NPASS Compound

Structure

NPC120776 OpenBabel07101719512D 27 27 0 0 1 0 0 0 0 0999 V2000 2.1271 14.0021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0919 0.3289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1285 13.9498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6745 13.0588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2191 12.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7651 11.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3098 10.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8558 9.5994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4004 8.7608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9464 7.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4911 7.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0371 6.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5817 5.3014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1277 4.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6724 3.5717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2184 2.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7630 1.8421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 0.7431 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 -1.5962 -0.2079 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 2 0 0 0 0 0 0 0 0 0 -2.5743 -0.4158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 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 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 2 0 0 0 0 8 9 1 0 0 0 0 9 10 2 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 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 2 1 6 0 0 0 22 26 1 0 0 0 0 23 3 1 6 0 0 0 23 27 1 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.28
Volume:	422.423
LogP:	4.769
LogD:	2.605
LogS:	-4.011
# Rotatable Bonds:	14
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	4.033
Fsp3:	0.696
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	3.412041405681521e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.153
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	96.8230972290039%
Volume Distribution (VD):	0.556
Pgp-substrate:	1.2713669538497925%

ADMET: Metabolism

CYP1A2-inhibitor:	0.181
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.423
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.408
CYP2C9-substrate:	0.996
CYP2D6-inhibitor:	0.757
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	2.044
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.464
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.629
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.958
Carcinogencity:	0.18
Eye Corrosion:	0.751
Eye Irritation:	0.817
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC120776

Natural Product ID:	NPC120776
*Common Name:**	Plakinic Acid F
IUPAC Name:	2-[(3R,5R)-5-[(9E,11E,13E)-hexadeca-9,11,13-trienyl]-3,5-dimethyldioxolan-3-yl]acetic acid
Synonyms:	Plakinic Acid F
Standard InCHIKey:	MIXTVNJOFJIRKQ-UGEDBMCTSA-N
Standard InCHI:	InChI=1S/C23H38O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(2)20-23(3,27-26-22)19-21(24)25/h5-10H,4,11-20H2,1-3H3,(H,24,25)/b6-5+,8-7+,10-9+/t22-,23+/m1/s1
SMILES:	CC/C=C/C=C/C=C/CCCCCCCC[C@@]1(C)OO[C@@](C1)(C)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459828
PubChem CID:	9842769
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000105] Dioxolanes [CHEMONTID:0001315] 1,2-dioxolanes

*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
NPO33157	Plakinastrella sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430018]
NPO33157	Plakinastrella sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868160]
NPO33157	Plakinastrella sp.	Species	Plakinidae	Eukaryota	n.a.	Philippine	n.a.	PMID[9868160]

☑ 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	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	25.0	ug.mL-1	PMID[463764]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	3.1	ug.mL-1	PMID[463764]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC90	=	25.0	ug.mL-1	PMID[463764]

☑ 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 NPC120776 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	165
0.1-0.2	1111
0.2-0.3	6073
0.3-0.4	15349
0.4-0.5	11584
0.5-0.6	6692
0.6-0.7	1641
0.7-0.8	79
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC240170
0.9189	High Similarity	NPC145898
0.8077	Intermediate Similarity	NPC469514
0.7887	Intermediate Similarity	NPC469921
0.7765	Intermediate Similarity	NPC477994
0.7765	Intermediate Similarity	NPC477993
0.775	Intermediate Similarity	NPC281296
0.7701	Intermediate Similarity	NPC118193
0.7701	Intermediate Similarity	NPC256902
0.7692	Intermediate Similarity	NPC326024
0.7683	Intermediate Similarity	NPC469920
0.7674	Intermediate Similarity	NPC86005
0.7674	Intermediate Similarity	NPC477959
0.7654	Intermediate Similarity	NPC121200
0.7634	Intermediate Similarity	NPC94487
0.7595	Intermediate Similarity	NPC330016
0.7561	Intermediate Similarity	NPC82488
0.7561	Intermediate Similarity	NPC308545
0.7561	Intermediate Similarity	NPC263574
0.7561	Intermediate Similarity	NPC469747
0.7558	Intermediate Similarity	NPC475753
0.7553	Intermediate Similarity	NPC474820
0.7553	Intermediate Similarity	NPC475978
0.7534	Intermediate Similarity	NPC125312
0.7534	Intermediate Similarity	NPC174560
0.75	Intermediate Similarity	NPC199445
0.7468	Intermediate Similarity	NPC167145
0.7439	Intermediate Similarity	NPC11796
0.7439	Intermediate Similarity	NPC218817
0.7416	Intermediate Similarity	NPC313670
0.7407	Intermediate Similarity	NPC239127
0.7381	Intermediate Similarity	NPC172309
0.7381	Intermediate Similarity	NPC117960
0.7381	Intermediate Similarity	NPC14044
0.7349	Intermediate Similarity	NPC113363
0.7324	Intermediate Similarity	NPC18951
0.7303	Intermediate Similarity	NPC97577
0.7297	Intermediate Similarity	NPC469923
0.7297	Intermediate Similarity	NPC469922
0.7284	Intermediate Similarity	NPC60718
0.7284	Intermediate Similarity	NPC255060
0.7273	Intermediate Similarity	NPC278895
0.7262	Intermediate Similarity	NPC472948
0.7241	Intermediate Similarity	NPC476628
0.7241	Intermediate Similarity	NPC475206
0.7237	Intermediate Similarity	NPC318420
0.7237	Intermediate Similarity	NPC320642
0.7237	Intermediate Similarity	NPC326268
0.7234	Intermediate Similarity	NPC244411
0.7209	Intermediate Similarity	NPC11620
0.7209	Intermediate Similarity	NPC69469
0.7195	Intermediate Similarity	NPC474447
0.7179	Intermediate Similarity	NPC476614
0.7174	Intermediate Similarity	NPC5418
0.7159	Intermediate Similarity	NPC164393
0.7159	Intermediate Similarity	NPC476982
0.7143	Intermediate Similarity	NPC184463
0.7143	Intermediate Similarity	NPC36491
0.7125	Intermediate Similarity	NPC320119
0.7125	Intermediate Similarity	NPC126061
0.7111	Intermediate Similarity	NPC307411
0.7108	Intermediate Similarity	NPC476325
0.7108	Intermediate Similarity	NPC476264
0.7105	Intermediate Similarity	NPC234767
0.7089	Intermediate Similarity	NPC469914
0.7083	Intermediate Similarity	NPC477201
0.7083	Intermediate Similarity	NPC472753
0.7083	Intermediate Similarity	NPC62670
0.7083	Intermediate Similarity	NPC116139
0.7079	Intermediate Similarity	NPC179659
0.7073	Intermediate Similarity	NPC476844
0.7067	Intermediate Similarity	NPC40082
0.7065	Intermediate Similarity	NPC476300
0.7059	Intermediate Similarity	NPC103634
0.7059	Intermediate Similarity	NPC200446
0.7051	Intermediate Similarity	NPC60120
0.7045	Intermediate Similarity	NPC471344
0.7045	Intermediate Similarity	NPC137033
0.7042	Intermediate Similarity	NPC281972
0.7042	Intermediate Similarity	NPC87564
0.7042	Intermediate Similarity	NPC85813
0.7042	Intermediate Similarity	NPC6095
0.7042	Intermediate Similarity	NPC290563
0.7042	Intermediate Similarity	NPC25417
0.7042	Intermediate Similarity	NPC88966
0.7042	Intermediate Similarity	NPC32467
0.7042	Intermediate Similarity	NPC424
0.7042	Intermediate Similarity	NPC261831
0.7042	Intermediate Similarity	NPC154245
0.7037	Intermediate Similarity	NPC474543
0.7037	Intermediate Similarity	NPC325627
0.7037	Intermediate Similarity	NPC238425
0.7037	Intermediate Similarity	NPC472018
0.7033	Intermediate Similarity	NPC51004
0.7033	Intermediate Similarity	NPC478004
0.7033	Intermediate Similarity	NPC476004
0.7033	Intermediate Similarity	NPC158388
0.7033	Intermediate Similarity	NPC478003
0.7033	Intermediate Similarity	NPC474761
0.7021	Intermediate Similarity	NPC180722
0.7021	Intermediate Similarity	NPC165332
0.7021	Intermediate Similarity	NPC195645
0.7021	Intermediate Similarity	NPC9812
0.7011	Intermediate Similarity	NPC310470
0.7011	Intermediate Similarity	NPC476983
0.7011	Intermediate Similarity	NPC477373
0.701	Intermediate Similarity	NPC66110
0.701	Intermediate Similarity	NPC474112
0.701	Intermediate Similarity	NPC472754
0.7	Intermediate Similarity	NPC201046
0.7	Intermediate Similarity	NPC202672
0.7	Intermediate Similarity	NPC69462
0.6988	Remote Similarity	NPC279537
0.6986	Remote Similarity	NPC225929
0.6979	Remote Similarity	NPC469871
0.6979	Remote Similarity	NPC469870
0.6977	Remote Similarity	NPC47031
0.6966	Remote Similarity	NPC470415
0.6966	Remote Similarity	NPC262085
0.6966	Remote Similarity	NPC122502
0.6966	Remote Similarity	NPC476104
0.6966	Remote Similarity	NPC239685
0.6962	Remote Similarity	NPC53302
0.6957	Remote Similarity	NPC472705
0.6957	Remote Similarity	NPC261607
0.6957	Remote Similarity	NPC300312
0.6957	Remote Similarity	NPC111114
0.6957	Remote Similarity	NPC30515
0.6951	Remote Similarity	NPC3753
0.6951	Remote Similarity	NPC237591
0.6951	Remote Similarity	NPC474551
0.6947	Remote Similarity	NPC40812
0.6941	Remote Similarity	NPC274996
0.6941	Remote Similarity	NPC196827
0.6941	Remote Similarity	NPC209995
0.6933	Remote Similarity	NPC251042
0.6933	Remote Similarity	NPC122521
0.6933	Remote Similarity	NPC174447
0.6932	Remote Similarity	NPC471343
0.6923	Remote Similarity	NPC117405
0.6923	Remote Similarity	NPC52198
0.6915	Remote Similarity	NPC36954
0.6915	Remote Similarity	NPC107476
0.6915	Remote Similarity	NPC475659
0.6914	Remote Similarity	NPC288667
0.6914	Remote Similarity	NPC474590
0.6907	Remote Similarity	NPC474742
0.6907	Remote Similarity	NPC47880
0.6905	Remote Similarity	NPC122847
0.6901	Remote Similarity	NPC1813
0.6901	Remote Similarity	NPC321062
0.6901	Remote Similarity	NPC139029
0.6901	Remote Similarity	NPC36061
0.6901	Remote Similarity	NPC70387
0.6901	Remote Similarity	NPC294548
0.6897	Remote Similarity	NPC7414
0.6889	Remote Similarity	NPC197333
0.6889	Remote Similarity	NPC471739
0.6889	Remote Similarity	NPC171722
0.6889	Remote Similarity	NPC248602
0.6882	Remote Similarity	NPC478037
0.6882	Remote Similarity	NPC475912
0.6882	Remote Similarity	NPC478036
0.6882	Remote Similarity	NPC212486
0.6875	Remote Similarity	NPC308567
0.6875	Remote Similarity	NPC317583
0.6875	Remote Similarity	NPC261377
0.6875	Remote Similarity	NPC107130
0.6875	Remote Similarity	NPC187761
0.6875	Remote Similarity	NPC83895
0.6875	Remote Similarity	NPC255592
0.6875	Remote Similarity	NPC64742
0.6867	Remote Similarity	NPC217725
0.6854	Remote Similarity	NPC125290
0.6854	Remote Similarity	NPC474369
0.6854	Remote Similarity	NPC76333
0.6848	Remote Similarity	NPC473448
0.6842	Remote Similarity	NPC473859
0.6842	Remote Similarity	NPC135576
0.6842	Remote Similarity	NPC93271
0.6842	Remote Similarity	NPC476315
0.6837	Remote Similarity	NPC474747
0.6837	Remote Similarity	NPC149371
0.6837	Remote Similarity	NPC478156
0.6835	Remote Similarity	NPC49863
0.6824	Remote Similarity	NPC470905
0.6824	Remote Similarity	NPC192006
0.6824	Remote Similarity	NPC127526
0.6824	Remote Similarity	NPC476627
0.6824	Remote Similarity	NPC469495
0.6824	Remote Similarity	NPC179028
0.6824	Remote Similarity	NPC321514
0.6824	Remote Similarity	NPC476986
0.6818	Remote Similarity	NPC250315
0.6818	Remote Similarity	NPC475989
0.6818	Remote Similarity	NPC170377
0.6813	Remote Similarity	NPC475101
0.6813	Remote Similarity	NPC476707
0.6813	Remote Similarity	NPC476706
0.6813	Remote Similarity	NPC476704

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 NPC120776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1779
0.2-0.3	4097
0.3-0.4	2111
0.4-0.5	645
0.5-0.6	314
0.6-0.7	44
0.7-0.8	11
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
0.7444	Intermediate Similarity	NPD5778	Approved
0.7444	Intermediate Similarity	NPD5779	Approved
0.7333	Intermediate Similarity	NPD7983	Approved
0.7303	Intermediate Similarity	NPD6101	Approved
0.7303	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5368	Approved
0.7176	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD7331	Phase 2
0.7093	Intermediate Similarity	NPD6435	Approved
0.7042	Intermediate Similarity	NPD3195	Phase 2
0.7042	Intermediate Similarity	NPD3194	Approved
0.7042	Intermediate Similarity	NPD4266	Approved
0.7042	Intermediate Similarity	NPD3196	Approved
0.7021	Intermediate Similarity	NPD7839	Suspended
0.6966	Remote Similarity	NPD5786	Approved
0.6901	Remote Similarity	NPD3172	Approved
0.6897	Remote Similarity	NPD4269	Approved
0.6897	Remote Similarity	NPD4270	Approved
0.6835	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6629	Remote Similarity	NPD7154	Phase 3
0.6628	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3732	Approved
0.662	Remote Similarity	NPD29	Approved
0.662	Remote Similarity	NPD28	Approved
0.6562	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5282	Discontinued
0.6456	Remote Similarity	NPD3197	Phase 1
0.6444	Remote Similarity	NPD5362	Discontinued
0.6437	Remote Similarity	NPD4271	Approved
0.6437	Remote Similarity	NPD4268	Approved
0.6421	Remote Similarity	NPD5284	Approved
0.6421	Remote Similarity	NPD5281	Approved
0.6421	Remote Similarity	NPD7637	Suspended
0.6344	Remote Similarity	NPD4251	Approved
0.6344	Remote Similarity	NPD4250	Approved
0.6338	Remote Similarity	NPD3173	Approved
0.6333	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5785	Approved
0.6304	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4249	Approved
0.6197	Remote Similarity	NPD622	Approved
0.6146	Remote Similarity	NPD46	Approved
0.6146	Remote Similarity	NPD7838	Discovery
0.6146	Remote Similarity	NPD6698	Approved
0.6106	Remote Similarity	NPD8513	Phase 3
0.6106	Remote Similarity	NPD8515	Approved
0.6106	Remote Similarity	NPD8517	Approved
0.6106	Remote Similarity	NPD8516	Approved
0.6087	Remote Similarity	NPD5332	Approved
0.6087	Remote Similarity	NPD5331	Approved
0.6044	Remote Similarity	NPD4790	Discontinued
0.6042	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD5048	Discontinued
0.5979	Remote Similarity	NPD5207	Approved
0.5955	Remote Similarity	NPD4756	Discovery
0.5941	Remote Similarity	NPD6084	Phase 2
0.5941	Remote Similarity	NPD6083	Phase 2
0.5938	Remote Similarity	NPD4518	Approved
0.5926	Remote Similarity	NPD6371	Approved
0.5918	Remote Similarity	NPD5694	Approved
0.5918	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6050	Approved
0.5915	Remote Similarity	NPD3174	Discontinued
0.5915	Remote Similarity	NPD4222	Approved
0.5915	Remote Similarity	NPD39	Approved
0.59	Remote Similarity	NPD5695	Phase 3
0.5895	Remote Similarity	NPD5280	Approved
0.5895	Remote Similarity	NPD6422	Discontinued
0.5895	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4694	Approved
0.5888	Remote Similarity	NPD6881	Approved
0.5888	Remote Similarity	NPD6899	Approved
0.5876	Remote Similarity	NPD1695	Approved
0.5876	Remote Similarity	NPD5346	Phase 2
0.5876	Remote Similarity	NPD5347	Phase 2
0.5872	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.587	Remote Similarity	NPD857	Phase 3
0.5859	Remote Similarity	NPD6399	Phase 3
0.5854	Remote Similarity	NPD7909	Approved
0.5849	Remote Similarity	NPD6402	Approved
0.5849	Remote Similarity	NPD5739	Approved
0.5849	Remote Similarity	NPD7128	Approved
0.5849	Remote Similarity	NPD6675	Approved
0.5847	Remote Similarity	NPD8074	Phase 3
0.5833	Remote Similarity	NPD3573	Approved
0.5833	Remote Similarity	NPD4793	Discontinued
0.5818	Remote Similarity	NPD6053	Discontinued
0.5816	Remote Similarity	NPD5692	Phase 3
0.5812	Remote Similarity	NPD7492	Approved
0.5812	Remote Similarity	NPD8340	Approved
0.5812	Remote Similarity	NPD8299	Approved
0.5812	Remote Similarity	NPD8342	Approved
0.5812	Remote Similarity	NPD8341	Approved
0.581	Remote Similarity	NPD5765	Approved
0.5806	Remote Similarity	NPD5209	Approved
0.5806	Remote Similarity	NPD4223	Phase 3
0.5806	Remote Similarity	NPD4221	Approved
0.58	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD6685	Approved
0.5789	Remote Similarity	NPD5329	Approved
0.578	Remote Similarity	NPD6883	Approved
0.578	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD7290	Approved
0.578	Remote Similarity	NPD4634	Approved
0.5778	Remote Similarity	NPD6932	Approved
0.5763	Remote Similarity	NPD6616	Approved
0.5763	Remote Similarity	NPD8451	Approved
0.5761	Remote Similarity	NPD6930	Phase 2
0.5761	Remote Similarity	NPD6931	Approved
0.5761	Remote Similarity	NPD4695	Discontinued
0.5761	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6079	Approved
0.5758	Remote Similarity	NPD7515	Phase 2
0.5745	Remote Similarity	NPD6695	Phase 3
0.5741	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7320	Approved
0.5739	Remote Similarity	NPD6319	Approved
0.5739	Remote Similarity	NPD6054	Approved
0.5732	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4623	Approved
0.5729	Remote Similarity	NPD5690	Phase 2
0.5729	Remote Similarity	NPD5279	Phase 3
0.5729	Remote Similarity	NPD6098	Approved
0.5729	Remote Similarity	NPD4519	Discontinued
0.5728	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5696	Approved
0.5727	Remote Similarity	NPD1719	Phase 1
0.5727	Remote Similarity	NPD8130	Phase 1
0.5727	Remote Similarity	NPD6617	Approved
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD6869	Approved
0.5727	Remote Similarity	NPD6847	Approved
0.5727	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD6080	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.57	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD226	Approved
0.5694	Remote Similarity	NPD634	Phase 3
0.569	Remote Similarity	NPD8444	Approved
0.5688	Remote Similarity	NPD6014	Approved
0.5688	Remote Similarity	NPD6013	Approved
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5688	Remote Similarity	NPD6012	Approved
0.5684	Remote Similarity	NPD4786	Approved
0.5684	Remote Similarity	NPD4197	Approved
0.5684	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8297	Approved
0.5676	Remote Similarity	NPD6882	Approved
0.5673	Remote Similarity	NPD5285	Approved
0.5673	Remote Similarity	NPD5286	Approved
0.5673	Remote Similarity	NPD4696	Approved
0.5667	Remote Similarity	NPD7736	Approved
0.5658	Remote Similarity	NPD3186	Phase 1
0.5657	Remote Similarity	NPD4096	Approved
0.5652	Remote Similarity	NPD6929	Approved
0.5648	Remote Similarity	NPD5701	Approved
0.5644	Remote Similarity	NPD7748	Approved
0.5641	Remote Similarity	NPD6370	Approved
0.5638	Remote Similarity	NPD3667	Approved
0.5638	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD5326	Phase 3
0.5631	Remote Similarity	NPD4755	Approved
0.5625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4632	Approved
0.5618	Remote Similarity	NPD6924	Approved
0.5618	Remote Similarity	NPD6926	Approved
0.5612	Remote Similarity	NPD6672	Approved
0.5612	Remote Similarity	NPD5737	Approved
0.561	Remote Similarity	NPD4194	Approved
0.561	Remote Similarity	NPD4191	Approved
0.561	Remote Similarity	NPD4193	Approved
0.561	Remote Similarity	NPD4192	Approved
0.5603	Remote Similarity	NPD6059	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