NPASS Compound

Structure

NPC147145 OpenBabel07101718182D 25 27 0 0 1 0 0 0 0 0999 V2000 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 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 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 -1.3660 3.3660 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 18 24 1 0 0 0 0 19 14 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.15
Volume:	360.172
LogP:	3.642
LogD:	3.462
LogS:	-4.738
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.908
Synthetic Accessibility Score:	3.13
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.527
MDCK Permeability:	1.3112551641825121e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	89.3440170288086%
Volume Distribution (VD):	0.332
Pgp-substrate:	4.739253520965576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.718
CYP1A2-substrate:	0.59
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.694
CYP2C9-inhibitor:	0.912
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.707
CYP2D6-substrate:	0.845
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	9.501
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.34
Rat Oral Acute Toxicity:	0.715
Maximum Recommended Daily Dose:	0.344
Skin Sensitization:	0.077
Carcinogencity:	0.8
Eye Corrosion:	0.003
Eye Irritation:	0.517
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC147145

Natural Product ID:	NPC147145
*Common Name:**	(2S)-2,3-Dihydrotephroapollin C
IUPAC Name:	(2S)-8-[(E)-3-hydroxy-3-methylbut-1-enyl]-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	DSOKHRJRTZPRBU-CVTTXWKISA-N
Standard InCHI:	InChI=1S/C21H22O4/c1-21(2,23)12-11-16-18(24-3)10-9-15-17(22)13-19(25-20(15)16)14-7-5-4-6-8-14/h4-12,19,23H,13H2,1-3H3/b12-11+/t19-/m0/s1
SMILES:	CC(C)(/C=C/c1c(ccc2C(=O)C[C@@H](c3ccccc3)Oc12)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408952
PubChem CID:	52316190
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	=	11.3	n.a.	PMID[544703]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47400.0	nM	PMID[544703]
NPT2	Others	Unspecified		CD	=	4.2	uM	PMID[544703]

☑ 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 NPC147145 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	371
0.1-0.2	1501
0.2-0.3	3736
0.3-0.4	9839
0.4-0.5	8703
0.5-0.6	3647
0.6-0.7	5891
0.7-0.8	5291
0.8-0.85	1927
0.85-0.9	1148
0.9-0.95	479
0.95-1	164

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC209040
0.9783	High Similarity	NPC143896
0.9783	High Similarity	NPC175504
0.9783	High Similarity	NPC316816
0.9783	High Similarity	NPC39329
0.9783	High Similarity	NPC149026
0.9783	High Similarity	NPC150408
0.9783	High Similarity	NPC310130
0.9783	High Similarity	NPC68104
0.9783	High Similarity	NPC478086
0.9783	High Similarity	NPC91560
0.9783	High Similarity	NPC164980
0.9783	High Similarity	NPC214166
0.9783	High Similarity	NPC169591
0.9783	High Similarity	NPC221432
0.9783	High Similarity	NPC75049
0.9783	High Similarity	NPC257097
0.9779	High Similarity	NPC11566
0.9714	High Similarity	NPC23728
0.9714	High Similarity	NPC110303
0.9712	High Similarity	NPC473015
0.9712	High Similarity	NPC131579
0.9712	High Similarity	NPC131568
0.9712	High Similarity	NPC236766
0.9712	High Similarity	NPC197252
0.9712	High Similarity	NPC473013
0.971	High Similarity	NPC40833
0.971	High Similarity	NPC194432
0.971	High Similarity	NPC227579
0.971	High Similarity	NPC76372
0.971	High Similarity	NPC166934
0.971	High Similarity	NPC64915
0.971	High Similarity	NPC223500
0.971	High Similarity	NPC265040
0.971	High Similarity	NPC166482
0.971	High Similarity	NPC107572
0.971	High Similarity	NPC10937
0.971	High Similarity	NPC328164
0.971	High Similarity	NPC32739
0.971	High Similarity	NPC78
0.971	High Similarity	NPC324134
0.971	High Similarity	NPC125855
0.971	High Similarity	NPC228504
0.971	High Similarity	NPC76338
0.971	High Similarity	NPC148757
0.971	High Similarity	NPC324436
0.971	High Similarity	NPC167624
0.971	High Similarity	NPC37496
0.971	High Similarity	NPC182852
0.971	High Similarity	NPC296917
0.971	High Similarity	NPC66515
0.971	High Similarity	NPC177354
0.971	High Similarity	NPC161506
0.971	High Similarity	NPC220998
0.971	High Similarity	NPC1089
0.971	High Similarity	NPC306829
0.9645	High Similarity	NPC132592
0.9645	High Similarity	NPC160821
0.9643	High Similarity	NPC176229
0.9643	High Similarity	NPC285630
0.9643	High Similarity	NPC475052
0.9643	High Similarity	NPC312973
0.9643	High Similarity	NPC470647
0.9643	High Similarity	NPC301276
0.9643	High Similarity	NPC267375
0.9643	High Similarity	NPC54577
0.9643	High Similarity	NPC246948
0.9643	High Similarity	NPC88964
0.9643	High Similarity	NPC111786
0.9643	High Similarity	NPC142405
0.9643	High Similarity	NPC83357
0.9643	High Similarity	NPC195621
0.9643	High Similarity	NPC20488
0.9643	High Similarity	NPC127059
0.9643	High Similarity	NPC67805
0.9643	High Similarity	NPC214774
0.964	High Similarity	NPC18585
0.964	High Similarity	NPC81697
0.964	High Similarity	NPC223812
0.964	High Similarity	NPC107177
0.964	High Similarity	NPC278249
0.964	High Similarity	NPC125894
0.964	High Similarity	NPC106985
0.964	High Similarity	NPC77794
0.964	High Similarity	NPC185276
0.964	High Similarity	NPC85162
0.964	High Similarity	NPC166138
0.9638	High Similarity	NPC96408
0.9638	High Similarity	NPC248372
0.9638	High Similarity	NPC279650
0.9638	High Similarity	NPC17170
0.9638	High Similarity	NPC258630
0.9638	High Similarity	NPC3188
0.9638	High Similarity	NPC156190
0.9638	High Similarity	NPC213322
0.9638	High Similarity	NPC103362
0.9638	High Similarity	NPC324386
0.9638	High Similarity	NPC166689
0.9638	High Similarity	NPC110038
0.9638	High Similarity	NPC4743
0.9638	High Similarity	NPC312391
0.9632	High Similarity	NPC259685
0.9574	High Similarity	NPC473077
0.9574	High Similarity	NPC283234
0.9574	High Similarity	NPC472627
0.9574	High Similarity	NPC296998
0.9571	High Similarity	NPC235217
0.9571	High Similarity	NPC124780
0.9571	High Similarity	NPC473014
0.9571	High Similarity	NPC87486
0.9568	High Similarity	NPC226636
0.9568	High Similarity	NPC11561
0.9568	High Similarity	NPC144499
0.9565	High Similarity	NPC69769
0.9565	High Similarity	NPC6407
0.9565	High Similarity	NPC110228
0.9565	High Similarity	NPC188243
0.9565	High Similarity	NPC472409
0.9565	High Similarity	NPC150522
0.9507	High Similarity	NPC161191
0.9504	High Similarity	NPC472629
0.9504	High Similarity	NPC109183
0.9504	High Similarity	NPC470134
0.9504	High Similarity	NPC473078
0.9504	High Similarity	NPC470133
0.9504	High Similarity	NPC470132
0.9504	High Similarity	NPC477955
0.9504	High Similarity	NPC470131
0.95	High Similarity	NPC59522
0.95	High Similarity	NPC38219
0.9496	High Similarity	NPC205006
0.9496	High Similarity	NPC156590
0.9496	High Similarity	NPC118840
0.9496	High Similarity	NPC64908
0.9496	High Similarity	NPC147688
0.9496	High Similarity	NPC110969
0.9493	High Similarity	NPC20709
0.9493	High Similarity	NPC140890
0.9493	High Similarity	NPC274784
0.9493	High Similarity	NPC265871
0.9493	High Similarity	NPC222342
0.9493	High Similarity	NPC150648
0.9493	High Similarity	NPC329203
0.9493	High Similarity	NPC310135
0.9493	High Similarity	NPC225153
0.9485	High Similarity	NPC99854
0.9444	High Similarity	NPC244577
0.9444	High Similarity	NPC263384
0.9444	High Similarity	NPC471676
0.9444	High Similarity	NPC472422
0.9444	High Similarity	NPC472420
0.9444	High Similarity	NPC472580
0.9441	High Similarity	NPC473016
0.9441	High Similarity	NPC472628
0.9437	High Similarity	NPC237635
0.9437	High Similarity	NPC300988
0.9437	High Similarity	NPC79469
0.9437	High Similarity	NPC201731
0.9437	High Similarity	NPC104406
0.9437	High Similarity	NPC10990
0.9437	High Similarity	NPC24673
0.9437	High Similarity	NPC97716
0.9433	High Similarity	NPC470135
0.9433	High Similarity	NPC271288
0.9433	High Similarity	NPC470136
0.9433	High Similarity	NPC234629
0.9433	High Similarity	NPC39045
0.9433	High Similarity	NPC470890
0.9433	High Similarity	NPC319752
0.9433	High Similarity	NPC311741
0.9424	High Similarity	NPC261227
0.9424	High Similarity	NPC241100
0.9424	High Similarity	NPC305355
0.9424	High Similarity	NPC270883
0.9424	High Similarity	NPC159275
0.9424	High Similarity	NPC235239
0.9424	High Similarity	NPC129853
0.9424	High Similarity	NPC475680
0.9424	High Similarity	NPC172986
0.9424	High Similarity	NPC76445
0.9424	High Similarity	NPC284550
0.942	High Similarity	NPC329225
0.942	High Similarity	NPC99333
0.942	High Similarity	NPC472460
0.942	High Similarity	NPC188947
0.942	High Similarity	NPC147686
0.942	High Similarity	NPC280284
0.942	High Similarity	NPC124269
0.9416	High Similarity	NPC161196
0.9412	High Similarity	NPC125269
0.9379	High Similarity	NPC477957
0.9379	High Similarity	NPC473996
0.9375	High Similarity	NPC472633
0.9375	High Similarity	NPC61258
0.9371	High Similarity	NPC321623
0.9371	High Similarity	NPC189087
0.9371	High Similarity	NPC266572
0.9371	High Similarity	NPC168085
0.9371	High Similarity	NPC6511
0.9371	High Similarity	NPC39195

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 NPC147145 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	957
0.2-0.3	1467
0.3-0.4	2572
0.4-0.5	1952
0.5-0.6	1186
0.6-0.7	473
0.7-0.8	167
0.8-0.85	30
0.85-0.9	18
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.942	High Similarity	NPD1549	Phase 2
0.9348	High Similarity	NPD1552	Clinical (unspecified phase)
0.9348	High Similarity	NPD1550	Clinical (unspecified phase)
0.9275	High Similarity	NPD2796	Approved
0.9178	High Similarity	NPD7411	Suspended
0.9161	High Similarity	NPD7410	Clinical (unspecified phase)
0.9161	High Similarity	NPD4378	Clinical (unspecified phase)
0.9054	High Similarity	NPD2393	Clinical (unspecified phase)
0.9054	High Similarity	NPD7096	Clinical (unspecified phase)
0.9	High Similarity	NPD7075	Discontinued
0.8993	High Similarity	NPD8443	Clinical (unspecified phase)
0.8986	High Similarity	NPD6801	Discontinued
0.898	High Similarity	NPD4380	Phase 2
0.8929	High Similarity	NPD1510	Phase 2
0.8926	High Similarity	NPD7819	Suspended
0.8913	High Similarity	NPD1240	Approved
0.8828	High Similarity	NPD6799	Approved
0.8786	High Similarity	NPD1607	Approved
0.8733	High Similarity	NPD1934	Approved
0.8681	High Similarity	NPD7421	Clinical (unspecified phase)
0.8627	High Similarity	NPD4381	Clinical (unspecified phase)
0.86	High Similarity	NPD6599	Discontinued
0.8535	High Similarity	NPD7852	Clinical (unspecified phase)
0.8516	High Similarity	NPD5494	Approved
0.8462	Intermediate Similarity	NPD6959	Discontinued
0.8442	Intermediate Similarity	NPD7768	Phase 2
0.84	Intermediate Similarity	NPD5403	Approved
0.8382	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3882	Suspended
0.8322	Intermediate Similarity	NPD1511	Approved
0.8312	Intermediate Similarity	NPD2801	Approved
0.8302	Intermediate Similarity	NPD6166	Phase 2
0.8302	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1243	Approved
0.8278	Intermediate Similarity	NPD920	Approved
0.8269	Intermediate Similarity	NPD3749	Approved
0.8267	Intermediate Similarity	NPD5401	Approved
0.8258	Intermediate Similarity	NPD3817	Phase 2
0.8255	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD3750	Approved
0.8219	Intermediate Similarity	NPD1551	Phase 2
0.8212	Intermediate Similarity	NPD1512	Approved
0.8176	Intermediate Similarity	NPD2800	Approved
0.8151	Intermediate Similarity	NPD2799	Discontinued
0.8151	Intermediate Similarity	NPD3748	Approved
0.8146	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD6651	Approved
0.811	Intermediate Similarity	NPD6559	Discontinued
0.8099	Intermediate Similarity	NPD6832	Phase 2
0.8098	Intermediate Similarity	NPD7074	Phase 3
0.8095	Intermediate Similarity	NPD2935	Discontinued
0.8089	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD3818	Discontinued
0.8049	Intermediate Similarity	NPD5953	Discontinued
0.8037	Intermediate Similarity	NPD5844	Phase 1
0.8037	Intermediate Similarity	NPD7054	Approved
0.8037	Intermediate Similarity	NPD7286	Phase 2
0.8027	Intermediate Similarity	NPD7033	Discontinued
0.8025	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7988	Intermediate Similarity	NPD7472	Approved
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2313	Discontinued
0.7952	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD5124	Phase 1
0.7945	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6797	Phase 2
0.7919	Intermediate Similarity	NPD2344	Approved
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7892	Intermediate Similarity	NPD7251	Discontinued
0.7887	Intermediate Similarity	NPD1203	Approved
0.7881	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD919	Approved
0.7852	Intermediate Similarity	NPD6099	Approved
0.7852	Intermediate Similarity	NPD6100	Approved
0.7847	Intermediate Similarity	NPD4908	Phase 1
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.784	Intermediate Similarity	NPD6232	Discontinued
0.7834	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2798	Approved
0.7821	Intermediate Similarity	NPD3226	Approved
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.7801	Intermediate Similarity	NPD9717	Approved
0.78	Intermediate Similarity	NPD2346	Discontinued
0.7785	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1247	Approved
0.7763	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3268	Approved
0.7738	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1610	Phase 2
0.7712	Intermediate Similarity	NPD2309	Approved
0.7703	Intermediate Similarity	NPD1933	Approved
0.7701	Intermediate Similarity	NPD4360	Phase 2
0.7701	Intermediate Similarity	NPD4363	Phase 3
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7697	Intermediate Similarity	NPD2654	Approved
0.7683	Intermediate Similarity	NPD3926	Phase 2
0.7676	Intermediate Similarity	NPD3972	Approved
0.7667	Intermediate Similarity	NPD4308	Phase 3
0.7639	Intermediate Similarity	NPD2797	Approved
0.7635	Intermediate Similarity	NPD943	Approved
0.7619	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5889	Approved
0.761	Intermediate Similarity	NPD5890	Approved
0.7595	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1241	Discontinued
0.7584	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1729	Discontinued
0.7551	Intermediate Similarity	NPD4625	Phase 3
0.7547	Intermediate Similarity	NPD6585	Discontinued
0.7517	Intermediate Similarity	NPD3266	Approved
0.7517	Intermediate Similarity	NPD4307	Phase 2
0.7517	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3887	Approved
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7471	Intermediate Similarity	NPD6104	Discontinued
0.7469	Intermediate Similarity	NPD4288	Approved
0.7466	Intermediate Similarity	NPD1019	Discontinued
0.7458	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4361	Phase 2
0.7452	Intermediate Similarity	NPD4661	Approved
0.7452	Intermediate Similarity	NPD4662	Approved
0.7448	Intermediate Similarity	NPD3225	Approved
0.7447	Intermediate Similarity	NPD9545	Approved
0.744	Intermediate Similarity	NPD3751	Discontinued
0.744	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7584	Approved
0.7425	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5711	Approved
0.741	Intermediate Similarity	NPD5710	Approved
0.7407	Intermediate Similarity	NPD1465	Phase 2
0.7403	Intermediate Similarity	NPD2424	Discontinued
0.74	Intermediate Similarity	NPD3142	Approved
0.74	Intermediate Similarity	NPD3140	Approved
0.74	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1613	Approved
0.7389	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1296	Phase 2
0.7346	Intermediate Similarity	NPD6844	Discontinued
0.7346	Intermediate Similarity	NPD7577	Discontinued
0.7338	Intermediate Similarity	NPD1471	Phase 3
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3823	Discontinued
0.731	Intermediate Similarity	NPD1608	Approved
0.7308	Intermediate Similarity	NPD7003	Approved
0.7305	Intermediate Similarity	NPD9493	Approved
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7301	Intermediate Similarity	NPD5761	Phase 2
0.7301	Intermediate Similarity	NPD5760	Phase 2
0.7296	Intermediate Similarity	NPD5049	Phase 3
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD4287	Approved
0.7267	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2354	Approved
0.726	Intermediate Similarity	NPD4749	Approved
0.7257	Intermediate Similarity	NPD8434	Phase 2
0.7248	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7239	Intermediate Similarity	NPD6279	Approved
0.7239	Intermediate Similarity	NPD6280	Approved
0.7237	Intermediate Similarity	NPD230	Phase 1
0.7237	Intermediate Similarity	NPD447	Suspended
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2353	Approved
0.7222	Intermediate Similarity	NPD17	Approved
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD2403	Approved
0.7211	Intermediate Similarity	NPD1876	Approved
0.7202	Intermediate Similarity	NPD6808	Phase 2
0.7198	Intermediate Similarity	NPD6778	Approved
0.7198	Intermediate Similarity	NPD6779	Approved
0.7198	Intermediate Similarity	NPD6777	Approved
0.7198	Intermediate Similarity	NPD6776	Approved
0.7198	Intermediate Similarity	NPD6782	Approved
0.7198	Intermediate Similarity	NPD6780	Approved
0.7198	Intermediate Similarity	NPD6781	Approved
0.7195	Intermediate Similarity	NPD8455	Phase 2
0.7188	Intermediate Similarity	NPD6273	Approved
0.7181	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2861	Phase 2
0.717	Intermediate Similarity	NPD7213	Phase 3

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