NPASS Compound

Structure

NPC78008 OpenBabel07101718292D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.5223 1.6702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9516 -3.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3633 0.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8176 -2.2559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6836 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6202 1.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0575 0.0229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9516 -0.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6266 0.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3144 0.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0856 -3.2559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9516 -1.7559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6836 -0.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0086 0.3319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3176 1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8176 -0.2559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2195 -3.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5497 -0.2559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9054 2.0920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0856 -2.2559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3176 1.2830 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 12 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 13 21 2 0 0 0 0 13 24 1 0 0 0 0 14 24 1 6 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 8 1 6 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 6 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	2.386
LogD:	2.037
LogS:	-4.192
# Rotatable Bonds:	6
TPSA:	82.2
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	5.041
Fsp3:	0.65
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:	-4.89
MDCK Permeability:	2.4153250706149265e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.132
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923
Plasma Protein Binding (PPB):	73.0845947265625%
Volume Distribution (VD):	0.501
Pgp-substrate:	34.00859832763672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.232
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.294
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	5.705
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.854
Drug-inuced Liver Injury (DILI):	0.493
AMES Toxicity:	0.734
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.67
Carcinogencity:	0.086
Eye Corrosion:	0.125
Eye Irritation:	0.072
Respiratory Toxicity:	0.295

Download Data

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

Natural Product: NPC78008

Natural Product ID:	NPC78008
*Common Name:**	(+)-Miliusane Xii/Xiii
IUPAC Name:	[(1R,5R,9S)-1-[(E)-4-[(2R)-3,3-dimethyloxiran-2-yl]-2-methylbut-1-enyl]-3,6-dioxo-2-oxaspiro[4.5]dec-7-en-9-yl] acetate
Synonyms:	(+)-Miliusane XII/XIII
Standard InCHIKey:	UXCNIXRKYHKHIF-VLADIYONSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-12(5-8-16-19(3,4)26-16)9-17-20(11-18(23)25-17)10-14(24-13(2)21)6-7-15(20)22/h6-7,9,14,16-17H,5,8,10-11H2,1-4H3/b12-9+/t14-,16-,17-,20+/m1/s1
SMILES:	C/C(=C[C@@H]1[C@@]2(C[C@@H](C=CC2=O)OC(=O)C)CC(=O)O1)/CC[C@@H]1C(C)(C)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL197594
PubChem CID:	44406800
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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	=	54970.0	nM	PMID[573543]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	9310.0	nM	PMID[573543]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	13430.0	nM	PMID[573543]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	51820.0	nM	PMID[573543]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12180.0	nM	PMID[573543]

☑ 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 NPC78008 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	221
0.1-0.2	1544
0.2-0.3	6483
0.3-0.4	13078
0.4-0.5	11666
0.5-0.6	6204
0.6-0.7	3072
0.7-0.8	405
0.8-0.85	15
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC155873
0.9432	High Similarity	NPC214694
0.9398	High Similarity	NPC38569
0.9398	High Similarity	NPC163615
0.9186	High Similarity	NPC153570
0.907	High Similarity	NPC473248
0.8977	High Similarity	NPC473455
0.8864	High Similarity	NPC87306
0.8588	High Similarity	NPC275507
0.8295	Intermediate Similarity	NPC219966
0.8261	Intermediate Similarity	NPC20713
0.8152	Intermediate Similarity	NPC62815
0.8085	Intermediate Similarity	NPC476267
0.8085	Intermediate Similarity	NPC140543
0.8065	Intermediate Similarity	NPC207641
0.8065	Intermediate Similarity	NPC233437
0.8043	Intermediate Similarity	NPC166919
0.8022	Intermediate Similarity	NPC231889
0.8022	Intermediate Similarity	NPC475703
0.7978	Intermediate Similarity	NPC52923
0.7978	Intermediate Similarity	NPC272814
0.7917	Intermediate Similarity	NPC476275
0.79	Intermediate Similarity	NPC169843
0.7895	Intermediate Similarity	NPC471147
0.7872	Intermediate Similarity	NPC284185
0.7812	Intermediate Similarity	NPC475659
0.7812	Intermediate Similarity	NPC474947
0.7778	Intermediate Similarity	NPC170377
0.7778	Intermediate Similarity	NPC318468
0.7766	Intermediate Similarity	NPC475748
0.7766	Intermediate Similarity	NPC469718
0.7766	Intermediate Similarity	NPC312042
0.7766	Intermediate Similarity	NPC329857
0.7766	Intermediate Similarity	NPC253144
0.7732	Intermediate Similarity	NPC21302
0.7732	Intermediate Similarity	NPC17585
0.7732	Intermediate Similarity	NPC11396
0.7732	Intermediate Similarity	NPC473859
0.7727	Intermediate Similarity	NPC473980
0.7727	Intermediate Similarity	NPC473981
0.7723	Intermediate Similarity	NPC474741
0.7717	Intermediate Similarity	NPC261253
0.7717	Intermediate Similarity	NPC469676
0.7717	Intermediate Similarity	NPC50637
0.7717	Intermediate Similarity	NPC474045
0.7708	Intermediate Similarity	NPC473316
0.7708	Intermediate Similarity	NPC473330
0.7684	Intermediate Similarity	NPC472705
0.7684	Intermediate Similarity	NPC123177
0.7684	Intermediate Similarity	NPC70595
0.7684	Intermediate Similarity	NPC150978
0.7684	Intermediate Similarity	NPC74103
0.7677	Intermediate Similarity	NPC288876
0.7677	Intermediate Similarity	NPC477512
0.7667	Intermediate Similarity	NPC475690
0.766	Intermediate Similarity	NPC151770
0.7653	Intermediate Similarity	NPC134454
0.7653	Intermediate Similarity	NPC17326
0.764	Intermediate Similarity	NPC474510
0.7634	Intermediate Similarity	NPC72513
0.7624	Intermediate Similarity	NPC110989
0.7614	Intermediate Similarity	NPC475699
0.7609	Intermediate Similarity	NPC215364
0.7609	Intermediate Similarity	NPC474547
0.7609	Intermediate Similarity	NPC473353
0.76	Intermediate Similarity	NPC264477
0.76	Intermediate Similarity	NPC477511
0.7582	Intermediate Similarity	NPC170286
0.7579	Intermediate Similarity	NPC51653
0.7579	Intermediate Similarity	NPC179394
0.7579	Intermediate Similarity	NPC49342
0.7579	Intermediate Similarity	NPC144133
0.7579	Intermediate Similarity	NPC251385
0.7576	Intermediate Similarity	NPC208233
0.7558	Intermediate Similarity	NPC294434
0.7558	Intermediate Similarity	NPC259599
0.7558	Intermediate Similarity	NPC15499
0.7558	Intermediate Similarity	NPC117746
0.7556	Intermediate Similarity	NPC141810
0.7553	Intermediate Similarity	NPC469653
0.7553	Intermediate Similarity	NPC475902
0.7553	Intermediate Similarity	NPC469628
0.7553	Intermediate Similarity	NPC475906
0.7553	Intermediate Similarity	NPC471047
0.7553	Intermediate Similarity	NPC469631
0.7551	Intermediate Similarity	NPC35498
0.7551	Intermediate Similarity	NPC230800
0.7549	Intermediate Similarity	NPC471143
0.7549	Intermediate Similarity	NPC203659
0.7549	Intermediate Similarity	NPC477510
0.7527	Intermediate Similarity	NPC284902
0.7527	Intermediate Similarity	NPC38576
0.7527	Intermediate Similarity	NPC122502
0.7527	Intermediate Similarity	NPC279859
0.7526	Intermediate Similarity	NPC474035
0.7526	Intermediate Similarity	NPC81386
0.7525	Intermediate Similarity	NPC149371
0.7525	Intermediate Similarity	NPC225353
0.7524	Intermediate Similarity	NPC41551
0.7524	Intermediate Similarity	NPC253906
0.75	Intermediate Similarity	NPC57744
0.75	Intermediate Similarity	NPC469551
0.75	Intermediate Similarity	NPC221282
0.7451	Intermediate Similarity	NPC475871
0.7451	Intermediate Similarity	NPC475945
0.7449	Intermediate Similarity	NPC270013
0.7449	Intermediate Similarity	NPC14961
0.7447	Intermediate Similarity	NPC160138
0.7444	Intermediate Similarity	NPC223904
0.7429	Intermediate Similarity	NPC469370
0.7426	Intermediate Similarity	NPC201718
0.7426	Intermediate Similarity	NPC47880
0.7426	Intermediate Similarity	NPC472753
0.7426	Intermediate Similarity	NPC474742
0.7426	Intermediate Similarity	NPC164598
0.7426	Intermediate Similarity	NPC474339
0.7423	Intermediate Similarity	NPC475838
0.7423	Intermediate Similarity	NPC475657
0.7423	Intermediate Similarity	NPC228451
0.7423	Intermediate Similarity	NPC212486
0.7423	Intermediate Similarity	NPC125674
0.7423	Intermediate Similarity	NPC165383
0.7419	Intermediate Similarity	NPC50362
0.7419	Intermediate Similarity	NPC319795
0.7419	Intermediate Similarity	NPC38468
0.7416	Intermediate Similarity	NPC253749
0.7416	Intermediate Similarity	NPC128276
0.7416	Intermediate Similarity	NPC471220
0.74	Intermediate Similarity	NPC54843
0.74	Intermediate Similarity	NPC141191
0.74	Intermediate Similarity	NPC264378
0.74	Intermediate Similarity	NPC23364
0.7396	Intermediate Similarity	NPC71533
0.7396	Intermediate Similarity	NPC106510
0.7396	Intermediate Similarity	NPC475855
0.7396	Intermediate Similarity	NPC51004
0.7391	Intermediate Similarity	NPC250315
0.7386	Intermediate Similarity	NPC27205
0.7379	Intermediate Similarity	NPC470297
0.7374	Intermediate Similarity	NPC476315
0.7374	Intermediate Similarity	NPC185553
0.7368	Intermediate Similarity	NPC202672
0.7364	Intermediate Similarity	NPC470420
0.7363	Intermediate Similarity	NPC286229
0.7363	Intermediate Similarity	NPC42470
0.7358	Intermediate Similarity	NPC50223
0.7356	Intermediate Similarity	NPC476355
0.7353	Intermediate Similarity	NPC474747
0.7353	Intermediate Similarity	NPC235369
0.7353	Intermediate Similarity	NPC472754
0.7347	Intermediate Similarity	NPC57405
0.7347	Intermediate Similarity	NPC303942
0.7347	Intermediate Similarity	NPC474247
0.734	Intermediate Similarity	NPC478112
0.734	Intermediate Similarity	NPC70555
0.734	Intermediate Similarity	NPC104961
0.734	Intermediate Similarity	NPC70422
0.7333	Intermediate Similarity	NPC617
0.7333	Intermediate Similarity	NPC178277
0.7333	Intermediate Similarity	NPC471299
0.7333	Intermediate Similarity	NPC270126
0.7327	Intermediate Similarity	NPC469402
0.7327	Intermediate Similarity	NPC54705
0.7327	Intermediate Similarity	NPC280963
0.7327	Intermediate Similarity	NPC476933
0.7327	Intermediate Similarity	NPC475949
0.732	Intermediate Similarity	NPC30515
0.732	Intermediate Similarity	NPC300312
0.732	Intermediate Similarity	NPC261607
0.732	Intermediate Similarity	NPC111114
0.7308	Intermediate Similarity	NPC475802
0.7308	Intermediate Similarity	NPC9303
0.7308	Intermediate Similarity	NPC16313
0.7303	Intermediate Similarity	NPC187568
0.7303	Intermediate Similarity	NPC41780
0.73	Intermediate Similarity	NPC213947
0.73	Intermediate Similarity	NPC70145
0.73	Intermediate Similarity	NPC170143
0.73	Intermediate Similarity	NPC108475
0.73	Intermediate Similarity	NPC471462
0.73	Intermediate Similarity	NPC40812
0.73	Intermediate Similarity	NPC47834
0.73	Intermediate Similarity	NPC91695
0.73	Intermediate Similarity	NPC471140
0.73	Intermediate Similarity	NPC169205
0.7297	Intermediate Similarity	NPC475520
0.7292	Intermediate Similarity	NPC307411
0.7292	Intermediate Similarity	NPC295312
0.7292	Intermediate Similarity	NPC83423
0.729	Intermediate Similarity	NPC475495
0.7283	Intermediate Similarity	NPC173609
0.7283	Intermediate Similarity	NPC85772
0.7282	Intermediate Similarity	NPC19239
0.7282	Intermediate Similarity	NPC474166
0.7282	Intermediate Similarity	NPC254202
0.7282	Intermediate Similarity	NPC475873
0.7282	Intermediate Similarity	NPC472755
0.7273	Intermediate Similarity	NPC469684
0.7273	Intermediate Similarity	NPC275960
0.7273	Intermediate Similarity	NPC48803

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 NPC78008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	2055
0.2-0.3	4221
0.3-0.4	1886
0.4-0.5	510
0.5-0.6	253
0.6-0.7	36
0.7-0.8	3
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
0.7473	Intermediate Similarity	NPD5209	Approved
0.7419	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1694	Approved
0.7024	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6008	Approved
0.6939	Remote Similarity	NPD1695	Approved
0.6881	Remote Similarity	NPD6371	Approved
0.6869	Remote Similarity	NPD5785	Approved
0.6869	Remote Similarity	NPD6698	Approved
0.6869	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD5282	Discontinued
0.6737	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8039	Approved
0.6606	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7838	Discovery
0.6522	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD7983	Approved
0.6465	Remote Similarity	NPD5786	Approved
0.6429	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4225	Approved
0.6408	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD5363	Approved
0.6262	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6686	Approved
0.6238	Remote Similarity	NPD3573	Approved
0.6228	Remote Similarity	NPD6650	Approved
0.6228	Remote Similarity	NPD6649	Approved
0.6218	Remote Similarity	NPD6319	Approved
0.6204	Remote Similarity	NPD6648	Approved
0.6204	Remote Similarity	NPD7640	Approved
0.6204	Remote Similarity	NPD7639	Approved
0.6198	Remote Similarity	NPD7642	Approved
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7900	Approved
0.619	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6053	Discontinued
0.6167	Remote Similarity	NPD8513	Phase 3
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6161	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD6411	Approved
0.6154	Remote Similarity	NPD7637	Suspended
0.6148	Remote Similarity	NPD7492	Approved
0.6147	Remote Similarity	NPD5344	Discontinued
0.6146	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7521	Approved
0.6139	Remote Similarity	NPD5330	Approved
0.6139	Remote Similarity	NPD6409	Approved
0.6139	Remote Similarity	NPD6684	Approved
0.6139	Remote Similarity	NPD7146	Approved
0.6139	Remote Similarity	NPD7334	Approved
0.6136	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5369	Approved
0.6121	Remote Similarity	NPD4632	Approved
0.6106	Remote Similarity	NPD6899	Approved
0.6106	Remote Similarity	NPD6011	Approved
0.6106	Remote Similarity	NPD6881	Approved
0.61	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6616	Approved
0.6095	Remote Similarity	NPD6399	Phase 3
0.6083	Remote Similarity	NPD6054	Approved
0.6075	Remote Similarity	NPD7839	Suspended
0.6061	Remote Similarity	NPD6435	Approved
0.6061	Remote Similarity	NPD4270	Approved
0.6061	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD5207	Approved
0.6053	Remote Similarity	NPD6372	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6373	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.6048	Remote Similarity	NPD7078	Approved
0.6033	Remote Similarity	NPD6016	Approved
0.6033	Remote Similarity	NPD6015	Approved
0.602	Remote Similarity	NPD4252	Approved
0.6019	Remote Similarity	NPD6903	Approved
0.6019	Remote Similarity	NPD7902	Approved
0.6019	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5984	Remote Similarity	NPD7260	Phase 2
0.598	Remote Similarity	NPD4249	Approved
0.5966	Remote Similarity	NPD6009	Approved
0.5965	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6847	Approved
0.5948	Remote Similarity	NPD8130	Phase 1
0.5948	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6617	Approved
0.5948	Remote Similarity	NPD6869	Approved
0.5935	Remote Similarity	NPD7829	Approved
0.5935	Remote Similarity	NPD7830	Approved
0.5935	Remote Similarity	NPD7604	Phase 2
0.5929	Remote Similarity	NPD5739	Approved
0.5929	Remote Similarity	NPD6675	Approved
0.5929	Remote Similarity	NPD7128	Approved
0.5929	Remote Similarity	NPD6402	Approved
0.5922	Remote Similarity	NPD4250	Approved
0.5922	Remote Similarity	NPD4251	Approved
0.592	Remote Similarity	NPD8074	Phase 3
0.5902	Remote Similarity	NPD5983	Phase 2
0.5897	Remote Similarity	NPD8297	Approved
0.5897	Remote Similarity	NPD6882	Approved
0.5888	Remote Similarity	NPD6001	Approved
0.5882	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5701	Approved
0.5862	Remote Similarity	NPD4634	Approved
0.5859	Remote Similarity	NPD5368	Approved
0.5849	Remote Similarity	NPD5281	Approved
0.5849	Remote Similarity	NPD5284	Approved
0.5849	Remote Similarity	NPD5694	Approved
0.5842	Remote Similarity	NPD7154	Phase 3
0.5833	Remote Similarity	NPD5695	Phase 3
0.5827	Remote Similarity	NPD7319	Approved
0.5826	Remote Similarity	NPD7320	Approved
0.582	Remote Similarity	NPD6059	Approved
0.5818	Remote Similarity	NPD5696	Approved
0.581	Remote Similarity	NPD6080	Approved
0.581	Remote Similarity	NPD6904	Approved
0.581	Remote Similarity	NPD6673	Approved
0.581	Remote Similarity	NPD6051	Approved
0.5804	Remote Similarity	NPD5211	Phase 2
0.5794	Remote Similarity	NPD8293	Discontinued
0.5772	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5285	Approved
0.5766	Remote Similarity	NPD4696	Approved
0.5766	Remote Similarity	NPD5286	Approved
0.5761	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5692	Phase 3
0.5741	Remote Similarity	NPD7748	Approved
0.5728	Remote Similarity	NPD1696	Phase 3
0.5727	Remote Similarity	NPD6084	Phase 2
0.5727	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD5223	Approved
0.5714	Remote Similarity	NPD6336	Discontinued
0.5714	Remote Similarity	NPD4756	Discovery
0.5714	Remote Similarity	NPD5208	Approved
0.5714	Remote Similarity	NPD7507	Approved
0.5702	Remote Similarity	NPD5141	Approved
0.5702	Remote Similarity	NPD7500	Approved
0.5702	Remote Similarity	NPD6317	Approved
0.5701	Remote Similarity	NPD6050	Approved
0.5701	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6079	Approved
0.57	Remote Similarity	NPD4820	Approved
0.57	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4819	Approved
0.57	Remote Similarity	NPD4821	Approved
0.57	Remote Similarity	NPD4822	Approved
0.57	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6845	Suspended
0.5686	Remote Similarity	NPD5362	Discontinued
0.568	Remote Similarity	NPD8328	Phase 3
0.5678	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4633	Approved
0.5664	Remote Similarity	NPD5224	Approved
0.5664	Remote Similarity	NPD7632	Discontinued
0.5664	Remote Similarity	NPD5225	Approved
0.5664	Remote Similarity	NPD5226	Approved
0.566	Remote Similarity	NPD5370	Suspended
0.5656	Remote Similarity	NPD6314	Approved
0.5656	Remote Similarity	NPD6335	Approved
0.5656	Remote Similarity	NPD6313	Approved
0.5652	Remote Similarity	NPD5048	Discontinued
0.5636	Remote Similarity	NPD5221	Approved
0.5636	Remote Similarity	NPD5222	Approved
0.5636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4697	Phase 3
0.562	Remote Similarity	NPD6274	Approved
0.5614	Remote Similarity	NPD5175	Approved
0.5614	Remote Similarity	NPD5174	Approved
0.561	Remote Similarity	NPD7101	Approved
0.561	Remote Similarity	NPD7100	Approved
0.5603	Remote Similarity	NPD6412	Phase 2

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