NPASS Compound

Structure

NPC470373 OpenBabel07101718302D 28 30 0 0 1 0 0 0 0 0999 V2000 1.4835 1.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6192 -1.4120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 -2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0874 3.0602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4357 0.2669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0213 1.1882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2963 0.7484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3355 -0.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4735 1.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4220 0.8871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5573 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1204 1.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9490 1.1099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0184 -0.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 -1.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6037 2.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -1.2930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3735 0.2070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2395 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 0.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0576 -0.7687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6036 2.2228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1055 -1.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5739 -1.6251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1202 1.3285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -0.2930 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 14 2 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 22 1 1 0 0 0 19 21 1 6 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 13 1 1 0 0 0 21 28 1 0 0 0 0 22 25 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	402.958
LogP:	3.201
LogD:	2.578
LogS:	-4.545
# Rotatable Bonds:	3
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	6.232
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.82
MDCK Permeability:	5.011996836401522e-05
Pgp-inhibitor:	0.101
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.396
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.632
Plasma Protein Binding (PPB):	82.62351989746094%
Volume Distribution (VD):	0.858
Pgp-substrate:	23.27496337890625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.294
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.313
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.628
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	7.402
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.525
Drug-inuced Liver Injury (DILI):	0.471
AMES Toxicity:	0.357
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.947
Carcinogencity:	0.244
Eye Corrosion:	0.013
Eye Irritation:	0.14
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC470373

Natural Product ID:	NPC470373
*Common Name:**	Durumhemiketalolide C
IUPAC Name:	n.a.
Synonyms:	Durumhemiketalolide C
Standard InCHIKey:	KMXSIXIXRFATQL-MGRIULBKSA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-14-7-5-8-15(2)12-22(25)18-11-19(27-20(24)16(18)3)21(28-22,10-6-9-14)13-26-17(4)23/h8-9,18-19,25H,3,5-7,10-13H2,1-2,4H3/b14-9+,15-8+/t18-,19+,21-,22+/m1/s1
SMILES:	CC1=CCCC2(C3CC(C(=C)C(=O)O3)C(O2)(CC(=CCC1)C)O)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2021460
PubChem CID:	70681304
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
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO5325	Lobophytum durum	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	0.0	%	PMID[540401]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	34.7	%	PMID[540401]

☑ 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 NPC470373 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	193
0.1-0.2	1125
0.2-0.3	3943
0.3-0.4	7104
0.4-0.5	14439
0.5-0.6	7679
0.6-0.7	7006
0.7-0.8	1179
0.8-0.85	21
0.85-0.9	5
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470379
0.977	High Similarity	NPC71589
0.8681	High Similarity	NPC184463
0.8667	High Similarity	NPC307411
0.8587	High Similarity	NPC476300
0.8587	High Similarity	NPC475912
0.8587	High Similarity	NPC212486
0.8571	High Similarity	NPC51004
0.8556	High Similarity	NPC202672
0.8526	High Similarity	NPC261377
0.8526	High Similarity	NPC83895
0.8526	High Similarity	NPC308567
0.8526	High Similarity	NPC187761
0.8526	High Similarity	NPC255592
0.8523	High Similarity	NPC9868
0.8523	High Similarity	NPC72464
0.8488	Intermediate Similarity	NPC233377
0.8478	Intermediate Similarity	NPC12172
0.8478	Intermediate Similarity	NPC30515
0.8478	Intermediate Similarity	NPC208886
0.8404	Intermediate Similarity	NPC14961
0.8404	Intermediate Similarity	NPC36954
0.8404	Intermediate Similarity	NPC270013
0.8387	Intermediate Similarity	NPC179746
0.8387	Intermediate Similarity	NPC81419
0.8316	Intermediate Similarity	NPC476315
0.8315	Intermediate Similarity	NPC70424
0.8315	Intermediate Similarity	NPC243618
0.8298	Intermediate Similarity	NPC474035
0.8298	Intermediate Similarity	NPC81386
0.8261	Intermediate Similarity	NPC151770
0.8242	Intermediate Similarity	NPC248602
0.8242	Intermediate Similarity	NPC231889
0.8229	Intermediate Similarity	NPC40812
0.8211	Intermediate Similarity	NPC475659
0.8202	Intermediate Similarity	NPC11620
0.8182	Intermediate Similarity	NPC472747
0.8182	Intermediate Similarity	NPC472750
0.8172	Intermediate Similarity	NPC476004
0.8172	Intermediate Similarity	NPC474761
0.8172	Intermediate Similarity	NPC475748
0.8152	Intermediate Similarity	NPC281516
0.8152	Intermediate Similarity	NPC153805
0.8152	Intermediate Similarity	NPC227379
0.8152	Intermediate Similarity	NPC474471
0.8144	Intermediate Similarity	NPC187268
0.8125	Intermediate Similarity	NPC473859
0.8105	Intermediate Similarity	NPC474338
0.8105	Intermediate Similarity	NPC57405
0.8105	Intermediate Similarity	NPC303942
0.81	Intermediate Similarity	NPC472748
0.8065	Intermediate Similarity	NPC474032
0.8061	Intermediate Similarity	NPC288876
0.8043	Intermediate Similarity	NPC186148
0.8039	Intermediate Similarity	NPC475960
0.8022	Intermediate Similarity	NPC21469
0.8022	Intermediate Similarity	NPC137033
0.8021	Intermediate Similarity	NPC471141
0.802	Intermediate Similarity	NPC472749
0.802	Intermediate Similarity	NPC472751
0.802	Intermediate Similarity	NPC476740
0.802	Intermediate Similarity	NPC476738
0.8	Intermediate Similarity	NPC473816
0.8	Intermediate Similarity	NPC162205
0.8	Intermediate Similarity	NPC475367
0.8	Intermediate Similarity	NPC295204
0.8	Intermediate Similarity	NPC474581
0.8	Intermediate Similarity	NPC273579
0.8	Intermediate Similarity	NPC170286
0.8	Intermediate Similarity	NPC309398
0.8	Intermediate Similarity	NPC288240
0.8	Intermediate Similarity	NPC272814
0.798	Intermediate Similarity	NPC473332
0.798	Intermediate Similarity	NPC476270
0.798	Intermediate Similarity	NPC47880
0.7979	Intermediate Similarity	NPC80875
0.7979	Intermediate Similarity	NPC474323
0.7979	Intermediate Similarity	NPC206614
0.7979	Intermediate Similarity	NPC473619
0.7959	Intermediate Similarity	NPC473326
0.7959	Intermediate Similarity	NPC279561
0.7957	Intermediate Similarity	NPC177629
0.7957	Intermediate Similarity	NPC58219
0.7938	Intermediate Similarity	NPC306041
0.7938	Intermediate Similarity	NPC279621
0.7935	Intermediate Similarity	NPC162071
0.7935	Intermediate Similarity	NPC311163
0.7917	Intermediate Similarity	NPC473316
0.7917	Intermediate Similarity	NPC473330
0.79	Intermediate Similarity	NPC474747
0.79	Intermediate Similarity	NPC149371
0.7895	Intermediate Similarity	NPC473321
0.7895	Intermediate Similarity	NPC133698
0.7895	Intermediate Similarity	NPC329952
0.7879	Intermediate Similarity	NPC475053
0.7872	Intermediate Similarity	NPC166919
0.7872	Intermediate Similarity	NPC92974
0.7872	Intermediate Similarity	NPC295312
0.7865	Intermediate Similarity	NPC103634
0.7864	Intermediate Similarity	NPC193765
0.7849	Intermediate Similarity	NPC190753
0.7849	Intermediate Similarity	NPC5130
0.7835	Intermediate Similarity	NPC471142
0.7835	Intermediate Similarity	NPC272050
0.7826	Intermediate Similarity	NPC47958
0.7826	Intermediate Similarity	NPC255307
0.7826	Intermediate Similarity	NPC304509
0.7826	Intermediate Similarity	NPC38468
0.7826	Intermediate Similarity	NPC50362
0.7826	Intermediate Similarity	NPC319795
0.7826	Intermediate Similarity	NPC149725
0.7822	Intermediate Similarity	NPC475871
0.7822	Intermediate Similarity	NPC475945
0.7812	Intermediate Similarity	NPC228451
0.7812	Intermediate Similarity	NPC125674
0.7812	Intermediate Similarity	NPC476049
0.7812	Intermediate Similarity	NPC475838
0.7812	Intermediate Similarity	NPC320089
0.7802	Intermediate Similarity	NPC44261
0.7802	Intermediate Similarity	NPC250315
0.78	Intermediate Similarity	NPC474742
0.7789	Intermediate Similarity	NPC144133
0.7789	Intermediate Similarity	NPC179394
0.7789	Intermediate Similarity	NPC475855
0.7789	Intermediate Similarity	NPC473448
0.7788	Intermediate Similarity	NPC315836
0.7788	Intermediate Similarity	NPC313668
0.7778	Intermediate Similarity	NPC471144
0.7778	Intermediate Similarity	NPC141810
0.7778	Intermediate Similarity	NPC474213
0.7767	Intermediate Similarity	NPC80338
0.7767	Intermediate Similarity	NPC148270
0.7767	Intermediate Similarity	NPC197813
0.7766	Intermediate Similarity	NPC473715
0.7753	Intermediate Similarity	NPC617
0.7745	Intermediate Similarity	NPC474741
0.7745	Intermediate Similarity	NPC100487
0.7745	Intermediate Similarity	NPC469869
0.7745	Intermediate Similarity	NPC474917
0.7742	Intermediate Similarity	NPC150755
0.7742	Intermediate Similarity	NPC122502
0.7742	Intermediate Similarity	NPC475461
0.7742	Intermediate Similarity	NPC164393
0.7742	Intermediate Similarity	NPC474762
0.7742	Intermediate Similarity	NPC469483
0.7742	Intermediate Similarity	NPC305475
0.7742	Intermediate Similarity	NPC475019
0.7742	Intermediate Similarity	NPC284902
0.7742	Intermediate Similarity	NPC50637
0.7742	Intermediate Similarity	NPC474949
0.7742	Intermediate Similarity	NPC476015
0.7732	Intermediate Similarity	NPC477131
0.7732	Intermediate Similarity	NPC190294
0.7732	Intermediate Similarity	NPC198853
0.7732	Intermediate Similarity	NPC471147
0.7732	Intermediate Similarity	NPC474247
0.7723	Intermediate Similarity	NPC13171
0.7723	Intermediate Similarity	NPC473596
0.7723	Intermediate Similarity	NPC313569
0.7723	Intermediate Similarity	NPC195510
0.7717	Intermediate Similarity	NPC191476
0.7717	Intermediate Similarity	NPC114979
0.7717	Intermediate Similarity	NPC474780
0.7714	Intermediate Similarity	NPC5103
0.7708	Intermediate Similarity	NPC472197
0.7708	Intermediate Similarity	NPC131209
0.7708	Intermediate Similarity	NPC70251
0.7708	Intermediate Similarity	NPC475881
0.7692	Intermediate Similarity	NPC473807
0.7692	Intermediate Similarity	NPC474291
0.7684	Intermediate Similarity	NPC212598
0.7677	Intermediate Similarity	NPC266842
0.7677	Intermediate Similarity	NPC20066
0.7677	Intermediate Similarity	NPC471462
0.767	Intermediate Similarity	NPC243998
0.767	Intermediate Similarity	NPC170432
0.767	Intermediate Similarity	NPC223450
0.766	Intermediate Similarity	NPC160138
0.766	Intermediate Similarity	NPC74139
0.766	Intermediate Similarity	NPC475703
0.7658	Intermediate Similarity	NPC470829
0.7658	Intermediate Similarity	NPC473228
0.7653	Intermediate Similarity	NPC477922
0.7653	Intermediate Similarity	NPC304886
0.7653	Intermediate Similarity	NPC475900
0.7653	Intermediate Similarity	NPC67584
0.7647	Intermediate Similarity	NPC472755
0.7647	Intermediate Similarity	NPC475928
0.7647	Intermediate Similarity	NPC475873
0.7647	Intermediate Similarity	NPC37240
0.7642	Intermediate Similarity	NPC179798
0.7642	Intermediate Similarity	NPC297945
0.7642	Intermediate Similarity	NPC304180
0.7642	Intermediate Similarity	NPC126897
0.7634	Intermediate Similarity	NPC471494
0.7634	Intermediate Similarity	NPC182383
0.7634	Intermediate Similarity	NPC329749
0.7634	Intermediate Similarity	NPC165162
0.7634	Intermediate Similarity	NPC99395
0.7634	Intermediate Similarity	NPC197903

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 NPC470373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1448
0.2-0.3	3550
0.3-0.4	2479
0.4-0.5	982
0.5-0.6	317
0.6-0.7	184
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7979	Intermediate Similarity	NPD6698	Approved
0.7979	Intermediate Similarity	NPD46	Approved
0.7959	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6686	Approved
0.7347	Intermediate Similarity	NPD7983	Approved
0.73	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5778	Approved
0.7273	Intermediate Similarity	NPD5779	Approved
0.7264	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7838	Discovery
0.7228	Intermediate Similarity	NPD7839	Suspended
0.7193	Intermediate Similarity	NPD8513	Phase 3
0.7193	Intermediate Similarity	NPD8517	Approved
0.7193	Intermediate Similarity	NPD8515	Approved
0.7193	Intermediate Similarity	NPD8516	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1695	Approved
0.7064	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6949	Remote Similarity	NPD8451	Approved
0.6937	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD7830	Approved
0.6923	Remote Similarity	NPD4225	Approved
0.6923	Remote Similarity	NPD7829	Approved
0.6891	Remote Similarity	NPD8074	Phase 3
0.6891	Remote Similarity	NPD8448	Approved
0.6863	Remote Similarity	NPD5282	Discontinued
0.6807	Remote Similarity	NPD7507	Approved
0.6792	Remote Similarity	NPD5344	Discontinued
0.6783	Remote Similarity	NPD7641	Discontinued
0.678	Remote Similarity	NPD7642	Approved
0.6771	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6435	Approved
0.6727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8299	Approved
0.6723	Remote Similarity	NPD8341	Approved
0.6723	Remote Similarity	NPD8342	Approved
0.6723	Remote Similarity	NPD8340	Approved
0.6721	Remote Similarity	NPD8390	Approved
0.6721	Remote Similarity	NPD8391	Approved
0.6721	Remote Similarity	NPD8392	Approved
0.6701	Remote Similarity	NPD7154	Phase 3
0.6698	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6422	Discontinued
0.6639	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD6412	Phase 2
0.6607	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6399	Phase 3
0.6579	Remote Similarity	NPD8133	Approved
0.6569	Remote Similarity	NPD5785	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD5368	Approved
0.6552	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5786	Approved
0.6495	Remote Similarity	NPD5369	Approved
0.6491	Remote Similarity	NPD6882	Approved
0.6491	Remote Similarity	NPD8297	Approved
0.6486	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD8444	Approved
0.6465	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7638	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6435	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD6899	Approved
0.6417	Remote Similarity	NPD8080	Discontinued
0.6404	Remote Similarity	NPD6650	Approved
0.6404	Remote Similarity	NPD7331	Phase 2
0.6404	Remote Similarity	NPD6649	Approved
0.64	Remote Similarity	NPD5363	Approved
0.64	Remote Similarity	NPD7260	Phase 2
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6008	Approved
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6393	Remote Similarity	NPD6616	Approved
0.6392	Remote Similarity	NPD4820	Approved
0.6392	Remote Similarity	NPD4819	Approved
0.6392	Remote Similarity	NPD4822	Approved
0.6392	Remote Similarity	NPD4821	Approved
0.6392	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7640	Approved
0.6389	Remote Similarity	NPD7639	Approved
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD6319	Approved
0.6372	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD6012	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6013	Approved
0.6372	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD5362	Discontinued
0.6355	Remote Similarity	NPD7902	Approved
0.6341	Remote Similarity	NPD7078	Approved
0.6339	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5701	Approved
0.6337	Remote Similarity	NPD4249	Approved
0.6333	Remote Similarity	NPD6015	Approved
0.6333	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8269	Approved
0.6333	Remote Similarity	NPD8268	Approved
0.6333	Remote Similarity	NPD8033	Approved
0.6333	Remote Similarity	NPD8266	Approved
0.6333	Remote Similarity	NPD6016	Approved
0.6333	Remote Similarity	NPD8267	Approved
0.6321	Remote Similarity	NPD5695	Phase 3
0.6316	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD7290	Approved
0.6316	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD5696	Approved
0.6292	Remote Similarity	NPD7341	Phase 2
0.6292	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7736	Approved
0.6283	Remote Similarity	NPD7320	Approved
0.6283	Remote Similarity	NPD6011	Approved
0.6281	Remote Similarity	NPD6370	Approved
0.6281	Remote Similarity	NPD5988	Approved
0.6275	Remote Similarity	NPD4250	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.6275	Remote Similarity	NPD3573	Approved
0.6263	Remote Similarity	NPD4270	Approved
0.6263	Remote Similarity	NPD4269	Approved
0.6261	Remote Similarity	NPD6847	Approved
0.6261	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD8415	Approved
0.625	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.6226	Remote Similarity	NPD7748	Approved
0.6218	Remote Similarity	NPD7328	Approved
0.6218	Remote Similarity	NPD7327	Approved
0.6211	Remote Similarity	NPD8039	Approved
0.621	Remote Similarity	NPD8293	Discontinued
0.6204	Remote Similarity	NPD6083	Phase 2
0.6204	Remote Similarity	NPD6084	Phase 2
0.6202	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD8378	Approved
0.6198	Remote Similarity	NPD8296	Approved
0.6198	Remote Similarity	NPD8380	Approved
0.6198	Remote Similarity	NPD8335	Approved
0.6198	Remote Similarity	NPD5983	Phase 2
0.6198	Remote Similarity	NPD8379	Approved
0.6198	Remote Similarity	NPD7503	Approved
0.619	Remote Similarity	NPD7637	Suspended
0.6186	Remote Similarity	NPD4268	Approved
0.6186	Remote Similarity	NPD4271	Approved
0.6167	Remote Similarity	NPD7516	Approved
0.6139	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7500	Approved
0.6129	Remote Similarity	NPD8273	Phase 1
0.6126	Remote Similarity	NPD5211	Phase 2
0.6117	Remote Similarity	NPD7524	Approved
0.6098	Remote Similarity	NPD7604	Phase 2
0.6095	Remote Similarity	NPD3168	Discontinued
0.6094	Remote Similarity	NPD6845	Suspended
0.6091	Remote Similarity	NPD4696	Approved
0.6091	Remote Similarity	NPD5285	Approved
0.6091	Remote Similarity	NPD5286	Approved
0.6082	Remote Similarity	NPD4756	Discovery
0.6075	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7900	Approved
0.6066	Remote Similarity	NPD6921	Approved
0.6061	Remote Similarity	NPD4695	Discontinued
0.6061	Remote Similarity	NPD4252	Approved
0.6055	Remote Similarity	NPD4755	Approved
0.605	Remote Similarity	NPD6274	Approved
0.604	Remote Similarity	NPD6695	Phase 3
0.604	Remote Similarity	NPD6110	Phase 1
0.6038	Remote Similarity	NPD7515	Phase 2
0.6038	Remote Similarity	NPD5284	Approved
0.6038	Remote Similarity	NPD5693	Phase 1
0.6038	Remote Similarity	NPD5281	Approved
0.6034	Remote Similarity	NPD4634	Approved
0.602	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD5330	Approved
0.6018	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD1779	Approved
0.6	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD1780	Approved
0.5983	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8083	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