NPASS Compound

Structure

NPC3744 OpenBabel07101718272D 25 27 0 0 0 0 0 0 0 0999 V2000 6.0622 -2.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 5.1962 -0.0000 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 5.1962 -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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 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 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 15 1 0 0 0 0 5 11 1 0 0 0 0 5 12 2 0 0 0 0 6 10 2 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 20 2 0 0 0 0 10 12 1 0 0 0 0 11 19 2 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.09
Volume:	340.524
LogP:	3.593
LogD:	2.871
LogS:	-4.221
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	2.45
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973
MDCK Permeability:	8.670926945342217e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.577

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	96.1774673461914%
Volume Distribution (VD):	0.525
Pgp-substrate:	5.193174362182617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.833
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.244
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.539
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.288
CYP2D6-substrate:	0.829
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	8.789
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.656
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.929
Carcinogencity:	0.109
Eye Corrosion:	0.011
Eye Irritation:	0.93
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC3744

Natural Product ID:	NPC3744
*Common Name:**	Vitexdoin E
IUPAC Name:	1,6-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphthalene-2-carbaldehyde
Synonyms:	vitexdoin E
Standard InCHIKey:	WFANYWPAAJRIFF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O6/c1-24-17-6-10(3-4-15(17)21)12-5-11(9-20)19(23)14-8-18(25-2)16(22)7-13(12)14/h3-9,21-23H,1-2H3
SMILES:	COc1cc2c(O)c(C=O)cc(c2cc1O)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078524
PubChem CID:	44479221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000325] Biphenols

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	150.0	nM	PMID[478988]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	84.19	%	PMID[478988]

☑ 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 NPC3744 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	425
0.1-0.2	1860
0.2-0.3	4069
0.3-0.4	11362
0.4-0.5	6688
0.5-0.6	3528
0.6-0.7	6594
0.7-0.8	7007
0.8-0.85	1086
0.85-0.9	66
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC137125
0.9795	High Similarity	NPC70320
0.9586	High Similarity	NPC39361
0.9448	High Similarity	NPC300603
0.9448	High Similarity	NPC91694
0.9396	High Similarity	NPC75377
0.9221	High Similarity	NPC141574
0.9161	High Similarity	NPC131905
0.915	High Similarity	NPC279605
0.9139	High Similarity	NPC473201
0.9139	High Similarity	NPC302783
0.9079	High Similarity	NPC164912
0.9026	High Similarity	NPC213401
0.9013	High Similarity	NPC118427
0.8987	High Similarity	NPC26386
0.8968	High Similarity	NPC143328
0.8926	High Similarity	NPC275278
0.8889	High Similarity	NPC306011
0.8889	High Similarity	NPC472838
0.8889	High Similarity	NPC144283
0.8882	High Similarity	NPC261322
0.8867	High Similarity	NPC73416
0.8867	High Similarity	NPC160777
0.8846	High Similarity	NPC167098
0.8846	High Similarity	NPC37543
0.8846	High Similarity	NPC178976
0.8846	High Similarity	NPC199463
0.8846	High Similarity	NPC296044
0.8805	High Similarity	NPC477689
0.8797	High Similarity	NPC311740
0.8782	High Similarity	NPC14561
0.8782	High Similarity	NPC77807
0.8782	High Similarity	NPC5379
0.8776	High Similarity	NPC141368
0.8774	High Similarity	NPC475770
0.8774	High Similarity	NPC93552
0.8774	High Similarity	NPC474000
0.8742	High Similarity	NPC68441
0.8734	High Similarity	NPC84571
0.8733	High Similarity	NPC50954
0.871	High Similarity	NPC149889
0.871	High Similarity	NPC312338
0.8701	High Similarity	NPC295977
0.8701	High Similarity	NPC31132
0.8701	High Similarity	NPC58310
0.8688	High Similarity	NPC101769
0.8667	High Similarity	NPC192597
0.8667	High Similarity	NPC141817
0.8667	High Similarity	NPC229218
0.8667	High Similarity	NPC176030
0.8667	High Similarity	NPC169214
0.8658	High Similarity	NPC78987
0.8658	High Similarity	NPC82336
0.8654	High Similarity	NPC107109
0.8649	High Similarity	NPC206207
0.8645	High Similarity	NPC78505
0.8645	High Similarity	NPC256406
0.8642	High Similarity	NPC469521
0.8634	High Similarity	NPC303174
0.8627	High Similarity	NPC58373
0.8616	High Similarity	NPC36217
0.8608	High Similarity	NPC35598
0.8608	High Similarity	NPC222689
0.86	High Similarity	NPC124365
0.8598	High Similarity	NPC4200
0.8591	High Similarity	NPC1268
0.859	High Similarity	NPC295646
0.859	High Similarity	NPC180388
0.859	High Similarity	NPC131121
0.8581	High Similarity	NPC85131
0.858	High Similarity	NPC43319
0.8571	High Similarity	NPC152209
0.8571	High Similarity	NPC270837
0.8571	High Similarity	NPC55327
0.8562	High Similarity	NPC469889
0.8553	High Similarity	NPC45846
0.8553	High Similarity	NPC309169
0.8553	High Similarity	NPC196941
0.8553	High Similarity	NPC85121
0.8544	High Similarity	NPC478223
0.8544	High Similarity	NPC288353
0.8544	High Similarity	NPC109765
0.8543	High Similarity	NPC11314
0.8537	High Similarity	NPC131866
0.8535	High Similarity	NPC62051
0.8528	High Similarity	NPC218226
0.8528	High Similarity	NPC186392
0.8526	High Similarity	NPC124842
0.8516	High Similarity	NPC472837
0.8516	High Similarity	NPC38545
0.8516	High Similarity	NPC171916
0.8509	High Similarity	NPC201800
0.8509	High Similarity	NPC469472
0.8509	High Similarity	NPC294965
0.8509	High Similarity	NPC116838
0.8509	High Similarity	NPC22130
0.8509	High Similarity	NPC144843
0.8509	High Similarity	NPC476247
0.8506	High Similarity	NPC52692
0.85	High Similarity	NPC472902
0.8493	Intermediate Similarity	NPC228843
0.8491	Intermediate Similarity	NPC291508
0.8491	Intermediate Similarity	NPC202495
0.8487	Intermediate Similarity	NPC16353
0.8487	Intermediate Similarity	NPC46161
0.8487	Intermediate Similarity	NPC239608
0.8481	Intermediate Similarity	NPC134287
0.8481	Intermediate Similarity	NPC39184
0.8481	Intermediate Similarity	NPC130589
0.8481	Intermediate Similarity	NPC180901
0.8481	Intermediate Similarity	NPC300757
0.8477	Intermediate Similarity	NPC149780
0.8477	Intermediate Similarity	NPC84273
0.8476	Intermediate Similarity	NPC300307
0.8476	Intermediate Similarity	NPC188079
0.8471	Intermediate Similarity	NPC323626
0.8471	Intermediate Similarity	NPC199773
0.8471	Intermediate Similarity	NPC474993
0.8471	Intermediate Similarity	NPC324233
0.8467	Intermediate Similarity	NPC223336
0.8462	Intermediate Similarity	NPC472279
0.8457	Intermediate Similarity	NPC186686
0.8457	Intermediate Similarity	NPC197168
0.8457	Intermediate Similarity	NPC236132
0.8452	Intermediate Similarity	NPC166036
0.8452	Intermediate Similarity	NPC203747
0.8452	Intermediate Similarity	NPC80710
0.8452	Intermediate Similarity	NPC203077
0.8452	Intermediate Similarity	NPC139364
0.8452	Intermediate Similarity	NPC238279
0.8452	Intermediate Similarity	NPC254702
0.8452	Intermediate Similarity	NPC194653
0.8447	Intermediate Similarity	NPC66288
0.8442	Intermediate Similarity	NPC300540
0.8438	Intermediate Similarity	NPC104876
0.8438	Intermediate Similarity	NPC245891
0.8438	Intermediate Similarity	NPC324736
0.8438	Intermediate Similarity	NPC210459
0.8434	Intermediate Similarity	NPC199357
0.8431	Intermediate Similarity	NPC472836
0.8428	Intermediate Similarity	NPC291878
0.8428	Intermediate Similarity	NPC195796
0.8428	Intermediate Similarity	NPC35038
0.8428	Intermediate Similarity	NPC227062
0.8428	Intermediate Similarity	NPC278778
0.8421	Intermediate Similarity	NPC69755
0.8418	Intermediate Similarity	NPC208806
0.8418	Intermediate Similarity	NPC124714
0.8418	Intermediate Similarity	NPC472905
0.8415	Intermediate Similarity	NPC474024
0.8405	Intermediate Similarity	NPC293319
0.8405	Intermediate Similarity	NPC25361
0.84	Intermediate Similarity	NPC61398
0.84	Intermediate Similarity	NPC416
0.8397	Intermediate Similarity	NPC139293
0.8397	Intermediate Similarity	NPC264550
0.8397	Intermediate Similarity	NPC264289
0.8397	Intermediate Similarity	NPC195763
0.8397	Intermediate Similarity	NPC40290
0.8397	Intermediate Similarity	NPC69430
0.8397	Intermediate Similarity	NPC200060
0.8397	Intermediate Similarity	NPC333691
0.8397	Intermediate Similarity	NPC329933
0.8397	Intermediate Similarity	NPC142876
0.8397	Intermediate Similarity	NPC300983
0.8395	Intermediate Similarity	NPC473445
0.8395	Intermediate Similarity	NPC472964
0.8395	Intermediate Similarity	NPC42797
0.8389	Intermediate Similarity	NPC141934
0.8389	Intermediate Similarity	NPC324929
0.8387	Intermediate Similarity	NPC34802
0.8385	Intermediate Similarity	NPC228785
0.8385	Intermediate Similarity	NPC155302
0.8385	Intermediate Similarity	NPC78944
0.8385	Intermediate Similarity	NPC161947
0.8385	Intermediate Similarity	NPC299436
0.8385	Intermediate Similarity	NPC47623
0.8385	Intermediate Similarity	NPC56085
0.8385	Intermediate Similarity	NPC474960
0.8385	Intermediate Similarity	NPC14353
0.8385	Intermediate Similarity	NPC321399
0.8377	Intermediate Similarity	NPC478019
0.8377	Intermediate Similarity	NPC157133
0.8375	Intermediate Similarity	NPC302258
0.8375	Intermediate Similarity	NPC299520
0.8375	Intermediate Similarity	NPC27337
0.8375	Intermediate Similarity	NPC474055
0.8375	Intermediate Similarity	NPC472598
0.8375	Intermediate Similarity	NPC129684
0.8375	Intermediate Similarity	NPC472963
0.8375	Intermediate Similarity	NPC136674
0.8375	Intermediate Similarity	NPC78103
0.8373	Intermediate Similarity	NPC158226
0.8366	Intermediate Similarity	NPC254659
0.8365	Intermediate Similarity	NPC226656
0.8365	Intermediate Similarity	NPC152951
0.8365	Intermediate Similarity	NPC117992
0.8365	Intermediate Similarity	NPC234255
0.8365	Intermediate Similarity	NPC472835
0.8365	Intermediate Similarity	NPC57674

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 NPC3744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	999
0.2-0.3	1523
0.3-0.4	2740
0.4-0.5	1782
0.5-0.6	1032
0.6-0.7	520
0.7-0.8	131
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD6232	Discontinued
0.8742	High Similarity	NPD7422	Clinical (unspecified phase)
0.858	High Similarity	NPD7473	Discontinued
0.8412	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD1934	Approved
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8075	Intermediate Similarity	NPD2801	Approved
0.8072	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7003	Approved
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7974	Intermediate Similarity	NPD5404	Approved
0.7974	Intermediate Similarity	NPD5406	Approved
0.7974	Intermediate Similarity	NPD5405	Approved
0.7974	Intermediate Similarity	NPD5408	Approved
0.7937	Intermediate Similarity	NPD3226	Approved
0.7922	Intermediate Similarity	NPD2346	Discontinued
0.7905	Intermediate Similarity	NPD9494	Approved
0.7888	Intermediate Similarity	NPD4380	Phase 2
0.7866	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1511	Approved
0.777	Intermediate Similarity	NPD1470	Approved
0.7765	Intermediate Similarity	NPD3818	Discontinued
0.7758	Intermediate Similarity	NPD7768	Phase 2
0.7755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1512	Approved
0.7744	Intermediate Similarity	NPD7819	Suspended
0.774	Intermediate Similarity	NPD1201	Approved
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7725	Intermediate Similarity	NPD5494	Approved
0.7716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8313	Approved
0.7701	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7688	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2533	Approved
0.7677	Intermediate Similarity	NPD1510	Phase 2
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7074	Phase 3
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7662	Intermediate Similarity	NPD1607	Approved
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7625	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7054	Approved
0.7607	Intermediate Similarity	NPD7458	Discontinued
0.7605	Intermediate Similarity	NPD7075	Discontinued
0.759	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1283	Approved
0.7578	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD7472	Approved
0.7564	Intermediate Similarity	NPD2799	Discontinued
0.7534	Intermediate Similarity	NPD1651	Approved
0.7532	Intermediate Similarity	NPD1240	Approved
0.7532	Intermediate Similarity	NPD943	Approved
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7515	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD2798	Approved
0.7471	Intermediate Similarity	NPD1247	Approved
0.7468	Intermediate Similarity	NPD2344	Approved
0.7456	Intermediate Similarity	NPD919	Approved
0.7455	Intermediate Similarity	NPD6599	Discontinued
0.7451	Intermediate Similarity	NPD3027	Phase 3
0.7442	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4966	Approved
0.744	Intermediate Similarity	NPD4967	Phase 2
0.744	Intermediate Similarity	NPD4965	Approved
0.7438	Intermediate Similarity	NPD8166	Discontinued
0.7429	Intermediate Similarity	NPD6797	Phase 2
0.7421	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1549	Phase 2
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7419	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2979	Phase 3
0.7419	Intermediate Similarity	NPD3620	Phase 2
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2313	Discontinued
0.7403	Intermediate Similarity	NPD3764	Approved
0.7396	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7251	Discontinued
0.7383	Intermediate Similarity	NPD1281	Approved
0.7378	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8127	Discontinued
0.7365	Intermediate Similarity	NPD6801	Discontinued
0.7365	Intermediate Similarity	NPD4626	Approved
0.7358	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7228	Approved
0.7356	Intermediate Similarity	NPD7177	Discontinued
0.7345	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7808	Phase 3
0.7342	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3750	Approved
0.7317	Intermediate Similarity	NPD6273	Approved
0.7301	Intermediate Similarity	NPD6799	Approved
0.7296	Intermediate Similarity	NPD2438	Suspended
0.7296	Intermediate Similarity	NPD2796	Approved
0.7294	Intermediate Similarity	NPD3749	Approved
0.729	Intermediate Similarity	NPD6798	Discontinued
0.7284	Intermediate Similarity	NPD2309	Approved
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7219	Intermediate Similarity	NPD3972	Approved
0.7219	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7039	Approved
0.7191	Intermediate Similarity	NPD7038	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7184	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5691	Approved
0.7178	Intermediate Similarity	NPD6190	Approved
0.7176	Intermediate Similarity	NPD5402	Approved
0.7176	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6674	Discontinued
0.716	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7134	Intermediate Similarity	NPD3300	Phase 2
0.7126	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD5711	Approved
0.7124	Intermediate Similarity	NPD1876	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7118	Intermediate Similarity	NPD8455	Phase 2
0.7115	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4625	Phase 3
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7103	Intermediate Similarity	NPD228	Approved
0.7097	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7088	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD2531	Phase 2
0.7078	Intermediate Similarity	NPD1203	Approved
0.7078	Intermediate Similarity	NPD1164	Approved
0.707	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7066	Intermediate Similarity	NPD920	Approved
0.7066	Intermediate Similarity	NPD5403	Approved
0.7062	Intermediate Similarity	NPD3751	Discontinued
0.7051	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7028	Phase 2
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD4308	Phase 3
0.7019	Intermediate Similarity	NPD3748	Approved
0.7017	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7697	Approved
0.7016	Intermediate Similarity	NPD7698	Approved
0.7016	Intermediate Similarity	NPD7696	Phase 3
0.7012	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD7008	Discontinued
0.7	Intermediate Similarity	NPD6873	Phase 2
0.7	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD6386	Approved
0.6982	Remote Similarity	NPD3455	Phase 2
0.698	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4476	Approved
0.6975	Remote Similarity	NPD4477	Approved
0.6962	Remote Similarity	NPD411	Approved
0.6959	Remote Similarity	NPD7701	Phase 2
0.6952	Remote Similarity	NPD6534	Approved
0.6952	Remote Similarity	NPD6535	Approved
0.6951	Remote Similarity	NPD2800	Approved
0.6946	Remote Similarity	NPD5401	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