NPASS Compound

Structure

NPC473353 OpenBabel07101719512D 30 32 0 0 1 0 0 0 0 0999 V2000 10.0266 -1.1112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6198 -0.1976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6253 -0.0931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2186 0.8205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2240 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8173 1.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8228 1.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4161 2.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4215 2.9611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0148 3.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0203 3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4325 3.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8392 2.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0759 -0.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 -0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2514 1.4476 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4771 -1.1885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2569 1.5522 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 25 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 23 28 2 0 0 0 0 24 13 1 6 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 19 1 6 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.29
Volume:	457.198
LogP:	6.387
LogD:	4.552
LogS:	-5.764
# Rotatable Bonds:	12
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	4.621
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	2.599622712295968e-05
Pgp-inhibitor:	0.44
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.641
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.706
Plasma Protein Binding (PPB):	98.29512023925781%
Volume Distribution (VD):	1.807
Pgp-substrate:	0.936820924282074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.349
CYP2C19-inhibitor:	0.787
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.569
CYP2C9-substrate:	0.481
CYP2D6-inhibitor:	0.807
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.834
CYP3A4-substrate:	0.588

ADMET: Excretion

Clearance (CL):	10.228
Half-life (T1/2):	0.446

ADMET: Toxicity

hERG Blockers:	0.65
Human Hepatotoxicity (H-HT):	0.722
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.969
Carcinogencity:	0.903
Eye Corrosion:	0.032
Eye Irritation:	0.674
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC473353

Natural Product ID:	NPC473353
*Common Name:**	(2R,6R)-2-Tridecyl-1,7-Dioxa-Dispiro[5.1.5.2]Pentadeca-9,12-Diene-4,11-Dione
IUPAC Name:	(4R,6R)-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-diene-2,11-dione
Synonyms:
Standard InCHIKey:	VEJOGRTUHYXNOZ-AOYPEHQESA-N
Standard InCHI:	InChI=1S/C26H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-24-20-23(28)21-26(29-24)19-18-25(30-26)16-14-22(27)15-17-25/h14-17,24H,2-13,18-21H2,1H3/t24-,26-/m1/s1
SMILES:	CCCCCCCCCCCCCC1CC(=O)CC2(O1)CCC3(O2)C=CC(=O)C=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402280
PubChem CID:	24853746
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	30.5	uM	PMID[508875]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	22.1	uM	PMID[508875]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	7.5	uM	PMID[508875]

☑ 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 NPC473353 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	178
0.1-0.2	1350
0.2-0.3	5612
0.3-0.4	11184
0.4-0.5	13301
0.5-0.6	7722
0.6-0.7	3222
0.7-0.8	119
0.8-0.85	0
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC471552
0.878	High Similarity	NPC473339
0.8778	High Similarity	NPC266842
0.8571	High Similarity	NPC27314
0.8571	High Similarity	NPC106912
0.8571	High Similarity	NPC2379
0.8571	High Similarity	NPC31019
0.8571	High Similarity	NPC263087
0.7976	Intermediate Similarity	NPC326753
0.7912	Intermediate Similarity	NPC471569
0.7816	Intermediate Similarity	NPC475690
0.7609	Intermediate Similarity	NPC205548
0.7609	Intermediate Similarity	NPC78008
0.7556	Intermediate Similarity	NPC155873
0.7528	Intermediate Similarity	NPC318468
0.7471	Intermediate Similarity	NPC473980
0.7471	Intermediate Similarity	NPC473981
0.7444	Intermediate Similarity	NPC38569
0.7444	Intermediate Similarity	NPC163615
0.7396	Intermediate Similarity	NPC227494
0.7356	Intermediate Similarity	NPC475699
0.7347	Intermediate Similarity	NPC187761
0.7347	Intermediate Similarity	NPC255592
0.7347	Intermediate Similarity	NPC83895
0.7347	Intermediate Similarity	NPC308567
0.7347	Intermediate Similarity	NPC261377
0.7333	Intermediate Similarity	NPC170286
0.7333	Intermediate Similarity	NPC471570
0.7326	Intermediate Similarity	NPC266119
0.7312	Intermediate Similarity	NPC153570
0.7292	Intermediate Similarity	NPC471496
0.7273	Intermediate Similarity	NPC54705
0.7263	Intermediate Similarity	NPC20713
0.7245	Intermediate Similarity	NPC471462
0.7245	Intermediate Similarity	NPC40812
0.7222	Intermediate Similarity	NPC85772
0.7216	Intermediate Similarity	NPC214694
0.7216	Intermediate Similarity	NPC473334
0.7212	Intermediate Similarity	NPC315836
0.7212	Intermediate Similarity	NPC313668
0.7204	Intermediate Similarity	NPC473248
0.7204	Intermediate Similarity	NPC72513
0.7174	Intermediate Similarity	NPC215364
0.7172	Intermediate Similarity	NPC203627
0.7158	Intermediate Similarity	NPC473455
0.7158	Intermediate Similarity	NPC179394
0.7158	Intermediate Similarity	NPC328935
0.7158	Intermediate Similarity	NPC327183
0.7158	Intermediate Similarity	NPC144133
0.7158	Intermediate Similarity	NPC62815
0.7157	Intermediate Similarity	NPC474917
0.7143	Intermediate Similarity	NPC475947
0.7143	Intermediate Similarity	NPC170377
0.7143	Intermediate Similarity	NPC311166
0.7126	Intermediate Similarity	NPC474447
0.7115	Intermediate Similarity	NPC475960
0.7113	Intermediate Similarity	NPC476267
0.7113	Intermediate Similarity	NPC474338
0.7113	Intermediate Similarity	NPC140543
0.7113	Intermediate Similarity	NPC475572
0.7111	Intermediate Similarity	NPC79277
0.7111	Intermediate Similarity	NPC475481
0.71	Intermediate Similarity	NPC473219
0.71	Intermediate Similarity	NPC470761
0.7097	Intermediate Similarity	NPC474045
0.7097	Intermediate Similarity	NPC50637
0.7097	Intermediate Similarity	NPC261253
0.7097	Intermediate Similarity	NPC279859
0.7097	Intermediate Similarity	NPC38576
0.7083	Intermediate Similarity	NPC473944
0.7083	Intermediate Similarity	NPC472705
0.7079	Intermediate Similarity	NPC150646
0.7071	Intermediate Similarity	NPC278506
0.7071	Intermediate Similarity	NPC91695
0.7071	Intermediate Similarity	NPC70145
0.7059	Intermediate Similarity	NPC472747
0.7059	Intermediate Similarity	NPC475367
0.7059	Intermediate Similarity	NPC474581
0.7059	Intermediate Similarity	NPC472750
0.7059	Intermediate Similarity	NPC473816
0.7059	Intermediate Similarity	NPC309398
0.7053	Intermediate Similarity	NPC471054
0.7053	Intermediate Similarity	NPC166919
0.7053	Intermediate Similarity	NPC87306
0.7045	Intermediate Similarity	NPC187568
0.7045	Intermediate Similarity	NPC41780
0.7021	Intermediate Similarity	NPC160138
0.7021	Intermediate Similarity	NPC231889
0.7021	Intermediate Similarity	NPC475703
0.7021	Intermediate Similarity	NPC313658
0.7021	Intermediate Similarity	NPC316138
0.7021	Intermediate Similarity	NPC74139
0.701	Intermediate Similarity	NPC475657
0.701	Intermediate Similarity	NPC320089
0.7	Intermediate Similarity	NPC472948
0.7	Intermediate Similarity	NPC469920
0.7	Intermediate Similarity	NPC474510
0.699	Remote Similarity	NPC472748
0.699	Remote Similarity	NPC305157
0.699	Remote Similarity	NPC146731
0.699	Remote Similarity	NPC307846
0.699	Remote Similarity	NPC169843
0.6989	Remote Similarity	NPC471060
0.6989	Remote Similarity	NPC99395
0.6989	Remote Similarity	NPC177932
0.6989	Remote Similarity	NPC197903
0.6989	Remote Similarity	NPC125290
0.6989	Remote Similarity	NPC261380
0.6989	Remote Similarity	NPC322529
0.6981	Remote Similarity	NPC89408
0.6981	Remote Similarity	NPC235014
0.6979	Remote Similarity	NPC473311
0.6979	Remote Similarity	NPC51004
0.6979	Remote Similarity	NPC475855
0.6979	Remote Similarity	NPC475748
0.6979	Remote Similarity	NPC473448
0.6979	Remote Similarity	NPC80875
0.6977	Remote Similarity	NPC474705
0.6977	Remote Similarity	NPC167145
0.697	Remote Similarity	NPC143446
0.697	Remote Similarity	NPC473291
0.697	Remote Similarity	NPC230800
0.697	Remote Similarity	NPC73858
0.697	Remote Similarity	NPC476275
0.6966	Remote Similarity	NPC128276
0.6961	Remote Similarity	NPC313569
0.6961	Remote Similarity	NPC149371
0.6961	Remote Similarity	NPC223834
0.6957	Remote Similarity	NPC272814
0.6957	Remote Similarity	NPC69469
0.6957	Remote Similarity	NPC250315
0.6952	Remote Similarity	NPC193765
0.6947	Remote Similarity	NPC469628
0.6947	Remote Similarity	NPC106051
0.6947	Remote Similarity	NPC471047
0.6947	Remote Similarity	NPC473151
0.6947	Remote Similarity	NPC469631
0.6947	Remote Similarity	NPC475906
0.6947	Remote Similarity	NPC469653
0.6939	Remote Similarity	NPC88507
0.6939	Remote Similarity	NPC471147
0.6939	Remote Similarity	NPC2003
0.6939	Remote Similarity	NPC256368
0.6939	Remote Similarity	NPC25701
0.6932	Remote Similarity	NPC27205
0.6923	Remote Similarity	NPC25684
0.6923	Remote Similarity	NPC275507
0.6923	Remote Similarity	NPC472751
0.6923	Remote Similarity	NPC471325
0.6923	Remote Similarity	NPC281949
0.6923	Remote Similarity	NPC141810
0.6923	Remote Similarity	NPC476740
0.6923	Remote Similarity	NPC301477
0.6923	Remote Similarity	NPC476738
0.6923	Remote Similarity	NPC472749
0.6915	Remote Similarity	NPC47937
0.6915	Remote Similarity	NPC284902
0.6915	Remote Similarity	NPC469483
0.6907	Remote Similarity	NPC65513
0.6907	Remote Similarity	NPC30515
0.6907	Remote Similarity	NPC32944
0.6907	Remote Similarity	NPC233437
0.6907	Remote Similarity	NPC284185
0.6907	Remote Similarity	NPC476705
0.6907	Remote Similarity	NPC193396
0.6907	Remote Similarity	NPC207641
0.6907	Remote Similarity	NPC477749
0.6907	Remote Similarity	NPC470373
0.6907	Remote Similarity	NPC470379
0.6907	Remote Similarity	NPC221282
0.6907	Remote Similarity	NPC473707
0.6905	Remote Similarity	NPC218477
0.69	Remote Similarity	NPC187159
0.69	Remote Similarity	NPC476612
0.69	Remote Similarity	NPC476613
0.6897	Remote Similarity	NPC330016
0.6897	Remote Similarity	NPC476355
0.6897	Remote Similarity	NPC140287
0.6893	Remote Similarity	NPC475945
0.6893	Remote Similarity	NPC471365
0.6893	Remote Similarity	NPC475871
0.6893	Remote Similarity	NPC132395
0.6893	Remote Similarity	NPC471364
0.6889	Remote Similarity	NPC254996
0.6889	Remote Similarity	NPC471299
0.6889	Remote Similarity	NPC268502
0.6889	Remote Similarity	NPC270126
0.6887	Remote Similarity	NPC112457
0.6882	Remote Similarity	NPC41856
0.6882	Remote Similarity	NPC156804
0.6875	Remote Similarity	NPC14901
0.6875	Remote Similarity	NPC307411
0.6875	Remote Similarity	NPC130359
0.6869	Remote Similarity	NPC473369
0.6869	Remote Similarity	NPC474947
0.6869	Remote Similarity	NPC475659
0.6869	Remote Similarity	NPC471141
0.6869	Remote Similarity	NPC304886
0.6869	Remote Similarity	NPC108141
0.6863	Remote Similarity	NPC474339

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 NPC473353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1746
0.2-0.3	4155
0.3-0.4	2115
0.4-0.5	624
0.5-0.6	293
0.6-0.7	57
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
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1694	Approved
0.6804	Remote Similarity	NPD46	Approved
0.6804	Remote Similarity	NPD6698	Approved
0.6792	Remote Similarity	NPD6686	Approved
0.6768	Remote Similarity	NPD5282	Discontinued
0.6633	Remote Similarity	NPD5785	Approved
0.6606	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8517	Approved
0.6522	Remote Similarity	NPD8515	Approved
0.6522	Remote Similarity	NPD8516	Approved
0.6522	Remote Similarity	NPD8513	Phase 3
0.6489	Remote Similarity	NPD5209	Approved
0.6489	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8039	Approved
0.6435	Remote Similarity	NPD6054	Approved
0.641	Remote Similarity	NPD7642	Approved
0.6389	Remote Similarity	NPD6412	Phase 2
0.6373	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6371	Approved
0.6364	Remote Similarity	NPD1695	Approved
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.6325	Remote Similarity	NPD6370	Approved
0.6316	Remote Similarity	NPD7500	Approved
0.6311	Remote Similarity	NPD7839	Suspended
0.6271	Remote Similarity	NPD7829	Approved
0.6271	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD8074	Phase 3
0.6239	Remote Similarity	NPD6016	Approved
0.6239	Remote Similarity	NPD6015	Approved
0.6238	Remote Similarity	NPD7983	Approved
0.6218	Remote Similarity	NPD7492	Approved
0.6211	Remote Similarity	NPD5369	Approved
0.6186	Remote Similarity	NPD5988	Approved
0.6167	Remote Similarity	NPD6616	Approved
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6059	Approved
0.6146	Remote Similarity	NPD4269	Approved
0.6146	Remote Similarity	NPD4270	Approved
0.6139	Remote Similarity	NPD7838	Discovery
0.6116	Remote Similarity	NPD7078	Approved
0.6106	Remote Similarity	NPD6053	Discontinued
0.6092	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7331	Phase 2
0.6066	Remote Similarity	NPD7736	Approved
0.6063	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7146	Approved
0.6061	Remote Similarity	NPD5330	Approved
0.6061	Remote Similarity	NPD5786	Approved
0.6061	Remote Similarity	NPD7521	Approved
0.6061	Remote Similarity	NPD6409	Approved
0.6061	Remote Similarity	NPD6684	Approved
0.6061	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7638	Approved
0.6034	Remote Similarity	NPD7115	Discovery
0.602	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD4251	Approved
0.5981	Remote Similarity	NPD7639	Approved
0.5981	Remote Similarity	NPD7640	Approved
0.5979	Remote Similarity	NPD6435	Approved
0.5966	Remote Similarity	NPD8444	Approved
0.5965	Remote Similarity	NPD6882	Approved
0.5946	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6672	Approved
0.5941	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5737	Approved
0.5941	Remote Similarity	NPD6903	Approved
0.5938	Remote Similarity	NPD4252	Approved
0.5922	Remote Similarity	NPD5693	Phase 1
0.5922	Remote Similarity	NPD6411	Approved
0.5918	Remote Similarity	NPD7154	Phase 3
0.5902	Remote Similarity	NPD7507	Approved
0.5902	Remote Similarity	NPD8451	Approved
0.59	Remote Similarity	NPD4249	Approved
0.5897	Remote Similarity	NPD6009	Approved
0.5895	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4225	Approved
0.5854	Remote Similarity	NPD8448	Approved
0.5854	Remote Similarity	NPD8293	Discontinued
0.5842	Remote Similarity	NPD3573	Approved
0.5841	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.584	Remote Similarity	NPD5956	Approved
0.5833	Remote Similarity	NPD6648	Approved
0.5833	Remote Similarity	NPD7503	Approved
0.581	Remote Similarity	NPD7900	Approved
0.581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD8336	Approved
0.5806	Remote Similarity	NPD8337	Approved
0.5806	Remote Similarity	NPD6033	Approved
0.5795	Remote Similarity	NPD7341	Phase 2
0.5789	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4756	Discovery
0.578	Remote Similarity	NPD5344	Discontinued
0.5773	Remote Similarity	NPD5368	Approved
0.5773	Remote Similarity	NPD4822	Approved
0.5773	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4821	Approved
0.5773	Remote Similarity	NPD4819	Approved
0.5773	Remote Similarity	NPD4820	Approved
0.5769	Remote Similarity	NPD7637	Suspended
0.5758	Remote Similarity	NPD5362	Discontinued
0.5755	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6899	Approved
0.5752	Remote Similarity	NPD6881	Approved
0.575	Remote Similarity	NPD6319	Approved
0.5748	Remote Similarity	NPD8338	Approved
0.5747	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8328	Phase 3
0.5728	Remote Similarity	NPD6673	Approved
0.5728	Remote Similarity	NPD6080	Approved
0.5728	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD8392	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD8391	Approved
0.5714	Remote Similarity	NPD6914	Discontinued
0.5714	Remote Similarity	NPD8390	Approved
0.5714	Remote Similarity	NPD7641	Discontinued
0.5691	Remote Similarity	NPD8299	Approved
0.5691	Remote Similarity	NPD8342	Approved
0.5691	Remote Similarity	NPD8341	Approved
0.5691	Remote Similarity	NPD8340	Approved
0.5673	Remote Similarity	NPD5207	Approved
0.5669	Remote Similarity	NPD7260	Phase 2
0.5664	Remote Similarity	NPD5697	Approved
0.566	Remote Similarity	NPD7748	Approved
0.5656	Remote Similarity	NPD8080	Discontinued
0.5652	Remote Similarity	NPD6883	Approved
0.5652	Remote Similarity	NPD7290	Approved
0.5652	Remote Similarity	NPD7102	Approved
0.5652	Remote Similarity	NPD4634	Approved
0.5648	Remote Similarity	NPD6083	Phase 2
0.5648	Remote Similarity	NPD6084	Phase 2
0.5648	Remote Similarity	NPD7902	Approved
0.5644	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD4632	Approved
0.5619	Remote Similarity	NPD6079	Approved
0.5619	Remote Similarity	NPD6050	Approved
0.5619	Remote Similarity	NPD5694	Approved
0.5619	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6011	Approved
0.5612	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6067	Discontinued
0.5607	Remote Similarity	NPD5695	Phase 3
0.5603	Remote Similarity	NPD6649	Approved
0.5603	Remote Similarity	NPD6650	Approved
0.5603	Remote Similarity	NPD6617	Approved
0.5603	Remote Similarity	NPD6869	Approved
0.5603	Remote Similarity	NPD6847	Approved
0.5603	Remote Similarity	NPD8130	Phase 1
0.56	Remote Similarity	NPD6110	Phase 1

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