NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	278.965
LogP:	3.236
LogD:	3.05
LogS:	-4.23
# Rotatable Bonds:	2
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.882
Synthetic Accessibility Score:	2.401
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	1.6618927475064993e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	97.02497100830078%
Volume Distribution (VD):	0.583
Pgp-substrate:	2.140547752380371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.886
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.548
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.294
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.44
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.405

ADMET: Excretion

Clearance (CL):	5.687
Half-life (T1/2):	0.388

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.298
AMES Toxicity:	0.518
Rat Oral Acute Toxicity:	0.388
Maximum Recommended Daily Dose:	0.339
Skin Sensitization:	0.567
Carcinogencity:	0.127
Eye Corrosion:	0.004
Eye Irritation:	0.791
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC143139

Natural Product ID:	NPC143139
*Common Name:**	Marylaurencinols A
IUPAC Name:	2,4-dimethoxy-9,10-dihydrophenanthrene-3,5-diol
Synonyms:	Marylaurencinols A
Standard InCHIKey:	HPDSFXKGXUGRME-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-19-12-8-10-7-6-9-4-3-5-11(17)13(9)14(10)16(20-2)15(12)18/h3-5,8,17-18H,6-7H2,1-2H3
SMILES:	COc1cc2CCc3cccc(c3-c2c(c1O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2042414
PubChem CID:	57408886
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO33438	cymbidium great flower marie laurencin	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537363]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	96800.0	nM	PMID[476194]

☑ 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 NPC143139 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	460
0.1-0.2	1796
0.2-0.3	4745
0.3-0.4	12538
0.4-0.5	5366
0.5-0.6	3772
0.6-0.7	7027
0.7-0.8	5408
0.8-0.85	815
0.85-0.9	461
0.9-0.95	273
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202846
0.9922	High Similarity	NPC294884
0.9922	High Similarity	NPC158142
0.9922	High Similarity	NPC200557
0.9922	High Similarity	NPC10314
0.9922	High Similarity	NPC108198
0.9922	High Similarity	NPC69029
0.9847	High Similarity	NPC212942
0.9847	High Similarity	NPC79622
0.9847	High Similarity	NPC29868
0.9845	High Similarity	NPC125649
0.9845	High Similarity	NPC160697
0.9773	High Similarity	NPC308768
0.9773	High Similarity	NPC12668
0.9771	High Similarity	NPC56329
0.9771	High Similarity	NPC242715
0.9769	High Similarity	NPC313081
0.9769	High Similarity	NPC241241
0.9697	High Similarity	NPC275061
0.9697	High Similarity	NPC220344
0.9697	High Similarity	NPC243996
0.9697	High Similarity	NPC218131
0.9697	High Similarity	NPC243759
0.9697	High Similarity	NPC184613
0.9697	High Similarity	NPC105847
0.9697	High Similarity	NPC132804
0.9695	High Similarity	NPC205442
0.9695	High Similarity	NPC30632
0.9627	High Similarity	NPC175838
0.9621	High Similarity	NPC22902
0.9621	High Similarity	NPC151656
0.9621	High Similarity	NPC266453
0.9621	High Similarity	NPC230919
0.9621	High Similarity	NPC266006
0.9621	High Similarity	NPC200935
0.9549	High Similarity	NPC6300
0.9549	High Similarity	NPC114171
0.9549	High Similarity	NPC230124
0.9542	High Similarity	NPC209199
0.9538	High Similarity	NPC14224
0.9538	High Similarity	NPC161958
0.9535	High Similarity	NPC126836
0.9481	High Similarity	NPC183709
0.9478	High Similarity	NPC73505
0.9478	High Similarity	NPC34431
0.9478	High Similarity	NPC295719
0.9478	High Similarity	NPC165026
0.9474	High Similarity	NPC90615
0.9474	High Similarity	NPC25111
0.9474	High Similarity	NPC6262
0.9474	High Similarity	NPC201145
0.9474	High Similarity	NPC73535
0.9474	High Similarity	NPC272157
0.9466	High Similarity	NPC32778
0.9398	High Similarity	NPC476639
0.9398	High Similarity	NPC300846
0.9398	High Similarity	NPC114155
0.9394	High Similarity	NPC469659
0.9394	High Similarity	NPC7515
0.9394	High Similarity	NPC289258
0.9394	High Similarity	NPC188378
0.9394	High Similarity	NPC276026
0.9394	High Similarity	NPC206737
0.9394	High Similarity	NPC56764
0.9394	High Similarity	NPC555
0.938	High Similarity	NPC154866
0.9323	High Similarity	NPC111655
0.9323	High Similarity	NPC180602
0.9323	High Similarity	NPC240279
0.9323	High Similarity	NPC256262
0.9323	High Similarity	NPC214853
0.9323	High Similarity	NPC55239
0.9323	High Similarity	NPC283009
0.9323	High Similarity	NPC261873
0.9313	High Similarity	NPC15543
0.9302	High Similarity	NPC282000
0.9302	High Similarity	NPC324112
0.9302	High Similarity	NPC169474
0.9302	High Similarity	NPC74817
0.9302	High Similarity	NPC471986
0.9302	High Similarity	NPC266555
0.9302	High Similarity	NPC293054
0.9302	High Similarity	NPC246620
0.9302	High Similarity	NPC159968
0.9302	High Similarity	NPC82679
0.9302	High Similarity	NPC124452
0.9302	High Similarity	NPC236791
0.9281	High Similarity	NPC262297
0.927	High Similarity	NPC469630
0.9265	High Similarity	NPC472089
0.9254	High Similarity	NPC133025
0.9248	High Similarity	NPC103967
0.9248	High Similarity	NPC311256
0.9242	High Similarity	NPC228843
0.9242	High Similarity	NPC6451
0.9237	High Similarity	NPC234488
0.9237	High Similarity	NPC299221
0.9237	High Similarity	NPC51840
0.9237	High Similarity	NPC311680
0.9231	High Similarity	NPC28765
0.9225	High Similarity	NPC170485
0.9225	High Similarity	NPC78974
0.9225	High Similarity	NPC214406
0.9225	High Similarity	NPC223136
0.9225	High Similarity	NPC223953
0.9225	High Similarity	NPC28730
0.9225	High Similarity	NPC103823
0.9225	High Similarity	NPC44748
0.9225	High Similarity	NPC18924
0.9209	High Similarity	NPC126291
0.9197	High Similarity	NPC470917
0.9197	High Similarity	NPC472087
0.9197	High Similarity	NPC191231
0.9197	High Similarity	NPC472088
0.9191	High Similarity	NPC472092
0.9191	High Similarity	NPC472090
0.9191	High Similarity	NPC472091
0.9185	High Similarity	NPC3072
0.9185	High Similarity	NPC301765
0.9185	High Similarity	NPC156948
0.9185	High Similarity	NPC86605
0.9185	High Similarity	NPC46277
0.9167	High Similarity	NPC45715
0.9167	High Similarity	NPC232275
0.9167	High Similarity	NPC471983
0.9167	High Similarity	NPC474356
0.9167	High Similarity	NPC12275
0.9167	High Similarity	NPC149337
0.916	High Similarity	NPC10225
0.916	High Similarity	NPC58164
0.9154	High Similarity	NPC252131
0.9154	High Similarity	NPC127587
0.9154	High Similarity	NPC21563
0.9154	High Similarity	NPC236760
0.9147	High Similarity	NPC221077
0.9147	High Similarity	NPC193544
0.9147	High Similarity	NPC17943
0.9147	High Similarity	NPC208950
0.9147	High Similarity	NPC60885
0.9147	High Similarity	NPC82483
0.9147	High Similarity	NPC475169
0.9147	High Similarity	NPC265483
0.9147	High Similarity	NPC233410
0.9147	High Similarity	NPC203133
0.9147	High Similarity	NPC105925
0.9147	High Similarity	NPC116907
0.9147	High Similarity	NPC234400
0.9147	High Similarity	NPC298757
0.9147	High Similarity	NPC251855
0.9147	High Similarity	NPC117214
0.9147	High Similarity	NPC105718
0.9147	High Similarity	NPC472093
0.9147	High Similarity	NPC278955
0.9147	High Similarity	NPC299584
0.9147	High Similarity	NPC57490
0.9124	High Similarity	NPC265075
0.9118	High Similarity	NPC260741
0.9118	High Similarity	NPC32630
0.9118	High Similarity	NPC55947
0.9118	High Similarity	NPC70682
0.9118	High Similarity	NPC471183
0.9111	High Similarity	NPC270456
0.9111	High Similarity	NPC234952
0.9111	High Similarity	NPC162659
0.9111	High Similarity	NPC265433
0.9111	High Similarity	NPC248727
0.9098	High Similarity	NPC202762
0.9098	High Similarity	NPC127624
0.9098	High Similarity	NPC86655
0.9098	High Similarity	NPC218884
0.9091	High Similarity	NPC192687
0.9091	High Similarity	NPC224157
0.9084	High Similarity	NPC23012
0.9084	High Similarity	NPC266691
0.9077	High Similarity	NPC76451
0.9071	High Similarity	NPC112251
0.9071	High Similarity	NPC233980
0.907	High Similarity	NPC206487
0.907	High Similarity	NPC228503
0.907	High Similarity	NPC138248
0.907	High Similarity	NPC5796
0.9065	High Similarity	NPC469795
0.9065	High Similarity	NPC50250
0.9065	High Similarity	NPC473108
0.9051	High Similarity	NPC266650
0.9044	High Similarity	NPC35550
0.9037	High Similarity	NPC112939
0.9037	High Similarity	NPC474206
0.9037	High Similarity	NPC470356
0.9037	High Similarity	NPC94750
0.9037	High Similarity	NPC121812
0.9037	High Similarity	NPC112246
0.903	High Similarity	NPC229442
0.903	High Similarity	NPC168059
0.9023	High Similarity	NPC474017
0.9023	High Similarity	NPC282508
0.9015	High Similarity	NPC190144
0.9015	High Similarity	NPC170844
0.9015	High Similarity	NPC476968
0.9015	High Similarity	NPC212015

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 NPC143139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	954
0.2-0.3	1723
0.3-0.4	2819
0.4-0.5	1620
0.5-0.6	853
0.6-0.7	629
0.7-0.8	133
0.8-0.85	10
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9015	High Similarity	NPD3027	Phase 3
0.8797	High Similarity	NPD1529	Clinical (unspecified phase)
0.8722	High Similarity	NPD1530	Clinical (unspecified phase)
0.8676	High Similarity	NPD1613	Approved
0.8676	High Similarity	NPD1612	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD4625	Phase 3
0.8261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD4908	Phase 1
0.8235	Intermediate Similarity	NPD6234	Discontinued
0.8194	Intermediate Similarity	NPD6232	Discontinued
0.8175	Intermediate Similarity	NPD3018	Phase 2
0.8146	Intermediate Similarity	NPD37	Approved
0.8143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD3620	Phase 2
0.8038	Intermediate Similarity	NPD7473	Discontinued
0.8015	Intermediate Similarity	NPD2982	Phase 2
0.8015	Intermediate Similarity	NPD2983	Phase 2
0.8	Intermediate Similarity	NPD5283	Phase 1
0.8	Intermediate Similarity	NPD1610	Phase 2
0.7987	Intermediate Similarity	NPD4966	Approved
0.7987	Intermediate Similarity	NPD4967	Phase 2
0.7987	Intermediate Similarity	NPD4965	Approved
0.7984	Intermediate Similarity	NPD228	Approved
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7908	Intermediate Similarity	NPD1934	Approved
0.7883	Intermediate Similarity	NPD4749	Approved
0.7883	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7228	Approved
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2801	Approved
0.7842	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1548	Phase 1
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7823	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6674	Discontinued
0.7762	Intermediate Similarity	NPD4060	Phase 1
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3022	Approved
0.7692	Intermediate Similarity	NPD3021	Approved
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.766	Intermediate Similarity	NPD2861	Phase 2
0.7643	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6166	Phase 2
0.7628	Intermediate Similarity	NPD1465	Phase 2
0.7616	Intermediate Similarity	NPD1511	Approved
0.7609	Intermediate Similarity	NPD3705	Approved
0.7597	Intermediate Similarity	NPD4005	Discontinued
0.7578	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3540	Phase 1
0.7534	Intermediate Similarity	NPD4097	Suspended
0.7532	Intermediate Similarity	NPD3882	Suspended
0.7532	Intermediate Similarity	NPD1653	Approved
0.7516	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3539	Phase 1
0.7484	Intermediate Similarity	NPD4055	Discovery
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD4626	Approved
0.744	Intermediate Similarity	NPD8053	Approved
0.744	Intermediate Similarity	NPD8054	Approved
0.7424	Intermediate Similarity	NPD4750	Phase 3
0.7397	Intermediate Similarity	NPD1558	Phase 1
0.7394	Intermediate Similarity	NPD3094	Phase 2
0.7383	Intermediate Similarity	NPD6100	Approved
0.7383	Intermediate Similarity	NPD6099	Approved
0.7365	Intermediate Similarity	NPD7240	Approved
0.7358	Intermediate Similarity	NPD3817	Phase 2
0.7349	Intermediate Similarity	NPD7074	Phase 3
0.7347	Intermediate Similarity	NPD3657	Discovery
0.7347	Intermediate Similarity	NPD5735	Approved
0.7346	Intermediate Similarity	NPD6959	Discontinued
0.7343	Intermediate Similarity	NPD4624	Approved
0.7338	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.7325	Intermediate Similarity	NPD4380	Phase 2
0.7324	Intermediate Similarity	NPD8651	Approved
0.7324	Intermediate Similarity	NPD6696	Suspended
0.732	Intermediate Similarity	NPD7124	Phase 2
0.7303	Intermediate Similarity	NPD3750	Approved
0.729	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7054	Approved
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7273	Intermediate Similarity	NPD2342	Discontinued
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1651	Approved
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5111	Phase 2
0.726	Intermediate Similarity	NPD5110	Phase 2
0.726	Intermediate Similarity	NPD5109	Approved
0.7259	Intermediate Similarity	NPD7635	Approved
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7246	Intermediate Similarity	NPD7472	Approved
0.7244	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5177	Phase 3
0.7234	Intermediate Similarity	NPD3092	Approved
0.7234	Intermediate Similarity	NPD422	Phase 1
0.7226	Intermediate Similarity	NPD6671	Approved
0.7226	Intermediate Similarity	NPD7447	Phase 1
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD5763	Approved
0.7215	Intermediate Similarity	NPD4678	Approved
0.7215	Intermediate Similarity	NPD4675	Approved
0.7209	Intermediate Similarity	NPD7906	Approved
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7203	Intermediate Similarity	NPD1283	Approved
0.72	Intermediate Similarity	NPD1510	Phase 2
0.7195	Intermediate Similarity	NPD7229	Phase 3
0.7193	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3892	Phase 2
0.7188	Intermediate Similarity	NPD7819	Suspended
0.7181	Intermediate Similarity	NPD1607	Approved
0.7178	Intermediate Similarity	NPD5494	Approved
0.7176	Intermediate Similarity	NPD4578	Approved
0.7176	Intermediate Similarity	NPD4577	Approved
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5090	Approved
0.717	Intermediate Similarity	NPD5089	Approved
0.7168	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD2238	Phase 2
0.7161	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7212	Phase 2
0.7161	Intermediate Similarity	NPD7041	Phase 2
0.7161	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD2935	Discontinued
0.7151	Intermediate Similarity	NPD4663	Approved
0.7143	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD5241	Discontinued
0.7133	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4536	Approved
0.7133	Intermediate Similarity	NPD1669	Approved
0.7133	Intermediate Similarity	NPD5327	Phase 3
0.7133	Intermediate Similarity	NPD4538	Approved
0.7133	Intermediate Similarity	NPD6111	Discontinued
0.7124	Intermediate Similarity	NPD3060	Approved
0.7118	Intermediate Similarity	NPD7549	Discontinued
0.7115	Intermediate Similarity	NPD2532	Approved
0.7115	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2534	Approved
0.7115	Intermediate Similarity	NPD2533	Approved
0.7113	Intermediate Similarity	NPD1611	Approved
0.7113	Intermediate Similarity	NPD1091	Approved
0.7108	Intermediate Similarity	NPD27	Approved
0.7108	Intermediate Similarity	NPD2489	Approved
0.7103	Intermediate Similarity	NPD6584	Phase 3
0.7101	Intermediate Similarity	NPD7157	Approved
0.7101	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD709	Approved
0.7101	Intermediate Similarity	NPD6797	Phase 2
0.7099	Intermediate Similarity	NPD7768	Phase 2
0.7095	Intermediate Similarity	NPD2674	Phase 3
0.7091	Intermediate Similarity	NPD3787	Discontinued
0.7091	Intermediate Similarity	NPD3051	Approved
0.709	Intermediate Similarity	NPD2684	Approved
0.7076	Intermediate Similarity	NPD7310	Approved
0.7076	Intermediate Similarity	NPD7311	Approved
0.7076	Intermediate Similarity	NPD7312	Approved
0.7076	Intermediate Similarity	NPD7313	Approved
0.7071	Intermediate Similarity	NPD3091	Approved
0.7063	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD2233	Approved
0.7063	Intermediate Similarity	NPD2230	Approved
0.7059	Intermediate Similarity	NPD6559	Discontinued
0.7059	Intermediate Similarity	NPD7251	Discontinued
0.7055	Intermediate Similarity	NPD7075	Discontinued
0.7051	Intermediate Similarity	NPD7390	Discontinued
0.7048	Intermediate Similarity	NPD2969	Approved
0.7048	Intermediate Similarity	NPD2970	Approved
0.7047	Intermediate Similarity	NPD943	Approved
0.7047	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5451	Approved
0.7035	Intermediate Similarity	NPD7309	Approved
0.7032	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6190	Approved
0.7027	Intermediate Similarity	NPD6798	Discontinued
0.7024	Intermediate Similarity	NPD8251	Approved
0.7024	Intermediate Similarity	NPD8099	Discontinued
0.7024	Intermediate Similarity	NPD8252	Approved
0.7021	Intermediate Similarity	NPD1357	Approved
0.7018	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7808	Phase 3
0.7013	Intermediate Similarity	NPD1652	Phase 2
0.7007	Intermediate Similarity	NPD7843	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