NPASS Compound

Structure

CID106040 OpenBabel06191715452D 24 26 0 0 1 0 0 0 0 0999 V2000 3.2121 2.7908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8144 -3.1142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3329 -2.2802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1052 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0175 -1.6697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 -1.1883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7823 2.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 1.6426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7306 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0175 -2.6327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7823 -0.6487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 1.7006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7306 1.9568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3496 0.2562 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1835 -0.2253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3496 1.2192 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6190 0.7377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0175 0.2562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8514 -3.1142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 -0.1672 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8514 -0.2253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8514 -4.0771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0175 1.2192 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 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 10 2 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 12 1 6 0 0 0 17 20 1 1 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 20 4 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	3.499
LogD:	2.89
LogS:	-3.408
# Rotatable Bonds:	2
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.093
Fsp3:	0.65
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:	-4.451
MDCK Permeability:	2.613083961477969e-05
Pgp-inhibitor:	0.133
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.757

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.244
Plasma Protein Binding (PPB):	73.91880798339844%
Volume Distribution (VD):	0.582
Pgp-substrate:	20.252517700195312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.397
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.153
CYP2D6-substrate:	0.251
CYP3A4-inhibitor:	0.653
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	11.67
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.22
Human Hepatotoxicity (H-HT):	0.904
Drug-inuced Liver Injury (DILI):	0.256
AMES Toxicity:	0.294
Rat Oral Acute Toxicity:	0.758
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.831
Carcinogencity:	0.901
Eye Corrosion:	0.032
Eye Irritation:	0.109
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC106040

Natural Product ID:	NPC106040
*Common Name:**	YXTOBXGODMEKLL-PDXUZGLRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YXTOBXGODMEKLL-PDXUZGLRSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-13-7-8-17-20(4,24-17)11-9-14-15(6-5-10-19(2,3)22)18(21)23-12-16(13)14/h5-6,10,14,16-17,22H,1,7-9,11-12H2,2-4H3/b10-5+,15-6-/t14-,16+,17+,20+/m1/s1
SMILES:	C=C1CC[C@H]2[C@](C)(CC[C@@H]3/C(=C/C=C/C(C)(C)O)/C(=O)OC[C@@H]13)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516549
PubChem CID:	11631337
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
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	Green Island, Taiwan	2002-MAY	PMID[16180809]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23536	Alsophila spinulosa	Species	Cyatheaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18067	Muehlenbeckia platyclada	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26130	Cordia latifolia	Species	Cordiaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.6	ug ml-1	PMID[533932]
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.7	ug ml-1	PMID[533932]

☑ 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 NPC106040 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	194
0.1-0.2	1082
0.2-0.3	4173
0.3-0.4	9860
0.4-0.5	15465
0.5-0.6	7535
0.6-0.7	3992
0.7-0.8	372
0.8-0.85	10
0.85-0.9	7
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC115179
0.9529	High Similarity	NPC212598
0.9286	High Similarity	NPC474369
0.9277	High Similarity	NPC53867
0.9176	High Similarity	NPC234038
0.9176	High Similarity	NPC116575
0.9167	High Similarity	NPC196487
0.9167	High Similarity	NPC14575
0.9022	High Similarity	NPC475053
0.9	High Similarity	NPC272050
0.8989	High Similarity	NPC476049
0.8706	High Similarity	NPC475936
0.8523	High Similarity	NPC122502
0.8452	Intermediate Similarity	NPC474341
0.8372	Intermediate Similarity	NPC325031
0.8353	Intermediate Similarity	NPC469617
0.8333	Intermediate Similarity	NPC107668
0.8315	Intermediate Similarity	NPC198314
0.8313	Intermediate Similarity	NPC475861
0.8295	Intermediate Similarity	NPC72464
0.8222	Intermediate Similarity	NPC474765
0.8202	Intermediate Similarity	NPC474547
0.8191	Intermediate Similarity	NPC107476
0.8182	Intermediate Similarity	NPC170377
0.8182	Intermediate Similarity	NPC475842
0.809	Intermediate Similarity	NPC70424
0.809	Intermediate Similarity	NPC243618
0.8068	Intermediate Similarity	NPC85772
0.8068	Intermediate Similarity	NPC145963
0.8046	Intermediate Similarity	NPC474510
0.8043	Intermediate Similarity	NPC83423
0.8	Intermediate Similarity	NPC261380
0.8	Intermediate Similarity	NPC12740
0.8	Intermediate Similarity	NPC110461
0.7955	Intermediate Similarity	NPC42470
0.7955	Intermediate Similarity	NPC141810
0.7912	Intermediate Similarity	NPC315395
0.7912	Intermediate Similarity	NPC316426
0.79	Intermediate Similarity	NPC309190
0.7895	Intermediate Similarity	NPC38830
0.7889	Intermediate Similarity	NPC9868
0.7872	Intermediate Similarity	NPC111114
0.7872	Intermediate Similarity	NPC300312
0.7872	Intermediate Similarity	NPC261607
0.7857	Intermediate Similarity	NPC135703
0.7841	Intermediate Similarity	NPC233377
0.7826	Intermediate Similarity	NPC160138
0.7826	Intermediate Similarity	NPC475703
0.7826	Intermediate Similarity	NPC72513
0.7816	Intermediate Similarity	NPC267231
0.7816	Intermediate Similarity	NPC108816
0.7816	Intermediate Similarity	NPC93763
0.7791	Intermediate Similarity	NPC61863
0.7791	Intermediate Similarity	NPC271070
0.7789	Intermediate Similarity	NPC125674
0.7789	Intermediate Similarity	NPC228451
0.7789	Intermediate Similarity	NPC475838
0.7778	Intermediate Similarity	NPC16488
0.7778	Intermediate Similarity	NPC250315
0.7778	Intermediate Similarity	NPC475989
0.7766	Intermediate Similarity	NPC62815
0.7766	Intermediate Similarity	NPC473448
0.7755	Intermediate Similarity	NPC64742
0.7753	Intermediate Similarity	NPC475481
0.7753	Intermediate Similarity	NPC79277
0.7732	Intermediate Similarity	NPC9812
0.7727	Intermediate Similarity	NPC617
0.7727	Intermediate Similarity	NPC471537
0.7717	Intermediate Similarity	NPC164393
0.7717	Intermediate Similarity	NPC475461
0.7717	Intermediate Similarity	NPC305475
0.7708	Intermediate Similarity	NPC474247
0.7708	Intermediate Similarity	NPC81386
0.7708	Intermediate Similarity	NPC475572
0.7708	Intermediate Similarity	NPC474035
0.7701	Intermediate Similarity	NPC316324
0.7692	Intermediate Similarity	NPC474776
0.7692	Intermediate Similarity	NPC82297
0.7684	Intermediate Similarity	NPC45579
0.7684	Intermediate Similarity	NPC219874
0.7684	Intermediate Similarity	NPC303697
0.7667	Intermediate Similarity	NPC35556
0.7667	Intermediate Similarity	NPC474291
0.766	Intermediate Similarity	NPC284561
0.766	Intermediate Similarity	NPC295312
0.766	Intermediate Similarity	NPC166919
0.7634	Intermediate Similarity	NPC475678
0.7634	Intermediate Similarity	NPC312561
0.7634	Intermediate Similarity	NPC231889
0.7634	Intermediate Similarity	NPC86005
0.7629	Intermediate Similarity	NPC209355
0.7629	Intermediate Similarity	NPC270013
0.7629	Intermediate Similarity	NPC14961
0.7629	Intermediate Similarity	NPC304886
0.7619	Intermediate Similarity	NPC475310
0.7614	Intermediate Similarity	NPC128276
0.7609	Intermediate Similarity	NPC99395
0.7609	Intermediate Similarity	NPC197903
0.7609	Intermediate Similarity	NPC137033
0.7609	Intermediate Similarity	NPC215364
0.7609	Intermediate Similarity	NPC255307
0.76	Intermediate Similarity	NPC206079
0.76	Intermediate Similarity	NPC116139
0.7582	Intermediate Similarity	NPC44261
0.7582	Intermediate Similarity	NPC272814
0.7579	Intermediate Similarity	NPC475855
0.7579	Intermediate Similarity	NPC469372
0.7579	Intermediate Similarity	NPC281942
0.7579	Intermediate Similarity	NPC179394
0.7579	Intermediate Similarity	NPC474761
0.7579	Intermediate Similarity	NPC476004
0.7579	Intermediate Similarity	NPC232426
0.7579	Intermediate Similarity	NPC77337
0.7579	Intermediate Similarity	NPC144133
0.7579	Intermediate Similarity	NPC469368
0.7576	Intermediate Similarity	NPC244411
0.7576	Intermediate Similarity	NPC316598
0.7558	Intermediate Similarity	NPC476355
0.7556	Intermediate Similarity	NPC471325
0.7556	Intermediate Similarity	NPC112868
0.7553	Intermediate Similarity	NPC475902
0.7553	Intermediate Similarity	NPC473658
0.7553	Intermediate Similarity	NPC153805
0.7553	Intermediate Similarity	NPC26078
0.7553	Intermediate Similarity	NPC474471
0.7553	Intermediate Similarity	NPC227379
0.7553	Intermediate Similarity	NPC281516
0.7551	Intermediate Similarity	NPC476315
0.7551	Intermediate Similarity	NPC279621
0.7551	Intermediate Similarity	NPC473291
0.7551	Intermediate Similarity	NPC230800
0.7528	Intermediate Similarity	NPC264227
0.7528	Intermediate Similarity	NPC178277
0.7528	Intermediate Similarity	NPC63649
0.7528	Intermediate Similarity	NPC472965
0.7527	Intermediate Similarity	NPC284902
0.7527	Intermediate Similarity	NPC474045
0.7527	Intermediate Similarity	NPC261253
0.7527	Intermediate Similarity	NPC261721
0.7527	Intermediate Similarity	NPC50637
0.7526	Intermediate Similarity	NPC477129
0.7526	Intermediate Similarity	NPC477130
0.7526	Intermediate Similarity	NPC167219
0.7526	Intermediate Similarity	NPC474338
0.7525	Intermediate Similarity	NPC66110
0.7525	Intermediate Similarity	NPC473596
0.75	Intermediate Similarity	NPC320630
0.75	Intermediate Similarity	NPC476794
0.75	Intermediate Similarity	NPC470373
0.75	Intermediate Similarity	NPC187568
0.75	Intermediate Similarity	NPC116177
0.75	Intermediate Similarity	NPC141831
0.75	Intermediate Similarity	NPC476804
0.75	Intermediate Similarity	NPC114979
0.75	Intermediate Similarity	NPC41780
0.75	Intermediate Similarity	NPC470240
0.75	Intermediate Similarity	NPC7563
0.75	Intermediate Similarity	NPC191476
0.75	Intermediate Similarity	NPC57744
0.75	Intermediate Similarity	NPC472705
0.75	Intermediate Similarity	NPC288876
0.75	Intermediate Similarity	NPC295799
0.75	Intermediate Similarity	NPC470379
0.75	Intermediate Similarity	NPC151481
0.75	Intermediate Similarity	NPC315394
0.7475	Intermediate Similarity	NPC208094
0.7475	Intermediate Similarity	NPC202705
0.7475	Intermediate Similarity	NPC40812
0.7475	Intermediate Similarity	NPC474343
0.7474	Intermediate Similarity	NPC307092
0.7474	Intermediate Similarity	NPC51358
0.7474	Intermediate Similarity	NPC36668
0.7474	Intermediate Similarity	NPC268298
0.7474	Intermediate Similarity	NPC118011
0.7473	Intermediate Similarity	NPC471326
0.7473	Intermediate Similarity	NPC471159
0.7473	Intermediate Similarity	NPC221231
0.7473	Intermediate Similarity	NPC123880
0.7473	Intermediate Similarity	NPC173609
0.7471	Intermediate Similarity	NPC329852
0.7471	Intermediate Similarity	NPC244166
0.7451	Intermediate Similarity	NPC473624
0.7449	Intermediate Similarity	NPC295347
0.7449	Intermediate Similarity	NPC474947
0.7447	Intermediate Similarity	NPC471738
0.7447	Intermediate Similarity	NPC316138
0.7447	Intermediate Similarity	NPC313658
0.7444	Intermediate Similarity	NPC103634
0.7426	Intermediate Similarity	NPC469851
0.7426	Intermediate Similarity	NPC244456
0.7426	Intermediate Similarity	NPC469657
0.7426	Intermediate Similarity	NPC62670
0.7426	Intermediate Similarity	NPC146822
0.7423	Intermediate Similarity	NPC475912
0.7423	Intermediate Similarity	NPC212486
0.7419	Intermediate Similarity	NPC125290
0.7419	Intermediate Similarity	NPC28887
0.7419	Intermediate Similarity	NPC96621
0.7419	Intermediate Similarity	NPC165162
0.7419	Intermediate Similarity	NPC65661

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 NPC106040 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1334
0.2-0.3	3481
0.3-0.4	2682
0.4-0.5	1050
0.5-0.6	369
0.6-0.7	57
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
0.7579	Intermediate Similarity	NPD6698	Approved
0.7579	Intermediate Similarity	NPD46	Approved
0.7423	Intermediate Similarity	NPD5778	Approved
0.7423	Intermediate Similarity	NPD5779	Approved
0.7396	Intermediate Similarity	NPD7838	Discovery
0.7327	Intermediate Similarity	NPD6648	Approved
0.7292	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6101	Approved
0.7283	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5209	Approved
0.7229	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD6411	Approved
0.71	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8039	Approved
0.7053	Intermediate Similarity	NPD1694	Approved
0.7053	Intermediate Similarity	NPD5363	Approved
0.7053	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7839	Suspended
0.7021	Intermediate Similarity	NPD5362	Discontinued
0.7021	Intermediate Similarity	NPD7154	Phase 3
0.697	Remote Similarity	NPD7983	Approved
0.6939	Remote Similarity	NPD1695	Approved
0.6923	Remote Similarity	NPD4756	Discovery
0.6923	Remote Similarity	NPD5344	Discontinued
0.6814	Remote Similarity	NPD7115	Discovery
0.6804	Remote Similarity	NPD5786	Approved
0.6737	Remote Similarity	NPD4270	Approved
0.6737	Remote Similarity	NPD4269	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6727	Remote Similarity	NPD6371	Approved
0.6702	Remote Similarity	NPD4820	Approved
0.6702	Remote Similarity	NPD4821	Approved
0.6702	Remote Similarity	NPD4819	Approved
0.6702	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5369	Approved
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3573	Approved
0.6562	Remote Similarity	NPD6435	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6526	Remote Similarity	NPD4252	Approved
0.6509	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD7640	Approved
0.6505	Remote Similarity	NPD5282	Discontinued
0.6495	Remote Similarity	NPD5331	Approved
0.6495	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD4271	Approved
0.6489	Remote Similarity	NPD4268	Approved
0.6471	Remote Similarity	NPD7637	Suspended
0.6465	Remote Similarity	NPD6422	Discontinued
0.646	Remote Similarity	NPD6053	Discontinued
0.6458	Remote Similarity	NPD4790	Discontinued
0.6415	Remote Similarity	NPD7638	Approved
0.6372	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1696	Phase 3
0.6364	Remote Similarity	NPD7331	Phase 2
0.6354	Remote Similarity	NPD5368	Approved
0.6346	Remote Similarity	NPD7748	Approved
0.6333	Remote Similarity	NPD7829	Approved
0.6333	Remote Similarity	NPD7830	Approved
0.633	Remote Similarity	NPD6647	Phase 2
0.6311	Remote Similarity	NPD5284	Approved
0.6311	Remote Similarity	NPD5281	Approved
0.6311	Remote Similarity	NPD5694	Approved
0.6311	Remote Similarity	NPD5693	Phase 1
0.6306	Remote Similarity	NPD5697	Approved
0.6303	Remote Similarity	NPD8517	Approved
0.6303	Remote Similarity	NPD8515	Approved
0.6303	Remote Similarity	NPD8513	Phase 3
0.6303	Remote Similarity	NPD8516	Approved
0.63	Remote Similarity	NPD6409	Approved
0.63	Remote Similarity	NPD4249	Approved
0.63	Remote Similarity	NPD7334	Approved
0.63	Remote Similarity	NPD7521	Approved
0.63	Remote Similarity	NPD7146	Approved
0.63	Remote Similarity	NPD5330	Approved
0.63	Remote Similarity	NPD6684	Approved
0.6292	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5695	Phase 3
0.6273	Remote Similarity	NPD5909	Discontinued
0.6263	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD6899	Approved
0.6238	Remote Similarity	NPD4250	Approved
0.6238	Remote Similarity	NPD4251	Approved
0.623	Remote Similarity	NPD8273	Phase 1
0.6228	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6008	Approved
0.6214	Remote Similarity	NPD5692	Phase 3
0.6214	Remote Similarity	NPD5207	Approved
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.6186	Remote Similarity	NPD4695	Discontinued
0.6176	Remote Similarity	NPD6672	Approved
0.6176	Remote Similarity	NPD5737	Approved
0.6176	Remote Similarity	NPD6903	Approved
0.6176	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6083	Phase 2
0.6168	Remote Similarity	NPD7902	Approved
0.6168	Remote Similarity	NPD6084	Phase 2
0.6163	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6050	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD4623	Approved
0.6139	Remote Similarity	NPD4519	Discontinued
0.6139	Remote Similarity	NPD5279	Phase 3
0.6136	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7260	Phase 2
0.6111	Remote Similarity	NPD5696	Approved
0.6092	Remote Similarity	NPD4191	Approved
0.6092	Remote Similarity	NPD4194	Approved
0.6092	Remote Similarity	NPD4193	Approved
0.6092	Remote Similarity	NPD4192	Approved
0.6091	Remote Similarity	NPD5211	Phase 2
0.6087	Remote Similarity	NPD6650	Approved
0.6087	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6087	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7128	Approved
0.6071	Remote Similarity	NPD5739	Approved
0.6071	Remote Similarity	NPD6402	Approved
0.6071	Remote Similarity	NPD6675	Approved
0.6066	Remote Similarity	NPD7642	Approved
0.6048	Remote Similarity	NPD8074	Phase 3
0.6038	Remote Similarity	NPD7900	Approved
0.6038	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6882	Approved
0.6034	Remote Similarity	NPD8297	Approved
0.602	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4518	Approved
0.6018	Remote Similarity	NPD5701	Approved
0.6018	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD2067	Discontinued
0.5982	Remote Similarity	NPD5141	Approved
0.5981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7500	Approved
0.5965	Remote Similarity	NPD7320	Approved
0.5962	Remote Similarity	NPD6673	Approved
0.5962	Remote Similarity	NPD6051	Approved
0.5962	Remote Similarity	NPD5370	Suspended
0.5962	Remote Similarity	NPD6904	Approved
0.5962	Remote Similarity	NPD6080	Approved
0.5946	Remote Similarity	NPD7632	Discontinued
0.5941	Remote Similarity	NPD3133	Approved
0.5941	Remote Similarity	NPD3665	Phase 1
0.5941	Remote Similarity	NPD3666	Approved
0.5941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5222	Approved
0.5926	Remote Similarity	NPD5221	Approved
0.5917	Remote Similarity	NPD7641	Discontinued
0.5913	Remote Similarity	NPD6373	Approved
0.5913	Remote Similarity	NPD6372	Approved
0.5913	Remote Similarity	NPD2182	Approved
0.5909	Remote Similarity	NPD6404	Discontinued
0.5909	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD5286	Approved
0.5909	Remote Similarity	NPD5285	Approved
0.5902	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3667	Approved
0.5888	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5173	Approved
0.5872	Remote Similarity	NPD5959	Approved
0.5865	Remote Similarity	NPD5208	Approved
0.5856	Remote Similarity	NPD5223	Approved
0.5847	Remote Similarity	NPD4632	Approved
0.5843	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6110	Phase 1
0.584	Remote Similarity	NPD7507	Approved
0.584	Remote Similarity	NPD8451	Approved
0.584	Remote Similarity	NPD6637	Approved
0.5833	Remote Similarity	NPD6317	Approved
0.5833	Remote Similarity	NPD8264	Approved
0.5833	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD4629	Approved
0.5833	Remote Similarity	NPD7505	Discontinued
0.5833	Remote Similarity	NPD5210	Approved
0.5825	Remote Similarity	NPD5690	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data