NPASS Compound

Structure

NPC472798 OpenBabel07101718252D 24 27 0 0 1 0 0 0 0 0999 V2000 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -4.3660 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 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 -1.7321 -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 1.7321 -4.0000 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 2 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 -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 2 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 0.0000 -1.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 20 1 0 0 0 0 3 20 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 13 1 0 0 0 0 9 10 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 14 9 1 6 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 1 0 0 0 17 19 1 0 0 0 0 19 21 1 1 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 21 4 1 6 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.22
Volume:	356.008
LogP:	6.521
LogD:	5.067
LogS:	-3.038
# Rotatable Bonds:	4
TPSA:	41.99
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	3.963
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.806
MDCK Permeability:	1.6496740499860607e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.468
Plasma Protein Binding (PPB):	99.3114242553711%
Volume Distribution (VD):	2.743
Pgp-substrate:	1.7764683961868286%

ADMET: Metabolism

CYP1A2-inhibitor:	0.184
CYP1A2-substrate:	0.862
CYP2C19-inhibitor:	0.45
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.519
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	3.867
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.735
Drug-inuced Liver Injury (DILI):	0.258
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.723
Carcinogencity:	0.049
Eye Corrosion:	0.044
Eye Irritation:	0.771
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC472798

Natural Product ID:	NPC472798
*Common Name:**	VSQGBNUBIDZRPJ-BWZSVYRMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VSQGBNUBIDZRPJ-BWZSVYRMSA-N
Standard InCHI:	InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-20(2,3)14-9-10-21(4)19(24-21)17(14)18/h11-12,14,17,19,22H,5-10H2,1-4H3/t14-,17-,19+,21-/m1/s1
SMILES:	CCCCCC1=CC(=C2C3C(CCC4(C3O4)C)C(OC2=C1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586109
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
Others	15

Activity Type	# Activity
Individual Protein	2
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	335.0	nM	PMID[566602]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	224.0	nM	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	T	=	4.58	degrees C	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	T	=	3.11	degrees C	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	T	=	3.75	degrees C	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	49.39	%	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	35.89	%	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	36.98	%	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	50.37	%	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	82.71	%	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	MPE	=	16.25	%	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	TIME	=	0.007639	hr	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	TIME	=	0.002444	hr	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	TIME	=	0.006611	hr	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	380.3	n.a.	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	291.2	n.a.	PMID[566602]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	213.4	n.a.	PMID[566602]

☑ 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 NPC472798 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	430
0.1-0.2	1592
0.2-0.3	3637
0.3-0.4	9881
0.4-0.5	9229
0.5-0.6	4326
0.6-0.7	9357
0.7-0.8	3786
0.8-0.85	382
0.85-0.9	72
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC472797
0.9449	High Similarity	NPC472796
0.9449	High Similarity	NPC472795
0.9389	High Similarity	NPC472800
0.937	High Similarity	NPC211179
0.937	High Similarity	NPC38604
0.9154	High Similarity	NPC160623
0.9147	High Similarity	NPC222108
0.9147	High Similarity	NPC96719
0.9127	High Similarity	NPC96940
0.9098	High Similarity	NPC327735
0.9098	High Similarity	NPC126101
0.9008	High Similarity	NPC472590
0.9	High Similarity	NPC16577
0.8992	High Similarity	NPC473134
0.8984	High Similarity	NPC131397
0.8984	High Similarity	NPC293801
0.8984	High Similarity	NPC476254
0.8947	High Similarity	NPC473107
0.8939	High Similarity	NPC13005
0.8931	High Similarity	NPC27187
0.8931	High Similarity	NPC470225
0.8923	High Similarity	NPC53986
0.8923	High Similarity	NPC38664
0.8915	High Similarity	NPC26879
0.8915	High Similarity	NPC283049
0.8915	High Similarity	NPC50315
0.8915	High Similarity	NPC230479
0.8872	High Similarity	NPC469610
0.8864	High Similarity	NPC129784
0.8864	High Similarity	NPC280653
0.8864	High Similarity	NPC164574
0.8864	High Similarity	NPC293203
0.8864	High Similarity	NPC196765
0.8864	High Similarity	NPC118683
0.8864	High Similarity	NPC12875
0.8864	High Similarity	NPC244888
0.8864	High Similarity	NPC228369
0.8864	High Similarity	NPC118114
0.8864	High Similarity	NPC476166
0.8864	High Similarity	NPC300875
0.8864	High Similarity	NPC206224
0.8864	High Similarity	NPC207892
0.8864	High Similarity	NPC129106
0.8864	High Similarity	NPC211413
0.8864	High Similarity	NPC17343
0.8864	High Similarity	NPC68205
0.8864	High Similarity	NPC164804
0.8864	High Similarity	NPC181497
0.8864	High Similarity	NPC268917
0.8864	High Similarity	NPC271945
0.8864	High Similarity	NPC236014
0.8864	High Similarity	NPC150011
0.8855	High Similarity	NPC93962
0.8846	High Similarity	NPC46978
0.8832	High Similarity	NPC265075
0.8806	High Similarity	NPC223008
0.8806	High Similarity	NPC97834
0.8806	High Similarity	NPC198154
0.8806	High Similarity	NPC115335
0.8806	High Similarity	NPC225696
0.8806	High Similarity	NPC296915
0.8797	High Similarity	NPC469611
0.8786	High Similarity	NPC471608
0.8779	High Similarity	NPC39064
0.8779	High Similarity	NPC274717
0.8779	High Similarity	NPC47283
0.876	High Similarity	NPC106914
0.876	High Similarity	NPC86502
0.876	High Similarity	NPC246648
0.876	High Similarity	NPC134195
0.876	High Similarity	NPC270030
0.876	High Similarity	NPC197351
0.875	High Similarity	NPC120638
0.875	High Similarity	NPC36016
0.875	High Similarity	NPC100099
0.875	High Similarity	NPC57199
0.874	High Similarity	NPC218753
0.8731	High Similarity	NPC77196
0.8731	High Similarity	NPC177712
0.8731	High Similarity	NPC24913
0.8731	High Similarity	NPC85435
0.8722	High Similarity	NPC8899
0.8722	High Similarity	NPC162801
0.8714	High Similarity	NPC90645
0.8714	High Similarity	NPC469557
0.8714	High Similarity	NPC472457
0.8702	High Similarity	NPC149796
0.8692	High Similarity	NPC105031
0.8692	High Similarity	NPC188022
0.8692	High Similarity	NPC103420
0.8692	High Similarity	NPC285040
0.8692	High Similarity	NPC102540
0.8692	High Similarity	NPC17809
0.8686	High Similarity	NPC32630
0.8682	High Similarity	NPC38761
0.8682	High Similarity	NPC76465
0.8676	High Similarity	NPC141717
0.8676	High Similarity	NPC234952
0.8672	High Similarity	NPC212965
0.8672	High Similarity	NPC54972
0.8672	High Similarity	NPC193364
0.8667	High Similarity	NPC117048
0.8667	High Similarity	NPC124085
0.8652	High Similarity	NPC233980
0.8647	High Similarity	NPC196193
0.8643	High Similarity	NPC473845
0.8636	High Similarity	NPC87224
0.8636	High Similarity	NPC222572
0.8626	High Similarity	NPC262573
0.8626	High Similarity	NPC82299
0.8626	High Similarity	NPC276212
0.8626	High Similarity	NPC170485
0.8626	High Similarity	NPC471215
0.8613	High Similarity	NPC474687
0.8605	High Similarity	NPC77789
0.8605	High Similarity	NPC74137
0.8605	High Similarity	NPC18128
0.8603	High Similarity	NPC473413
0.8603	High Similarity	NPC151224
0.8593	High Similarity	NPC11060
0.8593	High Similarity	NPC92805
0.8592	High Similarity	NPC474397
0.8583	High Similarity	NPC184302
0.8583	High Similarity	NPC85895
0.8583	High Similarity	NPC137294
0.8582	High Similarity	NPC103799
0.8571	High Similarity	NPC134360
0.8561	High Similarity	NPC473221
0.8561	High Similarity	NPC71046
0.8551	High Similarity	NPC471388
0.8551	High Similarity	NPC70682
0.8551	High Similarity	NPC475836
0.8551	High Similarity	NPC260741
0.855	High Similarity	NPC105718
0.855	High Similarity	NPC278955
0.8542	High Similarity	NPC158784
0.854	High Similarity	NPC230734
0.854	High Similarity	NPC18189
0.854	High Similarity	NPC173660
0.854	High Similarity	NPC262585
0.854	High Similarity	NPC162659
0.854	High Similarity	NPC3049
0.854	High Similarity	NPC227503
0.854	High Similarity	NPC265433
0.854	High Similarity	NPC470802
0.854	High Similarity	NPC248727
0.854	High Similarity	NPC270456
0.854	High Similarity	NPC474639
0.854	High Similarity	NPC20829
0.8538	High Similarity	NPC261992
0.8531	High Similarity	NPC212142
0.8516	High Similarity	NPC93398
0.8516	High Similarity	NPC282255
0.8516	High Similarity	NPC258979
0.8516	High Similarity	NPC8283
0.8516	High Similarity	NPC3239
0.8511	High Similarity	NPC473108
0.8511	High Similarity	NPC469795
0.8507	High Similarity	NPC470727
0.8504	High Similarity	NPC190514
0.85	High Similarity	NPC59841
0.85	High Similarity	NPC475891
0.85	High Similarity	NPC2613
0.85	High Similarity	NPC204347
0.8496	Intermediate Similarity	NPC38017
0.8496	Intermediate Similarity	NPC215300
0.8489	Intermediate Similarity	NPC27495
0.8489	Intermediate Similarity	NPC309124
0.8489	Intermediate Similarity	NPC259519
0.8489	Intermediate Similarity	NPC184797
0.8485	Intermediate Similarity	NPC470724
0.8483	Intermediate Similarity	NPC302915
0.8483	Intermediate Similarity	NPC2745
0.8478	Intermediate Similarity	NPC134260
0.8473	Intermediate Similarity	NPC256015
0.8473	Intermediate Similarity	NPC294156
0.8473	Intermediate Similarity	NPC138248
0.8473	Intermediate Similarity	NPC228503
0.8467	Intermediate Similarity	NPC94750
0.8467	Intermediate Similarity	NPC234333
0.8467	Intermediate Similarity	NPC112939
0.8467	Intermediate Similarity	NPC195022
0.8467	Intermediate Similarity	NPC121812
0.8467	Intermediate Similarity	NPC260898
0.8467	Intermediate Similarity	NPC61946
0.8467	Intermediate Similarity	NPC112246
0.8467	Intermediate Similarity	NPC47398
0.8467	Intermediate Similarity	NPC164787
0.8467	Intermediate Similarity	NPC11727
0.8467	Intermediate Similarity	NPC327382
0.8467	Intermediate Similarity	NPC15109
0.8467	Intermediate Similarity	NPC125579
0.8467	Intermediate Similarity	NPC470356
0.8467	Intermediate Similarity	NPC474206
0.8462	Intermediate Similarity	NPC188997
0.845	Intermediate Similarity	NPC102639
0.844	Intermediate Similarity	NPC47633
0.844	Intermediate Similarity	NPC85264
0.844	Intermediate Similarity	NPC102044

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 NPC472798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	903
0.2-0.3	1758
0.3-0.4	2759
0.4-0.5	1691
0.5-0.6	1013
0.6-0.7	579
0.7-0.8	77
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9127	High Similarity	NPD4749	Approved
0.9077	High Similarity	NPD6410	Clinical (unspecified phase)
0.9	High Similarity	NPD4625	Phase 3
0.8672	High Similarity	NPD1610	Phase 2
0.8647	High Similarity	NPD4907	Clinical (unspecified phase)
0.8636	High Similarity	NPD4908	Phase 1
0.8485	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD6099	Approved
0.8478	Intermediate Similarity	NPD6100	Approved
0.8421	Intermediate Similarity	NPD2861	Phase 2
0.8248	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD1613	Approved
0.8217	Intermediate Similarity	NPD1548	Phase 1
0.8148	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD6696	Suspended
0.8042	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD6671	Approved
0.7937	Intermediate Similarity	NPD4750	Phase 3
0.7923	Intermediate Similarity	NPD7340	Approved
0.7899	Intermediate Similarity	NPD3027	Phase 3
0.7829	Intermediate Similarity	NPD1398	Phase 1
0.7801	Intermediate Similarity	NPD5124	Phase 1
0.7801	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2238	Phase 2
0.7671	Intermediate Similarity	NPD6674	Discontinued
0.7643	Intermediate Similarity	NPD6959	Discontinued
0.7606	Intermediate Similarity	NPD4060	Phase 1
0.7597	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD5327	Phase 3
0.7591	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD422	Phase 1
0.7552	Intermediate Similarity	NPD5735	Approved
0.7533	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6353	Approved
0.75	Intermediate Similarity	NPD3892	Phase 2
0.75	Intermediate Similarity	NPD4097	Suspended
0.7483	Intermediate Similarity	NPD4140	Approved
0.7468	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7213	Phase 3
0.7467	Intermediate Similarity	NPD7212	Phase 2
0.7465	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1091	Approved
0.7436	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4626	Approved
0.7419	Intermediate Similarity	NPD1934	Approved
0.7419	Intermediate Similarity	NPD37	Approved
0.7417	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7447	Phase 1
0.7415	Intermediate Similarity	NPD5762	Approved
0.7415	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5763	Approved
0.7415	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6234	Discontinued
0.7391	Intermediate Similarity	NPD2232	Approved
0.7391	Intermediate Similarity	NPD2230	Approved
0.7391	Intermediate Similarity	NPD2233	Approved
0.7389	Intermediate Similarity	NPD4965	Approved
0.7389	Intermediate Similarity	NPD4966	Approved
0.7389	Intermediate Similarity	NPD4967	Phase 2
0.7383	Intermediate Similarity	NPD7466	Approved
0.7372	Intermediate Similarity	NPD7819	Suspended
0.7365	Intermediate Similarity	NPD1549	Phase 2
0.7362	Intermediate Similarity	NPD5844	Phase 1
0.7361	Intermediate Similarity	NPD3620	Phase 2
0.7361	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5691	Approved
0.7305	Intermediate Similarity	NPD6584	Phase 3
0.7305	Intermediate Similarity	NPD4624	Approved
0.7303	Intermediate Similarity	NPD2532	Approved
0.7303	Intermediate Similarity	NPD2534	Approved
0.7303	Intermediate Similarity	NPD2533	Approved
0.7299	Intermediate Similarity	NPD1778	Approved
0.7287	Intermediate Similarity	NPD968	Approved
0.7286	Intermediate Similarity	NPD8651	Approved
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3750	Approved
0.7266	Intermediate Similarity	NPD2235	Phase 2
0.7266	Intermediate Similarity	NPD2231	Phase 2
0.7248	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD940	Approved
0.7244	Intermediate Similarity	NPD846	Approved
0.7234	Intermediate Similarity	NPD2797	Approved
0.7231	Intermediate Similarity	NPD290	Approved
0.723	Intermediate Similarity	NPD2796	Approved
0.7226	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD7635	Approved
0.7211	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4536	Approved
0.7211	Intermediate Similarity	NPD4538	Approved
0.7211	Intermediate Similarity	NPD2200	Suspended
0.7206	Intermediate Similarity	NPD7644	Approved
0.72	Intermediate Similarity	NPD1652	Phase 2
0.7195	Intermediate Similarity	NPD7228	Approved
0.7194	Intermediate Similarity	NPD1611	Approved
0.7179	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD2684	Approved
0.7162	Intermediate Similarity	NPD7033	Discontinued
0.7162	Intermediate Similarity	NPD5960	Phase 3
0.7161	Intermediate Similarity	NPD1653	Approved
0.716	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7153	Intermediate Similarity	NPD3091	Approved
0.7152	Intermediate Similarity	NPD5929	Approved
0.7143	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD6090	Discontinued
0.7133	Intermediate Similarity	NPD1712	Approved
0.7133	Intermediate Similarity	NPD7037	Approved
0.7133	Intermediate Similarity	NPD3018	Phase 2
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7125	Intermediate Similarity	NPD7075	Discontinued
0.7124	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7041	Phase 2
0.7124	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3496	Discontinued
0.7114	Intermediate Similarity	NPD1551	Phase 2
0.7113	Intermediate Similarity	NPD3094	Phase 2
0.7105	Intermediate Similarity	NPD2677	Approved
0.7103	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5585	Approved
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7092	Intermediate Similarity	NPD6583	Phase 3
0.7092	Intermediate Similarity	NPD6582	Phase 2
0.7078	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6166	Phase 2
0.7073	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3092	Approved
0.7067	Intermediate Similarity	NPD6004	Phase 3
0.7067	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6005	Phase 3
0.7067	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6002	Phase 3
0.7063	Intermediate Similarity	NPD7768	Phase 2
0.7063	Intermediate Similarity	NPD288	Approved
0.7059	Intermediate Similarity	NPD5058	Phase 3
0.7059	Intermediate Similarity	NPD7157	Approved
0.7055	Intermediate Similarity	NPD6232	Discontinued
0.7047	Intermediate Similarity	NPD5588	Approved
0.7047	Intermediate Similarity	NPD1510	Phase 2
0.7044	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2801	Approved
0.7042	Intermediate Similarity	NPD1283	Approved
0.7041	Intermediate Similarity	NPD4578	Approved
0.7041	Intermediate Similarity	NPD4577	Approved
0.7037	Intermediate Similarity	NPD5494	Approved
0.7037	Intermediate Similarity	NPD5283	Phase 1
0.7031	Intermediate Similarity	NPD1242	Phase 1
0.703	Intermediate Similarity	NPD7473	Discontinued
0.7029	Intermediate Similarity	NPD7741	Discontinued
0.7027	Intermediate Similarity	NPD2157	Approved
0.7025	Intermediate Similarity	NPD7411	Suspended
0.702	Intermediate Similarity	NPD2424	Discontinued
0.7019	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2237	Approved
0.7013	Intermediate Similarity	NPD1511	Approved
0.7007	Intermediate Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD7199	Phase 2
0.6988	Remote Similarity	NPD3751	Discontinued
0.6986	Remote Similarity	NPD7985	Registered
0.6986	Remote Similarity	NPD3268	Approved
0.6984	Remote Similarity	NPD844	Approved
0.6978	Remote Similarity	NPD3444	Approved
0.6978	Remote Similarity	NPD1651	Approved
0.6978	Remote Similarity	NPD3445	Approved
0.6978	Remote Similarity	NPD3443	Approved
0.6974	Remote Similarity	NPD5177	Phase 3
0.6972	Remote Similarity	NPD2983	Phase 2
0.6972	Remote Similarity	NPD2982	Phase 2
0.697	Remote Similarity	NPD2342	Discontinued
0.6968	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7843	Approved
0.6959	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD2346	Discontinued
0.6953	Remote Similarity	NPD3020	Approved
0.695	Remote Similarity	NPD3705	Approved
0.6948	Remote Similarity	NPD6667	Approved
0.6948	Remote Similarity	NPD6815	Approved
0.6948	Remote Similarity	NPD6666	Approved
0.6944	Remote Similarity	NPD3690	Phase 2
0.6944	Remote Similarity	NPD3691	Phase 2
0.6941	Remote Similarity	NPD7312	Approved
0.6941	Remote Similarity	NPD7311	Approved
0.6941	Remote Similarity	NPD7310	Approved
0.6941	Remote Similarity	NPD7313	Approved
0.6933	Remote Similarity	NPD6746	Phase 2
0.6933	Remote Similarity	NPD3748	Approved
0.6933	Remote Similarity	NPD4108	Discontinued
0.6929	Remote Similarity	NPD2667	Approved
0.6929	Remote Similarity	NPD17	Approved
0.6929	Remote Similarity	NPD5125	Phase 3
0.6929	Remote Similarity	NPD2668	Approved
0.6929	Remote Similarity	NPD5126	Approved
0.6928	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD5261	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data