NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	594.4
Volume:	632.636
LogP:	4.089
LogD:	3.1
LogS:	-4.707
# Rotatable Bonds:	8
TPSA:	102.26
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	5.862
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
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:	-5.433
MDCK Permeability:	5.761913143942365e-06
Pgp-inhibitor:	0.044
Pgp-substrate:	0.775
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.701
Plasma Protein Binding (PPB):	69.24617004394531%
Volume Distribution (VD):	2.073
Pgp-substrate:	19.225961685180664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.413
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.983
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	9.498
Half-life (T1/2):	0.305

ADMET: Toxicity

hERG Blockers:	0.892
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.667
Skin Sensitization:	0.821
Carcinogencity:	0.584
Eye Corrosion:	0.003
Eye Irritation:	0.009
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: NPC476751

Natural Product ID:	NPC476751
*Common Name:**	buxmicrophylline G
IUPAC Name:	(E)-N-[(1S,3R,6S,7S,11S,12S,14R,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide
Synonyms:	Buxmicrophylline G
Standard InCHIKey:	PGSGUFFVLOKDAE-DQDJTOMWSA-N
Standard InCHI:	InChI=1S/C36H54N2O5/c1-22(38(5)6)31-25(41)19-34(4)28-12-11-27-32(2,21-39)29(14-15-35(27)20-36(28,35)17-16-33(31,34)3)37-30(42)13-9-23-8-10-26(43-7)24(40)18-23/h8-10,13,18,22,25,27-29,31,39-41H,11-12,14-17,19-21H2,1-7H3,(H,37,42)/b13-9+/t22-,25+,27?,28-,29-,31-,32-,33+,34-,35+,36-/m0/s1
SMILES:	C[C@@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CC[C@]34[C@H]2CCC5[C@]3(C4)CC[C@@H]([C@@]5(C)CO)NC(=O)/C=C/C6=CC(=C(C=C6)OC)O)C)C)O)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45267062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	leaves and stems	Kunming, Yunnan, China	2007-AUG	PMID[19133780]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24301	Buxus microphylla	Species	Buxaceae	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
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	890	nM	PMID[19133780]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	4440	nM	PMID[19133780]

☑ 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 NPC476751 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	315
0.1-0.2	1348
0.2-0.3	3721
0.3-0.4	10189
0.4-0.5	12088
0.5-0.6	11911
0.6-0.7	2985
0.7-0.8	139
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7898	Intermediate Similarity	NPC321502
0.7892	Intermediate Similarity	NPC273358
0.7892	Intermediate Similarity	NPC298647
0.7831	Intermediate Similarity	NPC32017
0.7831	Intermediate Similarity	NPC96930
0.7805	Intermediate Similarity	NPC5462
0.7797	Intermediate Similarity	NPC329969
0.7784	Intermediate Similarity	NPC292206
0.7759	Intermediate Similarity	NPC90984
0.7758	Intermediate Similarity	NPC19862
0.7758	Intermediate Similarity	NPC235195
0.773	Intermediate Similarity	NPC222039
0.773	Intermediate Similarity	NPC100478
0.7722	Intermediate Similarity	NPC305847
0.7702	Intermediate Similarity	NPC204848
0.7702	Intermediate Similarity	NPC14600
0.7702	Intermediate Similarity	NPC312770
0.7702	Intermediate Similarity	NPC160607
0.7702	Intermediate Similarity	NPC41473
0.768	Intermediate Similarity	NPC302449
0.7651	Intermediate Similarity	NPC271607
0.7651	Intermediate Similarity	NPC280717
0.761	Intermediate Similarity	NPC214869
0.7602	Intermediate Similarity	NPC107602
0.7595	Intermediate Similarity	NPC195749
0.7595	Intermediate Similarity	NPC35961
0.7595	Intermediate Similarity	NPC52029
0.758	Intermediate Similarity	NPC186898
0.7562	Intermediate Similarity	NPC132847
0.756	Intermediate Similarity	NPC470935
0.756	Intermediate Similarity	NPC471032
0.7558	Intermediate Similarity	NPC147091
0.7557	Intermediate Similarity	NPC124657
0.7547	Intermediate Similarity	NPC114102
0.7546	Intermediate Similarity	NPC299583
0.7532	Intermediate Similarity	NPC155838
0.7529	Intermediate Similarity	NPC27410
0.7529	Intermediate Similarity	NPC52475
0.7529	Intermediate Similarity	NPC145527
0.7529	Intermediate Similarity	NPC205167
0.7529	Intermediate Similarity	NPC208785
0.7529	Intermediate Similarity	NPC127402
0.7529	Intermediate Similarity	NPC166014
0.7529	Intermediate Similarity	NPC470618
0.7529	Intermediate Similarity	NPC470619
0.7514	Intermediate Similarity	NPC210140
0.7485	Intermediate Similarity	NPC18614
0.7472	Intermediate Similarity	NPC66573
0.7468	Intermediate Similarity	NPC153990
0.7468	Intermediate Similarity	NPC251571
0.7453	Intermediate Similarity	NPC325568
0.7443	Intermediate Similarity	NPC324144
0.7429	Intermediate Similarity	NPC226428
0.7429	Intermediate Similarity	NPC249274
0.7421	Intermediate Similarity	NPC277458
0.7421	Intermediate Similarity	NPC307050
0.7416	Intermediate Similarity	NPC306555
0.7416	Intermediate Similarity	NPC474931
0.7416	Intermediate Similarity	NPC117188
0.7416	Intermediate Similarity	NPC205421
0.7416	Intermediate Similarity	NPC81218
0.7416	Intermediate Similarity	NPC12053
0.7416	Intermediate Similarity	NPC158376
0.7416	Intermediate Similarity	NPC145832
0.7401	Intermediate Similarity	NPC136508
0.7401	Intermediate Similarity	NPC253043
0.7401	Intermediate Similarity	NPC134858
0.7401	Intermediate Similarity	NPC477563
0.7401	Intermediate Similarity	NPC78222
0.7401	Intermediate Similarity	NPC212794
0.7401	Intermediate Similarity	NPC255607
0.7401	Intermediate Similarity	NPC13504
0.7401	Intermediate Similarity	NPC306843
0.7401	Intermediate Similarity	NPC96603
0.7401	Intermediate Similarity	NPC3375
0.7401	Intermediate Similarity	NPC196447
0.7399	Intermediate Similarity	NPC205392
0.7399	Intermediate Similarity	NPC105942
0.7394	Intermediate Similarity	NPC477838
0.7394	Intermediate Similarity	NPC477837
0.7384	Intermediate Similarity	NPC275027
0.7384	Intermediate Similarity	NPC26601
0.7381	Intermediate Similarity	NPC327623
0.7378	Intermediate Similarity	NPC193528
0.7377	Intermediate Similarity	NPC99179
0.7371	Intermediate Similarity	NPC476750
0.736	Intermediate Similarity	NPC42549
0.736	Intermediate Similarity	NPC256012
0.736	Intermediate Similarity	NPC268503
0.736	Intermediate Similarity	NPC250846
0.736	Intermediate Similarity	NPC317272
0.736	Intermediate Similarity	NPC240841
0.736	Intermediate Similarity	NPC476749
0.7356	Intermediate Similarity	NPC186063
0.7353	Intermediate Similarity	NPC24233
0.7353	Intermediate Similarity	NPC135538
0.7353	Intermediate Similarity	NPC476571
0.7353	Intermediate Similarity	NPC428
0.7353	Intermediate Similarity	NPC246587
0.7353	Intermediate Similarity	NPC147390
0.7345	Intermediate Similarity	NPC233650
0.7342	Intermediate Similarity	NPC29008
0.7342	Intermediate Similarity	NPC266705
0.7342	Intermediate Similarity	NPC228771
0.7337	Intermediate Similarity	NPC307205
0.733	Intermediate Similarity	NPC475780
0.7321	Intermediate Similarity	NPC252133
0.731	Intermediate Similarity	NPC103379
0.731	Intermediate Similarity	NPC477565
0.7303	Intermediate Similarity	NPC470936
0.7301	Intermediate Similarity	NPC227719
0.7301	Intermediate Similarity	NPC218530
0.7299	Intermediate Similarity	NPC295691
0.7299	Intermediate Similarity	NPC189266
0.7299	Intermediate Similarity	NPC204828
0.7299	Intermediate Similarity	NPC278799
0.7299	Intermediate Similarity	NPC193949
0.7299	Intermediate Similarity	NPC469817
0.7299	Intermediate Similarity	NPC172765
0.7299	Intermediate Similarity	NPC249797
0.7299	Intermediate Similarity	NPC207757
0.7299	Intermediate Similarity	NPC184026
0.7299	Intermediate Similarity	NPC110416
0.7299	Intermediate Similarity	NPC2413
0.7299	Intermediate Similarity	NPC276588
0.7299	Intermediate Similarity	NPC54379
0.7299	Intermediate Similarity	NPC5238
0.7299	Intermediate Similarity	NPC127674
0.7299	Intermediate Similarity	NPC39701
0.7297	Intermediate Similarity	NPC229234
0.7296	Intermediate Similarity	NPC301713
0.7294	Intermediate Similarity	NPC191376
0.7294	Intermediate Similarity	NPC115144
0.7294	Intermediate Similarity	NPC179825
0.7294	Intermediate Similarity	NPC321505
0.7294	Intermediate Similarity	NPC277857
0.7293	Intermediate Similarity	NPC476331
0.7293	Intermediate Similarity	NPC231371
0.7288	Intermediate Similarity	NPC179250
0.7288	Intermediate Similarity	NPC50380
0.7283	Intermediate Similarity	NPC133011
0.7283	Intermediate Similarity	NPC82285
0.7277	Intermediate Similarity	NPC234318
0.7273	Intermediate Similarity	NPC68292
0.7267	Intermediate Similarity	NPC220858
0.7267	Intermediate Similarity	NPC192768
0.7267	Intermediate Similarity	NPC88249
0.7267	Intermediate Similarity	NPC97221
0.7267	Intermediate Similarity	NPC151895
0.7263	Intermediate Similarity	NPC35627
0.7263	Intermediate Similarity	NPC81247
0.7263	Intermediate Similarity	NPC476573
0.7262	Intermediate Similarity	NPC35212
0.7261	Intermediate Similarity	NPC321402
0.7256	Intermediate Similarity	NPC471942
0.7247	Intermediate Similarity	NPC1229
0.7243	Intermediate Similarity	NPC298339
0.7239	Intermediate Similarity	NPC6854
0.7239	Intermediate Similarity	NPC285078
0.7239	Intermediate Similarity	NPC313737
0.7233	Intermediate Similarity	NPC9067
0.7232	Intermediate Similarity	NPC4304
0.7229	Intermediate Similarity	NPC296898
0.7228	Intermediate Similarity	NPC118633
0.7228	Intermediate Similarity	NPC294790
0.7228	Intermediate Similarity	NPC320223
0.7228	Intermediate Similarity	NPC114364
0.7228	Intermediate Similarity	NPC148693
0.7222	Intermediate Similarity	NPC150879
0.7222	Intermediate Similarity	NPC298979
0.7219	Intermediate Similarity	NPC310621
0.7213	Intermediate Similarity	NPC229166
0.7213	Intermediate Similarity	NPC199465
0.7213	Intermediate Similarity	NPC128560
0.7212	Intermediate Similarity	NPC252343
0.7212	Intermediate Similarity	NPC167944
0.7212	Intermediate Similarity	NPC231884
0.7212	Intermediate Similarity	NPC42793
0.7207	Intermediate Similarity	NPC169743
0.7205	Intermediate Similarity	NPC201069
0.7202	Intermediate Similarity	NPC473612
0.7202	Intermediate Similarity	NPC470372
0.7198	Intermediate Similarity	NPC239775
0.7198	Intermediate Similarity	NPC286809
0.7193	Intermediate Similarity	NPC476151
0.7191	Intermediate Similarity	NPC60186
0.7186	Intermediate Similarity	NPC132723
0.7186	Intermediate Similarity	NPC76032
0.7184	Intermediate Similarity	NPC475311
0.7184	Intermediate Similarity	NPC118033
0.7184	Intermediate Similarity	NPC473680
0.7184	Intermediate Similarity	NPC473579
0.7184	Intermediate Similarity	NPC475454
0.7182	Intermediate Similarity	NPC470324
0.7181	Intermediate Similarity	NPC124626
0.7178	Intermediate Similarity	NPC93882
0.7178	Intermediate Similarity	NPC130595
0.7176	Intermediate Similarity	NPC26045
0.7176	Intermediate Similarity	NPC208994
0.7176	Intermediate Similarity	NPC185838

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 NPC476751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	634
0.2-0.3	955
0.3-0.4	2527
0.4-0.5	2863
0.5-0.6	1568
0.6-0.7	371
0.7-0.8	54
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
0.7941	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7833	Phase 2
0.7941	Intermediate Similarity	NPD7831	Phase 2
0.7898	Intermediate Similarity	NPD3620	Phase 2
0.7898	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD2489	Approved
0.7874	Intermediate Similarity	NPD27	Approved
0.7759	Intermediate Similarity	NPD3051	Approved
0.7722	Intermediate Similarity	NPD7313	Approved
0.7722	Intermediate Similarity	NPD7311	Approved
0.7722	Intermediate Similarity	NPD7312	Approved
0.7722	Intermediate Similarity	NPD7310	Approved
0.7714	Intermediate Similarity	NPD2969	Approved
0.7714	Intermediate Similarity	NPD2970	Approved
0.768	Intermediate Similarity	NPD7309	Approved
0.7636	Intermediate Similarity	NPD5241	Discontinued
0.7624	Intermediate Similarity	NPD4578	Approved
0.7624	Intermediate Similarity	NPD4577	Approved
0.7602	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7906	Approved
0.753	Intermediate Similarity	NPD8131	Suspended
0.75	Intermediate Similarity	NPD4663	Approved
0.747	Intermediate Similarity	NPD6331	Phase 2
0.7456	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD52	Approved
0.7456	Intermediate Similarity	NPD7526	Approved
0.7453	Intermediate Similarity	NPD3110	Approved
0.7453	Intermediate Similarity	NPD3109	Approved
0.7396	Intermediate Similarity	NPD3645	Discontinued
0.7356	Intermediate Similarity	NPD5773	Approved
0.7356	Intermediate Similarity	NPD5772	Approved
0.7305	Intermediate Similarity	NPD4237	Approved
0.7305	Intermediate Similarity	NPD4236	Phase 3
0.7301	Intermediate Similarity	NPD3657	Discovery
0.7287	Intermediate Similarity	NPD2490	Approved
0.7287	Intermediate Similarity	NPD2488	Approved
0.7262	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2161	Phase 2
0.7219	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6896	Approved
0.7212	Intermediate Similarity	NPD6895	Approved
0.7205	Intermediate Similarity	NPD2606	Approved
0.7205	Intermediate Similarity	NPD2605	Approved
0.72	Intermediate Similarity	NPD5722	Discontinued
0.7195	Intermediate Similarity	NPD5735	Approved
0.7182	Intermediate Similarity	NPD4481	Phase 3
0.7182	Intermediate Similarity	NPD2898	Approved
0.7181	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2674	Phase 3
0.716	Intermediate Similarity	NPD5156	Approved
0.716	Intermediate Similarity	NPD5155	Approved
0.7159	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7037	Approved
0.7117	Intermediate Similarity	NPD3145	Approved
0.7117	Intermediate Similarity	NPD3144	Approved
0.711	Intermediate Similarity	NPD2122	Discontinued
0.711	Intermediate Similarity	NPD4727	Phase 1
0.711	Intermediate Similarity	NPD5699	Approved
0.7107	Intermediate Similarity	NPD4583	Approved
0.7107	Intermediate Similarity	NPD4582	Approved
0.7107	Intermediate Similarity	NPD4040	Phase 1
0.7101	Intermediate Similarity	NPD3638	Discontinued
0.7099	Intermediate Similarity	NPD3594	Approved
0.7099	Intermediate Similarity	NPD3595	Approved
0.7056	Intermediate Similarity	NPD7497	Discontinued
0.7056	Intermediate Similarity	NPD4002	Approved
0.7056	Intermediate Similarity	NPD4004	Approved
0.7055	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2157	Approved
0.7045	Intermediate Similarity	NPD6072	Discontinued
0.7045	Intermediate Similarity	NPD4773	Phase 2
0.7045	Intermediate Similarity	NPD4772	Phase 2
0.7044	Intermediate Similarity	NPD2232	Approved
0.7044	Intermediate Similarity	NPD2233	Approved
0.7044	Intermediate Similarity	NPD2230	Approved
0.7039	Intermediate Similarity	NPD8070	Approved
0.7039	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3636	Approved
0.7037	Intermediate Similarity	NPD3635	Approved
0.7037	Intermediate Similarity	NPD3637	Approved
0.703	Intermediate Similarity	NPD2238	Phase 2
0.7029	Intermediate Similarity	NPD4005	Discontinued
0.7021	Intermediate Similarity	NPD8053	Approved
0.7021	Intermediate Similarity	NPD8054	Approved
0.7012	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5177	Phase 3
0.7	Intermediate Similarity	NPD5327	Phase 3
0.7	Intermediate Similarity	NPD3060	Approved
0.6994	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3092	Approved
0.6981	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4624	Approved
0.6966	Remote Similarity	NPD2978	Approved
0.6966	Remote Similarity	NPD2977	Approved
0.6964	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2668	Approved
0.6962	Remote Similarity	NPD2667	Approved
0.6957	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2493	Approved
0.6954	Remote Similarity	NPD2494	Approved
0.6946	Remote Similarity	NPD6353	Approved
0.6943	Remote Similarity	NPD3091	Approved
0.6941	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2421	Approved
0.6936	Remote Similarity	NPD2420	Approved
0.6928	Remote Similarity	NPD4140	Approved
0.6927	Remote Similarity	NPD7047	Phase 3
0.6923	Remote Similarity	NPD8127	Discontinued
0.6914	Remote Similarity	NPD3094	Phase 2
0.6909	Remote Similarity	NPD5109	Approved
0.6909	Remote Similarity	NPD5110	Phase 2
0.6909	Remote Similarity	NPD5718	Phase 2
0.6909	Remote Similarity	NPD5111	Phase 2
0.6904	Remote Similarity	NPD4580	Approved
0.6901	Remote Similarity	NPD4162	Approved
0.6897	Remote Similarity	NPD4584	Approved
0.6897	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4123	Phase 3
0.6894	Remote Similarity	NPD1669	Approved
0.689	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6071	Discontinued
0.6879	Remote Similarity	NPD7124	Phase 2
0.6878	Remote Similarity	NPD2968	Approved
0.6878	Remote Similarity	NPD2971	Approved
0.6869	Remote Similarity	NPD3450	Approved
0.6869	Remote Similarity	NPD3452	Approved
0.6863	Remote Similarity	NPD7827	Phase 1
0.6854	Remote Similarity	NPD6677	Suspended
0.6845	Remote Similarity	NPD4097	Suspended
0.6845	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6063	Approved
0.6833	Remote Similarity	NPD2563	Approved
0.6833	Remote Similarity	NPD2560	Approved
0.6829	Remote Similarity	NPD1712	Approved
0.6826	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5714	Approved
0.6805	Remote Similarity	NPD6111	Discontinued
0.6793	Remote Similarity	NPD7315	Approved
0.679	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4725	Approved
0.6784	Remote Similarity	NPD4726	Approved
0.6784	Remote Similarity	NPD4721	Approved
0.6782	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6584	Phase 3
0.6766	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4108	Discontinued
0.6763	Remote Similarity	NPD4110	Phase 3
0.6763	Remote Similarity	NPD5754	Discontinued
0.6763	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7438	Suspended
0.6753	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD2974	Approved
0.6751	Remote Similarity	NPD2973	Approved
0.6751	Remote Similarity	NPD2975	Approved
0.675	Remote Similarity	NPD3095	Discontinued
0.6748	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3027	Phase 3
0.6744	Remote Similarity	NPD7153	Discontinued
0.6726	Remote Similarity	NPD6346	Approved
0.6722	Remote Similarity	NPD7298	Approved
0.6705	Remote Similarity	NPD6419	Discontinued
0.6705	Remote Similarity	NPD7020	Approved
0.6705	Remote Similarity	NPD7019	Approved
0.6705	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4739	Approved
0.6704	Remote Similarity	NPD4678	Approved
0.6704	Remote Similarity	NPD7028	Phase 2
0.6704	Remote Similarity	NPD4675	Approved
0.6704	Remote Similarity	NPD5713	Approved
0.6703	Remote Similarity	NPD4010	Discontinued
0.6702	Remote Similarity	NPD8156	Discontinued
0.6702	Remote Similarity	NPD6042	Phase 2
0.6702	Remote Similarity	NPD42	Phase 2
0.6687	Remote Similarity	NPD4093	Discontinued
0.6686	Remote Similarity	NPD5763	Approved
0.6686	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5762	Approved
0.6685	Remote Similarity	NPD4666	Phase 3
0.6667	Remote Similarity	NPD1753	Discontinued
0.6667	Remote Similarity	NPD7905	Discontinued
0.6667	Remote Similarity	NPD1423	Approved
0.6667	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2491	Approved
0.6667	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD8166	Discontinued
0.6651	Remote Similarity	NPD6997	Phase 2
0.6649	Remote Similarity	NPD8252	Approved
0.6649	Remote Similarity	NPD8251	Approved
0.6649	Remote Similarity	NPD8099	Discontinued
0.6649	Remote Similarity	NPD6620	Discovery
0.6649	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3167	Approved
0.6647	Remote Similarity	NPD3164	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