NPASS Compound

Structure

NPC245521 OpenBabel07101719252D 34 34 0 0 1 0 0 0 0 0999 V2000 -6.4261 2.4774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8212 -1.6264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3838 -2.6557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4664 -1.5753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7968 3.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8091 3.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4508 2.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4631 2.0081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1047 1.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1170 0.9181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6132 -0.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6622 -0.3393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3564 0.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4877 1.6953 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 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0780 -2.2956 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 -0.8090 0.5878 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 -2.9190 -1.0084 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9680 -0.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3074 -0.2882 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 -0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.2859 -3.2737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6896 -3.0158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0506 0.3810 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 -0.1502 2.4757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5154 -1.2663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1270 -1.9865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -1.3685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 32 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 14 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 27 2 0 0 0 0 17 33 1 0 0 0 0 18 28 2 0 0 0 0 18 34 1 0 0 0 0 19 24 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 26 1 0 0 0 0 21 12 1 1 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 15 1 6 0 0 0 22 34 1 0 0 0 0 23 29 2 0 0 0 0 23 32 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.2
Volume:	499.477
LogP:	3.241
LogD:	2.659
LogS:	-4.357
# Rotatable Bonds:	17
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	4.319
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.735
MDCK Permeability:	5.6736604165052995e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.558
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.959
Plasma Protein Binding (PPB):	85.72623443603516%
Volume Distribution (VD):	0.677
Pgp-substrate:	14.50979995727539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.707
CYP2C19-substrate:	0.401
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.431
CYP2D6-inhibitor:	0.303
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	3.551
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.774
Drug-inuced Liver Injury (DILI):	0.392
AMES Toxicity:	0.819
Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.964
Carcinogencity:	0.862
Eye Corrosion:	0.013
Eye Irritation:	0.027
Respiratory Toxicity:	0.862

Download Data

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

Natural Product: NPC245521

Natural Product ID:	NPC245521
*Common Name:**	Punaglandin 4
IUPAC Name:	methyl (5S,6S,7E)-5,6-diacetyloxy-7-[(2R)-4-chloro-2-hydroxy-2-[(Z)-oct-2-enyl]-5-oxocyclopent-3-en-1-ylidene]heptanoate
Synonyms:	Punaglandin 4
Standard InCHIKey:	HMDYASDJIREJJW-ORSYJHFOSA-N
Standard InCHI:	InChI=1S/C25H35ClO8/c1-5-6-7-8-9-10-14-25(31)16-20(26)24(30)19(25)15-22(34-18(3)28)21(33-17(2)27)12-11-13-23(29)32-4/h9-10,15-16,21-22,31H,5-8,11-14H2,1-4H3/b10-9-,19-15-/t21-,22-,25+/m0/s1
SMILES:	CCCCC/C=CC[C@@]1(O)C=C(C(=O)/C/1=C/[C@@H]([C@@H](OC(=O)C)CCCC(=O)OC)OC(=O)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL65090
PubChem CID:	5283248
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0001021] Clavulones and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11893	Telesto riisei	Species	Telestidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7857405]
NPO11893	Telesto riisei	Species	Telestidae	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
EC50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6566	Cell Line	HCT cell line		EC50	=	330.0	nM	PMID[544680]
NPT6566	Cell Line	HCT cell line		EC50	=	350.0	nM	PMID[544680]
NPT6566	Cell Line	HCT cell line		EC50	=	340.0	nM	PMID[544680]
NPT6566	Cell Line	HCT cell line		EC50	=	280.0	nM	PMID[544680]
NPT2170	Cell Line	RKO	Homo sapiens	EC50	=	310.0	nM	PMID[544680]
NPT2170	Cell Line	RKO	Homo sapiens	EC50	=	370.0	nM	PMID[544680]

☑ 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 NPC245521 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	210
0.1-0.2	1468
0.2-0.3	5619
0.3-0.4	10146
0.4-0.5	16319
0.5-0.6	6148
0.6-0.7	2497
0.7-0.8	289
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.798	Intermediate Similarity	NPC471142
0.7938	Intermediate Similarity	NPC474761
0.7938	Intermediate Similarity	NPC476004
0.7864	Intermediate Similarity	NPC149371
0.7822	Intermediate Similarity	NPC40812
0.78	Intermediate Similarity	NPC477922
0.78	Intermediate Similarity	NPC36954
0.7789	Intermediate Similarity	NPC21469
0.7788	Intermediate Similarity	NPC472755
0.7778	Intermediate Similarity	NPC476300
0.7767	Intermediate Similarity	NPC474742
0.7767	Intermediate Similarity	NPC47880
0.7755	Intermediate Similarity	NPC51004
0.7755	Intermediate Similarity	NPC71533
0.7755	Intermediate Similarity	NPC106510
0.7745	Intermediate Similarity	NPC261377
0.7745	Intermediate Similarity	NPC255592
0.7745	Intermediate Similarity	NPC471144
0.7745	Intermediate Similarity	NPC308567
0.7732	Intermediate Similarity	NPC227379
0.7732	Intermediate Similarity	NPC474471
0.7723	Intermediate Similarity	NPC476315
0.7723	Intermediate Similarity	NPC477921
0.7714	Intermediate Similarity	NPC100487
0.7706	Intermediate Similarity	NPC95290
0.7706	Intermediate Similarity	NPC189338
0.7692	Intermediate Similarity	NPC472754
0.7677	Intermediate Similarity	NPC111114
0.7677	Intermediate Similarity	NPC300312
0.7677	Intermediate Similarity	NPC473321
0.7677	Intermediate Similarity	NPC30515
0.7677	Intermediate Similarity	NPC261607
0.767	Intermediate Similarity	NPC288876
0.7653	Intermediate Similarity	NPC307411
0.7653	Intermediate Similarity	NPC474032
0.7629	Intermediate Similarity	NPC72513
0.7629	Intermediate Similarity	NPC160138
0.7624	Intermediate Similarity	NPC475659
0.7619	Intermediate Similarity	NPC475945
0.7619	Intermediate Similarity	NPC475871
0.7604	Intermediate Similarity	NPC137033
0.76	Intermediate Similarity	NPC288240
0.76	Intermediate Similarity	NPC273579
0.76	Intermediate Similarity	NPC295204
0.76	Intermediate Similarity	NPC162205
0.76	Intermediate Similarity	NPC475912
0.7596	Intermediate Similarity	NPC472753
0.7579	Intermediate Similarity	NPC250315
0.7576	Intermediate Similarity	NPC179394
0.7576	Intermediate Similarity	NPC473619
0.7576	Intermediate Similarity	NPC313670
0.7576	Intermediate Similarity	NPC144133
0.7576	Intermediate Similarity	NPC473455
0.7573	Intermediate Similarity	NPC83895
0.7573	Intermediate Similarity	NPC161855
0.7573	Intermediate Similarity	NPC187761
0.757	Intermediate Similarity	NPC232969
0.757	Intermediate Similarity	NPC199107
0.7551	Intermediate Similarity	NPC153570
0.7551	Intermediate Similarity	NPC153805
0.7549	Intermediate Similarity	NPC473859
0.7547	Intermediate Similarity	NPC203659
0.7547	Intermediate Similarity	NPC474741
0.7545	Intermediate Similarity	NPC35069
0.7545	Intermediate Similarity	NPC258711
0.7526	Intermediate Similarity	NPC309211
0.7526	Intermediate Similarity	NPC477010
0.7526	Intermediate Similarity	NPC122502
0.7526	Intermediate Similarity	NPC164393
0.7526	Intermediate Similarity	NPC469483
0.7525	Intermediate Similarity	NPC81386
0.7525	Intermediate Similarity	NPC474035
0.7524	Intermediate Similarity	NPC474747
0.75	Intermediate Similarity	NPC184463
0.75	Intermediate Similarity	NPC475949
0.7476	Intermediate Similarity	NPC471462
0.7475	Intermediate Similarity	NPC477017
0.7475	Intermediate Similarity	NPC477011
0.7475	Intermediate Similarity	NPC295312
0.7475	Intermediate Similarity	NPC14901
0.7475	Intermediate Similarity	NPC130359
0.7475	Intermediate Similarity	NPC83423
0.7475	Intermediate Similarity	NPC87306
0.7475	Intermediate Similarity	NPC477016
0.7474	Intermediate Similarity	NPC85772
0.7453	Intermediate Similarity	NPC110989
0.7453	Intermediate Similarity	NPC475873
0.7451	Intermediate Similarity	NPC14961
0.7451	Intermediate Similarity	NPC270013
0.7451	Intermediate Similarity	NPC214694
0.7449	Intermediate Similarity	NPC477959
0.7449	Intermediate Similarity	NPC473248
0.7449	Intermediate Similarity	NPC179659
0.7449	Intermediate Similarity	NPC248602
0.7426	Intermediate Similarity	NPC11456
0.7426	Intermediate Similarity	NPC179746
0.7426	Intermediate Similarity	NPC81419
0.7423	Intermediate Similarity	NPC100921
0.7423	Intermediate Similarity	NPC197903
0.7423	Intermediate Similarity	NPC99395
0.7423	Intermediate Similarity	NPC11804
0.7423	Intermediate Similarity	NPC261380
0.7423	Intermediate Similarity	NPC477018
0.7419	Intermediate Similarity	NPC93763
0.7419	Intermediate Similarity	NPC108816
0.7419	Intermediate Similarity	NPC267231
0.74	Intermediate Similarity	NPC475855
0.74	Intermediate Similarity	NPC475748
0.74	Intermediate Similarity	NPC473448
0.74	Intermediate Similarity	NPC474232
0.7396	Intermediate Similarity	NPC161045
0.7396	Intermediate Similarity	NPC11620
0.7383	Intermediate Similarity	NPC472756
0.7379	Intermediate Similarity	NPC17585
0.7379	Intermediate Similarity	NPC230800
0.7379	Intermediate Similarity	NPC279621
0.7379	Intermediate Similarity	NPC473291
0.7374	Intermediate Similarity	NPC202672
0.7374	Intermediate Similarity	NPC475819
0.7374	Intermediate Similarity	NPC473715
0.7374	Intermediate Similarity	NPC89001
0.7368	Intermediate Similarity	NPC325031
0.7364	Intermediate Similarity	NPC477103
0.7358	Intermediate Similarity	NPC225353
0.7353	Intermediate Similarity	NPC57405
0.7353	Intermediate Similarity	NPC303942
0.7347	Intermediate Similarity	NPC112685
0.7333	Intermediate Similarity	NPC477512
0.7327	Intermediate Similarity	NPC208886
0.7327	Intermediate Similarity	NPC12172
0.732	Intermediate Similarity	NPC474780
0.732	Intermediate Similarity	NPC243618
0.732	Intermediate Similarity	NPC70424
0.732	Intermediate Similarity	NPC474251
0.7315	Intermediate Similarity	NPC166115
0.7315	Intermediate Similarity	NPC223450
0.7315	Intermediate Similarity	NPC472749
0.7315	Intermediate Similarity	NPC472751
0.73	Intermediate Similarity	NPC280612
0.7292	Intermediate Similarity	NPC26624
0.7292	Intermediate Similarity	NPC475690
0.729	Intermediate Similarity	NPC473816
0.729	Intermediate Similarity	NPC474581
0.729	Intermediate Similarity	NPC309398
0.729	Intermediate Similarity	NPC475367
0.7282	Intermediate Similarity	NPC304886
0.7282	Intermediate Similarity	NPC272050
0.7281	Intermediate Similarity	NPC471145
0.7281	Intermediate Similarity	NPC471146
0.7273	Intermediate Similarity	NPC473649
0.7273	Intermediate Similarity	NPC154097
0.7273	Intermediate Similarity	NPC477012
0.7273	Intermediate Similarity	NPC471738
0.7273	Intermediate Similarity	NPC477102
0.7273	Intermediate Similarity	NPC159750
0.7273	Intermediate Similarity	NPC470401
0.7273	Intermediate Similarity	NPC231889
0.7264	Intermediate Similarity	NPC128733
0.7264	Intermediate Similarity	NPC164598
0.7264	Intermediate Similarity	NPC185141
0.7264	Intermediate Similarity	NPC46998
0.7264	Intermediate Similarity	NPC110443
0.7264	Intermediate Similarity	NPC15993
0.7264	Intermediate Similarity	NPC474339
0.7264	Intermediate Similarity	NPC133907
0.7264	Intermediate Similarity	NPC201718
0.7255	Intermediate Similarity	NPC135776
0.7255	Intermediate Similarity	NPC212486
0.7255	Intermediate Similarity	NPC469645
0.7255	Intermediate Similarity	NPC476049
0.7255	Intermediate Similarity	NPC469692
0.7248	Intermediate Similarity	NPC26617
0.7248	Intermediate Similarity	NPC477513
0.7245	Intermediate Similarity	NPC125290
0.7245	Intermediate Similarity	NPC322529
0.7245	Intermediate Similarity	NPC155873
0.7245	Intermediate Similarity	NPC215364
0.7245	Intermediate Similarity	NPC329615
0.7245	Intermediate Similarity	NPC329838
0.7245	Intermediate Similarity	NPC470755
0.7238	Intermediate Similarity	NPC141191
0.7238	Intermediate Similarity	NPC300584
0.7234	Intermediate Similarity	NPC279532
0.7232	Intermediate Similarity	NPC66108
0.7228	Intermediate Similarity	NPC316228
0.7228	Intermediate Similarity	NPC77337
0.7228	Intermediate Similarity	NPC473904
0.7228	Intermediate Similarity	NPC166554
0.7222	Intermediate Similarity	NPC472748
0.7216	Intermediate Similarity	NPC253801
0.7216	Intermediate Similarity	NPC170377
0.7216	Intermediate Similarity	NPC144415
0.7216	Intermediate Similarity	NPC318468
0.7212	Intermediate Similarity	NPC158416
0.7212	Intermediate Similarity	NPC76862
0.7212	Intermediate Similarity	NPC470883
0.7212	Intermediate Similarity	NPC39859
0.7207	Intermediate Similarity	NPC257240
0.72	Intermediate Similarity	NPC21208
0.72	Intermediate Similarity	NPC280621

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 NPC245521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1933
0.2-0.3	3784
0.3-0.4	2217
0.4-0.5	790
0.5-0.6	204
0.6-0.7	30
0.7-0.8	3
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
0.75	Intermediate Similarity	NPD7983	Approved
0.7248	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD46	Approved
0.7228	Intermediate Similarity	NPD6698	Approved
0.7207	Intermediate Similarity	NPD6371	Approved
0.7059	Intermediate Similarity	NPD5785	Approved
0.6952	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5363	Approved
0.69	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7838	Discovery
0.6832	Remote Similarity	NPD5786	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6729	Remote Similarity	NPD7839	Suspended
0.67	Remote Similarity	NPD7154	Phase 3
0.66	Remote Similarity	NPD4269	Approved
0.66	Remote Similarity	NPD5209	Approved
0.66	Remote Similarity	NPD4270	Approved
0.6566	Remote Similarity	NPD4252	Approved
0.6535	Remote Similarity	NPD5362	Discontinued
0.65	Remote Similarity	NPD5369	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6435	Remote Similarity	NPD6686	Approved
0.6417	Remote Similarity	NPD7115	Discovery
0.641	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5282	Discontinued
0.6371	Remote Similarity	NPD7642	Approved
0.6344	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5344	Discontinued
0.6306	Remote Similarity	NPD4225	Approved
0.6286	Remote Similarity	NPD4251	Approved
0.6286	Remote Similarity	NPD4250	Approved
0.6281	Remote Similarity	NPD7500	Approved
0.6275	Remote Similarity	NPD6435	Approved
0.6273	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6336	Discontinued
0.625	Remote Similarity	NPD6648	Approved
0.624	Remote Similarity	NPD7829	Approved
0.624	Remote Similarity	NPD7830	Approved
0.6238	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8074	Phase 3
0.6218	Remote Similarity	NPD6053	Discontinued
0.6214	Remote Similarity	NPD6110	Phase 1
0.621	Remote Similarity	NPD5983	Phase 2
0.62	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4249	Approved
0.6168	Remote Similarity	NPD6101	Approved
0.6168	Remote Similarity	NPD1695	Approved
0.6168	Remote Similarity	NPD5370	Suspended
0.6168	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4632	Approved
0.6129	Remote Similarity	NPD6319	Approved
0.6106	Remote Similarity	NPD7639	Approved
0.6106	Remote Similarity	NPD7640	Approved
0.61	Remote Similarity	NPD4756	Discovery
0.6098	Remote Similarity	NPD6335	Approved
0.608	Remote Similarity	NPD8444	Approved
0.6078	Remote Similarity	NPD4821	Approved
0.6078	Remote Similarity	NPD5368	Approved
0.6078	Remote Similarity	NPD4822	Approved
0.6078	Remote Similarity	NPD4820	Approved
0.6078	Remote Similarity	NPD4819	Approved
0.6064	Remote Similarity	NPD7331	Phase 2
0.6055	Remote Similarity	NPD6411	Approved
0.6055	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7637	Suspended
0.6047	Remote Similarity	NPD6033	Approved
0.604	Remote Similarity	NPD4271	Approved
0.604	Remote Similarity	NPD4268	Approved
0.6031	Remote Similarity	NPD7260	Phase 2
0.6018	Remote Similarity	NPD7638	Approved
0.6016	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD7319	Approved
0.5968	Remote Similarity	NPD7641	Discontinued
0.5968	Remote Similarity	NPD6313	Approved
0.5968	Remote Similarity	NPD6314	Approved
0.5962	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8297	Approved
0.5943	Remote Similarity	NPD1694	Approved
0.5938	Remote Similarity	NPD7492	Approved
0.5935	Remote Similarity	NPD6868	Approved
0.5926	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7100	Approved
0.592	Remote Similarity	NPD7101	Approved
0.5905	Remote Similarity	NPD5331	Approved
0.5905	Remote Similarity	NPD5332	Approved
0.59	Remote Similarity	NPD8039	Approved
0.5891	Remote Similarity	NPD7507	Approved
0.5891	Remote Similarity	NPD8273	Phase 1
0.5891	Remote Similarity	NPD8451	Approved
0.5891	Remote Similarity	NPD6616	Approved
0.5882	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD6054	Approved
0.5868	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD1719	Phase 1
0.5865	Remote Similarity	NPD4790	Discontinued
0.5849	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD7078	Approved
0.5846	Remote Similarity	NPD8448	Approved
0.5814	Remote Similarity	NPD8340	Approved
0.5814	Remote Similarity	NPD8299	Approved
0.5814	Remote Similarity	NPD8342	Approved
0.5814	Remote Similarity	NPD8341	Approved
0.5812	Remote Similarity	NPD6647	Phase 2
0.5802	Remote Similarity	NPD7736	Approved
0.5794	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6421	Discontinued
0.5785	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6370	Approved
0.575	Remote Similarity	NPD6899	Approved
0.575	Remote Similarity	NPD6881	Approved
0.5741	Remote Similarity	NPD6422	Discontinued
0.5738	Remote Similarity	NPD6650	Approved
0.5738	Remote Similarity	NPD6649	Approved
0.5736	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD5956	Approved
0.5714	Remote Similarity	NPD8392	Approved
0.5714	Remote Similarity	NPD8390	Approved
0.5714	Remote Similarity	NPD8391	Approved
0.5703	Remote Similarity	NPD6016	Approved
0.5703	Remote Similarity	NPD6015	Approved
0.5702	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6882	Approved
0.5684	Remote Similarity	NPD3197	Phase 1
0.5667	Remote Similarity	NPD5697	Approved
0.5659	Remote Similarity	NPD5988	Approved
0.5659	Remote Similarity	NPD8080	Discontinued
0.5656	Remote Similarity	NPD7290	Approved
0.5656	Remote Similarity	NPD6883	Approved
0.5656	Remote Similarity	NPD7102	Approved
0.5656	Remote Similarity	NPD5169	Approved
0.5643	Remote Similarity	NPD8384	Approved
0.563	Remote Similarity	NPD6845	Suspended
0.5625	Remote Similarity	NPD7341	Phase 2
0.5625	Remote Similarity	NPD6059	Approved
0.562	Remote Similarity	NPD6011	Approved
0.5615	Remote Similarity	NPD8328	Phase 3
0.561	Remote Similarity	NPD2204	Approved
0.561	Remote Similarity	NPD8130	Phase 1
0.561	Remote Similarity	NPD6869	Approved
0.561	Remote Similarity	NPD6847	Approved
0.561	Remote Similarity	NPD6617	Approved
0.561	Remote Similarity	NPD5127	Approved
0.5606	Remote Similarity	NPD8293	Discontinued

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