NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	561.32
Volume:	575.478
LogP:	4.374
LogD:	4.127
LogS:	-2.701
# Rotatable Bonds:	13
TPSA:	117.44
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	4.928
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.479
MDCK Permeability:	4.830757916352013e-06
Pgp-inhibitor:	0.93
Pgp-substrate:	0.124
Human Intestinal Absorption (HIA):	0.798
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	97.84723663330078%
Volume Distribution (VD):	1.607
Pgp-substrate:	1.7820106744766235%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.369
CYP2C19-substrate:	0.182
CYP2C9-inhibitor:	0.789
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.794
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	5.187
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.536
Human Hepatotoxicity (H-HT):	0.694
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.928
Carcinogencity:	0.124
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC477119

Natural Product ID:	NPC477119
*Common Name:**	fasciospongine B
IUPAC Name:	[2-[2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-5-[1-[2-(1H-imidazol-5-yl)ethyl]-5-oxo-2H-pyrrol-3-yl]pentyl] hydrogen sulfate
Synonyms:	Fasciospongine B
Standard InCHIKey:	AVZWBTNFMAUZIC-CYPSKNEPSA-N
Standard InCHI:	InChI=1S/C30H47N3O5S/c1-22-10-11-26-27(9-6-14-29(26,2)3)30(22,4)15-12-23(20-38-39(35,36)37)7-5-8-24-17-28(34)33(19-24)16-13-25-18-31-21-32-25/h9,17-18,21-23,26H,5-8,10-16,19-20H2,1-4H3,(H,31,32)(H,35,36,37)/t22-,23?,26-,30-/m0/s1
SMILES:	C[C@H]1CC[C@H]2C(=CCCC2(C)C)[C@@]1(C)CCC(CCCC3=CC(=O)N(C3)CCC4=CN=CN4)COS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16755997
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0003455] Sulfuric acid esters [CHEMONTID:0001185] Sulfuric acid monoesters

*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
NPO33581	Fasciospongia sp.	Species	Thorectidae	Eukaryota	n.a.	at a depth of 1 m in Palau	2003-DEC	PMID[19178162]

☑ 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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	19	mm	PMID[19178162]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	17	mm	PMID[19178162]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	15	mm	PMID[19178162]

☑ 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 NPC477119 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	310
0.1-0.2	2426
0.2-0.3	25880
0.3-0.4	9953
0.4-0.5	3215
0.5-0.6	837
0.6-0.7	72
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9634	High Similarity	NPC477118
0.9576	High Similarity	NPC477120
0.6995	Remote Similarity	NPC54981
0.6847	Remote Similarity	NPC71238
0.6735	Remote Similarity	NPC201900
0.6704	Remote Similarity	NPC60537
0.6684	Remote Similarity	NPC101676
0.6667	Remote Similarity	NPC238945
0.6649	Remote Similarity	NPC473585
0.6615	Remote Similarity	NPC527
0.6615	Remote Similarity	NPC144474
0.6615	Remote Similarity	NPC133782
0.6566	Remote Similarity	NPC313504
0.6519	Remote Similarity	NPC472834
0.6513	Remote Similarity	NPC265111
0.6468	Remote Similarity	NPC233431
0.6468	Remote Similarity	NPC300139
0.6409	Remote Similarity	NPC69843
0.639	Remote Similarity	NPC300183
0.6378	Remote Similarity	NPC472832
0.6378	Remote Similarity	NPC18308
0.6368	Remote Similarity	NPC282247
0.6319	Remote Similarity	NPC282531
0.631	Remote Similarity	NPC180462
0.6304	Remote Similarity	NPC472833
0.6244	Remote Similarity	NPC323244
0.6236	Remote Similarity	NPC474986
0.6236	Remote Similarity	NPC476013
0.6236	Remote Similarity	NPC476522
0.6201	Remote Similarity	NPC476521
0.618	Remote Similarity	NPC8590
0.6173	Remote Similarity	NPC327613
0.6163	Remote Similarity	NPC25465
0.6158	Remote Similarity	NPC286696
0.6158	Remote Similarity	NPC470266
0.6145	Remote Similarity	NPC476520
0.6143	Remote Similarity	NPC473376
0.6142	Remote Similarity	NPC16659
0.6139	Remote Similarity	NPC155498
0.6133	Remote Similarity	NPC328924
0.6121	Remote Similarity	NPC320968
0.6121	Remote Similarity	NPC477419
0.6121	Remote Similarity	NPC477417
0.6102	Remote Similarity	NPC296437
0.6091	Remote Similarity	NPC265710
0.6089	Remote Similarity	NPC476433
0.6089	Remote Similarity	NPC476528
0.608	Remote Similarity	NPC237812
0.608	Remote Similarity	NPC18223
0.6077	Remote Similarity	NPC327477
0.6069	Remote Similarity	NPC235501
0.6068	Remote Similarity	NPC11445
0.6067	Remote Similarity	NPC167285
0.6067	Remote Similarity	NPC76544
0.6067	Remote Similarity	NPC185903
0.6067	Remote Similarity	NPC226184
0.6065	Remote Similarity	NPC54744
0.6061	Remote Similarity	NPC477121
0.6044	Remote Similarity	NPC476408
0.6041	Remote Similarity	NPC240088
0.6041	Remote Similarity	NPC473380
0.6019	Remote Similarity	NPC157828
0.6019	Remote Similarity	NPC195239
0.6013	Remote Similarity	NPC111132
0.6011	Remote Similarity	NPC244700
0.601	Remote Similarity	NPC213629
0.6	Remote Similarity	NPC156003
0.5989	Remote Similarity	NPC197068
0.5981	Remote Similarity	NPC258062
0.5981	Remote Similarity	NPC127677
0.5979	Remote Similarity	NPC201700
0.5972	Remote Similarity	NPC242923
0.5953	Remote Similarity	NPC271862
0.5943	Remote Similarity	NPC98715
0.5935	Remote Similarity	NPC225821
0.5935	Remote Similarity	NPC46225
0.5933	Remote Similarity	NPC473640
0.5933	Remote Similarity	NPC477044
0.5933	Remote Similarity	NPC477041
0.5922	Remote Similarity	NPC210947
0.592	Remote Similarity	NPC243319
0.5911	Remote Similarity	NPC94752
0.5905	Remote Similarity	NPC100321
0.5905	Remote Similarity	NPC477045
0.5879	Remote Similarity	NPC151939
0.5876	Remote Similarity	NPC126634
0.5864	Remote Similarity	NPC124276
0.5856	Remote Similarity	NPC308906
0.5849	Remote Similarity	NPC54537
0.5849	Remote Similarity	NPC475506
0.5847	Remote Similarity	NPC174020
0.5833	Remote Similarity	NPC470139
0.5833	Remote Similarity	NPC300238
0.5833	Remote Similarity	NPC116555
0.5822	Remote Similarity	NPC155143
0.5822	Remote Similarity	NPC64216
0.5821	Remote Similarity	NPC300688
0.5814	Remote Similarity	NPC15566
0.5799	Remote Similarity	NPC153980
0.5799	Remote Similarity	NPC87856
0.5799	Remote Similarity	NPC6865
0.5799	Remote Similarity	NPC151976
0.5798	Remote Similarity	NPC473646
0.5792	Remote Similarity	NPC132211
0.5792	Remote Similarity	NPC471192
0.5786	Remote Similarity	NPC326248
0.5786	Remote Similarity	NPC187191
0.5782	Remote Similarity	NPC171317
0.5773	Remote Similarity	NPC267965
0.5771	Remote Similarity	NPC213468
0.5767	Remote Similarity	NPC477043
0.5756	Remote Similarity	NPC476527
0.5755	Remote Similarity	NPC293917
0.5754	Remote Similarity	NPC477634
0.5754	Remote Similarity	NPC470140
0.5753	Remote Similarity	NPC72956
0.5746	Remote Similarity	NPC476491
0.5743	Remote Similarity	NPC477042
0.5735	Remote Similarity	NPC174281
0.5735	Remote Similarity	NPC228835
0.5735	Remote Similarity	NPC475286
0.5735	Remote Similarity	NPC208751
0.5721	Remote Similarity	NPC203614
0.5721	Remote Similarity	NPC204491
0.5714	Remote Similarity	NPC477420
0.5714	Remote Similarity	NPC54420
0.5714	Remote Similarity	NPC477418
0.5708	Remote Similarity	NPC265576
0.5707	Remote Similarity	NPC280290
0.57	Remote Similarity	NPC317054
0.5699	Remote Similarity	NPC469762
0.5695	Remote Similarity	NPC267811
0.5692	Remote Similarity	NPC470203
0.5688	Remote Similarity	NPC476525
0.5685	Remote Similarity	NPC49217
0.5685	Remote Similarity	NPC160105
0.5681	Remote Similarity	NPC136957
0.5681	Remote Similarity	NPC19696
0.567	Remote Similarity	NPC477714
0.5667	Remote Similarity	NPC474180
0.5667	Remote Similarity	NPC188821
0.5663	Remote Similarity	NPC311276
0.5662	Remote Similarity	NPC162860
0.5662	Remote Similarity	NPC478158
0.5662	Remote Similarity	NPC107077
0.5662	Remote Similarity	NPC223791
0.566	Remote Similarity	NPC229332
0.5659	Remote Similarity	NPC165495
0.5656	Remote Similarity	NPC75634
0.5656	Remote Similarity	NPC471194
0.5656	Remote Similarity	NPC471193
0.5652	Remote Similarity	NPC313514
0.5648	Remote Similarity	NPC469785
0.5647	Remote Similarity	NPC89987
0.5641	Remote Similarity	NPC470204
0.564	Remote Similarity	NPC280638
0.5636	Remote Similarity	NPC113369
0.5634	Remote Similarity	NPC470499
0.5631	Remote Similarity	NPC188387
0.5631	Remote Similarity	NPC163421
0.5625	Remote Similarity	NPC469765
0.5625	Remote Similarity	NPC65215
0.5625	Remote Similarity	NPC25008
0.5625	Remote Similarity	NPC73952
0.5625	Remote Similarity	NPC469786
0.5625	Remote Similarity	NPC469760
0.5625	Remote Similarity	NPC12100
0.5625	Remote Similarity	NPC259644
0.5625	Remote Similarity	NPC469763
0.5625	Remote Similarity	NPC173028
0.5622	Remote Similarity	NPC313897
0.5622	Remote Similarity	NPC217656
0.5616	Remote Similarity	NPC476524
0.5606	Remote Similarity	NPC474561
0.5606	Remote Similarity	NPC49954
0.5603	Remote Similarity	NPC475969
0.5603	Remote Similarity	NPC474877
0.5603	Remote Similarity	NPC475859
0.56	Remote Similarity	NPC89562

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 NPC477119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	559
0.2-0.3	2045
0.3-0.4	3140
0.4-0.5	2347
0.5-0.6	821
0.6-0.7	65
0.7-0.8	1
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
0.7305	Intermediate Similarity	NPD3706	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3105	Discontinued
0.7039	Intermediate Similarity	NPD3130	Discontinued
0.6872	Remote Similarity	NPD6850	Phase 2
0.6872	Remote Similarity	NPD6849	Phase 2
0.68	Remote Similarity	NPD8629	Discontinued
0.6774	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5768	Phase 2
0.6751	Remote Similarity	NPD8641	Approved
0.6751	Remote Similarity	NPD8113	Phase 2
0.6704	Remote Similarity	NPD2180	Approved
0.6699	Remote Similarity	NPD7465	Suspended
0.6667	Remote Similarity	NPD8271	Discontinued
0.6651	Remote Similarity	NPD8075	Discontinued
0.6648	Remote Similarity	NPD1030	Approved
0.6648	Remote Similarity	NPD1027	Approved
0.6648	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2604	Approved
0.6609	Remote Similarity	NPD5342	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8119	Discontinued
0.6575	Remote Similarity	NPD1303	Phase 1
0.6553	Remote Similarity	NPD7834	Approved
0.6527	Remote Similarity	NPD1807	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7981	Discontinued
0.651	Remote Similarity	NPD1327	Discontinued
0.6485	Remote Similarity	NPD1388	Phase 1
0.6485	Remote Similarity	NPD1390	Phase 1
0.6485	Remote Similarity	NPD1389	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD1731	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD875	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8256	Approved
0.6432	Remote Similarity	NPD8257	Approved
0.6432	Remote Similarity	NPD2813	Phase 3
0.6432	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD1042	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD1290	Phase 2
0.64	Remote Similarity	NPD6619	Phase 3
0.6364	Remote Similarity	NPD1451	Approved
0.6364	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3697	Discontinued
0.6354	Remote Similarity	NPD3108	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.631	Remote Similarity	NPD300	Approved
0.6304	Remote Similarity	NPD695	Discontinued
0.6292	Remote Similarity	NPD9627	Approved
0.6291	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD567	Approved
0.6236	Remote Similarity	NPD568	Approved
0.6236	Remote Similarity	NPD566	Approved
0.6233	Remote Similarity	NPD8317	Phase 2
0.6233	Remote Similarity	NPD8316	Phase 2
0.6226	Remote Similarity	NPD8261	Discontinued
0.6226	Remote Similarity	NPD5072	Discontinued
0.6221	Remote Similarity	NPD8105	Discontinued
0.6209	Remote Similarity	NPD2443	Approved
0.6209	Remote Similarity	NPD2442	Approved
0.6203	Remote Similarity	NPD5321	Phase 3
0.6196	Remote Similarity	NPD9132	Discontinued
0.6195	Remote Similarity	NPD2880	Discontinued
0.6188	Remote Similarity	NPD4182	Phase 3
0.6188	Remote Similarity	NPD4183	Phase 3
0.6183	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3405	Phase 3
0.618	Remote Similarity	NPD9183	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD8292	Phase 2
0.6161	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD994	Phase 2
0.6158	Remote Similarity	NPD996	Phase 2
0.6129	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3041	Approved
0.6111	Remote Similarity	NPD2526	Phase 2
0.6111	Remote Similarity	NPD2523	Phase 2
0.6099	Remote Similarity	NPD6164	Phase 2
0.6099	Remote Similarity	NPD6165	Phase 2
0.608	Remote Similarity	NPD3586	Phase 2
0.608	Remote Similarity	NPD9133	Approved
0.608	Remote Similarity	NPD9628	Approved
0.6065	Remote Similarity	NPD7277	Approved
0.6065	Remote Similarity	NPD7276	Approved
0.6051	Remote Similarity	NPD3081	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD3906	Approved
0.6041	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD2008	Discontinued
0.603	Remote Similarity	NPD1895	Discontinued
0.6029	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD2408	Discontinued
0.6023	Remote Similarity	NPD576	Discontinued
0.6019	Remote Similarity	NPD2411	Approved
0.6013	Remote Similarity	NPD8862	Approved
0.6013	Remote Similarity	NPD8861	Approved
0.6013	Remote Similarity	NPD8859	Approved
0.601	Remote Similarity	NPD3432	Approved
0.6	Remote Similarity	NPD8523	Approved
0.5991	Remote Similarity	NPD6714	Phase 3
0.5981	Remote Similarity	NPD4612	Discontinued
0.5979	Remote Similarity	NPD6906	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD2136	Approved
0.5959	Remote Similarity	NPD2135	Approved
0.5959	Remote Similarity	NPD2134	Approved
0.5956	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD7297	Phase 2
0.5933	Remote Similarity	NPD1982	Phase 1
0.5933	Remote Similarity	NPD1249	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4990	Clinical (unspecified phase)
0.592	Remote Similarity	NPD9081	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD2793	Discontinued
0.5899	Remote Similarity	NPD949	Phase 1
0.5896	Remote Similarity	NPD3497	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7415	Suspended
0.5894	Remote Similarity	NPD460	Discontinued
0.5891	Remote Similarity	NPD2456	Phase 2
0.5891	Remote Similarity	NPD2457	Phase 2
0.5888	Remote Similarity	NPD966	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD1288	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD6664	Approved
0.5882	Remote Similarity	NPD6470	Phase 3
0.5872	Remote Similarity	NPD7164	Discontinued
0.5871	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7887	Approved
0.5859	Remote Similarity	NPD7888	Approved
0.585	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD6718	Discontinued
0.5845	Remote Similarity	NPD3431	Approved
0.5845	Remote Similarity	NPD3430	Approved
0.5841	Remote Similarity	NPD8169	Discontinued
0.5837	Remote Similarity	NPD7471	Discontinued
0.5822	Remote Similarity	NPD7079	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD8030	Approved
0.5806	Remote Similarity	NPD4709	Approved
0.5805	Remote Similarity	NPD6418	Phase 1
0.58	Remote Similarity	NPD4155	Approved
0.5799	Remote Similarity	NPD7182	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD7656	Approved
0.5799	Remote Similarity	NPD7657	Approved
0.5795	Remote Similarity	NPD8120	Approved
0.5795	Remote Similarity	NPD8121	Phase 3
0.5792	Remote Similarity	NPD1233	Suspended
0.5787	Remote Similarity	NPD1506	Discontinued
0.5787	Remote Similarity	NPD7445	Phase 1
0.5775	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD7103	Approved
0.5767	Remote Similarity	NPD8272	Phase 2
0.576	Remote Similarity	NPD7689	Approved
0.5758	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD8250	Phase 2
0.5755	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD4863	Approved
0.5753	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6268	Phase 1
0.5747	Remote Similarity	NPD4395	Phase 1
0.5743	Remote Similarity	NPD5508	Phase 1
0.5742	Remote Similarity	NPD3460	Discontinued
0.5738	Remote Similarity	NPD2179	Discontinued
0.5737	Remote Similarity	NPD1257	Approved
0.5734	Remote Similarity	NPD1600	Suspended
0.5733	Remote Similarity	NPD8159	Discontinued
0.5733	Remote Similarity	NPD6970	Phase 2
0.5728	Remote Similarity	NPD3501	Phase 2
0.5727	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD4181	Approved
0.5721	Remote Similarity	NPD4892	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD2144	Approved
0.5714	Remote Similarity	NPD1641	Discontinued
0.5714	Remote Similarity	NPD5198	Approved
0.5714	Remote Similarity	NPD1354	Approved
0.5714	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3038	Discontinued
0.5714	Remote Similarity	NPD5199	Approved
0.5714	Remote Similarity	NPD1355	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1313	Approved
0.5714	Remote Similarity	NPD1356	Approved
0.5708	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5707	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6352	Phase 2
0.5702	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.57	Remote Similarity	NPD2928	Phase 2
0.5695	Remote Similarity	NPD6218	Discontinued
0.5694	Remote Similarity	NPD4615	Phase 2
0.5693	Remote Similarity	NPD40	Phase 2
0.5693	Remote Similarity	NPD5730	Phase 2
0.569	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.5689	Remote Similarity	NPD5827	Discontinued
0.5689	Remote Similarity	NPD6210	Phase 3

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