NPASS Compound

Structure

NPC1534 OpenBabel07101719522D 24 26 0 0 0 0 0 0 0 0999 V2000 -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 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 1.7321 2.0000 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 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 19 2 0 0 0 0 11 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 14 15 1 0 0 0 0 15 21 2 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.12
Volume:	340.24
LogP:	4.056
LogD:	3.015
LogS:	-4.281
# Rotatable Bonds:	4
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	2.357
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.836
MDCK Permeability:	1.7335216398350894e-05
Pgp-inhibitor:	0.502
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.502
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	98.81798553466797%
Volume Distribution (VD):	0.491
Pgp-substrate:	0.9279428124427795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.612
CYP2D6-substrate:	0.404
CYP3A4-inhibitor:	0.547
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	2.483
Half-life (T1/2):	0.64

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.41
Rat Oral Acute Toxicity:	0.702
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.267
Carcinogencity:	0.312
Eye Corrosion:	0.004
Eye Irritation:	0.794
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC1534

Natural Product ID:	NPC1534
*Common Name:**	Gramideoxybenzoin G
IUPAC Name:	5-hydroxy-7-phenacyl-2-propan-2-ylchromen-4-one
Synonyms:
Standard InCHIKey:	IEFNHUUCYJCWSV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O4/c1-12(2)18-11-17(23)20-16(22)9-13(10-19(20)24-18)8-15(21)14-6-4-3-5-7-14/h3-7,9-12,22H,8H2,1-2H3
SMILES:	CC(C)c1cc(=O)c2c(cc(CC(=O)c3ccccc3)cc2o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431353
PubChem CID:	72702042
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	>	10000.0	nM	PMID[568960]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[568960]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[568960]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[568960]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[568960]

☑ 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 NPC1534 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	424
0.1-0.2	1791
0.2-0.3	4553
0.3-0.4	11753
0.4-0.5	6383
0.5-0.6	4291
0.6-0.7	5732
0.7-0.8	4706
0.8-0.85	2279
0.85-0.9	715
0.9-0.95	69
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9504	High Similarity	NPC196114
0.9441	High Similarity	NPC474052
0.9366	High Similarity	NPC130176
0.9366	High Similarity	NPC99454
0.9357	High Similarity	NPC24075
0.9353	High Similarity	NPC109232
0.9348	High Similarity	NPC228661
0.9306	High Similarity	NPC269420
0.9286	High Similarity	NPC261227
0.9286	High Similarity	NPC172986
0.9286	High Similarity	NPC270883
0.9275	High Similarity	NPC13408
0.9231	High Similarity	NPC469758
0.922	High Similarity	NPC205006
0.922	High Similarity	NPC110969
0.922	High Similarity	NPC282300
0.922	High Similarity	NPC147688
0.922	High Similarity	NPC156590
0.922	High Similarity	NPC64908
0.922	High Similarity	NPC118840
0.9214	High Similarity	NPC216978
0.9214	High Similarity	NPC55018
0.9214	High Similarity	NPC220062
0.9214	High Similarity	NPC96565
0.9214	High Similarity	NPC301217
0.9214	High Similarity	NPC303633
0.9209	High Similarity	NPC266597
0.9209	High Similarity	NPC250266
0.9184	High Similarity	NPC72370
0.9178	High Similarity	NPC258249
0.9172	High Similarity	NPC158338
0.9172	High Similarity	NPC65589
0.9172	High Similarity	NPC97029
0.9172	High Similarity	NPC10027
0.9172	High Similarity	NPC288036
0.9172	High Similarity	NPC100985
0.9172	High Similarity	NPC97028
0.9172	High Similarity	NPC65775
0.9161	High Similarity	NPC326500
0.9161	High Similarity	NPC234629
0.9161	High Similarity	NPC469764
0.9161	High Similarity	NPC311741
0.9155	High Similarity	NPC202981
0.9155	High Similarity	NPC11561
0.9155	High Similarity	NPC226636
0.9155	High Similarity	NPC144499
0.9149	High Similarity	NPC159275
0.9149	High Similarity	NPC171094
0.9149	High Similarity	NPC76445
0.9149	High Similarity	NPC235239
0.9149	High Similarity	NPC129853
0.9149	High Similarity	NPC475680
0.9149	High Similarity	NPC305355
0.9149	High Similarity	NPC69769
0.9149	High Similarity	NPC284550
0.9149	High Similarity	NPC241100
0.9143	High Similarity	NPC201395
0.9143	High Similarity	NPC124269
0.9137	High Similarity	NPC47815
0.9137	High Similarity	NPC194281
0.9137	High Similarity	NPC124784
0.9137	High Similarity	NPC29353
0.9137	High Similarity	NPC473391
0.9137	High Similarity	NPC127447
0.9137	High Similarity	NPC473887
0.9137	High Similarity	NPC472364
0.9137	High Similarity	NPC234133
0.9137	High Similarity	NPC231772
0.913	High Similarity	NPC172262
0.9118	High Similarity	NPC137264
0.9116	High Similarity	NPC142527
0.9116	High Similarity	NPC45934
0.911	High Similarity	NPC167576
0.9103	High Similarity	NPC186397
0.9103	High Similarity	NPC37135
0.9103	High Similarity	NPC256672
0.9103	High Similarity	NPC27221
0.9103	High Similarity	NPC7025
0.9097	High Similarity	NPC154217
0.9097	High Similarity	NPC299011
0.9097	High Similarity	NPC477955
0.9091	High Similarity	NPC106985
0.9091	High Similarity	NPC38219
0.9091	High Similarity	NPC9117
0.9091	High Similarity	NPC11700
0.9091	High Similarity	NPC18585
0.9091	High Similarity	NPC219915
0.9091	High Similarity	NPC212932
0.9091	High Similarity	NPC24821
0.9091	High Similarity	NPC293053
0.9091	High Similarity	NPC166138
0.9091	High Similarity	NPC190637
0.9085	High Similarity	NPC103362
0.9078	High Similarity	NPC18260
0.9078	High Similarity	NPC53181
0.9078	High Similarity	NPC261234
0.9078	High Similarity	NPC217186
0.9078	High Similarity	NPC78913
0.9071	High Similarity	NPC7013
0.9071	High Similarity	NPC116632
0.9071	High Similarity	NPC212767
0.9071	High Similarity	NPC209560
0.9071	High Similarity	NPC294409
0.9071	High Similarity	NPC188879
0.9071	High Similarity	NPC162680
0.9071	High Similarity	NPC303644
0.9071	High Similarity	NPC181124
0.9065	High Similarity	NPC239495
0.9065	High Similarity	NPC9985
0.9058	High Similarity	NPC50898
0.9058	High Similarity	NPC57601
0.9058	High Similarity	NPC78540
0.9058	High Similarity	NPC213216
0.9058	High Similarity	NPC274121
0.9054	High Similarity	NPC329844
0.9054	High Similarity	NPC193200
0.9054	High Similarity	NPC210942
0.9054	High Similarity	NPC169990
0.9048	High Similarity	NPC154345
0.9044	High Similarity	NPC115998
0.9044	High Similarity	NPC39753
0.9041	High Similarity	NPC223988
0.9041	High Similarity	NPC266499
0.9034	High Similarity	NPC237635
0.9034	High Similarity	NPC123202
0.9034	High Similarity	NPC7943
0.9034	High Similarity	NPC22005
0.9034	High Similarity	NPC24673
0.9034	High Similarity	NPC79469
0.9034	High Similarity	NPC201731
0.9034	High Similarity	NPC104406
0.9034	High Similarity	NPC97716
0.9028	High Similarity	NPC271288
0.9028	High Similarity	NPC473015
0.9028	High Similarity	NPC184649
0.9028	High Similarity	NPC216538
0.9028	High Similarity	NPC311144
0.9028	High Similarity	NPC1886
0.9028	High Similarity	NPC273538
0.9028	High Similarity	NPC473013
0.9028	High Similarity	NPC196137
0.9028	High Similarity	NPC303185
0.9021	High Similarity	NPC62840
0.9021	High Similarity	NPC78803
0.9021	High Similarity	NPC59739
0.9021	High Similarity	NPC217083
0.9021	High Similarity	NPC159855
0.9021	High Similarity	NPC214236
0.9021	High Similarity	NPC73028
0.9021	High Similarity	NPC310340
0.9021	High Similarity	NPC473042
0.9021	High Similarity	NPC293852
0.9021	High Similarity	NPC299080
0.9021	High Similarity	NPC169479
0.9021	High Similarity	NPC200694
0.9014	High Similarity	NPC204985
0.9014	High Similarity	NPC265178
0.9014	High Similarity	NPC150522
0.9014	High Similarity	NPC215311
0.9014	High Similarity	NPC213659
0.9014	High Similarity	NPC144118
0.9014	High Similarity	NPC80962
0.9014	High Similarity	NPC281207
0.9014	High Similarity	NPC219917
0.9014	High Similarity	NPC145673
0.9014	High Similarity	NPC275734
0.9014	High Similarity	NPC110228
0.9014	High Similarity	NPC259166
0.9014	High Similarity	NPC188243
0.9014	High Similarity	NPC172250
0.9014	High Similarity	NPC6407
0.9014	High Similarity	NPC48624
0.9014	High Similarity	NPC326109
0.9014	High Similarity	NPC269652
0.9007	High Similarity	NPC188947
0.9007	High Similarity	NPC470668
0.9007	High Similarity	NPC18457
0.9007	High Similarity	NPC279668
0.9007	High Similarity	NPC90665
0.9007	High Similarity	NPC278323
0.9007	High Similarity	NPC118813
0.9007	High Similarity	NPC309154
0.9007	High Similarity	NPC12175
0.9007	High Similarity	NPC280284
0.9007	High Similarity	NPC99333
0.9007	High Similarity	NPC470669
0.9007	High Similarity	NPC55162
0.9	High Similarity	NPC213603
0.9	High Similarity	NPC254741
0.9	High Similarity	NPC240593
0.9	High Similarity	NPC193792
0.8993	High Similarity	NPC275575
0.8993	High Similarity	NPC286336
0.8986	High Similarity	NPC87708
0.8986	High Similarity	NPC154683
0.8986	High Similarity	NPC10971
0.8986	High Similarity	NPC40356
0.898	High Similarity	NPC158866
0.898	High Similarity	NPC37348
0.898	High Similarity	NPC3825

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 NPC1534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	976
0.2-0.3	1517
0.3-0.4	2710
0.4-0.5	1934
0.5-0.6	1121
0.6-0.7	319
0.7-0.8	116
0.8-0.85	36
0.85-0.9	18
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9028	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD1510	Phase 2
0.8921	High Similarity	NPD1607	Approved
0.8897	High Similarity	NPD7410	Clinical (unspecified phase)
0.8873	High Similarity	NPD1549	Phase 2
0.8865	High Similarity	NPD2796	Approved
0.8828	High Similarity	NPD1511	Approved
0.8803	High Similarity	NPD1550	Clinical (unspecified phase)
0.8803	High Similarity	NPD1552	Clinical (unspecified phase)
0.8777	High Similarity	NPD1240	Approved
0.8707	High Similarity	NPD1512	Approved
0.8675	High Similarity	NPD2801	Approved
0.8675	High Similarity	NPD2393	Clinical (unspecified phase)
0.8609	High Similarity	NPD1934	Approved
0.8601	High Similarity	NPD6099	Approved
0.8601	High Similarity	NPD6100	Approved
0.8601	High Similarity	NPD1551	Phase 2
0.8553	High Similarity	NPD7819	Suspended
0.8497	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD3750	Approved
0.8483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD4380	Phase 2
0.8442	Intermediate Similarity	NPD3882	Suspended
0.8421	Intermediate Similarity	NPD7411	Suspended
0.8387	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7075	Discontinued
0.8367	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8322	Intermediate Similarity	NPD6799	Approved
0.8312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD3226	Approved
0.8258	Intermediate Similarity	NPD3817	Phase 2
0.8247	Intermediate Similarity	NPD6801	Discontinued
0.8214	Intermediate Similarity	NPD2798	Approved
0.8199	Intermediate Similarity	NPD3818	Discontinued
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD2346	Discontinued
0.8158	Intermediate Similarity	NPD5403	Approved
0.8153	Intermediate Similarity	NPD3749	Approved
0.8151	Intermediate Similarity	NPD3748	Approved
0.8151	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD4308	Phase 3
0.8143	Intermediate Similarity	NPD1203	Approved
0.8141	Intermediate Similarity	NPD5402	Approved
0.8137	Intermediate Similarity	NPD7473	Discontinued
0.8121	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD2313	Discontinued
0.8112	Intermediate Similarity	NPD3268	Approved
0.8095	Intermediate Similarity	NPD2935	Discontinued
0.8089	Intermediate Similarity	NPD7768	Phase 2
0.8075	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8054	Intermediate Similarity	NPD2800	Approved
0.8054	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1243	Approved
0.805	Intermediate Similarity	NPD5494	Approved
0.8041	Intermediate Similarity	NPD2344	Approved
0.8037	Intermediate Similarity	NPD7054	Approved
0.8027	Intermediate Similarity	NPD2799	Discontinued
0.8026	Intermediate Similarity	NPD2532	Approved
0.8026	Intermediate Similarity	NPD5401	Approved
0.8026	Intermediate Similarity	NPD2534	Approved
0.8026	Intermediate Similarity	NPD2533	Approved
0.8014	Intermediate Similarity	NPD2797	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD4749	Approved
0.7988	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7986	Intermediate Similarity	NPD411	Approved
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6797	Phase 2
0.7929	Intermediate Similarity	NPD1608	Approved
0.7929	Intermediate Similarity	NPD9717	Approved
0.7927	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4625	Phase 3
0.7908	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7251	Discontinued
0.7891	Intermediate Similarity	NPD6651	Approved
0.7881	Intermediate Similarity	NPD4628	Phase 3
0.7877	Intermediate Similarity	NPD4307	Phase 2
0.7857	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6832	Phase 2
0.7844	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.7843	Intermediate Similarity	NPD7390	Discontinued
0.7829	Intermediate Similarity	NPD2309	Approved
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.7806	Intermediate Similarity	NPD920	Approved
0.7785	Intermediate Similarity	NPD7033	Discontinued
0.7778	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD3266	Approved
0.7762	Intermediate Similarity	NPD1470	Approved
0.7762	Intermediate Similarity	NPD3267	Approved
0.7738	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1201	Approved
0.7725	Intermediate Similarity	NPD5953	Discontinued
0.7724	Intermediate Similarity	NPD4908	Phase 1
0.7714	Intermediate Similarity	NPD17	Approved
0.7707	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD3225	Approved
0.7683	Intermediate Similarity	NPD3926	Phase 2
0.7677	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD919	Approved
0.7625	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1610	Phase 2
0.7606	Intermediate Similarity	NPD422	Phase 1
0.7605	Intermediate Similarity	NPD7286	Phase 2
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1548	Phase 1
0.7561	Intermediate Similarity	NPD1247	Approved
0.7552	Intermediate Similarity	NPD3972	Approved
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7485	Intermediate Similarity	NPD8312	Approved
0.7485	Intermediate Similarity	NPD8313	Approved
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4288	Approved
0.7467	Intermediate Similarity	NPD1933	Approved
0.7453	Intermediate Similarity	NPD6844	Discontinued
0.7451	Intermediate Similarity	NPD1471	Phase 3
0.744	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD9493	Approved
0.7415	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5710	Approved
0.741	Intermediate Similarity	NPD5711	Approved
0.7401	Intermediate Similarity	NPD4360	Phase 2
0.7401	Intermediate Similarity	NPD4363	Phase 3
0.7386	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.736	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4361	Phase 2
0.7355	Intermediate Similarity	NPD2654	Approved
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7343	Intermediate Similarity	NPD1778	Approved
0.7337	Intermediate Similarity	NPD7177	Discontinued
0.732	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7003	Approved
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1296	Phase 2
0.7267	Intermediate Similarity	NPD3764	Approved
0.7256	Intermediate Similarity	NPD2296	Approved
0.7246	Intermediate Similarity	NPD7199	Phase 2
0.7237	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3751	Discontinued
0.723	Intermediate Similarity	NPD1019	Discontinued
0.723	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6585	Discontinued
0.7219	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9545	Approved
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7198	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5760	Phase 2
0.7195	Intermediate Similarity	NPD5761	Phase 2
0.7188	Intermediate Similarity	NPD6273	Approved
0.7183	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2861	Phase 2
0.7178	Intermediate Similarity	NPD5890	Approved
0.7178	Intermediate Similarity	NPD5889	Approved
0.7178	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4287	Approved
0.7174	Intermediate Similarity	NPD4750	Phase 3
0.7169	Intermediate Similarity	NPD6971	Discontinued
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8150	Discontinued
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7125	Intermediate Similarity	NPD4662	Approved
0.7125	Intermediate Similarity	NPD4661	Approved
0.7113	Intermediate Similarity	NPD6671	Approved
0.7104	Intermediate Similarity	NPD6776	Approved
0.7104	Intermediate Similarity	NPD6782	Approved
0.7104	Intermediate Similarity	NPD6780	Approved
0.7104	Intermediate Similarity	NPD6781	Approved
0.7104	Intermediate Similarity	NPD6777	Approved
0.7104	Intermediate Similarity	NPD6779	Approved
0.7104	Intermediate Similarity	NPD6778	Approved
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7095	Intermediate Similarity	NPD1283	Approved
0.7095	Intermediate Similarity	NPD1876	Approved
0.7092	Intermediate Similarity	NPD1241	Discontinued
0.7086	Intermediate Similarity	NPD3027	Phase 3
0.7083	Intermediate Similarity	NPD6746	Phase 2
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data