NPASS Compound

Structure

NPC473241 OpenBabel07101719512D 43 45 0 0 1 0 0 0 0 0999 V2000 -8.6603 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 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -2.5981 -1.5000 0.0000 C 0 0 0 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 2 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 -6.9282 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 1 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 -1.5000 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 0.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 3.5000 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 -7.7942 -1.5000 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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 5.1962 0.0000 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 3.4641 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 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 1 1 1 0 0 0 9 17 1 0 0 0 0 9 28 1 0 0 0 0 10 2 1 1 0 0 0 10 18 1 0 0 0 0 10 29 1 0 0 0 0 11 25 1 0 0 0 0 12 41 1 0 0 0 0 13 42 1 0 0 0 0 14 16 2 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 43 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 1 0 0 0 18 21 1 0 0 0 0 18 32 1 1 0 0 0 19 22 1 0 0 0 0 19 33 2 0 0 0 0 20 23 1 0 0 0 0 20 34 1 1 0 0 0 21 24 1 0 0 0 0 21 35 1 6 0 0 0 22 25 2 0 0 0 0 22 36 1 0 0 0 0 23 26 1 0 0 0 0 23 37 1 1 0 0 0 24 27 1 0 0 0 0 24 38 1 1 0 0 0 25 43 1 0 0 0 0 26 39 2 0 0 0 0 26 41 1 0 0 0 0 27 40 2 0 0 0 0 27 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.15
Volume:	564.158
LogP:	-0.67
LogD:	0.092
LogS:	-3.074
# Rotatable Bonds:	13
TPSA:	285.11
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	3
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.058
Synthetic Accessibility Score:	4.821
Fsp3:	0.37
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.287
MDCK Permeability:	7.996759813977405e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.79
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	79.04198455810547%
Volume Distribution (VD):	0.582
Pgp-substrate:	12.498900413513184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.503
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.283
Half-life (T1/2):	0.674

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.543
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.016
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC473241

Natural Product ID:	NPC473241
*Common Name:**	[4-[3,5-Dihydroxy-4-Oxo-7-[(2S,3S,4R,5R)-2,3,4,5-Tetrahydroxyhexanoyl]Oxychromen-2-Yl]Phenyl] (2S,3S,4R,5R)-2,3,4,5-Tetrahydroxyhexanoate
IUPAC Name:	[4-[3,5-dihydroxy-4-oxo-7-[(2S,3S,4R,5R)-2,3,4,5-tetrahydroxyhexanoyl]oxychromen-2-yl]phenyl] (2S,3S,4R,5R)-2,3,4,5-tetrahydroxyhexanoate
Synonyms:
Standard InCHIKey:	GQVHWSCAXZGPOV-MVZRGGIPSA-N
Standard InCHI:	InChI=1S/C27H30O16/c1-9(28)17(31)20(34)23(37)26(39)41-12-5-3-11(4-6-12)25-22(36)19(33)16-14(30)7-13(8-15(16)43-25)42-27(40)24(38)21(35)18(32)10(2)29/h3-10,17-18,20-21,23-24,28-32,34-38H,1-2H3/t9-,10-,17-,18-,20+,21+,23+,24+/m1/s1
SMILES:	O[C@@H]([C@H]([C@@H]([C@H](O)C)O)O)C(=O)Oc1ccc(cc1)c1oc2cc(OC(=O)[C@H]([C@H]([C@@H]([C@H](O)C)O)O)O)cc(c2c(=O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL378564
PubChem CID:	44412799
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16644212]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	16.0	%	PMID[573612]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	6.0	%	PMID[573612]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	14.0	%	PMID[573612]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	27.0	%	PMID[573612]

☑ 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 NPC473241 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	372
0.1-0.2	1527
0.2-0.3	4058
0.3-0.4	9003
0.4-0.5	9303
0.5-0.6	4019
0.6-0.7	5528
0.7-0.8	4278
0.8-0.85	2720
0.85-0.9	1724
0.9-0.95	164
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC27942
0.9324	High Similarity	NPC153758
0.929	High Similarity	NPC259957
0.929	High Similarity	NPC216496
0.929	High Similarity	NPC85707
0.929	High Similarity	NPC129217
0.929	High Similarity	NPC48093
0.929	High Similarity	NPC159579
0.929	High Similarity	NPC224530
0.929	High Similarity	NPC282169
0.9272	High Similarity	NPC295650
0.9267	High Similarity	NPC477941
0.9262	High Similarity	NPC44721
0.9262	High Similarity	NPC40086
0.9262	High Similarity	NPC3779
0.9262	High Similarity	NPC176869
0.9262	High Similarity	NPC122828
0.9262	High Similarity	NPC211466
0.9262	High Similarity	NPC476182
0.9221	High Similarity	NPC182634
0.9221	High Similarity	NPC6985
0.9221	High Similarity	NPC108831
0.9216	High Similarity	NPC304745
0.9216	High Similarity	NPC111341
0.9189	High Similarity	NPC470216
0.9177	High Similarity	NPC64425
0.9172	High Similarity	NPC121703
0.9161	High Similarity	NPC320283
0.9161	High Similarity	NPC472459
0.9161	High Similarity	NPC104677
0.9161	High Similarity	NPC41121
0.9161	High Similarity	NPC111929
0.9156	High Similarity	NPC203500
0.9156	High Similarity	NPC307938
0.9156	High Similarity	NPC323593
0.9156	High Similarity	NPC127406
0.915	High Similarity	NPC268193
0.9145	High Similarity	NPC262039
0.9145	High Similarity	NPC319910
0.9145	High Similarity	NPC262038
0.9145	High Similarity	NPC278476
0.9145	High Similarity	NPC254412
0.9133	High Similarity	NPC472918
0.9128	High Similarity	NPC4152
0.9128	High Similarity	NPC326506
0.9128	High Similarity	NPC142731
0.9128	High Similarity	NPC208176
0.9128	High Similarity	NPC306607
0.9128	High Similarity	NPC62290
0.9128	High Similarity	NPC279417
0.9128	High Similarity	NPC49130
0.9114	High Similarity	NPC139060
0.9114	High Similarity	NPC72016
0.9108	High Similarity	NPC471745
0.9108	High Similarity	NPC298171
0.9103	High Similarity	NPC187379
0.9103	High Similarity	NPC136761
0.9097	High Similarity	NPC54802
0.9097	High Similarity	NPC77672
0.9097	High Similarity	NPC197304
0.9097	High Similarity	NPC288084
0.9097	High Similarity	NPC43638
0.9097	High Similarity	NPC78263
0.9097	High Similarity	NPC135391
0.9097	High Similarity	NPC133671
0.9091	High Similarity	NPC27408
0.9091	High Similarity	NPC95090
0.9091	High Similarity	NPC279218
0.9091	High Similarity	NPC48579
0.9091	High Similarity	NPC207809
0.9091	High Similarity	NPC259710
0.9091	High Similarity	NPC108937
0.9091	High Similarity	NPC304207
0.9091	High Similarity	NPC217706
0.9085	High Similarity	NPC244583
0.9085	High Similarity	NPC138288
0.9085	High Similarity	NPC56232
0.9085	High Similarity	NPC171651
0.9085	High Similarity	NPC10807
0.9085	High Similarity	NPC161881
0.9085	High Similarity	NPC35567
0.9085	High Similarity	NPC217149
0.9085	High Similarity	NPC243171
0.9085	High Similarity	NPC216035
0.9085	High Similarity	NPC150123
0.9079	High Similarity	NPC474735
0.9079	High Similarity	NPC105136
0.9067	High Similarity	NPC148011
0.9067	High Similarity	NPC1940
0.9054	High Similarity	NPC90582
0.9054	High Similarity	NPC262094
0.9051	High Similarity	NPC80068
0.9048	High Similarity	NPC152042
0.9048	High Similarity	NPC241838
0.9048	High Similarity	NPC143799
0.9045	High Similarity	NPC249281
0.9045	High Similarity	NPC476215
0.9045	High Similarity	NPC181465
0.9045	High Similarity	NPC246943
0.9045	High Similarity	NPC265885
0.9045	High Similarity	NPC163242
0.9045	High Similarity	NPC215710
0.9045	High Similarity	NPC139320
0.9045	High Similarity	NPC135846
0.9045	High Similarity	NPC473438
0.9045	High Similarity	NPC64305
0.9045	High Similarity	NPC101636
0.9045	High Similarity	NPC112418
0.9045	High Similarity	NPC297987
0.9045	High Similarity	NPC173582
0.9045	High Similarity	NPC253788
0.9045	High Similarity	NPC276377
0.9045	High Similarity	NPC170052
0.9045	High Similarity	NPC116458
0.9032	High Similarity	NPC475797
0.9032	High Similarity	NPC129053
0.9032	High Similarity	NPC20530
0.9032	High Similarity	NPC109967
0.9032	High Similarity	NPC215917
0.9032	High Similarity	NPC474738
0.9032	High Similarity	NPC10754
0.9032	High Similarity	NPC78554
0.9032	High Similarity	NPC469936
0.9032	High Similarity	NPC321372
0.9032	High Similarity	NPC474609
0.9026	High Similarity	NPC83283
0.9026	High Similarity	NPC106625
0.9026	High Similarity	NPC39360
0.9026	High Similarity	NPC210003
0.9026	High Similarity	NPC29763
0.9026	High Similarity	NPC143851
0.9026	High Similarity	NPC293286
0.9026	High Similarity	NPC248793
0.9026	High Similarity	NPC180301
0.902	High Similarity	NPC209846
0.902	High Similarity	NPC477897
0.902	High Similarity	NPC289774
0.902	High Similarity	NPC328740
0.902	High Similarity	NPC471229
0.9013	High Similarity	NPC277032
0.9006	High Similarity	NPC175429
0.9006	High Similarity	NPC277532
0.9006	High Similarity	NPC209550
0.9006	High Similarity	NPC138990
0.8994	High Similarity	NPC19240
0.8994	High Similarity	NPC287889
0.8994	High Similarity	NPC205824
0.8994	High Similarity	NPC85751
0.8994	High Similarity	NPC135358
0.8994	High Similarity	NPC129264
0.8987	High Similarity	NPC240306
0.8987	High Similarity	NPC150164
0.8987	High Similarity	NPC131745
0.8986	High Similarity	NPC281207
0.8986	High Similarity	NPC59951
0.8986	High Similarity	NPC103904
0.8986	High Similarity	NPC269652
0.8986	High Similarity	NPC184536
0.8986	High Similarity	NPC146679
0.8986	High Similarity	NPC230285
0.8986	High Similarity	NPC474037
0.8986	High Similarity	NPC103342
0.8981	High Similarity	NPC153342
0.8981	High Similarity	NPC471079
0.8981	High Similarity	NPC304741
0.8981	High Similarity	NPC471744
0.8981	High Similarity	NPC470405
0.898	High Similarity	NPC276905
0.8974	High Similarity	NPC473512
0.8974	High Similarity	NPC129827
0.8974	High Similarity	NPC60966
0.8974	High Similarity	NPC44931
0.8974	High Similarity	NPC65003
0.8968	High Similarity	NPC470681
0.8968	High Similarity	NPC476169
0.8968	High Similarity	NPC99233
0.8961	High Similarity	NPC259767
0.8961	High Similarity	NPC88484
0.8961	High Similarity	NPC259182
0.8961	High Similarity	NPC121001
0.8961	High Similarity	NPC210597
0.8961	High Similarity	NPC256141
0.8954	High Similarity	NPC267117
0.8954	High Similarity	NPC61258
0.8954	High Similarity	NPC191154
0.8951	High Similarity	NPC474522
0.8951	High Similarity	NPC190003
0.8951	High Similarity	NPC175107
0.8947	High Similarity	NPC218569
0.8947	High Similarity	NPC10097
0.894	High Similarity	NPC229190
0.894	High Similarity	NPC470458
0.8938	High Similarity	NPC476470
0.8938	High Similarity	NPC298666
0.8938	High Similarity	NPC186816
0.8938	High Similarity	NPC203145
0.8938	High Similarity	NPC221342
0.8938	High Similarity	NPC12013
0.8938	High Similarity	NPC256188
0.8938	High Similarity	NPC11432

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 NPC473241 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	886
0.2-0.3	1771
0.3-0.4	2639
0.4-0.5	1910
0.5-0.6	1042
0.6-0.7	391
0.7-0.8	116
0.8-0.85	38
0.85-0.9	26
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD6801	Discontinued
0.9097	High Similarity	NPD7075	Discontinued
0.906	High Similarity	NPD6799	Approved
0.9007	High Similarity	NPD5403	Approved
0.8968	High Similarity	NPD3817	Phase 2
0.8903	High Similarity	NPD7096	Clinical (unspecified phase)
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8874	High Similarity	NPD5401	Approved
0.8854	High Similarity	NPD4381	Clinical (unspecified phase)
0.8846	High Similarity	NPD5402	Approved
0.8831	High Similarity	NPD4380	Phase 2
0.8727	High Similarity	NPD4338	Clinical (unspecified phase)
0.872	High Similarity	NPD6797	Phase 2
0.8712	High Similarity	NPD7804	Clinical (unspecified phase)
0.871	High Similarity	NPD6599	Discontinued
0.8667	High Similarity	NPD7251	Discontinued
0.8662	High Similarity	NPD2801	Approved
0.8658	High Similarity	NPD1552	Clinical (unspecified phase)
0.8658	High Similarity	NPD1550	Clinical (unspecified phase)
0.8642	High Similarity	NPD6166	Phase 2
0.8642	High Similarity	NPD6168	Clinical (unspecified phase)
0.8642	High Similarity	NPD6167	Clinical (unspecified phase)
0.8614	High Similarity	NPD7808	Phase 3
0.86	High Similarity	NPD1549	Phase 2
0.8599	High Similarity	NPD1934	Approved
0.8571	High Similarity	NPD1512	Approved
0.8553	High Similarity	NPD3882	Suspended
0.8545	High Similarity	NPD7472	Approved
0.8544	High Similarity	NPD2393	Clinical (unspecified phase)
0.8537	High Similarity	NPD3818	Discontinued
0.8535	High Similarity	NPD7411	Suspended
0.8485	Intermediate Similarity	NPD7054	Approved
0.8467	Intermediate Similarity	NPD2796	Approved
0.8442	Intermediate Similarity	NPD1511	Approved
0.8438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8387	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7074	Phase 3
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1240	Approved
0.8243	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1607	Approved
0.8129	Intermediate Similarity	NPD3750	Approved
0.8129	Intermediate Similarity	NPD4628	Phase 3
0.8129	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6559	Discontinued
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1551	Phase 2
0.8084	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6232	Discontinued
0.8065	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD920	Approved
0.8049	Intermediate Similarity	NPD3749	Approved
0.8036	Intermediate Similarity	NPD7473	Discontinued
0.8034	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD6832	Phase 2
0.7941	Intermediate Similarity	NPD5844	Phase 1
0.7925	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7033	Discontinued
0.7905	Intermediate Similarity	NPD1203	Approved
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7892	Intermediate Similarity	NPD919	Approved
0.7881	Intermediate Similarity	NPD6798	Discontinued
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7849	Intermediate Similarity	NPD5953	Discontinued
0.7844	Intermediate Similarity	NPD5494	Approved
0.7836	Intermediate Similarity	NPD7286	Phase 2
0.7834	Intermediate Similarity	NPD1243	Approved
0.7834	Intermediate Similarity	NPD1652	Phase 2
0.7829	Intermediate Similarity	NPD6233	Phase 2
0.7812	Intermediate Similarity	NPD2533	Approved
0.7812	Intermediate Similarity	NPD2532	Approved
0.7812	Intermediate Similarity	NPD2534	Approved
0.7809	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3748	Approved
0.7799	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8434	Phase 2
0.7765	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3268	Approved
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.7755	Intermediate Similarity	NPD422	Phase 1
0.7736	Intermediate Similarity	NPD6190	Approved
0.773	Intermediate Similarity	NPD3226	Approved
0.7722	Intermediate Similarity	NPD2800	Approved
0.7703	Intermediate Similarity	NPD9717	Approved
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7667	Intermediate Similarity	NPD2797	Approved
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7613	Intermediate Similarity	NPD447	Suspended
0.7613	Intermediate Similarity	NPD5124	Phase 1
0.7613	Intermediate Similarity	NPD230	Phase 1
0.7613	Intermediate Similarity	NPD6355	Discontinued
0.7613	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3926	Phase 2
0.76	Intermediate Similarity	NPD3225	Approved
0.7588	Intermediate Similarity	NPD1247	Approved
0.7564	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD1653	Approved
0.7557	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD4062	Phase 3
0.7484	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.744	Intermediate Similarity	NPD8455	Phase 2
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD943	Approved
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3266	Approved
0.7434	Intermediate Similarity	NPD3267	Approved
0.7407	Intermediate Similarity	NPD2354	Approved
0.7407	Intermediate Similarity	NPD3887	Approved
0.7403	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7435	Discontinued
0.7389	Intermediate Similarity	NPD8150	Discontinued
0.7389	Intermediate Similarity	NPD4340	Discontinued
0.7386	Intermediate Similarity	NPD1019	Discontinued
0.7381	Intermediate Similarity	NPD37	Approved
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD7584	Approved
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD9545	Approved
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4360	Phase 2
0.7337	Intermediate Similarity	NPD4363	Phase 3
0.7333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7308	Intermediate Similarity	NPD1296	Phase 2
0.7303	Intermediate Similarity	NPD7685	Pre-registration
0.7301	Intermediate Similarity	NPD2309	Approved
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD5647	Approved
0.7273	Intermediate Similarity	NPD2798	Approved
0.725	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3027	Phase 3
0.7241	Intermediate Similarity	NPD5711	Approved
0.7241	Intermediate Similarity	NPD5710	Approved
0.724	Intermediate Similarity	NPD7585	Approved
0.7239	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9493	Approved
0.7229	Intermediate Similarity	NPD5049	Phase 3
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7215	Intermediate Similarity	NPD4307	Phase 2
0.7212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6099	Approved
0.7205	Intermediate Similarity	NPD6100	Approved
0.7202	Intermediate Similarity	NPD7458	Discontinued
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD411	Approved
0.7193	Intermediate Similarity	NPD4288	Approved
0.7188	Intermediate Similarity	NPD7583	Approved
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2654	Approved
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.7175	Intermediate Similarity	NPD7228	Approved
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.7169	Intermediate Similarity	NPD4662	Approved
0.7169	Intermediate Similarity	NPD4661	Approved
0.7165	Intermediate Similarity	NPD7874	Approved
0.7165	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2353	Approved
0.7159	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1481	Phase 2
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD4287	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7698	Approved
0.7117	Intermediate Similarity	NPD2424	Discontinued
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4361	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data