NPASS Compound

Structure

NPC304624 OpenBabel07101718302D 24 28 0 0 1 0 0 0 0 0999 V2000 4.6142 0.3148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7481 1.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2592 -0.7786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1998 0.7088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8821 -0.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5288 0.6711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7481 0.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8821 0.3148 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5175 0.3148 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1998 -0.8670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6378 1.1251 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5175 -0.4730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9604 0.8719 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0694 0.4180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3846 -0.4730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1725 -1.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9604 -1.0302 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8039 1.8596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3723 -0.3166 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1998 -1.8670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2102 -1.9540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5110 2.5667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1838 2.0161 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 2 0 0 0 0 2 7 1 0 0 0 0 3 19 1 0 0 0 0 4 8 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 19 1 0 0 0 0 8 7 1 6 0 0 0 9 4 1 1 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 20 2 0 0 0 0 11 6 1 1 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 10 1 6 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 1 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.15
Volume:	327.803
LogP:	1.266
LogD:	0.758
LogS:	-1.979
# Rotatable Bonds:	1
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	5.853
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781
MDCK Permeability:	7.433860446326435e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.528
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	57.10029602050781%
Volume Distribution (VD):	0.855
Pgp-substrate:	43.28001022338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.329
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.227
CYP3A4-inhibitor:	0.268
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	11.631
Half-life (T1/2):	0.69

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.723
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.453
Skin Sensitization:	0.085
Carcinogencity:	0.083
Eye Corrosion:	0.714
Eye Irritation:	0.107
Respiratory Toxicity:	0.341

Download Data

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

Natural Product: NPC304624

Natural Product ID:	NPC304624
*Common Name:**	Ineleganolide
IUPAC Name:	n.a.
Synonyms:	Ineleganolide
Standard InCHIKey:	PYPSGVNKYAOLQT-IRGFZFOGSA-N
Standard InCHI:	InChI=1S/C19H22O5/c1-7(2)8-4-9-12(10(20)5-8)17-16(21)15-14-11(6-19(15,3)24-17)23-18(22)13(9)14/h8-9,11-15,17H,1,4-6H2,2-3H3/t8-,9-,11+,12+,13-,14-,15-,17+,19+/m0/s1
SMILES:	C=C(C)[C@H]1C[C@H]2[C@H](C(=O)C1)[C@@H]1C(=O)[C@@H]3[C@H]4[C@@H](C[C@@]3(C)O1)OC(=O)[C@@H]24
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337939
PubChem CID:	10544394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO27826	Sinularia maxima	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23200246]
NPO27826	Sinularia maxima	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
IC50	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[541446]

☑ 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 NPC304624 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	312
0.1-0.2	2738
0.2-0.3	9442
0.3-0.4	14537
0.4-0.5	8131
0.5-0.6	6024
0.6-0.7	1428
0.7-0.8	80
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474053
0.9688	High Similarity	NPC469629
0.8269	Intermediate Similarity	NPC190867
0.7928	Intermediate Similarity	NPC54739
0.7835	Intermediate Similarity	NPC475491
0.7835	Intermediate Similarity	NPC469626
0.7745	Intermediate Similarity	NPC163228
0.7624	Intermediate Similarity	NPC191339
0.7624	Intermediate Similarity	NPC286341
0.7524	Intermediate Similarity	NPC470188
0.7522	Intermediate Similarity	NPC300051
0.75	Intermediate Similarity	NPC53158
0.75	Intermediate Similarity	NPC40608
0.7455	Intermediate Similarity	NPC469508
0.7451	Intermediate Similarity	NPC469627
0.7431	Intermediate Similarity	NPC474101
0.7426	Intermediate Similarity	NPC472872
0.7383	Intermediate Similarity	NPC471767
0.7383	Intermediate Similarity	NPC39683
0.7379	Intermediate Similarity	NPC475788
0.7347	Intermediate Similarity	NPC111409
0.7333	Intermediate Similarity	NPC142529
0.7333	Intermediate Similarity	NPC91771
0.7327	Intermediate Similarity	NPC315911
0.7315	Intermediate Similarity	NPC49393
0.7315	Intermediate Similarity	NPC105725
0.7315	Intermediate Similarity	NPC250594
0.73	Intermediate Similarity	NPC304558
0.7297	Intermediate Similarity	NPC117604
0.729	Intermediate Similarity	NPC108371
0.7281	Intermediate Similarity	NPC9848
0.7281	Intermediate Similarity	NPC312017
0.7281	Intermediate Similarity	NPC285086
0.7273	Intermediate Similarity	NPC291643
0.7255	Intermediate Similarity	NPC11611
0.7248	Intermediate Similarity	NPC469985
0.7248	Intermediate Similarity	NPC216114
0.7238	Intermediate Similarity	NPC476053
0.7234	Intermediate Similarity	NPC471491
0.7228	Intermediate Similarity	NPC24728
0.7228	Intermediate Similarity	NPC270270
0.7216	Intermediate Similarity	NPC258965
0.7216	Intermediate Similarity	NPC156658
0.7212	Intermediate Similarity	NPC473273
0.7212	Intermediate Similarity	NPC153590
0.7212	Intermediate Similarity	NPC473234
0.7212	Intermediate Similarity	NPC472874
0.7212	Intermediate Similarity	NPC60386
0.7212	Intermediate Similarity	NPC308656
0.7212	Intermediate Similarity	NPC473263
0.7207	Intermediate Similarity	NPC201908
0.7207	Intermediate Similarity	NPC176949
0.7196	Intermediate Similarity	NPC153792
0.7196	Intermediate Similarity	NPC271387
0.7184	Intermediate Similarity	NPC216284
0.7184	Intermediate Similarity	NPC65359
0.7182	Intermediate Similarity	NPC228669
0.7182	Intermediate Similarity	NPC244247
0.7182	Intermediate Similarity	NPC98603
0.7182	Intermediate Similarity	NPC84928
0.7182	Intermediate Similarity	NPC164835
0.7182	Intermediate Similarity	NPC310586
0.7168	Intermediate Similarity	NPC98633
0.7157	Intermediate Similarity	NPC471149
0.7157	Intermediate Similarity	NPC190718
0.7157	Intermediate Similarity	NPC79549
0.7157	Intermediate Similarity	NPC178875
0.7143	Intermediate Similarity	NPC255082
0.7143	Intermediate Similarity	NPC476722
0.7143	Intermediate Similarity	NPC470921
0.7143	Intermediate Similarity	NPC473331
0.713	Intermediate Similarity	NPC186861
0.713	Intermediate Similarity	NPC267921
0.713	Intermediate Similarity	NPC52634
0.7129	Intermediate Similarity	NPC238593
0.7117	Intermediate Similarity	NPC44004
0.7117	Intermediate Similarity	NPC196528
0.7117	Intermediate Similarity	NPC50535
0.7117	Intermediate Similarity	NPC37600
0.7115	Intermediate Similarity	NPC165180
0.7115	Intermediate Similarity	NPC184063
0.7115	Intermediate Similarity	NPC155215
0.7105	Intermediate Similarity	NPC470281
0.7103	Intermediate Similarity	NPC474313
0.7103	Intermediate Similarity	NPC253586
0.7103	Intermediate Similarity	NPC469810
0.7103	Intermediate Similarity	NPC471150
0.7091	Intermediate Similarity	NPC266
0.7091	Intermediate Similarity	NPC140723
0.7087	Intermediate Similarity	NPC283409
0.7087	Intermediate Similarity	NPC215556
0.7075	Intermediate Similarity	NPC475900
0.7075	Intermediate Similarity	NPC322188
0.7075	Intermediate Similarity	NPC472873
0.7071	Intermediate Similarity	NPC246076
0.7069	Intermediate Similarity	NPC473898
0.7064	Intermediate Similarity	NPC295276
0.7064	Intermediate Similarity	NPC171759
0.7059	Intermediate Similarity	NPC142882
0.7059	Intermediate Similarity	NPC265580
0.7059	Intermediate Similarity	NPC118601
0.7054	Intermediate Similarity	NPC251824
0.7054	Intermediate Similarity	NPC471246
0.7054	Intermediate Similarity	NPC86852
0.7048	Intermediate Similarity	NPC200237
0.7048	Intermediate Similarity	NPC258216
0.7043	Intermediate Similarity	NPC471933
0.7041	Intermediate Similarity	NPC51507
0.7041	Intermediate Similarity	NPC170038
0.7034	Intermediate Similarity	NPC106644
0.7034	Intermediate Similarity	NPC475372
0.7027	Intermediate Similarity	NPC474558
0.7027	Intermediate Similarity	NPC473701
0.7027	Intermediate Similarity	NPC473526
0.7027	Intermediate Similarity	NPC47281
0.7019	Intermediate Similarity	NPC19087
0.7019	Intermediate Similarity	NPC246173
0.7018	Intermediate Similarity	NPC49730
0.7018	Intermediate Similarity	NPC255655
0.7018	Intermediate Similarity	NPC98069
0.7009	Intermediate Similarity	NPC476009
0.7009	Intermediate Similarity	NPC118159
0.7	Intermediate Similarity	NPC128246
0.7	Intermediate Similarity	NPC78127
0.7	Intermediate Similarity	NPC15396
0.7	Intermediate Similarity	NPC471757
0.6991	Remote Similarity	NPC211224
0.6991	Remote Similarity	NPC470269
0.6991	Remote Similarity	NPC9013
0.699	Remote Similarity	NPC191221
0.6975	Remote Similarity	NPC312536
0.6972	Remote Similarity	NPC471381
0.6964	Remote Similarity	NPC295366
0.6964	Remote Similarity	NPC475571
0.6964	Remote Similarity	NPC285927
0.6964	Remote Similarity	NPC28791
0.6952	Remote Similarity	NPC133888
0.6952	Remote Similarity	NPC474065
0.6952	Remote Similarity	NPC470230
0.6952	Remote Similarity	NPC29821
0.6952	Remote Similarity	NPC293001
0.6952	Remote Similarity	NPC171360
0.6952	Remote Similarity	NPC63193
0.6952	Remote Similarity	NPC35959
0.6952	Remote Similarity	NPC57304
0.6949	Remote Similarity	NPC36754
0.6944	Remote Similarity	NPC190080
0.6944	Remote Similarity	NPC108475
0.6944	Remote Similarity	NPC170143
0.6944	Remote Similarity	NPC311904
0.6944	Remote Similarity	NPC111187
0.6944	Remote Similarity	NPC96839
0.6944	Remote Similarity	NPC213947
0.6942	Remote Similarity	NPC192309
0.6939	Remote Similarity	NPC118987
0.6937	Remote Similarity	NPC474775
0.6937	Remote Similarity	NPC87927
0.6937	Remote Similarity	NPC36321
0.6937	Remote Similarity	NPC475873
0.6937	Remote Similarity	NPC469350
0.693	Remote Similarity	NPC217041
0.693	Remote Similarity	NPC304495
0.6923	Remote Similarity	NPC123117
0.6923	Remote Similarity	NPC471382
0.6923	Remote Similarity	NPC38392
0.6917	Remote Similarity	NPC147635
0.6917	Remote Similarity	NPC109973
0.6917	Remote Similarity	NPC329008
0.6917	Remote Similarity	NPC163693
0.6917	Remote Similarity	NPC317635
0.6909	Remote Similarity	NPC52899
0.6909	Remote Similarity	NPC121218
0.6909	Remote Similarity	NPC475099
0.6909	Remote Similarity	NPC46848
0.6909	Remote Similarity	NPC163963
0.6909	Remote Similarity	NPC162024
0.6909	Remote Similarity	NPC477950
0.6909	Remote Similarity	NPC289148
0.6909	Remote Similarity	NPC253886
0.6903	Remote Similarity	NPC96333
0.6903	Remote Similarity	NPC220974
0.6903	Remote Similarity	NPC88833
0.6891	Remote Similarity	NPC161060
0.6891	Remote Similarity	NPC470420
0.6887	Remote Similarity	NPC228700
0.6887	Remote Similarity	NPC477615
0.6887	Remote Similarity	NPC475488
0.6887	Remote Similarity	NPC202824
0.6887	Remote Similarity	NPC477361
0.6885	Remote Similarity	NPC1538
0.6881	Remote Similarity	NPC476294
0.6881	Remote Similarity	NPC54843
0.6881	Remote Similarity	NPC89099
0.6881	Remote Similarity	NPC471038
0.6881	Remote Similarity	NPC469986
0.6881	Remote Similarity	NPC474793
0.6881	Remote Similarity	NPC474724
0.688	Remote Similarity	NPC13071
0.6875	Remote Similarity	NPC29705
0.6875	Remote Similarity	NPC13149

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 NPC304624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	3279
0.2-0.3	3849
0.3-0.4	1129
0.4-0.5	328
0.5-0.6	196
0.6-0.7	70
0.7-0.8	1
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
0.7222	Intermediate Similarity	NPD1700	Approved
0.7117	Intermediate Similarity	NPD6008	Approved
0.7037	Intermediate Similarity	NPD5696	Approved
0.693	Remote Similarity	NPD6372	Approved
0.693	Remote Similarity	NPD6373	Approved
0.6855	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD7320	Approved
0.6829	Remote Similarity	NPD7492	Approved
0.6814	Remote Similarity	NPD5739	Approved
0.6814	Remote Similarity	NPD6402	Approved
0.6814	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD7128	Approved
0.681	Remote Similarity	NPD6650	Approved
0.681	Remote Similarity	NPD6649	Approved
0.6777	Remote Similarity	NPD6319	Approved
0.6777	Remote Similarity	NPD6059	Approved
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6759	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD5697	Approved
0.6754	Remote Similarity	NPD5701	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.672	Remote Similarity	NPD8293	Discontinued
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6638	Remote Similarity	NPD6012	Approved
0.6638	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD6098	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6904	Approved
0.6604	Remote Similarity	NPD6673	Approved
0.6604	Remote Similarity	NPD1695	Approved
0.6604	Remote Similarity	NPD6080	Approved
0.6581	Remote Similarity	NPD6883	Approved
0.6581	Remote Similarity	NPD7102	Approved
0.6581	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6011	Approved
0.6542	Remote Similarity	NPD5692	Phase 3
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD8130	Phase 1
0.6525	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD5737	Approved
0.6481	Remote Similarity	NPD5693	Phase 1
0.6481	Remote Similarity	NPD6050	Approved
0.6481	Remote Similarity	NPD5694	Approved
0.6471	Remote Similarity	NPD6882	Approved
0.6471	Remote Similarity	NPD8297	Approved
0.6455	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6399	Phase 3
0.6417	Remote Similarity	NPD4632	Approved
0.6408	Remote Similarity	NPD6435	Approved
0.6393	Remote Similarity	NPD6009	Approved
0.6389	Remote Similarity	NPD5207	Approved
0.6387	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5282	Discontinued
0.6355	Remote Similarity	NPD6903	Approved
0.6339	Remote Similarity	NPD4755	Approved
0.633	Remote Similarity	NPD8035	Phase 2
0.633	Remote Similarity	NPD8034	Phase 2
0.6321	Remote Similarity	NPD7521	Approved
0.6321	Remote Similarity	NPD5330	Approved
0.6321	Remote Similarity	NPD7334	Approved
0.6321	Remote Similarity	NPD7146	Approved
0.6321	Remote Similarity	NPD6409	Approved
0.6321	Remote Similarity	NPD6684	Approved
0.632	Remote Similarity	NPD5983	Phase 2
0.6311	Remote Similarity	NPD6274	Approved
0.6306	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD5210	Approved
0.6303	Remote Similarity	NPD4634	Approved
0.6279	Remote Similarity	NPD6033	Approved
0.6271	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD4700	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.622	Remote Similarity	NPD7604	Phase 2
0.6216	Remote Similarity	NPD6001	Approved
0.6214	Remote Similarity	NPD5368	Approved
0.6204	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6614	Approved
0.6168	Remote Similarity	NPD5786	Approved
0.6161	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5654	Approved
0.616	Remote Similarity	NPD7100	Approved
0.616	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD5369	Approved
0.6147	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD6317	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD5211	Phase 2
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.608	Remote Similarity	NPD6314	Approved
0.608	Remote Similarity	NPD6335	Approved
0.608	Remote Similarity	NPD6313	Approved
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD6909	Approved
0.6063	Remote Similarity	NPD6908	Approved
0.6061	Remote Similarity	NPD5956	Approved
0.6055	Remote Similarity	NPD5208	Approved
0.6053	Remote Similarity	NPD5959	Approved
0.6036	Remote Similarity	NPD5284	Approved
0.6036	Remote Similarity	NPD5281	Approved
0.6034	Remote Similarity	NPD5223	Approved
0.6033	Remote Similarity	NPD6371	Approved
0.6019	Remote Similarity	NPD4249	Approved
0.6017	Remote Similarity	NPD5141	Approved
0.5985	Remote Similarity	NPD7319	Approved
0.5966	Remote Similarity	NPD4768	Approved
0.5966	Remote Similarity	NPD4767	Approved
0.5965	Remote Similarity	NPD4697	Phase 3
0.5963	Remote Similarity	NPD4250	Approved
0.5963	Remote Similarity	NPD4251	Approved
0.5938	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6052	Approved
0.5932	Remote Similarity	NPD4754	Approved
0.5918	Remote Similarity	NPD229	Approved
0.5917	Remote Similarity	NPD6412	Phase 2
0.5909	Remote Similarity	NPD8337	Approved
0.5909	Remote Similarity	NPD8336	Approved
0.59	Remote Similarity	NPD5777	Approved
0.5888	Remote Similarity	NPD4788	Approved
0.5882	Remote Similarity	NPD3702	Approved
0.5878	Remote Similarity	NPD7507	Approved
0.587	Remote Similarity	NPD6334	Approved
0.587	Remote Similarity	NPD6333	Approved
0.5868	Remote Similarity	NPD5128	Approved
0.5868	Remote Similarity	NPD4729	Approved
0.5868	Remote Similarity	NPD4730	Approved
0.5865	Remote Similarity	NPD4238	Approved
0.5865	Remote Similarity	NPD4802	Phase 2
0.5846	Remote Similarity	NPD8328	Phase 3
0.5841	Remote Similarity	NPD5779	Approved
0.5841	Remote Similarity	NPD5778	Approved
0.5833	Remote Similarity	NPD4197	Approved
0.5794	Remote Similarity	NPD4269	Approved
0.5794	Remote Similarity	NPD4270	Approved
0.5789	Remote Similarity	NPD7900	Approved
0.5789	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.578	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5329	Approved
0.5772	Remote Similarity	NPD5251	Approved
0.5772	Remote Similarity	NPD5248	Approved
0.5772	Remote Similarity	NPD5249	Phase 3
0.5772	Remote Similarity	NPD5247	Approved
0.5772	Remote Similarity	NPD5250	Approved
0.576	Remote Similarity	NPD8133	Approved
0.5748	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5362	Discontinued
0.5727	Remote Similarity	NPD4694	Approved
0.5727	Remote Similarity	NPD5280	Approved
0.5727	Remote Similarity	NPD5690	Phase 2
0.5726	Remote Similarity	NPD5217	Approved
0.5726	Remote Similarity	NPD7638	Approved
0.5726	Remote Similarity	NPD5215	Approved
0.5726	Remote Similarity	NPD5216	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6101	Approved
0.5702	Remote Similarity	NPD4202	Approved
0.5692	Remote Similarity	NPD6921	Approved
0.569	Remote Similarity	NPD5221	Approved
0.569	Remote Similarity	NPD5222	Approved
0.569	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD3666	Approved
0.5688	Remote Similarity	NPD3133	Approved
0.5688	Remote Similarity	NPD3665	Phase 1
0.5678	Remote Similarity	NPD7639	Approved
0.5678	Remote Similarity	NPD7640	Approved
0.5669	Remote Similarity	NPD6868	Approved
0.5659	Remote Similarity	NPD4522	Approved
0.5656	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD4223	Phase 3
0.5648	Remote Similarity	NPD4221	Approved
0.5645	Remote Similarity	NPD5169	Approved
0.5645	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD5135	Approved
0.5641	Remote Similarity	NPD5173	Approved
0.5641	Remote Similarity	NPD7902	Approved
0.5636	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5363	Approved
0.5625	Remote Similarity	NPD7115	Discovery

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