NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	266.942
LogP:	1.306
LogD:	1.232
LogS:	-2.798
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.728
Fsp3:	0.6
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:	-4.561
MDCK Permeability:	2.7339883672539145e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.078
20% Bioavailability (F20%):	0.667
30% Bioavailability (F30%):	0.431

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	58.563232421875%
Volume Distribution (VD):	0.643
Pgp-substrate:	44.54323196411133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.382
CYP3A4-substrate:	0.335

ADMET: Excretion

Clearance (CL):	10.298
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.581
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.875
Maximum Recommended Daily Dose:	0.577
Skin Sensitization:	0.595
Carcinogencity:	0.848
Eye Corrosion:	0.415
Eye Irritation:	0.324
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC48803

Natural Product ID:	NPC48803
*Common Name:**	8-Epihelenalin
IUPAC Name:	(3aS,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
Synonyms:	8-Epihelenalin
Standard InCHIKey:	ZVLOPMNVFLSSAA-GSNHZRAGSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10+,12-,13+,15+/m1/s1
SMILES:	C[C@@H]1C[C@H]2[C@@H](C(=C)C(=O)O2)[C@@H]([C@@]2(C)[C@H]1C=CC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911137
PubChem CID:	10400473
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
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21894898]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO13035	Helenium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[490173]
NPO13035	Helenium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7119807]
NPO26233.1	Helenium autumnale var. montanum	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26233	Helenium autumnale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13035	Helenium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26233	Helenium autumnale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13035	Helenium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26233.1	Helenium autumnale var. montanum	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26233	Helenium autumnale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21806	Helenium tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26233	Helenium autumnale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13035	Helenium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1100.0	nM	PMID[475898]

☑ 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 NPC48803 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	206
0.1-0.2	1196
0.2-0.3	5088
0.3-0.4	10183
0.4-0.5	13482
0.5-0.6	7165
0.6-0.7	4322
0.7-0.8	939
0.8-0.85	63
0.85-0.9	34
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193645
1.0	High Similarity	NPC90121
1.0	High Similarity	NPC275960
0.9778	High Similarity	NPC169205
0.967	High Similarity	NPC141191
0.9667	High Similarity	NPC185553
0.9438	High Similarity	NPC70595
0.9438	High Similarity	NPC123177
0.9438	High Similarity	NPC74103
0.9438	High Similarity	NPC150978
0.9432	High Similarity	NPC117405
0.9432	High Similarity	NPC52198
0.9326	High Similarity	NPC253144
0.9231	High Similarity	NPC167219
0.9222	High Similarity	NPC284185
0.9167	High Similarity	NPC203659
0.9158	High Similarity	NPC225353
0.9062	High Similarity	NPC110989
0.9011	High Similarity	NPC111114
0.9011	High Similarity	NPC300312
0.9011	High Similarity	NPC261607
0.9	High Similarity	NPC168679
0.9	High Similarity	NPC12872
0.8977	High Similarity	NPC161957
0.8977	High Similarity	NPC33570
0.8977	High Similarity	NPC21471
0.8876	High Similarity	NPC104961
0.8876	High Similarity	NPC70422
0.8876	High Similarity	NPC70555
0.8842	High Similarity	NPC54843
0.8817	High Similarity	NPC289004
0.875	High Similarity	NPC39588
0.8696	High Similarity	NPC129419
0.866	High Similarity	NPC171759
0.8587	High Similarity	NPC268298
0.8571	High Similarity	NPC474747
0.8539	High Similarity	NPC215294
0.8526	High Similarity	NPC304886
0.8511	High Similarity	NPC135776
0.8485	Intermediate Similarity	NPC475871
0.8485	Intermediate Similarity	NPC475945
0.8469	Intermediate Similarity	NPC477950
0.8462	Intermediate Similarity	NPC236692
0.8462	Intermediate Similarity	NPC238593
0.8462	Intermediate Similarity	NPC309757
0.8444	Intermediate Similarity	NPC165287
0.8438	Intermediate Similarity	NPC142529
0.8438	Intermediate Similarity	NPC91771
0.8409	Intermediate Similarity	NPC223904
0.8404	Intermediate Similarity	NPC131209
0.837	Intermediate Similarity	NPC201658
0.837	Intermediate Similarity	NPC237540
0.8352	Intermediate Similarity	NPC165162
0.8351	Intermediate Similarity	NPC108475
0.8351	Intermediate Similarity	NPC213947
0.8351	Intermediate Similarity	NPC170143
0.8316	Intermediate Similarity	NPC200237
0.8316	Intermediate Similarity	NPC153590
0.8298	Intermediate Similarity	NPC71533
0.8298	Intermediate Similarity	NPC106510
0.8283	Intermediate Similarity	NPC474742
0.8261	Intermediate Similarity	NPC107787
0.8247	Intermediate Similarity	NPC126156
0.8242	Intermediate Similarity	NPC115786
0.8229	Intermediate Similarity	NPC473331
0.8229	Intermediate Similarity	NPC477131
0.8222	Intermediate Similarity	NPC89555
0.8218	Intermediate Similarity	NPC309190
0.8218	Intermediate Similarity	NPC100487
0.8218	Intermediate Similarity	NPC474741
0.8211	Intermediate Similarity	NPC133698
0.8202	Intermediate Similarity	NPC74673
0.8202	Intermediate Similarity	NPC69271
0.8191	Intermediate Similarity	NPC32922
0.8152	Intermediate Similarity	NPC78089
0.8132	Intermediate Similarity	NPC54468
0.8125	Intermediate Similarity	NPC473273
0.8125	Intermediate Similarity	NPC60386
0.8125	Intermediate Similarity	NPC308656
0.8125	Intermediate Similarity	NPC475302
0.8125	Intermediate Similarity	NPC473234
0.8125	Intermediate Similarity	NPC473263
0.8119	Intermediate Similarity	NPC475873
0.8113	Intermediate Similarity	NPC209058
0.8111	Intermediate Similarity	NPC10276
0.8111	Intermediate Similarity	NPC35089
0.8105	Intermediate Similarity	NPC62815
0.8105	Intermediate Similarity	NPC469368
0.81	Intermediate Similarity	NPC110443
0.81	Intermediate Similarity	NPC133907
0.81	Intermediate Similarity	NPC46998
0.81	Intermediate Similarity	NPC128733
0.81	Intermediate Similarity	NPC185141
0.81	Intermediate Similarity	NPC472753
0.809	Intermediate Similarity	NPC470244
0.809	Intermediate Similarity	NPC470239
0.8085	Intermediate Similarity	NPC476805
0.8065	Intermediate Similarity	NPC305475
0.8065	Intermediate Similarity	NPC475461
0.8065	Intermediate Similarity	NPC150755
0.8061	Intermediate Similarity	NPC18019
0.8061	Intermediate Similarity	NPC24956
0.8043	Intermediate Similarity	NPC141193
0.8043	Intermediate Similarity	NPC96259
0.8043	Intermediate Similarity	NPC191476
0.8043	Intermediate Similarity	NPC114979
0.8041	Intermediate Similarity	NPC198853
0.8041	Intermediate Similarity	NPC469632
0.8041	Intermediate Similarity	NPC470013
0.8041	Intermediate Similarity	NPC323008
0.8041	Intermediate Similarity	NPC470010
0.8041	Intermediate Similarity	NPC262133
0.8021	Intermediate Similarity	NPC286341
0.8021	Intermediate Similarity	NPC191339
0.802	Intermediate Similarity	NPC472754
0.8	Intermediate Similarity	NPC295312
0.8	Intermediate Similarity	NPC51507
0.8	Intermediate Similarity	NPC302426
0.8	Intermediate Similarity	NPC73052
0.8	Intermediate Similarity	NPC276356
0.8	Intermediate Similarity	NPC293418
0.8	Intermediate Similarity	NPC155935
0.8	Intermediate Similarity	NPC290508
0.8	Intermediate Similarity	NPC6823
0.7981	Intermediate Similarity	NPC475960
0.798	Intermediate Similarity	NPC311904
0.798	Intermediate Similarity	NPC474343
0.798	Intermediate Similarity	NPC477949
0.7979	Intermediate Similarity	NPC72513
0.7979	Intermediate Similarity	NPC118601
0.7961	Intermediate Similarity	NPC243998
0.7957	Intermediate Similarity	NPC125290
0.7957	Intermediate Similarity	NPC470755
0.7957	Intermediate Similarity	NPC255307
0.7941	Intermediate Similarity	NPC472755
0.7938	Intermediate Similarity	NPC469645
0.7938	Intermediate Similarity	NPC469692
0.7921	Intermediate Similarity	NPC47880
0.7921	Intermediate Similarity	NPC244456
0.7921	Intermediate Similarity	NPC469657
0.7917	Intermediate Similarity	NPC54065
0.7917	Intermediate Similarity	NPC297474
0.7917	Intermediate Similarity	NPC77337
0.7917	Intermediate Similarity	NPC19087
0.7917	Intermediate Similarity	NPC35809
0.7917	Intermediate Similarity	NPC145666
0.7912	Intermediate Similarity	NPC255580
0.7912	Intermediate Similarity	NPC39411
0.7912	Intermediate Similarity	NPC470241
0.7912	Intermediate Similarity	NPC25684
0.7912	Intermediate Similarity	NPC281949
0.7912	Intermediate Similarity	NPC301477
0.7905	Intermediate Similarity	NPC47951
0.7895	Intermediate Similarity	NPC178875
0.7895	Intermediate Similarity	NPC91248
0.7895	Intermediate Similarity	NPC476803
0.7895	Intermediate Similarity	NPC202672
0.7879	Intermediate Similarity	NPC476009
0.7872	Intermediate Similarity	NPC470242
0.7872	Intermediate Similarity	NPC261721
0.7864	Intermediate Similarity	NPC472756
0.7857	Intermediate Similarity	NPC121825
0.7857	Intermediate Similarity	NPC53685
0.785	Intermediate Similarity	NPC123855
0.785	Intermediate Similarity	NPC138757
0.785	Intermediate Similarity	NPC76550
0.7849	Intermediate Similarity	NPC156485
0.7849	Intermediate Similarity	NPC158756
0.7849	Intermediate Similarity	NPC476804
0.7843	Intermediate Similarity	NPC149371
0.7843	Intermediate Similarity	NPC86077
0.7835	Intermediate Similarity	NPC12172
0.7835	Intermediate Similarity	NPC171360
0.7835	Intermediate Similarity	NPC475925
0.7835	Intermediate Similarity	NPC63193
0.7835	Intermediate Similarity	NPC133888
0.7835	Intermediate Similarity	NPC184063
0.7835	Intermediate Similarity	NPC208886
0.7835	Intermediate Similarity	NPC35959
0.7835	Intermediate Similarity	NPC184463
0.7835	Intermediate Similarity	NPC29821
0.7835	Intermediate Similarity	NPC219874
0.7835	Intermediate Similarity	NPC57304
0.7835	Intermediate Similarity	NPC293001
0.783	Intermediate Similarity	NPC471884
0.783	Intermediate Similarity	NPC477103
0.783	Intermediate Similarity	NPC257240
0.7826	Intermediate Similarity	NPC229825
0.7822	Intermediate Similarity	NPC469872
0.7822	Intermediate Similarity	NPC288876
0.7822	Intermediate Similarity	NPC469864
0.7812	Intermediate Similarity	NPC212664
0.7812	Intermediate Similarity	NPC38392
0.78	Intermediate Similarity	NPC91695
0.78	Intermediate Similarity	NPC70145
0.7789	Intermediate Similarity	NPC190753
0.7788	Intermediate Similarity	NPC223450
0.7778	Intermediate Similarity	NPC52044
0.7778	Intermediate Similarity	NPC209355
0.7778	Intermediate Similarity	NPC475900

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 NPC48803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1780
0.2-0.3	3741
0.3-0.4	2315
0.4-0.5	692
0.5-0.6	290
0.6-0.7	128
0.7-0.8	14
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1698	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5785	Approved
0.783	Intermediate Similarity	NPD6371	Approved
0.7714	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5282	Discontinued
0.7629	Intermediate Similarity	NPD1695	Approved
0.7396	Intermediate Similarity	NPD5363	Approved
0.7396	Intermediate Similarity	NPD1694	Approved
0.7379	Intermediate Similarity	NPD4225	Approved
0.732	Intermediate Similarity	NPD5786	Approved
0.73	Intermediate Similarity	NPD6411	Approved
0.7263	Intermediate Similarity	NPD5209	Approved
0.7263	Intermediate Similarity	NPD6435	Approved
0.7158	Intermediate Similarity	NPD5369	Approved
0.71	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4269	Approved
0.7083	Intermediate Similarity	NPD4270	Approved
0.7059	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD5778	Approved
0.7053	Intermediate Similarity	NPD5368	Approved
0.7041	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5362	Discontinued
0.701	Intermediate Similarity	NPD7154	Phase 3
0.6961	Remote Similarity	NPD7983	Approved
0.6957	Remote Similarity	NPD7115	Discovery
0.6909	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4252	Approved
0.6863	Remote Similarity	NPD6698	Approved
0.6863	Remote Similarity	NPD46	Approved
0.6847	Remote Similarity	NPD6899	Approved
0.6847	Remote Similarity	NPD6881	Approved
0.6842	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6649	Approved
0.6814	Remote Similarity	NPD6650	Approved
0.6786	Remote Similarity	NPD6012	Approved
0.6786	Remote Similarity	NPD6013	Approved
0.6786	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD6053	Discontinued
0.6731	Remote Similarity	NPD6399	Phase 3
0.6726	Remote Similarity	NPD7290	Approved
0.6726	Remote Similarity	NPD6883	Approved
0.6726	Remote Similarity	NPD7102	Approved
0.6701	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6637	Remote Similarity	NPD6372	Approved
0.6637	Remote Similarity	NPD6373	Approved
0.6634	Remote Similarity	NPD4249	Approved
0.6609	Remote Similarity	NPD8297	Approved
0.6609	Remote Similarity	NPD6882	Approved
0.6607	Remote Similarity	NPD5701	Approved
0.6569	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD4250	Approved
0.6557	Remote Similarity	NPD7492	Approved
0.6545	Remote Similarity	NPD5211	Phase 2
0.6542	Remote Similarity	NPD7839	Suspended
0.6531	Remote Similarity	NPD4822	Approved
0.6531	Remote Similarity	NPD4819	Approved
0.6531	Remote Similarity	NPD4821	Approved
0.6531	Remote Similarity	NPD4820	Approved
0.6518	Remote Similarity	NPD6008	Approved
0.6514	Remote Similarity	NPD5286	Approved
0.6514	Remote Similarity	NPD4696	Approved
0.6514	Remote Similarity	NPD5285	Approved
0.6504	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD6319	Approved
0.65	Remote Similarity	NPD6054	Approved
0.6495	Remote Similarity	NPD4271	Approved
0.6495	Remote Similarity	NPD4268	Approved
0.6481	Remote Similarity	NPD6084	Phase 2
0.6481	Remote Similarity	NPD7902	Approved
0.6481	Remote Similarity	NPD6083	Phase 2
0.6476	Remote Similarity	NPD7637	Suspended
0.6476	Remote Similarity	NPD6079	Approved
0.6452	Remote Similarity	NPD7078	Approved
0.6449	Remote Similarity	NPD5695	Phase 3
0.6446	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6016	Approved
0.6446	Remote Similarity	NPD6015	Approved
0.6429	Remote Similarity	NPD5141	Approved
0.6422	Remote Similarity	NPD7638	Approved
0.6422	Remote Similarity	NPD5696	Approved
0.6404	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7736	Approved
0.6396	Remote Similarity	NPD5226	Approved
0.6396	Remote Similarity	NPD5225	Approved
0.6396	Remote Similarity	NPD4633	Approved
0.6396	Remote Similarity	NPD5224	Approved
0.6393	Remote Similarity	NPD5988	Approved
0.6393	Remote Similarity	NPD6370	Approved
0.6389	Remote Similarity	NPD5222	Approved
0.6389	Remote Similarity	NPD5221	Approved
0.6389	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6355	Remote Similarity	NPD7748	Approved
0.6346	Remote Similarity	NPD6903	Approved
0.6339	Remote Similarity	NPD5175	Approved
0.6339	Remote Similarity	NPD5174	Approved
0.6337	Remote Similarity	NPD5332	Approved
0.6337	Remote Similarity	NPD5331	Approved
0.633	Remote Similarity	NPD5173	Approved
0.633	Remote Similarity	NPD4755	Approved
0.6321	Remote Similarity	NPD7515	Phase 2
0.6321	Remote Similarity	NPD5284	Approved
0.6321	Remote Similarity	NPD5281	Approved
0.6311	Remote Similarity	NPD8515	Approved
0.6311	Remote Similarity	NPD8513	Phase 3
0.6311	Remote Similarity	NPD7521	Approved
0.6311	Remote Similarity	NPD7146	Approved
0.6311	Remote Similarity	NPD7334	Approved
0.6311	Remote Similarity	NPD5330	Approved
0.6311	Remote Similarity	NPD3618	Phase 1
0.6311	Remote Similarity	NPD6409	Approved
0.6311	Remote Similarity	NPD6684	Approved
0.6311	Remote Similarity	NPD8516	Approved
0.6311	Remote Similarity	NPD8517	Approved
0.6306	Remote Similarity	NPD5223	Approved
0.6303	Remote Similarity	NPD6274	Approved
0.63	Remote Similarity	NPD4790	Discontinued
0.6296	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD4629	Approved
0.6293	Remote Similarity	NPD4634	Approved
0.6286	Remote Similarity	NPD5328	Approved
0.6286	Remote Similarity	NPD5370	Suspended
0.6281	Remote Similarity	NPD7100	Approved
0.6281	Remote Similarity	NPD7101	Approved
0.6275	Remote Similarity	NPD3133	Approved
0.6275	Remote Similarity	NPD3666	Approved
0.6275	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3665	Phase 1
0.6273	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD3573	Approved
0.625	Remote Similarity	NPD6317	Approved
0.6239	Remote Similarity	NPD4697	Phase 3
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD3667	Approved
0.623	Remote Similarity	NPD6059	Approved
0.6226	Remote Similarity	NPD5207	Approved
0.622	Remote Similarity	NPD7319	Approved
0.6216	Remote Similarity	NPD4700	Approved
0.6204	Remote Similarity	NPD7900	Approved
0.6204	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4695	Discontinued
0.6198	Remote Similarity	NPD6314	Approved
0.6198	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD6313	Approved
0.619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8293	Discontinued
0.619	Remote Similarity	NPD6672	Approved
0.619	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD8039	Approved
0.6168	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5693	Phase 1
0.6167	Remote Similarity	NPD6868	Approved
0.6161	Remote Similarity	NPD5344	Discontinued
0.6154	Remote Similarity	NPD5279	Phase 3
0.6154	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4753	Phase 2
0.6124	Remote Similarity	NPD7260	Phase 2
0.6121	Remote Similarity	NPD4729	Approved
0.6121	Remote Similarity	NPD4730	Approved
0.6117	Remote Similarity	NPD4786	Approved
0.6116	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD7507	Approved
0.608	Remote Similarity	NPD8328	Phase 3
0.608	Remote Similarity	NPD7642	Approved
0.6068	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8074	Phase 3
0.6058	Remote Similarity	NPD1696	Phase 3
0.6048	Remote Similarity	NPD5983	Phase 2
0.6034	Remote Similarity	NPD6412	Phase 2
0.6022	Remote Similarity	NPD7331	Phase 2
0.6017	Remote Similarity	NPD5250	Approved
0.6017	Remote Similarity	NPD5251	Approved
0.6017	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5249	Phase 3
0.6017	Remote Similarity	NPD5248	Approved
0.6017	Remote Similarity	NPD5247	Approved
0.6015	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD4623	Approved
0.5983	Remote Similarity	NPD5128	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