NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	464.28
Volume:	477.648
LogP:	3.611
LogD:	2.471
LogS:	-3.862
# Rotatable Bonds:	8
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.573
Synthetic Accessibility Score:	5.887
Fsp3:	0.885
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.591
MDCK Permeability:	1.1942782293772325e-05
Pgp-inhibitor:	0.752
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.805
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.309
Plasma Protein Binding (PPB):	64.20320129394531%
Volume Distribution (VD):	0.568
Pgp-substrate:	31.87211799621582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.488
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.331
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	1.874
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.2
AMES Toxicity:	0.136
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.51
Skin Sensitization:	0.084
Carcinogencity:	0.5
Eye Corrosion:	0.006
Eye Irritation:	0.069
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC477936

Natural Product ID:	NPC477936
*Common Name:**	(1S,4S,5R,9S,10R,13S,14S)-5-(acetyloxymethyl)-14-hydroxy-9-methyl-14-(2-methylpropanoyloxymethyl)tetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
IUPAC Name:	(1S,4S,5R,9S,10R,13S,14S)-5-(acetyloxymethyl)-14-hydroxy-9-methyl-14-(2-methylpropanoyloxymethyl)tetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
Synonyms:
Standard InCHIKey:	JRVDZOPVESPLJF-HWOBUYORSA-N
Standard InCHI:	InChI=1S/C26H40O7/c1-16(2)21(28)33-15-26(31)13-24-11-8-20-23(4,19(24)7-6-18(26)12-24)9-5-10-25(20,22(29)30)14-32-17(3)27/h16,18-20,31H,5-15H2,1-4H3,(H,29,30)/t18-,19-,20-,23-,24-,25-,26+/m0/s1
SMILES:	CC(C)C(=O)OC[C@@]1(C[C@@]23CC[C@H]4[C@]([C@@H]2CC[C@H]1C3)(CCC[C@@]4(COC(=O)C)C(=O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118708068
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	2

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	46.69	%	PMID[24997688]
NPT2	Others	Unspecified	IC50	>	10	ug/ml	PMID[24997688]
NPT2	Others	Unspecified	Inhibition	=	60.36	%	PMID[24997688]
NPT2	Others	Unspecified	IC50	=	6.82	ug/ml	PMID[24997688]

☑ 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 NPC477936 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	358
0.1-0.2	3009
0.2-0.3	10640
0.3-0.4	12585
0.4-0.5	6008
0.5-0.6	5721
0.6-0.7	3652
0.7-0.8	623
0.8-0.85	74
0.85-0.9	11
0.9-0.95	9
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC477935
0.9481	High Similarity	NPC472853
0.9221	High Similarity	NPC476732
0.9221	High Similarity	NPC199965
0.9125	High Similarity	NPC259173
0.9091	High Similarity	NPC477919
0.9091	High Similarity	NPC180199
0.9091	High Similarity	NPC477918
0.9079	High Similarity	NPC477934
0.8961	High Similarity	NPC477932
0.8961	High Similarity	NPC477933
0.8736	High Similarity	NPC206878
0.8701	High Similarity	NPC477930
0.8684	High Similarity	NPC469940
0.8608	High Similarity	NPC171658
0.8608	High Similarity	NPC474404
0.8571	High Similarity	NPC92139
0.8539	High Similarity	NPC116683
0.8462	Intermediate Similarity	NPC472854
0.8434	Intermediate Similarity	NPC292458
0.8434	Intermediate Similarity	NPC217559
0.8434	Intermediate Similarity	NPC268578
0.8415	Intermediate Similarity	NPC77311
0.8354	Intermediate Similarity	NPC24014
0.8354	Intermediate Similarity	NPC27349
0.8353	Intermediate Similarity	NPC474448
0.8333	Intermediate Similarity	NPC319909
0.8313	Intermediate Similarity	NPC164289
0.8313	Intermediate Similarity	NPC102156
0.8313	Intermediate Similarity	NPC148740
0.8313	Intermediate Similarity	NPC100366
0.8313	Intermediate Similarity	NPC242771
0.8313	Intermediate Similarity	NPC311642
0.8312	Intermediate Similarity	NPC477929
0.8256	Intermediate Similarity	NPC134197
0.8228	Intermediate Similarity	NPC472945
0.8228	Intermediate Similarity	NPC472944
0.8222	Intermediate Similarity	NPC215570
0.8214	Intermediate Similarity	NPC472744
0.8193	Intermediate Similarity	NPC12933
0.8182	Intermediate Similarity	NPC319671
0.8182	Intermediate Similarity	NPC252032
0.8182	Intermediate Similarity	NPC476734
0.8182	Intermediate Similarity	NPC469941
0.8171	Intermediate Similarity	NPC31302
0.8171	Intermediate Similarity	NPC245029
0.8148	Intermediate Similarity	NPC264602
0.814	Intermediate Similarity	NPC472272
0.814	Intermediate Similarity	NPC103782
0.814	Intermediate Similarity	NPC114378
0.8118	Intermediate Similarity	NPC471044
0.8118	Intermediate Similarity	NPC473336
0.8111	Intermediate Similarity	NPC470423
0.8095	Intermediate Similarity	NPC317066
0.8095	Intermediate Similarity	NPC13494
0.8072	Intermediate Similarity	NPC261616
0.8068	Intermediate Similarity	NPC24705
0.8068	Intermediate Similarity	NPC56962
0.8026	Intermediate Similarity	NPC42060
0.8026	Intermediate Similarity	NPC477931
0.8026	Intermediate Similarity	NPC268736
0.8025	Intermediate Similarity	NPC4209
0.8022	Intermediate Similarity	NPC470031
0.8	Intermediate Similarity	NPC476189
0.8	Intermediate Similarity	NPC280026
0.8	Intermediate Similarity	NPC472847
0.8	Intermediate Similarity	NPC167702
0.8	Intermediate Similarity	NPC228700
0.8	Intermediate Similarity	NPC15821
0.7976	Intermediate Similarity	NPC58631
0.7955	Intermediate Similarity	NPC56777
0.7955	Intermediate Similarity	NPC183374
0.7955	Intermediate Similarity	NPC201607
0.7955	Intermediate Similarity	NPC211162
0.7955	Intermediate Similarity	NPC255176
0.7955	Intermediate Similarity	NPC33398
0.7952	Intermediate Similarity	NPC80891
0.7952	Intermediate Similarity	NPC201276
0.7949	Intermediate Similarity	NPC64466
0.7949	Intermediate Similarity	NPC196197
0.7931	Intermediate Similarity	NPC472745
0.7927	Intermediate Similarity	NPC207010
0.7927	Intermediate Similarity	NPC317913
0.7927	Intermediate Similarity	NPC471151
0.7901	Intermediate Similarity	NPC472311
0.7901	Intermediate Similarity	NPC212733
0.7882	Intermediate Similarity	NPC61107
0.7882	Intermediate Similarity	NPC289486
0.7882	Intermediate Similarity	NPC121121
0.7875	Intermediate Similarity	NPC310766
0.7865	Intermediate Similarity	NPC215029
0.7865	Intermediate Similarity	NPC476733
0.7857	Intermediate Similarity	NPC470609
0.7848	Intermediate Similarity	NPC108131
0.7848	Intermediate Similarity	NPC477850
0.7841	Intermediate Similarity	NPC252714
0.7831	Intermediate Similarity	NPC34046
0.7831	Intermediate Similarity	NPC185465
0.7831	Intermediate Similarity	NPC80089
0.7831	Intermediate Similarity	NPC171426
0.7831	Intermediate Similarity	NPC471045
0.7831	Intermediate Similarity	NPC224802
0.7831	Intermediate Similarity	NPC329117
0.7831	Intermediate Similarity	NPC324700
0.7826	Intermediate Similarity	NPC205173
0.7816	Intermediate Similarity	NPC266651
0.7789	Intermediate Similarity	NPC178853
0.7765	Intermediate Similarity	NPC190940
0.7753	Intermediate Similarity	NPC229407
0.7753	Intermediate Similarity	NPC48824
0.7753	Intermediate Similarity	NPC254572
0.7753	Intermediate Similarity	NPC250687
0.775	Intermediate Similarity	NPC478227
0.775	Intermediate Similarity	NPC473267
0.775	Intermediate Similarity	NPC197701
0.7738	Intermediate Similarity	NPC472310
0.7738	Intermediate Similarity	NPC320144
0.7738	Intermediate Similarity	NPC476176
0.7738	Intermediate Similarity	NPC52951
0.7727	Intermediate Similarity	NPC472505
0.7727	Intermediate Similarity	NPC302111
0.7727	Intermediate Similarity	NPC80590
0.7727	Intermediate Similarity	NPC80700
0.7722	Intermediate Similarity	NPC324607
0.7722	Intermediate Similarity	NPC321732
0.7722	Intermediate Similarity	NPC474962
0.7711	Intermediate Similarity	NPC143133
0.7711	Intermediate Similarity	NPC298168
0.7708	Intermediate Similarity	NPC470172
0.7692	Intermediate Similarity	NPC474221
0.7692	Intermediate Similarity	NPC130459
0.7692	Intermediate Similarity	NPC478180
0.7692	Intermediate Similarity	NPC471901
0.7684	Intermediate Similarity	NPC108371
0.7683	Intermediate Similarity	NPC179858
0.7674	Intermediate Similarity	NPC202688
0.7674	Intermediate Similarity	NPC477286
0.7674	Intermediate Similarity	NPC60018
0.7674	Intermediate Similarity	NPC154043
0.7674	Intermediate Similarity	NPC328007
0.7674	Intermediate Similarity	NPC286719
0.7667	Intermediate Similarity	NPC24772
0.7667	Intermediate Similarity	NPC116146
0.7667	Intermediate Similarity	NPC269267
0.7662	Intermediate Similarity	NPC190827
0.7662	Intermediate Similarity	NPC243469
0.7662	Intermediate Similarity	NPC475943
0.766	Intermediate Similarity	NPC471241
0.764	Intermediate Similarity	NPC263802
0.764	Intermediate Similarity	NPC202937
0.7629	Intermediate Similarity	NPC471253
0.7629	Intermediate Similarity	NPC473406
0.7625	Intermediate Similarity	NPC476731
0.7614	Intermediate Similarity	NPC131350
0.7614	Intermediate Similarity	NPC201655
0.7609	Intermediate Similarity	NPC287118
0.7609	Intermediate Similarity	NPC472232
0.7609	Intermediate Similarity	NPC472237
0.7609	Intermediate Similarity	NPC471902
0.7609	Intermediate Similarity	NPC472231
0.7609	Intermediate Similarity	NPC473690
0.7609	Intermediate Similarity	NPC472238
0.7595	Intermediate Similarity	NPC473225
0.759	Intermediate Similarity	NPC471046
0.759	Intermediate Similarity	NPC470145
0.7586	Intermediate Similarity	NPC477285
0.7586	Intermediate Similarity	NPC327451
0.7586	Intermediate Similarity	NPC245866
0.7586	Intermediate Similarity	NPC111582
0.7586	Intermediate Similarity	NPC471037
0.7582	Intermediate Similarity	NPC77756
0.7558	Intermediate Similarity	NPC472230
0.7558	Intermediate Similarity	NPC472229
0.7556	Intermediate Similarity	NPC476379
0.7556	Intermediate Similarity	NPC471221
0.7551	Intermediate Similarity	NPC100078
0.7531	Intermediate Similarity	NPC58057
0.7531	Intermediate Similarity	NPC156277
0.7531	Intermediate Similarity	NPC320549
0.7531	Intermediate Similarity	NPC472309
0.7531	Intermediate Similarity	NPC151018
0.7528	Intermediate Similarity	NPC155531
0.7528	Intermediate Similarity	NPC476727
0.7528	Intermediate Similarity	NPC215968
0.7528	Intermediate Similarity	NPC477283
0.7528	Intermediate Similarity	NPC476726
0.7527	Intermediate Similarity	NPC477495
0.7527	Intermediate Similarity	NPC247877
0.7527	Intermediate Similarity	NPC470424
0.7527	Intermediate Similarity	NPC309127
0.7526	Intermediate Similarity	NPC473928
0.7526	Intermediate Similarity	NPC244969
0.7526	Intermediate Similarity	NPC213528
0.7525	Intermediate Similarity	NPC106760
0.75	Intermediate Similarity	NPC52756
0.75	Intermediate Similarity	NPC477434
0.75	Intermediate Similarity	NPC66105
0.75	Intermediate Similarity	NPC473066
0.75	Intermediate Similarity	NPC471747
0.75	Intermediate Similarity	NPC263974

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 NPC477936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	3304
0.2-0.3	3603
0.3-0.4	1110
0.4-0.5	333
0.5-0.6	246
0.6-0.7	142
0.7-0.8	25
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD3702	Approved
0.8205	Intermediate Similarity	NPD5777	Approved
0.8025	Intermediate Similarity	NPD6117	Approved
0.8	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6081	Approved
0.7927	Intermediate Similarity	NPD6116	Phase 1
0.7848	Intermediate Similarity	NPD4245	Approved
0.7848	Intermediate Similarity	NPD4244	Approved
0.7831	Intermediate Similarity	NPD6697	Approved
0.7831	Intermediate Similarity	NPD6118	Approved
0.7831	Intermediate Similarity	NPD6115	Approved
0.7831	Intermediate Similarity	NPD6114	Approved
0.7792	Intermediate Similarity	NPD4224	Phase 2
0.7722	Intermediate Similarity	NPD3698	Phase 2
0.7625	Intermediate Similarity	NPD4789	Approved
0.7595	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5360	Phase 3
0.7531	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6083	Phase 2
0.7292	Intermediate Similarity	NPD6084	Phase 2
0.7284	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4788	Approved
0.7128	Intermediate Similarity	NPD8035	Phase 2
0.7128	Intermediate Similarity	NPD8034	Phase 2
0.7108	Intermediate Similarity	NPD4758	Discontinued
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7041	Intermediate Similarity	NPD5696	Approved
0.7033	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5364	Discontinued
0.69	Remote Similarity	NPD1700	Approved
0.6875	Remote Similarity	NPD6399	Phase 3
0.686	Remote Similarity	NPD3703	Phase 2
0.6818	Remote Similarity	NPD4238	Approved
0.6818	Remote Similarity	NPD4802	Phase 2
0.6809	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6675	Approved
0.6796	Remote Similarity	NPD6402	Approved
0.6796	Remote Similarity	NPD5739	Approved
0.6796	Remote Similarity	NPD7128	Approved
0.6795	Remote Similarity	NPD3198	Approved
0.6786	Remote Similarity	NPD4787	Phase 1
0.6774	Remote Similarity	NPD7146	Approved
0.6774	Remote Similarity	NPD7521	Approved
0.6774	Remote Similarity	NPD6684	Approved
0.6774	Remote Similarity	NPD5330	Approved
0.6774	Remote Similarity	NPD6098	Approved
0.6774	Remote Similarity	NPD7334	Approved
0.6774	Remote Similarity	NPD6409	Approved
0.6737	Remote Similarity	NPD6673	Approved
0.6737	Remote Similarity	NPD6080	Approved
0.6737	Remote Similarity	NPD6904	Approved
0.6737	Remote Similarity	NPD4753	Phase 2
0.6729	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6632	Remote Similarity	NPD6903	Approved
0.6632	Remote Similarity	NPD6672	Approved
0.6632	Remote Similarity	NPD5737	Approved
0.6629	Remote Similarity	NPD3671	Phase 1
0.6607	Remote Similarity	NPD6319	Approved
0.6604	Remote Similarity	NPD6372	Approved
0.6604	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD6412	Phase 2
0.6571	Remote Similarity	NPD5697	Approved
0.6571	Remote Similarity	NPD5701	Approved
0.6566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6883	Approved
0.6542	Remote Similarity	NPD7102	Approved
0.6542	Remote Similarity	NPD7290	Approved
0.6531	Remote Similarity	NPD8171	Discontinued
0.6522	Remote Similarity	NPD4221	Approved
0.6522	Remote Similarity	NPD4223	Phase 3
0.6509	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5329	Approved
0.6484	Remote Similarity	NPD6928	Phase 2
0.6481	Remote Similarity	NPD6617	Approved
0.6481	Remote Similarity	NPD8130	Phase 1
0.6481	Remote Similarity	NPD6649	Approved
0.6481	Remote Similarity	NPD6847	Approved
0.6481	Remote Similarity	NPD6869	Approved
0.6481	Remote Similarity	NPD6650	Approved
0.6458	Remote Similarity	NPD5208	Approved
0.6449	Remote Similarity	NPD6014	Approved
0.6449	Remote Similarity	NPD6013	Approved
0.6449	Remote Similarity	NPD6012	Approved
0.6441	Remote Similarity	NPD7319	Approved
0.6429	Remote Similarity	NPD5284	Approved
0.6429	Remote Similarity	NPD5693	Phase 1
0.6429	Remote Similarity	NPD6050	Approved
0.6429	Remote Similarity	NPD5281	Approved
0.6422	Remote Similarity	NPD6882	Approved
0.6421	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4692	Approved
0.6413	Remote Similarity	NPD4139	Approved
0.64	Remote Similarity	NPD4629	Approved
0.64	Remote Similarity	NPD5210	Approved
0.6396	Remote Similarity	NPD6940	Discontinued
0.6383	Remote Similarity	NPD4197	Approved
0.6383	Remote Similarity	NPD3666	Approved
0.6383	Remote Similarity	NPD4786	Approved
0.6383	Remote Similarity	NPD3665	Phase 1
0.6383	Remote Similarity	NPD3133	Approved
0.6379	Remote Similarity	NPD7492	Approved
0.6373	Remote Similarity	NPD7638	Approved
0.6364	Remote Similarity	NPD4632	Approved
0.6356	Remote Similarity	NPD7736	Approved
0.6355	Remote Similarity	NPD6011	Approved
0.633	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5692	Phase 3
0.6325	Remote Similarity	NPD6616	Approved
0.6325	Remote Similarity	NPD7507	Approved
0.6316	Remote Similarity	NPD6054	Approved
0.6316	Remote Similarity	NPD6059	Approved
0.6311	Remote Similarity	NPD7640	Approved
0.6311	Remote Similarity	NPD7639	Approved
0.6311	Remote Similarity	NPD8418	Phase 2
0.63	Remote Similarity	NPD7748	Approved
0.6275	Remote Similarity	NPD4755	Approved
0.6271	Remote Similarity	NPD8293	Discontinued
0.6271	Remote Similarity	NPD7078	Approved
0.6263	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD4688	Approved
0.625	Remote Similarity	NPD4138	Approved
0.625	Remote Similarity	NPD4690	Approved
0.625	Remote Similarity	NPD4693	Phase 3
0.625	Remote Similarity	NPD4689	Approved
0.625	Remote Similarity	NPD5205	Approved
0.6239	Remote Similarity	NPD4634	Approved
0.6237	Remote Similarity	NPD5369	Approved
0.6226	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6051	Approved
0.6207	Remote Similarity	NPD6370	Approved
0.62	Remote Similarity	NPD4202	Approved
0.619	Remote Similarity	NPD7632	Discontinued
0.617	Remote Similarity	NPD3667	Approved
0.6162	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD4700	Approved
0.6154	Remote Similarity	NPD5286	Approved
0.6154	Remote Similarity	NPD3730	Approved
0.6154	Remote Similarity	NPD3728	Approved
0.6154	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6001	Approved
0.6122	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6015	Approved
0.6121	Remote Similarity	NPD6016	Approved
0.6117	Remote Similarity	NPD7902	Approved
0.6106	Remote Similarity	NPD6274	Approved
0.6105	Remote Similarity	NPD3669	Approved
0.6105	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7637	Suspended
0.61	Remote Similarity	NPD6411	Approved
0.61	Remote Similarity	NPD7515	Phase 2
0.6087	Remote Similarity	NPD7101	Approved
0.6087	Remote Similarity	NPD7100	Approved
0.6087	Remote Similarity	NPD3617	Approved
0.6082	Remote Similarity	NPD5280	Approved
0.6082	Remote Similarity	NPD4694	Approved
0.6082	Remote Similarity	NPD5690	Phase 2
0.6078	Remote Similarity	NPD5654	Approved
0.6071	Remote Similarity	NPD7909	Approved
0.6068	Remote Similarity	NPD5988	Approved
0.6064	Remote Similarity	NPD1780	Approved
0.6064	Remote Similarity	NPD1779	Approved
0.6061	Remote Similarity	NPD5328	Approved
0.6058	Remote Similarity	NPD4225	Approved
0.6055	Remote Similarity	NPD6686	Approved
0.6053	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6009	Approved
0.6038	Remote Similarity	NPD5211	Phase 2
0.6038	Remote Similarity	NPD5226	Approved
0.6038	Remote Similarity	NPD4633	Approved
0.6038	Remote Similarity	NPD5224	Approved
0.6038	Remote Similarity	NPD5225	Approved
0.6019	Remote Similarity	NPD6920	Discontinued
0.6019	Remote Similarity	NPD6008	Approved
0.6017	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD7328	Approved
0.5983	Remote Similarity	NPD6909	Approved
0.5983	Remote Similarity	NPD6908	Approved
0.5983	Remote Similarity	NPD5983	Phase 2
0.5981	Remote Similarity	NPD5175	Approved
0.5981	Remote Similarity	NPD5174	Approved
0.5981	Remote Similarity	NPD6052	Approved
0.5977	Remote Similarity	NPD229	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