NPASS Compound

Structure

NPC91694 OpenBabel07101719242D 24 26 0 0 0 0 0 0 0 0999 V2000 -3.4641 2.0000 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 -2.5000 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 -4.3301 -1.5000 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 -1.0000 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 -1.7321 -0.0000 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 -1.5000 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 -2.5981 -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 -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 -4.3301 0.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -4.3301 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 20 2 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 13 19 2 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 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.1
Volume:	331.734
LogP:	3.475
LogD:	3.15
LogS:	-4.49
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	2.356
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:	-4.799
MDCK Permeability:	1.585151767358184e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.277
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	97.00967407226562%
Volume Distribution (VD):	0.66
Pgp-substrate:	2.434537410736084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.911
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.714
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.655
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.483
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.693
CYP3A4-substrate:	0.329

ADMET: Excretion

Clearance (CL):	7.016
Half-life (T1/2):	0.655

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.832
AMES Toxicity:	0.771
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.703
Carcinogencity:	0.595
Eye Corrosion:	0.023
Eye Irritation:	0.942
Respiratory Toxicity:	0.746

Download Data

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

Natural Product: NPC91694

Natural Product ID:	NPC91694
*Common Name:**	Vitexdoin C
IUPAC Name:	7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxynaphthalene-2-carbaldehyde
Synonyms:	vitexdoin C
Standard InCHIKey:	TWPBLWBNALQAFO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O5/c1-23-17-8-12(5-6-15(17)21)19-13(10-20)4-3-11-7-18(24-2)16(22)9-14(11)19/h3-10,21-22H,1-2H3
SMILES:	COc1cc(ccc1O)c1c(ccc2cc(c(cc12)O)OC)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079038
PubChem CID:	44478949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols and derivatives

*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	=	570.0	nM	PMID[512720]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	61.71	%	PMID[512720]

☑ 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 NPC91694 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	384
0.1-0.2	1787
0.2-0.3	4087
0.3-0.4	11898
0.4-0.5	6104
0.5-0.6	3696
0.6-0.7	8623
0.7-0.8	5812
0.8-0.85	263
0.85-0.9	31
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300603
0.9856	High Similarity	NPC39361
0.9448	High Similarity	NPC3744
0.9448	High Similarity	NPC137125
0.9379	High Similarity	NPC70320
0.9375	High Similarity	NPC261322
0.9257	High Similarity	NPC213401
0.9178	High Similarity	NPC295977
0.9178	High Similarity	NPC58310
0.9155	High Similarity	NPC192597
0.9155	High Similarity	NPC169214
0.9155	High Similarity	NPC229218
0.9155	High Similarity	NPC141817
0.9155	High Similarity	NPC176030
0.9149	High Similarity	NPC78987
0.9149	High Similarity	NPC82336
0.9116	High Similarity	NPC306011
0.9116	High Similarity	NPC472838
0.9013	High Similarity	NPC131905
0.8926	High Similarity	NPC164912
0.8874	High Similarity	NPC279605
0.8859	High Similarity	NPC75377
0.8859	High Similarity	NPC118427
0.8844	High Similarity	NPC58373
0.8816	High Similarity	NPC143328
0.8767	High Similarity	NPC196941
0.8767	High Similarity	NPC309169
0.8767	High Similarity	NPC275278
0.875	High Similarity	NPC288353
0.8733	High Similarity	NPC144283
0.8733	High Similarity	NPC302783
0.8733	High Similarity	NPC473201
0.8725	High Similarity	NPC472837
0.8716	High Similarity	NPC52692
0.8707	High Similarity	NPC160777
0.8707	High Similarity	NPC73416
0.8701	High Similarity	NPC141574
0.8693	High Similarity	NPC296044
0.8693	High Similarity	NPC167098
0.8662	High Similarity	NPC88065
0.8662	High Similarity	NPC95485
0.8662	High Similarity	NPC89504
0.8639	High Similarity	NPC472836
0.8633	High Similarity	NPC304622
0.8623	High Similarity	NPC5018
0.8623	High Similarity	NPC276466
0.8623	High Similarity	NPC123228
0.8623	High Similarity	NPC123722
0.8623	High Similarity	NPC151167
0.8621	High Similarity	NPC29599
0.8618	High Similarity	NPC474000
0.8618	High Similarity	NPC475770
0.8609	High Similarity	NPC78505
0.8571	High Similarity	NPC50954
0.8571	High Similarity	NPC66905
0.8551	High Similarity	NPC303680
0.8551	High Similarity	NPC276014
0.8551	High Similarity	NPC84076
0.8551	High Similarity	NPC90128
0.8551	High Similarity	NPC179777
0.8533	High Similarity	NPC127827
0.8481	Intermediate Similarity	NPC26386
0.8478	Intermediate Similarity	NPC257589
0.8478	Intermediate Similarity	NPC29008
0.8478	Intermediate Similarity	NPC228771
0.8478	Intermediate Similarity	NPC266705
0.8478	Intermediate Similarity	NPC53305
0.8462	Intermediate Similarity	NPC144662
0.8462	Intermediate Similarity	NPC274876
0.8456	Intermediate Similarity	NPC225351
0.8452	Intermediate Similarity	NPC37543
0.8452	Intermediate Similarity	NPC199463
0.8452	Intermediate Similarity	NPC178976
0.8451	Intermediate Similarity	NPC228843
0.8446	Intermediate Similarity	NPC239608
0.8446	Intermediate Similarity	NPC46161
0.844	Intermediate Similarity	NPC245395
0.8435	Intermediate Similarity	NPC472410
0.8431	Intermediate Similarity	NPC131121
0.8429	Intermediate Similarity	NPC307050
0.8429	Intermediate Similarity	NPC277458
0.8417	Intermediate Similarity	NPC92207
0.8417	Intermediate Similarity	NPC127937
0.8414	Intermediate Similarity	NPC264022
0.8408	Intermediate Similarity	NPC469889
0.8403	Intermediate Similarity	NPC252343
0.8403	Intermediate Similarity	NPC152209
0.8397	Intermediate Similarity	NPC104876
0.8397	Intermediate Similarity	NPC245891
0.8389	Intermediate Similarity	NPC308006
0.8387	Intermediate Similarity	NPC5379
0.8387	Intermediate Similarity	NPC77807
0.8387	Intermediate Similarity	NPC14561
0.8387	Intermediate Similarity	NPC109765
0.8378	Intermediate Similarity	NPC11314
0.8377	Intermediate Similarity	NPC62051
0.8377	Intermediate Similarity	NPC93552
0.8366	Intermediate Similarity	NPC124842
0.8366	Intermediate Similarity	NPC267091
0.8357	Intermediate Similarity	NPC203719
0.8357	Intermediate Similarity	NPC428300
0.8357	Intermediate Similarity	NPC117237
0.8356	Intermediate Similarity	NPC206207
0.8355	Intermediate Similarity	NPC237441
0.8355	Intermediate Similarity	NPC475722
0.8354	Intermediate Similarity	NPC22130
0.8354	Intermediate Similarity	NPC116838
0.8345	Intermediate Similarity	NPC90431
0.8345	Intermediate Similarity	NPC9067
0.8333	Intermediate Similarity	NPC9370
0.8333	Intermediate Similarity	NPC202495
0.8333	Intermediate Similarity	NPC287495
0.8333	Intermediate Similarity	NPC257976
0.8333	Intermediate Similarity	NPC242372
0.8333	Intermediate Similarity	NPC4181
0.8333	Intermediate Similarity	NPC164778
0.8333	Intermediate Similarity	NPC157133
0.8323	Intermediate Similarity	NPC300757
0.8323	Intermediate Similarity	NPC180901
0.8322	Intermediate Similarity	NPC46880
0.8322	Intermediate Similarity	NPC239302
0.8322	Intermediate Similarity	NPC224884
0.8322	Intermediate Similarity	NPC16353
0.8322	Intermediate Similarity	NPC209085
0.8312	Intermediate Similarity	NPC312338
0.8312	Intermediate Similarity	NPC149889
0.8311	Intermediate Similarity	NPC84273
0.831	Intermediate Similarity	NPC244246
0.831	Intermediate Similarity	NPC311419
0.831	Intermediate Similarity	NPC172673
0.831	Intermediate Similarity	NPC65935
0.831	Intermediate Similarity	NPC319282
0.831	Intermediate Similarity	NPC215941
0.831	Intermediate Similarity	NPC275724
0.831	Intermediate Similarity	NPC137427
0.831	Intermediate Similarity	NPC123196
0.8302	Intermediate Similarity	NPC477689
0.8301	Intermediate Similarity	NPC475718
0.8301	Intermediate Similarity	NPC243891
0.8299	Intermediate Similarity	NPC223336
0.8298	Intermediate Similarity	NPC226661
0.8291	Intermediate Similarity	NPC311740
0.8289	Intermediate Similarity	NPC24193
0.8289	Intermediate Similarity	NPC472839
0.8289	Intermediate Similarity	NPC55327
0.8276	Intermediate Similarity	NPC204592
0.8273	Intermediate Similarity	NPC312404
0.8273	Intermediate Similarity	NPC273686
0.8264	Intermediate Similarity	NPC327410
0.8261	Intermediate Similarity	NPC114298
0.8258	Intermediate Similarity	NPC107109
0.8255	Intermediate Similarity	NPC69755
0.8255	Intermediate Similarity	NPC86455
0.8255	Intermediate Similarity	NPC137920
0.8255	Intermediate Similarity	NPC125134
0.825	Intermediate Similarity	NPC303174
0.8247	Intermediate Similarity	NPC256406
0.8247	Intermediate Similarity	NPC115869
0.8243	Intermediate Similarity	NPC28398
0.8239	Intermediate Similarity	NPC42797
0.8239	Intermediate Similarity	NPC149389
0.8239	Intermediate Similarity	NPC473445
0.8235	Intermediate Similarity	NPC300983
0.8231	Intermediate Similarity	NPC132804
0.8231	Intermediate Similarity	NPC76032
0.8231	Intermediate Similarity	NPC141368
0.8231	Intermediate Similarity	NPC132723
0.8231	Intermediate Similarity	NPC220344
0.8231	Intermediate Similarity	NPC275061
0.8231	Intermediate Similarity	NPC284409
0.8231	Intermediate Similarity	NPC243996
0.8228	Intermediate Similarity	NPC21046
0.8228	Intermediate Similarity	NPC84571
0.8227	Intermediate Similarity	NPC16651
0.8227	Intermediate Similarity	NPC32163
0.8224	Intermediate Similarity	NPC181464
0.8219	Intermediate Similarity	NPC324929
0.8219	Intermediate Similarity	NPC120852
0.8217	Intermediate Similarity	NPC35598
0.8217	Intermediate Similarity	NPC222689
0.8214	Intermediate Similarity	NPC87113
0.8212	Intermediate Similarity	NPC478019
0.8212	Intermediate Similarity	NPC68441
0.821	Intermediate Similarity	NPC117911
0.8207	Intermediate Similarity	NPC68779
0.8207	Intermediate Similarity	NPC176814
0.8207	Intermediate Similarity	NPC141023
0.8207	Intermediate Similarity	NPC4982
0.8207	Intermediate Similarity	NPC5310
0.8207	Intermediate Similarity	NPC300776
0.8205	Intermediate Similarity	NPC472835
0.8201	Intermediate Similarity	NPC160900
0.8201	Intermediate Similarity	NPC18984
0.8201	Intermediate Similarity	NPC106659
0.8201	Intermediate Similarity	NPC229084
0.8201	Intermediate Similarity	NPC163083
0.8199	Intermediate Similarity	NPC263212
0.8199	Intermediate Similarity	NPC43065
0.8194	Intermediate Similarity	NPC183103
0.8194	Intermediate Similarity	NPC50763

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 NPC91694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	1042
0.2-0.3	1339
0.3-0.4	2669
0.4-0.5	1909
0.5-0.6	1121
0.6-0.7	586
0.7-0.8	110
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8357	Intermediate Similarity	NPD9494	Approved
0.8239	Intermediate Similarity	NPD6232	Discontinued
0.8212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7003	Approved
0.8098	Intermediate Similarity	NPD5844	Phase 1
0.8086	Intermediate Similarity	NPD7473	Discontinued
0.8014	Intermediate Similarity	NPD1283	Approved
0.7971	Intermediate Similarity	NPD1651	Approved
0.7941	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD8166	Discontinued
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7823	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3620	Phase 2
0.7801	Intermediate Similarity	NPD1281	Approved
0.78	Intermediate Similarity	NPD2935	Discontinued
0.7799	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7458	Discontinued
0.7736	Intermediate Similarity	NPD1934	Approved
0.7703	Intermediate Similarity	NPD2979	Phase 3
0.7702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5536	Phase 2
0.7692	Intermediate Similarity	NPD6273	Approved
0.7682	Intermediate Similarity	NPD2438	Suspended
0.7647	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD3972	Approved
0.7607	Intermediate Similarity	NPD6234	Discontinued
0.7593	Intermediate Similarity	NPD3882	Suspended
0.759	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6166	Phase 2
0.759	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4060	Phase 1
0.7578	Intermediate Similarity	NPD2801	Approved
0.7568	Intermediate Similarity	NPD3764	Approved
0.7566	Intermediate Similarity	NPD5404	Approved
0.7566	Intermediate Similarity	NPD5408	Approved
0.7566	Intermediate Similarity	NPD5406	Approved
0.7566	Intermediate Similarity	NPD5405	Approved
0.7536	Intermediate Similarity	NPD5283	Phase 1
0.7535	Intermediate Similarity	NPD4626	Approved
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7518	Intermediate Similarity	NPD228	Approved
0.7517	Intermediate Similarity	NPD1876	Approved
0.7516	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7451	Intermediate Similarity	NPD2531	Phase 2
0.745	Intermediate Similarity	NPD6798	Discontinued
0.7438	Intermediate Similarity	NPD3226	Approved
0.7403	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7028	Phase 2
0.7391	Intermediate Similarity	NPD4380	Phase 2
0.7386	Intermediate Similarity	NPD2799	Discontinued
0.7383	Intermediate Similarity	NPD7008	Discontinued
0.7378	Intermediate Similarity	NPD7768	Phase 2
0.7378	Intermediate Similarity	NPD4965	Approved
0.7378	Intermediate Similarity	NPD4966	Approved
0.7378	Intermediate Similarity	NPD4967	Phase 2
0.7372	Intermediate Similarity	NPD4110	Phase 3
0.7372	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7819	Suspended
0.7356	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1470	Approved
0.7346	Intermediate Similarity	NPD6873	Phase 2
0.7343	Intermediate Similarity	NPD5691	Approved
0.7342	Intermediate Similarity	NPD1511	Approved
0.7329	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3455	Phase 2
0.7317	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1201	Approved
0.7305	Intermediate Similarity	NPD8127	Discontinued
0.7297	Intermediate Similarity	NPD2798	Approved
0.7294	Intermediate Similarity	NPD3818	Discontinued
0.7294	Intermediate Similarity	NPD7228	Approved
0.7294	Intermediate Similarity	NPD7177	Discontinued
0.7292	Intermediate Similarity	NPD3019	Approved
0.729	Intermediate Similarity	NPD2344	Approved
0.7285	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7267	Intermediate Similarity	NPD7095	Approved
0.7261	Intermediate Similarity	NPD3750	Approved
0.7255	Intermediate Similarity	NPD1607	Approved
0.725	Intermediate Similarity	NPD1512	Approved
0.7246	Intermediate Similarity	NPD3021	Approved
0.7246	Intermediate Similarity	NPD5494	Approved
0.7246	Intermediate Similarity	NPD3022	Approved
0.7241	Intermediate Similarity	NPD8312	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.7233	Intermediate Similarity	NPD7390	Discontinued
0.7229	Intermediate Similarity	NPD7075	Discontinued
0.7225	Intermediate Similarity	NPD7038	Approved
0.7225	Intermediate Similarity	NPD7039	Approved
0.7215	Intermediate Similarity	NPD6190	Approved
0.7212	Intermediate Similarity	NPD5977	Approved
0.7212	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3817	Phase 2
0.7212	Intermediate Similarity	NPD5978	Approved
0.7209	Intermediate Similarity	NPD7074	Phase 3
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.719	Intermediate Similarity	NPD230	Phase 1
0.719	Intermediate Similarity	NPD6355	Discontinued
0.719	Intermediate Similarity	NPD447	Suspended
0.7188	Intermediate Similarity	NPD2533	Approved
0.7188	Intermediate Similarity	NPD2534	Approved
0.7188	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2532	Approved
0.7172	Intermediate Similarity	NPD2932	Approved
0.7168	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7411	Suspended
0.7126	Intermediate Similarity	NPD7685	Pre-registration
0.7124	Intermediate Similarity	NPD1240	Approved
0.7124	Intermediate Similarity	NPD943	Approved
0.7118	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4476	Approved
0.7115	Intermediate Similarity	NPD1551	Phase 2
0.7115	Intermediate Similarity	NPD4477	Approved
0.7113	Intermediate Similarity	NPD5951	Approved
0.711	Intermediate Similarity	NPD7472	Approved
0.7107	Intermediate Similarity	NPD2309	Approved
0.7105	Intermediate Similarity	NPD2313	Discontinued
0.7089	Intermediate Similarity	NPD6674	Discontinued
0.7083	Intermediate Similarity	NPD919	Approved
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3657	Discovery
0.7078	Intermediate Similarity	NPD1933	Approved
0.7076	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6599	Discontinued
0.7063	Intermediate Similarity	NPD7440	Discontinued
0.7059	Intermediate Similarity	NPD6663	Approved
0.7059	Intermediate Similarity	NPD8032	Phase 2
0.7056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1241	Discontinued
0.7039	Intermediate Similarity	NPD4625	Phase 3
0.703	Intermediate Similarity	NPD6385	Approved
0.703	Intermediate Similarity	NPD6386	Approved
0.7025	Intermediate Similarity	NPD1549	Phase 2
0.7025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5736	Approved
0.7013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4140	Approved
0.7013	Intermediate Similarity	NPD1613	Approved
0.7012	Intermediate Similarity	NPD824	Approved
0.7006	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1247	Approved
0.7	Intermediate Similarity	NPD2797	Approved
0.6993	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6801	Discontinued
0.6983	Remote Similarity	NPD7693	Approved
0.6981	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2342	Discontinued
0.6974	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6797	Phase 2
0.6968	Remote Similarity	NPD5735	Approved
0.6962	Remote Similarity	NPD7266	Discontinued
0.6962	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4624	Approved
0.6954	Remote Similarity	NPD6584	Phase 3
0.6948	Remote Similarity	NPD4062	Phase 3
0.6946	Remote Similarity	NPD8455	Phase 2
0.6946	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3748	Approved
0.6939	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5049	Phase 3
0.6933	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7251	Discontinued
0.6923	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD4097	Suspended
0.6923	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3926	Phase 2
0.6918	Remote Similarity	NPD9545	Approved
0.6914	Remote Similarity	NPD6799	Approved
0.6913	Remote Similarity	NPD1608	Approved
0.6909	Remote Similarity	NPD2649	Approved
0.6909	Remote Similarity	NPD2651	Approved
0.6908	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4307	Phase 2
0.6901	Remote Similarity	NPD2821	Approved
0.6899	Remote Similarity	NPD2796	Approved
0.6894	Remote Similarity	NPD5241	Discontinued
0.6894	Remote Similarity	NPD2354	Approved
0.6893	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7808	Phase 3
0.6892	Remote Similarity	NPD3026	Approved
0.6892	Remote Similarity	NPD3023	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