NPASS Compound

Structure

NPC474472 OpenBabel07101718332D 28 31 0 0 1 0 0 0 0 0999 V2000 3.4252 2.5333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6126 2.3237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6564 4.3798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9831 5.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3498 1.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8852 3.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9753 2.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1944 3.8842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5054 4.0184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3932 1.2343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0091 3.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2894 1.3424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5263 2.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6468 2.2458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8072 2.1613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1307 2.9652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1944 4.8250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4503 0.8579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5160 3.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8239 3.8842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7549 4.6312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5178 0.8189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2315 1.3704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4074 4.3022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0964 3.0432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1251 4.5554 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 1.7822 4.6415 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 23 2 0 0 0 0 14 25 1 0 0 0 0 15 6 1 1 0 0 0 16 20 1 6 0 0 0 16 25 1 0 0 0 0 17 21 1 6 0 0 0 17 26 1 0 0 0 0 18 22 1 1 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 3 1 1 0 0 0 20 26 1 0 0 0 0 21 4 1 1 0 0 0 21 28 1 0 0 0 0 22 5 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	399.674
LogP:	3.431
LogD:	2.055
LogS:	-4.273
# Rotatable Bonds:	2
TPSA:	74.36
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	6.2
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.844
MDCK Permeability:	3.016508708242327e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.786
30% Bioavailability (F30%):	0.607

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	81.45223236083984%
Volume Distribution (VD):	1.581
Pgp-substrate:	18.138330459594727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.593
CYP2C9-inhibitor:	0.093
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	3.607
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.583
Drug-inuced Liver Injury (DILI):	0.86
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.424
Skin Sensitization:	0.959
Carcinogencity:	0.356
Eye Corrosion:	0.788
Eye Irritation:	0.457
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: NPC474472

Natural Product ID:	NPC474472
*Common Name:**	SBHQTFJDBYTNNZ-HZFQQVEYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SBHQTFJDBYTNNZ-HZFQQVEYSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-13-15-6-9-21(4,28-19(13)24)17-8-11-20(3,26-17)16(25-14(2)23)7-10-22(5)18(12-15)27-22/h15-18H,1,6-12H2,2-5H3/t15-,16+,17+,18-,20-,21-,22+/m1/s1
SMILES:	CC(=O)OC1CCC2(C(O2)CC3CCC(C4CCC1(O4)C)(OC(=O)C3=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469487
PubChem CID:	44560943
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	chinese soft coral	n.a.	PMID[18553926]
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30528697]
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644083]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[542997]

☑ 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 NPC474472 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	249
0.1-0.2	2235
0.2-0.3	7506
0.3-0.4	15545
0.4-0.5	9368
0.5-0.6	5541
0.6-0.7	1791
0.7-0.8	399
0.8-0.85	42
0.85-0.9	14
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC257358
0.961	High Similarity	NPC474981
0.9259	High Similarity	NPC304509
0.9259	High Similarity	NPC149725
0.9259	High Similarity	NPC47958
0.9146	High Similarity	NPC474762
0.9146	High Similarity	NPC476015
0.9146	High Similarity	NPC475019
0.9146	High Similarity	NPC474949
0.9024	High Similarity	NPC329749
0.881	High Similarity	NPC5130
0.881	High Similarity	NPC231889
0.8721	High Similarity	NPC475748
0.8675	High Similarity	NPC474780
0.8605	High Similarity	NPC474951
0.8605	High Similarity	NPC151770
0.8554	High Similarity	NPC272814
0.8488	Intermediate Similarity	NPC58219
0.8488	Intermediate Similarity	NPC281516
0.8488	Intermediate Similarity	NPC177629
0.8471	Intermediate Similarity	NPC470242
0.8452	Intermediate Similarity	NPC470238
0.8452	Intermediate Similarity	NPC151176
0.8452	Intermediate Similarity	NPC475963
0.8452	Intermediate Similarity	NPC3464
0.8452	Intermediate Similarity	NPC138647
0.8391	Intermediate Similarity	NPC92974
0.8391	Intermediate Similarity	NPC173926
0.8391	Intermediate Similarity	NPC307411
0.8372	Intermediate Similarity	NPC186148
0.8372	Intermediate Similarity	NPC248602
0.8315	Intermediate Similarity	NPC212486
0.8295	Intermediate Similarity	NPC51004
0.8276	Intermediate Similarity	NPC474471
0.8276	Intermediate Similarity	NPC227379
0.8242	Intermediate Similarity	NPC476315
0.8222	Intermediate Similarity	NPC473316
0.8222	Intermediate Similarity	NPC81386
0.8222	Intermediate Similarity	NPC474035
0.8222	Intermediate Similarity	NPC473330
0.8202	Intermediate Similarity	NPC70251
0.8202	Intermediate Similarity	NPC475881
0.8202	Intermediate Similarity	NPC30515
0.8202	Intermediate Similarity	NPC329952
0.8202	Intermediate Similarity	NPC184463
0.8182	Intermediate Similarity	NPC166919
0.8161	Intermediate Similarity	NPC475703
0.8161	Intermediate Similarity	NPC270270
0.814	Intermediate Similarity	NPC50362
0.814	Intermediate Similarity	NPC38468
0.814	Intermediate Similarity	NPC99395
0.814	Intermediate Similarity	NPC197903
0.814	Intermediate Similarity	NPC319795
0.8132	Intermediate Similarity	NPC270013
0.8132	Intermediate Similarity	NPC14961
0.8132	Intermediate Similarity	NPC475900
0.8118	Intermediate Similarity	NPC170377
0.8111	Intermediate Similarity	NPC476300
0.809	Intermediate Similarity	NPC469718
0.809	Intermediate Similarity	NPC62815
0.809	Intermediate Similarity	NPC476004
0.809	Intermediate Similarity	NPC329857
0.809	Intermediate Similarity	NPC474761
0.8068	Intermediate Similarity	NPC202672
0.8068	Intermediate Similarity	NPC153805
0.8046	Intermediate Similarity	NPC469676
0.8046	Intermediate Similarity	NPC50637
0.8022	Intermediate Similarity	NPC471147
0.8	Intermediate Similarity	NPC12172
0.8	Intermediate Similarity	NPC208886
0.8	Intermediate Similarity	NPC246076
0.8	Intermediate Similarity	NPC20713
0.7979	Intermediate Similarity	NPC186861
0.7978	Intermediate Similarity	NPC472872
0.7955	Intermediate Similarity	NPC118601
0.7955	Intermediate Similarity	NPC190753
0.7935	Intermediate Similarity	NPC475659
0.7935	Intermediate Similarity	NPC36954
0.7935	Intermediate Similarity	NPC476053
0.7931	Intermediate Similarity	NPC474547
0.7912	Intermediate Similarity	NPC81419
0.7912	Intermediate Similarity	NPC475912
0.7912	Intermediate Similarity	NPC179746
0.7907	Intermediate Similarity	NPC11620
0.7907	Intermediate Similarity	NPC128429
0.7889	Intermediate Similarity	NPC49342
0.7889	Intermediate Similarity	NPC312042
0.7889	Intermediate Similarity	NPC251385
0.7882	Intermediate Similarity	NPC141810
0.7882	Intermediate Similarity	NPC47635
0.7872	Intermediate Similarity	NPC279561
0.7872	Intermediate Similarity	NPC474213
0.7865	Intermediate Similarity	NPC178875
0.7857	Intermediate Similarity	NPC617
0.7849	Intermediate Similarity	NPC31645
0.7849	Intermediate Similarity	NPC76862
0.7849	Intermediate Similarity	NPC39859
0.7849	Intermediate Similarity	NPC158416
0.7849	Intermediate Similarity	NPC476009
0.7849	Intermediate Similarity	NPC470883
0.7849	Intermediate Similarity	NPC473859
0.7841	Intermediate Similarity	NPC469626
0.7841	Intermediate Similarity	NPC475491
0.7826	Intermediate Similarity	NPC476267
0.7826	Intermediate Similarity	NPC57405
0.7826	Intermediate Similarity	NPC190294
0.7826	Intermediate Similarity	NPC140543
0.7826	Intermediate Similarity	NPC476722
0.7826	Intermediate Similarity	NPC303942
0.7816	Intermediate Similarity	NPC72464
0.7789	Intermediate Similarity	NPC288876
0.7789	Intermediate Similarity	NPC471381
0.7766	Intermediate Similarity	NPC328562
0.7766	Intermediate Similarity	NPC323421
0.7766	Intermediate Similarity	NPC471150
0.7765	Intermediate Similarity	NPC474510
0.7742	Intermediate Similarity	NPC474947
0.7727	Intermediate Similarity	NPC235792
0.7727	Intermediate Similarity	NPC137033
0.7717	Intermediate Similarity	NPC472874
0.7708	Intermediate Similarity	NPC201718
0.7708	Intermediate Similarity	NPC264477
0.7708	Intermediate Similarity	NPC477511
0.7708	Intermediate Similarity	NPC476270
0.7701	Intermediate Similarity	NPC54468
0.7701	Intermediate Similarity	NPC170286
0.7692	Intermediate Similarity	NPC206614
0.7692	Intermediate Similarity	NPC474323
0.7684	Intermediate Similarity	NPC208233
0.7684	Intermediate Similarity	NPC473326
0.7674	Intermediate Similarity	NPC207188
0.7667	Intermediate Similarity	NPC224652
0.766	Intermediate Similarity	NPC476275
0.766	Intermediate Similarity	NPC279621
0.766	Intermediate Similarity	NPC17585
0.766	Intermediate Similarity	NPC35498
0.7653	Intermediate Similarity	NPC474741
0.764	Intermediate Similarity	NPC162071
0.764	Intermediate Similarity	NPC474045
0.764	Intermediate Similarity	NPC304558
0.764	Intermediate Similarity	NPC284902
0.764	Intermediate Similarity	NPC261253
0.764	Intermediate Similarity	NPC64153
0.764	Intermediate Similarity	NPC122502
0.7634	Intermediate Similarity	NPC66581
0.7619	Intermediate Similarity	NPC470240
0.7619	Intermediate Similarity	NPC476794
0.7614	Intermediate Similarity	NPC9868
0.7609	Intermediate Similarity	NPC165180
0.7609	Intermediate Similarity	NPC286341
0.7609	Intermediate Similarity	NPC155215
0.7609	Intermediate Similarity	NPC191339
0.759	Intermediate Similarity	NPC471491
0.7582	Intermediate Similarity	NPC4986
0.7582	Intermediate Similarity	NPC283409
0.7582	Intermediate Similarity	NPC474032
0.7579	Intermediate Similarity	NPC471140
0.7579	Intermediate Similarity	NPC474921
0.7576	Intermediate Similarity	NPC243998
0.7576	Intermediate Similarity	NPC223450
0.7576	Intermediate Similarity	NPC54737
0.7556	Intermediate Similarity	NPC24728
0.7553	Intermediate Similarity	NPC167893
0.7553	Intermediate Similarity	NPC163228
0.7553	Intermediate Similarity	NPC224689
0.7529	Intermediate Similarity	NPC264610
0.7527	Intermediate Similarity	NPC258216
0.7527	Intermediate Similarity	NPC135776
0.7527	Intermediate Similarity	NPC228451
0.7527	Intermediate Similarity	NPC125674
0.7527	Intermediate Similarity	NPC475838
0.7527	Intermediate Similarity	NPC153590
0.7526	Intermediate Similarity	NPC15993
0.75	Intermediate Similarity	NPC80875
0.75	Intermediate Similarity	NPC65359
0.75	Intermediate Similarity	NPC318468
0.75	Intermediate Similarity	NPC45125
0.75	Intermediate Similarity	NPC475842
0.7475	Intermediate Similarity	NPC477510
0.7475	Intermediate Similarity	NPC471143
0.7473	Intermediate Similarity	NPC217983
0.7473	Intermediate Similarity	NPC476704
0.7473	Intermediate Similarity	NPC79549
0.7473	Intermediate Similarity	NPC471149
0.7473	Intermediate Similarity	NPC207114
0.7471	Intermediate Similarity	NPC301477
0.7471	Intermediate Similarity	NPC25684
0.7471	Intermediate Similarity	NPC281949
0.7449	Intermediate Similarity	NPC320019
0.7449	Intermediate Similarity	NPC474747
0.7449	Intermediate Similarity	NPC324017
0.7447	Intermediate Similarity	NPC474247
0.7447	Intermediate Similarity	NPC476716
0.7444	Intermediate Similarity	NPC238593
0.7444	Intermediate Similarity	NPC204048
0.7444	Intermediate Similarity	NPC164393
0.7442	Intermediate Similarity	NPC80999
0.7442	Intermediate Similarity	NPC19841
0.7423	Intermediate Similarity	NPC477512
0.7419	Intermediate Similarity	NPC470373

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 NPC474472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	2964
0.2-0.3	3784
0.3-0.4	1481
0.4-0.5	455
0.5-0.6	167
0.6-0.7	9
0.7-0.8	2
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.814	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1695	Approved
0.7312	Intermediate Similarity	NPD46	Approved
0.7312	Intermediate Similarity	NPD6698	Approved
0.699	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7838	Discovery
0.6792	Remote Similarity	NPD6371	Approved
0.6701	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6053	Discontinued
0.6506	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6686	Approved
0.6415	Remote Similarity	NPD6008	Approved
0.6408	Remote Similarity	NPD6648	Approved
0.6355	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5344	Discontinued
0.6311	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6435	Approved
0.6273	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1694	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6105	Remote Similarity	NPD5209	Approved
0.6064	Remote Similarity	NPD5368	Approved
0.6044	Remote Similarity	NPD8039	Approved
0.6042	Remote Similarity	NPD7154	Phase 3
0.6018	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD7638	Approved
0.596	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4251	Approved
0.5943	Remote Similarity	NPD7639	Approved
0.5943	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD5785	Approved
0.5932	Remote Similarity	NPD8513	Phase 3
0.5932	Remote Similarity	NPD8516	Approved
0.5932	Remote Similarity	NPD8515	Approved
0.5932	Remote Similarity	NPD8268	Approved
0.5932	Remote Similarity	NPD8266	Approved
0.5932	Remote Similarity	NPD8269	Approved
0.5932	Remote Similarity	NPD8517	Approved
0.5932	Remote Similarity	NPD8267	Approved
0.5922	Remote Similarity	NPD5282	Discontinued
0.5918	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4632	Approved
0.5876	Remote Similarity	NPD5362	Discontinued
0.5868	Remote Similarity	NPD7507	Approved
0.5862	Remote Similarity	NPD7115	Discovery
0.5859	Remote Similarity	NPD5786	Approved
0.5859	Remote Similarity	NPD5330	Approved
0.5859	Remote Similarity	NPD7146	Approved
0.5859	Remote Similarity	NPD7521	Approved
0.5859	Remote Similarity	NPD6409	Approved
0.5859	Remote Similarity	NPD6684	Approved
0.5859	Remote Similarity	NPD4249	Approved
0.5859	Remote Similarity	NPD7334	Approved
0.5849	Remote Similarity	NPD4225	Approved
0.5842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6101	Approved
0.5833	Remote Similarity	NPD1780	Approved
0.5833	Remote Similarity	NPD7642	Approved
0.5833	Remote Similarity	NPD7829	Approved
0.5833	Remote Similarity	NPD7604	Phase 2
0.5833	Remote Similarity	NPD7830	Approved
0.5833	Remote Similarity	NPD1145	Discontinued
0.5833	Remote Similarity	NPD1779	Approved
0.5833	Remote Similarity	NPD5369	Approved
0.5814	Remote Similarity	NPD7909	Approved
0.581	Remote Similarity	NPD7839	Suspended
0.5789	Remote Similarity	NPD8297	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.5758	Remote Similarity	NPD5363	Approved
0.5747	Remote Similarity	NPD7341	Phase 2
0.5743	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6903	Approved
0.5743	Remote Similarity	NPD5737	Approved
0.5743	Remote Similarity	NPD6672	Approved
0.5738	Remote Similarity	NPD6616	Approved
0.5738	Remote Similarity	NPD8273	Phase 1
0.5729	Remote Similarity	NPD4820	Approved
0.5729	Remote Similarity	NPD4822	Approved
0.5729	Remote Similarity	NPD4819	Approved
0.5729	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4821	Approved
0.5728	Remote Similarity	NPD6411	Approved
0.5728	Remote Similarity	NPD8035	Phase 2
0.5728	Remote Similarity	NPD5693	Phase 1
0.5728	Remote Similarity	NPD8034	Phase 2
0.5726	Remote Similarity	NPD7319	Approved
0.5726	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD6319	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6422	Discontinued
0.5691	Remote Similarity	NPD7078	Approved
0.5691	Remote Similarity	NPD8074	Phase 3
0.5684	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7331	Phase 2
0.5676	Remote Similarity	NPD7128	Approved
0.5676	Remote Similarity	NPD6402	Approved
0.5676	Remote Similarity	NPD6675	Approved
0.5676	Remote Similarity	NPD5739	Approved
0.5673	Remote Similarity	NPD6399	Phase 3
0.5667	Remote Similarity	NPD5983	Phase 2
0.5659	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7736	Approved
0.5644	Remote Similarity	NPD3573	Approved
0.5635	Remote Similarity	NPD7260	Phase 2
0.5625	Remote Similarity	NPD5697	Approved
0.5625	Remote Similarity	NPD6412	Phase 2
0.562	Remote Similarity	NPD6370	Approved
0.5619	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD7900	Approved
0.5614	Remote Similarity	NPD7102	Approved
0.5614	Remote Similarity	NPD7290	Approved
0.5614	Remote Similarity	NPD6883	Approved
0.5612	Remote Similarity	NPD4269	Approved
0.5612	Remote Similarity	NPD4270	Approved
0.561	Remote Similarity	NPD6336	Discontinued

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