NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.003
LogD:	1.274
LogS:	-2.644
# 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:	0.531
Synthetic Accessibility Score:	4.613
Fsp3:	0.733
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:	-4.586
MDCK Permeability:	2.4502598535036668e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.231
Plasma Protein Binding (PPB):	61.306915283203125%
Volume Distribution (VD):	0.6
Pgp-substrate:	41.8119010925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.345
CYP1A2-substrate:	0.592
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	7.107
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.588
Drug-inuced Liver Injury (DILI):	0.542
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.743
Maximum Recommended Daily Dose:	0.436
Skin Sensitization:	0.296
Carcinogencity:	0.236
Eye Corrosion:	0.574
Eye Irritation:	0.39
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC178875

Natural Product ID:	NPC178875
*Common Name:**	(3As,6R,6Ar,9S,9Ar,9Br)-6-Hydroxy-6,9-Dimethyl-3-Methyleneoctahydroazuleno[4,5-B]Furan-2,8(3H,9Bh)-Dione
IUPAC Name:	(3aS,6R,6aR,9S,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
Synonyms:
Standard InCHIKey:	ZYSPQNWXTOPYEA-XCBWYEDLSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-7-9-4-5-15(3,18)10-6-11(16)8(2)12(10)13(9)19-14(7)17/h8-10,12-13,18H,1,4-6H2,2-3H3/t8-,9+,10-,12+,13+,15-/m1/s1
SMILES:	C[C@@H]1C(=O)C[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CC[C@@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463601
PubChem CID:	11139989
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 [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15635221]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067155]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10533	Ixeris chinensis	Species	Asteraceae	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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16400.0	nM	PMID[508927]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16800.0	nM	PMID[508927]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[508927]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	25000.0	nM	PMID[508927]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	27000.0	nM	PMID[508927]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22000.0	nM	PMID[508927]

☑ 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 NPC178875 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	240
0.1-0.2	1793
0.2-0.3	6609
0.3-0.4	14427
0.4-0.5	10291
0.5-0.6	6346
0.6-0.7	2431
0.7-0.8	395
0.8-0.85	78
0.85-0.9	73
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC118601
0.9318	High Similarity	NPC163228
0.931	High Similarity	NPC153590
0.9294	High Similarity	NPC79549
0.9286	High Similarity	NPC236692
0.9286	High Similarity	NPC309757
0.9186	High Similarity	NPC215556
0.9167	High Similarity	NPC300082
0.9167	High Similarity	NPC204105
0.9167	High Similarity	NPC284534
0.9091	High Similarity	NPC135776
0.908	High Similarity	NPC216284
0.9059	High Similarity	NPC470242
0.8977	High Similarity	NPC155215
0.8953	High Similarity	NPC270270
0.8889	High Similarity	NPC476053
0.8876	High Similarity	NPC473234
0.8876	High Similarity	NPC60386
0.8876	High Similarity	NPC308656
0.8876	High Similarity	NPC200237
0.8876	High Similarity	NPC258216
0.8876	High Similarity	NPC473263
0.8876	High Similarity	NPC473273
0.8851	High Similarity	NPC217983
0.8851	High Similarity	NPC207114
0.8837	High Similarity	NPC187661
0.8824	High Similarity	NPC194859
0.8824	High Similarity	NPC224386
0.881	High Similarity	NPC246076
0.8791	High Similarity	NPC142529
0.8791	High Similarity	NPC91771
0.8778	High Similarity	NPC473331
0.8764	High Similarity	NPC133698
0.8764	High Similarity	NPC131209
0.8764	High Similarity	NPC184063
0.875	High Similarity	NPC155935
0.875	High Similarity	NPC32922
0.875	High Similarity	NPC12872
0.875	High Similarity	NPC168679
0.8736	High Similarity	NPC190753
0.871	High Similarity	NPC471381
0.871	High Similarity	NPC186861
0.8706	High Similarity	NPC54468
0.8706	High Similarity	NPC245665
0.8696	High Similarity	NPC471150
0.8681	High Similarity	NPC472873
0.8659	High Similarity	NPC208223
0.8652	High Similarity	NPC54065
0.8652	High Similarity	NPC35809
0.8652	High Similarity	NPC19087
0.8652	High Similarity	NPC297474
0.8636	High Similarity	NPC91248
0.8621	High Similarity	NPC56593
0.8621	High Similarity	NPC67493
0.8571	High Similarity	NPC156658
0.8571	High Similarity	NPC323008
0.8571	High Similarity	NPC51507
0.8571	High Similarity	NPC293418
0.8571	High Similarity	NPC258965
0.8571	High Similarity	NPC198853
0.8571	High Similarity	NPC470013
0.8571	High Similarity	NPC262133
0.8571	High Similarity	NPC477131
0.8571	High Similarity	NPC73052
0.8571	High Similarity	NPC290508
0.8571	High Similarity	NPC470010
0.8556	High Similarity	NPC57304
0.8556	High Similarity	NPC35959
0.8556	High Similarity	NPC293001
0.8556	High Similarity	NPC286341
0.8556	High Similarity	NPC191339
0.8556	High Similarity	NPC171360
0.8556	High Similarity	NPC63193
0.8556	High Similarity	NPC29821
0.8556	High Similarity	NPC133888
0.8539	High Similarity	NPC472872
0.8539	High Similarity	NPC38392
0.8523	High Similarity	NPC201658
0.8523	High Similarity	NPC186148
0.8495	Intermediate Similarity	NPC108475
0.8495	Intermediate Similarity	NPC170143
0.8495	Intermediate Similarity	NPC213947
0.8495	Intermediate Similarity	NPC311904
0.8488	Intermediate Similarity	NPC111409
0.8488	Intermediate Similarity	NPC128246
0.8478	Intermediate Similarity	NPC475900
0.8478	Intermediate Similarity	NPC67584
0.8478	Intermediate Similarity	NPC52044
0.8471	Intermediate Similarity	NPC126248
0.8444	Intermediate Similarity	NPC37607
0.8444	Intermediate Similarity	NPC301969
0.8427	Intermediate Similarity	NPC177629
0.8427	Intermediate Similarity	NPC58219
0.8421	Intermediate Similarity	NPC171759
0.8409	Intermediate Similarity	NPC238593
0.8409	Intermediate Similarity	NPC64153
0.8409	Intermediate Similarity	NPC304558
0.8404	Intermediate Similarity	NPC45125
0.8387	Intermediate Similarity	NPC213078
0.8387	Intermediate Similarity	NPC476009
0.837	Intermediate Similarity	NPC127019
0.8352	Intermediate Similarity	NPC475925
0.8333	Intermediate Similarity	NPC92974
0.8315	Intermediate Similarity	NPC24728
0.8298	Intermediate Similarity	NPC181151
0.8298	Intermediate Similarity	NPC161493
0.8298	Intermediate Similarity	NPC474313
0.8295	Intermediate Similarity	NPC235792
0.8293	Intermediate Similarity	NPC215030
0.8293	Intermediate Similarity	NPC143979
0.8293	Intermediate Similarity	NPC320537
0.828	Intermediate Similarity	NPC170120
0.828	Intermediate Similarity	NPC213698
0.8265	Intermediate Similarity	NPC54737
0.8256	Intermediate Similarity	NPC47635
0.8242	Intermediate Similarity	NPC62815
0.8222	Intermediate Similarity	NPC202672
0.8222	Intermediate Similarity	NPC471149
0.8211	Intermediate Similarity	NPC221615
0.8202	Intermediate Similarity	NPC474762
0.8202	Intermediate Similarity	NPC162071
0.8202	Intermediate Similarity	NPC474949
0.8202	Intermediate Similarity	NPC476015
0.8202	Intermediate Similarity	NPC475019
0.8191	Intermediate Similarity	NPC24956
0.8191	Intermediate Similarity	NPC18019
0.8182	Intermediate Similarity	NPC156485
0.8152	Intermediate Similarity	NPC12172
0.8152	Intermediate Similarity	NPC208886
0.814	Intermediate Similarity	NPC6823
0.8132	Intermediate Similarity	NPC307411
0.8132	Intermediate Similarity	NPC283409
0.8132	Intermediate Similarity	NPC474951
0.8132	Intermediate Similarity	NPC4986
0.8132	Intermediate Similarity	NPC173926
0.809	Intermediate Similarity	NPC47958
0.809	Intermediate Similarity	NPC304509
0.809	Intermediate Similarity	NPC329749
0.809	Intermediate Similarity	NPC149725
0.8085	Intermediate Similarity	NPC304886
0.8081	Intermediate Similarity	NPC243998
0.8081	Intermediate Similarity	NPC223450
0.8065	Intermediate Similarity	NPC472874
0.8065	Intermediate Similarity	NPC81419
0.8065	Intermediate Similarity	NPC179746
0.8043	Intermediate Similarity	NPC51004
0.8022	Intermediate Similarity	NPC224652
0.802	Intermediate Similarity	NPC59489
0.802	Intermediate Similarity	NPC139838
0.8	Intermediate Similarity	NPC126156
0.7979	Intermediate Similarity	NPC190294
0.7978	Intermediate Similarity	NPC474780
0.7978	Intermediate Similarity	NPC470238
0.7978	Intermediate Similarity	NPC138647
0.7959	Intermediate Similarity	NPC86077
0.7959	Intermediate Similarity	NPC474747
0.7959	Intermediate Similarity	NPC80144
0.7957	Intermediate Similarity	NPC30515
0.7957	Intermediate Similarity	NPC184463
0.7957	Intermediate Similarity	NPC70251
0.7957	Intermediate Similarity	NPC475881
0.7941	Intermediate Similarity	NPC471884
0.7935	Intermediate Similarity	NPC295312
0.7935	Intermediate Similarity	NPC268298
0.7931	Intermediate Similarity	NPC276356
0.7931	Intermediate Similarity	NPC69271
0.7931	Intermediate Similarity	NPC74673
0.7931	Intermediate Similarity	NPC474981
0.7912	Intermediate Similarity	NPC5130
0.79	Intermediate Similarity	NPC44004
0.7895	Intermediate Similarity	NPC48803
0.7895	Intermediate Similarity	NPC275960
0.7895	Intermediate Similarity	NPC90121
0.7895	Intermediate Similarity	NPC193645
0.7885	Intermediate Similarity	NPC209058
0.7879	Intermediate Similarity	NPC475871
0.7879	Intermediate Similarity	NPC475945
0.7872	Intermediate Similarity	NPC476300
0.7872	Intermediate Similarity	NPC475912
0.7872	Intermediate Similarity	NPC212486
0.7872	Intermediate Similarity	NPC475788
0.7865	Intermediate Similarity	NPC257358
0.7865	Intermediate Similarity	NPC128429
0.7865	Intermediate Similarity	NPC272814
0.7865	Intermediate Similarity	NPC39588
0.7865	Intermediate Similarity	NPC474472
0.7857	Intermediate Similarity	NPC67296
0.7857	Intermediate Similarity	NPC474742
0.7857	Intermediate Similarity	NPC150923
0.7849	Intermediate Similarity	NPC106510
0.7849	Intermediate Similarity	NPC206614
0.7849	Intermediate Similarity	NPC246173
0.7849	Intermediate Similarity	NPC71533
0.7849	Intermediate Similarity	NPC474323
0.7849	Intermediate Similarity	NPC129419
0.7841	Intermediate Similarity	NPC35089
0.7841	Intermediate Similarity	NPC10276
0.7835	Intermediate Similarity	NPC49833
0.7835	Intermediate Similarity	NPC249171
0.7826	Intermediate Similarity	NPC53158

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 NPC178875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	2530
0.2-0.3	3926
0.3-0.4	1668
0.4-0.5	449
0.5-0.6	256
0.6-0.7	30
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD1695	Approved
0.7895	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7103	Intermediate Similarity	NPD6371	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6809	Remote Similarity	NPD6435	Approved
0.6771	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5785	Approved
0.6737	Remote Similarity	NPD5362	Discontinued
0.6733	Remote Similarity	NPD5282	Discontinued
0.6702	Remote Similarity	NPD5369	Approved
0.6701	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD4249	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD4251	Approved
0.66	Remote Similarity	NPD6698	Approved
0.66	Remote Similarity	NPD46	Approved
0.6598	Remote Similarity	NPD5363	Approved
0.6596	Remote Similarity	NPD5368	Approved
0.6458	Remote Similarity	NPD4269	Approved
0.6458	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD1694	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD7983	Approved
0.6373	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD4632	Approved
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD5779	Approved
0.6306	Remote Similarity	NPD7320	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6306	Remote Similarity	NPD6011	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6275	Remote Similarity	NPD7838	Discovery
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4819	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6224	Remote Similarity	NPD5331	Approved
0.6224	Remote Similarity	NPD5332	Approved
0.6224	Remote Similarity	NPD7154	Phase 3
0.6216	Remote Similarity	NPD5701	Approved
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.619	Remote Similarity	NPD5695	Phase 3
0.6186	Remote Similarity	NPD4790	Discontinued
0.6168	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5696	Approved
0.6161	Remote Similarity	NPD6686	Approved
0.6161	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD7115	Discovery
0.6148	Remote Similarity	NPD7507	Approved
0.6148	Remote Similarity	NPD6616	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6869	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6134	Remote Similarity	NPD6319	Approved
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6845	Suspended
0.6098	Remote Similarity	NPD7078	Approved
0.6087	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD8297	Approved
0.6083	Remote Similarity	NPD6016	Approved
0.6083	Remote Similarity	NPD6015	Approved
0.6083	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5983	Phase 2
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6061	Remote Similarity	NPD4788	Approved
0.6058	Remote Similarity	NPD5281	Approved
0.6058	Remote Similarity	NPD5284	Approved
0.6058	Remote Similarity	NPD5693	Phase 1
0.6048	Remote Similarity	NPD7736	Approved
0.6042	Remote Similarity	NPD4271	Approved
0.6042	Remote Similarity	NPD4268	Approved
0.6042	Remote Similarity	NPD4238	Approved
0.6042	Remote Similarity	NPD4802	Phase 2
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8133	Approved
0.6033	Remote Similarity	NPD6370	Approved
0.6033	Remote Similarity	NPD5988	Approved
0.6032	Remote Similarity	NPD7260	Phase 2
0.6019	Remote Similarity	NPD6101	Approved
0.6019	Remote Similarity	NPD4225	Approved
0.6019	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6059	Approved
0.5984	Remote Similarity	NPD7604	Phase 2
0.5968	Remote Similarity	NPD8293	Discontinued
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.5962	Remote Similarity	NPD5207	Approved
0.595	Remote Similarity	NPD8517	Approved
0.595	Remote Similarity	NPD8516	Approved
0.595	Remote Similarity	NPD8266	Approved
0.595	Remote Similarity	NPD8269	Approved
0.595	Remote Similarity	NPD8515	Approved
0.595	Remote Similarity	NPD8267	Approved
0.595	Remote Similarity	NPD8268	Approved
0.595	Remote Similarity	NPD8513	Phase 3
0.5941	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6274	Approved
0.5926	Remote Similarity	NPD4755	Approved
0.5922	Remote Similarity	NPD6903	Approved
0.5922	Remote Similarity	NPD5737	Approved
0.5922	Remote Similarity	NPD6672	Approved
0.5913	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD1700	Approved
0.5909	Remote Similarity	NPD5344	Discontinued
0.5909	Remote Similarity	NPD5223	Approved
0.5905	Remote Similarity	NPD7637	Suspended
0.5905	Remote Similarity	NPD6079	Approved
0.5905	Remote Similarity	NPD6411	Approved
0.5893	Remote Similarity	NPD5141	Approved
0.5887	Remote Similarity	NPD6336	Discontinued
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD6317	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5865	Remote Similarity	NPD5328	Approved
0.5856	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD5224	Approved
0.5856	Remote Similarity	NPD5225	Approved
0.5856	Remote Similarity	NPD7632	Discontinued
0.5842	Remote Similarity	NPD4786	Approved
0.5842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6314	Approved
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD6335	Approved
0.5833	Remote Similarity	NPD7839	Suspended
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4697	Phase 3
0.5833	Remote Similarity	NPD6313	Approved
0.5833	Remote Similarity	NPD5221	Approved
0.5826	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD4700	Approved
0.5818	Remote Similarity	NPD6648	Approved
0.5804	Remote Similarity	NPD5174	Approved
0.5804	Remote Similarity	NPD5175	Approved
0.58	Remote Similarity	NPD3667	Approved
0.58	Remote Similarity	NPD5209	Approved
0.58	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6001	Approved
0.5789	Remote Similarity	NPD6412	Phase 2
0.5785	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD7101	Approved
0.578	Remote Similarity	NPD7902	Approved
0.578	Remote Similarity	NPD5173	Approved
0.5778	Remote Similarity	NPD7341	Phase 2
0.5776	Remote Similarity	NPD4634	Approved
0.5769	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD3198	Approved
0.5743	Remote Similarity	NPD6695	Phase 3
0.5741	Remote Similarity	NPD5210	Approved
0.5741	Remote Similarity	NPD4629	Approved
0.5729	Remote Similarity	NPD3702	Approved
0.5728	Remote Similarity	NPD3618	Phase 1
0.5728	Remote Similarity	NPD5279	Phase 3
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD6080	Approved
0.5701	Remote Similarity	NPD4202	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