NPASS Compound

Structure

NPC279859 OpenBabel07101718182D 26 27 0 0 1 0 0 0 0 0999 V2000 4.0755 -2.2120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8704 -0.8352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3349 1.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2424 3.3150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6419 0.1302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5629 0.6543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1252 -0.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8053 1.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1032 -0.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7833 1.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3283 0.6643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0755 -1.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4857 -0.3763 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2643 1.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6318 -0.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2767 1.3969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4651 -0.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6442 -0.6539 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8886 1.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4228 0.8147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7686 -1.8661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1399 2.3045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0945 -1.0889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7835 1.5609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6181 2.6422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 12 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 13 12 1 6 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 9 1 1 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 3 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	374.286
LogP:	1.497
LogD:	0.172
LogS:	-2.658
# Rotatable Bonds:	3
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	5.511
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.653
MDCK Permeability:	5.769129711552523e-05
Pgp-inhibitor:	0.447
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	60.581932067871094%
Volume Distribution (VD):	0.422
Pgp-substrate:	52.83464813232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.571
CYP2C19-inhibitor:	0.304
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.524

ADMET: Excretion

Clearance (CL):	10.314
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.429
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.355
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.655
Skin Sensitization:	0.837
Carcinogencity:	0.249
Eye Corrosion:	0.055
Eye Irritation:	0.045
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC279859

Natural Product ID:	NPC279859
*Common Name:**	Norcembrene 5
IUPAC Name:	methyl (1R,5S,7Z,12S)-12-methyl-3,10,14-trioxo-5-prop-1-en-2-yl-15-oxabicyclo[10.2.1]pentadec-7-ene-8-carboxylate
Synonyms:	Norcembrene 5
Standard InCHIKey:	CCRQLJVTUBLUBL-ADOWRXFUSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-12(2)13-5-6-14(19(24)25-4)8-16(22)10-20(3)11-17(23)18(26-20)9-15(21)7-13/h6,13,18H,1,5,7-11H2,2-4H3/b14-6-/t13-,18+,20-/m0/s1
SMILES:	C=C(C)[C@H]1C/C=C(/CC(=O)C[C@@]2(C)CC(=O)[C@@H](CC(=O)C1)O2)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463053
PubChem CID:	21725162
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones

*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
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502336]
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620256]
NPO27826	Sinularia maxima	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23200246]
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27826	Sinularia maxima	Species	Alcyoniidae	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	2
IC50	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[470801]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	17.5	ug ml-1	PMID[470801]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[470802]

☑ 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 NPC279859 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	1546
0.2-0.3	6371
0.3-0.4	13535
0.4-0.5	11268
0.5-0.6	6219
0.6-0.7	2791
0.7-0.8	679
0.8-0.85	65
0.85-0.9	5
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38576
0.9059	High Similarity	NPC469631
0.9059	High Similarity	NPC471047
0.9059	High Similarity	NPC469628
0.9059	High Similarity	NPC475906
0.9059	High Similarity	NPC469653
0.8667	High Similarity	NPC474490
0.8605	High Similarity	NPC261721
0.8571	High Similarity	NPC173609
0.8571	High Similarity	NPC476275
0.8556	High Similarity	NPC121825
0.8556	High Similarity	NPC469632
0.8539	High Similarity	NPC20713
0.8537	High Similarity	NPC128276
0.8444	Intermediate Similarity	NPC469645
0.8444	Intermediate Similarity	NPC165383
0.8444	Intermediate Similarity	NPC475302
0.8444	Intermediate Similarity	NPC469692
0.8427	Intermediate Similarity	NPC329857
0.8427	Intermediate Similarity	NPC469718
0.8415	Intermediate Similarity	NPC57744
0.8409	Intermediate Similarity	NPC475902
0.8387	Intermediate Similarity	NPC54843
0.8353	Intermediate Similarity	NPC221231
0.8353	Intermediate Similarity	NPC471326
0.8272	Intermediate Similarity	NPC476355
0.8261	Intermediate Similarity	NPC474947
0.8256	Intermediate Similarity	NPC318468
0.8256	Intermediate Similarity	NPC474703
0.8256	Intermediate Similarity	NPC475947
0.8235	Intermediate Similarity	NPC42470
0.8235	Intermediate Similarity	NPC301477
0.8235	Intermediate Similarity	NPC471325
0.8235	Intermediate Similarity	NPC281949
0.8235	Intermediate Similarity	NPC25684
0.8235	Intermediate Similarity	NPC141810
0.8222	Intermediate Similarity	NPC471818
0.8214	Intermediate Similarity	NPC178277
0.8211	Intermediate Similarity	NPC185141
0.8211	Intermediate Similarity	NPC46998
0.8211	Intermediate Similarity	NPC133907
0.8211	Intermediate Similarity	NPC128733
0.8211	Intermediate Similarity	NPC110443
0.8193	Intermediate Similarity	NPC470240
0.8193	Intermediate Similarity	NPC476794
0.8193	Intermediate Similarity	NPC65603
0.8171	Intermediate Similarity	NPC244166
0.814	Intermediate Similarity	NPC85772
0.8118	Intermediate Similarity	NPC223904
0.809	Intermediate Similarity	NPC266957
0.8072	Intermediate Similarity	NPC123360
0.8072	Intermediate Similarity	NPC235906
0.8068	Intermediate Similarity	NPC125290
0.8068	Intermediate Similarity	NPC261380
0.8049	Intermediate Similarity	NPC140287
0.8049	Intermediate Similarity	NPC15499
0.8049	Intermediate Similarity	NPC117746
0.8049	Intermediate Similarity	NPC294434
0.8049	Intermediate Similarity	NPC259599
0.8041	Intermediate Similarity	NPC475873
0.8025	Intermediate Similarity	NPC163003
0.8023	Intermediate Similarity	NPC286229
0.8023	Intermediate Similarity	NPC275507
0.8021	Intermediate Similarity	NPC164598
0.8021	Intermediate Similarity	NPC474339
0.8	Intermediate Similarity	NPC617
0.8	Intermediate Similarity	NPC270126
0.7979	Intermediate Similarity	NPC301596
0.7979	Intermediate Similarity	NPC172998
0.7979	Intermediate Similarity	NPC299396
0.7978	Intermediate Similarity	NPC107787
0.7976	Intermediate Similarity	NPC41780
0.7976	Intermediate Similarity	NPC180290
0.7976	Intermediate Similarity	NPC187568
0.7959	Intermediate Similarity	NPC472756
0.7957	Intermediate Similarity	NPC148463
0.7955	Intermediate Similarity	NPC115786
0.7952	Intermediate Similarity	NPC226669
0.7952	Intermediate Similarity	NPC193351
0.7952	Intermediate Similarity	NPC138408
0.7952	Intermediate Similarity	NPC155587
0.7935	Intermediate Similarity	NPC111114
0.7935	Intermediate Similarity	NPC261607
0.7935	Intermediate Similarity	NPC300312
0.7935	Intermediate Similarity	NPC284185
0.7931	Intermediate Similarity	NPC475690
0.7907	Intermediate Similarity	NPC302426
0.7895	Intermediate Similarity	NPC471140
0.7889	Intermediate Similarity	NPC478145
0.7889	Intermediate Similarity	NPC478144
0.7889	Intermediate Similarity	NPC471739
0.7889	Intermediate Similarity	NPC475703
0.7889	Intermediate Similarity	NPC72513
0.7882	Intermediate Similarity	NPC108816
0.7882	Intermediate Similarity	NPC93763
0.7872	Intermediate Similarity	NPC234339
0.7872	Intermediate Similarity	NPC273197
0.7865	Intermediate Similarity	NPC215364
0.7865	Intermediate Similarity	NPC78089
0.7865	Intermediate Similarity	NPC33570
0.7865	Intermediate Similarity	NPC21471
0.7865	Intermediate Similarity	NPC96621
0.7857	Intermediate Similarity	NPC25666
0.7857	Intermediate Similarity	NPC271059
0.7841	Intermediate Similarity	NPC475989
0.7841	Intermediate Similarity	NPC128429
0.7841	Intermediate Similarity	NPC215294
0.7835	Intermediate Similarity	NPC474742
0.7835	Intermediate Similarity	NPC264477
0.7835	Intermediate Similarity	NPC476270
0.7835	Intermediate Similarity	NPC477511
0.7826	Intermediate Similarity	NPC253144
0.7791	Intermediate Similarity	NPC472965
0.7791	Intermediate Similarity	NPC63649
0.7791	Intermediate Similarity	NPC276647
0.7791	Intermediate Similarity	NPC264227
0.7791	Intermediate Similarity	NPC622
0.7791	Intermediate Similarity	NPC471740
0.7789	Intermediate Similarity	NPC17585
0.7778	Intermediate Similarity	NPC469483
0.7778	Intermediate Similarity	NPC284902
0.7778	Intermediate Similarity	NPC475461
0.7778	Intermediate Similarity	NPC50637
0.7778	Intermediate Similarity	NPC305475
0.7766	Intermediate Similarity	NPC476596
0.7766	Intermediate Similarity	NPC167219
0.7766	Intermediate Similarity	NPC476267
0.7766	Intermediate Similarity	NPC140543
0.7765	Intermediate Similarity	NPC474760
0.7765	Intermediate Similarity	NPC141789
0.7765	Intermediate Similarity	NPC171204
0.7765	Intermediate Similarity	NPC97516
0.7765	Intermediate Similarity	NPC476028
0.7755	Intermediate Similarity	NPC149371
0.7753	Intermediate Similarity	NPC149869
0.7753	Intermediate Similarity	NPC474359
0.7742	Intermediate Similarity	NPC74103
0.7742	Intermediate Similarity	NPC123177
0.7742	Intermediate Similarity	NPC166110
0.7742	Intermediate Similarity	NPC150978
0.7742	Intermediate Similarity	NPC70595
0.7717	Intermediate Similarity	NPC166919
0.7717	Intermediate Similarity	NPC280833
0.7717	Intermediate Similarity	NPC475971
0.7711	Intermediate Similarity	NPC295633
0.7711	Intermediate Similarity	NPC58956
0.7711	Intermediate Similarity	NPC269206
0.7701	Intermediate Similarity	NPC69271
0.7701	Intermediate Similarity	NPC74673
0.7701	Intermediate Similarity	NPC281132
0.7692	Intermediate Similarity	NPC160138
0.7692	Intermediate Similarity	NPC231889
0.7684	Intermediate Similarity	NPC31021
0.7677	Intermediate Similarity	NPC472755
0.7677	Intermediate Similarity	NPC475871
0.7677	Intermediate Similarity	NPC475945
0.7674	Intermediate Similarity	NPC267231
0.7667	Intermediate Similarity	NPC255307
0.7667	Intermediate Similarity	NPC472686
0.7667	Intermediate Similarity	NPC165162
0.7667	Intermediate Similarity	NPC290329
0.7667	Intermediate Similarity	NPC470755
0.766	Intermediate Similarity	NPC476598
0.766	Intermediate Similarity	NPC476597
0.766	Intermediate Similarity	NPC248193
0.7654	Intermediate Similarity	NPC470256
0.7653	Intermediate Similarity	NPC15993
0.7653	Intermediate Similarity	NPC472753
0.7653	Intermediate Similarity	NPC47880
0.7653	Intermediate Similarity	NPC201718
0.764	Intermediate Similarity	NPC222358
0.764	Intermediate Similarity	NPC272814
0.764	Intermediate Similarity	NPC39588
0.764	Intermediate Similarity	NPC53867
0.764	Intermediate Similarity	NPC250315
0.7634	Intermediate Similarity	NPC179394
0.7634	Intermediate Similarity	NPC62815
0.7634	Intermediate Similarity	NPC251385
0.7634	Intermediate Similarity	NPC144133
0.7634	Intermediate Similarity	NPC49342
0.7619	Intermediate Similarity	NPC474758
0.7614	Intermediate Similarity	NPC325031
0.7614	Intermediate Similarity	NPC10276
0.7614	Intermediate Similarity	NPC35089
0.7609	Intermediate Similarity	NPC476805
0.7609	Intermediate Similarity	NPC226863
0.7604	Intermediate Similarity	NPC121036
0.7604	Intermediate Similarity	NPC472674
0.7604	Intermediate Similarity	NPC230800
0.76	Intermediate Similarity	NPC471143
0.76	Intermediate Similarity	NPC477510
0.76	Intermediate Similarity	NPC474741
0.759	Intermediate Similarity	NPC129665
0.7586	Intermediate Similarity	NPC182550
0.7586	Intermediate Similarity	NPC473980
0.7586	Intermediate Similarity	NPC470239
0.7586	Intermediate Similarity	NPC473981
0.7586	Intermediate Similarity	NPC19841
0.7586	Intermediate Similarity	NPC470244
0.7582	Intermediate Similarity	NPC261253

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 NPC279859 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	2100
0.2-0.3	3879
0.3-0.4	2010
0.4-0.5	621
0.5-0.6	241
0.6-0.7	87
0.7-0.8	9
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
0.7473	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5209	Approved
0.732	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5785	Approved
0.7097	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5363	Approved
0.7073	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5693	Phase 1
0.6979	Remote Similarity	NPD1695	Approved
0.6931	Remote Similarity	NPD5696	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6672	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6848	Remote Similarity	NPD5369	Approved
0.6842	Remote Similarity	NPD5786	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6774	Remote Similarity	NPD4270	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6759	Remote Similarity	NPD6371	Approved
0.6634	Remote Similarity	NPD5695	Phase 3
0.6633	Remote Similarity	NPD6673	Approved
0.6633	Remote Similarity	NPD6080	Approved
0.6633	Remote Similarity	NPD6904	Approved
0.6596	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4756	Discovery
0.6566	Remote Similarity	NPD5692	Phase 3
0.6566	Remote Similarity	NPD6698	Approved
0.6566	Remote Similarity	NPD46	Approved
0.6559	Remote Similarity	NPD4252	Approved
0.6556	Remote Similarity	NPD8039	Approved
0.6526	Remote Similarity	NPD7154	Phase 3
0.6505	Remote Similarity	NPD6083	Phase 2
0.6505	Remote Similarity	NPD6084	Phase 2
0.65	Remote Similarity	NPD6050	Approved
0.65	Remote Similarity	NPD5694	Approved
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD7146	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6495	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD7115	Discovery
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6392	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7900	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5362	Discontinued
0.6344	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6614	Approved
0.633	Remote Similarity	NPD5697	Approved
0.6327	Remote Similarity	NPD6098	Approved
0.6311	Remote Similarity	NPD5210	Approved
0.6311	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5778	Approved
0.6275	Remote Similarity	NPD6399	Phase 3
0.6275	Remote Similarity	NPD5779	Approved
0.6273	Remote Similarity	NPD6011	Approved
0.6273	Remote Similarity	NPD6899	Approved
0.6273	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6435	Approved
0.6239	Remote Similarity	NPD6402	Approved
0.6239	Remote Similarity	NPD5739	Approved
0.6239	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD7128	Approved
0.6238	Remote Similarity	NPD7838	Discovery
0.6238	Remote Similarity	NPD5207	Approved
0.6216	Remote Similarity	NPD6013	Approved
0.6216	Remote Similarity	NPD6014	Approved
0.6216	Remote Similarity	NPD6012	Approved
0.6207	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7902	Approved
0.6182	Remote Similarity	NPD5701	Approved
0.6176	Remote Similarity	NPD7983	Approved
0.6161	Remote Similarity	NPD7290	Approved
0.6161	Remote Similarity	NPD7102	Approved
0.6161	Remote Similarity	NPD2067	Discontinued
0.6161	Remote Similarity	NPD6883	Approved
0.6154	Remote Similarity	NPD5654	Approved
0.6142	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6101	Approved
0.6139	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5370	Suspended
0.6132	Remote Similarity	NPD7638	Approved
0.6126	Remote Similarity	NPD7320	Approved
0.6126	Remote Similarity	NPD6686	Approved
0.6106	Remote Similarity	NPD6869	Approved
0.6106	Remote Similarity	NPD6847	Approved
0.6106	Remote Similarity	NPD8130	Phase 1
0.6106	Remote Similarity	NPD6617	Approved
0.61	Remote Similarity	NPD3573	Approved
0.6091	Remote Similarity	NPD6008	Approved
0.6075	Remote Similarity	NPD7640	Approved
0.6075	Remote Similarity	NPD7639	Approved
0.6058	Remote Similarity	NPD6001	Approved
0.6058	Remote Similarity	NPD7748	Approved
0.6053	Remote Similarity	NPD8297	Approved
0.6053	Remote Similarity	NPD6882	Approved
0.6042	Remote Similarity	NPD4695	Discontinued
0.6042	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4821	Approved
0.6042	Remote Similarity	NPD4820	Approved
0.6042	Remote Similarity	NPD4819	Approved
0.6042	Remote Similarity	NPD4822	Approved
0.6042	Remote Similarity	NPD5368	Approved
0.604	Remote Similarity	NPD5208	Approved
0.6038	Remote Similarity	NPD5959	Approved
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7331	Phase 2
0.6019	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6051	Approved
0.598	Remote Similarity	NPD4753	Phase 2
0.5966	Remote Similarity	NPD6319	Approved
0.5965	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7839	Suspended
0.5943	Remote Similarity	NPD4697	Phase 3
0.5913	Remote Similarity	NPD6053	Discontinued
0.5909	Remote Similarity	NPD7341	Phase 2
0.5902	Remote Similarity	NPD7492	Approved
0.5897	Remote Similarity	NPD6274	Approved
0.5877	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7260	Phase 2
0.5865	Remote Similarity	NPD5284	Approved
0.5865	Remote Similarity	NPD7515	Phase 2
0.5865	Remote Similarity	NPD5281	Approved
0.5862	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6110	Phase 1
0.5859	Remote Similarity	NPD5332	Approved
0.5859	Remote Similarity	NPD5331	Approved
0.5854	Remote Similarity	NPD6616	Approved
0.5847	Remote Similarity	NPD6317	Approved
0.5843	Remote Similarity	NPD3704	Approved
0.5842	Remote Similarity	NPD3618	Phase 1
0.5842	Remote Similarity	NPD5690	Phase 2
0.5842	Remote Similarity	NPD4249	Approved
0.5833	Remote Similarity	NPD6054	Approved
0.5833	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD4271	Approved
0.5826	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD4790	Discontinued
0.5806	Remote Similarity	NPD7078	Approved
0.58	Remote Similarity	NPD3666	Approved
0.58	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4197	Approved
0.58	Remote Similarity	NPD3665	Phase 1
0.58	Remote Similarity	NPD3133	Approved
0.5798	Remote Similarity	NPD6335	Approved
0.5798	Remote Similarity	NPD6314	Approved
0.5798	Remote Similarity	NPD6313	Approved
0.5795	Remote Similarity	NPD3197	Phase 1
0.5794	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7732	Phase 3
0.5794	Remote Similarity	NPD5222	Approved
0.5794	Remote Similarity	NPD5221	Approved
0.5785	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6016	Approved
0.5785	Remote Similarity	NPD6015	Approved
0.5784	Remote Similarity	NPD4251	Approved
0.5784	Remote Similarity	NPD4250	Approved
0.578	Remote Similarity	NPD6648	Approved
0.578	Remote Similarity	NPD4696	Approved
0.578	Remote Similarity	NPD5285	Approved
0.578	Remote Similarity	NPD5286	Approved
0.5766	Remote Similarity	NPD6052	Approved
0.5763	Remote Similarity	NPD6868	Approved
0.576	Remote Similarity	NPD7736	Approved
0.575	Remote Similarity	NPD7101	Approved
0.575	Remote Similarity	NPD7100	Approved
0.5743	Remote Similarity	NPD5329	Approved
0.5741	Remote Similarity	NPD4755	Approved
0.5741	Remote Similarity	NPD5173	Approved
0.5738	Remote Similarity	NPD6370	Approved
0.5738	Remote Similarity	NPD5988	Approved
0.5727	Remote Similarity	NPD5223	Approved
0.5727	Remote Similarity	NPD5344	Discontinued
0.5726	Remote Similarity	NPD4632	Approved
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5703	Remote Similarity	NPD6845	Suspended
0.5702	Remote Similarity	NPD6059	Approved
0.5702	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.569	Remote Similarity	NPD2204	Approved
0.5686	Remote Similarity	NPD4623	Approved
0.5686	Remote Similarity	NPD4694	Approved
0.5686	Remote Similarity	NPD6422	Discontinued
0.5686	Remote Similarity	NPD5280	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