NPASS Compound

Structure

CID286222 OpenBabel06191716092D 22 24 0 0 0 0 0 0 0 0999 V2000 2.0003 -2.4979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4534 -2.0775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4096 -2.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6792 -1.5021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8132 -0.0021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0677 -3.0880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8371 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3240 -0.3503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9338 -2.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3022 0.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7983 -1.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6113 -0.0921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7983 -2.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2020 0.0901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6330 -0.8856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0677 -1.0880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1581 -0.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9338 -1.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5886 -0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7998 -1.0880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9888 0.1490 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 13 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 15 20 2 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 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:	296.14
Volume:	319.426
LogP:	3.941
LogD:	3.335
LogS:	-4.119
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	4.114
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.877
MDCK Permeability:	1.6616846551187336e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.094
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.721

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	98.35548400878906%
Volume Distribution (VD):	0.686
Pgp-substrate:	1.4418656826019287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.627
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.927
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.436
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	12.583
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.276
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.723
Rat Oral Acute Toxicity:	0.555
Maximum Recommended Daily Dose:	0.837
Skin Sensitization:	0.814
Carcinogencity:	0.117
Eye Corrosion:	0.004
Eye Irritation:	0.698
Respiratory Toxicity:	0.128

Download Data

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

Natural Product: NPC286222

Natural Product ID:	NPC286222
*Common Name:**	Acerogenin E
IUPAC Name:	n.a.
Synonyms:	Acerogenin E
Standard InCHIKey:	HJJZJFOFYZSPGU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O3/c20-15-4-2-1-3-13-6-9-18(21)16(11-13)17-12-14(5-8-15)7-10-19(17)22/h6-7,9-12,21-22H,1-5,8H2
SMILES:	O=C1CCCCc2ccc(c(c3cc(CC1)ccc3O)c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517914
PubChem CID:	10402312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21550801]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13983	Acer maximowiczianum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	6

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	0.1	%	PMID[463108]
NPT2	Others	Unspecified	Inhibition	=	3.3	%	PMID[463108]
NPT2	Others	Unspecified	Inhibition	=	13.6	%	PMID[463108]
NPT2	Others	Unspecified	Inhibition	=	59.4	%	PMID[463108]
NPT2	Others	Unspecified	Inhibition	=	81.2	%	PMID[463108]
NPT2	Others	Unspecified	IC50	=	24000.0	nM	PMID[463108]
NPT2	Others	Unspecified	Activity	=	54.4	%	PMID[463109]

☑ 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 NPC286222 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	293
0.1-0.2	1507
0.2-0.3	3581
0.3-0.4	11594
0.4-0.5	7733
0.5-0.6	7140
0.6-0.7	8574
0.7-0.8	2049
0.8-0.85	180
0.85-0.9	33
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9369	High Similarity	NPC182240
0.9286	High Similarity	NPC473136
0.9231	High Similarity	NPC261573
0.9231	High Similarity	NPC288411
0.9231	High Similarity	NPC120693
0.9231	High Similarity	NPC8931
0.9151	High Similarity	NPC228737
0.9143	High Similarity	NPC138942
0.9135	High Similarity	NPC168829
0.9123	High Similarity	NPC31936
0.9057	High Similarity	NPC188677
0.8889	High Similarity	NPC262365
0.8889	High Similarity	NPC231767
0.8879	High Similarity	NPC176208
0.8879	High Similarity	NPC69332
0.8879	High Similarity	NPC95178
0.8879	High Similarity	NPC70843
0.8879	High Similarity	NPC29989
0.8814	High Similarity	NPC127975
0.8807	High Similarity	NPC88141
0.8793	High Similarity	NPC295034
0.8739	High Similarity	NPC228988
0.8727	High Similarity	NPC321252
0.8727	High Similarity	NPC252544
0.8727	High Similarity	NPC296683
0.8707	High Similarity	NPC32322
0.8707	High Similarity	NPC259703
0.8707	High Similarity	NPC164852
0.8707	High Similarity	NPC216216
0.8704	High Similarity	NPC54765
0.8673	High Similarity	NPC322197
0.8649	High Similarity	NPC177576
0.8649	High Similarity	NPC308689
0.8571	High Similarity	NPC260000
0.8559	High Similarity	NPC44732
0.8547	High Similarity	NPC241001
0.8545	High Similarity	NPC95344
0.8532	High Similarity	NPC271274
0.8496	Intermediate Similarity	NPC242136
0.8491	Intermediate Similarity	NPC280869
0.8487	Intermediate Similarity	NPC471187
0.8482	Intermediate Similarity	NPC95716
0.8476	Intermediate Similarity	NPC216520
0.8476	Intermediate Similarity	NPC82664
0.8476	Intermediate Similarity	NPC132271
0.8476	Intermediate Similarity	NPC292730
0.8475	Intermediate Similarity	NPC154696
0.8462	Intermediate Similarity	NPC128062
0.8462	Intermediate Similarity	NPC478121
0.8462	Intermediate Similarity	NPC151715
0.8455	Intermediate Similarity	NPC141523
0.8448	Intermediate Similarity	NPC328694
0.8443	Intermediate Similarity	NPC96024
0.8421	Intermediate Similarity	NPC473137
0.8421	Intermediate Similarity	NPC285350
0.8421	Intermediate Similarity	NPC12656
0.8411	Intermediate Similarity	NPC225506
0.8407	Intermediate Similarity	NPC46940
0.8403	Intermediate Similarity	NPC121168
0.8396	Intermediate Similarity	NPC77492
0.8393	Intermediate Similarity	NPC116842
0.8393	Intermediate Similarity	NPC21162
0.8381	Intermediate Similarity	NPC26244
0.8378	Intermediate Similarity	NPC68260
0.8378	Intermediate Similarity	NPC317305
0.8378	Intermediate Similarity	NPC279887
0.8376	Intermediate Similarity	NPC473767
0.8376	Intermediate Similarity	NPC79933
0.8376	Intermediate Similarity	NPC31296
0.8376	Intermediate Similarity	NPC258366
0.8376	Intermediate Similarity	NPC473974
0.8374	Intermediate Similarity	NPC276238
0.8365	Intermediate Similarity	NPC271440
0.8348	Intermediate Similarity	NPC23402
0.8333	Intermediate Similarity	NPC35344
0.8333	Intermediate Similarity	NPC198014
0.8333	Intermediate Similarity	NPC141003
0.8319	Intermediate Similarity	NPC162935
0.8319	Intermediate Similarity	NPC253627
0.8319	Intermediate Similarity	NPC249340
0.8318	Intermediate Similarity	NPC122005
0.8318	Intermediate Similarity	NPC252821
0.8318	Intermediate Similarity	NPC92730
0.8318	Intermediate Similarity	NPC245561
0.8305	Intermediate Similarity	NPC190501
0.8305	Intermediate Similarity	NPC318552
0.8304	Intermediate Similarity	NPC282855
0.8304	Intermediate Similarity	NPC58865
0.8304	Intermediate Similarity	NPC26013
0.8302	Intermediate Similarity	NPC473388
0.8291	Intermediate Similarity	NPC184527
0.8276	Intermediate Similarity	NPC299252
0.8276	Intermediate Similarity	NPC277394
0.8276	Intermediate Similarity	NPC61062
0.8273	Intermediate Similarity	NPC219286
0.8273	Intermediate Similarity	NPC99557
0.8269	Intermediate Similarity	NPC45040
0.8264	Intermediate Similarity	NPC164014
0.8264	Intermediate Similarity	NPC199273
0.8264	Intermediate Similarity	NPC181334
0.8257	Intermediate Similarity	NPC13426
0.8257	Intermediate Similarity	NPC68269
0.8257	Intermediate Similarity	NPC135784
0.825	Intermediate Similarity	NPC11250
0.8241	Intermediate Similarity	NPC52472
0.823	Intermediate Similarity	NPC208229
0.8224	Intermediate Similarity	NPC225464
0.8224	Intermediate Similarity	NPC201967
0.822	Intermediate Similarity	NPC42657
0.8214	Intermediate Similarity	NPC63698
0.8214	Intermediate Similarity	NPC61885
0.8214	Intermediate Similarity	NPC17525
0.8208	Intermediate Similarity	NPC274678
0.8208	Intermediate Similarity	NPC8392
0.8205	Intermediate Similarity	NPC299180
0.8197	Intermediate Similarity	NPC87985
0.8182	Intermediate Similarity	NPC273683
0.8174	Intermediate Similarity	NPC715
0.8167	Intermediate Similarity	NPC196976
0.8165	Intermediate Similarity	NPC51015
0.8165	Intermediate Similarity	NPC472585
0.8165	Intermediate Similarity	NPC12221
0.816	Intermediate Similarity	NPC245395
0.8158	Intermediate Similarity	NPC165770
0.8158	Intermediate Similarity	NPC4493
0.8158	Intermediate Similarity	NPC151537
0.8158	Intermediate Similarity	NPC476632
0.8158	Intermediate Similarity	NPC225679
0.8151	Intermediate Similarity	NPC34634
0.8151	Intermediate Similarity	NPC265454
0.8148	Intermediate Similarity	NPC128723
0.8148	Intermediate Similarity	NPC216468
0.8148	Intermediate Similarity	NPC78119
0.8148	Intermediate Similarity	NPC130193
0.8148	Intermediate Similarity	NPC51333
0.8148	Intermediate Similarity	NPC132078
0.8145	Intermediate Similarity	NPC48248
0.8142	Intermediate Similarity	NPC95172
0.8142	Intermediate Similarity	NPC314187
0.8136	Intermediate Similarity	NPC249435
0.8136	Intermediate Similarity	NPC273282
0.8136	Intermediate Similarity	NPC474890
0.8136	Intermediate Similarity	NPC161943
0.813	Intermediate Similarity	NPC71610
0.813	Intermediate Similarity	NPC267846
0.813	Intermediate Similarity	NPC254492
0.813	Intermediate Similarity	NPC62952
0.8125	Intermediate Similarity	NPC151477
0.8125	Intermediate Similarity	NPC152209
0.812	Intermediate Similarity	NPC19290
0.812	Intermediate Similarity	NPC28951
0.812	Intermediate Similarity	NPC325646
0.812	Intermediate Similarity	NPC471925
0.812	Intermediate Similarity	NPC471928
0.812	Intermediate Similarity	NPC471924
0.812	Intermediate Similarity	NPC477453
0.8113	Intermediate Similarity	NPC76938
0.8108	Intermediate Similarity	NPC243677
0.8108	Intermediate Similarity	NPC13495
0.8108	Intermediate Similarity	NPC303141
0.8108	Intermediate Similarity	NPC474839
0.8103	Intermediate Similarity	NPC195922
0.8103	Intermediate Similarity	NPC107240
0.8099	Intermediate Similarity	NPC282577
0.8095	Intermediate Similarity	NPC474517
0.8095	Intermediate Similarity	NPC72669
0.8095	Intermediate Similarity	NPC85342
0.8095	Intermediate Similarity	NPC244699
0.8095	Intermediate Similarity	NPC204210
0.8091	Intermediate Similarity	NPC470202
0.8091	Intermediate Similarity	NPC108497
0.8091	Intermediate Similarity	NPC233827
0.8087	Intermediate Similarity	NPC43525
0.8087	Intermediate Similarity	NPC228425
0.8083	Intermediate Similarity	NPC98305
0.8083	Intermediate Similarity	NPC474175
0.8083	Intermediate Similarity	NPC190971
0.8083	Intermediate Similarity	NPC131868
0.808	Intermediate Similarity	NPC474998
0.8073	Intermediate Similarity	NPC213730
0.807	Intermediate Similarity	NPC13482
0.807	Intermediate Similarity	NPC222905
0.8067	Intermediate Similarity	NPC188814
0.8067	Intermediate Similarity	NPC195262
0.8065	Intermediate Similarity	NPC100067
0.8065	Intermediate Similarity	NPC266689
0.8065	Intermediate Similarity	NPC30501
0.8065	Intermediate Similarity	NPC176130
0.8065	Intermediate Similarity	NPC84672
0.8065	Intermediate Similarity	NPC169250
0.8065	Intermediate Similarity	NPC162612
0.8065	Intermediate Similarity	NPC23126
0.8065	Intermediate Similarity	NPC105157
0.8065	Intermediate Similarity	NPC98254
0.8065	Intermediate Similarity	NPC72667
0.8065	Intermediate Similarity	NPC190043
0.8065	Intermediate Similarity	NPC78364
0.8065	Intermediate Similarity	NPC103356
0.8065	Intermediate Similarity	NPC116513
0.8065	Intermediate Similarity	NPC72158

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 NPC286222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	963
0.2-0.3	1139
0.3-0.4	2627
0.4-0.5	2181
0.5-0.6	1312
0.6-0.7	525
0.7-0.8	94
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8491	Intermediate Similarity	NPD3020	Approved
0.8381	Intermediate Similarity	NPD2859	Approved
0.8381	Intermediate Similarity	NPD2860	Approved
0.8305	Intermediate Similarity	NPD2932	Approved
0.8305	Intermediate Similarity	NPD3019	Approved
0.8286	Intermediate Similarity	NPD2933	Approved
0.8286	Intermediate Similarity	NPD2934	Approved
0.8197	Intermediate Similarity	NPD1164	Approved
0.8087	Intermediate Similarity	NPD7635	Approved
0.8067	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1809	Phase 2
0.8019	Intermediate Similarity	NPD845	Approved
0.8017	Intermediate Similarity	NPD1201	Approved
0.7965	Intermediate Similarity	NPD2342	Discontinued
0.7944	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1651	Approved
0.7826	Intermediate Similarity	NPD3021	Approved
0.7826	Intermediate Similarity	NPD3022	Approved
0.776	Intermediate Similarity	NPD1470	Approved
0.7748	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD844	Approved
0.768	Intermediate Similarity	NPD1283	Approved
0.7679	Intermediate Similarity	NPD940	Approved
0.7679	Intermediate Similarity	NPD846	Approved
0.7667	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD3026	Approved
0.7642	Intermediate Similarity	NPD3023	Approved
0.7636	Intermediate Similarity	NPD288	Approved
0.763	Intermediate Similarity	NPD3400	Discontinued
0.7623	Intermediate Similarity	NPD3025	Approved
0.7623	Intermediate Similarity	NPD3024	Approved
0.7594	Intermediate Similarity	NPD5408	Approved
0.7594	Intermediate Similarity	NPD2935	Discontinued
0.7594	Intermediate Similarity	NPD5404	Approved
0.7594	Intermediate Similarity	NPD5406	Approved
0.7594	Intermediate Similarity	NPD5405	Approved
0.7561	Intermediate Similarity	NPD4589	Approved
0.7541	Intermediate Similarity	NPD5304	Approved
0.7541	Intermediate Similarity	NPD5303	Approved
0.7519	Intermediate Similarity	NPD2799	Discontinued
0.748	Intermediate Similarity	NPD2797	Approved
0.7464	Intermediate Similarity	NPD7390	Discontinued
0.746	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1535	Discovery
0.744	Intermediate Similarity	NPD1281	Approved
0.7438	Intermediate Similarity	NPD256	Approved
0.7438	Intermediate Similarity	NPD255	Approved
0.7434	Intermediate Similarity	NPD1242	Phase 1
0.7429	Intermediate Similarity	NPD111	Approved
0.7422	Intermediate Similarity	NPD2798	Approved
0.7419	Intermediate Similarity	NPD2286	Discontinued
0.7417	Intermediate Similarity	NPD2229	Approved
0.7417	Intermediate Similarity	NPD2234	Approved
0.7417	Intermediate Similarity	NPD2228	Approved
0.7407	Intermediate Similarity	NPD2344	Approved
0.7405	Intermediate Similarity	NPD6663	Approved
0.7395	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1481	Phase 2
0.7373	Intermediate Similarity	NPD4750	Phase 3
0.7372	Intermediate Similarity	NPD7003	Approved
0.7364	Intermediate Similarity	NPD5736	Approved
0.735	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD943	Approved
0.7333	Intermediate Similarity	NPD4476	Approved
0.7333	Intermediate Similarity	NPD4477	Approved
0.7328	Intermediate Similarity	NPD2313	Discontinued
0.7328	Intermediate Similarity	NPD3764	Approved
0.7328	Intermediate Similarity	NPD3268	Approved
0.7323	Intermediate Similarity	NPD1755	Approved
0.7304	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD1929	Approved
0.7304	Intermediate Similarity	NPD1930	Approved
0.7293	Intermediate Similarity	NPD6355	Discontinued
0.7288	Intermediate Similarity	NPD9266	Approved
0.7288	Intermediate Similarity	NPD74	Approved
0.7286	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD3028	Approved
0.728	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1759	Phase 1
0.7258	Intermediate Similarity	NPD3091	Approved
0.7258	Intermediate Similarity	NPD1894	Discontinued
0.7244	Intermediate Similarity	NPD3972	Approved
0.7241	Intermediate Similarity	NPD1237	Approved
0.7236	Intermediate Similarity	NPD9568	Approved
0.7236	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3847	Discontinued
0.7218	Intermediate Similarity	NPD4060	Phase 1
0.7218	Intermediate Similarity	NPD1240	Approved
0.7218	Intermediate Similarity	NPD2979	Phase 3
0.7213	Intermediate Similarity	NPD5951	Approved
0.7213	Intermediate Similarity	NPD497	Approved
0.7203	Intermediate Similarity	NPD9264	Approved
0.7203	Intermediate Similarity	NPD9267	Approved
0.7203	Intermediate Similarity	NPD9263	Approved
0.72	Intermediate Similarity	NPD4093	Discontinued
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7194	Intermediate Similarity	NPD2309	Approved
0.7182	Intermediate Similarity	NPD1239	Approved
0.7177	Intermediate Similarity	NPD1758	Phase 1
0.7174	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6671	Approved
0.7153	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4059	Approved
0.7132	Intermediate Similarity	NPD1876	Approved
0.7132	Intermediate Similarity	NPD1510	Phase 2
0.7131	Intermediate Similarity	NPD498	Approved
0.7131	Intermediate Similarity	NPD496	Approved
0.7131	Intermediate Similarity	NPD495	Approved
0.7122	Intermediate Similarity	NPD3750	Approved
0.712	Intermediate Similarity	NPD7330	Discontinued
0.7111	Intermediate Similarity	NPD1607	Approved
0.7109	Intermediate Similarity	NPD1608	Approved
0.7099	Intermediate Similarity	NPD4208	Discontinued
0.7099	Intermediate Similarity	NPD2861	Phase 2
0.7097	Intermediate Similarity	NPD9493	Approved
0.7083	Intermediate Similarity	NPD1792	Phase 2
0.7073	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2066	Phase 3
0.7034	Intermediate Similarity	NPD4380	Phase 2
0.7031	Intermediate Similarity	NPD3092	Approved
0.7031	Intermediate Similarity	NPD1610	Phase 2
0.7029	Intermediate Similarity	NPD2346	Discontinued
0.7021	Intermediate Similarity	NPD3300	Phase 2
0.7009	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4625	Phase 3
0.6992	Remote Similarity	NPD1241	Discontinued
0.6984	Remote Similarity	NPD9545	Approved
0.6975	Remote Similarity	NPD1445	Approved
0.6975	Remote Similarity	NPD968	Approved
0.6975	Remote Similarity	NPD1444	Approved
0.6966	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD6099	Approved
0.6957	Remote Similarity	NPD6100	Approved
0.6949	Remote Similarity	NPD5909	Discontinued
0.6947	Remote Similarity	NPD3267	Approved
0.6947	Remote Similarity	NPD3094	Phase 2
0.6947	Remote Similarity	NPD3266	Approved
0.6947	Remote Similarity	NPD1203	Approved
0.6935	Remote Similarity	NPD2629	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1932	Approved
0.6917	Remote Similarity	NPD4908	Phase 1
0.6917	Remote Similarity	NPD2614	Approved
0.6917	Remote Similarity	NPD4207	Discontinued
0.6911	Remote Similarity	NPD5535	Approved
0.6906	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1611	Approved
0.6899	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD257	Approved
0.6894	Remote Similarity	NPD258	Approved
0.6892	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6233	Phase 2
0.6889	Remote Similarity	NPD6407	Approved
0.6889	Remote Similarity	NPD6405	Approved
0.6889	Remote Similarity	NPD8032	Phase 2
0.6884	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1751	Approved
0.6875	Remote Similarity	NPD3095	Discontinued
0.6875	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1566	Phase 3
0.687	Remote Similarity	NPD1565	Approved
0.687	Remote Similarity	NPD1564	Approved
0.6866	Remote Similarity	NPD7095	Approved
0.6864	Remote Similarity	NPD9261	Approved
0.6857	Remote Similarity	NPD1549	Phase 2
0.6855	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5283	Phase 1
0.685	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1548	Phase 1
0.6846	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1693	Approved
0.6835	Remote Similarity	NPD2438	Suspended
0.6835	Remote Similarity	NPD2531	Phase 2
0.6831	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7427	Discontinued
0.6822	Remote Similarity	NPD3143	Discontinued
0.6818	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9495	Approved
0.681	Remote Similarity	NPD9273	Approved
0.6807	Remote Similarity	NPD9610	Approved
0.6807	Remote Similarity	NPD9608	Approved
0.6803	Remote Similarity	NPD5451	Approved
0.68	Remote Similarity	NPD7768	Phase 2

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