NPASS Compound

Structure

NPC232295 OpenBabel07101718182D 30 31 0 0 1 0 0 0 0 0999 V2000 -10.1971 1.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9724 2.7074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 -1.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8510 0.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4368 -0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7297 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4028 -1.0870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5241 1.0343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7829 0.0684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2312 1.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 -1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1099 -0.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0758 -0.6387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3346 -1.6046 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 20 1 0 0 0 0 10 20 2 0 0 0 0 11 21 2 0 0 0 0 12 13 1 0 0 0 0 12 19 2 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 27 1 0 0 0 0 16 27 1 0 0 0 0 17 22 1 0 0 0 0 17 24 2 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 21 25 1 0 0 0 0 22 26 2 0 0 0 0 23 26 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 6 0 0 0 26 30 1 0 0 0 0 27 6 1 6 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.3
Volume:	468.987
LogP:	6.664
LogD:	4.882
LogS:	-3.963
# Rotatable Bonds:	9
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	4.035
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821
MDCK Permeability:	2.442923687340226e-05
Pgp-inhibitor:	0.244
Pgp-substrate:	0.827
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.901

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.39
Plasma Protein Binding (PPB):	98.33734893798828%
Volume Distribution (VD):	1.493
Pgp-substrate:	1.3240731954574585%

ADMET: Metabolism

CYP1A2-inhibitor:	0.453
CYP1A2-substrate:	0.439
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.677
CYP2C9-inhibitor:	0.321
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	7.684
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.294
Human Hepatotoxicity (H-HT):	0.746
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.937
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.192
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC232295

Natural Product ID:	NPC232295
*Common Name:**	Sargachromanol C
IUPAC Name:	(2R)-2-[(3E,7E,9R)-9-hydroxy-4,8,12-trimethyltrideca-3,7,11-trienyl]-2,8-dimethyl-3,4-dihydrochromen-6-ol
Synonyms:	Sargachromanol C
Standard InCHIKey:	RFIIOYJLKCYOCK-PUMPRSRSSA-N
Standard InCHI:	InChI=1S/C27H40O3/c1-19(2)12-13-25(29)21(4)11-7-9-20(3)10-8-15-27(6)16-14-23-18-24(28)17-22(5)26(23)30-27/h10-12,17-18,25,28-29H,7-9,13-16H2,1-6H3/b20-10+,21-11+/t25-,27-/m1/s1
SMILES:	C/C(=CCC[C@]1(C)CCc2c(O1)c(C)cc(c2)O)/CC/C=C(/[C@@H](CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465201
PubChem CID:	11177417
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0001546] Vitamin E compounds [CHEMONTID:0002092] Tocotrienols

*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
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	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	2
MIC	6
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	200.0	ug.mL-1	PMID[452417]
NPT1	Others	Radical scavenging activity		Activity	=	90.5	%	PMID[452416]
NPT2	Others	Unspecified		IC50	=	83100.0	nM	PMID[452417]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[452417]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[452417]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[452417]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[452417]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[452417]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[452417]

☑ 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 NPC232295 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	307
0.1-0.2	1447
0.2-0.3	4323
0.3-0.4	12547
0.4-0.5	6242
0.5-0.6	6301
0.6-0.7	9054
0.7-0.8	2279
0.8-0.85	133
0.85-0.9	37
0.9-0.95	17
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC32152
0.9823	High Similarity	NPC474131
0.9739	High Similarity	NPC46586
0.9739	High Similarity	NPC204535
0.9655	High Similarity	NPC474130
0.9643	High Similarity	NPC69539
0.9558	High Similarity	NPC187993
0.9558	High Similarity	NPC238176
0.9304	High Similarity	NPC283616
0.9244	High Similarity	NPC190086
0.9244	High Similarity	NPC276962
0.9231	High Similarity	NPC45663
0.9211	High Similarity	NPC473718
0.918	High Similarity	NPC59654
0.918	High Similarity	NPC271832
0.9153	High Similarity	NPC168707
0.9153	High Similarity	NPC48623
0.9106	High Similarity	NPC475880
0.9083	High Similarity	NPC147896
0.9068	High Similarity	NPC473875
0.9032	High Similarity	NPC474143
0.9032	High Similarity	NPC474246
0.8974	High Similarity	NPC139047
0.896	High Similarity	NPC27578
0.896	High Similarity	NPC289624
0.8947	High Similarity	NPC474920
0.8926	High Similarity	NPC474237
0.8898	High Similarity	NPC51341
0.8803	High Similarity	NPC290470
0.8803	High Similarity	NPC154256
0.8783	High Similarity	NPC98372
0.877	High Similarity	NPC61685
0.876	High Similarity	NPC302211
0.8739	High Similarity	NPC471449
0.873	High Similarity	NPC153019
0.8689	High Similarity	NPC261992
0.8673	High Similarity	NPC233320
0.8644	High Similarity	NPC126759
0.8644	High Similarity	NPC242580
0.8644	High Similarity	NPC236070
0.8618	High Similarity	NPC248557
0.8607	High Similarity	NPC188997
0.8595	High Similarity	NPC475529
0.8594	High Similarity	NPC211352
0.8571	High Similarity	NPC472796
0.8571	High Similarity	NPC472795
0.8559	High Similarity	NPC301321
0.8548	High Similarity	NPC477213
0.8548	High Similarity	NPC476254
0.8548	High Similarity	NPC131397
0.8534	High Similarity	NPC275627
0.8525	High Similarity	NPC476165
0.8516	High Similarity	NPC317601
0.8516	High Similarity	NPC329427
0.8504	High Similarity	NPC196621
0.8492	Intermediate Similarity	NPC38604
0.8492	Intermediate Similarity	NPC211179
0.8492	Intermediate Similarity	NPC47288
0.8443	Intermediate Similarity	NPC96423
0.8443	Intermediate Similarity	NPC129176
0.8435	Intermediate Similarity	NPC241549
0.8425	Intermediate Similarity	NPC97326
0.8425	Intermediate Similarity	NPC472797
0.8413	Intermediate Similarity	NPC95034
0.8413	Intermediate Similarity	NPC319422
0.8413	Intermediate Similarity	NPC477214
0.8413	Intermediate Similarity	NPC142087
0.8413	Intermediate Similarity	NPC477211
0.8413	Intermediate Similarity	NPC477212
0.84	Intermediate Similarity	NPC81641
0.8385	Intermediate Similarity	NPC477210
0.8374	Intermediate Similarity	NPC475839
0.8359	Intermediate Similarity	NPC325003
0.8346	Intermediate Similarity	NPC274717
0.8319	Intermediate Similarity	NPC108497
0.8319	Intermediate Similarity	NPC470837
0.8319	Intermediate Similarity	NPC161696
0.8306	Intermediate Similarity	NPC120638
0.8306	Intermediate Similarity	NPC150026
0.8296	Intermediate Similarity	NPC474154
0.8293	Intermediate Similarity	NPC212559
0.8268	Intermediate Similarity	NPC473993
0.8261	Intermediate Similarity	NPC469913
0.8258	Intermediate Similarity	NPC472800
0.8254	Intermediate Similarity	NPC470726
0.8254	Intermediate Similarity	NPC28476
0.8254	Intermediate Similarity	NPC133407
0.8235	Intermediate Similarity	NPC141003
0.8235	Intermediate Similarity	NPC35344
0.8231	Intermediate Similarity	NPC472798
0.8231	Intermediate Similarity	NPC51262
0.8231	Intermediate Similarity	NPC118253
0.8231	Intermediate Similarity	NPC85595
0.8226	Intermediate Similarity	NPC212965
0.8217	Intermediate Similarity	NPC196193
0.8217	Intermediate Similarity	NPC11089
0.8209	Intermediate Similarity	NPC473049
0.8209	Intermediate Similarity	NPC472794
0.8203	Intermediate Similarity	NPC176590
0.819	Intermediate Similarity	NPC474352
0.8189	Intermediate Similarity	NPC276212
0.8189	Intermediate Similarity	NPC470724
0.8182	Intermediate Similarity	NPC475011
0.8175	Intermediate Similarity	NPC106914
0.8175	Intermediate Similarity	NPC197351
0.8175	Intermediate Similarity	NPC86502
0.8175	Intermediate Similarity	NPC246648
0.8175	Intermediate Similarity	NPC134195
0.8174	Intermediate Similarity	NPC470393
0.8167	Intermediate Similarity	NPC474050
0.8167	Intermediate Similarity	NPC474114
0.8167	Intermediate Similarity	NPC473931
0.816	Intermediate Similarity	NPC49441
0.816	Intermediate Similarity	NPC57199
0.8154	Intermediate Similarity	NPC271945
0.8154	Intermediate Similarity	NPC103799
0.8154	Intermediate Similarity	NPC181497
0.8151	Intermediate Similarity	NPC228452
0.8145	Intermediate Similarity	NPC218753
0.8145	Intermediate Similarity	NPC277798
0.8145	Intermediate Similarity	NPC100108
0.8142	Intermediate Similarity	NPC129373
0.8142	Intermediate Similarity	NPC48730
0.8142	Intermediate Similarity	NPC248396
0.814	Intermediate Similarity	NPC93962
0.814	Intermediate Similarity	NPC158477
0.813	Intermediate Similarity	NPC163036
0.8125	Intermediate Similarity	NPC149796
0.812	Intermediate Similarity	NPC475628
0.812	Intermediate Similarity	NPC470802
0.812	Intermediate Similarity	NPC75440
0.811	Intermediate Similarity	NPC188022
0.811	Intermediate Similarity	NPC102540
0.811	Intermediate Similarity	NPC285040
0.811	Intermediate Similarity	NPC293801
0.811	Intermediate Similarity	NPC252962
0.811	Intermediate Similarity	NPC17809
0.811	Intermediate Similarity	NPC103420
0.8106	Intermediate Similarity	NPC16485
0.8103	Intermediate Similarity	NPC30416
0.8099	Intermediate Similarity	NPC283169
0.8095	Intermediate Similarity	NPC96940
0.8092	Intermediate Similarity	NPC13005
0.8092	Intermediate Similarity	NPC18842
0.8087	Intermediate Similarity	NPC108875
0.8087	Intermediate Similarity	NPC130817
0.8087	Intermediate Similarity	NPC38079
0.8083	Intermediate Similarity	NPC296144
0.8083	Intermediate Similarity	NPC28784
0.808	Intermediate Similarity	NPC290451
0.808	Intermediate Similarity	NPC127389
0.8077	Intermediate Similarity	NPC470727
0.8077	Intermediate Similarity	NPC262606
0.8077	Intermediate Similarity	NPC220935
0.8077	Intermediate Similarity	NPC470225
0.8077	Intermediate Similarity	NPC27187
0.8074	Intermediate Similarity	NPC76312
0.807	Intermediate Similarity	NPC477685
0.8062	Intermediate Similarity	NPC81261
0.8062	Intermediate Similarity	NPC40377
0.8062	Intermediate Similarity	NPC38664
0.8062	Intermediate Similarity	NPC53986
0.8053	Intermediate Similarity	NPC260775
0.8051	Intermediate Similarity	NPC473524
0.8047	Intermediate Similarity	NPC476006
0.8045	Intermediate Similarity	NPC475029
0.8045	Intermediate Similarity	NPC476018
0.8045	Intermediate Similarity	NPC473413
0.8034	Intermediate Similarity	NPC194034
0.803	Intermediate Similarity	NPC26394
0.803	Intermediate Similarity	NPC85435
0.8029	Intermediate Similarity	NPC329493
0.8016	Intermediate Similarity	NPC77789
0.8016	Intermediate Similarity	NPC18128
0.8016	Intermediate Similarity	NPC100099
0.8016	Intermediate Similarity	NPC152946
0.8016	Intermediate Similarity	NPC36016
0.8015	Intermediate Similarity	NPC206224
0.8015	Intermediate Similarity	NPC129784
0.8015	Intermediate Similarity	NPC472792
0.8015	Intermediate Similarity	NPC293203
0.8015	Intermediate Similarity	NPC150011
0.8015	Intermediate Similarity	NPC118114
0.8015	Intermediate Similarity	NPC160623
0.8015	Intermediate Similarity	NPC300875
0.8015	Intermediate Similarity	NPC211413
0.8015	Intermediate Similarity	NPC196765
0.8015	Intermediate Similarity	NPC164574
0.8015	Intermediate Similarity	NPC17343
0.8015	Intermediate Similarity	NPC236014
0.8015	Intermediate Similarity	NPC129106
0.8015	Intermediate Similarity	NPC472590
0.8015	Intermediate Similarity	NPC244888
0.8015	Intermediate Similarity	NPC118683
0.8015	Intermediate Similarity	NPC12875
0.8015	Intermediate Similarity	NPC472791
0.8015	Intermediate Similarity	NPC280653
0.8015	Intermediate Similarity	NPC268917
0.8015	Intermediate Similarity	NPC476166
0.8015	Intermediate Similarity	NPC68205

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 NPC232295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	987
0.2-0.3	1706
0.3-0.4	2698
0.4-0.5	1684
0.5-0.6	1101
0.6-0.7	578
0.7-0.8	108
0.8-0.85	6
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9381	High Similarity	NPD6671	Approved
0.8644	High Similarity	NPD7340	Approved
0.8547	High Similarity	NPD1398	Phase 1
0.8468	Intermediate Similarity	NPD6696	Suspended
0.8413	Intermediate Similarity	NPD2861	Phase 2
0.8359	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD968	Approved
0.8145	Intermediate Similarity	NPD3496	Discontinued
0.8095	Intermediate Similarity	NPD4749	Approved
0.8034	Intermediate Similarity	NPD290	Approved
0.8	Intermediate Similarity	NPD4625	Phase 3
0.7966	Intermediate Similarity	NPD2684	Approved
0.7874	Intermediate Similarity	NPD2231	Phase 2
0.7874	Intermediate Similarity	NPD2235	Phase 2
0.7851	Intermediate Similarity	NPD7843	Approved
0.7823	Intermediate Similarity	NPD7644	Approved
0.782	Intermediate Similarity	NPD4060	Phase 1
0.7812	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7157	Approved
0.7803	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7635	Approved
0.7687	Intermediate Similarity	NPD1613	Approved
0.7687	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7985	Registered
0.7656	Intermediate Similarity	NPD1611	Approved
0.7656	Intermediate Similarity	NPD1610	Phase 2
0.7656	Intermediate Similarity	NPD1091	Approved
0.7652	Intermediate Similarity	NPD4908	Phase 1
0.7638	Intermediate Similarity	NPD4626	Approved
0.7634	Intermediate Similarity	NPD3691	Phase 2
0.7634	Intermediate Similarity	NPD6584	Phase 3
0.7634	Intermediate Similarity	NPD3690	Phase 2
0.7626	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD8651	Approved
0.7597	Intermediate Similarity	NPD2232	Approved
0.7597	Intermediate Similarity	NPD2230	Approved
0.7597	Intermediate Similarity	NPD2233	Approved
0.7559	Intermediate Similarity	NPD5691	Approved
0.7554	Intermediate Similarity	NPD2424	Discontinued
0.7552	Intermediate Similarity	NPD6090	Discontinued
0.7538	Intermediate Similarity	NPD5327	Phase 3
0.7519	Intermediate Similarity	NPD596	Approved
0.7519	Intermediate Similarity	NPD600	Approved
0.75	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD1778	Approved
0.7482	Intermediate Similarity	NPD5763	Approved
0.7482	Intermediate Similarity	NPD5762	Approved
0.748	Intermediate Similarity	NPD1548	Phase 1
0.748	Intermediate Similarity	NPD228	Approved
0.7478	Intermediate Similarity	NPD844	Approved
0.7463	Intermediate Similarity	NPD3027	Phase 3
0.7445	Intermediate Similarity	NPD6353	Approved
0.7444	Intermediate Similarity	NPD2237	Approved
0.7444	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD2238	Phase 2
0.7426	Intermediate Similarity	NPD4140	Approved
0.7419	Intermediate Similarity	NPD821	Approved
0.741	Intermediate Similarity	NPD6099	Approved
0.741	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD6100	Approved
0.7405	Intermediate Similarity	NPD6583	Phase 3
0.7405	Intermediate Similarity	NPD6582	Phase 2
0.7391	Intermediate Similarity	NPD7097	Phase 1
0.7391	Intermediate Similarity	NPD4536	Approved
0.7391	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4538	Approved
0.7388	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2557	Approved
0.7376	Intermediate Similarity	NPD6674	Discontinued
0.7372	Intermediate Similarity	NPD5124	Phase 1
0.7372	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD839	Approved
0.7353	Intermediate Similarity	NPD840	Approved
0.7324	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2157	Approved
0.7319	Intermediate Similarity	NPD6653	Approved
0.7315	Intermediate Similarity	NPD5929	Approved
0.7313	Intermediate Similarity	NPD1712	Approved
0.7304	Intermediate Similarity	NPD845	Approved
0.7299	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3620	Phase 2
0.7287	Intermediate Similarity	NPD3443	Approved
0.7287	Intermediate Similarity	NPD5585	Approved
0.7287	Intermediate Similarity	NPD3444	Approved
0.7287	Intermediate Similarity	NPD3445	Approved
0.7287	Intermediate Similarity	NPD6382	Discontinued
0.7286	Intermediate Similarity	NPD6032	Approved
0.7273	Intermediate Similarity	NPD3685	Discontinued
0.7265	Intermediate Similarity	NPD288	Approved
0.7257	Intermediate Similarity	NPD9295	Approved
0.7252	Intermediate Similarity	NPD776	Approved
0.7246	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD558	Phase 2
0.7234	Intermediate Similarity	NPD6002	Phase 3
0.7234	Intermediate Similarity	NPD6005	Phase 3
0.7234	Intermediate Similarity	NPD6004	Phase 3
0.7234	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6516	Phase 2
0.7231	Intermediate Similarity	NPD5846	Approved
0.7226	Intermediate Similarity	NPD7477	Discontinued
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7222	Intermediate Similarity	NPD594	Approved
0.7222	Intermediate Similarity	NPD592	Approved
0.7214	Intermediate Similarity	NPD5588	Approved
0.7214	Intermediate Similarity	NPD5960	Phase 3
0.7214	Intermediate Similarity	NPD7033	Discontinued
0.7206	Intermediate Similarity	NPD7095	Approved
0.7192	Intermediate Similarity	NPD2676	Approved
0.7192	Intermediate Similarity	NPD2675	Approved
0.7179	Intermediate Similarity	NPD2860	Approved
0.7179	Intermediate Similarity	NPD1809	Phase 2
0.7179	Intermediate Similarity	NPD2859	Approved
0.7177	Intermediate Similarity	NPD4750	Phase 3
0.7172	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7041	Phase 2
0.7164	Intermediate Similarity	NPD4098	Discontinued
0.7164	Intermediate Similarity	NPD2797	Approved
0.7154	Intermediate Similarity	NPD1357	Approved
0.7154	Intermediate Similarity	NPD3049	Approved
0.7153	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD3020	Approved
0.7143	Intermediate Similarity	NPD1138	Approved
0.7133	Intermediate Similarity	NPD5177	Phase 3
0.7121	Intermediate Similarity	NPD422	Phase 1
0.7121	Intermediate Similarity	NPD1535	Discovery
0.7113	Intermediate Similarity	NPD7030	Discontinued
0.7111	Intermediate Similarity	NPD4624	Approved
0.7109	Intermediate Similarity	NPD709	Approved
0.7109	Intermediate Similarity	NPD6387	Discontinued
0.7103	Intermediate Similarity	NPD6666	Approved
0.7103	Intermediate Similarity	NPD5058	Phase 3
0.7103	Intermediate Similarity	NPD6667	Approved
0.7101	Intermediate Similarity	NPD6233	Phase 2
0.7099	Intermediate Similarity	NPD2556	Approved
0.7099	Intermediate Similarity	NPD2667	Approved
0.7099	Intermediate Similarity	NPD2668	Approved
0.7099	Intermediate Similarity	NPD2554	Approved
0.7094	Intermediate Similarity	NPD2933	Approved
0.7094	Intermediate Similarity	NPD2934	Approved
0.7092	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2155	Approved
0.7092	Intermediate Similarity	NPD2154	Approved
0.7092	Intermediate Similarity	NPD2156	Approved
0.7087	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4535	Phase 3
0.7077	Intermediate Similarity	NPD1182	Approved
0.7077	Intermediate Similarity	NPD3091	Approved
0.7071	Intermediate Similarity	NPD4097	Suspended
0.7068	Intermediate Similarity	NPD1608	Approved
0.7068	Intermediate Similarity	NPD1481	Phase 2
0.7063	Intermediate Similarity	NPD1137	Approved
0.7063	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1139	Approved
0.7054	Intermediate Similarity	NPD3596	Phase 2
0.705	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4477	Approved
0.7042	Intermediate Similarity	NPD4476	Approved
0.704	Intermediate Similarity	NPD5451	Approved
0.7037	Intermediate Similarity	NPD1794	Approved
0.7037	Intermediate Similarity	NPD6362	Approved
0.7034	Intermediate Similarity	NPD3692	Discontinued
0.7034	Intermediate Similarity	NPD2677	Approved
0.7029	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1651	Approved
0.702	Intermediate Similarity	NPD6844	Discontinued
0.7016	Intermediate Similarity	NPD2342	Discontinued
0.7015	Intermediate Similarity	NPD4359	Approved
0.7015	Intermediate Similarity	NPD1669	Approved
0.7007	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2346	Discontinued
0.6992	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9697	Approved
0.6992	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9365	Approved
0.698	Remote Similarity	NPD1653	Approved
0.6978	Remote Similarity	NPD3162	Approved
0.6978	Remote Similarity	NPD3163	Approved
0.6966	Remote Similarity	NPD6331	Phase 2
0.6963	Remote Similarity	NPD1283	Approved
0.6953	Remote Similarity	NPD1241	Discontinued
0.695	Remote Similarity	NPD3054	Approved
0.695	Remote Similarity	NPD3052	Approved
0.6949	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1894	Discontinued
0.6947	Remote Similarity	NPD6580	Approved
0.6947	Remote Similarity	NPD6581	Approved
0.6944	Remote Similarity	NPD7037	Approved
0.694	Remote Similarity	NPD1840	Phase 2

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