NPASS Compound

Structure

NPC179896 OpenBabel07101718192D 39 43 0 0 1 0 0 0 0 0999 V2000 3.8701 -1.3174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9013 0.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4890 1.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1227 -1.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -0.3904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8548 -4.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2861 -0.6007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4771 -2.0019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3080 -0.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9680 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2567 -2.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9887 -2.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9887 -5.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1227 -3.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 0.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9887 -3.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2567 -3.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1227 -4.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7111 -0.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 1.2569 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1759 -1.6775 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.2464 1.6170 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 2.2433 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8548 -3.5952 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 -1.2588 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3907 -1.5952 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8548 -1.5952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9887 -6.0952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3907 -3.5952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2567 -5.0952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3443 2.2351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6810 3.2614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6622 -0.3393 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 38 1 0 0 0 0 2 3 1 0 0 0 0 2 10 1 0 0 0 0 3 27 1 0 0 0 0 4 13 2 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 6 24 1 0 0 0 0 7 15 2 0 0 0 0 7 28 1 0 0 0 0 8 10 2 0 0 0 0 8 31 1 0 0 0 0 9 29 2 0 0 0 0 9 31 1 0 0 0 0 10 29 1 0 0 0 0 11 21 1 0 0 0 0 11 25 1 0 0 0 0 12 23 1 0 0 0 0 12 30 2 0 0 0 0 13 19 1 0 0 0 0 13 31 1 0 0 0 0 14 18 2 0 0 0 0 14 32 1 0 0 0 0 15 20 1 0 0 0 0 15 33 1 0 0 0 0 16 18 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 19 34 1 0 0 0 0 20 35 2 0 0 0 0 21 38 1 0 0 0 0 22 24 1 1 0 0 0 22 36 1 0 0 0 0 23 27 1 0 0 0 0 23 37 2 0 0 0 0 24 5 1 1 0 0 0 24 39 1 0 0 0 0 30 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.98
Volume:	515.75
LogP:	2.001
LogD:	1.014
LogS:	-5.346
# Rotatable Bonds:	7
TPSA:	191.52
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.213
Synthetic Accessibility Score:	5.078
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.676
MDCK Permeability:	1.203973533847602e-05
Pgp-inhibitor:	0.929
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.958
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	97.3150405883789%
Volume Distribution (VD):	0.745
Pgp-substrate:	5.565557479858398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.749
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.786
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.566
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	1.29
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.888
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.788
Rat Oral Acute Toxicity:	0.792
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.789
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC179896

Natural Product ID:	NPC179896
*Common Name:**	Ceratinadin A
IUPAC Name:	(5S,6R)-7,9-dibromo-6-hydroxy-8-methoxy-N-[2-[1-(3,5,8-trihydroxy-4-oxo-1H-quinolin-6-yl)imidazol-4-yl]ethyl]-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:
Standard InCHIKey:	ZWKWCDKTCUKSQC-LADGPHEKSA-N
Standard InCHI:	InChI=1S/C24H21Br2N5O8/c1-38-21-11(25)5-24(22(36)17(21)26)6-12(30-39-24)23(37)27-3-2-10-8-31(9-29-10)13-4-14(32)18-16(19(13)34)20(35)15(33)7-28-18/h4-5,7-9,22,32-34,36H,2-3,6H2,1H3,(H,27,37)(H,28,35)/t22-,24+/m0/s1
SMILES:	COC1=C([C@@H]([C@@]2(C=C1Br)CC(=NO2)C(=O)NCCc1cn(cn1)c1cc(c2c(c1O)c(=O)c(c[nH]2)O)O)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1210512
PubChem CID:	49863115
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000057] Hydroxyquinolines

*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
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18393464]
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[20584605]
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24964362]

☑ 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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	4.0	ug.mL-1	PMID[496040]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	2.0	ug.mL-1	PMID[496040]

☑ 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 NPC179896 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	669
0.1-0.2	4789
0.2-0.3	13001
0.3-0.4	13681
0.4-0.5	7258
0.5-0.6	2539
0.6-0.7	749
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7868	Intermediate Similarity	NPC185172
0.6862	Remote Similarity	NPC74619
0.677	Remote Similarity	NPC63109
0.6762	Remote Similarity	NPC477549
0.6756	Remote Similarity	NPC77101
0.675	Remote Similarity	NPC172222
0.6747	Remote Similarity	NPC478006
0.6733	Remote Similarity	NPC477634
0.672	Remote Similarity	NPC315499
0.67	Remote Similarity	NPC478010
0.6699	Remote Similarity	NPC207620
0.6667	Remote Similarity	NPC472068
0.6655	Remote Similarity	NPC475746
0.6655	Remote Similarity	NPC152620
0.6655	Remote Similarity	NPC132385
0.6655	Remote Similarity	NPC258048
0.6633	Remote Similarity	NPC314056
0.6631	Remote Similarity	NPC244536
0.6622	Remote Similarity	NPC117980
0.6621	Remote Similarity	NPC472031
0.6621	Remote Similarity	NPC472067
0.6621	Remote Similarity	NPC472066
0.6612	Remote Similarity	NPC477633
0.6612	Remote Similarity	NPC45048
0.6611	Remote Similarity	NPC315467
0.661	Remote Similarity	NPC314882
0.6589	Remote Similarity	NPC478012
0.6589	Remote Similarity	NPC478009
0.6579	Remote Similarity	NPC279589
0.6567	Remote Similarity	NPC478013
0.6555	Remote Similarity	NPC227824
0.6551	Remote Similarity	NPC148889
0.6549	Remote Similarity	NPC182222
0.6541	Remote Similarity	NPC67401
0.6538	Remote Similarity	NPC30540
0.6532	Remote Similarity	NPC282346
0.6531	Remote Similarity	NPC472435
0.6529	Remote Similarity	NPC63971
0.6529	Remote Similarity	NPC91868
0.6528	Remote Similarity	NPC171393
0.6528	Remote Similarity	NPC295452
0.652	Remote Similarity	NPC472436
0.652	Remote Similarity	NPC219087
0.6515	Remote Similarity	NPC196449
0.6515	Remote Similarity	NPC314222
0.6508	Remote Similarity	NPC53534
0.6507	Remote Similarity	NPC26543
0.6505	Remote Similarity	NPC316224
0.6487	Remote Similarity	NPC220851
0.648	Remote Similarity	NPC478011
0.6479	Remote Similarity	NPC328924
0.6467	Remote Similarity	NPC169716
0.6463	Remote Similarity	NPC471536
0.646	Remote Similarity	NPC178858
0.6459	Remote Similarity	NPC314176
0.6454	Remote Similarity	NPC257851
0.6446	Remote Similarity	NPC28945
0.6439	Remote Similarity	NPC74360
0.6431	Remote Similarity	NPC66777
0.6431	Remote Similarity	NPC471762
0.6429	Remote Similarity	NPC181081
0.6426	Remote Similarity	NPC208522
0.6424	Remote Similarity	NPC470784
0.6423	Remote Similarity	NPC242923
0.6421	Remote Similarity	NPC207686
0.6419	Remote Similarity	NPC303374
0.6416	Remote Similarity	NPC270515
0.6396	Remote Similarity	NPC157931
0.638	Remote Similarity	NPC308906
0.637	Remote Similarity	NPC472434
0.6367	Remote Similarity	NPC101350
0.6357	Remote Similarity	NPC128115
0.6346	Remote Similarity	NPC209981
0.6341	Remote Similarity	NPC323752
0.6341	Remote Similarity	NPC220852
0.6338	Remote Similarity	NPC323244
0.6336	Remote Similarity	NPC291609
0.6332	Remote Similarity	NPC235685
0.6332	Remote Similarity	NPC184225
0.6332	Remote Similarity	NPC285343
0.6331	Remote Similarity	NPC471192
0.6327	Remote Similarity	NPC161801
0.6325	Remote Similarity	NPC141428
0.6318	Remote Similarity	NPC282247
0.6316	Remote Similarity	NPC194740
0.6316	Remote Similarity	NPC156003
0.631	Remote Similarity	NPC470785
0.631	Remote Similarity	NPC474183
0.6307	Remote Similarity	NPC89987
0.6303	Remote Similarity	NPC24370
0.6303	Remote Similarity	NPC319232
0.6301	Remote Similarity	NPC473312
0.6301	Remote Similarity	NPC124300
0.6299	Remote Similarity	NPC276657
0.6293	Remote Similarity	NPC310618
0.6289	Remote Similarity	NPC41501
0.6287	Remote Similarity	NPC200836
0.6284	Remote Similarity	NPC477630
0.6284	Remote Similarity	NPC165964
0.6284	Remote Similarity	NPC134637
0.6284	Remote Similarity	NPC477635
0.6281	Remote Similarity	NPC110151
0.6276	Remote Similarity	NPC184680
0.6272	Remote Similarity	NPC160666
0.6271	Remote Similarity	NPC218388
0.6267	Remote Similarity	NPC99891
0.6263	Remote Similarity	NPC250178
0.6263	Remote Similarity	NPC473800
0.6259	Remote Similarity	NPC151781
0.6259	Remote Similarity	NPC316181
0.6259	Remote Similarity	NPC74562
0.6259	Remote Similarity	NPC78609
0.6255	Remote Similarity	NPC171787
0.625	Remote Similarity	NPC49547
0.6246	Remote Similarity	NPC216369
0.6237	Remote Similarity	NPC326363
0.6232	Remote Similarity	NPC174672
0.6232	Remote Similarity	NPC122436
0.6228	Remote Similarity	NPC284888
0.6228	Remote Similarity	NPC141053
0.6224	Remote Similarity	NPC57690
0.6223	Remote Similarity	NPC153980
0.6223	Remote Similarity	NPC6865
0.622	Remote Similarity	NPC472061
0.6218	Remote Similarity	NPC183777
0.6217	Remote Similarity	NPC201900
0.6215	Remote Similarity	NPC260434
0.6214	Remote Similarity	NPC147983
0.6214	Remote Similarity	NPC177996
0.6208	Remote Similarity	NPC473188
0.6207	Remote Similarity	NPC97902
0.6204	Remote Similarity	NPC472259
0.6194	Remote Similarity	NPC196718
0.6194	Remote Similarity	NPC321592
0.6194	Remote Similarity	NPC54803
0.619	Remote Similarity	NPC17487
0.619	Remote Similarity	NPC201831
0.6187	Remote Similarity	NPC72956
0.6186	Remote Similarity	NPC472789
0.6176	Remote Similarity	NPC470042
0.6172	Remote Similarity	NPC41982
0.6172	Remote Similarity	NPC473833
0.617	Remote Similarity	NPC264285
0.6169	Remote Similarity	NPC477806
0.6169	Remote Similarity	NPC477107
0.6169	Remote Similarity	NPC473639
0.6169	Remote Similarity	NPC477805
0.6169	Remote Similarity	NPC477108
0.6169	Remote Similarity	NPC477796
0.6169	Remote Similarity	NPC477795
0.6169	Remote Similarity	NPC477109
0.6168	Remote Similarity	NPC53144
0.6162	Remote Similarity	NPC107836
0.6159	Remote Similarity	NPC474701
0.6159	Remote Similarity	NPC477112
0.6159	Remote Similarity	NPC14288
0.6157	Remote Similarity	NPC142901
0.6157	Remote Similarity	NPC8022
0.6157	Remote Similarity	NPC470799
0.6156	Remote Similarity	NPC475844
0.6154	Remote Similarity	NPC122886
0.6151	Remote Similarity	NPC325976
0.6151	Remote Similarity	NPC85273
0.6148	Remote Similarity	NPC315804
0.6148	Remote Similarity	NPC313804
0.6146	Remote Similarity	NPC260909
0.6143	Remote Similarity	NPC82472
0.614	Remote Similarity	NPC478141
0.6139	Remote Similarity	NPC150447
0.6138	Remote Similarity	NPC200553
0.6138	Remote Similarity	NPC102593
0.6138	Remote Similarity	NPC469554
0.6138	Remote Similarity	NPC279189
0.6137	Remote Similarity	NPC287208
0.6136	Remote Similarity	NPC39092
0.6135	Remote Similarity	NPC27041
0.6135	Remote Similarity	NPC469727
0.6133	Remote Similarity	NPC189079
0.6131	Remote Similarity	NPC211813
0.613	Remote Similarity	NPC473187
0.613	Remote Similarity	NPC162002
0.6129	Remote Similarity	NPC146418
0.6128	Remote Similarity	NPC107123
0.6128	Remote Similarity	NPC58209
0.6125	Remote Similarity	NPC223409
0.6125	Remote Similarity	NPC95240
0.6125	Remote Similarity	NPC116622
0.6125	Remote Similarity	NPC316282
0.612	Remote Similarity	NPC476516
0.6117	Remote Similarity	NPC329631
0.6115	Remote Similarity	NPC174758
0.6113	Remote Similarity	NPC244543
0.6113	Remote Similarity	NPC314270
0.6113	Remote Similarity	NPC303658
0.6111	Remote Similarity	NPC74575
0.6111	Remote Similarity	NPC261251
0.6111	Remote Similarity	NPC187145
0.6111	Remote Similarity	NPC186351
0.6109	Remote Similarity	NPC15801
0.6109	Remote Similarity	NPC321939

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 NPC179896 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	731
0.2-0.3	1250
0.3-0.4	2458
0.4-0.5	2357
0.5-0.6	1626
0.6-0.7	425
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7194	Intermediate Similarity	NPD3959	Phase 2
0.7194	Intermediate Similarity	NPD3962	Phase 2
0.7133	Intermediate Similarity	NPD5116	Phase 1
0.6921	Remote Similarity	NPD1955	Discontinued
0.6857	Remote Similarity	NPD8357	Approved
0.6767	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3986	Discontinued
0.6701	Remote Similarity	NPD4558	Phase 2
0.669	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD3043	Approved
0.6679	Remote Similarity	NPD3042	Approved
0.6677	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6656	Remote Similarity	NPD8421	Discontinued
0.6655	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7689	Approved
0.6632	Remote Similarity	NPD4561	Discontinued
0.6631	Remote Similarity	NPD4086	Phase 1
0.6631	Remote Similarity	NPD4080	Discontinued
0.6625	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7923	Phase 2
0.6599	Remote Similarity	NPD6456	Discontinued
0.6596	Remote Similarity	NPD1572	Phase 2
0.659	Remote Similarity	NPD6231	Phase 3
0.6586	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7067	Approved
0.6562	Remote Similarity	NPD7068	Approved
0.6553	Remote Similarity	NPD8370	Discontinued
0.6553	Remote Similarity	NPD5532	Phase 2
0.6549	Remote Similarity	NPD6142	Phase 3
0.6548	Remote Similarity	NPD1571	Phase 2
0.6546	Remote Similarity	NPD6153	Approved
0.6537	Remote Similarity	NPD7031	Phase 1
0.6535	Remote Similarity	NPD7655	Discontinued
0.6528	Remote Similarity	NPD7022	Phase 2
0.6494	Remote Similarity	NPD7407	Discontinued
0.6488	Remote Similarity	NPD4894	Discontinued
0.6477	Remote Similarity	NPD7603	Discontinued
0.6475	Remote Similarity	NPD8442	Discontinued
0.6474	Remote Similarity	NPD8349	Phase 1
0.6473	Remote Similarity	NPD7398	Approved
0.6473	Remote Similarity	NPD7397	Approved
0.6469	Remote Similarity	NPD3006	Discontinued
0.6458	Remote Similarity	NPD7117	Phase 2
0.6456	Remote Similarity	NPD4373	Phase 2
0.6441	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD534	Phase 2
0.6439	Remote Similarity	NPD537	Phase 2
0.6434	Remote Similarity	NPD2951	Discontinued
0.6426	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD2813	Phase 3
0.6424	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5022	Discontinued
0.6396	Remote Similarity	NPD8292	Phase 2
0.6396	Remote Similarity	NPD4845	Discontinued
0.6395	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5482	Discontinued
0.6391	Remote Similarity	NPD6023	Discontinued
0.639	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5072	Discontinued
0.6385	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7996	Phase 2
0.6379	Remote Similarity	NPD6848	Phase 1
0.6379	Remote Similarity	NPD6790	Phase 1
0.6376	Remote Similarity	NPD8091	Phase 3
0.6364	Remote Similarity	NPD949	Phase 1
0.6361	Remote Similarity	NPD5509	Phase 1
0.636	Remote Similarity	NPD5640	Discontinued
0.6358	Remote Similarity	NPD3343	Phase 3
0.6357	Remote Similarity	NPD6856	Discontinued
0.6351	Remote Similarity	NPD4952	Phase 3
0.6348	Remote Similarity	NPD8375	Approved
0.6341	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7588	Discontinued
0.6338	Remote Similarity	NPD6164	Phase 2
0.6338	Remote Similarity	NPD6165	Phase 2
0.6335	Remote Similarity	NPD5506	Approved
0.6335	Remote Similarity	NPD5507	Approved
0.6333	Remote Similarity	NPD6531	Approved
0.6333	Remote Similarity	NPD6228	Discontinued
0.6333	Remote Similarity	NPD6530	Approved
0.6331	Remote Similarity	NPD6643	Discontinued
0.6327	Remote Similarity	NPD7897	Phase 3
0.6327	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8524	Approved
0.6316	Remote Similarity	NPD7925	Phase 2
0.6316	Remote Similarity	NPD7924	Phase 2
0.6305	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6742	Phase 2
0.6296	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6743	Phase 2
0.6294	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7486	Phase 1
0.6293	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7181	Phase 3
0.6289	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD1224	Phase 2
0.6287	Remote Similarity	NPD1225	Phase 2
0.6287	Remote Similarity	NPD5018	Phase 3
0.6286	Remote Similarity	NPD4429	Discontinued
0.6284	Remote Similarity	NPD3809	Discontinued
0.6283	Remote Similarity	NPD4442	Phase 2
0.6281	Remote Similarity	NPD2349	Phase 3
0.6279	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD4560	Suspended
0.6262	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5644	Phase 1
0.625	Remote Similarity	NPD1591	Approved
0.6242	Remote Similarity	NPD3811	Discontinued
0.6241	Remote Similarity	NPD5469	Phase 3
0.6241	Remote Similarity	NPD6242	Discontinued
0.6237	Remote Similarity	NPD4358	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4897	Phase 2
0.6233	Remote Similarity	NPD6458	Discontinued
0.6233	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8525	Approved
0.6219	Remote Similarity	NPD7726	Phase 1
0.6215	Remote Similarity	NPD1505	Phase 2
0.6214	Remote Similarity	NPD3353	Approved
0.6211	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD4938	Phase 2
0.6197	Remote Similarity	NPD5450	Discontinued
0.6192	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD3255	Phase 1
0.6189	Remote Similarity	NPD3254	Phase 1
0.6184	Remote Similarity	NPD8479	Phase 2
0.6182	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5149	Phase 2
0.6175	Remote Similarity	NPD2803	Discontinued
0.6169	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD6572	Phase 2
0.6169	Remote Similarity	NPD6573	Phase 3
0.6169	Remote Similarity	NPD7408	Phase 2
0.6164	Remote Similarity	NPD4368	Phase 2
0.6151	Remote Similarity	NPD2757	Phase 2
0.6151	Remote Similarity	NPD6970	Phase 2
0.6149	Remote Similarity	NPD6745	Discontinued
0.6148	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7887	Approved
0.6146	Remote Similarity	NPD7888	Approved
0.6146	Remote Similarity	NPD8460	Approved
0.6146	Remote Similarity	NPD8459	Approved
0.6145	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3947	Discontinued
0.6141	Remote Similarity	NPD7013	Phase 3
0.6141	Remote Similarity	NPD7012	Phase 3
0.614	Remote Similarity	NPD8356	Approved
0.6136	Remote Similarity	NPD1483	Discontinued
0.6136	Remote Similarity	NPD6716	Phase 1
0.6136	Remote Similarity	NPD3322	Phase 1
0.6136	Remote Similarity	NPD6517	Phase 3
0.6135	Remote Similarity	NPD8271	Discontinued
0.6132	Remote Similarity	NPD7426	Phase 1
0.6127	Remote Similarity	NPD245	Suspended
0.6126	Remote Similarity	NPD8255	Phase 2
0.6122	Remote Similarity	NPD5905	Phase 1
0.6122	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5293	Phase 2
0.6119	Remote Similarity	NPD6829	Phase 2
0.6117	Remote Similarity	NPD5459	Phase 2
0.6117	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6113	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6113	Remote Similarity	NPD5948	Phase 2
0.6113	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.6113	Remote Similarity	NPD4353	Phase 2
0.6111	Remote Similarity	NPD8430	Approved
0.6109	Remote Similarity	NPD6709	Phase 3
0.6103	Remote Similarity	NPD6962	Phase 2
0.6101	Remote Similarity	NPD796	Phase 2
0.61	Remote Similarity	NPD5878	Approved
0.61	Remote Similarity	NPD5875	Approved
0.6098	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD3838	Phase 3
0.6091	Remote Similarity	NPD7273	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD2984	Phase 2
0.6082	Remote Similarity	NPD3746	Discontinued
0.6082	Remote Similarity	NPD8119	Discontinued
0.6081	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD6473	Phase 1
0.6081	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD3256	Phase 2
0.6078	Remote Similarity	NPD5461	Discontinued
0.6076	Remote Similarity	NPD8289	Discontinued
0.6076	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD7051	Phase 3
0.6076	Remote Similarity	NPD1273	Discontinued
0.6076	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD5488	Discontinued
0.6074	Remote Similarity	NPD5807	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