NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	2.947
LogD:	2.812
LogS:	-3.442
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	2.529
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	1.4170971553539857e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.803
30% Bioavailability (F30%):	0.785

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	97.43917083740234%
Volume Distribution (VD):	0.61
Pgp-substrate:	1.8589788675308228%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.769
CYP2D6-inhibitor:	0.572
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.313
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	8.992
Half-life (T1/2):	0.632

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.439
AMES Toxicity:	0.758
Rat Oral Acute Toxicity:	0.495
Maximum Recommended Daily Dose:	0.276
Skin Sensitization:	0.911
Carcinogencity:	0.127
Eye Corrosion:	0.004
Eye Irritation:	0.927
Respiratory Toxicity:	0.324

Download Data

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

Natural Product: NPC160697

Natural Product ID:	NPC160697
*Common Name:**	Epheneranthol C
IUPAC Name:	4-methoxy-9,10-dihydrophenanthrene-2,3,5-triol
Synonyms:	Epheneranthol C
Standard InCHIKey:	LOICISWPCCICIA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-19-15-13-9(7-11(17)14(15)18)6-5-8-3-2-4-10(16)12(8)13/h2-4,7,16-18H,5-6H2,1H3
SMILES:	COc1c2c(CCc3c2c(O)ccc3)cc(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1085501
PubChem CID:	46871898
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
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16268553]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[16724831]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715978]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[20141173]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407005]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6178	Solanum euacanthum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13053	Corydalis conspersa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO326	Pittosporum brevicalyx	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15662	Ligustrum ovalifolium	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4581	Ungernia victoris	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15280	Sideritis grandiflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1575	Mikania luetzelburgii	Species	Asteraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	17600.0	nM	PMID[482575]

☑ 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 NPC160697 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	533
0.1-0.2	1874
0.2-0.3	5187
0.3-0.4	12547
0.4-0.5	4937
0.5-0.6	3789
0.6-0.7	7299
0.7-0.8	5056
0.8-0.85	783
0.85-0.9	439
0.9-0.95	212
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC202846
0.9845	High Similarity	NPC143139
0.9769	High Similarity	NPC151656
0.9767	High Similarity	NPC10314
0.9767	High Similarity	NPC200557
0.9767	High Similarity	NPC69029
0.9767	High Similarity	NPC108198
0.9767	High Similarity	NPC294884
0.9767	High Similarity	NPC158142
0.9695	High Similarity	NPC218131
0.9695	High Similarity	NPC243759
0.9695	High Similarity	NPC79622
0.9695	High Similarity	NPC29868
0.9695	High Similarity	NPC212942
0.9695	High Similarity	NPC105847
0.969	High Similarity	NPC125649
0.9621	High Similarity	NPC12668
0.9621	High Similarity	NPC308768
0.9618	High Similarity	NPC266453
0.9618	High Similarity	NPC56329
0.9618	High Similarity	NPC230919
0.9618	High Similarity	NPC200935
0.9618	High Similarity	NPC242715
0.9615	High Similarity	NPC241241
0.9615	High Similarity	NPC313081
0.9545	High Similarity	NPC243996
0.9545	High Similarity	NPC132804
0.9545	High Similarity	NPC275061
0.9545	High Similarity	NPC184613
0.9545	High Similarity	NPC220344
0.9542	High Similarity	NPC30632
0.9542	High Similarity	NPC205442
0.9478	High Similarity	NPC175838
0.947	High Similarity	NPC22902
0.947	High Similarity	NPC266006
0.9449	High Similarity	NPC266555
0.9398	High Similarity	NPC230124
0.9398	High Similarity	NPC6300
0.9398	High Similarity	NPC114171
0.9389	High Similarity	NPC209199
0.9385	High Similarity	NPC14224
0.9385	High Similarity	NPC161958
0.938	High Similarity	NPC126836
0.9375	High Similarity	NPC154866
0.9333	High Similarity	NPC183709
0.9328	High Similarity	NPC165026
0.9328	High Similarity	NPC73505
0.9328	High Similarity	NPC295719
0.9328	High Similarity	NPC34431
0.9323	High Similarity	NPC6262
0.9323	High Similarity	NPC73535
0.9323	High Similarity	NPC201145
0.9323	High Similarity	NPC90615
0.9323	High Similarity	NPC25111
0.9323	High Similarity	NPC272157
0.9313	High Similarity	NPC32778
0.9291	High Similarity	NPC105718
0.9291	High Similarity	NPC278955
0.9248	High Similarity	NPC114155
0.9248	High Similarity	NPC300846
0.9248	High Similarity	NPC476639
0.9242	High Similarity	NPC56764
0.9242	High Similarity	NPC206737
0.9242	High Similarity	NPC188378
0.9242	High Similarity	NPC276026
0.9242	High Similarity	NPC289258
0.9242	High Similarity	NPC7515
0.9242	High Similarity	NPC555
0.9242	High Similarity	NPC469659
0.9225	High Similarity	NPC23012
0.9219	High Similarity	NPC223953
0.9213	High Similarity	NPC228503
0.9213	High Similarity	NPC206487
0.9213	High Similarity	NPC138248
0.9213	High Similarity	NPC5796
0.9173	High Similarity	NPC111655
0.9173	High Similarity	NPC283009
0.9173	High Similarity	NPC55239
0.9173	High Similarity	NPC256262
0.9173	High Similarity	NPC240279
0.9173	High Similarity	NPC214853
0.9173	High Similarity	NPC180602
0.9173	High Similarity	NPC261873
0.916	High Similarity	NPC15543
0.9147	High Similarity	NPC236791
0.9147	High Similarity	NPC82679
0.9147	High Similarity	NPC471986
0.9147	High Similarity	NPC324112
0.9147	High Similarity	NPC246620
0.9147	High Similarity	NPC282000
0.9147	High Similarity	NPC169474
0.9147	High Similarity	NPC124452
0.9147	High Similarity	NPC74817
0.9147	High Similarity	NPC293054
0.9147	High Similarity	NPC159968
0.9137	High Similarity	NPC262297
0.9134	High Similarity	NPC84086
0.9124	High Similarity	NPC469630
0.9118	High Similarity	NPC472089
0.9104	High Similarity	NPC133025
0.9098	High Similarity	NPC103967
0.9098	High Similarity	NPC311256
0.9091	High Similarity	NPC228843
0.9091	High Similarity	NPC202762
0.9091	High Similarity	NPC86655
0.9091	High Similarity	NPC6451
0.9084	High Similarity	NPC234488
0.9084	High Similarity	NPC51840
0.9084	High Similarity	NPC299221
0.9084	High Similarity	NPC311680
0.9077	High Similarity	NPC38017
0.9077	High Similarity	NPC28765
0.907	High Similarity	NPC223136
0.907	High Similarity	NPC28730
0.907	High Similarity	NPC18924
0.907	High Similarity	NPC170485
0.907	High Similarity	NPC78974
0.907	High Similarity	NPC44748
0.907	High Similarity	NPC214406
0.907	High Similarity	NPC103823
0.9065	High Similarity	NPC126291
0.9051	High Similarity	NPC472087
0.9051	High Similarity	NPC470917
0.9051	High Similarity	NPC191231
0.9051	High Similarity	NPC472088
0.9044	High Similarity	NPC472090
0.9044	High Similarity	NPC472092
0.9044	High Similarity	NPC472091
0.9037	High Similarity	NPC46277
0.9037	High Similarity	NPC156948
0.9037	High Similarity	NPC86605
0.9037	High Similarity	NPC3072
0.9037	High Similarity	NPC301765
0.9015	High Similarity	NPC474356
0.9015	High Similarity	NPC149337
0.9015	High Similarity	NPC45715
0.9015	High Similarity	NPC471983
0.9015	High Similarity	NPC12275
0.9015	High Similarity	NPC232275
0.9008	High Similarity	NPC58164
0.9008	High Similarity	NPC10225
0.9	High Similarity	NPC21563
0.9	High Similarity	NPC236760
0.9	High Similarity	NPC53781
0.9	High Similarity	NPC252131
0.9	High Similarity	NPC127587
0.8992	High Similarity	NPC82483
0.8992	High Similarity	NPC475169
0.8992	High Similarity	NPC105925
0.8992	High Similarity	NPC17943
0.8992	High Similarity	NPC208950
0.8992	High Similarity	NPC60885
0.8992	High Similarity	NPC299584
0.8992	High Similarity	NPC57490
0.8992	High Similarity	NPC233410
0.8992	High Similarity	NPC234400
0.8992	High Similarity	NPC116907
0.8992	High Similarity	NPC298757
0.8992	High Similarity	NPC203133
0.8992	High Similarity	NPC472093
0.8992	High Similarity	NPC251855
0.8992	High Similarity	NPC221077
0.8992	High Similarity	NPC117214
0.8992	High Similarity	NPC193544
0.8992	High Similarity	NPC265483
0.8984	High Similarity	NPC121115
0.8984	High Similarity	NPC197757
0.8984	High Similarity	NPC228922
0.8978	High Similarity	NPC265075
0.8971	High Similarity	NPC70682
0.8971	High Similarity	NPC471183
0.8971	High Similarity	NPC32630
0.8971	High Similarity	NPC260741
0.8971	High Similarity	NPC55947
0.8963	High Similarity	NPC265433
0.8963	High Similarity	NPC270456
0.8963	High Similarity	NPC234952
0.8963	High Similarity	NPC248727
0.8963	High Similarity	NPC162659
0.8947	High Similarity	NPC127624
0.8947	High Similarity	NPC218884
0.8939	High Similarity	NPC192687
0.8939	High Similarity	NPC224157
0.8931	High Similarity	NPC46274
0.8931	High Similarity	NPC215300
0.8931	High Similarity	NPC226331
0.8931	High Similarity	NPC266691
0.8929	High Similarity	NPC112251
0.8929	High Similarity	NPC233980
0.8923	High Similarity	NPC76451
0.8921	High Similarity	NPC50250
0.8921	High Similarity	NPC473108
0.8921	High Similarity	NPC469795
0.8906	High Similarity	NPC41562
0.8905	High Similarity	NPC266650
0.8897	High Similarity	NPC35550
0.8889	High Similarity	NPC474206
0.8889	High Similarity	NPC112246
0.8889	High Similarity	NPC121812
0.8889	High Similarity	NPC112939

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 NPC160697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	458
0.1-0.2	953
0.2-0.3	1785
0.3-0.4	2821
0.4-0.5	1553
0.5-0.6	852
0.6-0.7	604
0.7-0.8	113
0.8-0.85	8
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD1529	Clinical (unspecified phase)
0.8864	High Similarity	NPD3027	Phase 3
0.8855	High Similarity	NPD1530	Clinical (unspecified phase)
0.8806	High Similarity	NPD1613	Approved
0.8806	High Similarity	NPD1612	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD4625	Phase 3
0.812	Intermediate Similarity	NPD1610	Phase 2
0.8116	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD228	Approved
0.8105	Intermediate Similarity	NPD6234	Discontinued
0.8102	Intermediate Similarity	NPD4908	Phase 1
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.8029	Intermediate Similarity	NPD3018	Phase 2
0.8013	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3620	Phase 2
0.7955	Intermediate Similarity	NPD1548	Phase 1
0.7911	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD1934	Approved
0.7868	Intermediate Similarity	NPD2983	Phase 2
0.7868	Intermediate Similarity	NPD2982	Phase 2
0.7857	Intermediate Similarity	NPD4967	Phase 2
0.7857	Intermediate Similarity	NPD4965	Approved
0.7857	Intermediate Similarity	NPD4966	Approved
0.7846	Intermediate Similarity	NPD5283	Phase 1
0.7794	Intermediate Similarity	NPD2981	Phase 2
0.775	Intermediate Similarity	NPD7228	Approved
0.7737	Intermediate Similarity	NPD4749	Approved
0.7737	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2801	Approved
0.7727	Intermediate Similarity	NPD1465	Phase 2
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1511	Approved
0.7702	Intermediate Similarity	NPD5844	Phase 1
0.7698	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6674	Discontinued
0.7687	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4060	Phase 1
0.7616	Intermediate Similarity	NPD1512	Approved
0.7609	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7199	Phase 2
0.7538	Intermediate Similarity	NPD3021	Approved
0.7538	Intermediate Similarity	NPD3022	Approved
0.7518	Intermediate Similarity	NPD2861	Phase 2
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD1653	Approved
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1558	Phase 1
0.7468	Intermediate Similarity	NPD4005	Discontinued
0.7464	Intermediate Similarity	NPD3705	Approved
0.7453	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3540	Phase 1
0.7405	Intermediate Similarity	NPD3882	Suspended
0.7397	Intermediate Similarity	NPD4097	Suspended
0.7365	Intermediate Similarity	NPD3539	Phase 1
0.7358	Intermediate Similarity	NPD4055	Discovery
0.7351	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7323	Intermediate Similarity	NPD1242	Phase 1
0.7321	Intermediate Similarity	NPD8054	Approved
0.7321	Intermediate Similarity	NPD8053	Approved
0.7319	Intermediate Similarity	NPD4626	Approved
0.7305	Intermediate Similarity	NPD1283	Approved
0.7297	Intermediate Similarity	NPD1510	Phase 2
0.7285	Intermediate Similarity	NPD3750	Approved
0.7279	Intermediate Similarity	NPD1607	Approved
0.7273	Intermediate Similarity	NPD4750	Phase 3
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.726	Intermediate Similarity	NPD1240	Approved
0.7254	Intermediate Similarity	NPD3094	Phase 2
0.7252	Intermediate Similarity	NPD2342	Discontinued
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7246	Intermediate Similarity	NPD1651	Approved
0.7246	Intermediate Similarity	NPD7240	Approved
0.7233	Intermediate Similarity	NPD3817	Phase 2
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7222	Intermediate Similarity	NPD6959	Discontinued
0.7219	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1611	Approved
0.7212	Intermediate Similarity	NPD3818	Discontinued
0.7211	Intermediate Similarity	NPD5735	Approved
0.7211	Intermediate Similarity	NPD3657	Discovery
0.7208	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD709	Approved
0.7203	Intermediate Similarity	NPD4624	Approved
0.7197	Intermediate Similarity	NPD4380	Phase 2
0.719	Intermediate Similarity	NPD7124	Phase 2
0.7183	Intermediate Similarity	NPD6696	Suspended
0.7183	Intermediate Similarity	NPD8651	Approved
0.7169	Intermediate Similarity	NPD7054	Approved
0.7161	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7472	Approved
0.7123	Intermediate Similarity	NPD5109	Approved
0.7123	Intermediate Similarity	NPD5110	Phase 2
0.7123	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5111	Phase 2
0.7115	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1669	Approved
0.7111	Intermediate Similarity	NPD7635	Approved
0.7105	Intermediate Similarity	NPD5177	Phase 3
0.7101	Intermediate Similarity	NPD5536	Phase 2
0.7097	Intermediate Similarity	NPD7447	Phase 1
0.7095	Intermediate Similarity	NPD230	Phase 1
0.7093	Intermediate Similarity	NPD7906	Approved
0.7092	Intermediate Similarity	NPD1091	Approved
0.7092	Intermediate Similarity	NPD3092	Approved
0.7092	Intermediate Similarity	NPD1281	Approved
0.7089	Intermediate Similarity	NPD4675	Approved
0.7089	Intermediate Similarity	NPD4678	Approved
0.7086	Intermediate Similarity	NPD5762	Approved
0.7086	Intermediate Similarity	NPD7266	Discontinued
0.7086	Intermediate Similarity	NPD5763	Approved
0.7086	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6671	Approved
0.7076	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7229	Phase 3
0.7067	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD4577	Approved
0.7059	Intermediate Similarity	NPD3892	Phase 2
0.7059	Intermediate Similarity	NPD4578	Approved
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7095	Approved
0.7055	Intermediate Similarity	NPD5494	Approved
0.7052	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5090	Approved
0.7044	Intermediate Similarity	NPD5089	Approved
0.7039	Intermediate Similarity	NPD1549	Phase 2
0.7035	Intermediate Similarity	NPD4663	Approved
0.7032	Intermediate Similarity	NPD7213	Phase 3
0.7032	Intermediate Similarity	NPD7041	Phase 2
0.7032	Intermediate Similarity	NPD7212	Phase 2
0.7032	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2238	Phase 2
0.702	Intermediate Similarity	NPD2935	Discontinued
0.7013	Intermediate Similarity	NPD5241	Discontinued
0.7013	Intermediate Similarity	NPD2219	Phase 1
0.7013	Intermediate Similarity	NPD2677	Approved
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD6111	Discontinued
0.7	Intermediate Similarity	NPD1357	Approved
0.7	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4536	Approved
0.7	Intermediate Similarity	NPD4538	Approved
0.6993	Remote Similarity	NPD1652	Phase 2
0.6993	Remote Similarity	NPD5327	Phase 3
0.6993	Remote Similarity	NPD3060	Approved
0.6992	Remote Similarity	NPD290	Approved
0.6988	Remote Similarity	NPD27	Approved
0.6988	Remote Similarity	NPD2489	Approved
0.6987	Remote Similarity	NPD2532	Approved
0.6987	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2533	Approved
0.6987	Remote Similarity	NPD2534	Approved
0.6982	Remote Similarity	NPD6797	Phase 2
0.6982	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7768	Phase 2
0.697	Remote Similarity	NPD3787	Discontinued
0.697	Remote Similarity	NPD3051	Approved
0.6966	Remote Similarity	NPD6584	Phase 3
0.6959	Remote Similarity	NPD2674	Phase 3
0.6959	Remote Similarity	NPD7311	Approved
0.6959	Remote Similarity	NPD7312	Approved
0.6959	Remote Similarity	NPD7313	Approved
0.6959	Remote Similarity	NPD7310	Approved
0.6957	Remote Similarity	NPD7157	Approved
0.6954	Remote Similarity	NPD3748	Approved
0.6954	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6559	Discontinued
0.6941	Remote Similarity	NPD7251	Discontinued
0.694	Remote Similarity	NPD2684	Approved
0.6934	Remote Similarity	NPD1398	Phase 1
0.6933	Remote Similarity	NPD7075	Discontinued
0.6929	Remote Similarity	NPD9296	Approved
0.6929	Remote Similarity	NPD3091	Approved
0.6928	Remote Similarity	NPD2969	Approved
0.6928	Remote Similarity	NPD2970	Approved
0.6927	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2233	Approved
0.6923	Remote Similarity	NPD2232	Approved
0.6923	Remote Similarity	NPD7390	Discontinued
0.6923	Remote Similarity	NPD2230	Approved
0.6919	Remote Similarity	NPD7309	Approved
0.6918	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD9494	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