NPASS Compound

Structure

CID290451 OpenBabel06191716102D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.2921 -1.3255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2950 -1.9857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7216 -0.9925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7173 -2.3193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0010 -1.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1524 -1.3277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1128 -1.7699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1482 0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 -2.3202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5744 -0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1133 -0.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1451 0.6611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5714 -0.3329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5790 -2.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7185 -0.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1470 -1.9866 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5778 -0.3336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5748 0.9938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0029 0.6602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1487 -1.2275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5765 1.7529 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 16 20 1 1 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.16
Volume:	322.063
LogP:	4.366
LogD:	3.564
LogS:	-5.619
# Rotatable Bonds:	0
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	4.622
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.842
MDCK Permeability:	1.911502840812318e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.923
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	98.15939331054688%
Volume Distribution (VD):	0.592
Pgp-substrate:	1.0872246026992798%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.535
CYP2C19-inhibitor:	0.931
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.679
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.263
CYP3A4-substrate:	0.503

ADMET: Excretion

Clearance (CL):	11.499
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.333
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.326
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.95
Carcinogencity:	0.466
Eye Corrosion:	0.011
Eye Irritation:	0.934
Respiratory Toxicity:	0.777

Download Data

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

Natural Product: NPC290451

Natural Product ID:	NPC290451
*Common Name:**	Acerogenin A
IUPAC Name:	n.a.
Synonyms:	Acerogenin A
Standard InCHIKey:	JHRMYLCWJWLUQL-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C19H22O3/c20-16-4-2-1-3-15-8-12-18(21)19(13-15)22-17-10-6-14(5-9-16)7-11-17/h6-8,10-13,16,20-21H,1-5,9H2/t16-/m1/s1
SMILES:	O[C@@H]1CCCCc2ccc(c(c2)Oc2ccc(CC1)cc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516665
PubChem CID:	12000158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003523] Meta,para-diphenylether diarylheptanoids

*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
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	Japan	n.a.	PMID[12542351]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21550801]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13983	Acer maximowiczianum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13983	Acer maximowiczianum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	7

Activity Type	# Activity
Individual Protein	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	92.7	%	PMID[569763]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	33.9	%	PMID[569763]
NPT2	Others	Unspecified		Inhibition	=	6.7	%	PMID[569762]
NPT2	Others	Unspecified		Inhibition	=	5.8	%	PMID[569762]
NPT2	Others	Unspecified		Inhibition	=	11.6	%	PMID[569762]
NPT2	Others	Unspecified		Inhibition	=	22.2	%	PMID[569762]
NPT2	Others	Unspecified		Inhibition	=	61.4	%	PMID[569762]
NPT2	Others	Unspecified		IC50	=	74000.0	nM	PMID[569762]

☑ 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 NPC290451 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	391
0.1-0.2	1683
0.2-0.3	5478
0.3-0.4	13566
0.4-0.5	4020
0.5-0.6	5237
0.6-0.7	8598
0.7-0.8	2835
0.8-0.85	585
0.85-0.9	261
0.9-0.95	40
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC127389
0.9569	High Similarity	NPC207613
0.9561	High Similarity	NPC86947
0.9496	High Similarity	NPC194519
0.9487	High Similarity	NPC470212
0.9487	High Similarity	NPC184651
0.9487	High Similarity	NPC54872
0.9487	High Similarity	NPC473853
0.9487	High Similarity	NPC113865
0.9487	High Similarity	NPC343720
0.9487	High Similarity	NPC262156
0.9487	High Similarity	NPC324571
0.9487	High Similarity	NPC312675
0.9417	High Similarity	NPC178284
0.9417	High Similarity	NPC191037
0.9417	High Similarity	NPC58607
0.9412	High Similarity	NPC293701
0.9412	High Similarity	NPC114901
0.9412	High Similarity	NPC48990
0.9391	High Similarity	NPC164386
0.9339	High Similarity	NPC163332
0.9339	High Similarity	NPC319625
0.9339	High Similarity	NPC292056
0.9339	High Similarity	NPC147821
0.9339	High Similarity	NPC183181
0.9339	High Similarity	NPC118787
0.9339	High Similarity	NPC111247
0.9339	High Similarity	NPC41706
0.9328	High Similarity	NPC471693
0.931	High Similarity	NPC470626
0.9262	High Similarity	NPC72529
0.925	High Similarity	NPC109822
0.925	High Similarity	NPC94276
0.9244	High Similarity	NPC71090
0.9244	High Similarity	NPC85488
0.9231	High Similarity	NPC24474
0.9231	High Similarity	NPC311595
0.9231	High Similarity	NPC310338
0.9231	High Similarity	NPC281298
0.9224	High Similarity	NPC293619
0.9187	High Similarity	NPC5851
0.9187	High Similarity	NPC86030
0.9174	High Similarity	NPC148627
0.9174	High Similarity	NPC87113
0.9167	High Similarity	NPC31344
0.9167	High Similarity	NPC317769
0.9167	High Similarity	NPC280704
0.9153	High Similarity	NPC227217
0.9153	High Similarity	NPC232316
0.9153	High Similarity	NPC95614
0.9153	High Similarity	NPC56214
0.9153	High Similarity	NPC242885
0.9153	High Similarity	NPC165133
0.9153	High Similarity	NPC117780
0.9145	High Similarity	NPC474214
0.912	High Similarity	NPC470752
0.9113	High Similarity	NPC472338
0.9106	High Similarity	NPC474178
0.9106	High Similarity	NPC252307
0.9106	High Similarity	NPC245826
0.9098	High Similarity	NPC17837
0.9098	High Similarity	NPC304630
0.9068	High Similarity	NPC474320
0.9048	High Similarity	NPC475840
0.904	High Similarity	NPC472597
0.904	High Similarity	NPC309787
0.9032	High Similarity	NPC475875
0.9024	High Similarity	NPC118533
0.9024	High Similarity	NPC165045
0.9016	High Similarity	NPC3221
0.9	High Similarity	NPC38996
0.9	High Similarity	NPC160380
0.8983	High Similarity	NPC474040
0.8976	High Similarity	NPC478085
0.8968	High Similarity	NPC184447
0.8968	High Similarity	NPC160991
0.8968	High Similarity	NPC16208
0.8968	High Similarity	NPC35932
0.8968	High Similarity	NPC7903
0.896	High Similarity	NPC257582
0.896	High Similarity	NPC242807
0.896	High Similarity	NPC42300
0.896	High Similarity	NPC187998
0.896	High Similarity	NPC64201
0.896	High Similarity	NPC153739
0.896	High Similarity	NPC77040
0.896	High Similarity	NPC241522
0.896	High Similarity	NPC174495
0.896	High Similarity	NPC92164
0.896	High Similarity	NPC145305
0.8957	High Similarity	NPC165646
0.8952	High Similarity	NPC206615
0.8952	High Similarity	NPC128208
0.8952	High Similarity	NPC98631
0.8952	High Similarity	NPC186843
0.8952	High Similarity	NPC45774
0.8952	High Similarity	NPC129570
0.8952	High Similarity	NPC11258
0.8952	High Similarity	NPC226661
0.8952	High Similarity	NPC21867
0.8952	High Similarity	NPC470213
0.8952	High Similarity	NPC184733
0.8952	High Similarity	NPC282703
0.8943	High Similarity	NPC134431
0.8943	High Similarity	NPC156854
0.8934	High Similarity	NPC228972
0.8934	High Similarity	NPC122792
0.8934	High Similarity	NPC74478
0.8889	High Similarity	NPC277804
0.888	High Similarity	NPC226788
0.888	High Similarity	NPC190629
0.888	High Similarity	NPC273295
0.888	High Similarity	NPC222004
0.888	High Similarity	NPC202582
0.888	High Similarity	NPC476968
0.888	High Similarity	NPC218856
0.888	High Similarity	NPC170844
0.888	High Similarity	NPC210623
0.888	High Similarity	NPC3439
0.888	High Similarity	NPC285339
0.888	High Similarity	NPC241354
0.888	High Similarity	NPC212015
0.888	High Similarity	NPC470258
0.8871	High Similarity	NPC474119
0.8871	High Similarity	NPC210355
0.8871	High Similarity	NPC5428
0.8871	High Similarity	NPC470699
0.887	High Similarity	NPC156840
0.887	High Similarity	NPC257124
0.887	High Similarity	NPC8547
0.887	High Similarity	NPC78918
0.887	High Similarity	NPC173746
0.887	High Similarity	NPC139617
0.887	High Similarity	NPC55300
0.886	High Similarity	NPC55617
0.886	High Similarity	NPC62258
0.8843	High Similarity	NPC470804
0.8843	High Similarity	NPC476343
0.8837	High Similarity	NPC263367
0.8837	High Similarity	NPC472334
0.8837	High Similarity	NPC177160
0.8837	High Similarity	NPC77861
0.8837	High Similarity	NPC302701
0.8837	High Similarity	NPC16435
0.8837	High Similarity	NPC209985
0.8837	High Similarity	NPC269091
0.8837	High Similarity	NPC477939
0.8837	High Similarity	NPC10737
0.8837	High Similarity	NPC54743
0.8837	High Similarity	NPC29799
0.8837	High Similarity	NPC306441
0.8837	High Similarity	NPC472336
0.8837	High Similarity	NPC156502
0.8828	High Similarity	NPC49603
0.8828	High Similarity	NPC310854
0.8828	High Similarity	NPC119060
0.8828	High Similarity	NPC476387
0.8828	High Similarity	NPC193026
0.8828	High Similarity	NPC170694
0.8828	High Similarity	NPC237594
0.8828	High Similarity	NPC187616
0.8828	High Similarity	NPC249791
0.8824	High Similarity	NPC255675
0.8819	High Similarity	NPC253105
0.8819	High Similarity	NPC201587
0.8814	High Similarity	NPC221049
0.881	High Similarity	NPC181079
0.881	High Similarity	NPC215941
0.881	High Similarity	NPC319282
0.881	High Similarity	NPC143483
0.881	High Similarity	NPC173308
0.881	High Similarity	NPC275724
0.881	High Similarity	NPC137427
0.881	High Similarity	NPC311419
0.881	High Similarity	NPC65935
0.881	High Similarity	NPC123196
0.881	High Similarity	NPC244246
0.88	High Similarity	NPC470084
0.88	High Similarity	NPC277458
0.88	High Similarity	NPC307050
0.879	High Similarity	NPC120225
0.879	High Similarity	NPC181361
0.879	High Similarity	NPC213552
0.8783	High Similarity	NPC226401
0.8783	High Similarity	NPC147634
0.8783	High Similarity	NPC120982
0.8783	High Similarity	NPC174096
0.8783	High Similarity	NPC79793
0.8783	High Similarity	NPC137685
0.877	High Similarity	NPC41562
0.8769	High Similarity	NPC474390
0.876	High Similarity	NPC112246
0.876	High Similarity	NPC61946
0.876	High Similarity	NPC214729
0.876	High Similarity	NPC234333
0.876	High Similarity	NPC121812
0.876	High Similarity	NPC112939
0.876	High Similarity	NPC472337
0.876	High Similarity	NPC260898
0.876	High Similarity	NPC470356

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 NPC290451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	965
0.2-0.3	1700
0.3-0.4	2674
0.4-0.5	1676
0.5-0.6	945
0.6-0.7	685
0.7-0.8	147
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.888	High Similarity	NPD3027	Phase 3
0.887	High Similarity	NPD228	Approved
0.8672	High Similarity	NPD1613	Approved
0.8672	High Similarity	NPD1612	Clinical (unspecified phase)
0.8609	High Similarity	NPD2684	Approved
0.8559	High Similarity	NPD5283	Phase 1
0.84	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3620	Phase 2
0.8359	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8319	Intermediate Similarity	NPD7843	Approved
0.8281	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD7157	Approved
0.8226	Intermediate Similarity	NPD5846	Approved
0.8226	Intermediate Similarity	NPD6516	Phase 2
0.822	Intermediate Similarity	NPD3022	Approved
0.822	Intermediate Similarity	NPD3021	Approved
0.8145	Intermediate Similarity	NPD1357	Approved
0.814	Intermediate Similarity	NPD2861	Phase 2
0.812	Intermediate Similarity	NPD968	Approved
0.8106	Intermediate Similarity	NPD4060	Phase 1
0.8106	Intermediate Similarity	NPD1558	Phase 1
0.8062	Intermediate Similarity	NPD6584	Phase 3
0.8051	Intermediate Similarity	NPD290	Approved
0.7967	Intermediate Similarity	NPD6671	Approved
0.7939	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD4162	Approved
0.7891	Intermediate Similarity	NPD2235	Phase 2
0.7891	Intermediate Similarity	NPD2231	Phase 2
0.7842	Intermediate Similarity	NPD6331	Phase 2
0.784	Intermediate Similarity	NPD5536	Phase 2
0.7829	Intermediate Similarity	NPD6582	Phase 2
0.7829	Intermediate Similarity	NPD6583	Phase 3
0.7812	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.7778	Intermediate Similarity	NPD291	Approved
0.7778	Intermediate Similarity	NPD5735	Approved
0.777	Intermediate Similarity	NPD3060	Approved
0.7761	Intermediate Similarity	NPD2674	Phase 3
0.7744	Intermediate Similarity	NPD7095	Approved
0.7714	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4110	Phase 3
0.7704	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6798	Discontinued
0.7681	Intermediate Similarity	NPD2161	Phase 2
0.7669	Intermediate Similarity	NPD4908	Phase 1
0.7664	Intermediate Similarity	NPD4536	Approved
0.7664	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4538	Approved
0.7652	Intermediate Similarity	NPD2859	Approved
0.7652	Intermediate Similarity	NPD2860	Approved
0.7647	Intermediate Similarity	NPD6355	Discontinued
0.763	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1934	Approved
0.7609	Intermediate Similarity	NPD5588	Approved
0.7609	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5960	Phase 3
0.7609	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3020	Approved
0.7594	Intermediate Similarity	NPD9494	Approved
0.7581	Intermediate Similarity	NPD5535	Approved
0.7581	Intermediate Similarity	NPD821	Approved
0.7574	Intermediate Similarity	NPD4140	Approved
0.7565	Intermediate Similarity	NPD2934	Approved
0.7565	Intermediate Similarity	NPD9296	Approved
0.7565	Intermediate Similarity	NPD2933	Approved
0.7557	Intermediate Similarity	NPD2983	Phase 2
0.7557	Intermediate Similarity	NPD5327	Phase 3
0.7557	Intermediate Similarity	NPD2982	Phase 2
0.7556	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3145	Approved
0.7556	Intermediate Similarity	NPD3144	Approved
0.7538	Intermediate Similarity	NPD1091	Approved
0.7538	Intermediate Similarity	NPD3705	Approved
0.7535	Intermediate Similarity	NPD5241	Discontinued
0.7518	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5177	Phase 3
0.7518	Intermediate Similarity	NPD6674	Discontinued
0.7518	Intermediate Similarity	NPD4236	Phase 3
0.7518	Intermediate Similarity	NPD4237	Approved
0.75	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1894	Discontinued
0.75	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD1182	Approved
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD4062	Phase 3
0.7481	Intermediate Similarity	NPD2981	Phase 2
0.748	Intermediate Similarity	NPD3596	Phase 2
0.748	Intermediate Similarity	NPD5451	Approved
0.7466	Intermediate Similarity	NPD1653	Approved
0.7465	Intermediate Similarity	NPD4628	Phase 3
0.7465	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3018	Phase 2
0.7456	Intermediate Similarity	NPD9365	Approved
0.745	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5110	Phase 2
0.7426	Intermediate Similarity	NPD5111	Phase 2
0.7426	Intermediate Similarity	NPD5109	Approved
0.7424	Intermediate Similarity	NPD3685	Discontinued
0.7379	Intermediate Similarity	NPD4123	Phase 3
0.7379	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5762	Approved
0.7376	Intermediate Similarity	NPD5763	Approved
0.7364	Intermediate Similarity	NPD6581	Approved
0.7364	Intermediate Similarity	NPD6580	Approved
0.7357	Intermediate Similarity	NPD2154	Approved
0.7357	Intermediate Similarity	NPD2155	Approved
0.7357	Intermediate Similarity	NPD2156	Approved
0.7355	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6166	Phase 2
0.7353	Intermediate Similarity	NPD4625	Phase 3
0.7351	Intermediate Similarity	NPD3882	Suspended
0.7351	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1840	Phase 2
0.7343	Intermediate Similarity	NPD4535	Phase 3
0.7338	Intermediate Similarity	NPD6353	Approved
0.7338	Intermediate Similarity	NPD3052	Approved
0.7338	Intermediate Similarity	NPD3054	Approved
0.7338	Intermediate Similarity	NPD6653	Approved
0.7333	Intermediate Similarity	NPD2801	Approved
0.7333	Intermediate Similarity	NPD2978	Approved
0.7333	Intermediate Similarity	NPD2977	Approved
0.7329	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7526	Approved
0.7329	Intermediate Similarity	NPD52	Approved
0.7328	Intermediate Similarity	NPD3496	Discontinued
0.7324	Intermediate Similarity	NPD5958	Discontinued
0.7324	Intermediate Similarity	NPD7037	Approved
0.7324	Intermediate Similarity	NPD4534	Discontinued
0.7324	Intermediate Similarity	NPD7153	Discontinued
0.7319	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1818	Approved
0.7313	Intermediate Similarity	NPD1817	Approved
0.7313	Intermediate Similarity	NPD1820	Approved
0.7313	Intermediate Similarity	NPD1819	Approved
0.731	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5585	Approved
0.7305	Intermediate Similarity	NPD6032	Approved
0.7299	Intermediate Similarity	NPD5718	Phase 2
0.7299	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4749	Approved
0.7292	Intermediate Similarity	NPD2677	Approved
0.7273	Intermediate Similarity	NPD3092	Approved
0.7273	Intermediate Similarity	NPD1535	Discovery
0.7266	Intermediate Similarity	NPD2557	Approved
0.7266	Intermediate Similarity	NPD3657	Discovery
0.7266	Intermediate Similarity	NPD4340	Discontinued
0.7261	Intermediate Similarity	NPD3818	Discontinued
0.7259	Intermediate Similarity	NPD3691	Phase 2
0.7259	Intermediate Similarity	NPD3690	Phase 2
0.7254	Intermediate Similarity	NPD1375	Discontinued
0.7252	Intermediate Similarity	NPD9384	Approved
0.7252	Intermediate Similarity	NPD2668	Approved
0.7252	Intermediate Similarity	NPD4626	Approved
0.7252	Intermediate Similarity	NPD9381	Approved
0.7252	Intermediate Similarity	NPD2667	Approved
0.7246	Intermediate Similarity	NPD3531	Approved
0.7246	Intermediate Similarity	NPD3532	Approved
0.7246	Intermediate Similarity	NPD3530	Approved
0.7244	Intermediate Similarity	NPD2489	Approved
0.7244	Intermediate Similarity	NPD27	Approved
0.7241	Intermediate Similarity	NPD5058	Phase 3
0.7239	Intermediate Similarity	NPD2922	Phase 1
0.7231	Intermediate Similarity	NPD3091	Approved
0.723	Intermediate Similarity	NPD3686	Approved
0.723	Intermediate Similarity	NPD3687	Approved
0.7226	Intermediate Similarity	NPD3166	Approved
0.7226	Intermediate Similarity	NPD3165	Approved
0.7226	Intermediate Similarity	NPD6179	Discontinued
0.7226	Intermediate Similarity	NPD3164	Approved
0.7226	Intermediate Similarity	NPD3167	Approved
0.7218	Intermediate Similarity	NPD1481	Phase 2
0.7218	Intermediate Similarity	NPD2230	Approved
0.7218	Intermediate Similarity	NPD2232	Approved
0.7218	Intermediate Similarity	NPD1608	Approved
0.7218	Intermediate Similarity	NPD2233	Approved
0.7203	Intermediate Similarity	NPD2424	Discontinued
0.72	Intermediate Similarity	NPD556	Approved
0.7197	Intermediate Similarity	NPD3847	Discontinued
0.7194	Intermediate Similarity	NPD2238	Phase 2
0.7194	Intermediate Similarity	NPD3059	Approved
0.7194	Intermediate Similarity	NPD3062	Approved
0.7194	Intermediate Similarity	NPD3061	Approved
0.7192	Intermediate Similarity	NPD1511	Approved
0.719	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7833	Phase 2
0.719	Intermediate Similarity	NPD7831	Phase 2
0.7177	Intermediate Similarity	NPD1358	Approved
0.7176	Intermediate Similarity	NPD3443	Approved
0.7176	Intermediate Similarity	NPD3444	Approved
0.7176	Intermediate Similarity	NPD3445	Approved
0.7176	Intermediate Similarity	NPD1651	Approved
0.7176	Intermediate Similarity	NPD5691	Approved
0.7174	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6190	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