NPASS Compound

Structure

NPC475773 OpenBabel07101718272D 24 27 0 0 1 0 0 0 0 0999 V2000 2.2240 2.9967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1547 0.3018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9077 0.9598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7103 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8806 3.0831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8966 3.2616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6884 0.0659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3544 2.2025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6884 0.0659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4502 2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1436 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9974 1.0169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5443 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1884 1.6047 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9614 1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0443 3.4268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6473 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 11 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 8 1 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 10 1 6 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 7 1 6 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 20 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 22 1 6 0 0 0 17 24 1 0 0 0 0 18 23 1 6 0 0 0 18 24 1 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	4.165
LogD:	4.136
LogS:	-4.921
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.587
Synthetic Accessibility Score:	4.973
Fsp3:	0.85
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:	-4.707
MDCK Permeability:	2.410598608548753e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.181
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	86.50231170654297%
Volume Distribution (VD):	1.56
Pgp-substrate:	12.118395805358887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.235
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.687
CYP2C9-inhibitor:	0.322
CYP2C9-substrate:	0.323
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.339
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	8.278
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.626
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.325
Maximum Recommended Daily Dose:	0.404
Skin Sensitization:	0.182
Carcinogencity:	0.099
Eye Corrosion:	0.006
Eye Irritation:	0.052
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC475773

Natural Product ID:	NPC475773
*Common Name:**	Dendrillolide A
IUPAC Name:	(2R,3R,3aR,6aR)-3-[(1R,3aR,8aS)-1,4,4-trimethyl-8-methylidene-3,3a,5,6,7,8a-hexahydro-2H-azulen-1-yl]-2-hydroxy-3,3a,4,6a-tetrahydro-2H-furo[2,3-b]furan-5-one
Synonyms:
Standard InCHIKey:	MQCRZIHSAFOQTA-XWJPXQAFSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-11-6-5-8-19(2,3)13-7-9-20(4,15(11)13)16-12-10-14(21)23-18(12)24-17(16)22/h12-13,15-18,22H,1,5-10H2,2-4H3/t12-,13-,15-,16+,17-,18+,20-/m1/s1
SMILES:	O=C1O[C@@H]2[C@H](C1)[C@@H]([C@@H](O2)O)[C@]1(C)CC[C@@H]2[C@H]1C(=C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515163
PubChem CID:	44584609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO33159	dendrilla sp.	Species	Darwinellidae	Eukaryota	n.a.	Palau	n.a.	Database[Title]

☑ 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
Others	1

Activity Type	# Activity
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24397	SINGLE PROTEIN	Phospholipase A2	Apis mellifera	Activity	=	48.0	%	PMID[542474]

☑ 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 NPC475773 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	258
0.1-0.2	2479
0.2-0.3	11162
0.3-0.4	13545
0.4-0.5	7386
0.5-0.6	6764
0.6-0.7	972
0.7-0.8	129
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8621	High Similarity	NPC265580
0.8	Intermediate Similarity	NPC261372
0.8	Intermediate Similarity	NPC263674
0.8	Intermediate Similarity	NPC58267
0.7955	Intermediate Similarity	NPC111409
0.7895	Intermediate Similarity	NPC474297
0.7816	Intermediate Similarity	NPC51507
0.7812	Intermediate Similarity	NPC304445
0.7812	Intermediate Similarity	NPC236580
0.7755	Intermediate Similarity	NPC67296
0.7753	Intermediate Similarity	NPC128246
0.7742	Intermediate Similarity	NPC297474
0.7742	Intermediate Similarity	NPC54065
0.7727	Intermediate Similarity	NPC126248
0.766	Intermediate Similarity	NPC171360
0.766	Intermediate Similarity	NPC57304
0.766	Intermediate Similarity	NPC133888
0.766	Intermediate Similarity	NPC35959
0.766	Intermediate Similarity	NPC29821
0.766	Intermediate Similarity	NPC63193
0.766	Intermediate Similarity	NPC293001
0.7653	Intermediate Similarity	NPC473146
0.7634	Intermediate Similarity	NPC155935
0.7614	Intermediate Similarity	NPC156658
0.7614	Intermediate Similarity	NPC258965
0.7553	Intermediate Similarity	NPC35809
0.7551	Intermediate Similarity	NPC249171
0.7551	Intermediate Similarity	NPC49833
0.7527	Intermediate Similarity	NPC217983
0.7527	Intermediate Similarity	NPC207114
0.7527	Intermediate Similarity	NPC178875
0.7526	Intermediate Similarity	NPC142529
0.7526	Intermediate Similarity	NPC91771
0.75	Intermediate Similarity	NPC49730
0.75	Intermediate Similarity	NPC98069
0.75	Intermediate Similarity	NPC309757
0.75	Intermediate Similarity	NPC236692
0.75	Intermediate Similarity	NPC473331
0.75	Intermediate Similarity	NPC80144
0.75	Intermediate Similarity	NPC56593
0.75	Intermediate Similarity	NPC98633
0.7451	Intermediate Similarity	NPC103172
0.7451	Intermediate Similarity	NPC164600
0.7447	Intermediate Similarity	NPC168679
0.7447	Intermediate Similarity	NPC12872
0.7447	Intermediate Similarity	NPC215556
0.7426	Intermediate Similarity	NPC473148
0.7419	Intermediate Similarity	NPC118601
0.7396	Intermediate Similarity	NPC153590
0.7396	Intermediate Similarity	NPC473234
0.7396	Intermediate Similarity	NPC200237
0.7396	Intermediate Similarity	NPC308656
0.7396	Intermediate Similarity	NPC60386
0.7396	Intermediate Similarity	NPC473273
0.7396	Intermediate Similarity	NPC473263
0.7368	Intermediate Similarity	NPC216284
0.7368	Intermediate Similarity	NPC19087
0.7363	Intermediate Similarity	NPC54468
0.7347	Intermediate Similarity	NPC24956
0.7347	Intermediate Similarity	NPC18019
0.734	Intermediate Similarity	NPC470009
0.734	Intermediate Similarity	NPC79549
0.732	Intermediate Similarity	NPC41649
0.732	Intermediate Similarity	NPC289004
0.7312	Intermediate Similarity	NPC187661
0.7292	Intermediate Similarity	NPC475925
0.7292	Intermediate Similarity	NPC184063
0.729	Intermediate Similarity	NPC285086
0.7283	Intermediate Similarity	NPC194859
0.7283	Intermediate Similarity	NPC224386
0.7273	Intermediate Similarity	NPC70996
0.7263	Intermediate Similarity	NPC38392
0.7262	Intermediate Similarity	NPC5714
0.7253	Intermediate Similarity	NPC246076
0.7245	Intermediate Similarity	NPC163228
0.7245	Intermediate Similarity	NPC167893
0.7245	Intermediate Similarity	NPC472873
0.7234	Intermediate Similarity	NPC24728
0.7228	Intermediate Similarity	NPC171759
0.7216	Intermediate Similarity	NPC277721
0.7216	Intermediate Similarity	NPC267266
0.7216	Intermediate Similarity	NPC470656
0.7216	Intermediate Similarity	NPC470576
0.7216	Intermediate Similarity	NPC475788
0.7212	Intermediate Similarity	NPC88833
0.7212	Intermediate Similarity	NPC96333
0.7204	Intermediate Similarity	NPC204105
0.7204	Intermediate Similarity	NPC300082
0.7204	Intermediate Similarity	NPC284534
0.7184	Intermediate Similarity	NPC472228
0.7184	Intermediate Similarity	NPC101842
0.7184	Intermediate Similarity	NPC472227
0.7159	Intermediate Similarity	NPC476601
0.7158	Intermediate Similarity	NPC471149
0.7157	Intermediate Similarity	NPC94919
0.7157	Intermediate Similarity	NPC106668
0.7156	Intermediate Similarity	NPC277583
0.7143	Intermediate Similarity	NPC232625
0.7143	Intermediate Similarity	NPC224414
0.7143	Intermediate Similarity	NPC96541
0.7128	Intermediate Similarity	NPC238593
0.7128	Intermediate Similarity	NPC162071
0.7128	Intermediate Similarity	NPC470242
0.7126	Intermediate Similarity	NPC215030
0.7115	Intermediate Similarity	NPC475217
0.7115	Intermediate Similarity	NPC285927
0.7113	Intermediate Similarity	NPC155215
0.7113	Intermediate Similarity	NPC133698
0.7113	Intermediate Similarity	NPC131209
0.7113	Intermediate Similarity	NPC191339
0.7113	Intermediate Similarity	NPC286341
0.7103	Intermediate Similarity	NPC471251
0.71	Intermediate Similarity	NPC213947
0.71	Intermediate Similarity	NPC311904
0.71	Intermediate Similarity	NPC108475
0.71	Intermediate Similarity	NPC170143
0.71	Intermediate Similarity	NPC471150
0.7087	Intermediate Similarity	NPC475928
0.7087	Intermediate Similarity	NPC27687
0.7083	Intermediate Similarity	NPC283409
0.7079	Intermediate Similarity	NPC238227
0.7075	Intermediate Similarity	NPC471250
0.7071	Intermediate Similarity	NPC476053
0.7059	Intermediate Similarity	NPC287539
0.7059	Intermediate Similarity	NPC3488
0.7053	Intermediate Similarity	NPC201658
0.7053	Intermediate Similarity	NPC186148
0.7053	Intermediate Similarity	NPC167877
0.7048	Intermediate Similarity	NPC61071
0.7045	Intermediate Similarity	NPC471491
0.7045	Intermediate Similarity	NPC217725
0.7045	Intermediate Similarity	NPC179922
0.7041	Intermediate Similarity	NPC258216
0.7033	Intermediate Similarity	NPC73052
0.7033	Intermediate Similarity	NPC293418
0.7033	Intermediate Similarity	NPC170038
0.7033	Intermediate Similarity	NPC290508
0.703	Intermediate Similarity	NPC37866
0.7019	Intermediate Similarity	NPC100955
0.7019	Intermediate Similarity	NPC223741
0.7019	Intermediate Similarity	NPC121566
0.7019	Intermediate Similarity	NPC244247
0.701	Intermediate Similarity	NPC474323
0.701	Intermediate Similarity	NPC471371
0.701	Intermediate Similarity	NPC206614
0.701	Intermediate Similarity	NPC471370
0.7009	Intermediate Similarity	NPC101450
0.7009	Intermediate Similarity	NPC130302
0.7009	Intermediate Similarity	NPC124053
0.7009	Intermediate Similarity	NPC255655
0.7009	Intermediate Similarity	NPC471884
0.7009	Intermediate Similarity	NPC106760
0.7	Intermediate Similarity	NPC126156
0.699	Remote Similarity	NPC35185
0.699	Remote Similarity	NPC4899
0.699	Remote Similarity	NPC86077
0.699	Remote Similarity	NPC177013
0.699	Remote Similarity	NPC474730
0.6989	Remote Similarity	NPC245665
0.6979	Remote Similarity	NPC177629
0.6979	Remote Similarity	NPC58219
0.6979	Remote Similarity	NPC33398
0.6979	Remote Similarity	NPC254572
0.6979	Remote Similarity	NPC48824
0.6979	Remote Similarity	NPC250687
0.6979	Remote Similarity	NPC229407
0.6979	Remote Similarity	NPC53158
0.6972	Remote Similarity	NPC209058
0.697	Remote Similarity	NPC90453
0.697	Remote Similarity	NPC477131
0.697	Remote Similarity	NPC63897
0.697	Remote Similarity	NPC198853
0.6961	Remote Similarity	NPC186861
0.6961	Remote Similarity	NPC267921
0.6961	Remote Similarity	NPC471381
0.6957	Remote Similarity	NPC47635
0.6952	Remote Similarity	NPC162033
0.6952	Remote Similarity	NPC252234
0.6952	Remote Similarity	NPC170432
0.6952	Remote Similarity	NPC63023
0.6952	Remote Similarity	NPC95243
0.6952	Remote Similarity	NPC127235
0.6947	Remote Similarity	NPC304558
0.6947	Remote Similarity	NPC64153
0.6947	Remote Similarity	NPC244174
0.6944	Remote Similarity	NPC474750
0.6944	Remote Similarity	NPC272242
0.6939	Remote Similarity	NPC235051
0.6939	Remote Similarity	NPC471747
0.6932	Remote Similarity	NPC472966
0.6931	Remote Similarity	NPC161493
0.6931	Remote Similarity	NPC253586
0.6931	Remote Similarity	NPC477949
0.6931	Remote Similarity	NPC474313
0.6923	Remote Similarity	NPC118987
0.6923	Remote Similarity	NPC37240
0.6923	Remote Similarity	NPC140723
0.6916	Remote Similarity	NPC118225
0.6915	Remote Similarity	NPC165287
0.6909	Remote Similarity	NPC123117

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 NPC475773 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	3295
0.2-0.3	3776
0.3-0.4	1167
0.4-0.5	374
0.5-0.6	218
0.6-0.7	16
0.7-0.8	0
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
0.6733	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8034	Phase 2
0.66	Remote Similarity	NPD8035	Phase 2
0.6535	Remote Similarity	NPD6399	Phase 3
0.6526	Remote Similarity	NPD6435	Approved
0.6458	Remote Similarity	NPD5362	Discontinued
0.6452	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6412	Phase 2
0.64	Remote Similarity	NPD1695	Approved
0.6372	Remote Similarity	NPD8133	Approved
0.6364	Remote Similarity	NPD6686	Approved
0.6327	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5368	Approved
0.6281	Remote Similarity	NPD8293	Discontinued
0.6263	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD5369	Approved
0.623	Remote Similarity	NPD7736	Approved
0.6218	Remote Similarity	NPD6370	Approved
0.62	Remote Similarity	NPD4251	Approved
0.62	Remote Similarity	NPD4250	Approved
0.6198	Remote Similarity	NPD7507	Approved
0.6182	Remote Similarity	NPD6008	Approved
0.6167	Remote Similarity	NPD7122	Discontinued
0.6154	Remote Similarity	NPD5282	Discontinued
0.6148	Remote Similarity	NPD7078	Approved
0.614	Remote Similarity	NPD6882	Approved
0.6132	Remote Similarity	NPD6084	Phase 2
0.6132	Remote Similarity	NPD6083	Phase 2
0.6126	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7492	Approved
0.6106	Remote Similarity	NPD6371	Approved
0.61	Remote Similarity	NPD5786	Approved
0.6095	Remote Similarity	NPD5695	Phase 3
0.6082	Remote Similarity	NPD4790	Discontinued
0.6075	Remote Similarity	NPD5696	Approved
0.6071	Remote Similarity	NPD7320	Approved
0.6068	Remote Similarity	NPD6009	Approved
0.6066	Remote Similarity	NPD6616	Approved
0.605	Remote Similarity	NPD6059	Approved
0.605	Remote Similarity	NPD6054	Approved
0.6048	Remote Similarity	NPD7319	Approved
0.6036	Remote Similarity	NPD6402	Approved
0.6036	Remote Similarity	NPD7128	Approved
0.6036	Remote Similarity	NPD5739	Approved
0.6036	Remote Similarity	NPD6675	Approved
0.602	Remote Similarity	NPD4270	Approved
0.602	Remote Similarity	NPD4269	Approved
0.6019	Remote Similarity	NPD5785	Approved
0.6018	Remote Similarity	NPD6373	Approved
0.6018	Remote Similarity	NPD6372	Approved
0.6018	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.5982	Remote Similarity	NPD5701	Approved
0.5982	Remote Similarity	NPD5697	Approved
0.598	Remote Similarity	NPD6672	Approved
0.598	Remote Similarity	NPD5737	Approved
0.5979	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6411	Approved
0.5962	Remote Similarity	NPD5281	Approved
0.5962	Remote Similarity	NPD5284	Approved
0.596	Remote Similarity	NPD4788	Approved
0.596	Remote Similarity	NPD5332	Approved
0.596	Remote Similarity	NPD7154	Phase 3
0.596	Remote Similarity	NPD5331	Approved
0.5957	Remote Similarity	NPD3702	Approved
0.595	Remote Similarity	NPD5988	Approved
0.5946	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4802	Phase 2
0.5938	Remote Similarity	NPD4238	Approved
0.5929	Remote Similarity	NPD6881	Approved
0.5929	Remote Similarity	NPD6011	Approved
0.5929	Remote Similarity	NPD6899	Approved
0.5926	Remote Similarity	NPD7638	Approved
0.5913	Remote Similarity	NPD6650	Approved
0.5913	Remote Similarity	NPD6649	Approved
0.5902	Remote Similarity	NPD6067	Discontinued
0.59	Remote Similarity	NPD4786	Approved
0.5877	Remote Similarity	NPD6013	Approved
0.5877	Remote Similarity	NPD6012	Approved
0.5877	Remote Similarity	NPD6014	Approved
0.5872	Remote Similarity	NPD7639	Approved
0.5872	Remote Similarity	NPD7640	Approved
0.5865	Remote Similarity	NPD5207	Approved
0.5859	Remote Similarity	NPD3667	Approved
0.5859	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5363	Approved
0.5833	Remote Similarity	NPD6116	Phase 1
0.5826	Remote Similarity	NPD7102	Approved
0.5826	Remote Similarity	NPD6883	Approved
0.5826	Remote Similarity	NPD7290	Approved
0.5825	Remote Similarity	NPD6903	Approved
0.5824	Remote Similarity	NPD229	Approved
0.5818	Remote Similarity	NPD1700	Approved
0.5816	Remote Similarity	NPD4822	Approved
0.5816	Remote Similarity	NPD4821	Approved
0.5816	Remote Similarity	NPD4820	Approved
0.5816	Remote Similarity	NPD4819	Approved
0.5816	Remote Similarity	NPD4252	Approved
0.5814	Remote Similarity	NPD3198	Approved
0.5812	Remote Similarity	NPD4632	Approved
0.581	Remote Similarity	NPD7637	Suspended
0.581	Remote Similarity	NPD7983	Approved
0.5798	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD2257	Approved
0.5784	Remote Similarity	NPD7146	Approved
0.5784	Remote Similarity	NPD6684	Approved
0.5784	Remote Similarity	NPD3618	Phase 1
0.5784	Remote Similarity	NPD5330	Approved
0.5784	Remote Similarity	NPD7521	Approved
0.5784	Remote Similarity	NPD5279	Phase 3
0.5784	Remote Similarity	NPD6409	Approved
0.5784	Remote Similarity	NPD7334	Approved
0.5776	Remote Similarity	NPD6869	Approved
0.5776	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD8130	Phase 1
0.5776	Remote Similarity	NPD6847	Approved
0.5776	Remote Similarity	NPD6617	Approved
0.5776	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6118	Approved
0.5773	Remote Similarity	NPD4268	Approved
0.5773	Remote Similarity	NPD6114	Approved
0.5773	Remote Similarity	NPD6697	Approved
0.5773	Remote Similarity	NPD4271	Approved
0.5773	Remote Similarity	NPD6115	Approved
0.5772	Remote Similarity	NPD8328	Phase 3
0.5769	Remote Similarity	NPD5328	Approved
0.5769	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6101	Approved
0.5769	Remote Similarity	NPD4753	Phase 2
0.5758	Remote Similarity	NPD1779	Approved
0.5758	Remote Similarity	NPD1780	Approved
0.5755	Remote Similarity	NPD5778	Approved
0.5755	Remote Similarity	NPD5779	Approved
0.575	Remote Similarity	NPD7327	Approved
0.575	Remote Similarity	NPD7328	Approved
0.5743	Remote Similarity	NPD3666	Approved
0.5743	Remote Similarity	NPD3665	Phase 1
0.5743	Remote Similarity	NPD3133	Approved
0.5741	Remote Similarity	NPD4697	Phase 3
0.5738	Remote Similarity	NPD8269	Approved
0.5738	Remote Similarity	NPD8268	Approved
0.5738	Remote Similarity	NPD8515	Approved
0.5738	Remote Similarity	NPD8516	Approved
0.5738	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8513	Phase 3
0.5738	Remote Similarity	NPD8517	Approved
0.5738	Remote Similarity	NPD8267	Approved
0.5738	Remote Similarity	NPD8266	Approved
0.5729	Remote Similarity	NPD6117	Approved
0.5726	Remote Similarity	NPD8297	Approved
0.5714	Remote Similarity	NPD46	Approved
0.5714	Remote Similarity	NPD6698	Approved
0.5714	Remote Similarity	NPD6033	Approved
0.5702	Remote Similarity	NPD7516	Approved
0.5701	Remote Similarity	NPD6001	Approved
0.5688	Remote Similarity	NPD4755	Approved
0.5688	Remote Similarity	NPD7902	Approved
0.5684	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6079	Approved
0.5656	Remote Similarity	NPD8377	Approved
0.5656	Remote Similarity	NPD6319	Approved
0.5656	Remote Similarity	NPD8294	Approved
0.5648	Remote Similarity	NPD5210	Approved
0.5648	Remote Similarity	NPD4629	Approved
0.5644	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD3669	Approved
0.5631	Remote Similarity	NPD6098	Approved
0.5619	Remote Similarity	NPD6904	Approved
0.5619	Remote Similarity	NPD6673	Approved
0.5619	Remote Similarity	NPD6080	Approved
0.561	Remote Similarity	NPD8296	Approved
0.561	Remote Similarity	NPD8380	Approved
0.561	Remote Similarity	NPD5983	Phase 2
0.561	Remote Similarity	NPD8335	Approved
0.561	Remote Similarity	NPD8033	Approved
0.561	Remote Similarity	NPD8379	Approved
0.561	Remote Similarity	NPD8378	Approved
0.5607	Remote Similarity	NPD4202	Approved
0.56	Remote Similarity	NPD857	Phase 3

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