NPASS Compound

Structure

NPC279218 OpenBabel07101719152D 30 33 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -5.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -4.4487 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 2.5981 -2.5000 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 0.2079 -3.9781 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 -1.5000 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 -0.0000 -3.0000 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 1.2024 -4.0827 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7024 -4.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -5.8147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -3.1691 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 4 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 8 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 25 2 0 0 0 0 17 24 1 6 0 0 0 17 29 1 0 0 0 0 18 26 2 0 0 0 0 18 30 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.16
Volume:	418.447
LogP:	5.066
LogD:	3.204
LogS:	-3.729
# Rotatable Bonds:	5
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	3.449
Fsp3:	0.333
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:	-4.746
MDCK Permeability:	2.3353652068180963e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.239

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	96.89928436279297%
Volume Distribution (VD):	0.572
Pgp-substrate:	1.7920928001403809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.395
CYP1A2-substrate:	0.389
CYP2C19-inhibitor:	0.531
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.795
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.348
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	5.871
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.386
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.258
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.479
Skin Sensitization:	0.331
Carcinogencity:	0.639
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.39

Download Data

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

Natural Product: NPC279218

Natural Product ID:	NPC279218
*Common Name:**	(2S)-5-Butanoyl-4-Hydroxy-2-(2-Hydroxypropan-2-Yl)-9-Phenyl-2,3-Dihydrofuro[2,3-F]Chromen-7-One
IUPAC Name:	(2S)-5-butanoyl-4-hydroxy-2-(2-hydroxypropan-2-yl)-9-phenyl-2,3-dihydrofuro[2,3-f]chromen-7-one
Synonyms:
Standard InCHIKey:	ADRUKWOHXVJUSH-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C24H24O6/c1-4-8-16(25)20-21(27)15-11-17(24(2,3)28)29-22(15)19-14(12-18(26)30-23(19)20)13-9-6-5-7-10-13/h5-7,9-10,12,17,27-28H,4,8,11H2,1-3H3/t17-/m0/s1
SMILES:	CCCC(=O)c1c(c2C[C@@H](C(C)(C)O)Oc2c2c(cc(=O)oc12)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478085
PubChem CID:	10476551
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374944]
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	GI50	=	50.0	%	PMID[487052]

☑ 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 NPC279218 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	370
0.1-0.2	1485
0.2-0.3	3386
0.3-0.4	8070
0.4-0.5	10602
0.5-0.6	4033
0.6-0.7	5546
0.7-0.8	4654
0.8-0.85	2839
0.85-0.9	1452
0.9-0.95	246
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108937
0.9932	High Similarity	NPC475797
0.9932	High Similarity	NPC109967
0.9932	High Similarity	NPC321372
0.9932	High Similarity	NPC469936
0.9932	High Similarity	NPC78554
0.9932	High Similarity	NPC129053
0.9932	High Similarity	NPC474738
0.9932	High Similarity	NPC474609
0.9662	High Similarity	NPC290671
0.9662	High Similarity	NPC471675
0.96	High Similarity	NPC469934
0.9597	High Similarity	NPC327269
0.9597	High Similarity	NPC31627
0.9597	High Similarity	NPC476238
0.953	High Similarity	NPC472636
0.9467	High Similarity	NPC285623
0.9467	High Similarity	NPC473996
0.9463	High Similarity	NPC321387
0.9463	High Similarity	NPC327059
0.9463	High Similarity	NPC472421
0.9463	High Similarity	NPC474735
0.9463	High Similarity	NPC470908
0.9416	High Similarity	NPC92589
0.94	High Similarity	NPC474772
0.94	High Similarity	NPC472423
0.94	High Similarity	NPC474744
0.94	High Similarity	NPC472580
0.9338	High Similarity	NPC256141
0.9338	High Similarity	NPC477957
0.9333	High Similarity	NPC180351
0.9329	High Similarity	NPC168085
0.9324	High Similarity	NPC470322
0.9276	High Similarity	NPC223701
0.9276	High Similarity	NPC248793
0.9276	High Similarity	NPC472583
0.9276	High Similarity	NPC7989
0.9276	High Similarity	NPC180301
0.9272	High Similarity	NPC244577
0.9272	High Similarity	NPC472420
0.9272	High Similarity	NPC471676
0.9272	High Similarity	NPC472422
0.9272	High Similarity	NPC471677
0.9272	High Similarity	NPC263384
0.9267	High Similarity	NPC104236
0.9267	High Similarity	NPC19238
0.9267	High Similarity	NPC317492
0.9267	High Similarity	NPC164205
0.9262	High Similarity	NPC14875
0.9262	High Similarity	NPC202494
0.9262	High Similarity	NPC285748
0.9262	High Similarity	NPC140120
0.9257	High Similarity	NPC196137
0.9257	High Similarity	NPC1886
0.9257	High Similarity	NPC469953
0.9252	High Similarity	NPC36181
0.9226	High Similarity	NPC328102
0.9216	High Similarity	NPC217706
0.9216	High Similarity	NPC207809
0.9216	High Similarity	NPC259710
0.9216	High Similarity	NPC470681
0.9216	High Similarity	NPC48579
0.9216	High Similarity	NPC304207
0.9211	High Similarity	NPC475790
0.9211	High Similarity	NPC10807
0.9211	High Similarity	NPC150123
0.9211	High Similarity	NPC244583
0.9211	High Similarity	NPC161881
0.9211	High Similarity	NPC56232
0.9205	High Similarity	NPC105136
0.9205	High Similarity	NPC321896
0.9205	High Similarity	NPC476185
0.92	High Similarity	NPC161864
0.92	High Similarity	NPC208303
0.9195	High Similarity	NPC57470
0.9195	High Similarity	NPC154217
0.9195	High Similarity	NPC181388
0.9189	High Similarity	NPC112791
0.9189	High Similarity	NPC196459
0.9189	High Similarity	NPC188632
0.9189	High Similarity	NPC94794
0.9189	High Similarity	NPC470296
0.9189	High Similarity	NPC87609
0.9184	High Similarity	NPC74397
0.9167	High Similarity	NPC14822
0.915	High Similarity	NPC469405
0.915	High Similarity	NPC311579
0.915	High Similarity	NPC236756
0.9145	High Similarity	NPC209846
0.9145	High Similarity	NPC262039
0.9145	High Similarity	NPC319910
0.9145	High Similarity	NPC312549
0.9145	High Similarity	NPC262038
0.9145	High Similarity	NPC328740
0.9145	High Similarity	NPC254412
0.9145	High Similarity	NPC278476
0.9145	High Similarity	NPC289774
0.9145	High Similarity	NPC474021
0.9145	High Similarity	NPC474023
0.9145	High Similarity	NPC477897
0.9145	High Similarity	NPC209142
0.9139	High Similarity	NPC164299
0.9139	High Similarity	NPC5173
0.9139	High Similarity	NPC469932
0.9139	High Similarity	NPC472628
0.9133	High Similarity	NPC297886
0.9133	High Similarity	NPC51070
0.9133	High Similarity	NPC85773
0.9133	High Similarity	NPC180477
0.9133	High Similarity	NPC296998
0.9133	High Similarity	NPC222298
0.9133	High Similarity	NPC472627
0.9133	High Similarity	NPC249942
0.9133	High Similarity	NPC473077
0.9128	High Similarity	NPC178627
0.9128	High Similarity	NPC297788
0.9128	High Similarity	NPC469935
0.9128	High Similarity	NPC224714
0.9125	High Similarity	NPC120220
0.9122	High Similarity	NPC112829
0.9122	High Similarity	NPC472344
0.9122	High Similarity	NPC294432
0.9122	High Similarity	NPC470556
0.9114	High Similarity	NPC204088
0.9114	High Similarity	NPC259007
0.9114	High Similarity	NPC329215
0.9103	High Similarity	NPC49009
0.9103	High Similarity	NPC472624
0.9103	High Similarity	NPC239270
0.9103	High Similarity	NPC303210
0.9103	High Similarity	NPC169
0.9103	High Similarity	NPC95472
0.9097	High Similarity	NPC210048
0.9091	High Similarity	NPC111341
0.9091	High Similarity	NPC477958
0.9091	High Similarity	NPC473241
0.9091	High Similarity	NPC476169
0.9091	High Similarity	NPC304745
0.9085	High Similarity	NPC138288
0.9085	High Similarity	NPC171651
0.9085	High Similarity	NPC210597
0.9085	High Similarity	NPC35567
0.9085	High Similarity	NPC217149
0.9085	High Similarity	NPC216035
0.9085	High Similarity	NPC243171
0.9079	High Similarity	NPC472633
0.9079	High Similarity	NPC476509
0.9079	High Similarity	NPC61258
0.9073	High Similarity	NPC10097
0.9073	High Similarity	NPC469933
0.9068	High Similarity	NPC472584
0.9067	High Similarity	NPC20488
0.9067	High Similarity	NPC124729
0.9067	High Similarity	NPC111786
0.9067	High Similarity	NPC83357
0.9067	High Similarity	NPC267375
0.9067	High Similarity	NPC88964
0.9067	High Similarity	NPC301276
0.9067	High Similarity	NPC195621
0.9067	High Similarity	NPC214774
0.9067	High Similarity	NPC472629
0.9067	High Similarity	NPC54577
0.9067	High Similarity	NPC475052
0.9067	High Similarity	NPC312973
0.9067	High Similarity	NPC470647
0.9067	High Similarity	NPC316769
0.9067	High Similarity	NPC67805
0.9067	High Similarity	NPC246948
0.9067	High Similarity	NPC142405
0.9067	High Similarity	NPC176229
0.9067	High Similarity	NPC474302
0.906	High Similarity	NPC470553
0.906	High Similarity	NPC470909
0.906	High Similarity	NPC184738
0.906	High Similarity	NPC316816
0.906	High Similarity	NPC96216
0.906	High Similarity	NPC474939
0.906	High Similarity	NPC307895
0.906	High Similarity	NPC478086
0.906	High Similarity	NPC214166
0.906	High Similarity	NPC33653
0.9057	High Similarity	NPC323137
0.9054	High Similarity	NPC110038
0.9054	High Similarity	NPC248372
0.9051	High Similarity	NPC91288
0.9048	High Similarity	NPC217186
0.9048	High Similarity	NPC53181
0.9045	High Similarity	NPC97812
0.9038	High Similarity	NPC470607
0.9038	High Similarity	NPC264932
0.9038	High Similarity	NPC311574
0.9032	High Similarity	NPC470625
0.9032	High Similarity	NPC20530
0.9032	High Similarity	NPC215917
0.9032	High Similarity	NPC10754
0.9032	High Similarity	NPC471787
0.9026	High Similarity	NPC112701
0.9026	High Similarity	NPC326592
0.9026	High Similarity	NPC100134
0.9026	High Similarity	NPC88983

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 NPC279218 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	882
0.2-0.3	1673
0.3-0.4	2553
0.4-0.5	2013
0.5-0.6	1098
0.6-0.7	400
0.7-0.8	137
0.8-0.85	53
0.85-0.9	17
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD7075	Discontinued
0.9026	High Similarity	NPD7096	Clinical (unspecified phase)
0.9	High Similarity	NPD4378	Clinical (unspecified phase)
0.8961	High Similarity	NPD6801	Discontinued
0.8954	High Similarity	NPD4380	Phase 2
0.8903	High Similarity	NPD2393	Clinical (unspecified phase)
0.875	High Similarity	NPD7410	Clinical (unspecified phase)
0.8734	High Similarity	NPD4381	Clinical (unspecified phase)
0.8718	High Similarity	NPD1934	Approved
0.8684	High Similarity	NPD6799	Approved
0.8658	High Similarity	NPD1550	Clinical (unspecified phase)
0.8658	High Similarity	NPD1552	Clinical (unspecified phase)
0.8654	High Similarity	NPD7411	Suspended
0.8608	High Similarity	NPD3817	Phase 2
0.86	High Similarity	NPD1549	Phase 2
0.8598	High Similarity	NPD7804	Clinical (unspecified phase)
0.8591	High Similarity	NPD2796	Approved
0.8544	High Similarity	NPD2801	Approved
0.8544	High Similarity	NPD7819	Suspended
0.8537	High Similarity	NPD3818	Discontinued
0.8523	High Similarity	NPD1510	Phase 2
0.8516	High Similarity	NPD920	Approved
0.8491	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6599	Discontinued
0.8443	Intermediate Similarity	NPD6559	Discontinued
0.8442	Intermediate Similarity	NPD1511	Approved
0.8438	Intermediate Similarity	NPD3882	Suspended
0.8421	Intermediate Similarity	NPD1243	Approved
0.8397	Intermediate Similarity	NPD5403	Approved
0.8387	Intermediate Similarity	NPD2532	Approved
0.8387	Intermediate Similarity	NPD2534	Approved
0.8387	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD2533	Approved
0.8385	Intermediate Similarity	NPD3749	Approved
0.8377	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD7768	Phase 2
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6166	Phase 2
0.8301	Intermediate Similarity	NPD2800	Approved
0.8301	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD5494	Approved
0.8269	Intermediate Similarity	NPD5401	Approved
0.8263	Intermediate Similarity	NPD7054	Approved
0.8261	Intermediate Similarity	NPD5402	Approved
0.8255	Intermediate Similarity	NPD1240	Approved
0.8247	Intermediate Similarity	NPD3750	Approved
0.8221	Intermediate Similarity	NPD919	Approved
0.8214	Intermediate Similarity	NPD7074	Phase 3
0.8214	Intermediate Similarity	NPD7472	Approved
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6797	Phase 2
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8146	Intermediate Similarity	NPD1607	Approved
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD4628	Phase 3
0.8121	Intermediate Similarity	NPD2313	Discontinued
0.8121	Intermediate Similarity	NPD6959	Discontinued
0.8121	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7251	Discontinued
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1551	Phase 2
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.807	Intermediate Similarity	NPD7808	Phase 3
0.8039	Intermediate Similarity	NPD7033	Discontinued
0.7965	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5124	Phase 1
0.7953	Intermediate Similarity	NPD5953	Discontinued
0.7941	Intermediate Similarity	NPD7286	Phase 2
0.7922	Intermediate Similarity	NPD3748	Approved
0.7922	Intermediate Similarity	NPD2799	Discontinued
0.7898	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3226	Approved
0.7833	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1247	Approved
0.7792	Intermediate Similarity	NPD6651	Approved
0.7785	Intermediate Similarity	NPD1203	Approved
0.7763	Intermediate Similarity	NPD3268	Approved
0.7758	Intermediate Similarity	NPD1465	Phase 2
0.7751	Intermediate Similarity	NPD5710	Approved
0.7751	Intermediate Similarity	NPD5711	Approved
0.7748	Intermediate Similarity	NPD6832	Phase 2
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2344	Approved
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD4308	Phase 3
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.7667	Intermediate Similarity	NPD2797	Approved
0.7647	Intermediate Similarity	NPD6798	Discontinued
0.7636	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD422	Phase 1
0.7613	Intermediate Similarity	NPD6355	Discontinued
0.761	Intermediate Similarity	NPD1652	Phase 2
0.7595	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7199	Phase 2
0.7584	Intermediate Similarity	NPD9717	Approved
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7584	Approved
0.7544	Intermediate Similarity	NPD7229	Phase 3
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4363	Phase 3
0.7527	Intermediate Similarity	NPD4360	Phase 2
0.7516	Intermediate Similarity	NPD2309	Approved
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7485	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6005	Phase 3
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7484	Intermediate Similarity	NPD6004	Phase 3
0.7484	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6002	Phase 3
0.7484	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3225	Approved
0.7456	Intermediate Similarity	NPD4967	Phase 2
0.7456	Intermediate Similarity	NPD4966	Approved
0.7456	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD8455	Phase 2
0.7439	Intermediate Similarity	NPD5049	Phase 3
0.7438	Intermediate Similarity	NPD2424	Discontinued
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD4307	Phase 2
0.7436	Intermediate Similarity	NPD943	Approved
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3266	Approved
0.7434	Intermediate Similarity	NPD3267	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7585	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7421	Intermediate Similarity	NPD6099	Approved
0.7419	Intermediate Similarity	NPD3764	Approved
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.74	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD2798	Approved
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7371	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7583	Approved
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7358	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1653	Approved
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7325	Intermediate Similarity	NPD4060	Phase 1
0.7321	Intermediate Similarity	NPD5889	Approved
0.7321	Intermediate Similarity	NPD5890	Approved
0.7317	Intermediate Similarity	NPD7390	Discontinued
0.7308	Intermediate Similarity	NPD1296	Phase 2
0.7308	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7783	Phase 2
0.7305	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7301	Intermediate Similarity	NPD2354	Approved
0.7301	Intermediate Similarity	NPD3887	Approved
0.7301	Intermediate Similarity	NPD6190	Approved
0.7294	Intermediate Similarity	NPD4288	Approved
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.729	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1729	Discontinued
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7284	Intermediate Similarity	NPD2654	Approved
0.7273	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.7262	Intermediate Similarity	NPD6585	Discontinued
0.7257	Intermediate Similarity	NPD2403	Approved
0.7248	Intermediate Similarity	NPD9545	Approved
0.7244	Intermediate Similarity	NPD3027	Phase 3
0.7237	Intermediate Similarity	NPD1608	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7229	Intermediate Similarity	NPD6273	Approved
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7205	Intermediate Similarity	NPD5406	Approved
0.7205	Intermediate Similarity	NPD5408	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