NPASS Compound

Structure

CID262365 OpenBabel06191716062D 22 24 0 0 1 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 3 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 1 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:	298.16
Volume:	322.063
LogP:	4.365
LogD:	3.527
LogS:	-3.923
# Rotatable Bonds:	0
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	4.521
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:	-4.722
MDCK Permeability:	1.961101224878803e-05
Pgp-inhibitor:	0.313
Pgp-substrate:	0.335
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	98.03638458251953%
Volume Distribution (VD):	0.798
Pgp-substrate:	1.5604734420776367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.843
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.296
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	12.443
Half-life (T1/2):	0.506

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.619
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.951
Carcinogencity:	0.074
Eye Corrosion:	0.007
Eye Irritation:	0.875
Respiratory Toxicity:	0.187

Download Data

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

Natural Product: NPC262365

Natural Product ID:	NPC262365
*Common Name:**	Acerogenin K
IUPAC Name:	n.a.
Synonyms:	Acerogenin K
Standard InCHIKey:	OUMFOFAOVINTGW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22O3/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/h6-7,9-12,15,20-22H,1-5,8H2
SMILES:	OC1CCCCc2ccc(c(c3cc(CC1)ccc3O)c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462921
PubChem CID:	9994854
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]
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	5

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	6.6	%	PMID[550639]
NPT2	Others	Unspecified	Inhibition	=	2.1	%	PMID[550639]
NPT2	Others	Unspecified	Inhibition	=	24.3	%	PMID[550639]
NPT2	Others	Unspecified	Inhibition	=	56.6	%	PMID[550639]
NPT2	Others	Unspecified	Inhibition	=	91.3	%	PMID[550639]
NPT2	Others	Unspecified	IC50	=	25000.0	nM	PMID[550639]

☑ 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 NPC262365 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	280
0.1-0.2	1511
0.2-0.3	4060
0.3-0.4	12774
0.4-0.5	6729
0.5-0.6	8816
0.6-0.7	6512
0.7-0.8	1711
0.8-0.85	208
0.85-0.9	72
0.9-0.95	19
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC308689
0.9612	High Similarity	NPC44732
0.96	High Similarity	NPC288411
0.9505	High Similarity	NPC138942
0.95	High Similarity	NPC168829
0.9434	High Similarity	NPC473137
0.9434	High Similarity	NPC12656
0.92	High Similarity	NPC216468
0.92	High Similarity	NPC78119
0.92	High Similarity	NPC51333
0.92	High Similarity	NPC132078
0.9109	High Similarity	NPC213730
0.9065	High Similarity	NPC228425
0.9065	High Similarity	NPC228988
0.9057	High Similarity	NPC296683
0.9038	High Similarity	NPC54765
0.902	High Similarity	NPC40258
0.902	High Similarity	NPC91461
0.902	High Similarity	NPC7686
0.901	High Similarity	NPC128723
0.9009	High Similarity	NPC182240
0.8929	High Similarity	NPC473136
0.8922	High Similarity	NPC294741
0.8889	High Similarity	NPC286222
0.8868	High Similarity	NPC95344
0.8857	High Similarity	NPC271274
0.8846	High Similarity	NPC323810
0.8812	High Similarity	NPC292730
0.8812	High Similarity	NPC82664
0.8812	High Similarity	NPC132271
0.8812	High Similarity	NPC216520
0.8807	High Similarity	NPC35344
0.8807	High Similarity	NPC141003
0.88	High Similarity	NPC128062
0.88	High Similarity	NPC151715
0.8796	High Similarity	NPC95716
0.8772	High Similarity	NPC31936
0.8762	High Similarity	NPC233396
0.8762	High Similarity	NPC154899
0.8739	High Similarity	NPC308828
0.8738	High Similarity	NPC225506
0.8725	High Similarity	NPC77492
0.8716	High Similarity	NPC46940
0.8713	High Similarity	NPC26244
0.8704	High Similarity	NPC475018
0.8704	High Similarity	NPC132720
0.87	High Similarity	NPC271440
0.8679	High Similarity	NPC135464
0.8679	High Similarity	NPC92623
0.8673	High Similarity	NPC151197
0.8661	High Similarity	NPC477136
0.8649	High Similarity	NPC147179
0.8641	High Similarity	NPC252821
0.8641	High Similarity	NPC92730
0.8641	High Similarity	NPC122005
0.8627	High Similarity	NPC473388
0.8611	High Similarity	NPC58865
0.8611	High Similarity	NPC55617
0.8611	High Similarity	NPC62258
0.86	High Similarity	NPC45040
0.8596	High Similarity	NPC223451
0.8585	High Similarity	NPC99557
0.8585	High Similarity	NPC219286
0.8584	High Similarity	NPC469609
0.8571	High Similarity	NPC308311
0.8571	High Similarity	NPC469663
0.8571	High Similarity	NPC219112
0.8571	High Similarity	NPC477137
0.8571	High Similarity	NPC38893
0.8571	High Similarity	NPC92
0.8559	High Similarity	NPC268160
0.8547	High Similarity	NPC231767
0.8544	High Similarity	NPC474073
0.8544	High Similarity	NPC225464
0.8532	High Similarity	NPC226401
0.8532	High Similarity	NPC79793
0.8532	High Similarity	NPC147634
0.8532	High Similarity	NPC174096
0.8532	High Similarity	NPC120982
0.8529	High Similarity	NPC274678
0.8529	High Similarity	NPC8392
0.8519	High Similarity	NPC63698
0.8519	High Similarity	NPC61885
0.8515	High Similarity	NPC325292
0.8515	High Similarity	NPC138117
0.8509	High Similarity	NPC469644
0.85	High Similarity	NPC300017
0.8496	Intermediate Similarity	NPC299180
0.8491	Intermediate Similarity	NPC475225
0.8482	Intermediate Similarity	NPC35797
0.8482	Intermediate Similarity	NPC474486
0.8482	Intermediate Similarity	NPC192948
0.8476	Intermediate Similarity	NPC51015
0.8476	Intermediate Similarity	NPC12221
0.8475	Intermediate Similarity	NPC127975
0.8468	Intermediate Similarity	NPC715
0.8455	Intermediate Similarity	NPC476632
0.8455	Intermediate Similarity	NPC187583
0.8455	Intermediate Similarity	NPC225679
0.8455	Intermediate Similarity	NPC165770
0.8455	Intermediate Similarity	NPC4493
0.8455	Intermediate Similarity	NPC151537
0.8455	Intermediate Similarity	NPC257430
0.8455	Intermediate Similarity	NPC179002
0.844	Intermediate Similarity	NPC314187
0.8431	Intermediate Similarity	NPC76938
0.8426	Intermediate Similarity	NPC151477
0.8421	Intermediate Similarity	NPC471671
0.8416	Intermediate Similarity	NPC204210
0.8411	Intermediate Similarity	NPC474839
0.8407	Intermediate Similarity	NPC474358
0.8407	Intermediate Similarity	NPC154511
0.8407	Intermediate Similarity	NPC247858
0.8407	Intermediate Similarity	NPC474387
0.8407	Intermediate Similarity	NPC257540
0.8407	Intermediate Similarity	NPC137496
0.8396	Intermediate Similarity	NPC108497
0.8396	Intermediate Similarity	NPC233827
0.8396	Intermediate Similarity	NPC235762
0.8396	Intermediate Similarity	NPC471228
0.8393	Intermediate Similarity	NPC195922
0.8393	Intermediate Similarity	NPC120280
0.8393	Intermediate Similarity	NPC107240
0.8381	Intermediate Similarity	NPC174911
0.8378	Intermediate Similarity	NPC302371
0.8378	Intermediate Similarity	NPC43525
0.8365	Intermediate Similarity	NPC32674
0.8365	Intermediate Similarity	NPC156313
0.8364	Intermediate Similarity	NPC252544
0.8364	Intermediate Similarity	NPC321252
0.8364	Intermediate Similarity	NPC13482
0.8364	Intermediate Similarity	NPC63345
0.8362	Intermediate Similarity	NPC131868
0.835	Intermediate Similarity	NPC313650
0.835	Intermediate Similarity	NPC144682
0.835	Intermediate Similarity	NPC32714
0.8349	Intermediate Similarity	NPC11554
0.8333	Intermediate Similarity	NPC248904
0.8333	Intermediate Similarity	NPC172219
0.8333	Intermediate Similarity	NPC476266
0.8333	Intermediate Similarity	NPC304510
0.8319	Intermediate Similarity	NPC81641
0.8318	Intermediate Similarity	NPC238696
0.8318	Intermediate Similarity	NPC119860
0.8304	Intermediate Similarity	NPC261343
0.8304	Intermediate Similarity	NPC322239
0.8304	Intermediate Similarity	NPC176730
0.8304	Intermediate Similarity	NPC117846
0.8304	Intermediate Similarity	NPC123175
0.8302	Intermediate Similarity	NPC101025
0.8302	Intermediate Similarity	NPC471578
0.83	Intermediate Similarity	NPC104216
0.8291	Intermediate Similarity	NPC295034
0.8291	Intermediate Similarity	NPC251259
0.8288	Intermediate Similarity	NPC177576
0.8276	Intermediate Similarity	NPC260832
0.8276	Intermediate Similarity	NPC475245
0.8276	Intermediate Similarity	NPC135467
0.8273	Intermediate Similarity	NPC265211
0.8273	Intermediate Similarity	NPC306045
0.8261	Intermediate Similarity	NPC154030
0.8257	Intermediate Similarity	NPC66834
0.8257	Intermediate Similarity	NPC320439
0.8252	Intermediate Similarity	NPC289769
0.8252	Intermediate Similarity	NPC27323
0.8252	Intermediate Similarity	NPC152415
0.8252	Intermediate Similarity	NPC316301
0.8246	Intermediate Similarity	NPC261973
0.8241	Intermediate Similarity	NPC117115
0.8235	Intermediate Similarity	NPC304541
0.8224	Intermediate Similarity	NPC168393
0.8224	Intermediate Similarity	NPC269212
0.822	Intermediate Similarity	NPC150026
0.822	Intermediate Similarity	NPC71094
0.8218	Intermediate Similarity	NPC70436
0.8218	Intermediate Similarity	NPC242240
0.8218	Intermediate Similarity	NPC318325
0.8218	Intermediate Similarity	NPC280347
0.8218	Intermediate Similarity	NPC177420
0.8218	Intermediate Similarity	NPC123273
0.8214	Intermediate Similarity	NPC42911
0.8214	Intermediate Similarity	NPC153795
0.8214	Intermediate Similarity	NPC250323
0.8214	Intermediate Similarity	NPC290353
0.8208	Intermediate Similarity	NPC129373
0.8208	Intermediate Similarity	NPC48730
0.8208	Intermediate Similarity	NPC130103
0.8208	Intermediate Similarity	NPC248396
0.8205	Intermediate Similarity	NPC129176
0.8205	Intermediate Similarity	NPC216216
0.8198	Intermediate Similarity	NPC141782
0.819	Intermediate Similarity	NPC152097
0.8182	Intermediate Similarity	NPC201959
0.8182	Intermediate Similarity	NPC233835
0.8174	Intermediate Similarity	NPC470760
0.8165	Intermediate Similarity	NPC67250
0.8165	Intermediate Similarity	NPC113457
0.8165	Intermediate Similarity	NPC21594
0.8148	Intermediate Similarity	NPC254965
0.8148	Intermediate Similarity	NPC261573

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 NPC262365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	956
0.2-0.3	1261
0.3-0.4	2837
0.4-0.5	1953
0.5-0.6	1215
0.6-0.7	525
0.7-0.8	96
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD3020	Approved
0.8713	High Similarity	NPD2860	Approved
0.8713	High Similarity	NPD2859	Approved
0.8614	High Similarity	NPD2934	Approved
0.8614	High Similarity	NPD2933	Approved
0.8378	Intermediate Similarity	NPD7635	Approved
0.835	Intermediate Similarity	NPD1809	Phase 2
0.8333	Intermediate Similarity	NPD845	Approved
0.8257	Intermediate Similarity	NPD2342	Discontinued
0.8252	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD3022	Approved
0.8108	Intermediate Similarity	NPD3021	Approved
0.8103	Intermediate Similarity	NPD3091	Approved
0.8037	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD844	Approved
0.7982	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD940	Approved
0.7963	Intermediate Similarity	NPD846	Approved
0.7925	Intermediate Similarity	NPD288	Approved
0.789	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD3092	Approved
0.7815	Intermediate Similarity	NPD4589	Approved
0.7797	Intermediate Similarity	NPD5304	Approved
0.7797	Intermediate Similarity	NPD5303	Approved
0.7742	Intermediate Similarity	NPD2861	Phase 2
0.7724	Intermediate Similarity	NPD3094	Phase 2
0.7723	Intermediate Similarity	NPD111	Approved
0.7706	Intermediate Similarity	NPD1242	Phase 1
0.7672	Intermediate Similarity	NPD2234	Approved
0.7672	Intermediate Similarity	NPD2229	Approved
0.7672	Intermediate Similarity	NPD2228	Approved
0.7672	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3095	Discontinued
0.7667	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2286	Discontinued
0.7638	Intermediate Similarity	NPD6407	Approved
0.7638	Intermediate Similarity	NPD6405	Approved
0.7632	Intermediate Similarity	NPD4750	Phase 3
0.7559	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3028	Approved
0.7541	Intermediate Similarity	NPD1610	Phase 2
0.7522	Intermediate Similarity	NPD968	Approved
0.7479	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3400	Discontinued
0.7458	Intermediate Similarity	NPD497	Approved
0.7442	Intermediate Similarity	NPD4060	Phase 1
0.744	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4103	Phase 2
0.744	Intermediate Similarity	NPD1164	Approved
0.7438	Intermediate Similarity	NPD4093	Discontinued
0.7419	Intermediate Similarity	NPD4659	Approved
0.7402	Intermediate Similarity	NPD4908	Phase 1
0.7398	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6671	Approved
0.7391	Intermediate Similarity	NPD2684	Approved
0.7377	Intermediate Similarity	NPD4626	Approved
0.7377	Intermediate Similarity	NPD3019	Approved
0.7377	Intermediate Similarity	NPD2932	Approved
0.7377	Intermediate Similarity	NPD4059	Approved
0.7373	Intermediate Similarity	NPD495	Approved
0.7373	Intermediate Similarity	NPD498	Approved
0.7373	Intermediate Similarity	NPD496	Approved
0.7355	Intermediate Similarity	NPD7330	Discontinued
0.7355	Intermediate Similarity	NPD1548	Phase 1
0.7344	Intermediate Similarity	NPD3027	Phase 3
0.7339	Intermediate Similarity	NPD2562	Approved
0.7339	Intermediate Similarity	NPD2561	Approved
0.7328	Intermediate Similarity	NPD1792	Phase 2
0.7323	Intermediate Similarity	NPD5736	Approved
0.7311	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1134	Approved
0.7302	Intermediate Similarity	NPD1129	Approved
0.7302	Intermediate Similarity	NPD1131	Approved
0.7302	Intermediate Similarity	NPD1135	Approved
0.7302	Intermediate Similarity	NPD1133	Approved
0.7273	Intermediate Similarity	NPD3554	Approved
0.7273	Intermediate Similarity	NPD3555	Approved
0.7273	Intermediate Similarity	NPD3552	Approved
0.7273	Intermediate Similarity	NPD3553	Approved
0.725	Intermediate Similarity	NPD7157	Approved
0.7227	Intermediate Similarity	NPD5283	Phase 1
0.7217	Intermediate Similarity	NPD1444	Approved
0.7217	Intermediate Similarity	NPD1445	Approved
0.7209	Intermediate Similarity	NPD4625	Phase 3
0.7179	Intermediate Similarity	NPD5451	Approved
0.7176	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1613	Approved
0.7167	Intermediate Similarity	NPD9618	Approved
0.7167	Intermediate Similarity	NPD9614	Approved
0.7155	Intermediate Similarity	NPD290	Approved
0.7154	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1651	Approved
0.7154	Intermediate Similarity	NPD5691	Approved
0.7154	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1669	Approved
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7132	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD16	Approved
0.7131	Intermediate Similarity	NPD856	Approved
0.712	Intermediate Similarity	NPD1201	Approved
0.7111	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3690	Phase 2
0.7109	Intermediate Similarity	NPD6584	Phase 3
0.7109	Intermediate Similarity	NPD3691	Phase 2
0.71	Intermediate Similarity	NPD9294	Approved
0.7099	Intermediate Similarity	NPD6663	Approved
0.7097	Intermediate Similarity	NPD1751	Approved
0.7097	Intermediate Similarity	NPD2667	Approved
0.7097	Intermediate Similarity	NPD9381	Approved
0.7097	Intermediate Similarity	NPD5846	Approved
0.7097	Intermediate Similarity	NPD2668	Approved
0.7097	Intermediate Similarity	NPD9384	Approved
0.7097	Intermediate Similarity	NPD6516	Phase 2
0.7087	Intermediate Similarity	NPD8651	Approved
0.7087	Intermediate Similarity	NPD1283	Approved
0.7073	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2235	Phase 2
0.7063	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD2233	Approved
0.7063	Intermediate Similarity	NPD2230	Approved
0.7063	Intermediate Similarity	NPD2231	Phase 2
0.7059	Intermediate Similarity	NPD228	Approved
0.7054	Intermediate Similarity	NPD4208	Discontinued
0.7054	Intermediate Similarity	NPD9273	Approved
0.7045	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3061	Approved
0.7045	Intermediate Similarity	NPD3062	Approved
0.7045	Intermediate Similarity	NPD3059	Approved
0.7045	Intermediate Similarity	NPD2238	Phase 2
0.7045	Intermediate Similarity	NPD3620	Phase 2
0.7043	Intermediate Similarity	NPD9608	Approved
0.7043	Intermediate Similarity	NPD9610	Approved
0.704	Intermediate Similarity	NPD3143	Discontinued
0.704	Intermediate Similarity	NPD3421	Phase 3
0.7037	Intermediate Similarity	NPD2935	Discontinued
0.7031	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4538	Approved
0.7015	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4536	Approved
0.6992	Remote Similarity	NPD317	Approved
0.6992	Remote Similarity	NPD9616	Approved
0.6992	Remote Similarity	NPD9613	Approved
0.6992	Remote Similarity	NPD9615	Approved
0.6992	Remote Similarity	NPD6355	Discontinued
0.6992	Remote Similarity	NPD318	Approved
0.6977	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6387	Discontinued
0.6967	Remote Similarity	NPD709	Approved
0.6963	Remote Similarity	NPD5960	Phase 3
0.6963	Remote Similarity	NPD5588	Approved
0.6963	Remote Similarity	NPD7742	Approved
0.6963	Remote Similarity	NPD7743	Approved
0.6957	Remote Similarity	NPD9500	Approved
0.694	Remote Similarity	NPD2568	Approved
0.694	Remote Similarity	NPD4097	Suspended
0.694	Remote Similarity	NPD5314	Approved
0.6935	Remote Similarity	NPD316	Approved
0.6929	Remote Similarity	NPD3070	Discontinued
0.6929	Remote Similarity	NPD7041	Phase 2
0.6929	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4140	Approved
0.6912	Remote Similarity	NPD4477	Approved
0.6912	Remote Similarity	NPD4476	Approved
0.6912	Remote Similarity	NPD5408	Approved
0.6912	Remote Similarity	NPD5406	Approved
0.6912	Remote Similarity	NPD5405	Approved
0.6912	Remote Similarity	NPD5404	Approved
0.6911	Remote Similarity	NPD7636	Approved
0.6905	Remote Similarity	NPD3847	Discontinued
0.6905	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1470	Approved
0.6897	Remote Similarity	NPD1237	Approved
0.6894	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6798	Discontinued
0.688	Remote Similarity	NPD3445	Approved
0.688	Remote Similarity	NPD3443	Approved
0.688	Remote Similarity	NPD3444	Approved
0.6875	Remote Similarity	NPD5327	Phase 3
0.6875	Remote Similarity	NPD9622	Approved
0.687	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5735	Approved
0.6864	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD9088	Approved
0.686	Remote Similarity	NPD9379	Approved
0.686	Remote Similarity	NPD5535	Approved
0.686	Remote Similarity	NPD1138	Approved
0.686	Remote Similarity	NPD821	Approved
0.686	Remote Similarity	NPD9377	Approved
0.6857	Remote Similarity	NPD6666	Approved
0.6857	Remote Similarity	NPD6667	Approved
0.685	Remote Similarity	NPD1091	Approved
0.685	Remote Similarity	NPD1281	Approved
0.685	Remote Similarity	NPD1611	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