NPASS Compound

Structure

NPC469727 OpenBabel07101719522D 24 28 0 0 0 0 0 0 0 0999 V2000 5.5897 -1.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7237 -1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5793 -1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1256 1.6898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7237 0.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5897 -0.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 0.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8576 -0.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8576 -1.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1152 -1.5374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1256 -0.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7521 -1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 -1.5374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1256 -1.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2596 0.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 -0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2400 -2.5262 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2596 1.1898 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 -1.8102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.4557 0.1898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1899 -2.5346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 8 1 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 6 1 0 0 0 0 4 12 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 23 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 11 22 2 0 0 0 0 12 14 1 0 0 0 0 12 24 2 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.1
Volume:	312.305
LogP:	0.2
LogD:	0.73
LogS:	-4.98
# Rotatable Bonds:	0
TPSA:	98.96
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	3.534
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.327
MDCK Permeability:	2.4989305984490784e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.743
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	92.87486267089844%
Volume Distribution (VD):	1.006
Pgp-substrate:	5.331536769866943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.631
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.549
CYP2D6-inhibitor:	0.573
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	1.82
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.75
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.566
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.412
Carcinogencity:	0.289
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC469727

Natural Product ID:	NPC469727
*Common Name:**	Cystodimine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TWKCVAGQKSOIEB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12N4O2/c19-15-14-12(24)4-6-21-18(14)17-13-9(3-5-20-17)10-7-8(23)1-2-11(10)22-16(13)15/h1-3,5,7,19,21,23H,4,6H2
SMILES:	Oc1ccc2c(c1)c1ccnc3c1c(n2)C(=N)C1=C3NCCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163843
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2600.0	nM	PMID[491458]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	10500.0	nM	PMID[491458]

☑ 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 NPC469727 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	460
0.1-0.2	3460
0.2-0.3	13373
0.3-0.4	9797
0.4-0.5	10831
0.5-0.6	2349
0.6-0.7	2153
0.7-0.8	269
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.849	Intermediate Similarity	NPC467063
0.81	Intermediate Similarity	NPC477549
0.8086	Intermediate Similarity	NPC309845
0.8082	Intermediate Similarity	NPC477112
0.8045	Intermediate Similarity	NPC207686
0.8019	Intermediate Similarity	NPC237740
0.801	Intermediate Similarity	NPC216550
0.8	Intermediate Similarity	NPC276657
0.7981	Intermediate Similarity	NPC477113
0.7946	Intermediate Similarity	NPC41679
0.7923	Intermediate Similarity	NPC211813
0.7905	Intermediate Similarity	NPC477111
0.7895	Intermediate Similarity	NPC178858
0.786	Intermediate Similarity	NPC27041
0.7854	Intermediate Similarity	NPC90229
0.784	Intermediate Similarity	NPC219087
0.7826	Intermediate Similarity	NPC213308
0.7826	Intermediate Similarity	NPC315491
0.7826	Intermediate Similarity	NPC45459
0.782	Intermediate Similarity	NPC171787
0.7767	Intermediate Similarity	NPC167710
0.7762	Intermediate Similarity	NPC475070
0.7745	Intermediate Similarity	NPC99666
0.7731	Intermediate Similarity	NPC477110
0.7711	Intermediate Similarity	NPC314002
0.77	Intermediate Similarity	NPC220765
0.7696	Intermediate Similarity	NPC304926
0.7696	Intermediate Similarity	NPC476041
0.7681	Intermediate Similarity	NPC77555
0.7681	Intermediate Similarity	NPC156704
0.7662	Intermediate Similarity	NPC204717
0.7659	Intermediate Similarity	NPC324149
0.7617	Intermediate Similarity	NPC476116
0.7609	Intermediate Similarity	NPC473312
0.7606	Intermediate Similarity	NPC270918
0.7586	Intermediate Similarity	NPC171171
0.7585	Intermediate Similarity	NPC276517
0.7583	Intermediate Similarity	NPC328318
0.7583	Intermediate Similarity	NPC328596
0.7581	Intermediate Similarity	NPC5145
0.7577	Intermediate Similarity	NPC97902
0.7547	Intermediate Similarity	NPC476098
0.7545	Intermediate Similarity	NPC6215
0.7545	Intermediate Similarity	NPC74360
0.7543	Intermediate Similarity	NPC208522
0.7536	Intermediate Similarity	NPC329541
0.7523	Intermediate Similarity	NPC193238
0.7523	Intermediate Similarity	NPC88008
0.75	Intermediate Similarity	NPC264285
0.75	Intermediate Similarity	NPC184964
0.7489	Intermediate Similarity	NPC322482
0.7477	Intermediate Similarity	NPC175602
0.7477	Intermediate Similarity	NPC317373
0.7465	Intermediate Similarity	NPC200836
0.7465	Intermediate Similarity	NPC53144
0.7452	Intermediate Similarity	NPC45850
0.7444	Intermediate Similarity	NPC216612
0.7435	Intermediate Similarity	NPC184225
0.743	Intermediate Similarity	NPC327592
0.7429	Intermediate Similarity	NPC78767
0.7429	Intermediate Similarity	NPC473814
0.7429	Intermediate Similarity	NPC74153
0.7413	Intermediate Similarity	NPC157583
0.7412	Intermediate Similarity	NPC279189
0.7412	Intermediate Similarity	NPC200553
0.7411	Intermediate Similarity	NPC130570
0.7407	Intermediate Similarity	NPC18348
0.7406	Intermediate Similarity	NPC249040
0.7393	Intermediate Similarity	NPC192315
0.7382	Intermediate Similarity	NPC171393
0.7382	Intermediate Similarity	NPC295452
0.7373	Intermediate Similarity	NPC61038
0.7368	Intermediate Similarity	NPC473821
0.7361	Intermediate Similarity	NPC53344
0.7361	Intermediate Similarity	NPC183777
0.7358	Intermediate Similarity	NPC476167
0.7352	Intermediate Similarity	NPC110182
0.735	Intermediate Similarity	NPC142385
0.7349	Intermediate Similarity	NPC470500
0.7344	Intermediate Similarity	NPC74619
0.7343	Intermediate Similarity	NPC32771
0.7339	Intermediate Similarity	NPC470020
0.7336	Intermediate Similarity	NPC49547
0.7333	Intermediate Similarity	NPC93390
0.733	Intermediate Similarity	NPC476161
0.733	Intermediate Similarity	NPC322064
0.7327	Intermediate Similarity	NPC82548
0.7321	Intermediate Similarity	NPC272458
0.7316	Intermediate Similarity	NPC162002
0.7315	Intermediate Similarity	NPC472064
0.7313	Intermediate Similarity	NPC74575
0.7311	Intermediate Similarity	NPC474916
0.731	Intermediate Similarity	NPC97367
0.7299	Intermediate Similarity	NPC128244
0.7295	Intermediate Similarity	NPC278434
0.7295	Intermediate Similarity	NPC46580
0.7289	Intermediate Similarity	NPC16352
0.7277	Intermediate Similarity	NPC472099
0.7273	Intermediate Similarity	NPC174489
0.7273	Intermediate Similarity	NPC182222
0.7269	Intermediate Similarity	NPC264166
0.7269	Intermediate Similarity	NPC274291
0.7269	Intermediate Similarity	NPC47059
0.7269	Intermediate Similarity	NPC118832
0.7269	Intermediate Similarity	NPC165349
0.7269	Intermediate Similarity	NPC329708
0.7264	Intermediate Similarity	NPC227582
0.726	Intermediate Similarity	NPC85273
0.7257	Intermediate Similarity	NPC229893
0.7252	Intermediate Similarity	NPC469928
0.725	Intermediate Similarity	NPC314940
0.725	Intermediate Similarity	NPC473764
0.7249	Intermediate Similarity	NPC326363
0.7244	Intermediate Similarity	NPC60621
0.7243	Intermediate Similarity	NPC176538
0.724	Intermediate Similarity	NPC477610
0.724	Intermediate Similarity	NPC317752
0.724	Intermediate Similarity	NPC207866
0.7237	Intermediate Similarity	NPC157931
0.7235	Intermediate Similarity	NPC472065
0.7232	Intermediate Similarity	NPC193267
0.7232	Intermediate Similarity	NPC213530
0.7227	Intermediate Similarity	NPC91868
0.7227	Intermediate Similarity	NPC63971
0.7217	Intermediate Similarity	NPC476451
0.7217	Intermediate Similarity	NPC242209
0.7212	Intermediate Similarity	NPC220851
0.721	Intermediate Similarity	NPC15801
0.721	Intermediate Similarity	NPC26641
0.7206	Intermediate Similarity	NPC232340
0.7204	Intermediate Similarity	NPC307963
0.7198	Intermediate Similarity	NPC325976
0.7195	Intermediate Similarity	NPC318299
0.7193	Intermediate Similarity	NPC470018
0.7193	Intermediate Similarity	NPC24370
0.7193	Intermediate Similarity	NPC319232
0.7191	Intermediate Similarity	NPC81175
0.7189	Intermediate Similarity	NPC472259
0.7188	Intermediate Similarity	NPC473310
0.7186	Intermediate Similarity	NPC471178
0.7181	Intermediate Similarity	NPC122436
0.7177	Intermediate Similarity	NPC103119
0.7177	Intermediate Similarity	NPC183805
0.7176	Intermediate Similarity	NPC470678
0.7172	Intermediate Similarity	NPC59779
0.7172	Intermediate Similarity	NPC471177
0.7172	Intermediate Similarity	NPC124542
0.7169	Intermediate Similarity	NPC476157
0.7167	Intermediate Similarity	NPC295228
0.7163	Intermediate Similarity	NPC315957
0.7163	Intermediate Similarity	NPC252338
0.7162	Intermediate Similarity	NPC316181
0.7162	Intermediate Similarity	NPC74562
0.7162	Intermediate Similarity	NPC151781
0.7162	Intermediate Similarity	NPC470126
0.7161	Intermediate Similarity	NPC72905
0.7154	Intermediate Similarity	NPC132385
0.715	Intermediate Similarity	NPC131887
0.7149	Intermediate Similarity	NPC37152
0.7143	Intermediate Similarity	NPC469734
0.7137	Intermediate Similarity	NPC235685
0.7136	Intermediate Similarity	NPC251090
0.7129	Intermediate Similarity	NPC252590
0.7121	Intermediate Similarity	NPC25899
0.7119	Intermediate Similarity	NPC53534
0.7118	Intermediate Similarity	NPC214980
0.7118	Intermediate Similarity	NPC132631
0.7118	Intermediate Similarity	NPC103687
0.7116	Intermediate Similarity	NPC284338
0.7111	Intermediate Similarity	NPC477609
0.7108	Intermediate Similarity	NPC150048
0.7108	Intermediate Similarity	NPC203754
0.7106	Intermediate Similarity	NPC101350
0.7104	Intermediate Similarity	NPC471304
0.7097	Intermediate Similarity	NPC472069
0.7097	Intermediate Similarity	NPC472063
0.7097	Intermediate Similarity	NPC472062
0.7095	Intermediate Similarity	NPC296527
0.7095	Intermediate Similarity	NPC255909
0.709	Intermediate Similarity	NPC63109
0.7089	Intermediate Similarity	NPC326634
0.7087	Intermediate Similarity	NPC478078
0.7085	Intermediate Similarity	NPC266931
0.7085	Intermediate Similarity	NPC48192
0.7081	Intermediate Similarity	NPC62749
0.708	Intermediate Similarity	NPC269270
0.7078	Intermediate Similarity	NPC476124
0.7078	Intermediate Similarity	NPC476121
0.7076	Intermediate Similarity	NPC41501
0.7074	Intermediate Similarity	NPC476818
0.7073	Intermediate Similarity	NPC237188
0.7072	Intermediate Similarity	NPC208284
0.707	Intermediate Similarity	NPC34837
0.707	Intermediate Similarity	NPC265576
0.707	Intermediate Similarity	NPC212213
0.7064	Intermediate Similarity	NPC98715
0.7062	Intermediate Similarity	NPC154339
0.7062	Intermediate Similarity	NPC76748
0.7059	Intermediate Similarity	NPC303225
0.7056	Intermediate Similarity	NPC477607

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 NPC469727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	643
0.2-0.3	840
0.3-0.4	1409
0.4-0.5	2704
0.5-0.6	2044
0.6-0.7	1140
0.7-0.8	108
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
0.8018	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD4845	Discontinued
0.7826	Intermediate Similarity	NPD484	Approved
0.7773	Intermediate Similarity	NPD3959	Phase 2
0.7773	Intermediate Similarity	NPD3962	Phase 2
0.7689	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD6242	Discontinued
0.758	Intermediate Similarity	NPD4429	Discontinued
0.7578	Intermediate Similarity	NPD7603	Discontinued
0.7438	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3928	Approved
0.7418	Intermediate Similarity	NPD3931	Approved
0.7401	Intermediate Similarity	NPD5022	Discontinued
0.7346	Intermediate Similarity	NPD7948	Phase 1
0.7336	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7112	Discontinued
0.7317	Intermediate Similarity	NPD6178	Phase 3
0.7309	Intermediate Similarity	NPD7404	Approved
0.7303	Intermediate Similarity	NPD8091	Phase 3
0.7286	Intermediate Similarity	NPD9695	Approved
0.7273	Intermediate Similarity	NPD3330	Phase 1
0.7269	Intermediate Similarity	NPD4034	Approved
0.7269	Intermediate Similarity	NPD4035	Approved
0.7269	Intermediate Similarity	NPD4122	Approved
0.7269	Intermediate Similarity	NPD32	Approved
0.7269	Intermediate Similarity	NPD4795	Phase 2
0.7269	Intermediate Similarity	NPD4039	Approved
0.7269	Intermediate Similarity	NPD4038	Approved
0.7269	Intermediate Similarity	NPD4037	Approved
0.7269	Intermediate Similarity	NPD4036	Approved
0.7269	Intermediate Similarity	NPD4033	Approved
0.7269	Intermediate Similarity	NPD31	Approved
0.7252	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7666	Phase 3
0.7248	Intermediate Similarity	NPD7665	Phase 2
0.7248	Intermediate Similarity	NPD2916	Discontinued
0.7243	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6165	Phase 2
0.7237	Intermediate Similarity	NPD6164	Phase 2
0.7236	Intermediate Similarity	NPD424	Approved
0.7236	Intermediate Similarity	NPD425	Approved
0.7228	Intermediate Similarity	NPD5065	Approved
0.722	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4897	Phase 2
0.7204	Intermediate Similarity	NPD1038	Approved
0.7204	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5901	Discontinued
0.7181	Intermediate Similarity	NPD3222	Phase 2
0.7175	Intermediate Similarity	NPD3393	Approved
0.7175	Intermediate Similarity	NPD3394	Approved
0.7175	Intermediate Similarity	NPD3389	Approved
0.7163	Intermediate Similarity	NPD1739	Approved
0.7163	Intermediate Similarity	NPD1740	Approved
0.7143	Intermediate Similarity	NPD8106	Phase 2
0.713	Intermediate Similarity	NPD4511	Phase 1
0.7118	Intermediate Similarity	NPD8289	Discontinued
0.7117	Intermediate Similarity	NPD8093	Discontinued
0.7112	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4051	Discontinued
0.7098	Intermediate Similarity	NPD5612	Discontinued
0.7093	Intermediate Similarity	NPD5506	Approved
0.7093	Intermediate Similarity	NPD5507	Approved
0.7087	Intermediate Similarity	NPD2479	Phase 3
0.7087	Intermediate Similarity	NPD2481	Approved
0.7085	Intermediate Similarity	NPD3794	Approved
0.7085	Intermediate Similarity	NPD3795	Approved
0.7076	Intermediate Similarity	NPD4561	Discontinued
0.7072	Intermediate Similarity	NPD5416	Discontinued
0.7072	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9690	Approved
0.7054	Intermediate Similarity	NPD3809	Discontinued
0.7053	Intermediate Similarity	NPD7867	Phase 1
0.7045	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6999	Discontinued
0.7037	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD9705	Discontinued
0.7035	Intermediate Similarity	NPD112	Approved
0.7033	Intermediate Similarity	NPD2762	Phase 2
0.7033	Intermediate Similarity	NPD6530	Approved
0.7033	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6531	Approved
0.7028	Intermediate Similarity	NPD2336	Approved
0.7026	Intermediate Similarity	NPD6968	Phase 2
0.7026	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6969	Phase 2
0.7019	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD925	Approved
0.7015	Intermediate Similarity	NPD926	Approved
0.7014	Intermediate Similarity	NPD6376	Discontinued
0.7012	Intermediate Similarity	NPD4558	Phase 2
0.7005	Intermediate Similarity	NPD6479	Discontinued
0.7005	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5475	Discontinued
0.6995	Remote Similarity	NPD3404	Approved
0.699	Remote Similarity	NPD6159	Phase 2
0.6986	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7797	Approved
0.6966	Remote Similarity	NPD7796	Approved
0.6963	Remote Similarity	NPD5428	Discontinued
0.696	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2177	Approved
0.6959	Remote Similarity	NPD2175	Phase 3
0.6959	Remote Similarity	NPD2176	Approved
0.6958	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2781	Approved
0.6937	Remote Similarity	NPD2509	Approved
0.6937	Remote Similarity	NPD2510	Approved
0.6936	Remote Similarity	NPD4850	Phase 1
0.6933	Remote Similarity	NPD2615	Phase 3
0.6933	Remote Similarity	NPD3243	Approved
0.6933	Remote Similarity	NPD2616	Phase 3
0.6933	Remote Similarity	NPD8094	Discontinued
0.6931	Remote Similarity	NPD2780	Approved
0.6931	Remote Similarity	NPD2782	Approved
0.693	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7010	Phase 3
0.692	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.692	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4989	Phase 2
0.6916	Remote Similarity	NPD6569	Phase 2
0.6913	Remote Similarity	NPD8356	Approved
0.691	Remote Similarity	NPD5559	Phase 2
0.6909	Remote Similarity	NPD4886	Phase 2
0.6905	Remote Similarity	NPD7564	Discontinued
0.6903	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5293	Phase 2
0.69	Remote Similarity	NPD5255	Approved
0.6898	Remote Similarity	NPD2307	Discontinued
0.6897	Remote Similarity	NPD7426	Phase 1
0.6895	Remote Similarity	NPD7923	Phase 2
0.6891	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7069	Discontinued
0.6886	Remote Similarity	NPD3354	Phase 2
0.6878	Remote Similarity	NPD5426	Phase 3
0.6878	Remote Similarity	NPD5469	Phase 3
0.687	Remote Similarity	NPD5147	Discontinued
0.6867	Remote Similarity	NPD8430	Approved
0.6864	Remote Similarity	NPD7187	Phase 2
0.6864	Remote Similarity	NPD6975	Discontinued
0.686	Remote Similarity	NPD2382	Approved
0.686	Remote Similarity	NPD2380	Approved
0.686	Remote Similarity	NPD2381	Approved
0.6844	Remote Similarity	NPD3986	Discontinued
0.6844	Remote Similarity	NPD5939	Approved
0.6844	Remote Similarity	NPD5936	Approved
0.6844	Remote Similarity	NPD8101	Phase 3
0.6842	Remote Similarity	NPD6961	Discontinued
0.684	Remote Similarity	NPD1856	Discontinued
0.684	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5505	Discontinued
0.6835	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1685	Approved
0.6832	Remote Similarity	NPD1684	Approved
0.6831	Remote Similarity	NPD6276	Discontinued
0.6828	Remote Similarity	NPD7188	Phase 3
0.6828	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3280	Approved
0.6825	Remote Similarity	NPD2091	Phase 2
0.6825	Remote Similarity	NPD2096	Phase 2
0.6822	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3321	Discontinued
0.6818	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6158	Phase 2
0.6816	Remote Similarity	NPD6290	Phase 2
0.6816	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD482	Approved
0.6812	Remote Similarity	NPD7395	Discontinued
0.6812	Remote Similarity	NPD4883	Approved
0.681	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7392	Phase 2
0.6804	Remote Similarity	NPD3825	Phase 3
0.6804	Remote Similarity	NPD8396	Approved
0.6804	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5999	Phase 2
0.6804	Remote Similarity	NPD8395	Approved
0.6802	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7924	Phase 2
0.6798	Remote Similarity	NPD6957	Approved
0.6798	Remote Similarity	NPD6958	Approved
0.6798	Remote Similarity	NPD7925	Phase 2
0.6792	Remote Similarity	NPD3082	Discontinued
0.679	Remote Similarity	NPD5488	Discontinued
0.6787	Remote Similarity	NPD6132	Phase 1
0.6787	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5529	Phase 1
0.6779	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2095	Phase 2
0.6777	Remote Similarity	NPD2092	Phase 2
0.6777	Remote Similarity	NPD2094	Phase 2
0.6774	Remote Similarity	NPD7618	Phase 3

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