NPASS Compound

Structure

NPC252095 OpenBabel07101719252D 27 27 0 0 0 0 0 0 0 0999 V2000 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 0.8660 -1.5000 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 1.7321 0.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 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 -0.8660 -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 6 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 20 21 2 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.25
Volume:	417.15
LogP:	6.635
LogD:	4.607
LogS:	-3.384
# Rotatable Bonds:	11
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	2.903
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	2.2627678845310584e-05
Pgp-inhibitor:	0.894
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.624

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	98.73782348632812%
Volume Distribution (VD):	2.172
Pgp-substrate:	1.9968926906585693%

ADMET: Metabolism

CYP1A2-inhibitor:	0.892
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.578
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.633
CYP2D6-substrate:	0.557
CYP3A4-inhibitor:	0.326
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	3.162
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.193
Skin Sensitization:	0.944
Carcinogencity:	0.044
Eye Corrosion:	0.008
Eye Irritation:	0.894
Respiratory Toxicity:	0.481

Download Data

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

Natural Product: NPC252095

Natural Product ID:	NPC252095
*Common Name:**	5-Acetyl-4-Hydroxycannabigerol
IUPAC Name:	[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,6-dihydroxy-5-pentylphenyl] acetate
Synonyms:
Standard InCHIKey:	NQWZDPKQSSITCN-GHRIWEEISA-N
Standard InCHI:	InChI=1S/C23H34O4/c1-6-7-8-12-19-15-21(25)20(23(22(19)26)27-18(5)24)14-13-17(4)11-9-10-16(2)3/h10,13,15,25-26H,6-9,11-12,14H2,1-5H3/b17-13+
SMILES:	CCCCCc1cc(c(C/C=C(C)/CCC=C(C)C)c(c1O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL553226
PubChem CID:	44139615
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
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50031a011]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18303850]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681481]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19344127]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21902175]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26000707]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32880179]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7513	Cannabis sativa	Species	Cannabaceae	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	4
Others	1

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6700.0	nM	PMID[454123]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7200.0	nM	PMID[454123]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	10700.0	nM	PMID[454123]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	18700.0	nM	PMID[454123]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	53400.0	nM	PMID[454123]

☑ 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 NPC252095 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	335
0.1-0.2	1589
0.2-0.3	5088
0.3-0.4	12579
0.4-0.5	5477
0.5-0.6	4739
0.6-0.7	8156
0.7-0.8	4185
0.8-0.85	471
0.85-0.9	62
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.969	High Similarity	NPC474810
0.9688	High Similarity	NPC147317
0.9545	High Similarity	NPC476171
0.9535	High Similarity	NPC142530
0.9462	High Similarity	NPC474635
0.9407	High Similarity	NPC469564
0.9398	High Similarity	NPC105493
0.916	High Similarity	NPC220935
0.9147	High Similarity	NPC474632
0.9137	High Similarity	NPC475896
0.9077	High Similarity	NPC474670
0.9077	High Similarity	NPC474821
0.9071	High Similarity	NPC170239
0.9071	High Similarity	NPC97937
0.9071	High Similarity	NPC275125
0.9065	High Similarity	NPC292256
0.9008	High Similarity	NPC474636
0.9	High Similarity	NPC112596
0.8963	High Similarity	NPC255147
0.8963	High Similarity	NPC281521
0.8963	High Similarity	NPC201357
0.8955	High Similarity	NPC277021
0.8947	High Similarity	NPC82503
0.8944	High Similarity	NPC113790
0.8929	High Similarity	NPC125617
0.8921	High Similarity	NPC256555
0.8921	High Similarity	NPC7439
0.8921	High Similarity	NPC91492
0.8921	High Similarity	NPC110067
0.8921	High Similarity	NPC34245
0.8872	High Similarity	NPC474617
0.8864	High Similarity	NPC474616
0.8855	High Similarity	NPC245060
0.8837	High Similarity	NPC246967
0.8837	High Similarity	NPC135414
0.8832	High Similarity	NPC52086
0.8832	High Similarity	NPC148835
0.8832	High Similarity	NPC20511
0.8832	High Similarity	NPC139548
0.8832	High Similarity	NPC95162
0.8832	High Similarity	NPC76336
0.8815	High Similarity	NPC269528
0.8815	High Similarity	NPC94236
0.8815	High Similarity	NPC37196
0.8788	High Similarity	NPC216836
0.8768	High Similarity	NPC13067
0.8759	High Similarity	NPC82271
0.8759	High Similarity	NPC126682
0.8741	High Similarity	NPC161203
0.8731	High Similarity	NPC214860
0.8722	High Similarity	NPC266691
0.8712	High Similarity	NPC476006
0.8696	High Similarity	NPC38874
0.8692	High Similarity	NPC474864
0.8686	High Similarity	NPC134968
0.8657	High Similarity	NPC45824
0.8657	High Similarity	NPC158477
0.8652	High Similarity	NPC236419
0.8647	High Similarity	NPC236760
0.8639	High Similarity	NPC7178
0.8639	High Similarity	NPC62903
0.8633	High Similarity	NPC19869
0.8633	High Similarity	NPC43500
0.8633	High Similarity	NPC164148
0.8623	High Similarity	NPC472336
0.8623	High Similarity	NPC472334
0.8623	High Similarity	NPC476698
0.8613	High Similarity	NPC92830
0.8603	High Similarity	NPC319969
0.8603	High Similarity	NPC127624
0.8603	High Similarity	NPC137949
0.8593	High Similarity	NPC51840
0.8593	High Similarity	NPC229231
0.8593	High Similarity	NPC311680
0.8593	High Similarity	NPC234488
0.8593	High Similarity	NPC299221
0.8582	High Similarity	NPC472335
0.8582	High Similarity	NPC472332
0.8582	High Similarity	NPC19694
0.8581	High Similarity	NPC292385
0.8581	High Similarity	NPC142479
0.8581	High Similarity	NPC125709
0.8581	High Similarity	NPC155015
0.8571	High Similarity	NPC181361
0.8561	High Similarity	NPC474530
0.8561	High Similarity	NPC102904
0.8561	High Similarity	NPC107551
0.8561	High Similarity	NPC176051
0.8561	High Similarity	NPC183446
0.8561	High Similarity	NPC474886
0.8561	High Similarity	NPC276490
0.8561	High Similarity	NPC103976
0.8561	High Similarity	NPC78446
0.8561	High Similarity	NPC474540
0.8561	High Similarity	NPC474282
0.8561	High Similarity	NPC474521
0.8561	High Similarity	NPC140521
0.8561	High Similarity	NPC326797
0.8552	High Similarity	NPC30688
0.8552	High Similarity	NPC176903
0.8551	High Similarity	NPC472337
0.8551	High Similarity	NPC261873
0.8551	High Similarity	NPC283009
0.8542	High Similarity	NPC178129
0.854	High Similarity	NPC26673
0.8529	High Similarity	NPC73738
0.8529	High Similarity	NPC469907
0.8521	High Similarity	NPC477616
0.8521	High Similarity	NPC6568
0.8521	High Similarity	NPC230157
0.8519	High Similarity	NPC10225
0.8519	High Similarity	NPC58164
0.8511	High Similarity	NPC300611
0.8507	High Similarity	NPC50368
0.8507	High Similarity	NPC470699
0.85	High Similarity	NPC319647
0.85	High Similarity	NPC25966
0.85	High Similarity	NPC127218
0.85	High Similarity	NPC245207
0.8496	Intermediate Similarity	NPC249836
0.8493	Intermediate Similarity	NPC120426
0.8493	Intermediate Similarity	NPC294522
0.8493	Intermediate Similarity	NPC21184
0.8493	Intermediate Similarity	NPC205727
0.8489	Intermediate Similarity	NPC286843
0.8489	Intermediate Similarity	NPC471719
0.8483	Intermediate Similarity	NPC139839
0.8478	Intermediate Similarity	NPC103967
0.8478	Intermediate Similarity	NPC106215
0.8478	Intermediate Similarity	NPC474600
0.8478	Intermediate Similarity	NPC111635
0.8472	Intermediate Similarity	NPC205361
0.8467	Intermediate Similarity	NPC6451
0.8467	Intermediate Similarity	NPC202762
0.8467	Intermediate Similarity	NPC86655
0.8462	Intermediate Similarity	NPC471763
0.8446	Intermediate Similarity	NPC476154
0.8444	Intermediate Similarity	NPC63179
0.844	Intermediate Similarity	NPC259519
0.844	Intermediate Similarity	NPC160283
0.844	Intermediate Similarity	NPC254759
0.8435	Intermediate Similarity	NPC225129
0.8429	Intermediate Similarity	NPC25111
0.8429	Intermediate Similarity	NPC6262
0.8429	Intermediate Similarity	NPC201145
0.8429	Intermediate Similarity	NPC90615
0.8429	Intermediate Similarity	NPC272157
0.8429	Intermediate Similarity	NPC73535
0.8417	Intermediate Similarity	NPC47398
0.8417	Intermediate Similarity	NPC260898
0.8417	Intermediate Similarity	NPC112246
0.8417	Intermediate Similarity	NPC470356
0.8417	Intermediate Similarity	NPC474206
0.8417	Intermediate Similarity	NPC234333
0.8417	Intermediate Similarity	NPC112939
0.8417	Intermediate Similarity	NPC94750
0.8417	Intermediate Similarity	NPC195022
0.8417	Intermediate Similarity	NPC121812
0.8417	Intermediate Similarity	NPC234865
0.8414	Intermediate Similarity	NPC476347
0.8414	Intermediate Similarity	NPC231149
0.8406	Intermediate Similarity	NPC241341
0.8406	Intermediate Similarity	NPC36661
0.8406	Intermediate Similarity	NPC36437
0.8406	Intermediate Similarity	NPC475840
0.8406	Intermediate Similarity	NPC229442
0.8406	Intermediate Similarity	NPC168059
0.8406	Intermediate Similarity	NPC233018
0.8394	Intermediate Similarity	NPC309787
0.8394	Intermediate Similarity	NPC474356
0.8394	Intermediate Similarity	NPC12275
0.8394	Intermediate Similarity	NPC232275
0.8394	Intermediate Similarity	NPC45715
0.8392	Intermediate Similarity	NPC138212
0.8389	Intermediate Similarity	NPC77430
0.838	Intermediate Similarity	NPC471389
0.838	Intermediate Similarity	NPC247291
0.838	Intermediate Similarity	NPC311530
0.8378	Intermediate Similarity	NPC120774
0.8378	Intermediate Similarity	NPC163598
0.8378	Intermediate Similarity	NPC221085
0.8378	Intermediate Similarity	NPC264875
0.8372	Intermediate Similarity	NPC471503
0.8372	Intermediate Similarity	NPC471498
0.837	Intermediate Similarity	NPC250432
0.837	Intermediate Similarity	NPC159968
0.837	Intermediate Similarity	NPC246620
0.837	Intermediate Similarity	NPC5447
0.837	Intermediate Similarity	NPC210355
0.837	Intermediate Similarity	NPC74817
0.837	Intermediate Similarity	NPC124452
0.837	Intermediate Similarity	NPC82679
0.837	Intermediate Similarity	NPC324112
0.837	Intermediate Similarity	NPC169474
0.837	Intermediate Similarity	NPC293054
0.837	Intermediate Similarity	NPC236791
0.837	Intermediate Similarity	NPC282000
0.8369	Intermediate Similarity	NPC292882
0.8357	Intermediate Similarity	NPC476639
0.8357	Intermediate Similarity	NPC248727

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 NPC252095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	948
0.2-0.3	2136
0.3-0.4	2780
0.4-0.5	1507
0.5-0.6	937
0.6-0.7	453
0.7-0.8	83
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1653	Approved
0.8116	Intermediate Similarity	NPD3027	Phase 3
0.8074	Intermediate Similarity	NPD4749	Approved
0.8071	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD422	Phase 1
0.7803	Intermediate Similarity	NPD6671	Approved
0.7801	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2801	Approved
0.7754	Intermediate Similarity	NPD6696	Suspended
0.773	Intermediate Similarity	NPD4625	Phase 3
0.7721	Intermediate Similarity	NPD3496	Discontinued
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6100	Approved
0.7671	Intermediate Similarity	NPD6099	Approved
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.7639	Intermediate Similarity	NPD447	Suspended
0.7613	Intermediate Similarity	NPD1934	Approved
0.7595	Intermediate Similarity	NPD6234	Discontinued
0.7566	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1465	Phase 2
0.7552	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1611	Approved
0.7518	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1778	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.7452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7434	Intermediate Similarity	NPD1511	Approved
0.7413	Intermediate Similarity	NPD4908	Phase 1
0.7405	Intermediate Similarity	NPD3817	Phase 2
0.74	Intermediate Similarity	NPD1652	Phase 2
0.7397	Intermediate Similarity	NPD230	Phase 1
0.7389	Intermediate Similarity	NPD37	Approved
0.7383	Intermediate Similarity	NPD5763	Approved
0.7383	Intermediate Similarity	NPD5762	Approved
0.7378	Intermediate Similarity	NPD7228	Approved
0.7358	Intermediate Similarity	NPD4965	Approved
0.7358	Intermediate Similarity	NPD4966	Approved
0.7358	Intermediate Similarity	NPD4967	Phase 2
0.7358	Intermediate Similarity	NPD3882	Suspended
0.7348	Intermediate Similarity	NPD4750	Phase 3
0.7346	Intermediate Similarity	NPD6232	Discontinued
0.7343	Intermediate Similarity	NPD3018	Phase 2
0.7343	Intermediate Similarity	NPD2237	Approved
0.7338	Intermediate Similarity	NPD1512	Approved
0.7317	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7985	Registered
0.731	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7644	Approved
0.7289	Intermediate Similarity	NPD7074	Phase 3
0.7286	Intermediate Similarity	NPD1610	Phase 2
0.7286	Intermediate Similarity	NPD1091	Approved
0.7285	Intermediate Similarity	NPD6674	Discontinued
0.7284	Intermediate Similarity	NPD7199	Phase 2
0.7279	Intermediate Similarity	NPD5124	Phase 1
0.7279	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4626	Approved
0.7262	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7549	Discontinued
0.7256	Intermediate Similarity	NPD6166	Phase 2
0.7256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1548	Phase 1
0.7241	Intermediate Similarity	NPD7095	Approved
0.723	Intermediate Similarity	NPD6653	Approved
0.7229	Intermediate Similarity	NPD7054	Approved
0.7226	Intermediate Similarity	NPD7340	Approved
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2797	Approved
0.72	Intermediate Similarity	NPD1551	Phase 2
0.7195	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5402	Approved
0.7186	Intermediate Similarity	NPD7472	Approved
0.7183	Intermediate Similarity	NPD2982	Phase 2
0.7183	Intermediate Similarity	NPD2983	Phase 2
0.7183	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7163	Intermediate Similarity	NPD3705	Approved
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.7161	Intermediate Similarity	NPD2533	Approved
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3687	Approved
0.7134	Intermediate Similarity	NPD3686	Approved
0.7133	Intermediate Similarity	NPD3225	Approved
0.7132	Intermediate Similarity	NPD1398	Phase 1
0.7124	Intermediate Similarity	NPD3750	Approved
0.7115	Intermediate Similarity	NPD2675	Approved
0.7115	Intermediate Similarity	NPD2676	Approved
0.7113	Intermediate Similarity	NPD1608	Approved
0.7113	Intermediate Similarity	NPD2981	Phase 2
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7075	Discontinued
0.7095	Intermediate Similarity	NPD1558	Phase 1
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7078	Intermediate Similarity	NPD2219	Phase 1
0.7075	Intermediate Similarity	NPD411	Approved
0.7075	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD5691	Approved
0.7068	Intermediate Similarity	NPD290	Approved
0.7059	Intermediate Similarity	NPD5535	Approved
0.7059	Intermediate Similarity	NPD7843	Approved
0.7055	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD6599	Discontinued
0.7029	Intermediate Similarity	NPD7157	Approved
0.7027	Intermediate Similarity	NPD6233	Phase 2
0.702	Intermediate Similarity	NPD4308	Phase 3
0.7019	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2684	Approved
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7013	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4110	Phase 3
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD7251	Discontinued
0.6993	Remote Similarity	NPD9717	Approved
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6799	Approved
0.6981	Remote Similarity	NPD3111	Phase 1
0.6974	Remote Similarity	NPD6032	Approved
0.6959	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD1296	Phase 2
0.6959	Remote Similarity	NPD7808	Phase 3
0.6948	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD846	Approved
0.6947	Remote Similarity	NPD940	Approved
0.6943	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6797	Phase 2
0.6928	Remote Similarity	NPD6005	Phase 3
0.6928	Remote Similarity	NPD6002	Phase 3
0.6928	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6004	Phase 3
0.6923	Remote Similarity	NPD1535	Discovery
0.6914	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7819	Suspended
0.6909	Remote Similarity	NPD5494	Approved
0.6908	Remote Similarity	NPD7033	Discontinued
0.6903	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6559	Discontinued
0.6901	Remote Similarity	NPD7240	Approved
0.6901	Remote Similarity	NPD17	Approved
0.6899	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8651	Approved
0.6894	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2653	Approved
0.6879	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3226	Approved
0.6875	Remote Similarity	NPD1481	Phase 2
0.6875	Remote Similarity	NPD9269	Phase 2
0.6867	Remote Similarity	NPD3620	Phase 2
0.6867	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8127	Discontinued
0.6866	Remote Similarity	NPD968	Approved
0.6859	Remote Similarity	NPD6190	Approved
0.6855	Remote Similarity	NPD5403	Approved
0.6855	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1203	Approved
0.6848	Remote Similarity	NPD919	Approved
0.6846	Remote Similarity	NPD1048	Approved
0.6842	Remote Similarity	NPD6111	Discontinued
0.6839	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3021	Approved
0.6838	Remote Similarity	NPD3022	Approved
0.6832	Remote Similarity	NPD4675	Approved
0.6832	Remote Similarity	NPD4678	Approved
0.6829	Remote Similarity	NPD7768	Phase 2
0.6822	Remote Similarity	NPD844	Approved
0.6818	Remote Similarity	NPD3540	Phase 1
0.6818	Remote Similarity	NPD1375	Discontinued
0.6807	Remote Similarity	NPD6746	Phase 2
0.6807	Remote Similarity	NPD5677	Discontinued
0.6797	Remote Similarity	NPD3748	Approved
0.6795	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD9697	Approved
0.679	Remote Similarity	NPD5089	Approved
0.679	Remote Similarity	NPD5090	Approved
0.6788	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1607	Approved
0.6772	Remote Similarity	NPD4357	Discontinued
0.677	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4307	Phase 2
0.6755	Remote Similarity	NPD4140	Approved
0.6753	Remote Similarity	NPD3539	Phase 1
0.6752	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6801	Discontinued
0.6742	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3267	Approved
0.6735	Remote Similarity	NPD3266	Approved
0.6735	Remote Similarity	NPD987	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