NPASS Compound

Structure

CID295613 OpenBabel06191716102D 42 46 0 0 1 0 0 0 0 0999 V2000 -8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -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 4.3301 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 5.1962 1.0000 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 -4.3301 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 2 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 5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -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 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 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 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 3.4641 1.0000 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 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 36 1 0 0 0 0 2 37 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 19 2 0 0 0 0 9 15 1 0 0 0 0 9 17 2 0 0 0 0 10 16 1 0 0 0 0 10 38 1 0 0 0 0 11 39 1 0 0 0 0 12 17 1 0 0 0 0 13 36 1 0 0 0 0 14 37 1 0 0 0 0 15 21 1 0 0 0 0 15 29 2 0 0 0 0 16 22 1 0 0 0 0 16 30 1 1 0 0 0 17 40 1 0 0 0 0 18 21 2 0 0 0 0 18 40 1 0 0 0 0 19 21 1 0 0 0 0 19 41 1 0 0 0 0 20 11 1 6 0 0 0 20 23 1 0 0 0 0 20 42 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 24 1 0 0 0 0 23 32 1 1 0 0 0 24 26 1 0 0 0 0 24 33 1 6 0 0 0 25 27 1 0 0 0 0 25 34 1 1 0 0 0 26 28 1 0 0 0 0 26 35 1 1 0 0 0 27 38 1 0 0 0 0 27 39 1 6 0 0 0 28 41 1 6 0 0 0 28 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.18
Volume:	552.033
LogP:	1.112
LogD:	0.777
LogS:	-4.471
# Rotatable Bonds:	8
TPSA:	206.97
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	4.496
Fsp3:	0.464
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.12
MDCK Permeability:	3.79053526557982e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.775
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	69.79442596435547%
Volume Distribution (VD):	0.669
Pgp-substrate:	13.683006286621094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.194
CYP2D6-inhibitor:	0.087
CYP2D6-substrate:	0.671
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	1.221
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.723
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.846
AMES Toxicity:	0.684
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.711
Carcinogencity:	0.172
Eye Corrosion:	0.003
Eye Irritation:	0.087
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC295613

Natural Product ID:	NPC295613
*Common Name:**	7-Methoxy-2-(4-Methoxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-Trihydroxyoxan-2-Yl]Oxymethyl]Oxan-2-Yl]Oxychromen-4-One
IUPAC Name:	7-methoxy-2-(4-methoxyphenyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	ZTYIRUZJISZADH-AQLOEVPPSA-N
Standard InCHI:	InChI=1S/C28H32O14/c1-36-13-5-3-12(4-6-13)17-9-15(29)21-18(40-17)7-14(37-2)8-19(21)41-28-26(35)24(33)23(32)20(42-28)11-39-27-25(34)22(31)16(30)10-38-27/h3-9,16,20,22-28,30-35H,10-11H2,1-2H3/t16-,20-,22+,23-,24+,25-,26-,27+,28-/m1/s1
SMILES:	COc1ccc(cc1)c1cc(=O)c2c(cc(cc2O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O2)O)O)O)OC)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451605
PubChem CID:	21582635
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075750]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759170]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[548190]

☑ 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 NPC295613 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	405
0.1-0.2	1620
0.2-0.3	3698
0.3-0.4	9345
0.4-0.5	9380
0.5-0.6	4923
0.6-0.7	6018
0.7-0.8	5462
0.8-0.85	1049
0.85-0.9	530
0.9-0.95	219
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473657
0.9867	High Similarity	NPC473634
0.9867	High Similarity	NPC138811
0.9867	High Similarity	NPC22062
0.9801	High Similarity	NPC473623
0.98	High Similarity	NPC129827
0.98	High Similarity	NPC65003
0.98	High Similarity	NPC44931
0.98	High Similarity	NPC473512
0.9737	High Similarity	NPC101636
0.9673	High Similarity	NPC298171
0.9673	High Similarity	NPC244875
0.9673	High Similarity	NPC475382
0.9673	High Similarity	NPC240306
0.9671	High Similarity	NPC271270
0.9671	High Similarity	NPC97285
0.9671	High Similarity	NPC142860
0.9671	High Similarity	NPC246469
0.9671	High Similarity	NPC187379
0.9667	High Similarity	NPC95090
0.9667	High Similarity	NPC27408
0.961	High Similarity	NPC124155
0.961	High Similarity	NPC311850
0.961	High Similarity	NPC257566
0.961	High Similarity	NPC473644
0.9608	High Similarity	NPC265885
0.9608	High Similarity	NPC246943
0.9608	High Similarity	NPC181465
0.9608	High Similarity	NPC215710
0.9608	High Similarity	NPC253788
0.9608	High Similarity	NPC139320
0.9608	High Similarity	NPC116458
0.9608	High Similarity	NPC303913
0.9608	High Similarity	NPC276377
0.9608	High Similarity	NPC173582
0.9608	High Similarity	NPC476215
0.9608	High Similarity	NPC249281
0.9608	High Similarity	NPC473438
0.9608	High Similarity	NPC163242
0.9603	High Similarity	NPC45165
0.9603	High Similarity	NPC206378
0.96	High Similarity	NPC39360
0.96	High Similarity	NPC143851
0.96	High Similarity	NPC83283
0.96	High Similarity	NPC210003
0.96	High Similarity	NPC29763
0.9548	High Similarity	NPC475366
0.9548	High Similarity	NPC284277
0.9548	High Similarity	NPC475497
0.9548	High Similarity	NPC135358
0.9548	High Similarity	NPC287889
0.9545	High Similarity	NPC44947
0.9545	High Similarity	NPC190450
0.9542	High Similarity	NPC136761
0.9542	High Similarity	NPC471079
0.9542	High Similarity	NPC470405
0.9542	High Similarity	NPC304741
0.9539	High Similarity	NPC108831
0.9539	High Similarity	NPC60966
0.9539	High Similarity	NPC182634
0.9536	High Similarity	NPC72649
0.9536	High Similarity	NPC97052
0.9536	High Similarity	NPC169248
0.9536	High Similarity	NPC26195
0.9536	High Similarity	NPC39351
0.953	High Similarity	NPC213723
0.9487	High Similarity	NPC68592
0.9487	High Similarity	NPC11432
0.9487	High Similarity	NPC12013
0.9487	High Similarity	NPC64425
0.9487	High Similarity	NPC476470
0.9487	High Similarity	NPC32641
0.9487	High Similarity	NPC186816
0.9487	High Similarity	NPC189564
0.9487	High Similarity	NPC256188
0.9487	High Similarity	NPC262222
0.9487	High Similarity	NPC298666
0.9487	High Similarity	NPC221342
0.9487	High Similarity	NPC142142
0.9487	High Similarity	NPC203145
0.9487	High Similarity	NPC477613
0.9481	High Similarity	NPC170052
0.9481	High Similarity	NPC297987
0.9481	High Similarity	NPC64305
0.9481	High Similarity	NPC135846
0.9481	High Similarity	NPC47923
0.9477	High Similarity	NPC41121
0.9477	High Similarity	NPC320283
0.9477	High Similarity	NPC472459
0.9477	High Similarity	NPC111929
0.9477	High Similarity	NPC43761
0.9477	High Similarity	NPC73511
0.9474	High Similarity	NPC203500
0.9474	High Similarity	NPC323593
0.9474	High Similarity	NPC307938
0.9474	High Similarity	NPC170475
0.947	High Similarity	NPC106625
0.9423	High Similarity	NPC289667
0.9423	High Similarity	NPC15358
0.9423	High Similarity	NPC292929
0.9423	High Similarity	NPC76831
0.9416	High Similarity	NPC153342
0.9412	High Similarity	NPC77672
0.9412	High Similarity	NPC78263
0.9412	High Similarity	NPC156457
0.9412	High Similarity	NPC135391
0.9412	High Similarity	NPC197304
0.9412	High Similarity	NPC122809
0.9412	High Similarity	NPC54802
0.9412	High Similarity	NPC161749
0.9412	High Similarity	NPC197896
0.9412	High Similarity	NPC313163
0.9412	High Similarity	NPC258035
0.9412	High Similarity	NPC133671
0.9408	High Similarity	NPC99233
0.9404	High Similarity	NPC121001
0.9404	High Similarity	NPC259767
0.9404	High Similarity	NPC259182
0.9404	High Similarity	NPC88484
0.94	High Similarity	NPC191154
0.9367	High Similarity	NPC195257
0.9367	High Similarity	NPC5319
0.9367	High Similarity	NPC209296
0.9363	High Similarity	NPC70441
0.9363	High Similarity	NPC210073
0.9363	High Similarity	NPC115674
0.9355	High Similarity	NPC259957
0.9355	High Similarity	NPC477628
0.9355	High Similarity	NPC48093
0.9355	High Similarity	NPC270675
0.9355	High Similarity	NPC472994
0.9355	High Similarity	NPC129217
0.9355	High Similarity	NPC195685
0.9355	High Similarity	NPC159579
0.9355	High Similarity	NPC210961
0.9355	High Similarity	NPC216496
0.9355	High Similarity	NPC477629
0.9355	High Similarity	NPC224530
0.9355	High Similarity	NPC182045
0.9355	High Similarity	NPC85707
0.9355	High Similarity	NPC470125
0.9351	High Similarity	NPC308265
0.9346	High Similarity	NPC261866
0.9346	High Similarity	NPC127406
0.9338	High Similarity	NPC134819
0.9329	High Similarity	NPC218685
0.9308	High Similarity	NPC175429
0.9308	High Similarity	NPC209550
0.9308	High Similarity	NPC138990
0.9308	High Similarity	NPC277532
0.9299	High Similarity	NPC139060
0.9295	High Similarity	NPC259834
0.9295	High Similarity	NPC27942
0.9295	High Similarity	NPC150164
0.9295	High Similarity	NPC131745
0.9295	High Similarity	NPC472876
0.929	High Similarity	NPC200708
0.929	High Similarity	NPC110349
0.929	High Similarity	NPC472320
0.929	High Similarity	NPC271479
0.9286	High Similarity	NPC6985
0.9286	High Similarity	NPC43638
0.9286	High Similarity	NPC23817
0.9267	High Similarity	NPC199335
0.925	High Similarity	NPC474522
0.925	High Similarity	NPC475155
0.9245	High Similarity	NPC86008
0.9245	High Similarity	NPC61791
0.9245	High Similarity	NPC43587
0.9245	High Similarity	NPC293629
0.9241	High Similarity	NPC473278
0.9241	High Similarity	NPC89809
0.9241	High Similarity	NPC260504
0.9241	High Similarity	NPC8856
0.9236	High Similarity	NPC278419
0.9236	High Similarity	NPC121703
0.9236	High Similarity	NPC243930
0.9236	High Similarity	NPC66087
0.9236	High Similarity	NPC88023
0.9236	High Similarity	NPC19709
0.9236	High Similarity	NPC179198
0.9236	High Similarity	NPC183672
0.9236	High Similarity	NPC80068
0.9236	High Similarity	NPC309025
0.9231	High Similarity	NPC282169
0.9226	High Similarity	NPC104677
0.9221	High Similarity	NPC149368
0.9221	High Similarity	NPC265480
0.9216	High Similarity	NPC268950
0.9216	High Similarity	NPC211158
0.9216	High Similarity	NPC108706
0.9216	High Similarity	NPC87304
0.9216	High Similarity	NPC78021
0.9211	High Similarity	NPC23253
0.92	High Similarity	NPC23084
0.9193	High Similarity	NPC208668
0.9193	High Similarity	NPC204693
0.9187	High Similarity	NPC177731
0.9187	High Similarity	NPC150767
0.9187	High Similarity	NPC210808

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 NPC295613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	897
0.2-0.3	1716
0.3-0.4	2754
0.4-0.5	2030
0.5-0.6	980
0.6-0.7	269
0.7-0.8	119
0.8-0.85	18
0.85-0.9	2
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD4381	Clinical (unspecified phase)
0.9367	High Similarity	NPD7054	Approved
0.9367	High Similarity	NPD7804	Clinical (unspecified phase)
0.9308	High Similarity	NPD7472	Approved
0.9193	High Similarity	NPD7251	Discontinued
0.9187	High Similarity	NPD7074	Phase 3
0.9136	High Similarity	NPD7808	Phase 3
0.913	High Similarity	NPD6797	Phase 2
0.8774	High Similarity	NPD4380	Phase 2
0.8712	High Similarity	NPD3818	Discontinued
0.8675	High Similarity	NPD4338	Clinical (unspecified phase)
0.8608	High Similarity	NPD7096	Clinical (unspecified phase)
0.8589	High Similarity	NPD6166	Phase 2
0.8589	High Similarity	NPD6167	Clinical (unspecified phase)
0.8589	High Similarity	NPD6168	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.8544	High Similarity	NPD6801	Discontinued
0.8506	High Similarity	NPD6799	Approved
0.8477	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD5403	Approved
0.8452	Intermediate Similarity	NPD5401	Approved
0.8438	Intermediate Similarity	NPD3817	Phase 2
0.8428	Intermediate Similarity	NPD1934	Approved
0.8421	Intermediate Similarity	NPD1549	Phase 2
0.8411	Intermediate Similarity	NPD2796	Approved
0.8393	Intermediate Similarity	NPD6559	Discontinued
0.8375	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8261	Intermediate Similarity	NPD2801	Approved
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD5402	Approved
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8153	Intermediate Similarity	NPD1511	Approved
0.8148	Intermediate Similarity	NPD8455	Phase 2
0.8105	Intermediate Similarity	NPD1510	Phase 2
0.8072	Intermediate Similarity	NPD6959	Discontinued
0.8067	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1512	Approved
0.8049	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5494	Approved
0.7977	Intermediate Similarity	NPD8313	Approved
0.7977	Intermediate Similarity	NPD8312	Approved
0.7966	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1240	Approved
0.7939	Intermediate Similarity	NPD3882	Suspended
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3787	Discontinued
0.7907	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7584	Approved
0.7857	Intermediate Similarity	NPD1607	Approved
0.7848	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD3751	Discontinued
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7736	Intermediate Similarity	NPD3750	Approved
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD6832	Phase 2
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7677	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD3748	Approved
0.763	Intermediate Similarity	NPD7228	Approved
0.7622	Intermediate Similarity	NPD1653	Approved
0.7619	Intermediate Similarity	NPD8151	Discontinued
0.761	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7584	Intermediate Similarity	NPD1091	Approved
0.7576	Intermediate Similarity	NPD7458	Discontinued
0.7574	Intermediate Similarity	NPD3749	Approved
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7568	Intermediate Similarity	NPD6782	Approved
0.7568	Intermediate Similarity	NPD6779	Approved
0.7568	Intermediate Similarity	NPD6776	Approved
0.7568	Intermediate Similarity	NPD6778	Approved
0.7568	Intermediate Similarity	NPD6781	Approved
0.7568	Intermediate Similarity	NPD6780	Approved
0.7568	Intermediate Similarity	NPD6777	Approved
0.7562	Intermediate Similarity	NPD1652	Phase 2
0.7561	Intermediate Similarity	NPD920	Approved
0.7557	Intermediate Similarity	NPD7685	Pre-registration
0.754	Intermediate Similarity	NPD7697	Approved
0.754	Intermediate Similarity	NPD7698	Approved
0.754	Intermediate Similarity	NPD7435	Discontinued
0.754	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7783	Phase 2
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.7514	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7583	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7474	Intermediate Similarity	NPD7585	Approved
0.7467	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7240	Approved
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1243	Approved
0.7451	Intermediate Similarity	NPD2798	Approved
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7266	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7871	Phase 2
0.7407	Intermediate Similarity	NPD7870	Phase 2
0.7405	Intermediate Similarity	NPD6651	Approved
0.7394	Intermediate Similarity	NPD6823	Phase 2
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7366	Intermediate Similarity	NPD7699	Phase 2
0.7366	Intermediate Similarity	NPD7700	Phase 2
0.7363	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7097	Phase 1
0.7346	Intermediate Similarity	NPD2800	Approved
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7337	Intermediate Similarity	NPD6844	Discontinued
0.7337	Intermediate Similarity	NPD37	Approved
0.7326	Intermediate Similarity	NPD919	Approved
0.7325	Intermediate Similarity	NPD6233	Phase 2
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.731	Intermediate Similarity	NPD4965	Approved
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4966	Approved
0.7306	Intermediate Similarity	NPD7874	Approved
0.7306	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5953	Discontinued
0.7297	Intermediate Similarity	NPD4360	Phase 2
0.7297	Intermediate Similarity	NPD6535	Approved
0.7297	Intermediate Similarity	NPD6534	Approved
0.7297	Intermediate Similarity	NPD4363	Phase 3
0.7278	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1613	Approved
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1203	Approved
0.7268	Intermediate Similarity	NPD7801	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7261	Intermediate Similarity	NPD3268	Approved
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7241	Intermediate Similarity	NPD1247	Approved
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7229	Intermediate Similarity	NPD2533	Approved
0.7229	Intermediate Similarity	NPD2534	Approved
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2532	Approved
0.7225	Intermediate Similarity	NPD8319	Approved
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.7225	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD3225	Approved
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9717	Approved
0.7161	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD3226	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2654	Approved
0.7126	Intermediate Similarity	NPD4662	Approved
0.7126	Intermediate Similarity	NPD4661	Approved
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD422	Phase 1
0.7117	Intermediate Similarity	NPD2344	Approved
0.7117	Intermediate Similarity	NPD2346	Discontinued
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.7066	Intermediate Similarity	NPD7390	Discontinued
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7063	Intermediate Similarity	NPD943	Approved
0.7059	Intermediate Similarity	NPD6213	Phase 3
0.7059	Intermediate Similarity	NPD6212	Phase 3
0.7059	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.703	Intermediate Similarity	NPD6674	Discontinued
0.7025	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD230	Phase 1
0.7019	Intermediate Similarity	NPD447	Suspended
0.7013	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD1019	Discontinued
0.7	Intermediate Similarity	NPD4062	Phase 3
0.6994	Remote Similarity	NPD4308	Phase 3
0.6988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3027	Phase 3
0.6978	Remote Similarity	NPD6104	Discontinued
0.6977	Remote Similarity	NPD5889	Approved
0.6977	Remote Similarity	NPD5890	Approved
0.6962	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4288	Approved
0.6946	Remote Similarity	NPD2354	Approved
0.6946	Remote Similarity	NPD8155	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