NPASS Compound

Structure

NPC121825 OpenBabel07101718182D 26 27 0 0 1 0 0 0 0 0999 V2000 4.8002 0.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7822 1.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3741 -2.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6524 -3.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6524 0.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1080 0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7068 -1.3688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3105 -0.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8867 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0432 -1.8319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3105 -1.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1080 -2.1779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6524 -2.0010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2886 -1.3031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2126 -3.1724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 -1.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1524 -2.8670 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 11 1 0 0 0 0 3 12 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 13 11 1 6 0 0 0 14 21 2 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 25 1 1 0 0 0 18 8 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 23 1 6 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	374.286
LogP:	1.589
LogD:	1.119
LogS:	-2.333
# Rotatable Bonds:	2
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	5.799
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.679
MDCK Permeability:	2.021938780671917e-05
Pgp-inhibitor:	0.101
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.299
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.677
Plasma Protein Binding (PPB):	76.42037963867188%
Volume Distribution (VD):	0.557
Pgp-substrate:	19.748144149780273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.587
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.361

ADMET: Excretion

Clearance (CL):	12.657
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.494
Drug-inuced Liver Injury (DILI):	0.261
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.926
Carcinogencity:	0.808
Eye Corrosion:	0.004
Eye Irritation:	0.096
Respiratory Toxicity:	0.624

Download Data

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

Natural Product: NPC121825

Natural Product ID:	NPC121825
*Common Name:**	Gyrosanolide C
IUPAC Name:	n.a.
Synonyms:	Gyrosanolide C
Standard InCHIKey:	WIWLIEUEOQQPHP-NOMAXEBQSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-11(2)13-5-6-15-19(23)18(26-20(15)24)8-12(3)7-16(22)17(25-4)10-14(21)9-13/h6-7,13,17-19,23H,1,5,8-10H2,2-4H3/b12-7+,15-6-/t13-,17+,18+,19-/m0/s1
SMILES:	CO[C@@H]1CC(=O)C[C@H](C/C=C2/[C@@H]([C@@H](C/C(=C/C1=O)/C)OC2=O)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096138
PubChem CID:	n.a.
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
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20430633]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499851]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	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
ED50	4
Others	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	20.0	ug ml-1	PMID[524113]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[524113]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[524113]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	10.6	%	PMID[524113]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	ED50	>	50.0	ug ml-1	PMID[524113]

☑ 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 NPC121825 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	198
0.1-0.2	1184
0.2-0.3	4589
0.3-0.4	8692
0.4-0.5	14863
0.5-0.6	7462
0.6-0.7	4250
0.7-0.8	1271
0.8-0.85	152
0.85-0.9	28
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9885	High Similarity	NPC469645
0.9885	High Similarity	NPC469692
0.9355	High Similarity	NPC110443
0.9355	High Similarity	NPC133907
0.9355	High Similarity	NPC46998
0.9355	High Similarity	NPC128733
0.9355	High Similarity	NPC185141
0.8977	High Similarity	NPC261721
0.8913	High Similarity	NPC469632
0.8763	High Similarity	NPC472755
0.875	High Similarity	NPC474339
0.875	High Similarity	NPC164598
0.8602	High Similarity	NPC475302
0.8571	High Similarity	NPC475945
0.8571	High Similarity	NPC475871
0.8571	High Similarity	NPC476803
0.8557	High Similarity	NPC474742
0.8557	High Similarity	NPC472753
0.8556	High Similarity	NPC279859
0.8556	High Similarity	NPC475461
0.8556	High Similarity	NPC469910
0.8556	High Similarity	NPC38576
0.8556	High Similarity	NPC305475
0.8485	Intermediate Similarity	NPC472756
0.8469	Intermediate Similarity	NPC472754
0.8469	Intermediate Similarity	NPC149371
0.8469	Intermediate Similarity	NPC474747
0.8469	Intermediate Similarity	NPC471148
0.8444	Intermediate Similarity	NPC470755
0.8444	Intermediate Similarity	NPC165162
0.8444	Intermediate Similarity	NPC255307
0.8404	Intermediate Similarity	NPC162205
0.8404	Intermediate Similarity	NPC288240
0.8404	Intermediate Similarity	NPC273579
0.8404	Intermediate Similarity	NPC475912
0.8404	Intermediate Similarity	NPC295204
0.8387	Intermediate Similarity	NPC474232
0.8384	Intermediate Similarity	NPC475873
0.837	Intermediate Similarity	NPC476805
0.837	Intermediate Similarity	NPC471047
0.837	Intermediate Similarity	NPC469653
0.837	Intermediate Similarity	NPC475906
0.837	Intermediate Similarity	NPC469628
0.837	Intermediate Similarity	NPC469631
0.8367	Intermediate Similarity	NPC201718
0.8367	Intermediate Similarity	NPC476270
0.8367	Intermediate Similarity	NPC47880
0.8352	Intermediate Similarity	NPC469483
0.8351	Intermediate Similarity	NPC471144
0.8333	Intermediate Similarity	NPC114979
0.8333	Intermediate Similarity	NPC96259
0.8333	Intermediate Similarity	NPC141193
0.8333	Intermediate Similarity	NPC191476
0.8333	Intermediate Similarity	NPC158756
0.8333	Intermediate Similarity	NPC38154
0.8317	Intermediate Similarity	NPC477513
0.83	Intermediate Similarity	NPC100487
0.83	Intermediate Similarity	NPC474741
0.8298	Intermediate Similarity	NPC261607
0.8298	Intermediate Similarity	NPC300312
0.8298	Intermediate Similarity	NPC111114
0.8276	Intermediate Similarity	NPC93763
0.8276	Intermediate Similarity	NPC108816
0.8265	Intermediate Similarity	NPC288876
0.8261	Intermediate Similarity	NPC472007
0.8242	Intermediate Similarity	NPC21469
0.8242	Intermediate Similarity	NPC261380
0.8229	Intermediate Similarity	NPC471142
0.8229	Intermediate Similarity	NPC36954
0.8229	Intermediate Similarity	NPC14961
0.8229	Intermediate Similarity	NPC270013
0.8222	Intermediate Similarity	NPC475947
0.8222	Intermediate Similarity	NPC169575
0.8222	Intermediate Similarity	NPC473390
0.8222	Intermediate Similarity	NPC131669
0.8222	Intermediate Similarity	NPC40746
0.8191	Intermediate Similarity	NPC474761
0.8191	Intermediate Similarity	NPC129419
0.8191	Intermediate Similarity	NPC476004
0.8172	Intermediate Similarity	NPC475819
0.8163	Intermediate Similarity	NPC187268
0.8163	Intermediate Similarity	NPC141191
0.8161	Intermediate Similarity	NPC320630
0.8161	Intermediate Similarity	NPC116177
0.8161	Intermediate Similarity	NPC7563
0.8152	Intermediate Similarity	NPC472009
0.8152	Intermediate Similarity	NPC150755
0.8144	Intermediate Similarity	NPC279621
0.8144	Intermediate Similarity	NPC230800
0.8144	Intermediate Similarity	NPC477921
0.8137	Intermediate Similarity	NPC469853
0.8132	Intermediate Similarity	NPC476804
0.8125	Intermediate Similarity	NPC474035
0.8125	Intermediate Similarity	NPC81386
0.8125	Intermediate Similarity	NPC167219
0.8119	Intermediate Similarity	NPC203659
0.8111	Intermediate Similarity	NPC229825
0.8111	Intermediate Similarity	NPC474291
0.8105	Intermediate Similarity	NPC30515
0.8105	Intermediate Similarity	NPC476705
0.8105	Intermediate Similarity	NPC184463
0.8105	Intermediate Similarity	NPC473321
0.81	Intermediate Similarity	NPC39996
0.81	Intermediate Similarity	NPC140591
0.81	Intermediate Similarity	NPC303653
0.81	Intermediate Similarity	NPC320019
0.81	Intermediate Similarity	NPC197835
0.81	Intermediate Similarity	NPC324017
0.81	Intermediate Similarity	NPC189609
0.81	Intermediate Similarity	NPC291500
0.8085	Intermediate Similarity	NPC295312
0.8085	Intermediate Similarity	NPC474032
0.8085	Intermediate Similarity	NPC268298
0.8081	Intermediate Similarity	NPC475949
0.8065	Intermediate Similarity	NPC266957
0.8065	Intermediate Similarity	NPC72513
0.8065	Intermediate Similarity	NPC179659
0.8061	Intermediate Similarity	NPC169205
0.8043	Intermediate Similarity	NPC125290
0.8043	Intermediate Similarity	NPC11804
0.8041	Intermediate Similarity	NPC477922
0.8039	Intermediate Similarity	NPC472749
0.8039	Intermediate Similarity	NPC469852
0.8039	Intermediate Similarity	NPC472751
0.8022	Intermediate Similarity	NPC474703
0.8021	Intermediate Similarity	NPC179746
0.8021	Intermediate Similarity	NPC475838
0.8021	Intermediate Similarity	NPC212486
0.8021	Intermediate Similarity	NPC165383
0.8021	Intermediate Similarity	NPC81419
0.8021	Intermediate Similarity	NPC476300
0.8021	Intermediate Similarity	NPC228451
0.8021	Intermediate Similarity	NPC125674
0.802	Intermediate Similarity	NPC472747
0.802	Intermediate Similarity	NPC110989
0.802	Intermediate Similarity	NPC472750
0.8	Intermediate Similarity	NPC71533
0.8	Intermediate Similarity	NPC106510
0.8	Intermediate Similarity	NPC473448
0.8	Intermediate Similarity	NPC475855
0.8	Intermediate Similarity	NPC15993
0.8	Intermediate Similarity	NPC51004
0.8	Intermediate Similarity	NPC25684
0.8	Intermediate Similarity	NPC471325
0.8	Intermediate Similarity	NPC24417
0.8	Intermediate Similarity	NPC179394
0.8	Intermediate Similarity	NPC469368
0.8	Intermediate Similarity	NPC301477
0.8	Intermediate Similarity	NPC473619
0.8	Intermediate Similarity	NPC281949
0.8	Intermediate Similarity	NPC144133
0.798	Intermediate Similarity	NPC161855
0.798	Intermediate Similarity	NPC159763
0.798	Intermediate Similarity	NPC124512
0.798	Intermediate Similarity	NPC278386
0.7979	Intermediate Similarity	NPC202672
0.7979	Intermediate Similarity	NPC472008
0.7979	Intermediate Similarity	NPC287089
0.7979	Intermediate Similarity	NPC475902
0.7978	Intermediate Similarity	NPC470239
0.7978	Intermediate Similarity	NPC470244
0.7978	Intermediate Similarity	NPC178277
0.7978	Intermediate Similarity	NPC19841
0.7963	Intermediate Similarity	NPC471146
0.7963	Intermediate Similarity	NPC471145
0.7961	Intermediate Similarity	NPC26617
0.7959	Intermediate Similarity	NPC476009
0.7959	Intermediate Similarity	NPC470883
0.7959	Intermediate Similarity	NPC473859
0.7959	Intermediate Similarity	NPC185553
0.7959	Intermediate Similarity	NPC76862
0.7959	Intermediate Similarity	NPC158416
0.7959	Intermediate Similarity	NPC476315
0.7959	Intermediate Similarity	NPC39859
0.7959	Intermediate Similarity	NPC473291
0.7941	Intermediate Similarity	NPC220964
0.7941	Intermediate Similarity	NPC475676
0.7941	Intermediate Similarity	NPC472748
0.7938	Intermediate Similarity	NPC65829
0.7938	Intermediate Similarity	NPC474247
0.7938	Intermediate Similarity	NPC190294
0.7935	Intermediate Similarity	NPC243618
0.7935	Intermediate Similarity	NPC70424
0.7921	Intermediate Similarity	NPC86077
0.7921	Intermediate Similarity	NPC225353
0.7917	Intermediate Similarity	NPC219874
0.7917	Intermediate Similarity	NPC20713
0.7917	Intermediate Similarity	NPC12172
0.7917	Intermediate Similarity	NPC208886
0.7912	Intermediate Similarity	NPC474959
0.7912	Intermediate Similarity	NPC475046
0.7912	Intermediate Similarity	NPC310450
0.7912	Intermediate Similarity	NPC475690
0.7912	Intermediate Similarity	NPC11383
0.7912	Intermediate Similarity	NPC85772
0.7912	Intermediate Similarity	NPC89555
0.7895	Intermediate Similarity	NPC14901
0.7895	Intermediate Similarity	NPC206001
0.7895	Intermediate Similarity	NPC173926
0.7895	Intermediate Similarity	NPC307411

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 NPC121825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1743
0.2-0.3	3572
0.3-0.4	2333
0.4-0.5	856
0.5-0.6	330
0.6-0.7	108
0.7-0.8	14
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
0.798	Intermediate Similarity	NPD4225	Approved
0.7961	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5785	Approved
0.7736	Intermediate Similarity	NPD6371	Approved
0.766	Intermediate Similarity	NPD5363	Approved
0.7629	Intermediate Similarity	NPD6698	Approved
0.7629	Intermediate Similarity	NPD46	Approved
0.7396	Intermediate Similarity	NPD5786	Approved
0.7374	Intermediate Similarity	NPD7983	Approved
0.734	Intermediate Similarity	NPD4269	Approved
0.734	Intermediate Similarity	NPD4270	Approved
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD7838	Discovery
0.7263	Intermediate Similarity	NPD7154	Phase 3
0.7182	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4252	Approved
0.7113	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5282	Discontinued
0.7053	Intermediate Similarity	NPD5369	Approved
0.6989	Remote Similarity	NPD4756	Discovery
0.6961	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD5778	Approved
0.6952	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1694	Approved
0.6909	Remote Similarity	NPD6686	Approved
0.6907	Remote Similarity	NPD5362	Discontinued
0.6804	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5209	Approved
0.6771	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6110	Phase 1
0.6698	Remote Similarity	NPD6083	Phase 2
0.6698	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5370	Suspended
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6636	Remote Similarity	NPD5696	Approved
0.6633	Remote Similarity	NPD6435	Approved
0.6604	Remote Similarity	NPD7839	Suspended
0.66	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4822	Approved
0.6598	Remote Similarity	NPD4819	Approved
0.6598	Remote Similarity	NPD4821	Approved
0.6598	Remote Similarity	NPD4820	Approved
0.6579	Remote Similarity	NPD6650	Approved
0.6579	Remote Similarity	NPD6649	Approved
0.6562	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4271	Approved
0.6562	Remote Similarity	NPD4268	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6549	Remote Similarity	NPD6373	Approved
0.6549	Remote Similarity	NPD6372	Approved
0.6538	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6411	Approved
0.6535	Remote Similarity	NPD4249	Approved
0.6522	Remote Similarity	NPD8297	Approved
0.6518	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD8516	Approved
0.65	Remote Similarity	NPD8517	Approved
0.65	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8513	Phase 3
0.6476	Remote Similarity	NPD6399	Phase 3
0.6471	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD4251	Approved
0.646	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD6899	Approved
0.6449	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6422	Remote Similarity	NPD7639	Approved
0.6422	Remote Similarity	NPD7640	Approved
0.6408	Remote Similarity	NPD5737	Approved
0.6408	Remote Similarity	NPD6672	Approved
0.6404	Remote Similarity	NPD6012	Approved
0.6404	Remote Similarity	NPD6014	Approved
0.6404	Remote Similarity	NPD6013	Approved
0.6404	Remote Similarity	NPD3197	Phase 1
0.64	Remote Similarity	NPD5331	Approved
0.64	Remote Similarity	NPD5332	Approved
0.6381	Remote Similarity	NPD5693	Phase 1
0.6381	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD4790	Discontinued
0.6348	Remote Similarity	NPD7290	Approved
0.6348	Remote Similarity	NPD7102	Approved
0.6348	Remote Similarity	NPD6883	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6333	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD6011	Approved
0.6293	Remote Similarity	NPD6847	Approved
0.6293	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6617	Approved
0.6293	Remote Similarity	NPD8130	Phase 1
0.6293	Remote Similarity	NPD6869	Approved
0.629	Remote Similarity	NPD6616	Approved
0.6281	Remote Similarity	NPD6054	Approved
0.6273	Remote Similarity	NPD6648	Approved
0.6264	Remote Similarity	NPD3704	Approved
0.6263	Remote Similarity	NPD4695	Discontinued
0.6261	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7642	Approved
0.626	Remote Similarity	NPD8328	Phase 3
0.624	Remote Similarity	NPD8074	Phase 3
0.624	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD7902	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.623	Remote Similarity	NPD6016	Approved
0.623	Remote Similarity	NPD6015	Approved
0.6214	Remote Similarity	NPD5279	Phase 3
0.6207	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2067	Discontinued
0.6204	Remote Similarity	NPD5210	Approved
0.6204	Remote Similarity	NPD4629	Approved
0.619	Remote Similarity	NPD7736	Approved
0.619	Remote Similarity	NPD4753	Phase 2
0.6186	Remote Similarity	NPD4632	Approved
0.6179	Remote Similarity	NPD6370	Approved
0.6179	Remote Similarity	NPD5988	Approved
0.6161	Remote Similarity	NPD5211	Phase 2
0.6154	Remote Similarity	NPD2204	Approved
0.6148	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6059	Approved
0.6147	Remote Similarity	NPD4697	Phase 3
0.6129	Remote Similarity	NPD7829	Approved
0.6129	Remote Similarity	NPD7830	Approved
0.6111	Remote Similarity	NPD8293	Discontinued
0.6111	Remote Similarity	NPD7748	Approved
0.6111	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6412	Phase 2
0.6083	Remote Similarity	NPD6274	Approved
0.6082	Remote Similarity	NPD8039	Approved
0.6075	Remote Similarity	NPD7515	Phase 2
0.6068	Remote Similarity	NPD4634	Approved
0.6058	Remote Similarity	NPD6684	Approved
0.6058	Remote Similarity	NPD7146	Approved
0.6058	Remote Similarity	NPD6409	Approved
0.6058	Remote Similarity	NPD7334	Approved
0.6058	Remote Similarity	NPD5330	Approved
0.6058	Remote Similarity	NPD3618	Phase 1
0.6058	Remote Similarity	NPD7521	Approved
0.6053	Remote Similarity	NPD5141	Approved
0.6048	Remote Similarity	NPD8080	Discontinued
0.6047	Remote Similarity	NPD7260	Phase 2
0.6038	Remote Similarity	NPD6904	Approved
0.6038	Remote Similarity	NPD6673	Approved
0.6038	Remote Similarity	NPD6080	Approved
0.6033	Remote Similarity	NPD6009	Approved
0.6033	Remote Similarity	NPD7500	Approved
0.6032	Remote Similarity	NPD8273	Phase 1
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6017	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5985	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7641	Discontinued
0.5982	Remote Similarity	NPD5286	Approved
0.5982	Remote Similarity	NPD4696	Approved
0.5982	Remote Similarity	NPD5285	Approved
0.5981	Remote Similarity	NPD5692	Phase 3
0.598	Remote Similarity	NPD3667	Approved
0.5968	Remote Similarity	NPD5983	Phase 2
0.5968	Remote Similarity	NPD8444	Approved
0.5965	Remote Similarity	NPD6647	Phase 2
0.5963	Remote Similarity	NPD7900	Approved
0.5963	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD1696	Phase 3
0.595	Remote Similarity	NPD2629	Approved
0.595	Remote Similarity	NPD6868	Approved
0.595	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4755	Approved
0.5946	Remote Similarity	NPD5173	Approved
0.5943	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6903	Approved
0.5941	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7100	Approved
0.5935	Remote Similarity	NPD7101	Approved
0.5926	Remote Similarity	NPD6050	Approved
0.5926	Remote Similarity	NPD5694	Approved
0.5914	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7331	Phase 2
0.5909	Remote Similarity	NPD8415	Approved
0.5906	Remote Similarity	NPD7507	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