NPASS Compound

Structure

NPC200446 OpenBabel07101718272D 28 28 0 0 1 0 0 0 0 0999 V2000 14.9202 10.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1771 11.5063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2260 11.1973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0181 10.2191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0671 9.9101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8591 8.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9081 8.6229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9570 8.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0060 8.0049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0549 7.6959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1039 7.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8959 6.4087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9449 6.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7370 5.1216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7859 4.8126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5780 3.8344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 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 2 0 0 0 0 6 7 1 0 0 0 0 7 8 3 0 0 0 0 8 9 1 0 0 0 0 9 10 3 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 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 20 1 6 0 0 0 23 25 1 0 0 0 0 24 22 1 6 0 0 0 24 28 1 0 0 0 0 25 27 2 0 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.28
Volume:	442.952
LogP:	7.196
LogD:	3.924
LogS:	-6.552
# Rotatable Bonds:	14
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	3.868
Fsp3:	0.72
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:	-4.452
MDCK Permeability:	4.4320488086668774e-05
Pgp-inhibitor:	0.194
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	101.4696044921875%
Volume Distribution (VD):	1.685
Pgp-substrate:	0.587806224822998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.267
CYP1A2-substrate:	0.223
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.765
CYP2C9-substrate:	0.995
CYP2D6-inhibitor:	0.39
CYP2D6-substrate:	0.422
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	4.741
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.547
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.974
Carcinogencity:	0.174
Eye Corrosion:	0.852
Eye Irritation:	0.822
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC200446

Natural Product ID:	NPC200446
*Common Name:**	Debilisone C
IUPAC Name:	(3S,5S)-5-(hydroxymethyl)-3-[(E)-icos-15-en-11,13-diynyl]oxolan-2-one
Synonyms:	Debilisone C
Standard InCHIKey:	BNUXTDGKOZEKSI-PESMWXFUSA-N
Standard InCHI:	InChI=1S/C25H38O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23-21-24(22-26)28-25(23)27/h5-6,23-24,26H,2-4,11-22H2,1H3/b6-5+/t23-,24-/m0/s1
SMILES:	CCCC/C=C/C#CC#CCCCCCCCCCC[C@H]1C[C@@H](CO)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215989
PubChem CID:	46919582
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16759	Polyalthia debilis	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[12762793]
NPO16759	Polyalthia debilis	Species	Annonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20795741]
NPO16759	Polyalthia debilis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	12.5	ug.mL-1	PMID[482944]

☑ 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 NPC200446 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	171
0.1-0.2	1165
0.2-0.3	5932
0.3-0.4	16018
0.4-0.5	8467
0.5-0.6	8102
0.6-0.7	2477
0.7-0.8	350
0.8-0.85	5
0.85-0.9	6
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC209995
0.973	High Similarity	NPC469495
0.9324	High Similarity	NPC81052
0.8961	High Similarity	NPC11796
0.8961	High Similarity	NPC218817
0.8659	High Similarity	NPC475206
0.8333	Intermediate Similarity	NPC217725
0.8267	Intermediate Similarity	NPC82315
0.8228	Intermediate Similarity	NPC470899
0.8182	Intermediate Similarity	NPC477983
0.8182	Intermediate Similarity	NPC477981
0.8049	Intermediate Similarity	NPC103634
0.8026	Intermediate Similarity	NPC273508
0.8026	Intermediate Similarity	NPC209327
0.8023	Intermediate Similarity	NPC179659
0.7975	Intermediate Similarity	NPC472966
0.7895	Intermediate Similarity	NPC148192
0.7895	Intermediate Similarity	NPC330426
0.7895	Intermediate Similarity	NPC271921
0.7895	Intermediate Similarity	NPC104537
0.7895	Intermediate Similarity	NPC22101
0.7895	Intermediate Similarity	NPC127091
0.7865	Intermediate Similarity	NPC30515
0.7865	Intermediate Similarity	NPC184463
0.7841	Intermediate Similarity	NPC307411
0.7821	Intermediate Similarity	NPC42526
0.7792	Intermediate Similarity	NPC141481
0.7792	Intermediate Similarity	NPC324981
0.7792	Intermediate Similarity	NPC473559
0.7792	Intermediate Similarity	NPC477980
0.7792	Intermediate Similarity	NPC48218
0.7791	Intermediate Similarity	NPC21469
0.7753	Intermediate Similarity	NPC476004
0.7753	Intermediate Similarity	NPC51004
0.7753	Intermediate Similarity	NPC478004
0.7753	Intermediate Similarity	NPC158388
0.7753	Intermediate Similarity	NPC478003
0.7753	Intermediate Similarity	NPC474761
0.7727	Intermediate Similarity	NPC202672
0.7692	Intermediate Similarity	NPC199557
0.7674	Intermediate Similarity	NPC474776
0.7674	Intermediate Similarity	NPC9868
0.7667	Intermediate Similarity	NPC12172
0.7667	Intermediate Similarity	NPC208886
0.7662	Intermediate Similarity	NPC475443
0.7662	Intermediate Similarity	NPC473829
0.764	Intermediate Similarity	NPC474032
0.7619	Intermediate Similarity	NPC233377
0.7619	Intermediate Similarity	NPC472948
0.7614	Intermediate Similarity	NPC248602
0.7609	Intermediate Similarity	NPC36954
0.7609	Intermediate Similarity	NPC107476
0.7595	Intermediate Similarity	NPC476660
0.7582	Intermediate Similarity	NPC476300
0.7582	Intermediate Similarity	NPC81419
0.7582	Intermediate Similarity	NPC475912
0.7582	Intermediate Similarity	NPC212486
0.7582	Intermediate Similarity	NPC179746
0.7561	Intermediate Similarity	NPC279537
0.7558	Intermediate Similarity	NPC11620
0.7556	Intermediate Similarity	NPC313670
0.7532	Intermediate Similarity	NPC477982
0.75	Intermediate Similarity	NPC477994
0.75	Intermediate Similarity	NPC89128
0.75	Intermediate Similarity	NPC81386
0.75	Intermediate Similarity	NPC470239
0.75	Intermediate Similarity	NPC477993
0.75	Intermediate Similarity	NPC474035
0.75	Intermediate Similarity	NPC470244
0.7471	Intermediate Similarity	NPC3464
0.7471	Intermediate Similarity	NPC474780
0.7471	Intermediate Similarity	NPC475963
0.7471	Intermediate Similarity	NPC70424
0.7471	Intermediate Similarity	NPC243618
0.7471	Intermediate Similarity	NPC151176
0.747	Intermediate Similarity	NPC116177
0.747	Intermediate Similarity	NPC7563
0.747	Intermediate Similarity	NPC320630
0.7468	Intermediate Similarity	NPC296522
0.7468	Intermediate Similarity	NPC28526
0.7468	Intermediate Similarity	NPC473772
0.7468	Intermediate Similarity	NPC144511
0.7467	Intermediate Similarity	NPC174560
0.7467	Intermediate Similarity	NPC201939
0.7467	Intermediate Similarity	NPC125312
0.7444	Intermediate Similarity	NPC473564
0.7442	Intermediate Similarity	NPC474291
0.7442	Intermediate Similarity	NPC474252
0.7439	Intermediate Similarity	NPC324762
0.7419	Intermediate Similarity	NPC270013
0.7419	Intermediate Similarity	NPC14961
0.7416	Intermediate Similarity	NPC474765
0.7412	Intermediate Similarity	NPC469920
0.7391	Intermediate Similarity	NPC295204
0.7391	Intermediate Similarity	NPC273579
0.7391	Intermediate Similarity	NPC288240
0.7391	Intermediate Similarity	NPC162205
0.7386	Intermediate Similarity	NPC329749
0.7386	Intermediate Similarity	NPC137033
0.7381	Intermediate Similarity	NPC267231
0.7381	Intermediate Similarity	NPC3852
0.7381	Intermediate Similarity	NPC192006
0.7375	Intermediate Similarity	NPC472955
0.7363	Intermediate Similarity	NPC473448
0.7363	Intermediate Similarity	NPC473619
0.7356	Intermediate Similarity	NPC1761
0.7356	Intermediate Similarity	NPC250315
0.7356	Intermediate Similarity	NPC52609
0.7356	Intermediate Similarity	NPC253801
0.734	Intermediate Similarity	NPC476315
0.7333	Intermediate Similarity	NPC476708
0.7333	Intermediate Similarity	NPC227379
0.7333	Intermediate Similarity	NPC177629
0.7333	Intermediate Similarity	NPC474471
0.7333	Intermediate Similarity	NPC243532
0.7333	Intermediate Similarity	NPC58219
0.7333	Intermediate Similarity	NPC153805
0.7333	Intermediate Similarity	NPC476706
0.7333	Intermediate Similarity	NPC476704
0.7333	Intermediate Similarity	NPC476707
0.7333	Intermediate Similarity	NPC281516
0.7326	Intermediate Similarity	NPC470241
0.7326	Intermediate Similarity	NPC191711
0.7326	Intermediate Similarity	NPC207188
0.7326	Intermediate Similarity	NPC47031
0.7317	Intermediate Similarity	NPC474321
0.7303	Intermediate Similarity	NPC309211
0.7303	Intermediate Similarity	NPC474949
0.7303	Intermediate Similarity	NPC475019
0.7303	Intermediate Similarity	NPC469483
0.7303	Intermediate Similarity	NPC475753
0.7303	Intermediate Similarity	NPC279267
0.7303	Intermediate Similarity	NPC112685
0.7303	Intermediate Similarity	NPC164393
0.7303	Intermediate Similarity	NPC69082
0.7297	Intermediate Similarity	NPC329819
0.7283	Intermediate Similarity	NPC473321
0.7273	Intermediate Similarity	NPC472957
0.7273	Intermediate Similarity	NPC68343
0.7273	Intermediate Similarity	NPC328089
0.7273	Intermediate Similarity	NPC472958
0.7273	Intermediate Similarity	NPC226592
0.7273	Intermediate Similarity	NPC470320
0.7273	Intermediate Similarity	NPC72464
0.7263	Intermediate Similarity	NPC40812
0.7253	Intermediate Similarity	NPC92974
0.7253	Intermediate Similarity	NPC295312
0.725	Intermediate Similarity	NPC317583
0.7241	Intermediate Similarity	NPC329829
0.7241	Intermediate Similarity	NPC473780
0.7241	Intermediate Similarity	NPC145914
0.7241	Intermediate Similarity	NPC7414
0.7241	Intermediate Similarity	NPC11332
0.7241	Intermediate Similarity	NPC89555
0.7241	Intermediate Similarity	NPC131002
0.7241	Intermediate Similarity	NPC475159
0.7241	Intermediate Similarity	NPC473712
0.7241	Intermediate Similarity	NPC180363
0.7241	Intermediate Similarity	NPC73310
0.7241	Intermediate Similarity	NPC94875
0.7241	Intermediate Similarity	NPC65930
0.7241	Intermediate Similarity	NPC473529
0.7237	Intermediate Similarity	NPC321838
0.7234	Intermediate Similarity	NPC472469
0.7222	Intermediate Similarity	NPC477959
0.7222	Intermediate Similarity	NPC86005
0.7222	Intermediate Similarity	NPC186148
0.7216	Intermediate Similarity	NPC472753
0.7215	Intermediate Similarity	NPC193029
0.7215	Intermediate Similarity	NPC26500
0.7215	Intermediate Similarity	NPC473357
0.7215	Intermediate Similarity	NPC99619
0.7204	Intermediate Similarity	NPC478036
0.7204	Intermediate Similarity	NPC478037
0.7204	Intermediate Similarity	NPC469692
0.7204	Intermediate Similarity	NPC469645
0.7195	Intermediate Similarity	NPC473775
0.7195	Intermediate Similarity	NPC475232
0.7195	Intermediate Similarity	NPC472956
0.7195	Intermediate Similarity	NPC475260
0.7195	Intermediate Similarity	NPC51249
0.7195	Intermediate Similarity	NPC473699
0.7195	Intermediate Similarity	NPC474100
0.7191	Intermediate Similarity	NPC329738
0.7191	Intermediate Similarity	NPC132496
0.7191	Intermediate Similarity	NPC100921
0.7191	Intermediate Similarity	NPC107986
0.7191	Intermediate Similarity	NPC231009
0.7191	Intermediate Similarity	NPC1083
0.7191	Intermediate Similarity	NPC82795
0.7191	Intermediate Similarity	NPC322529
0.7191	Intermediate Similarity	NPC473651
0.7191	Intermediate Similarity	NPC473669
0.7191	Intermediate Similarity	NPC473478
0.7191	Intermediate Similarity	NPC223871
0.7191	Intermediate Similarity	NPC47958
0.7191	Intermediate Similarity	NPC477018
0.7191	Intermediate Similarity	NPC125290
0.7191	Intermediate Similarity	NPC255307
0.7191	Intermediate Similarity	NPC304509

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 NPC200446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1871
0.2-0.3	4005
0.3-0.4	2144
0.4-0.5	553
0.5-0.6	352
0.6-0.7	55
0.7-0.8	17
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
0.7647	Intermediate Similarity	NPD6435	Approved
0.7529	Intermediate Similarity	NPD5369	Approved
0.75	Intermediate Similarity	NPD3197	Phase 1
0.7473	Intermediate Similarity	NPD7983	Approved
0.7412	Intermediate Similarity	NPD5368	Approved
0.7356	Intermediate Similarity	NPD7154	Phase 3
0.7303	Intermediate Similarity	NPD5786	Approved
0.7241	Intermediate Similarity	NPD4270	Approved
0.7241	Intermediate Similarity	NPD4269	Approved
0.7191	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD46	Approved
0.7174	Intermediate Similarity	NPD6698	Approved
0.7159	Intermediate Similarity	NPD5331	Approved
0.7159	Intermediate Similarity	NPD5332	Approved
0.7159	Intermediate Similarity	NPD5362	Discontinued
0.7011	Intermediate Similarity	NPD4252	Approved
0.7011	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5363	Approved
0.7	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6101	Approved
0.6848	Remote Similarity	NPD4250	Approved
0.6848	Remote Similarity	NPD4251	Approved
0.6842	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD4819	Approved
0.6818	Remote Similarity	NPD4820	Approved
0.6818	Remote Similarity	NPD4821	Approved
0.6818	Remote Similarity	NPD4822	Approved
0.6809	Remote Similarity	NPD5785	Approved
0.6782	Remote Similarity	NPD4268	Approved
0.6782	Remote Similarity	NPD4271	Approved
0.6757	Remote Similarity	NPD3196	Approved
0.6757	Remote Similarity	NPD3195	Phase 2
0.6757	Remote Similarity	NPD3194	Approved
0.6757	Remote Similarity	NPD4266	Approved
0.6739	Remote Similarity	NPD4249	Approved
0.6737	Remote Similarity	NPD6411	Approved
0.6701	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7839	Suspended
0.6632	Remote Similarity	NPD7838	Discovery
0.6625	Remote Similarity	NPD7909	Approved
0.6623	Remote Similarity	NPD6109	Phase 1
0.6622	Remote Similarity	NPD3172	Approved
0.6604	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4790	Discontinued
0.6538	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5370	Suspended
0.6495	Remote Similarity	NPD6399	Phase 3
0.6463	Remote Similarity	NPD7331	Phase 2
0.6456	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD8039	Approved
0.6404	Remote Similarity	NPD3732	Approved
0.6392	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6422	Discontinued
0.6355	Remote Similarity	NPD6371	Approved
0.6351	Remote Similarity	NPD29	Approved
0.6351	Remote Similarity	NPD28	Approved
0.6337	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4225	Approved
0.6329	Remote Similarity	NPD3198	Approved
0.6321	Remote Similarity	NPD6686	Approved
0.6316	Remote Similarity	NPD3728	Approved
0.6316	Remote Similarity	NPD3730	Approved
0.6277	Remote Similarity	NPD1694	Approved
0.6263	Remote Similarity	NPD5282	Discontinued
0.6237	Remote Similarity	NPD6110	Phase 1
0.6228	Remote Similarity	NPD8515	Approved
0.6228	Remote Similarity	NPD8517	Approved
0.6228	Remote Similarity	NPD8516	Approved
0.6228	Remote Similarity	NPD8513	Phase 3
0.6224	Remote Similarity	NPD7637	Suspended
0.6211	Remote Similarity	NPD7334	Approved
0.6211	Remote Similarity	NPD5330	Approved
0.6211	Remote Similarity	NPD6409	Approved
0.6211	Remote Similarity	NPD7146	Approved
0.6211	Remote Similarity	NPD6684	Approved
0.6211	Remote Similarity	NPD7521	Approved
0.6186	Remote Similarity	NPD1695	Approved
0.617	Remote Similarity	NPD4786	Approved
0.6162	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD7341	Phase 2
0.6139	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3667	Approved
0.6106	Remote Similarity	NPD7641	Discontinued
0.6104	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7748	Approved
0.6091	Remote Similarity	NPD8297	Approved
0.6082	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6903	Approved
0.6081	Remote Similarity	NPD3173	Approved
0.6078	Remote Similarity	NPD6084	Phase 2
0.6078	Remote Similarity	NPD6083	Phase 2
0.6078	Remote Similarity	NPD7902	Approved
0.6075	Remote Similarity	NPD6412	Phase 2
0.6061	Remote Similarity	NPD6079	Approved
0.6061	Remote Similarity	NPD7515	Phase 2
0.6042	Remote Similarity	NPD3618	Phase 1
0.6036	Remote Similarity	NPD4632	Approved
0.602	Remote Similarity	NPD5328	Approved
0.6019	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6649	Approved
0.5981	Remote Similarity	NPD6675	Approved
0.5981	Remote Similarity	NPD5739	Approved
0.5981	Remote Similarity	NPD7128	Approved
0.5981	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD8074	Phase 3
0.5963	Remote Similarity	NPD6373	Approved
0.5963	Remote Similarity	NPD6372	Approved
0.5962	Remote Similarity	NPD7639	Approved
0.5962	Remote Similarity	NPD7640	Approved
0.5957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5343	Approved
0.5946	Remote Similarity	NPD622	Approved
0.5938	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5697	Approved
0.5918	Remote Similarity	NPD6672	Approved
0.5918	Remote Similarity	NPD5737	Approved
0.5918	Remote Similarity	NPD5208	Approved
0.5909	Remote Similarity	NPD6883	Approved
0.5909	Remote Similarity	NPD6421	Discontinued
0.5909	Remote Similarity	NPD7102	Approved
0.5909	Remote Similarity	NPD7290	Approved
0.5905	Remote Similarity	NPD5344	Discontinued
0.59	Remote Similarity	NPD8034	Phase 2
0.59	Remote Similarity	NPD8035	Phase 2
0.5882	Remote Similarity	NPD5695	Phase 3
0.5876	Remote Similarity	NPD4519	Discontinued
0.5876	Remote Similarity	NPD5279	Phase 3
0.5876	Remote Similarity	NPD4623	Approved
0.5872	Remote Similarity	NPD6011	Approved
0.5872	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD5696	Approved
0.5862	Remote Similarity	NPD6319	Approved
0.5856	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD8130	Phase 1
0.5856	Remote Similarity	NPD6617	Approved
0.5856	Remote Similarity	NPD6847	Approved
0.5824	Remote Similarity	NPD6933	Approved
0.5818	Remote Similarity	NPD6013	Approved
0.5818	Remote Similarity	NPD6012	Approved
0.5818	Remote Similarity	NPD6014	Approved
0.5818	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7750	Discontinued
0.5816	Remote Similarity	NPD7524	Approved
0.5812	Remote Similarity	NPD8444	Approved
0.5806	Remote Similarity	NPD6683	Phase 2
0.5804	Remote Similarity	NPD6053	Discontinued
0.5804	Remote Similarity	NPD6882	Approved
0.58	Remote Similarity	NPD5207	Approved
0.5798	Remote Similarity	NPD8341	Approved
0.5798	Remote Similarity	NPD7492	Approved
0.5798	Remote Similarity	NPD8340	Approved
0.5798	Remote Similarity	NPD8299	Approved
0.5798	Remote Similarity	NPD8342	Approved
0.5789	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5209	Approved
0.5784	Remote Similarity	NPD7900	Approved
0.5784	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5701	Approved
0.578	Remote Similarity	NPD6685	Approved
0.5758	Remote Similarity	NPD4518	Approved
0.575	Remote Similarity	NPD6616	Approved
0.575	Remote Similarity	NPD8451	Approved
0.5745	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5284	Approved
0.5743	Remote Similarity	NPD5281	Approved
0.5739	Remote Similarity	NPD6009	Approved
0.5728	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD4689	Approved
0.5714	Remote Similarity	NPD8328	Phase 3
0.5714	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6098	Approved
0.5714	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD7830	Approved
0.5714	Remote Similarity	NPD4138	Approved
0.5714	Remote Similarity	NPD4693	Phase 3
0.5714	Remote Similarity	NPD7829	Approved
0.5714	Remote Similarity	NPD4690	Approved
0.5714	Remote Similarity	NPD5205	Approved
0.5714	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD4688	Approved
0.5714	Remote Similarity	NPD1719	Phase 1
0.5702	Remote Similarity	NPD7078	Approved
0.5702	Remote Similarity	NPD8448	Approved
0.57	Remote Similarity	NPD6051	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