NPASS Compound

Structure

NPC472799 OpenBabel07101718252D 30 32 0 0 1 0 0 0 0 0999 V2000 -6.0622 1.5000 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 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 1.7321 3.0000 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 -0.0000 3.0000 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 4.5000 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 0.8660 3.5000 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 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -2.5981 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 -1.7321 2.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 14 1 0 0 0 0 3 24 1 0 0 0 0 4 24 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 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 11 15 2 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 16 20 1 0 0 0 0 17 11 1 6 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 10 1 1 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 30 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 22 26 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	434.913
LogP:	6.339
LogD:	3.784
LogS:	-2.793
# Rotatable Bonds:	8
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	3.79
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025
MDCK Permeability:	1.968397009477485e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.554
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	100.13352966308594%
Volume Distribution (VD):	0.277
Pgp-substrate:	2.4764420986175537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.152
CYP2C9-inhibitor:	0.556
CYP2C9-substrate:	0.591
CYP2D6-inhibitor:	0.16
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	1.133
Half-life (T1/2):	0.521

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.901
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.524
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.106
Carcinogencity:	0.351
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC472799

Natural Product ID:	NPC472799
*Common Name:**	VVGKJYWKBQPUEW-QZTJIDSGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VVGKJYWKBQPUEW-QZTJIDSGSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-5-6-7-8-16-12-19-21(22(26)20(16)23(27)28)17-11-15(13-29-14(2)25)9-10-18(17)24(3,4)30-19/h11-12,17-18,26H,5-10,13H2,1-4H3,(H,27,28)/t17-,18-/m1/s1
SMILES:	CCCCCC1=CC2=C(C3C=C(CCC3C(O2)(C)C)COC(=O)C)C(=C1C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586110
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
Ki	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	912.0	nM	PMID[510585]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	47.0	nM	PMID[510585]

☑ 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 NPC472799 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	358
0.1-0.2	1544
0.2-0.3	3384
0.3-0.4	7724
0.4-0.5	10804
0.5-0.6	3780
0.6-0.7	5774
0.7-0.8	6497
0.8-0.85	2085
0.85-0.9	685
0.9-0.95	56
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC150928
0.9474	High Similarity	NPC474373
0.94	High Similarity	NPC217447
0.9396	High Similarity	NPC158866
0.9392	High Similarity	NPC37139
0.9342	High Similarity	NPC4547
0.9333	High Similarity	NPC478148
0.9329	High Similarity	NPC233267
0.9329	High Similarity	NPC291049
0.9272	High Similarity	NPC87708
0.9272	High Similarity	NPC273483
0.9262	High Similarity	NPC105415
0.9236	High Similarity	NPC125465
0.9211	High Similarity	NPC169990
0.9211	High Similarity	NPC210942
0.9205	High Similarity	NPC474417
0.9205	High Similarity	NPC149526
0.9205	High Similarity	NPC232645
0.9205	High Similarity	NPC133856
0.9205	High Similarity	NPC72958
0.9195	High Similarity	NPC125801
0.9184	High Similarity	NPC159721
0.9167	High Similarity	NPC473022
0.9156	High Similarity	NPC272196
0.915	High Similarity	NPC149618
0.915	High Similarity	NPC89625
0.9145	High Similarity	NPC271681
0.9128	High Similarity	NPC163846
0.9128	High Similarity	NPC225173
0.9128	High Similarity	NPC237208
0.9122	High Similarity	NPC151607
0.9122	High Similarity	NPC42540
0.911	High Similarity	NPC165172
0.9091	High Similarity	NPC146211
0.9085	High Similarity	NPC477669
0.9073	High Similarity	NPC158338
0.9073	High Similarity	NPC65589
0.9073	High Similarity	NPC288036
0.9073	High Similarity	NPC270160
0.9073	High Similarity	NPC97029
0.9073	High Similarity	NPC97028
0.9073	High Similarity	NPC237440
0.9073	High Similarity	NPC100985
0.906	High Similarity	NPC134621
0.906	High Similarity	NPC473692
0.906	High Similarity	NPC29577
0.9054	High Similarity	NPC469542
0.9054	High Similarity	NPC471731
0.9048	High Similarity	NPC1704
0.9048	High Similarity	NPC477272
0.9048	High Similarity	NPC67650
0.902	High Similarity	NPC40356
0.902	High Similarity	NPC154683
0.9013	High Similarity	NPC325983
0.9013	High Similarity	NPC202595
0.9007	High Similarity	NPC256672
0.9007	High Similarity	NPC27221
0.9007	High Similarity	NPC7025
0.9	High Similarity	NPC473132
0.9	High Similarity	NPC473023
0.9	High Similarity	NPC473135
0.9	High Similarity	NPC267509
0.9	High Similarity	NPC470676
0.8994	High Similarity	NPC472621
0.8993	High Similarity	NPC66404
0.8993	High Similarity	NPC95123
0.8986	High Similarity	NPC471733
0.8986	High Similarity	NPC469579
0.898	High Similarity	NPC472600
0.898	High Similarity	NPC472601
0.8974	High Similarity	NPC472617
0.8968	High Similarity	NPC472050
0.8968	High Similarity	NPC477674
0.8961	High Similarity	NPC329844
0.8954	High Similarity	NPC477672
0.8954	High Similarity	NPC477673
0.8947	High Similarity	NPC4423
0.8947	High Similarity	NPC77325
0.8947	High Similarity	NPC329933
0.894	High Similarity	NPC34802
0.894	High Similarity	NPC22005
0.894	High Similarity	NPC7943
0.894	High Similarity	NPC123202
0.8938	High Similarity	NPC472622
0.8933	High Similarity	NPC470674
0.8933	High Similarity	NPC470673
0.8933	High Similarity	NPC32470
0.8933	High Similarity	NPC117716
0.8933	High Similarity	NPC312789
0.8933	High Similarity	NPC75694
0.8933	High Similarity	NPC271288
0.8926	High Similarity	NPC310340
0.8926	High Similarity	NPC472006
0.8926	High Similarity	NPC51106
0.8919	High Similarity	NPC53649
0.8919	High Similarity	NPC472605
0.8919	High Similarity	NPC472604
0.8919	High Similarity	NPC472603
0.8917	High Similarity	NPC143050
0.8917	High Similarity	NPC472618
0.8912	High Similarity	NPC474487
0.8912	High Similarity	NPC470671
0.8912	High Similarity	NPC470672
0.8912	High Similarity	NPC88269
0.8912	High Similarity	NPC474504
0.8904	High Similarity	NPC135837
0.8904	High Similarity	NPC194579
0.8896	High Similarity	NPC175978
0.8896	High Similarity	NPC167903
0.8889	High Similarity	NPC119929
0.8889	High Similarity	NPC180351
0.8889	High Similarity	NPC309979
0.8889	High Similarity	NPC60413
0.8889	High Similarity	NPC307780
0.8882	High Similarity	NPC471642
0.8882	High Similarity	NPC240253
0.8882	High Similarity	NPC145467
0.8882	High Similarity	NPC471641
0.8882	High Similarity	NPC240622
0.8882	High Similarity	NPC472619
0.8874	High Similarity	NPC24136
0.8874	High Similarity	NPC290133
0.8874	High Similarity	NPC196114
0.8874	High Similarity	NPC285630
0.8874	High Similarity	NPC187282
0.8874	High Similarity	NPC260946
0.8874	High Similarity	NPC477955
0.8874	High Similarity	NPC473927
0.8874	High Similarity	NPC127059
0.8867	High Similarity	NPC5990
0.8859	High Similarity	NPC105648
0.8859	High Similarity	NPC474385
0.8859	High Similarity	NPC250755
0.8854	High Similarity	NPC239118
0.8854	High Similarity	NPC85121
0.8854	High Similarity	NPC470339
0.8844	High Similarity	NPC472602
0.8839	High Similarity	NPC135522
0.8839	High Similarity	NPC192189
0.8836	High Similarity	NPC158481
0.8831	High Similarity	NPC78835
0.8831	High Similarity	NPC209142
0.8831	High Similarity	NPC312549
0.8831	High Similarity	NPC470675
0.8831	High Similarity	NPC309512
0.8831	High Similarity	NPC316960
0.8831	High Similarity	NPC204561
0.8831	High Similarity	NPC473131
0.8831	High Similarity	NPC148945
0.8831	High Similarity	NPC317715
0.8827	High Similarity	NPC477573
0.8827	High Similarity	NPC477572
0.8827	High Similarity	NPC477571
0.8824	High Similarity	NPC65775
0.8824	High Similarity	NPC104236
0.8824	High Similarity	NPC6923
0.8824	High Similarity	NPC164205
0.8824	High Similarity	NPC473016
0.8824	High Similarity	NPC10027
0.882	High Similarity	NPC76647
0.8816	High Similarity	NPC137296
0.8816	High Similarity	NPC474108
0.8816	High Similarity	NPC12305
0.8816	High Similarity	NPC177995
0.8816	High Similarity	NPC8817
0.8816	High Similarity	NPC308200
0.8816	High Similarity	NPC471734
0.8816	High Similarity	NPC142863
0.8812	High Similarity	NPC314653
0.8812	High Similarity	NPC316262
0.8808	High Similarity	NPC131568
0.8808	High Similarity	NPC235217
0.8808	High Similarity	NPC131579
0.8808	High Similarity	NPC473014
0.88	High Similarity	NPC472610
0.88	High Similarity	NPC297600
0.88	High Similarity	NPC84266
0.88	High Similarity	NPC471639
0.88	High Similarity	NPC471643
0.8797	High Similarity	NPC472055
0.8797	High Similarity	NPC470810
0.8792	High Similarity	NPC471587
0.8792	High Similarity	NPC475730
0.8792	High Similarity	NPC37530
0.8792	High Similarity	NPC275734
0.8792	High Similarity	NPC16455
0.8792	High Similarity	NPC307990
0.8792	High Similarity	NPC220106
0.879	High Similarity	NPC158542
0.879	High Similarity	NPC281137
0.879	High Similarity	NPC282390
0.879	High Similarity	NPC246466
0.879	High Similarity	NPC201127
0.879	High Similarity	NPC263483
0.8784	High Similarity	NPC131130
0.8782	High Similarity	NPC477671
0.8782	High Similarity	NPC477687
0.878	High Similarity	NPC294149
0.8776	High Similarity	NPC156910
0.8776	High Similarity	NPC70380

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 NPC472799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	993
0.2-0.3	1701
0.3-0.4	2504
0.4-0.5	1915
0.5-0.6	1084
0.6-0.7	423
0.7-0.8	174
0.8-0.85	27
0.85-0.9	6
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD7819	Suspended
0.8933	High Similarity	NPD2532	Approved
0.8933	High Similarity	NPD2534	Approved
0.8933	High Similarity	NPD2533	Approved
0.8912	High Similarity	NPD970	Clinical (unspecified phase)
0.8792	High Similarity	NPD6398	Clinical (unspecified phase)
0.8625	High Similarity	NPD6959	Discontinued
0.8553	High Similarity	NPD7075	Discontinued
0.8544	High Similarity	NPD8443	Clinical (unspecified phase)
0.8528	High Similarity	NPD7473	Discontinued
0.8481	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8442	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6100	Approved
0.84	Intermediate Similarity	NPD6099	Approved
0.8375	Intermediate Similarity	NPD7768	Phase 2
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5710	Approved
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5711	Approved
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8301	Intermediate Similarity	NPD3750	Approved
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8242	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD3749	Approved
0.8205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1934	Approved
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8158	Intermediate Similarity	NPD1551	Phase 2
0.8117	Intermediate Similarity	NPD2800	Approved
0.8113	Intermediate Similarity	NPD3226	Approved
0.8105	Intermediate Similarity	NPD2346	Discontinued
0.8092	Intermediate Similarity	NPD1510	Phase 2
0.8079	Intermediate Similarity	NPD1607	Approved
0.8079	Intermediate Similarity	NPD6651	Approved
0.8075	Intermediate Similarity	NPD6801	Discontinued
0.8063	Intermediate Similarity	NPD4380	Phase 2
0.8054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8039	Intermediate Similarity	NPD2796	Approved
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7974	Intermediate Similarity	NPD3748	Approved
0.7974	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6559	Discontinued
0.7947	Intermediate Similarity	NPD1240	Approved
0.7945	Intermediate Similarity	NPD4749	Approved
0.7914	Intermediate Similarity	NPD2801	Approved
0.7911	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD5494	Approved
0.7885	Intermediate Similarity	NPD1243	Approved
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4625	Phase 3
0.7862	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7853	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7074	Phase 3
0.7834	Intermediate Similarity	NPD4628	Phase 3
0.7818	Intermediate Similarity	NPD3882	Suspended
0.7812	Intermediate Similarity	NPD1512	Approved
0.7811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6166	Phase 2
0.7811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1465	Phase 2
0.7799	Intermediate Similarity	NPD7390	Discontinued
0.7798	Intermediate Similarity	NPD7229	Phase 3
0.7778	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD920	Approved
0.7759	Intermediate Similarity	NPD8312	Approved
0.7759	Intermediate Similarity	NPD8313	Approved
0.7736	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7472	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5408	Approved
0.7692	Intermediate Similarity	NPD5405	Approved
0.7692	Intermediate Similarity	NPD5406	Approved
0.7692	Intermediate Similarity	NPD5404	Approved
0.7688	Intermediate Similarity	NPD5953	Discontinued
0.7674	Intermediate Similarity	NPD7286	Phase 2
0.7644	Intermediate Similarity	NPD7251	Discontinued
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8150	Discontinued
0.7619	Intermediate Similarity	NPD919	Approved
0.7616	Intermediate Similarity	NPD3818	Discontinued
0.761	Intermediate Similarity	NPD7003	Approved
0.76	Intermediate Similarity	NPD7808	Phase 3
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6797	Phase 2
0.7582	Intermediate Similarity	NPD411	Approved
0.7582	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4908	Phase 1
0.7566	Intermediate Similarity	NPD6832	Phase 2
0.7561	Intermediate Similarity	NPD7458	Discontinued
0.7551	Intermediate Similarity	NPD4626	Approved
0.755	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD230	Phase 1
0.7546	Intermediate Similarity	NPD5403	Approved
0.7545	Intermediate Similarity	NPD5402	Approved
0.7542	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1283	Approved
0.753	Intermediate Similarity	NPD37	Approved
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7517	Intermediate Similarity	NPD1608	Approved
0.7517	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.7514	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4966	Approved
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6273	Approved
0.7484	Intermediate Similarity	NPD4060	Phase 1
0.7483	Intermediate Similarity	NPD5691	Approved
0.7483	Intermediate Similarity	NPD2797	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.745	Intermediate Similarity	NPD422	Phase 1
0.745	Intermediate Similarity	NPD1610	Phase 2
0.7442	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4288	Approved
0.7435	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7783	Phase 2
0.7433	Intermediate Similarity	NPD7435	Discontinued
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7423	Intermediate Similarity	NPD5401	Approved
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7414	Intermediate Similarity	NPD7228	Approved
0.7372	Intermediate Similarity	NPD2979	Phase 3
0.7366	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD1281	Approved
0.7325	Intermediate Similarity	NPD447	Suspended
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD17	Approved
0.7315	Intermediate Similarity	NPD1778	Approved
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7312	Intermediate Similarity	NPD2344	Approved
0.7297	Intermediate Similarity	NPD9545	Approved
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7278	Intermediate Similarity	NPD5761	Phase 2
0.7278	Intermediate Similarity	NPD5760	Phase 2
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.7261	Intermediate Similarity	NPD4307	Phase 2
0.7256	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4287	Approved
0.725	Intermediate Similarity	NPD2438	Suspended
0.725	Intermediate Similarity	NPD4476	Approved
0.725	Intermediate Similarity	NPD4477	Approved
0.7249	Intermediate Similarity	NPD7698	Approved
0.7249	Intermediate Similarity	NPD7696	Phase 3
0.7249	Intermediate Similarity	NPD7697	Approved
0.7229	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1247	Approved
0.7219	Intermediate Similarity	NPD1201	Approved
0.7216	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7870	Phase 2
0.7211	Intermediate Similarity	NPD7871	Phase 2
0.7208	Intermediate Similarity	NPD2798	Approved
0.7205	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6005	Phase 3
0.7205	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6002	Phase 3
0.7205	Intermediate Similarity	NPD6004	Phase 3
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7874	Approved
0.7197	Intermediate Similarity	NPD8032	Phase 2
0.719	Intermediate Similarity	NPD6696	Suspended
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7162	Intermediate Similarity	NPD9493	Approved
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD943	Approved
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3926	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data