NPASS Compound

Structure

NPC467063 OpenBabel07101719512D 23 27 0 0 0 0 0 0 0 0999 V2000 5.5897 -0.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5897 -1.3102 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 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 3.8576 -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 -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 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 3 1 0 0 0 0 2 4 1 0 0 0 0 3 9 2 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 13 2 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 23 2 0 0 0 0 13 16 1 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 2 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:	187.07
Volume:	190.365
LogP:	0.287
LogD:	0.093
LogS:	-1.659
# Rotatable Bonds:	0
TPSA:	66.17
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	3.401
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.592
MDCK Permeability:	1.4334248589875642e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.092
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	53.583290100097656%
Volume Distribution (VD):	1.373
Pgp-substrate:	57.32221603393555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.474
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.262
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.529
CYP3A4-inhibitor:	0.278
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	1.221
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.621
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.857
Carcinogencity:	0.2
Eye Corrosion:	0.016
Eye Irritation:	0.756
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC467063

Natural Product ID:	NPC467063
*Common Name:**	Cystodimine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MYHPJEHBGONSAG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12N4O/c19-15-14-12(23)6-8-21-18(14)17-13-10(5-7-20-17)9-3-1-2-4-11(9)22-16(13)15/h1-5,7,19,21H,6,8H2
SMILES:	c1ccc2c(c1)c1ccnc3c1c(C(=N)C1=C3NCCC1=O)n2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163245
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	=	1200.0	nM	PMID[459556]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2400.0	nM	PMID[459556]

☑ 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 NPC467063 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	585
0.1-0.2	6485
0.2-0.3	17518
0.3-0.4	12214
0.4-0.5	2138
0.5-0.6	2100
0.6-0.7	1295
0.7-0.8	352
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9249	High Similarity	NPC216550
0.8933	High Similarity	NPC167710
0.85	High Similarity	NPC272458
0.849	Intermediate Similarity	NPC469727
0.8462	Intermediate Similarity	NPC128244
0.8343	Intermediate Similarity	NPC157583
0.8333	Intermediate Similarity	NPC103119
0.8239	Intermediate Similarity	NPC237188
0.8172	Intermediate Similarity	NPC34837
0.8	Intermediate Similarity	NPC191415
0.7957	Intermediate Similarity	NPC326422
0.7935	Intermediate Similarity	NPC255909
0.7931	Intermediate Similarity	NPC478184
0.7869	Intermediate Similarity	NPC99939
0.7869	Intermediate Similarity	NPC308931
0.7841	Intermediate Similarity	NPC56233
0.7833	Intermediate Similarity	NPC284775
0.776	Intermediate Similarity	NPC102755
0.7727	Intermediate Similarity	NPC21174
0.7727	Intermediate Similarity	NPC271797
0.7717	Intermediate Similarity	NPC477003
0.7672	Intermediate Similarity	NPC304203
0.7657	Intermediate Similarity	NPC293487
0.7627	Intermediate Similarity	NPC478182
0.7624	Intermediate Similarity	NPC297034
0.7611	Intermediate Similarity	NPC201634
0.7602	Intermediate Similarity	NPC472064
0.759	Intermediate Similarity	NPC317701
0.7584	Intermediate Similarity	NPC42372
0.7566	Intermediate Similarity	NPC476460
0.7542	Intermediate Similarity	NPC478183
0.7529	Intermediate Similarity	NPC325903
0.7528	Intermediate Similarity	NPC265100
0.7528	Intermediate Similarity	NPC317105
0.7527	Intermediate Similarity	NPC293216
0.7527	Intermediate Similarity	NPC21429
0.7526	Intermediate Similarity	NPC47190
0.7514	Intermediate Similarity	NPC122141
0.7513	Intermediate Similarity	NPC472065
0.75	Intermediate Similarity	NPC469811
0.7474	Intermediate Similarity	NPC237414
0.7473	Intermediate Similarity	NPC252572
0.7472	Intermediate Similarity	NPC225018
0.7472	Intermediate Similarity	NPC478185
0.7471	Intermediate Similarity	NPC70406
0.7459	Intermediate Similarity	NPC73994
0.7457	Intermediate Similarity	NPC321911
0.7449	Intermediate Similarity	NPC328318
0.7449	Intermediate Similarity	NPC328596
0.7447	Intermediate Similarity	NPC17273
0.7447	Intermediate Similarity	NPC135601
0.7447	Intermediate Similarity	NPC141612
0.7442	Intermediate Similarity	NPC63545
0.7429	Intermediate Similarity	NPC251391
0.7414	Intermediate Similarity	NPC40070
0.7405	Intermediate Similarity	NPC11126
0.7403	Intermediate Similarity	NPC70949
0.7399	Intermediate Similarity	NPC179787
0.7399	Intermediate Similarity	NPC201380
0.7385	Intermediate Similarity	NPC475914
0.7385	Intermediate Similarity	NPC220797
0.7385	Intermediate Similarity	NPC474318
0.7385	Intermediate Similarity	NPC284338
0.7385	Intermediate Similarity	NPC201266
0.7385	Intermediate Similarity	NPC268744
0.7385	Intermediate Similarity	NPC153123
0.7384	Intermediate Similarity	NPC467188
0.7374	Intermediate Similarity	NPC327592
0.7374	Intermediate Similarity	NPC88115
0.7371	Intermediate Similarity	NPC227582
0.7363	Intermediate Similarity	NPC32534
0.7363	Intermediate Similarity	NPC91895
0.736	Intermediate Similarity	NPC106757
0.736	Intermediate Similarity	NPC472062
0.736	Intermediate Similarity	NPC472069
0.736	Intermediate Similarity	NPC472063
0.736	Intermediate Similarity	NPC474492
0.7354	Intermediate Similarity	NPC62749
0.735	Intermediate Similarity	NPC116555
0.7347	Intermediate Similarity	NPC269203
0.7347	Intermediate Similarity	NPC13456
0.7347	Intermediate Similarity	NPC166209
0.7347	Intermediate Similarity	NPC77241
0.734	Intermediate Similarity	NPC228835
0.7337	Intermediate Similarity	NPC471579
0.7337	Intermediate Similarity	NPC317373
0.733	Intermediate Similarity	NPC324091
0.7326	Intermediate Similarity	NPC470677
0.7303	Intermediate Similarity	NPC193740
0.7302	Intermediate Similarity	NPC133003
0.73	Intermediate Similarity	NPC175916
0.7299	Intermediate Similarity	NPC105811
0.7297	Intermediate Similarity	NPC280852
0.7296	Intermediate Similarity	NPC81535
0.7296	Intermediate Similarity	NPC74413
0.7283	Intermediate Similarity	NPC86288
0.7282	Intermediate Similarity	NPC106824
0.7278	Intermediate Similarity	NPC314102
0.7278	Intermediate Similarity	NPC194881
0.7278	Intermediate Similarity	NPC105127
0.7278	Intermediate Similarity	NPC251722
0.7278	Intermediate Similarity	NPC470203
0.7278	Intermediate Similarity	NPC242116
0.7273	Intermediate Similarity	NPC470233
0.7268	Intermediate Similarity	NPC157828
0.7268	Intermediate Similarity	NPC195239
0.7267	Intermediate Similarity	NPC190296
0.7263	Intermediate Similarity	NPC475990
0.7259	Intermediate Similarity	NPC252338
0.7257	Intermediate Similarity	NPC123906
0.7243	Intermediate Similarity	NPC469529
0.7241	Intermediate Similarity	NPC72956
0.7241	Intermediate Similarity	NPC288838
0.7241	Intermediate Similarity	NPC143872
0.7233	Intermediate Similarity	NPC267811
0.7232	Intermediate Similarity	NPC281094
0.7231	Intermediate Similarity	NPC11445
0.7225	Intermediate Similarity	NPC17059
0.7222	Intermediate Similarity	NPC215584
0.7222	Intermediate Similarity	NPC100104
0.7222	Intermediate Similarity	NPC470204
0.7222	Intermediate Similarity	NPC44773
0.7222	Intermediate Similarity	NPC470680
0.7219	Intermediate Similarity	NPC96102
0.7219	Intermediate Similarity	NPC12649
0.7216	Intermediate Similarity	NPC313889
0.7208	Intermediate Similarity	NPC477004
0.7207	Intermediate Similarity	NPC236711
0.7206	Intermediate Similarity	NPC470702
0.7206	Intermediate Similarity	NPC153980
0.7206	Intermediate Similarity	NPC473218
0.7206	Intermediate Similarity	NPC6865
0.7206	Intermediate Similarity	NPC471193
0.7206	Intermediate Similarity	NPC471194
0.7204	Intermediate Similarity	NPC151635
0.7198	Intermediate Similarity	NPC473310
0.7196	Intermediate Similarity	NPC470205
0.7193	Intermediate Similarity	NPC110126
0.7191	Intermediate Similarity	NPC476219
0.7189	Intermediate Similarity	NPC161861
0.7186	Intermediate Similarity	NPC260900
0.7184	Intermediate Similarity	NPC314372
0.7184	Intermediate Similarity	NPC159856
0.7181	Intermediate Similarity	NPC88110
0.7181	Intermediate Similarity	NPC24864
0.7178	Intermediate Similarity	NPC66699
0.7176	Intermediate Similarity	NPC84911
0.7173	Intermediate Similarity	NPC118084
0.7171	Intermediate Similarity	NPC470703
0.7168	Intermediate Similarity	NPC20144
0.7167	Intermediate Similarity	NPC56765
0.7167	Intermediate Similarity	NPC80681
0.7167	Intermediate Similarity	NPC206819
0.7167	Intermediate Similarity	NPC92796
0.7167	Intermediate Similarity	NPC135141
0.7167	Intermediate Similarity	NPC318065
0.7166	Intermediate Similarity	NPC83774
0.7158	Intermediate Similarity	NPC114637
0.7157	Intermediate Similarity	NPC265576
0.7151	Intermediate Similarity	NPC469779
0.7151	Intermediate Similarity	NPC469768
0.7151	Intermediate Similarity	NPC469784
0.7151	Intermediate Similarity	NPC469780
0.7151	Intermediate Similarity	NPC469761
0.7151	Intermediate Similarity	NPC469767
0.7151	Intermediate Similarity	NPC469783
0.715	Intermediate Similarity	NPC472112
0.715	Intermediate Similarity	NPC154339
0.7143	Intermediate Similarity	NPC102592
0.7143	Intermediate Similarity	NPC472070
0.7143	Intermediate Similarity	NPC79356
0.7135	Intermediate Similarity	NPC138842
0.7135	Intermediate Similarity	NPC169433
0.7134	Intermediate Similarity	NPC166424
0.7134	Intermediate Similarity	NPC245244
0.7134	Intermediate Similarity	NPC146373
0.7128	Intermediate Similarity	NPC55772
0.7122	Intermediate Similarity	NPC318299
0.712	Intermediate Similarity	NPC63751
0.712	Intermediate Similarity	NPC78020
0.712	Intermediate Similarity	NPC15102
0.7119	Intermediate Similarity	NPC473878
0.7119	Intermediate Similarity	NPC53947
0.7119	Intermediate Similarity	NPC105818
0.7119	Intermediate Similarity	NPC24678
0.7118	Intermediate Similarity	NPC261195
0.7118	Intermediate Similarity	NPC29886
0.7117	Intermediate Similarity	NPC46358
0.7111	Intermediate Similarity	NPC286427
0.7111	Intermediate Similarity	NPC213914
0.711	Intermediate Similarity	NPC469766
0.7102	Intermediate Similarity	NPC470111
0.7101	Intermediate Similarity	NPC471192
0.7098	Intermediate Similarity	NPC321708
0.7095	Intermediate Similarity	NPC209362
0.7093	Intermediate Similarity	NPC73767
0.7093	Intermediate Similarity	NPC88097
0.7092	Intermediate Similarity	NPC202812
0.709	Intermediate Similarity	NPC61011
0.7087	Intermediate Similarity	NPC234078

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 NPC467063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	698
0.2-0.3	1014
0.3-0.4	2102
0.4-0.5	2087
0.5-0.6	1960
0.6-0.7	856
0.7-0.8	136
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8146	Intermediate Similarity	NPD2481	Approved
0.8146	Intermediate Similarity	NPD2479	Phase 3
0.8011	Intermediate Similarity	NPD7564	Discontinued
0.7897	Intermediate Similarity	NPD4051	Discontinued
0.7857	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD5446	Phase 2
0.7717	Intermediate Similarity	NPD6178	Phase 3
0.767	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7175	Phase 1
0.7551	Intermediate Similarity	NPD7209	Approved
0.7551	Intermediate Similarity	NPD7208	Approved
0.7551	Intermediate Similarity	NPD7207	Approved
0.7529	Intermediate Similarity	NPD2837	Discontinued
0.7528	Intermediate Similarity	NPD3583	Phase 2
0.7526	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4848	Phase 1
0.75	Intermediate Similarity	NPD1270	Approved
0.7472	Intermediate Similarity	NPD6771	Discontinued
0.7472	Intermediate Similarity	NPD5400	Approved
0.7448	Intermediate Similarity	NPD7618	Phase 3
0.7448	Intermediate Similarity	NPD7619	Phase 3
0.7444	Intermediate Similarity	NPD6446	Discontinued
0.7436	Intermediate Similarity	NPD6479	Discontinued
0.7435	Intermediate Similarity	NPD4922	Phase 2
0.7433	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7404	Approved
0.7403	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1343	Approved
0.7391	Intermediate Similarity	NPD4075	Phase 2
0.7382	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5473	Discontinued
0.7349	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4883	Approved
0.7327	Intermediate Similarity	NPD6152	Phase 1
0.731	Intermediate Similarity	NPD1722	Approved
0.73	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4547	Phase 3
0.7291	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD975	Approved
0.7288	Intermediate Similarity	NPD976	Approved
0.7288	Intermediate Similarity	NPD977	Approved
0.7287	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6664	Approved
0.7267	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7026	Phase 2
0.7256	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD991	Phase 2
0.725	Intermediate Similarity	NPD5489	Phase 1
0.725	Intermediate Similarity	NPD5491	Phase 3
0.7241	Intermediate Similarity	NPD7469	Discontinued
0.7238	Intermediate Similarity	NPD3323	Discontinued
0.7234	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7027	Phase 3
0.7225	Intermediate Similarity	NPD3961	Discontinued
0.7225	Intermediate Similarity	NPD4988	Discontinued
0.7219	Intermediate Similarity	NPD3077	Approved
0.7219	Intermediate Similarity	NPD3076	Approved
0.7219	Intermediate Similarity	NPD3079	Approved
0.7219	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3078	Approved
0.7213	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2411	Approved
0.7206	Intermediate Similarity	NPD6954	Phase 2
0.7202	Intermediate Similarity	NPD2336	Approved
0.7171	Intermediate Similarity	NPD5888	Phase 2
0.7168	Intermediate Similarity	NPD2006	Phase 2
0.7166	Intermediate Similarity	NPD4181	Approved
0.7165	Intermediate Similarity	NPD5505	Discontinued
0.7164	Intermediate Similarity	NPD2008	Discontinued
0.7159	Intermediate Similarity	NPD3100	Discontinued
0.7159	Intermediate Similarity	NPD2430	Phase 2
0.7158	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4128	Approved
0.7143	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6481	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7394	Phase 2
0.7129	Intermediate Similarity	NPD1506	Discontinued
0.7126	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD715	Phase 3
0.7112	Intermediate Similarity	NPD3348	Phase 2
0.7105	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2720	Phase 1
0.7104	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3393	Approved
0.7101	Intermediate Similarity	NPD3394	Approved
0.7101	Intermediate Similarity	NPD3389	Approved
0.7097	Intermediate Similarity	NPD7216	Approved
0.7097	Intermediate Similarity	NPD7217	Approved
0.7095	Intermediate Similarity	NPD2165	Phase 1
0.7094	Intermediate Similarity	NPD7666	Phase 3
0.7094	Intermediate Similarity	NPD2442	Approved
0.7094	Intermediate Similarity	NPD2443	Approved
0.7094	Intermediate Similarity	NPD7665	Phase 2
0.7093	Intermediate Similarity	NPD786	Approved
0.7092	Intermediate Similarity	NPD5853	Phase 3
0.7092	Intermediate Similarity	NPD5855	Phase 3
0.7092	Intermediate Similarity	NPD7406	Phase 2
0.709	Intermediate Similarity	NPD3927	Phase 2
0.7089	Intermediate Similarity	NPD6164	Phase 2
0.7089	Intermediate Similarity	NPD6165	Phase 2
0.7083	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4615	Phase 2
0.7074	Intermediate Similarity	NPD2753	Discontinued
0.7073	Intermediate Similarity	NPD5475	Discontinued
0.7069	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5065	Approved
0.7059	Intermediate Similarity	NPD482	Approved
0.7056	Intermediate Similarity	NPD2307	Discontinued
0.7056	Intermediate Similarity	NPD3114	Approved
0.7056	Intermediate Similarity	NPD3112	Approved
0.7056	Intermediate Similarity	NPD3115	Approved
0.7056	Intermediate Similarity	NPD3113	Approved
0.7056	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1683	Approved
0.7044	Intermediate Similarity	NPD3905	Phase 3
0.7039	Intermediate Similarity	NPD7455	Approved
0.7039	Intermediate Similarity	NPD7454	Approved
0.7035	Intermediate Similarity	NPD5854	Approved
0.703	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3238	Discontinued
0.7021	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1256	Approved
0.7018	Intermediate Similarity	NPD1254	Approved
0.7018	Intermediate Similarity	NPD1253	Approved
0.7018	Intermediate Similarity	NPD1255	Approved
0.7017	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6268	Phase 1
0.7015	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7187	Phase 2
0.701	Intermediate Similarity	NPD6459	Phase 2
0.7005	Intermediate Similarity	NPD750	Phase 2
0.7	Intermediate Similarity	NPD3944	Approved
0.7	Intermediate Similarity	NPD6285	Phase 2
0.7	Intermediate Similarity	NPD3942	Approved
0.6995	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5974	Approved
0.699	Remote Similarity	NPD5973	Phase 2
0.6985	Remote Similarity	NPD1982	Phase 1
0.698	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD2096	Phase 2
0.6979	Remote Similarity	NPD2091	Phase 2
0.6974	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD947	Approved
0.6959	Remote Similarity	NPD2770	Discontinued
0.6959	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3117	Approved
0.6952	Remote Similarity	NPD6470	Phase 3
0.6952	Remote Similarity	NPD3116	Approved
0.695	Remote Similarity	NPD2405	Phase 3
0.6947	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8115	Approved
0.6946	Remote Similarity	NPD8114	Approved
0.6946	Remote Similarity	NPD2118	Approved
0.6946	Remote Similarity	NPD2119	Approved
0.6943	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3830	Phase 1
0.6931	Remote Similarity	NPD2881	Approved
0.6931	Remote Similarity	NPD2879	Approved
0.6931	Remote Similarity	NPD6044	Discontinued
0.6931	Remote Similarity	NPD2751	Phase 1
0.6927	Remote Similarity	NPD2092	Phase 2
0.6927	Remote Similarity	NPD2509	Approved
0.6927	Remote Similarity	NPD3320	Approved
0.6927	Remote Similarity	NPD2095	Phase 2
0.6927	Remote Similarity	NPD2094	Phase 2
0.6927	Remote Similarity	NPD2510	Approved
0.6927	Remote Similarity	NPD3318	Approved
0.6927	Remote Similarity	NPD3319	Phase 1
0.6923	Remote Similarity	NPD3794	Approved
0.6923	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3795	Approved
0.6919	Remote Similarity	NPD5199	Approved
0.6919	Remote Similarity	NPD5198	Approved
0.6912	Remote Similarity	NPD7010	Phase 3
0.6912	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.691	Remote Similarity	NPD1661	Suspended
0.6908	Remote Similarity	NPD4863	Approved
0.6904	Remote Similarity	NPD3431	Approved
0.6904	Remote Similarity	NPD3430	Approved
0.6901	Remote Similarity	NPD3385	Approved
0.69	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3505	Approved
0.6895	Remote Similarity	NPD3506	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