NPASS Compound

Structure

NPC55527 OpenBabel07101718222D 22 25 0 0 1 0 0 0 0 0999 V2000 6.0191 -1.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 -1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0580 3.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 3.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8771 0.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1249 1.6238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3611 2.4194 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3482 2.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7036 3.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9801 1.8040 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 7 8 2 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 11 12 1 0 0 0 0 12 7 1 6 0 0 0 12 18 1 0 0 0 0 13 6 1 6 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 9 1 1 0 0 0 14 19 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 6 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	329.921
LogP:	6.115
LogD:	4.117
LogS:	-3.291
# Rotatable Bonds:	6
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	4.737
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.71
MDCK Permeability:	5.055725705460645e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.794
Plasma Protein Binding (PPB):	95.01935577392578%
Volume Distribution (VD):	0.64
Pgp-substrate:	2.888094186782837%

ADMET: Metabolism

CYP1A2-inhibitor:	0.585
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.372
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.322
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	2.367
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.652
Maximum Recommended Daily Dose:	0.092
Skin Sensitization:	0.157
Carcinogencity:	0.11
Eye Corrosion:	0.436
Eye Irritation:	0.432
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC55527

Natural Product ID:	NPC55527
*Common Name:**	Cryptobeilic Acid D
IUPAC Name:	n.a.
Synonyms:	Cryptobeilic Acid D
Standard InCHIKey:	XEQNTXMZKIDUJA-AQCKIFKESA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-2-3-4-5-6-13-14-9-10-15-16(20(21)22)8-7-12-11-17(13)19(14)18(12)15/h7-10,12-19H,2-6,11H2,1H3,(H,21,22)/t12-,13-,14-,15+,16-,17+,18-,19-/m1/s1
SMILES:	CCCCCC[C@@H]1[C@H]2C=C[C@@H]3[C@@H]4[C@H]2[C@H]1C[C@H]4C=C[C@H]3C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334428
PubChem CID:	71524396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001205] Carboxylic acids

*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	=	61000.0	nM	PMID[560043]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10800.0	nM	PMID[560043]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[560043]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	50.0	ug.mL-1	PMID[560043]
NPT3163	Organism	Acinetobacter calcoaceticus	Acinetobacter calcoaceticus	MIC	>	50.0	ug.mL-1	PMID[560043]

☑ 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 NPC55527 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	152
0.1-0.2	1228
0.2-0.3	9186
0.3-0.4	16049
0.4-0.5	8205
0.5-0.6	6236
0.6-0.7	1510
0.7-0.8	123
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8312	Intermediate Similarity	NPC196827
0.8312	Intermediate Similarity	NPC274996
0.8228	Intermediate Similarity	NPC260956
0.8125	Intermediate Similarity	NPC477852
0.8101	Intermediate Similarity	NPC201912
0.8101	Intermediate Similarity	NPC38350
0.8077	Intermediate Similarity	NPC477371
0.8072	Intermediate Similarity	NPC249889
0.8072	Intermediate Similarity	NPC193843
0.8	Intermediate Similarity	NPC296367
0.7976	Intermediate Similarity	NPC310236
0.7922	Intermediate Similarity	NPC69143
0.7901	Intermediate Similarity	NPC83569
0.7901	Intermediate Similarity	NPC310470
0.7901	Intermediate Similarity	NPC69279
0.7895	Intermediate Similarity	NPC283908
0.7895	Intermediate Similarity	NPC301065
0.7895	Intermediate Similarity	NPC103958
0.7895	Intermediate Similarity	NPC161923
0.7895	Intermediate Similarity	NPC183503
0.7875	Intermediate Similarity	NPC477372
0.7875	Intermediate Similarity	NPC147066
0.7857	Intermediate Similarity	NPC174560
0.7857	Intermediate Similarity	NPC125312
0.7848	Intermediate Similarity	NPC158846
0.7808	Intermediate Similarity	NPC60120
0.7792	Intermediate Similarity	NPC279666
0.7792	Intermediate Similarity	NPC192540
0.7778	Intermediate Similarity	NPC133391
0.7763	Intermediate Similarity	NPC321017
0.7711	Intermediate Similarity	NPC269638
0.7711	Intermediate Similarity	NPC29447
0.7703	Intermediate Similarity	NPC476614
0.7692	Intermediate Similarity	NPC309399
0.7683	Intermediate Similarity	NPC167103
0.7683	Intermediate Similarity	NPC477373
0.7683	Intermediate Similarity	NPC470015
0.7683	Intermediate Similarity	NPC168188
0.7662	Intermediate Similarity	NPC476046
0.7662	Intermediate Similarity	NPC241854
0.7662	Intermediate Similarity	NPC237591
0.7662	Intermediate Similarity	NPC3753
0.7662	Intermediate Similarity	NPC251970
0.7639	Intermediate Similarity	NPC234767
0.7632	Intermediate Similarity	NPC160817
0.7619	Intermediate Similarity	NPC155011
0.759	Intermediate Similarity	NPC164577
0.759	Intermediate Similarity	NPC165064
0.7564	Intermediate Similarity	NPC476844
0.7564	Intermediate Similarity	NPC201027
0.7561	Intermediate Similarity	NPC320514
0.7532	Intermediate Similarity	NPC35656
0.7529	Intermediate Similarity	NPC233836
0.7529	Intermediate Similarity	NPC187376
0.7529	Intermediate Similarity	NPC312215
0.7529	Intermediate Similarity	NPC128644
0.7529	Intermediate Similarity	NPC159046
0.75	Intermediate Similarity	NPC123319
0.75	Intermediate Similarity	NPC179028
0.75	Intermediate Similarity	NPC311702
0.75	Intermediate Similarity	NPC94531
0.75	Intermediate Similarity	NPC74410
0.7471	Intermediate Similarity	NPC46281
0.747	Intermediate Similarity	NPC97913
0.7468	Intermediate Similarity	NPC279537
0.7442	Intermediate Similarity	NPC48866
0.7442	Intermediate Similarity	NPC242864
0.7442	Intermediate Similarity	NPC247406
0.7442	Intermediate Similarity	NPC294480
0.7412	Intermediate Similarity	NPC55309
0.7412	Intermediate Similarity	NPC212843
0.7412	Intermediate Similarity	NPC28252
0.7407	Intermediate Similarity	NPC199595
0.7386	Intermediate Similarity	NPC26888
0.7386	Intermediate Similarity	NPC204341
0.7381	Intermediate Similarity	NPC194937
0.7381	Intermediate Similarity	NPC476038
0.7381	Intermediate Similarity	NPC472865
0.7375	Intermediate Similarity	NPC107039
0.7375	Intermediate Similarity	NPC471899
0.7375	Intermediate Similarity	NPC165711
0.7375	Intermediate Similarity	NPC137547
0.7375	Intermediate Similarity	NPC471897
0.7368	Intermediate Similarity	NPC199557
0.7356	Intermediate Similarity	NPC77168
0.7356	Intermediate Similarity	NPC102414
0.7356	Intermediate Similarity	NPC84271
0.7356	Intermediate Similarity	NPC128496
0.7356	Intermediate Similarity	NPC262043
0.7349	Intermediate Similarity	NPC73882
0.7342	Intermediate Similarity	NPC476795
0.7326	Intermediate Similarity	NPC136948
0.7326	Intermediate Similarity	NPC167877
0.7326	Intermediate Similarity	NPC96496
0.7326	Intermediate Similarity	NPC236618
0.7326	Intermediate Similarity	NPC474684
0.7326	Intermediate Similarity	NPC142361
0.7308	Intermediate Similarity	NPC330659
0.7308	Intermediate Similarity	NPC161187
0.7308	Intermediate Similarity	NPC244708
0.7294	Intermediate Similarity	NPC283733
0.7284	Intermediate Similarity	NPC169095
0.7284	Intermediate Similarity	NPC280654
0.7284	Intermediate Similarity	NPC321514
0.7284	Intermediate Similarity	NPC110094
0.7284	Intermediate Similarity	NPC260385
0.7273	Intermediate Similarity	NPC175628
0.7273	Intermediate Similarity	NPC111585
0.7273	Intermediate Similarity	NPC148414
0.7273	Intermediate Similarity	NPC123854
0.7262	Intermediate Similarity	NPC476082
0.7262	Intermediate Similarity	NPC278648
0.725	Intermediate Similarity	NPC180886
0.725	Intermediate Similarity	NPC89294
0.725	Intermediate Similarity	NPC41017
0.725	Intermediate Similarity	NPC246445
0.7241	Intermediate Similarity	NPC320665
0.7241	Intermediate Similarity	NPC183546
0.7229	Intermediate Similarity	NPC473420
0.7229	Intermediate Similarity	NPC88735
0.7215	Intermediate Similarity	NPC166797
0.7215	Intermediate Similarity	NPC213223
0.7215	Intermediate Similarity	NPC306928
0.7209	Intermediate Similarity	NPC264127
0.7209	Intermediate Similarity	NPC222613
0.7209	Intermediate Similarity	NPC6247
0.7209	Intermediate Similarity	NPC475022
0.7209	Intermediate Similarity	NPC118648
0.7209	Intermediate Similarity	NPC186975
0.7206	Intermediate Similarity	NPC1813
0.7206	Intermediate Similarity	NPC36061
0.7206	Intermediate Similarity	NPC139029
0.7206	Intermediate Similarity	NPC294548
0.72	Intermediate Similarity	NPC126899
0.72	Intermediate Similarity	NPC154728
0.72	Intermediate Similarity	NPC304665
0.7195	Intermediate Similarity	NPC16394
0.7195	Intermediate Similarity	NPC327674
0.7195	Intermediate Similarity	NPC215843
0.7195	Intermediate Similarity	NPC231431
0.7191	Intermediate Similarity	NPC45269
0.7183	Intermediate Similarity	NPC329819
0.7176	Intermediate Similarity	NPC473246
0.7176	Intermediate Similarity	NPC472864
0.7176	Intermediate Similarity	NPC221758
0.7176	Intermediate Similarity	NPC59453
0.7176	Intermediate Similarity	NPC19849
0.716	Intermediate Similarity	NPC66105
0.716	Intermediate Similarity	NPC68828
0.716	Intermediate Similarity	NPC61952
0.716	Intermediate Similarity	NPC97377
0.7159	Intermediate Similarity	NPC155479
0.7159	Intermediate Similarity	NPC214387
0.7159	Intermediate Similarity	NPC54689
0.7159	Intermediate Similarity	NPC474570
0.7159	Intermediate Similarity	NPC475921
0.7159	Intermediate Similarity	NPC474704
0.7159	Intermediate Similarity	NPC474889
0.7159	Intermediate Similarity	NPC66344
0.7143	Intermediate Similarity	NPC238991
0.7143	Intermediate Similarity	NPC251779
0.7143	Intermediate Similarity	NPC321289
0.7143	Intermediate Similarity	NPC151519
0.7143	Intermediate Similarity	NPC327969
0.7143	Intermediate Similarity	NPC100297
0.7143	Intermediate Similarity	NPC7414
0.7143	Intermediate Similarity	NPC302661
0.7143	Intermediate Similarity	NPC69101
0.7143	Intermediate Similarity	NPC240302
0.7143	Intermediate Similarity	NPC171395
0.7143	Intermediate Similarity	NPC193347
0.7126	Intermediate Similarity	NPC136548
0.7126	Intermediate Similarity	NPC58063
0.7125	Intermediate Similarity	NPC68624
0.7125	Intermediate Similarity	NPC113639
0.7111	Intermediate Similarity	NPC206810
0.7111	Intermediate Similarity	NPC152897
0.7111	Intermediate Similarity	NPC66429
0.7108	Intermediate Similarity	NPC104545
0.7108	Intermediate Similarity	NPC26139
0.7108	Intermediate Similarity	NPC37038
0.7108	Intermediate Similarity	NPC271104
0.7105	Intermediate Similarity	NPC476626
0.7105	Intermediate Similarity	NPC472875
0.7101	Intermediate Similarity	NPC87564
0.7101	Intermediate Similarity	NPC88966
0.7101	Intermediate Similarity	NPC261831
0.7101	Intermediate Similarity	NPC6095
0.7101	Intermediate Similarity	NPC154245
0.7101	Intermediate Similarity	NPC290563
0.7101	Intermediate Similarity	NPC25417
0.7101	Intermediate Similarity	NPC85813
0.7101	Intermediate Similarity	NPC424
0.7101	Intermediate Similarity	NPC281972
0.7101	Intermediate Similarity	NPC32467
0.7093	Intermediate Similarity	NPC474537
0.7093	Intermediate Similarity	NPC11711
0.7093	Intermediate Similarity	NPC474083
0.7093	Intermediate Similarity	NPC147921
0.7093	Intermediate Similarity	NPC469948

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 NPC55527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1850
0.2-0.3	4333
0.3-0.4	1929
0.4-0.5	506
0.5-0.6	284
0.6-0.7	99
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7386	Intermediate Similarity	NPD5284	Approved
0.7386	Intermediate Similarity	NPD5281	Approved
0.7284	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5362	Discontinued
0.7241	Intermediate Similarity	NPD4518	Approved
0.7229	Intermediate Similarity	NPD5369	Approved
0.7209	Intermediate Similarity	NPD5690	Phase 2
0.7206	Intermediate Similarity	NPD3172	Approved
0.7176	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD4270	Approved
0.7143	Intermediate Similarity	NPD4269	Approved
0.7111	Intermediate Similarity	NPD6399	Phase 3
0.7108	Intermediate Similarity	NPD5368	Approved
0.7101	Intermediate Similarity	NPD3194	Approved
0.7101	Intermediate Similarity	NPD3195	Phase 2
0.7101	Intermediate Similarity	NPD4266	Approved
0.7101	Intermediate Similarity	NPD3196	Approved
0.7024	Intermediate Similarity	NPD857	Phase 3
0.7011	Intermediate Similarity	NPD4694	Approved
0.7011	Intermediate Similarity	NPD5280	Approved
0.7011	Intermediate Similarity	NPD5279	Phase 3
0.6977	Remote Similarity	NPD4197	Approved
0.6966	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6101	Approved
0.6957	Remote Similarity	NPD5695	Phase 3
0.6941	Remote Similarity	NPD6435	Approved
0.6905	Remote Similarity	NPD4821	Approved
0.6905	Remote Similarity	NPD4822	Approved
0.6905	Remote Similarity	NPD4252	Approved
0.6905	Remote Similarity	NPD4819	Approved
0.6905	Remote Similarity	NPD4820	Approved
0.6897	Remote Similarity	NPD5363	Approved
0.6897	Remote Similarity	NPD5329	Approved
0.6889	Remote Similarity	NPD5207	Approved
0.6867	Remote Similarity	NPD4268	Approved
0.6867	Remote Similarity	NPD4271	Approved
0.686	Remote Similarity	NPD5331	Approved
0.686	Remote Similarity	NPD5332	Approved
0.6824	Remote Similarity	NPD4790	Discontinued
0.6824	Remote Similarity	NPD4139	Approved
0.6824	Remote Similarity	NPD4692	Approved
0.6818	Remote Similarity	NPD4690	Approved
0.6818	Remote Similarity	NPD4693	Phase 3
0.6818	Remote Similarity	NPD5205	Approved
0.6818	Remote Similarity	NPD4688	Approved
0.6818	Remote Similarity	NPD6098	Approved
0.6818	Remote Similarity	NPD4689	Approved
0.6818	Remote Similarity	NPD5786	Approved
0.6818	Remote Similarity	NPD4138	Approved
0.6813	Remote Similarity	NPD5694	Approved
0.6813	Remote Similarity	NPD6411	Approved
0.6782	Remote Similarity	NPD3665	Phase 1
0.6782	Remote Similarity	NPD3133	Approved
0.6782	Remote Similarity	NPD3666	Approved
0.6753	Remote Similarity	NPD7331	Phase 2
0.6739	Remote Similarity	NPD5778	Approved
0.6739	Remote Similarity	NPD5779	Approved
0.6706	Remote Similarity	NPD4695	Discontinued
0.6706	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4096	Approved
0.6703	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD28	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD29	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6632	Remote Similarity	NPD6084	Phase 2
0.6632	Remote Similarity	NPD6083	Phase 2
0.663	Remote Similarity	NPD6050	Approved
0.663	Remote Similarity	NPD6079	Approved
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD3618	Phase 1
0.6629	Remote Similarity	NPD6409	Approved
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD5330	Approved
0.6623	Remote Similarity	NPD7341	Phase 2
0.6618	Remote Similarity	NPD3173	Approved
0.6593	Remote Similarity	NPD6673	Approved
0.6593	Remote Similarity	NPD5328	Approved
0.6593	Remote Similarity	NPD6080	Approved
0.6593	Remote Similarity	NPD4753	Phase 2
0.6593	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6904	Approved
0.6591	Remote Similarity	NPD3668	Phase 3
0.6588	Remote Similarity	NPD4195	Approved
0.6585	Remote Similarity	NPD4784	Approved
0.6585	Remote Similarity	NPD4785	Approved
0.6585	Remote Similarity	NPD4687	Approved
0.6562	Remote Similarity	NPD5696	Approved
0.6543	Remote Similarity	NPD5276	Approved
0.6522	Remote Similarity	NPD5785	Approved
0.6517	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6903	Approved
0.6471	Remote Similarity	NPD622	Approved
0.6452	Remote Similarity	NPD5693	Phase 1
0.6444	Remote Similarity	NPD4519	Discontinued
0.6444	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4623	Approved
0.6421	Remote Similarity	NPD4629	Approved
0.6421	Remote Similarity	NPD5210	Approved
0.642	Remote Similarity	NPD4747	Approved
0.6404	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5733	Approved
0.6386	Remote Similarity	NPD6924	Approved
0.6386	Remote Similarity	NPD6926	Approved
0.6383	Remote Similarity	NPD4202	Approved
0.6383	Remote Similarity	NPD5133	Approved
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5221	Approved
0.6354	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5222	Approved
0.6341	Remote Similarity	NPD4243	Approved
0.6329	Remote Similarity	NPD4224	Phase 2
0.6316	Remote Similarity	NPD6001	Approved
0.631	Remote Similarity	NPD7339	Approved
0.631	Remote Similarity	NPD6942	Approved
0.631	Remote Similarity	NPD8039	Approved
0.6296	Remote Similarity	NPD4137	Phase 3
0.6289	Remote Similarity	NPD5173	Approved
0.6282	Remote Similarity	NPD3197	Phase 1
0.6277	Remote Similarity	NPD7637	Suspended
0.6277	Remote Similarity	NPD7515	Phase 2
0.6275	Remote Similarity	NPD5697	Approved
0.6264	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5654	Approved
0.6235	Remote Similarity	NPD6933	Approved
0.6235	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7143	Approved
0.622	Remote Similarity	NPD7144	Approved
0.622	Remote Similarity	NPD4691	Approved
0.6214	Remote Similarity	NPD6881	Approved
0.6214	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD6899	Approved
0.6196	Remote Similarity	NPD4251	Approved
0.6196	Remote Similarity	NPD3573	Approved
0.6196	Remote Similarity	NPD4250	Approved
0.619	Remote Similarity	NPD4058	Approved
0.6186	Remote Similarity	NPD4697	Phase 3
0.6184	Remote Similarity	NPD3198	Approved
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD3174	Discontinued
0.6176	Remote Similarity	NPD4222	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.6176	Remote Similarity	NPD634	Phase 3
0.6173	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5286	Approved
0.6162	Remote Similarity	NPD4696	Approved
0.6162	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6146	Remote Similarity	NPD7748	Approved
0.6146	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD7150	Approved
0.6145	Remote Similarity	NPD7152	Approved
0.6145	Remote Similarity	NPD6081	Approved
0.6145	Remote Similarity	NPD7151	Approved
0.6122	Remote Similarity	NPD5959	Approved
0.6122	Remote Similarity	NPD4755	Approved
0.6118	Remote Similarity	NPD4190	Phase 3
0.6118	Remote Similarity	NPD5275	Approved
0.6117	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD4788	Approved
0.6105	Remote Similarity	NPD8034	Phase 2
0.6105	Remote Similarity	NPD8035	Phase 2
0.61	Remote Similarity	NPD5223	Approved
0.6098	Remote Similarity	NPD6923	Approved
0.6098	Remote Similarity	NPD6922	Approved
0.6095	Remote Similarity	NPD7102	Approved
0.6095	Remote Similarity	NPD7290	Approved
0.6095	Remote Similarity	NPD6883	Approved
0.6092	Remote Similarity	NPD3732	Approved
0.6082	Remote Similarity	NPD1693	Approved
0.6058	Remote Similarity	NPD7320	Approved
0.6047	Remote Similarity	NPD1346	Approved
0.604	Remote Similarity	NPD5091	Approved
0.604	Remote Similarity	NPD5224	Approved
0.604	Remote Similarity	NPD5225	Approved
0.604	Remote Similarity	NPD5226	Approved
0.604	Remote Similarity	NPD4633	Approved
0.604	Remote Similarity	NPD5211	Phase 2
0.6038	Remote Similarity	NPD6617	Approved
0.6038	Remote Similarity	NPD6847	Approved
0.6038	Remote Similarity	NPD8130	Phase 1
0.6038	Remote Similarity	NPD6650	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