NPASS Compound

Structure

NPC476217 OpenBabel07101718272D 36 38 0 0 1 0 0 0 0 0999 V2000 7.7307 4.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0577 3.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3950 -1.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2256 -0.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0766 -1.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2031 0.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7997 -0.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6629 1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1270 -1.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3950 0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5289 -0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9931 -1.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5753 2.0384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2658 -1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9309 1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8341 1.0724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7969 1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0236 3.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2610 -1.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2610 -0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2824 2.7455 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6629 0.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2686 -1.7818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9931 -0.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9309 0.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2948 -0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1270 0.3653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7969 -0.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6629 1.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2314 -2.6478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8591 0.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1629 2.2314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5072 1.5207 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 8.2483 2.4867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 20 21 2 0 0 0 0 21 28 1 0 0 0 0 22 36 1 0 0 0 0 23 29 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 31 1 6 0 0 0 25 28 1 6 0 0 0 25 32 1 0 0 0 0 26 29 1 1 0 0 0 26 35 1 0 0 0 0 27 35 1 0 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 30 8 1 6 0 0 0 30 33 1 0 0 0 0 34 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.38
Volume:	549.235
LogP:	3.772
LogD:	3.077
LogS:	-2.842
# Rotatable Bonds:	8
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	5.382
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	1.2824623809137847e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.108
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	90.48966217041016%
Volume Distribution (VD):	1.647
Pgp-substrate:	5.14270544052124%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.307
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	9.027
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.685
Carcinogencity:	0.903
Eye Corrosion:	0.005
Eye Irritation:	0.013
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476217

Natural Product ID:	NPC476217
*Common Name:**	Siphonellinol E
IUPAC Name:	(3S,5aS,6S,7R,9aS)-6-[2-[(5R,6S)-6-(3-hydroperoxy-4-methylpent-4-enyl)-5-hydroxy-2,6-dimethylcyclohexen-1-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
Synonyms:	Siphonellinol E
Standard InCHIKey:	JKSNJIROFMMOOT-KXUXGMQWSA-N
Standard InCHI:	InChI=1S/C30H52O6/c1-19(2)22(36-34)13-16-28(6)21(20(3)9-12-25(28)32)10-11-23-29(7)17-14-24(31)27(4,5)35-26(29)15-18-30(23,8)33/h22-26,31-34H,1,9-18H2,2-8H3/t22?,23-,24-,25+,26-,28-,29-,30+/m0/s1
SMILES:	CC1=C(C(C(CC1)O)(C)CCC(C(=C)C)OO)CCC2C3(CCC(C(OC3CCC2(C)O)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554939
PubChem CID:	44234957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	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	4
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[489283]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	39000.0	nM	PMID[489283]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	31200.0	nM	PMID[489283]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	38994.2	nM	PMID[489283]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	0.8	n.a.	PMID[489282]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	100.0	n.a.	PMID[489282]

☑ 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 NPC476217 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	224
0.1-0.2	1799
0.2-0.3	5464
0.3-0.4	13668
0.4-0.5	10381
0.5-0.6	7075
0.6-0.7	3741
0.7-0.8	332
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC97103
0.963	High Similarity	NPC290731
0.9405	High Similarity	NPC115607
0.9167	High Similarity	NPC233744
0.9167	High Similarity	NPC189777
0.8539	High Similarity	NPC210268
0.8444	Intermediate Similarity	NPC119379
0.8427	Intermediate Similarity	NPC470832
0.8352	Intermediate Similarity	NPC473258
0.8161	Intermediate Similarity	NPC83702
0.8118	Intermediate Similarity	NPC287749
0.8085	Intermediate Similarity	NPC272451
0.8085	Intermediate Similarity	NPC26307
0.8072	Intermediate Similarity	NPC477925
0.8072	Intermediate Similarity	NPC274079
0.7979	Intermediate Similarity	NPC91439
0.7979	Intermediate Similarity	NPC103165
0.7979	Intermediate Similarity	NPC210717
0.7978	Intermediate Similarity	NPC255143
0.7976	Intermediate Similarity	NPC477924
0.7976	Intermediate Similarity	NPC130136
0.7957	Intermediate Similarity	NPC472360
0.7957	Intermediate Similarity	NPC472416
0.7957	Intermediate Similarity	NPC72817
0.7957	Intermediate Similarity	NPC477927
0.7952	Intermediate Similarity	NPC477923
0.7952	Intermediate Similarity	NPC66566
0.7935	Intermediate Similarity	NPC114389
0.7912	Intermediate Similarity	NPC477917
0.7912	Intermediate Similarity	NPC246028
0.7907	Intermediate Similarity	NPC96362
0.7895	Intermediate Similarity	NPC261807
0.7895	Intermediate Similarity	NPC473244
0.7889	Intermediate Similarity	NPC476948
0.7872	Intermediate Similarity	NPC8774
0.7857	Intermediate Similarity	NPC265588
0.7849	Intermediate Similarity	NPC137461
0.7826	Intermediate Similarity	NPC191323
0.7816	Intermediate Similarity	NPC471270
0.7816	Intermediate Similarity	NPC476646
0.7812	Intermediate Similarity	NPC470067
0.7812	Intermediate Similarity	NPC470066
0.7805	Intermediate Similarity	NPC164022
0.7802	Intermediate Similarity	NPC474668
0.7789	Intermediate Similarity	NPC12103
0.7789	Intermediate Similarity	NPC98457
0.7789	Intermediate Similarity	NPC284194
0.7789	Intermediate Similarity	NPC471765
0.7789	Intermediate Similarity	NPC90583
0.7789	Intermediate Similarity	NPC221801
0.7789	Intermediate Similarity	NPC227583
0.7789	Intermediate Similarity	NPC211810
0.7789	Intermediate Similarity	NPC72204
0.7789	Intermediate Similarity	NPC288970
0.7789	Intermediate Similarity	NPC129569
0.7778	Intermediate Similarity	NPC237344
0.7766	Intermediate Similarity	NPC65402
0.7766	Intermediate Similarity	NPC127718
0.7766	Intermediate Similarity	NPC305160
0.7765	Intermediate Similarity	NPC471798
0.7753	Intermediate Similarity	NPC319238
0.7753	Intermediate Similarity	NPC102048
0.7753	Intermediate Similarity	NPC46320
0.7742	Intermediate Similarity	NPC302584
0.7742	Intermediate Similarity	NPC97404
0.7742	Intermediate Similarity	NPC41554
0.7738	Intermediate Similarity	NPC291503
0.7732	Intermediate Similarity	NPC79303
0.7732	Intermediate Similarity	NPC64348
0.7732	Intermediate Similarity	NPC188968
0.7727	Intermediate Similarity	NPC7988
0.7727	Intermediate Similarity	NPC471408
0.7717	Intermediate Similarity	NPC470361
0.7717	Intermediate Similarity	NPC261320
0.7711	Intermediate Similarity	NPC95165
0.7708	Intermediate Similarity	NPC475033
0.7708	Intermediate Similarity	NPC475032
0.7708	Intermediate Similarity	NPC240372
0.7701	Intermediate Similarity	NPC474592
0.7701	Intermediate Similarity	NPC471266
0.7701	Intermediate Similarity	NPC236707
0.7701	Intermediate Similarity	NPC95124
0.7692	Intermediate Similarity	NPC245004
0.7684	Intermediate Similarity	NPC86893
0.7684	Intermediate Similarity	NPC292178
0.7683	Intermediate Similarity	NPC92801
0.766	Intermediate Similarity	NPC91654
0.766	Intermediate Similarity	NPC98193
0.766	Intermediate Similarity	NPC474792
0.766	Intermediate Similarity	NPC67398
0.7653	Intermediate Similarity	NPC472554
0.7653	Intermediate Similarity	NPC475617
0.7647	Intermediate Similarity	NPC293223
0.7647	Intermediate Similarity	NPC329626
0.7634	Intermediate Similarity	NPC291484
0.7634	Intermediate Similarity	NPC220216
0.7634	Intermediate Similarity	NPC80561
0.7634	Intermediate Similarity	NPC11216
0.7634	Intermediate Similarity	NPC48732
0.7634	Intermediate Similarity	NPC204188
0.7634	Intermediate Similarity	NPC329596
0.7634	Intermediate Similarity	NPC3345
0.7634	Intermediate Similarity	NPC295668
0.7629	Intermediate Similarity	NPC476895
0.7629	Intermediate Similarity	NPC477875
0.7629	Intermediate Similarity	NPC477928
0.7629	Intermediate Similarity	NPC247233
0.7629	Intermediate Similarity	NPC5358
0.7629	Intermediate Similarity	NPC216260
0.7629	Intermediate Similarity	NPC312325
0.7629	Intermediate Similarity	NPC477876
0.7619	Intermediate Similarity	NPC243342
0.7619	Intermediate Similarity	NPC306727
0.7619	Intermediate Similarity	NPC477138
0.7614	Intermediate Similarity	NPC249423
0.7614	Intermediate Similarity	NPC16090
0.7609	Intermediate Similarity	NPC476724
0.7609	Intermediate Similarity	NPC476723
0.7609	Intermediate Similarity	NPC133588
0.759	Intermediate Similarity	NPC242992
0.759	Intermediate Similarity	NPC167706
0.7586	Intermediate Similarity	NPC233295
0.7586	Intermediate Similarity	NPC476367
0.7586	Intermediate Similarity	NPC72755
0.7582	Intermediate Similarity	NPC94462
0.7582	Intermediate Similarity	NPC6391
0.7582	Intermediate Similarity	NPC261266
0.7582	Intermediate Similarity	NPC125399
0.7579	Intermediate Similarity	NPC105375
0.7579	Intermediate Similarity	NPC96736
0.7579	Intermediate Similarity	NPC178949
0.7579	Intermediate Similarity	NPC105490
0.7579	Intermediate Similarity	NPC182826
0.7576	Intermediate Similarity	NPC472552
0.7558	Intermediate Similarity	NPC283619
0.7556	Intermediate Similarity	NPC238992
0.7556	Intermediate Similarity	NPC166279
0.7556	Intermediate Similarity	NPC124172
0.7553	Intermediate Similarity	NPC94127
0.7553	Intermediate Similarity	NPC124374
0.7551	Intermediate Similarity	NPC38855
0.7551	Intermediate Similarity	NPC271295
0.7551	Intermediate Similarity	NPC473790
0.7551	Intermediate Similarity	NPC471242
0.7551	Intermediate Similarity	NPC475877
0.7529	Intermediate Similarity	NPC36479
0.7529	Intermediate Similarity	NPC32832
0.7529	Intermediate Similarity	NPC12696
0.7528	Intermediate Similarity	NPC30166
0.7527	Intermediate Similarity	NPC187785
0.7527	Intermediate Similarity	NPC128066
0.7527	Intermediate Similarity	NPC20946
0.7527	Intermediate Similarity	NPC259875
0.7527	Intermediate Similarity	NPC49783
0.7527	Intermediate Similarity	NPC105495
0.7527	Intermediate Similarity	NPC470819
0.7526	Intermediate Similarity	NPC254121
0.7526	Intermediate Similarity	NPC476021
0.7526	Intermediate Similarity	NPC474994
0.7526	Intermediate Similarity	NPC476893
0.7526	Intermediate Similarity	NPC476040
0.7525	Intermediate Similarity	NPC470767
0.7525	Intermediate Similarity	NPC470763
0.75	Intermediate Similarity	NPC135224
0.75	Intermediate Similarity	NPC194323
0.75	Intermediate Similarity	NPC476720
0.75	Intermediate Similarity	NPC471779
0.75	Intermediate Similarity	NPC22403
0.75	Intermediate Similarity	NPC474124
0.75	Intermediate Similarity	NPC476894
0.75	Intermediate Similarity	NPC475701
0.75	Intermediate Similarity	NPC477969
0.7475	Intermediate Similarity	NPC235920
0.7475	Intermediate Similarity	NPC476132
0.7475	Intermediate Similarity	NPC11974
0.7475	Intermediate Similarity	NPC155974
0.7475	Intermediate Similarity	NPC96784
0.7475	Intermediate Similarity	NPC97435
0.7475	Intermediate Similarity	NPC476896
0.7474	Intermediate Similarity	NPC310013
0.7474	Intermediate Similarity	NPC53555
0.7474	Intermediate Similarity	NPC99653
0.7474	Intermediate Similarity	NPC7349
0.7473	Intermediate Similarity	NPC35933
0.7473	Intermediate Similarity	NPC196911
0.7473	Intermediate Similarity	NPC471379
0.7473	Intermediate Similarity	NPC476725
0.7471	Intermediate Similarity	NPC68119
0.7471	Intermediate Similarity	NPC52755
0.7471	Intermediate Similarity	NPC476314
0.7471	Intermediate Similarity	NPC167891
0.7471	Intermediate Similarity	NPC83351
0.7471	Intermediate Similarity	NPC13823
0.7449	Intermediate Similarity	NPC470068
0.7449	Intermediate Similarity	NPC275865
0.7447	Intermediate Similarity	NPC192437
0.7447	Intermediate Similarity	NPC470390
0.7447	Intermediate Similarity	NPC270511
0.7447	Intermediate Similarity	NPC14380
0.7447	Intermediate Similarity	NPC159876

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 NPC476217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	2283
0.2-0.3	3898
0.3-0.4	1966
0.4-0.5	493
0.5-0.6	273
0.6-0.7	51
0.7-0.8	0
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
0.75	Intermediate Similarity	NPD7524	Approved
0.7363	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7525	Registered
0.7253	Intermediate Similarity	NPD6695	Phase 3
0.7191	Intermediate Similarity	NPD7645	Phase 2
0.7129	Intermediate Similarity	NPD5344	Discontinued
0.7045	Intermediate Similarity	NPD6933	Approved
0.6947	Remote Similarity	NPD7750	Discontinued
0.6932	Remote Similarity	NPD8264	Approved
0.6932	Remote Similarity	NPD6942	Approved
0.6932	Remote Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD6930	Phase 2
0.6923	Remote Similarity	NPD6931	Approved
0.6907	Remote Similarity	NPD3168	Discontinued
0.6854	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6924	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6813	Remote Similarity	NPD6929	Approved
0.6771	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7638	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6739	Remote Similarity	NPD7509	Discontinued
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6699	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6637	Remote Similarity	NPD7327	Approved
0.6637	Remote Similarity	NPD7328	Approved
0.6593	Remote Similarity	NPD6925	Approved
0.6593	Remote Similarity	NPD6932	Approved
0.6593	Remote Similarity	NPD5776	Phase 2
0.6579	Remote Similarity	NPD7516	Approved
0.6562	Remote Similarity	NPD6893	Approved
0.6559	Remote Similarity	NPD7332	Phase 2
0.6559	Remote Similarity	NPD4748	Discontinued
0.6559	Remote Similarity	NPD7514	Phase 3
0.6522	Remote Similarity	NPD7145	Approved
0.6514	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6898	Phase 1
0.6481	Remote Similarity	NPD6412	Phase 2
0.6476	Remote Similarity	NPD4159	Approved
0.6466	Remote Similarity	NPD8033	Approved
0.6458	Remote Similarity	NPD4786	Approved
0.6455	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6683	Phase 2
0.6444	Remote Similarity	NPD1810	Approved
0.6444	Remote Similarity	NPD1811	Approved
0.6436	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD4632	Approved
0.6422	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6686	Approved
0.6421	Remote Similarity	NPD3667	Approved
0.6404	Remote Similarity	NPD7151	Approved
0.6404	Remote Similarity	NPD7150	Approved
0.6404	Remote Similarity	NPD7152	Approved
0.6389	Remote Similarity	NPD5357	Phase 1
0.6379	Remote Similarity	NPD8294	Approved
0.6379	Remote Similarity	NPD8377	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD6923	Approved
0.6364	Remote Similarity	NPD6922	Approved
0.6353	Remote Similarity	NPD371	Approved
0.6346	Remote Similarity	NPD7902	Approved
0.6344	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7515	Phase 2
0.6327	Remote Similarity	NPD3618	Phase 1
0.6325	Remote Similarity	NPD8335	Approved
0.6325	Remote Similarity	NPD8379	Approved
0.6325	Remote Similarity	NPD8378	Approved
0.6325	Remote Similarity	NPD8380	Approved
0.6325	Remote Similarity	NPD7503	Approved
0.6325	Remote Similarity	NPD8296	Approved
0.6316	Remote Similarity	NPD6902	Approved
0.631	Remote Similarity	NPD368	Approved
0.63	Remote Similarity	NPD5328	Approved
0.6292	Remote Similarity	NPD7143	Approved
0.6292	Remote Similarity	NPD7144	Approved
0.6275	Remote Similarity	NPD5778	Approved
0.6275	Remote Similarity	NPD5779	Approved
0.6275	Remote Similarity	NPD4202	Approved
0.6264	Remote Similarity	NPD4784	Approved
0.6264	Remote Similarity	NPD4785	Approved
0.6262	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7632	Discontinued
0.6261	Remote Similarity	NPD7115	Discovery
0.6261	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD6054	Approved
0.6239	Remote Similarity	NPD6059	Approved
0.6239	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD6402	Approved
0.6239	Remote Similarity	NPD5739	Approved
0.6239	Remote Similarity	NPD7128	Approved
0.6238	Remote Similarity	NPD6698	Approved
0.6238	Remote Similarity	NPD7838	Discovery
0.6238	Remote Similarity	NPD46	Approved
0.6222	Remote Similarity	NPD4243	Approved
0.6195	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD4755	Approved
0.6182	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7637	Suspended
0.6176	Remote Similarity	NPD6411	Approved
0.6176	Remote Similarity	NPD6079	Approved
0.6161	Remote Similarity	NPD4634	Approved
0.614	Remote Similarity	NPD8133	Approved
0.6134	Remote Similarity	NPD6370	Approved
0.6126	Remote Similarity	NPD6899	Approved
0.6126	Remote Similarity	NPD7320	Approved
0.6126	Remote Similarity	NPD6881	Approved
0.6121	Remote Similarity	NPD6009	Approved
0.6116	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD5211	Phase 2
0.6111	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2686	Approved
0.6111	Remote Similarity	NPD2687	Approved
0.6111	Remote Similarity	NPD2254	Approved
0.6091	Remote Similarity	NPD6008	Approved
0.6091	Remote Similarity	NPD6640	Phase 3
0.6083	Remote Similarity	NPD8328	Phase 3
0.6083	Remote Similarity	NPD7604	Phase 2
0.6075	Remote Similarity	NPD5285	Approved
0.6075	Remote Similarity	NPD5286	Approved
0.6075	Remote Similarity	NPD4700	Approved
0.6075	Remote Similarity	NPD4696	Approved
0.6071	Remote Similarity	NPD6373	Approved
0.6071	Remote Similarity	NPD6372	Approved
0.6058	Remote Similarity	NPD7900	Approved
0.6058	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6053	Discontinued
0.605	Remote Similarity	NPD6016	Approved
0.605	Remote Similarity	NPD5983	Phase 2
0.605	Remote Similarity	NPD6015	Approved
0.6036	Remote Similarity	NPD5701	Approved
0.6036	Remote Similarity	NPD5697	Approved
0.6033	Remote Similarity	NPD7492	Approved
0.6019	Remote Similarity	NPD7983	Approved
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD8035	Phase 2
0.6019	Remote Similarity	NPD5223	Approved
0.6018	Remote Similarity	NPD6371	Approved
0.6018	Remote Similarity	NPD7102	Approved
0.6018	Remote Similarity	NPD7290	Approved
0.6018	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6336	Discontinued
0.5984	Remote Similarity	NPD6616	Approved
0.5982	Remote Similarity	NPD6011	Approved
0.5981	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6051	Approved
0.598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6101	Approved
0.5968	Remote Similarity	NPD7319	Approved
0.5965	Remote Similarity	NPD6617	Approved
0.5965	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6650	Approved
0.5965	Remote Similarity	NPD6869	Approved
0.5965	Remote Similarity	NPD6649	Approved
0.5965	Remote Similarity	NPD8130	Phase 1
0.5965	Remote Similarity	NPD6847	Approved
0.5963	Remote Similarity	NPD5225	Approved
0.5963	Remote Similarity	NPD4633	Approved
0.5963	Remote Similarity	NPD5224	Approved
0.5963	Remote Similarity	NPD5226	Approved
0.596	Remote Similarity	NPD3668	Phase 3
0.596	Remote Similarity	NPD3665	Phase 1
0.596	Remote Similarity	NPD3666	Approved
0.596	Remote Similarity	NPD3133	Approved
0.595	Remote Similarity	NPD6067	Discontinued
0.5943	Remote Similarity	NPD5222	Approved
0.5943	Remote Similarity	NPD4697	Phase 3
0.5943	Remote Similarity	NPD5221	Approved
0.5943	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8293	Discontinued
0.5935	Remote Similarity	NPD7078	Approved
0.5929	Remote Similarity	NPD6013	Approved
0.5929	Remote Similarity	NPD6014	Approved
0.5929	Remote Similarity	NPD6012	Approved
0.5922	Remote Similarity	NPD7136	Phase 2
0.5913	Remote Similarity	NPD6882	Approved
0.5909	Remote Similarity	NPD5174	Approved
0.5909	Remote Similarity	NPD4754	Approved
0.5909	Remote Similarity	NPD5175	Approved
0.5905	Remote Similarity	NPD5282	Discontinued
0.59	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6084	Phase 2
0.5888	Remote Similarity	NPD5173	Approved
0.5888	Remote Similarity	NPD6083	Phase 2
0.5887	Remote Similarity	NPD6033	Approved
0.5887	Remote Similarity	NPD7736	Approved
0.5876	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4695	Discontinued
0.5859	Remote Similarity	NPD3669	Approved
0.5859	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6110	Phase 1
0.5851	Remote Similarity	NPD5275	Approved
0.5851	Remote Similarity	NPD4190	Phase 3
0.5842	Remote Similarity	NPD5279	Phase 3

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