NPASS Compound

Structure

CID196487 OpenBabel06191715582D 23 24 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 2.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -3.8660 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 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5677 -0.5000 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 -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 -2.3748 -1.7660 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 -0.8660 0.5000 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 -1.7321 -1.0000 0.0000 C 0 0 2 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 0.0000 0.0000 C 0 0 1 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 1.7321 -3.0000 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 2.5981 -2.5000 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 14 1 0 0 0 0 2 15 2 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 15 18 1 0 0 0 0 16 11 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 13 1 6 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	350.552
LogP:	4.118
LogD:	3.565
LogS:	-4.373
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	4.703
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.535
MDCK Permeability:	2.909245631599333e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.303
Plasma Protein Binding (PPB):	89.1784439086914%
Volume Distribution (VD):	0.524
Pgp-substrate:	7.725088119506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.667
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.615
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.468
CYP2C9-substrate:	0.355
CYP2D6-inhibitor:	0.752
CYP2D6-substrate:	0.396
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	7.299
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.283
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.928
Carcinogencity:	0.788
Eye Corrosion:	0.018
Eye Irritation:	0.172
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC196487

Natural Product ID:	NPC196487
*Common Name:**	9-Deoxy-Isoxeniolide-A
IUPAC Name:	(4Z,4aS,7E,11aR)-4-[(E)-4-hydroxy-4-methylpent-2-enylidene]-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydro-1H-cyclonona[c]pyran-3-one
Synonyms:
Standard InCHIKey:	PGYRSUFCGXKLPM-NRTVDCPFSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-14-7-5-8-15(2)18-13-23-19(21)17(16(18)11-10-14)9-6-12-20(3,4)22/h6-7,9,12,16,18,22H,2,5,8,10-11,13H2,1,3-4H3/b12-6+,14-7+,17-9-/t16-,18+/m1/s1
SMILES:	C/C/1=CCCC(=C)[C@@H]2COC(=O)/C(=CC=CC(C)(C)O)/[C@H]2CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462887
PubChem CID:	11507961
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	=	8.7	ug ml-1	PMID[554487]
NPT168	Cell Line	P388	Mus musculus	ED50	>	20.0	ug ml-1	PMID[554487]

☑ 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 NPC196487 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	167
0.1-0.2	935
0.2-0.3	4011
0.3-0.4	9640
0.4-0.5	15444
0.5-0.6	7829
0.6-0.7	4072
0.7-0.8	568
0.8-0.85	14
0.85-0.9	12
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC14575
0.975	High Similarity	NPC234038
0.9167	High Similarity	NPC106040
0.9167	High Similarity	NPC115179
0.9167	High Similarity	NPC212598
0.9103	High Similarity	NPC107668
0.907	High Similarity	NPC476049
0.8916	High Similarity	NPC474369
0.881	High Similarity	NPC116575
0.8734	High Similarity	NPC110461
0.8734	High Similarity	NPC12740
0.8652	High Similarity	NPC272050
0.8642	High Similarity	NPC469617
0.859	High Similarity	NPC135703
0.8588	High Similarity	NPC198314
0.8519	High Similarity	NPC474341
0.85	High Similarity	NPC61863
0.8452	Intermediate Similarity	NPC53867
0.8434	Intermediate Similarity	NPC325031
0.828	Intermediate Similarity	NPC475053
0.8161	Intermediate Similarity	NPC122502
0.814	Intermediate Similarity	NPC70424
0.814	Intermediate Similarity	NPC243618
0.8118	Intermediate Similarity	NPC85772
0.8095	Intermediate Similarity	NPC233377
0.8072	Intermediate Similarity	NPC267231
0.7955	Intermediate Similarity	NPC315395
0.7955	Intermediate Similarity	NPC316426
0.7952	Intermediate Similarity	NPC316324
0.7931	Intermediate Similarity	NPC474776
0.7907	Intermediate Similarity	NPC475936
0.7865	Intermediate Similarity	NPC475678
0.7857	Intermediate Similarity	NPC108816
0.7857	Intermediate Similarity	NPC93763
0.7841	Intermediate Similarity	NPC261380
0.7816	Intermediate Similarity	NPC250315
0.7816	Intermediate Similarity	NPC170377
0.7816	Intermediate Similarity	NPC16488
0.7791	Intermediate Similarity	NPC42470
0.7789	Intermediate Similarity	NPC64742
0.7778	Intermediate Similarity	NPC26078
0.7778	Intermediate Similarity	NPC473658
0.7766	Intermediate Similarity	NPC9812
0.7765	Intermediate Similarity	NPC63649
0.7765	Intermediate Similarity	NPC264227
0.7765	Intermediate Similarity	NPC472965
0.7755	Intermediate Similarity	NPC309190
0.7753	Intermediate Similarity	NPC164393
0.7738	Intermediate Similarity	NPC7563
0.7738	Intermediate Similarity	NPC41780
0.7738	Intermediate Similarity	NPC116177
0.7738	Intermediate Similarity	NPC180290
0.7738	Intermediate Similarity	NPC187568
0.7738	Intermediate Similarity	NPC320630
0.7727	Intermediate Similarity	NPC9868
0.7727	Intermediate Similarity	NPC72464
0.7717	Intermediate Similarity	NPC261607
0.7717	Intermediate Similarity	NPC219874
0.7717	Intermediate Similarity	NPC300312
0.7717	Intermediate Similarity	NPC472705
0.7717	Intermediate Similarity	NPC303697
0.7717	Intermediate Similarity	NPC111114
0.7717	Intermediate Similarity	NPC45579
0.7711	Intermediate Similarity	NPC329852
0.7711	Intermediate Similarity	NPC475861
0.7701	Intermediate Similarity	NPC471326
0.7701	Intermediate Similarity	NPC474291
0.7701	Intermediate Similarity	NPC221231
0.7692	Intermediate Similarity	NPC83423
0.7692	Intermediate Similarity	NPC284561
0.7692	Intermediate Similarity	NPC307092
0.7692	Intermediate Similarity	NPC51358
0.7674	Intermediate Similarity	NPC474510
0.7667	Intermediate Similarity	NPC86005
0.7667	Intermediate Similarity	NPC160138
0.7667	Intermediate Similarity	NPC312561
0.766	Intermediate Similarity	NPC209355
0.7654	Intermediate Similarity	NPC316029
0.7647	Intermediate Similarity	NPC4436
0.7647	Intermediate Similarity	NPC128276
0.7647	Intermediate Similarity	NPC471220
0.764	Intermediate Similarity	NPC474547
0.764	Intermediate Similarity	NPC197903
0.764	Intermediate Similarity	NPC99395
0.7629	Intermediate Similarity	NPC116139
0.7629	Intermediate Similarity	NPC206079
0.7614	Intermediate Similarity	NPC52609
0.7614	Intermediate Similarity	NPC1761
0.7609	Intermediate Similarity	NPC473448
0.7609	Intermediate Similarity	NPC77337
0.7604	Intermediate Similarity	NPC244411
0.7595	Intermediate Similarity	NPC308294
0.7595	Intermediate Similarity	NPC142423
0.759	Intermediate Similarity	NPC476355
0.7586	Intermediate Similarity	NPC471325
0.7561	Intermediate Similarity	NPC163003
0.7561	Intermediate Similarity	NPC288667
0.7558	Intermediate Similarity	NPC178277
0.7556	Intermediate Similarity	NPC475461
0.7556	Intermediate Similarity	NPC305475
0.7553	Intermediate Similarity	NPC475572
0.7551	Intermediate Similarity	NPC66110
0.7531	Intermediate Similarity	NPC265574
0.7531	Intermediate Similarity	NPC151481
0.7529	Intermediate Similarity	NPC315394
0.7529	Intermediate Similarity	NPC57744
0.7528	Intermediate Similarity	NPC149869
0.7528	Intermediate Similarity	NPC476804
0.7528	Intermediate Similarity	NPC82297
0.75	Intermediate Similarity	NPC228978
0.75	Intermediate Similarity	NPC295312
0.75	Intermediate Similarity	NPC68624
0.75	Intermediate Similarity	NPC145963
0.75	Intermediate Similarity	NPC118011
0.75	Intermediate Similarity	NPC36668
0.75	Intermediate Similarity	NPC173609
0.75	Intermediate Similarity	NPC94200
0.75	Intermediate Similarity	NPC244166
0.75	Intermediate Similarity	NPC208094
0.7474	Intermediate Similarity	NPC295347
0.7474	Intermediate Similarity	NPC304886
0.7474	Intermediate Similarity	NPC107476
0.7473	Intermediate Similarity	NPC313658
0.7473	Intermediate Similarity	NPC72513
0.7473	Intermediate Similarity	NPC316138
0.7473	Intermediate Similarity	NPC474765
0.7471	Intermediate Similarity	NPC190008
0.7471	Intermediate Similarity	NPC47747
0.7449	Intermediate Similarity	NPC469851
0.7449	Intermediate Similarity	NPC62670
0.7444	Intermediate Similarity	NPC86316
0.7444	Intermediate Similarity	NPC215364
0.7444	Intermediate Similarity	NPC106416
0.7444	Intermediate Similarity	NPC470177
0.7444	Intermediate Similarity	NPC125290
0.7444	Intermediate Similarity	NPC28887
0.7444	Intermediate Similarity	NPC137033
0.7444	Intermediate Similarity	NPC65661
0.7444	Intermediate Similarity	NPC255307
0.7442	Intermediate Similarity	NPC63445
0.7442	Intermediate Similarity	NPC222210
0.7442	Intermediate Similarity	NPC192006
0.7442	Intermediate Similarity	NPC169095
0.7442	Intermediate Similarity	NPC471465
0.7442	Intermediate Similarity	NPC196653
0.7439	Intermediate Similarity	NPC475310
0.7439	Intermediate Similarity	NPC67183
0.7423	Intermediate Similarity	NPC316598
0.7419	Intermediate Similarity	NPC182136
0.7419	Intermediate Similarity	NPC232426
0.7419	Intermediate Similarity	NPC469372
0.7419	Intermediate Similarity	NPC475855
0.7419	Intermediate Similarity	NPC281942
0.7419	Intermediate Similarity	NPC179394
0.7419	Intermediate Similarity	NPC474761
0.7419	Intermediate Similarity	NPC144133
0.7419	Intermediate Similarity	NPC476004
0.7416	Intermediate Similarity	NPC40746
0.7416	Intermediate Similarity	NPC475842
0.7416	Intermediate Similarity	NPC193198
0.7416	Intermediate Similarity	NPC39588
0.7416	Intermediate Similarity	NPC118423
0.7416	Intermediate Similarity	NPC44261
0.7416	Intermediate Similarity	NPC169575
0.7412	Intermediate Similarity	NPC266159
0.7412	Intermediate Similarity	NPC472967
0.7412	Intermediate Similarity	NPC235906
0.7412	Intermediate Similarity	NPC271070
0.7412	Intermediate Similarity	NPC123360
0.7412	Intermediate Similarity	NPC473223
0.7412	Intermediate Similarity	NPC40353
0.7407	Intermediate Similarity	NPC218477
0.7407	Intermediate Similarity	NPC313444
0.7391	Intermediate Similarity	NPC227379
0.7391	Intermediate Similarity	NPC474471
0.7391	Intermediate Similarity	NPC153805
0.7391	Intermediate Similarity	NPC476805
0.7386	Intermediate Similarity	NPC475481
0.7386	Intermediate Similarity	NPC141810
0.7386	Intermediate Similarity	NPC112868
0.7386	Intermediate Similarity	NPC315731
0.7386	Intermediate Similarity	NPC79277
0.7381	Intermediate Similarity	NPC140287
0.7381	Intermediate Similarity	NPC474758
0.7374	Intermediate Similarity	NPC473596
0.7368	Intermediate Similarity	NPC477129
0.7368	Intermediate Similarity	NPC167219
0.7368	Intermediate Similarity	NPC476415
0.7368	Intermediate Similarity	NPC477130
0.7368	Intermediate Similarity	NPC38830
0.7368	Intermediate Similarity	NPC474338
0.7363	Intermediate Similarity	NPC261721
0.7363	Intermediate Similarity	NPC220478
0.7363	Intermediate Similarity	NPC284902
0.7356	Intermediate Similarity	NPC617
0.7356	Intermediate Similarity	NPC89128
0.7356	Intermediate Similarity	NPC471537
0.7356	Intermediate Similarity	NPC470239
0.7356	Intermediate Similarity	NPC469690
0.7356	Intermediate Similarity	NPC470244

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 NPC196487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1198
0.2-0.3	3396
0.3-0.4	2767
0.4-0.5	1113
0.5-0.6	416
0.6-0.7	93
0.7-0.8	12
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
0.75	Intermediate Similarity	NPD8039	Approved
0.7303	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5779	Approved
0.7263	Intermediate Similarity	NPD5778	Approved
0.7245	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5785	Approved
0.7234	Intermediate Similarity	NPD46	Approved
0.7234	Intermediate Similarity	NPD6698	Approved
0.7128	Intermediate Similarity	NPD6101	Approved
0.7128	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4756	Discovery
0.7111	Intermediate Similarity	NPD5209	Approved
0.7065	Intermediate Similarity	NPD5363	Approved
0.7065	Intermediate Similarity	NPD1694	Approved
0.7041	Intermediate Similarity	NPD7839	Suspended
0.7037	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5362	Discontinued
0.7033	Intermediate Similarity	NPD7154	Phase 3
0.6979	Remote Similarity	NPD6411	Approved
0.6979	Remote Similarity	NPD7983	Approved
0.6939	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7838	Discovery
0.6832	Remote Similarity	NPD6648	Approved
0.6809	Remote Similarity	NPD5786	Approved
0.6747	Remote Similarity	NPD7331	Phase 2
0.6739	Remote Similarity	NPD4269	Approved
0.6739	Remote Similarity	NPD4270	Approved
0.6737	Remote Similarity	NPD3573	Approved
0.6703	Remote Similarity	NPD4820	Approved
0.6703	Remote Similarity	NPD4821	Approved
0.6703	Remote Similarity	NPD4822	Approved
0.6703	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5369	Approved
0.6598	Remote Similarity	NPD1695	Approved
0.6571	Remote Similarity	NPD5909	Discontinued
0.6569	Remote Similarity	NPD4225	Approved
0.6559	Remote Similarity	NPD6435	Approved
0.6526	Remote Similarity	NPD1696	Phase 3
0.6522	Remote Similarity	NPD4252	Approved
0.6506	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD5331	Approved
0.6484	Remote Similarity	NPD4271	Approved
0.6484	Remote Similarity	NPD4268	Approved
0.6465	Remote Similarity	NPD7637	Suspended
0.6463	Remote Similarity	NPD4192	Approved
0.6463	Remote Similarity	NPD4193	Approved
0.6463	Remote Similarity	NPD4191	Approved
0.6463	Remote Similarity	NPD4194	Approved
0.6458	Remote Similarity	NPD6422	Discontinued
0.6452	Remote Similarity	NPD4790	Discontinued
0.6449	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5344	Discontinued
0.6429	Remote Similarity	NPD7341	Phase 2
0.6422	Remote Similarity	NPD6371	Approved
0.6389	Remote Similarity	NPD6686	Approved
0.6372	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD5207	Approved
0.6354	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6344	Remote Similarity	NPD5368	Approved
0.6341	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5282	Discontinued
0.6321	Remote Similarity	NPD6647	Phase 2
0.6306	Remote Similarity	NPD6053	Discontinued
0.63	Remote Similarity	NPD5693	Phase 1
0.63	Remote Similarity	NPD5284	Approved
0.63	Remote Similarity	NPD5694	Approved
0.63	Remote Similarity	NPD5281	Approved
0.6293	Remote Similarity	NPD8515	Approved
0.6293	Remote Similarity	NPD8516	Approved
0.6293	Remote Similarity	NPD8517	Approved
0.6293	Remote Similarity	NPD8513	Phase 3
0.6289	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD7334	Approved
0.6289	Remote Similarity	NPD6684	Approved
0.6289	Remote Similarity	NPD7146	Approved
0.6289	Remote Similarity	NPD7521	Approved
0.6289	Remote Similarity	NPD5330	Approved
0.6289	Remote Similarity	NPD4249	Approved
0.6289	Remote Similarity	NPD4519	Discontinued
0.6289	Remote Similarity	NPD4623	Approved
0.6279	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4250	Approved
0.6224	Remote Similarity	NPD4251	Approved
0.6216	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5692	Phase 3
0.6176	Remote Similarity	NPD7748	Approved
0.617	Remote Similarity	NPD4695	Discontinued
0.6163	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6672	Approved
0.6162	Remote Similarity	NPD4518	Approved
0.6162	Remote Similarity	NPD5737	Approved
0.6162	Remote Similarity	NPD6903	Approved
0.6162	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD6084	Phase 2
0.6147	Remote Similarity	NPD5697	Approved
0.6139	Remote Similarity	NPD6050	Approved
0.6122	Remote Similarity	NPD5279	Phase 3
0.61	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5696	Approved
0.6091	Remote Similarity	NPD6881	Approved
0.6091	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD6399	Phase 3
0.6076	Remote Similarity	NPD3172	Approved
0.605	Remote Similarity	NPD7830	Approved
0.605	Remote Similarity	NPD7829	Approved
0.604	Remote Similarity	NPD3673	Approved
0.604	Remote Similarity	NPD3672	Approved
0.6038	Remote Similarity	NPD6404	Discontinued
0.6038	Remote Similarity	NPD2066	Phase 3
0.6036	Remote Similarity	NPD6012	Approved
0.6036	Remote Similarity	NPD6014	Approved
0.6036	Remote Similarity	NPD2182	Approved
0.6036	Remote Similarity	NPD6013	Approved
0.6033	Remote Similarity	NPD8074	Phase 3
0.6019	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3194	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD3196	Approved
0.6	Remote Similarity	NPD3195	Phase 2
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4266	Approved
0.5982	Remote Similarity	NPD7102	Approved
0.5982	Remote Similarity	NPD7290	Approved
0.5982	Remote Similarity	NPD6883	Approved
0.5982	Remote Similarity	NPD2067	Discontinued
0.598	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6079	Approved
0.598	Remote Similarity	NPD7515	Phase 2
0.5978	Remote Similarity	NPD8264	Approved
0.5968	Remote Similarity	NPD7260	Phase 2
0.596	Remote Similarity	NPD5280	Approved
0.596	Remote Similarity	NPD4694	Approved
0.596	Remote Similarity	NPD5690	Phase 2
0.5957	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7500	Approved
0.5941	Remote Similarity	NPD6904	Approved
0.5941	Remote Similarity	NPD6080	Approved
0.5941	Remote Similarity	NPD6673	Approved
0.5941	Remote Similarity	NPD5370	Suspended
0.593	Remote Similarity	NPD3197	Phase 1
0.5929	Remote Similarity	NPD6617	Approved
0.5929	Remote Similarity	NPD6847	Approved
0.5929	Remote Similarity	NPD8130	Phase 1
0.5929	Remote Similarity	NPD6649	Approved
0.5929	Remote Similarity	NPD6869	Approved
0.5929	Remote Similarity	NPD6650	Approved
0.5926	Remote Similarity	NPD5211	Phase 2
0.5918	Remote Similarity	NPD3665	Phase 1
0.5918	Remote Similarity	NPD3666	Approved
0.5918	Remote Similarity	NPD3133	Approved
0.5909	Remote Similarity	NPD5739	Approved
0.5909	Remote Similarity	NPD7128	Approved
0.5909	Remote Similarity	NPD6402	Approved
0.5909	Remote Similarity	NPD6675	Approved
0.5897	Remote Similarity	NPD7641	Discontinued
0.5882	Remote Similarity	NPD368	Approved
0.5882	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD8297	Approved
0.5877	Remote Similarity	NPD6882	Approved
0.5876	Remote Similarity	NPD3667	Approved
0.5876	Remote Similarity	NPD4223	Phase 3
0.5876	Remote Similarity	NPD4221	Approved
0.587	Remote Similarity	NPD4058	Approved
0.5865	Remote Similarity	NPD7900	Approved
0.5865	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5701	Approved
0.5833	Remote Similarity	NPD7514	Phase 3
0.5833	Remote Similarity	NPD7332	Phase 2
0.5823	Remote Similarity	NPD28	Approved
0.5823	Remote Similarity	NPD6927	Phase 3
0.5823	Remote Similarity	NPD29	Approved
0.582	Remote Similarity	NPD8273	Phase 1
0.582	Remote Similarity	NPD6637	Approved
0.5818	Remote Similarity	NPD5141	Approved
0.5816	Remote Similarity	NPD6110	Phase 1
0.5816	Remote Similarity	NPD6695	Phase 3
0.581	Remote Similarity	NPD5654	Approved
0.581	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4629	Approved
0.581	Remote Similarity	NPD5210	Approved
0.5804	Remote Similarity	NPD7320	Approved
0.58	Remote Similarity	NPD3618	Phase 1
0.58	Remote Similarity	NPD6098	Approved
0.5795	Remote Similarity	NPD3704	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