NPASS Compound

Structure

CID232708 OpenBabel06191716032D 31 32 0 0 0 0 0 0 0 0999 V2000 -4.1989 -2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7183 1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 -1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0387 -1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7183 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0387 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8785 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0387 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8785 -0.4848 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 -5.8785 -2.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5580 0.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 2.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 -0.9697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0387 1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 2.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 -0.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7183 -0.9697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -0.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 6 22 2 0 0 0 0 7 13 1 0 0 0 0 7 23 2 0 0 0 0 8 14 1 0 0 0 0 8 24 2 0 0 0 0 9 15 1 0 0 0 0 9 25 2 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 2 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 21 2 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.11
Volume:	416.197
LogP:	3.519
LogD:	0.975
LogS:	-2.502
# Rotatable Bonds:	6
TPSA:	189.66
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	2.813
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-6.158
MDCK Permeability:	7.9352903412655e-06
Pgp-inhibitor:	0.846
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.792
20% Bioavailability (F20%):	0.696
30% Bioavailability (F30%):	0.598

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	96.51102447509766%
Volume Distribution (VD):	0.534
Pgp-substrate:	4.193136692047119%

ADMET: Metabolism

CYP1A2-inhibitor:	0.27
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.735
CYP2C9-substrate:	0.253
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	1.741
Half-life (T1/2):	0.339

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.183
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.919
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.825
Respiratory Toxicity:	0.113

Download Data

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

Natural Product: NPC232708

Natural Product ID:	NPC232708
*Common Name:**	Methylene-Bis-(3,5-Diacetyl-2,4,6-Trihydroxy Benzene)
IUPAC Name:	1-[3-acetyl-5-[(3,5-diacetyl-2,4,6-trihydroxyphenyl)methyl]-2,4,6-trihydroxyphenyl]ethanone
Synonyms:
Standard InCHIKey:	OQALYYVWRAPBOC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O10/c1-6(22)12-16(26)10(17(27)13(7(2)23)20(12)30)5-11-18(28)14(8(3)24)21(31)15(9(4)25)19(11)29/h26-31H,5H2,1-4H3
SMILES:	CC(=O)c1c(O)c(Cc2c(O)c(C(=O)C)c(c(c2O)C(=O)C)O)c(c(c1O)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598590
PubChem CID:	21119957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043412]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	collected at 50-60 m depth in the Kosterfjord on the Swedish west coast	2001-MAR	PMID[15043412]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067154]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271554]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222779]
NPO16974	Lonchocarpus heptaphyllus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14396	Hibiscus moscheutos	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16974	Lonchocarpus heptaphyllus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17387	Dentaria pinnata	n.a.	n.a.	n.a.	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
Others	7

Activity Type	# Activity
Cell Line	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	MNTD	=	0.23	uM	PMID[502854]
NPT369	Cell Line	ACHN	Homo sapiens	GI	=	46.0	%	PMID[502855]
NPT461	Cell Line	PANC-1	Homo sapiens	GI	=	22.0	%	PMID[502855]
NPT1307	Cell Line	Calu-1	Homo sapiens	GI	=	39.0	%	PMID[502855]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI	=	0.0	%	PMID[502855]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	8.0	%	PMID[502855]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	0.0	%	PMID[502854]

☑ 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 NPC232708 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	310
0.1-0.2	1592
0.2-0.3	4697
0.3-0.4	13158
0.4-0.5	6860
0.5-0.6	6591
0.6-0.7	6063
0.7-0.8	2939
0.8-0.85	364
0.85-0.9	94
0.9-0.95	27
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9826	High Similarity	NPC229649
0.9328	High Similarity	NPC66252
0.918	High Similarity	NPC267846
0.912	High Similarity	NPC275504
0.9106	High Similarity	NPC100067
0.9106	High Similarity	NPC30501
0.9106	High Similarity	NPC105157
0.9106	High Similarity	NPC23126
0.9106	High Similarity	NPC98254
0.9106	High Similarity	NPC162612
0.9106	High Similarity	NPC169250
0.9106	High Similarity	NPC190043
0.9106	High Similarity	NPC266689
0.9106	High Similarity	NPC103356
0.9106	High Similarity	NPC116513
0.9106	High Similarity	NPC72158
0.9098	High Similarity	NPC290466
0.9091	High Similarity	NPC306288
0.9083	High Similarity	NPC226275
0.904	High Similarity	NPC186628
0.9032	High Similarity	NPC473017
0.9032	High Similarity	NPC221777
0.9032	High Similarity	NPC21305
0.9024	High Similarity	NPC328983
0.9024	High Similarity	NPC62952
0.9008	High Similarity	NPC218333
0.9008	High Similarity	NPC91105
0.8968	High Similarity	NPC279566
0.896	High Similarity	NPC474998
0.8952	High Similarity	NPC316625
0.8952	High Similarity	NPC329205
0.8934	High Similarity	NPC65761
0.8934	High Similarity	NPC472029
0.8926	High Similarity	NPC215392
0.8843	High Similarity	NPC149246
0.8828	High Similarity	NPC215875
0.8828	High Similarity	NPC15834
0.8819	High Similarity	NPC475042
0.881	High Similarity	NPC476119
0.881	High Similarity	NPC73203
0.879	High Similarity	NPC475733
0.877	High Similarity	NPC196976
0.877	High Similarity	NPC303737
0.877	High Similarity	NPC242895
0.876	High Similarity	NPC16197
0.873	High Similarity	NPC470981
0.8699	High Similarity	NPC32032
0.8699	High Similarity	NPC309765
0.8699	High Similarity	NPC133909
0.8682	High Similarity	NPC139074
0.8682	High Similarity	NPC213485
0.8682	High Similarity	NPC40524
0.8618	High Similarity	NPC224273
0.8618	High Similarity	NPC156139
0.8618	High Similarity	NPC19174
0.8618	High Similarity	NPC115159
0.8618	High Similarity	NPC73532
0.8618	High Similarity	NPC45438
0.8618	High Similarity	NPC143427
0.8618	High Similarity	NPC267552
0.8615	High Similarity	NPC166480
0.8615	High Similarity	NPC475088
0.8615	High Similarity	NPC282780
0.8607	High Similarity	NPC294037
0.8605	High Similarity	NPC175738
0.8595	High Similarity	NPC209486
0.8595	High Similarity	NPC40649
0.8594	High Similarity	NPC21378
0.8594	High Similarity	NPC470987
0.8583	High Similarity	NPC164894
0.8583	High Similarity	NPC475553
0.855	High Similarity	NPC103842
0.855	High Similarity	NPC283590
0.855	High Similarity	NPC70859
0.855	High Similarity	NPC61153
0.855	High Similarity	NPC470210
0.855	High Similarity	NPC130899
0.8538	High Similarity	NPC285054
0.8537	High Similarity	NPC297186
0.8537	High Similarity	NPC146642
0.8525	High Similarity	NPC195262
0.8525	High Similarity	NPC188814
0.8516	High Similarity	NPC92624
0.8496	Intermediate Similarity	NPC255801
0.8496	Intermediate Similarity	NPC322301
0.8492	Intermediate Similarity	NPC10926
0.8485	Intermediate Similarity	NPC156092
0.8485	Intermediate Similarity	NPC131039
0.8485	Intermediate Similarity	NPC264112
0.8485	Intermediate Similarity	NPC65005
0.8485	Intermediate Similarity	NPC191976
0.8485	Intermediate Similarity	NPC13575
0.8485	Intermediate Similarity	NPC194764
0.8473	Intermediate Similarity	NPC474117
0.8473	Intermediate Similarity	NPC474224
0.8462	Intermediate Similarity	NPC474109
0.8462	Intermediate Similarity	NPC185624
0.8455	Intermediate Similarity	NPC159525
0.845	Intermediate Similarity	NPC259942
0.8433	Intermediate Similarity	NPC254168
0.8433	Intermediate Similarity	NPC272844
0.8433	Intermediate Similarity	NPC248995
0.8425	Intermediate Similarity	NPC8745
0.8421	Intermediate Similarity	NPC168105
0.8421	Intermediate Similarity	NPC44960
0.8421	Intermediate Similarity	NPC474110
0.8421	Intermediate Similarity	NPC150399
0.8421	Intermediate Similarity	NPC186838
0.8421	Intermediate Similarity	NPC477243
0.8421	Intermediate Similarity	NPC477242
0.8421	Intermediate Similarity	NPC66349
0.8421	Intermediate Similarity	NPC249606
0.8421	Intermediate Similarity	NPC274109
0.8421	Intermediate Similarity	NPC12165
0.8421	Intermediate Similarity	NPC477244
0.8421	Intermediate Similarity	NPC1486
0.8421	Intermediate Similarity	NPC25287
0.8421	Intermediate Similarity	NPC41461
0.8421	Intermediate Similarity	NPC98115
0.8413	Intermediate Similarity	NPC13238
0.8409	Intermediate Similarity	NPC475917
0.8397	Intermediate Similarity	NPC470988
0.8397	Intermediate Similarity	NPC267205
0.8397	Intermediate Similarity	NPC103105
0.8382	Intermediate Similarity	NPC193555
0.8374	Intermediate Similarity	NPC161617
0.8374	Intermediate Similarity	NPC158222
0.8372	Intermediate Similarity	NPC109123
0.837	Intermediate Similarity	NPC240305
0.837	Intermediate Similarity	NPC275903
0.8361	Intermediate Similarity	NPC121259
0.8358	Intermediate Similarity	NPC472419
0.8358	Intermediate Similarity	NPC153979
0.8358	Intermediate Similarity	NPC317119
0.8358	Intermediate Similarity	NPC473622
0.8346	Intermediate Similarity	NPC118919
0.8346	Intermediate Similarity	NPC477454
0.8333	Intermediate Similarity	NPC82225
0.8333	Intermediate Similarity	NPC18877
0.8333	Intermediate Similarity	NPC144051
0.8333	Intermediate Similarity	NPC28753
0.8333	Intermediate Similarity	NPC470984
0.8333	Intermediate Similarity	NPC20560
0.8333	Intermediate Similarity	NPC159623
0.8333	Intermediate Similarity	NPC294593
0.8333	Intermediate Similarity	NPC204960
0.8308	Intermediate Similarity	NPC84772
0.8296	Intermediate Similarity	NPC243528
0.8296	Intermediate Similarity	NPC251681
0.8296	Intermediate Similarity	NPC138099
0.8296	Intermediate Similarity	NPC242994
0.8296	Intermediate Similarity	NPC471620
0.8296	Intermediate Similarity	NPC21350
0.8296	Intermediate Similarity	NPC19622
0.8296	Intermediate Similarity	NPC112789
0.8284	Intermediate Similarity	NPC147691
0.8284	Intermediate Similarity	NPC470985
0.8284	Intermediate Similarity	NPC470989
0.8284	Intermediate Similarity	NPC471905
0.8281	Intermediate Similarity	NPC473751
0.8281	Intermediate Similarity	NPC473691
0.8271	Intermediate Similarity	NPC286336
0.8261	Intermediate Similarity	NPC172182
0.8261	Intermediate Similarity	NPC262935
0.8261	Intermediate Similarity	NPC251182
0.8258	Intermediate Similarity	NPC48036
0.8248	Intermediate Similarity	NPC476508
0.8248	Intermediate Similarity	NPC157497
0.8248	Intermediate Similarity	NPC81337
0.8248	Intermediate Similarity	NPC285659
0.8244	Intermediate Similarity	NPC324482
0.8244	Intermediate Similarity	NPC250057
0.8235	Intermediate Similarity	NPC470211
0.8235	Intermediate Similarity	NPC283429
0.8235	Intermediate Similarity	NPC301217
0.8235	Intermediate Similarity	NPC169452
0.8235	Intermediate Similarity	NPC477956
0.8235	Intermediate Similarity	NPC470986
0.8235	Intermediate Similarity	NPC55018
0.8235	Intermediate Similarity	NPC220062
0.8235	Intermediate Similarity	NPC53181
0.8235	Intermediate Similarity	NPC181560
0.8235	Intermediate Similarity	NPC217186
0.8235	Intermediate Similarity	NPC216978
0.8235	Intermediate Similarity	NPC472366
0.8235	Intermediate Similarity	NPC303633
0.8235	Intermediate Similarity	NPC96565
0.8231	Intermediate Similarity	NPC120488
0.8231	Intermediate Similarity	NPC102829
0.8231	Intermediate Similarity	NPC230818
0.8209	Intermediate Similarity	NPC254847
0.8209	Intermediate Similarity	NPC101752
0.8201	Intermediate Similarity	NPC12402
0.8195	Intermediate Similarity	NPC175098
0.8195	Intermediate Similarity	NPC312318
0.8195	Intermediate Similarity	NPC474519
0.8195	Intermediate Similarity	NPC472365
0.8195	Intermediate Similarity	NPC27643
0.8195	Intermediate Similarity	NPC242294
0.8195	Intermediate Similarity	NPC337373

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 NPC232708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	1048
0.2-0.3	1908
0.3-0.4	3145
0.4-0.5	1779
0.5-0.6	745
0.6-0.7	176
0.7-0.8	49
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
0.8473	Intermediate Similarity	NPD6651	Approved
0.8209	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7390	Discontinued
0.8071	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1240	Approved
0.8045	Intermediate Similarity	NPD943	Approved
0.7943	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1607	Approved
0.7862	Intermediate Similarity	NPD7411	Suspended
0.7842	Intermediate Similarity	NPD2800	Approved
0.7823	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1510	Phase 2
0.7698	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4380	Phase 2
0.7656	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1549	Phase 2
0.7519	Intermediate Similarity	NPD1164	Approved
0.7517	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7483	Intermediate Similarity	NPD7075	Discontinued
0.7481	Intermediate Similarity	NPD1201	Approved
0.745	Intermediate Similarity	NPD6801	Discontinued
0.7448	Intermediate Similarity	NPD2534	Approved
0.7448	Intermediate Similarity	NPD2533	Approved
0.7448	Intermediate Similarity	NPD2532	Approved
0.7419	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7819	Suspended
0.7388	Intermediate Similarity	NPD1470	Approved
0.7376	Intermediate Similarity	NPD2796	Approved
0.7376	Intermediate Similarity	NPD2935	Discontinued
0.7343	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6799	Approved
0.726	Intermediate Similarity	NPD1511	Approved
0.7219	Intermediate Similarity	NPD1934	Approved
0.7179	Intermediate Similarity	NPD6232	Discontinued
0.7171	Intermediate Similarity	NPD2801	Approved
0.7162	Intermediate Similarity	NPD1512	Approved
0.7152	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD846	Approved
0.7131	Intermediate Similarity	NPD940	Approved
0.7103	Intermediate Similarity	NPD1243	Approved
0.7095	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6599	Discontinued
0.7078	Intermediate Similarity	NPD7768	Phase 2
0.7078	Intermediate Similarity	NPD3882	Suspended
0.7063	Intermediate Similarity	NPD9266	Approved
0.7063	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD74	Approved
0.7063	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD3750	Approved
0.7023	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9264	Approved
0.6984	Remote Similarity	NPD9267	Approved
0.6984	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9263	Approved
0.6981	Remote Similarity	NPD6166	Phase 2
0.6981	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5953	Discontinued
0.6966	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD7286	Phase 2
0.6939	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3749	Approved
0.6912	Remote Similarity	NPD9269	Phase 2
0.6908	Remote Similarity	NPD3226	Approved
0.6903	Remote Similarity	NPD3817	Phase 2
0.6897	Remote Similarity	NPD1551	Phase 2
0.6894	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD920	Approved
0.6884	Remote Similarity	NPD1203	Approved
0.6879	Remote Similarity	NPD2313	Discontinued
0.6879	Remote Similarity	NPD3268	Approved
0.6871	Remote Similarity	NPD2654	Approved
0.6866	Remote Similarity	NPD9268	Approved
0.6855	Remote Similarity	NPD5711	Approved
0.6855	Remote Similarity	NPD5710	Approved
0.6835	Remote Similarity	NPD2798	Approved
0.681	Remote Similarity	NPD7074	Phase 3
0.6791	Remote Similarity	NPD9545	Approved
0.679	Remote Similarity	NPD3818	Discontinued
0.6788	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2309	Approved
0.6776	Remote Similarity	NPD5403	Approved
0.6752	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7054	Approved
0.6748	Remote Similarity	NPD6020	Phase 2
0.6744	Remote Similarity	NPD4750	Phase 3
0.6742	Remote Similarity	NPD9281	Approved
0.6738	Remote Similarity	NPD6832	Phase 2
0.6736	Remote Similarity	NPD230	Phase 1
0.6733	Remote Similarity	NPD643	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5494	Approved
0.6727	Remote Similarity	NPD6559	Discontinued
0.6721	Remote Similarity	NPD2860	Approved
0.6721	Remote Similarity	NPD2859	Approved
0.6712	Remote Similarity	NPD3748	Approved
0.6707	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6645	Remote Similarity	NPD5401	Approved
0.6645	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3764	Approved
0.664	Remote Similarity	NPD1242	Phase 1
0.6639	Remote Similarity	NPD2934	Approved
0.6639	Remote Similarity	NPD2933	Approved
0.6627	Remote Similarity	NPD7251	Discontinued
0.6623	Remote Similarity	NPD3300	Phase 2
0.6622	Remote Similarity	NPD2346	Discontinued
0.66	Remote Similarity	NPD3400	Discontinued
0.6599	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7808	Phase 3
0.6585	Remote Similarity	NPD1809	Phase 2
0.6584	Remote Similarity	NPD1247	Approved
0.6582	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3019	Approved
0.6569	Remote Similarity	NPD2932	Approved
0.656	Remote Similarity	NPD3020	Approved
0.6558	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD2797	Approved
0.6525	Remote Similarity	NPD3266	Approved
0.6525	Remote Similarity	NPD3267	Approved
0.6519	Remote Similarity	NPD1465	Phase 2
0.6507	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5124	Phase 1
0.6506	Remote Similarity	NPD1729	Discontinued
0.6503	Remote Similarity	NPD3926	Phase 2
0.6497	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4628	Phase 3
0.649	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1237	Approved
0.6478	Remote Similarity	NPD5402	Approved
0.6475	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD422	Phase 1
0.6474	Remote Similarity	NPD7458	Discontinued
0.646	Remote Similarity	NPD919	Approved
0.6446	Remote Similarity	NPD5844	Phase 1
0.6433	Remote Similarity	NPD6585	Discontinued
0.6423	Remote Similarity	NPD845	Approved
0.642	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1929	Approved
0.6406	Remote Similarity	NPD1930	Approved
0.64	Remote Similarity	NPD4360	Phase 2
0.64	Remote Similarity	NPD4363	Phase 3
0.64	Remote Similarity	NPD1471	Phase 3
0.6392	Remote Similarity	NPD5889	Approved
0.6392	Remote Similarity	NPD5890	Approved
0.6389	Remote Similarity	NPD4908	Phase 1
0.6382	Remote Similarity	NPD7003	Approved
0.6376	Remote Similarity	NPD4308	Phase 3
0.6376	Remote Similarity	NPD7033	Discontinued
0.637	Remote Similarity	NPD520	Approved
0.637	Remote Similarity	NPD5951	Approved
0.6369	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2403	Approved
0.6364	Remote Similarity	NPD4361	Phase 2
0.6364	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD3225	Approved
0.6331	Remote Similarity	NPD5637	Discontinued
0.6308	Remote Similarity	NPD5048	Discontinued
0.6304	Remote Similarity	NPD1548	Phase 1
0.6289	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5049	Phase 3
0.6273	Remote Similarity	NPD2296	Approved
0.6269	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8150	Discontinued
0.6241	Remote Similarity	NPD3021	Approved
0.6241	Remote Similarity	NPD1610	Phase 2
0.6241	Remote Similarity	NPD3022	Approved
0.6235	Remote Similarity	NPD6104	Discontinued
0.6234	Remote Similarity	NPD6190	Approved
0.6233	Remote Similarity	NPD4625	Phase 3
0.6224	Remote Similarity	NPD1876	Approved
0.6222	Remote Similarity	NPD7635	Approved
0.6215	Remote Similarity	NPD6534	Approved
0.6215	Remote Similarity	NPD6535	Approved
0.6207	Remote Similarity	NPD4208	Discontinued
0.6197	Remote Similarity	NPD1608	Approved
0.619	Remote Similarity	NPD411	Approved
0.619	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1296	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