NPASS Compound

Structure

CID17840 OpenBabel06191715342D 28 28 0 0 0 0 0 0 0 0999 V2000 9.5263 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 5.1962 -1.0000 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 3.4641 -1.0000 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 -0.8660 -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 -1.0000 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 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 -1.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.28
Volume:	437.082
LogP:	7.36
LogD:	4.433
LogS:	-2.487
# Rotatable Bonds:	16
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	2.481
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.226
MDCK Permeability:	2.688913809834048e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	100.08592987060547%
Volume Distribution (VD):	0.558
Pgp-substrate:	0.309255450963974%

ADMET: Metabolism

CYP1A2-inhibitor:	0.433
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.485
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.9
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	2.154
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.115
Drug-inuced Liver Injury (DILI):	0.577
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.926
Carcinogencity:	0.045
Eye Corrosion:	0.008
Eye Irritation:	0.892
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC17840

Natural Product ID:	NPC17840
*Common Name:**	Merulinic Acid A
IUPAC Name:	2-[(Z)-heptadec-8-enyl]-4,6-dihydroxybenzoic acid
Synonyms:
Standard InCHIKey:	IXDZSQUQSCLSSD-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C24H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-18-21(25)19-22(26)23(20)24(27)28/h9-10,18-19,25-26H,2-8,11-17H2,1H3,(H,27,28)/b10-9-
SMILES:	CCCCCCCC/C=CCCCCCCCc1cc(cc(c1C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476715
PubChem CID:	21591019
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid 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
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1801	Koenigia polystachya	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16152	Phlebia radiata	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO32809	merulius tremellosus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO16152	Phlebia radiata	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1801	Koenigia polystachya	Species	Polygonaceae	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1388	Organism	Arthrobacter citreus	Arthrobacter citreus	MIC	=	0.4	ug.mL-1	PMID[492532]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.4	ug.mL-1	PMID[492532]
NPT1389	Organism	Clavibacter michiganensis subsp. insidiosus	Clavibacter michiganensis subsp. insidiosus	MIC	=	0.4	ug.mL-1	PMID[492532]
NPT1390	Organism	Kocuria rosea	Kocuria rosea	MIC	=	0.4	ug.mL-1	PMID[492532]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.4	ug.mL-1	PMID[492532]

☑ 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 NPC17840 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	307
0.1-0.2	1458
0.2-0.3	3369
0.3-0.4	9209
0.4-0.5	10119
0.5-0.6	4667
0.6-0.7	7739
0.7-0.8	5031
0.8-0.85	524
0.85-0.9	207
0.9-0.95	57
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC247477
0.9606	High Similarity	NPC180261
0.9606	High Similarity	NPC37299
0.9593	High Similarity	NPC201728
0.9593	High Similarity	NPC262671
0.9516	High Similarity	NPC473691
0.9462	High Similarity	NPC71256
0.9435	High Similarity	NPC477454
0.9385	High Similarity	NPC118919
0.937	High Similarity	NPC259942
0.9365	High Similarity	NPC41263
0.9313	High Similarity	NPC194579
0.9308	High Similarity	NPC290803
0.9291	High Similarity	NPC92624
0.9286	High Similarity	NPC209959
0.9187	High Similarity	NPC179092
0.9187	High Similarity	NPC292665
0.9187	High Similarity	NPC178395
0.9187	High Similarity	NPC35856
0.9187	High Similarity	NPC244994
0.9187	High Similarity	NPC272454
0.9187	High Similarity	NPC115188
0.9187	High Similarity	NPC26433
0.9187	High Similarity	NPC222876
0.9187	High Similarity	NPC159760
0.9187	High Similarity	NPC301987
0.9167	High Similarity	NPC178467
0.9167	High Similarity	NPC474771
0.9167	High Similarity	NPC65837
0.9167	High Similarity	NPC474849
0.9167	High Similarity	NPC70380
0.9167	High Similarity	NPC149372
0.9154	High Similarity	NPC48036
0.9147	High Similarity	NPC219892
0.9147	High Similarity	NPC189823
0.9098	High Similarity	NPC478200
0.9098	High Similarity	NPC9121
0.9098	High Similarity	NPC177307
0.9098	High Similarity	NPC191835
0.9098	High Similarity	NPC212693
0.9098	High Similarity	NPC94248
0.9098	High Similarity	NPC33144
0.9098	High Similarity	NPC475974
0.9084	High Similarity	NPC166480
0.9084	High Similarity	NPC282780
0.9037	High Similarity	NPC313123
0.9037	High Similarity	NPC478217
0.9032	High Similarity	NPC149246
0.9024	High Similarity	NPC184579
0.9024	High Similarity	NPC233165
0.9015	High Similarity	NPC278375
0.9008	High Similarity	NPC153783
0.8976	High Similarity	NPC167055
0.8976	High Similarity	NPC240744
0.8971	High Similarity	NPC250755
0.8963	High Similarity	NPC158472
0.8955	High Similarity	NPC472602
0.8955	High Similarity	NPC472403
0.8947	High Similarity	NPC223836
0.8947	High Similarity	NPC191976
0.8947	High Similarity	NPC158481
0.8939	High Similarity	NPC175943
0.8939	High Similarity	NPC474394
0.8905	High Similarity	NPC478202
0.8897	High Similarity	NPC67650
0.8897	High Similarity	NPC472035
0.8897	High Similarity	NPC475730
0.8897	High Similarity	NPC158634
0.8897	High Similarity	NPC478201
0.8897	High Similarity	NPC53649
0.8897	High Similarity	NPC1704
0.8889	High Similarity	NPC91105
0.8889	High Similarity	NPC474655
0.8889	High Similarity	NPC105456
0.8889	High Similarity	NPC139634
0.8889	High Similarity	NPC244351
0.8889	High Similarity	NPC283514
0.8889	High Similarity	NPC472903
0.8881	High Similarity	NPC290030
0.888	High Similarity	NPC146642
0.8872	High Similarity	NPC180905
0.8872	High Similarity	NPC182496
0.8862	High Similarity	NPC125252
0.8841	High Similarity	NPC151607
0.8841	High Similarity	NPC42540
0.8837	High Similarity	NPC116513
0.8832	High Similarity	NPC474385
0.8828	High Similarity	NPC475733
0.8824	High Similarity	NPC472601
0.8824	High Similarity	NPC472600
0.8819	High Similarity	NPC472029
0.8819	High Similarity	NPC65761
0.881	High Similarity	NPC215392
0.881	High Similarity	NPC198336
0.8806	High Similarity	NPC474726
0.8806	High Similarity	NPC235115
0.8806	High Similarity	NPC50455
0.8806	High Similarity	NPC475955
0.88	High Similarity	NPC294037
0.879	High Similarity	NPC40649
0.879	High Similarity	NPC209486
0.879	High Similarity	NPC241089
0.8788	High Similarity	NPC175738
0.8786	High Similarity	NPC125801
0.8779	High Similarity	NPC62219
0.8777	High Similarity	NPC29577
0.8777	High Similarity	NPC83272
0.8769	High Similarity	NPC95537
0.8768	High Similarity	NPC472006
0.8768	High Similarity	NPC51106
0.8768	High Similarity	NPC159721
0.8768	High Similarity	NPC354984
0.876	High Similarity	NPC267846
0.876	High Similarity	NPC8745
0.8759	High Similarity	NPC472604
0.8759	High Similarity	NPC472904
0.8759	High Similarity	NPC472603
0.8759	High Similarity	NPC472605
0.875	High Similarity	NPC13238
0.875	High Similarity	NPC32360
0.875	High Similarity	NPC138099
0.875	High Similarity	NPC52358
0.875	High Similarity	NPC162939
0.875	High Similarity	NPC242994
0.8741	High Similarity	NPC135837
0.874	High Similarity	NPC309765
0.8722	High Similarity	NPC267205
0.872	High Similarity	NPC161617
0.8714	High Similarity	NPC237208
0.8714	High Similarity	NPC225173
0.8714	High Similarity	NPC163846
0.8714	High Similarity	NPC473023
0.871	High Similarity	NPC121259
0.8705	High Similarity	NPC126882
0.8705	High Similarity	NPC277426
0.8705	High Similarity	NPC86373
0.8705	High Similarity	NPC280404
0.8705	High Similarity	NPC210966
0.8705	High Similarity	NPC210425
0.8705	High Similarity	NPC478203
0.8702	High Similarity	NPC474998
0.8702	High Similarity	NPC109123
0.8692	High Similarity	NPC23126
0.8692	High Similarity	NPC72158
0.8692	High Similarity	NPC30501
0.8692	High Similarity	NPC105157
0.8692	High Similarity	NPC162612
0.8692	High Similarity	NPC103356
0.8692	High Similarity	NPC100067
0.8692	High Similarity	NPC98254
0.8692	High Similarity	NPC266689
0.8692	High Similarity	NPC169250
0.8692	High Similarity	NPC190043
0.8686	High Similarity	NPC165172
0.8686	High Similarity	NPC181560
0.8686	High Similarity	NPC169452
0.8686	High Similarity	NPC99441
0.8686	High Similarity	NPC155205
0.8682	High Similarity	NPC10926
0.8661	High Similarity	NPC303737
0.8661	High Similarity	NPC196976
0.8661	High Similarity	NPC242895
0.8657	High Similarity	NPC474519
0.8657	High Similarity	NPC44437
0.8643	High Similarity	NPC134621
0.8643	High Similarity	NPC472034
0.8643	High Similarity	NPC257558
0.8636	High Similarity	NPC147757
0.8633	High Similarity	NPC471731
0.8633	High Similarity	NPC469542
0.8633	High Similarity	NPC472610
0.8629	High Similarity	NPC477453
0.8626	High Similarity	NPC473017
0.8626	High Similarity	NPC179898
0.8626	High Similarity	NPC21305
0.8626	High Similarity	NPC221777
0.8623	High Similarity	NPC37530
0.8623	High Similarity	NPC244923
0.8615	High Similarity	NPC95309
0.8615	High Similarity	NPC62952
0.8615	High Similarity	NPC473751
0.8613	High Similarity	NPC275356
0.8613	High Similarity	NPC92655
0.8613	High Similarity	NPC88269
0.8613	High Similarity	NPC268052
0.8613	High Similarity	NPC471819
0.8603	High Similarity	NPC53414
0.8603	High Similarity	NPC53001
0.8603	High Similarity	NPC471905
0.8603	High Similarity	NPC53206
0.8594	High Similarity	NPC32032
0.8594	High Similarity	NPC133909
0.8593	High Similarity	NPC27407
0.8593	High Similarity	NPC161632
0.8593	High Similarity	NPC142027
0.8592	High Similarity	NPC37139
0.8592	High Similarity	NPC221352
0.8582	High Similarity	NPC472033
0.8582	High Similarity	NPC107625
0.8571	High Similarity	NPC95123

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 NPC17840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	927
0.2-0.3	1596
0.3-0.4	2727
0.4-0.5	1988
0.5-0.6	1108
0.6-0.7	393
0.7-0.8	99
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8613	High Similarity	NPD970	Clinical (unspecified phase)
0.8529	High Similarity	NPD1509	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD943	Approved
0.8333	Intermediate Similarity	NPD5408	Approved
0.8333	Intermediate Similarity	NPD5406	Approved
0.8333	Intermediate Similarity	NPD5405	Approved
0.8333	Intermediate Similarity	NPD5404	Approved
0.831	Intermediate Similarity	NPD7390	Discontinued
0.8252	Intermediate Similarity	NPD2533	Approved
0.8252	Intermediate Similarity	NPD2534	Approved
0.8252	Intermediate Similarity	NPD2532	Approved
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8092	Intermediate Similarity	NPD1201	Approved
0.803	Intermediate Similarity	NPD9269	Phase 2
0.8	Intermediate Similarity	NPD9268	Approved
0.7985	Intermediate Similarity	NPD1164	Approved
0.7985	Intermediate Similarity	NPD1470	Approved
0.7984	Intermediate Similarity	NPD9266	Approved
0.7984	Intermediate Similarity	NPD74	Approved
0.7971	Intermediate Similarity	NPD1240	Approved
0.7943	Intermediate Similarity	NPD2935	Discontinued
0.7922	Intermediate Similarity	NPD6232	Discontinued
0.7907	Intermediate Similarity	NPD9493	Approved
0.7907	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD9267	Approved
0.7903	Intermediate Similarity	NPD9263	Approved
0.7903	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD9264	Approved
0.7885	Intermediate Similarity	NPD7473	Discontinued
0.7872	Intermediate Similarity	NPD1510	Phase 2
0.7857	Intermediate Similarity	NPD1607	Approved
0.7847	Intermediate Similarity	NPD3750	Approved
0.7786	Intermediate Similarity	NPD230	Phase 1
0.7755	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3749	Approved
0.7662	Intermediate Similarity	NPD7075	Discontinued
0.7652	Intermediate Similarity	NPD9545	Approved
0.7642	Intermediate Similarity	NPD940	Approved
0.7642	Intermediate Similarity	NPD846	Approved
0.7639	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD9281	Approved
0.7603	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7768	Phase 2
0.7594	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1549	Phase 2
0.7582	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD9261	Approved
0.7571	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3764	Approved
0.7568	Intermediate Similarity	NPD6799	Approved
0.7568	Intermediate Similarity	NPD1511	Approved
0.7566	Intermediate Similarity	NPD7411	Suspended
0.7532	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD6599	Discontinued
0.7483	Intermediate Similarity	NPD6651	Approved
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5711	Approved
0.7468	Intermediate Similarity	NPD2801	Approved
0.7468	Intermediate Similarity	NPD5710	Approved
0.7467	Intermediate Similarity	NPD1512	Approved
0.7448	Intermediate Similarity	NPD1551	Phase 2
0.7448	Intermediate Similarity	NPD2796	Approved
0.7419	Intermediate Similarity	NPD3817	Phase 2
0.7415	Intermediate Similarity	NPD2800	Approved
0.7405	Intermediate Similarity	NPD6959	Discontinued
0.7386	Intermediate Similarity	NPD4380	Phase 2
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7375	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3882	Suspended
0.7338	Intermediate Similarity	NPD1203	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7329	Intermediate Similarity	NPD6099	Approved
0.7324	Intermediate Similarity	NPD411	Approved
0.732	Intermediate Similarity	NPD3226	Approved
0.7297	Intermediate Similarity	NPD1243	Approved
0.7292	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD6801	Discontinued
0.7285	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3019	Approved
0.7279	Intermediate Similarity	NPD4626	Approved
0.7279	Intermediate Similarity	NPD2346	Discontinued
0.7279	Intermediate Similarity	NPD2932	Approved
0.7267	Intermediate Similarity	NPD3300	Phase 2
0.7261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1465	Phase 2
0.7239	Intermediate Similarity	NPD5844	Phase 1
0.7215	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7074	Phase 3
0.7183	Intermediate Similarity	NPD6832	Phase 2
0.7181	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD422	Phase 1
0.7163	Intermediate Similarity	NPD2798	Approved
0.7162	Intermediate Similarity	NPD2344	Approved
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.7134	Intermediate Similarity	NPD7054	Approved
0.7133	Intermediate Similarity	NPD4628	Phase 3
0.7122	Intermediate Similarity	NPD1608	Approved
0.7113	Intermediate Similarity	NPD5736	Approved
0.7092	Intermediate Similarity	NPD2797	Approved
0.7091	Intermediate Similarity	NPD7472	Approved
0.7083	Intermediate Similarity	NPD3268	Approved
0.7078	Intermediate Similarity	NPD920	Approved
0.7078	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3818	Discontinued
0.7067	Intermediate Similarity	NPD2654	Approved
0.7048	Intermediate Similarity	NPD5953	Discontinued
0.7039	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD520	Approved
0.703	Intermediate Similarity	NPD7286	Phase 2
0.703	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6020	Phase 2
0.7027	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1283	Approved
0.702	Intermediate Similarity	NPD7003	Approved
0.7007	Intermediate Similarity	NPD1759	Phase 1
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.6981	Remote Similarity	NPD5402	Approved
0.6981	Remote Similarity	NPD4288	Approved
0.6974	Remote Similarity	NPD2309	Approved
0.6968	Remote Similarity	NPD5403	Approved
0.6966	Remote Similarity	NPD2313	Discontinued
0.6964	Remote Similarity	NPD7808	Phase 3
0.6964	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5951	Approved
0.696	Remote Similarity	NPD844	Approved
0.6957	Remote Similarity	NPD5691	Approved
0.6957	Remote Similarity	NPD919	Approved
0.6948	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6797	Phase 2
0.6939	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1758	Phase 1
0.6933	Remote Similarity	NPD7229	Phase 3
0.6929	Remote Similarity	NPD3020	Approved
0.6914	Remote Similarity	NPD5494	Approved
0.6913	Remote Similarity	NPD4308	Phase 3
0.6912	Remote Similarity	NPD255	Approved
0.6912	Remote Similarity	NPD256	Approved
0.6908	Remote Similarity	NPD8166	Discontinued
0.6908	Remote Similarity	NPD3400	Discontinued
0.6906	Remote Similarity	NPD17	Approved
0.6905	Remote Similarity	NPD6559	Discontinued
0.6905	Remote Similarity	NPD288	Approved
0.6901	Remote Similarity	NPD8150	Discontinued
0.6883	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7458	Discontinued
0.6875	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7199	Phase 2
0.6863	Remote Similarity	NPD6190	Approved
0.6857	Remote Similarity	NPD3023	Approved
0.6857	Remote Similarity	NPD3026	Approved
0.6855	Remote Similarity	NPD37	Approved
0.6849	Remote Similarity	NPD1296	Phase 2
0.6842	Remote Similarity	NPD3021	Approved
0.6842	Remote Similarity	NPD3022	Approved
0.6839	Remote Similarity	NPD5401	Approved
0.6839	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3024	Approved
0.6835	Remote Similarity	NPD3025	Approved
0.6831	Remote Similarity	NPD1755	Approved
0.6825	Remote Similarity	NPD2859	Approved
0.6825	Remote Similarity	NPD2860	Approved
0.6815	Remote Similarity	NPD7635	Approved
0.6809	Remote Similarity	NPD1281	Approved
0.6806	Remote Similarity	NPD257	Approved
0.6806	Remote Similarity	NPD258	Approved
0.6806	Remote Similarity	NPD1019	Discontinued
0.68	Remote Similarity	NPD7033	Discontinued
0.6788	Remote Similarity	NPD3926	Phase 2
0.6788	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4625	Phase 3
0.6765	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3972	Approved
0.6759	Remote Similarity	NPD9494	Approved
0.6757	Remote Similarity	NPD4060	Phase 1
0.6748	Remote Similarity	NPD6234	Discontinued
0.6746	Remote Similarity	NPD2934	Approved
0.6746	Remote Similarity	NPD2933	Approved
0.6746	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3267	Approved
0.6736	Remote Similarity	NPD3266	Approved
0.6728	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD4965	Approved
0.6728	Remote Similarity	NPD4967	Phase 2

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