NPASS Compound

Structure

CID279537 OpenBabel06191716082D 24 24 0 0 1 0 0 0 0 0999 V2000 -6.8292 4.3568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8347 4.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2469 3.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -1.3685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 -2.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2524 3.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9680 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6896 -3.0158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6646 2.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8975 -3.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 2.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6701 3.0523 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 2 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 -0.1544 -4.6631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2634 3.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7967 -4.3540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3623 -5.6412 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 6 1 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 17 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 17 21 1 6 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 19 22 2 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	373.171
LogP:	3.874
LogD:	2.533
LogS:	-4.139
# Rotatable Bonds:	13
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	3.5
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.165
MDCK Permeability:	3.945683783967979e-05
Pgp-inhibitor:	0.203
Pgp-substrate:	0.464
Human Intestinal Absorption (HIA):	0.765
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	89.35767364501953%
Volume Distribution (VD):	0.586
Pgp-substrate:	1.5114134550094604%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.548
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	3.35
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.441
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.783
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.42
Carcinogencity:	0.098
Eye Corrosion:	0.004
Eye Irritation:	0.073
Respiratory Toxicity:	0.451

Download Data

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

Natural Product: NPC279537

Natural Product ID:	NPC279537
*Common Name:**	L-Prostaglandin E1
IUPAC Name:	7-[(1R,2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
Synonyms:
Standard InCHIKey:	DPNOTBLPQOITGU-LDDQNKHRSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12,14,16-18,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1
SMILES:	CCCCC[C@@H](/C=C/[C@H]1CCC(=O)[C@@H]1CCCCCCC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3246389
PubChem CID:	5283055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO3722	Litoria subglandulosa	Species	Hylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23535	Naganishia albida	Species	Filobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6508	Dendrilla cactos	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5554	Quercus lanceaefolia	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4629	Angelica tschimganica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10218	Gracilariopsis longissima	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO932	Myrceugenia exsucca	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24	Gypsophila patrinii	Species	Caryophyllaceae	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
ED50	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT938	Organism	Cavia porcellus	Cavia porcellus	ED50	=	1.07	g/Kg	PMID[507709]
NPT938	Organism	Cavia porcellus	Cavia porcellus	ED50	=	7.0	g/Kg	PMID[507709]
NPT938	Organism	Cavia porcellus	Cavia porcellus	ED50	=	3.3	g/Kg	PMID[507709]

☑ 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 NPC279537 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	148
0.1-0.2	955
0.2-0.3	5444
0.3-0.4	15563
0.4-0.5	9226
0.5-0.6	6688
0.6-0.7	3872
0.7-0.8	758
0.8-0.85	30
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC47031
0.9211	High Similarity	NPC7414
0.9189	High Similarity	NPC192006
0.9079	High Similarity	NPC88735
0.9067	High Similarity	NPC201225
0.8947	High Similarity	NPC115418
0.8684	High Similarity	NPC323249
0.8684	High Similarity	NPC39547
0.8684	High Similarity	NPC260814
0.8684	High Similarity	NPC27949
0.8378	Intermediate Similarity	NPC67076
0.8378	Intermediate Similarity	NPC319163
0.8354	Intermediate Similarity	NPC316844
0.8182	Intermediate Similarity	NPC469646
0.8158	Intermediate Similarity	NPC227396
0.8125	Intermediate Similarity	NPC470241
0.8101	Intermediate Similarity	NPC164308
0.8082	Intermediate Similarity	NPC60120
0.8082	Intermediate Similarity	NPC99619
0.8082	Intermediate Similarity	NPC26500
0.8077	Intermediate Similarity	NPC281296
0.8056	Intermediate Similarity	NPC245947
0.8056	Intermediate Similarity	NPC136164
0.8056	Intermediate Similarity	NPC255863
0.8049	Intermediate Similarity	NPC165064
0.8	Intermediate Similarity	NPC477215
0.8	Intermediate Similarity	NPC310236
0.8	Intermediate Similarity	NPC476388
0.8	Intermediate Similarity	NPC214387
0.7975	Intermediate Similarity	NPC121200
0.7973	Intermediate Similarity	NPC476614
0.7955	Intermediate Similarity	NPC472469
0.7952	Intermediate Similarity	NPC125290
0.7917	Intermediate Similarity	NPC470320
0.7907	Intermediate Similarity	NPC477149
0.7907	Intermediate Similarity	NPC477147
0.7887	Intermediate Similarity	NPC174560
0.7887	Intermediate Similarity	NPC125312
0.7882	Intermediate Similarity	NPC249889
0.7882	Intermediate Similarity	NPC193843
0.7875	Intermediate Similarity	NPC89128
0.7867	Intermediate Similarity	NPC143396
0.7867	Intermediate Similarity	NPC469677
0.7865	Intermediate Similarity	NPC301534
0.7865	Intermediate Similarity	NPC250757
0.7848	Intermediate Similarity	NPC476439
0.7821	Intermediate Similarity	NPC474011
0.7821	Intermediate Similarity	NPC199445
0.7808	Intermediate Similarity	NPC326268
0.7808	Intermediate Similarity	NPC318420
0.7792	Intermediate Similarity	NPC321017
0.7792	Intermediate Similarity	NPC275098
0.7778	Intermediate Similarity	NPC107243
0.7765	Intermediate Similarity	NPC128644
0.7765	Intermediate Similarity	NPC316629
0.7765	Intermediate Similarity	NPC237540
0.7765	Intermediate Similarity	NPC287079
0.7763	Intermediate Similarity	NPC318766
0.7763	Intermediate Similarity	NPC4299
0.7753	Intermediate Similarity	NPC54905
0.7753	Intermediate Similarity	NPC314009
0.7753	Intermediate Similarity	NPC476174
0.775	Intermediate Similarity	NPC218817
0.775	Intermediate Similarity	NPC239098
0.775	Intermediate Similarity	NPC11796
0.7746	Intermediate Similarity	NPC243532
0.7738	Intermediate Similarity	NPC474083
0.7738	Intermediate Similarity	NPC28887
0.7738	Intermediate Similarity	NPC261380
0.7738	Intermediate Similarity	NPC269638
0.7738	Intermediate Similarity	NPC471224
0.7722	Intermediate Similarity	NPC61863
0.7722	Intermediate Similarity	NPC12740
0.7722	Intermediate Similarity	NPC469514
0.7722	Intermediate Similarity	NPC110461
0.7711	Intermediate Similarity	NPC69469
0.7703	Intermediate Similarity	NPC126899
0.7703	Intermediate Similarity	NPC154728
0.7703	Intermediate Similarity	NPC304665
0.7701	Intermediate Similarity	NPC145666
0.7701	Intermediate Similarity	NPC473448
0.7692	Intermediate Similarity	NPC472966
0.7683	Intermediate Similarity	NPC191711
0.7683	Intermediate Similarity	NPC52861
0.7683	Intermediate Similarity	NPC325031
0.7671	Intermediate Similarity	NPC226592
0.7667	Intermediate Similarity	NPC456
0.7667	Intermediate Similarity	NPC472941
0.7662	Intermediate Similarity	NPC29328
0.7654	Intermediate Similarity	NPC469690
0.7654	Intermediate Similarity	NPC226226
0.7654	Intermediate Similarity	NPC55304
0.7654	Intermediate Similarity	NPC469620
0.7647	Intermediate Similarity	NPC116575
0.7647	Intermediate Similarity	NPC322159
0.7647	Intermediate Similarity	NPC202394
0.764	Intermediate Similarity	NPC469406
0.7639	Intermediate Similarity	NPC201939
0.7632	Intermediate Similarity	NPC67608
0.7632	Intermediate Similarity	NPC101622
0.7632	Intermediate Similarity	NPC236208
0.7625	Intermediate Similarity	NPC116177
0.7625	Intermediate Similarity	NPC107668
0.7625	Intermediate Similarity	NPC7563
0.7625	Intermediate Similarity	NPC320630
0.7619	Intermediate Similarity	NPC96259
0.7619	Intermediate Similarity	NPC476804
0.7619	Intermediate Similarity	NPC141193
0.7619	Intermediate Similarity	NPC295799
0.7619	Intermediate Similarity	NPC474776
0.7619	Intermediate Similarity	NPC194937
0.7619	Intermediate Similarity	NPC476038
0.7614	Intermediate Similarity	NPC45269
0.7614	Intermediate Similarity	NPC473986
0.7614	Intermediate Similarity	NPC474018
0.7609	Intermediate Similarity	NPC266955
0.76	Intermediate Similarity	NPC278895
0.76	Intermediate Similarity	NPC472875
0.759	Intermediate Similarity	NPC85772
0.759	Intermediate Similarity	NPC89555
0.759	Intermediate Similarity	NPC474252
0.7586	Intermediate Similarity	NPC123912
0.7586	Intermediate Similarity	NPC281524
0.7586	Intermediate Similarity	NPC155479
0.7586	Intermediate Similarity	NPC2983
0.7582	Intermediate Similarity	NPC475894
0.7582	Intermediate Similarity	NPC57416
0.7582	Intermediate Similarity	NPC253826
0.7568	Intermediate Similarity	NPC474329
0.7568	Intermediate Similarity	NPC474304
0.7561	Intermediate Similarity	NPC271104
0.7561	Intermediate Similarity	NPC306095
0.7561	Intermediate Similarity	NPC103634
0.7561	Intermediate Similarity	NPC200446
0.7558	Intermediate Similarity	NPC96496
0.7558	Intermediate Similarity	NPC86005
0.7558	Intermediate Similarity	NPC477959
0.7558	Intermediate Similarity	NPC312215
0.7558	Intermediate Similarity	NPC179659
0.7556	Intermediate Similarity	NPC173875
0.7556	Intermediate Similarity	NPC318282
0.7556	Intermediate Similarity	NPC476488
0.7556	Intermediate Similarity	NPC469995
0.7556	Intermediate Similarity	NPC174948
0.7556	Intermediate Similarity	NPC476487
0.7531	Intermediate Similarity	NPC127526
0.7531	Intermediate Similarity	NPC267231
0.7531	Intermediate Similarity	NPC231739
0.7531	Intermediate Similarity	NPC297996
0.7531	Intermediate Similarity	NPC93763
0.7531	Intermediate Similarity	NPC475994
0.7531	Intermediate Similarity	NPC108816
0.7531	Intermediate Similarity	NPC128276
0.7529	Intermediate Similarity	NPC255307
0.7529	Intermediate Similarity	NPC165162
0.7529	Intermediate Similarity	NPC283733
0.7529	Intermediate Similarity	NPC475206
0.7529	Intermediate Similarity	NPC137033
0.7528	Intermediate Similarity	NPC243866
0.7527	Intermediate Similarity	NPC115899
0.7527	Intermediate Similarity	NPC476240
0.7527	Intermediate Similarity	NPC224720
0.7527	Intermediate Similarity	NPC476223
0.7527	Intermediate Similarity	NPC282524
0.75	Intermediate Similarity	NPC166745
0.75	Intermediate Similarity	NPC310470
0.75	Intermediate Similarity	NPC108368
0.75	Intermediate Similarity	NPC320026
0.75	Intermediate Similarity	NPC235464
0.75	Intermediate Similarity	NPC469400
0.75	Intermediate Similarity	NPC232202
0.75	Intermediate Similarity	NPC46281
0.75	Intermediate Similarity	NPC97913
0.75	Intermediate Similarity	NPC469688
0.75	Intermediate Similarity	NPC57079
0.75	Intermediate Similarity	NPC197386
0.75	Intermediate Similarity	NPC224532
0.75	Intermediate Similarity	NPC271070
0.75	Intermediate Similarity	NPC273508
0.75	Intermediate Similarity	NPC209327
0.75	Intermediate Similarity	NPC474447
0.75	Intermediate Similarity	NPC327112
0.75	Intermediate Similarity	NPC215893
0.7473	Intermediate Similarity	NPC328371
0.7473	Intermediate Similarity	NPC29152
0.7473	Intermediate Similarity	NPC155676
0.7471	Intermediate Similarity	NPC294480
0.7471	Intermediate Similarity	NPC48866
0.7471	Intermediate Similarity	NPC247406
0.7471	Intermediate Similarity	NPC104560
0.747	Intermediate Similarity	NPC112868
0.747	Intermediate Similarity	NPC471325
0.747	Intermediate Similarity	NPC101012
0.7468	Intermediate Similarity	NPC55527
0.7444	Intermediate Similarity	NPC474690
0.7444	Intermediate Similarity	NPC8993
0.7444	Intermediate Similarity	NPC7165
0.7444	Intermediate Similarity	NPC65829
0.7444	Intermediate Similarity	NPC299100
0.7442	Intermediate Similarity	NPC316426

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 NPC279537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	1607
0.2-0.3	3922
0.3-0.4	2358
0.4-0.5	639
0.5-0.6	309
0.6-0.7	152
0.7-0.8	15
0.8-0.85	6
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9452	High Similarity	NPD5784	Clinical (unspecified phase)
0.9211	High Similarity	NPD4269	Approved
0.9211	High Similarity	NPD4270	Approved
0.8947	High Similarity	NPD4252	Approved
0.8861	High Similarity	NPD5363	Approved
0.8846	High Similarity	NPD5362	Discontinued
0.875	High Similarity	NPD5786	Approved
0.8701	High Similarity	NPD5368	Approved
0.8701	High Similarity	NPD4822	Approved
0.8701	High Similarity	NPD4820	Approved
0.8701	High Similarity	NPD4821	Approved
0.8701	High Similarity	NPD4819	Approved
0.8684	High Similarity	NPD4268	Approved
0.8684	High Similarity	NPD4271	Approved
0.859	High Similarity	NPD5369	Approved
0.8481	Intermediate Similarity	NPD6435	Approved
0.8462	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD5332	Approved
0.8375	Intermediate Similarity	NPD7154	Phase 3
0.8375	Intermediate Similarity	NPD5331	Approved
0.8354	Intermediate Similarity	NPD4790	Discontinued
0.8333	Intermediate Similarity	NPD5785	Approved
0.7765	Intermediate Similarity	NPD4250	Approved
0.7765	Intermediate Similarity	NPD4251	Approved
0.7647	Intermediate Similarity	NPD4249	Approved
0.7586	Intermediate Similarity	NPD5370	Suspended
0.7529	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3197	Phase 1
0.7416	Intermediate Similarity	NPD4810	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3198	Approved
0.7333	Intermediate Similarity	NPD5778	Approved
0.7333	Intermediate Similarity	NPD5779	Approved
0.7222	Intermediate Similarity	NPD7983	Approved
0.7222	Intermediate Similarity	NPD7637	Suspended
0.7209	Intermediate Similarity	NPD4786	Approved
0.7176	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3195	Phase 2
0.7143	Intermediate Similarity	NPD3196	Approved
0.7143	Intermediate Similarity	NPD3194	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD4266	Approved
0.7011	Intermediate Similarity	NPD5766	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD3172	Approved
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6915	Remote Similarity	NPD7839	Suspended
0.6875	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD7639	Approved
0.6854	Remote Similarity	NPD7334	Approved
0.6854	Remote Similarity	NPD6409	Approved
0.6854	Remote Similarity	NPD5330	Approved
0.6854	Remote Similarity	NPD6684	Approved
0.6854	Remote Similarity	NPD7146	Approved
0.6854	Remote Similarity	NPD3618	Phase 1
0.6854	Remote Similarity	NPD5279	Phase 3
0.6854	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD6411	Approved
0.6848	Remote Similarity	NPD7515	Phase 2
0.6848	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD6083	Phase 2
0.6842	Remote Similarity	NPD6084	Phase 2
0.6813	Remote Similarity	NPD5328	Approved
0.6809	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7331	Phase 2
0.6771	Remote Similarity	NPD7638	Approved
0.6765	Remote Similarity	NPD6420	Discontinued
0.6747	Remote Similarity	NPD8039	Approved
0.6742	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD28	Approved
0.6714	Remote Similarity	NPD29	Approved
0.6706	Remote Similarity	NPD3732	Approved
0.6703	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5737	Approved
0.6703	Remote Similarity	NPD6903	Approved
0.6703	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5695	Phase 3
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD3668	Phase 3
0.6591	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5209	Approved
0.6588	Remote Similarity	NPD4756	Discovery
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD6899	Approved
0.6566	Remote Similarity	NPD5211	Phase 2
0.6562	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5221	Approved
0.6562	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5222	Approved
0.6556	Remote Similarity	NPD1694	Approved
0.6552	Remote Similarity	NPD7514	Phase 3
0.6542	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6526	Remote Similarity	NPD7748	Approved
0.6512	Remote Similarity	NPD7145	Approved
0.6512	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6647	Phase 2
0.65	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5173	Approved
0.6494	Remote Similarity	NPD368	Approved
0.6484	Remote Similarity	NPD4519	Discontinued
0.6484	Remote Similarity	NPD4623	Approved
0.6477	Remote Similarity	NPD6902	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6463	Remote Similarity	NPD7144	Approved
0.6463	Remote Similarity	NPD7143	Approved
0.6458	Remote Similarity	NPD5210	Approved
0.6458	Remote Similarity	NPD4629	Approved
0.6456	Remote Similarity	NPD7341	Phase 2
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD7102	Approved
0.6442	Remote Similarity	NPD6371	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6437	Remote Similarity	NPD6929	Approved
0.6436	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD3173	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD6926	Approved
0.6429	Remote Similarity	NPD6924	Approved
0.6421	Remote Similarity	NPD4202	Approved
0.6408	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD6011	Approved
0.6404	Remote Similarity	NPD4223	Phase 3
0.6404	Remote Similarity	NPD4221	Approved
0.6395	Remote Similarity	NPD5776	Phase 2
0.6395	Remote Similarity	NPD6925	Approved
0.6392	Remote Similarity	NPD4697	Phase 3
0.6386	Remote Similarity	NPD7151	Approved
0.6386	Remote Similarity	NPD7150	Approved
0.6386	Remote Similarity	NPD7152	Approved
0.6383	Remote Similarity	NPD7838	Discovery
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6617	Approved
0.6381	Remote Similarity	NPD6869	Approved
0.6381	Remote Similarity	NPD6650	Approved
0.6381	Remote Similarity	NPD8130	Phase 1
0.6381	Remote Similarity	NPD6649	Approved
0.6374	Remote Similarity	NPD5329	Approved
0.6364	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6364	Remote Similarity	NPD7332	Phase 2
0.6364	Remote Similarity	NPD6930	Phase 2
0.6364	Remote Similarity	NPD6931	Approved
0.6353	Remote Similarity	NPD8264	Approved
0.6346	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD6372	Approved
0.6346	Remote Similarity	NPD6014	Approved
0.6346	Remote Similarity	NPD6373	Approved
0.6346	Remote Similarity	NPD6012	Approved
0.6341	Remote Similarity	NPD6923	Approved
0.6341	Remote Similarity	NPD6922	Approved
0.6333	Remote Similarity	NPD4788	Approved
0.6333	Remote Similarity	NPD6695	Phase 3
0.6333	Remote Similarity	NPD6110	Phase 1
0.6329	Remote Similarity	NPD7909	Approved
0.6327	Remote Similarity	NPD4755	Approved
0.6327	Remote Similarity	NPD7902	Approved
0.6321	Remote Similarity	NPD6882	Approved
0.6321	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD8034	Phase 2
0.6316	Remote Similarity	NPD8035	Phase 2
0.6311	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5701	Approved
0.6304	Remote Similarity	NPD6422	Discontinued
0.6304	Remote Similarity	NPD5690	Phase 2
0.6304	Remote Similarity	NPD6098	Approved
0.63	Remote Similarity	NPD5223	Approved
0.6286	Remote Similarity	NPD622	Approved
0.6279	Remote Similarity	NPD6117	Approved
0.6279	Remote Similarity	NPD6933	Approved
0.6277	Remote Similarity	NPD6904	Approved
0.6277	Remote Similarity	NPD6673	Approved
0.6277	Remote Similarity	NPD6080	Approved
0.6264	Remote Similarity	NPD4197	Approved
0.6264	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6686	Approved
0.6238	Remote Similarity	NPD5225	Approved
0.6238	Remote Similarity	NPD4633	Approved
0.6238	Remote Similarity	NPD7632	Discontinued
0.6238	Remote Similarity	NPD5224	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