NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.07
Volume:	266.912
LogP:	2.214
LogD:	2.149
LogS:	-4.638
# Rotatable Bonds:	1
TPSA:	52.08
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	2.458
Fsp3:	0.062
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:	-4.787
MDCK Permeability:	2.169010986108333e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.18

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.87
Plasma Protein Binding (PPB):	92.76531982421875%
Volume Distribution (VD):	1.061
Pgp-substrate:	4.433141231536865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.899
CYP1A2-substrate:	0.826
CYP2C19-inhibitor:	0.63
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.28
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.835
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	3.236
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.77
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.943
Rat Oral Acute Toxicity:	0.511
Maximum Recommended Daily Dose:	0.328
Skin Sensitization:	0.208
Carcinogencity:	0.851
Eye Corrosion:	0.004
Eye Irritation:	0.89
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC322482

Natural Product ID:	NPC322482
*Common Name:**	ZLDFQCLGYOKBIH-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	11-Methoxysampangine
Standard InCHIKey:	ZLDFQCLGYOKBIH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10N2O2/c1-20-11-4-2-3-10-13(11)14-12-9(5-7-17-14)6-8-18-15(12)16(10)19/h2-8H,1H3
SMILES:	COc1cccc2c1c1nccc3c1c(C2=O)ncc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801765
PubChem CID:	53262837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003019] 1-azaoxoaporphines

*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
NPO13611	Ambavia gerrardii	Species	Annonaceae	Eukaryota	n.a.	Madagascar Dry Forest	n.a.	PMID[21504145]
NPO13611	Ambavia gerrardii	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[21504145]
NPO13611	Ambavia gerrardii	Species	Annonaceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	570.0	nM	PMID[521229]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10300.0	nM	PMID[521229]

☑ 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 NPC322482 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	630
0.1-0.2	3326
0.2-0.3	12452
0.3-0.4	4895
0.4-0.5	15387
0.5-0.6	4073
0.6-0.7	1631
0.7-0.8	270
0.8-0.85	26
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9082	High Similarity	NPC216612
0.901	High Similarity	NPC470020
0.872	High Similarity	NPC210434
0.8598	High Similarity	NPC470018
0.8565	High Similarity	NPC24019
0.8565	High Similarity	NPC237740
0.8558	High Similarity	NPC74575
0.8514	High Similarity	NPC72905
0.8475	Intermediate Similarity	NPC142385
0.8447	Intermediate Similarity	NPC22481
0.8402	Intermediate Similarity	NPC49547
0.8394	Intermediate Similarity	NPC278525
0.8389	Intermediate Similarity	NPC146976
0.8341	Intermediate Similarity	NPC236668
0.8333	Intermediate Similarity	NPC189903
0.8333	Intermediate Similarity	NPC137353
0.8333	Intermediate Similarity	NPC182907
0.8326	Intermediate Similarity	NPC90875
0.8318	Intermediate Similarity	NPC233334
0.8288	Intermediate Similarity	NPC108342
0.8288	Intermediate Similarity	NPC470017
0.8251	Intermediate Similarity	NPC470022
0.8246	Intermediate Similarity	NPC270515
0.8221	Intermediate Similarity	NPC327592
0.8182	Intermediate Similarity	NPC317373
0.815	Intermediate Similarity	NPC15406
0.8133	Intermediate Similarity	NPC166722
0.8114	Intermediate Similarity	NPC124313
0.8106	Intermediate Similarity	NPC84164
0.8106	Intermediate Similarity	NPC207283
0.8089	Intermediate Similarity	NPC472061
0.8062	Intermediate Similarity	NPC210296
0.8038	Intermediate Similarity	NPC328596
0.8038	Intermediate Similarity	NPC328318
0.8035	Intermediate Similarity	NPC208522
0.798	Intermediate Similarity	NPC237188
0.7962	Intermediate Similarity	NPC36229
0.7962	Intermediate Similarity	NPC476581
0.7962	Intermediate Similarity	NPC16452
0.7953	Intermediate Similarity	NPC318299
0.794	Intermediate Similarity	NPC183537
0.793	Intermediate Similarity	NPC235685
0.7919	Intermediate Similarity	NPC122436
0.7917	Intermediate Similarity	NPC317752
0.7907	Intermediate Similarity	NPC220337
0.7904	Intermediate Similarity	NPC119134
0.7895	Intermediate Similarity	NPC101350
0.7895	Intermediate Similarity	NPC287437
0.7882	Intermediate Similarity	NPC118084
0.7863	Intermediate Similarity	NPC77878
0.7833	Intermediate Similarity	NPC132385
0.782	Intermediate Similarity	NPC31930
0.7804	Intermediate Similarity	NPC193238
0.7783	Intermediate Similarity	NPC41501
0.7757	Intermediate Similarity	NPC323345
0.7757	Intermediate Similarity	NPC470164
0.7725	Intermediate Similarity	NPC4071
0.7725	Intermediate Similarity	NPC476582
0.7725	Intermediate Similarity	NPC476578
0.7706	Intermediate Similarity	NPC202768
0.7706	Intermediate Similarity	NPC202605
0.7706	Intermediate Similarity	NPC53069
0.7706	Intermediate Similarity	NPC112206
0.7706	Intermediate Similarity	NPC296482
0.7699	Intermediate Similarity	NPC246381
0.7686	Intermediate Similarity	NPC253675
0.7674	Intermediate Similarity	NPC472064
0.7661	Intermediate Similarity	NPC208284
0.7657	Intermediate Similarity	NPC478083
0.7657	Intermediate Similarity	NPC53534
0.7655	Intermediate Similarity	NPC478078
0.765	Intermediate Similarity	NPC174672
0.7642	Intermediate Similarity	NPC329631
0.7632	Intermediate Similarity	NPC260434
0.7626	Intermediate Similarity	NPC251160
0.7626	Intermediate Similarity	NPC96405
0.7626	Intermediate Similarity	NPC171409
0.7624	Intermediate Similarity	NPC157583
0.7608	Intermediate Similarity	NPC195268
0.7608	Intermediate Similarity	NPC133140
0.7604	Intermediate Similarity	NPC82548
0.7593	Intermediate Similarity	NPC472065
0.7569	Intermediate Similarity	NPC174758
0.7557	Intermediate Similarity	NPC235076
0.7553	Intermediate Similarity	NPC91868
0.7553	Intermediate Similarity	NPC63971
0.7547	Intermediate Similarity	NPC106824
0.75	Intermediate Similarity	NPC17565
0.7489	Intermediate Similarity	NPC469727
0.7478	Intermediate Similarity	NPC477112
0.7477	Intermediate Similarity	NPC313189
0.7477	Intermediate Similarity	NPC284338
0.7469	Intermediate Similarity	NPC152620
0.7469	Intermediate Similarity	NPC478045
0.7466	Intermediate Similarity	NPC264176
0.7466	Intermediate Similarity	NPC472098
0.7465	Intermediate Similarity	NPC285558
0.7455	Intermediate Similarity	NPC23614
0.7455	Intermediate Similarity	NPC290689
0.7455	Intermediate Similarity	NPC123976
0.7455	Intermediate Similarity	NPC309845
0.7455	Intermediate Similarity	NPC100079
0.7455	Intermediate Similarity	NPC471304
0.7455	Intermediate Similarity	NPC167860
0.7454	Intermediate Similarity	NPC472063
0.7454	Intermediate Similarity	NPC472069
0.7454	Intermediate Similarity	NPC472062
0.7447	Intermediate Similarity	NPC148889
0.7442	Intermediate Similarity	NPC234197
0.7437	Intermediate Similarity	NPC161801
0.7434	Intermediate Similarity	NPC280799
0.7422	Intermediate Similarity	NPC46451
0.7397	Intermediate Similarity	NPC135549
0.7389	Intermediate Similarity	NPC472099
0.7387	Intermediate Similarity	NPC474428
0.7383	Intermediate Similarity	NPC224928
0.7376	Intermediate Similarity	NPC188420
0.7368	Intermediate Similarity	NPC65277
0.7366	Intermediate Similarity	NPC274982
0.7361	Intermediate Similarity	NPC477019
0.7357	Intermediate Similarity	NPC60621
0.7354	Intermediate Similarity	NPC162530
0.7352	Intermediate Similarity	NPC45190
0.7352	Intermediate Similarity	NPC300156
0.7348	Intermediate Similarity	NPC157931
0.7325	Intermediate Similarity	NPC118121
0.7325	Intermediate Similarity	NPC122463
0.7318	Intermediate Similarity	NPC4687
0.7318	Intermediate Similarity	NPC249583
0.7316	Intermediate Similarity	NPC471762
0.7315	Intermediate Similarity	NPC123395
0.7309	Intermediate Similarity	NPC308137
0.7309	Intermediate Similarity	NPC310211
0.7308	Intermediate Similarity	NPC39370
0.7306	Intermediate Similarity	NPC289086
0.7303	Intermediate Similarity	NPC134637
0.7302	Intermediate Similarity	NPC90229
0.7301	Intermediate Similarity	NPC46561
0.7301	Intermediate Similarity	NPC96321
0.73	Intermediate Similarity	NPC477066
0.7299	Intermediate Similarity	NPC255909
0.7296	Intermediate Similarity	NPC207686
0.7294	Intermediate Similarity	NPC295898
0.7293	Intermediate Similarity	NPC94842
0.7289	Intermediate Similarity	NPC148183
0.7289	Intermediate Similarity	NPC152768
0.7285	Intermediate Similarity	NPC287208
0.7281	Intermediate Similarity	NPC176538
0.7277	Intermediate Similarity	NPC280964
0.7277	Intermediate Similarity	NPC114335
0.7277	Intermediate Similarity	NPC141915
0.7277	Intermediate Similarity	NPC149471
0.7277	Intermediate Similarity	NPC271215
0.7269	Intermediate Similarity	NPC478082
0.7269	Intermediate Similarity	NPC213530
0.7269	Intermediate Similarity	NPC193267
0.7269	Intermediate Similarity	NPC478081
0.7269	Intermediate Similarity	NPC477067
0.7269	Intermediate Similarity	NPC34837
0.7257	Intermediate Similarity	NPC169402
0.7257	Intermediate Similarity	NPC473513
0.7256	Intermediate Similarity	NPC194967
0.7252	Intermediate Similarity	NPC472070
0.7251	Intermediate Similarity	NPC206186
0.7249	Intermediate Similarity	NPC144452
0.7248	Intermediate Similarity	NPC232727
0.7244	Intermediate Similarity	NPC116238
0.7244	Intermediate Similarity	NPC16066
0.7243	Intermediate Similarity	NPC329541
0.7237	Intermediate Similarity	NPC225279
0.7237	Intermediate Similarity	NPC323969
0.7237	Intermediate Similarity	NPC469439
0.7236	Intermediate Similarity	NPC26850
0.7233	Intermediate Similarity	NPC84347
0.7227	Intermediate Similarity	NPC264166
0.7227	Intermediate Similarity	NPC165349
0.7227	Intermediate Similarity	NPC329708
0.7227	Intermediate Similarity	NPC274291
0.7227	Intermediate Similarity	NPC47059
0.7227	Intermediate Similarity	NPC118832
0.7225	Intermediate Similarity	NPC173080
0.7225	Intermediate Similarity	NPC473041
0.7222	Intermediate Similarity	NPC196718
0.7222	Intermediate Similarity	NPC473186
0.722	Intermediate Similarity	NPC17437
0.722	Intermediate Similarity	NPC269367
0.7217	Intermediate Similarity	NPC103119
0.7214	Intermediate Similarity	NPC177404
0.7205	Intermediate Similarity	NPC198503
0.7203	Intermediate Similarity	NPC477549
0.7202	Intermediate Similarity	NPC315957
0.72	Intermediate Similarity	NPC324361
0.72	Intermediate Similarity	NPC39500
0.7196	Intermediate Similarity	NPC216550
0.7195	Intermediate Similarity	NPC175602
0.7193	Intermediate Similarity	NPC208084
0.7188	Intermediate Similarity	NPC146418
0.7188	Intermediate Similarity	NPC87413
0.7188	Intermediate Similarity	NPC187501
0.7186	Intermediate Similarity	NPC473449

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 NPC322482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	664
0.2-0.3	888
0.3-0.4	1456
0.4-0.5	2625
0.5-0.6	2171
0.6-0.7	889
0.7-0.8	73
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
0.7982	Intermediate Similarity	NPD6790	Phase 1
0.7936	Intermediate Similarity	NPD4429	Discontinued
0.787	Intermediate Similarity	NPD7069	Discontinued
0.7864	Intermediate Similarity	NPD6242	Discontinued
0.7745	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3816	Phase 1
0.7706	Intermediate Similarity	NPD3815	Phase 1
0.7699	Intermediate Similarity	NPD8091	Phase 3
0.765	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD5488	Discontinued
0.7611	Intermediate Similarity	NPD7426	Phase 1
0.7608	Intermediate Similarity	NPD3923	Approved
0.7608	Intermediate Similarity	NPD3922	Approved
0.7608	Intermediate Similarity	NPD3921	Approved
0.7608	Intermediate Similarity	NPD3924	Approved
0.7595	Intermediate Similarity	NPD5482	Discontinued
0.7588	Intermediate Similarity	NPD5022	Discontinued
0.7565	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6568	Discontinued
0.75	Intermediate Similarity	NPD5513	Phase 2
0.75	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7395	Discontinued
0.7435	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD3763	Approved
0.7406	Intermediate Similarity	NPD4558	Phase 2
0.7359	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6569	Phase 2
0.7352	Intermediate Similarity	NPD7010	Phase 3
0.7352	Intermediate Similarity	NPD5530	Phase 1
0.735	Intermediate Similarity	NPD5891	Approved
0.7347	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5883	Phase 2
0.7333	Intermediate Similarity	NPD4989	Phase 2
0.7333	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4795	Phase 2
0.7294	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7467	Discontinued
0.7284	Intermediate Similarity	NPD4952	Phase 3
0.7281	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3259	Approved
0.7273	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7886	Phase 2
0.7257	Intermediate Similarity	NPD7885	Phase 2
0.725	Intermediate Similarity	NPD8100	Phase 3
0.7246	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7924	Phase 2
0.724	Intermediate Similarity	NPD7925	Phase 2
0.724	Intermediate Similarity	NPD5429	Discontinued
0.7238	Intermediate Similarity	NPD4889	Approved
0.7237	Intermediate Similarity	NPD8479	Phase 2
0.7229	Intermediate Similarity	NPD5450	Discontinued
0.7227	Intermediate Similarity	NPD4035	Approved
0.7227	Intermediate Similarity	NPD32	Approved
0.7227	Intermediate Similarity	NPD31	Approved
0.7227	Intermediate Similarity	NPD4033	Approved
0.7227	Intermediate Similarity	NPD4122	Approved
0.7227	Intermediate Similarity	NPD4034	Approved
0.7227	Intermediate Similarity	NPD4039	Approved
0.7227	Intermediate Similarity	NPD4038	Approved
0.7227	Intermediate Similarity	NPD4037	Approved
0.7227	Intermediate Similarity	NPD4036	Approved
0.722	Intermediate Similarity	NPD8358	Approved
0.7213	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3394	Approved
0.7212	Intermediate Similarity	NPD3389	Approved
0.7212	Intermediate Similarity	NPD3393	Approved
0.7205	Intermediate Similarity	NPD4923	Phase 1
0.7202	Intermediate Similarity	NPD1739	Approved
0.7202	Intermediate Similarity	NPD1740	Approved
0.7191	Intermediate Similarity	NPD4373	Phase 2
0.7176	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3477	Phase 2
0.7171	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3920	Phase 2
0.7162	Intermediate Similarity	NPD5850	Phase 3
0.716	Intermediate Similarity	NPD8101	Phase 3
0.716	Intermediate Similarity	NPD3809	Discontinued
0.7155	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7675	Phase 3
0.7155	Intermediate Similarity	NPD7674	Phase 3
0.7149	Intermediate Similarity	NPD3354	Phase 2
0.7149	Intermediate Similarity	NPD5632	Approved
0.7137	Intermediate Similarity	NPD6531	Approved
0.7137	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD6230	Discontinued
0.7137	Intermediate Similarity	NPD6530	Approved
0.7137	Intermediate Similarity	NPD5479	Discontinued
0.7131	Intermediate Similarity	NPD7673	Phase 3
0.713	Intermediate Similarity	NPD5147	Discontinued
0.713	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1483	Discontinued
0.7123	Intermediate Similarity	NPD4375	Approved
0.7119	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4369	Phase 2
0.7118	Intermediate Similarity	NPD7404	Approved
0.7116	Intermediate Similarity	NPD4372	Phase 1
0.7111	Intermediate Similarity	NPD5475	Discontinued
0.7093	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3257	Approved
0.7093	Intermediate Similarity	NPD5293	Phase 2
0.7089	Intermediate Similarity	NPD2757	Phase 2
0.7083	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7417	Discontinued
0.7083	Intermediate Similarity	NPD1038	Approved
0.708	Intermediate Similarity	NPD5866	Approved
0.7078	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6968	Phase 2
0.7064	Intermediate Similarity	NPD6969	Phase 2
0.7062	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3006	Discontinued
0.7054	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3795	Approved
0.7048	Intermediate Similarity	NPD3794	Approved
0.7046	Intermediate Similarity	NPD6494	Phase 2
0.7043	Intermediate Similarity	NPD3217	Phase 2
0.7039	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6281	Approved
0.7022	Intermediate Similarity	NPD4437	Phase 3
0.7017	Intermediate Similarity	NPD6963	Approved
0.7017	Intermediate Similarity	NPD2951	Discontinued
0.7017	Intermediate Similarity	NPD6964	Approved
0.7016	Intermediate Similarity	NPD6961	Discontinued
0.7014	Intermediate Similarity	NPD3386	Phase 2
0.7013	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8289	Discontinued
0.7004	Intermediate Similarity	NPD4885	Approved
0.7	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD3947	Discontinued
0.699	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6716	Phase 1
0.6979	Remote Similarity	NPD4845	Discontinued
0.6978	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5529	Phase 1
0.6974	Remote Similarity	NPD3945	Discontinued
0.6972	Remote Similarity	NPD4418	Discontinued
0.6971	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8016	Phase 3
0.697	Remote Similarity	NPD3258	Approved
0.697	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD6709	Phase 3
0.6964	Remote Similarity	NPD5601	Phase 2
0.696	Remote Similarity	NPD5416	Discontinued
0.696	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7803	Approved
0.6953	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1856	Discontinued
0.6953	Remote Similarity	NPD6209	Approved
0.6952	Remote Similarity	NPD7176	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4044	Discontinued
0.6949	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7555	Discontinued
0.6941	Remote Similarity	NPD5512	Phase 3
0.6939	Remote Similarity	NPD6276	Discontinued
0.6933	Remote Similarity	NPD7222	Phase 2
0.6932	Remote Similarity	NPD7708	Approved
0.6932	Remote Similarity	NPD6228	Discontinued
0.693	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4551	Phase 2
0.6923	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.692	Remote Similarity	NPD1659	Phase 1
0.6917	Remote Similarity	NPD5469	Phase 3
0.6914	Remote Similarity	NPD7408	Phase 2
0.6914	Remote Similarity	NPD5459	Phase 2
0.6912	Remote Similarity	NPD2334	Discontinued
0.6911	Remote Similarity	NPD8102	Discontinued
0.6907	Remote Similarity	NPD7994	Phase 2
0.6903	Remote Similarity	NPD2509	Approved
0.6903	Remote Similarity	NPD2510	Approved
0.6903	Remote Similarity	NPD5658	Approved
0.6903	Remote Similarity	NPD2916	Discontinued
0.69	Remote Similarity	NPD5945	Phase 1
0.69	Remote Similarity	NPD5944	Phase 1
0.6895	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3925	Approved
0.6892	Remote Similarity	NPD7956	Approved
0.6892	Remote Similarity	NPD7955	Approved
0.6889	Remote Similarity	NPD3507	Phase 2
0.6884	Remote Similarity	NPD4921	Phase 3
0.6884	Remote Similarity	NPD4919	Phase 3
0.6884	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8463	Approved
0.6866	Remote Similarity	NPD4081	Clinical (unspecified phase)

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