NPASS Compound

Structure

NPC206205 OpenBabel07101718192D 35 35 0 0 1 0 0 0 0 0999 V2000 -6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9282 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 6.5000 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 0.8660 0.5000 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 -5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 6.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 6.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 15 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 21 1 0 0 0 0 14 17 2 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 28 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 25 2 0 0 0 0 22 25 1 0 0 0 0 23 30 2 0 0 0 0 23 35 1 0 0 0 0 24 26 2 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 13 1 1 0 0 0 27 29 1 0 0 0 0 27 35 1 0 0 0 0 28 6 1 1 0 0 0 28 33 1 0 0 0 0 29 7 1 6 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.31
Volume:	535.87
LogP:	5.579
LogD:	4.033
LogS:	-3.858
# Rotatable Bonds:	14
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.152
Synthetic Accessibility Score:	4.426
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.661
MDCK Permeability:	1.9420629541855305e-05
Pgp-inhibitor:	0.892
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.805
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	98.9120101928711%
Volume Distribution (VD):	1.939
Pgp-substrate:	3.6948020458221436%

ADMET: Metabolism

CYP1A2-inhibitor:	0.204
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.253
CYP2C19-substrate:	0.162
CYP2C9-inhibitor:	0.356
CYP2C9-substrate:	0.637
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	11.914
Half-life (T1/2):	0.517

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.805
Skin Sensitization:	0.76
Carcinogencity:	0.092
Eye Corrosion:	0.004
Eye Irritation:	0.135
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC206205

Natural Product ID:	NPC206205
*Common Name:**	Chabrolohydroxybenzoquinone G
IUPAC Name:	[(6S,7R,10E,14S,15Z)-16-(2,5-dihydroxy-4-methylphenyl)-6,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,10,15-trien-7-yl] acetate
Synonyms:	Chabrolohydroxybenzoquinone G
Standard InCHIKey:	IWXGRDWGOJXZGA-ZYOATYPXSA-N
Standard InCHI:	InChI=1S/C29H44O6/c1-20(2)10-8-16-29(7,34)27(35-23(5)30)13-12-21(3)11-9-15-28(6,33)17-14-24-19-25(31)22(4)18-26(24)32/h10-11,14,17-19,27,31-34H,8-9,12-13,15-16H2,1-7H3/b17-14-,21-11+/t27-,28+,29+/m1/s1
SMILES:	CC(=CCC[C@@](C)([C@@H](CC/C(=C/CC[C@@](C)(/C=Cc1cc(c(C)cc1O)O)O)/C)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465563
PubChem CID:	44566533
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
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16309317]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	18000.0	nM	PMID[527333]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	18400.0	nM	PMID[527333]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	26800.0	nM	PMID[527333]

☑ 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 NPC206205 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	221
0.1-0.2	1059
0.2-0.3	3068
0.3-0.4	8562
0.4-0.5	11383
0.5-0.6	8623
0.6-0.7	8151
0.7-0.8	1538
0.8-0.85	78
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9217	High Similarity	NPC160235
0.8908	High Similarity	NPC327070
0.8829	High Similarity	NPC474352
0.8814	High Similarity	NPC328485
0.8772	High Similarity	NPC26615
0.875	High Similarity	NPC325301
0.8696	High Similarity	NPC190212
0.8673	High Similarity	NPC473524
0.8621	High Similarity	NPC41851
0.8559	High Similarity	NPC320864
0.8545	High Similarity	NPC477685
0.8545	High Similarity	NPC80800
0.8462	Intermediate Similarity	NPC197513
0.8455	Intermediate Similarity	NPC129373
0.8455	Intermediate Similarity	NPC469568
0.8455	Intermediate Similarity	NPC248396
0.8455	Intermediate Similarity	NPC48730
0.8407	Intermediate Similarity	NPC53740
0.8403	Intermediate Similarity	NPC200988
0.8403	Intermediate Similarity	NPC145023
0.8403	Intermediate Similarity	NPC175799
0.8403	Intermediate Similarity	NPC610
0.8364	Intermediate Similarity	NPC260775
0.8362	Intermediate Similarity	NPC228609
0.8333	Intermediate Similarity	NPC86198
0.832	Intermediate Similarity	NPC476022
0.832	Intermediate Similarity	NPC474945
0.8319	Intermediate Similarity	NPC123559
0.8319	Intermediate Similarity	NPC47284
0.8305	Intermediate Similarity	NPC114918
0.8305	Intermediate Similarity	NPC473931
0.8305	Intermediate Similarity	NPC474050
0.8305	Intermediate Similarity	NPC474114
0.8304	Intermediate Similarity	NPC471228
0.8304	Intermediate Similarity	NPC235762
0.8304	Intermediate Similarity	NPC108497
0.8293	Intermediate Similarity	NPC132518
0.8293	Intermediate Similarity	NPC478058
0.8293	Intermediate Similarity	NPC477151
0.8288	Intermediate Similarity	NPC12931
0.8288	Intermediate Similarity	NPC174911
0.8288	Intermediate Similarity	NPC70677
0.8288	Intermediate Similarity	NPC130756
0.8276	Intermediate Similarity	NPC471535
0.8273	Intermediate Similarity	NPC152097
0.8273	Intermediate Similarity	NPC475078
0.8264	Intermediate Similarity	NPC70084
0.8264	Intermediate Similarity	NPC470214
0.8264	Intermediate Similarity	NPC109371
0.8264	Intermediate Similarity	NPC470215
0.823	Intermediate Similarity	NPC93831
0.823	Intermediate Similarity	NPC475225
0.8226	Intermediate Similarity	NPC474130
0.822	Intermediate Similarity	NPC28784
0.822	Intermediate Similarity	NPC296144
0.8205	Intermediate Similarity	NPC54373
0.819	Intermediate Similarity	NPC98392
0.8182	Intermediate Similarity	NPC203124
0.8182	Intermediate Similarity	NPC309434
0.8174	Intermediate Similarity	NPC66834
0.8145	Intermediate Similarity	NPC204535
0.8145	Intermediate Similarity	NPC469927
0.8145	Intermediate Similarity	NPC46586
0.8136	Intermediate Similarity	NPC228452
0.8136	Intermediate Similarity	NPC302371
0.8125	Intermediate Similarity	NPC72729
0.812	Intermediate Similarity	NPC208229
0.812	Intermediate Similarity	NPC63345
0.8115	Intermediate Similarity	NPC476020
0.811	Intermediate Similarity	NPC66331
0.811	Intermediate Similarity	NPC257947
0.8108	Intermediate Similarity	NPC474073
0.8087	Intermediate Similarity	NPC469913
0.8087	Intermediate Similarity	NPC155072
0.8083	Intermediate Similarity	NPC474486
0.8083	Intermediate Similarity	NPC232165
0.8067	Intermediate Similarity	NPC264558
0.8053	Intermediate Similarity	NPC252105
0.8051	Intermediate Similarity	NPC469912
0.8034	Intermediate Similarity	NPC282855
0.8034	Intermediate Similarity	NPC26013
0.8031	Intermediate Similarity	NPC474944
0.803	Intermediate Similarity	NPC475029
0.803	Intermediate Similarity	NPC476018
0.8017	Intermediate Similarity	NPC281277
0.8016	Intermediate Similarity	NPC474237
0.8	Intermediate Similarity	NPC302211
0.7984	Intermediate Similarity	NPC470849
0.7984	Intermediate Similarity	NPC473875
0.7984	Intermediate Similarity	NPC470848
0.7984	Intermediate Similarity	NPC475529
0.7967	Intermediate Similarity	NPC121866
0.7965	Intermediate Similarity	NPC130103
0.7953	Intermediate Similarity	NPC472592
0.7949	Intermediate Similarity	NPC279887
0.7949	Intermediate Similarity	NPC31274
0.7949	Intermediate Similarity	NPC68260
0.7946	Intermediate Similarity	NPC6597
0.7946	Intermediate Similarity	NPC79241
0.7939	Intermediate Similarity	NPC317601
0.7939	Intermediate Similarity	NPC329427
0.7937	Intermediate Similarity	NPC477152
0.7937	Intermediate Similarity	NPC236981
0.7934	Intermediate Similarity	NPC233669
0.7913	Intermediate Similarity	NPC272029
0.7913	Intermediate Similarity	NPC130817
0.791	Intermediate Similarity	NPC476171
0.7909	Intermediate Similarity	NPC210497
0.7909	Intermediate Similarity	NPC147284
0.7909	Intermediate Similarity	NPC306884
0.7909	Intermediate Similarity	NPC162314
0.7909	Intermediate Similarity	NPC29373
0.7909	Intermediate Similarity	NPC94139
0.7909	Intermediate Similarity	NPC3358
0.7907	Intermediate Similarity	NPC476024
0.7903	Intermediate Similarity	NPC477037
0.7903	Intermediate Similarity	NPC232295
0.7903	Intermediate Similarity	NPC318581
0.7903	Intermediate Similarity	NPC325544
0.7899	Intermediate Similarity	NPC470355
0.7899	Intermediate Similarity	NPC139946
0.7895	Intermediate Similarity	NPC279463
0.7895	Intermediate Similarity	NPC475011
0.7895	Intermediate Similarity	NPC252095
0.7879	Intermediate Similarity	NPC472591
0.7876	Intermediate Similarity	NPC299762
0.7876	Intermediate Similarity	NPC33675
0.7874	Intermediate Similarity	NPC20443
0.7874	Intermediate Similarity	NPC146886
0.7874	Intermediate Similarity	NPC265413
0.7874	Intermediate Similarity	NPC10154
0.7874	Intermediate Similarity	NPC60517
0.7874	Intermediate Similarity	NPC117794
0.7869	Intermediate Similarity	NPC290470
0.7869	Intermediate Similarity	NPC154256
0.7863	Intermediate Similarity	NPC320439
0.7863	Intermediate Similarity	NPC204901
0.7863	Intermediate Similarity	NPC232523
0.7863	Intermediate Similarity	NPC233320
0.7863	Intermediate Similarity	NPC158253
0.7857	Intermediate Similarity	NPC259512
0.7857	Intermediate Similarity	NPC312132
0.7851	Intermediate Similarity	NPC261453
0.7851	Intermediate Similarity	NPC328593
0.7851	Intermediate Similarity	NPC33749
0.7846	Intermediate Similarity	NPC158477
0.784	Intermediate Similarity	NPC165197
0.7833	Intermediate Similarity	NPC177962
0.7833	Intermediate Similarity	NPC48525
0.7833	Intermediate Similarity	NPC62867
0.7829	Intermediate Similarity	NPC473993
0.7829	Intermediate Similarity	NPC142087
0.7829	Intermediate Similarity	NPC95034
0.7826	Intermediate Similarity	NPC269212
0.7823	Intermediate Similarity	NPC472593
0.7823	Intermediate Similarity	NPC98748
0.7823	Intermediate Similarity	NPC263386
0.7823	Intermediate Similarity	NPC471449
0.7823	Intermediate Similarity	NPC323074
0.7823	Intermediate Similarity	NPC32152
0.7823	Intermediate Similarity	NPC141791
0.7823	Intermediate Similarity	NPC151197
0.782	Intermediate Similarity	NPC211164
0.7818	Intermediate Similarity	NPC231150
0.7815	Intermediate Similarity	NPC132720
0.7812	Intermediate Similarity	NPC287473
0.7812	Intermediate Similarity	NPC170749
0.781	Intermediate Similarity	NPC469564
0.7807	Intermediate Similarity	NPC294741
0.7805	Intermediate Similarity	NPC122117
0.7805	Intermediate Similarity	NPC65791
0.7805	Intermediate Similarity	NPC325295
0.7805	Intermediate Similarity	NPC160199
0.7805	Intermediate Similarity	NPC76308
0.7797	Intermediate Similarity	NPC169450
0.7795	Intermediate Similarity	NPC261992
0.7788	Intermediate Similarity	NPC88420
0.7787	Intermediate Similarity	NPC474967
0.7786	Intermediate Similarity	NPC472936
0.7786	Intermediate Similarity	NPC472937
0.7786	Intermediate Similarity	NPC123
0.7786	Intermediate Similarity	NPC472938
0.7786	Intermediate Similarity	NPC163169
0.7786	Intermediate Similarity	NPC475880
0.7786	Intermediate Similarity	NPC11089
0.7778	Intermediate Similarity	NPC99836
0.7778	Intermediate Similarity	NPC12640
0.7778	Intermediate Similarity	NPC310456
0.7778	Intermediate Similarity	NPC201662
0.7778	Intermediate Similarity	NPC25168
0.7769	Intermediate Similarity	NPC95381
0.7769	Intermediate Similarity	NPC176590
0.7769	Intermediate Similarity	NPC261343
0.7769	Intermediate Similarity	NPC148969
0.776	Intermediate Similarity	NPC474131
0.776	Intermediate Similarity	NPC14177
0.776	Intermediate Similarity	NPC478121
0.776	Intermediate Similarity	NPC223451
0.7759	Intermediate Similarity	NPC475580
0.7759	Intermediate Similarity	NPC323810

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 NPC206205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	778
0.2-0.3	1707
0.3-0.4	2717
0.4-0.5	1934
0.5-0.6	1240
0.6-0.7	532
0.7-0.8	49
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
0.8091	Intermediate Similarity	NPD844	Approved
0.7984	Intermediate Similarity	NPD3496	Discontinued
0.7965	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD6671	Approved
0.7857	Intermediate Similarity	NPD288	Approved
0.7833	Intermediate Similarity	NPD7635	Approved
0.7669	Intermediate Similarity	NPD4060	Phase 1
0.7619	Intermediate Similarity	NPD4626	Approved
0.7557	Intermediate Similarity	NPD5736	Approved
0.754	Intermediate Similarity	NPD5691	Approved
0.748	Intermediate Similarity	NPD1778	Approved
0.7464	Intermediate Similarity	NPD5763	Approved
0.7464	Intermediate Similarity	NPD5762	Approved
0.7438	Intermediate Similarity	NPD3021	Approved
0.7438	Intermediate Similarity	NPD4750	Phase 3
0.7438	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD6653	Approved
0.7388	Intermediate Similarity	NPD7985	Registered
0.7364	Intermediate Similarity	NPD1611	Approved
0.736	Intermediate Similarity	NPD4198	Discontinued
0.7353	Intermediate Similarity	NPD6355	Discontinued
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7333	Intermediate Similarity	NPD6663	Approved
0.7333	Intermediate Similarity	NPD4248	Discontinued
0.7328	Intermediate Similarity	NPD6696	Suspended
0.7313	Intermediate Similarity	NPD7095	Approved
0.7304	Intermediate Similarity	NPD2860	Approved
0.7304	Intermediate Similarity	NPD2859	Approved
0.7293	Intermediate Similarity	NPD2237	Approved
0.7281	Intermediate Similarity	NPD845	Approved
0.728	Intermediate Similarity	NPD2629	Approved
0.7273	Intermediate Similarity	NPD290	Approved
0.7266	Intermediate Similarity	NPD6032	Approved
0.7265	Intermediate Similarity	NPD3020	Approved
0.7259	Intermediate Similarity	NPD6798	Discontinued
0.7258	Intermediate Similarity	NPD7843	Approved
0.7222	Intermediate Similarity	NPD7157	Approved
0.7217	Intermediate Similarity	NPD2934	Approved
0.7217	Intermediate Similarity	NPD2933	Approved
0.7217	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2684	Approved
0.7206	Intermediate Similarity	NPD6233	Phase 2
0.7177	Intermediate Similarity	NPD228	Approved
0.7172	Intermediate Similarity	NPD2676	Approved
0.7172	Intermediate Similarity	NPD2675	Approved
0.7165	Intermediate Similarity	NPD7340	Approved
0.7164	Intermediate Similarity	NPD2861	Phase 2
0.7153	Intermediate Similarity	NPD826	Approved
0.7153	Intermediate Similarity	NPD825	Approved
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD940	Approved
0.7143	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.7131	Intermediate Similarity	NPD2342	Discontinued
0.7131	Intermediate Similarity	NPD1358	Approved
0.7122	Intermediate Similarity	NPD7097	Phase 1
0.7109	Intermediate Similarity	NPD7644	Approved
0.7099	Intermediate Similarity	NPD3092	Approved
0.7063	Intermediate Similarity	NPD8166	Discontinued
0.7063	Intermediate Similarity	NPD1398	Phase 1
0.7063	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7054	Intermediate Similarity	NPD3091	Approved
0.7049	Intermediate Similarity	NPD968	Approved
0.704	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6190	Approved
0.7009	Intermediate Similarity	NPD1809	Phase 2
0.7008	Intermediate Similarity	NPD497	Approved
0.7007	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4749	Approved
0.6986	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1091	Approved
0.6944	Remote Similarity	NPD4628	Phase 3
0.6944	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD498	Approved
0.6929	Remote Similarity	NPD496	Approved
0.6929	Remote Similarity	NPD495	Approved
0.6911	Remote Similarity	NPD3134	Approved
0.6911	Remote Similarity	NPD1444	Approved
0.6911	Remote Similarity	NPD1445	Approved
0.6906	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1613	Approved
0.6906	Remote Similarity	NPD4140	Approved
0.6899	Remote Similarity	NPD9493	Approved
0.6891	Remote Similarity	NPD9495	Approved
0.6884	Remote Similarity	NPD1048	Approved
0.6884	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD111	Approved
0.6875	Remote Similarity	NPD9614	Approved
0.6875	Remote Similarity	NPD9618	Approved
0.687	Remote Similarity	NPD5585	Approved
0.6866	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD555	Phase 2
0.685	Remote Similarity	NPD5535	Approved
0.6846	Remote Similarity	NPD1653	Approved
0.6842	Remote Similarity	NPD1535	Discovery
0.6842	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD257	Approved
0.6838	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD258	Approved
0.6838	Remote Similarity	NPD5647	Approved
0.6835	Remote Similarity	NPD4062	Phase 3
0.6831	Remote Similarity	NPD7033	Discontinued
0.6828	Remote Similarity	NPD4110	Phase 3
0.6828	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3095	Discontinued
0.6818	Remote Similarity	NPD3019	Approved
0.6818	Remote Similarity	NPD2932	Approved
0.6815	Remote Similarity	NPD1283	Approved
0.6812	Remote Similarity	NPD4625	Phase 3
0.6806	Remote Similarity	NPD2424	Discontinued
0.6803	Remote Similarity	NPD6647	Phase 2
0.6797	Remote Similarity	NPD5283	Phase 1
0.6794	Remote Similarity	NPD9545	Approved
0.6794	Remote Similarity	NPD1759	Phase 1
0.6791	Remote Similarity	NPD1481	Phase 2
0.6791	Remote Similarity	NPD2233	Approved
0.6791	Remote Similarity	NPD2232	Approved
0.6791	Remote Similarity	NPD2230	Approved
0.6786	Remote Similarity	NPD2979	Phase 3
0.6783	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD969	Suspended
0.6769	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3847	Discontinued
0.6765	Remote Similarity	NPD2797	Approved
0.6765	Remote Similarity	NPD987	Approved
0.6765	Remote Similarity	NPD6362	Approved
0.6763	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1792	Phase 2
0.6746	Remote Similarity	NPD2067	Discontinued
0.6742	Remote Similarity	NPD1357	Approved
0.6739	Remote Similarity	NPD596	Approved
0.6739	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD600	Approved
0.6738	Remote Similarity	NPD447	Suspended
0.6738	Remote Similarity	NPD230	Phase 1
0.6736	Remote Similarity	NPD6005	Phase 3
0.6736	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6004	Phase 3
0.6736	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6002	Phase 3
0.6732	Remote Similarity	NPD5929	Approved
0.6731	Remote Similarity	NPD4666	Phase 3
0.6718	Remote Similarity	NPD9615	Approved
0.6718	Remote Similarity	NPD9613	Approved
0.6718	Remote Similarity	NPD9616	Approved
0.6718	Remote Similarity	NPD1758	Phase 1
0.6716	Remote Similarity	NPD4807	Approved
0.6716	Remote Similarity	NPD4806	Approved
0.6716	Remote Similarity	NPD422	Phase 1
0.6714	Remote Similarity	NPD839	Approved
0.6714	Remote Similarity	NPD259	Phase 1
0.6714	Remote Similarity	NPD840	Approved
0.6713	Remote Similarity	NPD4308	Phase 3
0.6692	Remote Similarity	NPD255	Approved
0.6692	Remote Similarity	NPD5126	Approved
0.6692	Remote Similarity	NPD5306	Approved
0.6692	Remote Similarity	NPD5125	Phase 3
0.6692	Remote Similarity	NPD4059	Approved
0.6692	Remote Similarity	NPD5305	Approved
0.6692	Remote Similarity	NPD9381	Approved
0.6692	Remote Similarity	NPD9384	Approved
0.6692	Remote Similarity	NPD256	Approved
0.6691	Remote Similarity	NPD8651	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2229	Approved
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD74	Approved
0.6667	Remote Similarity	NPD2228	Approved
0.6667	Remote Similarity	NPD6346	Approved
0.6667	Remote Similarity	NPD2231	Phase 2
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9266	Approved
0.6667	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5709	Phase 3
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD2234	Approved
0.6667	Remote Similarity	NPD2235	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD316	Approved
0.6644	Remote Similarity	NPD1652	Phase 2
0.6644	Remote Similarity	NPD6674	Discontinued
0.6643	Remote Similarity	NPD3268	Approved
0.6643	Remote Similarity	NPD411	Approved
0.6642	Remote Similarity	NPD4106	Approved
0.6642	Remote Similarity	NPD4135	Approved
0.6642	Remote Similarity	NPD4136	Approved
0.664	Remote Similarity	NPD6685	Approved
0.6639	Remote Similarity	NPD1242	Phase 1
0.6623	Remote Similarity	NPD2370	Clinical (unspecified phase)

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