NPASS Compound

Structure

NPC52923 OpenBabel07101718192D 25 26 0 0 1 0 0 0 0 0999 V2000 -3.5509 3.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0157 5.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2330 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 2.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6488 3.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8567 4.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6977 3.0085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8078 4.6046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4898 2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4487 -0.1636 0.0000 C 0 0 2 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 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3147 4.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 2.8364 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 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 15 21 2 0 0 0 0 15 24 1 0 0 0 0 16 24 1 6 0 0 0 17 20 1 1 0 0 0 17 22 1 0 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	368.132
LogP:	3.248
LogD:	2.395
LogS:	-3.92
# Rotatable Bonds:	6
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	5.11
Fsp3:	0.6
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:	-5.059
MDCK Permeability:	7.184423157013953e-05
Pgp-inhibitor:	0.405
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.184
20% Bioavailability (F20%):	0.415
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.695
Plasma Protein Binding (PPB):	87.11541748046875%
Volume Distribution (VD):	1.634
Pgp-substrate:	10.233956336975098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.629
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	6.412
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.297
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.489
Skin Sensitization:	0.173
Carcinogencity:	0.041
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC52923

Natural Product ID:	NPC52923
*Common Name:**	(+)-Miliusane Ix
IUPAC Name:	[(1R,5S,6R,9S)-1-[(1E)-2,6-dimethylhepta-1,5-dienyl]-6-hydroxy-3-oxo-2-oxaspiro[4.5]dec-7-en-9-yl] acetate
Synonyms:	(+)-Miliusane IX
Standard InCHIKey:	NKLDAIQKFGVGAV-ZXSMNVAJSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-13(2)6-5-7-14(3)10-18-20(12-19(23)25-18)11-16(24-15(4)21)8-9-17(20)22/h6,8-10,16-18,22H,5,7,11-12H2,1-4H3/b14-10+/t16-,17-,18-,20+/m1/s1
SMILES:	CC(=CCC/C(=C/[C@@H]1[C@@]2(C[C@@H](C=C[C@H]2O)OC(=O)C)CC(=O)O1)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL380413
PubChem CID:	11552004
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	9

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	57400.0	nM	PMID[482891]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	>	57400.0	nM	PMID[482891]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	46010.0	nM	PMID[482891]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	57400.0	nM	PMID[482891]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	52560.0	nM	PMID[482891]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3280.0	nM	PMID[482891]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	18300.0	nM	PMID[482892]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	7240.0	nM	PMID[482892]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	13300.0	nM	PMID[482892]

☑ 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 NPC52923 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	159
0.1-0.2	1216
0.2-0.3	5262
0.3-0.4	12954
0.4-0.5	11447
0.5-0.6	7387
0.6-0.7	3718
0.7-0.8	533
0.8-0.85	15
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC87306
0.8941	High Similarity	NPC473455
0.881	High Similarity	NPC473248
0.8706	High Similarity	NPC153570
0.8539	High Similarity	NPC214694
0.8452	Intermediate Similarity	NPC163615
0.8452	Intermediate Similarity	NPC38569
0.8452	Intermediate Similarity	NPC219966
0.8353	Intermediate Similarity	NPC155873
0.8256	Intermediate Similarity	NPC278283
0.8256	Intermediate Similarity	NPC478112
0.8072	Intermediate Similarity	NPC475210
0.8068	Intermediate Similarity	NPC473715
0.8023	Intermediate Similarity	NPC32676
0.8	Intermediate Similarity	NPC473321
0.8	Intermediate Similarity	NPC235369
0.8	Intermediate Similarity	NPC474252
0.7978	Intermediate Similarity	NPC78008
0.7952	Intermediate Similarity	NPC127526
0.7931	Intermediate Similarity	NPC21469
0.7912	Intermediate Similarity	NPC475912
0.7889	Intermediate Similarity	NPC475855
0.7889	Intermediate Similarity	NPC473619
0.7849	Intermediate Similarity	NPC11396
0.7849	Intermediate Similarity	NPC21302
0.7831	Intermediate Similarity	NPC474278
0.7816	Intermediate Similarity	NPC212363
0.7778	Intermediate Similarity	NPC474032
0.7778	Intermediate Similarity	NPC295312
0.7766	Intermediate Similarity	NPC134454
0.7766	Intermediate Similarity	NPC17326
0.7742	Intermediate Similarity	NPC471142
0.7742	Intermediate Similarity	NPC36954
0.7742	Intermediate Similarity	NPC477922
0.7742	Intermediate Similarity	NPC270013
0.7742	Intermediate Similarity	NPC14961
0.7717	Intermediate Similarity	NPC162205
0.7717	Intermediate Similarity	NPC273579
0.7717	Intermediate Similarity	NPC295204
0.7717	Intermediate Similarity	NPC288240
0.7701	Intermediate Similarity	NPC169575
0.7701	Intermediate Similarity	NPC473390
0.7701	Intermediate Similarity	NPC40746
0.7701	Intermediate Similarity	NPC250315
0.7701	Intermediate Similarity	NPC131669
0.7701	Intermediate Similarity	NPC116543
0.7692	Intermediate Similarity	NPC144133
0.7692	Intermediate Similarity	NPC179394
0.7684	Intermediate Similarity	NPC23364
0.7674	Intermediate Similarity	NPC52861
0.7674	Intermediate Similarity	NPC275507
0.7674	Intermediate Similarity	NPC24417
0.7667	Intermediate Similarity	NPC202672
0.766	Intermediate Similarity	NPC477921
0.766	Intermediate Similarity	NPC476315
0.7653	Intermediate Similarity	NPC220964
0.7653	Intermediate Similarity	NPC258532
0.7653	Intermediate Similarity	NPC475676
0.7647	Intermediate Similarity	NPC321728
0.7634	Intermediate Similarity	NPC250075
0.7634	Intermediate Similarity	NPC303942
0.7634	Intermediate Similarity	NPC57405
0.7634	Intermediate Similarity	NPC474035
0.7634	Intermediate Similarity	NPC81386
0.7624	Intermediate Similarity	NPC5103
0.7619	Intermediate Similarity	NPC7563
0.7619	Intermediate Similarity	NPC116177
0.7619	Intermediate Similarity	NPC320630
0.7614	Intermediate Similarity	NPC158756
0.7614	Intermediate Similarity	NPC476804
0.7614	Intermediate Similarity	NPC31086
0.7609	Intermediate Similarity	NPC30515
0.7609	Intermediate Similarity	NPC184463
0.7586	Intermediate Similarity	NPC229825
0.7582	Intermediate Similarity	NPC478110
0.7579	Intermediate Similarity	NPC70145
0.7579	Intermediate Similarity	NPC91695
0.7556	Intermediate Similarity	NPC160138
0.7553	Intermediate Similarity	NPC304886
0.7551	Intermediate Similarity	NPC4620
0.7551	Intermediate Similarity	NPC110989
0.7529	Intermediate Similarity	NPC108816
0.7529	Intermediate Similarity	NPC267231
0.7529	Intermediate Similarity	NPC93763
0.7528	Intermediate Similarity	NPC255307
0.7528	Intermediate Similarity	NPC470755
0.7527	Intermediate Similarity	NPC81419
0.7527	Intermediate Similarity	NPC475838
0.7527	Intermediate Similarity	NPC125674
0.7527	Intermediate Similarity	NPC212486
0.7527	Intermediate Similarity	NPC228451
0.7527	Intermediate Similarity	NPC179746
0.7527	Intermediate Similarity	NPC476300
0.75	Intermediate Similarity	NPC476004
0.75	Intermediate Similarity	NPC469368
0.75	Intermediate Similarity	NPC51004
0.75	Intermediate Similarity	NPC474761
0.75	Intermediate Similarity	NPC141191
0.75	Intermediate Similarity	NPC68819
0.7475	Intermediate Similarity	NPC203659
0.7474	Intermediate Similarity	NPC185553
0.7474	Intermediate Similarity	NPC473859
0.7473	Intermediate Similarity	NPC475819
0.7471	Intermediate Similarity	NPC297440
0.747	Intermediate Similarity	NPC114727
0.747	Intermediate Similarity	NPC476590
0.747	Intermediate Similarity	NPC474280
0.7449	Intermediate Similarity	NPC225353
0.7447	Intermediate Similarity	NPC475927
0.7447	Intermediate Similarity	NPC474247
0.7447	Intermediate Similarity	NPC475832
0.7444	Intermediate Similarity	NPC475461
0.7444	Intermediate Similarity	NPC469910
0.7444	Intermediate Similarity	NPC305475
0.7442	Intermediate Similarity	NPC167881
0.7442	Intermediate Similarity	NPC98557
0.7439	Intermediate Similarity	NPC477086
0.7439	Intermediate Similarity	NPC477087
0.7426	Intermediate Similarity	NPC14862
0.7426	Intermediate Similarity	NPC233379
0.7426	Intermediate Similarity	NPC474664
0.7423	Intermediate Similarity	NPC288876
0.7419	Intermediate Similarity	NPC233437
0.7419	Intermediate Similarity	NPC207641
0.7419	Intermediate Similarity	NPC9447
0.7419	Intermediate Similarity	NPC12172
0.7419	Intermediate Similarity	NPC208886
0.7416	Intermediate Similarity	NPC96259
0.7416	Intermediate Similarity	NPC472957
0.7416	Intermediate Similarity	NPC474865
0.7416	Intermediate Similarity	NPC191476
0.7416	Intermediate Similarity	NPC472958
0.7416	Intermediate Similarity	NPC114979
0.7416	Intermediate Similarity	NPC141193
0.7404	Intermediate Similarity	NPC469496
0.7404	Intermediate Similarity	NPC9848
0.7404	Intermediate Similarity	NPC469463
0.7404	Intermediate Similarity	NPC312017
0.7404	Intermediate Similarity	NPC469454
0.74	Intermediate Similarity	NPC475802
0.74	Intermediate Similarity	NPC469607
0.74	Intermediate Similarity	NPC472749
0.74	Intermediate Similarity	NPC472751
0.7396	Intermediate Similarity	NPC40812
0.7396	Intermediate Similarity	NPC169205
0.7391	Intermediate Similarity	NPC218927
0.7391	Intermediate Similarity	NPC206001
0.7391	Intermediate Similarity	NPC307411
0.7386	Intermediate Similarity	NPC89555
0.7381	Intermediate Similarity	NPC473948
0.7379	Intermediate Similarity	NPC304180
0.7379	Intermediate Similarity	NPC179798
0.7374	Intermediate Similarity	NPC475321
0.7374	Intermediate Similarity	NPC474775
0.7374	Intermediate Similarity	NPC69171
0.7374	Intermediate Similarity	NPC474165
0.7374	Intermediate Similarity	NPC472747
0.7374	Intermediate Similarity	NPC472750
0.7368	Intermediate Similarity	NPC475659
0.7363	Intermediate Similarity	NPC477959
0.7363	Intermediate Similarity	NPC179659
0.7363	Intermediate Similarity	NPC142583
0.7363	Intermediate Similarity	NPC86005
0.7353	Intermediate Similarity	NPC15218
0.7349	Intermediate Similarity	NPC477085
0.7347	Intermediate Similarity	NPC244456
0.7347	Intermediate Similarity	NPC469657
0.7347	Intermediate Similarity	NPC472753
0.7333	Intermediate Similarity	NPC137033
0.7333	Intermediate Similarity	NPC165162
0.7327	Intermediate Similarity	NPC194620
0.7327	Intermediate Similarity	NPC326994
0.7327	Intermediate Similarity	NPC72813
0.7327	Intermediate Similarity	NPC474421
0.7327	Intermediate Similarity	NPC324327
0.7326	Intermediate Similarity	NPC474816
0.7326	Intermediate Similarity	NPC471465
0.7326	Intermediate Similarity	NPC196653
0.7326	Intermediate Similarity	NPC209135
0.732	Intermediate Similarity	NPC61630
0.732	Intermediate Similarity	NPC81483
0.732	Intermediate Similarity	NPC471144
0.732	Intermediate Similarity	NPC83895
0.732	Intermediate Similarity	NPC216478
0.732	Intermediate Similarity	NPC255592
0.732	Intermediate Similarity	NPC169468
0.732	Intermediate Similarity	NPC261377
0.732	Intermediate Similarity	NPC307517
0.732	Intermediate Similarity	NPC308567
0.732	Intermediate Similarity	NPC187761
0.7312	Intermediate Similarity	NPC71533
0.7312	Intermediate Similarity	NPC106510
0.7312	Intermediate Similarity	NPC158488
0.7312	Intermediate Similarity	NPC473448
0.7312	Intermediate Similarity	NPC474232
0.7308	Intermediate Similarity	NPC126691
0.7303	Intermediate Similarity	NPC69469
0.7303	Intermediate Similarity	NPC59097
0.7303	Intermediate Similarity	NPC474809
0.73	Intermediate Similarity	NPC472748

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 NPC52923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1734
0.2-0.3	4000
0.3-0.4	2314
0.4-0.5	587
0.5-0.6	303
0.6-0.7	65
0.7-0.8	9
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
0.7253	Intermediate Similarity	NPD4249	Approved
0.7234	Intermediate Similarity	NPD7983	Approved
0.7188	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4251	Approved
0.7174	Intermediate Similarity	NPD4250	Approved
0.716	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5779	Approved
0.7158	Intermediate Similarity	NPD5778	Approved
0.7128	Intermediate Similarity	NPD46	Approved
0.7128	Intermediate Similarity	NPD6698	Approved
0.6966	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7154	Phase 3
0.6875	Remote Similarity	NPD7637	Suspended
0.6848	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6435	Approved
0.6782	Remote Similarity	NPD8039	Approved
0.6774	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5785	Approved
0.6768	Remote Similarity	NPD7839	Suspended
0.6742	Remote Similarity	NPD4268	Approved
0.6742	Remote Similarity	NPD4271	Approved
0.6739	Remote Similarity	NPD6110	Phase 1
0.6733	Remote Similarity	NPD7640	Approved
0.6733	Remote Similarity	NPD7639	Approved
0.6729	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD6411	Approved
0.6637	Remote Similarity	NPD8516	Approved
0.6637	Remote Similarity	NPD8517	Approved
0.6637	Remote Similarity	NPD8515	Approved
0.6637	Remote Similarity	NPD8513	Phase 3
0.6636	Remote Similarity	NPD6371	Approved
0.6634	Remote Similarity	NPD7638	Approved
0.6634	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6686	Approved
0.6598	Remote Similarity	NPD7838	Discovery
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD4822	Approved
0.6593	Remote Similarity	NPD4819	Approved
0.6593	Remote Similarity	NPD4821	Approved
0.6593	Remote Similarity	NPD4252	Approved
0.6593	Remote Similarity	NPD4820	Approved
0.6593	Remote Similarity	NPD5368	Approved
0.6566	Remote Similarity	NPD5282	Discontinued
0.6559	Remote Similarity	NPD5362	Discontinued
0.6514	Remote Similarity	NPD6053	Discontinued
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6101	Approved
0.6452	Remote Similarity	NPD5209	Approved
0.6452	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4270	Approved
0.642	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8074	Phase 3
0.6355	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1695	Approved
0.63	Remote Similarity	NPD6399	Phase 3
0.6277	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5048	Discontinued
0.625	Remote Similarity	NPD5363	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.62	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5344	Discontinued
0.619	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4732	Discontinued
0.617	Remote Similarity	NPD5369	Approved
0.617	Remote Similarity	NPD4790	Discontinued
0.6162	Remote Similarity	NPD5370	Suspended
0.6147	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6881	Approved
0.6147	Remote Similarity	NPD6899	Approved
0.614	Remote Similarity	NPD7115	Discovery
0.6132	Remote Similarity	NPD7632	Discontinued
0.6126	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD6650	Approved
0.6118	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7128	Approved
0.6111	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD6008	Approved
0.6111	Remote Similarity	NPD6402	Approved
0.6111	Remote Similarity	NPD5739	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6055	Remote Similarity	NPD5701	Approved
0.6036	Remote Similarity	NPD7102	Approved
0.6036	Remote Similarity	NPD6883	Approved
0.6036	Remote Similarity	NPD7290	Approved
0.6036	Remote Similarity	NPD6421	Discontinued
0.6018	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD7320	Approved
0.5983	Remote Similarity	NPD6319	Approved
0.5982	Remote Similarity	NPD2204	Approved
0.5982	Remote Similarity	NPD6617	Approved
0.5982	Remote Similarity	NPD8130	Phase 1
0.5982	Remote Similarity	NPD6869	Approved
0.5982	Remote Similarity	NPD6847	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.5979	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6010	Discontinued
0.5952	Remote Similarity	NPD368	Approved
0.5943	Remote Similarity	NPD6648	Approved
0.5929	Remote Similarity	NPD8297	Approved
0.5929	Remote Similarity	NPD6882	Approved
0.5917	Remote Similarity	NPD7492	Approved
0.5914	Remote Similarity	NPD4756	Discovery
0.5909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6412	Phase 2
0.5905	Remote Similarity	NPD6084	Phase 2
0.5905	Remote Similarity	NPD6083	Phase 2
0.5905	Remote Similarity	NPD7902	Approved
0.5897	Remote Similarity	NPD6927	Phase 3
0.5895	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7514	Phase 3
0.5895	Remote Similarity	NPD7332	Phase 2
0.5887	Remote Similarity	NPD7260	Phase 2
0.5876	Remote Similarity	NPD6695	Phase 3
0.5872	Remote Similarity	NPD5141	Approved
0.5868	Remote Similarity	NPD6616	Approved
0.5865	Remote Similarity	NPD5695	Phase 3
0.5862	Remote Similarity	NPD6009	Approved
0.5862	Remote Similarity	NPD7331	Phase 2
0.5859	Remote Similarity	NPD6422	Discontinued
0.5854	Remote Similarity	NPD7319	Approved
0.5851	Remote Similarity	NPD7145	Approved
0.5849	Remote Similarity	NPD5696	Approved
0.5847	Remote Similarity	NPD6054	Approved
0.5844	Remote Similarity	NPD3173	Approved
0.5833	Remote Similarity	NPD6902	Approved
0.582	Remote Similarity	NPD7078	Approved
0.5814	Remote Similarity	NPD3197	Phase 1
0.581	Remote Similarity	NPD4228	Discovery
0.5798	Remote Similarity	NPD8444	Approved
0.5798	Remote Similarity	NPD6015	Approved
0.5798	Remote Similarity	NPD5983	Phase 2
0.5798	Remote Similarity	NPD6016	Approved
0.5794	Remote Similarity	NPD5286	Approved
0.5794	Remote Similarity	NPD4696	Approved
0.5794	Remote Similarity	NPD5285	Approved
0.5773	Remote Similarity	NPD3667	Approved
0.5772	Remote Similarity	NPD7736	Approved
0.5769	Remote Similarity	NPD7748	Approved
0.5765	Remote Similarity	NPD4194	Approved
0.5765	Remote Similarity	NPD4193	Approved
0.5765	Remote Similarity	NPD4191	Approved
0.5765	Remote Similarity	NPD4192	Approved
0.5755	Remote Similarity	NPD4755	Approved
0.575	Remote Similarity	NPD6370	Approved
0.575	Remote Similarity	NPD5988	Approved
0.5745	Remote Similarity	NPD6925	Approved
0.5745	Remote Similarity	NPD5776	Phase 2
0.5738	Remote Similarity	NPD8451	Approved
0.5728	Remote Similarity	NPD6079	Approved
0.5728	Remote Similarity	NPD7515	Phase 2
0.5728	Remote Similarity	NPD5284	Approved
0.5728	Remote Similarity	NPD5281	Approved
0.5714	Remote Similarity	NPD6059	Approved
0.5702	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7642	Approved
0.5702	Remote Similarity	NPD7604	Phase 2
0.5702	Remote Similarity	NPD8328	Phase 3
0.5702	Remote Similarity	NPD7829	Approved
0.5702	Remote Similarity	NPD7830	Approved
0.57	Remote Similarity	NPD6409	Approved
0.57	Remote Similarity	NPD5330	Approved
0.57	Remote Similarity	NPD7334	Approved
0.57	Remote Similarity	NPD3618	Phase 1
0.57	Remote Similarity	NPD7521	Approved
0.57	Remote Similarity	NPD6684	Approved
0.57	Remote Similarity	NPD7146	Approved
0.5699	Remote Similarity	NPD8264	Approved
0.5691	Remote Similarity	NPD8448	Approved
0.5691	Remote Similarity	NPD8293	Discontinued
0.5688	Remote Similarity	NPD5226	Approved
0.5688	Remote Similarity	NPD4633	Approved
0.5688	Remote Similarity	NPD5225	Approved
0.5688	Remote Similarity	NPD5224	Approved
0.5686	Remote Similarity	NPD5328	Approved
0.5686	Remote Similarity	NPD6051	Approved
0.5678	Remote Similarity	NPD7641	Discontinued
0.5667	Remote Similarity	NPD7503	Approved
0.5667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5221	Approved
0.566	Remote Similarity	NPD4697	Phase 3
0.566	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5222	Approved
0.566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3133	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