NPASS Compound

Structure

CID259685 OpenBabel06191716062D 26 28 0 0 1 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 3.4641 -0.0000 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 2.5981 -0.5000 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 -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 -2.5981 -1.5000 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 1.7321 -0.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 -1.7321 -2.0000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 15 1 6 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.17
Volume:	377.468
LogP:	5.157
LogD:	3.924
LogS:	-6.157
# Rotatable Bonds:	5
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	2.989
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.601
MDCK Permeability:	1.745774716255255e-05
Pgp-inhibitor:	0.781
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.212
Plasma Protein Binding (PPB):	82.19051361083984%
Volume Distribution (VD):	1.17
Pgp-substrate:	10.141534805297852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.364
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.73
CYP2C9-inhibitor:	0.935
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.358
CYP2D6-substrate:	0.811
CYP3A4-inhibitor:	0.807
CYP3A4-substrate:	0.514

ADMET: Excretion

Clearance (CL):	11.737
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.227
Skin Sensitization:	0.225
Carcinogencity:	0.214
Eye Corrosion:	0.003
Eye Irritation:	0.097
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC259685

Natural Product ID:	NPC259685
*Common Name:**	Candidone
IUPAC Name:	(2S)-5,7-dimethoxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:	Candidone
Standard InCHIKey:	JYESOAFLKFHYHP-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C22H24O4/c1-14(2)10-11-16-19(24-3)13-20(25-4)21-17(23)12-18(26-22(16)21)15-8-6-5-7-9-15/h5-10,13,18H,11-12H2,1-4H3/t18-/m0/s1
SMILES:	COc1cc(OC)c2c(c1CC=C(C)C)O[C@@H](CC2=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454844
PubChem CID:	157102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	flower	n.a.	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	bark	an elevation of 850 m (171725? S; 484030? E), Toamasina, Madagascar	2002-JAN	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15043430]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23002924]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29799195]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14502	Pogonolepis muelleriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9663	Artemisia igniaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	23.0	ug.mL-1	PMID[500198]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	4.7	ug ml-1	PMID[500199]
NPT27	Others	Unspecified		IC50	=	4.1	ug.mL-1	PMID[500199]
NPT2	Others	Unspecified		Ratio	=	0.9	n.a.	PMID[500199]

☑ 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 NPC259685 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	422
0.1-0.2	1560
0.2-0.3	4153
0.3-0.4	10864
0.4-0.5	7455
0.5-0.6	3916
0.6-0.7	6100
0.7-0.8	5247
0.8-0.85	1648
0.85-0.9	919
0.9-0.95	311
0.95-1	102

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC11566
0.9847	High Similarity	NPC99854
0.9704	High Similarity	NPC22467
0.9632	High Similarity	NPC182852
0.9632	High Similarity	NPC32739
0.9632	High Similarity	NPC296917
0.9632	High Similarity	NPC166482
0.9632	High Similarity	NPC76372
0.9632	High Similarity	NPC66515
0.9632	High Similarity	NPC148757
0.9632	High Similarity	NPC147145
0.9632	High Similarity	NPC107572
0.9632	High Similarity	NPC324134
0.9632	High Similarity	NPC37496
0.9632	High Similarity	NPC166934
0.9632	High Similarity	NPC306829
0.9632	High Similarity	NPC194432
0.9632	High Similarity	NPC10937
0.9632	High Similarity	NPC220998
0.9632	High Similarity	NPC177354
0.9632	High Similarity	NPC324436
0.9632	High Similarity	NPC76338
0.9632	High Similarity	NPC125855
0.9632	High Similarity	NPC167624
0.9632	High Similarity	NPC227579
0.9632	High Similarity	NPC78
0.9632	High Similarity	NPC40833
0.9632	High Similarity	NPC161506
0.9632	High Similarity	NPC265040
0.9632	High Similarity	NPC223500
0.9632	High Similarity	NPC1089
0.9632	High Similarity	NPC328164
0.9632	High Similarity	NPC228504
0.9632	High Similarity	NPC64915
0.963	High Similarity	NPC472409
0.9624	High Similarity	NPC161196
0.9621	High Similarity	NPC125269
0.9562	High Similarity	NPC59522
0.9562	High Similarity	NPC143896
0.9562	High Similarity	NPC107177
0.9562	High Similarity	NPC278249
0.9562	High Similarity	NPC478086
0.9562	High Similarity	NPC316816
0.9562	High Similarity	NPC175504
0.9562	High Similarity	NPC221432
0.9562	High Similarity	NPC39329
0.9562	High Similarity	NPC185276
0.9562	High Similarity	NPC149026
0.9562	High Similarity	NPC214166
0.9562	High Similarity	NPC310130
0.9562	High Similarity	NPC164980
0.9562	High Similarity	NPC169591
0.9562	High Similarity	NPC125894
0.9562	High Similarity	NPC68104
0.9562	High Similarity	NPC77794
0.9562	High Similarity	NPC81697
0.9562	High Similarity	NPC91560
0.9562	High Similarity	NPC75049
0.9562	High Similarity	NPC257097
0.9562	High Similarity	NPC85162
0.9562	High Similarity	NPC150408
0.9562	High Similarity	NPC223812
0.9559	High Similarity	NPC4743
0.9559	High Similarity	NPC96408
0.9559	High Similarity	NPC258630
0.9559	High Similarity	NPC324386
0.9559	High Similarity	NPC156190
0.9559	High Similarity	NPC312391
0.9559	High Similarity	NPC213322
0.9559	High Similarity	NPC248372
0.9559	High Similarity	NPC279650
0.9559	High Similarity	NPC166689
0.9559	High Similarity	NPC110038
0.9559	High Similarity	NPC52576
0.9559	High Similarity	NPC17170
0.9493	High Similarity	NPC87486
0.9493	High Similarity	NPC236766
0.9493	High Similarity	NPC473015
0.9493	High Similarity	NPC131568
0.9493	High Similarity	NPC473013
0.9493	High Similarity	NPC124780
0.9493	High Similarity	NPC235217
0.9493	High Similarity	NPC209040
0.9493	High Similarity	NPC131579
0.9493	High Similarity	NPC473014
0.9493	High Similarity	NPC197252
0.9485	High Similarity	NPC188243
0.9485	High Similarity	NPC6407
0.9485	High Similarity	NPC110228
0.9481	High Similarity	NPC17848
0.9478	High Similarity	NPC254741
0.947	High Similarity	NPC101294
0.947	High Similarity	NPC473655
0.9424	High Similarity	NPC83357
0.9424	High Similarity	NPC142405
0.9424	High Similarity	NPC195621
0.9424	High Similarity	NPC267375
0.9424	High Similarity	NPC20488
0.9424	High Similarity	NPC470133
0.9424	High Similarity	NPC127059
0.9424	High Similarity	NPC285630
0.9424	High Similarity	NPC111786
0.9424	High Similarity	NPC214774
0.9424	High Similarity	NPC470134
0.9424	High Similarity	NPC67805
0.9424	High Similarity	NPC473078
0.9424	High Similarity	NPC176229
0.9424	High Similarity	NPC301276
0.9424	High Similarity	NPC470131
0.9424	High Similarity	NPC470132
0.9424	High Similarity	NPC312973
0.9424	High Similarity	NPC472629
0.9424	High Similarity	NPC470647
0.9424	High Similarity	NPC88964
0.9424	High Similarity	NPC475052
0.9424	High Similarity	NPC54577
0.9424	High Similarity	NPC109183
0.9424	High Similarity	NPC246948
0.9416	High Similarity	NPC3188
0.9412	High Similarity	NPC140890
0.9412	High Similarity	NPC265871
0.9412	High Similarity	NPC274784
0.9412	High Similarity	NPC150648
0.9412	High Similarity	NPC329203
0.9412	High Similarity	NPC222342
0.9412	High Similarity	NPC310135
0.9412	High Similarity	NPC225153
0.9412	High Similarity	NPC20709
0.9403	High Similarity	NPC46869
0.9394	High Similarity	NPC278556
0.9389	High Similarity	NPC228184
0.9357	High Similarity	NPC283234
0.9357	High Similarity	NPC471285
0.9357	High Similarity	NPC296998
0.9357	High Similarity	NPC473077
0.9357	High Similarity	NPC23728
0.9357	High Similarity	NPC300988
0.9357	High Similarity	NPC10990
0.9357	High Similarity	NPC472627
0.9357	High Similarity	NPC110303
0.9353	High Similarity	NPC319752
0.9353	High Similarity	NPC470135
0.9353	High Similarity	NPC39045
0.9353	High Similarity	NPC470136
0.9353	High Similarity	NPC470890
0.9353	High Similarity	NPC271288
0.9343	High Similarity	NPC69769
0.9343	High Similarity	NPC284550
0.9343	High Similarity	NPC241100
0.9343	High Similarity	NPC76445
0.9343	High Similarity	NPC129853
0.9343	High Similarity	NPC150522
0.9343	High Similarity	NPC159275
0.9291	High Similarity	NPC132592
0.9291	High Similarity	NPC476342
0.9291	High Similarity	NPC161191
0.9291	High Similarity	NPC160821
0.9286	High Similarity	NPC187282
0.9286	High Similarity	NPC476088
0.9286	High Similarity	NPC228779
0.9286	High Similarity	NPC215885
0.9286	High Similarity	NPC24136
0.9286	High Similarity	NPC2416
0.9286	High Similarity	NPC474161
0.9286	High Similarity	NPC476153
0.9286	High Similarity	NPC290133
0.9281	High Similarity	NPC166138
0.9281	High Similarity	NPC18585
0.9281	High Similarity	NPC471621
0.9281	High Similarity	NPC106985
0.9275	High Similarity	NPC282300
0.9275	High Similarity	NPC110969
0.9275	High Similarity	NPC103362
0.927	High Similarity	NPC217186
0.927	High Similarity	NPC18260
0.927	High Similarity	NPC55018
0.927	High Similarity	NPC78913
0.927	High Similarity	NPC96565
0.927	High Similarity	NPC53181
0.927	High Similarity	NPC301217
0.927	High Similarity	NPC216978
0.927	High Similarity	NPC220062
0.927	High Similarity	NPC303633
0.9265	High Similarity	NPC79943
0.9265	High Similarity	NPC243083
0.9265	High Similarity	NPC107586
0.9265	High Similarity	NPC296490
0.9265	High Similarity	NPC157855
0.9265	High Similarity	NPC287246
0.9265	High Similarity	NPC32441
0.9265	High Similarity	NPC12296
0.9265	High Similarity	NPC295261
0.9265	High Similarity	NPC13768
0.9254	High Similarity	NPC292998
0.9254	High Similarity	NPC223354
0.9248	High Similarity	NPC284424
0.9225	High Similarity	NPC164299
0.9225	High Similarity	NPC472628
0.9225	High Similarity	NPC3642
0.9225	High Similarity	NPC473016

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 NPC259685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	962
0.2-0.3	1491
0.3-0.4	2642
0.4-0.5	1882
0.5-0.6	1159
0.6-0.7	462
0.7-0.8	145
0.8-0.85	27
0.85-0.9	17
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9478	High Similarity	NPD2796	Approved
0.9265	High Similarity	NPD1550	Clinical (unspecified phase)
0.9265	High Similarity	NPD1552	Clinical (unspecified phase)
0.9197	High Similarity	NPD1549	Phase 2
0.9078	High Similarity	NPD4378	Clinical (unspecified phase)
0.8973	High Similarity	NPD2393	Clinical (unspecified phase)
0.8973	High Similarity	NPD7096	Clinical (unspecified phase)
0.8966	High Similarity	NPD7411	Suspended
0.8912	High Similarity	NPD8443	Clinical (unspecified phase)
0.8844	High Similarity	NPD7819	Suspended
0.8811	High Similarity	NPD7410	Clinical (unspecified phase)
0.8792	High Similarity	NPD7075	Discontinued
0.8776	High Similarity	NPD6801	Discontinued
0.8767	High Similarity	NPD4380	Phase 2
0.8741	High Similarity	NPD6799	Approved
0.8705	High Similarity	NPD1510	Phase 2
0.8686	High Similarity	NPD1240	Approved
0.8675	High Similarity	NPD5494	Approved
0.8649	High Similarity	NPD1934	Approved
0.8561	High Similarity	NPD1547	Clinical (unspecified phase)
0.8561	High Similarity	NPD1607	Approved
0.8514	High Similarity	NPD6599	Discontinued
0.8462	Intermediate Similarity	NPD1243	Approved
0.8462	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD920	Approved
0.8421	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3748	Approved
0.8299	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD3817	Phase 2
0.8261	Intermediate Similarity	NPD6832	Phase 2
0.8235	Intermediate Similarity	NPD7768	Phase 2
0.8231	Intermediate Similarity	NPD1511	Approved
0.8224	Intermediate Similarity	NPD2801	Approved
0.8217	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6166	Phase 2
0.8188	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD5401	Approved
0.8121	Intermediate Similarity	NPD1512	Approved
0.8117	Intermediate Similarity	NPD3882	Suspended
0.8082	Intermediate Similarity	NPD2800	Approved
0.8056	Intermediate Similarity	NPD2799	Discontinued
0.8042	Intermediate Similarity	NPD6651	Approved
0.8027	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7959	Intermediate Similarity	NPD2654	Approved
0.795	Intermediate Similarity	NPD7054	Approved
0.7949	Intermediate Similarity	NPD3749	Approved
0.7914	Intermediate Similarity	NPD6559	Discontinued
0.7911	Intermediate Similarity	NPD1247	Approved
0.7901	Intermediate Similarity	NPD7472	Approved
0.7891	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD3818	Discontinued
0.7887	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD2313	Discontinued
0.7885	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD2935	Discontinued
0.7866	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6797	Phase 2
0.7853	Intermediate Similarity	NPD5953	Discontinued
0.7847	Intermediate Similarity	NPD1933	Approved
0.784	Intermediate Similarity	NPD5844	Phase 1
0.784	Intermediate Similarity	NPD7286	Phase 2
0.7826	Intermediate Similarity	NPD3972	Approved
0.7821	Intermediate Similarity	NPD5402	Approved
0.7815	Intermediate Similarity	NPD2533	Approved
0.7815	Intermediate Similarity	NPD2532	Approved
0.7815	Intermediate Similarity	NPD2534	Approved
0.7812	Intermediate Similarity	NPD3926	Phase 2
0.7808	Intermediate Similarity	NPD7033	Discontinued
0.7805	Intermediate Similarity	NPD7251	Discontinued
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7758	Intermediate Similarity	NPD7808	Phase 3
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7746	Intermediate Similarity	NPD4908	Phase 1
0.7744	Intermediate Similarity	NPD1241	Discontinued
0.7742	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5889	Approved
0.7742	Intermediate Similarity	NPD5890	Approved
0.773	Intermediate Similarity	NPD2798	Approved
0.7724	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD5124	Phase 1
0.7724	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7712	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2344	Approved
0.7703	Intermediate Similarity	NPD2346	Discontinued
0.7667	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1203	Approved
0.7651	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1296	Phase 2
0.7639	Intermediate Similarity	NPD3268	Approved
0.7635	Intermediate Similarity	NPD6099	Approved
0.7635	Intermediate Similarity	NPD6100	Approved
0.7626	Intermediate Similarity	NPD1610	Phase 2
0.7616	Intermediate Similarity	NPD4360	Phase 2
0.7616	Intermediate Similarity	NPD4363	Phase 3
0.7613	Intermediate Similarity	NPD3226	Approved
0.7606	Intermediate Similarity	NPD1019	Discontinued
0.7591	Intermediate Similarity	NPD1548	Phase 1
0.7571	Intermediate Similarity	NPD9717	Approved
0.7568	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6585	Discontinued
0.7561	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD2797	Approved
0.7534	Intermediate Similarity	NPD3140	Approved
0.7534	Intermediate Similarity	NPD4307	Phase 2
0.7534	Intermediate Similarity	NPD3142	Approved
0.7517	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD3887	Approved
0.7482	Intermediate Similarity	NPD17	Approved
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1471	Phase 3
0.7434	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD943	Approved
0.7403	Intermediate Similarity	NPD7390	Discontinued
0.7389	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6104	Discontinued
0.7376	Intermediate Similarity	NPD422	Phase 1
0.7371	Intermediate Similarity	NPD4361	Phase 2
0.7371	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1729	Discontinued
0.7358	Intermediate Similarity	NPD6279	Approved
0.7358	Intermediate Similarity	NPD6280	Approved
0.7355	Intermediate Similarity	NPD4662	Approved
0.7355	Intermediate Similarity	NPD4661	Approved
0.7343	Intermediate Similarity	NPD3225	Approved
0.7343	Intermediate Similarity	NPD1876	Approved
0.7333	Intermediate Similarity	NPD4308	Phase 3
0.7333	Intermediate Similarity	NPD2403	Approved
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7324	Intermediate Similarity	NPD1608	Approved
0.7317	Intermediate Similarity	NPD7229	Phase 3
0.7317	Intermediate Similarity	NPD6808	Phase 2
0.7317	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD5710	Approved
0.7303	Intermediate Similarity	NPD2424	Discontinued
0.7297	Intermediate Similarity	NPD1613	Approved
0.7297	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1651	Approved
0.7279	Intermediate Similarity	NPD5535	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD4288	Approved
0.726	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1652	Phase 2
0.725	Intermediate Similarity	NPD6844	Discontinued
0.7248	Intermediate Similarity	NPD6355	Discontinued
0.7237	Intermediate Similarity	NPD2353	Approved
0.7237	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD9545	Approved
0.7212	Intermediate Similarity	NPD3787	Discontinued
0.7207	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD8455	Phase 2
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.72	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4477	Approved
0.7171	Intermediate Similarity	NPD4476	Approved
0.717	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7584	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4618	Approved
0.7133	Intermediate Similarity	NPD4622	Approved
0.7097	Intermediate Similarity	NPD7003	Approved
0.7093	Intermediate Similarity	NPD8312	Approved
0.7093	Intermediate Similarity	NPD8313	Approved
0.7092	Intermediate Similarity	NPD1894	Discontinued
0.7089	Intermediate Similarity	NPD6273	Approved
0.7089	Intermediate Similarity	NPD5049	Phase 3
0.7075	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2861	Phase 2
0.7071	Intermediate Similarity	NPD9493	Approved
0.707	Intermediate Similarity	NPD7212	Phase 2
0.707	Intermediate Similarity	NPD7213	Phase 3
0.707	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2979	Phase 3
0.7066	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5242	Approved
0.7059	Intermediate Similarity	NPD2438	Suspended
0.7055	Intermediate Similarity	NPD5353	Approved
0.7051	Intermediate Similarity	NPD2354	Approved
0.7047	Intermediate Similarity	NPD411	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