NPASS Compound

Structure

NPC78492 OpenBabel07101718202D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 1.7321 -2.0000 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 0.8660 2.5000 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 2.5981 2.5000 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 -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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -0.0000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 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 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 31 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 28 2 0 0 0 0 20 23 1 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 31 1 0 0 0 0 23 25 2 0 0 0 0 24 15 1 6 0 0 0 24 32 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.14
Volume:	439.261
LogP:	3.77
LogD:	3.071
LogS:	-4.472
# Rotatable Bonds:	5
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	3.573
Fsp3:	0.16
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:	-5.235
MDCK Permeability:	7.253124294948066e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.667
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	99.61134338378906%
Volume Distribution (VD):	0.557
Pgp-substrate:	0.8132247924804688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.87
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.356
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.874
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.703
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	11.129
Half-life (T1/2):	0.648

ADMET: Toxicity

hERG Blockers:	0.193
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.43
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.795
Skin Sensitization:	0.946
Carcinogencity:	0.186
Eye Corrosion:	0.003
Eye Irritation:	0.769
Respiratory Toxicity:	0.275

Download Data

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

Natural Product: NPC78492

Natural Product ID:	NPC78492
*Common Name:**	8-[(E)-4-Phenylprop-2-En-1-One]-(2S,3R)-2-(3,5-Dihydroxyphenyl)-3,4-Dihydro-2H-2-Benzopyran-5-Methoxyl-3,7-Diol
IUPAC Name:	(E)-1-[(2S,3R)-2-(3,5-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-3,4-dihydro-2H-chromen-8-yl]-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	BARBUPBDCQNXQJ-BXDPLHIOSA-N
Standard InCHI:	InChI=1S/C25H22O7/c1-31-22-13-20(29)23(19(28)8-7-14-5-3-2-4-6-14)25-18(22)12-21(30)24(32-25)15-9-16(26)11-17(27)10-15/h2-11,13,21,24,26-27,29-30H,12H2,1H3/b8-7+/t21-,24+/m1/s1
SMILES:	COc1cc(c(C(=O)/C=C/c2ccccc2)c2c1C[C@H]([C@H](c1cc(cc(c1)O)O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561568
PubChem CID:	42638983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]

☑ 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
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7100.0	nM	PMID[514396]

☑ 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 NPC78492 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	396
0.1-0.2	1573
0.2-0.3	3691
0.3-0.4	9064
0.4-0.5	9291
0.5-0.6	3368
0.6-0.7	5099
0.7-0.8	5073
0.8-0.85	2580
0.85-0.9	2010
0.9-0.95	540
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208152
0.9673	High Similarity	NPC476247
0.9608	High Similarity	NPC142252
0.96	High Similarity	NPC244250
0.96	High Similarity	NPC472583
0.96	High Similarity	NPC223701
0.96	High Similarity	NPC20907
0.96	High Similarity	NPC7989
0.9597	High Similarity	NPC244577
0.9597	High Similarity	NPC472420
0.9597	High Similarity	NPC263384
0.9597	High Similarity	NPC472422
0.9597	High Similarity	NPC471676
0.9542	High Similarity	NPC471976
0.9536	High Similarity	NPC477958
0.9533	High Similarity	NPC243171
0.9533	High Similarity	NPC56232
0.9533	High Similarity	NPC244583
0.9533	High Similarity	NPC171651
0.9533	High Similarity	NPC161881
0.9533	High Similarity	NPC35567
0.9533	High Similarity	NPC150123
0.9533	High Similarity	NPC475790
0.9533	High Similarity	NPC10807
0.9481	High Similarity	NPC3629
0.9474	High Similarity	NPC471787
0.947	High Similarity	NPC293286
0.947	High Similarity	NPC469405
0.9467	High Similarity	NPC262039
0.9467	High Similarity	NPC278476
0.9467	High Similarity	NPC319910
0.9467	High Similarity	NPC289774
0.9467	High Similarity	NPC471677
0.9467	High Similarity	NPC474023
0.9467	High Similarity	NPC477897
0.9467	High Similarity	NPC254412
0.9467	High Similarity	NPC209846
0.9467	High Similarity	NPC474021
0.9467	High Similarity	NPC328740
0.9467	High Similarity	NPC262038
0.9463	High Similarity	NPC89442
0.9419	High Similarity	NPC474033
0.9419	High Similarity	NPC474034
0.9416	High Similarity	NPC475784
0.9412	High Similarity	NPC474055
0.9412	High Similarity	NPC291508
0.9412	High Similarity	NPC472598
0.9408	High Similarity	NPC470681
0.9408	High Similarity	NPC259710
0.9408	High Similarity	NPC207809
0.9408	High Similarity	NPC48579
0.9408	High Similarity	NPC111341
0.9408	High Similarity	NPC304207
0.9408	High Similarity	NPC321779
0.9408	High Similarity	NPC217706
0.9408	High Similarity	NPC304745
0.9404	High Similarity	NPC138288
0.9404	High Similarity	NPC216035
0.9404	High Similarity	NPC473996
0.9404	High Similarity	NPC217149
0.94	High Similarity	NPC105136
0.94	High Similarity	NPC472633
0.94	High Similarity	NPC124478
0.94	High Similarity	NPC177308
0.9392	High Similarity	NPC470134
0.9392	High Similarity	NPC470133
0.9392	High Similarity	NPC109183
0.9392	High Similarity	NPC24136
0.9392	High Similarity	NPC473078
0.9392	High Similarity	NPC290133
0.9392	High Similarity	NPC187282
0.9392	High Similarity	NPC470132
0.9392	High Similarity	NPC470131
0.9392	High Similarity	NPC472629
0.9355	High Similarity	NPC472632
0.9355	High Similarity	NPC74854
0.9355	High Similarity	NPC97812
0.9355	High Similarity	NPC45124
0.9355	High Similarity	NPC26326
0.9355	High Similarity	NPC30655
0.9355	High Similarity	NPC158188
0.9355	High Similarity	NPC474038
0.9351	High Similarity	NPC53545
0.9351	High Similarity	NPC123544
0.9351	High Similarity	NPC117418
0.9351	High Similarity	NPC473990
0.9351	High Similarity	NPC22192
0.9346	High Similarity	NPC195796
0.9346	High Similarity	NPC35038
0.9346	High Similarity	NPC291878
0.9346	High Similarity	NPC278778
0.9342	High Similarity	NPC248793
0.9342	High Similarity	NPC112701
0.9342	High Similarity	NPC192083
0.9342	High Similarity	NPC180301
0.9342	High Similarity	NPC213896
0.9342	High Similarity	NPC109594
0.9342	High Similarity	NPC268193
0.9342	High Similarity	NPC326592
0.9338	High Similarity	NPC472636
0.9338	High Similarity	NPC474772
0.9338	High Similarity	NPC472423
0.9338	High Similarity	NPC472580
0.9338	High Similarity	NPC474744
0.9333	High Similarity	NPC472628
0.9329	High Similarity	NPC472627
0.9324	High Similarity	NPC124780
0.9324	High Similarity	NPC470890
0.9324	High Similarity	NPC39045
0.9324	High Similarity	NPC470135
0.9324	High Similarity	NPC87486
0.9324	High Similarity	NPC470136
0.9304	High Similarity	NPC260266
0.9299	High Similarity	NPC471788
0.929	High Similarity	NPC118256
0.929	High Similarity	NPC282009
0.929	High Similarity	NPC174953
0.929	High Similarity	NPC192686
0.929	High Similarity	NPC119209
0.929	High Similarity	NPC287328
0.9286	High Similarity	NPC284820
0.9286	High Similarity	NPC27337
0.9286	High Similarity	NPC473272
0.9286	High Similarity	NPC183851
0.9286	High Similarity	NPC471209
0.9286	High Similarity	NPC63454
0.9281	High Similarity	NPC477503
0.9281	High Similarity	NPC45849
0.9281	High Similarity	NPC470327
0.9281	High Similarity	NPC200761
0.9281	High Similarity	NPC477530
0.9281	High Similarity	NPC226025
0.9276	High Similarity	NPC477957
0.9276	High Similarity	NPC31627
0.9276	High Similarity	NPC285623
0.9276	High Similarity	NPC106976
0.9276	High Similarity	NPC327269
0.9276	High Similarity	NPC476238
0.9272	High Similarity	NPC472421
0.9272	High Similarity	NPC37348
0.9267	High Similarity	NPC218569
0.9267	High Similarity	NPC10097
0.9262	High Similarity	NPC228779
0.9262	High Similarity	NPC316769
0.9257	High Similarity	NPC91560
0.9257	High Similarity	NPC68104
0.9257	High Similarity	NPC75049
0.9257	High Similarity	NPC150408
0.9257	High Similarity	NPC164980
0.9257	High Similarity	NPC169591
0.9257	High Similarity	NPC39329
0.9257	High Similarity	NPC257097
0.9257	High Similarity	NPC175504
0.9257	High Similarity	NPC149026
0.9257	High Similarity	NPC310130
0.9257	High Similarity	NPC143896
0.9257	High Similarity	NPC221432
0.9245	High Similarity	NPC475212
0.9236	High Similarity	NPC472625
0.9236	High Similarity	NPC124038
0.9231	High Similarity	NPC472634
0.9231	High Similarity	NPC471210
0.9231	High Similarity	NPC113163
0.9231	High Similarity	NPC305987
0.9231	High Similarity	NPC84324
0.9231	High Similarity	NPC288131
0.9231	High Similarity	NPC471499
0.9231	High Similarity	NPC165970
0.9231	High Similarity	NPC289771
0.9231	High Similarity	NPC134783
0.9231	High Similarity	NPC66618
0.9226	High Similarity	NPC284127
0.9226	High Similarity	NPC172202
0.9226	High Similarity	NPC476410
0.9221	High Similarity	NPC472626
0.9221	High Similarity	NPC209614
0.9221	High Similarity	NPC215917
0.9221	High Similarity	NPC470328
0.9221	High Similarity	NPC10754
0.9221	High Similarity	NPC20530
0.9216	High Similarity	NPC18727
0.9216	High Similarity	NPC311579
0.9216	High Similarity	NPC74924
0.9216	High Similarity	NPC236756
0.9216	High Similarity	NPC298692
0.9211	High Similarity	NPC178484
0.9211	High Similarity	NPC471675
0.9205	High Similarity	NPC307052
0.9205	High Similarity	NPC5173
0.9205	High Similarity	NPC266499
0.9205	High Similarity	NPC3642
0.9205	High Similarity	NPC139966
0.92	High Similarity	NPC23728
0.92	High Similarity	NPC476182
0.92	High Similarity	NPC176869
0.92	High Similarity	NPC110303
0.92	High Similarity	NPC122828
0.92	High Similarity	NPC473133
0.92	High Similarity	NPC473077
0.92	High Similarity	NPC3779

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 NPC78492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	900
0.2-0.3	1655
0.3-0.4	2596
0.4-0.5	1844
0.5-0.6	1078
0.6-0.7	490
0.7-0.8	162
0.8-0.85	32
0.85-0.9	26
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.94	High Similarity	NPD4380	Phase 2
0.9342	High Similarity	NPD2393	Clinical (unspecified phase)
0.9177	High Similarity	NPD6166	Phase 2
0.9177	High Similarity	NPD6168	Clinical (unspecified phase)
0.9177	High Similarity	NPD6167	Clinical (unspecified phase)
0.915	High Similarity	NPD1934	Approved
0.9038	High Similarity	NPD7075	Discontinued
0.9038	High Similarity	NPD4381	Clinical (unspecified phase)
0.9032	High Similarity	NPD8443	Clinical (unspecified phase)
0.8968	High Similarity	NPD7096	Clinical (unspecified phase)
0.8961	High Similarity	NPD7411	Suspended
0.894	High Similarity	NPD4378	Clinical (unspecified phase)
0.894	High Similarity	NPD7410	Clinical (unspecified phase)
0.8919	High Similarity	NPD1549	Phase 2
0.8868	High Similarity	NPD6959	Discontinued
0.8854	High Similarity	NPD4868	Clinical (unspecified phase)
0.8851	High Similarity	NPD1552	Clinical (unspecified phase)
0.8851	High Similarity	NPD1550	Clinical (unspecified phase)
0.8782	High Similarity	NPD6801	Discontinued
0.8773	High Similarity	NPD7804	Clinical (unspecified phase)
0.8727	High Similarity	NPD6559	Discontinued
0.8726	High Similarity	NPD2801	Approved
0.8726	High Similarity	NPD7819	Suspended
0.872	High Similarity	NPD7074	Phase 3
0.8688	High Similarity	NPD5494	Approved
0.8659	High Similarity	NPD5844	Phase 1
0.8659	High Similarity	NPD7054	Approved
0.8658	High Similarity	NPD2796	Approved
0.8627	High Similarity	NPD1511	Approved
0.8616	High Similarity	NPD3882	Suspended
0.8606	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD3818	Discontinued
0.8591	High Similarity	NPD1510	Phase 2
0.8589	High Similarity	NPD7852	Clinical (unspecified phase)
0.8554	High Similarity	NPD6797	Phase 2
0.8516	High Similarity	NPD1512	Approved
0.8506	High Similarity	NPD6799	Approved
0.8503	High Similarity	NPD7251	Discontinued
0.85	High Similarity	NPD7768	Phase 2
0.8452	Intermediate Similarity	NPD7808	Phase 3
0.8446	Intermediate Similarity	NPD1240	Approved
0.8443	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5402	Approved
0.8438	Intermediate Similarity	NPD3817	Phase 2
0.8366	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD5403	Approved
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1607	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8302	Intermediate Similarity	NPD6599	Discontinued
0.8221	Intermediate Similarity	NPD3749	Approved
0.8217	Intermediate Similarity	NPD5401	Approved
0.817	Intermediate Similarity	NPD2935	Discontinued
0.8081	Intermediate Similarity	NPD8313	Approved
0.8081	Intermediate Similarity	NPD8312	Approved
0.8077	Intermediate Similarity	NPD3750	Approved
0.8077	Intermediate Similarity	NPD4628	Phase 3
0.8068	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2800	Approved
0.7989	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7961	Intermediate Similarity	NPD1613	Approved
0.7961	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3751	Discontinued
0.7935	Intermediate Similarity	NPD1551	Phase 2
0.7933	Intermediate Similarity	NPD4908	Phase 1
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7925	Intermediate Similarity	NPD7390	Discontinued
0.7901	Intermediate Similarity	NPD3226	Approved
0.7901	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD920	Approved
0.7875	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1247	Approved
0.7844	Intermediate Similarity	NPD919	Approved
0.7843	Intermediate Similarity	NPD943	Approved
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3787	Discontinued
0.7803	Intermediate Similarity	NPD5953	Discontinued
0.7791	Intermediate Similarity	NPD7286	Phase 2
0.7785	Intermediate Similarity	NPD1243	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4360	Phase 2
0.7778	Intermediate Similarity	NPD4363	Phase 3
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD2344	Approved
0.7765	Intermediate Similarity	NPD3926	Phase 2
0.7764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD6780	Approved
0.776	Intermediate Similarity	NPD6776	Approved
0.776	Intermediate Similarity	NPD6779	Approved
0.776	Intermediate Similarity	NPD6778	Approved
0.776	Intermediate Similarity	NPD6782	Approved
0.776	Intermediate Similarity	NPD6777	Approved
0.776	Intermediate Similarity	NPD6781	Approved
0.7756	Intermediate Similarity	NPD2799	Discontinued
0.7756	Intermediate Similarity	NPD3748	Approved
0.7753	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6651	Approved
0.7736	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD8151	Discontinued
0.7712	Intermediate Similarity	NPD2313	Discontinued
0.7711	Intermediate Similarity	NPD8455	Phase 2
0.7707	Intermediate Similarity	NPD6099	Approved
0.7707	Intermediate Similarity	NPD6100	Approved
0.7703	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7584	Approved
0.7697	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.764	Intermediate Similarity	NPD8150	Discontinued
0.7634	Intermediate Similarity	NPD7435	Discontinued
0.7632	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6798	Discontinued
0.7594	Intermediate Similarity	NPD7871	Phase 2
0.7594	Intermediate Similarity	NPD7870	Phase 2
0.7578	Intermediate Similarity	NPD2309	Approved
0.7576	Intermediate Similarity	NPD7458	Discontinued
0.7568	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD5124	Phase 1
0.7564	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD230	Phase 1
0.7545	Intermediate Similarity	NPD6844	Discontinued
0.754	Intermediate Similarity	NPD7697	Approved
0.754	Intermediate Similarity	NPD7696	Phase 3
0.754	Intermediate Similarity	NPD7698	Approved
0.7539	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7783	Phase 2
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD2424	Discontinued
0.7487	Intermediate Similarity	NPD6823	Phase 2
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6534	Approved
0.7486	Intermediate Similarity	NPD6535	Approved
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5404	Approved
0.7484	Intermediate Similarity	NPD5408	Approved
0.7484	Intermediate Similarity	NPD5406	Approved
0.7484	Intermediate Similarity	NPD5405	Approved
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7469	Intermediate Similarity	NPD6190	Approved
0.7468	Intermediate Similarity	NPD6832	Phase 2
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD447	Suspended
0.7452	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.744	Intermediate Similarity	NPD37	Approved
0.7436	Intermediate Similarity	NPD6233	Phase 2
0.7429	Intermediate Similarity	NPD7228	Approved
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.7412	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD1653	Approved
0.7401	Intermediate Similarity	NPD3823	Discontinued
0.7396	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7874	Approved
0.7394	Intermediate Similarity	NPD6273	Approved
0.7366	Intermediate Similarity	NPD7699	Phase 2
0.7366	Intermediate Similarity	NPD7700	Phase 2
0.7358	Intermediate Similarity	NPD7801	Approved
0.7351	Intermediate Similarity	NPD4361	Phase 2
0.7351	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1652	Phase 2
0.7346	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1933	Approved
0.7338	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4661	Approved
0.7333	Intermediate Similarity	NPD4662	Approved
0.733	Intermediate Similarity	NPD7177	Discontinued
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7312	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD9717	Approved
0.7301	Intermediate Similarity	NPD7003	Approved
0.7294	Intermediate Similarity	NPD5760	Phase 2
0.7294	Intermediate Similarity	NPD5761	Phase 2
0.7292	Intermediate Similarity	NPD7585	Approved
0.729	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD1470	Approved
0.7268	Intermediate Similarity	NPD4287	Approved
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7261	Intermediate Similarity	NPD3268	Approved
0.7261	Intermediate Similarity	NPD6410	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