NPASS Compound

Structure

NPC262085 OpenBabel07101719252D 28 30 0 0 1 0 0 0 0 0999 V2000 -4.3320 -2.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8966 3.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8320 2.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3320 1.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5832 -0.6651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9659 -1.4732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5999 1.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5999 0.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1980 -0.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1980 0.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4659 2.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4659 -0.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3320 -1.1072 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1554 2.3801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3320 0.8928 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4659 0.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 1.6730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3320 1.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.2588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4659 -0.6072 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8284 2.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3801 1.1554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 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 16 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 19 2 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 24 1 6 0 0 0 17 2 1 6 0 0 0 17 21 1 0 0 0 0 18 10 1 1 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 20 17 1 1 0 0 0 20 27 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 23 5 1 1 0 0 0 23 28 1 0 0 0 0 24 6 1 1 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.29
Volume:	427.879
LogP:	6.189
LogD:	4.468
LogS:	-5.573
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	4.93
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	1.8967408323078416e-05
Pgp-inhibitor:	0.07
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241
Plasma Protein Binding (PPB):	97.78761291503906%
Volume Distribution (VD):	0.834
Pgp-substrate:	2.6910595893859863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.714
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	2.766
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.535
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.469
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.533
Carcinogencity:	0.386
Eye Corrosion:	0.786
Eye Irritation:	0.329
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC262085

Natural Product ID:	NPC262085
*Common Name:**	Mycaperoxide H
IUPAC Name:	(2S)-2-[(3S,6R)-6-[2-[(1R,2R,4aS)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-6-methyldioxan-3-yl]propanoic acid
Synonyms:	Mycaperoxide H
Standard InCHIKey:	GDGRBTCRWIRALV-LXCIQGLGSA-N
Standard InCHI:	InChI=1S/C24H40O4/c1-16-9-10-18-19(8-7-12-22(18,3)4)24(16,6)15-14-23(5)13-11-20(27-28-23)17(2)21(25)26/h8,16-18,20H,7,9-15H2,1-6H3,(H,25,26)/t16-,17+,18-,20+,23+,24-/m1/s1
SMILES:	OC(=O)[C@H]([C@@H]1CC[C@@](OO1)(C)CC[C@]1(C)[C@H](C)CC[C@@H]2C1=CCCC2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516950
PubChem CID:	11741259
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[10843597]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	Thai	n.a.	PMID[12608869]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19845338]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31833368]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599273]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[558123]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[558124]

☑ 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 NPC262085 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	191
0.1-0.2	1112
0.2-0.3	4939
0.3-0.4	13113
0.4-0.5	9367
0.5-0.6	6384
0.6-0.7	5420
0.7-0.8	1916
0.8-0.85	215
0.85-0.9	24
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC476100
0.9375	High Similarity	NPC172309
0.9375	High Similarity	NPC117960
0.9375	High Similarity	NPC14044
0.9277	High Similarity	NPC475181
0.9259	High Similarity	NPC476292
0.9259	High Similarity	NPC474605
0.9157	High Similarity	NPC471344
0.9136	High Similarity	NPC476988
0.9048	High Similarity	NPC476104
0.9	High Similarity	NPC470905
0.9	High Similarity	NPC476986
0.8953	High Similarity	NPC469866
0.8953	High Similarity	NPC471342
0.8916	High Similarity	NPC476983
0.8889	High Similarity	NPC82488
0.8889	High Similarity	NPC308545
0.8824	High Similarity	NPC476982
0.881	High Similarity	NPC475193
0.881	High Similarity	NPC120158
0.878	High Similarity	NPC476265
0.878	High Similarity	NPC274522
0.8765	High Similarity	NPC321514
0.8675	High Similarity	NPC327002
0.8605	High Similarity	NPC73038
0.8571	High Similarity	NPC476984
0.8571	High Similarity	NPC132824
0.8571	High Similarity	NPC475395
0.8554	High Similarity	NPC37038
0.8539	High Similarity	NPC155120
0.8539	High Similarity	NPC6255
0.8539	High Similarity	NPC288833
0.8539	High Similarity	NPC228784
0.8539	High Similarity	NPC471588
0.8539	High Similarity	NPC324341
0.8539	High Similarity	NPC282616
0.8539	High Similarity	NPC966
0.8519	High Similarity	NPC152754
0.8519	High Similarity	NPC476985
0.8519	High Similarity	NPC59602
0.8519	High Similarity	NPC469514
0.8519	High Similarity	NPC474316
0.8519	High Similarity	NPC475744
0.8519	High Similarity	NPC476987
0.8506	High Similarity	NPC158141
0.8506	High Similarity	NPC173089
0.8506	High Similarity	NPC96496
0.8488	Intermediate Similarity	NPC76333
0.8471	Intermediate Similarity	NPC477373
0.8444	Intermediate Similarity	NPC118490
0.8434	Intermediate Similarity	NPC327674
0.8434	Intermediate Similarity	NPC231431
0.8427	Intermediate Similarity	NPC86372
0.8427	Intermediate Similarity	NPC172361
0.8427	Intermediate Similarity	NPC130278
0.8415	Intermediate Similarity	NPC476325
0.8415	Intermediate Similarity	NPC476264
0.8415	Intermediate Similarity	NPC469867
0.8409	Intermediate Similarity	NPC1753
0.8409	Intermediate Similarity	NPC474511
0.8391	Intermediate Similarity	NPC324063
0.8387	Intermediate Similarity	NPC174663
0.8372	Intermediate Similarity	NPC471343
0.837	Intermediate Similarity	NPC201657
0.8352	Intermediate Similarity	NPC6818
0.8352	Intermediate Similarity	NPC114159
0.8352	Intermediate Similarity	NPC78580
0.8352	Intermediate Similarity	NPC23621
0.8352	Intermediate Similarity	NPC222047
0.8352	Intermediate Similarity	NPC148964
0.8352	Intermediate Similarity	NPC191412
0.8352	Intermediate Similarity	NPC184006
0.8333	Intermediate Similarity	NPC104545
0.8315	Intermediate Similarity	NPC59263
0.8315	Intermediate Similarity	NPC475921
0.8315	Intermediate Similarity	NPC127689
0.8315	Intermediate Similarity	NPC130520
0.8315	Intermediate Similarity	NPC121798
0.8315	Intermediate Similarity	NPC263393
0.8315	Intermediate Similarity	NPC61543
0.8315	Intermediate Similarity	NPC474704
0.8315	Intermediate Similarity	NPC225585
0.8315	Intermediate Similarity	NPC474570
0.8315	Intermediate Similarity	NPC474700
0.8315	Intermediate Similarity	NPC25906
0.8315	Intermediate Similarity	NPC293048
0.8315	Intermediate Similarity	NPC234346
0.8315	Intermediate Similarity	NPC64872
0.8315	Intermediate Similarity	NPC270768
0.8315	Intermediate Similarity	NPC290972
0.8313	Intermediate Similarity	NPC260385
0.8313	Intermediate Similarity	NPC280654
0.8313	Intermediate Similarity	NPC179028
0.8313	Intermediate Similarity	NPC121200
0.8313	Intermediate Similarity	NPC110094
0.8298	Intermediate Similarity	NPC35239
0.8295	Intermediate Similarity	NPC477926
0.828	Intermediate Similarity	NPC187933
0.828	Intermediate Similarity	NPC261935
0.828	Intermediate Similarity	NPC106112
0.8261	Intermediate Similarity	NPC23241
0.8261	Intermediate Similarity	NPC263347
0.8261	Intermediate Similarity	NPC148523
0.8261	Intermediate Similarity	NPC195715
0.825	Intermediate Similarity	NPC160817
0.8242	Intermediate Similarity	NPC202728
0.8242	Intermediate Similarity	NPC158059
0.8242	Intermediate Similarity	NPC118519
0.8242	Intermediate Similarity	NPC229281
0.8242	Intermediate Similarity	NPC298554
0.8235	Intermediate Similarity	NPC278459
0.8235	Intermediate Similarity	NPC473420
0.8235	Intermediate Similarity	NPC142244
0.8222	Intermediate Similarity	NPC126369
0.8222	Intermediate Similarity	NPC193750
0.8222	Intermediate Similarity	NPC111110
0.8222	Intermediate Similarity	NPC18872
0.8222	Intermediate Similarity	NPC120968
0.8222	Intermediate Similarity	NPC210037
0.8222	Intermediate Similarity	NPC290614
0.8222	Intermediate Similarity	NPC477872
0.8222	Intermediate Similarity	NPC470589
0.8222	Intermediate Similarity	NPC7260
0.8222	Intermediate Similarity	NPC227467
0.8222	Intermediate Similarity	NPC273621
0.8214	Intermediate Similarity	NPC268502
0.8214	Intermediate Similarity	NPC254996
0.8214	Intermediate Similarity	NPC199595
0.8202	Intermediate Similarity	NPC470417
0.8202	Intermediate Similarity	NPC182797
0.8202	Intermediate Similarity	NPC52169
0.8193	Intermediate Similarity	NPC281296
0.8193	Intermediate Similarity	NPC471897
0.8193	Intermediate Similarity	NPC471899
0.8193	Intermediate Similarity	NPC107039
0.8191	Intermediate Similarity	NPC111214
0.8191	Intermediate Similarity	NPC271614
0.8191	Intermediate Similarity	NPC29765
0.8191	Intermediate Similarity	NPC164349
0.8182	Intermediate Similarity	NPC325594
0.8182	Intermediate Similarity	NPC473226
0.8182	Intermediate Similarity	NPC155011
0.8182	Intermediate Similarity	NPC322159
0.8182	Intermediate Similarity	NPC470955
0.8172	Intermediate Similarity	NPC116457
0.8172	Intermediate Similarity	NPC469528
0.8172	Intermediate Similarity	NPC167193
0.8172	Intermediate Similarity	NPC469369
0.8172	Intermediate Similarity	NPC98874
0.8172	Intermediate Similarity	NPC472806
0.8171	Intermediate Similarity	NPC192540
0.8171	Intermediate Similarity	NPC279666
0.8161	Intermediate Similarity	NPC156981
0.8161	Intermediate Similarity	NPC165064
0.8152	Intermediate Similarity	NPC299996
0.8152	Intermediate Similarity	NPC209868
0.8152	Intermediate Similarity	NPC263548
0.8152	Intermediate Similarity	NPC88116
0.8152	Intermediate Similarity	NPC32407
0.8152	Intermediate Similarity	NPC231063
0.8152	Intermediate Similarity	NPC474529
0.8152	Intermediate Similarity	NPC282395
0.8152	Intermediate Similarity	NPC20235
0.8152	Intermediate Similarity	NPC145667
0.814	Intermediate Similarity	NPC73882
0.8132	Intermediate Similarity	NPC38754
0.8132	Intermediate Similarity	NPC154101
0.8132	Intermediate Similarity	NPC105189
0.8132	Intermediate Similarity	NPC36491
0.8132	Intermediate Similarity	NPC187722
0.8118	Intermediate Similarity	NPC477057
0.8111	Intermediate Similarity	NPC281524
0.8111	Intermediate Similarity	NPC198664
0.8111	Intermediate Similarity	NPC274330
0.8111	Intermediate Similarity	NPC54689
0.8111	Intermediate Similarity	NPC143232
0.8105	Intermediate Similarity	NPC475156
0.8105	Intermediate Similarity	NPC473576
0.809	Intermediate Similarity	NPC242468
0.809	Intermediate Similarity	NPC474684
0.809	Intermediate Similarity	NPC233836
0.809	Intermediate Similarity	NPC130577
0.809	Intermediate Similarity	NPC171722
0.809	Intermediate Similarity	NPC187376
0.809	Intermediate Similarity	NPC159046
0.809	Intermediate Similarity	NPC51700
0.809	Intermediate Similarity	NPC167877
0.809	Intermediate Similarity	NPC142415
0.809	Intermediate Similarity	NPC88716
0.809	Intermediate Similarity	NPC68160
0.809	Intermediate Similarity	NPC102683
0.809	Intermediate Similarity	NPC18064
0.809	Intermediate Similarity	NPC293564
0.809	Intermediate Similarity	NPC142361
0.809	Intermediate Similarity	NPC171203
0.809	Intermediate Similarity	NPC307426
0.809	Intermediate Similarity	NPC98442
0.809	Intermediate Similarity	NPC71507
0.809	Intermediate Similarity	NPC90652
0.809	Intermediate Similarity	NPC312215

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 NPC262085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1562
0.2-0.3	3780
0.3-0.4	2381
0.4-0.5	721
0.5-0.6	233
0.6-0.7	197
0.7-0.8	108
0.8-0.85	1
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	NPD6411	Approved
0.8043	Intermediate Similarity	NPD6399	Phase 3
0.7935	Intermediate Similarity	NPD7515	Phase 2
0.7912	Intermediate Similarity	NPD6101	Approved
0.7912	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7748	Approved
0.7753	Intermediate Similarity	NPD4786	Approved
0.7727	Intermediate Similarity	NPD3667	Approved
0.7708	Intermediate Similarity	NPD6084	Phase 2
0.7708	Intermediate Similarity	NPD6083	Phase 2
0.7708	Intermediate Similarity	NPD7902	Approved
0.7684	Intermediate Similarity	NPD5695	Phase 3
0.7582	Intermediate Similarity	NPD5330	Approved
0.7582	Intermediate Similarity	NPD6409	Approved
0.7582	Intermediate Similarity	NPD6684	Approved
0.7582	Intermediate Similarity	NPD7521	Approved
0.7582	Intermediate Similarity	NPD7334	Approved
0.7582	Intermediate Similarity	NPD7146	Approved
0.7556	Intermediate Similarity	NPD3665	Phase 1
0.7556	Intermediate Similarity	NPD3666	Approved
0.7556	Intermediate Similarity	NPD3133	Approved
0.7553	Intermediate Similarity	NPD5281	Approved
0.7553	Intermediate Similarity	NPD5284	Approved
0.7527	Intermediate Similarity	NPD4753	Phase 2
0.7525	Intermediate Similarity	NPD7128	Approved
0.7525	Intermediate Similarity	NPD6402	Approved
0.7525	Intermediate Similarity	NPD5739	Approved
0.7525	Intermediate Similarity	NPD6675	Approved
0.7449	Intermediate Similarity	NPD5696	Approved
0.7419	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD6903	Approved
0.7419	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7900	Approved
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7391	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6881	Approved
0.7379	Intermediate Similarity	NPD6899	Approved
0.7379	Intermediate Similarity	NPD7320	Approved
0.7363	Intermediate Similarity	NPD3668	Phase 3
0.7347	Intermediate Similarity	NPD4755	Approved
0.734	Intermediate Similarity	NPD5328	Approved
0.734	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4221	Approved
0.7333	Intermediate Similarity	NPD4223	Phase 3
0.7308	Intermediate Similarity	NPD6373	Approved
0.7308	Intermediate Similarity	NPD6372	Approved
0.7303	Intermediate Similarity	NPD4695	Discontinued
0.7292	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD5778	Approved
0.7292	Intermediate Similarity	NPD4202	Approved
0.7283	Intermediate Similarity	NPD5329	Approved
0.7283	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5697	Approved
0.7282	Intermediate Similarity	NPD5701	Approved
0.7238	Intermediate Similarity	NPD7102	Approved
0.7238	Intermediate Similarity	NPD6883	Approved
0.7238	Intermediate Similarity	NPD7290	Approved
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.7204	Intermediate Similarity	NPD6098	Approved
0.72	Intermediate Similarity	NPD5286	Approved
0.72	Intermediate Similarity	NPD4700	Approved
0.72	Intermediate Similarity	NPD4696	Approved
0.72	Intermediate Similarity	NPD5285	Approved
0.7188	Intermediate Similarity	NPD8035	Phase 2
0.7188	Intermediate Similarity	NPD8034	Phase 2
0.7188	Intermediate Similarity	NPD6079	Approved
0.7174	Intermediate Similarity	NPD4197	Approved
0.717	Intermediate Similarity	NPD6869	Approved
0.717	Intermediate Similarity	NPD6617	Approved
0.717	Intermediate Similarity	NPD8130	Phase 1
0.717	Intermediate Similarity	NPD6650	Approved
0.717	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD6847	Approved
0.7158	Intermediate Similarity	NPD6673	Approved
0.7158	Intermediate Similarity	NPD6080	Approved
0.7158	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7128	Intermediate Similarity	NPD3573	Approved
0.7115	Intermediate Similarity	NPD6412	Phase 2
0.7111	Intermediate Similarity	NPD7525	Registered
0.7103	Intermediate Similarity	NPD8297	Approved
0.7103	Intermediate Similarity	NPD6882	Approved
0.7059	Intermediate Similarity	NPD5225	Approved
0.7059	Intermediate Similarity	NPD5226	Approved
0.7059	Intermediate Similarity	NPD4633	Approved
0.7059	Intermediate Similarity	NPD5224	Approved
0.7059	Intermediate Similarity	NPD5211	Phase 2
0.7048	Intermediate Similarity	NPD6686	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.7021	Intermediate Similarity	NPD4519	Discontinued
0.7021	Intermediate Similarity	NPD4694	Approved
0.7021	Intermediate Similarity	NPD5280	Approved
0.7021	Intermediate Similarity	NPD4693	Phase 3
0.7021	Intermediate Similarity	NPD4690	Approved
0.7021	Intermediate Similarity	NPD4138	Approved
0.7021	Intermediate Similarity	NPD5690	Phase 2
0.7021	Intermediate Similarity	NPD4688	Approved
0.7021	Intermediate Similarity	NPD5205	Approved
0.7021	Intermediate Similarity	NPD4689	Approved
0.7021	Intermediate Similarity	NPD4623	Approved
0.701	Intermediate Similarity	NPD6050	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7645	Phase 2
0.7	Intermediate Similarity	NPD7115	Discovery
0.699	Remote Similarity	NPD5175	Approved
0.699	Remote Similarity	NPD5174	Approved
0.697	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7339	Approved
0.6932	Remote Similarity	NPD6942	Approved
0.6931	Remote Similarity	NPD7638	Approved
0.6923	Remote Similarity	NPD5368	Approved
0.6923	Remote Similarity	NPD5141	Approved
0.6916	Remote Similarity	NPD4634	Approved
0.6907	Remote Similarity	NPD5692	Phase 3
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7614	Phase 1
0.69	Remote Similarity	NPD4697	Phase 3
0.6889	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3617	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD5208	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6863	Remote Similarity	NPD7640	Approved
0.6863	Remote Similarity	NPD7639	Approved
0.6857	Remote Similarity	NPD4768	Approved
0.6857	Remote Similarity	NPD4767	Approved
0.6854	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4692	Approved
0.6848	Remote Similarity	NPD4139	Approved
0.6837	Remote Similarity	NPD5693	Phase 1
0.6837	Remote Similarity	NPD5694	Approved
0.6837	Remote Similarity	NPD7637	Suspended
0.6832	Remote Similarity	NPD5173	Approved
0.6827	Remote Similarity	NPD4754	Approved
0.6822	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6319	Approved
0.6804	Remote Similarity	NPD6051	Approved
0.6783	Remote Similarity	NPD8328	Phase 3
0.6782	Remote Similarity	NPD4243	Approved
0.6778	Remote Similarity	NPD6116	Phase 1
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6774	Remote Similarity	NPD6435	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD6274	Approved
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4820	Approved
0.6739	Remote Similarity	NPD4822	Approved
0.6735	Remote Similarity	NPD5207	Approved
0.6729	Remote Similarity	NPD4730	Approved
0.6729	Remote Similarity	NPD4729	Approved
0.6729	Remote Similarity	NPD5128	Approved
0.6727	Remote Similarity	NPD4632	Approved
0.6726	Remote Similarity	NPD7101	Approved
0.6726	Remote Similarity	NPD7100	Approved
0.6724	Remote Similarity	NPD7492	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6335	Approved
0.6636	Remote Similarity	NPD6053	Discontinued
0.6634	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4195	Approved
0.6629	Remote Similarity	NPD6924	Approved
0.6629	Remote Similarity	NPD4784	Approved
0.6629	Remote Similarity	NPD6926	Approved
0.6629	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4785	Approved
0.661	Remote Similarity	NPD7078	Approved
0.661	Remote Similarity	NPD8293	Discontinued
0.6609	Remote Similarity	NPD6908	Approved
0.6609	Remote Similarity	NPD6909	Approved
0.6606	Remote Similarity	NPD5251	Approved
0.6606	Remote Similarity	NPD5250	Approved
0.6606	Remote Similarity	NPD5249	Phase 3
0.6606	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5247	Approved
0.6606	Remote Similarity	NPD5248	Approved
0.6588	Remote Similarity	NPD7331	Phase 2
0.6569	Remote Similarity	NPD7732	Phase 3
0.6566	Remote Similarity	NPD46	Approved
0.6566	Remote Similarity	NPD6698	Approved
0.6566	Remote Similarity	NPD5785	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