NPASS Compound

Structure

NPC265178 OpenBabel07101718192D 30 32 0 0 1 0 0 0 0 0999 V2000 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 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 4.3301 0.5000 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 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -0.0000 3.0000 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 1.7321 3.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 30 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 18 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 19 1 1 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 28 1 0 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:	6.961
LogD:	4.541
LogS:	-4.264
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	3.591
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:	-4.761
MDCK Permeability:	1.5406774764414877e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	100.00860595703125%
Volume Distribution (VD):	1.938
Pgp-substrate:	1.1423171758651733%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.721
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.207
CYP2C9-inhibitor:	0.947
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.63
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.199

ADMET: Excretion

Clearance (CL):	7.951
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.443
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.399
Carcinogencity:	0.556
Eye Corrosion:	0.003
Eye Irritation:	0.196
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC265178

Natural Product ID:	NPC265178
*Common Name:**	(1'r,6'r)-(2,6-Dihydroxy-4-Methoxyphenyl)-(3'-Isohexenyl-1'-Phenylcyclohex-3'-Enyl)Methanone
IUPAC Name:	(2,6-dihydroxy-4-methoxyphenyl)-[(1R,6R)-4-(4-methylpent-3-enyl)-6-phenylcyclohex-3-en-1-yl]methanone
Synonyms:	(+/-)-nicolaioidesin C
Standard InCHIKey:	VJYZXZFPGQYBKT-YADHBBJMSA-N
Standard InCHI:	InChI=1S/C26H30O4/c1-17(2)8-7-9-18-12-13-21(22(14-18)19-10-5-4-6-11-19)26(29)25-23(27)15-20(30-3)16-24(25)28/h4-6,8,10-12,15-16,21-22,27-28H,7,9,13-14H2,1-3H3/t21-,22+/m1/s1
SMILES:	CC(=CCCC1=CC[C@H]([C@@H](C1)c1ccccc1)C(=O)c1c(cc(cc1O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465443
PubChem CID:	11729201
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]
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]
NPO8788	Renealmia nicolaioides	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27600	Boesenbergia pandurata	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[478313]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	0.84	uM	PMID[478314]

☑ 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 NPC265178 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
0.9926	High Similarity	NPC232021
0.9926	High Similarity	NPC40118
0.9926	High Similarity	NPC126534
0.9853	High Similarity	NPC297600
0.9556	High Similarity	NPC213603
0.9489	High Similarity	NPC477956
0.9485	High Similarity	NPC153979
0.9481	High Similarity	NPC13575
0.9478	High Similarity	NPC20560
0.9478	High Similarity	NPC18877
0.9478	High Similarity	NPC28753
0.9478	High Similarity	NPC144051
0.9478	High Similarity	NPC294593
0.9478	High Similarity	NPC159623
0.9478	High Similarity	NPC82225
0.9478	High Similarity	NPC204960
0.9429	High Similarity	NPC271288
0.942	High Similarity	NPC172250
0.942	High Similarity	NPC80962
0.942	High Similarity	NPC326109
0.942	High Similarity	NPC144118
0.942	High Similarity	NPC219917
0.942	High Similarity	NPC259166
0.942	High Similarity	NPC48624
0.942	High Similarity	NPC213659
0.942	High Similarity	NPC11056
0.942	High Similarity	NPC215311
0.942	High Similarity	NPC204985
0.9416	High Similarity	NPC251681
0.9416	High Similarity	NPC21350
0.9416	High Similarity	NPC472368
0.9416	High Similarity	NPC243528
0.9412	High Similarity	NPC186838
0.9412	High Similarity	NPC24394
0.9412	High Similarity	NPC66349
0.9412	High Similarity	NPC1486
0.9412	High Similarity	NPC168105
0.9412	High Similarity	NPC249606
0.9412	High Similarity	NPC41461
0.9412	High Similarity	NPC25287
0.9412	High Similarity	NPC274109
0.9412	High Similarity	NPC477242
0.9412	High Similarity	NPC150399
0.9412	High Similarity	NPC477243
0.9412	High Similarity	NPC98115
0.9412	High Similarity	NPC477244
0.9412	High Similarity	NPC12165
0.9407	High Similarity	NPC103842
0.9407	High Similarity	NPC286336
0.9362	High Similarity	NPC25844
0.9362	High Similarity	NPC477955
0.9353	High Similarity	NPC26051
0.9353	High Similarity	NPC469404
0.9353	High Similarity	NPC55832
0.9353	High Similarity	NPC268204
0.9353	High Similarity	NPC52789
0.9353	High Similarity	NPC282300
0.9348	High Similarity	NPC295384
0.9348	High Similarity	NPC283429
0.9348	High Similarity	NPC472366
0.9348	High Similarity	NPC109232
0.9343	High Similarity	NPC116632
0.9343	High Similarity	NPC303644
0.9343	High Similarity	NPC294409
0.9343	High Similarity	NPC209560
0.9343	High Similarity	NPC7013
0.9343	High Similarity	NPC162680
0.9343	High Similarity	NPC317119
0.9343	High Similarity	NPC181124
0.9343	High Similarity	NPC472419
0.9338	High Similarity	NPC156092
0.9338	High Similarity	NPC131039
0.9333	High Similarity	NPC56031
0.9333	High Similarity	NPC192304
0.9333	High Similarity	NPC139813
0.9333	High Similarity	NPC337373
0.9333	High Similarity	NPC188646
0.9333	High Similarity	NPC175098
0.9333	High Similarity	NPC472365
0.9333	High Similarity	NPC263670
0.9333	High Similarity	NPC242294
0.9333	High Similarity	NPC312318
0.9328	High Similarity	NPC475008
0.9328	High Similarity	NPC186097
0.9328	High Similarity	NPC475009
0.9301	High Similarity	NPC329933
0.9296	High Similarity	NPC308200
0.9296	High Similarity	NPC475348
0.9296	High Similarity	NPC261271
0.9291	High Similarity	NPC311144
0.9291	High Similarity	NPC476055
0.9286	High Similarity	NPC202981
0.9281	High Similarity	NPC159275
0.9281	High Similarity	NPC241100
0.9281	High Similarity	NPC253822
0.9281	High Similarity	NPC284550
0.9281	High Similarity	NPC101366
0.9281	High Similarity	NPC129853
0.9281	High Similarity	NPC76445
0.9275	High Similarity	NPC55162
0.9275	High Similarity	NPC279668
0.9275	High Similarity	NPC90665
0.9275	High Similarity	NPC12175
0.9275	High Similarity	NPC278323
0.9275	High Similarity	NPC309154
0.927	High Similarity	NPC476333
0.927	High Similarity	NPC472364
0.927	High Similarity	NPC472367
0.927	High Similarity	NPC473391
0.9259	High Similarity	NPC205468
0.9259	High Similarity	NPC87231
0.9259	High Similarity	NPC257756
0.9259	High Similarity	NPC212631
0.9259	High Similarity	NPC129132
0.9231	High Similarity	NPC152233
0.9231	High Similarity	NPC39195
0.9231	High Similarity	NPC145467
0.9225	High Similarity	NPC299011
0.922	High Similarity	NPC81697
0.922	High Similarity	NPC18585
0.922	High Similarity	NPC117836
0.922	High Similarity	NPC166138
0.922	High Similarity	NPC125894
0.922	High Similarity	NPC113770
0.922	High Similarity	NPC107177
0.922	High Similarity	NPC223812
0.922	High Similarity	NPC106985
0.922	High Similarity	NPC85162
0.922	High Similarity	NPC475705
0.922	High Similarity	NPC77794
0.922	High Similarity	NPC11700
0.922	High Similarity	NPC51887
0.922	High Similarity	NPC476178
0.922	High Similarity	NPC278249
0.9214	High Similarity	NPC321980
0.9214	High Similarity	NPC470087
0.9214	High Similarity	NPC26238
0.9214	High Similarity	NPC470089
0.9214	High Similarity	NPC110969
0.9214	High Similarity	NPC49108
0.9209	High Similarity	NPC55018
0.9209	High Similarity	NPC18260
0.9209	High Similarity	NPC220062
0.9209	High Similarity	NPC301217
0.9209	High Similarity	NPC303633
0.9209	High Similarity	NPC53181
0.9209	High Similarity	NPC96565
0.9209	High Similarity	NPC217186
0.9209	High Similarity	NPC316480
0.9209	High Similarity	NPC470211
0.9209	High Similarity	NPC216978
0.9209	High Similarity	NPC78913
0.9203	High Similarity	NPC322301
0.9203	High Similarity	NPC23870
0.9203	High Similarity	NPC255801
0.9197	High Similarity	NPC234560
0.9197	High Similarity	NPC39426
0.9191	High Similarity	NPC27643
0.9185	High Similarity	NPC64359
0.9185	High Similarity	NPC189106
0.9185	High Similarity	NPC112192
0.9185	High Similarity	NPC262359
0.9185	High Similarity	NPC128348
0.9185	High Similarity	NPC309717
0.9185	High Similarity	NPC164236
0.9185	High Similarity	NPC27490
0.9185	High Similarity	NPC175738
0.9185	High Similarity	NPC308037
0.9185	High Similarity	NPC313618
0.9185	High Similarity	NPC66384
0.9167	High Similarity	NPC473016
0.9167	High Similarity	NPC471114
0.9161	High Similarity	NPC34802
0.9161	High Similarity	NPC10990
0.9161	High Similarity	NPC300988
0.9155	High Similarity	NPC131568
0.9155	High Similarity	NPC216538
0.9155	High Similarity	NPC303185
0.9155	High Similarity	NPC131579
0.9155	High Similarity	NPC473013
0.9155	High Similarity	NPC311741
0.9155	High Similarity	NPC184649
0.9155	High Similarity	NPC326500
0.9155	High Similarity	NPC473015
0.9155	High Similarity	NPC328623
0.9155	High Similarity	NPC235217
0.9155	High Similarity	NPC473014
0.9155	High Similarity	NPC273538
0.9155	High Similarity	NPC234629
0.9149	High Similarity	NPC32739
0.9149	High Similarity	NPC265040
0.9149	High Similarity	NPC10937
0.9149	High Similarity	NPC324436
0.9149	High Similarity	NPC76372
0.9149	High Similarity	NPC223500
0.9149	High Similarity	NPC220998
0.9149	High Similarity	NPC296917
0.9149	High Similarity	NPC64915
0.9149	High Similarity	NPC66515
0.9149	High Similarity	NPC182852

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 NPC265178 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
0.9197	High Similarity	NPD1510	Phase 2
0.9191	High Similarity	NPD1607	Approved
0.9185	High Similarity	NPD1240	Approved
0.9155	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD1550	Clinical (unspecified phase)
0.8929	High Similarity	NPD1552	Clinical (unspecified phase)
0.8865	High Similarity	NPD1549	Phase 2
0.8859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8759	High Similarity	NPD7410	Clinical (unspecified phase)
0.8723	High Similarity	NPD2796	Approved
0.8716	High Similarity	NPD4380	Phase 2
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8643	High Similarity	NPD6651	Approved
0.8601	High Similarity	NPD970	Clinical (unspecified phase)
0.8543	High Similarity	NPD7819	Suspended
0.8533	High Similarity	NPD7411	Suspended
0.8497	Intermediate Similarity	NPD7075	Discontinued
0.8483	Intermediate Similarity	NPD3750	Approved
0.8477	Intermediate Similarity	NPD1934	Approved
0.8471	Intermediate Similarity	NPD7473	Discontinued
0.8435	Intermediate Similarity	NPD1511	Approved
0.8421	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD2801	Approved
0.8414	Intermediate Similarity	NPD2800	Approved
0.8397	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8322	Intermediate Similarity	NPD1512	Approved
0.8312	Intermediate Similarity	NPD7768	Phase 2
0.8311	Intermediate Similarity	NPD6799	Approved
0.8291	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2533	Approved
0.8255	Intermediate Similarity	NPD2534	Approved
0.8255	Intermediate Similarity	NPD2532	Approved
0.8235	Intermediate Similarity	NPD6801	Discontinued
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8201	Intermediate Similarity	NPD2798	Approved
0.8194	Intermediate Similarity	NPD3882	Suspended
0.8163	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD3749	Approved
0.8138	Intermediate Similarity	NPD2799	Discontinued
0.8138	Intermediate Similarity	NPD3748	Approved
0.8108	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6100	Approved
0.8082	Intermediate Similarity	NPD6099	Approved
0.8067	Intermediate Similarity	NPD7390	Discontinued
0.8063	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6166	Phase 2
0.8063	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5494	Approved
0.8027	Intermediate Similarity	NPD2344	Approved
0.8025	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3817	Phase 2
0.7987	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD943	Approved
0.7972	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD4908	Phase 1
0.7919	Intermediate Similarity	NPD1243	Approved
0.7914	Intermediate Similarity	NPD3972	Approved
0.7867	Intermediate Similarity	NPD4628	Phase 3
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7853	Intermediate Similarity	NPD3818	Discontinued
0.7847	Intermediate Similarity	NPD3268	Approved
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.7842	Intermediate Similarity	NPD1201	Approved
0.7818	Intermediate Similarity	NPD5953	Discontinued
0.7815	Intermediate Similarity	NPD2309	Approved
0.7806	Intermediate Similarity	NPD3226	Approved
0.7806	Intermediate Similarity	NPD7458	Discontinued
0.7805	Intermediate Similarity	NPD7054	Approved
0.78	Intermediate Similarity	NPD2654	Approved
0.7792	Intermediate Similarity	NPD5403	Approved
0.7792	Intermediate Similarity	NPD920	Approved
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7472	Approved
0.7748	Intermediate Similarity	NPD7003	Approved
0.7746	Intermediate Similarity	NPD2797	Approved
0.7746	Intermediate Similarity	NPD1470	Approved
0.7746	Intermediate Similarity	NPD1203	Approved
0.7736	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2313	Discontinued
0.7711	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD7286	Phase 2
0.7677	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7665	Intermediate Similarity	NPD7251	Discontinued
0.7662	Intermediate Similarity	NPD5401	Approved
0.7662	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7808	Phase 3
0.7607	Intermediate Similarity	NPD5710	Approved
0.7607	Intermediate Similarity	NPD5711	Approved
0.7606	Intermediate Similarity	NPD4749	Approved
0.76	Intermediate Similarity	NPD5404	Approved
0.76	Intermediate Similarity	NPD5408	Approved
0.76	Intermediate Similarity	NPD5406	Approved
0.76	Intermediate Similarity	NPD5405	Approved
0.7589	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD6832	Phase 2
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.7562	Intermediate Similarity	NPD5402	Approved
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7554	Intermediate Similarity	NPD1548	Phase 1
0.7552	Intermediate Similarity	NPD1876	Approved
0.7548	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4361	Phase 2
0.7543	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9493	Approved
0.7535	Intermediate Similarity	NPD9717	Approved
0.7535	Intermediate Similarity	NPD1608	Approved
0.7534	Intermediate Similarity	NPD4625	Phase 3
0.7533	Intermediate Similarity	NPD4308	Phase 3
0.7533	Intermediate Similarity	NPD7033	Discontinued
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3764	Approved
0.7465	Intermediate Similarity	NPD422	Phase 1
0.7453	Intermediate Similarity	NPD4288	Approved
0.7448	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD37	Approved
0.7431	Intermediate Similarity	NPD1283	Approved
0.7429	Intermediate Similarity	NPD9545	Approved
0.7423	Intermediate Similarity	NPD919	Approved
0.7417	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7376	Intermediate Similarity	NPD1651	Approved
0.7375	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5124	Phase 1
0.7324	Intermediate Similarity	NPD17	Approved
0.732	Intermediate Similarity	NPD1471	Phase 3
0.7317	Intermediate Similarity	NPD6234	Discontinued
0.731	Intermediate Similarity	NPD3225	Approved
0.7305	Intermediate Similarity	NPD2403	Approved
0.7301	Intermediate Similarity	NPD4967	Phase 2
0.7301	Intermediate Similarity	NPD4965	Approved
0.7301	Intermediate Similarity	NPD4966	Approved
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD4307	Phase 2
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD411	Approved
0.7241	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8434	Phase 2
0.7239	Intermediate Similarity	NPD2296	Approved
0.7235	Intermediate Similarity	NPD1729	Discontinued
0.723	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7199	Phase 2
0.7222	Intermediate Similarity	NPD1281	Approved
0.7219	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD1933	Approved
0.7215	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2932	Approved
0.7203	Intermediate Similarity	NPD4626	Approved
0.7197	Intermediate Similarity	NPD3300	Phase 2
0.7194	Intermediate Similarity	NPD1241	Discontinued
0.7182	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5760	Phase 2
0.7178	Intermediate Similarity	NPD5761	Phase 2
0.717	Intermediate Similarity	NPD6273	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7163	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2861	Phase 2
0.7162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4287	Approved
0.7153	Intermediate Similarity	NPD4750	Phase 3
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD1296	Phase 2
0.7123	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7105	Intermediate Similarity	NPD447	Suspended
0.7088	Intermediate Similarity	NPD6780	Approved
0.7088	Intermediate Similarity	NPD6776	Approved
0.7088	Intermediate Similarity	NPD6781	Approved

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