NPASS Compound

Structure

NPC474369 OpenBabel07101718322D 25 26 0 0 1 0 0 0 0 0999 V2000 -4.9917 -2.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8748 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5677 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0677 0.3660 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 -5.5677 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 2 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 15 2 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 15 16 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 17 25 1 0 0 0 0 18 14 1 6 0 0 0 18 19 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	368.132
LogP:	2.357
LogD:	2.046
LogS:	-2.915
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.353
Synthetic Accessibility Score:	5.298
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.512
MDCK Permeability:	5.9282800066284835e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.681
30% Bioavailability (F30%):	0.302

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.812
Plasma Protein Binding (PPB):	54.16978454589844%
Volume Distribution (VD):	0.687
Pgp-substrate:	44.2706298828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.696
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	6.53
Half-life (T1/2):	0.086

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.778
Drug-inuced Liver Injury (DILI):	0.369
AMES Toxicity:	0.647
Rat Oral Acute Toxicity:	0.702
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.096
Carcinogencity:	0.952
Eye Corrosion:	0.032
Eye Irritation:	0.1
Respiratory Toxicity:	0.726

Download Data

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

Natural Product: NPC474369

Natural Product ID:	NPC474369
*Common Name:**	Xeniolide-G
IUPAC Name:	(4E,4aS,11aR)-8-hydroperoxy-4-[(E)-4-hydroxy-4-methylpent-2-enylidene]-7,11-dimethylidene-5,6,8,9,10,11a-hexahydro-4aH-cyclonona[c]pyran-1-one
Synonyms:	Xeniolide-G
Standard InCHIKey:	RBMLFMIIGOFFQM-YSSVXLFKSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-13-7-9-16-15(6-5-11-20(3,4)22)12-24-19(21)18(16)14(2)8-10-17(13)25-23/h5-6,11,16-18,22-23H,1-2,7-10,12H2,3-4H3/b11-5+,15-6-/t16-,17?,18+/m1/s1
SMILES:	CC(C)(C=CC=C1COC(=O)C2C1CCC(=C)C(CCC2=C)OO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465676
PubChem CID:	10247161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[12502332]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562830]
NPO14298	Xenia umbellata	Species	Xeniidae	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
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.77	ug ml-1	PMID[515555]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	8.31	ug ml-1	PMID[515555]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.04	ug ml-1	PMID[515555]

☑ 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 NPC474369 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	184
0.1-0.2	969
0.2-0.3	4006
0.3-0.4	9973
0.4-0.5	15360
0.5-0.6	7952
0.6-0.7	3944
0.7-0.8	287
0.8-0.85	11
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC116575
0.9286	High Similarity	NPC106040
0.9286	High Similarity	NPC212598
0.9286	High Similarity	NPC115179
0.8929	High Similarity	NPC234038
0.8916	High Similarity	NPC14575
0.8916	High Similarity	NPC196487
0.8764	High Similarity	NPC272050
0.875	High Similarity	NPC476049
0.875	High Similarity	NPC107668
0.8706	High Similarity	NPC198314
0.8675	High Similarity	NPC475936
0.8571	High Similarity	NPC53867
0.8415	Intermediate Similarity	NPC474341
0.8395	Intermediate Similarity	NPC12740
0.8395	Intermediate Similarity	NPC110461
0.8387	Intermediate Similarity	NPC475053
0.8272	Intermediate Similarity	NPC475861
0.825	Intermediate Similarity	NPC135703
0.8182	Intermediate Similarity	NPC474765
0.8171	Intermediate Similarity	NPC61863
0.8152	Intermediate Similarity	NPC107476
0.814	Intermediate Similarity	NPC475842
0.8118	Intermediate Similarity	NPC325031
0.8095	Intermediate Similarity	NPC469617
0.8046	Intermediate Similarity	NPC243618
0.8046	Intermediate Similarity	NPC70424
0.8046	Intermediate Similarity	NPC474776
0.7978	Intermediate Similarity	NPC86005
0.7907	Intermediate Similarity	NPC475481
0.7907	Intermediate Similarity	NPC79277
0.7865	Intermediate Similarity	NPC122502
0.7841	Intermediate Similarity	NPC72464
0.7841	Intermediate Similarity	NPC9868
0.7841	Intermediate Similarity	NPC295799
0.7816	Intermediate Similarity	NPC85772
0.7791	Intermediate Similarity	NPC103634
0.7791	Intermediate Similarity	NPC233377
0.7765	Intermediate Similarity	NPC121200
0.7765	Intermediate Similarity	NPC267231
0.7753	Intermediate Similarity	NPC261380
0.7738	Intermediate Similarity	NPC474447
0.7738	Intermediate Similarity	NPC271070
0.7727	Intermediate Similarity	NPC250315
0.7727	Intermediate Similarity	NPC475989
0.7701	Intermediate Similarity	NPC42470
0.7677	Intermediate Similarity	NPC309190
0.7674	Intermediate Similarity	NPC471537
0.7674	Intermediate Similarity	NPC89128
0.7667	Intermediate Similarity	NPC315395
0.7667	Intermediate Similarity	NPC316426
0.7667	Intermediate Similarity	NPC476982
0.766	Intermediate Similarity	NPC475572
0.7653	Intermediate Similarity	NPC475091
0.7647	Intermediate Similarity	NPC316324
0.7647	Intermediate Similarity	NPC281296
0.7634	Intermediate Similarity	NPC111114
0.7634	Intermediate Similarity	NPC300312
0.7634	Intermediate Similarity	NPC261607
0.7634	Intermediate Similarity	NPC475972
0.7619	Intermediate Similarity	NPC60718
0.7619	Intermediate Similarity	NPC255060
0.7614	Intermediate Similarity	NPC89555
0.7614	Intermediate Similarity	NPC474252
0.7609	Intermediate Similarity	NPC97577
0.7609	Intermediate Similarity	NPC284561
0.7582	Intermediate Similarity	NPC160138
0.7582	Intermediate Similarity	NPC312561
0.7582	Intermediate Similarity	NPC477959
0.7561	Intermediate Similarity	NPC4299
0.7561	Intermediate Similarity	NPC475310
0.7558	Intermediate Similarity	NPC93763
0.7558	Intermediate Similarity	NPC108816
0.7558	Intermediate Similarity	NPC127526
0.7556	Intermediate Similarity	NPC137033
0.7556	Intermediate Similarity	NPC255307
0.7556	Intermediate Similarity	NPC215364
0.7556	Intermediate Similarity	NPC474547
0.7529	Intermediate Similarity	NPC239127
0.7529	Intermediate Similarity	NPC469514
0.7528	Intermediate Similarity	NPC16488
0.7528	Intermediate Similarity	NPC170377
0.7528	Intermediate Similarity	NPC222358
0.7527	Intermediate Similarity	NPC474761
0.7527	Intermediate Similarity	NPC281942
0.7527	Intermediate Similarity	NPC476004
0.7527	Intermediate Similarity	NPC473448
0.7527	Intermediate Similarity	NPC214844
0.7527	Intermediate Similarity	NPC232426
0.7527	Intermediate Similarity	NPC469372
0.7526	Intermediate Similarity	NPC64742
0.75	Intermediate Similarity	NPC330016
0.75	Intermediate Similarity	NPC229584
0.75	Intermediate Similarity	NPC227379
0.75	Intermediate Similarity	NPC474551
0.75	Intermediate Similarity	NPC473151
0.75	Intermediate Similarity	NPC141810
0.75	Intermediate Similarity	NPC24816
0.75	Intermediate Similarity	NPC153805
0.75	Intermediate Similarity	NPC239162
0.75	Intermediate Similarity	NPC26078
0.75	Intermediate Similarity	NPC474471
0.75	Intermediate Similarity	NPC112868
0.75	Intermediate Similarity	NPC14203
0.75	Intermediate Similarity	NPC473658
0.75	Intermediate Similarity	NPC9812
0.75	Intermediate Similarity	NPC52861
0.7475	Intermediate Similarity	NPC478156
0.7474	Intermediate Similarity	NPC38830
0.7473	Intermediate Similarity	NPC475461
0.7473	Intermediate Similarity	NPC202394
0.7473	Intermediate Similarity	NPC284902
0.7473	Intermediate Similarity	NPC476104
0.7473	Intermediate Similarity	NPC164393
0.7473	Intermediate Similarity	NPC305475
0.7447	Intermediate Similarity	NPC470379
0.7447	Intermediate Similarity	NPC303697
0.7447	Intermediate Similarity	NPC470373
0.7447	Intermediate Similarity	NPC141831
0.7447	Intermediate Similarity	NPC45579
0.7447	Intermediate Similarity	NPC36491
0.7447	Intermediate Similarity	NPC219874
0.7444	Intermediate Similarity	NPC114979
0.7444	Intermediate Similarity	NPC476804
0.7444	Intermediate Similarity	NPC82297
0.7444	Intermediate Similarity	NPC191476
0.7442	Intermediate Similarity	NPC470240
0.7442	Intermediate Similarity	NPC476439
0.7442	Intermediate Similarity	NPC116177
0.7442	Intermediate Similarity	NPC476794
0.7442	Intermediate Similarity	NPC315394
0.7442	Intermediate Similarity	NPC7563
0.7442	Intermediate Similarity	NPC320630
0.7439	Intermediate Similarity	NPC101622
0.7423	Intermediate Similarity	NPC208094
0.7423	Intermediate Similarity	NPC254496
0.7419	Intermediate Similarity	NPC307092
0.7419	Intermediate Similarity	NPC256902
0.7419	Intermediate Similarity	NPC36668
0.7419	Intermediate Similarity	NPC295312
0.7419	Intermediate Similarity	NPC51358
0.7419	Intermediate Similarity	NPC118193
0.7419	Intermediate Similarity	NPC83423
0.7419	Intermediate Similarity	NPC118011
0.7416	Intermediate Similarity	NPC471159
0.7416	Intermediate Similarity	NPC474291
0.7416	Intermediate Similarity	NPC145963
0.7416	Intermediate Similarity	NPC123880
0.7416	Intermediate Similarity	NPC35556
0.7412	Intermediate Similarity	NPC199445
0.7412	Intermediate Similarity	NPC228978
0.7396	Intermediate Similarity	NPC295347
0.7396	Intermediate Similarity	NPC209355
0.7396	Intermediate Similarity	NPC304886
0.7391	Intermediate Similarity	NPC231599
0.7391	Intermediate Similarity	NPC181327
0.7391	Intermediate Similarity	NPC475678
0.7386	Intermediate Similarity	NPC190008
0.7386	Intermediate Similarity	NPC474510
0.7381	Intermediate Similarity	NPC238425
0.7381	Intermediate Similarity	NPC472018
0.7381	Intermediate Similarity	NPC474543
0.7381	Intermediate Similarity	NPC167145
0.7374	Intermediate Similarity	NPC116139
0.7374	Intermediate Similarity	NPC206079
0.7374	Intermediate Similarity	NPC244456
0.7374	Intermediate Similarity	NPC469657
0.7368	Intermediate Similarity	NPC475912
0.7363	Intermediate Similarity	NPC197903
0.7363	Intermediate Similarity	NPC99395
0.7363	Intermediate Similarity	NPC165162
0.7363	Intermediate Similarity	NPC471344
0.7356	Intermediate Similarity	NPC474005
0.7356	Intermediate Similarity	NPC128276
0.7356	Intermediate Similarity	NPC4436
0.7349	Intermediate Similarity	NPC69462
0.7347	Intermediate Similarity	NPC244411
0.7347	Intermediate Similarity	NPC316598
0.734	Intermediate Similarity	NPC475855
0.734	Intermediate Similarity	NPC77337
0.734	Intermediate Similarity	NPC316228
0.734	Intermediate Similarity	NPC144133
0.734	Intermediate Similarity	NPC179394
0.734	Intermediate Similarity	NPC469368
0.734	Intermediate Similarity	NPC220454
0.734	Intermediate Similarity	NPC212679
0.734	Intermediate Similarity	NPC51004
0.734	Intermediate Similarity	NPC469595
0.734	Intermediate Similarity	NPC51653
0.734	Intermediate Similarity	NPC313670
0.7333	Intermediate Similarity	NPC473390
0.7333	Intermediate Similarity	NPC11620
0.7333	Intermediate Similarity	NPC49208
0.7333	Intermediate Similarity	NPC474703
0.7333	Intermediate Similarity	NPC193198
0.7333	Intermediate Similarity	NPC170286
0.7333	Intermediate Similarity	NPC131669
0.7333	Intermediate Similarity	NPC69469
0.7333	Intermediate Similarity	NPC23748
0.7333	Intermediate Similarity	NPC44261

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 NPC474369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1245
0.2-0.3	3477
0.3-0.4	2679
0.4-0.5	1084
0.5-0.6	425
0.6-0.7	69
0.7-0.8	8
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
0.7742	Intermediate Similarity	NPD5778	Approved
0.7742	Intermediate Similarity	NPD5779	Approved
0.7609	Intermediate Similarity	NPD6101	Approved
0.7609	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6411	Approved
0.7412	Intermediate Similarity	NPD8039	Approved
0.7333	Intermediate Similarity	NPD7154	Phase 3
0.7333	Intermediate Similarity	NPD5362	Discontinued
0.732	Intermediate Similarity	NPD7839	Suspended
0.7263	Intermediate Similarity	NPD7983	Approved
0.7158	Intermediate Similarity	NPD46	Approved
0.7158	Intermediate Similarity	NPD6698	Approved
0.7097	Intermediate Similarity	NPD5786	Approved
0.7033	Intermediate Similarity	NPD4269	Approved
0.7033	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4270	Approved
0.7	Intermediate Similarity	NPD4821	Approved
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4822	Approved
0.7	Intermediate Similarity	NPD4819	Approved
0.7	Intermediate Similarity	NPD4820	Approved
0.7	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5785	Approved
0.6966	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5369	Approved
0.6869	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6435	Approved
0.6848	Remote Similarity	NPD5209	Approved
0.6813	Remote Similarity	NPD4252	Approved
0.6809	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD1694	Approved
0.6804	Remote Similarity	NPD7838	Discovery
0.6778	Remote Similarity	NPD4271	Approved
0.6778	Remote Similarity	NPD4268	Approved
0.6774	Remote Similarity	NPD5331	Approved
0.6774	Remote Similarity	NPD5332	Approved
0.6765	Remote Similarity	NPD6648	Approved
0.6747	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4790	Discontinued
0.6737	Remote Similarity	NPD6422	Discontinued
0.6735	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD4756	Discovery
0.6632	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5368	Approved
0.6606	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4249	Approved
0.6531	Remote Similarity	NPD1695	Approved
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
0.6505	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD6399	Phase 3
0.6495	Remote Similarity	NPD4250	Approved
0.6495	Remote Similarity	NPD4251	Approved
0.6463	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6436	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6053	Discontinued
0.6389	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD6371	Approved
0.6346	Remote Similarity	NPD7638	Approved
0.633	Remote Similarity	NPD6686	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD7115	Discovery
0.6279	Remote Similarity	NPD7331	Phase 2
0.6275	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD6695	Phase 3
0.6238	Remote Similarity	NPD5284	Approved
0.6238	Remote Similarity	NPD5693	Phase 1
0.6238	Remote Similarity	NPD5694	Approved
0.6238	Remote Similarity	NPD5281	Approved
0.6238	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7334	Approved
0.6224	Remote Similarity	NPD6684	Approved
0.6224	Remote Similarity	NPD6409	Approved
0.6224	Remote Similarity	NPD7146	Approved
0.6224	Remote Similarity	NPD5330	Approved
0.6224	Remote Similarity	NPD7521	Approved
0.6214	Remote Similarity	NPD5695	Phase 3
0.6204	Remote Similarity	NPD5909	Discontinued
0.62	Remote Similarity	NPD6051	Approved
0.62	Remote Similarity	NPD5370	Suspended
0.6186	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8273	Phase 1
0.6163	Remote Similarity	NPD7341	Phase 2
0.6146	Remote Similarity	NPD3667	Approved
0.6139	Remote Similarity	NPD5692	Phase 3
0.6139	Remote Similarity	NPD5207	Approved
0.6111	Remote Similarity	NPD6647	Phase 2
0.61	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD6672	Approved
0.61	Remote Similarity	NPD6903	Approved
0.6095	Remote Similarity	NPD6084	Phase 2
0.6095	Remote Similarity	NPD6083	Phase 2
0.6095	Remote Similarity	NPD7902	Approved
0.6091	Remote Similarity	NPD5697	Approved
0.6087	Remote Similarity	NPD8264	Approved
0.6078	Remote Similarity	NPD6050	Approved
0.6078	Remote Similarity	NPD7515	Phase 2
0.6064	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD4623	Approved
0.6061	Remote Similarity	NPD4519	Discontinued
0.6047	Remote Similarity	NPD3197	Phase 1
0.604	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5696	Approved
0.6036	Remote Similarity	NPD6011	Approved
0.6036	Remote Similarity	NPD6899	Approved
0.6036	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD8451	Approved
0.602	Remote Similarity	NPD3668	Phase 3
0.602	Remote Similarity	NPD4786	Approved
0.6018	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6	Remote Similarity	NPD368	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD4191	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5984	Remote Similarity	NPD8448	Approved
0.5982	Remote Similarity	NPD6014	Approved
0.5982	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD6013	Approved
0.598	Remote Similarity	NPD3673	Approved
0.598	Remote Similarity	NPD3672	Approved
0.5978	Remote Similarity	NPD6926	Approved
0.5978	Remote Similarity	NPD6924	Approved
0.5966	Remote Similarity	NPD8444	Approved
0.5962	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7900	Approved
0.596	Remote Similarity	NPD1696	Phase 3
0.595	Remote Similarity	NPD8299	Approved
0.595	Remote Similarity	NPD8340	Approved
0.595	Remote Similarity	NPD8341	Approved
0.595	Remote Similarity	NPD8342	Approved
0.5948	Remote Similarity	NPD2629	Approved
0.5946	Remote Similarity	NPD5701	Approved
0.5941	Remote Similarity	NPD4518	Approved
0.5938	Remote Similarity	NPD6931	Approved
0.5938	Remote Similarity	NPD7514	Phase 3
0.5938	Remote Similarity	NPD7332	Phase 2
0.5938	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4695	Discontinued
0.5938	Remote Similarity	NPD6930	Phase 2
0.5929	Remote Similarity	NPD7290	Approved
0.5929	Remote Similarity	NPD2067	Discontinued
0.5929	Remote Similarity	NPD6420	Discontinued
0.5929	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD7102	Approved
0.5926	Remote Similarity	NPD3196	Approved
0.5926	Remote Similarity	NPD4266	Approved
0.5926	Remote Similarity	NPD3194	Approved
0.5926	Remote Similarity	NPD3195	Phase 2
0.592	Remote Similarity	NPD7260	Phase 2
0.59	Remote Similarity	NPD6098	Approved
0.5893	Remote Similarity	NPD7320	Approved
0.5893	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6673	Approved
0.5882	Remote Similarity	NPD6904	Approved
0.5882	Remote Similarity	NPD6080	Approved
0.5877	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6650	Approved
0.5877	Remote Similarity	NPD8130	Phase 1
0.5877	Remote Similarity	NPD6847	Approved
0.5877	Remote Similarity	NPD6649	Approved
0.5877	Remote Similarity	NPD6869	Approved
0.5877	Remote Similarity	NPD6617	Approved
0.5872	Remote Similarity	NPD7632	Discontinued
0.5872	Remote Similarity	NPD5211	Phase 2
0.5868	Remote Similarity	NPD7830	Approved
0.5868	Remote Similarity	NPD7829	Approved
0.5859	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD3133	Approved
0.5859	Remote Similarity	NPD3666	Approved
0.5856	Remote Similarity	NPD5048	Discontinued
0.5856	Remote Similarity	NPD6008	Approved
0.5851	Remote Similarity	NPD6933	Approved
0.5849	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6372	Approved
0.5841	Remote Similarity	NPD6373	Approved
0.5841	Remote Similarity	NPD6413	Approved
0.584	Remote Similarity	NPD8390	Approved
0.584	Remote Similarity	NPD8392	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