NPASS Compound

Structure

CID42965 OpenBabel06191715372D 51 58 0 0 1 0 0 0 0 0999 V2000 0.8234 -3.3279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6469 3.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 5.2295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 -0.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6469 0.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7640 5.2295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5875 3.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1172 2.3770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9406 0.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 4.2787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6469 5.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2937 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5875 5.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4109 4.2787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9406 2.8525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7640 1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.8525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8234 1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 -1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4703 -1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 4.2787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6469 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7640 4.2787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1172 1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 5.2295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2937 0.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4109 5.2295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7640 2.3770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8234 2.3770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6469 0.9508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 -0.4754 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6469 -1.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4703 -0.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6469 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4703 1.4262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8234 -1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4703 2.3770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2937 0.9508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8234 -0.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2937 5.7049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1172 1.4262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2343 5.7049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5875 2.8525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6469 -2.8525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6469 2.8525 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 3.2937 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 48 1 0 0 0 0 2 11 1 0 0 0 0 2 23 2 0 0 0 0 3 12 2 0 0 0 0 3 23 1 0 0 0 0 4 19 1 0 0 0 0 4 23 1 0 0 0 0 5 13 1 0 0 0 0 5 24 2 0 0 0 0 6 14 2 0 0 0 0 6 24 1 0 0 0 0 7 15 1 0 0 0 0 7 25 2 0 0 0 0 8 16 2 0 0 0 0 8 25 1 0 0 0 0 9 17 1 0 0 0 0 9 26 2 0 0 0 0 10 18 2 0 0 0 0 10 26 1 0 0 0 0 11 27 2 0 0 0 0 12 27 1 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 15 29 2 0 0 0 0 16 29 1 0 0 0 0 17 30 2 0 0 0 0 18 30 1 0 0 0 0 20 31 1 0 0 0 0 21 33 1 0 0 0 0 21 34 1 0 0 0 0 22 35 2 0 0 0 0 22 36 1 0 0 0 0 24 34 1 0 0 0 0 25 40 1 0 0 0 0 26 41 1 0 0 0 0 27 43 1 0 0 0 0 28 44 1 0 0 0 0 29 45 1 0 0 0 0 30 46 1 0 0 0 0 31 19 1 6 0 0 0 31 49 1 0 0 0 0 32 20 1 6 0 0 0 32 37 1 0 0 0 0 32 38 1 0 0 0 0 33 39 1 0 0 0 0 33 47 2 0 0 0 0 34 50 1 0 0 0 0 35 39 1 0 0 0 0 35 48 1 0 0 0 0 36 37 2 0 0 0 0 36 51 1 0 0 0 0 37 42 1 0 0 0 0 38 40 1 0 0 0 0 38 41 1 0 0 0 0 39 42 2 0 0 0 0 40 49 1 0 0 0 0 41 51 1 0 0 0 0 42 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	686.25
Volume:	703.465
LogP:	6.856
LogD:	4.491
LogS:	-4.701
# Rotatable Bonds:	7
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.134
Synthetic Accessibility Score:	4.643
Fsp3:	0.262
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.014
MDCK Permeability:	1.1465850548120216e-05
Pgp-inhibitor:	0.092
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	99.67549133300781%
Volume Distribution (VD):	0.256
Pgp-substrate:	1.1823921203613281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.954
CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.527
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.609

ADMET: Excretion

Clearance (CL):	11.134
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.437
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.843
Skin Sensitization:	0.937
Carcinogencity:	0.523
Eye Corrosion:	0.003
Eye Irritation:	0.352
Respiratory Toxicity:	0.157

Download Data

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

Natural Product: NPC42965

Natural Product ID:	NPC42965
*Common Name:**	Calyxin J
IUPAC Name:	n.a.
Synonyms:	Calyxin J
Standard InCHIKey:	VIDHFKRYBXNWLN-OMQYIVAFSA-N
Standard InCHI:	InChI=1S/C42H38O9/c1-48-35-22-36-37(42-39(35)33(47)21-34(50-42)24-5-13-28(44)14-6-24)32-20-31(19-4-23-2-11-27(43)12-3-23)49-40(25-7-15-29(45)16-8-25)38(32)41(51-36)26-9-17-30(46)18-10-26/h2-3,5-18,22,31-32,34,38,40-41,43-46H,4,19-21H2,1H3/t31-,32-,34?,38-,40+,41-/m0/s1
SMILES:	COc1cc2c([C@@H]3C[C@H](CCc4ccc(cc4)O)O[C@H](c4ccc(cc4)O)[C@H]3[C@H](c3ccc(cc3)O)O2)c2c1C(=O)CC(c1ccc(cc1)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510115
PubChem CID:	11765183
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	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
ED50	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	8.19	uM	PMID[501571]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	0.32	uM	PMID[501572]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	23.2	uM	PMID[501571]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	13.7	uM	PMID[501572]

☑ 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 NPC42965 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	400
0.1-0.2	1479
0.2-0.3	3297
0.3-0.4	8594
0.4-0.5	10395
0.5-0.6	3781
0.6-0.7	5965
0.7-0.8	5361
0.8-0.85	2274
0.85-0.9	873
0.9-0.95	244
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC226462
0.9868	High Similarity	NPC1796
0.9868	High Similarity	NPC98023
0.9803	High Similarity	NPC51247
0.9737	High Similarity	NPC257166
0.9673	High Similarity	NPC15815
0.9669	High Similarity	NPC121568
0.961	High Similarity	NPC195136
0.9608	High Similarity	NPC475184
0.9608	High Similarity	NPC208258
0.9605	High Similarity	NPC37253
0.9605	High Similarity	NPC79375
0.9603	High Similarity	NPC208011
0.9603	High Similarity	NPC78324
0.9603	High Similarity	NPC115601
0.9603	High Similarity	NPC39154
0.9545	High Similarity	NPC105584
0.9542	High Similarity	NPC69531
0.9536	High Similarity	NPC178484
0.949	High Similarity	NPC473010
0.9487	High Similarity	NPC473012
0.9484	High Similarity	NPC121647
0.9481	High Similarity	NPC322459
0.9481	High Similarity	NPC324358
0.9481	High Similarity	NPC323627
0.9481	High Similarity	NPC318527
0.9481	High Similarity	NPC287789
0.9481	High Similarity	NPC271741
0.9477	High Similarity	NPC300668
0.9477	High Similarity	NPC134171
0.9427	High Similarity	NPC473009
0.9423	High Similarity	NPC301256
0.9423	High Similarity	NPC312273
0.9419	High Similarity	NPC51760
0.9416	High Similarity	NPC198489
0.9416	High Similarity	NPC61112
0.9416	High Similarity	NPC32867
0.9404	High Similarity	NPC3642
0.9404	High Similarity	NPC132345
0.9351	High Similarity	NPC258474
0.9351	High Similarity	NPC201227
0.9351	High Similarity	NPC182555
0.9351	High Similarity	NPC66441
0.9346	High Similarity	NPC174086
0.9346	High Similarity	NPC43345
0.9338	High Similarity	NPC122894
0.9308	High Similarity	NPC251336
0.9295	High Similarity	NPC295090
0.929	High Similarity	NPC56049
0.929	High Similarity	NPC309648
0.929	High Similarity	NPC54830
0.9286	High Similarity	NPC324447
0.9281	High Similarity	NPC476552
0.9281	High Similarity	NPC476553
0.9281	High Similarity	NPC476551
0.9276	High Similarity	NPC473016
0.9272	High Similarity	NPC475348
0.9272	High Similarity	NPC261271
0.9226	High Similarity	NPC150908
0.9226	High Similarity	NPC205026
0.9226	High Similarity	NPC265624
0.9226	High Similarity	NPC158027
0.9226	High Similarity	NPC159707
0.9226	High Similarity	NPC215203
0.9226	High Similarity	NPC52611
0.9226	High Similarity	NPC100049
0.9226	High Similarity	NPC121649
0.9226	High Similarity	NPC248739
0.9226	High Similarity	NPC14606
0.9226	High Similarity	NPC186227
0.9211	High Similarity	NPC152233
0.9205	High Similarity	NPC473078
0.9205	High Similarity	NPC470133
0.9205	High Similarity	NPC470131
0.9205	High Similarity	NPC470132
0.9205	High Similarity	NPC470134
0.9205	High Similarity	NPC228779
0.9205	High Similarity	NPC109183
0.9182	High Similarity	NPC63438
0.9177	High Similarity	NPC18380
0.9172	High Similarity	NPC195167
0.9161	High Similarity	NPC303485
0.9161	High Similarity	NPC71061
0.9161	High Similarity	NPC290830
0.9161	High Similarity	NPC72425
0.9161	High Similarity	NPC194593
0.9156	High Similarity	NPC309512
0.9156	High Similarity	NPC204561
0.9156	High Similarity	NPC148945
0.9156	High Similarity	NPC317715
0.9156	High Similarity	NPC78835
0.9156	High Similarity	NPC316960
0.9141	High Similarity	NPC168789
0.9139	High Similarity	NPC470135
0.9139	High Similarity	NPC470136
0.9139	High Similarity	NPC271288
0.9139	High Similarity	NPC282957
0.9139	High Similarity	NPC39045
0.9139	High Similarity	NPC473014
0.9139	High Similarity	NPC194949
0.9139	High Similarity	NPC235217
0.9119	High Similarity	NPC15374
0.9119	High Similarity	NPC473011
0.9114	High Similarity	NPC292863
0.9114	High Similarity	NPC184326
0.9085	High Similarity	NPC145467
0.908	High Similarity	NPC477529
0.9079	High Similarity	NPC127059
0.9079	High Similarity	NPC285630
0.9073	High Similarity	NPC185276
0.9073	High Similarity	NPC223812
0.9073	High Similarity	NPC81697
0.9073	High Similarity	NPC125894
0.9073	High Similarity	NPC85162
0.9073	High Similarity	NPC77794
0.9073	High Similarity	NPC278249
0.9073	High Similarity	NPC107177
0.9068	High Similarity	NPC224851
0.9057	High Similarity	NPC137232
0.9057	High Similarity	NPC114652
0.9057	High Similarity	NPC175513
0.9051	High Similarity	NPC55443
0.9051	High Similarity	NPC18699
0.9051	High Similarity	NPC123544
0.9051	High Similarity	NPC90497
0.9032	High Similarity	NPC209142
0.9032	High Similarity	NPC325429
0.9032	High Similarity	NPC67322
0.9032	High Similarity	NPC138299
0.9032	High Similarity	NPC222713
0.9032	High Similarity	NPC312549
0.9032	High Similarity	NPC111112
0.9026	High Similarity	NPC291746
0.9026	High Similarity	NPC288840
0.902	High Similarity	NPC283234
0.902	High Similarity	NPC473077
0.902	High Similarity	NPC296998
0.902	High Similarity	NPC10990
0.902	High Similarity	NPC300988
0.902	High Similarity	NPC308200
0.9013	High Similarity	NPC473015
0.9013	High Similarity	NPC471473
0.9013	High Similarity	NPC131579
0.9013	High Similarity	NPC473013
0.9013	High Similarity	NPC471523
0.9013	High Similarity	NPC236766
0.9013	High Similarity	NPC197252
0.9013	High Similarity	NPC131568
0.9013	High Similarity	NPC471524
0.9007	High Similarity	NPC227579
0.9007	High Similarity	NPC324436
0.9007	High Similarity	NPC194432
0.9007	High Similarity	NPC223500
0.9007	High Similarity	NPC76372
0.9007	High Similarity	NPC66515
0.9007	High Similarity	NPC167624
0.9007	High Similarity	NPC182852
0.9007	High Similarity	NPC228504
0.9007	High Similarity	NPC265040
0.9007	High Similarity	NPC328164
0.9007	High Similarity	NPC306829
0.9007	High Similarity	NPC177354
0.9007	High Similarity	NPC40833
0.9007	High Similarity	NPC166934
0.9007	High Similarity	NPC125855
0.9007	High Similarity	NPC296917
0.9007	High Similarity	NPC324134
0.9007	High Similarity	NPC148757
0.9007	High Similarity	NPC161506
0.9007	High Similarity	NPC37496
0.9007	High Similarity	NPC78
0.9007	High Similarity	NPC166482
0.9007	High Similarity	NPC1089
0.9007	High Similarity	NPC107572
0.9007	High Similarity	NPC10937
0.9007	High Similarity	NPC220998
0.9007	High Similarity	NPC76338
0.9007	High Similarity	NPC64915
0.9007	High Similarity	NPC32739
0.8974	High Similarity	NPC166067
0.8968	High Similarity	NPC29777
0.8968	High Similarity	NPC471115
0.8961	High Similarity	NPC160821
0.8961	High Similarity	NPC132592
0.8961	High Similarity	NPC161191
0.8961	High Similarity	NPC39195
0.8954	High Similarity	NPC111786
0.8954	High Similarity	NPC214774
0.8954	High Similarity	NPC301276
0.8954	High Similarity	NPC475052
0.8954	High Similarity	NPC312973
0.8954	High Similarity	NPC54577
0.8954	High Similarity	NPC176229
0.8954	High Similarity	NPC476088
0.8954	High Similarity	NPC88964
0.8954	High Similarity	NPC477955
0.8954	High Similarity	NPC470647
0.8954	High Similarity	NPC472629
0.8954	High Similarity	NPC246948
0.8954	High Similarity	NPC195621

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 NPC42965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	905
0.2-0.3	1492
0.3-0.4	2584
0.4-0.5	2048
0.5-0.6	1153
0.6-0.7	431
0.7-0.8	157
0.8-0.85	24
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9477	High Similarity	NPD8443	Clinical (unspecified phase)
0.9057	High Similarity	NPD6959	Discontinued
0.9006	High Similarity	NPD7852	Clinical (unspecified phase)
0.8805	High Similarity	NPD7768	Phase 2
0.879	High Similarity	NPD7411	Suspended
0.8766	High Similarity	NPD7410	Clinical (unspecified phase)
0.8679	High Similarity	NPD7819	Suspended
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8634	High Similarity	NPD7075	Discontinued
0.8618	High Similarity	NPD1549	Phase 2
0.8614	High Similarity	NPD7804	Clinical (unspecified phase)
0.8608	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8545	High Similarity	NPD6166	Phase 2
0.8545	High Similarity	NPD6168	Clinical (unspecified phase)
0.8545	High Similarity	NPD6167	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD2796	Approved
0.8343	Intermediate Similarity	NPD7074	Phase 3
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8293	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD1934	Approved
0.8193	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD3749	Approved
0.8176	Intermediate Similarity	NPD7054	Approved
0.816	Intermediate Similarity	NPD6801	Discontinued
0.8158	Intermediate Similarity	NPD1240	Approved
0.815	Intermediate Similarity	NPD8312	Approved
0.815	Intermediate Similarity	NPD8313	Approved
0.8146	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7472	Approved
0.8113	Intermediate Similarity	NPD7390	Discontinued
0.8092	Intermediate Similarity	NPD7808	Phase 3
0.8089	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7473	Discontinued
0.8052	Intermediate Similarity	NPD1607	Approved
0.8035	Intermediate Similarity	NPD7251	Discontinued
0.8013	Intermediate Similarity	NPD4908	Phase 1
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6797	Phase 2
0.7935	Intermediate Similarity	NPD6651	Approved
0.7925	Intermediate Similarity	NPD3750	Approved
0.7892	Intermediate Similarity	NPD2801	Approved
0.7892	Intermediate Similarity	NPD8455	Phase 2
0.7888	Intermediate Similarity	NPD6799	Approved
0.7888	Intermediate Similarity	NPD1511	Approved
0.7882	Intermediate Similarity	NPD6232	Discontinued
0.7862	Intermediate Similarity	NPD2800	Approved
0.7861	Intermediate Similarity	NPD5844	Phase 1
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7818	Intermediate Similarity	NPD6599	Discontinued
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3882	Suspended
0.7792	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1512	Approved
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7458	Discontinued
0.7744	Intermediate Similarity	NPD5403	Approved
0.7738	Intermediate Similarity	NPD3817	Phase 2
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2799	Discontinued
0.7701	Intermediate Similarity	NPD3818	Discontinued
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD6100	Approved
0.7673	Intermediate Similarity	NPD6099	Approved
0.767	Intermediate Similarity	NPD5953	Discontinued
0.7663	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD4363	Phase 3
0.765	Intermediate Similarity	NPD4360	Phase 2
0.7625	Intermediate Similarity	NPD2344	Approved
0.7622	Intermediate Similarity	NPD2533	Approved
0.7622	Intermediate Similarity	NPD5401	Approved
0.7622	Intermediate Similarity	NPD2534	Approved
0.7622	Intermediate Similarity	NPD2532	Approved
0.7622	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3748	Approved
0.7593	Intermediate Similarity	NPD7003	Approved
0.7592	Intermediate Similarity	NPD8151	Discontinued
0.7584	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2935	Discontinued
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.755	Intermediate Similarity	NPD1610	Phase 2
0.7545	Intermediate Similarity	NPD3226	Approved
0.7545	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7456	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2309	Approved
0.7436	Intermediate Similarity	NPD6832	Phase 2
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7783	Phase 2
0.7423	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7698	Approved
0.7421	Intermediate Similarity	NPD7697	Approved
0.7421	Intermediate Similarity	NPD5124	Phase 1
0.7421	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7696	Phase 3
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD1465	Phase 2
0.7346	Intermediate Similarity	NPD5404	Approved
0.7346	Intermediate Similarity	NPD5405	Approved
0.7346	Intermediate Similarity	NPD5406	Approved
0.7346	Intermediate Similarity	NPD5408	Approved
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7342	Intermediate Similarity	NPD3268	Approved
0.733	Intermediate Similarity	NPD3926	Phase 2
0.7326	Intermediate Similarity	NPD4361	Phase 2
0.7326	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD2798	Approved
0.7301	Intermediate Similarity	NPD2346	Discontinued
0.7284	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7268	Intermediate Similarity	NPD7701	Phase 2
0.7263	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD6781	Approved
0.7263	Intermediate Similarity	NPD6779	Approved
0.7263	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6776	Approved
0.7263	Intermediate Similarity	NPD6778	Approved
0.7263	Intermediate Similarity	NPD6780	Approved
0.7263	Intermediate Similarity	NPD6782	Approved
0.7244	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD1203	Approved
0.7243	Intermediate Similarity	NPD4287	Approved
0.724	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7584	Approved
0.7216	Intermediate Similarity	NPD7199	Phase 2
0.7209	Intermediate Similarity	NPD7577	Discontinued
0.7207	Intermediate Similarity	NPD7228	Approved
0.7207	Intermediate Similarity	NPD7177	Discontinued
0.7207	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3751	Discontinued
0.7202	Intermediate Similarity	NPD7447	Phase 1
0.7202	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8319	Approved
0.72	Intermediate Similarity	NPD919	Approved
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD5710	Approved
0.7174	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.717	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD6273	Approved
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD7213	Phase 3
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6798	Discontinued
0.7119	Intermediate Similarity	NPD1247	Approved
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.7107	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7098	Intermediate Similarity	NPD6823	Phase 2
0.7095	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD5761	Phase 2
0.7051	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD1608	Approved
0.7044	Intermediate Similarity	NPD2861	Phase 2
0.7037	Intermediate Similarity	NPD1613	Approved
0.7037	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD1729	Discontinued
0.7029	Intermediate Similarity	NPD4288	Approved
0.7025	Intermediate Similarity	NPD3267	Approved
0.7025	Intermediate Similarity	NPD3266	Approved
0.7019	Intermediate Similarity	NPD3764	Approved
0.7011	Intermediate Similarity	NPD6844	Discontinued
0.7011	Intermediate Similarity	NPD37	Approved
0.7006	Intermediate Similarity	NPD6234	Discontinued
0.7006	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD6535	Approved
0.6989	Remote Similarity	NPD4965	Approved
0.6989	Remote Similarity	NPD4967	Phase 2
0.6989	Remote Similarity	NPD4966	Approved
0.6987	Remote Similarity	NPD422	Phase 1
0.6987	Remote Similarity	NPD1201	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