NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	472.32
Volume:	509.319
LogP:	5.594
LogD:	4.568
LogS:	-4.466
# Rotatable Bonds:	6
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	4.621
Fsp3:	0.759
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.082
MDCK Permeability:	3.59E-05
Pgp-inhibitor:	0.792
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	99.24%
Volume Distribution (VD):	0.26
Pgp-substrate:	2.18%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.843
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.548
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.147
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	2.977
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.495
Carcinogencity:	0.021
Eye Corrosion:	0.004
Eye Irritation:	0.255
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC477595

Natural Product ID:	NPC477595
*Common Name:**	Comnastin D
IUPAC Name:	3-[[(3R,3aR,5aS,6R,7R,9aS,9bR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl]-4-hydroxybenzoic acid
Synonyms:	comnastin D
Standard InCHIKey:	NGZCNRIYOUJSLA-XYUNQWHOSA-N
Standard InCHI:	InChI=1S/C29H44O5/c1-18-10-13-26(2)22(27(18,3)17-20-16-19(24(31)32)8-9-21(20)30)11-14-28(4)23(26)12-15-29(28,5)25(33-6)34-7/h8-9,16,18,22-23,25,30H,10-15,17H2,1-7H3,(H,31,32)/t18-,22-,23-,26+,27-,28-,29+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@H]3CC[C@@]([C@@]3(CC[C@H]2[C@]1(C)CC4=C(C=CC(=C4)C(=O)O)O)C)(C)C(OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583757
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10096870]
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	n.a.	Mellingen, Switzerland	1965	PMID[10757714]
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	16	ppm	PMID[10757714]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	32	ppm	PMID[10757714]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128	ppm	PMID[10757714]

☑ 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 NPC477595 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	295
0.1-0.2	1270
0.2-0.3	2380
0.3-0.4	4709
0.4-0.5	10094
0.5-0.6	10814
0.6-0.7	10649
0.7-0.8	2425
0.8-0.85	38
0.85-0.9	18
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC477592
0.9485	High Similarity	NPC477593
0.9478	High Similarity	NPC477594
0.9407	High Similarity	NPC477596
0.903	High Similarity	NPC229894
0.8971	High Similarity	NPC18798
0.8963	High Similarity	NPC117899
0.8889	High Similarity	NPC193203
0.8759	High Similarity	NPC208293
0.875	High Similarity	NPC100242
0.8707	High Similarity	NPC279442
0.8649	High Similarity	NPC162569
0.8649	High Similarity	NPC116292
0.8649	High Similarity	NPC35160
0.8649	High Similarity	NPC267469
0.8649	High Similarity	NPC87630
0.8649	High Similarity	NPC179128
0.8523	High Similarity	NPC142654
0.8519	High Similarity	NPC174991
0.8425	Intermediate Similarity	NPC477209
0.8403	Intermediate Similarity	NPC248287
0.8403	Intermediate Similarity	NPC234548
0.8394	Intermediate Similarity	NPC137416
0.8389	Intermediate Similarity	NPC5568
0.8378	Intermediate Similarity	NPC75295
0.8355	Intermediate Similarity	NPC257847
0.8322	Intermediate Similarity	NPC477208
0.831	Intermediate Similarity	NPC49742
0.8298	Intermediate Similarity	NPC471851
0.8288	Intermediate Similarity	NPC172311
0.8278	Intermediate Similarity	NPC247219
0.8273	Intermediate Similarity	NPC176130
0.8273	Intermediate Similarity	NPC78364
0.8273	Intermediate Similarity	NPC84672
0.8273	Intermediate Similarity	NPC69424
0.8267	Intermediate Similarity	NPC477483
0.8267	Intermediate Similarity	NPC325032
0.8255	Intermediate Similarity	NPC258856
0.8252	Intermediate Similarity	NPC202225
0.8243	Intermediate Similarity	NPC477207
0.8214	Intermediate Similarity	NPC3009
0.8209	Intermediate Similarity	NPC474890
0.8209	Intermediate Similarity	NPC161943
0.8209	Intermediate Similarity	NPC273282
0.8194	Intermediate Similarity	NPC470210
0.8182	Intermediate Similarity	NPC477139
0.8182	Intermediate Similarity	NPC78307
0.8175	Intermediate Similarity	NPC475192
0.8158	Intermediate Similarity	NPC327962
0.8156	Intermediate Similarity	NPC276238
0.8143	Intermediate Similarity	NPC72667
0.8125	Intermediate Similarity	NPC194970
0.8121	Intermediate Similarity	NPC271451
0.8108	Intermediate Similarity	NPC272907
0.8108	Intermediate Similarity	NPC2681
0.8105	Intermediate Similarity	NPC140133
0.8099	Intermediate Similarity	NPC108129
0.8092	Intermediate Similarity	NPC17600
0.8092	Intermediate Similarity	NPC477206
0.8085	Intermediate Similarity	NPC473744
0.8082	Intermediate Similarity	NPC475957
0.8082	Intermediate Similarity	NPC170718
0.8079	Intermediate Similarity	NPC470330
0.8071	Intermediate Similarity	NPC254492
0.8071	Intermediate Similarity	NPC471929
0.8071	Intermediate Similarity	NPC471930
0.8071	Intermediate Similarity	NPC204579
0.8071	Intermediate Similarity	NPC471935
0.8069	Intermediate Similarity	NPC173569
0.8069	Intermediate Similarity	NPC477874
0.8069	Intermediate Similarity	NPC279463
0.8065	Intermediate Similarity	NPC62051
0.806	Intermediate Similarity	NPC83718
0.8058	Intermediate Similarity	NPC184219
0.8058	Intermediate Similarity	NPC265413
0.8058	Intermediate Similarity	NPC10154
0.8056	Intermediate Similarity	NPC475457
0.8056	Intermediate Similarity	NPC18982
0.8056	Intermediate Similarity	NPC475346
0.8056	Intermediate Similarity	NPC475627
0.8054	Intermediate Similarity	NPC184935
0.8052	Intermediate Similarity	NPC48671
0.8052	Intermediate Similarity	NPC124842
0.8043	Intermediate Similarity	NPC121168
0.8043	Intermediate Similarity	NPC67300
0.8042	Intermediate Similarity	NPC476847
0.8041	Intermediate Similarity	NPC471853
0.8041	Intermediate Similarity	NPC469911
0.8041	Intermediate Similarity	NPC315578
0.8039	Intermediate Similarity	NPC52931
0.8038	Intermediate Similarity	NPC130489
0.8038	Intermediate Similarity	NPC208676
0.8028	Intermediate Similarity	NPC194979
0.8028	Intermediate Similarity	NPC303910
0.8028	Intermediate Similarity	NPC171460
0.8026	Intermediate Similarity	NPC66991
0.8014	Intermediate Similarity	NPC249817
0.8013	Intermediate Similarity	NPC8102
0.8013	Intermediate Similarity	NPC66894
0.8013	Intermediate Similarity	NPC472835
0.8012	Intermediate Similarity	NPC469396
0.8012	Intermediate Similarity	NPC149002
0.8012	Intermediate Similarity	NPC469419
0.8012	Intermediate Similarity	NPC88176
0.8012	Intermediate Similarity	NPC469458
0.8	Intermediate Similarity	NPC11266
0.8	Intermediate Similarity	NPC202391
0.8	Intermediate Similarity	NPC296659
0.8	Intermediate Similarity	NPC161151
0.8	Intermediate Similarity	NPC137750
0.7987	Intermediate Similarity	NPC477627
0.7987	Intermediate Similarity	NPC37642
0.7987	Intermediate Similarity	NPC477275
0.7987	Intermediate Similarity	NPC289021
0.7987	Intermediate Similarity	NPC158546
0.7986	Intermediate Similarity	NPC302844
0.7974	Intermediate Similarity	NPC161955
0.7973	Intermediate Similarity	NPC112789
0.7973	Intermediate Similarity	NPC26924
0.7973	Intermediate Similarity	NPC19622
0.7972	Intermediate Similarity	NPC72915
0.7971	Intermediate Similarity	NPC249340
0.7971	Intermediate Similarity	NPC162935
0.7961	Intermediate Similarity	NPC286038
0.7959	Intermediate Similarity	NPC22676
0.7959	Intermediate Similarity	NPC216940
0.7959	Intermediate Similarity	NPC198621
0.7959	Intermediate Similarity	NPC475482
0.7958	Intermediate Similarity	NPC96024
0.7949	Intermediate Similarity	NPC205172
0.7949	Intermediate Similarity	NPC209393
0.7947	Intermediate Similarity	NPC260152
0.7945	Intermediate Similarity	NPC475917
0.7943	Intermediate Similarity	NPC473751
0.7943	Intermediate Similarity	NPC110211
0.7935	Intermediate Similarity	NPC477276
0.7935	Intermediate Similarity	NPC11892
0.7935	Intermediate Similarity	NPC475093
0.7933	Intermediate Similarity	NPC248068
0.7933	Intermediate Similarity	NPC308572
0.7931	Intermediate Similarity	NPC126516
0.7931	Intermediate Similarity	NPC48929
0.7931	Intermediate Similarity	NPC329913
0.7929	Intermediate Similarity	NPC199273
0.7919	Intermediate Similarity	NPC275903
0.7919	Intermediate Similarity	NPC476534
0.7919	Intermediate Similarity	NPC3218
0.7919	Intermediate Similarity	NPC470035
0.7919	Intermediate Similarity	NPC168471
0.7917	Intermediate Similarity	NPC125153
0.7917	Intermediate Similarity	NPC473777
0.7905	Intermediate Similarity	NPC20210
0.7902	Intermediate Similarity	NPC288290
0.7902	Intermediate Similarity	NPC131684
0.7901	Intermediate Similarity	NPC469459
0.7901	Intermediate Similarity	NPC200726
0.7899	Intermediate Similarity	NPC164852
0.7899	Intermediate Similarity	NPC241001
0.7899	Intermediate Similarity	NPC216216
0.7898	Intermediate Similarity	NPC472807
0.7895	Intermediate Similarity	NPC478160
0.7895	Intermediate Similarity	NPC470038
0.7895	Intermediate Similarity	NPC320734
0.7895	Intermediate Similarity	NPC97188
0.7891	Intermediate Similarity	NPC118919
0.7888	Intermediate Similarity	NPC100420
0.7887	Intermediate Similarity	NPC51448
0.7887	Intermediate Similarity	NPC115797
0.7883	Intermediate Similarity	NPC42657
0.7881	Intermediate Similarity	NPC96447
0.7877	Intermediate Similarity	NPC213122
0.7877	Intermediate Similarity	NPC293454
0.7877	Intermediate Similarity	NPC475088
0.7875	Intermediate Similarity	NPC117943
0.7875	Intermediate Similarity	NPC293568
0.7872	Intermediate Similarity	NPC87985
0.7871	Intermediate Similarity	NPC77310
0.7868	Intermediate Similarity	NPC174087
0.7867	Intermediate Similarity	NPC106519
0.7867	Intermediate Similarity	NPC91019
0.7862	Intermediate Similarity	NPC175738
0.7857	Intermediate Similarity	NPC275145
0.7857	Intermediate Similarity	NPC96599
0.7857	Intermediate Similarity	NPC473719
0.7857	Intermediate Similarity	NPC85511
0.7853	Intermediate Similarity	NPC177362
0.7848	Intermediate Similarity	NPC283480
0.7848	Intermediate Similarity	NPC148323
0.7843	Intermediate Similarity	NPC469498
0.7843	Intermediate Similarity	NPC147250
0.7843	Intermediate Similarity	NPC25844
0.7842	Intermediate Similarity	NPC295034
0.7842	Intermediate Similarity	NPC253627
0.7838	Intermediate Similarity	NPC36868
0.7838	Intermediate Similarity	NPC53001
0.7838	Intermediate Similarity	NPC471152
0.7838	Intermediate Similarity	NPC119542
0.7834	Intermediate Similarity	NPC470102
0.7829	Intermediate Similarity	NPC126707
0.7826	Intermediate Similarity	NPC318552

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 NPC477595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	773
0.2-0.3	1354
0.3-0.4	2506
0.4-0.5	2439
0.5-0.6	1372
0.6-0.7	403
0.7-0.8	44
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
0.8278	Intermediate Similarity	NPD7458	Discontinued
0.8042	Intermediate Similarity	NPD6663	Approved
0.8014	Intermediate Similarity	NPD5736	Approved
0.7867	Intermediate Similarity	NPD7003	Approved
0.7826	Intermediate Similarity	NPD3019	Approved
0.78	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3764	Approved
0.7718	Intermediate Similarity	NPD5406	Approved
0.7718	Intermediate Similarity	NPD5404	Approved
0.7718	Intermediate Similarity	NPD5408	Approved
0.7718	Intermediate Similarity	NPD5405	Approved
0.7698	Intermediate Similarity	NPD2932	Approved
0.7655	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD8166	Discontinued
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7626	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6273	Approved
0.7554	Intermediate Similarity	NPD9545	Approved
0.7533	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7236	Approved
0.7518	Intermediate Similarity	NPD5951	Approved
0.75	Intermediate Similarity	NPD1470	Approved
0.7465	Intermediate Similarity	NPD1201	Approved
0.7453	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3023	Approved
0.7394	Intermediate Similarity	NPD3026	Approved
0.7391	Intermediate Similarity	NPD7819	Suspended
0.7388	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1164	Approved
0.7376	Intermediate Similarity	NPD3025	Approved
0.7376	Intermediate Similarity	NPD3024	Approved
0.7368	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8127	Discontinued
0.7329	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3091	Approved
0.7303	Intermediate Similarity	NPD2799	Discontinued
0.7301	Intermediate Similarity	NPD7768	Phase 2
0.7296	Intermediate Similarity	NPD7239	Suspended
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7262	Intermediate Similarity	NPD7473	Discontinued
0.7261	Intermediate Similarity	NPD7390	Discontinued
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7075	Discontinued
0.7239	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3092	Approved
0.7219	Intermediate Similarity	NPD7799	Discontinued
0.7215	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2533	Approved
0.7215	Intermediate Similarity	NPD2532	Approved
0.7215	Intermediate Similarity	NPD2534	Approved
0.7203	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8032	Phase 2
0.7192	Intermediate Similarity	NPD1876	Approved
0.719	Intermediate Similarity	NPD1510	Phase 2
0.7186	Intermediate Similarity	NPD6232	Discontinued
0.7181	Intermediate Similarity	NPD7008	Discontinued
0.7179	Intermediate Similarity	NPD3750	Approved
0.7179	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3972	Approved
0.7161	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7107	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7028	Phase 2
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7095	Intermediate Similarity	NPD2798	Approved
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7961	Discontinued
0.7083	Intermediate Similarity	NPD3095	Discontinued
0.7083	Intermediate Similarity	NPD4059	Approved
0.7079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5844	Phase 1
0.7075	Intermediate Similarity	NPD1283	Approved
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD8312	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD1607	Approved
0.7048	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD9493	Approved
0.7041	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4140	Approved
0.7039	Intermediate Similarity	NPD1240	Approved
0.7025	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4380	Phase 2
0.6993	Remote Similarity	NPD7610	Discontinued
0.6987	Remote Similarity	NPD2346	Discontinued
0.6987	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8455	Phase 2
0.6966	Remote Similarity	NPD4626	Approved
0.6966	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6559	Discontinued
0.6948	Remote Similarity	NPD6651	Approved
0.6946	Remote Similarity	NPD3749	Approved
0.6943	Remote Similarity	NPD1549	Phase 2
0.6928	Remote Similarity	NPD943	Approved
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6919	Remote Similarity	NPD7177	Discontinued
0.6913	Remote Similarity	NPD2797	Approved
0.6909	Remote Similarity	NPD6801	Discontinued
0.6908	Remote Similarity	NPD3268	Approved
0.6908	Remote Similarity	NPD2313	Discontinued
0.6905	Remote Similarity	NPD6234	Discontinued
0.6886	Remote Similarity	NPD7058	Phase 2
0.6886	Remote Similarity	NPD4967	Phase 2
0.6886	Remote Similarity	NPD4965	Approved
0.6886	Remote Similarity	NPD7057	Phase 3
0.6886	Remote Similarity	NPD4966	Approved
0.6886	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD230	Phase 1
0.6879	Remote Similarity	NPD5762	Approved
0.6879	Remote Similarity	NPD7266	Discontinued
0.6879	Remote Similarity	NPD6004	Phase 3
0.6879	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2344	Approved
0.6879	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7094	Approved
0.6879	Remote Similarity	NPD6002	Phase 3
0.6879	Remote Similarity	NPD5763	Approved
0.6879	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6005	Phase 3
0.6879	Remote Similarity	NPD6858	Approved
0.6871	Remote Similarity	NPD1281	Approved
0.6867	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7033	Discontinued
0.6859	Remote Similarity	NPD3748	Approved
0.6859	Remote Similarity	NPD4308	Phase 3
0.6854	Remote Similarity	NPD8150	Discontinued
0.6838	Remote Similarity	NPD1930	Approved
0.6838	Remote Similarity	NPD1929	Approved
0.6838	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD74	Approved
0.6835	Remote Similarity	NPD9266	Approved
0.6832	Remote Similarity	NPD6799	Approved
0.6828	Remote Similarity	NPD7741	Discontinued
0.6824	Remote Similarity	NPD1608	Approved
0.6824	Remote Similarity	NPD6959	Discontinued
0.6821	Remote Similarity	NPD3818	Discontinued
0.6821	Remote Similarity	NPD7228	Approved
0.6818	Remote Similarity	NPD2979	Phase 3
0.6818	Remote Similarity	NPD4060	Phase 1
0.6815	Remote Similarity	NPD4476	Approved
0.6815	Remote Similarity	NPD4477	Approved
0.6815	Remote Similarity	NPD1551	Phase 2
0.6815	Remote Similarity	NPD2796	Approved
0.6813	Remote Similarity	NPD6190	Approved
0.6806	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6798	Discontinued
0.6795	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2800	Approved
0.6784	Remote Similarity	NPD7229	Phase 3
0.6783	Remote Similarity	NPD2629	Approved
0.6781	Remote Similarity	NPD5691	Approved
0.6776	Remote Similarity	NPD6832	Phase 2
0.677	Remote Similarity	NPD3300	Phase 2
0.6763	Remote Similarity	NPD9264	Approved
0.6763	Remote Similarity	NPD9267	Approved
0.6763	Remote Similarity	NPD9263	Approved
0.6761	Remote Similarity	NPD6764	Approved
0.6761	Remote Similarity	NPD6765	Approved
0.676	Remote Similarity	NPD8434	Phase 2
0.6755	Remote Similarity	NPD4624	Approved
0.6755	Remote Similarity	NPD8320	Phase 1
0.6755	Remote Similarity	NPD8319	Approved
0.6752	Remote Similarity	NPD7305	Phase 1
0.6752	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4110	Phase 3
0.675	Remote Similarity	NPD3400	Discontinued
0.675	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7074	Phase 3
0.6741	Remote Similarity	NPD3020	Approved
0.6711	Remote Similarity	NPD9269	Phase 2
0.6708	Remote Similarity	NPD2309	Approved
0.6702	Remote Similarity	NPD7497	Discontinued
0.6702	Remote Similarity	NPD7435	Discontinued
0.669	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1203	Approved
0.6688	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5711	Approved
0.6686	Remote Similarity	NPD5710	Approved
0.6686	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD5735	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