NPASS Compound

Structure

CID131799 OpenBabel06191715492D 22 22 0 0 0 0 0 0 0 0999 V2000 6.9282 -1.0000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 5.1962 -0.0000 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 -0.0000 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 -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 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 -2.5981 -1.5000 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 1.7321 -0.0000 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 1.7321 -1.0000 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 -0.0000 2.0000 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.2
Volume:	341.812
LogP:	6.36
LogD:	4.652
LogS:	-4.283
# Rotatable Bonds:	9
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.392
Synthetic Accessibility Score:	2.967
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.693
MDCK Permeability:	2.7331450837664306e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.567
Plasma Protein Binding (PPB):	98.94764709472656%
Volume Distribution (VD):	5.519
Pgp-substrate:	1.6032010316848755%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.301
CYP2C19-inhibitor:	0.687
CYP2C19-substrate:	0.191
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.565
CYP2D6-substrate:	0.705
CYP3A4-inhibitor:	0.346
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	5.681
Half-life (T1/2):	0.362

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.528
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.245
Skin Sensitization:	0.934
Carcinogencity:	0.216
Eye Corrosion:	0.442
Eye Irritation:	0.939
Respiratory Toxicity:	0.6

Download Data

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

Natural Product: NPC131799

Natural Product ID:	NPC131799
*Common Name:**	Flavoglaucin
IUPAC Name:	2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde
Synonyms:	Flavoglaucin
Standard InCHIKey:	RGRXZGKXEJHPQQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H28O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h10,12-13,21-22H,4-9,11H2,1-3H3
SMILES:	CCCCCCCc1c(C=O)c(c(CC=C(C)C)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813664
PubChem CID:	119037
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones

*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
NPO30824	Eurotium repens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667972]

☑ 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	5
Others	5

Activity Type	# Activity
Individual Protein	5
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Activity	=	52.5	%	PMID[496364]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	=	48.0	%	PMID[496364]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Activity	=	67.1	%	PMID[496364]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	<	40.0	%	PMID[496364]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	<	40.0	%	PMID[496364]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.7	ug.mL-1	PMID[496365]
NPT1666	Organism	Plasmodium falciparum D6	Plasmodium falciparum D6	IC50	=	3.0	ug.mL-1	PMID[496365]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	23.0	ug.mL-1	PMID[496365]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	10.41	ug.mL-1	PMID[496365]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	14.32	ug.mL-1	PMID[496365]

☑ 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 NPC131799 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	268
0.1-0.2	1526
0.2-0.3	3589
0.3-0.4	11151
0.4-0.5	8753
0.5-0.6	7117
0.6-0.7	8136
0.7-0.8	1865
0.8-0.85	223
0.85-0.9	61
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC227741
0.9916	High Similarity	NPC136342
0.9916	High Similarity	NPC49647
0.9916	High Similarity	NPC295202
0.936	High Similarity	NPC85342
0.9106	High Similarity	NPC68756
0.9106	High Similarity	NPC152525
0.9008	High Similarity	NPC206207
0.896	High Similarity	NPC306765
0.8837	High Similarity	NPC246693
0.8837	High Similarity	NPC242358
0.8837	High Similarity	NPC110609
0.8833	High Similarity	NPC477453
0.8806	High Similarity	NPC187843
0.88	High Similarity	NPC234890
0.88	High Similarity	NPC74507
0.879	High Similarity	NPC307174
0.876	High Similarity	NPC269414
0.876	High Similarity	NPC41847
0.875	High Similarity	NPC474546
0.875	High Similarity	NPC278928
0.8741	High Similarity	NPC329493
0.874	High Similarity	NPC471530
0.872	High Similarity	NPC275145
0.8689	High Similarity	NPC41567
0.8682	High Similarity	NPC62219
0.8672	High Similarity	NPC3009
0.8672	High Similarity	NPC48248
0.8667	High Similarity	NPC163154
0.8647	High Similarity	NPC305060
0.8615	High Similarity	NPC205992
0.8595	High Similarity	NPC240163
0.8595	High Similarity	NPC161304
0.8582	High Similarity	NPC141368
0.8571	High Similarity	NPC272268
0.8571	High Similarity	NPC472308
0.8548	High Similarity	NPC7151
0.8548	High Similarity	NPC473662
0.8548	High Similarity	NPC285829
0.8548	High Similarity	NPC206778
0.8548	High Similarity	NPC216297
0.8538	High Similarity	NPC198305
0.8538	High Similarity	NPC199253
0.8538	High Similarity	NPC31539
0.8538	High Similarity	NPC136588
0.8516	High Similarity	NPC472047
0.8516	High Similarity	NPC96915
0.8507	High Similarity	NPC245923
0.8504	High Similarity	NPC173978
0.8504	High Similarity	NPC142956
0.8496	Intermediate Similarity	NPC281513
0.8496	Intermediate Similarity	NPC22222
0.8485	Intermediate Similarity	NPC314048
0.848	Intermediate Similarity	NPC244994
0.848	Intermediate Similarity	NPC272454
0.848	Intermediate Similarity	NPC115188
0.848	Intermediate Similarity	NPC292665
0.848	Intermediate Similarity	NPC26433
0.848	Intermediate Similarity	NPC159760
0.848	Intermediate Similarity	NPC35856
0.848	Intermediate Similarity	NPC179092
0.848	Intermediate Similarity	NPC472046
0.848	Intermediate Similarity	NPC178395
0.848	Intermediate Similarity	NPC301987
0.848	Intermediate Similarity	NPC222876
0.8468	Intermediate Similarity	NPC233165
0.8468	Intermediate Similarity	NPC184579
0.8462	Intermediate Similarity	NPC146647
0.8462	Intermediate Similarity	NPC34414
0.8438	Intermediate Similarity	NPC240744
0.8438	Intermediate Similarity	NPC167055
0.8433	Intermediate Similarity	NPC86524
0.8433	Intermediate Similarity	NPC155211
0.8433	Intermediate Similarity	NPC474813
0.8425	Intermediate Similarity	NPC477153
0.8421	Intermediate Similarity	NPC474519
0.8409	Intermediate Similarity	NPC70622
0.84	Intermediate Similarity	NPC294964
0.8397	Intermediate Similarity	NPC55949
0.8385	Intermediate Similarity	NPC282923
0.8382	Intermediate Similarity	NPC476477
0.8382	Intermediate Similarity	NPC111422
0.8382	Intermediate Similarity	NPC306835
0.8382	Intermediate Similarity	NPC256463
0.8382	Intermediate Similarity	NPC299405
0.8382	Intermediate Similarity	NPC471602
0.8382	Intermediate Similarity	NPC29771
0.8382	Intermediate Similarity	NPC162939
0.8382	Intermediate Similarity	NPC216312
0.8372	Intermediate Similarity	NPC160499
0.8372	Intermediate Similarity	NPC1991
0.8359	Intermediate Similarity	NPC4012
0.8359	Intermediate Similarity	NPC199273
0.8359	Intermediate Similarity	NPC310540
0.8358	Intermediate Similarity	NPC278375
0.8346	Intermediate Similarity	NPC11250
0.8346	Intermediate Similarity	NPC282577
0.8346	Intermediate Similarity	NPC52407
0.8346	Intermediate Similarity	NPC477139
0.8346	Intermediate Similarity	NPC300274
0.8346	Intermediate Similarity	NPC115458
0.8333	Intermediate Similarity	NPC471851
0.8333	Intermediate Similarity	NPC7012
0.8321	Intermediate Similarity	NPC37992
0.8321	Intermediate Similarity	NPC147542
0.8321	Intermediate Similarity	NPC327916
0.8321	Intermediate Similarity	NPC32749
0.8321	Intermediate Similarity	NPC220496
0.8321	Intermediate Similarity	NPC42262
0.8321	Intermediate Similarity	NPC241349
0.832	Intermediate Similarity	NPC232178
0.8319	Intermediate Similarity	NPC68260
0.8319	Intermediate Similarity	NPC279887
0.8306	Intermediate Similarity	NPC125252
0.8306	Intermediate Similarity	NPC160199
0.8295	Intermediate Similarity	NPC137750
0.8284	Intermediate Similarity	NPC202225
0.8284	Intermediate Similarity	NPC474394
0.8281	Intermediate Similarity	NPC375356
0.8279	Intermediate Similarity	NPC296144
0.8279	Intermediate Similarity	NPC28784
0.8271	Intermediate Similarity	NPC58685
0.8271	Intermediate Similarity	NPC309430
0.8261	Intermediate Similarity	NPC471444
0.8261	Intermediate Similarity	NPC257003
0.8261	Intermediate Similarity	NPC124365
0.8258	Intermediate Similarity	NPC31799
0.8258	Intermediate Similarity	NPC108129
0.825	Intermediate Similarity	NPC26013
0.825	Intermediate Similarity	NPC98392
0.825	Intermediate Similarity	NPC282855
0.8244	Intermediate Similarity	NPC237225
0.824	Intermediate Similarity	NPC184527
0.8231	Intermediate Similarity	NPC3224
0.8231	Intermediate Similarity	NPC231774
0.8231	Intermediate Similarity	NPC254492
0.8227	Intermediate Similarity	NPC476535
0.8226	Intermediate Similarity	NPC108288
0.8222	Intermediate Similarity	NPC283088
0.8217	Intermediate Similarity	NPC236189
0.8217	Intermediate Similarity	NPC117794
0.8211	Intermediate Similarity	NPC473931
0.8211	Intermediate Similarity	NPC474050
0.8211	Intermediate Similarity	NPC474114
0.8209	Intermediate Similarity	NPC225051
0.8209	Intermediate Similarity	NPC53896
0.8209	Intermediate Similarity	NPC37299
0.8209	Intermediate Similarity	NPC180261
0.8203	Intermediate Similarity	NPC244351
0.8201	Intermediate Similarity	NPC474961
0.8201	Intermediate Similarity	NPC474300
0.8197	Intermediate Similarity	NPC302371
0.8195	Intermediate Similarity	NPC72669
0.8195	Intermediate Similarity	NPC244699
0.8195	Intermediate Similarity	NPC474517
0.8195	Intermediate Similarity	NPC17083
0.8189	Intermediate Similarity	NPC165197
0.8189	Intermediate Similarity	NPC190971
0.8188	Intermediate Similarity	NPC183345
0.8182	Intermediate Similarity	NPC208229
0.8182	Intermediate Similarity	NPC99731
0.8168	Intermediate Similarity	NPC69424
0.8168	Intermediate Similarity	NPC84672
0.8168	Intermediate Similarity	NPC72667
0.8168	Intermediate Similarity	NPC78364
0.8168	Intermediate Similarity	NPC176130
0.8162	Intermediate Similarity	NPC315275
0.816	Intermediate Similarity	NPC174087
0.8156	Intermediate Similarity	NPC68441
0.8154	Intermediate Similarity	NPC477454
0.8154	Intermediate Similarity	NPC287473
0.8154	Intermediate Similarity	NPC123506
0.8154	Intermediate Similarity	NPC472592
0.8154	Intermediate Similarity	NPC103540
0.8148	Intermediate Similarity	NPC12070
0.8148	Intermediate Similarity	NPC50924
0.8148	Intermediate Similarity	NPC472262
0.8148	Intermediate Similarity	NPC274876
0.8148	Intermediate Similarity	NPC287604
0.8148	Intermediate Similarity	NPC161964
0.8143	Intermediate Similarity	NPC476473
0.814	Intermediate Similarity	NPC471187
0.814	Intermediate Similarity	NPC273683
0.8136	Intermediate Similarity	NPC272029
0.8134	Intermediate Similarity	NPC118253
0.8134	Intermediate Similarity	NPC477406
0.8134	Intermediate Similarity	NPC88864
0.8129	Intermediate Similarity	NPC149780
0.8125	Intermediate Similarity	NPC295034
0.8125	Intermediate Similarity	NPC25168
0.8125	Intermediate Similarity	NPC154696
0.8125	Intermediate Similarity	NPC253627
0.812	Intermediate Similarity	NPC475741
0.8116	Intermediate Similarity	NPC143438
0.811	Intermediate Similarity	NPC478121
0.8106	Intermediate Similarity	NPC96024
0.8099	Intermediate Similarity	NPC300540
0.8099	Intermediate Similarity	NPC63918
0.8092	Intermediate Similarity	NPC51037
0.8092	Intermediate Similarity	NPC473691

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 NPC131799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	1012
0.2-0.3	1510
0.3-0.4	2858
0.4-0.5	1963
0.5-0.6	1128
0.6-0.7	366
0.7-0.8	37
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8268	Intermediate Similarity	NPD1201	Approved
0.8226	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1470	Approved
0.7899	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD2935	Discontinued
0.776	Intermediate Similarity	NPD7635	Approved
0.7714	Intermediate Similarity	NPD5406	Approved
0.7714	Intermediate Similarity	NPD5404	Approved
0.7714	Intermediate Similarity	NPD5408	Approved
0.7714	Intermediate Similarity	NPD5405	Approved
0.7708	Intermediate Similarity	NPD7390	Discontinued
0.766	Intermediate Similarity	NPD2346	Discontinued
0.7655	Intermediate Similarity	NPD2534	Approved
0.7655	Intermediate Similarity	NPD2532	Approved
0.7655	Intermediate Similarity	NPD2533	Approved
0.7615	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD9493	Approved
0.7517	Intermediate Similarity	NPD3300	Phase 2
0.7481	Intermediate Similarity	NPD1164	Approved
0.744	Intermediate Similarity	NPD9266	Approved
0.744	Intermediate Similarity	NPD74	Approved
0.7438	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3019	Approved
0.7424	Intermediate Similarity	NPD2932	Approved
0.7424	Intermediate Similarity	NPD4626	Approved
0.7395	Intermediate Similarity	NPD844	Approved
0.736	Intermediate Similarity	NPD9263	Approved
0.736	Intermediate Similarity	NPD9264	Approved
0.736	Intermediate Similarity	NPD9267	Approved
0.7333	Intermediate Similarity	NPD288	Approved
0.7333	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5951	Approved
0.7222	Intermediate Similarity	NPD2342	Discontinued
0.7218	Intermediate Similarity	NPD5691	Approved
0.7174	Intermediate Similarity	NPD2798	Approved
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7153	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD7003	Approved
0.7123	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD943	Approved
0.7109	Intermediate Similarity	NPD4750	Phase 3
0.7092	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2313	Discontinued
0.709	Intermediate Similarity	NPD1651	Approved
0.7089	Intermediate Similarity	NPD6959	Discontinued
0.7083	Intermediate Similarity	NPD845	Approved
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6663	Approved
0.704	Intermediate Similarity	NPD9261	Approved
0.7034	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6696	Suspended
0.7019	Intermediate Similarity	NPD7473	Discontinued
0.7014	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD5736	Approved
0.6993	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1551	Phase 2
0.6972	Remote Similarity	NPD411	Approved
0.697	Remote Similarity	NPD497	Approved
0.697	Remote Similarity	NPD9281	Approved
0.6967	Remote Similarity	NPD1809	Phase 2
0.6954	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD447	Suspended
0.6939	Remote Similarity	NPD2344	Approved
0.6937	Remote Similarity	NPD5710	Approved
0.6937	Remote Similarity	NPD5711	Approved
0.6934	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7819	Suspended
0.6912	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1398	Phase 1
0.6894	Remote Similarity	NPD498	Approved
0.6894	Remote Similarity	NPD495	Approved
0.6894	Remote Similarity	NPD496	Approved
0.6889	Remote Similarity	NPD3091	Approved
0.6889	Remote Similarity	NPD9545	Approved
0.6884	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD1240	Approved
0.6875	Remote Similarity	NPD2979	Phase 3
0.6866	Remote Similarity	NPD7340	Approved
0.6861	Remote Similarity	NPD3026	Approved
0.6861	Remote Similarity	NPD3023	Approved
0.6861	Remote Similarity	NPD3496	Discontinued
0.6853	Remote Similarity	NPD3764	Approved
0.6838	Remote Similarity	NPD3024	Approved
0.6838	Remote Similarity	NPD3025	Approved
0.6824	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2801	Approved
0.6812	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8150	Discontinued
0.6803	Remote Similarity	NPD1510	Phase 2
0.68	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3020	Approved
0.6794	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6671	Approved
0.6783	Remote Similarity	NPD7008	Discontinued
0.6783	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2182	Approved
0.6766	Remote Similarity	NPD36	Approved
0.6766	Remote Similarity	NPD4955	Approved
0.6766	Remote Similarity	NPD5034	Approved
0.6766	Remote Similarity	NPD5028	Approved
0.6766	Remote Similarity	NPD4954	Approved
0.6766	Remote Similarity	NPD5026	Approved
0.6763	Remote Similarity	NPD3972	Approved
0.6761	Remote Similarity	NPD4208	Discontinued
0.6755	Remote Similarity	NPD2309	Approved
0.6752	Remote Similarity	NPD6844	Discontinued
0.6748	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1203	Approved
0.6733	Remote Similarity	NPD2800	Approved
0.6731	Remote Similarity	NPD4380	Phase 2
0.6727	Remote Similarity	NPD5844	Phase 1
0.6726	Remote Similarity	NPD8313	Approved
0.6726	Remote Similarity	NPD8312	Approved
0.6719	Remote Similarity	NPD1237	Approved
0.6714	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1755	Approved
0.6713	Remote Similarity	NPD6832	Phase 2
0.6712	Remote Similarity	NPD230	Phase 1
0.6712	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5030	Phase 2
0.6707	Remote Similarity	NPD6559	Discontinued
0.6694	Remote Similarity	NPD2860	Approved
0.6694	Remote Similarity	NPD2859	Approved
0.6691	Remote Similarity	NPD1611	Approved
0.6691	Remote Similarity	NPD3092	Approved
0.669	Remote Similarity	NPD520	Approved
0.6689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD8166	Discontinued
0.6688	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD3317	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1934	Approved
0.6644	Remote Similarity	NPD4477	Approved
0.6644	Remote Similarity	NPD6100	Approved
0.6644	Remote Similarity	NPD4060	Phase 1
0.6644	Remote Similarity	NPD4476	Approved
0.6644	Remote Similarity	NPD6099	Approved
0.6643	Remote Similarity	NPD9269	Phase 2
0.6642	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1930	Approved
0.6641	Remote Similarity	NPD1929	Approved
0.6641	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7768	Phase 2
0.6623	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7985	Registered
0.662	Remote Similarity	NPD3094	Phase 2
0.662	Remote Similarity	NPD2797	Approved
0.6618	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2933	Approved
0.6613	Remote Similarity	NPD2934	Approved
0.6609	Remote Similarity	NPD6212	Phase 3
0.6609	Remote Similarity	NPD6213	Phase 3
0.6609	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5038	Approved
0.6608	Remote Similarity	NPD5037	Approved
0.6607	Remote Similarity	NPD5027	Approved
0.6607	Remote Similarity	NPD5029	Approved
0.6607	Remote Similarity	NPD5031	Approved
0.6605	Remote Similarity	NPD5494	Approved
0.66	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1471	Phase 3
0.6594	Remote Similarity	NPD9268	Approved
0.6591	Remote Similarity	NPD3021	Approved
0.6591	Remote Similarity	NPD3022	Approved
0.6589	Remote Similarity	NPD164	Approved
0.6579	Remote Similarity	NPD3400	Discontinued
0.6579	Remote Similarity	NPD4628	Phase 3
0.6577	Remote Similarity	NPD4308	Phase 3
0.6573	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1019	Discontinued
0.6571	Remote Similarity	NPD6535	Approved
0.6571	Remote Similarity	NPD6534	Approved
0.6562	Remote Similarity	NPD940	Approved
0.6562	Remote Similarity	NPD5402	Approved
0.6562	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD846	Approved
0.6556	Remote Similarity	NPD1549	Phase 2
0.6554	Remote Similarity	NPD6651	Approved
0.6552	Remote Similarity	NPD4625	Phase 3
0.655	Remote Similarity	NPD5036	Approved
0.6547	Remote Similarity	NPD4059	Approved
0.6547	Remote Similarity	NPD2286	Discontinued
0.6547	Remote Similarity	NPD3095	Discontinued
0.6536	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2066	Phase 3

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