NPASS Compound

Structure

NPC473248 OpenBabel07101719132D 22 23 0 0 1 0 0 0 0 0999 V2000 -5.0180 -1.7080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3527 -3.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7398 -0.5884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0557 -2.0946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7136 -2.8476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0745 -2.2878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5785 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0275 -0.0501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4354 -1.7280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6115 -0.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1838 -2.0640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6947 -2.6544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4166 -1.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8673 -0.7521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -0.9749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0320 -2.5937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2185 -1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6491 -1.3756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9974 -3.5931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9148 -2.1240 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 12 1 0 0 0 0 3 13 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 14 7 1 6 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 18 1 1 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.17
Volume:	324.75
LogP:	3.217
LogD:	1.886
LogS:	-3.778
# Rotatable Bonds:	6
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	5.146
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.244
MDCK Permeability:	2.2079118934925646e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.177
Human Intestinal Absorption (HIA):	0.309
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.247
Plasma Protein Binding (PPB):	94.2582015991211%
Volume Distribution (VD):	0.317
Pgp-substrate:	5.354269027709961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.575
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	7.404
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.246
Skin Sensitization:	0.679
Carcinogencity:	0.118
Eye Corrosion:	0.006
Eye Irritation:	0.08
Respiratory Toxicity:	0.621

Download Data

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

Natural Product: NPC473248

Natural Product ID:	NPC473248
*Common Name:**	(+)-Miliusane Xx
IUPAC Name:	2-[(1S,5R,6R)-6-[(1E)-2,6-dimethylhepta-1,5-dienyl]-4-oxo-7-oxabicyclo[3.2.1]oct-2-en-5-yl]acetic acid
Synonyms:	(+)-Miliusane XX
Standard InCHIKey:	WAUSUAIPUGCTAF-FWDDYHNSSA-N
Standard InCHI:	InChI=1S/C18H24O4/c1-12(2)5-4-6-13(3)9-16-18(11-17(20)21)10-14(22-16)7-8-15(18)19/h5,7-9,14,16H,4,6,10-11H2,1-3H3,(H,20,21)/b13-9+/t14-,16-,18+/m1/s1
SMILES:	CC(=CCCC(=CC1C2(CC(O1)C=CC2=O)CC(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL383494
PubChem CID:	44406793
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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	59000.0	nM	PMID[471461]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	>	59000.0	nM	PMID[471461]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	59000.0	nM	PMID[471461]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	59000.0	nM	PMID[471461]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	59000.0	nM	PMID[471461]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	57010.0	nM	PMID[471461]

☑ 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 NPC473248 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	179
0.1-0.2	1290
0.2-0.3	5656
0.3-0.4	11322
0.4-0.5	13348
0.5-0.6	6725
0.6-0.7	3597
0.7-0.8	567
0.8-0.85	1
0.85-0.9	5
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC87306
0.9643	High Similarity	NPC473455
0.9639	High Similarity	NPC153570
0.963	High Similarity	NPC163615
0.963	High Similarity	NPC38569
0.9512	High Similarity	NPC155873
0.9205	High Similarity	NPC214694
0.9157	High Similarity	NPC219966
0.907	High Similarity	NPC78008
0.881	High Similarity	NPC52923
0.8795	High Similarity	NPC275507
0.8085	Intermediate Similarity	NPC11396
0.8085	Intermediate Similarity	NPC21302
0.8	Intermediate Similarity	NPC134454
0.8	Intermediate Similarity	NPC17326
0.7959	Intermediate Similarity	NPC110989
0.7889	Intermediate Similarity	NPC478112
0.7879	Intermediate Similarity	NPC203659
0.7857	Intermediate Similarity	NPC225353
0.7849	Intermediate Similarity	NPC207641
0.7849	Intermediate Similarity	NPC233437
0.7849	Intermediate Similarity	NPC472705
0.7789	Intermediate Similarity	NPC471142
0.7789	Intermediate Similarity	NPC477922
0.7742	Intermediate Similarity	NPC71533
0.7742	Intermediate Similarity	NPC473619
0.7742	Intermediate Similarity	NPC179394
0.7742	Intermediate Similarity	NPC106510
0.7742	Intermediate Similarity	NPC144133
0.7732	Intermediate Similarity	NPC23364
0.7732	Intermediate Similarity	NPC141191
0.7727	Intermediate Similarity	NPC297440
0.7727	Intermediate Similarity	NPC474980
0.7708	Intermediate Similarity	NPC477921
0.7708	Intermediate Similarity	NPC185553
0.7692	Intermediate Similarity	NPC278283
0.7677	Intermediate Similarity	NPC149371
0.7677	Intermediate Similarity	NPC235369
0.766	Intermediate Similarity	NPC284185
0.766	Intermediate Similarity	NPC473321
0.7634	Intermediate Similarity	NPC295312
0.7629	Intermediate Similarity	NPC70145
0.7629	Intermediate Similarity	NPC91695
0.7629	Intermediate Similarity	NPC169205
0.7609	Intermediate Similarity	NPC160138
0.7604	Intermediate Similarity	NPC475659
0.7604	Intermediate Similarity	NPC48803
0.7604	Intermediate Similarity	NPC193645
0.7604	Intermediate Similarity	NPC90121
0.7604	Intermediate Similarity	NPC275960
0.76	Intermediate Similarity	NPC475871
0.76	Intermediate Similarity	NPC475945
0.7586	Intermediate Similarity	NPC93763
0.7586	Intermediate Similarity	NPC108816
0.7582	Intermediate Similarity	NPC470755
0.7582	Intermediate Similarity	NPC21469
0.7579	Intermediate Similarity	NPC295204
0.7579	Intermediate Similarity	NPC162205
0.7579	Intermediate Similarity	NPC273579
0.7579	Intermediate Similarity	NPC288240
0.7576	Intermediate Similarity	NPC171759
0.7576	Intermediate Similarity	NPC474742
0.7576	Intermediate Similarity	NPC47880
0.7576	Intermediate Similarity	NPC472753
0.7556	Intermediate Similarity	NPC318468
0.7556	Intermediate Similarity	NPC250315
0.7553	Intermediate Similarity	NPC253144
0.7553	Intermediate Similarity	NPC475855
0.7553	Intermediate Similarity	NPC51004
0.7551	Intermediate Similarity	NPC471144
0.7527	Intermediate Similarity	NPC119740
0.7527	Intermediate Similarity	NPC150063
0.7527	Intermediate Similarity	NPC202672
0.7527	Intermediate Similarity	NPC475819
0.7527	Intermediate Similarity	NPC473715
0.7526	Intermediate Similarity	NPC473859
0.7525	Intermediate Similarity	NPC474741
0.75	Intermediate Similarity	NPC472754
0.75	Intermediate Similarity	NPC473980
0.75	Intermediate Similarity	NPC474747
0.75	Intermediate Similarity	NPC284902
0.75	Intermediate Similarity	NPC475927
0.75	Intermediate Similarity	NPC475832
0.75	Intermediate Similarity	NPC473981
0.7476	Intermediate Similarity	NPC89171
0.7476	Intermediate Similarity	NPC476802
0.7475	Intermediate Similarity	NPC288876
0.7475	Intermediate Similarity	NPC280963
0.7475	Intermediate Similarity	NPC54705
0.7474	Intermediate Similarity	NPC261607
0.7474	Intermediate Similarity	NPC30515
0.7474	Intermediate Similarity	NPC111114
0.7474	Intermediate Similarity	NPC300312
0.7474	Intermediate Similarity	NPC20713
0.7474	Intermediate Similarity	NPC123177
0.7474	Intermediate Similarity	NPC150978
0.7474	Intermediate Similarity	NPC74103
0.7474	Intermediate Similarity	NPC70595
0.7473	Intermediate Similarity	NPC474251
0.7473	Intermediate Similarity	NPC32676
0.7473	Intermediate Similarity	NPC472957
0.7473	Intermediate Similarity	NPC472958
0.7473	Intermediate Similarity	NPC158756
0.7449	Intermediate Similarity	NPC471462
0.7449	Intermediate Similarity	NPC108475
0.7449	Intermediate Similarity	NPC170143
0.7449	Intermediate Similarity	NPC213947
0.7449	Intermediate Similarity	NPC40812
0.7449	Intermediate Similarity	NPC245521
0.7447	Intermediate Similarity	NPC474032
0.7447	Intermediate Similarity	NPC307411
0.7444	Intermediate Similarity	NPC475690
0.7426	Intermediate Similarity	NPC475873
0.7426	Intermediate Similarity	NPC472755
0.7419	Intermediate Similarity	NPC72513
0.74	Intermediate Similarity	NPC475099
0.7396	Intermediate Similarity	NPC135776
0.7396	Intermediate Similarity	NPC475912
0.7396	Intermediate Similarity	NPC179746
0.7396	Intermediate Similarity	NPC81419
0.7396	Intermediate Similarity	NPC476300
0.7391	Intermediate Similarity	NPC215364
0.7391	Intermediate Similarity	NPC125290
0.7386	Intermediate Similarity	NPC475699
0.7386	Intermediate Similarity	NPC267231
0.7386	Intermediate Similarity	NPC127526
0.7374	Intermediate Similarity	NPC83895
0.7374	Intermediate Similarity	NPC255592
0.7374	Intermediate Similarity	NPC261377
0.7374	Intermediate Similarity	NPC187761
0.7374	Intermediate Similarity	NPC308567
0.7368	Intermediate Similarity	NPC62815
0.7363	Intermediate Similarity	NPC116543
0.7363	Intermediate Similarity	NPC169575
0.7363	Intermediate Similarity	NPC16488
0.7363	Intermediate Similarity	NPC40746
0.7353	Intermediate Similarity	NPC146731
0.7353	Intermediate Similarity	NPC100487
0.7353	Intermediate Similarity	NPC472756
0.7347	Intermediate Similarity	NPC230800
0.7347	Intermediate Similarity	NPC126156
0.734	Intermediate Similarity	NPC476805
0.7333	Intermediate Similarity	NPC5103
0.7333	Intermediate Similarity	NPC41551
0.7326	Intermediate Similarity	NPC15499
0.7326	Intermediate Similarity	NPC114727
0.7326	Intermediate Similarity	NPC476355
0.7326	Intermediate Similarity	NPC294434
0.7326	Intermediate Similarity	NPC259599
0.7326	Intermediate Similarity	NPC117746
0.7326	Intermediate Similarity	NPC476590
0.732	Intermediate Similarity	NPC476415
0.732	Intermediate Similarity	NPC469632
0.732	Intermediate Similarity	NPC476267
0.732	Intermediate Similarity	NPC167219
0.732	Intermediate Similarity	NPC81386
0.732	Intermediate Similarity	NPC474035
0.732	Intermediate Similarity	NPC140543
0.7312	Intermediate Similarity	NPC469483
0.7312	Intermediate Similarity	NPC309211
0.7312	Intermediate Similarity	NPC122502
0.7312	Intermediate Similarity	NPC261721
0.7312	Intermediate Similarity	NPC469910
0.7312	Intermediate Similarity	NPC477010
0.7312	Intermediate Similarity	NPC112685
0.7308	Intermediate Similarity	NPC275539
0.7308	Intermediate Similarity	NPC189075
0.7303	Intermediate Similarity	NPC270126
0.73	Intermediate Similarity	NPC306856
0.73	Intermediate Similarity	NPC174314
0.73	Intermediate Similarity	NPC475949
0.7292	Intermediate Similarity	NPC184463
0.7292	Intermediate Similarity	NPC12172
0.7292	Intermediate Similarity	NPC208886
0.7292	Intermediate Similarity	NPC221282
0.7283	Intermediate Similarity	NPC31086
0.7283	Intermediate Similarity	NPC212363
0.7282	Intermediate Similarity	NPC469607
0.7273	Intermediate Similarity	NPC7563
0.7273	Intermediate Similarity	NPC57744
0.7273	Intermediate Similarity	NPC266842
0.7273	Intermediate Similarity	NPC474343
0.7273	Intermediate Similarity	NPC320630
0.7273	Intermediate Similarity	NPC116177
0.7264	Intermediate Similarity	NPC474750
0.7264	Intermediate Similarity	NPC179798
0.7264	Intermediate Similarity	NPC304180
0.7263	Intermediate Similarity	NPC52198
0.7263	Intermediate Similarity	NPC117405
0.7263	Intermediate Similarity	NPC14901
0.7263	Intermediate Similarity	NPC477017
0.7263	Intermediate Similarity	NPC477011
0.7263	Intermediate Similarity	NPC280612
0.7263	Intermediate Similarity	NPC166919
0.7263	Intermediate Similarity	NPC477016
0.7263	Intermediate Similarity	NPC130359
0.7262	Intermediate Similarity	NPC476591
0.7262	Intermediate Similarity	NPC88877
0.7255	Intermediate Similarity	NPC474581
0.7255	Intermediate Similarity	NPC475321

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 NPC473248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1868
0.2-0.3	4030
0.3-0.4	2122
0.4-0.5	614
0.5-0.6	282
0.6-0.7	77
0.7-0.8	2
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
0.7604	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5209	Approved
0.7188	Intermediate Similarity	NPD5785	Approved
0.7021	Intermediate Similarity	NPD1694	Approved
0.697	Remote Similarity	NPD5282	Discontinued
0.6852	Remote Similarity	NPD6371	Approved
0.6837	Remote Similarity	NPD46	Approved
0.6837	Remote Similarity	NPD6698	Approved
0.6771	Remote Similarity	NPD5786	Approved
0.6768	Remote Similarity	NPD7983	Approved
0.6729	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5778	Approved
0.67	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6110	Phase 1
0.6538	Remote Similarity	NPD7638	Approved
0.6526	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6686	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.6489	Remote Similarity	NPD4252	Approved
0.6484	Remote Similarity	NPD8039	Approved
0.6476	Remote Similarity	NPD7639	Approved
0.6476	Remote Similarity	NPD7640	Approved
0.6452	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7637	Suspended
0.6436	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD4249	Approved
0.6392	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD4250	Approved
0.6364	Remote Similarity	NPD4251	Approved
0.6354	Remote Similarity	NPD4270	Approved
0.6354	Remote Similarity	NPD6435	Approved
0.6354	Remote Similarity	NPD4269	Approved
0.6348	Remote Similarity	NPD7115	Discovery
0.6346	Remote Similarity	NPD7839	Suspended
0.6339	Remote Similarity	NPD6650	Approved
0.6339	Remote Similarity	NPD6649	Approved
0.633	Remote Similarity	NPD6008	Approved
0.6325	Remote Similarity	NPD6319	Approved
0.6286	Remote Similarity	NPD7902	Approved
0.6283	Remote Similarity	NPD6053	Discontinued
0.6273	Remote Similarity	NPD5697	Approved
0.6271	Remote Similarity	NPD8513	Phase 3
0.6271	Remote Similarity	NPD8517	Approved
0.6271	Remote Similarity	NPD8515	Approved
0.6271	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD7492	Approved
0.6238	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6101	Approved
0.6238	Remote Similarity	NPD1695	Approved
0.6228	Remote Similarity	NPD4632	Approved
0.6216	Remote Similarity	NPD6881	Approved
0.6216	Remote Similarity	NPD6899	Approved
0.6216	Remote Similarity	NPD6011	Approved
0.621	Remote Similarity	NPD7260	Phase 2
0.6207	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6616	Approved
0.6186	Remote Similarity	NPD6054	Approved
0.617	Remote Similarity	NPD4756	Discovery
0.6162	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6373	Approved
0.6161	Remote Similarity	NPD6014	Approved
0.6161	Remote Similarity	NPD6012	Approved
0.6161	Remote Similarity	NPD6372	Approved
0.6161	Remote Similarity	NPD6013	Approved
0.6148	Remote Similarity	NPD7078	Approved
0.6146	Remote Similarity	NPD5368	Approved
0.6146	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7331	Phase 2
0.6134	Remote Similarity	NPD6015	Approved
0.6134	Remote Similarity	NPD6016	Approved
0.6122	Remote Similarity	NPD7154	Phase 3
0.6117	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7290	Approved
0.6106	Remote Similarity	NPD6883	Approved
0.6106	Remote Similarity	NPD7102	Approved
0.6098	Remote Similarity	NPD7736	Approved
0.6083	Remote Similarity	NPD5988	Approved
0.6083	Remote Similarity	NPD6370	Approved
0.6078	Remote Similarity	NPD5370	Suspended
0.6071	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6009	Approved
0.6053	Remote Similarity	NPD6847	Approved
0.6053	Remote Similarity	NPD6869	Approved
0.6053	Remote Similarity	NPD6617	Approved
0.6053	Remote Similarity	NPD8130	Phase 1
0.6053	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6402	Approved
0.6036	Remote Similarity	NPD7128	Approved
0.6036	Remote Similarity	NPD5739	Approved
0.6036	Remote Similarity	NPD6675	Approved
0.6033	Remote Similarity	NPD7642	Approved
0.6018	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD8297	Approved
0.5982	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5701	Approved
0.5979	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4634	Approved
0.5963	Remote Similarity	NPD5344	Discontinued
0.5962	Remote Similarity	NPD5281	Approved
0.5962	Remote Similarity	NPD6079	Approved
0.5962	Remote Similarity	NPD5284	Approved
0.596	Remote Similarity	NPD5362	Discontinued
0.5943	Remote Similarity	NPD5695	Phase 3
0.5941	Remote Similarity	NPD7334	Approved
0.5941	Remote Similarity	NPD5330	Approved
0.5941	Remote Similarity	NPD6684	Approved
0.5941	Remote Similarity	NPD7521	Approved
0.5941	Remote Similarity	NPD7146	Approved
0.5941	Remote Similarity	NPD6409	Approved
0.5938	Remote Similarity	NPD4268	Approved
0.5938	Remote Similarity	NPD4271	Approved
0.5932	Remote Similarity	NPD7500	Approved
0.5929	Remote Similarity	NPD7320	Approved
0.5926	Remote Similarity	NPD5696	Approved
0.592	Remote Similarity	NPD7319	Approved
0.5917	Remote Similarity	NPD6059	Approved
0.5913	Remote Similarity	NPD2204	Approved
0.5909	Remote Similarity	NPD5211	Phase 2
0.5909	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7632	Discontinued
0.5906	Remote Similarity	NPD6845	Suspended
0.5902	Remote Similarity	NPD7604	Phase 2
0.5902	Remote Similarity	NPD8328	Phase 3
0.5902	Remote Similarity	NPD7830	Approved
0.5902	Remote Similarity	NPD7829	Approved
0.5893	Remote Similarity	NPD5048	Discontinued
0.5888	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4697	Phase 3
0.5888	Remote Similarity	NPD5221	Approved
0.5888	Remote Similarity	NPD5222	Approved
0.5887	Remote Similarity	NPD8293	Discontinued
0.5882	Remote Similarity	NPD3573	Approved
0.5872	Remote Similarity	NPD6648	Approved
0.5872	Remote Similarity	NPD5286	Approved
0.5872	Remote Similarity	NPD4696	Approved
0.5872	Remote Similarity	NPD5285	Approved
0.5868	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD5173	Approved
0.5833	Remote Similarity	NPD6084	Phase 2
0.5825	Remote Similarity	NPD5737	Approved
0.5825	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6903	Approved
0.5825	Remote Similarity	NPD6672	Approved
0.5818	Remote Similarity	NPD5223	Approved
0.5816	Remote Similarity	NPD4822	Approved
0.5816	Remote Similarity	NPD4821	Approved
0.5816	Remote Similarity	NPD4820	Approved
0.5816	Remote Similarity	NPD4819	Approved
0.581	Remote Similarity	NPD5693	Phase 1
0.581	Remote Similarity	NPD7515	Phase 2
0.5806	Remote Similarity	NPD6336	Discontinued
0.5806	Remote Similarity	NPD7507	Approved
0.5804	Remote Similarity	NPD5141	Approved
0.5798	Remote Similarity	NPD6317	Approved
0.5784	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD3618	Phase 1
0.5776	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5328	Approved
0.5766	Remote Similarity	NPD5225	Approved
0.5766	Remote Similarity	NPD4633	Approved
0.5766	Remote Similarity	NPD5226	Approved
0.5766	Remote Similarity	NPD5224	Approved
0.5763	Remote Similarity	NPD6010	Discontinued
0.575	Remote Similarity	NPD6314	Approved
0.575	Remote Similarity	NPD7641	Discontinued
0.575	Remote Similarity	NPD6335	Approved
0.575	Remote Similarity	NPD6313	Approved
0.5747	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD3666	Approved
0.5743	Remote Similarity	NPD3133	Approved
0.5743	Remote Similarity	NPD3665	Phase 1
0.5738	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5714	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD6868	Approved
0.5702	Remote Similarity	NPD7100	Approved
0.5702	Remote Similarity	NPD7101	Approved
0.57	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4755	Approved
0.5686	Remote Similarity	NPD1696	Phase 3

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