NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	1.753
LogD:	0.886
LogS:	-2.704
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	3.123
Fsp3:	0.133
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:	-4.861
MDCK Permeability:	6.9106140472285915e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	82.4144515991211%
Volume Distribution (VD):	1.45
Pgp-substrate:	21.819705963134766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.156
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.152
CYP2D6-substrate:	0.718
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	4.561
Half-life (T1/2):	0.555

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.309
Skin Sensitization:	0.411
Carcinogencity:	0.037
Eye Corrosion:	0.004
Eye Irritation:	0.253
Respiratory Toxicity:	0.199

Download Data

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

Natural Product: NPC148011

Natural Product ID:	NPC148011
*Common Name:**	(2R,3R)-3,7-Dihydroxyflavanone
IUPAC Name:	(2R,3R)-3,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:	(2R,3R)-3,7-Dihydroxyflavanone
Standard InCHIKey:	LVCUVLHYCYWHDY-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C15H12O4/c16-10-6-7-11-12(8-10)19-15(14(18)13(11)17)9-4-2-1-3-5-9/h1-8,14-16,18H/t14-,15+/m0/s1
SMILES:	Oc1ccc2c(c1)O[C@@H]([C@H](C2=O)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252667
PubChem CID:	14730799
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26690274]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO8159	Digenea simplex	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117523]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]
NPO8159	Digenea simplex	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8159	Digenea simplex	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12862	Lunasia amara	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8159	Digenea simplex	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12010	Ectropis obliqua	Species	Geometridae	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	6
Others	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[538002]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[538003]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[538003]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[538003]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[538003]
NPT2	Others	Unspecified		%max	=	11.73	%	PMID[538004]

☑ 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 NPC148011 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	417
0.1-0.2	1670
0.2-0.3	4382
0.3-0.4	10171
0.4-0.5	7703
0.5-0.6	3784
0.6-0.7	5493
0.7-0.8	5023
0.8-0.85	2423
0.85-0.9	1304
0.9-0.95	285
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC1940
0.9928	High Similarity	NPC4152
0.9928	High Similarity	NPC62290
0.9928	High Similarity	NPC208176
0.9928	High Similarity	NPC306607
0.9928	High Similarity	NPC279417
0.9928	High Similarity	NPC49130
0.9928	High Similarity	NPC326506
0.9928	High Similarity	NPC142731
0.9787	High Similarity	NPC176869
0.9787	High Similarity	NPC3779
0.9787	High Similarity	NPC476182
0.9787	High Similarity	NPC211466
0.9787	High Similarity	NPC40086
0.9787	High Similarity	NPC44721
0.9787	High Similarity	NPC122828
0.9718	High Similarity	NPC218569
0.9716	High Similarity	NPC229190
0.9712	High Similarity	NPC150023
0.9648	High Similarity	NPC21835
0.9586	High Similarity	NPC171651
0.9586	High Similarity	NPC35567
0.9586	High Similarity	NPC243171
0.9521	High Similarity	NPC256346
0.9521	High Similarity	NPC293286
0.9521	High Similarity	NPC325028
0.9521	High Similarity	NPC27532
0.9521	High Similarity	NPC246328
0.9517	High Similarity	NPC262038
0.9517	High Similarity	NPC254412
0.9517	High Similarity	NPC319910
0.9517	High Similarity	NPC262039
0.9517	High Similarity	NPC278476
0.951	High Similarity	NPC472918
0.9496	High Similarity	NPC329225
0.9496	High Similarity	NPC472460
0.9496	High Similarity	NPC147686
0.9452	High Similarity	NPC240476
0.9452	High Similarity	NPC216035
0.9452	High Similarity	NPC138288
0.9452	High Similarity	NPC61506
0.9452	High Similarity	NPC9743
0.9452	High Similarity	NPC246162
0.9452	High Similarity	NPC217149
0.9452	High Similarity	NPC260491
0.9452	High Similarity	NPC36835
0.9448	High Similarity	NPC105136
0.9448	High Similarity	NPC267117
0.9424	High Similarity	NPC476480
0.9424	High Similarity	NPC295261
0.9424	High Similarity	NPC79943
0.9424	High Similarity	NPC296490
0.9424	High Similarity	NPC32441
0.9424	High Similarity	NPC84585
0.9424	High Similarity	NPC243083
0.9424	High Similarity	NPC287246
0.9424	High Similarity	NPC107586
0.9424	High Similarity	NPC13768
0.9424	High Similarity	NPC12296
0.9388	High Similarity	NPC20907
0.9388	High Similarity	NPC244250
0.9388	High Similarity	NPC203080
0.9388	High Similarity	NPC268193
0.9384	High Similarity	NPC472422
0.9384	High Similarity	NPC471676
0.9384	High Similarity	NPC263384
0.9384	High Similarity	NPC244577
0.9384	High Similarity	NPC471229
0.9384	High Similarity	NPC472420
0.9379	High Similarity	NPC477941
0.9379	High Similarity	NPC277032
0.9329	High Similarity	NPC52530
0.9324	High Similarity	NPC111341
0.9324	High Similarity	NPC207809
0.9324	High Similarity	NPC304207
0.9324	High Similarity	NPC304745
0.9324	High Similarity	NPC217706
0.9324	High Similarity	NPC259710
0.9324	High Similarity	NPC48579
0.932	High Similarity	NPC19721
0.9291	High Similarity	NPC274784
0.9291	High Similarity	NPC310135
0.9291	High Similarity	NPC20709
0.9291	High Similarity	NPC225153
0.9291	High Similarity	NPC150648
0.9291	High Similarity	NPC329203
0.9291	High Similarity	NPC261234
0.9291	High Similarity	NPC265871
0.9291	High Similarity	NPC222342
0.9286	High Similarity	NPC275055
0.9286	High Similarity	NPC299379
0.9286	High Similarity	NPC290291
0.9286	High Similarity	NPC287068
0.9281	High Similarity	NPC9985
0.9281	High Similarity	NPC239495
0.9262	High Similarity	NPC20530
0.9262	High Similarity	NPC326037
0.9262	High Similarity	NPC201837
0.9262	High Similarity	NPC215917
0.9262	High Similarity	NPC13858
0.9262	High Similarity	NPC10754
0.9262	High Similarity	NPC320825
0.9257	High Similarity	NPC141212
0.9257	High Similarity	NPC223701
0.9257	High Similarity	NPC248793
0.9257	High Similarity	NPC7989
0.9257	High Similarity	NPC180301
0.9257	High Similarity	NPC472583
0.9252	High Similarity	NPC289774
0.9252	High Similarity	NPC295650
0.9252	High Similarity	NPC209846
0.9252	High Similarity	NPC477897
0.9252	High Similarity	NPC471677
0.9252	High Similarity	NPC328740
0.9247	High Similarity	NPC183959
0.9247	High Similarity	NPC89442
0.9247	High Similarity	NPC472628
0.9247	High Similarity	NPC1612
0.9241	High Similarity	NPC472627
0.9225	High Similarity	NPC281207
0.9225	High Similarity	NPC110228
0.9225	High Similarity	NPC188243
0.9225	High Similarity	NPC182421
0.9225	High Similarity	NPC269652
0.9225	High Similarity	NPC6407
0.922	High Similarity	NPC118813
0.922	High Similarity	NPC99333
0.922	High Similarity	NPC280284
0.922	High Similarity	NPC188947
0.9214	High Similarity	NPC281917
0.9214	High Similarity	NPC256042
0.9214	High Similarity	NPC216361
0.9214	High Similarity	NPC116775
0.9214	High Similarity	NPC187432
0.9205	High Similarity	NPC306978
0.92	High Similarity	NPC6985
0.9195	High Similarity	NPC477958
0.9195	High Similarity	NPC99233
0.9189	High Similarity	NPC259182
0.9189	High Similarity	NPC475790
0.9189	High Similarity	NPC121001
0.9189	High Similarity	NPC161881
0.9189	High Similarity	NPC210597
0.9189	High Similarity	NPC88484
0.9189	High Similarity	NPC244583
0.9189	High Similarity	NPC56232
0.9189	High Similarity	NPC150123
0.9189	High Similarity	NPC259767
0.9189	High Similarity	NPC10807
0.9189	High Similarity	NPC473996
0.9184	High Similarity	NPC61258
0.9184	High Similarity	NPC177308
0.9184	High Similarity	NPC124478
0.9178	High Similarity	NPC321011
0.9178	High Similarity	NPC294852
0.9178	High Similarity	NPC188679
0.9172	High Similarity	NPC472629
0.9167	High Similarity	NPC39329
0.9167	High Similarity	NPC257097
0.9167	High Similarity	NPC310130
0.9167	High Similarity	NPC143896
0.9167	High Similarity	NPC169591
0.9167	High Similarity	NPC164980
0.9167	High Similarity	NPC175504
0.9167	High Similarity	NPC149026
0.9167	High Similarity	NPC221432
0.9167	High Similarity	NPC150408
0.9167	High Similarity	NPC91560
0.9167	High Similarity	NPC75049
0.9167	High Similarity	NPC68104
0.9161	High Similarity	NPC3188
0.9161	High Similarity	NPC213322
0.9161	High Similarity	NPC312391
0.9161	High Similarity	NPC136840
0.9161	High Similarity	NPC4743
0.9161	High Similarity	NPC324386
0.9155	High Similarity	NPC241838
0.9155	High Similarity	NPC143799
0.9155	High Similarity	NPC152042
0.9155	High Similarity	NPC316480
0.9155	High Similarity	NPC140890
0.9145	High Similarity	NPC308992
0.9139	High Similarity	NPC22192
0.9139	High Similarity	NPC123544
0.9133	High Similarity	NPC203500
0.9133	High Similarity	NPC471500
0.9133	High Similarity	NPC78492
0.9133	High Similarity	NPC250922
0.9133	High Similarity	NPC208152
0.9133	High Similarity	NPC474638
0.9133	High Similarity	NPC307938
0.9133	High Similarity	NPC170475
0.9133	High Similarity	NPC323593
0.9128	High Similarity	NPC106625
0.9128	High Similarity	NPC236756
0.9128	High Similarity	NPC209760
0.9128	High Similarity	NPC100134
0.9128	High Similarity	NPC469405
0.9128	High Similarity	NPC112701
0.9128	High Similarity	NPC109594

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 NPC148011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	879
0.2-0.3	1759
0.3-0.4	2633
0.4-0.5	1785
0.5-0.6	1063
0.6-0.7	426
0.7-0.8	137
0.8-0.85	31
0.85-0.9	22
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9496	High Similarity	NPD1549	Phase 2
0.9424	High Similarity	NPD1550	Clinical (unspecified phase)
0.9424	High Similarity	NPD1552	Clinical (unspecified phase)
0.9184	High Similarity	NPD4380	Phase 2
0.9073	High Similarity	NPD7075	Discontinued
0.9073	High Similarity	NPD4381	Clinical (unspecified phase)
0.906	High Similarity	NPD1934	Approved
0.9007	High Similarity	NPD1510	Phase 2
0.9	High Similarity	NPD7096	Clinical (unspecified phase)
0.8973	High Similarity	NPD4378	Clinical (unspecified phase)
0.8933	High Similarity	NPD6801	Discontinued
0.8912	High Similarity	NPD1512	Approved
0.8904	High Similarity	NPD6799	Approved
0.8874	High Similarity	NPD2393	Clinical (unspecified phase)
0.8857	High Similarity	NPD1240	Approved
0.8846	High Similarity	NPD6168	Clinical (unspecified phase)
0.8846	High Similarity	NPD6167	Clinical (unspecified phase)
0.8846	High Similarity	NPD6166	Phase 2
0.8776	High Similarity	NPD1511	Approved
0.8732	High Similarity	NPD1607	Approved
0.8725	High Similarity	NPD5403	Approved
0.8716	High Similarity	NPD5401	Approved
0.8681	High Similarity	NPD2796	Approved
0.8679	High Similarity	NPD7804	Clinical (unspecified phase)
0.8675	High Similarity	NPD6599	Discontinued
0.8636	High Similarity	NPD3882	Suspended
0.8506	High Similarity	NPD2801	Approved
0.85	High Similarity	NPD3818	Discontinued
0.8497	Intermediate Similarity	NPD7411	Suspended
0.8467	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD6797	Phase 2
0.8452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD5402	Approved
0.8452	Intermediate Similarity	NPD3817	Phase 2
0.8405	Intermediate Similarity	NPD7251	Discontinued
0.8397	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7074	Phase 3
0.8354	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7808	Phase 3
0.8333	Intermediate Similarity	NPD7054	Approved
0.8299	Intermediate Similarity	NPD1551	Phase 2
0.8282	Intermediate Similarity	NPD7472	Approved
0.8269	Intermediate Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8125	Intermediate Similarity	NPD5494	Approved
0.8113	Intermediate Similarity	NPD3749	Approved
0.8082	Intermediate Similarity	NPD1613	Approved
0.8082	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD4628	Phase 3
0.8075	Intermediate Similarity	NPD6959	Discontinued
0.8037	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1203	Approved
0.7959	Intermediate Similarity	NPD943	Approved
0.7947	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3751	Discontinued
0.7937	Intermediate Similarity	NPD7768	Phase 2
0.7925	Intermediate Similarity	NPD1465	Phase 2
0.7895	Intermediate Similarity	NPD2800	Approved
0.7892	Intermediate Similarity	NPD5844	Phase 1
0.7885	Intermediate Similarity	NPD920	Approved
0.7871	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3748	Approved
0.7857	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1247	Approved
0.7843	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD919	Approved
0.7817	Intermediate Similarity	NPD1610	Phase 2
0.7808	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1548	Phase 1
0.7784	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1243	Approved
0.7763	Intermediate Similarity	NPD2344	Approved
0.774	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2313	Discontinued
0.7703	Intermediate Similarity	NPD6798	Discontinued
0.7697	Intermediate Similarity	NPD3787	Discontinued
0.7697	Intermediate Similarity	NPD6232	Discontinued
0.7697	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD7286	Phase 2
0.7665	Intermediate Similarity	NPD7473	Discontinued
0.7657	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3926	Phase 2
0.7639	Intermediate Similarity	NPD9717	Approved
0.7632	Intermediate Similarity	NPD7033	Discontinued
0.7632	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6651	Approved
0.7602	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5953	Discontinued
0.7568	Intermediate Similarity	NPD4908	Phase 1
0.7568	Intermediate Similarity	NPD6832	Phase 2
0.7564	Intermediate Similarity	NPD2309	Approved
0.755	Intermediate Similarity	NPD1933	Approved
0.755	Intermediate Similarity	NPD230	Phase 1
0.7548	Intermediate Similarity	NPD1652	Phase 2
0.7533	Intermediate Similarity	NPD6233	Phase 2
0.7532	Intermediate Similarity	NPD2534	Approved
0.7532	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7472	Intermediate Similarity	NPD4360	Phase 2
0.7472	Intermediate Similarity	NPD4363	Phase 3
0.7468	Intermediate Similarity	NPD6100	Approved
0.7468	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8313	Approved
0.7457	Intermediate Similarity	NPD8312	Approved
0.7453	Intermediate Similarity	NPD3226	Approved
0.7452	Intermediate Similarity	NPD2354	Approved
0.7452	Intermediate Similarity	NPD6190	Approved
0.7448	Intermediate Similarity	NPD422	Phase 1
0.7434	Intermediate Similarity	NPD6355	Discontinued
0.7434	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD8434	Phase 2
0.7421	Intermediate Similarity	NPD4662	Approved
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4661	Approved
0.7419	Intermediate Similarity	NPD2346	Discontinued
0.7413	Intermediate Similarity	NPD9545	Approved
0.7405	Intermediate Similarity	NPD7584	Approved
0.74	Intermediate Similarity	NPD3027	Phase 3
0.7396	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1653	Approved
0.7363	Intermediate Similarity	NPD6780	Approved
0.7363	Intermediate Similarity	NPD6776	Approved
0.7363	Intermediate Similarity	NPD6778	Approved
0.7363	Intermediate Similarity	NPD6777	Approved
0.7363	Intermediate Similarity	NPD6781	Approved
0.7363	Intermediate Similarity	NPD6782	Approved
0.7363	Intermediate Similarity	NPD6779	Approved
0.7362	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3268	Approved
0.7342	Intermediate Similarity	NPD3887	Approved
0.7329	Intermediate Similarity	NPD1091	Approved
0.7329	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5124	Phase 1
0.7315	Intermediate Similarity	NPD2798	Approved
0.7315	Intermediate Similarity	NPD1019	Discontinued
0.7305	Intermediate Similarity	NPD1241	Discontinued
0.7297	Intermediate Similarity	NPD3225	Approved
0.729	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7261	Intermediate Similarity	NPD2424	Discontinued
0.7248	Intermediate Similarity	NPD2797	Approved
0.7243	Intermediate Similarity	NPD7435	Discontinued
0.7239	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7235	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8150	Discontinued
0.7229	Intermediate Similarity	NPD4288	Approved
0.7225	Intermediate Similarity	NPD1729	Discontinued
0.7219	Intermediate Similarity	NPD7199	Phase 2
0.7215	Intermediate Similarity	NPD2654	Approved
0.7212	Intermediate Similarity	NPD6844	Discontinued
0.7197	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1471	Phase 3
0.7197	Intermediate Similarity	NPD2353	Approved
0.7193	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4062	Phase 3
0.7184	Intermediate Similarity	NPD3823	Discontinued
0.7175	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1481	Phase 2
0.7162	Intermediate Similarity	NPD1608	Approved
0.7162	Intermediate Similarity	NPD3972	Approved
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7151	Intermediate Similarity	NPD4287	Approved
0.7151	Intermediate Similarity	NPD7697	Approved
0.7151	Intermediate Similarity	NPD7698	Approved
0.7151	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD1470	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7124	Intermediate Similarity	NPD3764	Approved
0.7124	Intermediate Similarity	NPD411	Approved
0.7112	Intermediate Similarity	NPD7871	Phase 2
0.7112	Intermediate Similarity	NPD7870	Phase 2
0.7097	Intermediate Similarity	NPD4340	Discontinued
0.7095	Intermediate Similarity	NPD1201	Approved
0.7095	Intermediate Similarity	NPD1535	Discovery
0.709	Intermediate Similarity	NPD7701	Phase 2
0.7088	Intermediate Similarity	NPD6535	Approved
0.7088	Intermediate Similarity	NPD6534	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