NPASS Compound

Structure

NPC207641 OpenBabel07101718222D 27 28 0 0 1 0 0 0 0 0999 V2000 6.1678 3.3772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6510 1.7868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2605 2.3342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2092 -3.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5538 -3.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8145 2.3835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5320 3.0295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8962 2.6818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3795 1.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7177 -1.1610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0453 -2.1265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1633 -1.5537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4503 2.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1787 2.0358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0453 -4.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7177 -2.1265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8815 -2.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8815 -0.6782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9444 -0.2007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4828 -0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0453 -1.1610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0453 -5.0230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8815 0.2873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4430 -0.9371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5538 -2.6092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8815 -3.5748 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 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 15 22 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 1 0 0 0 17 26 1 1 0 0 0 18 21 1 0 0 0 0 18 23 2 0 0 0 0 19 21 1 6 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.2
Volume:	394.218
LogP:	3.024
LogD:	2.539
LogS:	-4.346
# Rotatable Bonds:	7
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	4.873
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	4.615015132003464e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.523
Human Intestinal Absorption (HIA):	0.57
20% Bioavailability (F20%):	0.753
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.834
Plasma Protein Binding (PPB):	86.89049530029297%
Volume Distribution (VD):	1.725
Pgp-substrate:	10.559976577758789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.549
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	7.325
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.737
AMES Toxicity:	0.499
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.08
Skin Sensitization:	0.411
Carcinogencity:	0.057
Eye Corrosion:	0.005
Eye Irritation:	0.043
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC207641

Natural Product ID:	NPC207641
*Common Name:**	(+)-Miliusane Vi
IUPAC Name:	[(1R,5R,8R,9S)-1-[(1E)-2,6-dimethylhepta-1,5-dienyl]-8-methoxy-3,6-dioxo-2-oxaspiro[4.5]decan-9-yl] acetate
Synonyms:	(+)-Miliusane VI
Standard InCHIKey:	YGWPHAWAXUILGD-QZOSWBQSSA-N
Standard InCHI:	InChI=1S/C21H30O6/c1-13(2)7-6-8-14(3)9-19-21(12-20(24)27-19)11-17(26-15(4)22)16(25-5)10-18(21)23/h7,9,16-17,19H,6,8,10-12H2,1-5H3/b14-9+/t16-,17+,19-,21+/m1/s1
SMILES:	CC(=CCC/C(=C/[C@@H]1[C@@]2(C[C@@H]([C@@H](CC2=O)OC)OC(=O)C)CC(=O)O1)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL201741
PubChem CID:	11559903
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO22093	Miliusa sinensis	Species	Annonaceae	Eukaryota	dried leaves, twigs, and flowers	Vietnam	n.a.	PMID[16420055]
NPO22093	Miliusa sinensis	Species	Annonaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3970.0	nM	PMID[460000]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	6610.0	nM	PMID[460000]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	4230.0	nM	PMID[460000]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	5290.0	nM	PMID[460000]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4760.0	nM	PMID[460000]

☑ 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 NPC207641 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	206
0.1-0.2	1310
0.2-0.3	4602
0.3-0.4	8400
0.4-0.5	14432
0.5-0.6	7610
0.6-0.7	5373
0.7-0.8	754
0.8-0.85	4
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233437
0.9444	High Similarity	NPC17326
0.9444	High Similarity	NPC134454
0.9333	High Similarity	NPC11396
0.9333	High Similarity	NPC21302
0.8222	Intermediate Similarity	NPC155873
0.8144	Intermediate Similarity	NPC471932
0.8111	Intermediate Similarity	NPC38569
0.8111	Intermediate Similarity	NPC163615
0.8065	Intermediate Similarity	NPC78008
0.8043	Intermediate Similarity	NPC231889
0.7941	Intermediate Similarity	NPC230541
0.7895	Intermediate Similarity	NPC20713
0.7885	Intermediate Similarity	NPC253906
0.7849	Intermediate Similarity	NPC473248
0.7843	Intermediate Similarity	NPC470975
0.7843	Intermediate Similarity	NPC103088
0.7843	Intermediate Similarity	NPC470979
0.783	Intermediate Similarity	NPC470120
0.7822	Intermediate Similarity	NPC110989
0.7802	Intermediate Similarity	NPC318468
0.7789	Intermediate Similarity	NPC51004
0.7789	Intermediate Similarity	NPC473455
0.7789	Intermediate Similarity	NPC475748
0.7788	Intermediate Similarity	NPC469370
0.7788	Intermediate Similarity	NPC141350
0.7767	Intermediate Similarity	NPC475510
0.7767	Intermediate Similarity	NPC475587
0.7767	Intermediate Similarity	NPC133422
0.7767	Intermediate Similarity	NPC474716
0.7767	Intermediate Similarity	NPC180744
0.7766	Intermediate Similarity	NPC153570
0.7757	Intermediate Similarity	NPC117712
0.7745	Intermediate Similarity	NPC203659
0.7732	Intermediate Similarity	NPC471147
0.7732	Intermediate Similarity	NPC250075
0.7723	Intermediate Similarity	NPC225353
0.7723	Intermediate Similarity	NPC183571
0.7708	Intermediate Similarity	NPC30515
0.7708	Intermediate Similarity	NPC284185
0.7692	Intermediate Similarity	NPC94377
0.7692	Intermediate Similarity	NPC473939
0.7692	Intermediate Similarity	NPC473595
0.7684	Intermediate Similarity	NPC151770
0.7684	Intermediate Similarity	NPC87306
0.7684	Intermediate Similarity	NPC307411
0.767	Intermediate Similarity	NPC102352
0.7653	Intermediate Similarity	NPC475659
0.7653	Intermediate Similarity	NPC214694
0.7647	Intermediate Similarity	NPC19239
0.7647	Intermediate Similarity	NPC69171
0.7647	Intermediate Similarity	NPC474165
0.7647	Intermediate Similarity	NPC254202
0.7647	Intermediate Similarity	NPC475321
0.7647	Intermediate Similarity	NPC474166
0.7642	Intermediate Similarity	NPC194619
0.7642	Intermediate Similarity	NPC188738
0.7636	Intermediate Similarity	NPC470186
0.7634	Intermediate Similarity	NPC110405
0.7629	Intermediate Similarity	NPC475912
0.7629	Intermediate Similarity	NPC179746
0.7629	Intermediate Similarity	NPC476300
0.7629	Intermediate Similarity	NPC81419
0.7624	Intermediate Similarity	NPC472753
0.7619	Intermediate Similarity	NPC42662
0.7615	Intermediate Similarity	NPC53396
0.7615	Intermediate Similarity	NPC98249
0.7615	Intermediate Similarity	NPC469684
0.7609	Intermediate Similarity	NPC222358
0.7609	Intermediate Similarity	NPC272814
0.7609	Intermediate Similarity	NPC170286
0.7604	Intermediate Similarity	NPC253144
0.7604	Intermediate Similarity	NPC51653
0.7579	Intermediate Similarity	NPC202672
0.7579	Intermediate Similarity	NPC477128
0.7576	Intermediate Similarity	NPC473859
0.7573	Intermediate Similarity	NPC470297
0.757	Intermediate Similarity	NPC476801
0.757	Intermediate Similarity	NPC269530
0.7553	Intermediate Similarity	NPC284902
0.7551	Intermediate Similarity	NPC140543
0.7551	Intermediate Similarity	NPC81386
0.7551	Intermediate Similarity	NPC473316
0.7551	Intermediate Similarity	NPC473330
0.7551	Intermediate Similarity	NPC476267
0.7551	Intermediate Similarity	NPC470697
0.7551	Intermediate Similarity	NPC474035
0.7549	Intermediate Similarity	NPC472754
0.7549	Intermediate Similarity	NPC49393
0.7549	Intermediate Similarity	NPC105725
0.7549	Intermediate Similarity	NPC149371
0.7549	Intermediate Similarity	NPC474709
0.7547	Intermediate Similarity	NPC473594
0.7547	Intermediate Similarity	NPC474586
0.7547	Intermediate Similarity	NPC473975
0.7547	Intermediate Similarity	NPC473843
0.7547	Intermediate Similarity	NPC281624
0.7545	Intermediate Similarity	NPC284707
0.7526	Intermediate Similarity	NPC74103
0.7526	Intermediate Similarity	NPC12172
0.7526	Intermediate Similarity	NPC70595
0.7526	Intermediate Similarity	NPC184463
0.7526	Intermediate Similarity	NPC208886
0.7526	Intermediate Similarity	NPC473944
0.7526	Intermediate Similarity	NPC150978
0.7526	Intermediate Similarity	NPC221282
0.7526	Intermediate Similarity	NPC123177
0.7525	Intermediate Similarity	NPC469551
0.7525	Intermediate Similarity	NPC306856
0.7525	Intermediate Similarity	NPC476933
0.7525	Intermediate Similarity	NPC288876
0.7525	Intermediate Similarity	NPC474718
0.7524	Intermediate Similarity	NPC154608
0.7524	Intermediate Similarity	NPC192813
0.7524	Intermediate Similarity	NPC277017
0.7523	Intermediate Similarity	NPC476710
0.7523	Intermediate Similarity	NPC477509
0.7523	Intermediate Similarity	NPC478216
0.7523	Intermediate Similarity	NPC476711
0.75	Intermediate Similarity	NPC166919
0.75	Intermediate Similarity	NPC478212
0.75	Intermediate Similarity	NPC469607
0.75	Intermediate Similarity	NPC474032
0.75	Intermediate Similarity	NPC474343
0.75	Intermediate Similarity	NPC127609
0.7477	Intermediate Similarity	NPC469655
0.7477	Intermediate Similarity	NPC132790
0.7477	Intermediate Similarity	NPC97939
0.7477	Intermediate Similarity	NPC474846
0.7477	Intermediate Similarity	NPC100329
0.7477	Intermediate Similarity	NPC247031
0.7477	Intermediate Similarity	NPC469656
0.7476	Intermediate Similarity	NPC474775
0.7476	Intermediate Similarity	NPC475945
0.7476	Intermediate Similarity	NPC472755
0.7476	Intermediate Similarity	NPC475871
0.7476	Intermediate Similarity	NPC4620
0.7475	Intermediate Similarity	NPC36954
0.7475	Intermediate Similarity	NPC270013
0.7475	Intermediate Similarity	NPC14961
0.7475	Intermediate Similarity	NPC471142
0.7474	Intermediate Similarity	NPC475703
0.7455	Intermediate Similarity	NPC58662
0.7455	Intermediate Similarity	NPC476713
0.7455	Intermediate Similarity	NPC478204
0.7455	Intermediate Similarity	NPC476712
0.7453	Intermediate Similarity	NPC273433
0.7453	Intermediate Similarity	NPC478210
0.7451	Intermediate Similarity	NPC264477
0.7451	Intermediate Similarity	NPC477511
0.7451	Intermediate Similarity	NPC476478
0.7451	Intermediate Similarity	NPC47880
0.7451	Intermediate Similarity	NPC474742
0.7449	Intermediate Similarity	NPC471571
0.7449	Intermediate Similarity	NPC475657
0.7449	Intermediate Similarity	NPC212486
0.7434	Intermediate Similarity	NPC312833
0.7431	Intermediate Similarity	NPC73314
0.7429	Intermediate Similarity	NPC144854
0.7429	Intermediate Similarity	NPC3316
0.7429	Intermediate Similarity	NPC469558
0.7426	Intermediate Similarity	NPC470188
0.7426	Intermediate Similarity	NPC23364
0.7426	Intermediate Similarity	NPC264378
0.7426	Intermediate Similarity	NPC208233
0.7423	Intermediate Similarity	NPC474761
0.7423	Intermediate Similarity	NPC62815
0.7423	Intermediate Similarity	NPC158488
0.7423	Intermediate Similarity	NPC476004
0.7423	Intermediate Similarity	NPC469718
0.7423	Intermediate Similarity	NPC152467
0.7423	Intermediate Similarity	NPC329857
0.7423	Intermediate Similarity	NPC80875
0.7423	Intermediate Similarity	NPC232202
0.7419	Intermediate Similarity	NPC52923
0.7419	Intermediate Similarity	NPC475947
0.7411	Intermediate Similarity	NPC475003
0.7407	Intermediate Similarity	NPC222834
0.7407	Intermediate Similarity	NPC473877
0.7407	Intermediate Similarity	NPC472002
0.7407	Intermediate Similarity	NPC265391
0.7407	Intermediate Similarity	NPC471933
0.7404	Intermediate Similarity	NPC220964
0.7404	Intermediate Similarity	NPC169843
0.7404	Intermediate Similarity	NPC100487
0.7404	Intermediate Similarity	NPC258532
0.7404	Intermediate Similarity	NPC146731
0.7404	Intermediate Similarity	NPC472756
0.7404	Intermediate Similarity	NPC477127
0.7404	Intermediate Similarity	NPC474741
0.7404	Intermediate Similarity	NPC475676
0.74	Intermediate Similarity	NPC476315
0.74	Intermediate Similarity	NPC118159
0.74	Intermediate Similarity	NPC17585
0.74	Intermediate Similarity	NPC35498
0.74	Intermediate Similarity	NPC476275
0.7396	Intermediate Similarity	NPC475906
0.7396	Intermediate Similarity	NPC469631
0.7396	Intermediate Similarity	NPC469653
0.7396	Intermediate Similarity	NPC471047

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 NPC207641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1736
0.2-0.3	3840
0.3-0.4	2210
0.4-0.5	790
0.5-0.6	271
0.6-0.7	130
0.7-0.8	1
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
0.7263	Intermediate Similarity	NPD1694	Approved
0.7263	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4225	Approved
0.7037	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD7983	Approved
0.6947	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6371	Approved
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.69	Remote Similarity	NPD46	Approved
0.69	Remote Similarity	NPD6698	Approved
0.6789	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5779	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6765	Remote Similarity	NPD6399	Phase 3
0.6762	Remote Similarity	NPD7638	Approved
0.6739	Remote Similarity	NPD8039	Approved
0.6727	Remote Similarity	NPD6686	Approved
0.6699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7900	Approved
0.6699	Remote Similarity	NPD5282	Discontinued
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1695	Approved
0.661	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD8517	Approved
0.661	Remote Similarity	NPD8515	Approved
0.661	Remote Similarity	NPD8516	Approved
0.6598	Remote Similarity	NPD5209	Approved
0.6569	Remote Similarity	NPD5785	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6525	Remote Similarity	NPD6319	Approved
0.6509	Remote Similarity	NPD7902	Approved
0.6505	Remote Similarity	NPD6411	Approved
0.6504	Remote Similarity	NPD7319	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6435	Remote Similarity	NPD4632	Approved
0.6404	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7507	Approved
0.6393	Remote Similarity	NPD6616	Approved
0.6389	Remote Similarity	NPD6648	Approved
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD6059	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6372	Approved
0.6372	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8328	Phase 3
0.6341	Remote Similarity	NPD8074	Phase 3
0.6341	Remote Similarity	NPD8293	Discontinued
0.6341	Remote Similarity	NPD7078	Approved
0.6337	Remote Similarity	NPD7521	Approved
0.6337	Remote Similarity	NPD6684	Approved
0.6337	Remote Similarity	NPD5330	Approved
0.6337	Remote Similarity	NPD7334	Approved
0.6337	Remote Similarity	NPD7146	Approved
0.6337	Remote Similarity	NPD6409	Approved
0.6333	Remote Similarity	NPD6015	Approved
0.6333	Remote Similarity	NPD6921	Approved
0.6333	Remote Similarity	NPD6016	Approved
0.633	Remote Similarity	NPD5344	Discontinued
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7736	Approved
0.6281	Remote Similarity	NPD6370	Approved
0.6281	Remote Similarity	NPD5988	Approved
0.6275	Remote Similarity	NPD3573	Approved
0.6271	Remote Similarity	NPD6009	Approved
0.6263	Remote Similarity	NPD4269	Approved
0.6263	Remote Similarity	NPD4270	Approved
0.6263	Remote Similarity	NPD6435	Approved
0.6262	Remote Similarity	NPD7839	Suspended
0.6261	Remote Similarity	NPD6650	Approved
0.6261	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD7128	Approved
0.6226	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD6672	Approved
0.6214	Remote Similarity	NPD6903	Approved
0.6214	Remote Similarity	NPD5737	Approved
0.6214	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8297	Approved
0.6198	Remote Similarity	NPD5983	Phase 2
0.6195	Remote Similarity	NPD5697	Approved
0.6195	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD8035	Phase 2
0.619	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD8034	Phase 2
0.6186	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5369	Approved
0.614	Remote Similarity	NPD6899	Approved
0.614	Remote Similarity	NPD6881	Approved
0.614	Remote Similarity	NPD6011	Approved
0.614	Remote Similarity	NPD7320	Approved
0.6134	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD4697	Phase 3
0.6111	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7604	Phase 2
0.6087	Remote Similarity	NPD6014	Approved
0.6087	Remote Similarity	NPD6012	Approved
0.6087	Remote Similarity	NPD6013	Approved
0.6078	Remote Similarity	NPD5363	Approved
0.6078	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6053	Discontinued
0.6061	Remote Similarity	NPD5368	Approved
0.6061	Remote Similarity	NPD4252	Approved
0.6053	Remote Similarity	NPD6412	Phase 2
0.604	Remote Similarity	NPD7154	Phase 3
0.6038	Remote Similarity	NPD7515	Phase 2
0.6034	Remote Similarity	NPD7102	Approved
0.6034	Remote Similarity	NPD6883	Approved
0.6034	Remote Similarity	NPD7290	Approved
0.6034	Remote Similarity	NPD4634	Approved
0.6032	Remote Similarity	NPD6033	Approved
0.6031	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD3618	Phase 1
0.6017	Remote Similarity	NPD8133	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD6336	Discontinued
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6869	Approved
0.5983	Remote Similarity	NPD8130	Phase 1
0.5983	Remote Similarity	NPD6617	Approved
0.5983	Remote Similarity	NPD6847	Approved
0.598	Remote Similarity	NPD3668	Phase 3
0.5962	Remote Similarity	NPD4251	Approved
0.5962	Remote Similarity	NPD4250	Approved
0.5943	Remote Similarity	NPD5207	Approved
0.5941	Remote Similarity	NPD3667	Approved
0.5935	Remote Similarity	NPD8444	Approved
0.5932	Remote Similarity	NPD6882	Approved
0.5926	Remote Similarity	NPD6001	Approved
0.5914	Remote Similarity	NPD229	Approved
0.5909	Remote Similarity	NPD4755	Approved
0.5902	Remote Similarity	NPD7516	Approved
0.5897	Remote Similarity	NPD2067	Discontinued
0.5893	Remote Similarity	NPD1700	Approved
0.5888	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6079	Approved
0.5882	Remote Similarity	NPD6110	Phase 1
0.5882	Remote Similarity	NPD5362	Discontinued
0.5873	Remote Similarity	NPD8451	Approved
0.5872	Remote Similarity	NPD5695	Phase 3
0.5865	Remote Similarity	NPD6098	Approved
0.5865	Remote Similarity	NPD6422	Discontinued
0.5856	Remote Similarity	NPD5696	Approved
0.5849	Remote Similarity	NPD6673	Approved
0.5849	Remote Similarity	NPD6080	Approved
0.5849	Remote Similarity	NPD6904	Approved
0.5846	Remote Similarity	NPD6845	Suspended
0.5841	Remote Similarity	NPD5211	Phase 2
0.584	Remote Similarity	NPD7642	Approved
0.5827	Remote Similarity	NPD8448	Approved
0.5825	Remote Similarity	NPD4786	Approved
0.5824	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7328	Approved
0.582	Remote Similarity	NPD7327	Approved
0.5818	Remote Similarity	NPD5221	Approved
0.5818	Remote Similarity	NPD5222	Approved
0.5818	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5285	Approved
0.5804	Remote Similarity	NPD4700	Approved
0.5804	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4696	Approved
0.5794	Remote Similarity	NPD5692	Phase 3
0.5785	Remote Similarity	NPD6274	Approved
0.5784	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5173	Approved
0.5766	Remote Similarity	NPD6083	Phase 2
0.5766	Remote Similarity	NPD6084	Phase 2
0.5755	Remote Similarity	NPD5208	Approved
0.5752	Remote Similarity	NPD5223	Approved
0.5743	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6050	Approved
0.5741	Remote Similarity	NPD5694	Approved
0.5741	Remote Similarity	NPD5284	Approved
0.5741	Remote Similarity	NPD5281	Approved
0.5739	Remote Similarity	NPD5141	Approved
0.5738	Remote Similarity	NPD6317	Approved
0.5726	Remote Similarity	NPD8294	Approved
0.5726	Remote Similarity	NPD8377	Approved
0.5725	Remote Similarity	NPD8338	Approved
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7830	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