NPASS Compound

Structure

CID316769 OpenBabel06191716132D 29 30 0 0 1 0 0 0 0 0999 V2000 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.6340 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 -1.0981 2.3660 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 -1.5000 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 -0.8660 -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 -1.7321 1.0000 0.0000 C 0 0 3 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 0.0000 -0.0000 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 6.9282 -2.0000 0.0000 O 0 0 0 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 -1.7321 -2.0000 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 -0.0000 1.0000 0.0000 O 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 -2.0981 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 28 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	412.395
LogP:	2.968
LogD:	2.514
LogS:	-3.379
# Rotatable Bonds:	8
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	3.325
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.993
MDCK Permeability:	1.2385447917040437e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.777
Human Intestinal Absorption (HIA):	0.132
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	98.79703521728516%
Volume Distribution (VD):	0.461
Pgp-substrate:	1.4572439193725586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.806
CYP1A2-substrate:	0.679
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.42
CYP2D6-substrate:	0.645
CYP3A4-inhibitor:	0.282
CYP3A4-substrate:	0.329

ADMET: Excretion

Clearance (CL):	12.451
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.315
AMES Toxicity:	0.299
Rat Oral Acute Toxicity:	0.596
Maximum Recommended Daily Dose:	0.584
Skin Sensitization:	0.945
Carcinogencity:	0.425
Eye Corrosion:	0.003
Eye Irritation:	0.079
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC316769

Natural Product ID:	NPC316769
*Common Name:**	(+/-)-1-[2,4-Dihydroxy-3-(3-Hydroxy-2-Methoxy-3-Methylbutyl)-6-Methoxyphenyl]-3-(4-Hydroxyphenyl)Propenone
IUPAC Name:	(E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	YXGBQKBRCDLZMP-JXMROGBWSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-22(2,29-4)19(26)11-15-17(25)12-18(28-3)20(21(15)27)16(24)10-7-13-5-8-14(23)9-6-13/h5-10,12,19,23,25-27H,11H2,1-4H3/b10-7+
SMILES:	COC(C(Cc1c(O)cc(c(c1O)C(=O)/C=C/c1ccc(cc1)O)OC)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481442
PubChem CID:	11258152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13879	Humulus lupulus	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6500.0	nM	PMID[555939]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	95.0	%	PMID[555939]

☑ 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 NPC316769 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	363
0.1-0.2	1357
0.2-0.3	3470
0.3-0.4	8351
0.4-0.5	10112
0.5-0.6	3726
0.6-0.7	5253
0.7-0.8	5941
0.8-0.85	2479
0.85-0.9	1202
0.9-0.95	419
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC222298
0.9787	High Similarity	NPC51070
0.9712	High Similarity	NPC321980
0.9712	High Similarity	NPC470087
0.9653	High Similarity	NPC472422
0.9653	High Similarity	NPC263384
0.9653	High Similarity	NPC471676
0.9653	High Similarity	NPC244577
0.9653	High Similarity	NPC472423
0.9653	High Similarity	NPC474772
0.9653	High Similarity	NPC474744
0.9653	High Similarity	NPC472420
0.965	High Similarity	NPC89442
0.9583	High Similarity	NPC472421
0.9574	High Similarity	NPC51887
0.9574	High Similarity	NPC301751
0.9574	High Similarity	NPC245482
0.9574	High Similarity	NPC475705
0.9574	High Similarity	NPC117836
0.9574	High Similarity	NPC476178
0.9571	High Similarity	NPC470089
0.9568	High Similarity	NPC470211
0.9521	High Similarity	NPC223701
0.9521	High Similarity	NPC472583
0.9521	High Similarity	NPC7989
0.9517	High Similarity	NPC471677
0.9504	High Similarity	NPC148545
0.9496	High Similarity	NPC21350
0.9456	High Similarity	NPC477958
0.9456	High Similarity	NPC470681
0.9452	High Similarity	NPC243171
0.9452	High Similarity	NPC475790
0.9452	High Similarity	NPC473996
0.9452	High Similarity	NPC171651
0.9452	High Similarity	NPC476238
0.9452	High Similarity	NPC327269
0.9452	High Similarity	NPC35567
0.9452	High Similarity	NPC31627
0.9452	High Similarity	NPC285623
0.9448	High Similarity	NPC124478
0.9448	High Similarity	NPC177308
0.9433	High Similarity	NPC469404
0.9424	High Similarity	NPC317119
0.9388	High Similarity	NPC293286
0.9388	High Similarity	NPC469405
0.9384	High Similarity	NPC474023
0.9384	High Similarity	NPC474021
0.9384	High Similarity	NPC472636
0.9384	High Similarity	NPC319910
0.9384	High Similarity	NPC471675
0.9384	High Similarity	NPC472580
0.9384	High Similarity	NPC262039
0.9384	High Similarity	NPC262038
0.9384	High Similarity	NPC278476
0.9384	High Similarity	NPC254412
0.9379	High Similarity	NPC472628
0.9375	High Similarity	NPC473133
0.9375	High Similarity	NPC91902
0.9375	High Similarity	NPC47388
0.9375	High Similarity	NPC14875
0.9375	High Similarity	NPC472627
0.9375	High Similarity	NPC470670
0.9362	High Similarity	NPC213659
0.9362	High Similarity	NPC204985
0.9362	High Similarity	NPC215311
0.9362	High Similarity	NPC48624
0.9362	High Similarity	NPC172250
0.9362	High Similarity	NPC144118
0.9362	High Similarity	NPC80962
0.9362	High Similarity	NPC326109
0.9362	High Similarity	NPC219917
0.9362	High Similarity	NPC259166
0.9353	High Similarity	NPC41461
0.9353	High Similarity	NPC25287
0.9353	High Similarity	NPC168105
0.9353	High Similarity	NPC477243
0.9353	High Similarity	NPC66349
0.9353	High Similarity	NPC186838
0.9353	High Similarity	NPC1486
0.9353	High Similarity	NPC98115
0.9353	High Similarity	NPC249606
0.9353	High Similarity	NPC12165
0.9353	High Similarity	NPC150399
0.9353	High Similarity	NPC477242
0.9353	High Similarity	NPC477244
0.9353	High Similarity	NPC274109
0.9324	High Similarity	NPC217706
0.9324	High Similarity	NPC207809
0.9324	High Similarity	NPC304207
0.9324	High Similarity	NPC48579
0.9324	High Similarity	NPC259710
0.932	High Similarity	NPC324233
0.932	High Similarity	NPC477957
0.932	High Similarity	NPC56232
0.932	High Similarity	NPC323626
0.932	High Similarity	NPC244583
0.932	High Similarity	NPC138288
0.932	High Similarity	NPC150123
0.932	High Similarity	NPC161881
0.932	High Similarity	NPC10807
0.932	High Similarity	NPC217149
0.932	High Similarity	NPC216035
0.9315	High Similarity	NPC105136
0.9315	High Similarity	NPC61258
0.9306	High Similarity	NPC472629
0.9296	High Similarity	NPC55832
0.9296	High Similarity	NPC268204
0.9296	High Similarity	NPC26051
0.9296	High Similarity	NPC52789
0.9291	High Similarity	NPC283429
0.9291	High Similarity	NPC477956
0.9291	High Similarity	NPC295384
0.9286	High Similarity	NPC153979
0.9286	High Similarity	NPC472419
0.9281	High Similarity	NPC84699
0.9281	High Similarity	NPC131039
0.9281	High Similarity	NPC13575
0.9281	High Similarity	NPC156092
0.9262	High Similarity	NPC20530
0.9262	High Similarity	NPC215917
0.9262	High Similarity	NPC208152
0.9262	High Similarity	NPC10754
0.9262	High Similarity	NPC471787
0.9262	High Similarity	NPC78492
0.9257	High Similarity	NPC248793
0.9257	High Similarity	NPC180301
0.9252	High Similarity	NPC289774
0.9252	High Similarity	NPC209846
0.9252	High Similarity	NPC477897
0.9252	High Similarity	NPC328740
0.9247	High Similarity	NPC5173
0.9241	High Similarity	NPC85773
0.9241	High Similarity	NPC202494
0.9236	High Similarity	NPC87486
0.9236	High Similarity	NPC124780
0.9236	High Similarity	NPC328623
0.9236	High Similarity	NPC470890
0.9236	High Similarity	NPC224714
0.9236	High Similarity	NPC209040
0.9225	High Similarity	NPC101366
0.9225	High Similarity	NPC253822
0.9225	High Similarity	NPC11056
0.922	High Similarity	NPC471620
0.9209	High Similarity	NPC286336
0.9209	High Similarity	NPC103842
0.9209	High Similarity	NPC164136
0.9205	High Similarity	NPC471976
0.9195	High Similarity	NPC111341
0.9195	High Similarity	NPC477530
0.9195	High Similarity	NPC304745
0.9189	High Similarity	NPC256141
0.9189	High Similarity	NPC210597
0.9178	High Similarity	NPC6511
0.9178	High Similarity	NPC168085
0.9178	High Similarity	NPC10097
0.9172	High Similarity	NPC474302
0.9167	High Similarity	NPC39329
0.9167	High Similarity	NPC18886
0.9167	High Similarity	NPC257097
0.9167	High Similarity	NPC166138
0.9167	High Similarity	NPC214166
0.9167	High Similarity	NPC310130
0.9167	High Similarity	NPC169591
0.9167	High Similarity	NPC91560
0.9167	High Similarity	NPC221432
0.9167	High Similarity	NPC478086
0.9167	High Similarity	NPC95751
0.9167	High Similarity	NPC164980
0.9167	High Similarity	NPC106985
0.9167	High Similarity	NPC175504
0.9167	High Similarity	NPC143896
0.9167	High Similarity	NPC149026
0.9167	High Similarity	NPC316816
0.9167	High Similarity	NPC150408
0.9167	High Similarity	NPC18585
0.9167	High Similarity	NPC68104
0.9167	High Similarity	NPC75049
0.9155	High Similarity	NPC201541
0.9155	High Similarity	NPC472366
0.9149	High Similarity	NPC162680
0.9149	High Similarity	NPC209560
0.9149	High Similarity	NPC294409
0.9149	High Similarity	NPC181124
0.9149	High Similarity	NPC7013
0.9149	High Similarity	NPC116632
0.9149	High Similarity	NPC303644
0.9145	High Similarity	NPC3629
0.9137	High Similarity	NPC144051
0.9137	High Similarity	NPC472365
0.9137	High Similarity	NPC263670
0.9137	High Similarity	NPC159623
0.9137	High Similarity	NPC242294
0.9137	High Similarity	NPC82225
0.9137	High Similarity	NPC18877
0.9137	High Similarity	NPC56031
0.9137	High Similarity	NPC294593
0.9137	High Similarity	NPC28753
0.9137	High Similarity	NPC192304
0.9137	High Similarity	NPC204960
0.9137	High Similarity	NPC175098

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 NPC316769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	839
0.2-0.3	1617
0.3-0.4	2604
0.4-0.5	1955
0.5-0.6	1121
0.6-0.7	471
0.7-0.8	160
0.8-0.85	38
0.85-0.9	16
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9448	High Similarity	NPD4380	Phase 2
0.9007	High Similarity	NPD1510	Phase 2
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.8993	High Similarity	NPD1240	Approved
0.8973	High Similarity	NPD4378	Clinical (unspecified phase)
0.8947	High Similarity	NPD7075	Discontinued
0.8874	High Similarity	NPD7096	Clinical (unspecified phase)
0.8865	High Similarity	NPD1607	Approved
0.8824	High Similarity	NPD4381	Clinical (unspecified phase)
0.8819	High Similarity	NPD1549	Phase 2
0.8808	High Similarity	NPD1934	Approved
0.8808	High Similarity	NPD6801	Discontinued
0.875	High Similarity	NPD1552	Clinical (unspecified phase)
0.875	High Similarity	NPD1550	Clinical (unspecified phase)
0.8716	High Similarity	NPD7410	Clinical (unspecified phase)
0.8681	High Similarity	NPD2796	Approved
0.8649	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8562	High Similarity	NPD7804	Clinical (unspecified phase)
0.8516	High Similarity	NPD3882	Suspended
0.8506	High Similarity	NPD2801	Approved
0.8497	Intermediate Similarity	NPD7411	Suspended
0.8491	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6166	Phase 2
0.8491	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD6599	Discontinued
0.8425	Intermediate Similarity	NPD2935	Discontinued
0.84	Intermediate Similarity	NPD1511	Approved
0.8387	Intermediate Similarity	NPD7819	Suspended
0.8385	Intermediate Similarity	NPD3818	Discontinued
0.8293	Intermediate Similarity	NPD6559	Discontinued
0.8289	Intermediate Similarity	NPD1512	Approved
0.8282	Intermediate Similarity	NPD7074	Phase 3
0.825	Intermediate Similarity	NPD6232	Discontinued
0.8239	Intermediate Similarity	NPD5494	Approved
0.8235	Intermediate Similarity	NPD5403	Approved
0.8221	Intermediate Similarity	NPD7054	Approved
0.8219	Intermediate Similarity	NPD6651	Approved
0.8217	Intermediate Similarity	NPD3817	Phase 2
0.821	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD4628	Phase 3
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8171	Intermediate Similarity	NPD7472	Approved
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7768	Phase 2
0.8148	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2800	Approved
0.8133	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6797	Phase 2
0.8105	Intermediate Similarity	NPD2533	Approved
0.8105	Intermediate Similarity	NPD2532	Approved
0.8105	Intermediate Similarity	NPD2534	Approved
0.8105	Intermediate Similarity	NPD5401	Approved
0.8101	Intermediate Similarity	NPD5402	Approved
0.8082	Intermediate Similarity	NPD943	Approved
0.8072	Intermediate Similarity	NPD7251	Discontinued
0.8067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1551	Phase 2
0.8024	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD920	Approved
0.7961	Intermediate Similarity	NPD3750	Approved
0.7945	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD5953	Discontinued
0.7895	Intermediate Similarity	NPD1243	Approved
0.7892	Intermediate Similarity	NPD7286	Phase 2
0.7888	Intermediate Similarity	NPD3749	Approved
0.7877	Intermediate Similarity	NPD3027	Phase 3
0.7871	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2799	Discontinued
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2344	Approved
0.7744	Intermediate Similarity	NPD1247	Approved
0.773	Intermediate Similarity	NPD919	Approved
0.7703	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD7390	Discontinued
0.7684	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7458	Discontinued
0.7671	Intermediate Similarity	NPD2798	Approved
0.7667	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3748	Approved
0.7632	Intermediate Similarity	NPD7033	Discontinued
0.7603	Intermediate Similarity	NPD1203	Approved
0.76	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1613	Approved
0.7597	Intermediate Similarity	NPD2424	Discontinued
0.7596	Intermediate Similarity	NPD7584	Approved
0.7584	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4360	Phase 2
0.7571	Intermediate Similarity	NPD4363	Phase 3
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6832	Phase 2
0.7564	Intermediate Similarity	NPD2309	Approved
0.7562	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD6776	Approved
0.7556	Intermediate Similarity	NPD6777	Approved
0.7556	Intermediate Similarity	NPD6780	Approved
0.7556	Intermediate Similarity	NPD6779	Approved
0.7556	Intermediate Similarity	NPD6778	Approved
0.7556	Intermediate Similarity	NPD6782	Approved
0.7556	Intermediate Similarity	NPD6781	Approved
0.7548	Intermediate Similarity	NPD2654	Approved
0.7545	Intermediate Similarity	NPD3926	Phase 2
0.7517	Intermediate Similarity	NPD3972	Approved
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD5711	Approved
0.7468	Intermediate Similarity	NPD6100	Approved
0.7468	Intermediate Similarity	NPD6099	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7457	Intermediate Similarity	NPD8312	Approved
0.7452	Intermediate Similarity	NPD6190	Approved
0.745	Intermediate Similarity	NPD4908	Phase 1
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5124	Phase 1
0.7434	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7435	Discontinued
0.7429	Intermediate Similarity	NPD8150	Discontinued
0.7429	Intermediate Similarity	NPD8434	Phase 2
0.7423	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD4662	Approved
0.7421	Intermediate Similarity	NPD4661	Approved
0.7419	Intermediate Similarity	NPD2346	Discontinued
0.7413	Intermediate Similarity	NPD9545	Approved
0.7397	Intermediate Similarity	NPD9717	Approved
0.7394	Intermediate Similarity	NPD9493	Approved
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3823	Discontinued
0.7383	Intermediate Similarity	NPD9494	Approved
0.7381	Intermediate Similarity	NPD3787	Discontinued
0.7365	Intermediate Similarity	NPD1164	Approved
0.7362	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6798	Discontinued
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7698	Approved
0.7337	Intermediate Similarity	NPD7697	Approved
0.7337	Intermediate Similarity	NPD7696	Phase 3
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4361	Phase 2
0.7329	Intermediate Similarity	NPD1610	Phase 2
0.7326	Intermediate Similarity	NPD1729	Discontinued
0.7326	Intermediate Similarity	NPD8151	Discontinued
0.732	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD447	Suspended
0.7305	Intermediate Similarity	NPD6234	Discontinued
0.7297	Intermediate Similarity	NPD7871	Phase 2
0.7297	Intermediate Similarity	NPD7870	Phase 2
0.7292	Intermediate Similarity	NPD1548	Phase 1
0.729	Intermediate Similarity	NPD4308	Phase 3
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7289	Intermediate Similarity	NPD4966	Approved
0.7283	Intermediate Similarity	NPD6823	Phase 2
0.7278	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD6535	Approved
0.7278	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD7701	Phase 2
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5049	Phase 3
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1470	Approved
0.7244	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD5406	Approved
0.7244	Intermediate Similarity	NPD5408	Approved
0.7244	Intermediate Similarity	NPD5405	Approved
0.7239	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3764	Approved
0.7237	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD2354	Approved
0.7233	Intermediate Similarity	NPD3887	Approved
0.7219	Intermediate Similarity	NPD7199	Phase 2
0.7215	Intermediate Similarity	NPD1652	Phase 2
0.7211	Intermediate Similarity	NPD422	Phase 1
0.7211	Intermediate Similarity	NPD1201	Approved
0.7208	Intermediate Similarity	NPD1933	Approved
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7874	Approved
0.7196	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2403	Approved
0.719	Intermediate Similarity	NPD6233	Phase 2
0.7181	Intermediate Similarity	NPD7585	Approved
0.7181	Intermediate Similarity	NPD1876	Approved
0.7171	Intermediate Similarity	NPD4625	Phase 3
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	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