NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	278.369
LogP:	2.564
LogD:	2.08
LogS:	-3.093
# Rotatable Bonds:	0
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	4.747
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.366
MDCK Permeability:	4.6030218072701246e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.117

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	96.20838165283203%
Volume Distribution (VD):	0.929
Pgp-substrate:	5.653400897979736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.231
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.841
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	8.361
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.824
Maximum Recommended Daily Dose:	0.15
Skin Sensitization:	0.364
Carcinogencity:	0.275
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC469872

Natural Product ID:	NPC469872
*Common Name:**	Subvellerolactones D
IUPAC Name:	(1S,4R,5R,5aR,6R)-1,4,6-trihydroxy-5,7,7-trimethyl-1,4,5,5a,6,8-hexahydroazuleno[5,6-c]furan-3-one
Synonyms:	subvellerolactones D
Standard InCHIKey:	JPUWZJIHLKKYKJ-FXBUQDJQSA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-6-9-7(5-15(2,3)12(9)17)4-8-10(11(6)16)14(19)20-13(8)18/h4,6,9,11-13,16-18H,5H2,1-3H3/t6-,9-,11-,12-,13+/m1/s1
SMILES:	C[C@H]1[C@@H](O)C2=C(C=C3[C@@H]1[C@@H](O)C(C3)(C)C)[C@H](OC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223948
PubChem CID:	46933997
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO32977	lactarius subvellereus	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20719504]

☑ 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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	25100.0	nM	PMID[515222]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[515222]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[515222]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	17800.0	nM	PMID[515222]

☑ 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 NPC469872 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	211
0.1-0.2	1130
0.2-0.3	4528
0.3-0.4	10043
0.4-0.5	13894
0.5-0.6	7746
0.6-0.7	4454
0.7-0.8	668
0.8-0.85	17
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469864
0.8842	High Similarity	NPC96541
0.8557	High Similarity	NPC476487
0.8557	High Similarity	NPC469873
0.8557	High Similarity	NPC476488
0.8431	Intermediate Similarity	NPC309190
0.8421	Intermediate Similarity	NPC212664
0.82	Intermediate Similarity	NPC477949
0.82	Intermediate Similarity	NPC475709
0.8137	Intermediate Similarity	NPC477950
0.8119	Intermediate Similarity	NPC64742
0.8021	Intermediate Similarity	NPC475678
0.8	Intermediate Similarity	NPC245434
0.7965	Intermediate Similarity	NPC470829
0.7965	Intermediate Similarity	NPC473228
0.7959	Intermediate Similarity	NPC281942
0.7959	Intermediate Similarity	NPC232426
0.7941	Intermediate Similarity	NPC141191
0.7921	Intermediate Similarity	NPC9812
0.7905	Intermediate Similarity	NPC121099
0.79	Intermediate Similarity	NPC474555
0.79	Intermediate Similarity	NPC167219
0.79	Intermediate Similarity	NPC53685
0.79	Intermediate Similarity	NPC475572
0.7879	Intermediate Similarity	NPC141831
0.7872	Intermediate Similarity	NPC89555
0.7857	Intermediate Similarity	NPC225283
0.7857	Intermediate Similarity	NPC13710
0.7843	Intermediate Similarity	NPC169205
0.7822	Intermediate Similarity	NPC90121
0.7822	Intermediate Similarity	NPC275960
0.7822	Intermediate Similarity	NPC52044
0.7822	Intermediate Similarity	NPC37408
0.7822	Intermediate Similarity	NPC48803
0.7822	Intermediate Similarity	NPC193645
0.7812	Intermediate Similarity	NPC471185
0.7812	Intermediate Similarity	NPC165162
0.78	Intermediate Similarity	NPC59646
0.7788	Intermediate Similarity	NPC116139
0.7788	Intermediate Similarity	NPC206079
0.7788	Intermediate Similarity	NPC244456
0.7788	Intermediate Similarity	NPC469657
0.7778	Intermediate Similarity	NPC47951
0.7778	Intermediate Similarity	NPC477782
0.7778	Intermediate Similarity	NPC129419
0.7778	Intermediate Similarity	NPC3436
0.7767	Intermediate Similarity	NPC244411
0.7745	Intermediate Similarity	NPC17578
0.7745	Intermediate Similarity	NPC470801
0.7745	Intermediate Similarity	NPC185553
0.7745	Intermediate Similarity	NPC240673
0.7727	Intermediate Similarity	NPC138757
0.7727	Intermediate Similarity	NPC123855
0.7727	Intermediate Similarity	NPC76550
0.7723	Intermediate Similarity	NPC470521
0.7714	Intermediate Similarity	NPC66110
0.77	Intermediate Similarity	NPC472814
0.77	Intermediate Similarity	NPC470520
0.77	Intermediate Similarity	NPC2882
0.77	Intermediate Similarity	NPC177037
0.77	Intermediate Similarity	NPC477783
0.7692	Intermediate Similarity	NPC477720
0.7685	Intermediate Similarity	NPC220155
0.7684	Intermediate Similarity	NPC471296
0.7677	Intermediate Similarity	NPC268298
0.767	Intermediate Similarity	NPC161493
0.7658	Intermediate Similarity	NPC46269
0.7658	Intermediate Similarity	NPC106395
0.7653	Intermediate Similarity	NPC237540
0.7653	Intermediate Similarity	NPC312561
0.7647	Intermediate Similarity	NPC67584
0.7647	Intermediate Similarity	NPC170120
0.7647	Intermediate Similarity	NPC209355
0.7624	Intermediate Similarity	NPC115021
0.7624	Intermediate Similarity	NPC472954
0.7619	Intermediate Similarity	NPC171759
0.7619	Intermediate Similarity	NPC150923
0.7619	Intermediate Similarity	NPC62670
0.76	Intermediate Similarity	NPC469368
0.76	Intermediate Similarity	NPC145666
0.76	Intermediate Similarity	NPC475879
0.7596	Intermediate Similarity	NPC471610
0.7596	Intermediate Similarity	NPC221615
0.7589	Intermediate Similarity	NPC67290
0.7589	Intermediate Similarity	NPC133677
0.7589	Intermediate Similarity	NPC138303
0.7586	Intermediate Similarity	NPC287236
0.7579	Intermediate Similarity	NPC78677
0.7579	Intermediate Similarity	NPC59994
0.7579	Intermediate Similarity	NPC470241
0.7576	Intermediate Similarity	NPC472810
0.7576	Intermediate Similarity	NPC472809
0.7576	Intermediate Similarity	NPC476805
0.7573	Intermediate Similarity	NPC24956
0.7573	Intermediate Similarity	NPC242848
0.7573	Intermediate Similarity	NPC213078
0.7573	Intermediate Similarity	NPC18019
0.7551	Intermediate Similarity	NPC261721
0.7551	Intermediate Similarity	NPC475461
0.7551	Intermediate Similarity	NPC305475
0.7549	Intermediate Similarity	NPC470255
0.7549	Intermediate Similarity	NPC474554
0.7545	Intermediate Similarity	NPC257240
0.7526	Intermediate Similarity	NPC165287
0.7526	Intermediate Similarity	NPC114979
0.7526	Intermediate Similarity	NPC156485
0.7526	Intermediate Similarity	NPC191476
0.7526	Intermediate Similarity	NPC82297
0.7525	Intermediate Similarity	NPC261607
0.7525	Intermediate Similarity	NPC32494
0.7525	Intermediate Similarity	NPC175842
0.7525	Intermediate Similarity	NPC475925
0.7525	Intermediate Similarity	NPC111114
0.7525	Intermediate Similarity	NPC300312
0.7524	Intermediate Similarity	NPC280963
0.7524	Intermediate Similarity	NPC472644
0.75	Intermediate Similarity	NPC12872
0.75	Intermediate Similarity	NPC251528
0.75	Intermediate Similarity	NPC213947
0.75	Intermediate Similarity	NPC470734
0.75	Intermediate Similarity	NPC108475
0.75	Intermediate Similarity	NPC69385
0.75	Intermediate Similarity	NPC53844
0.75	Intermediate Similarity	NPC170143
0.75	Intermediate Similarity	NPC202705
0.75	Intermediate Similarity	NPC153095
0.75	Intermediate Similarity	NPC471462
0.75	Intermediate Similarity	NPC179891
0.75	Intermediate Similarity	NPC168679
0.7477	Intermediate Similarity	NPC183570
0.7476	Intermediate Similarity	NPC304886
0.7476	Intermediate Similarity	NPC213698
0.7475	Intermediate Similarity	NPC201658
0.7453	Intermediate Similarity	NPC471075
0.7451	Intermediate Similarity	NPC472812
0.7451	Intermediate Similarity	NPC166346
0.7451	Intermediate Similarity	NPC242069
0.7449	Intermediate Similarity	NPC471300
0.7449	Intermediate Similarity	NPC287015
0.7449	Intermediate Similarity	NPC255307
0.7449	Intermediate Similarity	NPC470755
0.7449	Intermediate Similarity	NPC146850
0.7449	Intermediate Similarity	NPC78089
0.7449	Intermediate Similarity	NPC474860
0.7429	Intermediate Similarity	NPC474440
0.7429	Intermediate Similarity	NPC222011
0.7426	Intermediate Similarity	NPC37607
0.7426	Intermediate Similarity	NPC77337
0.7426	Intermediate Similarity	NPC51486
0.7426	Intermediate Similarity	NPC301969
0.7426	Intermediate Similarity	NPC473448
0.7407	Intermediate Similarity	NPC100487
0.7407	Intermediate Similarity	NPC203659
0.7407	Intermediate Similarity	NPC474917
0.74	Intermediate Similarity	NPC472378
0.74	Intermediate Similarity	NPC260343
0.74	Intermediate Similarity	NPC476803
0.7396	Intermediate Similarity	NPC325031
0.7396	Intermediate Similarity	NPC52861
0.7387	Intermediate Similarity	NPC235014
0.7379	Intermediate Similarity	NPC470010
0.7379	Intermediate Similarity	NPC104925
0.7379	Intermediate Similarity	NPC470013
0.7379	Intermediate Similarity	NPC474338
0.7379	Intermediate Similarity	NPC475927
0.7379	Intermediate Similarity	NPC298973
0.7379	Intermediate Similarity	NPC127019
0.7379	Intermediate Similarity	NPC262133
0.7379	Intermediate Similarity	NPC65829
0.7379	Intermediate Similarity	NPC323008
0.7379	Intermediate Similarity	NPC477131
0.7379	Intermediate Similarity	NPC475832
0.7379	Intermediate Similarity	NPC469697
0.7379	Intermediate Similarity	NPC469632
0.7374	Intermediate Similarity	NPC107787
0.7374	Intermediate Similarity	NPC474062
0.7374	Intermediate Similarity	NPC469483
0.7368	Intermediate Similarity	NPC470239
0.7368	Intermediate Similarity	NPC470244
0.7364	Intermediate Similarity	NPC90946
0.7364	Intermediate Similarity	NPC475960
0.7364	Intermediate Similarity	NPC308191
0.7364	Intermediate Similarity	NPC300614
0.7364	Intermediate Similarity	NPC476765
0.7358	Intermediate Similarity	NPC474012
0.7358	Intermediate Similarity	NPC476299
0.7353	Intermediate Similarity	NPC70595
0.7353	Intermediate Similarity	NPC123177
0.7353	Intermediate Similarity	NPC472811
0.7353	Intermediate Similarity	NPC74103
0.7353	Intermediate Similarity	NPC472705
0.7353	Intermediate Similarity	NPC284185
0.7353	Intermediate Similarity	NPC150978
0.7353	Intermediate Similarity	NPC131209
0.735	Intermediate Similarity	NPC470418
0.7347	Intermediate Similarity	NPC158756
0.7347	Intermediate Similarity	NPC31086
0.7347	Intermediate Similarity	NPC141193
0.7347	Intermediate Similarity	NPC476804
0.7347	Intermediate Similarity	NPC96259

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 NPC469872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1601
0.2-0.3	3661
0.3-0.4	2506
0.4-0.5	759
0.5-0.6	332
0.6-0.7	100
0.7-0.8	9
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
0.7822	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5785	Approved
0.7545	Intermediate Similarity	NPD6371	Approved
0.7245	Intermediate Similarity	NPD5362	Discontinued
0.7207	Intermediate Similarity	NPD6686	Approved
0.7172	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5363	Approved
0.7019	Intermediate Similarity	NPD7637	Suspended
0.697	Remote Similarity	NPD4270	Approved
0.697	Remote Similarity	NPD5209	Approved
0.697	Remote Similarity	NPD4269	Approved
0.6964	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5778	Approved
0.6952	Remote Similarity	NPD5779	Approved
0.6944	Remote Similarity	NPD4225	Approved
0.6939	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7319	Approved
0.6931	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5786	Approved
0.6857	Remote Similarity	NPD6411	Approved
0.6857	Remote Similarity	NPD7983	Approved
0.6829	Remote Similarity	NPD7507	Approved
0.681	Remote Similarity	NPD6053	Discontinued
0.68	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4820	Approved
0.6768	Remote Similarity	NPD4821	Approved
0.6768	Remote Similarity	NPD4252	Approved
0.6768	Remote Similarity	NPD4822	Approved
0.6768	Remote Similarity	NPD4819	Approved
0.6762	Remote Similarity	NPD46	Approved
0.6762	Remote Similarity	NPD6698	Approved
0.6759	Remote Similarity	NPD7839	Suspended
0.6735	Remote Similarity	NPD4268	Approved
0.6735	Remote Similarity	NPD4271	Approved
0.6733	Remote Similarity	NPD7154	Phase 3
0.6733	Remote Similarity	NPD5332	Approved
0.6733	Remote Similarity	NPD5331	Approved
0.6723	Remote Similarity	NPD7115	Discovery
0.67	Remote Similarity	NPD4790	Discontinued
0.67	Remote Similarity	NPD5369	Approved
0.6699	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD1695	Approved
0.6635	Remote Similarity	NPD4250	Approved
0.6635	Remote Similarity	NPD4251	Approved
0.6634	Remote Similarity	NPD6435	Approved
0.6604	Remote Similarity	NPD7838	Discovery
0.6577	Remote Similarity	NPD7640	Approved
0.6577	Remote Similarity	NPD7639	Approved
0.6574	Remote Similarity	NPD5282	Discontinued
0.6545	Remote Similarity	NPD6083	Phase 2
0.6545	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD7327	Approved
0.6529	Remote Similarity	NPD7328	Approved
0.6522	Remote Similarity	NPD6412	Phase 2
0.6514	Remote Similarity	NPD5695	Phase 3
0.6504	Remote Similarity	NPD8513	Phase 3
0.6504	Remote Similarity	NPD8033	Approved
0.6504	Remote Similarity	NPD8516	Approved
0.6504	Remote Similarity	NPD8517	Approved
0.6504	Remote Similarity	NPD8515	Approved
0.6486	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7638	Approved
0.6481	Remote Similarity	NPD6399	Phase 3
0.6475	Remote Similarity	NPD7516	Approved
0.6466	Remote Similarity	NPD7320	Approved
0.6442	Remote Similarity	NPD1694	Approved
0.6436	Remote Similarity	NPD5368	Approved
0.6435	Remote Similarity	NPD6402	Approved
0.6435	Remote Similarity	NPD5739	Approved
0.6435	Remote Similarity	NPD7128	Approved
0.6435	Remote Similarity	NPD6675	Approved
0.6423	Remote Similarity	NPD8294	Approved
0.6423	Remote Similarity	NPD8377	Approved
0.6389	Remote Similarity	NPD5281	Approved
0.6389	Remote Similarity	NPD5284	Approved
0.6387	Remote Similarity	NPD6882	Approved
0.6381	Remote Similarity	NPD5279	Phase 3
0.6379	Remote Similarity	NPD5697	Approved
0.6379	Remote Similarity	NPD5701	Approved
0.6378	Remote Similarity	NPD8293	Discontinued
0.6371	Remote Similarity	NPD7503	Approved
0.6371	Remote Similarity	NPD8296	Approved
0.6371	Remote Similarity	NPD8380	Approved
0.6371	Remote Similarity	NPD8335	Approved
0.6371	Remote Similarity	NPD8379	Approved
0.6371	Remote Similarity	NPD8378	Approved
0.6346	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5696	Approved
0.6328	Remote Similarity	NPD7736	Approved
0.6325	Remote Similarity	NPD6881	Approved
0.6325	Remote Similarity	NPD6899	Approved
0.632	Remote Similarity	NPD6370	Approved
0.6271	Remote Similarity	NPD6014	Approved
0.6271	Remote Similarity	NPD6012	Approved
0.6271	Remote Similarity	NPD6373	Approved
0.6271	Remote Similarity	NPD6013	Approved
0.6271	Remote Similarity	NPD6372	Approved
0.6263	Remote Similarity	NPD8039	Approved
0.6262	Remote Similarity	NPD6903	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6239	Remote Similarity	NPD5693	Phase 1
0.6226	Remote Similarity	NPD7521	Approved
0.6226	Remote Similarity	NPD7334	Approved
0.6226	Remote Similarity	NPD6684	Approved
0.6226	Remote Similarity	NPD6409	Approved
0.6226	Remote Similarity	NPD7146	Approved
0.6226	Remote Similarity	NPD5330	Approved
0.622	Remote Similarity	NPD7492	Approved
0.6218	Remote Similarity	NPD7290	Approved
0.6218	Remote Similarity	NPD6883	Approved
0.6218	Remote Similarity	NPD7102	Approved
0.6204	Remote Similarity	NPD4753	Phase 2
0.6204	Remote Similarity	NPD5370	Suspended
0.619	Remote Similarity	NPD3133	Approved
0.619	Remote Similarity	NPD3666	Approved
0.619	Remote Similarity	NPD3665	Phase 1
0.6186	Remote Similarity	NPD6011	Approved
0.6174	Remote Similarity	NPD5211	Phase 2
0.6172	Remote Similarity	NPD6616	Approved
0.6167	Remote Similarity	NPD6617	Approved
0.6167	Remote Similarity	NPD6649	Approved
0.6167	Remote Similarity	NPD6650	Approved
0.6167	Remote Similarity	NPD6869	Approved
0.6167	Remote Similarity	NPD6847	Approved
0.6167	Remote Similarity	NPD8130	Phase 1
0.6167	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6059	Approved
0.616	Remote Similarity	NPD6054	Approved
0.6147	Remote Similarity	NPD5692	Phase 3
0.6147	Remote Similarity	NPD5207	Approved
0.6142	Remote Similarity	NPD7830	Approved
0.6142	Remote Similarity	NPD7829	Approved
0.6134	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7078	Approved
0.6116	Remote Similarity	NPD8297	Approved
0.6111	Remote Similarity	NPD6672	Approved
0.6111	Remote Similarity	NPD6015	Approved
0.6111	Remote Similarity	NPD6016	Approved
0.6111	Remote Similarity	NPD5737	Approved
0.6111	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4755	Approved
0.6091	Remote Similarity	NPD6050	Approved
0.6091	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5694	Approved
0.6068	Remote Similarity	NPD5141	Approved
0.6066	Remote Similarity	NPD8133	Approved
0.6063	Remote Similarity	NPD5988	Approved
0.6038	Remote Similarity	NPD4786	Approved
0.6036	Remote Similarity	NPD4202	Approved
0.6034	Remote Similarity	NPD7632	Discontinued
0.6033	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6319	Approved
0.6019	Remote Similarity	NPD7524	Approved
0.6019	Remote Similarity	NPD6929	Approved
0.6019	Remote Similarity	NPD7750	Discontinued
0.6017	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.5984	Remote Similarity	NPD8444	Approved
0.5982	Remote Similarity	NPD7748	Approved
0.5981	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4756	Discovery
0.5968	Remote Similarity	NPD6274	Approved
0.5965	Remote Similarity	NPD7902	Approved
0.5963	Remote Similarity	NPD4518	Approved
0.5962	Remote Similarity	NPD6930	Phase 2
0.5962	Remote Similarity	NPD6931	Approved
0.595	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5344	Discontinued
0.5946	Remote Similarity	NPD7515	Phase 2
0.5929	Remote Similarity	NPD4629	Approved
0.5929	Remote Similarity	NPD5210	Approved
0.5929	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5280	Approved
0.5926	Remote Similarity	NPD4694	Approved
0.5926	Remote Similarity	NPD3618	Phase 1
0.5923	Remote Similarity	NPD8451	Approved
0.592	Remote Similarity	NPD6009	Approved
0.5909	Remote Similarity	NPD5328	Approved
0.5909	Remote Similarity	NPD6051	Approved
0.5909	Remote Similarity	NPD6080	Approved
0.5909	Remote Similarity	NPD6904	Approved
0.5909	Remote Similarity	NPD6673	Approved
0.5897	Remote Similarity	NPD4633	Approved
0.5897	Remote Similarity	NPD5224	Approved
0.5897	Remote Similarity	NPD5225	Approved
0.5897	Remote Similarity	NPD5226	Approved
0.5891	Remote Similarity	NPD8328	Phase 3
0.5878	Remote Similarity	NPD8448	Approved
0.5862	Remote Similarity	NPD6404	Discontinued
0.5849	Remote Similarity	NPD4223	Phase 3
0.5849	Remote Similarity	NPD4221	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