NPASS Compound

Structure

CID230285 OpenBabel06191716022D 22 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 -3.5000 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 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 -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 -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 -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 20 1 0 0 0 0 2 21 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 10 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	3.212
LogD:	2.992
LogS:	-3.747
# Rotatable Bonds:	3
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	2.171
Fsp3:	0.118
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:	-4.756
MDCK Permeability:	1.9887367670889944e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	92.45188903808594%
Volume Distribution (VD):	0.788
Pgp-substrate:	7.318953990936279%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.924
CYP2C19-substrate:	0.157
CYP2C9-inhibitor:	0.811
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.767
CYP2D6-substrate:	0.802
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	4.89
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.638
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.276
Skin Sensitization:	0.265
Carcinogencity:	0.147
Eye Corrosion:	0.007
Eye Irritation:	0.873
Respiratory Toxicity:	0.24

Download Data

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

Natural Product: NPC230285

Natural Product ID:	NPC230285
*Common Name:**	7-Hydroxy-3,5-Dimethoxy-2-Phenylchromen-4-One
IUPAC Name:	7-hydroxy-3,5-dimethoxy-2-phenylchromen-4-one
Synonyms:
Standard InCHIKey:	BUNIGAWIPPRWMH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-20-12-8-11(18)9-13-14(12)15(19)17(21-2)16(22-13)10-6-4-3-5-7-10/h3-9,18H,1-2H3
SMILES:	COc1cc(cc2c1c(=O)c(c(c1ccccc1)o2)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL183723
PubChem CID:	44392177
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]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	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
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	=	6.8	n.a.	PMID[469345]

☑ 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 NPC230285 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	438
0.1-0.2	1903
0.2-0.3	5033
0.3-0.4	11227
0.4-0.5	6190
0.5-0.6	4177
0.6-0.7	5677
0.7-0.8	3945
0.8-0.85	2182
0.85-0.9	1448
0.9-0.95	428
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC59951
1.0	High Similarity	NPC146679
1.0	High Similarity	NPC184536
1.0	High Similarity	NPC103342
1.0	High Similarity	NPC103904
0.9926	High Similarity	NPC136840
0.9926	High Similarity	NPC90582
0.9926	High Similarity	NPC262094
0.9925	High Similarity	NPC152042
0.9925	High Similarity	NPC143799
0.9925	High Similarity	NPC241838
0.9852	High Similarity	NPC269652
0.9852	High Similarity	NPC281207
0.9781	High Similarity	NPC470216
0.9704	High Similarity	NPC276905
0.9701	High Similarity	NPC29353
0.9701	High Similarity	NPC216361
0.9701	High Similarity	NPC281917
0.9701	High Similarity	NPC194281
0.9701	High Similarity	NPC47815
0.9701	High Similarity	NPC127447
0.9701	High Similarity	NPC187432
0.9701	High Similarity	NPC234133
0.9701	High Similarity	NPC256042
0.9701	High Similarity	NPC116775
0.9701	High Similarity	NPC473887
0.9701	High Similarity	NPC124784
0.9701	High Similarity	NPC231772
0.964	High Similarity	NPC178343
0.964	High Similarity	NPC306488
0.964	High Similarity	NPC5820
0.9638	High Similarity	NPC158874
0.963	High Similarity	NPC266597
0.963	High Similarity	NPC299379
0.963	High Similarity	NPC250266
0.9568	High Similarity	NPC273538
0.9568	High Similarity	NPC216538
0.9565	High Similarity	NPC200694
0.9565	High Similarity	NPC473042
0.9556	High Similarity	NPC61546
0.9556	High Similarity	NPC72452
0.9556	High Similarity	NPC13408
0.9552	High Similarity	NPC248872
0.95	High Similarity	NPC153758
0.95	High Similarity	NPC470458
0.95	High Similarity	NPC124729
0.9496	High Similarity	NPC212932
0.9496	High Similarity	NPC9117
0.9496	High Similarity	NPC293053
0.9496	High Similarity	NPC24821
0.9496	High Similarity	NPC190637
0.9489	High Similarity	NPC18260
0.9489	High Similarity	NPC78913
0.9478	High Similarity	NPC78540
0.9478	High Similarity	NPC274121
0.9478	High Similarity	NPC50898
0.9478	High Similarity	NPC213216
0.9437	High Similarity	NPC470461
0.9433	High Similarity	NPC259632
0.9429	High Similarity	NPC326500
0.9429	High Similarity	NPC71210
0.942	High Similarity	NPC159275
0.942	High Similarity	NPC241100
0.9416	High Similarity	NPC99333
0.9416	High Similarity	NPC188947
0.9416	High Similarity	NPC201395
0.9416	High Similarity	NPC280284
0.9407	High Similarity	NPC172262
0.9403	High Similarity	NPC128216
0.9371	High Similarity	NPC149127
0.9371	High Similarity	NPC286342
0.9371	High Similarity	NPC188871
0.9366	High Similarity	NPC244407
0.9366	High Similarity	NPC296869
0.9366	High Similarity	NPC470460
0.9353	High Similarity	NPC282300
0.9353	High Similarity	NPC110969
0.9348	High Similarity	NPC222342
0.9348	High Similarity	NPC150648
0.9348	High Similarity	NPC225153
0.9348	High Similarity	NPC53181
0.9348	High Similarity	NPC217186
0.9348	High Similarity	NPC96565
0.9348	High Similarity	NPC301217
0.9348	High Similarity	NPC220062
0.9348	High Similarity	NPC216978
0.9348	High Similarity	NPC303633
0.9348	High Similarity	NPC310135
0.9348	High Similarity	NPC274784
0.9348	High Similarity	NPC20709
0.9348	High Similarity	NPC329203
0.9348	High Similarity	NPC265871
0.9348	High Similarity	NPC55018
0.9343	High Similarity	NPC290291
0.9343	High Similarity	NPC188879
0.9343	High Similarity	NPC228661
0.9343	High Similarity	NPC275055
0.9343	High Similarity	NPC254841
0.9333	High Similarity	NPC57601
0.9328	High Similarity	NPC473584
0.9328	High Similarity	NPC113006
0.9328	High Similarity	NPC475589
0.9328	High Similarity	NPC31872
0.9328	High Similarity	NPC278556
0.9306	High Similarity	NPC236769
0.9306	High Similarity	NPC260895
0.9301	High Similarity	NPC477941
0.9301	High Similarity	NPC159103
0.9301	High Similarity	NPC270465
0.9301	High Similarity	NPC87125
0.9296	High Similarity	NPC476182
0.9296	High Similarity	NPC211466
0.9296	High Similarity	NPC166757
0.9296	High Similarity	NPC44721
0.9296	High Similarity	NPC472918
0.9296	High Similarity	NPC122828
0.9296	High Similarity	NPC40086
0.9296	High Similarity	NPC176869
0.9296	High Similarity	NPC14001
0.9296	High Similarity	NPC3779
0.9286	High Similarity	NPC11561
0.9286	High Similarity	NPC226636
0.9281	High Similarity	NPC150522
0.9281	High Similarity	NPC188243
0.9281	High Similarity	NPC284550
0.9281	High Similarity	NPC261227
0.9281	High Similarity	NPC172986
0.9281	High Similarity	NPC129853
0.9281	High Similarity	NPC110228
0.9281	High Similarity	NPC6407
0.9281	High Similarity	NPC270883
0.9281	High Similarity	NPC76445
0.9275	High Similarity	NPC124269
0.9275	High Similarity	NPC118813
0.927	High Similarity	NPC121243
0.927	High Similarity	NPC240593
0.927	High Similarity	NPC240147
0.9259	High Similarity	NPC10971
0.9259	High Similarity	NPC205468
0.9259	High Similarity	NPC87231
0.9259	High Similarity	NPC257756
0.9259	High Similarity	NPC25937
0.9259	High Similarity	NPC101294
0.9259	High Similarity	NPC473655
0.9259	High Similarity	NPC212631
0.9259	High Similarity	NPC129132
0.9254	High Similarity	NPC5515
0.9254	High Similarity	NPC270369
0.9254	High Similarity	NPC137264
0.9241	High Similarity	NPC279989
0.9241	High Similarity	NPC82325
0.9236	High Similarity	NPC50728
0.9236	High Similarity	NPC61258
0.9236	High Similarity	NPC166753
0.9225	High Similarity	NPC220418
0.9225	High Similarity	NPC229190
0.922	High Similarity	NPC113770
0.9214	High Similarity	NPC64908
0.9214	High Similarity	NPC147688
0.9214	High Similarity	NPC156590
0.9214	High Similarity	NPC213322
0.9214	High Similarity	NPC103362
0.9214	High Similarity	NPC205006
0.9214	High Similarity	NPC118840
0.9214	High Similarity	NPC312391
0.9214	High Similarity	NPC324386
0.9214	High Similarity	NPC310128
0.9214	High Similarity	NPC3188
0.9214	High Similarity	NPC4743
0.9209	High Similarity	NPC140890
0.9209	High Similarity	NPC261234
0.9209	High Similarity	NPC49242
0.9203	High Similarity	NPC13768
0.9203	High Similarity	NPC32441
0.9203	High Similarity	NPC181124
0.9203	High Similarity	NPC116632
0.9203	High Similarity	NPC107586
0.9203	High Similarity	NPC287246
0.9203	High Similarity	NPC294409
0.9203	High Similarity	NPC209560
0.9203	High Similarity	NPC296490
0.9203	High Similarity	NPC303644
0.9203	High Similarity	NPC162680
0.9203	High Similarity	NPC12296
0.9203	High Similarity	NPC243083
0.9203	High Similarity	NPC7013
0.9203	High Similarity	NPC79943
0.9203	High Similarity	NPC295261
0.9197	High Similarity	NPC9985
0.9197	High Similarity	NPC239495
0.9191	High Similarity	NPC223457
0.9191	High Similarity	NPC472365
0.9191	High Similarity	NPC159623
0.9191	High Similarity	NPC82225
0.9191	High Similarity	NPC263670
0.9191	High Similarity	NPC188646
0.9191	High Similarity	NPC56031
0.9191	High Similarity	NPC294593
0.9191	High Similarity	NPC204960
0.9191	High Similarity	NPC242294

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 NPC230285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	967
0.2-0.3	1691
0.3-0.4	2701
0.4-0.5	1828
0.5-0.6	1037
0.6-0.7	346
0.7-0.8	103
0.8-0.85	37
0.85-0.9	18
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD4378	Clinical (unspecified phase)
0.9203	High Similarity	NPD1552	Clinical (unspecified phase)
0.9203	High Similarity	NPD1550	Clinical (unspecified phase)
0.9137	High Similarity	NPD1549	Phase 2
0.9091	High Similarity	NPD1512	Approved
0.9058	High Similarity	NPD1510	Phase 2
0.9044	High Similarity	NPD1240	Approved
0.8951	High Similarity	NPD6799	Approved
0.8951	High Similarity	NPD1511	Approved
0.8913	High Similarity	NPD1607	Approved
0.8889	High Similarity	NPD7410	Clinical (unspecified phase)
0.8857	High Similarity	NPD2796	Approved
0.8792	High Similarity	NPD2801	Approved
0.8742	High Similarity	NPD7075	Discontinued
0.8733	High Similarity	NPD3817	Phase 2
0.8725	High Similarity	NPD6801	Discontinued
0.8725	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD3882	Suspended
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.8591	High Similarity	NPD6599	Discontinued
0.8591	High Similarity	NPD4380	Phase 2
0.8533	High Similarity	NPD7411	Suspended
0.8514	High Similarity	NPD5403	Approved
0.8503	High Similarity	NPD5401	Approved
0.8497	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD3750	Approved
0.8481	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6166	Phase 2
0.8408	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6797	Phase 2
0.8357	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1551	Phase 2
0.8323	Intermediate Similarity	NPD7251	Discontinued
0.8301	Intermediate Similarity	NPD7819	Suspended
0.8288	Intermediate Similarity	NPD2800	Approved
0.8272	Intermediate Similarity	NPD7808	Phase 3
0.8247	Intermediate Similarity	NPD5402	Approved
0.8163	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD3749	Approved
0.8138	Intermediate Similarity	NPD3748	Approved
0.8137	Intermediate Similarity	NPD7054	Approved
0.8129	Intermediate Similarity	NPD1203	Approved
0.8108	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6959	Discontinued
0.8086	Intermediate Similarity	NPD7472	Approved
0.8077	Intermediate Similarity	NPD7768	Phase 2
0.8075	Intermediate Similarity	NPD3818	Discontinued
0.8074	Intermediate Similarity	NPD1548	Phase 1
0.8063	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1243	Approved
0.8027	Intermediate Similarity	NPD2344	Approved
0.8026	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD6651	Approved
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7972	Intermediate Similarity	NPD2313	Discontinued
0.7971	Intermediate Similarity	NPD422	Phase 1
0.7959	Intermediate Similarity	NPD2935	Discontinued
0.7914	Intermediate Similarity	NPD9717	Approved
0.7895	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1247	Approved
0.7862	Intermediate Similarity	NPD919	Approved
0.7848	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD3268	Approved
0.7842	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6832	Phase 2
0.7831	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6232	Discontinued
0.7815	Intermediate Similarity	NPD2309	Approved
0.7812	Intermediate Similarity	NPD5494	Approved
0.7805	Intermediate Similarity	NPD7286	Phase 2
0.7801	Intermediate Similarity	NPD3225	Approved
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.777	Intermediate Similarity	NPD2799	Discontinued
0.777	Intermediate Similarity	NPD7033	Discontinued
0.7746	Intermediate Similarity	NPD2797	Approved
0.774	Intermediate Similarity	NPD943	Approved
0.7718	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD6100	Approved
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7711	Intermediate Similarity	NPD5953	Discontinued
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD2798	Approved
0.7692	Intermediate Similarity	NPD3226	Approved
0.7682	Intermediate Similarity	NPD2654	Approved
0.7669	Intermediate Similarity	NPD3926	Phase 2
0.7665	Intermediate Similarity	NPD6559	Discontinued
0.7651	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4308	Phase 3
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD3266	Approved
0.7622	Intermediate Similarity	NPD3267	Approved
0.7605	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6798	Discontinued
0.7603	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1933	Approved
0.7554	Intermediate Similarity	NPD9545	Approved
0.7551	Intermediate Similarity	NPD6233	Phase 2
0.755	Intermediate Similarity	NPD2346	Discontinued
0.7536	Intermediate Similarity	NPD9493	Approved
0.7533	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3751	Discontinued
0.7515	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7486	Intermediate Similarity	NPD4363	Phase 3
0.7486	Intermediate Similarity	NPD4360	Phase 2
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7484	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7468	Intermediate Similarity	NPD2354	Approved
0.7466	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4288	Approved
0.745	Intermediate Similarity	NPD447	Suspended
0.745	Intermediate Similarity	NPD230	Phase 1
0.7448	Intermediate Similarity	NPD1019	Discontinued
0.7445	Intermediate Similarity	NPD1241	Discontinued
0.7434	Intermediate Similarity	NPD1471	Phase 3
0.7413	Intermediate Similarity	NPD1608	Approved
0.7413	Intermediate Similarity	NPD3972	Approved
0.7413	Intermediate Similarity	NPD1481	Phase 2
0.741	Intermediate Similarity	NPD2403	Approved
0.7403	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7383	Intermediate Similarity	NPD4307	Phase 2
0.7383	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1613	Approved
0.7375	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD411	Approved
0.7345	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4361	Phase 2
0.7343	Intermediate Similarity	NPD1535	Discovery
0.7342	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5124	Phase 1
0.732	Intermediate Similarity	NPD2353	Approved
0.732	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3764	Approved
0.7246	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3887	Approved
0.7239	Intermediate Similarity	NPD2296	Approved
0.7235	Intermediate Similarity	NPD1729	Discontinued
0.723	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1652	Phase 2
0.7222	Intermediate Similarity	NPD6844	Discontinued
0.7222	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD4340	Discontinued
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD17	Approved
0.72	Intermediate Similarity	NPD4062	Phase 3
0.7186	Intermediate Similarity	NPD5711	Approved
0.7186	Intermediate Similarity	NPD5710	Approved
0.7183	Intermediate Similarity	NPD1894	Discontinued
0.7181	Intermediate Similarity	NPD4625	Phase 3
0.717	Intermediate Similarity	NPD5049	Phase 3
0.7159	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD1470	Approved
0.7134	Intermediate Similarity	NPD6190	Approved
0.7123	Intermediate Similarity	NPD4749	Approved
0.7097	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7440	Discontinued
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.7075	Intermediate Similarity	NPD1876	Approved
0.7067	Intermediate Similarity	NPD3027	Phase 3
0.7055	Intermediate Similarity	NPD5890	Approved
0.7055	Intermediate Similarity	NPD5889	Approved
0.7048	Intermediate Similarity	NPD6971	Discontinued
0.7047	Intermediate Similarity	NPD2861	Phase 2
0.7045	Intermediate Similarity	NPD8434	Phase 2
0.7044	Intermediate Similarity	NPD7213	Phase 3
0.7044	Intermediate Similarity	NPD7212	Phase 2
0.7043	Intermediate Similarity	NPD7584	Approved
0.7039	Intermediate Similarity	NPD3140	Approved
0.7039	Intermediate Similarity	NPD4060	Phase 1
0.7039	Intermediate Similarity	NPD3142	Approved
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.7027	Intermediate Similarity	NPD1164	Approved
0.7024	Intermediate Similarity	NPD7199	Phase 2
0.7018	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7447	Phase 1
0.7	Intermediate Similarity	NPD4661	Approved
0.7	Intermediate Similarity	NPD4662	Approved
0.6995	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6585	Discontinued
0.6962	Remote Similarity	NPD7003	Approved
0.6957	Remote Similarity	NPD74	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