NPASS Compound

Structure

NPC171094 OpenBabel07101718292D 26 28 0 0 0 0 0 0 0 0999 V2000 0.1589 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7899 0.8827 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 -2.5000 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 -1.7321 -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 -1.7321 0.0000 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 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -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 -2.5981 -2.5000 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 -2.5000 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 14 16 1 0 0 0 0 15 24 1 0 0 0 0 16 22 2 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 20 2 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	3.282
LogD:	3.147
LogS:	-5.176
# Rotatable Bonds:	5
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	2.312
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.632
MDCK Permeability:	2.2000907847541384e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.263
Plasma Protein Binding (PPB):	87.79596710205078%
Volume Distribution (VD):	0.844
Pgp-substrate:	3.7299964427948%

ADMET: Metabolism

CYP1A2-inhibitor:	0.548
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.368
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.703

ADMET: Excretion

Clearance (CL):	10.184
Half-life (T1/2):	0.218

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.82
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.042
Carcinogencity:	0.656
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.339

Download Data

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

Natural Product: NPC171094

Natural Product ID:	NPC171094
*Common Name:**	Gramideoxybenzoin B
IUPAC Name:	5-methoxy-7-[2-(4-methoxyphenyl)-2-oxoethyl]-2,2-dimethyl-3H-chromen-4-one
Synonyms:
Standard InCHIKey:	PTIRDEKWBHJXNN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-21(2)12-17(23)20-18(25-4)10-13(11-19(20)26-21)9-16(22)14-5-7-15(24-3)8-6-14/h5-8,10-11H,9,12H2,1-4H3
SMILES:	COc1ccc(cc1)C(=O)Cc1cc(OC)c2c(c1)OC(CC2=O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431359
PubChem CID:	72702037
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO6006	Arundina graminifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24063582]
NPO6006	Arundina graminifolia	Species	Orchidaceae	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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8500.0	nM	PMID[500907]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[500907]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6400.0	nM	PMID[500907]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[500907]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[500907]

☑ 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 NPC171094 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	465
0.1-0.2	1689
0.2-0.3	4377
0.3-0.4	11223
0.4-0.5	6789
0.5-0.6	3737
0.6-0.7	5791
0.7-0.8	5472
0.8-0.85	2215
0.85-0.9	876
0.9-0.95	61
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC196114
0.9412	High Similarity	NPC254741
0.9407	High Similarity	NPC125269
0.9348	High Similarity	NPC11566
0.9338	High Similarity	NPC99854
0.9333	High Similarity	NPC292998
0.9301	High Similarity	NPC474052
0.927	High Similarity	NPC161196
0.9259	High Similarity	NPC101294
0.9259	High Similarity	NPC473655
0.9225	High Similarity	NPC130176
0.9225	High Similarity	NPC99454
0.9225	High Similarity	NPC469758
0.922	High Similarity	NPC293201
0.922	High Similarity	NPC166138
0.922	High Similarity	NPC18585
0.922	High Similarity	NPC189650
0.922	High Similarity	NPC106985
0.9214	High Similarity	NPC24075
0.9203	High Similarity	NPC259685
0.9191	High Similarity	NPC223354
0.9185	High Similarity	NPC278556
0.9185	High Similarity	NPC284424
0.9161	High Similarity	NPC470511
0.9155	High Similarity	NPC471590
0.9155	High Similarity	NPC469764
0.9149	High Similarity	NPC1534
0.9149	High Similarity	NPC147145
0.9149	High Similarity	NPC144499
0.9143	High Similarity	NPC472409
0.9137	High Similarity	NPC17848
0.9118	High Similarity	NPC182428
0.9111	High Similarity	NPC301717
0.9104	High Similarity	NPC211120
0.9097	High Similarity	NPC10304
0.9097	High Similarity	NPC63256
0.9091	High Similarity	NPC477955
0.9085	High Similarity	NPC59522
0.9085	High Similarity	NPC113089
0.9078	High Similarity	NPC103362
0.9071	High Similarity	NPC136095
0.9071	High Similarity	NPC109232
0.9065	High Similarity	NPC157855
0.9065	High Similarity	NPC103001
0.9058	High Similarity	NPC46869
0.9034	High Similarity	NPC266499
0.9028	High Similarity	NPC471285
0.9021	High Similarity	NPC311741
0.9021	High Similarity	NPC136278
0.9021	High Similarity	NPC49282
0.9021	High Similarity	NPC234629
0.9021	High Similarity	NPC209040
0.9021	High Similarity	NPC179970
0.9014	High Similarity	NPC310340
0.9014	High Similarity	NPC73028
0.9014	High Similarity	NPC11561
0.9014	High Similarity	NPC226636
0.9014	High Similarity	NPC70853
0.9014	High Similarity	NPC9966
0.9014	High Similarity	NPC167663
0.9014	High Similarity	NPC202981
0.9007	High Similarity	NPC110228
0.9007	High Similarity	NPC6407
0.9007	High Similarity	NPC129853
0.9007	High Similarity	NPC188243
0.9007	High Similarity	NPC150522
0.9007	High Similarity	NPC76445
0.9007	High Similarity	NPC284550
0.9007	High Similarity	NPC69769
0.9	High Similarity	NPC188947
0.9	High Similarity	NPC99333
0.9	High Similarity	NPC280284
0.9	High Similarity	NPC124269
0.8993	High Similarity	NPC473391
0.8993	High Similarity	NPC72452
0.8993	High Similarity	NPC61546
0.8993	High Similarity	NPC472364
0.898	High Similarity	NPC40033
0.898	High Similarity	NPC142527
0.8978	High Similarity	NPC229646
0.8973	High Similarity	NPC5840
0.8973	High Similarity	NPC189270
0.8973	High Similarity	NPC472633
0.8973	High Similarity	NPC474660
0.8966	High Similarity	NPC186397
0.8966	High Similarity	NPC37135
0.8966	High Similarity	NPC476342
0.8958	High Similarity	NPC187282
0.8958	High Similarity	NPC231013
0.8958	High Similarity	NPC290133
0.8958	High Similarity	NPC299011
0.8958	High Similarity	NPC473927
0.8958	High Similarity	NPC24136
0.8951	High Similarity	NPC150408
0.8951	High Similarity	NPC169591
0.8951	High Similarity	NPC257097
0.8951	High Similarity	NPC164980
0.8951	High Similarity	NPC38219
0.8951	High Similarity	NPC221432
0.8951	High Similarity	NPC39329
0.8951	High Similarity	NPC149026
0.8951	High Similarity	NPC17262
0.8951	High Similarity	NPC478086
0.8951	High Similarity	NPC175504
0.8951	High Similarity	NPC68104
0.8951	High Similarity	NPC91560
0.8951	High Similarity	NPC143896
0.8951	High Similarity	NPC310130
0.8951	High Similarity	NPC214166
0.8951	High Similarity	NPC75049
0.8951	High Similarity	NPC316816
0.8951	High Similarity	NPC219915
0.8944	High Similarity	NPC110969
0.8944	High Similarity	NPC147688
0.8944	High Similarity	NPC3188
0.8944	High Similarity	NPC205006
0.8944	High Similarity	NPC52576
0.8944	High Similarity	NPC185607
0.8944	High Similarity	NPC22467
0.8944	High Similarity	NPC64908
0.8944	High Similarity	NPC29536
0.8944	High Similarity	NPC156590
0.8944	High Similarity	NPC118840
0.8936	High Similarity	NPC20709
0.8936	High Similarity	NPC310135
0.8936	High Similarity	NPC222342
0.8936	High Similarity	NPC329203
0.8936	High Similarity	NPC265871
0.8936	High Similarity	NPC140890
0.8936	High Similarity	NPC150648
0.8936	High Similarity	NPC261234
0.8936	High Similarity	NPC274784
0.8936	High Similarity	NPC225153
0.8929	High Similarity	NPC250266
0.8929	High Similarity	NPC275055
0.8929	High Similarity	NPC290291
0.8929	High Similarity	NPC188879
0.8929	High Similarity	NPC266597
0.8929	High Similarity	NPC228661
0.8929	High Similarity	NPC44573
0.8921	High Similarity	NPC239495
0.8921	High Similarity	NPC9985
0.8919	High Similarity	NPC210942
0.8919	High Similarity	NPC169990
0.8919	High Similarity	NPC72370
0.8919	High Similarity	NPC329844
0.8912	High Similarity	NPC149526
0.8912	High Similarity	NPC478148
0.8912	High Similarity	NPC72958
0.8912	High Similarity	NPC232645
0.8912	High Similarity	NPC474417
0.8904	High Similarity	NPC474648
0.8904	High Similarity	NPC223988
0.8904	High Similarity	NPC238366
0.8904	High Similarity	NPC65589
0.8904	High Similarity	NPC288036
0.8904	High Similarity	NPC97029
0.8904	High Similarity	NPC158338
0.8904	High Similarity	NPC269420
0.8904	High Similarity	NPC97028
0.8904	High Similarity	NPC65775
0.8904	High Similarity	NPC100985
0.8904	High Similarity	NPC10027
0.8897	High Similarity	NPC205522
0.8897	High Similarity	NPC299923
0.8897	High Similarity	NPC24673
0.8897	High Similarity	NPC473077
0.8897	High Similarity	NPC97716
0.8897	High Similarity	NPC228184
0.8897	High Similarity	NPC104406
0.8897	High Similarity	NPC201731
0.8897	High Similarity	NPC23728
0.8897	High Similarity	NPC237635
0.8897	High Similarity	NPC110303
0.8897	High Similarity	NPC296998
0.8897	High Similarity	NPC79469
0.8889	High Similarity	NPC124780
0.8889	High Similarity	NPC87486
0.8889	High Similarity	NPC131579
0.8889	High Similarity	NPC473013
0.8889	High Similarity	NPC303185
0.8889	High Similarity	NPC184649
0.8889	High Similarity	NPC475017
0.8889	High Similarity	NPC473907
0.8889	High Similarity	NPC271288
0.8889	High Similarity	NPC311144
0.8889	High Similarity	NPC473015
0.8889	High Similarity	NPC197252
0.8889	High Similarity	NPC131568
0.8889	High Similarity	NPC236766
0.8881	High Similarity	NPC161506
0.8881	High Similarity	NPC148757
0.8881	High Similarity	NPC10937
0.8881	High Similarity	NPC37496
0.8881	High Similarity	NPC194432
0.8881	High Similarity	NPC324134
0.8881	High Similarity	NPC76338
0.8881	High Similarity	NPC182852
0.8881	High Similarity	NPC296917
0.8881	High Similarity	NPC169479

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 NPC171094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	972
0.2-0.3	1564
0.3-0.4	2592
0.4-0.5	1898
0.5-0.6	1079
0.6-0.7	449
0.7-0.8	144
0.8-0.85	38
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.927	High Similarity	NPD2796	Approved
0.8865	High Similarity	NPD1549	Phase 2
0.8794	High Similarity	NPD1550	Clinical (unspecified phase)
0.8794	High Similarity	NPD1552	Clinical (unspecified phase)
0.8792	High Similarity	NPD7819	Suspended
0.8777	High Similarity	NPD1607	Approved
0.8759	High Similarity	NPD4378	Clinical (unspecified phase)
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8652	High Similarity	NPD1510	Phase 2
0.8633	High Similarity	NPD1240	Approved
0.863	High Similarity	NPD7410	Clinical (unspecified phase)
0.86	High Similarity	NPD1934	Approved
0.8591	High Similarity	NPD6599	Discontinued
0.8562	High Similarity	NPD6799	Approved
0.8543	High Similarity	NPD7096	Clinical (unspecified phase)
0.8533	High Similarity	NPD7411	Suspended
0.8506	High Similarity	NPD5494	Approved
0.8435	Intermediate Similarity	NPD1511	Approved
0.8421	Intermediate Similarity	NPD2801	Approved
0.8392	Intermediate Similarity	NPD3748	Approved
0.8377	Intermediate Similarity	NPD7075	Discontinued
0.8366	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD3817	Phase 2
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8322	Intermediate Similarity	NPD1512	Approved
0.8312	Intermediate Similarity	NPD3882	Suspended
0.8288	Intermediate Similarity	NPD1243	Approved
0.8258	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6801	Discontinued
0.8235	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8207	Intermediate Similarity	NPD6100	Approved
0.8207	Intermediate Similarity	NPD6099	Approved
0.8176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6166	Phase 2
0.8176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD920	Approved
0.8141	Intermediate Similarity	NPD3749	Approved
0.8121	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD3926	Phase 2
0.8108	Intermediate Similarity	NPD3750	Approved
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD6832	Phase 2
0.8063	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD3972	Approved
0.8041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2346	Discontinued
0.8026	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4307	Phase 2
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7975	Intermediate Similarity	NPD919	Approved
0.7963	Intermediate Similarity	NPD3818	Discontinued
0.7962	Intermediate Similarity	NPD7768	Phase 2
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2935	Discontinued
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7931	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3226	Approved
0.7914	Intermediate Similarity	NPD5844	Phase 1
0.7914	Intermediate Similarity	NPD7054	Approved
0.7908	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7898	Intermediate Similarity	NPD5402	Approved
0.7895	Intermediate Similarity	NPD5401	Approved
0.7895	Intermediate Similarity	NPD2532	Approved
0.7895	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD2534	Approved
0.7891	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2799	Discontinued
0.7875	Intermediate Similarity	NPD1247	Approved
0.7867	Intermediate Similarity	NPD4628	Phase 3
0.7866	Intermediate Similarity	NPD7472	Approved
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.7817	Intermediate Similarity	NPD2798	Approved
0.7808	Intermediate Similarity	NPD1933	Approved
0.7805	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2654	Approved
0.78	Intermediate Similarity	NPD2800	Approved
0.7785	Intermediate Similarity	NPD2344	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.777	Intermediate Similarity	NPD4308	Phase 3
0.774	Intermediate Similarity	NPD943	Approved
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7724	Intermediate Similarity	NPD2313	Discontinued
0.7698	Intermediate Similarity	NPD17	Approved
0.7667	Intermediate Similarity	NPD1471	Phase 3
0.7662	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4625	Phase 3
0.7635	Intermediate Similarity	NPD6651	Approved
0.7632	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3266	Approved
0.7622	Intermediate Similarity	NPD1203	Approved
0.7622	Intermediate Similarity	NPD3267	Approved
0.7619	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4749	Approved
0.7605	Intermediate Similarity	NPD5953	Discontinued
0.7603	Intermediate Similarity	NPD411	Approved
0.7597	Intermediate Similarity	NPD7390	Discontinued
0.7586	Intermediate Similarity	NPD4908	Phase 1
0.7582	Intermediate Similarity	NPD2309	Approved
0.7574	Intermediate Similarity	NPD1241	Discontinued
0.7535	Intermediate Similarity	NPD9717	Approved
0.7535	Intermediate Similarity	NPD1608	Approved
0.7533	Intermediate Similarity	NPD7033	Discontinued
0.7515	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1610	Phase 2
0.7448	Intermediate Similarity	NPD1019	Discontinued
0.7431	Intermediate Similarity	NPD1876	Approved
0.7425	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6585	Discontinued
0.741	Intermediate Similarity	NPD2403	Approved
0.7394	Intermediate Similarity	NPD5711	Approved
0.7394	Intermediate Similarity	NPD5710	Approved
0.7383	Intermediate Similarity	NPD3140	Approved
0.7383	Intermediate Similarity	NPD3142	Approved
0.7379	Intermediate Similarity	NPD2797	Approved
0.7375	Intermediate Similarity	NPD5890	Approved
0.7375	Intermediate Similarity	NPD5889	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3887	Approved
0.7347	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD447	Suspended
0.7329	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD6279	Approved
0.7329	Intermediate Similarity	NPD6280	Approved
0.7321	Intermediate Similarity	NPD3751	Discontinued
0.732	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2353	Approved
0.7305	Intermediate Similarity	NPD1548	Phase 1
0.7305	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3787	Discontinued
0.7279	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1470	Approved
0.7256	Intermediate Similarity	NPD6971	Discontinued
0.7255	Intermediate Similarity	NPD5404	Approved
0.7255	Intermediate Similarity	NPD5408	Approved
0.7255	Intermediate Similarity	NPD5406	Approved
0.7255	Intermediate Similarity	NPD5405	Approved
0.7251	Intermediate Similarity	NPD6104	Discontinued
0.725	Intermediate Similarity	NPD7458	Discontinued
0.7246	Intermediate Similarity	NPD5242	Approved
0.7234	Intermediate Similarity	NPD5536	Phase 2
0.7229	Intermediate Similarity	NPD7199	Phase 2
0.7222	Intermediate Similarity	NPD1281	Approved
0.7222	Intermediate Similarity	NPD422	Phase 1
0.7222	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7203	Intermediate Similarity	NPD1778	Approved
0.7192	Intermediate Similarity	NPD3225	Approved
0.7191	Intermediate Similarity	NPD4363	Phase 3
0.7191	Intermediate Similarity	NPD4360	Phase 2
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7186	Intermediate Similarity	NPD6808	Phase 2
0.7182	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7003	Approved
0.717	Intermediate Similarity	NPD6273	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2354	Approved
0.7134	Intermediate Similarity	NPD5353	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD5691	Approved
0.7133	Intermediate Similarity	NPD3764	Approved
0.7122	Intermediate Similarity	NPD5535	Approved
0.7118	Intermediate Similarity	NPD7177	Discontinued
0.7118	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4662	Approved
0.7107	Intermediate Similarity	NPD4661	Approved
0.7091	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6780	Approved
0.7088	Intermediate Similarity	NPD6776	Approved
0.7088	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD6781	Approved
0.7088	Intermediate Similarity	NPD6778	Approved
0.7088	Intermediate Similarity	NPD6779	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