NPASS Compound

Structure

NPC189054 OpenBabel07101718272D 27 32 0 0 1 0 0 0 0 0999 V2000 -2.3801 -1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8771 0.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3778 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9319 0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8862 3.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3395 1.5110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1249 1.6238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3611 2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0580 3.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 0.0694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 0.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3482 2.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6827 4.0802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9801 1.8040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7036 3.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4959 0.5233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3518 1.6675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 10 1 0 0 0 0 2 3 2 0 0 0 0 4 18 1 0 0 0 0 5 10 1 0 0 0 0 6 10 2 0 0 0 0 6 19 1 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 26 1 0 0 0 0 9 27 1 0 0 0 0 11 2 1 6 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 3 1 6 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 5 1 1 0 0 0 13 14 1 0 0 0 0 14 7 1 6 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 7 1 1 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.13
Volume:	363.225
LogP:	4.91
LogD:	3.206
LogS:	-3.668
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.872
Synthetic Accessibility Score:	4.069
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.321
MDCK Permeability:	8.385715773329139e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.332

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	99.1426010131836%
Volume Distribution (VD):	0.341
Pgp-substrate:	1.1421509981155396%

ADMET: Metabolism

CYP1A2-inhibitor:	0.236
CYP1A2-substrate:	0.494
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.514
CYP2C9-substrate:	0.555
CYP2D6-inhibitor:	0.681
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	11.471
Half-life (T1/2):	0.39

ADMET: Toxicity

hERG Blockers:	0.254
Human Hepatotoxicity (H-HT):	0.504
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.039
Carcinogencity:	0.601
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC189054

Natural Product ID:	NPC189054
*Common Name:**	Cryptobeilic Acid C
IUPAC Name:	n.a.
Synonyms:	Cryptobeilic Acid C
Standard InCHIKey:	WIFSTHBLXUMVNG-OQBXOKOHSA-N
Standard InCHI:	InChI=1S/C22H20O5/c23-17-8-15(22(24)25)12-3-2-11-13(14-7-16(17)21(12)20(11)14)5-10-1-4-18-19(6-10)27-9-26-18/h1-4,6,8,11-14,16,20-21H,5,7,9H2,(H,24,25)/t11-,12+,13-,14+,16+,20-,21+/m1/s1
SMILES:	O=C1C=C(C(=O)O)[C@H]2[C@H]3[C@H]1C[C@@H]1[C@H]3[C@@H]([C@H]1Cc1ccc3c(c1)OCO3)C=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334427
PubChem CID:	71521968
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO33452	beilschmiedia cryptocaryoides	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23320609]

☑ 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	2
MIC	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	59300.0	nM	PMID[458889]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	14000.0	nM	PMID[458889]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[458889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	50.0	ug.mL-1	PMID[458889]
NPT3163	Organism	Acinetobacter calcoaceticus	Acinetobacter calcoaceticus	MIC	>	50.0	ug.mL-1	PMID[458889]

☑ 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 NPC189054 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	339
0.1-0.2	1453
0.2-0.3	3062
0.3-0.4	8000
0.4-0.5	11481
0.5-0.6	5828
0.6-0.7	11258
0.7-0.8	1223
0.8-0.85	46
0.85-0.9	2
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC323601
0.9493	High Similarity	NPC318575
0.942	High Similarity	NPC52968
0.942	High Similarity	NPC231719
0.8716	High Similarity	NPC476336
0.8643	High Similarity	NPC477705
0.8643	High Similarity	NPC477694
0.8582	High Similarity	NPC477706
0.8435	Intermediate Similarity	NPC28398
0.8429	Intermediate Similarity	NPC64948
0.8421	Intermediate Similarity	NPC12854
0.8403	Intermediate Similarity	NPC471913
0.8323	Intermediate Similarity	NPC476364
0.8322	Intermediate Similarity	NPC472564
0.8322	Intermediate Similarity	NPC137920
0.8322	Intermediate Similarity	NPC125134
0.8322	Intermediate Similarity	NPC86455
0.8311	Intermediate Similarity	NPC162851
0.8311	Intermediate Similarity	NPC246474
0.8311	Intermediate Similarity	NPC166137
0.8311	Intermediate Similarity	NPC282291
0.8311	Intermediate Similarity	NPC218092
0.8288	Intermediate Similarity	NPC102260
0.8288	Intermediate Similarity	NPC230968
0.8267	Intermediate Similarity	NPC46880
0.8255	Intermediate Similarity	NPC104956
0.8212	Intermediate Similarity	NPC247221
0.8207	Intermediate Similarity	NPC205915
0.8188	Intermediate Similarity	NPC29599
0.817	Intermediate Similarity	NPC40654
0.817	Intermediate Similarity	NPC262804
0.8163	Intermediate Similarity	NPC90431
0.8158	Intermediate Similarity	NPC472560
0.8151	Intermediate Similarity	NPC110958
0.8151	Intermediate Similarity	NPC19890
0.8146	Intermediate Similarity	NPC327623
0.8141	Intermediate Similarity	NPC205392
0.8141	Intermediate Similarity	NPC105942
0.8138	Intermediate Similarity	NPC239302
0.8133	Intermediate Similarity	NPC52664
0.8121	Intermediate Similarity	NPC470855
0.8117	Intermediate Similarity	NPC127827
0.8113	Intermediate Similarity	NPC68619
0.8099	Intermediate Similarity	NPC471929
0.8099	Intermediate Similarity	NPC471930
0.8099	Intermediate Similarity	NPC471935
0.8095	Intermediate Similarity	NPC252343
0.8092	Intermediate Similarity	NPC327052
0.8092	Intermediate Similarity	NPC271607
0.8092	Intermediate Similarity	NPC280717
0.8085	Intermediate Similarity	NPC471927
0.8082	Intermediate Similarity	NPC327410
0.8071	Intermediate Similarity	NPC256167
0.8067	Intermediate Similarity	NPC78987
0.8067	Intermediate Similarity	NPC82336
0.8065	Intermediate Similarity	NPC37220
0.8063	Intermediate Similarity	NPC476337
0.8054	Intermediate Similarity	NPC178290
0.8043	Intermediate Similarity	NPC57501
0.8039	Intermediate Similarity	NPC3982
0.8027	Intermediate Similarity	NPC4982
0.8027	Intermediate Similarity	NPC300776
0.8027	Intermediate Similarity	NPC176814
0.8027	Intermediate Similarity	NPC5310
0.8027	Intermediate Similarity	NPC68779
0.8026	Intermediate Similarity	NPC15743
0.8025	Intermediate Similarity	NPC100420
0.8014	Intermediate Similarity	NPC227002
0.8013	Intermediate Similarity	NPC475311
0.8013	Intermediate Similarity	NPC178048
0.8013	Intermediate Similarity	NPC473680
0.8013	Intermediate Similarity	NPC473579
0.8013	Intermediate Similarity	NPC475454
0.8012	Intermediate Similarity	NPC473467
0.8012	Intermediate Similarity	NPC475197
0.8	Intermediate Similarity	NPC472565
0.8	Intermediate Similarity	NPC475095
0.8	Intermediate Similarity	NPC179914
0.8	Intermediate Similarity	NPC472567
0.8	Intermediate Similarity	NPC172673
0.8	Intermediate Similarity	NPC24193
0.8	Intermediate Similarity	NPC275150
0.7987	Intermediate Similarity	NPC109765
0.7987	Intermediate Similarity	NPC166184
0.7975	Intermediate Similarity	NPC474301
0.7975	Intermediate Similarity	NPC103197
0.7975	Intermediate Similarity	NPC30009
0.7974	Intermediate Similarity	NPC235195
0.7974	Intermediate Similarity	NPC19862
0.7961	Intermediate Similarity	NPC229218
0.7961	Intermediate Similarity	NPC141817
0.7961	Intermediate Similarity	NPC169214
0.7961	Intermediate Similarity	NPC176030
0.7961	Intermediate Similarity	NPC192597
0.7949	Intermediate Similarity	NPC261322
0.7949	Intermediate Similarity	NPC475722
0.7949	Intermediate Similarity	NPC177830
0.7947	Intermediate Similarity	NPC51681
0.7937	Intermediate Similarity	NPC202495
0.7935	Intermediate Similarity	NPC181464
0.7931	Intermediate Similarity	NPC304622
0.7925	Intermediate Similarity	NPC476363
0.7917	Intermediate Similarity	NPC123228
0.7917	Intermediate Similarity	NPC151167
0.7917	Intermediate Similarity	NPC223807
0.7917	Intermediate Similarity	NPC276466
0.7917	Intermediate Similarity	NPC177167
0.7917	Intermediate Similarity	NPC5018
0.7917	Intermediate Similarity	NPC123722
0.7914	Intermediate Similarity	NPC69670
0.7911	Intermediate Similarity	NPC245948
0.7905	Intermediate Similarity	NPC45404
0.7902	Intermediate Similarity	NPC17348
0.7898	Intermediate Similarity	NPC477700
0.7898	Intermediate Similarity	NPC32079
0.7898	Intermediate Similarity	NPC118033
0.7898	Intermediate Similarity	NPC163002
0.7887	Intermediate Similarity	NPC249788
0.7887	Intermediate Similarity	NPC164778
0.7887	Intermediate Similarity	NPC4181
0.7887	Intermediate Similarity	NPC257976
0.7887	Intermediate Similarity	NPC242372
0.7885	Intermediate Similarity	NPC145569
0.7885	Intermediate Similarity	NPC216223
0.7875	Intermediate Similarity	NPC32373
0.7875	Intermediate Similarity	NPC237946
0.7872	Intermediate Similarity	NPC114845
0.7871	Intermediate Similarity	NPC476338
0.7871	Intermediate Similarity	NPC65574
0.7871	Intermediate Similarity	NPC101755
0.7871	Intermediate Similarity	NPC304687
0.7871	Intermediate Similarity	NPC476359
0.7871	Intermediate Similarity	NPC80230
0.7871	Intermediate Similarity	NPC104024
0.7867	Intermediate Similarity	NPC471152
0.7857	Intermediate Similarity	NPC229787
0.7857	Intermediate Similarity	NPC469438
0.7857	Intermediate Similarity	NPC474158
0.7853	Intermediate Similarity	NPC22130
0.7853	Intermediate Similarity	NPC116838
0.7852	Intermediate Similarity	NPC95485
0.7852	Intermediate Similarity	NPC88065
0.7852	Intermediate Similarity	NPC89504
0.7848	Intermediate Similarity	NPC475579
0.7848	Intermediate Similarity	NPC473773
0.7847	Intermediate Similarity	NPC274356
0.7847	Intermediate Similarity	NPC90128
0.7847	Intermediate Similarity	NPC84076
0.7847	Intermediate Similarity	NPC179777
0.7847	Intermediate Similarity	NPC213711
0.7847	Intermediate Similarity	NPC303680
0.7847	Intermediate Similarity	NPC40352
0.7842	Intermediate Similarity	NPC205502
0.784	Intermediate Similarity	NPC239818
0.784	Intermediate Similarity	NPC218471
0.7832	Intermediate Similarity	NPC273686
0.7832	Intermediate Similarity	NPC312404
0.7826	Intermediate Similarity	NPC115281
0.7826	Intermediate Similarity	NPC163527
0.7826	Intermediate Similarity	NPC181168
0.7826	Intermediate Similarity	NPC207584
0.7826	Intermediate Similarity	NPC19947
0.7821	Intermediate Similarity	NPC32017
0.7821	Intermediate Similarity	NPC96930
0.7818	Intermediate Similarity	NPC476277
0.7817	Intermediate Similarity	NPC114298
0.7815	Intermediate Similarity	NPC132723
0.7815	Intermediate Similarity	NPC76032
0.7811	Intermediate Similarity	NPC469397
0.7808	Intermediate Similarity	NPC476748
0.7793	Intermediate Similarity	NPC286683
0.7792	Intermediate Similarity	NPC224884
0.7792	Intermediate Similarity	NPC209085
0.7792	Intermediate Similarity	NPC475000
0.7791	Intermediate Similarity	NPC288149
0.7785	Intermediate Similarity	NPC37065
0.7785	Intermediate Similarity	NPC471110
0.7778	Intermediate Similarity	NPC76211
0.7778	Intermediate Similarity	NPC176586
0.7778	Intermediate Similarity	NPC280767
0.7778	Intermediate Similarity	NPC85830
0.7778	Intermediate Similarity	NPC472410
0.7778	Intermediate Similarity	NPC53305
0.7778	Intermediate Similarity	NPC257589
0.7778	Intermediate Similarity	NPC210354
0.7771	Intermediate Similarity	NPC474556
0.7771	Intermediate Similarity	NPC668
0.7771	Intermediate Similarity	NPC298647
0.7771	Intermediate Similarity	NPC174512
0.7771	Intermediate Similarity	NPC177476
0.7771	Intermediate Similarity	NPC273358
0.7771	Intermediate Similarity	NPC292206
0.7771	Intermediate Similarity	NPC262455
0.7771	Intermediate Similarity	NPC474965
0.7771	Intermediate Similarity	NPC477695
0.7771	Intermediate Similarity	NPC293757
0.777	Intermediate Similarity	NPC199209
0.777	Intermediate Similarity	NPC212643
0.7762	Intermediate Similarity	NPC163083
0.7756	Intermediate Similarity	NPC88345

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 NPC189054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	882
0.2-0.3	1598
0.3-0.4	2633
0.4-0.5	2184
0.5-0.6	1164
0.6-0.7	373
0.7-0.8	25
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8859	High Similarity	NPD7028	Phase 2
0.8212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD37	Approved
0.7875	Intermediate Similarity	NPD4967	Phase 2
0.7875	Intermediate Similarity	NPD4966	Approved
0.7875	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD8127	Discontinued
0.7662	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4110	Phase 3
0.7662	Intermediate Similarity	NPD8166	Discontinued
0.7616	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7458	Discontinued
0.7517	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD8032	Phase 2
0.7466	Intermediate Similarity	NPD1283	Approved
0.7456	Intermediate Similarity	NPD7228	Approved
0.7421	Intermediate Similarity	NPD6273	Approved
0.7394	Intermediate Similarity	NPD5536	Phase 2
0.7361	Intermediate Similarity	NPD2932	Approved
0.7361	Intermediate Similarity	NPD4626	Approved
0.7347	Intermediate Similarity	NPD1876	Approved
0.7303	Intermediate Similarity	NPD3620	Phase 2
0.7303	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1357	Approved
0.7283	Intermediate Similarity	NPD7685	Pre-registration
0.726	Intermediate Similarity	NPD1281	Approved
0.726	Intermediate Similarity	NPD3705	Approved
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7241	Intermediate Similarity	NPD3019	Approved
0.7237	Intermediate Similarity	NPD6663	Approved
0.7234	Intermediate Similarity	NPD5283	Phase 1
0.7215	Intermediate Similarity	NPD7003	Approved
0.7193	Intermediate Similarity	NPD7473	Discontinued
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4140	Approved
0.7184	Intermediate Similarity	NPD7240	Approved
0.7179	Intermediate Similarity	NPD2935	Discontinued
0.7172	Intermediate Similarity	NPD1651	Approved
0.7159	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3818	Discontinued
0.7133	Intermediate Similarity	NPD2798	Approved
0.7118	Intermediate Similarity	NPD6232	Discontinued
0.7115	Intermediate Similarity	NPD2799	Discontinued
0.7107	Intermediate Similarity	NPD4628	Phase 3
0.7107	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD5736	Approved
0.7078	Intermediate Similarity	NPD2979	Phase 3
0.7078	Intermediate Similarity	NPD4060	Phase 1
0.707	Intermediate Similarity	NPD2438	Suspended
0.7067	Intermediate Similarity	NPD2797	Approved
0.7066	Intermediate Similarity	NPD5977	Approved
0.7066	Intermediate Similarity	NPD5978	Approved
0.7059	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD5691	Approved
0.7032	Intermediate Similarity	NPD447	Suspended
0.7032	Intermediate Similarity	NPD1933	Approved
0.7025	Intermediate Similarity	NPD5763	Approved
0.7025	Intermediate Similarity	NPD5762	Approved
0.7025	Intermediate Similarity	NPD2346	Discontinued
0.702	Intermediate Similarity	NPD5647	Approved
0.702	Intermediate Similarity	NPD4624	Approved
0.7011	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD3750	Approved
0.6993	Remote Similarity	NPD7095	Approved
0.6988	Remote Similarity	NPD6873	Phase 2
0.6987	Remote Similarity	NPD6653	Approved
0.6972	Remote Similarity	NPD228	Approved
0.697	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3023	Approved
0.6959	Remote Similarity	NPD3026	Approved
0.6957	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6798	Discontinued
0.6939	Remote Similarity	NPD3025	Approved
0.6939	Remote Similarity	NPD3024	Approved
0.6937	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3657	Discovery
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6005	Phase 3
0.6918	Remote Similarity	NPD7266	Discontinued
0.6918	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6002	Phase 3
0.6909	Remote Similarity	NPD1653	Approved
0.6905	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD2492	Phase 1
0.6875	Remote Similarity	NPD5958	Discontinued
0.6875	Remote Similarity	NPD1241	Discontinued
0.6867	Remote Similarity	NPD1608	Approved
0.6867	Remote Similarity	NPD3972	Approved
0.6855	Remote Similarity	NPD2531	Phase 2
0.6846	Remote Similarity	NPD3847	Discontinued
0.6839	Remote Similarity	NPD2313	Discontinued
0.6835	Remote Similarity	NPD7097	Phase 1
0.6832	Remote Similarity	NPD6674	Discontinued
0.6829	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3882	Suspended
0.6824	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2614	Approved
0.6816	Remote Similarity	NPD8312	Approved
0.6816	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7281	Phase 3
0.6816	Remote Similarity	NPD7280	Phase 3
0.6816	Remote Similarity	NPD8313	Approved
0.6815	Remote Similarity	NPD5735	Approved
0.6813	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1358	Approved
0.6805	Remote Similarity	NPD7819	Suspended
0.6802	Remote Similarity	NPD5494	Approved
0.6798	Remote Similarity	NPD6764	Approved
0.6798	Remote Similarity	NPD6765	Approved
0.6795	Remote Similarity	NPD6233	Phase 2
0.6792	Remote Similarity	NPD3748	Approved
0.678	Remote Similarity	NPD7074	Phase 3
0.6772	Remote Similarity	NPD6353	Approved
0.677	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3226	Approved
0.6765	Remote Similarity	NPD3817	Phase 2
0.676	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1894	Discontinued
0.6748	Remote Similarity	NPD6190	Approved
0.6746	Remote Similarity	NPD1934	Approved
0.6743	Remote Similarity	NPD2898	Approved
0.6738	Remote Similarity	NPD3134	Approved
0.6732	Remote Similarity	NPD3267	Approved
0.6732	Remote Similarity	NPD3266	Approved
0.6727	Remote Similarity	NPD2533	Approved
0.6727	Remote Similarity	NPD2534	Approved
0.6727	Remote Similarity	NPD2532	Approved
0.6723	Remote Similarity	NPD7054	Approved
0.6711	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5327	Phase 3
0.6706	Remote Similarity	NPD2801	Approved
0.6706	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8455	Phase 2
0.6706	Remote Similarity	NPD1465	Phase 2
0.6703	Remote Similarity	NPD8434	Phase 2
0.6702	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1535	Discovery
0.6688	Remote Similarity	NPD4062	Phase 3
0.6687	Remote Similarity	NPD4308	Phase 3
0.6687	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7680	Approved
0.6648	Remote Similarity	NPD6784	Approved
0.6648	Remote Similarity	NPD6785	Approved
0.6647	Remote Similarity	NPD919	Approved
0.6646	Remote Similarity	NPD4476	Approved
0.6646	Remote Similarity	NPD4477	Approved
0.6645	Remote Similarity	NPD2861	Phase 2
0.6645	Remote Similarity	NPD1481	Phase 2
0.6629	Remote Similarity	NPD7315	Approved
0.6623	Remote Similarity	NPD3496	Discontinued
0.6608	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7236	Approved
0.6605	Remote Similarity	NPD2344	Approved
0.6604	Remote Similarity	NPD230	Phase 1
0.66	Remote Similarity	NPD5585	Approved
0.6599	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3021	Approved
0.6597	Remote Similarity	NPD3022	Approved
0.659	Remote Similarity	NPD7075	Discontinued
0.6588	Remote Similarity	NPD6385	Approved
0.6588	Remote Similarity	NPD6386	Approved
0.6585	Remote Similarity	NPD6331	Phase 2
0.6584	Remote Similarity	NPD4108	Discontinued
0.6584	Remote Similarity	NPD1510	Phase 2
0.6581	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5535	Approved
0.6575	Remote Similarity	NPD7808	Phase 3
0.6573	Remote Similarity	NPD7799	Discontinued
0.6573	Remote Similarity	NPD3751	Discontinued
0.6571	Remote Similarity	NPD2821	Approved
0.6568	Remote Similarity	NPD3455	Phase 2
0.6566	Remote Similarity	NPD4357	Discontinued
0.6566	Remote Similarity	NPD1511	Approved
0.6564	Remote Similarity	NPD4534	Discontinued
0.6562	Remote Similarity	NPD2157	Approved
0.6559	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1778	Approved
0.6556	Remote Similarity	NPD6797	Phase 2
0.6552	Remote Similarity	NPD6315	Phase 2
0.6548	Remote Similarity	NPD3639	Approved
0.6548	Remote Similarity	NPD3641	Approved
0.6548	Remote Similarity	NPD3640	Phase 3
0.6545	Remote Similarity	NPD2354	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