NPASS Compound

Structure

NPC470908 OpenBabel07101718282D 29 31 0 0 1 0 0 0 0 0999 V2000 1.7321 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 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 3 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 -1.7321 -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 -0.0000 2.0000 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 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 0 0 0 0 0 0 0 0 0 0 -5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 0.8660 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 -5.6369 1.8660 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 10 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 10 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 23 1 1 0 0 0 14 22 1 0 0 0 0 14 28 1 0 0 0 0 15 24 2 0 0 0 0 15 29 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 25 2 0 0 0 0 19 26 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	409.112
LogP:	2.916
LogD:	2.13
LogS:	-3.472
# Rotatable Bonds:	6
TPSA:	124.27
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	4.315
Fsp3:	0.5
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:	-5.079
MDCK Permeability:	1.1548555448825937e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.581
20% Bioavailability (F20%):	0.116
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	82.40650177001953%
Volume Distribution (VD):	1.416
Pgp-substrate:	13.08865737915039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.398
CYP2C9-substrate:	0.666
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	6.634
Half-life (T1/2):	0.426

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.598
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.243
Rat Oral Acute Toxicity:	0.362
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.179
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC470908

Natural Product ID:	NPC470908
*Common Name:**	4-Hydroxy-2-(2-Hydroxypropan-2-Yl)-9-((S)-1-Hydroxypropyl)-5-(2-Methylbutanoyl)-2H-Furo[2,3-F]Chromen-7(3H)-One
IUPAC Name:	4-hydroxy-2-(2-hydroxypropan-2-yl)-9-[(1S)-1-hydroxypropyl]-5-(2-methylbutanoyl)-2,3-dihydrofuro[2,3-f]chromen-7-one
Synonyms:
Standard InCHIKey:	SQQGGJWEISSOFM-AWAWDMARSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-6-10(3)18(25)17-19(26)12-8-14(22(4,5)27)28-20(12)16-11(13(23)7-2)9-15(24)29-21(16)17/h9-10,13-14,23,26-27H,6-8H2,1-5H3/t10?,13-,14?/m0/s1
SMILES:	CCC(C)C(=O)C1=C2C(=C3C(=C1O)CC(O3)C(C)(C)O)C(=CC(=O)O2)C(CC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2311548
PubChem CID:	11589499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002568] Angular furanocoumarins

*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
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22831798]
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	flower	n.a.	n.a.	PMID[23206866]

☑ 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	9

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[550453]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	50000.0	nM	PMID[550453]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	50000.0	nM	PMID[550453]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	40590.0	nM	PMID[550453]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	33350.0	nM	PMID[550453]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	29160.0	nM	PMID[550453]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[550453]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[550453]

☑ 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 NPC470908 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	358
0.1-0.2	1468
0.2-0.3	3530
0.3-0.4	7880
0.4-0.5	10750
0.5-0.6	4396
0.6-0.7	5717
0.7-0.8	5219
0.8-0.85	2609
0.85-0.9	585
0.9-0.95	177
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC321387
0.9861	High Similarity	NPC327059
0.958	High Similarity	NPC96216
0.958	High Similarity	NPC470909
0.958	High Similarity	NPC474939
0.953	High Similarity	NPC474609
0.953	High Similarity	NPC129053
0.953	High Similarity	NPC109967
0.953	High Similarity	NPC474738
0.953	High Similarity	NPC469936
0.953	High Similarity	NPC321372
0.953	High Similarity	NPC475797
0.953	High Similarity	NPC78554
0.9514	High Similarity	NPC288910
0.9514	High Similarity	NPC133060
0.9514	High Similarity	NPC118059
0.9514	High Similarity	NPC470554
0.951	High Similarity	NPC472344
0.951	High Similarity	NPC294432
0.951	High Similarity	NPC470556
0.9463	High Similarity	NPC279218
0.9463	High Similarity	NPC108937
0.9448	High Similarity	NPC470910
0.9444	High Similarity	NPC18886
0.9444	High Similarity	NPC33653
0.9444	High Similarity	NPC184738
0.9444	High Similarity	NPC307895
0.9444	High Similarity	NPC470553
0.9441	High Similarity	NPC74397
0.9384	High Similarity	NPC202494
0.9384	High Similarity	NPC285748
0.9375	High Similarity	NPC112829
0.9329	High Similarity	NPC256141
0.932	High Similarity	NPC472345
0.9262	High Similarity	NPC290671
0.9252	High Similarity	NPC47388
0.9252	High Similarity	NPC470670
0.9252	High Similarity	NPC474108
0.9252	High Similarity	NPC177995
0.9252	High Similarity	NPC473133
0.9247	High Similarity	NPC297788
0.9231	High Similarity	NPC183639
0.9231	High Similarity	NPC199458
0.9205	High Similarity	NPC469934
0.9195	High Similarity	NPC180351
0.9195	High Similarity	NPC476509
0.9195	High Similarity	NPC474735
0.9167	High Similarity	NPC241975
0.9167	High Similarity	NPC19476
0.9161	High Similarity	NPC474624
0.9161	High Similarity	NPC131782
0.9161	High Similarity	NPC138047
0.9133	High Similarity	NPC474772
0.9133	High Similarity	NPC472423
0.9133	High Similarity	NPC471675
0.9133	High Similarity	NPC474744
0.9128	High Similarity	NPC307052
0.9128	High Similarity	NPC139966
0.9122	High Similarity	NPC91902
0.9122	High Similarity	NPC85773
0.911	High Similarity	NPC276565
0.9097	High Similarity	NPC219584
0.9097	High Similarity	NPC470083
0.9073	High Similarity	NPC31627
0.9073	High Similarity	NPC476238
0.9073	High Similarity	NPC285623
0.9073	High Similarity	NPC327269
0.9067	High Similarity	NPC472421
0.906	High Similarity	NPC10097
0.9054	High Similarity	NPC474302
0.9041	High Similarity	NPC470555
0.9032	High Similarity	NPC92589
0.9032	High Similarity	NPC14822
0.9026	High Similarity	NPC470607
0.9007	High Similarity	NPC472636
0.8986	High Similarity	NPC294365
0.8986	High Similarity	NPC316535
0.898	High Similarity	NPC130206
0.8973	High Similarity	NPC221173
0.8968	High Similarity	NPC303210
0.8968	High Similarity	NPC239270
0.8968	High Similarity	NPC49009
0.8968	High Similarity	NPC169
0.8968	High Similarity	NPC95472
0.8961	High Similarity	NPC470606
0.8947	High Similarity	NPC473996
0.894	High Similarity	NPC38775
0.8926	High Similarity	NPC470322
0.8919	High Similarity	NPC112749
0.8912	High Similarity	NPC171870
0.8904	High Similarity	NPC472343
0.8904	High Similarity	NPC471697
0.8904	High Similarity	NPC139554
0.8896	High Similarity	NPC17521
0.8889	High Similarity	NPC223701
0.8889	High Similarity	NPC248793
0.8889	High Similarity	NPC180301
0.8889	High Similarity	NPC7989
0.8889	High Similarity	NPC472583
0.8889	High Similarity	NPC469405
0.8889	High Similarity	NPC101752
0.8882	High Similarity	NPC472580
0.8882	High Similarity	NPC471677
0.8882	High Similarity	NPC244577
0.8882	High Similarity	NPC474023
0.8882	High Similarity	NPC471676
0.8882	High Similarity	NPC263384
0.8882	High Similarity	NPC474021
0.8882	High Similarity	NPC472420
0.8882	High Similarity	NPC472422
0.8874	High Similarity	NPC164205
0.8874	High Similarity	NPC104236
0.8874	High Similarity	NPC19238
0.8867	High Similarity	NPC14875
0.8861	High Similarity	NPC473908
0.8859	High Similarity	NPC1886
0.8859	High Similarity	NPC196137
0.8859	High Similarity	NPC171656
0.8859	High Similarity	NPC224714
0.8839	High Similarity	NPC269495
0.8836	High Similarity	NPC131130
0.8831	High Similarity	NPC470603
0.8831	High Similarity	NPC207809
0.8831	High Similarity	NPC217706
0.8831	High Similarity	NPC470604
0.8831	High Similarity	NPC304207
0.8831	High Similarity	NPC259710
0.8831	High Similarity	NPC470605
0.8831	High Similarity	NPC48579
0.8831	High Similarity	NPC470681
0.8828	High Similarity	NPC470983
0.8828	High Similarity	NPC470982
0.8824	High Similarity	NPC216035
0.8824	High Similarity	NPC475790
0.8824	High Similarity	NPC161881
0.8824	High Similarity	NPC150123
0.8824	High Similarity	NPC56232
0.8824	High Similarity	NPC244583
0.8824	High Similarity	NPC477957
0.8824	High Similarity	NPC10807
0.8824	High Similarity	NPC217149
0.8816	High Similarity	NPC105136
0.8816	High Similarity	NPC179178
0.8812	High Similarity	NPC102810
0.8808	High Similarity	NPC208303
0.8808	High Similarity	NPC161864
0.8808	High Similarity	NPC168085
0.88	High Similarity	NPC181388
0.88	High Similarity	NPC154217
0.88	High Similarity	NPC316769
0.8797	High Similarity	NPC91288
0.8797	High Similarity	NPC471286
0.8792	High Similarity	NPC112791
0.8792	High Similarity	NPC470296
0.8792	High Similarity	NPC196459
0.8792	High Similarity	NPC242100
0.8792	High Similarity	NPC255133
0.8792	High Similarity	NPC188632
0.8792	High Similarity	NPC94794
0.8792	High Similarity	NPC87609
0.879	High Similarity	NPC97812
0.8784	High Similarity	NPC201820
0.8776	High Similarity	NPC37206
0.8776	High Similarity	NPC23257
0.8774	High Similarity	NPC215917
0.8774	High Similarity	NPC20530
0.8774	High Similarity	NPC10754
0.8766	High Similarity	NPC301233
0.8766	High Similarity	NPC87304
0.8766	High Similarity	NPC268950
0.8766	High Similarity	NPC108706
0.8766	High Similarity	NPC211158
0.8766	High Similarity	NPC78021
0.8758	High Similarity	NPC278476
0.8758	High Similarity	NPC312549
0.8758	High Similarity	NPC477897
0.8758	High Similarity	NPC289774
0.8758	High Similarity	NPC209142
0.8758	High Similarity	NPC319910
0.8758	High Similarity	NPC254412
0.8758	High Similarity	NPC209846
0.8758	High Similarity	NPC190217
0.8758	High Similarity	NPC328740
0.8758	High Similarity	NPC262038
0.8758	High Similarity	NPC262039
0.875	High Similarity	NPC472628
0.875	High Similarity	NPC469932
0.875	High Similarity	NPC5173
0.875	High Similarity	NPC317492
0.8742	High Similarity	NPC259007
0.8742	High Similarity	NPC329215
0.8742	High Similarity	NPC140120
0.8742	High Similarity	NPC8817
0.8742	High Similarity	NPC472627
0.8742	High Similarity	NPC204088
0.8742	High Similarity	NPC297886
0.8742	High Similarity	NPC249942
0.8742	High Similarity	NPC51070
0.8742	High Similarity	NPC222298
0.8733	High Similarity	NPC469953

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 NPC470908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	881
0.2-0.3	1890
0.3-0.4	2580
0.4-0.5	1929
0.5-0.6	1024
0.6-0.7	366
0.7-0.8	130
0.8-0.85	34
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD2533	Approved
0.8609	High Similarity	NPD2532	Approved
0.8609	High Similarity	NPD2534	Approved
0.8599	High Similarity	NPD7075	Discontinued
0.8581	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD2800	Approved
0.8487	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD6799	Approved
0.8278	Intermediate Similarity	NPD1243	Approved
0.8258	Intermediate Similarity	NPD920	Approved
0.8247	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1934	Approved
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5124	Phase 1
0.8165	Intermediate Similarity	NPD7411	Suspended
0.8146	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6651	Approved
0.8117	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8095	Intermediate Similarity	NPD6559	Discontinued
0.8092	Intermediate Similarity	NPD1549	Phase 2
0.8079	Intermediate Similarity	NPD2796	Approved
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8063	Intermediate Similarity	NPD2801	Approved
0.8063	Intermediate Similarity	NPD7819	Suspended
0.8025	Intermediate Similarity	NPD5403	Approved
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.7975	Intermediate Similarity	NPD919	Approved
0.7963	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6166	Phase 2
0.7952	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1511	Approved
0.7939	Intermediate Similarity	NPD5711	Approved
0.7939	Intermediate Similarity	NPD5710	Approved
0.7927	Intermediate Similarity	NPD5494	Approved
0.7917	Intermediate Similarity	NPD7054	Approved
0.7914	Intermediate Similarity	NPD3749	Approved
0.7901	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD5401	Approved
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4628	Phase 3
0.787	Intermediate Similarity	NPD7074	Phase 3
0.787	Intermediate Similarity	NPD7472	Approved
0.7867	Intermediate Similarity	NPD1240	Approved
0.7853	Intermediate Similarity	NPD7768	Phase 2
0.7848	Intermediate Similarity	NPD1512	Approved
0.7844	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6797	Phase 2
0.7811	Intermediate Similarity	NPD5844	Phase 1
0.7806	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7763	Intermediate Similarity	NPD1607	Approved
0.7756	Intermediate Similarity	NPD3750	Approved
0.7733	Intermediate Similarity	NPD7808	Phase 3
0.7733	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2935	Discontinued
0.7727	Intermediate Similarity	NPD1551	Phase 2
0.7725	Intermediate Similarity	NPD6232	Discontinued
0.7662	Intermediate Similarity	NPD7033	Discontinued
0.7662	Intermediate Similarity	NPD2799	Discontinued
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5953	Discontinued
0.7602	Intermediate Similarity	NPD7286	Phase 2
0.7564	Intermediate Similarity	NPD6005	Phase 3
0.7564	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6002	Phase 3
0.7564	Intermediate Similarity	NPD6004	Phase 3
0.756	Intermediate Similarity	NPD1247	Approved
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD1652	Phase 2
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.7436	Intermediate Similarity	NPD3748	Approved
0.7432	Intermediate Similarity	NPD9717	Approved
0.741	Intermediate Similarity	NPD1465	Phase 2
0.7405	Intermediate Similarity	NPD2424	Discontinued
0.74	Intermediate Similarity	NPD1203	Approved
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3268	Approved
0.7378	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7355	Intermediate Similarity	NPD447	Suspended
0.7353	Intermediate Similarity	NPD7199	Phase 2
0.7349	Intermediate Similarity	NPD37	Approved
0.7342	Intermediate Similarity	NPD2344	Approved
0.7342	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7326	Intermediate Similarity	NPD2403	Approved
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD4363	Phase 3
0.7308	Intermediate Similarity	NPD4360	Phase 2
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8312	Approved
0.7288	Intermediate Similarity	NPD8313	Approved
0.7285	Intermediate Similarity	NPD2797	Approved
0.7278	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD6099	Approved
0.7268	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4361	Phase 2
0.7256	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2654	Approved
0.7249	Intermediate Similarity	NPD7584	Approved
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2346	Discontinued
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7212	Intermediate Similarity	NPD1653	Approved
0.7209	Intermediate Similarity	NPD7229	Phase 3
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7168	Intermediate Similarity	NPD3926	Phase 2
0.7168	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1296	Phase 2
0.7161	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5647	Approved
0.7124	Intermediate Similarity	NPD1019	Discontinued
0.712	Intermediate Similarity	NPD7585	Approved
0.7111	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8455	Phase 2
0.7095	Intermediate Similarity	NPD9545	Approved
0.7091	Intermediate Similarity	NPD5049	Phase 3
0.7088	Intermediate Similarity	NPD4287	Approved
0.7088	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.707	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1613	Approved
0.707	Intermediate Similarity	NPD943	Approved
0.707	Intermediate Similarity	NPD4060	Phase 1
0.7068	Intermediate Similarity	NPD7583	Approved
0.7066	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1729	Discontinued
0.7059	Intermediate Similarity	NPD3267	Approved
0.7059	Intermediate Similarity	NPD3266	Approved
0.7051	Intermediate Similarity	NPD411	Approved
0.7045	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.7013	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD3787	Discontinued
0.701	Intermediate Similarity	NPD7783	Phase 2
0.701	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5760	Phase 2
0.6995	Remote Similarity	NPD8151	Discontinued
0.6993	Remote Similarity	NPD3225	Approved
0.6988	Remote Similarity	NPD6273	Approved
0.6987	Remote Similarity	NPD3027	Phase 3
0.6983	Remote Similarity	NPD7685	Pre-registration
0.6974	Remote Similarity	NPD1608	Approved
0.697	Remote Similarity	NPD7390	Discontinued
0.6962	Remote Similarity	NPD4307	Phase 2
0.6959	Remote Similarity	NPD9493	Approved
0.6959	Remote Similarity	NPD5353	Approved
0.6951	Remote Similarity	NPD3887	Approved
0.6951	Remote Similarity	NPD2354	Approved
0.6951	Remote Similarity	NPD6190	Approved
0.6943	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3764	Approved
0.6943	Remote Similarity	NPD7985	Registered
0.6932	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6777	Approved
0.6931	Remote Similarity	NPD6776	Approved
0.6931	Remote Similarity	NPD6782	Approved
0.6931	Remote Similarity	NPD6780	Approved
0.6931	Remote Similarity	NPD6781	Approved
0.6931	Remote Similarity	NPD6779	Approved
0.6931	Remote Similarity	NPD6778	Approved
0.6918	Remote Similarity	NPD1933	Approved
0.6908	Remote Similarity	NPD1547	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