NPASS Compound

Structure

NPC473996 OpenBabel07101718222D 26 29 0 0 1 0 0 0 0 0999 V2000 -4.3005 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3005 1.4487 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 -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 -2.5981 -1.5000 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 -1.9400 0.9781 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 1.0000 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 -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 1.7321 1.0000 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 -2.5981 -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 1 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 1.9487 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 0.8660 1.5000 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 -2.9345 2.8147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 0.1691 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 20 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 15 1 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 12 19 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 25 1 0 0 0 0 17 11 1 6 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	354.536
LogP:	3.071
LogD:	2.465
LogS:	-3.961
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	3.7
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.877
MDCK Permeability:	1.4016030945640523e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	93.51602172851562%
Volume Distribution (VD):	0.457
Pgp-substrate:	5.7378315925598145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.315
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.682
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.756
CYP2D6-substrate:	0.718
CYP3A4-inhibitor:	0.324
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	13.82
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.605
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.806
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.79
Carcinogencity:	0.697
Eye Corrosion:	0.003
Eye Irritation:	0.407
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC473996

Natural Product ID:	NPC473996
*Common Name:**	(2S)-2',4'-Dihydroxy-2' '-(1-Hydroxy-1-Methylethyl)Dihydrofuro[2,3-H]Flavanone
IUPAC Name:	(2S)-2-(2,4-dihydroxyphenyl)-8-(2-hydroxypropan-2-yl)-2,3,8,9-tetrahydrofuro[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	JXVOAHGNNBAJCD-ZENAZSQFSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-20(2,24)18-8-13-16(25-18)6-5-12-15(23)9-17(26-19(12)13)11-4-3-10(21)7-14(11)22/h3-7,17-18,21-22,24H,8-9H2,1-2H3/t17-,18?/m0/s1
SMILES:	Oc1ccc(c(c1)O)[C@@H]1CC(=O)c2c(O1)c1CC(Oc1cc2)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457678
PubChem CID:	10291777
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	100.0	nM	PMID[573960]

☑ 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 NPC473996 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	377
0.1-0.2	1453
0.2-0.3	3463
0.3-0.4	8716
0.4-0.5	9842
0.5-0.6	3588
0.6-0.7	5259
0.7-0.8	5471
0.8-0.85	2616
0.85-0.9	1331
0.9-0.95	528
0.95-1	53

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC472636
0.9931	High Similarity	NPC472580
0.9863	High Similarity	NPC327269
0.9863	High Similarity	NPC476238
0.9863	High Similarity	NPC477957
0.9863	High Similarity	NPC31627
0.9862	High Similarity	NPC472421
0.9795	High Similarity	NPC263384
0.9795	High Similarity	NPC472423
0.9795	High Similarity	NPC471675
0.9795	High Similarity	NPC471676
0.9795	High Similarity	NPC474744
0.9795	High Similarity	NPC472422
0.9795	High Similarity	NPC474772
0.9795	High Similarity	NPC244577
0.9795	High Similarity	NPC472420
0.9728	High Similarity	NPC285623
0.9662	High Similarity	NPC223701
0.9662	High Similarity	NPC7989
0.9662	High Similarity	NPC472583
0.966	High Similarity	NPC471677
0.9655	High Similarity	NPC14875
0.9597	High Similarity	NPC477958
0.9595	High Similarity	NPC475790
0.9595	High Similarity	NPC243171
0.9595	High Similarity	NPC171651
0.9595	High Similarity	NPC35567
0.9589	High Similarity	NPC168085
0.953	High Similarity	NPC293286
0.953	High Similarity	NPC469405
0.9527	High Similarity	NPC319910
0.9527	High Similarity	NPC474021
0.9527	High Similarity	NPC262039
0.9527	High Similarity	NPC278476
0.9527	High Similarity	NPC474023
0.9527	High Similarity	NPC262038
0.9527	High Similarity	NPC254412
0.9524	High Similarity	NPC89442
0.9524	High Similarity	NPC317492
0.9524	High Similarity	NPC472628
0.9521	High Similarity	NPC472627
0.9517	High Similarity	NPC209040
0.9474	High Similarity	NPC472624
0.9474	High Similarity	NPC328102
0.9467	High Similarity	NPC217706
0.9467	High Similarity	NPC279218
0.9467	High Similarity	NPC470681
0.9467	High Similarity	NPC207809
0.9467	High Similarity	NPC259710
0.9467	High Similarity	NPC48579
0.9467	High Similarity	NPC108937
0.9467	High Similarity	NPC304207
0.9463	High Similarity	NPC217149
0.9463	High Similarity	NPC150123
0.9463	High Similarity	NPC216035
0.9463	High Similarity	NPC10807
0.9463	High Similarity	NPC161881
0.9463	High Similarity	NPC244583
0.9463	High Similarity	NPC138288
0.9463	High Similarity	NPC56232
0.9463	High Similarity	NPC210597
0.9459	High Similarity	NPC105136
0.9452	High Similarity	NPC316769
0.9452	High Similarity	NPC472629
0.9448	High Similarity	NPC214166
0.9448	High Similarity	NPC143896
0.9448	High Similarity	NPC149026
0.9448	High Similarity	NPC316816
0.9448	High Similarity	NPC478086
0.9448	High Similarity	NPC75049
0.9448	High Similarity	NPC39329
0.9448	High Similarity	NPC310130
0.9448	High Similarity	NPC18585
0.9448	High Similarity	NPC68104
0.9448	High Similarity	NPC175504
0.9448	High Similarity	NPC91560
0.9448	High Similarity	NPC169591
0.9448	High Similarity	NPC257097
0.9448	High Similarity	NPC166138
0.9448	High Similarity	NPC150408
0.9448	High Similarity	NPC164980
0.9448	High Similarity	NPC106985
0.9448	High Similarity	NPC221432
0.9416	High Similarity	NPC472581
0.9416	High Similarity	NPC124038
0.9412	High Similarity	NPC45124
0.9412	High Similarity	NPC30655
0.9412	High Similarity	NPC74854
0.9412	High Similarity	NPC92589
0.9404	High Similarity	NPC78554
0.9404	High Similarity	NPC474609
0.9404	High Similarity	NPC20530
0.9404	High Similarity	NPC469936
0.9404	High Similarity	NPC109967
0.9404	High Similarity	NPC129053
0.9404	High Similarity	NPC321372
0.9404	High Similarity	NPC475797
0.9404	High Similarity	NPC474738
0.9404	High Similarity	NPC10754
0.9404	High Similarity	NPC215917
0.9404	High Similarity	NPC78492
0.9404	High Similarity	NPC208152
0.94	High Similarity	NPC180301
0.94	High Similarity	NPC209760
0.94	High Similarity	NPC100134
0.94	High Similarity	NPC236756
0.94	High Similarity	NPC311579
0.94	High Similarity	NPC248793
0.9396	High Similarity	NPC471229
0.9396	High Similarity	NPC477897
0.9396	High Similarity	NPC289774
0.9396	High Similarity	NPC328740
0.9396	High Similarity	NPC209846
0.9388	High Similarity	NPC23728
0.9388	High Similarity	NPC202494
0.9388	High Similarity	NPC473077
0.9388	High Similarity	NPC85773
0.9388	High Similarity	NPC472918
0.9388	High Similarity	NPC51070
0.9388	High Similarity	NPC470670
0.9388	High Similarity	NPC296998
0.9388	High Similarity	NPC473133
0.9388	High Similarity	NPC110303
0.9388	High Similarity	NPC91902
0.9388	High Similarity	NPC222298
0.9388	High Similarity	NPC47388
0.9384	High Similarity	NPC236766
0.9384	High Similarity	NPC124780
0.9384	High Similarity	NPC131568
0.9384	High Similarity	NPC470890
0.9384	High Similarity	NPC87486
0.9384	High Similarity	NPC473015
0.9384	High Similarity	NPC197252
0.9384	High Similarity	NPC131579
0.9384	High Similarity	NPC473013
0.9379	High Similarity	NPC166934
0.9379	High Similarity	NPC220998
0.9379	High Similarity	NPC37496
0.9379	High Similarity	NPC107572
0.9379	High Similarity	NPC227579
0.9379	High Similarity	NPC40833
0.9379	High Similarity	NPC223500
0.9379	High Similarity	NPC76338
0.9379	High Similarity	NPC167624
0.9379	High Similarity	NPC265040
0.9379	High Similarity	NPC1089
0.9379	High Similarity	NPC177354
0.9379	High Similarity	NPC78
0.9379	High Similarity	NPC76372
0.9379	High Similarity	NPC324436
0.9379	High Similarity	NPC161506
0.9379	High Similarity	NPC32739
0.9379	High Similarity	NPC66515
0.9379	High Similarity	NPC166482
0.9379	High Similarity	NPC306829
0.9379	High Similarity	NPC147145
0.9379	High Similarity	NPC194432
0.9379	High Similarity	NPC144499
0.9379	High Similarity	NPC64915
0.9379	High Similarity	NPC148757
0.9379	High Similarity	NPC125855
0.9379	High Similarity	NPC328164
0.9379	High Similarity	NPC296917
0.9379	High Similarity	NPC228504
0.9379	High Similarity	NPC324134
0.9379	High Similarity	NPC182852
0.9379	High Similarity	NPC10937
0.9355	High Similarity	NPC300053
0.9355	High Similarity	NPC108433
0.9351	High Similarity	NPC472635
0.9346	High Similarity	NPC471976
0.9346	High Similarity	NPC306978
0.9342	High Similarity	NPC27337
0.9342	High Similarity	NPC291508
0.9338	High Similarity	NPC476169
0.9338	High Similarity	NPC111341
0.9338	High Similarity	NPC304745
0.9338	High Similarity	NPC471116
0.9338	High Similarity	NPC477530
0.9333	High Similarity	NPC256141
0.9329	High Similarity	NPC61258
0.9329	High Similarity	NPC124478
0.9329	High Similarity	NPC476185
0.9329	High Similarity	NPC177308
0.9329	High Similarity	NPC267117
0.9329	High Similarity	NPC472633
0.9329	High Similarity	NPC180351
0.9329	High Similarity	NPC321896
0.9324	High Similarity	NPC10097
0.9324	High Similarity	NPC39195
0.9324	High Similarity	NPC132592
0.9324	High Similarity	NPC160821
0.932	High Similarity	NPC24136
0.932	High Similarity	NPC229190
0.932	High Similarity	NPC88964
0.932	High Similarity	NPC246948
0.932	High Similarity	NPC475052
0.932	High Similarity	NPC187282
0.932	High Similarity	NPC477955
0.932	High Similarity	NPC127059

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 NPC473996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	865
0.2-0.3	1607
0.3-0.4	2572
0.4-0.5	1959
0.5-0.6	1142
0.6-0.7	454
0.7-0.8	170
0.8-0.85	36
0.85-0.9	18
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD4380	Phase 2
0.9272	High Similarity	NPD2393	Clinical (unspecified phase)
0.9216	High Similarity	NPD7075	Discontinued
0.9145	High Similarity	NPD7096	Clinical (unspecified phase)
0.9122	High Similarity	NPD4378	Clinical (unspecified phase)
0.9103	High Similarity	NPD1549	Phase 2
0.9079	High Similarity	NPD1934	Approved
0.9034	High Similarity	NPD1552	Clinical (unspecified phase)
0.9034	High Similarity	NPD1550	Clinical (unspecified phase)
0.8968	High Similarity	NPD4381	Clinical (unspecified phase)
0.8867	High Similarity	NPD7410	Clinical (unspecified phase)
0.8839	High Similarity	NPD8443	Clinical (unspecified phase)
0.8836	High Similarity	NPD2796	Approved
0.8831	High Similarity	NPD6801	Discontinued
0.8782	High Similarity	NPD3882	Suspended
0.8767	High Similarity	NPD1510	Phase 2
0.8766	High Similarity	NPD7411	Suspended
0.8734	High Similarity	NPD5494	Approved
0.8704	High Similarity	NPD7804	Clinical (unspecified phase)
0.8675	High Similarity	NPD6799	Approved
0.8659	High Similarity	NPD6559	Discontinued
0.8654	High Similarity	NPD7819	Suspended
0.8654	High Similarity	NPD2801	Approved
0.8642	High Similarity	NPD3818	Discontinued
0.8634	High Similarity	NPD6167	Clinical (unspecified phase)
0.8634	High Similarity	NPD6166	Phase 2
0.8634	High Similarity	NPD6168	Clinical (unspecified phase)
0.8621	High Similarity	NPD1240	Approved
0.8553	High Similarity	NPD1511	Approved
0.8503	High Similarity	NPD1607	Approved
0.8462	Intermediate Similarity	NPD6599	Discontinued
0.8447	Intermediate Similarity	NPD6959	Discontinued
0.8442	Intermediate Similarity	NPD1512	Approved
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7074	Phase 3
0.8411	Intermediate Similarity	NPD2800	Approved
0.8405	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD3749	Approved
0.8365	Intermediate Similarity	NPD3817	Phase 2
0.8364	Intermediate Similarity	NPD7054	Approved
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8313	Intermediate Similarity	NPD7472	Approved
0.8289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD920	Approved
0.8269	Intermediate Similarity	NPD5403	Approved
0.8263	Intermediate Similarity	NPD6797	Phase 2
0.8214	Intermediate Similarity	NPD7251	Discontinued
0.817	Intermediate Similarity	NPD1243	Approved
0.8166	Intermediate Similarity	NPD7808	Phase 3
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8141	Intermediate Similarity	NPD5401	Approved
0.8141	Intermediate Similarity	NPD2532	Approved
0.8141	Intermediate Similarity	NPD2534	Approved
0.8141	Intermediate Similarity	NPD2533	Approved
0.8141	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5402	Approved
0.8129	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD3750	Approved
0.8117	Intermediate Similarity	NPD4628	Phase 3
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8092	Intermediate Similarity	NPD1551	Phase 2
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8059	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2344	Approved
0.8024	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.7988	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5953	Discontinued
0.7941	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7286	Phase 2
0.7908	Intermediate Similarity	NPD2799	Discontinued
0.7895	Intermediate Similarity	NPD6651	Approved
0.7871	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7862	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2309	Approved
0.7798	Intermediate Similarity	NPD3926	Phase 2
0.7797	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD7033	Discontinued
0.7771	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1613	Approved
0.7763	Intermediate Similarity	NPD943	Approved
0.7763	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2424	Discontinued
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7742	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD6099	Approved
0.7733	Intermediate Similarity	NPD4908	Phase 1
0.773	Intermediate Similarity	NPD7584	Approved
0.7722	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3226	Approved
0.7709	Intermediate Similarity	NPD4363	Phase 3
0.7709	Intermediate Similarity	NPD4360	Phase 2
0.7702	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2346	Discontinued
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8434	Phase 2
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1203	Approved
0.7633	Intermediate Similarity	NPD5711	Approved
0.7633	Intermediate Similarity	NPD5710	Approved
0.7622	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7616	Intermediate Similarity	NPD6832	Phase 2
0.7616	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8312	Approved
0.76	Intermediate Similarity	NPD8313	Approved
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.7572	Intermediate Similarity	NPD1729	Discontinued
0.7569	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4361	Phase 2
0.755	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3823	Discontinued
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD6776	Approved
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD2654	Approved
0.7484	Intermediate Similarity	NPD6355	Discontinued
0.7484	Intermediate Similarity	NPD1933	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7452	Intermediate Similarity	NPD4308	Phase 3
0.7451	Intermediate Similarity	NPD3027	Phase 3
0.7451	Intermediate Similarity	NPD4625	Phase 3
0.745	Intermediate Similarity	NPD9717	Approved
0.7442	Intermediate Similarity	NPD2403	Approved
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7425	Intermediate Similarity	NPD5761	Phase 2
0.7425	Intermediate Similarity	NPD5760	Phase 2
0.7425	Intermediate Similarity	NPD8455	Phase 2
0.7407	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3764	Approved
0.7403	Intermediate Similarity	NPD3268	Approved
0.7394	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4287	Approved
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7435	Discontinued
0.7375	Intermediate Similarity	NPD1652	Phase 2
0.7374	Intermediate Similarity	NPD8150	Discontinued
0.7372	Intermediate Similarity	NPD447	Suspended
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD37	Approved
0.7362	Intermediate Similarity	NPD4662	Approved
0.7362	Intermediate Similarity	NPD4661	Approved
0.7356	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6233	Phase 2
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.732	Intermediate Similarity	NPD2861	Phase 2
0.7317	Intermediate Similarity	NPD5049	Phase 3
0.7316	Intermediate Similarity	NPD7585	Approved
0.7303	Intermediate Similarity	NPD2797	Approved
0.7287	Intermediate Similarity	NPD7696	Phase 3
0.7287	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD7697	Approved
0.7284	Intermediate Similarity	NPD3887	Approved
0.7284	Intermediate Similarity	NPD6190	Approved
0.7284	Intermediate Similarity	NPD2354	Approved
0.7278	Intermediate Similarity	NPD2296	Approved
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7263	Intermediate Similarity	NPD7583	Approved
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.7257	Intermediate Similarity	NPD7228	Approved
0.725	Intermediate Similarity	NPD6004	Phase 3
0.725	Intermediate Similarity	NPD1471	Phase 3
0.725	Intermediate Similarity	NPD6005	Phase 3
0.725	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6002	Phase 3
0.7249	Intermediate Similarity	NPD7870	Phase 2
0.7249	Intermediate Similarity	NPD7871	Phase 2
0.7241	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5058	Phase 3
0.7234	Intermediate Similarity	NPD6823	Phase 2
0.7233	Intermediate Similarity	NPD651	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