NPASS Compound

Structure

NPC35556 OpenBabel07101718302D 26 28 0 0 1 0 0 0 0 0999 V2000 4.2983 -5.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6981 -4.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8718 -2.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8769 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0028 -3.1854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4635 -2.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0722 -3.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4720 -2.9243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9531 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7459 2.0731 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 3.6895 -4.5110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8633 -2.1310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9531 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6201 -2.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2459 1.2071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2459 1.2071 0.0000 C 0 0 2 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 3.2459 -1.2071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2459 -1.2071 0.0000 C 0 0 2 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 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2288 -1.4682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 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 3.6286 -2.1310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 11 18 1 0 0 0 0 11 25 1 0 0 0 0 13 3 1 1 0 0 0 14 4 1 1 0 0 0 14 16 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 10 1 6 0 0 0 16 17 1 0 0 0 0 17 10 1 6 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 13 1 6 0 0 0 21 22 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	388.014
LogP:	6.079
LogD:	5.166
LogS:	-3.948
# Rotatable Bonds:	6
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	4.822
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	2.1276067855069414e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.683

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	95.84335327148438%
Volume Distribution (VD):	3.357
Pgp-substrate:	4.053701400756836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.451
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.526

ADMET: Excretion

Clearance (CL):	10.763
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.871
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.745

Download Data

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

Natural Product: NPC35556

Natural Product ID:	NPC35556
*Common Name:**	Acetoxycrenulide
IUPAC Name:	n.a.
Synonyms:	Acetoxycrenulide
Standard InCHIKey:	OGYMASQTERCZQQ-BSISXJFESA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-12(2)7-6-8-13(3)20-18-11-25-22(24)21(18)17-10-16(17)14(4)9-19(20)26-15(5)23/h7,13-14,16-17,19-20H,6,8-11H2,1-5H3/t13-,14+,16-,17-,19+,20-/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@@H]1C2=C([C@@H]3C[C@@H]3[C@@H](C)C[C@@H]1OC(=O)C)C(=O)OC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478102
PubChem CID:	44584501
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277314]
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[489512]
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[489512]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[489512]

☑ 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 NPC35556 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	222
0.1-0.2	1381
0.2-0.3	5801
0.3-0.4	15427
0.4-0.5	10310
0.5-0.6	6001
0.6-0.7	2961
0.7-0.8	567
0.8-0.85	23
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC82297
0.8642	High Similarity	NPC471325
0.85	High Similarity	NPC128276
0.8415	Intermediate Similarity	NPC141810
0.8395	Intermediate Similarity	NPC178277
0.8375	Intermediate Similarity	NPC57744
0.825	Intermediate Similarity	NPC123360
0.8235	Intermediate Similarity	NPC78089
0.8228	Intermediate Similarity	NPC140287
0.8228	Intermediate Similarity	NPC476355
0.8228	Intermediate Similarity	NPC474758
0.8214	Intermediate Similarity	NPC193198
0.8214	Intermediate Similarity	NPC53867
0.8193	Intermediate Similarity	NPC42470
0.8193	Intermediate Similarity	NPC281949
0.8193	Intermediate Similarity	NPC325031
0.8193	Intermediate Similarity	NPC25684
0.8193	Intermediate Similarity	NPC301477
0.8171	Intermediate Similarity	NPC617
0.8158	Intermediate Similarity	NPC472266
0.8148	Intermediate Similarity	NPC97516
0.8148	Intermediate Similarity	NPC470240
0.8148	Intermediate Similarity	NPC476794
0.814	Intermediate Similarity	NPC261253
0.814	Intermediate Similarity	NPC474045
0.814	Intermediate Similarity	NPC107787
0.8125	Intermediate Similarity	NPC244166
0.8095	Intermediate Similarity	NPC173609
0.8049	Intermediate Similarity	NPC299235
0.8046	Intermediate Similarity	NPC475703
0.8025	Intermediate Similarity	NPC235906
0.8023	Intermediate Similarity	NPC474547
0.8	Intermediate Similarity	NPC475989
0.8	Intermediate Similarity	NPC15499
0.8	Intermediate Similarity	NPC475842
0.8	Intermediate Similarity	NPC474703
0.8	Intermediate Similarity	NPC475947
0.8	Intermediate Similarity	NPC117746
0.8	Intermediate Similarity	NPC259599
0.8	Intermediate Similarity	NPC294434
0.7978	Intermediate Similarity	NPC469368
0.7978	Intermediate Similarity	NPC473448
0.7976	Intermediate Similarity	NPC475481
0.7976	Intermediate Similarity	NPC79277
0.7975	Intermediate Similarity	NPC84038
0.7975	Intermediate Similarity	NPC163003
0.7955	Intermediate Similarity	NPC475902
0.7952	Intermediate Similarity	NPC270126
0.7952	Intermediate Similarity	NPC469620
0.7952	Intermediate Similarity	NPC469690
0.7952	Intermediate Similarity	NPC471299
0.7931	Intermediate Similarity	NPC284902
0.7931	Intermediate Similarity	NPC50637
0.7931	Intermediate Similarity	NPC469483
0.7931	Intermediate Similarity	NPC305475
0.7931	Intermediate Similarity	NPC261721
0.7931	Intermediate Similarity	NPC475461
0.7927	Intermediate Similarity	NPC187568
0.7927	Intermediate Similarity	NPC41780
0.7927	Intermediate Similarity	NPC65603
0.7927	Intermediate Similarity	NPC141789
0.7927	Intermediate Similarity	NPC171204
0.7927	Intermediate Similarity	NPC476028
0.7907	Intermediate Similarity	NPC115786
0.7907	Intermediate Similarity	NPC474359
0.7889	Intermediate Similarity	NPC221282
0.7882	Intermediate Similarity	NPC475936
0.7882	Intermediate Similarity	NPC89555
0.7882	Intermediate Similarity	NPC200513
0.7875	Intermediate Similarity	NPC474705
0.7865	Intermediate Similarity	NPC166919
0.7857	Intermediate Similarity	NPC281132
0.7848	Intermediate Similarity	NPC469660
0.7841	Intermediate Similarity	NPC231889
0.7841	Intermediate Similarity	NPC312561
0.7831	Intermediate Similarity	NPC474341
0.7831	Intermediate Similarity	NPC471220
0.7831	Intermediate Similarity	NPC108816
0.7831	Intermediate Similarity	NPC93763
0.7826	Intermediate Similarity	NPC33473
0.7821	Intermediate Similarity	NPC218477
0.7821	Intermediate Similarity	NPC276290
0.7816	Intermediate Similarity	NPC189311
0.7816	Intermediate Similarity	NPC255307
0.7816	Intermediate Similarity	NPC215364
0.7802	Intermediate Similarity	NPC476597
0.7802	Intermediate Similarity	NPC476598
0.7792	Intermediate Similarity	NPC248125
0.7791	Intermediate Similarity	NPC272814
0.7791	Intermediate Similarity	NPC474193
0.7791	Intermediate Similarity	NPC12283
0.7791	Intermediate Similarity	NPC475622
0.7791	Intermediate Similarity	NPC170377
0.7791	Intermediate Similarity	NPC108045
0.7778	Intermediate Similarity	NPC475748
0.7778	Intermediate Similarity	NPC312042
0.7778	Intermediate Similarity	NPC62815
0.7778	Intermediate Similarity	NPC281942
0.7778	Intermediate Similarity	NPC232426
0.7765	Intermediate Similarity	NPC255580
0.7765	Intermediate Similarity	NPC39411
0.7753	Intermediate Similarity	NPC226863
0.775	Intermediate Similarity	NPC129665
0.7738	Intermediate Similarity	NPC182550
0.7727	Intermediate Similarity	NPC220478
0.7727	Intermediate Similarity	NPC469676
0.7727	Intermediate Similarity	NPC150755
0.7727	Intermediate Similarity	NPC64153
0.7722	Intermediate Similarity	NPC265574
0.7717	Intermediate Similarity	NPC473316
0.7717	Intermediate Similarity	NPC473330
0.7717	Intermediate Similarity	NPC476267
0.7717	Intermediate Similarity	NPC140543
0.7717	Intermediate Similarity	NPC476596
0.7711	Intermediate Similarity	NPC474760
0.7701	Intermediate Similarity	NPC30486
0.7701	Intermediate Similarity	NPC114979
0.7701	Intermediate Similarity	NPC476804
0.7701	Intermediate Similarity	NPC149869
0.7701	Intermediate Similarity	NPC191476
0.7701	Intermediate Similarity	NPC159635
0.7692	Intermediate Similarity	NPC141831
0.7683	Intermediate Similarity	NPC138408
0.7683	Intermediate Similarity	NPC155587
0.7683	Intermediate Similarity	NPC324762
0.7683	Intermediate Similarity	NPC329852
0.7683	Intermediate Similarity	NPC226669
0.7683	Intermediate Similarity	NPC193351
0.7667	Intermediate Similarity	NPC115179
0.7667	Intermediate Similarity	NPC284561
0.7667	Intermediate Similarity	NPC106040
0.7667	Intermediate Similarity	NPC295312
0.7654	Intermediate Similarity	NPC295633
0.7654	Intermediate Similarity	NPC269206
0.7654	Intermediate Similarity	NPC135703
0.7654	Intermediate Similarity	NPC58956
0.7647	Intermediate Similarity	NPC74673
0.7647	Intermediate Similarity	NPC302426
0.7647	Intermediate Similarity	NPC474510
0.7647	Intermediate Similarity	NPC69271
0.7647	Intermediate Similarity	NPC276356
0.764	Intermediate Similarity	NPC474765
0.764	Intermediate Similarity	NPC476600
0.764	Intermediate Similarity	NPC478144
0.764	Intermediate Similarity	NPC160138
0.7634	Intermediate Similarity	NPC470974
0.7634	Intermediate Similarity	NPC470978
0.7625	Intermediate Similarity	NPC475310
0.7625	Intermediate Similarity	NPC472955
0.7625	Intermediate Similarity	NPC67183
0.7619	Intermediate Similarity	NPC184737
0.7619	Intermediate Similarity	NPC253749
0.7614	Intermediate Similarity	NPC165162
0.7614	Intermediate Similarity	NPC65661
0.7609	Intermediate Similarity	NPC475838
0.7609	Intermediate Similarity	NPC125674
0.7609	Intermediate Similarity	NPC475657
0.7609	Intermediate Similarity	NPC228451
0.759	Intermediate Similarity	NPC301525
0.759	Intermediate Similarity	NPC271070
0.759	Intermediate Similarity	NPC27205
0.7586	Intermediate Similarity	NPC169575
0.7586	Intermediate Similarity	NPC473390
0.7586	Intermediate Similarity	NPC39588
0.7586	Intermediate Similarity	NPC40746
0.7586	Intermediate Similarity	NPC222358
0.7586	Intermediate Similarity	NPC131669
0.7586	Intermediate Similarity	NPC318468
0.7582	Intermediate Similarity	NPC220454
0.7582	Intermediate Similarity	NPC51004
0.7582	Intermediate Similarity	NPC471818
0.7582	Intermediate Similarity	NPC212679
0.7582	Intermediate Similarity	NPC469372
0.7582	Intermediate Similarity	NPC469595
0.7579	Intermediate Similarity	NPC471610
0.7579	Intermediate Similarity	NPC98868
0.7558	Intermediate Similarity	NPC52861
0.7558	Intermediate Similarity	NPC112868
0.7556	Intermediate Similarity	NPC476805
0.7556	Intermediate Similarity	NPC469653
0.7556	Intermediate Similarity	NPC475906
0.7556	Intermediate Similarity	NPC469631
0.7556	Intermediate Similarity	NPC469628
0.7556	Intermediate Similarity	NPC471047
0.7556	Intermediate Similarity	NPC477128
0.7531	Intermediate Similarity	NPC477084
0.7531	Intermediate Similarity	NPC186531
0.7529	Intermediate Similarity	NPC470244
0.7529	Intermediate Similarity	NPC264227
0.7529	Intermediate Similarity	NPC89128
0.7529	Intermediate Similarity	NPC63649
0.7529	Intermediate Similarity	NPC472965
0.7529	Intermediate Similarity	NPC470239
0.7528	Intermediate Similarity	NPC38576
0.7528	Intermediate Similarity	NPC279859
0.7527	Intermediate Similarity	NPC477129
0.7527	Intermediate Similarity	NPC477130
0.7527	Intermediate Similarity	NPC477131
0.7527	Intermediate Similarity	NPC474247
0.75	Intermediate Similarity	NPC474776

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 NPC35556 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	1966
0.2-0.3	3893
0.3-0.4	2130
0.4-0.5	677
0.5-0.6	219
0.6-0.7	54
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7882	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6698	Approved
0.7582	Intermediate Similarity	NPD46	Approved
0.7471	Intermediate Similarity	NPD5209	Approved
0.7436	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1695	Approved
0.7222	Intermediate Similarity	NPD1694	Approved
0.7204	Intermediate Similarity	NPD5785	Approved
0.7191	Intermediate Similarity	NPD5362	Discontinued
0.7191	Intermediate Similarity	NPD7154	Phase 3
0.7083	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8039	Approved
0.7045	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5363	Approved
0.7021	Intermediate Similarity	NPD7838	Discovery
0.7019	Intermediate Similarity	NPD6371	Approved
0.6957	Remote Similarity	NPD7521	Approved
0.6957	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD7334	Approved
0.6957	Remote Similarity	NPD5330	Approved
0.6957	Remote Similarity	NPD7146	Approved
0.6957	Remote Similarity	NPD6684	Approved
0.6893	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6435	Approved
0.6889	Remote Similarity	NPD4270	Approved
0.6889	Remote Similarity	NPD4269	Approved
0.6854	Remote Similarity	NPD4820	Approved
0.6854	Remote Similarity	NPD4821	Approved
0.6854	Remote Similarity	NPD4822	Approved
0.6854	Remote Similarity	NPD4819	Approved
0.6827	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD4268	Approved
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4271	Approved
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD6903	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.6809	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5369	Approved
0.6774	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD6399	Phase 3
0.6701	Remote Similarity	NPD5779	Approved
0.6701	Remote Similarity	NPD5778	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6633	Remote Similarity	NPD7900	Approved
0.6633	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5331	Approved
0.663	Remote Similarity	NPD5332	Approved
0.6598	Remote Similarity	NPD7983	Approved
0.6598	Remote Similarity	NPD5693	Phase 1
0.6593	Remote Similarity	NPD4790	Discontinued
0.6574	Remote Similarity	NPD6053	Discontinued
0.6566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4225	Approved
0.6526	Remote Similarity	NPD4251	Approved
0.6526	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD6648	Approved
0.6465	Remote Similarity	NPD7748	Approved
0.6436	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD6411	Approved
0.6421	Remote Similarity	NPD4249	Approved
0.6415	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5344	Discontinued
0.6392	Remote Similarity	NPD6904	Approved
0.6392	Remote Similarity	NPD6051	Approved
0.6392	Remote Similarity	NPD6673	Approved
0.6392	Remote Similarity	NPD6080	Approved
0.6373	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7115	Discovery
0.6321	Remote Similarity	NPD6008	Approved
0.63	Remote Similarity	NPD5282	Discontinued
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6084	Phase 2
0.6275	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6050	Approved
0.6263	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD6422	Discontinued
0.6239	Remote Similarity	NPD2067	Discontinued
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5695	Phase 3
0.6184	Remote Similarity	NPD6927	Phase 3
0.6182	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7839	Suspended
0.6168	Remote Similarity	NPD7128	Approved
0.6168	Remote Similarity	NPD5739	Approved
0.6168	Remote Similarity	NPD6675	Approved
0.6168	Remote Similarity	NPD6402	Approved
0.6162	Remote Similarity	NPD5692	Phase 3
0.6154	Remote Similarity	NPD4756	Discovery
0.6139	Remote Similarity	NPD6001	Approved
0.6122	Remote Similarity	NPD5208	Approved
0.6118	Remote Similarity	NPD7331	Phase 2
0.61	Remote Similarity	NPD7637	Suspended
0.61	Remote Similarity	NPD5694	Approved
0.6082	Remote Similarity	NPD6098	Approved
0.6071	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5370	Suspended
0.6058	Remote Similarity	NPD5696	Approved
0.6055	Remote Similarity	NPD6899	Approved
0.6055	Remote Similarity	NPD7320	Approved
0.6055	Remote Similarity	NPD6881	Approved
0.6042	Remote Similarity	NPD3665	Phase 1
0.6042	Remote Similarity	NPD3666	Approved
0.6042	Remote Similarity	NPD3133	Approved
0.6042	Remote Similarity	NPD3668	Phase 3
0.6042	Remote Similarity	NPD4786	Approved
0.6038	Remote Similarity	NPD7632	Discontinued
0.602	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5974	Remote Similarity	NPD28	Approved
0.5974	Remote Similarity	NPD29	Approved
0.5963	Remote Similarity	NPD5697	Approved
0.5963	Remote Similarity	NPD5701	Approved
0.5962	Remote Similarity	NPD5959	Approved
0.5957	Remote Similarity	NPD4695	Discontinued
0.5946	Remote Similarity	NPD7290	Approved
0.5946	Remote Similarity	NPD7102	Approved
0.5946	Remote Similarity	NPD6883	Approved
0.5941	Remote Similarity	NPD8034	Phase 2
0.5941	Remote Similarity	NPD8035	Phase 2
0.5941	Remote Similarity	NPD5284	Approved
0.5941	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5281	Approved
0.593	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD3618	Phase 1
0.5918	Remote Similarity	NPD5279	Phase 3
0.5917	Remote Similarity	NPD7507	Approved
0.5909	Remote Similarity	NPD6011	Approved
0.59	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5328	Approved
0.5893	Remote Similarity	NPD6847	Approved
0.5893	Remote Similarity	NPD8130	Phase 1
0.5893	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6649	Approved
0.5893	Remote Similarity	NPD6869	Approved
0.5893	Remote Similarity	NPD6617	Approved
0.5893	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD3197	Phase 1
0.5865	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6013	Approved
0.5856	Remote Similarity	NPD6014	Approved
0.5856	Remote Similarity	NPD6012	Approved
0.5841	Remote Similarity	NPD6882	Approved
0.5841	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD6647	Phase 2
0.5833	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6412	Phase 2
0.5804	Remote Similarity	NPD6420	Discontinued
0.5784	Remote Similarity	NPD6079	Approved
0.5772	Remote Similarity	NPD7319	Approved
0.5769	Remote Similarity	NPD5654	Approved
0.5758	Remote Similarity	NPD4519	Discontinued
0.5758	Remote Similarity	NPD4623	Approved
0.575	Remote Similarity	NPD4266	Approved
0.575	Remote Similarity	NPD3196	Approved
0.575	Remote Similarity	NPD3195	Phase 2
0.575	Remote Similarity	NPD3194	Approved
0.5743	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD4202	Approved
0.5728	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8516	Approved
0.5714	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2182	Approved
0.5714	Remote Similarity	NPD7732	Phase 3
0.5714	Remote Similarity	NPD8513	Phase 3
0.5714	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8515	Approved
0.5714	Remote Similarity	NPD8517	Approved
0.5688	Remote Similarity	NPD6052	Approved
0.5682	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7260	Phase 2
0.567	Remote Similarity	NPD4221	Approved
0.567	Remote Similarity	NPD4223	Phase 3
0.566	Remote Similarity	NPD4755	Approved
0.5657	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD1696	Phase 3
0.5657	Remote Similarity	NPD5329	Approved
0.5641	Remote Similarity	NPD7505	Discontinued
0.5636	Remote Similarity	NPD5909	Discontinued
0.5625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3172	Approved
0.562	Remote Similarity	NPD7829	Approved
0.562	Remote Similarity	NPD7604	Phase 2
0.562	Remote Similarity	NPD7830	Approved
0.5614	Remote Similarity	NPD7116	Clinical (unspecified phase)

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