NPASS Compound

Structure

NPC178277 OpenBabel07101718322D 27 28 0 0 1 0 0 0 0 0999 V2000 2.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -2.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 1.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6366 2.0444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 -1.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 0.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 -1.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 -1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 0.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7231 2.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 -1.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 0.8688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5257 0.6920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6185 3.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 -2.8634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 1.8634 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 22 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 19 26 1 1 0 0 0 20 12 1 1 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 13 1 1 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	400.088
LogP:	4.099
LogD:	3.603
LogS:	-4.806
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	5.105
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	2.57223000517115e-05
Pgp-inhibitor:	0.241
Pgp-substrate:	0.125
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	92.5252456665039%
Volume Distribution (VD):	0.431
Pgp-substrate:	8.771538734436035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.373
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.291
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.115
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	2.919
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.877
Carcinogencity:	0.69
Eye Corrosion:	0.028
Eye Irritation:	0.272
Respiratory Toxicity:	0.892

Download Data

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

Natural Product: NPC178277

Natural Product ID:	NPC178277
*Common Name:**	Sarcophytonolide R
IUPAC Name:	[(1R,2R,3R,5E,8Z)-5,9-dimethyl-11,14-dioxo-2-propan-2-yl-15-oxabicyclo[11.2.1]hexadeca-5,8,13(16)-trien-3-yl] acetate
Synonyms:
Standard InCHIKey:	WYZRLZZDCWHGLN-GNDBRSTBSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-13(2)21-19(26-16(5)23)10-15(4)8-6-7-14(3)9-18(24)11-17-12-20(21)27-22(17)25/h7-8,12-13,19-21H,6,9-11H2,1-5H3/b14-7-,15-8+/t19-,20-,21-/m1/s1
SMILES:	CC(C)[C@@H]1[C@@H](C/C(=C/C/C=C(/C)CC(=O)CC2=C[C@H]1OC2=O)/C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2414201
PubChem CID:	71770419
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10923847]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23859780]
NPO20809	Sarcophyton trocheliophorum	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>=	20.0	ug.mL-1	PMID[564880]

☑ 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 NPC178277 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	209
0.1-0.2	1351
0.2-0.3	5934
0.3-0.4	13785
0.4-0.5	11325
0.5-0.6	6110
0.6-0.7	3116
0.7-0.8	772
0.8-0.85	72
0.85-0.9	14
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC471325
0.9726	High Similarity	NPC57744
0.9595	High Similarity	NPC128276
0.9315	High Similarity	NPC294434
0.9315	High Similarity	NPC259599
0.9315	High Similarity	NPC15499
0.9315	High Similarity	NPC117746
0.9221	High Similarity	NPC42470
0.9067	High Similarity	NPC123360
0.9054	High Similarity	NPC476355
0.8961	High Similarity	NPC270126
0.8861	High Similarity	NPC173609
0.88	High Similarity	NPC140287
0.88	High Similarity	NPC474758
0.8784	High Similarity	NPC163003
0.8734	High Similarity	NPC301477
0.8734	High Similarity	NPC25684
0.8734	High Similarity	NPC281949
0.8701	High Similarity	NPC97516
0.8701	High Similarity	NPC141789
0.8701	High Similarity	NPC476028
0.8701	High Similarity	NPC171204
0.8684	High Similarity	NPC244166
0.8659	High Similarity	NPC107787
0.8608	High Similarity	NPC281132
0.859	High Similarity	NPC108816
0.859	High Similarity	NPC93763
0.8537	High Similarity	NPC78089
0.8519	High Similarity	NPC475947
0.8519	High Similarity	NPC474703
0.85	High Similarity	NPC141810
0.85	High Similarity	NPC325031
0.8462	Intermediate Similarity	NPC187568
0.8462	Intermediate Similarity	NPC65603
0.8462	Intermediate Similarity	NPC41780
0.8462	Intermediate Similarity	NPC470240
0.8462	Intermediate Similarity	NPC476794
0.8442	Intermediate Similarity	NPC226669
0.8442	Intermediate Similarity	NPC155587
0.8442	Intermediate Similarity	NPC329852
0.8442	Intermediate Similarity	NPC138408
0.8442	Intermediate Similarity	NPC193351
0.8434	Intermediate Similarity	NPC261721
0.8421	Intermediate Similarity	NPC58956
0.8421	Intermediate Similarity	NPC295633
0.8421	Intermediate Similarity	NPC269206
0.8415	Intermediate Similarity	NPC115786
0.8415	Intermediate Similarity	NPC476804
0.8395	Intermediate Similarity	NPC35556
0.8378	Intermediate Similarity	NPC470256
0.8354	Intermediate Similarity	NPC299235
0.8333	Intermediate Similarity	NPC235906
0.8313	Intermediate Similarity	NPC215364
0.8293	Intermediate Similarity	NPC40746
0.8293	Intermediate Similarity	NPC193198
0.8293	Intermediate Similarity	NPC318468
0.8293	Intermediate Similarity	NPC169575
0.8289	Intermediate Similarity	NPC129665
0.8267	Intermediate Similarity	NPC88877
0.8267	Intermediate Similarity	NPC476591
0.825	Intermediate Similarity	NPC472965
0.825	Intermediate Similarity	NPC617
0.825	Intermediate Similarity	NPC471299
0.825	Intermediate Similarity	NPC63649
0.825	Intermediate Similarity	NPC264227
0.8243	Intermediate Similarity	NPC194871
0.8235	Intermediate Similarity	NPC469631
0.8235	Intermediate Similarity	NPC475906
0.8235	Intermediate Similarity	NPC469628
0.8235	Intermediate Similarity	NPC476805
0.8235	Intermediate Similarity	NPC469653
0.8235	Intermediate Similarity	NPC471047
0.8228	Intermediate Similarity	NPC320630
0.8228	Intermediate Similarity	NPC7563
0.8228	Intermediate Similarity	NPC116177
0.8228	Intermediate Similarity	NPC474760
0.8214	Intermediate Similarity	NPC279859
0.8214	Intermediate Similarity	NPC469483
0.8214	Intermediate Similarity	NPC475461
0.8214	Intermediate Similarity	NPC305475
0.8214	Intermediate Similarity	NPC284902
0.8214	Intermediate Similarity	NPC38576
0.8193	Intermediate Similarity	NPC96259
0.8193	Intermediate Similarity	NPC149869
0.8193	Intermediate Similarity	NPC141193
0.8182	Intermediate Similarity	NPC476596
0.8158	Intermediate Similarity	NPC67183
0.8148	Intermediate Similarity	NPC74673
0.8148	Intermediate Similarity	NPC302426
0.8148	Intermediate Similarity	NPC69271
0.8148	Intermediate Similarity	NPC223904
0.8133	Intermediate Similarity	NPC218477
0.8125	Intermediate Similarity	NPC267231
0.8125	Intermediate Similarity	NPC471220
0.8118	Intermediate Similarity	NPC160138
0.8118	Intermediate Similarity	NPC475703
0.8108	Intermediate Similarity	NPC248125
0.8095	Intermediate Similarity	NPC189311
0.8095	Intermediate Similarity	NPC165162
0.8095	Intermediate Similarity	NPC255307
0.8095	Intermediate Similarity	NPC470755
0.8072	Intermediate Similarity	NPC39588
0.8072	Intermediate Similarity	NPC53867
0.8072	Intermediate Similarity	NPC131669
0.8072	Intermediate Similarity	NPC473390
0.8072	Intermediate Similarity	NPC59097
0.8068	Intermediate Similarity	NPC469645
0.8068	Intermediate Similarity	NPC469692
0.8068	Intermediate Similarity	NPC476597
0.8068	Intermediate Similarity	NPC476598
0.8052	Intermediate Similarity	NPC84038
0.8049	Intermediate Similarity	NPC24417
0.8049	Intermediate Similarity	NPC39411
0.8049	Intermediate Similarity	NPC255580
0.8049	Intermediate Similarity	NPC52861
0.8046	Intermediate Similarity	NPC144133
0.8046	Intermediate Similarity	NPC179394
0.8046	Intermediate Similarity	NPC471818
0.8025	Intermediate Similarity	NPC182550
0.8025	Intermediate Similarity	NPC469620
0.8025	Intermediate Similarity	NPC167881
0.8025	Intermediate Similarity	NPC469690
0.8025	Intermediate Similarity	NPC98557
0.8023	Intermediate Similarity	NPC475902
0.8023	Intermediate Similarity	NPC226863
0.8023	Intermediate Similarity	NPC476803
0.8	Intermediate Similarity	NPC150755
0.8	Intermediate Similarity	NPC472266
0.8	Intermediate Similarity	NPC50637
0.8	Intermediate Similarity	NPC10572
0.7978	Intermediate Similarity	NPC470697
0.7978	Intermediate Similarity	NPC121825
0.7976	Intermediate Similarity	NPC159635
0.7976	Intermediate Similarity	NPC114979
0.7976	Intermediate Similarity	NPC475100
0.7976	Intermediate Similarity	NPC158756
0.7976	Intermediate Similarity	NPC191476
0.7976	Intermediate Similarity	NPC82297
0.7976	Intermediate Similarity	NPC30486
0.7955	Intermediate Similarity	NPC261607
0.7955	Intermediate Similarity	NPC123177
0.7955	Intermediate Similarity	NPC150978
0.7955	Intermediate Similarity	NPC70595
0.7955	Intermediate Similarity	NPC74103
0.7955	Intermediate Similarity	NPC111114
0.7955	Intermediate Similarity	NPC300312
0.7955	Intermediate Similarity	NPC284185
0.7952	Intermediate Similarity	NPC200513
0.7952	Intermediate Similarity	NPC475690
0.7952	Intermediate Similarity	NPC229825
0.7952	Intermediate Similarity	NPC89555
0.7952	Intermediate Similarity	NPC85772
0.7949	Intermediate Similarity	NPC474705
0.7949	Intermediate Similarity	NPC472956
0.7931	Intermediate Similarity	NPC166919
0.7931	Intermediate Similarity	NPC295312
0.7927	Intermediate Similarity	NPC276356
0.7922	Intermediate Similarity	NPC469660
0.7922	Intermediate Similarity	NPC472955
0.7907	Intermediate Similarity	NPC478144
0.7901	Intermediate Similarity	NPC196653
0.7901	Intermediate Similarity	NPC472960
0.7901	Intermediate Similarity	NPC471465
0.7882	Intermediate Similarity	NPC33570
0.7882	Intermediate Similarity	NPC161957
0.7882	Intermediate Similarity	NPC125290
0.7882	Intermediate Similarity	NPC474547
0.7882	Intermediate Similarity	NPC21471
0.7875	Intermediate Similarity	NPC472967
0.7875	Intermediate Similarity	NPC473223
0.7875	Intermediate Similarity	NPC27205
0.7875	Intermediate Similarity	NPC266159
0.7865	Intermediate Similarity	NPC475657
0.7857	Intermediate Similarity	NPC475989
0.7857	Intermediate Similarity	NPC250315
0.7841	Intermediate Similarity	NPC473448
0.7841	Intermediate Similarity	NPC253144
0.7841	Intermediate Similarity	NPC469368
0.7841	Intermediate Similarity	NPC475855
0.7841	Intermediate Similarity	NPC129419
0.7841	Intermediate Similarity	NPC62815
0.7841	Intermediate Similarity	NPC312042
0.7831	Intermediate Similarity	NPC35089
0.7831	Intermediate Similarity	NPC10276
0.7821	Intermediate Similarity	NPC186531
0.7816	Intermediate Similarity	NPC475819
0.7808	Intermediate Similarity	NPC151648
0.7805	Intermediate Similarity	NPC473980
0.7805	Intermediate Similarity	NPC470239
0.7805	Intermediate Similarity	NPC19841
0.7805	Intermediate Similarity	NPC470244
0.7805	Intermediate Similarity	NPC473981
0.7802	Intermediate Similarity	NPC172998
0.7802	Intermediate Similarity	NPC299396
0.7802	Intermediate Similarity	NPC301596
0.7792	Intermediate Similarity	NPC265574
0.7792	Intermediate Similarity	NPC144511
0.7792	Intermediate Similarity	NPC296522
0.7791	Intermediate Similarity	NPC469910
0.7791	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 NPC178277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1921
0.2-0.3	3875
0.3-0.4	2114
0.4-0.5	716
0.5-0.6	256
0.6-0.7	62
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
0.7952	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1694	Approved
0.764	Intermediate Similarity	NPD5785	Approved
0.7529	Intermediate Similarity	NPD5209	Approved
0.75	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5363	Approved
0.7471	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1695	Approved
0.7273	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6698	Approved
0.7253	Intermediate Similarity	NPD46	Approved
0.7241	Intermediate Similarity	NPD7154	Phase 3
0.7191	Intermediate Similarity	NPD5786	Approved
0.7126	Intermediate Similarity	NPD4269	Approved
0.7126	Intermediate Similarity	NPD4270	Approved
0.7045	Intermediate Similarity	NPD5362	Discontinued
0.7011	Intermediate Similarity	NPD5369	Approved
0.6932	Remote Similarity	NPD6435	Approved
0.6931	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4225	Approved
0.6905	Remote Similarity	NPD8039	Approved
0.6897	Remote Similarity	NPD4252	Approved
0.6897	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6371	Approved
0.6889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7146	Approved
0.6813	Remote Similarity	NPD7521	Approved
0.6813	Remote Similarity	NPD5330	Approved
0.6813	Remote Similarity	NPD6409	Approved
0.6813	Remote Similarity	NPD7334	Approved
0.6813	Remote Similarity	NPD6684	Approved
0.6737	Remote Similarity	NPD6399	Phase 3
0.6705	Remote Similarity	NPD4820	Approved
0.6705	Remote Similarity	NPD5368	Approved
0.6705	Remote Similarity	NPD4821	Approved
0.6705	Remote Similarity	NPD4822	Approved
0.6705	Remote Similarity	NPD4819	Approved
0.6702	Remote Similarity	NPD7838	Discovery
0.6699	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6632	Remote Similarity	NPD5693	Phase 1
0.6593	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5779	Approved
0.6562	Remote Similarity	NPD5778	Approved
0.6552	Remote Similarity	NPD4756	Discovery
0.6514	Remote Similarity	NPD7115	Discovery
0.6495	Remote Similarity	NPD5282	Discontinued
0.6484	Remote Similarity	NPD5332	Approved
0.6484	Remote Similarity	NPD5331	Approved
0.6465	Remote Similarity	NPD7902	Approved
0.6458	Remote Similarity	NPD7983	Approved
0.6452	Remote Similarity	NPD4249	Approved
0.6444	Remote Similarity	NPD4790	Discontinued
0.6442	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5695	Phase 3
0.6421	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6101	Approved
0.64	Remote Similarity	NPD7638	Approved
0.64	Remote Similarity	NPD5696	Approved
0.6383	Remote Similarity	NPD4250	Approved
0.6383	Remote Similarity	NPD4251	Approved
0.6337	Remote Similarity	NPD7640	Approved
0.6337	Remote Similarity	NPD7639	Approved
0.6327	Remote Similarity	NPD7748	Approved
0.63	Remote Similarity	NPD6083	Phase 2
0.63	Remote Similarity	NPD6084	Phase 2
0.6296	Remote Similarity	NPD6053	Discontinued
0.6289	Remote Similarity	NPD6411	Approved
0.6263	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2067	Discontinued
0.6262	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5370	Suspended
0.625	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD6080	Approved
0.6216	Remote Similarity	NPD6927	Phase 3
0.6211	Remote Similarity	NPD3573	Approved
0.6204	Remote Similarity	NPD6649	Approved
0.6204	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6650	Approved
0.62	Remote Similarity	NPD7839	Suspended
0.619	Remote Similarity	NPD6008	Approved
0.6186	Remote Similarity	NPD5207	Approved
0.6186	Remote Similarity	NPD5692	Phase 3
0.6176	Remote Similarity	NPD6648	Approved
0.6168	Remote Similarity	NPD6373	Approved
0.6168	Remote Similarity	NPD6372	Approved
0.6154	Remote Similarity	NPD4695	Discontinued
0.6146	Remote Similarity	NPD5208	Approved
0.6145	Remote Similarity	NPD7331	Phase 2
0.6145	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5697	Approved
0.6122	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7515	Phase 2
0.6122	Remote Similarity	NPD7637	Suspended
0.6122	Remote Similarity	NPD5694	Approved
0.6122	Remote Similarity	NPD6050	Approved
0.6117	Remote Similarity	NPD5344	Discontinued
0.6105	Remote Similarity	NPD3618	Phase 1
0.6105	Remote Similarity	NPD6422	Discontinued
0.6082	Remote Similarity	NPD6051	Approved
0.6075	Remote Similarity	NPD6899	Approved
0.6075	Remote Similarity	NPD6881	Approved
0.6064	Remote Similarity	NPD3133	Approved
0.6064	Remote Similarity	NPD3668	Phase 3
0.6064	Remote Similarity	NPD3665	Phase 1
0.6064	Remote Similarity	NPD3666	Approved
0.6055	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6402	Approved
0.6038	Remote Similarity	NPD7128	Approved
0.6038	Remote Similarity	NPD5739	Approved
0.6038	Remote Similarity	NPD6675	Approved
0.6022	Remote Similarity	NPD3667	Approved
0.6022	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6012	Approved
0.6019	Remote Similarity	NPD2182	Approved
0.6019	Remote Similarity	NPD6014	Approved
0.6019	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6647	Phase 2
0.6	Remote Similarity	NPD6001	Approved
0.5981	Remote Similarity	NPD5701	Approved
0.5976	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD9298	Approved
0.5963	Remote Similarity	NPD7102	Approved
0.5963	Remote Similarity	NPD7290	Approved
0.5963	Remote Similarity	NPD6883	Approved
0.596	Remote Similarity	NPD5284	Approved
0.596	Remote Similarity	NPD5281	Approved
0.5957	Remote Similarity	NPD6110	Phase 1
0.5941	Remote Similarity	NPD4629	Approved
0.5941	Remote Similarity	NPD5210	Approved
0.5938	Remote Similarity	NPD5279	Phase 3
0.5938	Remote Similarity	NPD6098	Approved
0.5926	Remote Similarity	NPD7320	Approved
0.5926	Remote Similarity	NPD6011	Approved
0.5918	Remote Similarity	NPD4753	Phase 2
0.5909	Remote Similarity	NPD6617	Approved
0.5909	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD8130	Phase 1
0.5909	Remote Similarity	NPD6869	Approved
0.5904	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4786	Approved
0.5882	Remote Similarity	NPD4697	Phase 3
0.5862	Remote Similarity	NPD4691	Approved
0.5856	Remote Similarity	NPD6882	Approved
0.5856	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD7341	Phase 2
0.58	Remote Similarity	NPD8034	Phase 2
0.58	Remote Similarity	NPD8035	Phase 2
0.58	Remote Similarity	NPD6079	Approved
0.5789	Remote Similarity	NPD28	Approved
0.5789	Remote Similarity	NPD29	Approved
0.5784	Remote Similarity	NPD5654	Approved
0.5773	Remote Similarity	NPD4623	Approved
0.5773	Remote Similarity	NPD4519	Discontinued
0.5773	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD3704	Approved
0.5758	Remote Similarity	NPD5328	Approved
0.5758	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5211	Phase 2
0.5755	Remote Similarity	NPD7632	Discontinued
0.5747	Remote Similarity	NPD4137	Phase 3
0.5732	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5222	Approved
0.5728	Remote Similarity	NPD5221	Approved
0.5728	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD7732	Phase 3
0.5726	Remote Similarity	NPD8515	Approved
0.5726	Remote Similarity	NPD8516	Approved
0.5726	Remote Similarity	NPD8513	Phase 3
0.5726	Remote Similarity	NPD8517	Approved
0.5714	Remote Similarity	NPD3197	Phase 1
0.5714	Remote Similarity	NPD5286	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5702	Remote Similarity	NPD6274	Approved
0.5701	Remote Similarity	NPD6052	Approved
0.5698	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7260	Phase 2
0.5688	Remote Similarity	NPD6614	Approved
0.5688	Remote Similarity	NPD6412	Phase 2
0.5684	Remote Similarity	NPD4223	Phase 3
0.5684	Remote Similarity	NPD4221	Approved
0.5682	Remote Similarity	NPD4747	Approved
0.5673	Remote Similarity	NPD5173	Approved
0.5673	Remote Similarity	NPD4755	Approved
0.5673	Remote Similarity	NPD5959	Approved
0.567	Remote Similarity	NPD1696	Phase 3

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