NPASS Compound

Structure

NPC470216 OpenBabel07101718292D 24 26 0 0 0 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -1.7321 1.0000 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 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 -1.7321 -3.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 10 1 0 0 0 0 2 22 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 11 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 19 2 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.08
Volume:	323.228
LogP:	2.964
LogD:	2.558
LogS:	-3.828
# Rotatable Bonds:	4
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	2.276
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.766
MDCK Permeability:	2.5389521397300996e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	91.39148712158203%
Volume Distribution (VD):	1.004
Pgp-substrate:	12.309989929199219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.351
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.471
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	2.376
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.486
Rat Oral Acute Toxicity:	0.323
Maximum Recommended Daily Dose:	0.52
Skin Sensitization:	0.577
Carcinogencity:	0.142
Eye Corrosion:	0.012
Eye Irritation:	0.835
Respiratory Toxicity:	0.342

Download Data

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

Natural Product: NPC470216

Natural Product ID:	NPC470216
*Common Name:**	(7-Hydroxy-5-Methoxy-4-Oxo-2-Phenylchromen-3-Yl) Acetate
IUPAC Name:	(7-hydroxy-5-methoxy-4-oxo-2-phenylchromen-3-yl) acetate
Synonyms:
Standard InCHIKey:	TWNIURHOTMBPGZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O6/c1-10(19)23-18-16(21)15-13(22-2)8-12(20)9-14(15)24-17(18)11-6-4-3-5-7-11/h3-9,20H,1-2H3
SMILES:	CC(=O)OC1=C(OC2=C(C1=O)C(=CC(=C2)O)OC)C3=CC=CC=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL182759
PubChem CID:	44392276
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-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
NPO33252	heliotropium sinuatum	Species	Heliotropiaceae	Eukaryota	resinous exudate	n.a.	n.a.	PMID[15603945]

☑ 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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		Ratio	=	160.0	n.a.	PMID[570875]

☑ 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 NPC470216 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	393
0.1-0.2	1882
0.2-0.3	4890
0.3-0.4	10417
0.4-0.5	7215
0.5-0.6	4042
0.6-0.7	5894
0.7-0.8	3893
0.8-0.85	2648
0.85-0.9	1159
0.9-0.95	251
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9781	High Similarity	NPC103342
0.9781	High Similarity	NPC146679
0.9781	High Similarity	NPC103904
0.9781	High Similarity	NPC59951
0.9781	High Similarity	NPC230285
0.9781	High Similarity	NPC184536
0.9714	High Similarity	NPC153758
0.971	High Similarity	NPC136840
0.971	High Similarity	NPC90582
0.971	High Similarity	NPC262094
0.9708	High Similarity	NPC152042
0.9708	High Similarity	NPC143799
0.9708	High Similarity	NPC241838
0.9638	High Similarity	NPC281207
0.9638	High Similarity	NPC269652
0.951	High Similarity	NPC477941
0.9493	High Similarity	NPC276905
0.9489	High Similarity	NPC216361
0.9489	High Similarity	NPC127447
0.9489	High Similarity	NPC281917
0.9489	High Similarity	NPC187432
0.9489	High Similarity	NPC234133
0.9489	High Similarity	NPC29353
0.9489	High Similarity	NPC256042
0.9489	High Similarity	NPC116775
0.9489	High Similarity	NPC473887
0.9489	High Similarity	NPC231772
0.9489	High Similarity	NPC47815
0.9489	High Similarity	NPC194281
0.9489	High Similarity	NPC124784
0.9437	High Similarity	NPC306488
0.9437	High Similarity	NPC178343
0.9437	High Similarity	NPC5820
0.9433	High Similarity	NPC158874
0.942	High Similarity	NPC266597
0.942	High Similarity	NPC299379
0.942	High Similarity	NPC250266
0.9379	High Similarity	NPC295650
0.9366	High Similarity	NPC216538
0.9366	High Similarity	NPC273538
0.9366	High Similarity	NPC71210
0.9362	High Similarity	NPC473042
0.9362	High Similarity	NPC200694
0.9357	High Similarity	NPC474037
0.9348	High Similarity	NPC72452
0.9348	High Similarity	NPC61546
0.9348	High Similarity	NPC13408
0.9343	High Similarity	NPC248872
0.9301	High Similarity	NPC470458
0.9301	High Similarity	NPC124729
0.9296	High Similarity	NPC190637
0.9296	High Similarity	NPC9117
0.9296	High Similarity	NPC212932
0.9296	High Similarity	NPC293053
0.9296	High Similarity	NPC24821
0.9286	High Similarity	NPC18260
0.9286	High Similarity	NPC78913
0.9286	High Similarity	NPC230902
0.927	High Similarity	NPC78540
0.927	High Similarity	NPC274121
0.927	High Similarity	NPC213216
0.927	High Similarity	NPC50898
0.9241	High Similarity	NPC470461
0.9236	High Similarity	NPC259632
0.9231	High Similarity	NPC326500
0.9231	High Similarity	NPC469953
0.9225	High Similarity	NPC36181
0.922	High Similarity	NPC241100
0.922	High Similarity	NPC159275
0.9214	High Similarity	NPC201395
0.9214	High Similarity	NPC280284
0.9214	High Similarity	NPC188947
0.9214	High Similarity	NPC99333
0.9203	High Similarity	NPC172262
0.9197	High Similarity	NPC128216
0.9189	High Similarity	NPC473241
0.9178	High Similarity	NPC149127
0.9178	High Similarity	NPC286342
0.9178	High Similarity	NPC188871
0.9178	High Similarity	NPC295036
0.9172	High Similarity	NPC296869
0.9172	High Similarity	NPC470460
0.9172	High Similarity	NPC211811
0.9172	High Similarity	NPC244407
0.9167	High Similarity	NPC470322
0.9167	High Similarity	NPC154217
0.9161	High Similarity	NPC94794
0.9161	High Similarity	NPC112791
0.9161	High Similarity	NPC188632
0.9161	High Similarity	NPC196459
0.9161	High Similarity	NPC87609
0.9161	High Similarity	NPC470296
0.9155	High Similarity	NPC310128
0.9155	High Similarity	NPC282300
0.9155	High Similarity	NPC110969
0.9149	High Similarity	NPC303633
0.9149	High Similarity	NPC96565
0.9149	High Similarity	NPC274784
0.9149	High Similarity	NPC53181
0.9149	High Similarity	NPC216978
0.9149	High Similarity	NPC222342
0.9149	High Similarity	NPC20709
0.9149	High Similarity	NPC310135
0.9149	High Similarity	NPC220062
0.9149	High Similarity	NPC55018
0.9149	High Similarity	NPC265871
0.9149	High Similarity	NPC329203
0.9149	High Similarity	NPC150648
0.9149	High Similarity	NPC217186
0.9149	High Similarity	NPC225153
0.9149	High Similarity	NPC301217
0.9143	High Similarity	NPC254841
0.9143	High Similarity	NPC228661
0.9143	High Similarity	NPC275055
0.9143	High Similarity	NPC290291
0.9143	High Similarity	NPC188879
0.9133	High Similarity	NPC104677
0.913	High Similarity	NPC57601
0.9124	High Similarity	NPC278556
0.9124	High Similarity	NPC31872
0.9124	High Similarity	NPC473584
0.9124	High Similarity	NPC113006
0.9124	High Similarity	NPC475589
0.9116	High Similarity	NPC236769
0.9116	High Similarity	NPC260895
0.911	High Similarity	NPC87125
0.911	High Similarity	NPC270465
0.911	High Similarity	NPC159103
0.9103	High Similarity	NPC211466
0.9103	High Similarity	NPC3779
0.9103	High Similarity	NPC40086
0.9103	High Similarity	NPC476182
0.9103	High Similarity	NPC472918
0.9103	High Similarity	NPC166757
0.9103	High Similarity	NPC44721
0.9103	High Similarity	NPC176869
0.9103	High Similarity	NPC14001
0.9103	High Similarity	NPC122828
0.9097	High Similarity	NPC196137
0.9097	High Similarity	NPC469935
0.9097	High Similarity	NPC178627
0.9097	High Similarity	NPC1886
0.9091	High Similarity	NPC11561
0.9091	High Similarity	NPC226636
0.9091	High Similarity	NPC471520
0.9085	High Similarity	NPC172986
0.9085	High Similarity	NPC129853
0.9085	High Similarity	NPC110228
0.9085	High Similarity	NPC188243
0.9085	High Similarity	NPC150522
0.9085	High Similarity	NPC6407
0.9085	High Similarity	NPC284550
0.9085	High Similarity	NPC270883
0.9085	High Similarity	NPC76445
0.9085	High Similarity	NPC261227
0.9078	High Similarity	NPC118813
0.9078	High Similarity	NPC124269
0.9071	High Similarity	NPC121243
0.9071	High Similarity	NPC240593
0.9071	High Similarity	NPC240147
0.9058	High Similarity	NPC473655
0.9058	High Similarity	NPC101294
0.9058	High Similarity	NPC25937
0.9058	High Similarity	NPC87231
0.9058	High Similarity	NPC205468
0.9058	High Similarity	NPC129132
0.9058	High Similarity	NPC10971
0.9058	High Similarity	NPC212631
0.9058	High Similarity	NPC257756
0.9054	High Similarity	NPC82325
0.9054	High Similarity	NPC279989
0.9051	High Similarity	NPC137264
0.9051	High Similarity	NPC5515
0.9051	High Similarity	NPC270369
0.9048	High Similarity	NPC166753
0.9048	High Similarity	NPC61258
0.9048	High Similarity	NPC50728
0.9048	High Similarity	NPC474735
0.9034	High Similarity	NPC181388
0.9034	High Similarity	NPC220418
0.9034	High Similarity	NPC57470
0.9034	High Similarity	NPC229190
0.9028	High Similarity	NPC113770
0.9021	High Similarity	NPC312391
0.9021	High Similarity	NPC205006
0.9021	High Similarity	NPC213322
0.9021	High Similarity	NPC103362
0.9021	High Similarity	NPC324386
0.9021	High Similarity	NPC147688
0.9021	High Similarity	NPC64908
0.9021	High Similarity	NPC156590
0.9021	High Similarity	NPC118840
0.9021	High Similarity	NPC3188
0.9021	High Similarity	NPC4743
0.9014	High Similarity	NPC140890
0.9014	High Similarity	NPC49242
0.9014	High Similarity	NPC136095
0.9014	High Similarity	NPC261234
0.9013	High Similarity	NPC85707
0.9013	High Similarity	NPC48093

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 NPC470216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	973
0.2-0.3	1760
0.3-0.4	2645
0.4-0.5	1847
0.5-0.6	1024
0.6-0.7	351
0.7-0.8	97
0.8-0.85	51
0.85-0.9	19
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9366	High Similarity	NPD4378	Clinical (unspecified phase)
0.9161	High Similarity	NPD6799	Approved
0.9007	High Similarity	NPD1550	Clinical (unspecified phase)
0.9007	High Similarity	NPD1552	Clinical (unspecified phase)
0.8944	High Similarity	NPD1549	Phase 2
0.894	High Similarity	NPD7075	Discontinued
0.8933	High Similarity	NPD3817	Phase 2
0.8926	High Similarity	NPD6801	Discontinued
0.8904	High Similarity	NPD1512	Approved
0.8867	High Similarity	NPD7096	Clinical (unspecified phase)
0.8865	High Similarity	NPD1510	Phase 2
0.8849	High Similarity	NPD1240	Approved
0.8792	High Similarity	NPD6599	Discontinued
0.8767	High Similarity	NPD1511	Approved
0.8733	High Similarity	NPD7411	Suspended
0.8723	High Similarity	NPD1607	Approved
0.8716	High Similarity	NPD5403	Approved
0.8707	High Similarity	NPD7410	Clinical (unspecified phase)
0.8707	High Similarity	NPD5401	Approved
0.869	High Similarity	NPD3750	Approved
0.8681	High Similarity	NPD970	Clinical (unspecified phase)
0.8671	High Similarity	NPD2796	Approved
0.8618	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD6859	Clinical (unspecified phase)
0.8553	High Similarity	NPD1934	Approved
0.8542	High Similarity	NPD1551	Phase 2
0.8506	High Similarity	NPD3882	Suspended
0.8497	Intermediate Similarity	NPD7819	Suspended
0.8497	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD5402	Approved
0.8438	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD4380	Phase 2
0.8367	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD3748	Approved
0.8345	Intermediate Similarity	NPD1203	Approved
0.8344	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD6797	Phase 2
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7251	Discontinued
0.8269	Intermediate Similarity	NPD7768	Phase 2
0.825	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6166	Phase 2
0.825	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1243	Approved
0.8232	Intermediate Similarity	NPD7808	Phase 3
0.8224	Intermediate Similarity	NPD920	Approved
0.8188	Intermediate Similarity	NPD422	Phase 1
0.8182	Intermediate Similarity	NPD2313	Discontinued
0.8163	Intermediate Similarity	NPD2935	Discontinued
0.8129	Intermediate Similarity	NPD9717	Approved
0.8121	Intermediate Similarity	NPD2800	Approved
0.8098	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD3268	Approved
0.805	Intermediate Similarity	NPD919	Approved
0.8049	Intermediate Similarity	NPD7472	Approved
0.8042	Intermediate Similarity	NPD6832	Phase 2
0.8038	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8014	Intermediate Similarity	NPD3225	Approved
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7974	Intermediate Similarity	NPD2534	Approved
0.7974	Intermediate Similarity	NPD2533	Approved
0.7974	Intermediate Similarity	NPD2532	Approved
0.7973	Intermediate Similarity	NPD2799	Discontinued
0.7973	Intermediate Similarity	NPD7033	Discontinued
0.7958	Intermediate Similarity	NPD2797	Approved
0.795	Intermediate Similarity	NPD6959	Discontinued
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7899	Intermediate Similarity	NPD1548	Phase 1
0.7892	Intermediate Similarity	NPD5953	Discontinued
0.7885	Intermediate Similarity	NPD3226	Approved
0.7867	Intermediate Similarity	NPD2344	Approved
0.7852	Intermediate Similarity	NPD4308	Phase 3
0.7838	Intermediate Similarity	NPD6651	Approved
0.7832	Intermediate Similarity	NPD3267	Approved
0.7832	Intermediate Similarity	NPD3266	Approved
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7808	Intermediate Similarity	NPD6798	Discontinued
0.7784	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1933	Approved
0.777	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD9545	Approved
0.7755	Intermediate Similarity	NPD6233	Phase 2
0.7754	Intermediate Similarity	NPD9493	Approved
0.7748	Intermediate Similarity	NPD2346	Discontinued
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.773	Intermediate Similarity	NPD1247	Approved
0.7697	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1465	Phase 2
0.7687	Intermediate Similarity	NPD1296	Phase 2
0.7676	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5494	Approved
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD2309	Approved
0.7662	Intermediate Similarity	NPD2354	Approved
0.7655	Intermediate Similarity	NPD2798	Approved
0.7655	Intermediate Similarity	NPD1019	Discontinued
0.7651	Intermediate Similarity	NPD230	Phase 1
0.7651	Intermediate Similarity	NPD447	Suspended
0.764	Intermediate Similarity	NPD4288	Approved
0.7622	Intermediate Similarity	NPD1608	Approved
0.7622	Intermediate Similarity	NPD1481	Phase 2
0.7597	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD943	Approved
0.7584	Intermediate Similarity	NPD4307	Phase 2
0.7568	Intermediate Similarity	NPD411	Approved
0.7566	Intermediate Similarity	NPD6099	Approved
0.7566	Intermediate Similarity	NPD6100	Approved
0.7562	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1535	Discovery
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7551	Intermediate Similarity	NPD4908	Phase 1
0.7533	Intermediate Similarity	NPD6355	Discontinued
0.7533	Intermediate Similarity	NPD5124	Phase 1
0.7533	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2654	Approved
0.753	Intermediate Similarity	NPD3926	Phase 2
0.7516	Intermediate Similarity	NPD2353	Approved
0.7516	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3764	Approved
0.7443	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3887	Approved
0.7432	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1652	Phase 2
0.7417	Intermediate Similarity	NPD4340	Discontinued
0.7413	Intermediate Similarity	NPD17	Approved
0.7405	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4062	Phase 3
0.7394	Intermediate Similarity	NPD1894	Discontinued
0.7386	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD5710	Approved
0.7365	Intermediate Similarity	NPD3787	Discontinued
0.736	Intermediate Similarity	NPD4363	Phase 3
0.736	Intermediate Similarity	NPD4360	Phase 2
0.7358	Intermediate Similarity	NPD5049	Phase 3
0.7342	Intermediate Similarity	NPD7390	Discontinued
0.7342	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4287	Approved
0.7325	Intermediate Similarity	NPD6190	Approved
0.7315	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1471	Phase 3
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1241	Discontinued
0.7278	Intermediate Similarity	NPD7440	Discontinued
0.7278	Intermediate Similarity	NPD2403	Approved
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.726	Intermediate Similarity	NPD3972	Approved
0.7248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5890	Approved
0.7239	Intermediate Similarity	NPD5889	Approved
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7237	Intermediate Similarity	NPD1613	Approved
0.7237	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1164	Approved
0.7229	Intermediate Similarity	NPD6971	Discontinued
0.7222	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4361	Phase 2
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.7178	Intermediate Similarity	NPD6585	Discontinued
0.7174	Intermediate Similarity	NPD74	Approved
0.7174	Intermediate Similarity	NPD9266	Approved
0.7152	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD7003	Approved
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5404	Approved
0.7115	Intermediate Similarity	NPD5406	Approved
0.7115	Intermediate Similarity	NPD5405	Approved
0.7115	Intermediate Similarity	NPD5408	Approved
0.711	Intermediate Similarity	NPD1729	Discontinued
0.7108	Intermediate Similarity	NPD2296	Approved
0.7101	Intermediate Similarity	NPD9267	Approved
0.7101	Intermediate Similarity	NPD9264	Approved
0.7101	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD9263	Approved
0.7092	Intermediate Similarity	NPD5535	Approved
0.7091	Intermediate Similarity	NPD6844	Discontinued
0.7079	Intermediate Similarity	NPD1898	Discontinued
0.7075	Intermediate Similarity	NPD1201	Approved
0.7055	Intermediate Similarity	NPD1653	Approved
0.7055	Intermediate Similarity	NPD1778	Approved
0.7045	Intermediate Similarity	NPD8312	Approved
0.7045	Intermediate Similarity	NPD8313	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