NPASS Compound

Structure

NPC469483 OpenBabel07101718282D 34 34 0 0 1 0 0 0 0 0999 V2000 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 13.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1603 13.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2942 10.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 7.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 8.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 9.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 10.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 10.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.5622 13.0388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.2942 13.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 10.5388 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 -4.6962 11.5388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.5622 12.0388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.8301 12.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2942 12.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 10.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 13.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 11.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 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 -6.4282 13.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 11.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 32 1 0 0 0 0 19 24 1 0 0 0 0 19 33 1 0 0 0 0 20 27 2 0 0 0 0 20 33 1 0 0 0 0 21 28 2 0 0 0 0 21 34 1 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 34 1 0 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.29
Volume:	506.835
LogP:	5.829
LogD:	3.124
LogS:	-3.936
# Rotatable Bonds:	20
TPSA:	123.27
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.201
Synthetic Accessibility Score:	3.863
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.251
MDCK Permeability:	2.572721496107988e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.084
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	96.8905258178711%
Volume Distribution (VD):	0.634
Pgp-substrate:	2.356219530105591%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.187
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.714
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	1.819
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.364
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.773
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.75
Carcinogencity:	0.131
Eye Corrosion:	0.039
Eye Irritation:	0.043
Respiratory Toxicity:	0.138

Download Data

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

Natural Product: NPC469483

Natural Product ID:	NPC469483
*Common Name:**	2-(13-Carboxy-14,15-Diacetoxyhexadecanyl)-2-Penten-4-Olide
IUPAC Name:	2-(1,2-diacetyloxypropyl)-14-(2-methyl-5-oxo-2H-furan-4-yl)tetradecanoic acid
Synonyms:
Standard InCHIKey:	NZDLKRNSMSJUTP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H42O8/c1-18-17-22(26(31)32-18)15-13-11-9-7-5-6-8-10-12-14-16-23(25(29)30)24(34-21(4)28)19(2)33-20(3)27/h17-19,23-24H,5-16H2,1-4H3,(H,29,30)
SMILES:	CC1C=C(C(=O)O1)CCCCCCCCCCCCC(C(C(C)OC(=O)C)OC(=O)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080095
PubChem CID:	46879378
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO13341	Bryopsis pennata	Species	Bryopsidaceae	Eukaryota	n.a.	Hawaiian	n.a.	PMID[19916528]
NPO13341	Bryopsis pennata	Species	Bryopsidaceae	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
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT267	Individual Protein	Neuropeptide Y receptor type 1	Homo sapiens	Activity	=	100.0	%	PMID[568632]
NPT267	Individual Protein	Neuropeptide Y receptor type 1	Homo sapiens	Activity	=	86.0	%	PMID[568632]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	Activity	=	98.0	%	PMID[568632]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	Activity	=	79.0	%	PMID[568632]

☑ 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 NPC469483 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	202
0.1-0.2	1178
0.2-0.3	4885
0.3-0.4	9674
0.4-0.5	14542
0.5-0.6	7257
0.6-0.7	3658
0.7-0.8	1212
0.8-0.85	84
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC475947
0.8621	High Similarity	NPC476805
0.8488	Intermediate Similarity	NPC470755
0.8452	Intermediate Similarity	NPC471325
0.8444	Intermediate Similarity	NPC476300
0.8444	Intermediate Similarity	NPC469645
0.8444	Intermediate Similarity	NPC469692
0.8434	Intermediate Similarity	NPC19841
0.8427	Intermediate Similarity	NPC473448
0.8427	Intermediate Similarity	NPC474232
0.8415	Intermediate Similarity	NPC97516
0.8409	Intermediate Similarity	NPC476803
0.8409	Intermediate Similarity	NPC475819
0.8391	Intermediate Similarity	NPC305475
0.8391	Intermediate Similarity	NPC469910
0.8391	Intermediate Similarity	NPC261721
0.8391	Intermediate Similarity	NPC475461
0.8372	Intermediate Similarity	NPC158756
0.8352	Intermediate Similarity	NPC121825
0.8315	Intermediate Similarity	NPC130359
0.8315	Intermediate Similarity	NPC14901
0.8313	Intermediate Similarity	NPC108816
0.8313	Intermediate Similarity	NPC128276
0.8313	Intermediate Similarity	NPC93763
0.8295	Intermediate Similarity	NPC178215
0.828	Intermediate Similarity	NPC40812
0.8276	Intermediate Similarity	NPC477014
0.8276	Intermediate Similarity	NPC477013
0.8276	Intermediate Similarity	NPC255307
0.8261	Intermediate Similarity	NPC475659
0.8261	Intermediate Similarity	NPC471142
0.8261	Intermediate Similarity	NPC36954
0.8256	Intermediate Similarity	NPC40746
0.8256	Intermediate Similarity	NPC169575
0.8222	Intermediate Similarity	NPC51004
0.8214	Intermediate Similarity	NPC178277
0.8202	Intermediate Similarity	NPC233551
0.8202	Intermediate Similarity	NPC21208
0.8202	Intermediate Similarity	NPC280621
0.8202	Intermediate Similarity	NPC20339
0.8202	Intermediate Similarity	NPC48338
0.8202	Intermediate Similarity	NPC40376
0.8193	Intermediate Similarity	NPC57744
0.8191	Intermediate Similarity	NPC261377
0.8191	Intermediate Similarity	NPC308567
0.8191	Intermediate Similarity	NPC255592
0.8182	Intermediate Similarity	NPC134865
0.8182	Intermediate Similarity	NPC150755
0.8182	Intermediate Similarity	NPC477015
0.8182	Intermediate Similarity	NPC103523
0.8172	Intermediate Similarity	NPC476315
0.8172	Intermediate Similarity	NPC473859
0.8172	Intermediate Similarity	NPC230800
0.8172	Intermediate Similarity	NPC279621
0.8171	Intermediate Similarity	NPC329852
0.8161	Intermediate Similarity	NPC476804
0.8161	Intermediate Similarity	NPC96259
0.8161	Intermediate Similarity	NPC163093
0.8161	Intermediate Similarity	NPC191476
0.8161	Intermediate Similarity	NPC141193
0.8161	Intermediate Similarity	NPC114979
0.8148	Intermediate Similarity	NPC144419
0.814	Intermediate Similarity	NPC85772
0.814	Intermediate Similarity	NPC474291
0.8132	Intermediate Similarity	NPC184463
0.8132	Intermediate Similarity	NPC30515
0.8125	Intermediate Similarity	NPC149371
0.8125	Intermediate Similarity	NPC67183
0.8111	Intermediate Similarity	NPC307411
0.8111	Intermediate Similarity	NPC280612
0.8105	Intermediate Similarity	NPC288876
0.8095	Intermediate Similarity	NPC11796
0.8095	Intermediate Similarity	NPC218817
0.8085	Intermediate Similarity	NPC471462
0.8072	Intermediate Similarity	NPC123360
0.8068	Intermediate Similarity	NPC471567
0.8068	Intermediate Similarity	NPC473669
0.8068	Intermediate Similarity	NPC231009
0.8068	Intermediate Similarity	NPC283085
0.8068	Intermediate Similarity	NPC1083
0.8068	Intermediate Similarity	NPC107986
0.8068	Intermediate Similarity	NPC329838
0.8068	Intermediate Similarity	NPC223871
0.8068	Intermediate Similarity	NPC182383
0.8068	Intermediate Similarity	NPC132496
0.8068	Intermediate Similarity	NPC120398
0.8068	Intermediate Similarity	NPC473651
0.8068	Intermediate Similarity	NPC165162
0.8068	Intermediate Similarity	NPC103284
0.8068	Intermediate Similarity	NPC286338
0.8068	Intermediate Similarity	NPC66346
0.8068	Intermediate Similarity	NPC82795
0.8068	Intermediate Similarity	NPC329615
0.8068	Intermediate Similarity	NPC261380
0.8068	Intermediate Similarity	NPC110710
0.8068	Intermediate Similarity	NPC473478
0.8065	Intermediate Similarity	NPC477922
0.8065	Intermediate Similarity	NPC471141
0.8049	Intermediate Similarity	NPC140287
0.8049	Intermediate Similarity	NPC476355
0.8049	Intermediate Similarity	NPC474758
0.8046	Intermediate Similarity	NPC131669
0.8046	Intermediate Similarity	NPC473390
0.8046	Intermediate Similarity	NPC59097
0.8043	Intermediate Similarity	NPC273579
0.8043	Intermediate Similarity	NPC162205
0.8043	Intermediate Similarity	NPC295204
0.8043	Intermediate Similarity	NPC288240
0.8043	Intermediate Similarity	NPC475302
0.8043	Intermediate Similarity	NPC475912
0.8041	Intermediate Similarity	NPC472755
0.8023	Intermediate Similarity	NPC25684
0.8023	Intermediate Similarity	NPC301477
0.8023	Intermediate Similarity	NPC141810
0.8023	Intermediate Similarity	NPC325031
0.8023	Intermediate Similarity	NPC281949
0.8023	Intermediate Similarity	NPC24417
0.8022	Intermediate Similarity	NPC475748
0.8022	Intermediate Similarity	NPC473619
0.8022	Intermediate Similarity	NPC239517
0.8021	Intermediate Similarity	NPC47880
0.8021	Intermediate Similarity	NPC128733
0.8021	Intermediate Similarity	NPC185141
0.8021	Intermediate Similarity	NPC133907
0.8021	Intermediate Similarity	NPC164598
0.8021	Intermediate Similarity	NPC474339
0.8021	Intermediate Similarity	NPC46998
0.8021	Intermediate Similarity	NPC110443
0.8	Intermediate Similarity	NPC161855
0.8	Intermediate Similarity	NPC260343
0.8	Intermediate Similarity	NPC89001
0.8	Intermediate Similarity	NPC320458
0.8	Intermediate Similarity	NPC167881
0.8	Intermediate Similarity	NPC187761
0.8	Intermediate Similarity	NPC270126
0.8	Intermediate Similarity	NPC98557
0.8	Intermediate Similarity	NPC473905
0.8	Intermediate Similarity	NPC471144
0.8	Intermediate Similarity	NPC83895
0.798	Intermediate Similarity	NPC26617
0.7979	Intermediate Similarity	NPC477921
0.7978	Intermediate Similarity	NPC142117
0.7978	Intermediate Similarity	NPC308412
0.7978	Intermediate Similarity	NPC107717
0.7978	Intermediate Similarity	NPC62118
0.7978	Intermediate Similarity	NPC69082
0.7978	Intermediate Similarity	NPC210218
0.7978	Intermediate Similarity	NPC171174
0.7978	Intermediate Similarity	NPC232555
0.7978	Intermediate Similarity	NPC240695
0.7978	Intermediate Similarity	NPC114694
0.7978	Intermediate Similarity	NPC112685
0.7978	Intermediate Similarity	NPC475581
0.7978	Intermediate Similarity	NPC134885
0.7978	Intermediate Similarity	NPC473687
0.7978	Intermediate Similarity	NPC204686
0.7978	Intermediate Similarity	NPC231096
0.7978	Intermediate Similarity	NPC134807
0.7978	Intermediate Similarity	NPC219498
0.7978	Intermediate Similarity	NPC279267
0.7978	Intermediate Similarity	NPC47937
0.7976	Intermediate Similarity	NPC141789
0.7976	Intermediate Similarity	NPC171204
0.7976	Intermediate Similarity	NPC320630
0.7976	Intermediate Similarity	NPC474760
0.7976	Intermediate Similarity	NPC476028
0.7976	Intermediate Similarity	NPC116177
0.7976	Intermediate Similarity	NPC7563
0.7959	Intermediate Similarity	NPC472756
0.7957	Intermediate Similarity	NPC474247
0.7957	Intermediate Similarity	NPC469632
0.7955	Intermediate Similarity	NPC70424
0.7955	Intermediate Similarity	NPC243618
0.7955	Intermediate Similarity	NPC156804
0.7955	Intermediate Similarity	NPC9868
0.7955	Intermediate Similarity	NPC82297
0.7952	Intermediate Similarity	NPC329826
0.7952	Intermediate Similarity	NPC469414
0.7938	Intermediate Similarity	NPC472754
0.7935	Intermediate Similarity	NPC158061
0.7935	Intermediate Similarity	NPC472814
0.7935	Intermediate Similarity	NPC261607
0.7935	Intermediate Similarity	NPC177037
0.7935	Intermediate Similarity	NPC300312
0.7935	Intermediate Similarity	NPC476705
0.7935	Intermediate Similarity	NPC111114
0.7935	Intermediate Similarity	NPC473321
0.7931	Intermediate Similarity	NPC35556
0.7931	Intermediate Similarity	NPC473780
0.7931	Intermediate Similarity	NPC473529
0.7931	Intermediate Similarity	NPC94875
0.7931	Intermediate Similarity	NPC11332
0.7931	Intermediate Similarity	NPC475159
0.7931	Intermediate Similarity	NPC475690
0.7931	Intermediate Similarity	NPC89555
0.7931	Intermediate Similarity	NPC145914
0.7931	Intermediate Similarity	NPC73310
0.7931	Intermediate Similarity	NPC65930
0.7931	Intermediate Similarity	NPC180363
0.7931	Intermediate Similarity	NPC229825

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 NPC469483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1774
0.2-0.3	3664
0.3-0.4	2284
0.4-0.5	858
0.5-0.6	314
0.6-0.7	65
0.7-0.8	14
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
0.8222	Intermediate Similarity	NPD46	Approved
0.8222	Intermediate Similarity	NPD6698	Approved
0.798	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5785	Approved
0.7742	Intermediate Similarity	NPD7983	Approved
0.7684	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5363	Approved
0.7634	Intermediate Similarity	NPD7838	Discovery
0.7573	Intermediate Similarity	NPD6371	Approved
0.7549	Intermediate Similarity	NPD6686	Approved
0.7449	Intermediate Similarity	NPD4225	Approved
0.7444	Intermediate Similarity	NPD7154	Phase 3
0.7333	Intermediate Similarity	NPD4269	Approved
0.7333	Intermediate Similarity	NPD4270	Approved
0.7333	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5369	Approved
0.7204	Intermediate Similarity	NPD5786	Approved
0.7143	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD5209	Approved
0.7111	Intermediate Similarity	NPD4252	Approved
0.7111	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.7	Intermediate Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD5779	Approved
0.6939	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD4821	Approved
0.6923	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD5368	Approved
0.6923	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD1694	Approved
0.69	Remote Similarity	NPD7839	Suspended
0.6889	Remote Similarity	NPD4268	Approved
0.6889	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4271	Approved
0.6867	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6101	Approved
0.6804	Remote Similarity	NPD1695	Approved
0.6759	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8039	Approved
0.67	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6411	Approved
0.6635	Remote Similarity	NPD5344	Discontinued
0.6633	Remote Similarity	NPD5370	Suspended
0.6609	Remote Similarity	NPD8517	Approved
0.6609	Remote Similarity	NPD8515	Approved
0.6609	Remote Similarity	NPD8516	Approved
0.6609	Remote Similarity	NPD8513	Phase 3
0.6602	Remote Similarity	NPD7638	Approved
0.66	Remote Similarity	NPD6399	Phase 3
0.6598	Remote Similarity	NPD4251	Approved
0.6598	Remote Similarity	NPD4250	Approved
0.6538	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD7639	Approved
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5331	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7319	Approved
0.6496	Remote Similarity	NPD7830	Approved
0.6496	Remote Similarity	NPD7829	Approved
0.6496	Remote Similarity	NPD7642	Approved
0.6495	Remote Similarity	NPD4249	Approved
0.6489	Remote Similarity	NPD4790	Discontinued
0.6486	Remote Similarity	NPD6053	Discontinued
0.6486	Remote Similarity	NPD8297	Approved
0.6481	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4756	Discovery
0.6404	Remote Similarity	NPD7500	Approved
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6395	Remote Similarity	NPD7331	Phase 2
0.6387	Remote Similarity	NPD7507	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6353	Remote Similarity	NPD3197	Phase 1
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6333	Remote Similarity	NPD8074	Phase 3
0.6327	Remote Similarity	NPD7334	Approved
0.6327	Remote Similarity	NPD7521	Approved
0.6327	Remote Similarity	NPD5330	Approved
0.6327	Remote Similarity	NPD6409	Approved
0.6327	Remote Similarity	NPD7146	Approved
0.6327	Remote Similarity	NPD6684	Approved
0.6311	Remote Similarity	NPD5695	Phase 3
0.6306	Remote Similarity	NPD2067	Discontinued
0.6286	Remote Similarity	NPD5696	Approved
0.6273	Remote Similarity	NPD6899	Approved
0.6273	Remote Similarity	NPD6881	Approved
0.627	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD5739	Approved
0.6239	Remote Similarity	NPD6402	Approved
0.6239	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD7900	Approved
0.6214	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7641	Discontinued
0.62	Remote Similarity	NPD5737	Approved
0.62	Remote Similarity	NPD6672	Approved
0.62	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6903	Approved
0.6195	Remote Similarity	NPD6882	Approved
0.6186	Remote Similarity	NPD8444	Approved
0.6186	Remote Similarity	NPD6110	Phase 1
0.6182	Remote Similarity	NPD6412	Phase 2
0.6182	Remote Similarity	NPD5697	Approved
0.6176	Remote Similarity	NPD7515	Phase 2
0.617	Remote Similarity	NPD3732	Approved
0.6162	Remote Similarity	NPD6422	Discontinued
0.6161	Remote Similarity	NPD7290	Approved
0.6161	Remote Similarity	NPD6883	Approved
0.6161	Remote Similarity	NPD7102	Approved
0.6129	Remote Similarity	NPD7260	Phase 2
0.6126	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7320	Approved
0.6121	Remote Similarity	NPD7505	Discontinued
0.6116	Remote Similarity	NPD8451	Approved
0.6116	Remote Similarity	NPD8273	Phase 1
0.6106	Remote Similarity	NPD2204	Approved
0.6106	Remote Similarity	NPD6869	Approved
0.6106	Remote Similarity	NPD6617	Approved
0.6106	Remote Similarity	NPD6847	Approved
0.6106	Remote Similarity	NPD8130	Phase 1
0.6092	Remote Similarity	NPD7341	Phase 2
0.6083	Remote Similarity	NPD8328	Phase 3
0.6071	Remote Similarity	NPD6013	Approved
0.6071	Remote Similarity	NPD6014	Approved
0.6071	Remote Similarity	NPD6012	Approved
0.6068	Remote Similarity	NPD7328	Approved
0.6068	Remote Similarity	NPD7327	Approved
0.6066	Remote Similarity	NPD8448	Approved
0.6055	Remote Similarity	NPD6647	Phase 2
0.6049	Remote Similarity	NPD4266	Approved
0.6049	Remote Similarity	NPD3194	Approved
0.6049	Remote Similarity	NPD3195	Phase 2
0.6049	Remote Similarity	NPD3196	Approved
0.6036	Remote Similarity	NPD5701	Approved
0.6033	Remote Similarity	NPD7492	Approved
0.6019	Remote Similarity	NPD8035	Phase 2
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD5281	Approved
0.6019	Remote Similarity	NPD5693	Phase 1
0.6019	Remote Similarity	NPD5284	Approved
0.6017	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6616	Approved
0.5982	Remote Similarity	NPD6011	Approved
0.5966	Remote Similarity	NPD8294	Approved
0.5966	Remote Similarity	NPD6054	Approved
0.5966	Remote Similarity	NPD8377	Approved
0.5963	Remote Similarity	NPD7632	Discontinued
0.596	Remote Similarity	NPD3665	Phase 1
0.596	Remote Similarity	NPD3666	Approved
0.596	Remote Similarity	NPD3133	Approved
0.5943	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7078	Approved
0.5929	Remote Similarity	NPD6413	Approved
0.5926	Remote Similarity	NPD3172	Approved
0.592	Remote Similarity	NPD8390	Approved
0.592	Remote Similarity	NPD8392	Approved
0.592	Remote Similarity	NPD8391	Approved
0.5917	Remote Similarity	NPD8335	Approved
0.5917	Remote Similarity	NPD8378	Approved
0.5917	Remote Similarity	NPD7503	Approved
0.5917	Remote Similarity	NPD8380	Approved
0.5917	Remote Similarity	NPD8033	Approved
0.5917	Remote Similarity	NPD8379	Approved
0.5917	Remote Similarity	NPD8296	Approved
0.5902	Remote Similarity	NPD8341	Approved
0.5902	Remote Similarity	NPD8342	Approved
0.5902	Remote Similarity	NPD8340	Approved
0.5902	Remote Similarity	NPD8299	Approved
0.5887	Remote Similarity	NPD7736	Approved
0.5877	Remote Similarity	NPD6421	Discontinued
0.5876	Remote Similarity	NPD4695	Discontinued
0.5875	Remote Similarity	NPD6927	Phase 3
0.5868	Remote Similarity	NPD6370	Approved
0.5868	Remote Similarity	NPD8080	Discontinued
0.5865	Remote Similarity	NPD6079	Approved
0.5862	Remote Similarity	NPD4632	Approved
0.5862	Remote Similarity	NPD8133	Approved
0.5862	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3728	Approved
0.5854	Remote Similarity	NPD3730	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