NPASS Compound

Structure

CID91730 OpenBabel06191715432D 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 0 0 0 0 0 0 0 0 0 0 -1.5489 -0.8943 0.0000 C 0 0 1 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 2 0 0 0 0 18 27 1 6 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:	540.2
Volume:	531.532
LogP:	2.273
LogD:	1.843
LogS:	-4.682
# 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:	0.426
Synthetic Accessibility Score:	5.352
Fsp3:	0.552
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:	-5.328
MDCK Permeability:	4.172603439656086e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.5
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.614
Plasma Protein Binding (PPB):	71.9985580444336%
Volume Distribution (VD):	1.014
Pgp-substrate:	19.056371688842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.328
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.182
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.359
CYP3A4-substrate:	0.418

ADMET: Excretion

Clearance (CL):	6.534
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.27
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.514
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.85
Skin Sensitization:	0.272
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC91730

Natural Product ID:	NPC91730
*Common Name:**	QVDGHPMALHVSBN-WTLWSZCSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QVDGHPMALHVSBN-WTLWSZCSSA-N
Standard InCHI:	InChI=1S/C29H32O10/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/h6-10,18-19,22,24,32,36H,11-13H2,1-5H3/t18-,19+,22-,24-,27+,28-,29+/m0/s1
SMILES:	CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)CC(=O)C(=C(C2(C)C)C(=O)C1=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450706
PubChem CID:	44575404
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
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11554	Taxus sumatrana	Species	Taxaceae	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
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT376	Cell Line	A498	Homo sapiens	Inhibition	=	79.1	%	PMID[463311]
NPT405	Cell Line	NCI-H226	Homo sapiens	Inhibition	=	97.3	%	PMID[463311]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	54.7	%	PMID[463311]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	=	100.0	%	PMID[463311]

☑ 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 NPC91730 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	335
0.1-0.2	1180
0.2-0.3	2584
0.3-0.4	5707
0.4-0.5	10021
0.5-0.6	10574
0.6-0.7	10350
0.7-0.8	1643
0.8-0.85	243
0.85-0.9	45
0.9-0.95	3
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC197037
0.9857	High Similarity	NPC217918
0.979	High Similarity	NPC11588
0.979	High Similarity	NPC134685
0.979	High Similarity	NPC248265
0.979	High Similarity	NPC219419
0.979	High Similarity	NPC229545
0.9722	High Similarity	NPC114357
0.9722	High Similarity	NPC155329
0.9722	High Similarity	NPC259144
0.9504	High Similarity	NPC38696
0.9362	High Similarity	NPC34012
0.9301	High Similarity	NPC127857
0.9247	High Similarity	NPC471103
0.9241	High Similarity	NPC81698
0.9241	High Similarity	NPC60509
0.9241	High Similarity	NPC250046
0.9211	High Similarity	NPC471493
0.9189	High Similarity	NPC21410
0.9189	High Similarity	NPC473670
0.9178	High Similarity	NPC7095
0.9178	High Similarity	NPC198455
0.9178	High Similarity	NPC161239
0.9178	High Similarity	NPC165260
0.9116	High Similarity	NPC306799
0.9116	High Similarity	NPC51602
0.9116	High Similarity	NPC101043
0.9085	High Similarity	NPC472547
0.9067	High Similarity	NPC472393
0.906	High Similarity	NPC228204
0.906	High Similarity	NPC26033
0.9054	High Similarity	NPC472548
0.9048	High Similarity	NPC112216
0.9028	High Similarity	NPC477894
0.9021	High Similarity	NPC27377
0.9021	High Similarity	NPC97947
0.9021	High Similarity	NPC41481
0.9021	High Similarity	NPC291599
0.9021	High Similarity	NPC472576
0.9021	High Similarity	NPC87448
0.9021	High Similarity	NPC118080
0.9	High Similarity	NPC106895
0.9	High Similarity	NPC217091
0.8993	High Similarity	NPC304876
0.8993	High Similarity	NPC249471
0.8993	High Similarity	NPC257213
0.8993	High Similarity	NPC1173
0.8993	High Similarity	NPC472022
0.8993	High Similarity	NPC133430
0.8993	High Similarity	NPC473414
0.8993	High Similarity	NPC265395
0.8993	High Similarity	NPC472005
0.8993	High Similarity	NPC469477
0.8993	High Similarity	NPC242262
0.8993	High Similarity	NPC237549
0.8993	High Similarity	NPC256142
0.8993	High Similarity	NPC472030
0.8993	High Similarity	NPC158333
0.8973	High Similarity	NPC474935
0.8958	High Similarity	NPC182869
0.8951	High Similarity	NPC275592
0.8951	High Similarity	NPC97667
0.8951	High Similarity	NPC100913
0.8951	High Similarity	NPC90614
0.8951	High Similarity	NPC171207
0.8944	High Similarity	NPC39549
0.8933	High Similarity	NPC282239
0.8933	High Similarity	NPC112523
0.8933	High Similarity	NPC473632
0.8933	High Similarity	NPC114410
0.8933	High Similarity	NPC469730
0.8933	High Similarity	NPC132599
0.8933	High Similarity	NPC472549
0.8926	High Similarity	NPC477905
0.8904	High Similarity	NPC471107
0.8904	High Similarity	NPC471100
0.8889	High Similarity	NPC16912
0.8882	High Similarity	NPC469399
0.8873	High Similarity	NPC472551
0.8873	High Similarity	NPC472372
0.8873	High Similarity	NPC472374
0.8873	High Similarity	NPC472545
0.8867	High Similarity	NPC77719
0.8857	High Similarity	NPC80599
0.8836	High Similarity	NPC470152
0.8836	High Similarity	NPC475759
0.8836	High Similarity	NPC241951
0.8819	High Similarity	NPC183270
0.8819	High Similarity	NPC477904
0.8816	High Similarity	NPC469771
0.8816	High Similarity	NPC469417
0.8808	High Similarity	NPC473611
0.8808	High Similarity	NPC5115
0.8803	High Similarity	NPC477893
0.8803	High Similarity	NPC477896
0.8784	High Similarity	NPC132652
0.8776	High Similarity	NPC473088
0.8776	High Similarity	NPC472575
0.8776	High Similarity	NPC469349
0.8776	High Similarity	NPC158663
0.8776	High Similarity	NPC171525
0.8776	High Similarity	NPC471104
0.8776	High Similarity	NPC277053
0.8776	High Similarity	NPC70403
0.8776	High Similarity	NPC311825
0.8776	High Similarity	NPC29704
0.8776	High Similarity	NPC174982
0.8776	High Similarity	NPC177940
0.8776	High Similarity	NPC472572
0.8776	High Similarity	NPC301946
0.8776	High Similarity	NPC472571
0.8776	High Similarity	NPC184817
0.8776	High Similarity	NPC472568
0.8776	High Similarity	NPC200471
0.8776	High Similarity	NPC476973
0.8776	High Similarity	NPC470157
0.8776	High Similarity	NPC92867
0.8776	High Similarity	NPC470159
0.8776	High Similarity	NPC96903
0.8767	High Similarity	NPC163087
0.8758	High Similarity	NPC471102
0.875	High Similarity	NPC11410
0.8733	High Similarity	NPC470153
0.8723	High Similarity	NPC209851
0.8723	High Similarity	NPC472394
0.8716	High Similarity	NPC20255
0.8716	High Similarity	NPC469513
0.8707	High Similarity	NPC476974
0.8707	High Similarity	NPC472569
0.8707	High Similarity	NPC475122
0.8707	High Similarity	NPC472570
0.8707	High Similarity	NPC25768
0.8707	High Similarity	NPC57628
0.8707	High Similarity	NPC163719
0.8707	High Similarity	NPC11685
0.8707	High Similarity	NPC95265
0.8707	High Similarity	NPC70716
0.8707	High Similarity	NPC125106
0.8707	High Similarity	NPC80895
0.8707	High Similarity	NPC471912
0.8707	High Similarity	NPC472573
0.8707	High Similarity	NPC95810
0.8707	High Similarity	NPC188865
0.8699	High Similarity	NPC472546
0.8684	High Similarity	NPC251139
0.8671	High Similarity	NPC291638
0.8671	High Similarity	NPC472577
0.8671	High Similarity	NPC17877
0.8671	High Similarity	NPC195647
0.8671	High Similarity	NPC66761
0.8667	High Similarity	NPC470245
0.8667	High Similarity	NPC254558
0.8667	High Similarity	NPC473214
0.8658	High Similarity	NPC473760
0.8649	High Similarity	NPC125882
0.8649	High Similarity	NPC472556
0.8639	High Similarity	NPC95449
0.863	High Similarity	NPC224491
0.8601	High Similarity	NPC474608
0.86	High Similarity	NPC476975
0.86	High Similarity	NPC301556
0.86	High Similarity	NPC471101
0.86	High Similarity	NPC270590
0.86	High Similarity	NPC92293
0.86	High Similarity	NPC473215
0.86	High Similarity	NPC266265
0.8591	High Similarity	NPC477737
0.8591	High Similarity	NPC209592
0.8591	High Similarity	NPC478263
0.8591	High Similarity	NPC48599
0.8582	High Similarity	NPC473443
0.8581	High Similarity	NPC34943
0.8553	High Similarity	NPC22571
0.8553	High Similarity	NPC469647
0.8553	High Similarity	NPC469648
0.8553	High Similarity	NPC138641
0.8553	High Similarity	NPC283875
0.8533	High Similarity	NPC281717
0.8533	High Similarity	NPC327031
0.8526	High Similarity	NPC476077
0.8523	High Similarity	NPC478264
0.8514	High Similarity	NPC91703
0.8511	High Similarity	NPC225103
0.8503	High Similarity	NPC213567
0.8487	Intermediate Similarity	NPC469415
0.8487	Intermediate Similarity	NPC472398
0.8471	Intermediate Similarity	NPC43304
0.8471	Intermediate Similarity	NPC477188
0.8471	Intermediate Similarity	NPC477190
0.8467	Intermediate Similarity	NPC473602
0.8467	Intermediate Similarity	NPC240115
0.8451	Intermediate Similarity	NPC472388
0.8446	Intermediate Similarity	NPC192658
0.8442	Intermediate Similarity	NPC469422
0.8442	Intermediate Similarity	NPC469456
0.8442	Intermediate Similarity	NPC34066
0.844	Intermediate Similarity	NPC195224
0.8438	Intermediate Similarity	NPC102465
0.8435	Intermediate Similarity	NPC473613
0.8435	Intermediate Similarity	NPC43241

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 NPC91730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	782
0.2-0.3	1729
0.3-0.4	2864
0.4-0.5	2218
0.5-0.6	985
0.6-0.7	270
0.7-0.8	16
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD8368	Discontinued
0.8537	High Similarity	NPD8407	Phase 2
0.8434	Intermediate Similarity	NPD8434	Phase 2
0.8333	Intermediate Similarity	NPD8361	Approved
0.8333	Intermediate Similarity	NPD8435	Approved
0.8333	Intermediate Similarity	NPD8360	Approved
0.8171	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD8485	Approved
0.8039	Intermediate Similarity	NPD7236	Approved
0.8	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7239	Suspended
0.7892	Intermediate Similarity	NPD7799	Discontinued
0.7586	Intermediate Similarity	NPD8150	Discontinued
0.7455	Intermediate Similarity	NPD7057	Phase 3
0.7455	Intermediate Similarity	NPD7058	Phase 2
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.7447	Intermediate Similarity	NPD8462	Phase 1
0.7434	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7819	Suspended
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD7075	Discontinued
0.7296	Intermediate Similarity	NPD6190	Approved
0.7292	Intermediate Similarity	NPD8404	Phase 2
0.7256	Intermediate Similarity	NPD6599	Discontinued
0.7256	Intermediate Similarity	NPD4380	Phase 2
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2629	Approved
0.7169	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6232	Discontinued
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD8166	Discontinued
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3817	Phase 2
0.7083	Intermediate Similarity	NPD5402	Approved
0.7041	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4198	Discontinued
0.7024	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5760	Phase 2
0.7024	Intermediate Similarity	NPD5761	Phase 2
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.7018	Intermediate Similarity	NPD5494	Approved
0.7013	Intermediate Similarity	NPD7008	Discontinued
0.7	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6799	Approved
0.6988	Remote Similarity	NPD7458	Discontinued
0.6988	Remote Similarity	NPD3226	Approved
0.6977	Remote Similarity	NPD8127	Discontinued
0.6971	Remote Similarity	NPD3818	Discontinued
0.6964	Remote Similarity	NPD1934	Approved
0.6959	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6534	Approved
0.6957	Remote Similarity	NPD6535	Approved
0.6951	Remote Similarity	NPD2533	Approved
0.6951	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2532	Approved
0.6951	Remote Similarity	NPD2534	Approved
0.6943	Remote Similarity	NPD230	Phase 1
0.6937	Remote Similarity	NPD2346	Discontinued
0.6935	Remote Similarity	NPD7700	Phase 2
0.6935	Remote Similarity	NPD7699	Phase 2
0.6931	Remote Similarity	NPD7435	Discontinued
0.6923	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7961	Discontinued
0.6923	Remote Similarity	NPD2801	Approved
0.6923	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7305	Phase 1
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6764	Approved
0.691	Remote Similarity	NPD6765	Approved
0.6905	Remote Similarity	NPD7411	Suspended
0.6901	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2182	Approved
0.6897	Remote Similarity	NPD6010	Discontinued
0.6895	Remote Similarity	NPD8320	Phase 1
0.6895	Remote Similarity	NPD8319	Approved
0.6893	Remote Similarity	NPD7074	Phase 3
0.6892	Remote Similarity	NPD7741	Discontinued
0.6882	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5403	Approved
0.6864	Remote Similarity	NPD37	Approved
0.6859	Remote Similarity	NPD3764	Approved
0.6857	Remote Similarity	NPD6166	Phase 2
0.6857	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5951	Approved
0.6848	Remote Similarity	NPD5401	Approved
0.6842	Remote Similarity	NPD4967	Phase 2
0.6842	Remote Similarity	NPD4966	Approved
0.6842	Remote Similarity	NPD4965	Approved
0.6836	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7054	Approved
0.6816	Remote Similarity	NPD7685	Pre-registration
0.6816	Remote Similarity	NPD6559	Discontinued
0.6813	Remote Similarity	NPD2799	Discontinued
0.6807	Remote Similarity	NPD6273	Approved
0.68	Remote Similarity	NPD5125	Phase 3
0.68	Remote Similarity	NPD5126	Approved
0.6798	Remote Similarity	NPD7472	Approved
0.679	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6782	Approved
0.6772	Remote Similarity	NPD6776	Approved
0.6772	Remote Similarity	NPD6779	Approved
0.6772	Remote Similarity	NPD6778	Approved
0.6772	Remote Similarity	NPD6777	Approved
0.6772	Remote Similarity	NPD6781	Approved
0.6772	Remote Similarity	NPD6780	Approved
0.677	Remote Similarity	NPD2796	Approved
0.677	Remote Similarity	NPD2935	Discontinued
0.6768	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6234	Discontinued
0.676	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6785	Approved
0.6758	Remote Similarity	NPD6784	Approved
0.6755	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7497	Discontinued
0.6752	Remote Similarity	NPD2313	Discontinued
0.6747	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3882	Suspended
0.6743	Remote Similarity	NPD3787	Discontinued
0.6728	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7251	Discontinued
0.6718	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7874	Approved
0.6713	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6287	Discontinued
0.6708	Remote Similarity	NPD1510	Phase 2
0.6707	Remote Similarity	NPD3750	Approved
0.669	Remote Similarity	NPD5048	Discontinued
0.6689	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1549	Phase 2
0.6687	Remote Similarity	NPD6651	Approved
0.6686	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6959	Discontinued
0.6685	Remote Similarity	NPD7228	Approved
0.6685	Remote Similarity	NPD7808	Phase 3
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD9545	Approved
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7768	Phase 2
0.6647	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2800	Approved
0.6632	Remote Similarity	NPD7870	Phase 2
0.6632	Remote Similarity	NPD7871	Phase 2
0.6631	Remote Similarity	NPD6212	Phase 3
0.6631	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD6213	Phase 3
0.6628	Remote Similarity	NPD1465	Phase 2
0.6627	Remote Similarity	NPD3300	Phase 2
0.6626	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7266	Discontinued
0.6626	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD690	Clinical (unspecified phase)
0.662	Remote Similarity	NPD164	Approved
0.6615	Remote Similarity	NPD7701	Phase 2
0.6615	Remote Similarity	NPD6823	Phase 2
0.6609	Remote Similarity	NPD3749	Approved
0.6606	Remote Similarity	NPD7003	Approved
0.6606	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7033	Discontinued
0.6605	Remote Similarity	NPD3748	Approved
0.6605	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6085	Phase 2
0.6599	Remote Similarity	NPD7094	Approved
0.6599	Remote Similarity	NPD6858	Approved
0.6599	Remote Similarity	NPD7801	Approved
0.6591	Remote Similarity	NPD7199	Phase 2
0.6588	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1511	Approved
0.6584	Remote Similarity	NPD1607	Approved
0.6582	Remote Similarity	NPD8151	Discontinued
0.6577	Remote Similarity	NPD7115	Discovery
0.6564	Remote Similarity	NPD5408	Approved
0.6564	Remote Similarity	NPD5406	Approved
0.6564	Remote Similarity	NPD5404	Approved
0.6564	Remote Similarity	NPD5405	Approved
0.6562	Remote Similarity	NPD943	Approved
0.6562	Remote Similarity	NPD1240	Approved
0.6549	Remote Similarity	NPD1929	Approved
0.6549	Remote Similarity	NPD1930	Approved
0.6549	Remote Similarity	NPD1931	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