NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.16
Volume:	298.613
LogP:	4.331
LogD:	3.724
LogS:	-4.907
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	3.441
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.924
MDCK Permeability:	1.8863876903196797e-05
Pgp-inhibitor:	0.379
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.819
30% Bioavailability (F30%):	0.391

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	96.42304229736328%
Volume Distribution (VD):	0.984
Pgp-substrate:	4.3194355964660645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.828
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.764
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.487
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.564
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.524
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	11.421
Half-life (T1/2):	0.257

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.178
Rat Oral Acute Toxicity:	0.42
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.193
Carcinogencity:	0.755
Eye Corrosion:	0.032
Eye Irritation:	0.898
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC254492

Natural Product ID:	NPC254492
*Common Name:**	12-Hydroxy-13-Methyl-5,8,11,13-Podocarpatetraen-7-One
IUPAC Name:	(4aS)-6-hydroxy-1,1,4a,7-tetramethyl-3,4-dihydro-2H-phenanthren-9-one
Synonyms:
Standard InCHIKey:	HSBIYLUTRHKDDM-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C18H22O2/c1-11-8-12-13(9-14(11)19)18(4)7-5-6-17(2,3)16(18)10-15(12)20/h8-10,19H,5-7H2,1-4H3/t18-/m1/s1
SMILES:	O=C1C=C2C(C)(C)CCC[C@@]2(c2c1cc(C)c(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261110
PubChem CID:	90675898
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	Roots	Yucatan Peninsula	n.a.	PMID[24709561]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	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	6
Others	2

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	45600.0	nM	PMID[531344]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	39600.0	nM	PMID[531344]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	70000.0	nM	PMID[531344]
NPT165	Cell Line	HeLa	Homo sapiens	Ratio IC50	>	1.5	n.a.	PMID[531344]
NPT165	Cell Line	HeLa	Homo sapiens	Ratio IC50	>	1.8	n.a.	PMID[531344]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	70000.0	nM	PMID[531344]

☑ 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 NPC254492 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	322
0.1-0.2	1619
0.2-0.3	3121
0.3-0.4	8485
0.4-0.5	10400
0.5-0.6	6714
0.6-0.7	8703
0.7-0.8	2883
0.8-0.85	328
0.85-0.9	89
0.9-0.95	22
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC72667
0.9754	High Similarity	NPC171460
0.9752	High Similarity	NPC84672
0.9752	High Similarity	NPC176130
0.9752	High Similarity	NPC69424
0.9752	High Similarity	NPC78364
0.9667	High Similarity	NPC199273
0.9516	High Similarity	NPC108129
0.9512	High Similarity	NPC96024
0.95	High Similarity	NPC282577
0.944	High Similarity	NPC471851
0.9435	High Similarity	NPC276238
0.9435	High Similarity	NPC303910
0.9417	High Similarity	NPC154696
0.9355	High Similarity	NPC3009
0.9291	High Similarity	NPC138472
0.9291	High Similarity	NPC78307
0.9291	High Similarity	NPC477139
0.9268	High Similarity	NPC123506
0.9219	High Similarity	NPC202225
0.9174	High Similarity	NPC259703
0.9174	High Similarity	NPC32322
0.9154	High Similarity	NPC36868
0.9141	High Similarity	NPC111845
0.9024	High Similarity	NPC176208
0.9008	High Similarity	NPC53001
0.9008	High Similarity	NPC475957
0.8976	High Similarity	NPC117899
0.896	High Similarity	NPC137750
0.8952	High Similarity	NPC273683
0.8939	High Similarity	NPC87723
0.8939	High Similarity	NPC230811
0.8931	High Similarity	NPC471670
0.8923	High Similarity	NPC12070
0.8923	High Similarity	NPC50924
0.8898	High Similarity	NPC193203
0.8889	High Similarity	NPC15837
0.8889	High Similarity	NPC71610
0.8855	High Similarity	NPC249272
0.8855	High Similarity	NPC153088
0.8846	High Similarity	NPC114183
0.8837	High Similarity	NPC18798
0.8837	High Similarity	NPC239134
0.88	High Similarity	NPC471187
0.88	High Similarity	NPC275145
0.879	High Similarity	NPC162935
0.879	High Similarity	NPC120545
0.879	High Similarity	NPC249340
0.8788	High Similarity	NPC474311
0.8779	High Similarity	NPC270899
0.875	High Similarity	NPC48248
0.875	High Similarity	NPC229894
0.873	High Similarity	NPC181334
0.8722	High Similarity	NPC277559
0.872	High Similarity	NPC307174
0.872	High Similarity	NPC11250
0.872	High Similarity	NPC91478
0.8712	High Similarity	NPC283088
0.871	High Similarity	NPC190971
0.871	High Similarity	NPC241001
0.8702	High Similarity	NPC4170
0.8702	High Similarity	NPC53896
0.8692	High Similarity	NPC93015
0.8692	High Similarity	NPC17083
0.8692	High Similarity	NPC244699
0.8692	High Similarity	NPC164295
0.8682	High Similarity	NPC34414
0.8682	High Similarity	NPC146647
0.8676	High Similarity	NPC308572
0.8672	High Similarity	NPC471530
0.8667	High Similarity	NPC471853
0.8667	High Similarity	NPC242136
0.8651	High Similarity	NPC174991
0.8647	High Similarity	NPC191976
0.8626	High Similarity	NPC165612
0.8615	High Similarity	NPC253488
0.8615	High Similarity	NPC27659
0.8613	High Similarity	NPC100242
0.8594	High Similarity	NPC160499
0.8593	High Similarity	NPC242994
0.8593	High Similarity	NPC138099
0.8583	High Similarity	NPC173978
0.8583	High Similarity	NPC231717
0.8583	High Similarity	NPC142956
0.8583	High Similarity	NPC164014
0.8582	High Similarity	NPC471905
0.8582	High Similarity	NPC49911
0.8571	High Similarity	NPC477596
0.8571	High Similarity	NPC121168
0.8571	High Similarity	NPC22644
0.8571	High Similarity	NPC80035
0.8561	High Similarity	NPC225051
0.8561	High Similarity	NPC59459
0.8561	High Similarity	NPC52407
0.8561	High Similarity	NPC267205
0.856	High Similarity	NPC472981
0.855	High Similarity	NPC476847
0.855	High Similarity	NPC474517
0.855	High Similarity	NPC72669
0.855	High Similarity	NPC41847
0.854	High Similarity	NPC477209
0.854	High Similarity	NPC201297
0.854	High Similarity	NPC248068
0.8538	High Similarity	NPC99731
0.8538	High Similarity	NPC25736
0.8537	High Similarity	NPC174087
0.8529	High Similarity	NPC181560
0.8529	High Similarity	NPC169452
0.8527	High Similarity	NPC19432
0.8525	High Similarity	NPC322197
0.8519	High Similarity	NPC4214
0.8519	High Similarity	NPC13715
0.8507	High Similarity	NPC7464
0.8507	High Similarity	NPC472308
0.8507	High Similarity	NPC254847
0.8504	High Similarity	NPC198014
0.8496	Intermediate Similarity	NPC166480
0.8496	Intermediate Similarity	NPC282780
0.8496	Intermediate Similarity	NPC477594
0.8492	Intermediate Similarity	NPC253627
0.8489	Intermediate Similarity	NPC478160
0.8485	Intermediate Similarity	NPC58685
0.8485	Intermediate Similarity	NPC183103
0.848	Intermediate Similarity	NPC285829
0.848	Intermediate Similarity	NPC206778
0.848	Intermediate Similarity	NPC190501
0.848	Intermediate Similarity	NPC478121
0.848	Intermediate Similarity	NPC318552
0.8473	Intermediate Similarity	NPC55949
0.8462	Intermediate Similarity	NPC282923
0.8455	Intermediate Similarity	NPC477453
0.845	Intermediate Similarity	NPC474737
0.845	Intermediate Similarity	NPC306765
0.845	Intermediate Similarity	NPC3224
0.8444	Intermediate Similarity	NPC119542
0.8444	Intermediate Similarity	NPC53206
0.8444	Intermediate Similarity	NPC53414
0.8438	Intermediate Similarity	NPC68756
0.8438	Intermediate Similarity	NPC152525
0.8433	Intermediate Similarity	NPC290803
0.8433	Intermediate Similarity	NPC258502
0.843	Intermediate Similarity	NPC250323
0.8425	Intermediate Similarity	NPC300274
0.8421	Intermediate Similarity	NPC115458
0.8421	Intermediate Similarity	NPC49742
0.8421	Intermediate Similarity	NPC263817
0.8417	Intermediate Similarity	NPC196941
0.8417	Intermediate Similarity	NPC309169
0.8413	Intermediate Similarity	NPC216216
0.8409	Intermediate Similarity	NPC291001
0.8409	Intermediate Similarity	NPC85342
0.8406	Intermediate Similarity	NPC19631
0.8406	Intermediate Similarity	NPC135524
0.8406	Intermediate Similarity	NPC239136
0.8406	Intermediate Similarity	NPC184935
0.8406	Intermediate Similarity	NPC193555
0.84	Intermediate Similarity	NPC42657
0.84	Intermediate Similarity	NPC473767
0.8397	Intermediate Similarity	NPC92624
0.8394	Intermediate Similarity	NPC476534
0.8382	Intermediate Similarity	NPC297797
0.8382	Intermediate Similarity	NPC28592
0.8382	Intermediate Similarity	NPC245760
0.8382	Intermediate Similarity	NPC157284
0.8382	Intermediate Similarity	NPC477849
0.8382	Intermediate Similarity	NPC46242
0.8382	Intermediate Similarity	NPC165191
0.8382	Intermediate Similarity	NPC61398
0.8382	Intermediate Similarity	NPC23667
0.8382	Intermediate Similarity	NPC51531
0.8382	Intermediate Similarity	NPC469857
0.8382	Intermediate Similarity	NPC473779
0.8382	Intermediate Similarity	NPC289358
0.8382	Intermediate Similarity	NPC42384
0.8382	Intermediate Similarity	NPC416
0.8382	Intermediate Similarity	NPC149773
0.8382	Intermediate Similarity	NPC50615
0.8382	Intermediate Similarity	NPC114333
0.8382	Intermediate Similarity	NPC91887
0.8382	Intermediate Similarity	NPC473479
0.8382	Intermediate Similarity	NPC5014
0.8372	Intermediate Similarity	NPC477454
0.8372	Intermediate Similarity	NPC87985
0.837	Intermediate Similarity	NPC315275
0.837	Intermediate Similarity	NPC118919
0.837	Intermediate Similarity	NPC155211
0.8369	Intermediate Similarity	NPC5568
0.8359	Intermediate Similarity	NPC375356
0.8357	Intermediate Similarity	NPC12402
0.8347	Intermediate Similarity	NPC260323
0.8347	Intermediate Similarity	NPC176279
0.8346	Intermediate Similarity	NPC295034
0.8346	Intermediate Similarity	NPC312560
0.8346	Intermediate Similarity	NPC175738
0.8345	Intermediate Similarity	NPC478164
0.8333	Intermediate Similarity	NPC204045
0.8333	Intermediate Similarity	NPC259942
0.8333	Intermediate Similarity	NPC246638
0.8333	Intermediate Similarity	NPC95172
0.8333	Intermediate Similarity	NPC136588

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 NPC254492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	980
0.2-0.3	1243
0.3-0.4	2586
0.4-0.5	2273
0.5-0.6	1204
0.6-0.7	454
0.7-0.8	80
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8699	High Similarity	NPD4196	Clinical (unspecified phase)
0.8629	High Similarity	NPD2932	Approved
0.8507	High Similarity	NPD1509	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD3019	Approved
0.8346	Intermediate Similarity	NPD1201	Approved
0.8231	Intermediate Similarity	NPD1470	Approved
0.816	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD7390	Discontinued
0.8043	Intermediate Similarity	NPD5408	Approved
0.8043	Intermediate Similarity	NPD5404	Approved
0.8043	Intermediate Similarity	NPD5405	Approved
0.8043	Intermediate Similarity	NPD5406	Approved
0.8	Intermediate Similarity	NPD5951	Approved
0.7943	Intermediate Similarity	NPD7003	Approved
0.7863	Intermediate Similarity	NPD3972	Approved
0.7846	Intermediate Similarity	NPD3023	Approved
0.7846	Intermediate Similarity	NPD3026	Approved
0.7829	Intermediate Similarity	NPD3025	Approved
0.7829	Intermediate Similarity	NPD3024	Approved
0.7769	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1164	Approved
0.7635	Intermediate Similarity	NPD7458	Discontinued
0.7609	Intermediate Similarity	NPD6663	Approved
0.7606	Intermediate Similarity	NPD2346	Discontinued
0.7603	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3300	Phase 2
0.7581	Intermediate Similarity	NPD2342	Discontinued
0.7574	Intermediate Similarity	NPD5736	Approved
0.7569	Intermediate Similarity	NPD8166	Discontinued
0.7559	Intermediate Similarity	NPD7635	Approved
0.7557	Intermediate Similarity	NPD1651	Approved
0.7554	Intermediate Similarity	NPD943	Approved
0.7535	Intermediate Similarity	NPD6100	Approved
0.7535	Intermediate Similarity	NPD6099	Approved
0.7535	Intermediate Similarity	NPD2935	Discontinued
0.752	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3091	Approved
0.7481	Intermediate Similarity	NPD1283	Approved
0.7479	Intermediate Similarity	NPD1809	Phase 2
0.7447	Intermediate Similarity	NPD1607	Approved
0.744	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3764	Approved
0.7407	Intermediate Similarity	NPD1755	Approved
0.74	Intermediate Similarity	NPD3226	Approved
0.7379	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD4059	Approved
0.7361	Intermediate Similarity	NPD2344	Approved
0.7343	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD844	Approved
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7329	Intermediate Similarity	NPD3750	Approved
0.7323	Intermediate Similarity	NPD4750	Phase 3
0.732	Intermediate Similarity	NPD7819	Suspended
0.7315	Intermediate Similarity	NPD6273	Approved
0.7305	Intermediate Similarity	NPD1240	Approved
0.7295	Intermediate Similarity	NPD3020	Approved
0.7273	Intermediate Similarity	NPD3495	Discontinued
0.7273	Intermediate Similarity	NPD288	Approved
0.7261	Intermediate Similarity	NPD6959	Discontinued
0.7259	Intermediate Similarity	NPD3092	Approved
0.7259	Intermediate Similarity	NPD1281	Approved
0.725	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2532	Approved
0.7248	Intermediate Similarity	NPD2533	Approved
0.7248	Intermediate Similarity	NPD2534	Approved
0.7236	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1876	Approved
0.7222	Intermediate Similarity	NPD1510	Phase 2
0.7218	Intermediate Similarity	NPD9545	Approved
0.7215	Intermediate Similarity	NPD6232	Discontinued
0.7214	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7008	Discontinued
0.7209	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4878	Approved
0.7192	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2859	Approved
0.719	Intermediate Similarity	NPD2860	Approved
0.7188	Intermediate Similarity	NPD7473	Discontinued
0.7171	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5691	Approved
0.7162	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD7610	Discontinued
0.7143	Intermediate Similarity	NPD2800	Approved
0.7133	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1930	Approved
0.712	Intermediate Similarity	NPD1929	Approved
0.7113	Intermediate Similarity	NPD8032	Phase 2
0.7111	Intermediate Similarity	NPD2286	Discontinued
0.7111	Intermediate Similarity	NPD3095	Discontinued
0.7109	Intermediate Similarity	NPD74	Approved
0.7109	Intermediate Similarity	NPD9266	Approved
0.7107	Intermediate Similarity	NPD2934	Approved
0.7107	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6651	Approved
0.7071	Intermediate Similarity	NPD4208	Discontinued
0.7068	Intermediate Similarity	NPD9493	Approved
0.7054	Intermediate Similarity	NPD3021	Approved
0.7054	Intermediate Similarity	NPD3022	Approved
0.705	Intermediate Similarity	NPD3094	Phase 2
0.7047	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2313	Discontinued
0.7031	Intermediate Similarity	NPD9263	Approved
0.7031	Intermediate Similarity	NPD9264	Approved
0.7031	Intermediate Similarity	NPD9267	Approved
0.7029	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD845	Approved
0.7016	Intermediate Similarity	NPD2066	Phase 3
0.7013	Intermediate Similarity	NPD4380	Phase 2
0.6994	Remote Similarity	NPD5844	Phase 1
0.6986	Remote Similarity	NPD3748	Approved
0.6986	Remote Similarity	NPD4308	Phase 3
0.6985	Remote Similarity	NPD1751	Approved
0.6966	Remote Similarity	NPD4097	Suspended
0.6963	Remote Similarity	NPD7009	Phase 2
0.6959	Remote Similarity	NPD1549	Phase 2
0.6957	Remote Similarity	NPD9269	Phase 2
0.695	Remote Similarity	NPD9494	Approved
0.6947	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2979	Phase 3
0.6943	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2796	Approved
0.6929	Remote Similarity	NPD2797	Approved
0.6929	Remote Similarity	NPD1237	Approved
0.6923	Remote Similarity	NPD3268	Approved
0.6912	Remote Similarity	NPD4093	Discontinued
0.6912	Remote Similarity	NPD9268	Approved
0.6903	Remote Similarity	NPD6599	Discontinued
0.6901	Remote Similarity	NPD4207	Discontinued
0.6892	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1471	Phase 3
0.6892	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6020	Phase 2
0.6887	Remote Similarity	NPD7236	Approved
0.6887	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4589	Approved
0.6859	Remote Similarity	NPD7411	Suspended
0.6857	Remote Similarity	NPD6696	Suspended
0.6855	Remote Similarity	NPD7075	Discontinued
0.6853	Remote Similarity	NPD4625	Phase 3
0.6842	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1511	Approved
0.6842	Remote Similarity	NPD1241	Discontinued
0.6835	Remote Similarity	NPD1608	Approved
0.6831	Remote Similarity	NPD3636	Approved
0.6831	Remote Similarity	NPD3635	Approved
0.6831	Remote Similarity	NPD3637	Approved
0.6829	Remote Similarity	NPD7177	Discontinued
0.6828	Remote Similarity	NPD4060	Phase 1
0.6824	Remote Similarity	NPD4476	Approved
0.6824	Remote Similarity	NPD4477	Approved
0.6815	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1934	Approved
0.6812	Remote Similarity	NPD4879	Approved
0.6797	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7028	Phase 2
0.6791	Remote Similarity	NPD497	Approved
0.6786	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2605	Approved
0.6783	Remote Similarity	NPD2606	Approved
0.6781	Remote Similarity	NPD230	Phase 1
0.6779	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7239	Suspended
0.6772	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD940	Approved
0.6772	Remote Similarity	NPD2801	Approved
0.6772	Remote Similarity	NPD1932	Approved
0.6772	Remote Similarity	NPD846	Approved
0.6765	Remote Similarity	NPD8150	Discontinued
0.6763	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2194	Approved
0.6761	Remote Similarity	NPD2195	Approved
0.6761	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4624	Approved
0.6753	Remote Similarity	NPD1512	Approved
0.675	Remote Similarity	NPD3749	Approved
0.6739	Remote Similarity	NPD1778	Approved
0.6736	Remote Similarity	NPD5155	Approved
0.6736	Remote Similarity	NPD5156	Approved
0.6721	Remote Similarity	NPD7609	Phase 3
0.6719	Remote Similarity	NPD9261	Approved
0.6716	Remote Similarity	NPD496	Approved
0.6716	Remote Similarity	NPD495	Approved
0.6716	Remote Similarity	NPD498	Approved
0.6713	Remote Similarity	NPD4212	Discontinued
0.6712	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3620	Phase 2
0.6712	Remote Similarity	NPD4140	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