NPASS Compound

Structure

NPC39361 OpenBabel07101718182D 24 26 0 0 0 0 0 0 0 0999 V2000 -1.7321 2.0000 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 1.7321 -1.0000 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 -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 -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 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -0.8660 -1.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 0.0000 -0.0000 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 -4.3301 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 -2.5981 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 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 12 14 1 0 0 0 0 13 18 2 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.1
Volume:	331.734
LogP:	3.451
LogD:	2.995
LogS:	-4.267
# 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:	2.418
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:	-4.828
MDCK Permeability:	1.2155079275544267e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	97.74359893798828%
Volume Distribution (VD):	0.501
Pgp-substrate:	2.6314282417297363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.593
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.467
CYP2D6-substrate:	0.841
CYP3A4-inhibitor:	0.57
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	7.215
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.392
AMES Toxicity:	0.588
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.562
Skin Sensitization:	0.82
Carcinogencity:	0.314
Eye Corrosion:	0.045
Eye Irritation:	0.937
Respiratory Toxicity:	0.755

Download Data

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

Natural Product: NPC39361

Natural Product ID:	NPC39361
*Common Name:**	Vitexdoin B
IUPAC Name:	6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-5-methoxynaphthalene-2-carbaldehyde
Synonyms:	vitexdoin B
Standard InCHIKey:	HWWOGKWMIOQRRX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O5/c1-23-17-9-12(3-5-15(17)21)14-8-11(10-20)7-13-4-6-16(22)19(24-2)18(13)14/h3-10,21-22H,1-2H3
SMILES:	COc1cc(ccc1O)c1cc(cc2ccc(c(c12)OC)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079037
PubChem CID:	44478948
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	=	200.0	nM	PMID[514149]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	80.85	%	PMID[514149]

☑ 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 NPC39361 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	392
0.1-0.2	1843
0.2-0.3	4115
0.3-0.4	11857
0.4-0.5	6098
0.5-0.6	3657
0.6-0.7	7945
0.7-0.8	6412
0.8-0.85	325
0.85-0.9	39
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC300603
0.9856	High Similarity	NPC91694
0.9586	High Similarity	NPC3744
0.9586	High Similarity	NPC137125
0.9517	High Similarity	NPC70320
0.9392	High Similarity	NPC213401
0.9252	High Similarity	NPC472838
0.9252	High Similarity	NPC306011
0.9247	High Similarity	NPC261322
0.9145	High Similarity	NPC131905
0.906	High Similarity	NPC164912
0.9054	High Similarity	NPC295977
0.9054	High Similarity	NPC58310
0.9028	High Similarity	NPC176030
0.9028	High Similarity	NPC141817
0.9028	High Similarity	NPC192597
0.9028	High Similarity	NPC229218
0.9028	High Similarity	NPC169214
0.9021	High Similarity	NPC82336
0.9021	High Similarity	NPC78987
0.9007	High Similarity	NPC279605
0.8993	High Similarity	NPC118427
0.8993	High Similarity	NPC75377
0.898	High Similarity	NPC58373
0.8947	High Similarity	NPC143328
0.8904	High Similarity	NPC309169
0.8904	High Similarity	NPC196941
0.8904	High Similarity	NPC275278
0.8882	High Similarity	NPC288353
0.8867	High Similarity	NPC473201
0.8867	High Similarity	NPC144283
0.8867	High Similarity	NPC302783
0.8859	High Similarity	NPC472837
0.8851	High Similarity	NPC52692
0.8844	High Similarity	NPC73416
0.8844	High Similarity	NPC160777
0.8831	High Similarity	NPC141574
0.8824	High Similarity	NPC167098
0.8824	High Similarity	NPC296044
0.8776	High Similarity	NPC472836
0.875	High Similarity	NPC475770
0.875	High Similarity	NPC474000
0.8742	High Similarity	NPC78505
0.8707	High Similarity	NPC50954
0.8608	High Similarity	NPC26386
0.8601	High Similarity	NPC274876
0.8592	High Similarity	NPC228843
0.8591	High Similarity	NPC225351
0.8582	High Similarity	NPC245395
0.8581	High Similarity	NPC178976
0.8581	High Similarity	NPC199463
0.8581	High Similarity	NPC37543
0.8562	High Similarity	NPC131121
0.8542	High Similarity	NPC152209
0.8542	High Similarity	NPC95485
0.8542	High Similarity	NPC88065
0.8542	High Similarity	NPC89504
0.8535	High Similarity	NPC469889
0.8526	High Similarity	NPC245891
0.8526	High Similarity	NPC104876
0.8523	High Similarity	NPC308006
0.8516	High Similarity	NPC77807
0.8516	High Similarity	NPC5379
0.8516	High Similarity	NPC14561
0.8516	High Similarity	NPC109765
0.8514	High Similarity	NPC11314
0.8511	High Similarity	NPC304622
0.8506	High Similarity	NPC62051
0.8506	High Similarity	NPC93552
0.8503	High Similarity	NPC29599
0.85	High Similarity	NPC276466
0.85	High Similarity	NPC151167
0.85	High Similarity	NPC5018
0.85	High Similarity	NPC123722
0.85	High Similarity	NPC123228
0.8497	Intermediate Similarity	NPC124842
0.8493	Intermediate Similarity	NPC206207
0.8481	Intermediate Similarity	NPC116838
0.8481	Intermediate Similarity	NPC22130
0.8467	Intermediate Similarity	NPC157133
0.8462	Intermediate Similarity	NPC202495
0.8456	Intermediate Similarity	NPC16353
0.8452	Intermediate Similarity	NPC300757
0.8452	Intermediate Similarity	NPC180901
0.8451	Intermediate Similarity	NPC66905
0.8446	Intermediate Similarity	NPC84273
0.8442	Intermediate Similarity	NPC312338
0.8442	Intermediate Similarity	NPC149889
0.8435	Intermediate Similarity	NPC223336
0.8431	Intermediate Similarity	NPC475718
0.8429	Intermediate Similarity	NPC90128
0.8429	Intermediate Similarity	NPC179777
0.8429	Intermediate Similarity	NPC84076
0.8429	Intermediate Similarity	NPC303680
0.8429	Intermediate Similarity	NPC276014
0.8428	Intermediate Similarity	NPC477689
0.8421	Intermediate Similarity	NPC55327
0.8421	Intermediate Similarity	NPC472839
0.8421	Intermediate Similarity	NPC127827
0.8418	Intermediate Similarity	NPC311740
0.8389	Intermediate Similarity	NPC69755
0.8387	Intermediate Similarity	NPC107109
0.8377	Intermediate Similarity	NPC115869
0.8377	Intermediate Similarity	NPC256406
0.8375	Intermediate Similarity	NPC303174
0.8367	Intermediate Similarity	NPC141368
0.8367	Intermediate Similarity	NPC275061
0.8367	Intermediate Similarity	NPC243996
0.8367	Intermediate Similarity	NPC132804
0.8367	Intermediate Similarity	NPC220344
0.8366	Intermediate Similarity	NPC300983
0.8365	Intermediate Similarity	NPC42797
0.8365	Intermediate Similarity	NPC149389
0.8365	Intermediate Similarity	NPC473445
0.8357	Intermediate Similarity	NPC266705
0.8357	Intermediate Similarity	NPC228771
0.8357	Intermediate Similarity	NPC29008
0.8357	Intermediate Similarity	NPC257589
0.8357	Intermediate Similarity	NPC53305
0.8356	Intermediate Similarity	NPC324929
0.8354	Intermediate Similarity	NPC84571
0.8354	Intermediate Similarity	NPC21046
0.8345	Intermediate Similarity	NPC141023
0.8345	Intermediate Similarity	NPC144662
0.8344	Intermediate Similarity	NPC222689
0.8344	Intermediate Similarity	NPC68441
0.8344	Intermediate Similarity	NPC35598
0.8344	Intermediate Similarity	NPC478019
0.8333	Intermediate Similarity	NPC209085
0.8333	Intermediate Similarity	NPC239608
0.8333	Intermediate Similarity	NPC117911
0.8333	Intermediate Similarity	NPC472835
0.8333	Intermediate Similarity	NPC183103
0.8333	Intermediate Similarity	NPC224884
0.8333	Intermediate Similarity	NPC46161
0.8323	Intermediate Similarity	NPC263212
0.8323	Intermediate Similarity	NPC43065
0.8322	Intermediate Similarity	NPC149780
0.8322	Intermediate Similarity	NPC472410
0.8313	Intermediate Similarity	NPC291977
0.8313	Intermediate Similarity	NPC101769
0.8312	Intermediate Similarity	NPC31132
0.8312	Intermediate Similarity	NPC85131
0.8311	Intermediate Similarity	NPC308768
0.8311	Intermediate Similarity	NPC470407
0.8311	Intermediate Similarity	NPC1268
0.8311	Intermediate Similarity	NPC12668
0.831	Intermediate Similarity	NPC277458
0.831	Intermediate Similarity	NPC307050
0.831	Intermediate Similarity	NPC478215
0.8302	Intermediate Similarity	NPC216916
0.8301	Intermediate Similarity	NPC474556
0.8299	Intermediate Similarity	NPC230919
0.8299	Intermediate Similarity	NPC22902
0.8299	Intermediate Similarity	NPC56329
0.8299	Intermediate Similarity	NPC266453
0.8299	Intermediate Similarity	NPC242715
0.8299	Intermediate Similarity	NPC200935
0.8299	Intermediate Similarity	NPC264022
0.8299	Intermediate Similarity	NPC186647
0.8298	Intermediate Similarity	NPC127937
0.8298	Intermediate Similarity	NPC92207
0.8289	Intermediate Similarity	NPC58752
0.8288	Intermediate Similarity	NPC153088
0.8288	Intermediate Similarity	NPC252343
0.8278	Intermediate Similarity	NPC105213
0.8278	Intermediate Similarity	NPC207732
0.8276	Intermediate Similarity	NPC470406
0.8272	Intermediate Similarity	NPC469521
0.8261	Intermediate Similarity	NPC41689
0.8258	Intermediate Similarity	NPC118332
0.8258	Intermediate Similarity	NPC272566
0.8258	Intermediate Similarity	NPC267091
0.8255	Intermediate Similarity	NPC19158
0.8255	Intermediate Similarity	NPC476534
0.8253	Intermediate Similarity	NPC47191
0.8252	Intermediate Similarity	NPC261759
0.825	Intermediate Similarity	NPC469472
0.825	Intermediate Similarity	NPC198796
0.8247	Intermediate Similarity	NPC475722
0.8247	Intermediate Similarity	NPC37220
0.8247	Intermediate Similarity	NPC237441
0.8247	Intermediate Similarity	NPC38545
0.8247	Intermediate Similarity	NPC171916
0.8243	Intermediate Similarity	NPC105847
0.8243	Intermediate Similarity	NPC243759
0.8243	Intermediate Similarity	NPC218131
0.8243	Intermediate Similarity	NPC76032
0.8243	Intermediate Similarity	NPC132723
0.8242	Intermediate Similarity	NPC193377
0.8239	Intermediate Similarity	NPC36217
0.8239	Intermediate Similarity	NPC203719
0.8239	Intermediate Similarity	NPC117237
0.8239	Intermediate Similarity	NPC428300
0.8235	Intermediate Similarity	NPC470757
0.8235	Intermediate Similarity	NPC77598
0.8232	Intermediate Similarity	NPC4200
0.8231	Intermediate Similarity	NPC90431
0.8231	Intermediate Similarity	NPC30632
0.8227	Intermediate Similarity	NPC9067

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 NPC39361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	1053
0.2-0.3	1390
0.3-0.4	2679
0.4-0.5	1843
0.5-0.6	1095
0.6-0.7	580
0.7-0.8	130
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
0.8365	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD7003	Approved
0.8239	Intermediate Similarity	NPD9494	Approved
0.8221	Intermediate Similarity	NPD5844	Phase 1
0.821	Intermediate Similarity	NPD7473	Discontinued
0.8085	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7925	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1283	Approved
0.7898	Intermediate Similarity	NPD7458	Discontinued
0.7862	Intermediate Similarity	NPD1934	Approved
0.7857	Intermediate Similarity	NPD1651	Approved
0.7826	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2346	Discontinued
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7727	Intermediate Similarity	NPD8166	Discontinued
0.7718	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD3620	Phase 2
0.7718	Intermediate Similarity	NPD4060	Phase 1
0.7716	Intermediate Similarity	NPD3882	Suspended
0.7711	Intermediate Similarity	NPD6166	Phase 2
0.7711	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2801	Approved
0.7697	Intermediate Similarity	NPD5408	Approved
0.7697	Intermediate Similarity	NPD5405	Approved
0.7697	Intermediate Similarity	NPD5406	Approved
0.7697	Intermediate Similarity	NPD5404	Approved
0.7692	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1281	Approved
0.7676	Intermediate Similarity	NPD4626	Approved
0.7647	Intermediate Similarity	NPD6559	Discontinued
0.7636	Intermediate Similarity	NPD6959	Discontinued
0.7622	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD2979	Phase 3
0.7595	Intermediate Similarity	NPD6273	Approved
0.7593	Intermediate Similarity	NPD1465	Phase 2
0.7589	Intermediate Similarity	NPD5536	Phase 2
0.7584	Intermediate Similarity	NPD6798	Discontinued
0.7582	Intermediate Similarity	NPD2438	Suspended
0.7562	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD37	Approved
0.7517	Intermediate Similarity	NPD3972	Approved
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD1470	Approved
0.7483	Intermediate Similarity	NPD5691	Approved
0.7468	Intermediate Similarity	NPD1511	Approved
0.7467	Intermediate Similarity	NPD3764	Approved
0.7466	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1201	Approved
0.7439	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2798	Approved
0.7429	Intermediate Similarity	NPD5283	Phase 1
0.7419	Intermediate Similarity	NPD2344	Approved
0.7415	Intermediate Similarity	NPD1876	Approved
0.7412	Intermediate Similarity	NPD7177	Discontinued
0.7412	Intermediate Similarity	NPD3818	Discontinued
0.741	Intermediate Similarity	NPD228	Approved
0.7403	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1510	Phase 2
0.74	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3027	Phase 3
0.7394	Intermediate Similarity	NPD4965	Approved
0.7394	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD3750	Approved
0.7386	Intermediate Similarity	NPD1607	Approved
0.7375	Intermediate Similarity	NPD1512	Approved
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5494	Approved
0.7358	Intermediate Similarity	NPD7390	Discontinued
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7355	Intermediate Similarity	NPD2531	Phase 2
0.7349	Intermediate Similarity	NPD7075	Discontinued
0.7333	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7074	Phase 3
0.7321	Intermediate Similarity	NPD8127	Discontinued
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD447	Suspended
0.7312	Intermediate Similarity	NPD2534	Approved
0.7312	Intermediate Similarity	NPD2533	Approved
0.7312	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2532	Approved
0.7312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7228	Approved
0.7301	Intermediate Similarity	NPD7028	Phase 2
0.729	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD7008	Discontinued
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7054	Approved
0.7257	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7411	Suspended
0.7256	Intermediate Similarity	NPD6873	Phase 2
0.7255	Intermediate Similarity	NPD943	Approved
0.7255	Intermediate Similarity	NPD1240	Approved
0.7244	Intermediate Similarity	NPD1551	Phase 2
0.7244	Intermediate Similarity	NPD4476	Approved
0.7244	Intermediate Similarity	NPD4477	Approved
0.7239	Intermediate Similarity	NPD3455	Phase 2
0.7237	Intermediate Similarity	NPD2313	Discontinued
0.7235	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD7472	Approved
0.7215	Intermediate Similarity	NPD6674	Discontinued
0.7208	Intermediate Similarity	NPD1933	Approved
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD919	Approved
0.7195	Intermediate Similarity	NPD6599	Discontinued
0.7193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3019	Approved
0.719	Intermediate Similarity	NPD6233	Phase 2
0.7171	Intermediate Similarity	NPD7095	Approved
0.7171	Intermediate Similarity	NPD4625	Phase 3
0.7167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3021	Approved
0.7133	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD5978	Approved
0.7126	Intermediate Similarity	NPD5977	Approved
0.7125	Intermediate Similarity	NPD6190	Approved
0.7124	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2342	Discontinued
0.7118	Intermediate Similarity	NPD1247	Approved
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7107	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6797	Phase 2
0.7075	Intermediate Similarity	NPD2932	Approved
0.707	Intermediate Similarity	NPD3748	Approved
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5049	Phase 3
0.7051	Intermediate Similarity	NPD4097	Suspended
0.7045	Intermediate Similarity	NPD7685	Pre-registration
0.7045	Intermediate Similarity	NPD7251	Discontinued
0.7041	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3749	Approved
0.7039	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6799	Approved
0.7035	Intermediate Similarity	NPD3926	Phase 2
0.7032	Intermediate Similarity	NPD4307	Phase 2
0.703	Intermediate Similarity	NPD2651	Approved
0.703	Intermediate Similarity	NPD2649	Approved
0.7025	Intermediate Similarity	NPD2796	Approved
0.702	Intermediate Similarity	NPD1203	Approved
0.702	Intermediate Similarity	NPD1164	Approved
0.7014	Intermediate Similarity	NPD5951	Approved
0.7013	Intermediate Similarity	NPD3268	Approved
0.7012	Intermediate Similarity	NPD7427	Discontinued
0.7006	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7808	Phase 3
0.6993	Remote Similarity	NPD6832	Phase 2
0.6993	Remote Similarity	NPD4908	Phase 1
0.6989	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3657	Discovery
0.698	Remote Similarity	NPD1611	Approved
0.6975	Remote Similarity	NPD7440	Discontinued
0.6968	Remote Similarity	NPD8032	Phase 2
0.6968	Remote Similarity	NPD6663	Approved
0.6962	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6385	Approved
0.6946	Remote Similarity	NPD6386	Approved
0.6944	Remote Similarity	NPD1241	Discontinued
0.6944	Remote Similarity	NPD8150	Discontinued
0.6933	Remote Similarity	NPD7041	Phase 2
0.6933	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD824	Approved
0.6928	Remote Similarity	NPD5736	Approved
0.6927	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4140	Approved
0.6918	Remote Similarity	NPD6100	Approved
0.6918	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6099	Approved
0.6915	Remote Similarity	NPD2491	Approved
0.6906	Remote Similarity	NPD7693	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