NPASS Compound

Structure

CID245891 OpenBabel06191716042D 23 25 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 18 2 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 15 1 0 0 0 0 15 19 2 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.307
LogD:	2.034
LogS:	-4.3
# Rotatable Bonds:	3
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.937
Synthetic Accessibility Score:	2.651
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.852
MDCK Permeability:	3.189230847056024e-05
Pgp-inhibitor:	0.908
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	89.1490249633789%
Volume Distribution (VD):	0.507
Pgp-substrate:	11.203329086303711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.729
CYP2C19-substrate:	0.365
CYP2C9-inhibitor:	0.758
CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	0.558
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	6.142
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.729
Drug-inuced Liver Injury (DILI):	0.689
AMES Toxicity:	0.705
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.695
Carcinogencity:	0.862
Eye Corrosion:	0.012
Eye Irritation:	0.364
Respiratory Toxicity:	0.817

Download Data

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

Natural Product: NPC245891

Natural Product ID:	NPC245891
*Common Name:**	Calanquinone B
IUPAC Name:	6-hydroxy-3,5,7-trimethoxyphenanthrene-1,4-dione
Synonyms:
Standard InCHIKey:	NLLWAXZZCLBWDL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-21-11-6-8-4-5-9-10(18)7-12(22-2)15(19)14(9)13(8)17(23-3)16(11)20/h4-7,20H,1-3H3
SMILES:	COc1cc2ccc3C(=O)C=C(C(=O)c3c2c(c1O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562748
PubChem CID:	25243457
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
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]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	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	=	4.54	ug.mL-1	PMID[469638]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	1.55	ug.mL-1	PMID[469638]
NPT90	Cell Line	DU-145	Homo sapiens	EC50	=	6.45	ug.mL-1	PMID[469638]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	4.56	ug.mL-1	PMID[469638]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	1.81	ug.mL-1	PMID[469638]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	6.46	ug.mL-1	PMID[469638]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	13.28	ug.mL-1	PMID[469638]

☑ 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 NPC245891 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	431
0.1-0.2	1903
0.2-0.3	4334
0.3-0.4	11109
0.4-0.5	6797
0.5-0.6	3463
0.6-0.7	5282
0.7-0.8	6812
0.8-0.85	1901
0.85-0.9	629
0.9-0.95	32
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC104876
0.947	High Similarity	NPC474414
0.947	High Similarity	NPC78505
0.9467	High Similarity	NPC80370
0.9416	High Similarity	NPC178976
0.9351	High Similarity	NPC77807
0.9351	High Similarity	NPC14561
0.9351	High Similarity	NPC5379
0.9342	High Similarity	NPC230848
0.9333	High Similarity	NPC58373
0.929	High Similarity	NPC199463
0.929	High Similarity	NPC37543
0.9236	High Similarity	NPC311740
0.9221	High Similarity	NPC107109
0.9205	High Similarity	NPC77598
0.9172	High Similarity	NPC84571
0.9156	High Similarity	NPC149889
0.9156	High Similarity	NPC312338
0.9108	High Similarity	NPC477410
0.9091	High Similarity	NPC302783
0.9091	High Similarity	NPC472838
0.9091	High Similarity	NPC473201
0.9091	High Similarity	NPC306011
0.9073	High Similarity	NPC157133
0.9062	High Similarity	NPC26386
0.9038	High Similarity	NPC234485
0.9026	High Similarity	NPC58310
0.9026	High Similarity	NPC295977
0.9024	High Similarity	NPC245975
0.9007	High Similarity	NPC207732
0.9007	High Similarity	NPC105213
0.9	High Similarity	NPC312256
0.8974	High Similarity	NPC93552
0.8974	High Similarity	NPC127172
0.8968	High Similarity	NPC118427
0.8968	High Similarity	NPC272566
0.8961	High Similarity	NPC134293
0.8938	High Similarity	NPC149389
0.8938	High Similarity	NPC294965
0.8933	High Similarity	NPC110419
0.891	High Similarity	NPC28103
0.891	High Similarity	NPC164912
0.8903	High Similarity	NPC472279
0.8896	High Similarity	NPC472841
0.8882	High Similarity	NPC270837
0.8861	High Similarity	NPC288353
0.8861	High Similarity	NPC279605
0.8846	High Similarity	NPC256406
0.8846	High Similarity	NPC144283
0.8839	High Similarity	NPC142876
0.8839	High Similarity	NPC264550
0.8839	High Similarity	NPC139293
0.8839	High Similarity	NPC333691
0.8839	High Similarity	NPC200060
0.8839	High Similarity	NPC40290
0.8839	High Similarity	NPC69430
0.8839	High Similarity	NPC264289
0.8839	High Similarity	NPC195763
0.8831	High Similarity	NPC126767
0.8831	High Similarity	NPC56433
0.8831	High Similarity	NPC312929
0.8831	High Similarity	NPC190648
0.8831	High Similarity	NPC118027
0.8831	High Similarity	NPC289042
0.8831	High Similarity	NPC245584
0.8827	High Similarity	NPC303174
0.8824	High Similarity	NPC28632
0.8816	High Similarity	NPC50954
0.8816	High Similarity	NPC16353
0.8805	High Similarity	NPC136674
0.8797	High Similarity	NPC152951
0.8797	High Similarity	NPC168247
0.8797	High Similarity	NPC230149
0.8797	High Similarity	NPC38898
0.8797	High Similarity	NPC117992
0.8797	High Similarity	NPC39184
0.8797	High Similarity	NPC57674
0.8782	High Similarity	NPC103509
0.8782	High Similarity	NPC290954
0.8782	High Similarity	NPC255641
0.8782	High Similarity	NPC85131
0.878	High Similarity	NPC165979
0.878	High Similarity	NPC163130
0.8774	High Similarity	NPC194653
0.8774	High Similarity	NPC139364
0.8774	High Similarity	NPC80710
0.8774	High Similarity	NPC254702
0.8774	High Similarity	NPC203747
0.8773	High Similarity	NPC477517
0.8766	High Similarity	NPC165389
0.8765	High Similarity	NPC236132
0.8765	High Similarity	NPC101769
0.8765	High Similarity	NPC476822
0.8758	High Similarity	NPC66288
0.8758	High Similarity	NPC142165
0.875	High Similarity	NPC45846
0.875	High Similarity	NPC55738
0.875	High Similarity	NPC235448
0.8743	High Similarity	NPC8127
0.8743	High Similarity	NPC49667
0.8742	High Similarity	NPC265511
0.8742	High Similarity	NPC470762
0.8742	High Similarity	NPC472455
0.8742	High Similarity	NPC474167
0.8734	High Similarity	NPC227337
0.8734	High Similarity	NPC273462
0.8734	High Similarity	NPC70433
0.8734	High Similarity	NPC49402
0.8734	High Similarity	NPC33051
0.872	High Similarity	NPC234331
0.872	High Similarity	NPC95715
0.8718	High Similarity	NPC38545
0.8718	High Similarity	NPC171916
0.871	High Similarity	NPC125449
0.871	High Similarity	NPC188074
0.8701	High Similarity	NPC160777
0.8701	High Similarity	NPC73416
0.8696	High Similarity	NPC246478
0.8696	High Similarity	NPC56085
0.8696	High Similarity	NPC14353
0.8696	High Similarity	NPC471973
0.8696	High Similarity	NPC228785
0.8696	High Similarity	NPC36217
0.8693	High Similarity	NPC254659
0.8693	High Similarity	NPC287722
0.869	High Similarity	NPC23553
0.869	High Similarity	NPC77179
0.8688	High Similarity	NPC187745
0.8688	High Similarity	NPC161960
0.8688	High Similarity	NPC474637
0.8688	High Similarity	NPC273843
0.8688	High Similarity	NPC180011
0.8688	High Similarity	NPC219867
0.8688	High Similarity	NPC296044
0.8688	High Similarity	NPC472963
0.8688	High Similarity	NPC304008
0.8688	High Similarity	NPC167098
0.8679	High Similarity	NPC56786
0.8679	High Similarity	NPC133392
0.8679	High Similarity	NPC234255
0.8679	High Similarity	NPC130589
0.8679	High Similarity	NPC134287
0.8679	High Similarity	NPC80534
0.8679	High Similarity	NPC256925
0.8679	High Similarity	NPC226656
0.8679	High Similarity	NPC66508
0.8679	High Similarity	NPC472280
0.8675	High Similarity	NPC158226
0.8675	High Similarity	NPC230619
0.8675	High Similarity	NPC54098
0.8671	High Similarity	NPC82325
0.8671	High Similarity	NPC100971
0.8671	High Similarity	NPC121522
0.8671	High Similarity	NPC131266
0.8671	High Similarity	NPC291802
0.8671	High Similarity	NPC269451
0.8671	High Similarity	NPC181209
0.8671	High Similarity	NPC55205
0.8671	High Similarity	NPC209487
0.8671	High Similarity	NPC304954
0.8671	High Similarity	NPC216769
0.8671	High Similarity	NPC279989
0.8671	High Similarity	NPC474993
0.8671	High Similarity	NPC245382
0.8671	High Similarity	NPC100263
0.8671	High Similarity	NPC35763
0.8667	High Similarity	NPC264022
0.8662	High Similarity	NPC151473
0.8662	High Similarity	NPC147735
0.8662	High Similarity	NPC470568
0.8662	High Similarity	NPC29231
0.8662	High Similarity	NPC294646
0.8662	High Similarity	NPC280295
0.8659	High Similarity	NPC43319
0.8659	High Similarity	NPC29160
0.8659	High Similarity	NPC37870
0.8654	High Similarity	NPC166036
0.8654	High Similarity	NPC183655
0.8654	High Similarity	NPC237904
0.8654	High Similarity	NPC287395
0.8654	High Similarity	NPC238279
0.8654	High Similarity	NPC474903
0.8654	High Similarity	NPC203077
0.865	High Similarity	NPC220313
0.865	High Similarity	NPC197168
0.8647	High Similarity	NPC228209
0.8645	High Similarity	NPC12377
0.8642	High Similarity	NPC278052
0.8642	High Similarity	NPC40491
0.8642	High Similarity	NPC318081
0.8642	High Similarity	NPC61010
0.8636	High Similarity	NPC19896
0.8636	High Similarity	NPC474982
0.8636	High Similarity	NPC472836
0.8636	High Similarity	NPC275278
0.8634	High Similarity	NPC85121
0.8634	High Similarity	NPC100123
0.8634	High Similarity	NPC204879
0.8627	High Similarity	NPC284556
0.8627	High Similarity	NPC192597

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 NPC245891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	1045
0.2-0.3	1629
0.3-0.4	2737
0.4-0.5	1756
0.5-0.6	1004
0.6-0.7	405
0.7-0.8	143
0.8-0.85	21
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.882	High Similarity	NPD6232	Discontinued
0.8773	High Similarity	NPD7473	Discontinued
0.8625	High Similarity	NPD3882	Suspended
0.8438	Intermediate Similarity	NPD1934	Approved
0.8385	Intermediate Similarity	NPD2801	Approved
0.8385	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8291	Intermediate Similarity	NPD1512	Approved
0.8272	Intermediate Similarity	NPD1465	Phase 2
0.8165	Intermediate Similarity	NPD1511	Approved
0.8155	Intermediate Similarity	NPD6166	Phase 2
0.8155	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7075	Discontinued
0.8117	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3817	Phase 2
0.8105	Intermediate Similarity	NPD1607	Approved
0.8061	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7975	Intermediate Similarity	NPD4380	Phase 2
0.7975	Intermediate Similarity	NPD3750	Approved
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7974	Intermediate Similarity	NPD1240	Approved
0.7974	Intermediate Similarity	NPD943	Approved
0.7953	Intermediate Similarity	NPD3818	Discontinued
0.7939	Intermediate Similarity	NPD7819	Suspended
0.7917	Intermediate Similarity	NPD5494	Approved
0.7885	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3926	Phase 2
0.7879	Intermediate Similarity	NPD6801	Discontinued
0.787	Intermediate Similarity	NPD1247	Approved
0.787	Intermediate Similarity	NPD6959	Discontinued
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6799	Approved
0.7816	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6797	Phase 2
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7759	Intermediate Similarity	NPD7074	Phase 3
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.7746	Intermediate Similarity	NPD3751	Discontinued
0.7736	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1549	Phase 2
0.7727	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD230	Phase 1
0.7674	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD37	Approved
0.7658	Intermediate Similarity	NPD3748	Approved
0.7657	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD9494	Approved
0.7607	Intermediate Similarity	NPD7390	Discontinued
0.76	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3749	Approved
0.7574	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6559	Discontinued
0.7548	Intermediate Similarity	NPD3027	Phase 3
0.7531	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD6099	Approved
0.7485	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5402	Approved
0.7469	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2800	Approved
0.7457	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7443	Intermediate Similarity	NPD7228	Approved
0.7436	Intermediate Similarity	NPD4625	Phase 3
0.7429	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7768	Phase 2
0.7423	Intermediate Similarity	NPD7003	Approved
0.7423	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1613	Approved
0.7403	Intermediate Similarity	NPD1470	Approved
0.7394	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6777	Approved
0.7394	Intermediate Similarity	NPD6776	Approved
0.7394	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6782	Approved
0.7394	Intermediate Similarity	NPD6779	Approved
0.7394	Intermediate Similarity	NPD6780	Approved
0.7394	Intermediate Similarity	NPD6781	Approved
0.7394	Intermediate Similarity	NPD6778	Approved
0.7389	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7365	Intermediate Similarity	NPD5403	Approved
0.7363	Intermediate Similarity	NPD8150	Discontinued
0.7349	Intermediate Similarity	NPD5401	Approved
0.7346	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD1283	Approved
0.7317	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3787	Discontinued
0.7312	Intermediate Similarity	NPD6651	Approved
0.7296	Intermediate Similarity	NPD4060	Phase 1
0.7285	Intermediate Similarity	NPD1651	Approved
0.7284	Intermediate Similarity	NPD1551	Phase 2
0.7284	Intermediate Similarity	NPD5408	Approved
0.7284	Intermediate Similarity	NPD5404	Approved
0.7284	Intermediate Similarity	NPD5405	Approved
0.7284	Intermediate Similarity	NPD5406	Approved
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8434	Phase 2
0.7268	Intermediate Similarity	NPD8151	Discontinued
0.7239	Intermediate Similarity	NPD1471	Phase 3
0.7216	Intermediate Similarity	NPD5711	Approved
0.7216	Intermediate Similarity	NPD5710	Approved
0.7208	Intermediate Similarity	NPD3972	Approved
0.7208	Intermediate Similarity	NPD9269	Phase 2
0.7188	Intermediate Similarity	NPD7696	Phase 3
0.7188	Intermediate Similarity	NPD7697	Approved
0.7188	Intermediate Similarity	NPD7698	Approved
0.7175	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2309	Approved
0.716	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD1243	Approved
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD6535	Approved
0.7128	Intermediate Similarity	NPD7701	Phase 2
0.7128	Intermediate Similarity	NPD6534	Approved
0.7127	Intermediate Similarity	NPD5953	Discontinued
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7117	Intermediate Similarity	NPD2799	Discontinued
0.7115	Intermediate Similarity	NPD1876	Approved
0.7108	Intermediate Similarity	NPD8166	Discontinued
0.7104	Intermediate Similarity	NPD8313	Approved
0.7104	Intermediate Similarity	NPD8312	Approved
0.7093	Intermediate Similarity	NPD5090	Approved
0.7093	Intermediate Similarity	NPD5089	Approved
0.7088	Intermediate Similarity	NPD7685	Pre-registration
0.7083	Intermediate Similarity	NPD4357	Discontinued
0.7069	Intermediate Similarity	NPD4288	Approved
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7177	Discontinued
0.7041	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5536	Phase 2
0.7024	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7801	Approved
0.7016	Intermediate Similarity	NPD7700	Phase 2
0.7016	Intermediate Similarity	NPD7699	Phase 2
0.7013	Intermediate Similarity	NPD4626	Approved
0.7012	Intermediate Similarity	NPD4308	Phase 3
0.6995	Remote Similarity	NPD7240	Approved
0.6995	Remote Similarity	NPD2493	Approved
0.6995	Remote Similarity	NPD2494	Approved
0.6981	Remote Similarity	NPD3018	Phase 2
0.6974	Remote Similarity	NPD8320	Phase 1
0.6974	Remote Similarity	NPD8319	Approved
0.6971	Remote Similarity	NPD5978	Approved
0.6971	Remote Similarity	NPD5977	Approved
0.697	Remote Similarity	NPD2438	Suspended
0.6964	Remote Similarity	NPD2354	Approved
0.6963	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7907	Approved
0.6959	Remote Similarity	NPD3057	Approved
0.6957	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD2313	Discontinued
0.6957	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD9268	Approved
0.6943	Remote Similarity	NPD4749	Approved
0.6937	Remote Similarity	NPD4908	Phase 1
0.6936	Remote Similarity	NPD7028	Phase 2
0.6933	Remote Similarity	NPD1933	Approved
0.6933	Remote Similarity	NPD6355	Discontinued
0.6928	Remote Similarity	NPD2343	Clinical (unspecified phase)

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