NPASS Compound

Structure

NPC197037 OpenBabel07101718332D 39 43 0 0 1 0 0 0 0 0999 V2000 -2.9930 0.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8970 1.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3983 3.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5117 3.1430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2067 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 2.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6633 2.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4611 3.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7767 2.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5745 3.5469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7745 -1.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0588 1.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8943 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3726 1.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0332 2.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2323 2.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6740 0.9504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5489 -0.8943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.8943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6284 1.8697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8598 1.0059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7745 0.4471 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4127 0.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5430 1.3109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3457 2.6040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8539 2.3168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5489 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9901 2.0854 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5703 3.8561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5573 0.0638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3234 -1.3414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7465 0.8892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9571 -0.4780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8013 3.3135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6720 2.9212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8943 -0.8943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0035 1.7778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2315 0.8638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 29 1 0 0 0 0 13 28 1 0 0 0 0 13 37 1 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 30 2 0 0 0 0 15 39 1 0 0 0 0 16 25 1 0 0 0 0 17 31 1 6 0 0 0 18 27 1 1 0 0 0 18 32 1 0 0 0 0 19 28 1 6 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 33 2 0 0 0 0 22 24 1 0 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 34 2 0 0 0 0 24 29 1 1 0 0 0 24 38 1 0 0 0 0 25 35 2 0 0 0 0 25 38 1 0 0 0 0 26 29 1 0 0 0 0 27 5 1 6 0 0 0 28 39 1 1 0 0 0 29 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.22
Volume:	534.168
LogP:	2.256
LogD:	1.21
LogS:	-4.614
# Rotatable Bonds:	5
TPSA:	153.5
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	5.569
Fsp3:	0.621
Lipinski Rule-of-5:	Accepted
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:	-5.363
MDCK Permeability:	4.941959196003154e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.115
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.709
Plasma Protein Binding (PPB):	66.53248596191406%
Volume Distribution (VD):	0.474
Pgp-substrate:	25.903648376464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.394
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.407

ADMET: Excretion

Clearance (CL):	5.944
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.766
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.365
Maximum Recommended Daily Dose:	0.333
Skin Sensitization:	0.109
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC197037

Natural Product ID:	NPC197037
*Common Name:**	UEDMLPVUDFCAQM-IWVNULRZSA-N
IUPAC Name:	n.a.
Synonyms:	7-epi-10-oxo-10-DAB
Standard InCHIKey:	UEDMLPVUDFCAQM-IWVNULRZSA-N
Standard InCHI:	InChI=1S/C29H34O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,22,24,31-32,36H,11-13H2,1-5H3/t17-,18+,19+,22-,24-,27+,28-,29+/m0/s1
SMILES:	CC1=C2C(=O)C(=O)[C@]3(C)[C@@H](C[C@@H]4[C@@](CO4)([C@H]3[C@@H]([C@](C[C@@H]1O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250045
PubChem CID:	5316369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027752]
NPO32766	luteibacter sp.	Species	Rhodanobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[18001087]
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20527910]
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014347]
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	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	7
Others	1

Activity Type	# Activity
Cell Line	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	<	10000.0	nM	PMID[517917]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	<	10000.0	nM	PMID[517917]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	1380.0	nM	PMID[517917]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[517917]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	4890.0	nM	PMID[517917]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	60000.0	nM	PMID[517919]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	60000.0	nM	PMID[517920]
NPT2	Others	Unspecified		ID50	>	100.0	uM	PMID[517918]

☑ 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 NPC197037 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	336
0.1-0.2	1173
0.2-0.3	2585
0.3-0.4	5714
0.4-0.5	9932
0.5-0.6	10502
0.6-0.7	10337
0.7-0.8	1822
0.8-0.85	242
0.85-0.9	39
0.9-0.95	3
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC91730
0.986	High Similarity	NPC229545
0.986	High Similarity	NPC248265
0.986	High Similarity	NPC11588
0.986	High Similarity	NPC134685
0.9792	High Similarity	NPC259144
0.9792	High Similarity	NPC114357
0.9792	High Similarity	NPC155329
0.9787	High Similarity	NPC217918
0.9722	High Similarity	NPC219419
0.9574	High Similarity	NPC38696
0.9296	High Similarity	NPC34012
0.9276	High Similarity	NPC471493
0.9257	High Similarity	NPC21410
0.9257	High Similarity	NPC473670
0.9236	High Similarity	NPC127857
0.9184	High Similarity	NPC471103
0.9178	High Similarity	NPC250046
0.9178	High Similarity	NPC60509
0.9178	High Similarity	NPC81698
0.9116	High Similarity	NPC7095
0.9116	High Similarity	NPC161239
0.9116	High Similarity	NPC198455
0.9116	High Similarity	NPC165260
0.9097	High Similarity	NPC477894
0.9054	High Similarity	NPC51602
0.9054	High Similarity	NPC101043
0.9054	High Similarity	NPC306799
0.9021	High Similarity	NPC472547
0.9007	High Similarity	NPC472393
0.9	High Similarity	NPC132599
0.9	High Similarity	NPC469730
0.9	High Similarity	NPC473632
0.9	High Similarity	NPC228204
0.9	High Similarity	NPC26033
0.8993	High Similarity	NPC472548
0.8986	High Similarity	NPC112216
0.8958	High Similarity	NPC472576
0.8958	High Similarity	NPC27377
0.8958	High Similarity	NPC41481
0.8958	High Similarity	NPC87448
0.8958	High Similarity	NPC97947
0.8958	High Similarity	NPC291599
0.8958	High Similarity	NPC118080
0.8944	High Similarity	NPC472374
0.8944	High Similarity	NPC472372
0.894	High Similarity	NPC106895
0.894	High Similarity	NPC217091
0.8933	High Similarity	NPC472022
0.8933	High Similarity	NPC472030
0.8933	High Similarity	NPC237549
0.8933	High Similarity	NPC304876
0.8933	High Similarity	NPC249471
0.8933	High Similarity	NPC265395
0.8933	High Similarity	NPC469477
0.8933	High Similarity	NPC472005
0.8933	High Similarity	NPC133430
0.8933	High Similarity	NPC242262
0.8933	High Similarity	NPC473414
0.8933	High Similarity	NPC158333
0.8933	High Similarity	NPC257213
0.8933	High Similarity	NPC256142
0.8933	High Similarity	NPC1173
0.8912	High Similarity	NPC474935
0.8897	High Similarity	NPC182869
0.8889	High Similarity	NPC100913
0.8889	High Similarity	NPC171207
0.8889	High Similarity	NPC97667
0.8889	High Similarity	NPC275592
0.8889	High Similarity	NPC90614
0.8881	High Similarity	NPC39549
0.8874	High Similarity	NPC472549
0.8874	High Similarity	NPC282239
0.8874	High Similarity	NPC112523
0.8874	High Similarity	NPC473611
0.8874	High Similarity	NPC114410
0.8873	High Similarity	NPC477893
0.8873	High Similarity	NPC477896
0.8867	High Similarity	NPC477905
0.8851	High Similarity	NPC132652
0.8844	High Similarity	NPC471100
0.8844	High Similarity	NPC92867
0.8844	High Similarity	NPC311825
0.8844	High Similarity	NPC471107
0.8828	High Similarity	NPC16912
0.8824	High Similarity	NPC469399
0.8816	High Similarity	NPC11410
0.8811	High Similarity	NPC472551
0.8811	High Similarity	NPC472545
0.8808	High Similarity	NPC77719
0.88	High Similarity	NPC470153
0.8794	High Similarity	NPC80599
0.8784	High Similarity	NPC20255
0.8776	High Similarity	NPC241951
0.8776	High Similarity	NPC470152
0.8776	High Similarity	NPC475759
0.8759	High Similarity	NPC183270
0.8759	High Similarity	NPC477904
0.8758	High Similarity	NPC469771
0.8758	High Similarity	NPC469417
0.875	High Similarity	NPC5115
0.875	High Similarity	NPC251139
0.8716	High Similarity	NPC473088
0.8716	High Similarity	NPC472568
0.8716	High Similarity	NPC472575
0.8716	High Similarity	NPC469349
0.8716	High Similarity	NPC472556
0.8716	High Similarity	NPC471104
0.8716	High Similarity	NPC277053
0.8716	High Similarity	NPC158663
0.8716	High Similarity	NPC29704
0.8716	High Similarity	NPC470159
0.8716	High Similarity	NPC70403
0.8716	High Similarity	NPC184817
0.8716	High Similarity	NPC174982
0.8716	High Similarity	NPC301946
0.8716	High Similarity	NPC171525
0.8716	High Similarity	NPC472572
0.8716	High Similarity	NPC472571
0.8716	High Similarity	NPC177940
0.8716	High Similarity	NPC200471
0.8716	High Similarity	NPC476973
0.8716	High Similarity	NPC470157
0.8716	High Similarity	NPC96903
0.8716	High Similarity	NPC125882
0.8707	High Similarity	NPC95449
0.8707	High Similarity	NPC163087
0.8701	High Similarity	NPC471102
0.8662	High Similarity	NPC472394
0.8662	High Similarity	NPC209851
0.8658	High Similarity	NPC469513
0.8649	High Similarity	NPC188865
0.8649	High Similarity	NPC25768
0.8649	High Similarity	NPC11685
0.8649	High Similarity	NPC472573
0.8649	High Similarity	NPC163719
0.8649	High Similarity	NPC95265
0.8649	High Similarity	NPC475122
0.8649	High Similarity	NPC70716
0.8649	High Similarity	NPC125106
0.8649	High Similarity	NPC57628
0.8649	High Similarity	NPC34943
0.8649	High Similarity	NPC95810
0.8649	High Similarity	NPC471912
0.8649	High Similarity	NPC472569
0.8649	High Similarity	NPC476974
0.8649	High Similarity	NPC80895
0.8649	High Similarity	NPC472570
0.8639	High Similarity	NPC472546
0.8618	High Similarity	NPC22571
0.8618	High Similarity	NPC469648
0.8618	High Similarity	NPC138641
0.8618	High Similarity	NPC469647
0.8618	High Similarity	NPC283875
0.8611	High Similarity	NPC291638
0.8611	High Similarity	NPC17877
0.8611	High Similarity	NPC472577
0.8611	High Similarity	NPC66761
0.8611	High Similarity	NPC195647
0.8609	High Similarity	NPC470245
0.8609	High Similarity	NPC254558
0.8609	High Similarity	NPC473214
0.86	High Similarity	NPC473760
0.859	High Similarity	NPC476077
0.8581	High Similarity	NPC91703
0.8571	High Similarity	NPC224491
0.8553	High Similarity	NPC472398
0.8543	High Similarity	NPC270590
0.8543	High Similarity	NPC301556
0.8543	High Similarity	NPC92293
0.8543	High Similarity	NPC471101
0.8543	High Similarity	NPC473215
0.8543	High Similarity	NPC476975
0.8543	High Similarity	NPC266265
0.8542	High Similarity	NPC474608
0.8533	High Similarity	NPC477737
0.8533	High Similarity	NPC240115
0.8533	High Similarity	NPC48599
0.8533	High Similarity	NPC478263
0.8533	High Similarity	NPC209592
0.8521	High Similarity	NPC473443
0.8521	High Similarity	NPC472388
0.8514	High Similarity	NPC192658
0.8497	Intermediate Similarity	NPC233581
0.8497	Intermediate Similarity	NPC145649
0.8481	Intermediate Similarity	NPC478073
0.8477	Intermediate Similarity	NPC327031
0.8477	Intermediate Similarity	NPC281717
0.8467	Intermediate Similarity	NPC478264
0.8451	Intermediate Similarity	NPC225103
0.8446	Intermediate Similarity	NPC213567
0.8435	Intermediate Similarity	NPC9905
0.8431	Intermediate Similarity	NPC469415
0.8428	Intermediate Similarity	NPC471134
0.8428	Intermediate Similarity	NPC477627
0.8418	Intermediate Similarity	NPC477190
0.8418	Intermediate Similarity	NPC43304
0.8418	Intermediate Similarity	NPC477188
0.8411	Intermediate Similarity	NPC312393
0.8411	Intermediate Similarity	NPC473602

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 NPC197037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	783
0.2-0.3	1717
0.3-0.4	2876
0.4-0.5	2210
0.5-0.6	987
0.6-0.7	272
0.7-0.8	17
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD8368	Discontinued
0.8494	Intermediate Similarity	NPD8434	Phase 2
0.8485	Intermediate Similarity	NPD8407	Phase 2
0.8393	Intermediate Similarity	NPD8360	Approved
0.8393	Intermediate Similarity	NPD8361	Approved
0.8284	Intermediate Similarity	NPD8435	Approved
0.8121	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD8485	Approved
0.7987	Intermediate Similarity	NPD7236	Approved
0.7966	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7239	Suspended
0.7844	Intermediate Similarity	NPD7799	Discontinued
0.7644	Intermediate Similarity	NPD8150	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7417	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7058	Phase 2
0.741	Intermediate Similarity	NPD7057	Phase 3
0.7407	Intermediate Similarity	NPD8462	Phase 1
0.7386	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7473	Discontinued
0.7365	Intermediate Similarity	NPD7075	Discontinued
0.7358	Intermediate Similarity	NPD6190	Approved
0.7344	Intermediate Similarity	NPD8404	Phase 2
0.7317	Intermediate Similarity	NPD4380	Phase 2
0.7289	Intermediate Similarity	NPD7819	Suspended
0.7289	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2629	Approved
0.7229	Intermediate Similarity	NPD6801	Discontinued
0.7212	Intermediate Similarity	NPD6599	Discontinued
0.7193	Intermediate Similarity	NPD6232	Discontinued
0.7188	Intermediate Similarity	NPD8166	Discontinued
0.7184	Intermediate Similarity	NPD5844	Phase 1
0.7167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5402	Approved
0.7105	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5760	Phase 2
0.7083	Intermediate Similarity	NPD5761	Phase 2
0.7083	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7078	Intermediate Similarity	NPD7008	Discontinued
0.7059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7048	Intermediate Similarity	NPD3226	Approved
0.7041	Intermediate Similarity	NPD3817	Phase 2
0.7029	Intermediate Similarity	NPD3818	Discontinued
0.7024	Intermediate Similarity	NPD1934	Approved
0.7012	Intermediate Similarity	NPD2532	Approved
0.7012	Intermediate Similarity	NPD2534	Approved
0.7012	Intermediate Similarity	NPD2533	Approved
0.7011	Intermediate Similarity	NPD6535	Approved
0.7011	Intermediate Similarity	NPD6534	Approved
0.7006	Intermediate Similarity	NPD230	Phase 1
0.6989	Remote Similarity	NPD7699	Phase 2
0.6989	Remote Similarity	NPD7700	Phase 2
0.6986	Remote Similarity	NPD4198	Discontinued
0.6984	Remote Similarity	NPD7435	Discontinued
0.6982	Remote Similarity	NPD2801	Approved
0.6981	Remote Similarity	NPD7305	Phase 1
0.6977	Remote Similarity	NPD5494	Approved
0.6975	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7411	Suspended
0.6959	Remote Similarity	NPD7741	Discontinued
0.6951	Remote Similarity	NPD6799	Approved
0.6949	Remote Similarity	NPD7074	Phase 3
0.6947	Remote Similarity	NPD8320	Phase 1
0.6947	Remote Similarity	NPD8319	Approved
0.6941	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8127	Discontinued
0.6932	Remote Similarity	NPD3751	Discontinued
0.6928	Remote Similarity	NPD5403	Approved
0.6927	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3764	Approved
0.6923	Remote Similarity	NPD37	Approved
0.6919	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5951	Approved
0.6914	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6166	Phase 2
0.6914	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4965	Approved
0.6901	Remote Similarity	NPD4967	Phase 2
0.6901	Remote Similarity	NPD4966	Approved
0.6894	Remote Similarity	NPD2346	Discontinued
0.6893	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7054	Approved
0.6879	Remote Similarity	NPD7961	Discontinued
0.6875	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7685	Pre-registration
0.6872	Remote Similarity	NPD6765	Approved
0.6872	Remote Similarity	NPD6764	Approved
0.6872	Remote Similarity	NPD6559	Discontinued
0.6854	Remote Similarity	NPD7472	Approved
0.6853	Remote Similarity	NPD2182	Approved
0.6852	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6010	Discontinued
0.6832	Remote Similarity	NPD2935	Discontinued
0.6829	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6782	Approved
0.6825	Remote Similarity	NPD6781	Approved
0.6825	Remote Similarity	NPD6780	Approved
0.6825	Remote Similarity	NPD6778	Approved
0.6825	Remote Similarity	NPD6779	Approved
0.6825	Remote Similarity	NPD6777	Approved
0.6825	Remote Similarity	NPD6776	Approved
0.6821	Remote Similarity	NPD6234	Discontinued
0.6816	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5401	Approved
0.6807	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3882	Suspended
0.6778	Remote Similarity	NPD7251	Discontinued
0.677	Remote Similarity	NPD2799	Discontinued
0.677	Remote Similarity	NPD1510	Phase 2
0.6769	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7874	Approved
0.6768	Remote Similarity	NPD3750	Approved
0.6766	Remote Similarity	NPD6273	Approved
0.6761	Remote Similarity	NPD5048	Discontinued
0.6755	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5126	Approved
0.6755	Remote Similarity	NPD5125	Phase 3
0.675	Remote Similarity	NPD6651	Approved
0.6748	Remote Similarity	NPD1549	Phase 2
0.6746	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6959	Discontinued
0.6742	Remote Similarity	NPD7228	Approved
0.674	Remote Similarity	NPD7808	Phase 3
0.6733	Remote Similarity	NPD9545	Approved
0.6728	Remote Similarity	NPD2796	Approved
0.6728	Remote Similarity	NPD6100	Approved
0.6728	Remote Similarity	NPD6099	Approved
0.6723	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6797	Phase 2
0.6721	Remote Similarity	NPD6784	Approved
0.6721	Remote Similarity	NPD6785	Approved
0.6719	Remote Similarity	NPD7696	Phase 3
0.6719	Remote Similarity	NPD7497	Discontinued
0.6719	Remote Similarity	NPD7698	Approved
0.6719	Remote Similarity	NPD7697	Approved
0.6711	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2313	Discontinued
0.6707	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2800	Approved
0.6705	Remote Similarity	NPD3787	Discontinued
0.6705	Remote Similarity	NPD7768	Phase 2
0.6689	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3300	Phase 2
0.6687	Remote Similarity	NPD7266	Discontinued
0.6686	Remote Similarity	NPD1465	Phase 2
0.6684	Remote Similarity	NPD7871	Phase 2
0.6684	Remote Similarity	NPD7870	Phase 2
0.6684	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6213	Phase 3
0.6684	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD6287	Discontinued
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7033	Discontinued
0.665	Remote Similarity	NPD7801	Approved
0.6647	Remote Similarity	NPD1511	Approved
0.6647	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1607	Approved
0.6644	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD8151	Discontinued
0.6627	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5406	Approved
0.6626	Remote Similarity	NPD5408	Approved
0.6626	Remote Similarity	NPD5404	Approved
0.6626	Remote Similarity	NPD5405	Approved
0.6625	Remote Similarity	NPD943	Approved
0.6625	Remote Similarity	NPD1240	Approved
0.6603	Remote Similarity	NPD1470	Approved
0.6573	Remote Similarity	NPD164	Approved
0.6568	Remote Similarity	NPD1512	Approved
0.6564	Remote Similarity	NPD3748	Approved
0.6562	Remote Similarity	NPD6663	Approved
0.6554	Remote Similarity	NPD6858	Approved
0.6554	Remote Similarity	NPD7199	Phase 2
0.6554	Remote Similarity	NPD7094	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data