NPASS Compound

Structure

NPC92623 OpenBabel07101719152D 24 25 0 0 1 0 0 0 0 0999 V2000 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 18 2 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 6 0 0 0 21 15 1 1 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.19
Volume:	362.575
LogP:	3.773
LogD:	3.697
LogS:	-4.284
# Rotatable Bonds:	9
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	3.073
Fsp3:	0.333
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:	-4.758
MDCK Permeability:	1.4109785297478084e-05
Pgp-inhibitor:	0.05
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	96.84565734863281%
Volume Distribution (VD):	0.416
Pgp-substrate:	1.5532087087631226%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.422
CYP2D6-substrate:	0.75
CYP3A4-inhibitor:	0.659
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	9.888
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.51
Human Hepatotoxicity (H-HT):	0.751
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.701
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.933
Carcinogencity:	0.474
Eye Corrosion:	0.165
Eye Irritation:	0.97
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC92623

Natural Product ID:	NPC92623
*Common Name:**	4-[(E,3S,5R)-5-Ethoxy-3-Hydroxy-7-Phenylhept-6-Enyl]Phenol
IUPAC Name:	4-[(E,3S,5R)-5-ethoxy-3-hydroxy-7-phenylhept-6-enyl]phenol
Synonyms:
Standard InCHIKey:	IADMDBFYOJAYAV-SJSVYFIFSA-N
Standard InCHI:	InChI=1S/C21H26O3/c1-2-24-21(15-11-17-6-4-3-5-7-17)16-20(23)14-10-18-8-12-19(22)13-9-18/h3-9,11-13,15,20-23H,2,10,14,16H2,1H3/b15-11+/t20-,21-/m0/s1
SMILES:	CCO[C@@H](/C=C/c1ccccc1)C[C@H](CCc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478570
PubChem CID:	10616133
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear 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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	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
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	100.0	uM	PMID[483239]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	100.0	uM	PMID[483239]

☑ 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 NPC92623 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	234
0.1-0.2	1159
0.2-0.3	3795
0.3-0.4	11303
0.4-0.5	7993
0.5-0.6	8180
0.6-0.7	7423
0.7-0.8	2320
0.8-0.85	234
0.85-0.9	40
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135464
0.9898	High Similarity	NPC154899
0.9898	High Similarity	NPC233396
0.949	High Similarity	NPC213730
0.9394	High Similarity	NPC91461
0.9394	High Similarity	NPC40258
0.9394	High Similarity	NPC7686
0.9388	High Similarity	NPC132078
0.9388	High Similarity	NPC216468
0.9388	High Similarity	NPC51333
0.9388	High Similarity	NPC78119
0.9238	High Similarity	NPC290353
0.9238	High Similarity	NPC153795
0.9238	High Similarity	NPC42911
0.9231	High Similarity	NPC63345
0.9135	High Similarity	NPC474272
0.9135	High Similarity	NPC306045
0.9135	High Similarity	NPC265211
0.9082	High Similarity	NPC26244
0.9029	High Similarity	NPC113457
0.8991	High Similarity	NPC476266
0.899	High Similarity	NPC473388
0.898	High Similarity	NPC151715
0.8972	High Similarity	NPC123175
0.8972	High Similarity	NPC176730
0.8911	High Similarity	NPC294741
0.8899	High Similarity	NPC473556
0.8899	High Similarity	NPC301651
0.8878	High Similarity	NPC138117
0.8878	High Similarity	NPC325292
0.8776	High Similarity	NPC45040
0.87	High Similarity	NPC313650
0.8692	High Similarity	NPC475018
0.8692	High Similarity	NPC183700
0.8679	High Similarity	NPC75440
0.8679	High Similarity	NPC262365
0.8679	High Similarity	NPC201959
0.8673	High Similarity	NPC300017
0.8627	High Similarity	NPC92730
0.8627	High Similarity	NPC128723
0.8614	High Similarity	NPC132271
0.8614	High Similarity	NPC216520
0.8614	High Similarity	NPC292730
0.8614	High Similarity	NPC82664
0.8611	High Similarity	NPC187583
0.8611	High Similarity	NPC257430
0.8611	High Similarity	NPC179002
0.86	High Similarity	NPC128062
0.8598	High Similarity	NPC62258
0.8598	High Similarity	NPC55617
0.8585	High Similarity	NPC260952
0.8571	High Similarity	NPC123273
0.8571	High Similarity	NPC318325
0.8571	High Similarity	NPC470393
0.8571	High Similarity	NPC280347
0.8571	High Similarity	NPC242240
0.8571	High Similarity	NPC177420
0.8558	High Similarity	NPC62351
0.8529	High Similarity	NPC474073
0.8529	High Similarity	NPC225464
0.8519	High Similarity	NPC321252
0.8519	High Similarity	NPC226401
0.8519	High Similarity	NPC147634
0.8519	High Similarity	NPC252544
0.8519	High Similarity	NPC174096
0.8519	High Similarity	NPC79793
0.8519	High Similarity	NPC44732
0.8519	High Similarity	NPC120982
0.8515	High Similarity	NPC274678
0.8505	High Similarity	NPC206341
0.8496	Intermediate Similarity	NPC109371
0.8496	Intermediate Similarity	NPC470214
0.8496	Intermediate Similarity	NPC470215
0.8485	Intermediate Similarity	NPC55561
0.8476	Intermediate Similarity	NPC108875
0.8476	Intermediate Similarity	NPC38079
0.8476	Intermediate Similarity	NPC323810
0.8469	Intermediate Similarity	NPC104216
0.8469	Intermediate Similarity	NPC25493
0.8469	Intermediate Similarity	NPC113460
0.8462	Intermediate Similarity	NPC471578
0.8462	Intermediate Similarity	NPC101025
0.8455	Intermediate Similarity	NPC35344
0.8455	Intermediate Similarity	NPC141003
0.8447	Intermediate Similarity	NPC171843
0.8447	Intermediate Similarity	NPC100870
0.844	Intermediate Similarity	NPC177576
0.844	Intermediate Similarity	NPC308689
0.844	Intermediate Similarity	NPC139946
0.8435	Intermediate Similarity	NPC113865
0.8435	Intermediate Similarity	NPC343720
0.8435	Intermediate Similarity	NPC470212
0.8435	Intermediate Similarity	NPC324571
0.8435	Intermediate Similarity	NPC312675
0.8435	Intermediate Similarity	NPC473853
0.8435	Intermediate Similarity	NPC54872
0.8435	Intermediate Similarity	NPC262156
0.8435	Intermediate Similarity	NPC184651
0.8416	Intermediate Similarity	NPC76938
0.8407	Intermediate Similarity	NPC86198
0.8407	Intermediate Similarity	NPC474214
0.8396	Intermediate Similarity	NPC138942
0.8396	Intermediate Similarity	NPC474839
0.8393	Intermediate Similarity	NPC85292
0.8393	Intermediate Similarity	NPC229147
0.8393	Intermediate Similarity	NPC54507
0.8384	Intermediate Similarity	NPC258219
0.8381	Intermediate Similarity	NPC192596
0.8381	Intermediate Similarity	NPC168829
0.8378	Intermediate Similarity	NPC12656
0.8378	Intermediate Similarity	NPC473137
0.8367	Intermediate Similarity	NPC23167
0.8364	Intermediate Similarity	NPC228425
0.8362	Intermediate Similarity	NPC174977
0.8362	Intermediate Similarity	NPC100099
0.8362	Intermediate Similarity	NPC36016
0.8348	Intermediate Similarity	NPC207613
0.8333	Intermediate Similarity	NPC163036
0.8333	Intermediate Similarity	NPC61885
0.8333	Intermediate Similarity	NPC474320
0.8333	Intermediate Similarity	NPC63698
0.8333	Intermediate Similarity	NPC317305
0.8333	Intermediate Similarity	NPC70084
0.8333	Intermediate Similarity	NPC32714
0.8319	Intermediate Similarity	NPC175799
0.8319	Intermediate Similarity	NPC200988
0.8319	Intermediate Similarity	NPC610
0.8319	Intermediate Similarity	NPC474933
0.8319	Intermediate Similarity	NPC145023
0.8305	Intermediate Similarity	NPC81641
0.8304	Intermediate Similarity	NPC185541
0.8304	Intermediate Similarity	NPC23402
0.8304	Intermediate Similarity	NPC464
0.8302	Intermediate Similarity	NPC8931
0.8302	Intermediate Similarity	NPC12987
0.8302	Intermediate Similarity	NPC288411
0.8302	Intermediate Similarity	NPC474603
0.8302	Intermediate Similarity	NPC119860
0.8302	Intermediate Similarity	NPC120693
0.8302	Intermediate Similarity	NPC261573
0.83	Intermediate Similarity	NPC300478
0.8291	Intermediate Similarity	NPC76465
0.8291	Intermediate Similarity	NPC473451
0.8291	Intermediate Similarity	NPC38761
0.8286	Intermediate Similarity	NPC51633
0.8276	Intermediate Similarity	NPC290451
0.8276	Intermediate Similarity	NPC127389
0.8265	Intermediate Similarity	NPC197783
0.8257	Intermediate Similarity	NPC79543
0.8246	Intermediate Similarity	NPC131118
0.8241	Intermediate Similarity	NPC251306
0.8241	Intermediate Similarity	NPC61033
0.8241	Intermediate Similarity	NPC305603
0.8235	Intermediate Similarity	NPC27323
0.8235	Intermediate Similarity	NPC316301
0.8235	Intermediate Similarity	NPC276212
0.823	Intermediate Similarity	NPC141090
0.823	Intermediate Similarity	NPC148055
0.822	Intermediate Similarity	NPC246648
0.822	Intermediate Similarity	NPC293701
0.822	Intermediate Similarity	NPC134195
0.822	Intermediate Similarity	NPC48990
0.822	Intermediate Similarity	NPC197351
0.822	Intermediate Similarity	NPC114901
0.822	Intermediate Similarity	NPC86502
0.822	Intermediate Similarity	NPC106914
0.8218	Intermediate Similarity	NPC304541
0.8218	Intermediate Similarity	NPC270547
0.8214	Intermediate Similarity	NPC120280
0.8214	Intermediate Similarity	NPC285350
0.8208	Intermediate Similarity	NPC135784
0.8208	Intermediate Similarity	NPC304638
0.8208	Intermediate Similarity	NPC305205
0.8205	Intermediate Similarity	NPC150026
0.8205	Intermediate Similarity	NPC255026
0.82	Intermediate Similarity	NPC98772
0.8198	Intermediate Similarity	NPC228452
0.819	Intermediate Similarity	NPC470849
0.819	Intermediate Similarity	NPC469703
0.819	Intermediate Similarity	NPC201402
0.819	Intermediate Similarity	NPC160854
0.819	Intermediate Similarity	NPC469704
0.819	Intermediate Similarity	NPC470848
0.8182	Intermediate Similarity	NPC46844
0.8182	Intermediate Similarity	NPC184169
0.8174	Intermediate Similarity	NPC311595
0.8174	Intermediate Similarity	NPC24474
0.8173	Intermediate Similarity	NPC201967
0.8165	Intermediate Similarity	NPC169450
0.8165	Intermediate Similarity	NPC31274
0.8165	Intermediate Similarity	NPC11554
0.8163	Intermediate Similarity	NPC248817
0.8163	Intermediate Similarity	NPC175313
0.8158	Intermediate Similarity	NPC164386
0.8158	Intermediate Similarity	NPC122117
0.8151	Intermediate Similarity	NPC188022
0.8151	Intermediate Similarity	NPC102540
0.8151	Intermediate Similarity	NPC285040
0.8151	Intermediate Similarity	NPC17809
0.8151	Intermediate Similarity	NPC103420

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 NPC92623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	844
0.2-0.3	1285
0.3-0.4	2682
0.4-0.5	2050
0.5-0.6	1200
0.6-0.7	724
0.7-0.8	133
0.8-0.85	4
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9082	High Similarity	NPD2860	Approved
0.9082	High Similarity	NPD2859	Approved
0.898	High Similarity	NPD2934	Approved
0.898	High Similarity	NPD2933	Approved
0.8812	High Similarity	NPD3020	Approved
0.8333	Intermediate Similarity	NPD2684	Approved
0.8235	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD968	Approved
0.8113	Intermediate Similarity	NPD940	Approved
0.8113	Intermediate Similarity	NPD846	Approved
0.8091	Intermediate Similarity	NPD3021	Approved
0.8091	Intermediate Similarity	NPD3022	Approved
0.8061	Intermediate Similarity	NPD111	Approved
0.8036	Intermediate Similarity	NPD7843	Approved
0.7983	Intermediate Similarity	NPD6583	Phase 3
0.7983	Intermediate Similarity	NPD6582	Phase 2
0.7949	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1548	Phase 1
0.7931	Intermediate Similarity	NPD3091	Approved
0.7928	Intermediate Similarity	NPD5451	Approved
0.7909	Intermediate Similarity	NPD290	Approved
0.7886	Intermediate Similarity	NPD3027	Phase 3
0.785	Intermediate Similarity	NPD1242	Phase 1
0.785	Intermediate Similarity	NPD3028	Approved
0.7826	Intermediate Similarity	NPD7157	Approved
0.7815	Intermediate Similarity	NPD1610	Phase 2
0.781	Intermediate Similarity	NPD844	Approved
0.781	Intermediate Similarity	NPD1809	Phase 2
0.7805	Intermediate Similarity	NPD4908	Phase 1
0.7797	Intermediate Similarity	NPD5846	Approved
0.7797	Intermediate Similarity	NPD6516	Phase 2
0.7788	Intermediate Similarity	NPD845	Approved
0.7787	Intermediate Similarity	NPD6584	Phase 3
0.7724	Intermediate Similarity	NPD2861	Phase 2
0.7719	Intermediate Similarity	NPD5535	Approved
0.7719	Intermediate Similarity	NPD821	Approved
0.7686	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD4659	Approved
0.768	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6671	Approved
0.7667	Intermediate Similarity	NPD3092	Approved
0.7652	Intermediate Similarity	NPD2229	Approved
0.7652	Intermediate Similarity	NPD2228	Approved
0.7652	Intermediate Similarity	NPD5283	Phase 1
0.7652	Intermediate Similarity	NPD2234	Approved
0.7632	Intermediate Similarity	NPD228	Approved
0.7611	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3596	Phase 2
0.7603	Intermediate Similarity	NPD2561	Approved
0.7603	Intermediate Similarity	NPD2562	Approved
0.7583	Intermediate Similarity	NPD3847	Discontinued
0.757	Intermediate Similarity	NPD288	Approved
0.7561	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4103	Phase 2
0.7561	Intermediate Similarity	NPD3094	Phase 2
0.7541	Intermediate Similarity	NPD3685	Discontinued
0.7523	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2668	Approved
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3134	Approved
0.75	Intermediate Similarity	NPD2667	Approved
0.75	Intermediate Similarity	NPD3095	Discontinued
0.748	Intermediate Similarity	NPD6407	Approved
0.748	Intermediate Similarity	NPD6405	Approved
0.7479	Intermediate Similarity	NPD6580	Approved
0.7479	Intermediate Similarity	NPD1894	Discontinued
0.7479	Intermediate Similarity	NPD6581	Approved
0.7478	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2235	Phase 2
0.7459	Intermediate Similarity	NPD2231	Phase 2
0.7456	Intermediate Similarity	NPD4750	Phase 3
0.7442	Intermediate Similarity	NPD3052	Approved
0.7442	Intermediate Similarity	NPD3054	Approved
0.744	Intermediate Similarity	NPD5736	Approved
0.7422	Intermediate Similarity	NPD1613	Approved
0.7422	Intermediate Similarity	NPD4060	Phase 1
0.7422	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7635	Approved
0.7402	Intermediate Similarity	NPD6798	Discontinued
0.7402	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD16	Approved
0.7395	Intermediate Similarity	NPD856	Approved
0.7387	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4538	Approved
0.7385	Intermediate Similarity	NPD4536	Approved
0.7377	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2557	Approved
0.7364	Intermediate Similarity	NPD2553	Approved
0.7364	Intermediate Similarity	NPD2552	Approved
0.7364	Intermediate Similarity	NPD2555	Approved
0.7364	Intermediate Similarity	NPD2549	Approved
0.7364	Intermediate Similarity	NPD2558	Approved
0.7364	Intermediate Similarity	NPD2550	Approved
0.736	Intermediate Similarity	NPD3690	Phase 2
0.736	Intermediate Similarity	NPD3691	Phase 2
0.7348	Intermediate Similarity	NPD7266	Discontinued
0.7344	Intermediate Similarity	NPD6233	Phase 2
0.7339	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5303	Approved
0.7333	Intermediate Similarity	NPD5304	Approved
0.7333	Intermediate Similarity	NPD9545	Approved
0.7321	Intermediate Similarity	NPD9608	Approved
0.7321	Intermediate Similarity	NPD9610	Approved
0.7304	Intermediate Similarity	NPD1792	Phase 2
0.7297	Intermediate Similarity	NPD4188	Approved
0.7297	Intermediate Similarity	NPD4189	Approved
0.7295	Intermediate Similarity	NPD3421	Phase 3
0.7287	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2238	Phase 2
0.7287	Intermediate Similarity	NPD4140	Approved
0.7287	Intermediate Similarity	NPD3620	Phase 2
0.7281	Intermediate Similarity	NPD2342	Discontinued
0.7281	Intermediate Similarity	NPD1358	Approved
0.728	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD1357	Approved
0.7273	Intermediate Similarity	NPD4093	Discontinued
0.7266	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5327	Phase 3
0.725	Intermediate Similarity	NPD318	Approved
0.725	Intermediate Similarity	NPD317	Approved
0.7245	Intermediate Similarity	NPD9294	Approved
0.7236	Intermediate Similarity	NPD1535	Discovery
0.7236	Intermediate Similarity	NPD422	Phase 1
0.7236	Intermediate Similarity	NPD1091	Approved
0.7231	Intermediate Similarity	NPD5735	Approved
0.7231	Intermediate Similarity	NPD6355	Discontinued
0.7213	Intermediate Similarity	NPD4626	Approved
0.7213	Intermediate Similarity	NPD2932	Approved
0.7213	Intermediate Similarity	NPD4059	Approved
0.7213	Intermediate Similarity	NPD3019	Approved
0.7213	Intermediate Similarity	NPD4589	Approved
0.7209	Intermediate Similarity	NPD6663	Approved
0.7209	Intermediate Similarity	NPD4062	Phase 3
0.7203	Intermediate Similarity	NPD1241	Discontinued
0.7197	Intermediate Similarity	NPD5588	Approved
0.7197	Intermediate Similarity	NPD5960	Phase 3
0.7197	Intermediate Similarity	NPD7033	Discontinued
0.7193	Intermediate Similarity	NPD1445	Approved
0.7193	Intermediate Similarity	NPD1444	Approved
0.719	Intermediate Similarity	NPD7741	Discontinued
0.7188	Intermediate Similarity	NPD5163	Phase 2
0.7188	Intermediate Similarity	NPD6179	Discontinued
0.7188	Intermediate Similarity	NPD4625	Phase 3
0.7177	Intermediate Similarity	NPD1481	Phase 2
0.7177	Intermediate Similarity	NPD2233	Approved
0.7177	Intermediate Similarity	NPD2232	Approved
0.7177	Intermediate Similarity	NPD2230	Approved
0.7168	Intermediate Similarity	NPD3047	Approved
0.7168	Intermediate Similarity	NPD3048	Approved
0.7168	Intermediate Similarity	NPD3046	Approved
0.7143	Intermediate Similarity	NPD1133	Approved
0.7143	Intermediate Similarity	NPD1129	Approved
0.7143	Intermediate Similarity	NPD1135	Approved
0.7143	Intermediate Similarity	NPD9618	Approved
0.7143	Intermediate Similarity	NPD9614	Approved
0.7143	Intermediate Similarity	NPD1134	Approved
0.7143	Intermediate Similarity	NPD1131	Approved
0.7132	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD3444	Approved
0.7131	Intermediate Similarity	NPD3049	Approved
0.7131	Intermediate Similarity	NPD3445	Approved
0.7131	Intermediate Similarity	NPD1651	Approved
0.7131	Intermediate Similarity	NPD5691	Approved
0.7131	Intermediate Similarity	NPD3443	Approved
0.7121	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3554	Approved
0.7121	Intermediate Similarity	NPD3555	Approved
0.7121	Intermediate Similarity	NPD3553	Approved
0.7121	Intermediate Similarity	NPD3552	Approved
0.712	Intermediate Similarity	NPD6542	Approved
0.712	Intermediate Similarity	NPD2429	Approved
0.712	Intermediate Similarity	NPD1669	Approved
0.712	Intermediate Similarity	NPD4749	Approved
0.712	Intermediate Similarity	NPD2428	Approved
0.712	Intermediate Similarity	NPD6540	Phase 3
0.712	Intermediate Similarity	NPD6543	Approved
0.712	Intermediate Similarity	NPD6539	Approved
0.7111	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4624	Approved
0.7077	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD9295	Approved
0.7073	Intermediate Similarity	NPD5126	Approved
0.7073	Intermediate Similarity	NPD2556	Approved
0.7073	Intermediate Similarity	NPD2554	Approved
0.7073	Intermediate Similarity	NPD2286	Discontinued
0.7073	Intermediate Similarity	NPD5125	Phase 3
0.7063	Intermediate Similarity	NPD6541	Approved
0.7063	Intermediate Similarity	NPD8651	Approved
0.7063	Intermediate Similarity	NPD6538	Approved
0.7063	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD4535	Phase 3
0.7059	Intermediate Similarity	NPD4628	Phase 3

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