NPASS Compound

Structure

CID232021 OpenBabel06191716032D 30 32 0 0 1 0 0 0 0 0999 V2000 0.8398 -4.3636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3591 -2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3591 2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1989 2.4242 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 4.1989 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 -2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1989 -1.4545 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 4.1989 -0.4848 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 -0.8398 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -3.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3591 -1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3591 0.9697 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 2.5193 -1.4545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3591 -0.0000 0.0000 C 0 0 1 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 -0.0000 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 -0.4848 0.0000 C 0 0 2 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 0.8398 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 -1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 30 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 17 20 1 0 0 0 0 19 30 1 0 0 0 0 20 12 1 6 0 0 0 20 24 1 0 0 0 0 21 18 1 6 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 28 1 0 0 0 0 24 26 1 1 0 0 0 25 26 1 0 0 0 0 26 29 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.21
Volume:	444.015
LogP:	6.861
LogD:	4.61
LogS:	-4.022
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	3.824
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	1.5308787624235265e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.57916259765625%
Volume Distribution (VD):	1.842
Pgp-substrate:	3.4070701599121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.343
CYP2C9-inhibitor:	0.941
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.51
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	11.25
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.673
Drug-inuced Liver Injury (DILI):	0.479
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.729
Skin Sensitization:	0.593
Carcinogencity:	0.049
Eye Corrosion:	0.004
Eye Irritation:	0.739
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC232021

Natural Product ID:	NPC232021
*Common Name:**	(1'r,2'r,6'r*)-(2,6-Dihydroxy-4-Methoxyphenyl)-(3'-Methyl-6'-Phenyl-2'-Prenylcyclohex-3'-Enyl)Methanone
IUPAC Name:	(2,6-dihydroxy-4-methoxyphenyl)-[(1R,2R,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]methanone
Synonyms:	(+/-)-nicolaioidesin A
Standard InCHIKey:	LYDZCXVWCFJAKQ-AWRGLXIESA-N
Standard InCHI:	InChI=1S/C26H30O4/c1-16(2)10-12-20-17(3)11-13-21(18-8-6-5-7-9-18)24(20)26(29)25-22(27)14-19(30-4)15-23(25)28/h5-11,14-15,20-21,24,27-28H,12-13H2,1-4H3/t20-,21-,24+/m0/s1
SMILES:	CC(=CC[C@H]1C(=CC[C@@H](c2ccccc2)[C@@H]1C(=O)c1c(cc(cc1O)OC)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465442
PubChem CID:	10894788
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO8788	Renealmia nicolaioides	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444686]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930750]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	rhizomes	Pindaya Township, Shan State, Myanmar	2004-NOV	PMID[17896818]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27508308]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28099006]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24946	Kaempferia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8788	Renealmia nicolaioides	Species	Zingiberaceae	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
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	10.0	ug ml-1	PMID[490217]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	7.2	uM	PMID[490218]

☑ 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 NPC232021 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	1496
0.2-0.3	3508
0.3-0.4	9017
0.4-0.5	9508
0.5-0.6	3500
0.6-0.7	5921
0.7-0.8	5885
0.8-0.85	2060
0.85-0.9	1078
0.9-0.95	350
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126534
1.0	High Similarity	NPC40118
0.9926	High Similarity	NPC265178
0.9781	High Similarity	NPC297600
0.9489	High Similarity	NPC472368
0.9485	High Similarity	NPC213603
0.942	High Similarity	NPC472366
0.942	High Similarity	NPC477956
0.9416	High Similarity	NPC153979
0.9412	High Similarity	NPC13575
0.9407	High Similarity	NPC144051
0.9407	High Similarity	NPC28753
0.9407	High Similarity	NPC159623
0.9407	High Similarity	NPC82225
0.9407	High Similarity	NPC18877
0.9407	High Similarity	NPC20560
0.9407	High Similarity	NPC204960
0.9407	High Similarity	NPC294593
0.9371	High Similarity	NPC329933
0.9362	High Similarity	NPC271288
0.9353	High Similarity	NPC48624
0.9353	High Similarity	NPC172250
0.9353	High Similarity	NPC144118
0.9353	High Similarity	NPC80962
0.9353	High Similarity	NPC259166
0.9353	High Similarity	NPC219917
0.9353	High Similarity	NPC215311
0.9353	High Similarity	NPC326109
0.9353	High Similarity	NPC213659
0.9353	High Similarity	NPC204985
0.9353	High Similarity	NPC11056
0.9348	High Similarity	NPC21350
0.9348	High Similarity	NPC243528
0.9348	High Similarity	NPC251681
0.9343	High Similarity	NPC186838
0.9343	High Similarity	NPC476333
0.9343	High Similarity	NPC249606
0.9343	High Similarity	NPC98115
0.9343	High Similarity	NPC12165
0.9343	High Similarity	NPC150399
0.9343	High Similarity	NPC1486
0.9343	High Similarity	NPC274109
0.9343	High Similarity	NPC477242
0.9343	High Similarity	NPC24394
0.9343	High Similarity	NPC477244
0.9343	High Similarity	NPC41461
0.9343	High Similarity	NPC477243
0.9343	High Similarity	NPC168105
0.9343	High Similarity	NPC25287
0.9343	High Similarity	NPC472367
0.9343	High Similarity	NPC66349
0.9338	High Similarity	NPC286336
0.9338	High Similarity	NPC103842
0.9296	High Similarity	NPC477955
0.9296	High Similarity	NPC25844
0.9286	High Similarity	NPC469404
0.9286	High Similarity	NPC52789
0.9286	High Similarity	NPC26051
0.9286	High Similarity	NPC268204
0.9286	High Similarity	NPC282300
0.9286	High Similarity	NPC49108
0.9286	High Similarity	NPC55832
0.9281	High Similarity	NPC295384
0.9281	High Similarity	NPC109232
0.9281	High Similarity	NPC283429
0.9275	High Similarity	NPC303644
0.9275	High Similarity	NPC162680
0.9275	High Similarity	NPC7013
0.9275	High Similarity	NPC317119
0.9275	High Similarity	NPC472419
0.9275	High Similarity	NPC116632
0.9275	High Similarity	NPC209560
0.9275	High Similarity	NPC294409
0.9275	High Similarity	NPC181124
0.927	High Similarity	NPC156092
0.927	High Similarity	NPC131039
0.9265	High Similarity	NPC312318
0.9265	High Similarity	NPC472365
0.9265	High Similarity	NPC188646
0.9265	High Similarity	NPC337373
0.9265	High Similarity	NPC242294
0.9265	High Similarity	NPC56031
0.9265	High Similarity	NPC175098
0.9265	High Similarity	NPC263670
0.9265	High Similarity	NPC192304
0.9265	High Similarity	NPC139813
0.9259	High Similarity	NPC186097
0.9259	High Similarity	NPC475009
0.9259	High Similarity	NPC475008
0.9259	High Similarity	NPC175738
0.9231	High Similarity	NPC475348
0.9231	High Similarity	NPC261271
0.9231	High Similarity	NPC308200
0.9231	High Similarity	NPC34802
0.9225	High Similarity	NPC311144
0.9225	High Similarity	NPC476055
0.922	High Similarity	NPC202981
0.922	High Similarity	NPC84266
0.9214	High Similarity	NPC101366
0.9214	High Similarity	NPC129853
0.9214	High Similarity	NPC241100
0.9214	High Similarity	NPC76445
0.9214	High Similarity	NPC159275
0.9214	High Similarity	NPC284550
0.9214	High Similarity	NPC253822
0.9209	High Similarity	NPC12175
0.9209	High Similarity	NPC309154
0.9209	High Similarity	NPC278323
0.9209	High Similarity	NPC55162
0.9209	High Similarity	NPC279668
0.9209	High Similarity	NPC90665
0.9203	High Similarity	NPC473391
0.9203	High Similarity	NPC472364
0.9191	High Similarity	NPC257756
0.9191	High Similarity	NPC205468
0.9191	High Similarity	NPC129132
0.9191	High Similarity	NPC87231
0.9191	High Similarity	NPC212631
0.9167	High Similarity	NPC39195
0.9167	High Similarity	NPC152233
0.9167	High Similarity	NPC145467
0.9161	High Similarity	NPC225173
0.9161	High Similarity	NPC163846
0.9161	High Similarity	NPC299011
0.9155	High Similarity	NPC11700
0.9155	High Similarity	NPC81697
0.9155	High Similarity	NPC51887
0.9155	High Similarity	NPC476178
0.9155	High Similarity	NPC19896
0.9155	High Similarity	NPC475705
0.9155	High Similarity	NPC125894
0.9155	High Similarity	NPC223812
0.9155	High Similarity	NPC113770
0.9155	High Similarity	NPC107177
0.9155	High Similarity	NPC18585
0.9155	High Similarity	NPC85162
0.9155	High Similarity	NPC166138
0.9155	High Similarity	NPC117836
0.9155	High Similarity	NPC106985
0.9155	High Similarity	NPC77794
0.9155	High Similarity	NPC278249
0.9149	High Similarity	NPC26238
0.9149	High Similarity	NPC94076
0.9149	High Similarity	NPC321980
0.9149	High Similarity	NPC470087
0.9149	High Similarity	NPC250755
0.9149	High Similarity	NPC110969
0.9149	High Similarity	NPC182255
0.9149	High Similarity	NPC470089
0.9143	High Similarity	NPC303633
0.9143	High Similarity	NPC470211
0.9143	High Similarity	NPC96565
0.9143	High Similarity	NPC53181
0.9143	High Similarity	NPC216978
0.9143	High Similarity	NPC220062
0.9143	High Similarity	NPC316480
0.9143	High Similarity	NPC18260
0.9143	High Similarity	NPC78913
0.9143	High Similarity	NPC217186
0.9143	High Similarity	NPC55018
0.9143	High Similarity	NPC301217
0.9137	High Similarity	NPC23870
0.9137	High Similarity	NPC255801
0.9137	High Similarity	NPC322301
0.913	High Similarity	NPC39426
0.913	High Similarity	NPC234560
0.9124	High Similarity	NPC27643
0.9118	High Similarity	NPC308037
0.9118	High Similarity	NPC128348
0.9118	High Similarity	NPC309717
0.9118	High Similarity	NPC262359
0.9118	High Similarity	NPC313618
0.9118	High Similarity	NPC64359
0.9118	High Similarity	NPC164236
0.9118	High Similarity	NPC27490
0.9118	High Similarity	NPC112192
0.9118	High Similarity	NPC189106
0.9118	High Similarity	NPC66384
0.9103	High Similarity	NPC158338
0.9103	High Similarity	NPC100985
0.9103	High Similarity	NPC471114
0.9103	High Similarity	NPC473016
0.9103	High Similarity	NPC97028
0.9103	High Similarity	NPC65589
0.9103	High Similarity	NPC288036
0.9103	High Similarity	NPC97029
0.9097	High Similarity	NPC190648
0.9097	High Similarity	NPC289042
0.9097	High Similarity	NPC118027
0.9097	High Similarity	NPC312929
0.9097	High Similarity	NPC245584
0.9097	High Similarity	NPC300988
0.9097	High Similarity	NPC125801
0.9097	High Similarity	NPC126767
0.9097	High Similarity	NPC56433
0.9097	High Similarity	NPC10990
0.9091	High Similarity	NPC473013
0.9091	High Similarity	NPC273538
0.9091	High Similarity	NPC326500
0.9091	High Similarity	NPC473014

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 NPC232021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	940
0.2-0.3	1397
0.3-0.4	2509
0.4-0.5	2054
0.5-0.6	1240
0.6-0.7	486
0.7-0.8	142
0.8-0.85	42
0.85-0.9	10
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD1510	Phase 2
0.9124	High Similarity	NPD1607	Approved
0.9118	High Similarity	NPD1240	Approved
0.9091	High Similarity	NPD4378	Clinical (unspecified phase)
0.8865	High Similarity	NPD1552	Clinical (unspecified phase)
0.8865	High Similarity	NPD1550	Clinical (unspecified phase)
0.8803	High Similarity	NPD1549	Phase 2
0.88	High Similarity	NPD8443	Clinical (unspecified phase)
0.8699	High Similarity	NPD7410	Clinical (unspecified phase)
0.8671	High Similarity	NPD970	Clinical (unspecified phase)
0.8662	High Similarity	NPD2796	Approved
0.8658	High Similarity	NPD4380	Phase 2
0.8609	High Similarity	NPD2393	Clinical (unspecified phase)
0.8609	High Similarity	NPD7819	Suspended
0.8582	High Similarity	NPD6651	Approved
0.8552	High Similarity	NPD3750	Approved
0.8535	High Similarity	NPD7473	Discontinued
0.8477	Intermediate Similarity	NPD7411	Suspended
0.8462	Intermediate Similarity	NPD6232	Discontinued
0.8442	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD1934	Approved
0.8397	Intermediate Similarity	NPD6959	Discontinued
0.8378	Intermediate Similarity	NPD1511	Approved
0.8366	Intermediate Similarity	NPD2801	Approved
0.8366	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2533	Approved
0.8322	Intermediate Similarity	NPD2534	Approved
0.8322	Intermediate Similarity	NPD2532	Approved
0.8289	Intermediate Similarity	NPD6599	Discontinued
0.8276	Intermediate Similarity	NPD2935	Discontinued
0.8267	Intermediate Similarity	NPD1512	Approved
0.8258	Intermediate Similarity	NPD7768	Phase 2
0.8255	Intermediate Similarity	NPD6799	Approved
0.8239	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD3748	Approved
0.8205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3749	Approved
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8151	Intermediate Similarity	NPD6099	Approved
0.8151	Intermediate Similarity	NPD6100	Approved
0.8151	Intermediate Similarity	NPD1551	Phase 2
0.8143	Intermediate Similarity	NPD2798	Approved
0.8141	Intermediate Similarity	NPD3882	Suspended
0.8133	Intermediate Similarity	NPD7390	Discontinued
0.8108	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD2799	Discontinued
0.8054	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5494	Approved
0.7975	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2344	Approved
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7933	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD943	Approved
0.7917	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1201	Approved
0.7902	Intermediate Similarity	NPD4908	Phase 1
0.7871	Intermediate Similarity	NPD3226	Approved
0.7867	Intermediate Similarity	NPD1243	Approved
0.7857	Intermediate Similarity	NPD3972	Approved
0.7818	Intermediate Similarity	NPD7074	Phase 3
0.7817	Intermediate Similarity	NPD1470	Approved
0.7815	Intermediate Similarity	NPD7003	Approved
0.7815	Intermediate Similarity	NPD4628	Phase 3
0.7805	Intermediate Similarity	NPD3818	Discontinued
0.7793	Intermediate Similarity	NPD3268	Approved
0.7786	Intermediate Similarity	NPD1610	Phase 2
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.7763	Intermediate Similarity	NPD2309	Approved
0.7758	Intermediate Similarity	NPD7054	Approved
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7756	Intermediate Similarity	NPD7458	Discontinued
0.7748	Intermediate Similarity	NPD2654	Approved
0.7742	Intermediate Similarity	NPD5403	Approved
0.7742	Intermediate Similarity	NPD920	Approved
0.7733	Intermediate Similarity	NPD2346	Discontinued
0.7725	Intermediate Similarity	NPD6559	Discontinued
0.7712	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7472	Approved
0.7692	Intermediate Similarity	NPD1203	Approved
0.7692	Intermediate Similarity	NPD2797	Approved
0.7688	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2313	Discontinued
0.7669	Intermediate Similarity	NPD5710	Approved
0.7669	Intermediate Similarity	NPD5711	Approved
0.7667	Intermediate Similarity	NPD5406	Approved
0.7667	Intermediate Similarity	NPD5404	Approved
0.7667	Intermediate Similarity	NPD5408	Approved
0.7667	Intermediate Similarity	NPD5405	Approved
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7651	Intermediate Similarity	NPD7286	Phase 2
0.7628	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1876	Approved
0.7619	Intermediate Similarity	NPD7251	Discontinued
0.7613	Intermediate Similarity	NPD5401	Approved
0.7613	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4625	Phase 3
0.7574	Intermediate Similarity	NPD7808	Phase 3
0.7552	Intermediate Similarity	NPD4749	Approved
0.7551	Intermediate Similarity	NPD3764	Approved
0.7543	Intermediate Similarity	NPD4360	Phase 2
0.7543	Intermediate Similarity	NPD4363	Phase 3
0.7535	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5402	Approved
0.7516	Intermediate Similarity	NPD4288	Approved
0.7515	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD4361	Phase 2
0.75	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1283	Approved
0.7483	Intermediate Similarity	NPD9717	Approved
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1608	Approved
0.7483	Intermediate Similarity	NPD4308	Phase 3
0.7482	Intermediate Similarity	NPD9493	Approved
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.7448	Intermediate Similarity	NPD3266	Approved
0.7448	Intermediate Similarity	NPD1164	Approved
0.7448	Intermediate Similarity	NPD3267	Approved
0.7447	Intermediate Similarity	NPD1651	Approved
0.7432	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD422	Phase 1
0.7386	Intermediate Similarity	NPD1471	Phase 3
0.7378	Intermediate Similarity	NPD919	Approved
0.7378	Intermediate Similarity	NPD6234	Discontinued
0.7376	Intermediate Similarity	NPD9545	Approved
0.7362	Intermediate Similarity	NPD4965	Approved
0.7362	Intermediate Similarity	NPD4967	Phase 2
0.7362	Intermediate Similarity	NPD4966	Approved
0.7349	Intermediate Similarity	NPD7229	Phase 3
0.7329	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8434	Phase 2
0.7292	Intermediate Similarity	NPD1281	Approved
0.7289	Intermediate Similarity	NPD1247	Approved
0.7289	Intermediate Similarity	NPD7199	Phase 2
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7285	Intermediate Similarity	NPD5124	Phase 1
0.7285	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD2932	Approved
0.7262	Intermediate Similarity	NPD2403	Approved
0.7261	Intermediate Similarity	NPD3300	Phase 2
0.726	Intermediate Similarity	NPD3225	Approved
0.7251	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3027	Phase 3
0.7239	Intermediate Similarity	NPD5761	Phase 2
0.7239	Intermediate Similarity	NPD5760	Phase 2
0.7238	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6273	Approved
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7219	Intermediate Similarity	NPD4307	Phase 2
0.7216	Intermediate Similarity	NPD4287	Approved
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD8150	Discontinued
0.7195	Intermediate Similarity	NPD2296	Approved
0.7193	Intermediate Similarity	NPD1729	Discontinued
0.7181	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1933	Approved
0.7167	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3019	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6020	Phase 2
0.7114	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.7105	Intermediate Similarity	NPD2979	Phase 3

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