NPASS Compound

Structure

CID1796 OpenBabel06191715322D 43 48 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 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 -0.8660 2.5000 0.0000 C 0 0 1 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 41 1 0 0 0 0 2 9 1 0 0 0 0 2 20 2 0 0 0 0 3 10 2 0 0 0 0 3 20 1 0 0 0 0 4 15 1 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 5 21 2 0 0 0 0 6 12 2 0 0 0 0 6 21 1 0 0 0 0 7 13 1 0 0 0 0 7 22 2 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 24 2 0 0 0 0 10 24 1 0 0 0 0 11 25 2 0 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 16 23 1 0 0 0 0 16 27 1 0 0 0 0 17 23 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 18 31 1 0 0 0 0 19 28 2 0 0 0 0 19 32 1 0 0 0 0 22 31 1 0 0 0 0 23 33 1 1 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 27 15 1 1 0 0 0 27 42 1 0 0 0 0 28 33 1 0 0 0 0 28 39 1 0 0 0 0 29 34 1 0 0 0 0 29 40 2 0 0 0 0 30 21 1 1 0 0 0 30 42 1 0 0 0 0 31 43 1 0 0 0 0 32 34 2 0 0 0 0 32 41 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 35 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.23
Volume:	598.625
LogP:	5.638
LogD:	4.009
LogS:	-4.672
# Rotatable Bonds:	7
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.186
Synthetic Accessibility Score:	4.132
Fsp3:	0.286
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:	-4.904
MDCK Permeability:	1.0538608876231592e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.15
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	99.2936782836914%
Volume Distribution (VD):	0.307
Pgp-substrate:	1.3736852407455444%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.956
CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.752
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.627

ADMET: Excretion

Clearance (CL):	12.899
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.241
Human Hepatotoxicity (H-HT):	0.607
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.957
Carcinogencity:	0.416
Eye Corrosion:	0.003
Eye Irritation:	0.821
Respiratory Toxicity:	0.717

Download Data

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

Natural Product: NPC1796

Natural Product ID:	NPC1796
*Common Name:**	Calyxin K
IUPAC Name:	7-hydroxy-2-(4-hydroxyphenyl)-8-[(2S,4R,6S)-2-(4-hydroxyphenyl)-6-[2-(4-hydroxyphenyl)ethyl]oxan-4-yl]-5-methoxy-2,3-dihydrochromen-4-one
Synonyms:	Calyxin K; Epicalyxin K
Standard InCHIKey:	JHPJOKVLYIDVMB-DXOCUVQASA-N
Standard InCHI:	InChI=1S/C35H34O8/c1-41-32-19-28(39)33(35-34(32)29(40)18-31(43-35)22-7-13-26(38)14-8-22)23-16-27(15-4-20-2-9-24(36)10-3-20)42-30(17-23)21-5-11-25(37)12-6-21/h2-3,5-14,19,23,27,30-31,36-39H,4,15-18H2,1H3/t23-,27+,30+,31?/m1/s1
SMILES:	COc1cc(c([C@@H]2C[C@H](CCc3ccc(cc3)O)O[C@@H](C2)c2ccc(cc2)O)c2c1C(=O)CC(c1ccc(cc1)O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455334
PubChem CID:	10348279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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	=	5.09	uM	PMID[531536]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	4.75	uM	PMID[531537]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	7.73	uM	PMID[531536]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	33.0	uM	PMID[531537]

☑ 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 NPC1796 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
0.9933	High Similarity	NPC51247
0.9868	High Similarity	NPC42965
0.9868	High Similarity	NPC226462
0.9868	High Similarity	NPC98023
0.9867	High Similarity	NPC257166
0.9801	High Similarity	NPC15815
0.9799	High Similarity	NPC121568
0.9737	High Similarity	NPC195136
0.9735	High Similarity	NPC475184
0.9733	High Similarity	NPC37253
0.9733	High Similarity	NPC79375
0.9671	High Similarity	NPC105584
0.9669	High Similarity	NPC69531
0.9664	High Similarity	NPC178484
0.9613	High Similarity	NPC473010
0.961	High Similarity	NPC473012
0.9608	High Similarity	NPC121647
0.9605	High Similarity	NPC322459
0.9605	High Similarity	NPC318527
0.9605	High Similarity	NPC324358
0.9605	High Similarity	NPC208258
0.9605	High Similarity	NPC323627
0.9605	High Similarity	NPC287789
0.9605	High Similarity	NPC271741
0.9603	High Similarity	NPC300668
0.9603	High Similarity	NPC134171
0.96	High Similarity	NPC115601
0.96	High Similarity	NPC78324
0.96	High Similarity	NPC208011
0.96	High Similarity	NPC39154
0.9548	High Similarity	NPC473009
0.9545	High Similarity	NPC301256
0.9545	High Similarity	NPC312273
0.9542	High Similarity	NPC51760
0.9539	High Similarity	NPC198489
0.9539	High Similarity	NPC32867
0.9539	High Similarity	NPC61112
0.953	High Similarity	NPC3642
0.9474	High Similarity	NPC258474
0.9474	High Similarity	NPC201227
0.9474	High Similarity	NPC66441
0.9474	High Similarity	NPC182555
0.947	High Similarity	NPC43345
0.947	High Similarity	NPC174086
0.9463	High Similarity	NPC122894
0.9427	High Similarity	NPC251336
0.9416	High Similarity	NPC295090
0.9412	High Similarity	NPC56049
0.9412	High Similarity	NPC309648
0.9412	High Similarity	NPC54830
0.9408	High Similarity	NPC324447
0.9404	High Similarity	NPC476551
0.9404	High Similarity	NPC476552
0.9404	High Similarity	NPC476553
0.94	High Similarity	NPC132345
0.94	High Similarity	NPC473016
0.9396	High Similarity	NPC475348
0.9396	High Similarity	NPC261271
0.9346	High Similarity	NPC215203
0.9346	High Similarity	NPC186227
0.9346	High Similarity	NPC52611
0.9346	High Similarity	NPC265624
0.9346	High Similarity	NPC14606
0.9346	High Similarity	NPC159707
0.9346	High Similarity	NPC100049
0.9346	High Similarity	NPC158027
0.9346	High Similarity	NPC121649
0.9346	High Similarity	NPC248739
0.9346	High Similarity	NPC150908
0.9346	High Similarity	NPC205026
0.9333	High Similarity	NPC152233
0.9329	High Similarity	NPC470132
0.9329	High Similarity	NPC470134
0.9329	High Similarity	NPC228779
0.9329	High Similarity	NPC470131
0.9329	High Similarity	NPC473078
0.9329	High Similarity	NPC470133
0.9329	High Similarity	NPC109183
0.9299	High Similarity	NPC63438
0.9281	High Similarity	NPC71061
0.9281	High Similarity	NPC290830
0.9281	High Similarity	NPC303485
0.9281	High Similarity	NPC194593
0.9281	High Similarity	NPC72425
0.9276	High Similarity	NPC148945
0.9276	High Similarity	NPC316960
0.9276	High Similarity	NPC204561
0.9276	High Similarity	NPC78835
0.9276	High Similarity	NPC317715
0.9276	High Similarity	NPC309512
0.9262	High Similarity	NPC282957
0.9262	High Similarity	NPC473014
0.9262	High Similarity	NPC194949
0.9262	High Similarity	NPC271288
0.9262	High Similarity	NPC470136
0.9262	High Similarity	NPC470135
0.9262	High Similarity	NPC235217
0.9262	High Similarity	NPC39045
0.9236	High Similarity	NPC15374
0.9236	High Similarity	NPC473011
0.9205	High Similarity	NPC145467
0.92	High Similarity	NPC285630
0.92	High Similarity	NPC127059
0.9195	High Similarity	NPC185276
0.9195	High Similarity	NPC81697
0.9195	High Similarity	NPC223812
0.9195	High Similarity	NPC107177
0.9195	High Similarity	NPC125894
0.9195	High Similarity	NPC77794
0.9195	High Similarity	NPC85162
0.9195	High Similarity	NPC278249
0.9193	High Similarity	NPC477529
0.9182	High Similarity	NPC224851
0.9172	High Similarity	NPC175513
0.9172	High Similarity	NPC114652
0.9172	High Similarity	NPC18380
0.9167	High Similarity	NPC90497
0.9167	High Similarity	NPC55443
0.9167	High Similarity	NPC18699
0.9167	High Similarity	NPC195167
0.9167	High Similarity	NPC123544
0.915	High Similarity	NPC67322
0.915	High Similarity	NPC209142
0.915	High Similarity	NPC111112
0.915	High Similarity	NPC312549
0.915	High Similarity	NPC222713
0.915	High Similarity	NPC138299
0.9145	High Similarity	NPC291746
0.9145	High Similarity	NPC288840
0.9139	High Similarity	NPC300988
0.9139	High Similarity	NPC296998
0.9139	High Similarity	NPC308200
0.9139	High Similarity	NPC10990
0.9139	High Similarity	NPC283234
0.9139	High Similarity	NPC473077
0.9136	High Similarity	NPC168789
0.9133	High Similarity	NPC471473
0.9133	High Similarity	NPC236766
0.9133	High Similarity	NPC131579
0.9133	High Similarity	NPC473013
0.9133	High Similarity	NPC197252
0.9133	High Similarity	NPC471524
0.9133	High Similarity	NPC473015
0.9133	High Similarity	NPC471523
0.9133	High Similarity	NPC131568
0.9128	High Similarity	NPC1089
0.9128	High Similarity	NPC78
0.9128	High Similarity	NPC328164
0.9128	High Similarity	NPC220998
0.9128	High Similarity	NPC228504
0.9128	High Similarity	NPC265040
0.9128	High Similarity	NPC32739
0.9128	High Similarity	NPC227579
0.9128	High Similarity	NPC324436
0.9128	High Similarity	NPC223500
0.9128	High Similarity	NPC66515
0.9128	High Similarity	NPC324134
0.9128	High Similarity	NPC37496
0.9128	High Similarity	NPC182852
0.9128	High Similarity	NPC161506
0.9128	High Similarity	NPC107572
0.9128	High Similarity	NPC166482
0.9128	High Similarity	NPC76338
0.9128	High Similarity	NPC40833
0.9128	High Similarity	NPC306829
0.9128	High Similarity	NPC177354
0.9128	High Similarity	NPC296917
0.9128	High Similarity	NPC76372
0.9128	High Similarity	NPC166934
0.9128	High Similarity	NPC125855
0.9128	High Similarity	NPC64915
0.9128	High Similarity	NPC194432
0.9128	High Similarity	NPC10937
0.9128	High Similarity	NPC148757
0.9128	High Similarity	NPC167624
0.9108	High Similarity	NPC292863
0.9108	High Similarity	NPC184326
0.9085	High Similarity	NPC29777
0.9085	High Similarity	NPC471115
0.9079	High Similarity	NPC132592
0.9079	High Similarity	NPC161191
0.9079	High Similarity	NPC39195
0.9079	High Similarity	NPC160821
0.9073	High Similarity	NPC470647
0.9073	High Similarity	NPC474161
0.9073	High Similarity	NPC246948
0.9073	High Similarity	NPC83357
0.9073	High Similarity	NPC142405
0.9073	High Similarity	NPC176229
0.9073	High Similarity	NPC476088
0.9073	High Similarity	NPC477955
0.9073	High Similarity	NPC88964
0.9073	High Similarity	NPC20488
0.9073	High Similarity	NPC111786
0.9073	High Similarity	NPC267375
0.9073	High Similarity	NPC301276
0.9073	High Similarity	NPC214774
0.9073	High Similarity	NPC195621
0.9073	High Similarity	NPC472629
0.9073	High Similarity	NPC475052

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 NPC1796 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
0.9603	High Similarity	NPD8443	Clinical (unspecified phase)
0.9172	High Similarity	NPD6959	Discontinued
0.9119	High Similarity	NPD7852	Clinical (unspecified phase)
0.8917	High Similarity	NPD7768	Phase 2
0.8903	High Similarity	NPD7411	Suspended
0.8882	High Similarity	NPD7410	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.879	High Similarity	NPD7819	Suspended
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8742	High Similarity	NPD7075	Discontinued
0.8733	High Similarity	NPD1549	Phase 2
0.872	High Similarity	NPD7804	Clinical (unspecified phase)
0.8718	High Similarity	NPD4380	Phase 2
0.8671	High Similarity	NPD2393	Clinical (unspecified phase)
0.865	High Similarity	NPD6168	Clinical (unspecified phase)
0.865	High Similarity	NPD6167	Clinical (unspecified phase)
0.865	High Similarity	NPD6166	Phase 2
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD2796	Approved
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8395	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD7074	Phase 3
0.8293	Intermediate Similarity	NPD5494	Approved
0.8282	Intermediate Similarity	NPD3749	Approved
0.8274	Intermediate Similarity	NPD7054	Approved
0.8267	Intermediate Similarity	NPD1240	Approved
0.8261	Intermediate Similarity	NPD6801	Discontinued
0.8255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7472	Approved
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7808	Phase 3
0.8176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1607	Approved
0.8155	Intermediate Similarity	NPD7473	Discontinued
0.814	Intermediate Similarity	NPD8312	Approved
0.814	Intermediate Similarity	NPD8313	Approved
0.8129	Intermediate Similarity	NPD7251	Discontinued
0.8121	Intermediate Similarity	NPD4908	Phase 1
0.811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7390	Discontinued
0.807	Intermediate Similarity	NPD6797	Phase 2
0.8039	Intermediate Similarity	NPD6651	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.7988	Intermediate Similarity	NPD2801	Approved
0.7988	Intermediate Similarity	NPD8455	Phase 2
0.7987	Intermediate Similarity	NPD1511	Approved
0.7987	Intermediate Similarity	NPD6799	Approved
0.7976	Intermediate Similarity	NPD6232	Discontinued
0.7962	Intermediate Similarity	NPD2800	Approved
0.7953	Intermediate Similarity	NPD5844	Phase 1
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7914	Intermediate Similarity	NPD6599	Discontinued
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3882	Suspended
0.7888	Intermediate Similarity	NPD1512	Approved
0.7874	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5403	Approved
0.7831	Intermediate Similarity	NPD3817	Phase 2
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3818	Discontinued
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD6100	Approved
0.7771	Intermediate Similarity	NPD6099	Approved
0.7759	Intermediate Similarity	NPD5953	Discontinued
0.7747	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7458	Discontinued
0.7735	Intermediate Similarity	NPD4363	Phase 3
0.7735	Intermediate Similarity	NPD4360	Phase 2
0.7722	Intermediate Similarity	NPD2344	Approved
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD2532	Approved
0.7716	Intermediate Similarity	NPD5401	Approved
0.7716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3748	Approved
0.767	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2935	Discontinued
0.7651	Intermediate Similarity	NPD1610	Phase 2
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.7636	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3226	Approved
0.7625	Intermediate Similarity	NPD1243	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.7619	Intermediate Similarity	NPD5402	Approved
0.7595	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD8151	Discontinued
0.7578	Intermediate Similarity	NPD7003	Approved
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7545	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6832	Phase 2
0.7531	Intermediate Similarity	NPD2309	Approved
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7696	Phase 3
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7871	Phase 2
0.746	Intermediate Similarity	NPD7870	Phase 2
0.7457	Intermediate Similarity	NPD7229	Phase 3
0.7456	Intermediate Similarity	NPD1465	Phase 2
0.7438	Intermediate Similarity	NPD5406	Approved
0.7438	Intermediate Similarity	NPD5405	Approved
0.7438	Intermediate Similarity	NPD5408	Approved
0.7438	Intermediate Similarity	NPD5404	Approved
0.7436	Intermediate Similarity	NPD3268	Approved
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7414	Intermediate Similarity	NPD3926	Phase 2
0.7409	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7783	Phase 2
0.7405	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4361	Phase 2
0.7403	Intermediate Similarity	NPD2798	Approved
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7391	Intermediate Similarity	NPD2346	Discontinued
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7344	Intermediate Similarity	NPD7701	Phase 2
0.734	Intermediate Similarity	NPD6777	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7322	Intermediate Similarity	NPD4287	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7305	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7199	Phase 2
0.7294	Intermediate Similarity	NPD7577	Discontinued
0.7292	Intermediate Similarity	NPD7584	Approved
0.7289	Intermediate Similarity	NPD7447	Phase 1
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3751	Discontinued
0.7288	Intermediate Similarity	NPD7228	Approved
0.7288	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7177	Discontinued
0.7283	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7261	Intermediate Similarity	NPD4625	Phase 3
0.7257	Intermediate Similarity	NPD5711	Approved
0.7257	Intermediate Similarity	NPD5710	Approved
0.7253	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6273	Approved
0.7234	Intermediate Similarity	NPD7700	Phase 2
0.7234	Intermediate Similarity	NPD7699	Phase 2
0.7233	Intermediate Similarity	NPD943	Approved
0.7231	Intermediate Similarity	NPD7801	Approved
0.7229	Intermediate Similarity	NPD7212	Phase 2
0.7229	Intermediate Similarity	NPD7213	Phase 3
0.7216	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8434	Phase 2
0.7205	Intermediate Similarity	NPD7097	Phase 1
0.72	Intermediate Similarity	NPD1247	Approved
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD8319	Approved
0.7188	Intermediate Similarity	NPD8320	Phase 1
0.7179	Intermediate Similarity	NPD7874	Approved
0.7179	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7151	Intermediate Similarity	NPD5760	Phase 2
0.7151	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7134	Intermediate Similarity	NPD2861	Phase 2
0.7125	Intermediate Similarity	NPD1613	Approved
0.7125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD3266	Approved
0.7111	Intermediate Similarity	NPD1729	Discontinued
0.711	Intermediate Similarity	NPD4288	Approved
0.7107	Intermediate Similarity	NPD3764	Approved
0.7097	Intermediate Similarity	NPD4749	Approved
0.7093	Intermediate Similarity	NPD6844	Discontinued
0.7093	Intermediate Similarity	NPD37	Approved
0.7091	Intermediate Similarity	NPD2654	Approved
0.7086	Intermediate Similarity	NPD6234	Discontinued
0.7078	Intermediate Similarity	NPD422	Phase 1
0.7078	Intermediate Similarity	NPD1201	Approved
0.7074	Intermediate Similarity	NPD6534	Approved
0.7074	Intermediate Similarity	NPD6535	Approved
0.7069	Intermediate Similarity	NPD4965	Approved
0.7069	Intermediate Similarity	NPD4966	Approved
0.7069	Intermediate Similarity	NPD4967	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data