NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	278.965
LogP:	3.019
LogD:	3.224
LogS:	-3.953
# 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:	2.362
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:	-4.864
MDCK Permeability:	1.5243944289977662e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.569
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.829
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	93.0698013305664%
Volume Distribution (VD):	0.814
Pgp-substrate:	4.931869029998779%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.403
CYP2C19-substrate:	0.153
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.785
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	11.553
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.472
AMES Toxicity:	0.37
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.657
Carcinogencity:	0.028
Eye Corrosion:	0.004
Eye Irritation:	0.731
Respiratory Toxicity:	0.592

Download Data

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

Natural Product: NPC125649

Natural Product ID:	NPC125649
*Common Name:**	3,5-Dimethoxy-9,10-Dihydrophenanthrene-2,7-Diol
IUPAC Name:	3,5-dimethoxy-9,10-dihydrophenanthrene-2,7-diol
Synonyms:
Standard InCHIKey:	BHEGXSNCDUBUFA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-19-14-8-12-9(6-13(14)18)3-4-10-5-11(17)7-15(20-2)16(10)12/h5-8,17-18H,3-4H2,1-2H3
SMILES:	COc1cc(O)cc2c1c1cc(OC)c(cc1CC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562498
PubChem CID:	45267920
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
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18640035]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193043]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23707257]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5001	Ramalina calicaris	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5822	Suberites massa	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14623	Senecio clevelandi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	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
EC50	7

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	4.24	ug.mL-1	PMID[453422]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	2.67	ug.mL-1	PMID[453422]
NPT90	Cell Line	DU-145	Homo sapiens	EC50	=	5.38	ug.mL-1	PMID[453422]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	4.55	ug.mL-1	PMID[453422]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	2.59	ug.mL-1	PMID[453422]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	3.9	ug.mL-1	PMID[453422]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	5.84	ug.mL-1	PMID[453422]

☑ 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 NPC125649 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	447
0.1-0.2	1843
0.2-0.3	4939
0.3-0.4	12742
0.4-0.5	5111
0.5-0.6	3861
0.6-0.7	7198
0.7-0.8	5088
0.8-0.85	817
0.85-0.9	412
0.9-0.95	206
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC294884
0.9922	High Similarity	NPC158142
0.9922	High Similarity	NPC200557
0.9922	High Similarity	NPC10314
0.9922	High Similarity	NPC69029
0.9922	High Similarity	NPC108198
0.9845	High Similarity	NPC202846
0.9845	High Similarity	NPC143139
0.9769	High Similarity	NPC22902
0.9769	High Similarity	NPC242715
0.9769	High Similarity	NPC56329
0.9767	High Similarity	NPC313081
0.9767	High Similarity	NPC241241
0.9695	High Similarity	NPC275061
0.9695	High Similarity	NPC220344
0.9695	High Similarity	NPC132804
0.9695	High Similarity	NPC243996
0.9695	High Similarity	NPC79622
0.9695	High Similarity	NPC29868
0.9695	High Similarity	NPC212942
0.9692	High Similarity	NPC30632
0.969	High Similarity	NPC209199
0.969	High Similarity	NPC160697
0.9688	High Similarity	NPC161958
0.9688	High Similarity	NPC14224
0.9621	High Similarity	NPC12668
0.9621	High Similarity	NPC308768
0.9618	High Similarity	NPC266453
0.9618	High Similarity	NPC230919
0.9618	High Similarity	NPC200935
0.9545	High Similarity	NPC6300
0.9545	High Similarity	NPC105847
0.9545	High Similarity	NPC243759
0.9545	High Similarity	NPC114171
0.9545	High Similarity	NPC230124
0.9545	High Similarity	NPC184613
0.9545	High Similarity	NPC218131
0.9542	High Similarity	NPC205442
0.9531	High Similarity	NPC126836
0.9478	High Similarity	NPC175838
0.9478	High Similarity	NPC183709
0.947	High Similarity	NPC151656
0.947	High Similarity	NPC266006
0.9462	High Similarity	NPC32778
0.9449	High Similarity	NPC471986
0.9389	High Similarity	NPC56764
0.9389	High Similarity	NPC7515
0.9389	High Similarity	NPC188378
0.9389	High Similarity	NPC206737
0.9389	High Similarity	NPC555
0.9389	High Similarity	NPC469659
0.9389	High Similarity	NPC289258
0.9389	High Similarity	NPC276026
0.9385	High Similarity	NPC228843
0.9375	High Similarity	NPC154866
0.9375	High Similarity	NPC28765
0.9333	High Similarity	NPC191231
0.9328	High Similarity	NPC165026
0.9328	High Similarity	NPC73505
0.9328	High Similarity	NPC295719
0.9328	High Similarity	NPC34431
0.9323	High Similarity	NPC90615
0.9323	High Similarity	NPC73535
0.9323	High Similarity	NPC6262
0.9323	High Similarity	NPC201145
0.9323	High Similarity	NPC25111
0.9323	High Similarity	NPC272157
0.9318	High Similarity	NPC55239
0.9318	High Similarity	NPC180602
0.9318	High Similarity	NPC214853
0.9318	High Similarity	NPC240279
0.9308	High Similarity	NPC15543
0.9297	High Similarity	NPC169474
0.9297	High Similarity	NPC82679
0.9297	High Similarity	NPC159968
0.9297	High Similarity	NPC282000
0.9297	High Similarity	NPC74817
0.9297	High Similarity	NPC236791
0.9297	High Similarity	NPC246620
0.9297	High Similarity	NPC266555
0.9297	High Similarity	NPC293054
0.9297	High Similarity	NPC324112
0.9297	High Similarity	NPC124452
0.9297	High Similarity	NPC252131
0.9259	High Similarity	NPC472089
0.9248	High Similarity	NPC114155
0.9248	High Similarity	NPC133025
0.9248	High Similarity	NPC300846
0.9248	High Similarity	NPC476639
0.9219	High Similarity	NPC103823
0.9219	High Similarity	NPC44748
0.9219	High Similarity	NPC18924
0.9219	High Similarity	NPC76451
0.9219	High Similarity	NPC78974
0.9219	High Similarity	NPC214406
0.9219	High Similarity	NPC170485
0.9219	High Similarity	NPC223953
0.9219	High Similarity	NPC223136
0.9219	High Similarity	NPC28730
0.9191	High Similarity	NPC470917
0.9191	High Similarity	NPC472087
0.9191	High Similarity	NPC472088
0.9185	High Similarity	NPC472090
0.9185	High Similarity	NPC472091
0.9185	High Similarity	NPC472092
0.9179	High Similarity	NPC86605
0.9179	High Similarity	NPC46277
0.9179	High Similarity	NPC156948
0.9179	High Similarity	NPC301765
0.9179	High Similarity	NPC3072
0.9173	High Similarity	NPC283009
0.9173	High Similarity	NPC111655
0.9173	High Similarity	NPC256262
0.9173	High Similarity	NPC261873
0.916	High Similarity	NPC471983
0.916	High Similarity	NPC149337
0.9147	High Similarity	NPC127587
0.9147	High Similarity	NPC236760
0.9141	High Similarity	NPC221077
0.9141	High Similarity	NPC193544
0.9141	High Similarity	NPC17943
0.9141	High Similarity	NPC208950
0.9141	High Similarity	NPC60885
0.9141	High Similarity	NPC475169
0.9141	High Similarity	NPC82483
0.9141	High Similarity	NPC265483
0.9141	High Similarity	NPC233410
0.9141	High Similarity	NPC203133
0.9141	High Similarity	NPC105925
0.9141	High Similarity	NPC116907
0.9141	High Similarity	NPC234400
0.9141	High Similarity	NPC298757
0.9141	High Similarity	NPC251855
0.9141	High Similarity	NPC117214
0.9141	High Similarity	NPC472093
0.9141	High Similarity	NPC299584
0.9141	High Similarity	NPC57490
0.9137	High Similarity	NPC262297
0.9124	High Similarity	NPC469630
0.9111	High Similarity	NPC55947
0.9111	High Similarity	NPC471183
0.9098	High Similarity	NPC311256
0.9098	High Similarity	NPC103967
0.9091	High Similarity	NPC127624
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
0.9065	High Similarity	NPC126291
0.9065	High Similarity	NPC112251
0.9062	High Similarity	NPC206487
0.9062	High Similarity	NPC228503
0.9062	High Similarity	NPC5796
0.9062	High Similarity	NPC138248
0.9058	High Similarity	NPC469795
0.9037	High Similarity	NPC35550
0.9015	High Similarity	NPC474356
0.9015	High Similarity	NPC282508
0.9015	High Similarity	NPC232275
0.9015	High Similarity	NPC45715
0.9015	High Similarity	NPC12275
0.9008	High Similarity	NPC58164
0.9008	High Similarity	NPC212015
0.9008	High Similarity	NPC10225
0.9	High Similarity	NPC21563
0.8992	High Similarity	NPC266705
0.8992	High Similarity	NPC228771
0.8992	High Similarity	NPC113495
0.8992	High Similarity	NPC105718
0.8992	High Similarity	NPC29008
0.8992	High Similarity	NPC278955
0.8984	High Similarity	NPC121115
0.8984	High Similarity	NPC95168
0.8984	High Similarity	NPC197757
0.8984	High Similarity	NPC136319
0.8984	High Similarity	NPC84086
0.8984	High Similarity	NPC228922
0.8984	High Similarity	NPC282496
0.8984	High Similarity	NPC233526
0.8978	High Similarity	NPC265075
0.8971	High Similarity	NPC70682
0.8971	High Similarity	NPC32630
0.8971	High Similarity	NPC260741
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
0.8955	High Similarity	NPC317380
0.8947	High Similarity	NPC102256
0.8947	High Similarity	NPC86655
0.8947	High Similarity	NPC218884
0.8947	High Similarity	NPC202762
0.8939	High Similarity	NPC192687
0.8939	High Similarity	NPC224157
0.8931	High Similarity	NPC98631
0.8931	High Similarity	NPC215300
0.8931	High Similarity	NPC206615
0.8931	High Similarity	NPC186843

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 NPC125649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	997
0.2-0.3	1787
0.3-0.4	2820
0.4-0.5	1571
0.5-0.6	846
0.6-0.7	602
0.7-0.8	121
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD3027	Phase 3
0.8712	High Similarity	NPD1530	Clinical (unspecified phase)
0.8647	High Similarity	NPD1529	Clinical (unspecified phase)
0.8529	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD1612	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD4625	Phase 3
0.8261	Intermediate Similarity	NPD3620	Phase 2
0.8261	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4908	Phase 1
0.8224	Intermediate Similarity	NPD6234	Discontinued
0.8162	Intermediate Similarity	NPD3018	Phase 2
0.8133	Intermediate Similarity	NPD37	Approved
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD2983	Phase 2
0.8	Intermediate Similarity	NPD4749	Approved
0.8	Intermediate Similarity	NPD2982	Phase 2
0.7985	Intermediate Similarity	NPD1610	Phase 2
0.7984	Intermediate Similarity	NPD5283	Phase 1
0.7974	Intermediate Similarity	NPD4965	Approved
0.7974	Intermediate Similarity	NPD4967	Phase 2
0.7974	Intermediate Similarity	NPD4966	Approved
0.7969	Intermediate Similarity	NPD228	Approved
0.7956	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD2981	Phase 2
0.7911	Intermediate Similarity	NPD7473	Discontinued
0.7868	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7228	Approved
0.7857	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1548	Phase 1
0.7808	Intermediate Similarity	NPD6674	Discontinued
0.7778	Intermediate Similarity	NPD1934	Approved
0.7746	Intermediate Similarity	NPD4060	Phase 1
0.7737	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2801	Approved
0.7702	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD4005	Discontinued
0.7687	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3021	Approved
0.7674	Intermediate Similarity	NPD3022	Approved
0.7658	Intermediate Similarity	NPD7199	Phase 2
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1465	Phase 2
0.7591	Intermediate Similarity	NPD3705	Approved
0.7562	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3540	Phase 1
0.7538	Intermediate Similarity	NPD4750	Phase 3
0.7518	Intermediate Similarity	NPD2861	Phase 2
0.7517	Intermediate Similarity	NPD4097	Suspended
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	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD6100	Approved
0.7483	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD3539	Phase 1
0.7483	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD4055	Discovery
0.7448	Intermediate Similarity	NPD3657	Discovery
0.7445	Intermediate Similarity	NPD4626	Approved
0.7432	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD8053	Approved
0.7425	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD8054	Approved
0.7403	Intermediate Similarity	NPD1653	Approved
0.7386	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1512	Approved
0.7379	Intermediate Similarity	NPD1558	Phase 1
0.7351	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7240	Approved
0.7329	Intermediate Similarity	NPD5735	Approved
0.7329	Intermediate Similarity	NPD6959	Discontinued
0.7324	Intermediate Similarity	NPD4624	Approved
0.7305	Intermediate Similarity	NPD6696	Suspended
0.7305	Intermediate Similarity	NPD8651	Approved
0.7303	Intermediate Similarity	NPD7124	Phase 2
0.7285	Intermediate Similarity	NPD3750	Approved
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.7261	Intermediate Similarity	NPD5090	Approved
0.7261	Intermediate Similarity	NPD5089	Approved
0.7255	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4357	Discontinued
0.7254	Intermediate Similarity	NPD3094	Phase 2
0.7252	Intermediate Similarity	NPD2342	Discontinued
0.7246	Intermediate Similarity	NPD1651	Approved
0.7241	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5109	Approved
0.7241	Intermediate Similarity	NPD5111	Phase 2
0.7241	Intermediate Similarity	NPD5110	Phase 2
0.7233	Intermediate Similarity	NPD3817	Phase 2
0.723	Intermediate Similarity	NPD6111	Discontinued
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7226	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3092	Approved
0.7214	Intermediate Similarity	NPD422	Phase 1
0.7212	Intermediate Similarity	NPD3818	Discontinued
0.7208	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7447	Phase 1
0.7208	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5762	Approved
0.72	Intermediate Similarity	NPD5763	Approved
0.7197	Intermediate Similarity	NPD4380	Phase 2
0.7188	Intermediate Similarity	NPD1242	Phase 1
0.7183	Intermediate Similarity	NPD1283	Approved
0.7181	Intermediate Similarity	NPD1510	Phase 2
0.7172	Intermediate Similarity	NPD7095	Approved
0.7171	Intermediate Similarity	NPD3892	Phase 2
0.717	Intermediate Similarity	NPD7819	Suspended
0.7169	Intermediate Similarity	NPD7054	Approved
0.7162	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD7041	Phase 2
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7213	Phase 3
0.7143	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1240	Approved
0.7126	Intermediate Similarity	NPD7472	Approved
0.7124	Intermediate Similarity	NPD2219	Phase 1
0.7124	Intermediate Similarity	NPD5241	Discontinued
0.7122	Intermediate Similarity	NPD5691	Approved
0.7113	Intermediate Similarity	NPD1669	Approved
0.7113	Intermediate Similarity	NPD5327	Phase 3
0.7111	Intermediate Similarity	NPD7635	Approved
0.7105	Intermediate Similarity	NPD5177	Phase 3
0.7105	Intermediate Similarity	NPD3060	Approved
0.7097	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2533	Approved
0.7097	Intermediate Similarity	NPD2532	Approved
0.7097	Intermediate Similarity	NPD2534	Approved
0.7093	Intermediate Similarity	NPD7906	Approved
0.7091	Intermediate Similarity	NPD27	Approved
0.7091	Intermediate Similarity	NPD2489	Approved
0.7089	Intermediate Similarity	NPD4678	Approved
0.7089	Intermediate Similarity	NPD4675	Approved
0.7086	Intermediate Similarity	NPD7266	Discontinued
0.7083	Intermediate Similarity	NPD6584	Phase 3
0.7083	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7768	Phase 2
0.708	Intermediate Similarity	NPD7157	Approved
0.708	Intermediate Similarity	NPD709	Approved
0.708	Intermediate Similarity	NPD6671	Approved
0.7076	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2674	Phase 3
0.7073	Intermediate Similarity	NPD7229	Phase 3
0.7073	Intermediate Similarity	NPD3051	Approved
0.7068	Intermediate Similarity	NPD2684	Approved
0.7067	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4577	Approved
0.7059	Intermediate Similarity	NPD4578	Approved
0.7055	Intermediate Similarity	NPD5494	Approved
0.7052	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3091	Approved
0.7037	Intermediate Similarity	NPD7075	Discontinued
0.7035	Intermediate Similarity	NPD4663	Approved
0.7032	Intermediate Similarity	NPD7390	Discontinued
0.703	Intermediate Similarity	NPD2969	Approved
0.703	Intermediate Similarity	NPD2970	Approved
0.7027	Intermediate Similarity	NPD2238	Phase 2
0.7027	Intermediate Similarity	NPD4140	Approved
0.7027	Intermediate Similarity	NPD943	Approved
0.7025	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2935	Discontinued
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5451	Approved
0.7013	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2677	Approved
0.7007	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD8099	Discontinued
0.7006	Intermediate Similarity	NPD8252	Approved
0.7006	Intermediate Similarity	NPD8251	Approved
0.7	Intermediate Similarity	NPD1357	Approved
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4536	Approved
0.7	Intermediate Similarity	NPD4538	Approved
0.6987	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7843	Approved
0.6982	Remote Similarity	NPD6797	Phase 2
0.698	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5124	Phase 1
0.698	Remote Similarity	NPD230	Phase 1
0.6977	Remote Similarity	NPD3020	Approved
0.6975	Remote Similarity	NPD6788	Approved
0.6974	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1091	Approved
0.6972	Remote Similarity	NPD1611	Approved
0.6972	Remote Similarity	NPD1281	Approved
0.697	Remote Similarity	NPD3787	Discontinued
0.6964	Remote Similarity	NPD8156	Discontinued
0.6959	Remote Similarity	NPD7312	Approved
0.6959	Remote Similarity	NPD7313	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