NPASS Compound

Structure

NPC11566 OpenBabel07101719142D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 2.5000 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 -2.3660 1.6340 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 -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 -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 -1.5000 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 -0.8660 -1.5000 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 0.0000 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 1 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 -0.8660 2.5000 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 -1.8660 2.5000 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 22 1 0 0 0 0 2 22 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 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 19 24 1 0 0 0 0 20 15 1 6 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.17
Volume:	377.468
LogP:	4.403
LogD:	3.836
LogS:	-6.053
# 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:	0.772
Synthetic Accessibility Score:	3.264
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:	-4.519
MDCK Permeability:	1.2578101632243488e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.154
Plasma Protein Binding (PPB):	92.00605010986328%
Volume Distribution (VD):	0.351
Pgp-substrate:	3.831305980682373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.726
CYP1A2-substrate:	0.79
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.92
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.736
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.736

ADMET: Excretion

Clearance (CL):	7.037
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.269
Rat Oral Acute Toxicity:	0.742
Maximum Recommended Daily Dose:	0.412
Skin Sensitization:	0.095
Carcinogencity:	0.732
Eye Corrosion:	0.003
Eye Irritation:	0.187
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC11566

Natural Product ID:	NPC11566
*Common Name:**	(2S)-7-Methoxy-8-(3-Methoxy-3-Methylbut-1-Enyl)Flavanone
IUPAC Name:	(2S)-7-methoxy-8-[(E)-3-methoxy-3-methylbut-1-enyl]-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	VGCABPVIACQUCY-SJFMBGHLSA-N
Standard InCHI:	InChI=1S/C22H24O4/c1-22(2,25-4)13-12-17-19(24-3)11-10-16-18(23)14-20(26-21(16)17)15-8-6-5-7-9-15/h5-13,20H,14H2,1-4H3/b13-12+/t20-/m0/s1
SMILES:	COC(/C=C/c1c(OC)ccc2c1O[C@@H](CC2=O)c1ccccc1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408953
PubChem CID:	73349082
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO22730	Indigofera spicata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23895019]
NPO22730	Indigofera spicata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio	=	5.9	n.a.	PMID[566073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	49000.0	nM	PMID[566073]
NPT2	Others	Unspecified		CD	=	8.3	uM	PMID[566073]

☑ 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 NPC11566 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	434
0.1-0.2	1571
0.2-0.3	4167
0.3-0.4	10579
0.4-0.5	7714
0.5-0.6	3903
0.6-0.7	6150
0.7-0.8	5186
0.8-0.85	1660
0.85-0.9	928
0.9-0.95	364
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC259685
0.9779	High Similarity	NPC147145
0.9778	High Similarity	NPC472409
0.9708	High Similarity	NPC59522
0.9699	High Similarity	NPC99854
0.9638	High Similarity	NPC209040
0.9627	High Similarity	NPC161196
0.9624	High Similarity	NPC125269
0.9565	High Similarity	NPC143896
0.9565	High Similarity	NPC221432
0.9565	High Similarity	NPC91560
0.9565	High Similarity	NPC310130
0.9565	High Similarity	NPC478086
0.9565	High Similarity	NPC316816
0.9565	High Similarity	NPC39329
0.9565	High Similarity	NPC75049
0.9565	High Similarity	NPC149026
0.9565	High Similarity	NPC214166
0.9565	High Similarity	NPC169591
0.9565	High Similarity	NPC175504
0.9565	High Similarity	NPC68104
0.9565	High Similarity	NPC257097
0.9565	High Similarity	NPC150408
0.9565	High Similarity	NPC164980
0.9562	High Similarity	NPC52576
0.9562	High Similarity	NPC22467
0.95	High Similarity	NPC23728
0.95	High Similarity	NPC471285
0.95	High Similarity	NPC110303
0.9496	High Similarity	NPC236766
0.9496	High Similarity	NPC473015
0.9496	High Similarity	NPC131568
0.9496	High Similarity	NPC473013
0.9496	High Similarity	NPC131579
0.9496	High Similarity	NPC197252
0.9493	High Similarity	NPC78
0.9493	High Similarity	NPC166482
0.9493	High Similarity	NPC194432
0.9493	High Similarity	NPC324436
0.9493	High Similarity	NPC223500
0.9493	High Similarity	NPC328164
0.9493	High Similarity	NPC265040
0.9493	High Similarity	NPC177354
0.9493	High Similarity	NPC10937
0.9493	High Similarity	NPC76372
0.9493	High Similarity	NPC228504
0.9493	High Similarity	NPC182852
0.9493	High Similarity	NPC66515
0.9493	High Similarity	NPC148757
0.9493	High Similarity	NPC64915
0.9493	High Similarity	NPC40833
0.9493	High Similarity	NPC1089
0.9493	High Similarity	NPC125855
0.9493	High Similarity	NPC324134
0.9493	High Similarity	NPC107572
0.9493	High Similarity	NPC306829
0.9493	High Similarity	NPC161506
0.9493	High Similarity	NPC32739
0.9493	High Similarity	NPC37496
0.9493	High Similarity	NPC166934
0.9493	High Similarity	NPC167624
0.9493	High Similarity	NPC76338
0.9493	High Similarity	NPC227579
0.9493	High Similarity	NPC220998
0.9493	High Similarity	NPC296917
0.9485	High Similarity	NPC17848
0.9481	High Similarity	NPC254741
0.9433	High Similarity	NPC132592
0.9433	High Similarity	NPC160821
0.9429	High Similarity	NPC83357
0.9429	High Similarity	NPC127059
0.9429	High Similarity	NPC267375
0.9429	High Similarity	NPC20488
0.9429	High Similarity	NPC142405
0.9429	High Similarity	NPC312973
0.9429	High Similarity	NPC285630
0.9429	High Similarity	NPC214774
0.9429	High Similarity	NPC111786
0.9429	High Similarity	NPC67805
0.9429	High Similarity	NPC176229
0.9429	High Similarity	NPC195621
0.9429	High Similarity	NPC301276
0.9429	High Similarity	NPC470647
0.9429	High Similarity	NPC88964
0.9429	High Similarity	NPC475052
0.9429	High Similarity	NPC54577
0.9429	High Similarity	NPC246948
0.9424	High Similarity	NPC125894
0.9424	High Similarity	NPC77794
0.9424	High Similarity	NPC223812
0.9424	High Similarity	NPC185276
0.9424	High Similarity	NPC18585
0.9424	High Similarity	NPC107177
0.9424	High Similarity	NPC166138
0.9424	High Similarity	NPC106985
0.9424	High Similarity	NPC81697
0.9424	High Similarity	NPC85162
0.9424	High Similarity	NPC278249
0.942	High Similarity	NPC166689
0.942	High Similarity	NPC110038
0.942	High Similarity	NPC4743
0.942	High Similarity	NPC213322
0.942	High Similarity	NPC96408
0.942	High Similarity	NPC156190
0.942	High Similarity	NPC103362
0.942	High Similarity	NPC279650
0.942	High Similarity	NPC312391
0.942	High Similarity	NPC17170
0.942	High Similarity	NPC258630
0.942	High Similarity	NPC248372
0.942	High Similarity	NPC3188
0.942	High Similarity	NPC324386
0.9412	High Similarity	NPC157855
0.9407	High Similarity	NPC46869
0.9362	High Similarity	NPC472627
0.9362	High Similarity	NPC283234
0.9362	High Similarity	NPC296998
0.9362	High Similarity	NPC473077
0.9357	High Similarity	NPC235217
0.9357	High Similarity	NPC179970
0.9357	High Similarity	NPC473014
0.9357	High Similarity	NPC87486
0.9357	High Similarity	NPC124780
0.9353	High Similarity	NPC11561
0.9353	High Similarity	NPC144499
0.9353	High Similarity	NPC226636
0.9348	High Similarity	NPC69769
0.9348	High Similarity	NPC188243
0.9348	High Similarity	NPC171094
0.9348	High Similarity	NPC110228
0.9348	High Similarity	NPC6407
0.9348	High Similarity	NPC150522
0.9328	High Similarity	NPC473655
0.9328	High Similarity	NPC229646
0.9328	High Similarity	NPC101294
0.9296	High Similarity	NPC161191
0.9291	High Similarity	NPC470134
0.9291	High Similarity	NPC470133
0.9291	High Similarity	NPC109183
0.9291	High Similarity	NPC470131
0.9291	High Similarity	NPC477955
0.9291	High Similarity	NPC472629
0.9291	High Similarity	NPC470132
0.9291	High Similarity	NPC473078
0.9286	High Similarity	NPC38219
0.9281	High Similarity	NPC147688
0.9281	High Similarity	NPC64908
0.9281	High Similarity	NPC205006
0.9281	High Similarity	NPC110969
0.9281	High Similarity	NPC156590
0.9281	High Similarity	NPC118840
0.9275	High Similarity	NPC20709
0.9275	High Similarity	NPC140890
0.9275	High Similarity	NPC310135
0.9275	High Similarity	NPC225153
0.9275	High Similarity	NPC329203
0.9275	High Similarity	NPC265871
0.9275	High Similarity	NPC150648
0.9275	High Similarity	NPC274784
0.9275	High Similarity	NPC222342
0.9259	High Similarity	NPC292998
0.9259	High Similarity	NPC223354
0.9254	High Similarity	NPC278556
0.9254	High Similarity	NPC284424
0.9248	High Similarity	NPC228184
0.9236	High Similarity	NPC263384
0.9236	High Similarity	NPC472580
0.9236	High Similarity	NPC244577
0.9236	High Similarity	NPC472420
0.9236	High Similarity	NPC472422
0.9236	High Similarity	NPC471676
0.9231	High Similarity	NPC473016
0.9231	High Similarity	NPC472628
0.9231	High Similarity	NPC164299
0.9225	High Similarity	NPC79469
0.9225	High Similarity	NPC10990
0.9225	High Similarity	NPC237635
0.9225	High Similarity	NPC24673
0.9225	High Similarity	NPC218300
0.9225	High Similarity	NPC282335
0.9225	High Similarity	NPC104406
0.9225	High Similarity	NPC300988
0.9225	High Similarity	NPC97716
0.9225	High Similarity	NPC201731
0.922	High Similarity	NPC319752
0.922	High Similarity	NPC470136
0.922	High Similarity	NPC271288
0.922	High Similarity	NPC470135
0.922	High Similarity	NPC39045
0.922	High Similarity	NPC470890
0.922	High Similarity	NPC171656
0.922	High Similarity	NPC234629
0.922	High Similarity	NPC311741
0.9209	High Similarity	NPC235239
0.9209	High Similarity	NPC241100
0.9209	High Similarity	NPC76445
0.9209	High Similarity	NPC284550
0.9209	High Similarity	NPC305355
0.9209	High Similarity	NPC261227
0.9209	High Similarity	NPC129853

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 NPC11566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	959
0.2-0.3	1525
0.3-0.4	2609
0.4-0.5	1898
0.5-0.6	1160
0.6-0.7	439
0.7-0.8	143
0.8-0.85	26
0.85-0.9	15
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD2796	Approved
0.9203	High Similarity	NPD1549	Phase 2
0.913	High Similarity	NPD1550	Clinical (unspecified phase)
0.913	High Similarity	NPD1552	Clinical (unspecified phase)
0.898	High Similarity	NPD7096	Clinical (unspecified phase)
0.8973	High Similarity	NPD7411	Suspended
0.8951	High Similarity	NPD7410	Clinical (unspecified phase)
0.8951	High Similarity	NPD4378	Clinical (unspecified phase)
0.8851	High Similarity	NPD7819	Suspended
0.8851	High Similarity	NPD2393	Clinical (unspecified phase)
0.88	High Similarity	NPD7075	Discontinued
0.8792	High Similarity	NPD8443	Clinical (unspecified phase)
0.8784	High Similarity	NPD6801	Discontinued
0.8776	High Similarity	NPD4380	Phase 2
0.875	High Similarity	NPD6799	Approved
0.8714	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD1240	Approved
0.8684	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD1547	Clinical (unspecified phase)
0.8571	High Similarity	NPD1607	Approved
0.8533	High Similarity	NPD1934	Approved
0.8523	High Similarity	NPD6599	Discontinued
0.8472	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1243	Approved
0.8446	Intermediate Similarity	NPD920	Approved
0.8431	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD3748	Approved
0.8311	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD6832	Phase 2
0.8269	Intermediate Similarity	NPD6959	Discontinued
0.8247	Intermediate Similarity	NPD7768	Phase 2
0.82	Intermediate Similarity	NPD5403	Approved
0.8188	Intermediate Similarity	NPD5401	Approved
0.8187	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.8129	Intermediate Similarity	NPD3882	Suspended
0.8121	Intermediate Similarity	NPD1511	Approved
0.8117	Intermediate Similarity	NPD2801	Approved
0.8113	Intermediate Similarity	NPD6166	Phase 2
0.8113	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3749	Approved
0.8069	Intermediate Similarity	NPD2799	Discontinued
0.8041	Intermediate Similarity	NPD3750	Approved
0.8025	Intermediate Similarity	NPD919	Approved
0.8014	Intermediate Similarity	NPD1551	Phase 2
0.8013	Intermediate Similarity	NPD1512	Approved
0.7973	Intermediate Similarity	NPD2800	Approved
0.7931	Intermediate Similarity	NPD6651	Approved
0.7927	Intermediate Similarity	NPD6559	Discontinued
0.7925	Intermediate Similarity	NPD1247	Approved
0.7914	Intermediate Similarity	NPD7074	Phase 3
0.7902	Intermediate Similarity	NPD2313	Discontinued
0.7901	Intermediate Similarity	NPD3818	Discontinued
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7866	Intermediate Similarity	NPD5953	Discontinued
0.7862	Intermediate Similarity	NPD1933	Approved
0.7853	Intermediate Similarity	NPD7286	Phase 2
0.7853	Intermediate Similarity	NPD7054	Approved
0.7853	Intermediate Similarity	NPD5844	Phase 1
0.7852	Intermediate Similarity	NPD2654	Approved
0.7842	Intermediate Similarity	NPD3972	Approved
0.7834	Intermediate Similarity	NPD5402	Approved
0.7826	Intermediate Similarity	NPD3926	Phase 2
0.7823	Intermediate Similarity	NPD7033	Discontinued
0.7805	Intermediate Similarity	NPD7472	Approved
0.78	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1241	Discontinued
0.7758	Intermediate Similarity	NPD6797	Phase 2
0.7756	Intermediate Similarity	NPD5889	Approved
0.7756	Intermediate Similarity	NPD5890	Approved
0.7746	Intermediate Similarity	NPD2798	Approved
0.774	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5124	Phase 1
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7718	Intermediate Similarity	NPD2344	Approved
0.7712	Intermediate Similarity	NPD2534	Approved
0.7712	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD2532	Approved
0.7711	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD6585	Discontinued
0.7682	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1203	Approved
0.7676	Intermediate Similarity	NPD3266	Approved
0.7676	Intermediate Similarity	NPD3267	Approved
0.7671	Intermediate Similarity	NPD4307	Phase 2
0.7665	Intermediate Similarity	NPD7808	Phase 3
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.7651	Intermediate Similarity	NPD6100	Approved
0.7651	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4908	Phase 1
0.7632	Intermediate Similarity	NPD3887	Approved
0.7628	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD7473	Discontinued
0.7622	Intermediate Similarity	NPD1019	Discontinued
0.7589	Intermediate Similarity	NPD9717	Approved
0.7584	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3142	Approved
0.7551	Intermediate Similarity	NPD3140	Approved
0.7534	Intermediate Similarity	NPD1296	Phase 2
0.7534	Intermediate Similarity	NPD3268	Approved
0.7529	Intermediate Similarity	NPD4360	Phase 2
0.7529	Intermediate Similarity	NPD4363	Phase 3
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD2309	Approved
0.7483	Intermediate Similarity	NPD1471	Phase 3
0.7482	Intermediate Similarity	NPD1548	Phase 1
0.7467	Intermediate Similarity	NPD4308	Phase 3
0.7443	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD943	Approved
0.7431	Intermediate Similarity	NPD2797	Approved
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.7405	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6104	Discontinued
0.7381	Intermediate Similarity	NPD1729	Discontinued
0.7376	Intermediate Similarity	NPD17	Approved
0.7375	Intermediate Similarity	NPD6280	Approved
0.7375	Intermediate Similarity	NPD6279	Approved
0.7372	Intermediate Similarity	NPD4662	Approved
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4661	Approved
0.7368	Intermediate Similarity	NPD2353	Approved
0.7368	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1876	Approved
0.7349	Intermediate Similarity	NPD2403	Approved
0.7347	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD6808	Phase 2
0.732	Intermediate Similarity	NPD2424	Discontinued
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7296	Intermediate Similarity	NPD7458	Discontinued
0.7288	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4361	Phase 2
0.7284	Intermediate Similarity	NPD4288	Approved
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7268	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7262	Intermediate Similarity	NPD3751	Discontinued
0.7255	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3225	Approved
0.7239	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD9545	Approved
0.7229	Intermediate Similarity	NPD3787	Discontinued
0.7229	Intermediate Similarity	NPD7229	Phase 3
0.7229	Intermediate Similarity	NPD5710	Approved
0.7229	Intermediate Similarity	NPD5711	Approved
0.7222	Intermediate Similarity	NPD1465	Phase 2
0.7222	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1608	Approved
0.7215	Intermediate Similarity	NPD5049	Phase 3
0.72	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1613	Approved
0.7183	Intermediate Similarity	NPD1651	Approved
0.7179	Intermediate Similarity	NPD2354	Approved
0.7174	Intermediate Similarity	NPD5535	Approved
0.7162	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD7577	Discontinued
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7135	Intermediate Similarity	NPD3823	Discontinued
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7117	Intermediate Similarity	NPD5761	Phase 2
0.7117	Intermediate Similarity	NPD5760	Phase 2
0.7117	Intermediate Similarity	NPD8455	Phase 2
0.7115	Intermediate Similarity	NPD7003	Approved
0.711	Intermediate Similarity	NPD8312	Approved
0.711	Intermediate Similarity	NPD8313	Approved
0.7107	Intermediate Similarity	NPD6273	Approved
0.7102	Intermediate Similarity	NPD4287	Approved
0.7092	Intermediate Similarity	NPD9493	Approved
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7083	Intermediate Similarity	NPD5242	Approved
0.7081	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4476	Approved
0.7078	Intermediate Similarity	NPD4477	Approved
0.7073	Intermediate Similarity	NPD5353	Approved
0.7067	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3764	Approved
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7063	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4749	Approved
0.7047	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD447	Suspended

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