NPASS Compound

Structure

CID319422 OpenBabel06191716142D 33 33 0 0 1 0 0 0 0 0999 V2000 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 5.1962 -3.0000 0.0000 C 0 0 3 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 6.9282 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 33 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 20 2 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 26 1 0 0 0 0 14 19 2 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 16 25 2 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 21 28 1 0 0 0 0 22 27 2 0 0 0 0 23 27 1 0 0 0 0 24 29 2 0 0 0 0 25 33 1 0 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 28 32 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.29
Volume:	507.147
LogP:	5.323
LogD:	3.922
LogS:	-5.273
# Rotatable Bonds:	14
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	3.678
Fsp3:	0.536
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	1.8957392967422493e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.243

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	95.88024139404297%
Volume Distribution (VD):	0.181
Pgp-substrate:	0.6813147664070129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.149
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.933
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.46
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	8.775
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.49
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.436
Skin Sensitization:	0.94
Carcinogencity:	0.705
Eye Corrosion:	0.021
Eye Irritation:	0.679
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC319422

Natural Product ID:	NPC319422
*Common Name:**	13-Hydroxy-1-(2-Hydroxy-5-Methoxy-3-Methylphenyl)-3,7,11,15-Tetramethylhexadeca-2,6,14-Triene-5,12-Dione
IUPAC Name:	(2E,6Z)-13-hydroxy-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-5,12-dione
Synonyms:
Standard InCHIKey:	HBKSTRSDLUAESY-PKVUCGNLSA-N
Standard InCHI:	InChI=1S/C28H40O5/c1-18(2)13-26(30)28(32)21(5)10-8-9-19(3)14-24(29)15-20(4)11-12-23-17-25(33-7)16-22(6)27(23)31/h11,13-14,16-17,21,26,30-31H,8-10,12,15H2,1-7H3/b19-14-,20-11+
SMILES:	CC1=CC(=CC(=C1O)CC=C(C)CC(=O)C=C(C)CCCC(C)C(=O)C(C=C(C)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453071
PubChem CID:	24970395
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO19868	Halidrys siliquosa	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18529079]
NPO19868	Halidrys siliquosa	Species	Sargassaceae	Eukaryota	blades and thalli	Saint-Gunol, Brittany, France; (4747' N, 423' W)	2004-MAY	PMID[18529079]
NPO19868	Halidrys siliquosa	Species	Sargassaceae	Eukaryota	n.a.	Saint-Gunol, Brittany, France (4747' N, 423' W)	2004-MAY	PMID[18529079]
NPO19868	Halidrys siliquosa	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
EC50	1
MIC	4
Others	1

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6038	Organism	Cobetia marina	Cobetia marina	MIC	=	0.5	ug.mL-1	PMID[571590]
NPT6039	Organism	Marinobacterium stanieri	Marinobacterium stanieri	MIC	=	1.0	ug.mL-1	PMID[571590]
NPT6040	Organism	Vibrio fischeri	Aliivibrio fischeri	MIC	=	0.5	ug.mL-1	PMID[571590]
NPT6041	Organism	Pseudoalteromonas haloplanktis	Pseudoalteromonas haloplanktis	MIC	=	1.0	ug.mL-1	PMID[571590]
NPT2540	Organism	Balanus amphitrite	Balanus amphitrite	EC50	=	1.0	ug.mL-1	PMID[571590]
NPT2540	Organism	Balanus amphitrite	Balanus amphitrite	LC50	=	5.0	ug.mL-1	PMID[571590]

☑ 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 NPC319422 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	262
0.1-0.2	1197
0.2-0.3	3274
0.3-0.4	8165
0.4-0.5	10928
0.5-0.6	4411
0.6-0.7	10953
0.7-0.8	3385
0.8-0.85	74
0.85-0.9	22
0.9-0.95	21
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477211
1.0	High Similarity	NPC477214
1.0	High Similarity	NPC477212
0.9833	High Similarity	NPC477213
0.9365	High Similarity	NPC474246
0.9365	High Similarity	NPC474143
0.9262	High Similarity	NPC49441
0.9206	High Similarity	NPC59654
0.9147	High Similarity	NPC477210
0.9134	High Similarity	NPC475880
0.9055	High Similarity	NPC271832
0.8833	High Similarity	NPC473931
0.8833	High Similarity	NPC474050
0.8833	High Similarity	NPC474114
0.875	High Similarity	NPC28784
0.875	High Similarity	NPC296144
0.8741	High Similarity	NPC475063
0.8741	High Similarity	NPC475044
0.8702	High Similarity	NPC251549
0.8682	High Similarity	NPC201419
0.8629	High Similarity	NPC476020
0.8593	High Similarity	NPC475005
0.8593	High Similarity	NPC475028
0.8593	High Similarity	NPC476025
0.8593	High Similarity	NPC474943
0.8582	High Similarity	NPC278832
0.8582	High Similarity	NPC64157
0.855	High Similarity	NPC163169
0.855	High Similarity	NPC196621
0.855	High Similarity	NPC123
0.8538	High Similarity	NPC476024
0.8529	High Similarity	NPC475045
0.8516	High Similarity	NPC190086
0.8516	High Similarity	NPC276962
0.85	High Similarity	NPC208229
0.8496	Intermediate Similarity	NPC470871
0.8485	Intermediate Similarity	NPC258073
0.8478	Intermediate Similarity	NPC474154
0.8473	Intermediate Similarity	NPC206028
0.8433	Intermediate Similarity	NPC27394
0.8421	Intermediate Similarity	NPC329427
0.8421	Intermediate Similarity	NPC317601
0.8421	Intermediate Similarity	NPC312560
0.8417	Intermediate Similarity	NPC26013
0.8417	Intermediate Similarity	NPC282855
0.8413	Intermediate Similarity	NPC474131
0.8413	Intermediate Similarity	NPC232295
0.8385	Intermediate Similarity	NPC474944
0.8372	Intermediate Similarity	NPC474237
0.8372	Intermediate Similarity	NPC147896
0.837	Intermediate Similarity	NPC475011
0.8359	Intermediate Similarity	NPC204535
0.8359	Intermediate Similarity	NPC46586
0.8357	Intermediate Similarity	NPC477409
0.8333	Intermediate Similarity	NPC32152
0.8333	Intermediate Similarity	NPC68260
0.8333	Intermediate Similarity	NPC279887
0.8321	Intermediate Similarity	NPC142087
0.8321	Intermediate Similarity	NPC95034
0.8295	Intermediate Similarity	NPC474130
0.8284	Intermediate Similarity	NPC118253
0.8271	Intermediate Similarity	NPC470725
0.8261	Intermediate Similarity	NPC477408
0.8248	Intermediate Similarity	NPC98804
0.8235	Intermediate Similarity	NPC22222
0.8235	Intermediate Similarity	NPC281513
0.8226	Intermediate Similarity	NPC114918
0.8214	Intermediate Similarity	NPC329493
0.8211	Intermediate Similarity	NPC98372
0.8201	Intermediate Similarity	NPC477535
0.8175	Intermediate Similarity	NPC238176
0.8175	Intermediate Similarity	NPC187993
0.8175	Intermediate Similarity	NPC194847
0.8175	Intermediate Similarity	NPC21797
0.8162	Intermediate Similarity	NPC265793
0.8148	Intermediate Similarity	NPC470160
0.8134	Intermediate Similarity	NPC253488
0.8129	Intermediate Similarity	NPC322021
0.812	Intermediate Similarity	NPC278308
0.8116	Intermediate Similarity	NPC470721
0.8116	Intermediate Similarity	NPC6100
0.8116	Intermediate Similarity	NPC156888
0.8116	Intermediate Similarity	NPC470722
0.8106	Intermediate Similarity	NPC474945
0.8106	Intermediate Similarity	NPC476022
0.8102	Intermediate Similarity	NPC475029
0.8102	Intermediate Similarity	NPC476018
0.8099	Intermediate Similarity	NPC233320
0.8095	Intermediate Similarity	NPC69539
0.8092	Intermediate Similarity	NPC4012
0.8092	Intermediate Similarity	NPC474803
0.808	Intermediate Similarity	NPC197513
0.8077	Intermediate Similarity	NPC477151
0.8077	Intermediate Similarity	NPC132518
0.8071	Intermediate Similarity	NPC477537
0.8062	Intermediate Similarity	NPC474175
0.8058	Intermediate Similarity	NPC98395
0.8045	Intermediate Similarity	NPC12022
0.8045	Intermediate Similarity	NPC293641
0.8045	Intermediate Similarity	NPC20287
0.8045	Intermediate Similarity	NPC470841
0.8045	Intermediate Similarity	NPC20404
0.8043	Intermediate Similarity	NPC84699
0.8028	Intermediate Similarity	NPC316691
0.8028	Intermediate Similarity	NPC148545
0.8015	Intermediate Similarity	NPC239302
0.8015	Intermediate Similarity	NPC244876
0.8	Intermediate Similarity	NPC476165
0.8	Intermediate Similarity	NPC195292
0.8	Intermediate Similarity	NPC172673
0.8	Intermediate Similarity	NPC475012
0.7986	Intermediate Similarity	NPC309452
0.7984	Intermediate Similarity	NPC473136
0.7984	Intermediate Similarity	NPC275627
0.7972	Intermediate Similarity	NPC245482
0.7972	Intermediate Similarity	NPC274085
0.7972	Intermediate Similarity	NPC89664
0.7972	Intermediate Similarity	NPC471600
0.7972	Intermediate Similarity	NPC301751
0.7971	Intermediate Similarity	NPC22644
0.7955	Intermediate Similarity	NPC273686
0.7955	Intermediate Similarity	NPC312404
0.7953	Intermediate Similarity	NPC19290
0.7941	Intermediate Similarity	NPC473982
0.7939	Intermediate Similarity	NPC302211
0.7937	Intermediate Similarity	NPC114144
0.7929	Intermediate Similarity	NPC475104
0.7926	Intermediate Similarity	NPC939
0.7917	Intermediate Similarity	NPC474799
0.7914	Intermediate Similarity	NPC474610
0.7914	Intermediate Similarity	NPC471670
0.791	Intermediate Similarity	NPC71525
0.7907	Intermediate Similarity	NPC473767
0.7899	Intermediate Similarity	NPC471110
0.7891	Intermediate Similarity	NPC37348
0.7887	Intermediate Similarity	NPC124365
0.7886	Intermediate Similarity	NPC241549
0.7883	Intermediate Similarity	NPC165612
0.7879	Intermediate Similarity	NPC4181
0.7879	Intermediate Similarity	NPC257976
0.7879	Intermediate Similarity	NPC163083
0.7879	Intermediate Similarity	NPC242372
0.7879	Intermediate Similarity	NPC164778
0.7874	Intermediate Similarity	NPC473718
0.7872	Intermediate Similarity	NPC268691
0.7872	Intermediate Similarity	NPC470855
0.7872	Intermediate Similarity	NPC76312
0.7868	Intermediate Similarity	NPC319282
0.7868	Intermediate Similarity	NPC311419
0.7868	Intermediate Similarity	NPC275724
0.7868	Intermediate Similarity	NPC215941
0.7868	Intermediate Similarity	NPC245395
0.7868	Intermediate Similarity	NPC123196
0.7868	Intermediate Similarity	NPC137427
0.7868	Intermediate Similarity	NPC65935
0.7868	Intermediate Similarity	NPC142985
0.7868	Intermediate Similarity	NPC244246
0.7863	Intermediate Similarity	NPC31936
0.7863	Intermediate Similarity	NPC251259
0.7863	Intermediate Similarity	NPC48623
0.7863	Intermediate Similarity	NPC168707
0.7863	Intermediate Similarity	NPC201777
0.7862	Intermediate Similarity	NPC300540
0.7857	Intermediate Similarity	NPC130976
0.7852	Intermediate Similarity	NPC81261
0.7852	Intermediate Similarity	NPC473744
0.7852	Intermediate Similarity	NPC193200
0.7847	Intermediate Similarity	NPC474982
0.7847	Intermediate Similarity	NPC469642
0.7842	Intermediate Similarity	NPC152209
0.784	Intermediate Similarity	NPC228609
0.7836	Intermediate Similarity	NPC303680
0.7836	Intermediate Similarity	NPC90128
0.7836	Intermediate Similarity	NPC84076
0.7832	Intermediate Similarity	NPC470087
0.7832	Intermediate Similarity	NPC321980
0.7832	Intermediate Similarity	NPC201297
0.7832	Intermediate Similarity	NPC229916
0.7829	Intermediate Similarity	NPC283616
0.7826	Intermediate Similarity	NPC59459
0.7823	Intermediate Similarity	NPC98392
0.7817	Intermediate Similarity	NPC136649
0.7812	Intermediate Similarity	NPC28951
0.7812	Intermediate Similarity	NPC325646
0.781	Intermediate Similarity	NPC469480
0.781	Intermediate Similarity	NPC205360
0.781	Intermediate Similarity	NPC141549
0.7808	Intermediate Similarity	NPC61284
0.7808	Intermediate Similarity	NPC478163
0.7808	Intermediate Similarity	NPC113428
0.7803	Intermediate Similarity	NPC114298
0.7794	Intermediate Similarity	NPC304622
0.7793	Intermediate Similarity	NPC328623
0.7786	Intermediate Similarity	NPC475549
0.7786	Intermediate Similarity	NPC129176
0.7786	Intermediate Similarity	NPC131868
0.7786	Intermediate Similarity	NPC158949
0.7786	Intermediate Similarity	NPC45663
0.7778	Intermediate Similarity	NPC158871
0.7778	Intermediate Similarity	NPC5018

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 NPC319422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	892
0.2-0.3	1585
0.3-0.4	2489
0.4-0.5	2050
0.5-0.6	1209
0.6-0.7	597
0.7-0.8	80
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
0.8116	Intermediate Similarity	NPD2935	Discontinued
0.7923	Intermediate Similarity	NPD3496	Discontinued
0.7874	Intermediate Similarity	NPD6671	Approved
0.771	Intermediate Similarity	NPD4626	Approved
0.7698	Intermediate Similarity	NPD6355	Discontinued
0.7626	Intermediate Similarity	NPD4060	Phase 1
0.7552	Intermediate Similarity	NPD6005	Phase 3
0.7552	Intermediate Similarity	NPD6002	Phase 3
0.7552	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6004	Phase 3
0.7551	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.7482	Intermediate Similarity	NPD6798	Discontinued
0.7482	Intermediate Similarity	NPD3268	Approved
0.7481	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2798	Approved
0.7429	Intermediate Similarity	NPD6233	Phase 2
0.7426	Intermediate Similarity	NPD1283	Approved
0.7426	Intermediate Similarity	NPD6696	Suspended
0.7413	Intermediate Similarity	NPD2799	Discontinued
0.7405	Intermediate Similarity	NPD7340	Approved
0.7394	Intermediate Similarity	NPD6653	Approved
0.7391	Intermediate Similarity	NPD2861	Phase 2
0.7386	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2424	Discontinued
0.7361	Intermediate Similarity	NPD6099	Approved
0.7361	Intermediate Similarity	NPD6100	Approved
0.7357	Intermediate Similarity	NPD2313	Discontinued
0.7357	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6844	Discontinued
0.7319	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1778	Approved
0.731	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2346	Discontinued
0.731	Intermediate Similarity	NPD5762	Approved
0.731	Intermediate Similarity	NPD5763	Approved
0.7308	Intermediate Similarity	NPD1241	Discontinued
0.7303	Intermediate Similarity	NPD4380	Phase 2
0.7254	Intermediate Similarity	NPD2979	Phase 3
0.7244	Intermediate Similarity	NPD7075	Discontinued
0.7237	Intermediate Similarity	NPD7458	Discontinued
0.7234	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7985	Registered
0.7231	Intermediate Similarity	NPD7635	Approved
0.7226	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5402	Approved
0.7206	Intermediate Similarity	NPD1281	Approved
0.7206	Intermediate Similarity	NPD1535	Discovery
0.7206	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2532	Approved
0.72	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD2533	Approved
0.7194	Intermediate Similarity	NPD5647	Approved
0.7177	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1398	Phase 1
0.7172	Intermediate Similarity	NPD1510	Phase 2
0.7165	Intermediate Similarity	NPD968	Approved
0.7162	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7003	Approved
0.7161	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9717	Approved
0.7153	Intermediate Similarity	NPD1608	Approved
0.7153	Intermediate Similarity	NPD6651	Approved
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1240	Approved
0.7122	Intermediate Similarity	NPD3267	Approved
0.7122	Intermediate Similarity	NPD3266	Approved
0.7122	Intermediate Similarity	NPD6362	Approved
0.7113	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5585	Approved
0.7109	Intermediate Similarity	NPD290	Approved
0.7099	Intermediate Similarity	NPD7843	Approved
0.7097	Intermediate Similarity	NPD1934	Approved
0.7092	Intermediate Similarity	NPD600	Approved
0.7092	Intermediate Similarity	NPD6832	Phase 2
0.7092	Intermediate Similarity	NPD596	Approved
0.709	Intermediate Similarity	NPD5536	Phase 2
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD447	Suspended
0.7081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6166	Phase 2
0.708	Intermediate Similarity	NPD1611	Approved
0.7075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7157	Approved
0.7063	Intermediate Similarity	NPD4062	Phase 3
0.7063	Intermediate Similarity	NPD839	Approved
0.7063	Intermediate Similarity	NPD840	Approved
0.7059	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3019	Approved
0.7059	Intermediate Similarity	NPD2932	Approved
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2684	Approved
0.7051	Intermediate Similarity	NPD7819	Suspended
0.7051	Intermediate Similarity	NPD2801	Approved
0.705	Intermediate Similarity	NPD1876	Approved
0.7047	Intermediate Similarity	NPD8166	Discontinued
0.7047	Intermediate Similarity	NPD4628	Phase 3
0.7042	Intermediate Similarity	NPD7095	Approved
0.7042	Intermediate Similarity	NPD3027	Phase 3
0.7039	Intermediate Similarity	NPD6273	Approved
0.7034	Intermediate Similarity	NPD1607	Approved
0.7031	Intermediate Similarity	NPD3134	Approved
0.7029	Intermediate Similarity	NPD3972	Approved
0.7029	Intermediate Similarity	NPD2235	Phase 2
0.7029	Intermediate Similarity	NPD2233	Approved
0.7029	Intermediate Similarity	NPD2230	Approved
0.7029	Intermediate Similarity	NPD2232	Approved
0.7029	Intermediate Similarity	NPD2231	Phase 2
0.7027	Intermediate Similarity	NPD1549	Phase 2
0.7023	Intermediate Similarity	NPD228	Approved
0.7021	Intermediate Similarity	NPD2237	Approved
0.7013	Intermediate Similarity	NPD3226	Approved
0.7007	Intermediate Similarity	NPD6032	Approved
0.7007	Intermediate Similarity	NPD4476	Approved
0.7007	Intermediate Similarity	NPD2438	Suspended
0.7007	Intermediate Similarity	NPD4477	Approved
0.7007	Intermediate Similarity	NPD3847	Discontinued
0.7	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD6959	Discontinued
0.6993	Remote Similarity	NPD411	Approved
0.6993	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD844	Approved
0.6992	Remote Similarity	NPD2629	Approved
0.6987	Remote Similarity	NPD6801	Discontinued
0.6987	Remote Similarity	NPD37	Approved
0.6986	Remote Similarity	NPD7097	Phase 1
0.6978	Remote Similarity	NPD4749	Approved
0.697	Remote Similarity	NPD1138	Approved
0.6967	Remote Similarity	NPD845	Approved
0.6966	Remote Similarity	NPD5124	Phase 1
0.6966	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7644	Approved
0.6962	Remote Similarity	NPD3882	Suspended
0.6959	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD1201	Approved
0.6951	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD6663	Approved
0.6944	Remote Similarity	NPD8032	Phase 2
0.6939	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4308	Phase 3
0.6937	Remote Similarity	NPD5494	Approved
0.6935	Remote Similarity	NPD288	Approved
0.6934	Remote Similarity	NPD17	Approved
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7473	Discontinued
0.6933	Remote Similarity	NPD4110	Phase 3
0.6928	Remote Similarity	NPD6090	Discontinued
0.6928	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5283	Phase 1
0.6912	Remote Similarity	NPD9545	Approved
0.6912	Remote Similarity	NPD1894	Discontinued
0.6901	Remote Similarity	NPD5736	Approved
0.6897	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2238	Phase 2
0.6897	Remote Similarity	NPD3620	Phase 2
0.6897	Remote Similarity	NPD4140	Approved
0.6894	Remote Similarity	NPD8127	Discontinued
0.6894	Remote Similarity	NPD1139	Approved
0.6894	Remote Similarity	NPD1137	Approved
0.6892	Remote Similarity	NPD2531	Phase 2
0.6892	Remote Similarity	NPD2796	Approved
0.6889	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6190	Approved
0.6883	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD1470	Approved
0.6875	Remote Similarity	NPD1237	Approved
0.687	Remote Similarity	NPD2067	Discontinued
0.6867	Remote Similarity	NPD2800	Approved
0.6864	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4359	Approved
0.6855	Remote Similarity	NPD4967	Phase 2
0.6855	Remote Similarity	NPD4966	Approved
0.6855	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4965	Approved
0.6855	Remote Similarity	NPD7768	Phase 2
0.6853	Remote Similarity	NPD4908	Phase 1
0.6846	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1358	Approved
0.6845	Remote Similarity	NPD8313	Approved
0.6845	Remote Similarity	NPD8312	Approved
0.6842	Remote Similarity	NPD3300	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