NPASS Compound

Structure

NPC213698 OpenBabel07101718272D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.0533 1.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2704 -2.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2387 -0.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4545 -2.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6195 0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6320 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3600 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7517 0.8435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9960 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2389 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2430 -0.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2185 -1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0204 -1.0646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1195 -1.4985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3930 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8789 -1.5775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2646 1.7019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1195 -2.4985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3680 -1.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4585 -2.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7518 0.8584 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 7 1 0 0 0 0 2 8 2 0 0 0 0 3 9 1 0 0 0 0 5 7 1 0 0 0 0 6 11 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 8 16 1 0 0 0 0 9 18 2 0 0 0 0 9 22 1 0 0 0 0 10 5 1 1 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 6 0 0 0 12 14 1 0 0 0 0 13 8 1 1 0 0 0 13 15 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 1 0 0 0 15 19 1 6 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 4 1 1 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.14
Volume:	319.114
LogP:	0.971
LogD:	1.187
LogS:	-2.425
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.804
Fsp3:	0.647
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:	-4.997
MDCK Permeability:	0.00019993804744444788
Pgp-inhibitor:	0.001
Pgp-substrate:	0.196
Human Intestinal Absorption (HIA):	0.441
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.518

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.671
Plasma Protein Binding (PPB):	54.22956085205078%
Volume Distribution (VD):	0.813
Pgp-substrate:	45.565860748291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	5.401
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.844
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.25
Skin Sensitization:	0.314
Carcinogencity:	0.719
Eye Corrosion:	0.628
Eye Irritation:	0.203
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC213698

Natural Product ID:	NPC213698
*Common Name:**	6Alpha-Hydroxyinuchinenolide B
IUPAC Name:	[(3aR,6S,8R,8aS,9S,9aS)-8,9-dihydroxy-5,8-dimethyl-1-methylidene-2-oxo-4,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-6-yl] acetate
Synonyms:
Standard InCHIKey:	DCPZHDYUXBYXIR-QCAZCHCXSA-N
Standard InCHI:	InChI=1S/C17H22O6/c1-7-5-10-13(8(2)16(20)23-10)15(19)14-12(7)11(22-9(3)18)6-17(14,4)21/h10-11,13-15,19,21H,2,5-6H2,1,3-4H3/t10-,11+,13-,14+,15+,17-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@]([C@H]2C1=C(C)C[C@@H]1[C@H]([C@@H]2O)C(=C)C(=O)O1)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426509
PubChem CID:	72708558
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones

*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
NPO32526	lineariifolia turcz	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24044895]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	>	50000.0	nM	PMID[529978]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[529978]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[529978]

☑ 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 NPC213698 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	223
0.1-0.2	1333
0.2-0.3	5246
0.3-0.4	12636
0.4-0.5	11047
0.5-0.6	7252
0.6-0.7	3798
0.7-0.8	1006
0.8-0.85	106
0.85-0.9	37
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC127019
0.9778	High Similarity	NPC161493
0.9775	High Similarity	NPC170120
0.9667	High Similarity	NPC213078
0.9556	High Similarity	NPC52044
0.9556	High Similarity	NPC67584
0.9255	High Similarity	NPC150923
0.9247	High Similarity	NPC221615
0.9111	High Similarity	NPC301969
0.9111	High Similarity	NPC216284
0.9111	High Similarity	NPC37607
0.9091	High Similarity	NPC67493
0.9032	High Similarity	NPC18019
0.9032	High Similarity	NPC24956
0.9011	High Similarity	NPC29821
0.9011	High Similarity	NPC57304
0.9011	High Similarity	NPC293001
0.9011	High Similarity	NPC35959
0.9011	High Similarity	NPC133888
0.9011	High Similarity	NPC63193
0.9011	High Similarity	NPC171360
0.9	High Similarity	NPC215556
0.8977	High Similarity	NPC235792
0.8947	High Similarity	NPC70865
0.8925	High Similarity	NPC472873
0.8901	High Similarity	NPC297474
0.8901	High Similarity	NPC54065
0.8901	High Similarity	NPC35809
0.8889	High Similarity	NPC217983
0.8889	High Similarity	NPC207114
0.8889	High Similarity	NPC79549
0.8889	High Similarity	NPC224652
0.8864	High Similarity	NPC156485
0.8817	High Similarity	NPC323008
0.8817	High Similarity	NPC477131
0.8817	High Similarity	NPC470013
0.8817	High Similarity	NPC198853
0.8817	High Similarity	NPC262133
0.8817	High Similarity	NPC470010
0.8804	High Similarity	NPC475925
0.8804	High Similarity	NPC155215
0.8804	High Similarity	NPC184063
0.8804	High Similarity	NPC131209
0.8804	High Similarity	NPC133698
0.8791	High Similarity	NPC155935
0.8737	High Similarity	NPC471150
0.8723	High Similarity	NPC476053
0.8723	High Similarity	NPC224689
0.8723	High Similarity	NPC304886
0.871	High Similarity	NPC258216
0.8696	High Similarity	NPC19087
0.8673	High Similarity	NPC124881
0.8667	High Similarity	NPC187661
0.8587	High Similarity	NPC472872
0.8587	High Similarity	NPC38392
0.8571	High Similarity	NPC24728
0.8556	High Similarity	NPC300082
0.8556	High Similarity	NPC204105
0.8556	High Similarity	NPC284534
0.8526	High Similarity	NPC163228
0.8526	High Similarity	NPC37408
0.8511	High Similarity	NPC135776
0.85	High Similarity	NPC54737
0.8478	Intermediate Similarity	NPC471149
0.8478	Intermediate Similarity	NPC91248
0.8469	Intermediate Similarity	NPC171759
0.8462	Intermediate Similarity	NPC64153
0.8462	Intermediate Similarity	NPC56593
0.8444	Intermediate Similarity	NPC224386
0.8444	Intermediate Similarity	NPC194859
0.8438	Intermediate Similarity	NPC142529
0.8438	Intermediate Similarity	NPC91771
0.8427	Intermediate Similarity	NPC89555
0.8427	Intermediate Similarity	NPC246076
0.84	Intermediate Similarity	NPC100487
0.8387	Intermediate Similarity	NPC283409
0.8384	Intermediate Similarity	NPC86077
0.837	Intermediate Similarity	NPC118601
0.8367	Intermediate Similarity	NPC186861
0.8367	Intermediate Similarity	NPC471381
0.8352	Intermediate Similarity	NPC165162
0.8351	Intermediate Similarity	NPC108475
0.8351	Intermediate Similarity	NPC213947
0.8351	Intermediate Similarity	NPC170143
0.8351	Intermediate Similarity	NPC474313
0.8351	Intermediate Similarity	NPC311904
0.8333	Intermediate Similarity	NPC111409
0.8333	Intermediate Similarity	NPC245665
0.8333	Intermediate Similarity	NPC128246
0.8333	Intermediate Similarity	NPC469873
0.8317	Intermediate Similarity	NPC243998
0.8316	Intermediate Similarity	NPC473273
0.8316	Intermediate Similarity	NPC60386
0.8316	Intermediate Similarity	NPC475838
0.8316	Intermediate Similarity	NPC125674
0.8316	Intermediate Similarity	NPC475912
0.8316	Intermediate Similarity	NPC473234
0.8316	Intermediate Similarity	NPC308656
0.8316	Intermediate Similarity	NPC228451
0.8316	Intermediate Similarity	NPC179746
0.8316	Intermediate Similarity	NPC81419
0.8316	Intermediate Similarity	NPC473263
0.8298	Intermediate Similarity	NPC475855
0.8298	Intermediate Similarity	NPC129419
0.828	Intermediate Similarity	NPC202672
0.828	Intermediate Similarity	NPC178875
0.8265	Intermediate Similarity	NPC45125
0.8261	Intermediate Similarity	NPC304558
0.8261	Intermediate Similarity	NPC107787
0.8252	Intermediate Similarity	NPC59489
0.8252	Intermediate Similarity	NPC139838
0.8235	Intermediate Similarity	NPC26617
0.8229	Intermediate Similarity	NPC474338
0.8229	Intermediate Similarity	NPC474247
0.8211	Intermediate Similarity	NPC30515
0.8211	Intermediate Similarity	NPC208886
0.8211	Intermediate Similarity	NPC12172
0.8211	Intermediate Similarity	NPC184463
0.8191	Intermediate Similarity	NPC32922
0.8191	Intermediate Similarity	NPC295312
0.8191	Intermediate Similarity	NPC212664
0.8191	Intermediate Similarity	NPC268298
0.8191	Intermediate Similarity	NPC4986
0.8172	Intermediate Similarity	NPC160138
0.8163	Intermediate Similarity	NPC477949
0.8163	Intermediate Similarity	NPC181151
0.8152	Intermediate Similarity	NPC255307
0.8152	Intermediate Similarity	NPC78089
0.8148	Intermediate Similarity	NPC161060
0.8144	Intermediate Similarity	NPC36954
0.8144	Intermediate Similarity	NPC270013
0.8144	Intermediate Similarity	NPC14961
0.8137	Intermediate Similarity	NPC166115
0.8137	Intermediate Similarity	NPC223450
0.8132	Intermediate Similarity	NPC250315
0.8125	Intermediate Similarity	NPC153590
0.8125	Intermediate Similarity	NPC212486
0.8125	Intermediate Similarity	NPC200237
0.8125	Intermediate Similarity	NPC472874
0.8125	Intermediate Similarity	NPC476300
0.8119	Intermediate Similarity	NPC474775
0.8111	Intermediate Similarity	NPC301477
0.8111	Intermediate Similarity	NPC281949
0.8111	Intermediate Similarity	NPC25684
0.8111	Intermediate Similarity	NPC126248
0.8105	Intermediate Similarity	NPC144133
0.8105	Intermediate Similarity	NPC51004
0.8105	Intermediate Similarity	NPC179394
0.81	Intermediate Similarity	NPC477950
0.809	Intermediate Similarity	NPC470244
0.809	Intermediate Similarity	NPC470239
0.809	Intermediate Similarity	NPC182550
0.8081	Intermediate Similarity	NPC187268
0.8065	Intermediate Similarity	NPC470242
0.8065	Intermediate Similarity	NPC309757
0.8065	Intermediate Similarity	NPC162071
0.8065	Intermediate Similarity	NPC236692
0.8065	Intermediate Similarity	NPC305475
0.8065	Intermediate Similarity	NPC475461
0.8065	Intermediate Similarity	NPC50637
0.8061	Intermediate Similarity	NPC279621
0.8061	Intermediate Similarity	NPC126156
0.8061	Intermediate Similarity	NPC230800
0.8061	Intermediate Similarity	NPC476315
0.8056	Intermediate Similarity	NPC36754
0.8043	Intermediate Similarity	NPC154893
0.8043	Intermediate Similarity	NPC115786
0.8043	Intermediate Similarity	NPC37005
0.8043	Intermediate Similarity	NPC53011
0.8043	Intermediate Similarity	NPC191476
0.8043	Intermediate Similarity	NPC165287
0.8043	Intermediate Similarity	NPC114979
0.8043	Intermediate Similarity	NPC16887
0.8043	Intermediate Similarity	NPC476804
0.8041	Intermediate Similarity	NPC81386
0.8041	Intermediate Similarity	NPC473331
0.8041	Intermediate Similarity	NPC474035
0.8021	Intermediate Similarity	NPC286341
0.8021	Intermediate Similarity	NPC191339
0.8	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC258965
0.8	Intermediate Similarity	NPC156658
0.8	Intermediate Similarity	NPC473564
0.8	Intermediate Similarity	NPC280963
0.7981	Intermediate Similarity	NPC117604
0.7979	Intermediate Similarity	NPC186148
0.7979	Intermediate Similarity	NPC270270
0.7979	Intermediate Similarity	NPC316629
0.7979	Intermediate Similarity	NPC237540
0.7979	Intermediate Similarity	NPC201658
0.7961	Intermediate Similarity	NPC44004
0.7961	Intermediate Similarity	NPC190867
0.7957	Intermediate Similarity	NPC215364
0.7944	Intermediate Similarity	NPC273242
0.7941	Intermediate Similarity	NPC475945
0.7941	Intermediate Similarity	NPC475871
0.7938	Intermediate Similarity	NPC475788
0.7935	Intermediate Similarity	NPC473390
0.7935	Intermediate Similarity	NPC318468
0.7935	Intermediate Similarity	NPC131669

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 NPC213698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	2012
0.2-0.3	3800
0.3-0.4	2207
0.4-0.5	527
0.5-0.6	268
0.6-0.7	92
0.7-0.8	21
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD1695	Approved
0.8065	Intermediate Similarity	NPD4249	Approved
0.7979	Intermediate Similarity	NPD4250	Approved
0.7979	Intermediate Similarity	NPD4251	Approved
0.785	Intermediate Similarity	NPD6053	Discontinued
0.783	Intermediate Similarity	NPD6371	Approved
0.7609	Intermediate Similarity	NPD4822	Approved
0.7609	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4821	Approved
0.7609	Intermediate Similarity	NPD4820	Approved
0.7609	Intermediate Similarity	NPD4819	Approved
0.76	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5362	Discontinued
0.7551	Intermediate Similarity	NPD5785	Approved
0.7447	Intermediate Similarity	NPD6435	Approved
0.7396	Intermediate Similarity	NPD5363	Approved
0.7391	Intermediate Similarity	NPD4268	Approved
0.7391	Intermediate Similarity	NPD4271	Approved
0.7374	Intermediate Similarity	NPD6698	Approved
0.7374	Intermediate Similarity	NPD46	Approved
0.7368	Intermediate Similarity	NPD7154	Phase 3
0.734	Intermediate Similarity	NPD5369	Approved
0.7263	Intermediate Similarity	NPD4270	Approved
0.7263	Intermediate Similarity	NPD4269	Approved
0.7234	Intermediate Similarity	NPD5368	Approved
0.7216	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5786	Approved
0.7053	Intermediate Similarity	NPD4252	Approved
0.7048	Intermediate Similarity	NPD7638	Approved
0.703	Intermediate Similarity	NPD7838	Discovery
0.701	Intermediate Similarity	NPD5332	Approved
0.701	Intermediate Similarity	NPD5331	Approved
0.699	Remote Similarity	NPD5282	Discontinued
0.6981	Remote Similarity	NPD7640	Approved
0.6981	Remote Similarity	NPD7639	Approved
0.6979	Remote Similarity	NPD4790	Discontinued
0.6847	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD6008	Approved
0.6814	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7983	Approved
0.6731	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD5779	Approved
0.6729	Remote Similarity	NPD4225	Approved
0.6729	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6607	Remote Similarity	NPD5697	Approved
0.6606	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD5695	Phase 3
0.6574	Remote Similarity	NPD5696	Approved
0.6571	Remote Similarity	NPD6399	Phase 3
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7320	Approved
0.6549	Remote Similarity	NPD6881	Approved
0.6549	Remote Similarity	NPD6899	Approved
0.6545	Remote Similarity	NPD7632	Discontinued
0.6535	Remote Similarity	NPD1694	Approved
0.6525	Remote Similarity	NPD7115	Discovery
0.6522	Remote Similarity	NPD6649	Approved
0.6522	Remote Similarity	NPD6650	Approved
0.6518	Remote Similarity	NPD6675	Approved
0.6518	Remote Similarity	NPD5739	Approved
0.6518	Remote Similarity	NPD6402	Approved
0.6518	Remote Similarity	NPD7128	Approved
0.6491	Remote Similarity	NPD6012	Approved
0.6491	Remote Similarity	NPD6373	Approved
0.6491	Remote Similarity	NPD6372	Approved
0.6491	Remote Similarity	NPD6013	Approved
0.6491	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6014	Approved
0.648	Remote Similarity	NPD7319	Approved
0.6476	Remote Similarity	NPD7637	Suspended
0.646	Remote Similarity	NPD6412	Phase 2
0.646	Remote Similarity	NPD5701	Approved
0.6446	Remote Similarity	NPD8033	Approved
0.6435	Remote Similarity	NPD6883	Approved
0.6435	Remote Similarity	NPD7102	Approved
0.6435	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD7492	Approved
0.641	Remote Similarity	NPD4632	Approved
0.6404	Remote Similarity	NPD6011	Approved
0.6379	Remote Similarity	NPD6617	Approved
0.6379	Remote Similarity	NPD6869	Approved
0.6379	Remote Similarity	NPD6847	Approved
0.6379	Remote Similarity	NPD8130	Phase 1
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD6648	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD6319	Approved
0.6346	Remote Similarity	NPD6903	Approved
0.6333	Remote Similarity	NPD7327	Approved
0.6333	Remote Similarity	NPD7328	Approved
0.6325	Remote Similarity	NPD6882	Approved
0.6325	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD5693	Phase 1
0.6321	Remote Similarity	NPD5284	Approved
0.6321	Remote Similarity	NPD5281	Approved
0.632	Remote Similarity	NPD7078	Approved
0.6316	Remote Similarity	NPD6685	Approved
0.6311	Remote Similarity	NPD7334	Approved
0.6311	Remote Similarity	NPD8516	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD7521	Approved
0.6311	Remote Similarity	NPD8515	Approved
0.6311	Remote Similarity	NPD8513	Phase 3
0.6311	Remote Similarity	NPD5330	Approved
0.6311	Remote Similarity	NPD6016	Approved
0.6311	Remote Similarity	NPD7146	Approved
0.6311	Remote Similarity	NPD6409	Approved
0.6311	Remote Similarity	NPD6684	Approved
0.6311	Remote Similarity	NPD8517	Approved
0.6299	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD4629	Approved
0.6286	Remote Similarity	NPD6101	Approved
0.6286	Remote Similarity	NPD4753	Phase 2
0.6286	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7516	Approved
0.6275	Remote Similarity	NPD3665	Phase 1
0.6275	Remote Similarity	NPD3133	Approved
0.6275	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3666	Approved
0.627	Remote Similarity	NPD7736	Approved
0.626	Remote Similarity	NPD5988	Approved
0.626	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD7839	Suspended
0.6238	Remote Similarity	NPD5209	Approved
0.623	Remote Similarity	NPD6059	Approved
0.623	Remote Similarity	NPD8294	Approved
0.623	Remote Similarity	NPD8377	Approved
0.6226	Remote Similarity	NPD5207	Approved
0.6216	Remote Similarity	NPD5285	Approved
0.6216	Remote Similarity	NPD5286	Approved
0.6216	Remote Similarity	NPD4696	Approved
0.619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8293	Discontinued
0.6182	Remote Similarity	NPD4755	Approved
0.6179	Remote Similarity	NPD7503	Approved
0.6179	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD8335	Approved
0.6179	Remote Similarity	NPD8379	Approved
0.6179	Remote Similarity	NPD8380	Approved
0.6179	Remote Similarity	NPD5983	Phase 2
0.6179	Remote Similarity	NPD8296	Approved
0.6179	Remote Similarity	NPD8378	Approved
0.6176	Remote Similarity	NPD6695	Phase 3
0.6174	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6411	Approved
0.6167	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD5141	Approved
0.6134	Remote Similarity	NPD8133	Approved
0.6132	Remote Similarity	NPD6051	Approved
0.6132	Remote Similarity	NPD5370	Suspended
0.6111	Remote Similarity	NPD4202	Approved
0.6106	Remote Similarity	NPD5224	Approved
0.6106	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD4633	Approved
0.6106	Remote Similarity	NPD5226	Approved
0.6102	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7604	Phase 2
0.6078	Remote Similarity	NPD3667	Approved
0.6077	Remote Similarity	NPD6845	Suspended
0.6071	Remote Similarity	NPD4700	Approved
0.6067	Remote Similarity	NPD3198	Approved
0.6063	Remote Similarity	NPD8074	Phase 3
0.6055	Remote Similarity	NPD6001	Approved
0.6053	Remote Similarity	NPD5175	Approved
0.6053	Remote Similarity	NPD5174	Approved
0.6053	Remote Similarity	NPD5765	Approved
0.6019	Remote Similarity	NPD8035	Phase 2
0.6019	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD4788	Approved
0.6018	Remote Similarity	NPD5223	Approved
0.6017	Remote Similarity	NPD4634	Approved
0.6017	Remote Similarity	NPD6420	Discontinued
0.6016	Remote Similarity	NPD7100	Approved
0.6016	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD7260	Phase 2
0.5985	Remote Similarity	NPD6004	Phase 3
0.5985	Remote Similarity	NPD6002	Phase 3
0.5985	Remote Similarity	NPD6005	Phase 3
0.5985	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6336	Discontinued
0.5984	Remote Similarity	NPD6317	Approved
0.5981	Remote Similarity	NPD6080	Approved
0.5981	Remote Similarity	NPD6904	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