NPASS Compound

Structure

NPC476238 OpenBabel07101718182D 33 36 0 0 1 0 0 0 0 0999 V2000 1.8171 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 31 1 0 0 0 0 6 11 1 0 0 0 0 6 13 2 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 32 1 0 0 0 0 14 17 1 0 0 0 0 15 27 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 18 23 2 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 28 1 0 0 0 0 21 29 2 0 0 0 0 22 33 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 24 31 1 6 0 0 0 25 26 1 1 0 0 0 25 33 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.18
Volume:	461.83
LogP:	5.314
LogD:	2.798
LogS:	-3.17
# Rotatable Bonds:	5
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	4.009
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.774
MDCK Permeability:	1.0377956641605124e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.348
Human Intestinal Absorption (HIA):	0.174
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	91.47578430175781%
Volume Distribution (VD):	0.617
Pgp-substrate:	8.546770095825195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.144
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.328
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.713
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.158
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	2.726
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.53
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.901
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.371
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC476238

Natural Product ID:	NPC476238
*Common Name:**	5,4'-Dihydroxy-6-(3''-Methylbut-2''-Enyl)-2'''-(4'''-Hydroxy-4'''-Methylethyl)-3'''-Methoxydihydrofurano-[4''',5''';7,8]Isoflavone
IUPAC Name:	(8R,9R)-5-hydroxy-3-(4-hydroxyphenyl)-8-(2-hydroxypropan-2-yl)-9-methoxy-6-(3-methylbut-2-enyl)-8,9-dihydrofuro[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	DTTYOIOSVDOSOG-JWQCQUIFSA-N
Standard InCHI:	InChI=1S/C26H28O7/c1-13(2)6-11-16-20(28)18-21(29)17(14-7-9-15(27)10-8-14)12-32-23(18)19-22(16)33-25(24(19)31-5)26(3,4)30/h6-10,12,24-25,27-28,30H,11H2,1-5H3/t24-,25-/m1/s1
SMILES:	CC(=CCC1=C(C2=C(C3=C1OC(C3OC)C(C)(C)O)OC=C(C2=O)C4=CC=C(C=C4)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557289
PubChem CID:	25195224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	11800.0	nM	PMID[528735]

☑ 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 NPC476238 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	406
0.1-0.2	1524
0.2-0.3	3460
0.3-0.4	8774
0.4-0.5	9908
0.5-0.6	3891
0.6-0.7	5316
0.7-0.8	4811
0.8-0.85	2269
0.85-0.9	1958
0.9-0.95	345
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC327269
1.0	High Similarity	NPC31627
0.9931	High Similarity	NPC471675
0.9863	High Similarity	NPC285623
0.9863	High Similarity	NPC473996
0.9862	High Similarity	NPC472421
0.9795	High Similarity	NPC472423
0.9795	High Similarity	NPC472580
0.9795	High Similarity	NPC474744
0.9795	High Similarity	NPC472636
0.9795	High Similarity	NPC474772
0.9728	High Similarity	NPC477957
0.9724	High Similarity	NPC168085
0.9662	High Similarity	NPC223701
0.9662	High Similarity	NPC7989
0.9662	High Similarity	NPC472583
0.966	High Similarity	NPC244577
0.966	High Similarity	NPC472422
0.966	High Similarity	NPC263384
0.966	High Similarity	NPC472420
0.966	High Similarity	NPC471676
0.9658	High Similarity	NPC317492
0.9655	High Similarity	NPC14875
0.9603	High Similarity	NPC328102
0.9597	High Similarity	NPC279218
0.9597	High Similarity	NPC108937
0.9597	High Similarity	NPC470681
0.9533	High Similarity	NPC109967
0.9533	High Similarity	NPC78554
0.9533	High Similarity	NPC475797
0.9533	High Similarity	NPC469936
0.9533	High Similarity	NPC129053
0.9533	High Similarity	NPC321372
0.9533	High Similarity	NPC474609
0.9533	High Similarity	NPC474738
0.953	High Similarity	NPC469405
0.9527	High Similarity	NPC471677
0.9521	High Similarity	NPC51070
0.9521	High Similarity	NPC222298
0.9521	High Similarity	NPC202494
0.9467	High Similarity	NPC217706
0.9467	High Similarity	NPC207809
0.9467	High Similarity	NPC259710
0.9467	High Similarity	NPC48579
0.9467	High Similarity	NPC304207
0.9467	High Similarity	NPC477958
0.9463	High Similarity	NPC475790
0.9463	High Similarity	NPC150123
0.9463	High Similarity	NPC171651
0.9463	High Similarity	NPC10807
0.9463	High Similarity	NPC161881
0.9463	High Similarity	NPC35567
0.9463	High Similarity	NPC243171
0.9463	High Similarity	NPC244583
0.9463	High Similarity	NPC56232
0.9459	High Similarity	NPC321896
0.9459	High Similarity	NPC476185
0.9459	High Similarity	NPC61258
0.9452	High Similarity	NPC316769
0.9412	High Similarity	NPC92589
0.94	High Similarity	NPC293286
0.94	High Similarity	NPC180301
0.94	High Similarity	NPC236756
0.94	High Similarity	NPC311579
0.94	High Similarity	NPC248793
0.9396	High Similarity	NPC474021
0.9396	High Similarity	NPC254412
0.9396	High Similarity	NPC262038
0.9396	High Similarity	NPC319910
0.9396	High Similarity	NPC262039
0.9396	High Similarity	NPC474023
0.9396	High Similarity	NPC477897
0.9396	High Similarity	NPC278476
0.9396	High Similarity	NPC289774
0.9396	High Similarity	NPC328740
0.9396	High Similarity	NPC209846
0.9392	High Similarity	NPC472628
0.9392	High Similarity	NPC89442
0.9392	High Similarity	NPC5173
0.9388	High Similarity	NPC23728
0.9388	High Similarity	NPC473077
0.9388	High Similarity	NPC85773
0.9388	High Similarity	NPC24673
0.9388	High Similarity	NPC237635
0.9388	High Similarity	NPC472627
0.9388	High Similarity	NPC201731
0.9388	High Similarity	NPC296998
0.9388	High Similarity	NPC104406
0.9388	High Similarity	NPC110303
0.9388	High Similarity	NPC79469
0.9388	High Similarity	NPC97716
0.9384	High Similarity	NPC234629
0.9384	High Similarity	NPC311741
0.9384	High Similarity	NPC224714
0.9384	High Similarity	NPC209040
0.9384	High Similarity	NPC297788
0.9379	High Similarity	NPC11561
0.9379	High Similarity	NPC226636
0.9351	High Similarity	NPC219861
0.9346	High Similarity	NPC472624
0.9338	High Similarity	NPC476169
0.9338	High Similarity	NPC304745
0.9338	High Similarity	NPC477530
0.9338	High Similarity	NPC111341
0.9333	High Similarity	NPC138288
0.9333	High Similarity	NPC256141
0.9333	High Similarity	NPC216035
0.9333	High Similarity	NPC217149
0.9333	High Similarity	NPC210597
0.9329	High Similarity	NPC124478
0.9329	High Similarity	NPC177308
0.9329	High Similarity	NPC105136
0.9329	High Similarity	NPC472633
0.9329	High Similarity	NPC180351
0.9324	High Similarity	NPC6511
0.9324	High Similarity	NPC10097
0.9324	High Similarity	NPC266572
0.9324	High Similarity	NPC132592
0.9324	High Similarity	NPC160821
0.932	High Similarity	NPC88964
0.932	High Similarity	NPC246948
0.932	High Similarity	NPC176229
0.932	High Similarity	NPC472629
0.932	High Similarity	NPC475052
0.932	High Similarity	NPC124729
0.932	High Similarity	NPC312973
0.932	High Similarity	NPC111786
0.932	High Similarity	NPC142405
0.932	High Similarity	NPC83357
0.932	High Similarity	NPC301276
0.932	High Similarity	NPC474302
0.932	High Similarity	NPC54577
0.932	High Similarity	NPC214774
0.932	High Similarity	NPC470647
0.932	High Similarity	NPC20488
0.932	High Similarity	NPC67805
0.932	High Similarity	NPC267375
0.932	High Similarity	NPC195621
0.9315	High Similarity	NPC175504
0.9315	High Similarity	NPC51887
0.9315	High Similarity	NPC149026
0.9315	High Similarity	NPC169591
0.9315	High Similarity	NPC475705
0.9315	High Similarity	NPC68104
0.9315	High Similarity	NPC257097
0.9315	High Similarity	NPC310130
0.9315	High Similarity	NPC478086
0.9315	High Similarity	NPC476178
0.9315	High Similarity	NPC150408
0.9315	High Similarity	NPC166138
0.9315	High Similarity	NPC214166
0.9315	High Similarity	NPC18585
0.9315	High Similarity	NPC39329
0.9315	High Similarity	NPC143896
0.9315	High Similarity	NPC221432
0.9315	High Similarity	NPC91560
0.9315	High Similarity	NPC117836
0.9315	High Similarity	NPC316816
0.9315	High Similarity	NPC75049
0.9315	High Similarity	NPC164980
0.9315	High Similarity	NPC106985
0.931	High Similarity	NPC156590
0.931	High Similarity	NPC103362
0.931	High Similarity	NPC118840
0.931	High Similarity	NPC74397
0.931	High Similarity	NPC205006
0.931	High Similarity	NPC147688
0.931	High Similarity	NPC110969
0.931	High Similarity	NPC171870
0.931	High Similarity	NPC469404
0.931	High Similarity	NPC64908
0.929	High Similarity	NPC124038
0.929	High Similarity	NPC472581
0.9286	High Similarity	NPC74854
0.9286	High Similarity	NPC30655
0.9286	High Similarity	NPC45124
0.9276	High Similarity	NPC215917
0.9276	High Similarity	NPC10754
0.9276	High Similarity	NPC208152
0.9276	High Similarity	NPC20530
0.9276	High Similarity	NPC78492
0.9272	High Similarity	NPC109594
0.9272	High Similarity	NPC268193
0.9272	High Similarity	NPC326592
0.9272	High Similarity	NPC209760
0.9272	High Similarity	NPC112701
0.9272	High Similarity	NPC100134
0.9267	High Similarity	NPC290671
0.9267	High Similarity	NPC471229
0.9262	High Similarity	NPC221868
0.9262	High Similarity	NPC307052
0.9262	High Similarity	NPC139966
0.9262	High Similarity	NPC37208
0.9257	High Similarity	NPC47388
0.9257	High Similarity	NPC473133
0.9257	High Similarity	NPC470670
0.9257	High Similarity	NPC472918
0.9257	High Similarity	NPC91902
0.9257	High Similarity	NPC283234
0.9252	High Similarity	NPC197252

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 NPC476238 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	890
0.2-0.3	1615
0.3-0.4	2615
0.4-0.5	1986
0.5-0.6	1101
0.6-0.7	389
0.7-0.8	139
0.8-0.85	38
0.85-0.9	22
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD4380	Phase 2
0.9252	High Similarity	NPD4378	Clinical (unspecified phase)
0.9145	High Similarity	NPD2393	Clinical (unspecified phase)
0.9091	High Similarity	NPD7075	Discontinued
0.902	High Similarity	NPD7096	Clinical (unspecified phase)
0.8993	High Similarity	NPD7410	Clinical (unspecified phase)
0.8973	High Similarity	NPD1549	Phase 2
0.8968	High Similarity	NPD4381	Clinical (unspecified phase)
0.8966	High Similarity	NPD2796	Approved
0.8954	High Similarity	NPD1934	Approved
0.8954	High Similarity	NPD6801	Discontinued
0.8904	High Similarity	NPD1552	Clinical (unspecified phase)
0.8904	High Similarity	NPD1550	Clinical (unspecified phase)
0.8897	High Similarity	NPD1510	Phase 2
0.8782	High Similarity	NPD3882	Suspended
0.8774	High Similarity	NPD2801	Approved
0.8758	High Similarity	NPD3818	Discontinued
0.8718	High Similarity	NPD8443	Clinical (unspecified phase)
0.8704	High Similarity	NPD7804	Clinical (unspecified phase)
0.8675	High Similarity	NPD6799	Approved
0.8675	High Similarity	NPD1511	Approved
0.8645	High Similarity	NPD7411	Suspended
0.8621	High Similarity	NPD1240	Approved
0.8616	High Similarity	NPD5494	Approved
0.8562	High Similarity	NPD1512	Approved
0.8545	High Similarity	NPD6559	Discontinued
0.8535	High Similarity	NPD7819	Suspended
0.8519	High Similarity	NPD6167	Clinical (unspecified phase)
0.8519	High Similarity	NPD6168	Clinical (unspecified phase)
0.8519	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD1607	Approved
0.8481	Intermediate Similarity	NPD3817	Phase 2
0.8462	Intermediate Similarity	NPD6599	Discontinued
0.8411	Intermediate Similarity	NPD2800	Approved
0.8387	Intermediate Similarity	NPD920	Approved
0.8387	Intermediate Similarity	NPD5403	Approved
0.8364	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8313	Intermediate Similarity	NPD7074	Phase 3
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7472	Approved
0.8293	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1243	Approved
0.8289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD6797	Phase 2
0.8261	Intermediate Similarity	NPD3749	Approved
0.8258	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD5401	Approved
0.825	Intermediate Similarity	NPD5402	Approved
0.8247	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3750	Approved
0.8214	Intermediate Similarity	NPD7251	Discontinued
0.8166	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7808	Phase 3
0.8141	Intermediate Similarity	NPD2532	Approved
0.8141	Intermediate Similarity	NPD2534	Approved
0.8141	Intermediate Similarity	NPD2533	Approved
0.8117	Intermediate Similarity	NPD4628	Phase 3
0.811	Intermediate Similarity	NPD1247	Approved
0.8098	Intermediate Similarity	NPD919	Approved
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8092	Intermediate Similarity	NPD1551	Phase 2
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2344	Approved
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8024	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2313	Discontinued
0.7987	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5953	Discontinued
0.7929	Intermediate Similarity	NPD7286	Phase 2
0.7908	Intermediate Similarity	NPD2799	Discontinued
0.7908	Intermediate Similarity	NPD3748	Approved
0.7908	Intermediate Similarity	NPD7033	Discontinued
0.7895	Intermediate Similarity	NPD6651	Approved
0.7885	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2309	Approved
0.7821	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3926	Phase 2
0.7763	Intermediate Similarity	NPD943	Approved
0.7748	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7584	Approved
0.7716	Intermediate Similarity	NPD3226	Approved
0.7709	Intermediate Similarity	NPD4360	Phase 2
0.7709	Intermediate Similarity	NPD4363	Phase 3
0.7702	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8434	Phase 2
0.7667	Intermediate Similarity	NPD4361	Phase 2
0.7667	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1203	Approved
0.7647	Intermediate Similarity	NPD1613	Approved
0.7647	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2424	Discontinued
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7628	Intermediate Similarity	NPD6099	Approved
0.7628	Intermediate Similarity	NPD6100	Approved
0.7616	Intermediate Similarity	NPD4908	Phase 1
0.7616	Intermediate Similarity	NPD6832	Phase 2
0.76	Intermediate Similarity	NPD2798	Approved
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.7586	Intermediate Similarity	NPD1548	Phase 1
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7572	Intermediate Similarity	NPD1729	Discontinued
0.7564	Intermediate Similarity	NPD4308	Phase 3
0.7558	Intermediate Similarity	NPD3751	Discontinued
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5711	Approved
0.7529	Intermediate Similarity	NPD5710	Approved
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD3268	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD8313	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7484	Intermediate Similarity	NPD2654	Approved
0.7484	Intermediate Similarity	NPD6355	Discontinued
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7451	Intermediate Similarity	NPD3027	Phase 3
0.745	Intermediate Similarity	NPD9717	Approved
0.7442	Intermediate Similarity	NPD2403	Approved
0.7434	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3823	Discontinued
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7425	Intermediate Similarity	NPD5761	Phase 2
0.7425	Intermediate Similarity	NPD5760	Phase 2
0.7417	Intermediate Similarity	NPD2797	Approved
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6780	Approved
0.7405	Intermediate Similarity	NPD6778	Approved
0.7405	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6782	Approved
0.7405	Intermediate Similarity	NPD6779	Approved
0.7405	Intermediate Similarity	NPD6781	Approved
0.7405	Intermediate Similarity	NPD6777	Approved
0.7405	Intermediate Similarity	NPD6776	Approved
0.7403	Intermediate Similarity	NPD3764	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD422	Phase 1
0.7375	Intermediate Similarity	NPD1652	Phase 2
0.7372	Intermediate Similarity	NPD1933	Approved
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	NPD7004	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4661	Approved
0.7356	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6233	Phase 2
0.7341	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD8455	Phase 2
0.7317	Intermediate Similarity	NPD5049	Phase 3
0.7316	Intermediate Similarity	NPD7585	Approved
0.7308	Intermediate Similarity	NPD4307	Phase 2
0.7293	Intermediate Similarity	NPD4287	Approved
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7435	Discontinued
0.7284	Intermediate Similarity	NPD3887	Approved
0.7284	Intermediate Similarity	NPD6190	Approved
0.7284	Intermediate Similarity	NPD2354	Approved
0.7278	Intermediate Similarity	NPD4288	Approved
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD2296	Approved
0.7263	Intermediate Similarity	NPD7583	Approved
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.725	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
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	NPD6006	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6002	Phase 3
0.7241	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3225	Approved
0.7233	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9545	Approved
0.7229	Intermediate Similarity	NPD1653	Approved
0.7219	Intermediate Similarity	NPD3972	Approved
0.7208	Intermediate Similarity	NPD2861	Phase 2
0.7202	Intermediate Similarity	NPD5889	Approved
0.7202	Intermediate Similarity	NPD5890	Approved
0.7197	Intermediate Similarity	NPD4060	Phase 1

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