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2438	Suspended
0.7169	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7158	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7151	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7081	Intermediate Similarity	NPD3926	Phase 2
0.7072	Intermediate Similarity	NPD4288	Approved
0.7068	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8127	Discontinued
0.7062	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7097	Phase 1
0.7052	Intermediate Similarity	NPD1652	Phase 2
0.7048	Intermediate Similarity	NPD4908	Phase 1
0.7041	Intermediate Similarity	NPD6355	Discontinued
0.7023	Intermediate Similarity	NPD8067	Phase 3
0.7018	Intermediate Similarity	NPD4308	Phase 3
0.7012	Intermediate Similarity	NPD1283	Approved
0.6988	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2979	Phase 3

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