NPASS Compound

Structure

NPC329842 OpenBabel07101718182D 27 30 0 0 1 0 0 0 0 0999 V2000 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7812 0.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1472 1.3090 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 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 1 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 4.4152 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 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 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 22 1 0 0 0 0 12 1 1 6 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 23 2 0 0 0 0 13 26 1 0 0 0 0 14 9 1 6 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 1 0 0 0 17 19 1 0 0 0 0 17 26 1 6 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 1 0 0 0 21 5 1 1 0 0 0 22 25 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	390.884
LogP:	4.554
LogD:	4.076
LogS:	-4.747
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	4.853
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.72
MDCK Permeability:	1.8629132682690397e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.891
Plasma Protein Binding (PPB):	89.82597351074219%
Volume Distribution (VD):	1.779
Pgp-substrate:	16.5576229095459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.289
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.471
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.707
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	5.867
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.587
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.829
Maximum Recommended Daily Dose:	0.803
Skin Sensitization:	0.87
Carcinogencity:	0.654
Eye Corrosion:	0.093
Eye Irritation:	0.068
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC329842

Natural Product ID:	NPC329842
*Common Name:**	Sucutinirane A
IUPAC Name:	[(4aS,5S,6aS,7R,10aR,11aS,11bR)-10a-hydroxy-4,4,7,11b-tetramethyl-9-oxo-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-5-yl] acetate
Synonyms:
Standard InCHIKey:	SBMJOOYWCLPOPY-RTVASPDHSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-12-14-9-17(26-13(2)23)19-20(3,4)7-6-8-21(19,5)16(14)11-22(25)15(12)10-18(24)27-22/h10,12,14,16-17,19,25H,6-9,11H2,1-5H3/t12-,14+,16+,17+,19+,21-,22-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@H](C)C3=CC(=O)O[C@@]3(C[C@@H]2[C@@]2([C@@H]1C(C)(C)CCC2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514119
PubChem CID:	24863609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524584]
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361174]
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO28335	Bowdichia nitida	Species	Fabaceae	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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	14000.0	nM	PMID[483329]
NPT27	Others	Unspecified		IC50	=	37.3	ug.mL-1	PMID[483328]

☑ 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 NPC329842 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	185
0.1-0.2	1251
0.2-0.3	4248
0.3-0.4	10484
0.4-0.5	12221
0.5-0.6	6592
0.6-0.7	5580
0.7-0.8	1889
0.8-0.85	198
0.85-0.9	40
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC474013
0.9205	High Similarity	NPC78973
0.9101	High Similarity	NPC472811
0.9011	High Similarity	NPC472441
0.9	High Similarity	NPC472303
0.9	High Similarity	NPC472812
0.8966	High Similarity	NPC131813
0.8925	High Similarity	NPC275086
0.8925	High Similarity	NPC325229
0.8901	High Similarity	NPC469697
0.8889	High Similarity	NPC289479
0.8837	High Similarity	NPC476927
0.883	High Similarity	NPC324841
0.8824	High Similarity	NPC170303
0.8817	High Similarity	NPC477719
0.8817	High Similarity	NPC477718
0.8817	High Similarity	NPC51499
0.8791	High Similarity	NPC7349
0.8791	High Similarity	NPC53555
0.8764	High Similarity	NPC472809
0.8764	High Similarity	NPC472810
0.875	High Similarity	NPC45897
0.875	High Similarity	NPC281378
0.8721	High Similarity	NPC256112
0.871	High Similarity	NPC162346
0.8696	High Similarity	NPC470255
0.8696	High Similarity	NPC298973
0.8696	High Similarity	NPC324078
0.8696	High Similarity	NPC104925
0.8696	High Similarity	NPC105490
0.8673	High Similarity	NPC471205
0.8667	High Similarity	NPC470734
0.8652	High Similarity	NPC166857
0.8632	High Similarity	NPC251680
0.8632	High Similarity	NPC472826
0.8632	High Similarity	NPC476767
0.8632	High Similarity	NPC477716
0.8632	High Similarity	NPC477721
0.8621	High Similarity	NPC311070
0.8602	High Similarity	NPC276110
0.8587	High Similarity	NPC38232
0.8571	High Similarity	NPC51719
0.8571	High Similarity	NPC280149
0.8571	High Similarity	NPC221111
0.8556	High Similarity	NPC474629
0.8556	High Similarity	NPC93411
0.8542	High Similarity	NPC268829
0.8542	High Similarity	NPC222875
0.8542	High Similarity	NPC247701
0.8542	High Similarity	NPC25177
0.8542	High Similarity	NPC295110
0.8542	High Similarity	NPC477717
0.8526	High Similarity	NPC218107
0.8523	High Similarity	NPC96055
0.8523	High Similarity	NPC306951
0.8506	High Similarity	NPC471218
0.8506	High Similarity	NPC2524
0.8495	Intermediate Similarity	NPC201725
0.8488	Intermediate Similarity	NPC10636
0.8488	Intermediate Similarity	NPC281880
0.8485	Intermediate Similarity	NPC122816
0.8454	Intermediate Similarity	NPC472815
0.8454	Intermediate Similarity	NPC476769
0.8438	Intermediate Similarity	NPC477972
0.8438	Intermediate Similarity	NPC477968
0.8438	Intermediate Similarity	NPC228251
0.8438	Intermediate Similarity	NPC161527
0.8438	Intermediate Similarity	NPC20113
0.8438	Intermediate Similarity	NPC38855
0.8438	Intermediate Similarity	NPC477971
0.8438	Intermediate Similarity	NPC16601
0.8438	Intermediate Similarity	NPC219285
0.8438	Intermediate Similarity	NPC201406
0.8438	Intermediate Similarity	NPC117685
0.8427	Intermediate Similarity	NPC42586
0.8427	Intermediate Similarity	NPC473251
0.8421	Intermediate Similarity	NPC231751
0.8409	Intermediate Similarity	NPC42476
0.8391	Intermediate Similarity	NPC159148
0.8387	Intermediate Similarity	NPC205034
0.8387	Intermediate Similarity	NPC472640
0.8387	Intermediate Similarity	NPC162615
0.8387	Intermediate Similarity	NPC139692
0.8387	Intermediate Similarity	NPC152778
0.8387	Intermediate Similarity	NPC476304
0.8387	Intermediate Similarity	NPC472641
0.8384	Intermediate Similarity	NPC472818
0.837	Intermediate Similarity	NPC310479
0.837	Intermediate Similarity	NPC182136
0.837	Intermediate Similarity	NPC302280
0.837	Intermediate Similarity	NPC472642
0.8367	Intermediate Similarity	NPC160583
0.8367	Intermediate Similarity	NPC471208
0.8367	Intermediate Similarity	NPC189588
0.8367	Intermediate Similarity	NPC196471
0.8367	Intermediate Similarity	NPC97487
0.8367	Intermediate Similarity	NPC180204
0.8367	Intermediate Similarity	NPC112009
0.8367	Intermediate Similarity	NPC120009
0.8367	Intermediate Similarity	NPC187302
0.8367	Intermediate Similarity	NPC10232
0.8351	Intermediate Similarity	NPC11974
0.8333	Intermediate Similarity	NPC473154
0.8333	Intermediate Similarity	NPC474440
0.8333	Intermediate Similarity	NPC175145
0.8333	Intermediate Similarity	NPC475069
0.8333	Intermediate Similarity	NPC278673
0.8317	Intermediate Similarity	NPC475030
0.8316	Intermediate Similarity	NPC473153
0.8316	Intermediate Similarity	NPC134072
0.8316	Intermediate Similarity	NPC242848
0.8316	Intermediate Similarity	NPC165632
0.8316	Intermediate Similarity	NPC234993
0.8316	Intermediate Similarity	NPC190713
0.8316	Intermediate Similarity	NPC16967
0.8315	Intermediate Similarity	NPC471302
0.8315	Intermediate Similarity	NPC318515
0.83	Intermediate Similarity	NPC472820
0.8298	Intermediate Similarity	NPC476186
0.8298	Intermediate Similarity	NPC57117
0.8298	Intermediate Similarity	NPC477722
0.8283	Intermediate Similarity	NPC472819
0.828	Intermediate Similarity	NPC74296
0.828	Intermediate Similarity	NPC72845
0.828	Intermediate Similarity	NPC477122
0.828	Intermediate Similarity	NPC177641
0.828	Intermediate Similarity	NPC110923
0.828	Intermediate Similarity	NPC78594
0.8265	Intermediate Similarity	NPC475038
0.8265	Intermediate Similarity	NPC109195
0.8261	Intermediate Similarity	NPC170633
0.8261	Intermediate Similarity	NPC82876
0.8261	Intermediate Similarity	NPC472240
0.8261	Intermediate Similarity	NPC474396
0.8261	Intermediate Similarity	NPC262858
0.8261	Intermediate Similarity	NPC50488
0.8247	Intermediate Similarity	NPC474190
0.8247	Intermediate Similarity	NPC471413
0.8247	Intermediate Similarity	NPC477720
0.8235	Intermediate Similarity	NPC177047
0.8229	Intermediate Similarity	NPC132753
0.8229	Intermediate Similarity	NPC121402
0.8229	Intermediate Similarity	NPC253826
0.8229	Intermediate Similarity	NPC224356
0.8229	Intermediate Similarity	NPC151681
0.8229	Intermediate Similarity	NPC476768
0.8229	Intermediate Similarity	NPC175351
0.8222	Intermediate Similarity	NPC253604
0.8222	Intermediate Similarity	NPC473659
0.8222	Intermediate Similarity	NPC30984
0.8222	Intermediate Similarity	NPC474694
0.8222	Intermediate Similarity	NPC475860
0.8222	Intermediate Similarity	NPC472442
0.8222	Intermediate Similarity	NPC35933
0.8218	Intermediate Similarity	NPC38948
0.8202	Intermediate Similarity	NPC471297
0.8202	Intermediate Similarity	NPC472440
0.8202	Intermediate Similarity	NPC79945
0.82	Intermediate Similarity	NPC220217
0.82	Intermediate Similarity	NPC186668
0.82	Intermediate Similarity	NPC119855
0.8182	Intermediate Similarity	NPC471938
0.8182	Intermediate Similarity	NPC472821
0.8172	Intermediate Similarity	NPC232426
0.8172	Intermediate Similarity	NPC281942
0.8172	Intermediate Similarity	NPC477782
0.8172	Intermediate Similarity	NPC8062
0.8163	Intermediate Similarity	NPC471412
0.8163	Intermediate Similarity	NPC303559
0.8163	Intermediate Similarity	NPC473160
0.8163	Intermediate Similarity	NPC471075
0.8161	Intermediate Similarity	NPC242767
0.8152	Intermediate Similarity	NPC472378
0.8152	Intermediate Similarity	NPC106332
0.8144	Intermediate Similarity	NPC92275
0.814	Intermediate Similarity	NPC132542
0.814	Intermediate Similarity	NPC189206
0.8137	Intermediate Similarity	NPC206618
0.8132	Intermediate Similarity	NPC329692
0.8132	Intermediate Similarity	NPC471219
0.8132	Intermediate Similarity	NPC474970
0.8125	Intermediate Similarity	NPC472363
0.8125	Intermediate Similarity	NPC114743
0.8125	Intermediate Similarity	NPC94905
0.8125	Intermediate Similarity	NPC154526
0.8125	Intermediate Similarity	NPC195366
0.8125	Intermediate Similarity	NPC472362
0.8125	Intermediate Similarity	NPC8954
0.8125	Intermediate Similarity	NPC194132
0.8125	Intermediate Similarity	NPC88009
0.8119	Intermediate Similarity	NPC475570
0.8119	Intermediate Similarity	NPC475074
0.8111	Intermediate Similarity	NPC102048
0.8111	Intermediate Similarity	NPC32223
0.8111	Intermediate Similarity	NPC474693
0.8105	Intermediate Similarity	NPC140277
0.8105	Intermediate Similarity	NPC279410
0.8105	Intermediate Similarity	NPC191521
0.8105	Intermediate Similarity	NPC84893
0.8105	Intermediate Similarity	NPC91010

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 NPC329842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1432
0.2-0.3	3752
0.3-0.4	2524
0.4-0.5	821
0.5-0.6	247
0.6-0.7	182
0.7-0.8	28
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD7640	Approved
0.8632	High Similarity	NPD7639	Approved
0.8526	High Similarity	NPD7638	Approved
0.7959	Intermediate Similarity	NPD4225	Approved
0.7917	Intermediate Similarity	NPD7748	Approved
0.79	Intermediate Similarity	NPD7632	Discontinued
0.7717	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7515	Phase 2
0.7706	Intermediate Similarity	NPD7328	Approved
0.7706	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7902	Approved
0.7636	Intermediate Similarity	NPD7516	Approved
0.7568	Intermediate Similarity	NPD8377	Approved
0.7568	Intermediate Similarity	NPD8294	Approved
0.7524	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD6051	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7473	Intermediate Similarity	NPD7525	Registered
0.7374	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7900	Approved
0.7363	Intermediate Similarity	NPD7645	Phase 2
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7241	Intermediate Similarity	NPD7507	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6409	Approved
0.7188	Intermediate Similarity	NPD7521	Approved
0.7188	Intermediate Similarity	NPD7334	Approved
0.7188	Intermediate Similarity	NPD6684	Approved
0.7188	Intermediate Similarity	NPD7146	Approved
0.7188	Intermediate Similarity	NPD5330	Approved
0.7188	Intermediate Similarity	NPD3618	Phase 1
0.7172	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD8034	Phase 2
0.717	Intermediate Similarity	NPD6675	Approved
0.717	Intermediate Similarity	NPD7128	Approved
0.717	Intermediate Similarity	NPD6402	Approved
0.717	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6882	Approved
0.7083	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1694	Approved
0.7064	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7319	Approved
0.7043	Intermediate Similarity	NPD7503	Approved
0.7041	Intermediate Similarity	NPD6672	Approved
0.7041	Intermediate Similarity	NPD6903	Approved
0.7041	Intermediate Similarity	NPD5737	Approved
0.7037	Intermediate Similarity	NPD7320	Approved
0.7037	Intermediate Similarity	NPD6899	Approved
0.7037	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD6079	Approved
0.699	Remote Similarity	NPD6084	Phase 2
0.699	Remote Similarity	NPD6083	Phase 2
0.6972	Remote Similarity	NPD6373	Approved
0.6972	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD5344	Discontinued
0.6944	Remote Similarity	NPD5701	Approved
0.6944	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD6942	Approved
0.6909	Remote Similarity	NPD7290	Approved
0.6909	Remote Similarity	NPD7102	Approved
0.6909	Remote Similarity	NPD6883	Approved
0.6881	Remote Similarity	NPD6011	Approved
0.6857	Remote Similarity	NPD6648	Approved
0.6848	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6650	Approved
0.6847	Remote Similarity	NPD6869	Approved
0.6847	Remote Similarity	NPD6649	Approved
0.6847	Remote Similarity	NPD6847	Approved
0.6847	Remote Similarity	NPD8130	Phase 1
0.6847	Remote Similarity	NPD6617	Approved
0.6832	Remote Similarity	NPD5693	Phase 1
0.6832	Remote Similarity	NPD7637	Suspended
0.6818	Remote Similarity	NPD6013	Approved
0.6818	Remote Similarity	NPD6014	Approved
0.6818	Remote Similarity	NPD6012	Approved
0.6804	Remote Similarity	NPD3666	Approved
0.6804	Remote Similarity	NPD4786	Approved
0.6804	Remote Similarity	NPD3665	Phase 1
0.6804	Remote Similarity	NPD3133	Approved
0.6796	Remote Similarity	NPD5695	Phase 3
0.6796	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8297	Approved
0.6771	Remote Similarity	NPD3667	Approved
0.6768	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD4202	Approved
0.6762	Remote Similarity	NPD5696	Approved
0.6731	Remote Similarity	NPD4697	Phase 3
0.6731	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5222	Approved
0.6731	Remote Similarity	NPD5221	Approved
0.6729	Remote Similarity	NPD5211	Phase 2
0.6701	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6636	Remote Similarity	NPD6412	Phase 2
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6634	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4195	Approved
0.6609	Remote Similarity	NPD6868	Approved
0.6606	Remote Similarity	NPD5141	Approved
0.66	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8133	Approved
0.6569	Remote Similarity	NPD5785	Approved
0.6559	Remote Similarity	NPD8264	Approved
0.6552	Remote Similarity	NPD6009	Approved
0.6545	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD4700	Approved
0.6542	Remote Similarity	NPD4696	Approved
0.6542	Remote Similarity	NPD5285	Approved
0.6542	Remote Similarity	NPD5286	Approved
0.6505	Remote Similarity	NPD6411	Approved
0.65	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8328	Phase 3
0.6496	Remote Similarity	NPD6335	Approved
0.6489	Remote Similarity	NPD6117	Approved
0.6481	Remote Similarity	NPD5223	Approved
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4753	Phase 2
0.6466	Remote Similarity	NPD6274	Approved
0.6465	Remote Similarity	NPD3668	Phase 3
0.6458	Remote Similarity	NPD6929	Approved
0.6452	Remote Similarity	NPD6926	Approved
0.6452	Remote Similarity	NPD6924	Approved
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5290	Discontinued
0.6446	Remote Similarity	NPD7492	Approved
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6441	Remote Similarity	NPD7101	Approved
0.6441	Remote Similarity	NPD7100	Approved
0.6436	Remote Similarity	NPD7750	Discontinued
0.6436	Remote Similarity	NPD7524	Approved
0.6435	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD4221	Approved
0.6429	Remote Similarity	NPD4223	Phase 3
0.6423	Remote Similarity	NPD7736	Approved
0.6422	Remote Similarity	NPD5226	Approved
0.6422	Remote Similarity	NPD5224	Approved
0.6422	Remote Similarity	NPD5225	Approved
0.6422	Remote Similarity	NPD4633	Approved
0.6421	Remote Similarity	NPD6116	Phase 1
0.6413	Remote Similarity	NPD4243	Approved
0.641	Remote Similarity	NPD6317	Approved
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5329	Approved
0.6393	Remote Similarity	NPD6616	Approved
0.6392	Remote Similarity	NPD6931	Approved
0.6392	Remote Similarity	NPD4695	Discontinued
0.6392	Remote Similarity	NPD6930	Phase 2
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD6059	Approved
0.6381	Remote Similarity	NPD6001	Approved
0.6373	Remote Similarity	NPD5208	Approved
0.6372	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD6313	Approved
0.6356	Remote Similarity	NPD6314	Approved
0.6354	Remote Similarity	NPD6114	Approved
0.6354	Remote Similarity	NPD6115	Approved
0.6354	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6697	Approved
0.6354	Remote Similarity	NPD6118	Approved
0.6348	Remote Similarity	NPD6053	Discontinued
0.6346	Remote Similarity	NPD5281	Approved
0.6346	Remote Similarity	NPD6050	Approved
0.6346	Remote Similarity	NPD5284	Approved
0.6341	Remote Similarity	NPD8293	Discontinued
0.6341	Remote Similarity	NPD7078	Approved
0.6337	Remote Similarity	NPD5279	Phase 3
0.6337	Remote Similarity	NPD6098	Approved
0.6333	Remote Similarity	NPD6908	Approved
0.6333	Remote Similarity	NPD6909	Approved
0.6316	Remote Similarity	NPD6933	Approved
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4197	Approved
0.6283	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6370	Approved
0.6277	Remote Similarity	NPD4784	Approved
0.6277	Remote Similarity	NPD6113	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