NPASS Compound

Structure

CID77598 OpenBabel06191715412D 21 23 0 0 0 0 0 0 0 0999 V2000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 1.7321 -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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 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 -1.7321 -4.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 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 17 2 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	3.168
LogD:	2.855
LogS:	-3.947
# Rotatable Bonds:	2
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	2.472
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.012
MDCK Permeability:	1.3547460184781812e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	93.8902359008789%
Volume Distribution (VD):	0.524
Pgp-substrate:	10.524110794067383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.619
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.392
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	11.05
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.019
Drug-inuced Liver Injury (DILI):	0.84
AMES Toxicity:	0.757
Rat Oral Acute Toxicity:	0.41
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.939
Carcinogencity:	0.646
Eye Corrosion:	0.145
Eye Irritation:	0.964
Respiratory Toxicity:	0.565

Download Data

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

Natural Product: NPC77598

Natural Product ID:	NPC77598
*Common Name:**	Calanquinone C
IUPAC Name:	6-hydroxy-5,7-dimethoxy-9,10-dihydrophenanthrene-1,4-dione
Synonyms:	Calanquinone C
Standard InCHIKey:	PQDQTDFITALYGL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-20-12-7-8-3-4-9-10(17)5-6-11(18)14(9)13(8)16(21-2)15(12)19/h5-7,19H,3-4H2,1-2H3
SMILES:	COc1cc2CCC3=C(C(=O)C=CC3=O)c2c(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL538130
PubChem CID:	25243460
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]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
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]
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]

☑ 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	=	3.58	ug.mL-1	PMID[572073]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	2.07	ug.mL-1	PMID[572073]
NPT90	Cell Line	DU-145	Homo sapiens	EC50	=	4.34	ug.mL-1	PMID[572073]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	4.14	ug.mL-1	PMID[572073]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	2.12	ug.mL-1	PMID[572073]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	2.97	ug.mL-1	PMID[572073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	4.68	ug.mL-1	PMID[572073]

☑ 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 NPC77598 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	396
0.1-0.2	1521
0.2-0.3	3888
0.3-0.4	9498
0.4-0.5	8810
0.5-0.6	3157
0.6-0.7	5507
0.7-0.8	7557
0.8-0.85	2039
0.85-0.9	301
0.9-0.95	22
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9452	High Similarity	NPC78505
0.9315	High Similarity	NPC134293
0.9205	High Similarity	NPC245891
0.9205	High Similarity	NPC104876
0.9139	High Similarity	NPC178976
0.9128	High Similarity	NPC312338
0.9128	High Similarity	NPC149889
0.9103	High Similarity	NPC207732
0.9097	High Similarity	NPC312256
0.9073	High Similarity	NPC14561
0.9073	High Similarity	NPC77807
0.9073	High Similarity	NPC5379
0.9041	High Similarity	NPC157133
0.9028	High Similarity	NPC110419
0.9021	High Similarity	NPC144284
0.9013	High Similarity	NPC37543
0.9013	High Similarity	NPC199463
0.9007	High Similarity	NPC234485
0.898	High Similarity	NPC30720
0.8973	High Similarity	NPC105213
0.8961	High Similarity	NPC311740
0.8954	High Similarity	NPC477410
0.894	High Similarity	NPC107109
0.894	High Similarity	NPC127172
0.8933	High Similarity	NPC272566
0.8926	High Similarity	NPC69430
0.8926	High Similarity	NPC200060
0.8926	High Similarity	NPC264550
0.8926	High Similarity	NPC40290
0.8926	High Similarity	NPC264289
0.8926	High Similarity	NPC195763
0.8926	High Similarity	NPC142876
0.8926	High Similarity	NPC333691
0.8926	High Similarity	NPC139293
0.8904	High Similarity	NPC16353
0.8903	High Similarity	NPC149389
0.8896	High Similarity	NPC84571
0.8882	High Similarity	NPC38898
0.8873	High Similarity	NPC208760
0.8867	High Similarity	NPC472279
0.8867	High Similarity	NPC85131
0.8859	High Similarity	NPC80710
0.8859	High Similarity	NPC139364
0.8859	High Similarity	NPC194653
0.8859	High Similarity	NPC203747
0.8859	High Similarity	NPC254702
0.8851	High Similarity	NPC165389
0.8844	High Similarity	NPC142165
0.8828	High Similarity	NPC50823
0.8824	High Similarity	NPC470762
0.8824	High Similarity	NPC474167
0.8816	High Similarity	NPC93552
0.8808	High Similarity	NPC302783
0.8808	High Similarity	NPC473201
0.8808	High Similarity	NPC46882
0.8808	High Similarity	NPC256406
0.8808	High Similarity	NPC132990
0.8792	High Similarity	NPC125449
0.8792	High Similarity	NPC188074
0.8776	High Similarity	NPC287722
0.8776	High Similarity	NPC254659
0.8767	High Similarity	NPC84273
0.8766	High Similarity	NPC472963
0.8766	High Similarity	NPC136674
0.8758	High Similarity	NPC57674
0.8758	High Similarity	NPC152951
0.8758	High Similarity	NPC230149
0.8758	High Similarity	NPC117992
0.8758	High Similarity	NPC39184
0.8758	High Similarity	NPC168247
0.875	High Similarity	NPC216769
0.875	High Similarity	NPC291802
0.875	High Similarity	NPC474993
0.875	High Similarity	NPC35763
0.875	High Similarity	NPC121522
0.875	High Similarity	NPC209487
0.875	High Similarity	NPC131266
0.875	High Similarity	NPC100263
0.875	High Similarity	NPC100971
0.875	High Similarity	NPC269451
0.875	High Similarity	NPC245382
0.875	High Similarity	NPC181209
0.8742	High Similarity	NPC151473
0.8742	High Similarity	NPC29231
0.8742	High Similarity	NPC225854
0.8733	High Similarity	NPC287395
0.8733	High Similarity	NPC183655
0.8733	High Similarity	NPC474903
0.8725	High Similarity	NPC12377
0.8716	High Similarity	NPC475201
0.871	High Similarity	NPC235448
0.8707	High Similarity	NPC229218
0.8707	High Similarity	NPC192597
0.8707	High Similarity	NPC301178
0.8707	High Similarity	NPC141817
0.8707	High Similarity	NPC176030
0.8707	High Similarity	NPC169214
0.8707	High Similarity	NPC284556
0.8701	High Similarity	NPC472050
0.8701	High Similarity	NPC472455
0.8701	High Similarity	NPC472907
0.8699	High Similarity	NPC19158
0.8693	High Similarity	NPC469550
0.8693	High Similarity	NPC273462
0.8693	High Similarity	NPC124714
0.8693	High Similarity	NPC70433
0.8693	High Similarity	NPC49402
0.8693	High Similarity	NPC155686
0.8693	High Similarity	NPC33051
0.8693	High Similarity	NPC227337
0.8693	High Similarity	NPC472905
0.869	High Similarity	NPC470962
0.8684	High Similarity	NPC118427
0.8684	High Similarity	NPC144283
0.8684	High Similarity	NPC45291
0.8684	High Similarity	NPC31363
0.8684	High Similarity	NPC474414
0.8684	High Similarity	NPC19980
0.8675	High Similarity	NPC38545
0.8675	High Similarity	NPC171916
0.8675	High Similarity	NPC80370
0.8675	High Similarity	NPC102003
0.8675	High Similarity	NPC92722
0.8671	High Similarity	NPC26386
0.8671	High Similarity	NPC191930
0.8671	High Similarity	NPC303174
0.8662	High Similarity	NPC294965
0.8658	High Similarity	NPC73416
0.8658	High Similarity	NPC160777
0.8654	High Similarity	NPC14353
0.8654	High Similarity	NPC56085
0.8654	High Similarity	NPC161947
0.8654	High Similarity	NPC155302
0.8654	High Similarity	NPC471973
0.8654	High Similarity	NPC228785
0.8654	High Similarity	NPC474960
0.8654	High Similarity	NPC36217
0.8649	High Similarity	NPC119663
0.8649	High Similarity	NPC50954
0.8649	High Similarity	NPC471417
0.8645	High Similarity	NPC304008
0.8645	High Similarity	NPC129684
0.8645	High Similarity	NPC299520
0.8645	High Similarity	NPC161960
0.8645	High Similarity	NPC187745
0.8645	High Similarity	NPC219867
0.8645	High Similarity	NPC180011
0.8645	High Similarity	NPC300727
0.8645	High Similarity	NPC241904
0.8636	High Similarity	NPC256925
0.8636	High Similarity	NPC472280
0.8636	High Similarity	NPC130589
0.8636	High Similarity	NPC134287
0.8636	High Similarity	NPC234255
0.8636	High Similarity	NPC472048
0.863	High Similarity	NPC4796
0.8627	High Similarity	NPC39732
0.8627	High Similarity	NPC477231
0.8627	High Similarity	NPC470340
0.8627	High Similarity	NPC180944
0.8627	High Similarity	NPC260979
0.8627	High Similarity	NPC257648
0.8627	High Similarity	NPC60972
0.8627	High Similarity	NPC164912
0.8618	High Similarity	NPC103509
0.8618	High Similarity	NPC10467
0.8618	High Similarity	NPC156953
0.8609	High Similarity	NPC43669
0.8609	High Similarity	NPC166036
0.8609	High Similarity	NPC15329
0.8609	High Similarity	NPC238279
0.8609	High Similarity	NPC196277
0.8609	High Similarity	NPC272721
0.8609	High Similarity	NPC203077
0.8609	High Similarity	NPC131451
0.8608	High Similarity	NPC476822
0.8608	High Similarity	NPC270837
0.8608	High Similarity	NPC249181
0.8608	High Similarity	NPC236132
0.8608	High Similarity	NPC220313
0.86	High Similarity	NPC143903
0.86	High Similarity	NPC226987
0.8599	High Similarity	NPC278052
0.8599	High Similarity	NPC61010
0.8599	High Similarity	NPC40491
0.8599	High Similarity	NPC87431
0.8591	High Similarity	NPC19896
0.8591	High Similarity	NPC242893
0.8591	High Similarity	NPC38065
0.859	High Similarity	NPC476242
0.859	High Similarity	NPC100123
0.859	High Similarity	NPC55738
0.859	High Similarity	NPC204879
0.8581	High Similarity	NPC274730
0.8581	High Similarity	NPC5322
0.8581	High Similarity	NPC6633
0.8581	High Similarity	NPC49108
0.8581	High Similarity	NPC299154
0.8581	High Similarity	NPC115853
0.8581	High Similarity	NPC469474

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 NPC77598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	937
0.2-0.3	1664
0.3-0.4	2676
0.4-0.5	1830
0.5-0.6	983
0.6-0.7	535
0.7-0.8	138
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8506	High Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD2801	Approved
0.8428	Intermediate Similarity	NPD6232	Discontinued
0.8385	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD1465	Phase 2
0.8117	Intermediate Similarity	NPD1512	Approved
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8054	Intermediate Similarity	NPD1510	Phase 2
0.8041	Intermediate Similarity	NPD1607	Approved
0.8027	Intermediate Similarity	NPD943	Approved
0.8027	Intermediate Similarity	NPD1240	Approved
0.8026	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD230	Phase 1
0.7933	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD9494	Approved
0.7925	Intermediate Similarity	NPD37	Approved
0.7911	Intermediate Similarity	NPD4380	Phase 2
0.7875	Intermediate Similarity	NPD7819	Suspended
0.7853	Intermediate Similarity	NPD5494	Approved
0.7834	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3817	Phase 2
0.7823	Intermediate Similarity	NPD3027	Phase 3
0.7821	Intermediate Similarity	NPD2532	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7821	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2533	Approved
0.7815	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7074	Phase 3
0.7792	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD4965	Approved
0.7763	Intermediate Similarity	NPD6099	Approved
0.7763	Intermediate Similarity	NPD6100	Approved
0.7755	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7054	Approved
0.7733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7075	Discontinued
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD7472	Approved
0.7687	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7228	Approved
0.7667	Intermediate Similarity	NPD1613	Approved
0.7667	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2800	Approved
0.7605	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6959	Discontinued
0.7578	Intermediate Similarity	NPD6599	Discontinued
0.7558	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6797	Phase 2
0.7532	Intermediate Similarity	NPD2796	Approved
0.7532	Intermediate Similarity	NPD6799	Approved
0.7515	Intermediate Similarity	NPD3749	Approved
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.747	Intermediate Similarity	NPD919	Approved
0.7466	Intermediate Similarity	NPD9269	Phase 2
0.7457	Intermediate Similarity	NPD7808	Phase 3
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.7452	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8166	Discontinued
0.7451	Intermediate Similarity	NPD6651	Approved
0.7423	Intermediate Similarity	NPD7411	Suspended
0.7419	Intermediate Similarity	NPD2935	Discontinued
0.7417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD6190	Approved
0.7389	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD447	Suspended
0.7362	Intermediate Similarity	NPD7028	Phase 2
0.7357	Intermediate Similarity	NPD228	Approved
0.7351	Intermediate Similarity	NPD4625	Phase 3
0.7346	Intermediate Similarity	NPD1653	Approved
0.7322	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1470	Approved
0.7312	Intermediate Similarity	NPD7390	Discontinued
0.7312	Intermediate Similarity	NPD4357	Discontinued
0.7299	Intermediate Similarity	NPD6559	Discontinued
0.7297	Intermediate Similarity	NPD4749	Approved
0.7292	Intermediate Similarity	NPD5536	Phase 2
0.7273	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2346	Discontinued
0.726	Intermediate Similarity	NPD4626	Approved
0.7251	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1283	Approved
0.7246	Intermediate Similarity	NPD7768	Phase 2
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD5711	Approved
0.7225	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3018	Phase 2
0.7212	Intermediate Similarity	NPD5089	Approved
0.7212	Intermediate Similarity	NPD5090	Approved
0.7208	Intermediate Similarity	NPD3620	Phase 2
0.7208	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7240	Approved
0.7197	Intermediate Similarity	NPD1551	Phase 2
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7193	Intermediate Similarity	NPD5242	Approved
0.7192	Intermediate Similarity	NPD9268	Approved
0.7192	Intermediate Similarity	NPD1651	Approved
0.719	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3764	Approved
0.7186	Intermediate Similarity	NPD5402	Approved
0.7171	Intermediate Similarity	NPD4908	Phase 1
0.7162	Intermediate Similarity	NPD1610	Phase 2
0.7162	Intermediate Similarity	NPD422	Phase 1
0.7162	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7125	Intermediate Similarity	NPD7003	Approved
0.7114	Intermediate Similarity	NPD1608	Approved
0.7114	Intermediate Similarity	NPD3972	Approved
0.7102	Intermediate Similarity	NPD7685	Pre-registration
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7095	Intermediate Similarity	NPD8150	Discontinued
0.7083	Intermediate Similarity	NPD4288	Approved
0.7083	Intermediate Similarity	NPD5353	Approved
0.7078	Intermediate Similarity	NPD3268	Approved
0.7076	Intermediate Similarity	NPD8127	Discontinued
0.7073	Intermediate Similarity	NPD920	Approved
0.7073	Intermediate Similarity	NPD5403	Approved
0.7067	Intermediate Similarity	NPD2983	Phase 2
0.7067	Intermediate Similarity	NPD2982	Phase 2
0.7063	Intermediate Similarity	NPD1243	Approved
0.7055	Intermediate Similarity	NPD5401	Approved
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1281	Approved
0.7027	Intermediate Similarity	NPD2932	Approved
0.7025	Intermediate Similarity	NPD2799	Discontinued
0.702	Intermediate Similarity	NPD1876	Approved
0.7014	Intermediate Similarity	NPD5283	Phase 1
0.7014	Intermediate Similarity	NPD1241	Discontinued
0.7007	Intermediate Similarity	NPD9545	Approved
0.7007	Intermediate Similarity	NPD1548	Phase 1
0.7005	Intermediate Similarity	NPD2494	Approved
0.7005	Intermediate Similarity	NPD2493	Approved
0.7	Intermediate Similarity	NPD2981	Phase 2
0.7	Intermediate Similarity	NPD8434	Phase 2
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5977	Approved
0.6982	Remote Similarity	NPD5978	Approved
0.6981	Remote Similarity	NPD5404	Approved
0.6981	Remote Similarity	NPD5405	Approved
0.6981	Remote Similarity	NPD5406	Approved
0.6981	Remote Similarity	NPD5408	Approved
0.6975	Remote Similarity	NPD2309	Approved
0.6974	Remote Similarity	NPD2797	Approved
0.6959	Remote Similarity	NPD5691	Approved
0.6954	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6782	Approved
0.6952	Remote Similarity	NPD6780	Approved
0.6952	Remote Similarity	NPD6781	Approved
0.6952	Remote Similarity	NPD6777	Approved
0.6952	Remote Similarity	NPD6778	Approved
0.6952	Remote Similarity	NPD6776	Approved
0.6952	Remote Similarity	NPD6779	Approved
0.6951	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5953	Discontinued
0.6943	Remote Similarity	NPD1933	Approved
0.6933	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3300	Phase 2
0.6928	Remote Similarity	NPD2798	Approved
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6927	Remote Similarity	NPD8151	Discontinued
0.6923	Remote Similarity	NPD4585	Approved
0.6918	Remote Similarity	NPD4308	Phase 3
0.6918	Remote Similarity	NPD3299	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