NPASS Compound

Structure

NPC476020 OpenBabel07101718312D 32 32 0 0 1 0 0 0 0 0999 V2000 -6.9282 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -7.0000 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 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 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 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 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 -2.5981 -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 -6.0622 -8.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -7.5000 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 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 -5.1962 -9.0000 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 -4.3301 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 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 -5.1962 -10.0000 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 -3.4641 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -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 27 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 13 1 0 0 0 0 9 19 1 0 0 0 0 10 19 2 0 0 0 0 11 20 2 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 27 1 0 0 0 0 15 18 2 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 23 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 20 26 1 0 0 0 0 21 25 2 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 24 26 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 31 2 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	492.488
LogP:	4.54
LogD:	3.641
LogS:	-4.701
# Rotatable Bonds:	13
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	4.158
Fsp3:	0.556
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:	-4.694
MDCK Permeability:	2.105266321450472e-05
Pgp-inhibitor:	0.114
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	98.90709686279297%
Volume Distribution (VD):	0.218
Pgp-substrate:	0.7432089447975159%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.544
CYP2C19-inhibitor:	0.534
CYP2C19-substrate:	0.313
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.711
CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	11.168
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.459
Skin Sensitization:	0.726
Carcinogencity:	0.028
Eye Corrosion:	0.009
Eye Irritation:	0.43
Respiratory Toxicity:	0.376

Download Data

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

Natural Product: NPC476020

Natural Product ID:	NPC476020
*Common Name:**	(6E,10E)-16-(2,5-Dihydroxy-3-Methylphenyl)-4,14-Dihydroxy-2,6,10,14-Tetramethylhexadeca-2,6,10-Trien-5-One
IUPAC Name:	(6E,10E)-16-(2,5-dihydroxy-3-methylphenyl)-4,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,10-trien-5-one
Synonyms:
Standard InCHIKey:	BVUCFQIGMWEXII-ROUMAOROSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-18(2)15-24(29)26(31)20(4)11-7-9-19(3)10-8-13-27(6,32)14-12-22-17-23(28)16-21(5)25(22)30/h10-11,15-17,24,28-30,32H,7-9,12-14H2,1-6H3/b19-10+,20-11+
SMILES:	C/C(=CCCC(CCc1cc(O)cc(c1O)C)(O)C)/CC/C=C(/C(=O)C(C=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522088
PubChem CID:	25136229
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
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
Others	1

Activity Type	# Activity
Individual Protein	1
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	=	50.0	ug.mL-1	PMID[452442]
NPT2	Others	Unspecified		IC50	>	200.0	ug.mL-1	PMID[452442]
NPT1	Others	Radical scavenging activity		RC50	=	0.24	ug ml-1	PMID[452442]

☑ 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 NPC476020 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	225
0.1-0.2	1178
0.2-0.3	3293
0.3-0.4	9344
0.4-0.5	10674
0.5-0.6	7498
0.6-0.7	9204
0.7-0.8	1200
0.8-0.85	52
0.85-0.9	23
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC473931
0.9375	High Similarity	NPC474050
0.9375	High Similarity	NPC474114
0.9286	High Similarity	NPC296144
0.9286	High Similarity	NPC28784
0.9018	High Similarity	NPC208229
0.8929	High Similarity	NPC26013
0.8929	High Similarity	NPC282855
0.8871	High Similarity	NPC123
0.8871	High Similarity	NPC163169
0.8839	High Similarity	NPC279887
0.8839	High Similarity	NPC68260
0.879	High Similarity	NPC271832
0.8707	High Similarity	NPC114918
0.8684	High Similarity	NPC471535
0.8661	High Similarity	NPC469913
0.864	High Similarity	NPC59654
0.8629	High Similarity	NPC477211
0.8629	High Similarity	NPC319422
0.8629	High Similarity	NPC477214
0.8629	High Similarity	NPC477212
0.8596	High Similarity	NPC98392
0.8596	High Similarity	NPC473524
0.856	High Similarity	NPC476024
0.8547	High Similarity	NPC197513
0.8468	Intermediate Similarity	NPC477213
0.8421	Intermediate Similarity	NPC474352
0.84	Intermediate Similarity	NPC474944
0.8393	Intermediate Similarity	NPC108497
0.8291	Intermediate Similarity	NPC228609
0.8291	Intermediate Similarity	NPC469912
0.8281	Intermediate Similarity	NPC475880
0.8254	Intermediate Similarity	NPC474945
0.8254	Intermediate Similarity	NPC476022
0.8217	Intermediate Similarity	NPC474143
0.8217	Intermediate Similarity	NPC474246
0.8214	Intermediate Similarity	NPC248396
0.8214	Intermediate Similarity	NPC130103
0.8214	Intermediate Similarity	NPC129373
0.8214	Intermediate Similarity	NPC48730
0.8182	Intermediate Similarity	NPC320864
0.8154	Intermediate Similarity	NPC110609
0.8154	Intermediate Similarity	NPC246693
0.8154	Intermediate Similarity	NPC242358
0.8145	Intermediate Similarity	NPC31936
0.8142	Intermediate Similarity	NPC477685
0.8125	Intermediate Similarity	NPC260775
0.8115	Intermediate Similarity	NPC206205
0.8095	Intermediate Similarity	NPC276962
0.8095	Intermediate Similarity	NPC147896
0.8095	Intermediate Similarity	NPC474803
0.8095	Intermediate Similarity	NPC190086
0.808	Intermediate Similarity	NPC49441
0.808	Intermediate Similarity	NPC475192
0.807	Intermediate Similarity	NPC269212
0.8067	Intermediate Similarity	NPC302371
0.8053	Intermediate Similarity	NPC70677
0.8053	Intermediate Similarity	NPC12931
0.8053	Intermediate Similarity	NPC130756
0.8049	Intermediate Similarity	NPC473767
0.8036	Intermediate Similarity	NPC152097
0.8036	Intermediate Similarity	NPC474073
0.8036	Intermediate Similarity	NPC475078
0.803	Intermediate Similarity	NPC204582
0.803	Intermediate Similarity	NPC477210
0.8017	Intermediate Similarity	NPC474486
0.8	Intermediate Similarity	NPC475045
0.8	Intermediate Similarity	NPC93831
0.7984	Intermediate Similarity	NPC223451
0.7984	Intermediate Similarity	NPC232295
0.7984	Intermediate Similarity	NPC473136
0.7983	Intermediate Similarity	NPC54373
0.7982	Intermediate Similarity	NPC80800
0.7949	Intermediate Similarity	NPC305603
0.7949	Intermediate Similarity	NPC61033
0.7941	Intermediate Similarity	NPC475063
0.7941	Intermediate Similarity	NPC475044
0.7937	Intermediate Similarity	NPC204535
0.7937	Intermediate Similarity	NPC132518
0.7937	Intermediate Similarity	NPC477151
0.7937	Intermediate Similarity	NPC46586
0.7934	Intermediate Similarity	NPC41851
0.7934	Intermediate Similarity	NPC12656
0.7926	Intermediate Similarity	NPC475005
0.7926	Intermediate Similarity	NPC474943
0.792	Intermediate Similarity	NPC474175
0.7913	Intermediate Similarity	NPC471228
0.7913	Intermediate Similarity	NPC235762
0.7903	Intermediate Similarity	NPC32152
0.7899	Intermediate Similarity	NPC132720
0.7895	Intermediate Similarity	NPC174911
0.7891	Intermediate Similarity	NPC127975
0.7886	Intermediate Similarity	NPC269414
0.7879	Intermediate Similarity	NPC317601
0.7879	Intermediate Similarity	NPC329427
0.7874	Intermediate Similarity	NPC474130
0.7863	Intermediate Similarity	NPC155072
0.7863	Intermediate Similarity	NPC53740
0.7857	Intermediate Similarity	NPC472892
0.7846	Intermediate Similarity	NPC24869
0.7845	Intermediate Similarity	NPC272029
0.7845	Intermediate Similarity	NPC475225
0.784	Intermediate Similarity	NPC474131
0.7836	Intermediate Similarity	NPC130899
0.7836	Intermediate Similarity	NPC283590
0.7836	Intermediate Similarity	NPC70859
0.7836	Intermediate Similarity	NPC61153
0.7823	Intermediate Similarity	NPC9592
0.7823	Intermediate Similarity	NPC48781
0.7823	Intermediate Similarity	NPC41567
0.7812	Intermediate Similarity	NPC469568
0.7807	Intermediate Similarity	NPC128723
0.7805	Intermediate Similarity	NPC141001
0.7797	Intermediate Similarity	NPC66834
0.7795	Intermediate Similarity	NPC327070
0.7795	Intermediate Similarity	NPC325301
0.7794	Intermediate Similarity	NPC475028
0.7794	Intermediate Similarity	NPC476025
0.7787	Intermediate Similarity	NPC473137
0.7786	Intermediate Similarity	NPC474546
0.7786	Intermediate Similarity	NPC278928
0.7778	Intermediate Similarity	NPC243677
0.7778	Intermediate Similarity	NPC303141
0.7778	Intermediate Similarity	NPC471350
0.7778	Intermediate Similarity	NPC47284
0.7769	Intermediate Similarity	NPC95034
0.7769	Intermediate Similarity	NPC228425
0.7769	Intermediate Similarity	NPC228988
0.7769	Intermediate Similarity	NPC142087
0.776	Intermediate Similarity	NPC182240
0.776	Intermediate Similarity	NPC469644
0.776	Intermediate Similarity	NPC323074
0.776	Intermediate Similarity	NPC151197
0.7752	Intermediate Similarity	NPC131799
0.7752	Intermediate Similarity	NPC472592
0.7744	Intermediate Similarity	NPC251549
0.7739	Intermediate Similarity	NPC294741
0.7734	Intermediate Similarity	NPC477153
0.7734	Intermediate Similarity	NPC273683
0.7731	Intermediate Similarity	NPC262365
0.7731	Intermediate Similarity	NPC95344
0.7727	Intermediate Similarity	NPC196621
0.7724	Intermediate Similarity	NPC232165
0.7724	Intermediate Similarity	NPC240163
0.7721	Intermediate Similarity	NPC305060
0.7719	Intermediate Similarity	NPC88420
0.7717	Intermediate Similarity	NPC476165
0.7712	Intermediate Similarity	NPC12640
0.7712	Intermediate Similarity	NPC99836
0.7712	Intermediate Similarity	NPC201662
0.771	Intermediate Similarity	NPC473744
0.7705	Intermediate Similarity	NPC319803
0.7705	Intermediate Similarity	NPC261343
0.7698	Intermediate Similarity	NPC325544
0.7698	Intermediate Similarity	NPC477037
0.7698	Intermediate Similarity	NPC318581
0.7692	Intermediate Similarity	NPC136342
0.7692	Intermediate Similarity	NPC49647
0.7692	Intermediate Similarity	NPC227741
0.7692	Intermediate Similarity	NPC306765
0.7692	Intermediate Similarity	NPC323810
0.7692	Intermediate Similarity	NPC295202
0.7687	Intermediate Similarity	NPC40524
0.7687	Intermediate Similarity	NPC213485
0.7687	Intermediate Similarity	NPC78307
0.7687	Intermediate Similarity	NPC139074
0.7686	Intermediate Similarity	NPC470355
0.7686	Intermediate Similarity	NPC308689
0.768	Intermediate Similarity	NPC154030
0.768	Intermediate Similarity	NPC471671
0.768	Intermediate Similarity	NPC469609
0.7679	Intermediate Similarity	NPC29373
0.7679	Intermediate Similarity	NPC147284
0.7679	Intermediate Similarity	NPC162314
0.7679	Intermediate Similarity	NPC3358
0.7679	Intermediate Similarity	NPC94139
0.7679	Intermediate Similarity	NPC210497
0.7679	Intermediate Similarity	NPC306884
0.7674	Intermediate Similarity	NPC152525
0.7674	Intermediate Similarity	NPC117794
0.7674	Intermediate Similarity	NPC231767
0.7674	Intermediate Similarity	NPC68756
0.7674	Intermediate Similarity	NPC474237
0.7672	Intermediate Similarity	NPC166313
0.7672	Intermediate Similarity	NPC147310
0.7672	Intermediate Similarity	NPC294186
0.7672	Intermediate Similarity	NPC24407
0.7672	Intermediate Similarity	NPC11280
0.7672	Intermediate Similarity	NPC192032
0.7672	Intermediate Similarity	NPC137415
0.7669	Intermediate Similarity	NPC473777
0.7669	Intermediate Similarity	NPC476847
0.7667	Intermediate Similarity	NPC471954
0.7667	Intermediate Similarity	NPC75272
0.7661	Intermediate Similarity	NPC69539
0.7661	Intermediate Similarity	NPC123559
0.7656	Intermediate Similarity	NPC297193
0.7647	Intermediate Similarity	NPC278832
0.7647	Intermediate Similarity	NPC232523
0.7647	Intermediate Similarity	NPC204901

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 NPC476020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	853
0.2-0.3	1715
0.3-0.4	2834
0.4-0.5	1972
0.5-0.6	1143
0.6-0.7	400
0.7-0.8	19
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
0.7739	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7635	Approved
0.7544	Intermediate Similarity	NPD844	Approved
0.744	Intermediate Similarity	NPD6671	Approved
0.7377	Intermediate Similarity	NPD4750	Phase 3
0.7368	Intermediate Similarity	NPD845	Approved
0.7364	Intermediate Similarity	NPD3496	Discontinued
0.7328	Intermediate Similarity	NPD288	Approved
0.728	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7258	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1809	Phase 2
0.7227	Intermediate Similarity	NPD846	Approved
0.7227	Intermediate Similarity	NPD940	Approved
0.7218	Intermediate Similarity	NPD1470	Approved
0.7214	Intermediate Similarity	NPD2935	Discontinued
0.7209	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1201	Approved
0.7154	Intermediate Similarity	NPD4626	Approved
0.7094	Intermediate Similarity	NPD2860	Approved
0.7094	Intermediate Similarity	NPD2859	Approved
0.7059	Intermediate Similarity	NPD3020	Approved
0.7009	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2934	Approved
0.7009	Intermediate Similarity	NPD2933	Approved
0.7	Intermediate Similarity	NPD3091	Approved
0.6985	Remote Similarity	NPD2861	Phase 2
0.6978	Remote Similarity	NPD4060	Phase 1
0.6977	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1237	Approved
0.6966	Remote Similarity	NPD6190	Approved
0.6963	Remote Similarity	NPD3094	Phase 2
0.696	Remote Similarity	NPD3021	Approved
0.696	Remote Similarity	NPD3022	Approved
0.6957	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5691	Approved
0.6935	Remote Similarity	NPD2342	Discontinued
0.6923	Remote Similarity	NPD5763	Approved
0.6923	Remote Similarity	NPD7266	Discontinued
0.6923	Remote Similarity	NPD5762	Approved
0.6918	Remote Similarity	NPD3300	Phase 2
0.6917	Remote Similarity	NPD3092	Approved
0.6912	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3019	Approved
0.6894	Remote Similarity	NPD2932	Approved
0.6875	Remote Similarity	NPD2424	Discontinued
0.6861	Remote Similarity	NPD5736	Approved
0.6861	Remote Similarity	NPD4208	Discontinued
0.6846	Remote Similarity	NPD7340	Approved
0.6824	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9618	Approved
0.6822	Remote Similarity	NPD497	Approved
0.6822	Remote Similarity	NPD9614	Approved
0.6815	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4248	Discontinued
0.6786	Remote Similarity	NPD6405	Approved
0.6786	Remote Similarity	NPD6407	Approved
0.6783	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3095	Discontinued
0.6763	Remote Similarity	NPD3027	Phase 3
0.6757	Remote Similarity	NPD7390	Discontinued
0.6748	Remote Similarity	NPD6647	Phase 2
0.6748	Remote Similarity	NPD9500	Approved
0.6744	Remote Similarity	NPD496	Approved
0.6744	Remote Similarity	NPD1398	Phase 1
0.6744	Remote Similarity	NPD495	Approved
0.6744	Remote Similarity	NPD498	Approved
0.6742	Remote Similarity	NPD9545	Approved
0.6738	Remote Similarity	NPD943	Approved
0.6736	Remote Similarity	NPD5405	Approved
0.6736	Remote Similarity	NPD5406	Approved
0.6736	Remote Similarity	NPD5408	Approved
0.6736	Remote Similarity	NPD5404	Approved
0.6721	Remote Similarity	NPD1242	Phase 1
0.672	Remote Similarity	NPD1444	Approved
0.672	Remote Similarity	NPD1445	Approved
0.6718	Remote Similarity	NPD9493	Approved
0.6715	Remote Similarity	NPD1133	Approved
0.6715	Remote Similarity	NPD1129	Approved
0.6715	Remote Similarity	NPD1135	Approved
0.6715	Remote Similarity	NPD1134	Approved
0.6715	Remote Similarity	NPD1131	Approved
0.6712	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4380	Phase 2
0.6711	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2629	Approved
0.6691	Remote Similarity	NPD4207	Discontinued
0.6691	Remote Similarity	NPD4749	Approved
0.669	Remote Similarity	NPD5124	Phase 1
0.669	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6002	Phase 3
0.669	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6005	Phase 3
0.669	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6004	Phase 3
0.6688	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9616	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD9613	Approved
0.6667	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD9615	Approved
0.6645	Remote Similarity	NPD5402	Approved
0.6643	Remote Similarity	NPD4625	Phase 3
0.6642	Remote Similarity	NPD1778	Approved
0.6642	Remote Similarity	NPD9381	Approved
0.6642	Remote Similarity	NPD9384	Approved
0.6642	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6100	Approved
0.6621	Remote Similarity	NPD6099	Approved
0.662	Remote Similarity	NPD2238	Phase 2
0.6617	Remote Similarity	NPD316	Approved
0.6614	Remote Similarity	NPD74	Approved
0.6614	Remote Similarity	NPD9266	Approved
0.6614	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7985	Registered
0.6596	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD1164	Approved
0.6591	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD968	Approved
0.6587	Remote Similarity	NPD8150	Discontinued
0.6581	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD230	Phase 1
0.6573	Remote Similarity	NPD6355	Discontinued
0.6571	Remote Similarity	NPD596	Approved
0.6571	Remote Similarity	NPD600	Approved
0.6569	Remote Similarity	NPD9622	Approved
0.6562	Remote Similarity	NPD1792	Phase 2
0.6557	Remote Similarity	NPD9495	Approved
0.6554	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7033	Discontinued
0.6552	Remote Similarity	NPD1510	Phase 2
0.6549	Remote Similarity	NPD840	Approved
0.6549	Remote Similarity	NPD839	Approved
0.6547	Remote Similarity	NPD858	Approved
0.6547	Remote Similarity	NPD859	Approved
0.6547	Remote Similarity	NPD602	Approved
0.6547	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD599	Approved
0.6544	Remote Similarity	NPD1611	Approved
0.6541	Remote Similarity	NPD5536	Phase 2
0.6541	Remote Similarity	NPD856	Approved
0.6541	Remote Similarity	NPD16	Approved
0.6538	Remote Similarity	NPD7843	Approved
0.6535	Remote Similarity	NPD9264	Approved
0.6535	Remote Similarity	NPD9267	Approved
0.6535	Remote Similarity	NPD290	Approved
0.6535	Remote Similarity	NPD9263	Approved
0.6529	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6653	Approved
0.6525	Remote Similarity	NPD7095	Approved
0.6522	Remote Similarity	NPD8651	Approved
0.6519	Remote Similarity	NPD4059	Approved
0.6516	Remote Similarity	NPD6844	Discontinued
0.6515	Remote Similarity	NPD7157	Approved
0.6512	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1240	Approved
0.6503	Remote Similarity	NPD1613	Approved
0.65	Remote Similarity	NPD4212	Discontinued
0.6496	Remote Similarity	NPD2233	Approved
0.6496	Remote Similarity	NPD2230	Approved
0.6496	Remote Similarity	NPD2232	Approved
0.6496	Remote Similarity	NPD9269	Phase 2
0.6493	Remote Similarity	NPD7741	Discontinued
0.6493	Remote Similarity	NPD7330	Discontinued
0.649	Remote Similarity	NPD2533	Approved
0.649	Remote Similarity	NPD2532	Approved
0.649	Remote Similarity	NPD2534	Approved
0.6489	Remote Similarity	NPD2234	Approved
0.6489	Remote Similarity	NPD2229	Approved
0.6489	Remote Similarity	NPD2228	Approved
0.6486	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5039	Approved
0.6484	Remote Similarity	NPD2684	Approved
0.648	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2313	Discontinued
0.6479	Remote Similarity	NPD3764	Approved
0.6479	Remote Similarity	NPD6798	Discontinued
0.6475	Remote Similarity	NPD4103	Phase 2
0.6475	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7819	Suspended
0.6471	Remote Similarity	NPD1653	Approved
0.6471	Remote Similarity	NPD3026	Approved
0.6471	Remote Similarity	NPD3023	Approved
0.6463	Remote Similarity	NPD2346	Discontinued
0.6462	Remote Similarity	NPD228	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