NPASS Compound

Structure

NPC52756 OpenBabel07101718292D 32 37 0 0 1 0 0 0 0 0999 V2000 -2.1961 2.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8687 2.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7493 2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9491 2.2730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9278 1.2082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8918 0.9422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2699 0.4551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 26 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 24 1 0 0 0 0 12 19 1 0 0 0 0 13 26 1 0 0 0 0 13 27 1 0 0 0 0 14 1 1 1 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 6 0 0 0 16 11 1 1 0 0 0 16 21 1 0 0 0 0 16 32 1 0 0 0 0 17 23 1 0 0 0 0 17 26 1 6 0 0 0 18 23 1 0 0 0 0 18 29 2 0 0 0 0 19 25 1 6 0 0 0 19 30 1 0 0 0 0 20 31 2 0 0 0 0 20 32 1 0 0 0 0 21 25 1 6 0 0 0 22 24 1 1 0 0 0 22 27 1 0 0 0 0 24 25 1 1 0 0 0 25 5 1 6 0 0 0 26 27 1 1 0 0 0 27 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	462.888
LogP:	3.213
LogD:	3.487
LogS:	-4.091
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	6.086
Fsp3:	0.926
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:	-5.256
MDCK Permeability:	3.576460585463792e-05
Pgp-inhibitor:	0.168
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.58
Plasma Protein Binding (PPB):	82.20790100097656%
Volume Distribution (VD):	0.651
Pgp-substrate:	13.213094711303711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.716
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.509

ADMET: Excretion

Clearance (CL):	5.165
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.89
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.674
Carcinogencity:	0.107
Eye Corrosion:	0.017
Eye Irritation:	0.033
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC52756

Natural Product ID:	NPC52756
*Common Name:**	Lancifodilactone H
IUPAC Name:	n.a.
Synonyms:	lancifodilactone H
Standard InCHIKey:	VOQMBAJQSRMTML-CMXOSDEXSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-14-6-7-20(31)32-16-11-24(4)22-15(28)10-17-23(2,3)18(29)8-9-26(17)13-27(22,26)12-19(30)25(24,5)21(14)16/h14-17,19,21-22,28,30H,6-13H2,1-5H3/t14-,15+,16-,17+,19-,21+,22+,24+,25-,26-,27+/m1/s1
SMILES:	O=C1CC[C@H]([C@H]2[C@H](O1)C[C@@]1([C@]2(C)[C@H](O)C[C@@]23[C@H]1[C@@H](O)C[C@@H]1[C@]3(C2)CCC(=O)C1(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481455
PubChem CID:	11669451
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499331]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643044]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	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	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200.0	ug.mL-1	PMID[542414]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	16.6	ug.mL-1	PMID[542414]

☑ 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 NPC52756 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	435
0.1-0.2	3533
0.2-0.3	9749
0.3-0.4	13499
0.4-0.5	5505
0.5-0.6	5657
0.6-0.7	3488
0.7-0.8	757
0.8-0.85	67
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9425	High Similarity	NPC77756
0.9	High Similarity	NPC476189
0.8824	High Similarity	NPC469745
0.875	High Similarity	NPC472272
0.8736	High Similarity	NPC471044
0.8736	High Similarity	NPC473336
0.8706	High Similarity	NPC477851
0.8696	High Similarity	NPC470423
0.8696	High Similarity	NPC470424
0.8652	High Similarity	NPC239938
0.8588	High Similarity	NPC201276
0.8588	High Similarity	NPC320144
0.8588	High Similarity	NPC80891
0.8539	High Similarity	NPC302111
0.8506	High Similarity	NPC61107
0.8506	High Similarity	NPC289486
0.8471	Intermediate Similarity	NPC224802
0.8471	Intermediate Similarity	NPC324700
0.8471	Intermediate Similarity	NPC80089
0.8471	Intermediate Similarity	NPC171426
0.8471	Intermediate Similarity	NPC34046
0.8471	Intermediate Similarity	NPC185465
0.8404	Intermediate Similarity	NPC470031
0.8404	Intermediate Similarity	NPC287354
0.8404	Intermediate Similarity	NPC62407
0.8404	Intermediate Similarity	NPC305808
0.8387	Intermediate Similarity	NPC161035
0.8372	Intermediate Similarity	NPC476176
0.8353	Intermediate Similarity	NPC207010
0.8353	Intermediate Similarity	NPC317913
0.8333	Intermediate Similarity	NPC476727
0.8333	Intermediate Similarity	NPC476726
0.8333	Intermediate Similarity	NPC472745
0.8316	Intermediate Similarity	NPC476728
0.8315	Intermediate Similarity	NPC319909
0.8315	Intermediate Similarity	NPC237938
0.8315	Intermediate Similarity	NPC219535
0.8298	Intermediate Similarity	NPC477495
0.8295	Intermediate Similarity	NPC121121
0.8261	Intermediate Similarity	NPC471459
0.8261	Intermediate Similarity	NPC56962
0.8261	Intermediate Similarity	NPC200580
0.8261	Intermediate Similarity	NPC67653
0.8261	Intermediate Similarity	NPC24705
0.8256	Intermediate Similarity	NPC471045
0.8235	Intermediate Similarity	NPC4209
0.8229	Intermediate Similarity	NPC471241
0.8222	Intermediate Similarity	NPC473350
0.8202	Intermediate Similarity	NPC327451
0.8191	Intermediate Similarity	NPC472231
0.8191	Intermediate Similarity	NPC472232
0.8182	Intermediate Similarity	NPC12933
0.8163	Intermediate Similarity	NPC121218
0.8163	Intermediate Similarity	NPC253886
0.8152	Intermediate Similarity	NPC226491
0.8152	Intermediate Similarity	NPC477614
0.814	Intermediate Similarity	NPC475031
0.8132	Intermediate Similarity	NPC80700
0.8132	Intermediate Similarity	NPC83242
0.8125	Intermediate Similarity	NPC29410
0.8125	Intermediate Similarity	NPC200054
0.8125	Intermediate Similarity	NPC116683
0.8125	Intermediate Similarity	NPC234564
0.8118	Intermediate Similarity	NPC273366
0.8118	Intermediate Similarity	NPC159789
0.8118	Intermediate Similarity	NPC212733
0.8111	Intermediate Similarity	NPC473299
0.8111	Intermediate Similarity	NPC477434
0.8111	Intermediate Similarity	NPC50438
0.81	Intermediate Similarity	NPC327093
0.81	Intermediate Similarity	NPC29705
0.809	Intermediate Similarity	NPC30583
0.8081	Intermediate Similarity	NPC470172
0.8081	Intermediate Similarity	NPC170615
0.8081	Intermediate Similarity	NPC244969
0.8081	Intermediate Similarity	NPC213528
0.8068	Intermediate Similarity	NPC261616
0.8068	Intermediate Similarity	NPC470609
0.8065	Intermediate Similarity	NPC61688
0.8061	Intermediate Similarity	NPC41843
0.8061	Intermediate Similarity	NPC94906
0.8043	Intermediate Similarity	NPC202937
0.8041	Intermediate Similarity	NPC472273
0.8039	Intermediate Similarity	NPC211224
0.8023	Intermediate Similarity	NPC472487
0.8023	Intermediate Similarity	NPC471046
0.8023	Intermediate Similarity	NPC472486
0.8022	Intermediate Similarity	NPC266651
0.8021	Intermediate Similarity	NPC205173
0.8021	Intermediate Similarity	NPC98639
0.802	Intermediate Similarity	NPC278628
0.802	Intermediate Similarity	NPC231530
0.8	Intermediate Similarity	NPC473406
0.8	Intermediate Similarity	NPC280026
0.8	Intermediate Similarity	NPC167702
0.8	Intermediate Similarity	NPC469985
0.7981	Intermediate Similarity	NPC470281
0.798	Intermediate Similarity	NPC75941
0.7978	Intermediate Similarity	NPC77311
0.7978	Intermediate Similarity	NPC58631
0.7978	Intermediate Similarity	NPC73515
0.7961	Intermediate Similarity	NPC227879
0.7961	Intermediate Similarity	NPC208333
0.7959	Intermediate Similarity	NPC28864
0.7959	Intermediate Similarity	NPC20479
0.7959	Intermediate Similarity	NPC472028
0.7959	Intermediate Similarity	NPC38296
0.7959	Intermediate Similarity	NPC471038
0.7959	Intermediate Similarity	NPC162459
0.7959	Intermediate Similarity	NPC38471
0.7959	Intermediate Similarity	NPC98837
0.7957	Intermediate Similarity	NPC236459
0.7957	Intermediate Similarity	NPC131104
0.7957	Intermediate Similarity	NPC473319
0.7957	Intermediate Similarity	NPC3032
0.7955	Intermediate Similarity	NPC472310
0.7938	Intermediate Similarity	NPC329910
0.7938	Intermediate Similarity	NPC193785
0.7935	Intermediate Similarity	NPC474448
0.7935	Intermediate Similarity	NPC248216
0.7931	Intermediate Similarity	NPC474404
0.7931	Intermediate Similarity	NPC143133
0.7931	Intermediate Similarity	NPC298168
0.7931	Intermediate Similarity	NPC221420
0.7921	Intermediate Similarity	NPC47281
0.7921	Intermediate Similarity	NPC100078
0.7921	Intermediate Similarity	NPC310586
0.7907	Intermediate Similarity	NPC125767
0.7907	Intermediate Similarity	NPC179858
0.7907	Intermediate Similarity	NPC186851
0.7907	Intermediate Similarity	NPC21220
0.79	Intermediate Similarity	NPC15396
0.79	Intermediate Similarity	NPC124544
0.7895	Intermediate Similarity	NPC475878
0.7895	Intermediate Similarity	NPC473066
0.7889	Intermediate Similarity	NPC317066
0.7889	Intermediate Similarity	NPC268040
0.7882	Intermediate Similarity	NPC232112
0.7879	Intermediate Similarity	NPC108371
0.7879	Intermediate Similarity	NPC180733
0.7879	Intermediate Similarity	NPC293866
0.7879	Intermediate Similarity	NPC41971
0.7879	Intermediate Similarity	NPC37047
0.7872	Intermediate Similarity	NPC477443
0.7872	Intermediate Similarity	NPC477440
0.7865	Intermediate Similarity	NPC472853
0.7865	Intermediate Similarity	NPC474714
0.7864	Intermediate Similarity	NPC94529
0.7864	Intermediate Similarity	NPC472079
0.7864	Intermediate Similarity	NPC316930
0.7849	Intermediate Similarity	NPC470920
0.7849	Intermediate Similarity	NPC263802
0.7849	Intermediate Similarity	NPC5943
0.7843	Intermediate Similarity	NPC37600
0.7843	Intermediate Similarity	NPC265127
0.7843	Intermediate Similarity	NPC166079
0.7843	Intermediate Similarity	NPC50535
0.7843	Intermediate Similarity	NPC306776
0.7843	Intermediate Similarity	NPC28791
0.7843	Intermediate Similarity	NPC295366
0.7841	Intermediate Similarity	NPC476732
0.7841	Intermediate Similarity	NPC199965
0.7835	Intermediate Similarity	NPC470232
0.7835	Intermediate Similarity	NPC288906
0.7835	Intermediate Similarity	NPC470229
0.7835	Intermediate Similarity	NPC17336
0.7835	Intermediate Similarity	NPC263135
0.7822	Intermediate Similarity	NPC471253
0.7822	Intermediate Similarity	NPC470310
0.7822	Intermediate Similarity	NPC87927
0.7822	Intermediate Similarity	NPC140723
0.7816	Intermediate Similarity	NPC5767
0.7816	Intermediate Similarity	NPC475742
0.7812	Intermediate Similarity	NPC244356
0.7812	Intermediate Similarity	NPC224060
0.7802	Intermediate Similarity	NPC15091
0.7802	Intermediate Similarity	NPC259173
0.78	Intermediate Similarity	NPC289148
0.78	Intermediate Similarity	NPC52899
0.78	Intermediate Similarity	NPC46848
0.78	Intermediate Similarity	NPC163963
0.78	Intermediate Similarity	NPC252614
0.78	Intermediate Similarity	NPC295276
0.7789	Intermediate Similarity	NPC88337
0.7789	Intermediate Similarity	NPC475211
0.7789	Intermediate Similarity	NPC477444
0.7789	Intermediate Similarity	NPC477442
0.7789	Intermediate Similarity	NPC477433
0.7789	Intermediate Similarity	NPC476296
0.7788	Intermediate Similarity	NPC320475
0.7788	Intermediate Similarity	NPC321661
0.7778	Intermediate Similarity	NPC474793
0.7778	Intermediate Similarity	NPC476294
0.7778	Intermediate Similarity	NPC89099
0.7778	Intermediate Similarity	NPC476071
0.7767	Intermediate Similarity	NPC86852
0.7767	Intermediate Similarity	NPC251824
0.7766	Intermediate Similarity	NPC191221
0.7766	Intermediate Similarity	NPC476379
0.7765	Intermediate Similarity	NPC58057

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 NPC52756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	451
0.1-0.2	3650
0.2-0.3	3443
0.3-0.4	962
0.4-0.5	287
0.5-0.6	183
0.6-0.7	149
0.7-0.8	20
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD6118	Approved
0.8471	Intermediate Similarity	NPD6114	Approved
0.8471	Intermediate Similarity	NPD6697	Approved
0.8471	Intermediate Similarity	NPD6115	Approved
0.8353	Intermediate Similarity	NPD6116	Phase 1
0.8235	Intermediate Similarity	NPD6117	Approved
0.8118	Intermediate Similarity	NPD3703	Phase 2
0.8	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5777	Approved
0.7765	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD3702	Approved
0.7647	Intermediate Similarity	NPD4245	Approved
0.7647	Intermediate Similarity	NPD4244	Approved
0.7573	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3698	Phase 2
0.7529	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6081	Approved
0.7347	Intermediate Similarity	NPD8035	Phase 2
0.7347	Intermediate Similarity	NPD8034	Phase 2
0.7333	Intermediate Similarity	NPD6402	Approved
0.7333	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD7128	Approved
0.7333	Intermediate Similarity	NPD6675	Approved
0.7283	Intermediate Similarity	NPD6928	Phase 2
0.7263	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4789	Approved
0.7209	Intermediate Similarity	NPD5360	Phase 3
0.7209	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6881	Approved
0.7196	Intermediate Similarity	NPD6899	Approved
0.7196	Intermediate Similarity	NPD7320	Approved
0.7176	Intermediate Similarity	NPD4224	Phase 2
0.717	Intermediate Similarity	NPD6008	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.7115	Intermediate Similarity	NPD1700	Approved
0.7103	Intermediate Similarity	NPD5697	Approved
0.7103	Intermediate Similarity	NPD5701	Approved
0.7087	Intermediate Similarity	NPD7638	Approved
0.7069	Intermediate Similarity	NPD7604	Phase 2
0.7064	Intermediate Similarity	NPD7102	Approved
0.7064	Intermediate Similarity	NPD7290	Approved
0.7064	Intermediate Similarity	NPD6883	Approved
0.7059	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6011	Approved
0.7027	Intermediate Similarity	NPD4632	Approved
0.7019	Intermediate Similarity	NPD7640	Approved
0.7019	Intermediate Similarity	NPD7639	Approved
0.7	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD8130	Phase 1
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6847	Approved
0.7	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6014	Approved
0.6972	Remote Similarity	NPD6012	Approved
0.6972	Remote Similarity	NPD6013	Approved
0.6937	Remote Similarity	NPD6882	Approved
0.6937	Remote Similarity	NPD8297	Approved
0.6931	Remote Similarity	NPD6399	Phase 3
0.6887	Remote Similarity	NPD7632	Discontinued
0.6882	Remote Similarity	NPD3671	Phase 1
0.6857	Remote Similarity	NPD8418	Phase 2
0.6842	Remote Similarity	NPD6009	Approved
0.6827	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD6319	Approved
0.68	Remote Similarity	NPD5328	Approved
0.6778	Remote Similarity	NPD4758	Discontinued
0.6752	Remote Similarity	NPD5983	Phase 2
0.6742	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7492	Approved
0.6702	Remote Similarity	NPD5364	Discontinued
0.6701	Remote Similarity	NPD4788	Approved
0.6698	Remote Similarity	NPD5285	Approved
0.6698	Remote Similarity	NPD5286	Approved
0.6698	Remote Similarity	NPD4700	Approved
0.6698	Remote Similarity	NPD4696	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD6079	Approved
0.6638	Remote Similarity	NPD6335	Approved
0.6636	Remote Similarity	NPD5223	Approved
0.6635	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7078	Approved
0.6612	Remote Similarity	NPD8293	Discontinued
0.6609	Remote Similarity	NPD6274	Approved
0.6602	Remote Similarity	NPD8171	Discontinued
0.6602	Remote Similarity	NPD4202	Approved
0.6581	Remote Similarity	NPD7100	Approved
0.6581	Remote Similarity	NPD7101	Approved
0.6579	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD4633	Approved
0.6574	Remote Similarity	NPD5225	Approved
0.6574	Remote Similarity	NPD5211	Phase 2
0.6574	Remote Similarity	NPD5224	Approved
0.6574	Remote Similarity	NPD5226	Approved
0.6555	Remote Similarity	NPD6370	Approved
0.6552	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD7748	Approved
0.6535	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4238	Approved
0.6526	Remote Similarity	NPD4802	Phase 2
0.6514	Remote Similarity	NPD5174	Approved
0.6514	Remote Similarity	NPD4754	Approved
0.6514	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD7902	Approved
0.6505	Remote Similarity	NPD7515	Phase 2
0.6504	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD7146	Approved
0.65	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD7334	Approved
0.65	Remote Similarity	NPD7521	Approved
0.65	Remote Similarity	NPD5330	Approved
0.65	Remote Similarity	NPD6684	Approved
0.6496	Remote Similarity	NPD6314	Approved
0.6496	Remote Similarity	NPD6313	Approved
0.6495	Remote Similarity	NPD1780	Approved
0.6495	Remote Similarity	NPD1779	Approved
0.6491	Remote Similarity	NPD6053	Discontinued
0.6486	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD3198	Approved
0.6471	Remote Similarity	NPD6015	Approved
0.6471	Remote Similarity	NPD6909	Approved
0.6471	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6940	Discontinued
0.6465	Remote Similarity	NPD4786	Approved
0.646	Remote Similarity	NPD4634	Approved
0.6455	Remote Similarity	NPD5141	Approved
0.6417	Remote Similarity	NPD5988	Approved
0.6415	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD5222	Approved
0.6415	Remote Similarity	NPD4697	Phase 3
0.6415	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4767	Approved
0.6396	Remote Similarity	NPD4768	Approved
0.6373	Remote Similarity	NPD6903	Approved
0.6372	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3669	Approved
0.6364	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5173	Approved
0.6337	Remote Similarity	NPD3618	Phase 1
0.6333	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6868	Approved
0.6321	Remote Similarity	NPD5695	Phase 3
0.6321	Remote Similarity	NPD7991	Discontinued
0.63	Remote Similarity	NPD3666	Approved
0.63	Remote Similarity	NPD3665	Phase 1
0.63	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD5696	Approved
0.629	Remote Similarity	NPD6033	Approved
0.6283	Remote Similarity	NPD5128	Approved
0.6283	Remote Similarity	NPD4730	Approved
0.6283	Remote Similarity	NPD4729	Approved
0.6271	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6435	Approved
0.6263	Remote Similarity	NPD3667	Approved
0.6226	Remote Similarity	NPD7900	Approved
0.6226	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6001	Approved
0.6224	Remote Similarity	NPD7525	Registered
0.6214	Remote Similarity	NPD6672	Approved
0.6214	Remote Similarity	NPD5737	Approved
0.6176	Remote Similarity	NPD6098	Approved
0.6174	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5169	Approved
0.6174	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5249	Phase 3
0.6174	Remote Similarity	NPD5248	Approved
0.6174	Remote Similarity	NPD5247	Approved
0.6174	Remote Similarity	NPD5250	Approved
0.6174	Remote Similarity	NPD5135	Approved
0.6174	Remote Similarity	NPD5251	Approved
0.6154	Remote Similarity	NPD8298	Phase 2
0.6154	Remote Similarity	NPD6904	Approved
0.6154	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD6080	Approved
0.6134	Remote Similarity	NPD7115	Discovery
0.6121	Remote Similarity	NPD5216	Approved
0.6121	Remote Similarity	NPD5127	Approved
0.6121	Remote Similarity	NPD5217	Approved
0.6121	Remote Similarity	NPD5215	Approved
0.6106	Remote Similarity	NPD6920	Discontinued
0.6098	Remote Similarity	NPD6067	Discontinued
0.6098	Remote Similarity	NPD8328	Phase 3
0.6083	Remote Similarity	NPD7327	Approved
0.6083	Remote Similarity	NPD7328	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