NPASS Compound

Structure

CID241891 OpenBabel06191716042D 24 25 0 0 0 0 0 0 0 0999 V2000 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 7.7942 1.5000 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 12.1244 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 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 11.2583 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 1.5000 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 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 12 19 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.22
Volume:	373.717
LogP:	6.877
LogD:	4.532
LogS:	-3.81
# Rotatable Bonds:	11
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	1.916
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.037
MDCK Permeability:	1.2109974704799242e-05
Pgp-inhibitor:	0.209
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	98.96817779541016%
Volume Distribution (VD):	2.147
Pgp-substrate:	0.42286860942840576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.914
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	8.431
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.437
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.785
Skin Sensitization:	0.969
Carcinogencity:	0.031
Eye Corrosion:	0.929
Eye Irritation:	0.983
Respiratory Toxicity:	0.678

Download Data

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

Natural Product: NPC241891

Natural Product ID:	NPC241891
*Common Name:**	5-(10'-Phenyldecyl)-Resorcinol
IUPAC Name:	5-(10-phenyldecyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	DOAKROJPUDWPEL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H30O2/c23-21-16-20(17-22(24)18-21)15-9-6-4-2-1-3-5-8-12-19-13-10-7-11-14-19/h7,10-11,13-14,16-18,23-24H,1-6,8-9,12,15H2
SMILES:	C(CCCCCc1cc(cc(c1)O)O)CCCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479019
PubChem CID:	44575634
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO11253	Knema glomerata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201311]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11344	Pilea cavaleriei	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6734	Gladiolus atroviolaceus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO987	Cruciata taurica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12319	Xanthogaleruca luteola	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4632	Crataegus pyracantha	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4339	Carthamus oxyacanthus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7911	Bignonia gracilis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7502	Salpa thompsoni	Species	Salpidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10974	Acarus immobilis	Species	Acaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO561	Lindsaea chienii	Species	Lindsaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11121	Myrothamnus flabellifolia	Species	Myrothamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10410	Zephyranthes andersoniana	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2600	Alicyclobacillus acidoterrestris	Species	Alicyclobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11253	Knema glomerata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7774	Cliona copiosa	Species	Clionaidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9687	Evernia esorediosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1623	Acarospora gobiensis	Species	Acarosporaceae	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
ED50	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.49	ug ml-1	PMID[479454]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.69	ug ml-1	PMID[479454]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	3.24	ug ml-1	PMID[479454]
NPT140	Organism	Artemia	Artemia	LC50	=	0.47	ug.mL-1	PMID[479454]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	T/C	=	62.0	%	PMID[479454]

☑ 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 NPC241891 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	306
0.1-0.2	1703
0.2-0.3	4962
0.3-0.4	14154
0.4-0.5	4792
0.5-0.6	8241
0.6-0.7	6428
0.7-0.8	1747
0.8-0.85	215
0.85-0.9	71
0.9-0.95	58
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC134829
0.9796	High Similarity	NPC118286
0.9796	High Similarity	NPC470700
0.9796	High Similarity	NPC302681
0.9796	High Similarity	NPC39097
0.9796	High Similarity	NPC39664
0.9796	High Similarity	NPC109691
0.9792	High Similarity	NPC100340
0.9792	High Similarity	NPC143659
0.9697	High Similarity	NPC54844
0.9694	High Similarity	NPC246056
0.9688	High Similarity	NPC10588
0.9592	High Similarity	NPC102216
0.9592	High Similarity	NPC30506
0.9588	High Similarity	NPC284011
0.9588	High Similarity	NPC72947
0.9505	High Similarity	NPC19808
0.9505	High Similarity	NPC33728
0.949	High Similarity	NPC249828
0.949	High Similarity	NPC302219
0.949	High Similarity	NPC146798
0.949	High Similarity	NPC94351
0.949	High Similarity	NPC24404
0.949	High Similarity	NPC168303
0.949	High Similarity	NPC71002
0.949	High Similarity	NPC85479
0.949	High Similarity	NPC242342
0.949	High Similarity	NPC222522
0.949	High Similarity	NPC53051
0.949	High Similarity	NPC313030
0.949	High Similarity	NPC106396
0.9485	High Similarity	NPC166761
0.9479	High Similarity	NPC291789
0.9406	High Similarity	NPC174981
0.9388	High Similarity	NPC24407
0.9388	High Similarity	NPC11280
0.9388	High Similarity	NPC294186
0.9388	High Similarity	NPC192032
0.9388	High Similarity	NPC166313
0.9388	High Similarity	NPC137415
0.9388	High Similarity	NPC147310
0.932	High Similarity	NPC224527
0.932	High Similarity	NPC225679
0.932	High Similarity	NPC4493
0.932	High Similarity	NPC476632
0.932	High Similarity	NPC165770
0.93	High Similarity	NPC474839
0.9286	High Similarity	NPC161571
0.9286	High Similarity	NPC275053
0.9286	High Similarity	NPC248573
0.9231	High Similarity	NPC166995
0.9231	High Similarity	NPC43525
0.92	High Similarity	NPC119860
0.9167	High Similarity	NPC76938
0.9143	High Similarity	NPC261343
0.9143	High Similarity	NPC117846
0.9118	High Similarity	NPC61033
0.9118	High Similarity	NPC204901
0.9118	High Similarity	NPC232523
0.9118	High Similarity	NPC158253
0.9118	High Similarity	NPC305603
0.9109	High Similarity	NPC292452
0.9109	High Similarity	NPC37802
0.9072	High Similarity	NPC32714
0.9057	High Similarity	NPC107240
0.9029	High Similarity	NPC63698
0.9029	High Similarity	NPC61885
0.902	High Similarity	NPC99836
0.902	High Similarity	NPC248904
0.902	High Similarity	NPC12640
0.902	High Similarity	NPC201662
0.901	High Similarity	NPC227458
0.901	High Similarity	NPC244513
0.901	High Similarity	NPC218879
0.8972	High Similarity	NPC53906
0.8972	High Similarity	NPC84999
0.8972	High Similarity	NPC246760
0.8962	High Similarity	NPC23804
0.8952	High Similarity	NPC268032
0.8942	High Similarity	NPC186385
0.8942	High Similarity	NPC202647
0.8942	High Similarity	NPC299568
0.89	High Similarity	NPC294741
0.8879	High Similarity	NPC276737
0.8879	High Similarity	NPC22610
0.8878	High Similarity	NPC274678
0.8866	High Similarity	NPC295295
0.8857	High Similarity	NPC475018
0.8854	High Similarity	NPC192
0.8807	High Similarity	NPC69261
0.8807	High Similarity	NPC219070
0.8807	High Similarity	NPC470759
0.8807	High Similarity	NPC33270
0.8807	High Similarity	NPC15860
0.8807	High Similarity	NPC470760
0.8807	High Similarity	NPC474933
0.8807	High Similarity	NPC127894
0.8796	High Similarity	NPC808
0.8776	High Similarity	NPC151715
0.875	High Similarity	NPC176527
0.8727	High Similarity	NPC144343
0.8727	High Similarity	NPC190514
0.8725	High Similarity	NPC168393
0.8716	High Similarity	NPC150624
0.8716	High Similarity	NPC141090
0.8716	High Similarity	NPC115808
0.8716	High Similarity	NPC114064
0.8687	High Similarity	NPC26244
0.8673	High Similarity	NPC210497
0.8673	High Similarity	NPC94139
0.8673	High Similarity	NPC3358
0.8673	High Similarity	NPC147284
0.8673	High Similarity	NPC306884
0.8673	High Similarity	NPC162314
0.8667	High Similarity	NPC114392
0.8667	High Similarity	NPC34864
0.8667	High Similarity	NPC105727
0.8667	High Similarity	NPC58427
0.8649	High Similarity	NPC184302
0.8641	High Similarity	NPC323810
0.8636	High Similarity	NPC277588
0.8624	High Similarity	NPC167934
0.8614	High Similarity	NPC80027
0.8611	High Similarity	NPC319803
0.86	High Similarity	NPC132271
0.86	High Similarity	NPC292730
0.86	High Similarity	NPC473388
0.86	High Similarity	NPC216520
0.86	High Similarity	NPC82664
0.8571	High Similarity	NPC45040
0.8571	High Similarity	NPC223451
0.8571	High Similarity	NPC69006
0.8559	High Similarity	NPC48781
0.8559	High Similarity	NPC9592
0.8532	High Similarity	NPC228287
0.8532	High Similarity	NPC180508
0.8529	High Similarity	NPC213730
0.8505	High Similarity	NPC94045
0.8505	High Similarity	NPC168657
0.8505	High Similarity	NPC2682
0.8496	Intermediate Similarity	NPC24125
0.8482	Intermediate Similarity	NPC217174
0.8482	Intermediate Similarity	NPC191866
0.8476	Intermediate Similarity	NPC67250
0.8468	Intermediate Similarity	NPC50521
0.8468	Intermediate Similarity	NPC195466
0.8468	Intermediate Similarity	NPC244816
0.8468	Intermediate Similarity	NPC221549
0.8455	Intermediate Similarity	NPC472893
0.8454	Intermediate Similarity	NPC27974
0.8447	Intermediate Similarity	NPC91461
0.8447	Intermediate Similarity	NPC12221
0.8447	Intermediate Similarity	NPC7686
0.8447	Intermediate Similarity	NPC40258
0.844	Intermediate Similarity	NPC162113
0.844	Intermediate Similarity	NPC263753
0.844	Intermediate Similarity	NPC62546
0.8431	Intermediate Similarity	NPC92730
0.8431	Intermediate Similarity	NPC132078
0.8431	Intermediate Similarity	NPC51333
0.8431	Intermediate Similarity	NPC216468
0.8431	Intermediate Similarity	NPC78119
0.8426	Intermediate Similarity	NPC296920
0.8426	Intermediate Similarity	NPC90520
0.8421	Intermediate Similarity	NPC237667
0.8421	Intermediate Similarity	NPC476633
0.84	Intermediate Similarity	NPC128062
0.8393	Intermediate Similarity	NPC206
0.8378	Intermediate Similarity	NPC54507
0.8378	Intermediate Similarity	NPC229147
0.8378	Intermediate Similarity	NPC85292
0.8378	Intermediate Similarity	NPC123559
0.8365	Intermediate Similarity	NPC315022
0.8365	Intermediate Similarity	NPC168829
0.8364	Intermediate Similarity	NPC249270
0.835	Intermediate Similarity	NPC248396
0.835	Intermediate Similarity	NPC48730
0.835	Intermediate Similarity	NPC129373
0.8349	Intermediate Similarity	NPC473521
0.8349	Intermediate Similarity	NPC280606
0.8348	Intermediate Similarity	NPC120172
0.8348	Intermediate Similarity	NPC77789
0.8348	Intermediate Similarity	NPC18128
0.8333	Intermediate Similarity	NPC474073
0.8333	Intermediate Similarity	NPC32674
0.8333	Intermediate Similarity	NPC152097
0.8333	Intermediate Similarity	NPC156313
0.8333	Intermediate Similarity	NPC242178
0.8333	Intermediate Similarity	NPC224870
0.8333	Intermediate Similarity	NPC225464
0.8333	Intermediate Similarity	NPC102639
0.8318	Intermediate Similarity	NPC95344
0.8318	Intermediate Similarity	NPC11554
0.83	Intermediate Similarity	NPC55903
0.83	Intermediate Similarity	NPC271440
0.8288	Intermediate Similarity	NPC185541
0.8288	Intermediate Similarity	NPC464
0.8288	Intermediate Similarity	NPC232165
0.8286	Intermediate Similarity	NPC471511
0.8286	Intermediate Similarity	NPC288411

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 NPC241891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	1011
0.2-0.3	1278
0.3-0.4	2952
0.4-0.5	1930
0.5-0.6	1159
0.6-0.7	446
0.7-0.8	54
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD1242	Phase 1
0.8942	High Similarity	NPD4750	Phase 3
0.8812	High Similarity	NPD846	Approved
0.8812	High Similarity	NPD940	Approved
0.8687	High Similarity	NPD2860	Approved
0.8687	High Similarity	NPD2859	Approved
0.8614	High Similarity	NPD3020	Approved
0.8586	High Similarity	NPD2933	Approved
0.8586	High Similarity	NPD2934	Approved
0.8317	Intermediate Similarity	NPD844	Approved
0.8241	Intermediate Similarity	NPD3021	Approved
0.8241	Intermediate Similarity	NPD3022	Approved
0.8058	Intermediate Similarity	NPD288	Approved
0.8039	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD9089	Approved
0.789	Intermediate Similarity	NPD2342	Discontinued
0.7869	Intermediate Similarity	NPD4625	Phase 3
0.7869	Intermediate Similarity	NPD3027	Phase 3
0.7857	Intermediate Similarity	NPD7635	Approved
0.7815	Intermediate Similarity	NPD4749	Approved
0.7812	Intermediate Similarity	NPD9093	Approved
0.7797	Intermediate Similarity	NPD1610	Phase 2
0.7767	Intermediate Similarity	NPD845	Approved
0.7759	Intermediate Similarity	NPD1548	Phase 1
0.7748	Intermediate Similarity	NPD1792	Phase 2
0.7677	Intermediate Similarity	NPD111	Approved
0.7642	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4908	Phase 1
0.7636	Intermediate Similarity	NPD1445	Approved
0.7636	Intermediate Similarity	NPD1444	Approved
0.7561	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD6671	Approved
0.748	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD2228	Approved
0.7478	Intermediate Similarity	NPD2234	Approved
0.7478	Intermediate Similarity	NPD2229	Approved
0.7458	Intermediate Similarity	NPD3091	Approved
0.7453	Intermediate Similarity	NPD1809	Phase 2
0.7451	Intermediate Similarity	NPD9094	Approved
0.7422	Intermediate Similarity	NPD2568	Approved
0.7414	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD943	Approved
0.7402	Intermediate Similarity	NPD1613	Approved
0.7402	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4093	Discontinued
0.7381	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3092	Approved
0.7355	Intermediate Similarity	NPD1201	Approved
0.7333	Intermediate Similarity	NPD4059	Approved
0.7333	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2286	Discontinued
0.7333	Intermediate Similarity	NPD3019	Approved
0.7333	Intermediate Similarity	NPD2932	Approved
0.7321	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD9273	Approved
0.728	Intermediate Similarity	NPD2861	Phase 2
0.7258	Intermediate Similarity	NPD3094	Phase 2
0.7236	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD2983	Phase 2
0.7236	Intermediate Similarity	NPD2982	Phase 2
0.7213	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD422	Phase 1
0.7207	Intermediate Similarity	NPD9500	Approved
0.72	Intermediate Similarity	NPD858	Approved
0.72	Intermediate Similarity	NPD859	Approved
0.72	Intermediate Similarity	NPD602	Approved
0.72	Intermediate Similarity	NPD599	Approved
0.7179	Intermediate Similarity	NPD5283	Phase 1
0.7167	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD228	Approved
0.7154	Intermediate Similarity	NPD2981	Phase 2
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.713	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6099	Approved
0.7121	Intermediate Similarity	NPD6100	Approved
0.712	Intermediate Similarity	NPD1470	Approved
0.7119	Intermediate Similarity	NPD1791	Approved
0.7119	Intermediate Similarity	NPD1793	Approved
0.7097	Intermediate Similarity	NPD4659	Approved
0.7094	Intermediate Similarity	NPD9379	Approved
0.7094	Intermediate Similarity	NPD9377	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7069	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6584	Phase 3
0.7054	Intermediate Similarity	NPD6405	Approved
0.7054	Intermediate Similarity	NPD6407	Approved
0.7049	Intermediate Similarity	NPD4589	Approved
0.7049	Intermediate Similarity	NPD1751	Approved
0.7049	Intermediate Similarity	NPD3095	Discontinued
0.7045	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5310	Approved
0.704	Intermediate Similarity	NPD5311	Approved
0.7025	Intermediate Similarity	NPD5303	Approved
0.7025	Intermediate Similarity	NPD5304	Approved
0.7016	Intermediate Similarity	NPD2233	Approved
0.7016	Intermediate Similarity	NPD2232	Approved
0.7016	Intermediate Similarity	NPD2562	Approved
0.7016	Intermediate Similarity	NPD1608	Approved
0.7016	Intermediate Similarity	NPD2230	Approved
0.7016	Intermediate Similarity	NPD2561	Approved
0.7	Intermediate Similarity	NPD2238	Phase 2
0.7	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1240	Approved
0.6992	Remote Similarity	NPD1980	Approved
0.6992	Remote Similarity	NPD1981	Approved
0.6992	Remote Similarity	NPD1983	Approved
0.6991	Remote Similarity	NPD9608	Approved
0.6991	Remote Similarity	NPD9610	Approved
0.6984	Remote Similarity	NPD3053	Approved
0.6984	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4103	Phase 2
0.6984	Remote Similarity	NPD3055	Approved
0.6983	Remote Similarity	NPD5451	Approved
0.6977	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD9618	Approved
0.6975	Remote Similarity	NPD497	Approved
0.697	Remote Similarity	NPD9088	Approved
0.6917	Remote Similarity	NPD709	Approved
0.6917	Remote Similarity	NPD1510	Phase 2
0.6912	Remote Similarity	NPD3892	Phase 2
0.6911	Remote Similarity	NPD9384	Approved
0.6911	Remote Similarity	NPD9381	Approved
0.6903	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2684	Approved
0.6894	Remote Similarity	NPD1607	Approved
0.6891	Remote Similarity	NPD498	Approved
0.6891	Remote Similarity	NPD495	Approved
0.6891	Remote Similarity	NPD496	Approved
0.6885	Remote Similarity	NPD7330	Discontinued
0.6884	Remote Similarity	NPD7390	Discontinued
0.688	Remote Similarity	NPD2235	Phase 2
0.688	Remote Similarity	NPD9269	Phase 2
0.688	Remote Similarity	NPD2231	Phase 2
0.6875	Remote Similarity	NPD5736	Approved
0.687	Remote Similarity	NPD1555	Discontinued
0.687	Remote Similarity	NPD3059	Approved
0.687	Remote Similarity	NPD3061	Approved
0.687	Remote Similarity	NPD3062	Approved
0.6869	Remote Similarity	NPD9294	Approved
0.6866	Remote Similarity	NPD5404	Approved
0.6866	Remote Similarity	NPD5406	Approved
0.6866	Remote Similarity	NPD5408	Approved
0.6866	Remote Similarity	NPD5405	Approved
0.6864	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.686	Remote Similarity	NPD405	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2797	Approved
0.685	Remote Similarity	NPD1164	Approved
0.6846	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD9268	Approved
0.6825	Remote Similarity	NPD6582	Phase 2
0.6825	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6583	Phase 3
0.6825	Remote Similarity	NPD1755	Approved
0.681	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5535	Approved
0.6803	Remote Similarity	NPD16	Approved
0.6803	Remote Similarity	NPD9616	Approved
0.6803	Remote Similarity	NPD9615	Approved
0.6803	Remote Similarity	NPD856	Approved
0.6803	Remote Similarity	NPD9613	Approved
0.6797	Remote Similarity	NPD2195	Approved
0.6797	Remote Similarity	NPD2194	Approved
0.6788	Remote Similarity	NPD3750	Approved
0.6788	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2667	Approved
0.6774	Remote Similarity	NPD17	Approved
0.6774	Remote Similarity	NPD2668	Approved
0.6774	Remote Similarity	NPD4626	Approved
0.6772	Remote Similarity	NPD6696	Suspended
0.6769	Remote Similarity	NPD5156	Approved
0.6769	Remote Similarity	NPD5155	Approved
0.6767	Remote Similarity	NPD5314	Approved
0.6754	Remote Similarity	NPD4658	Approved
0.6754	Remote Similarity	NPD4656	Approved
0.6752	Remote Similarity	NPD74	Approved
0.6752	Remote Similarity	NPD9266	Approved
0.675	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1759	Phase 1
0.6748	Remote Similarity	NPD316	Approved
0.6746	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3635	Approved
0.6744	Remote Similarity	NPD3636	Approved
0.6744	Remote Similarity	NPD3637	Approved
0.6742	Remote Similarity	NPD4060	Phase 1
0.6742	Remote Similarity	NPD6346	Approved
0.6741	Remote Similarity	NPD2935	Discontinued
0.6726	Remote Similarity	NPD1616	Discontinued
0.672	Remote Similarity	NPD3023	Approved
0.672	Remote Similarity	NPD3026	Approved
0.672	Remote Similarity	NPD3847	Discontinued
0.672	Remote Similarity	NPD3421	Phase 3
0.6719	Remote Similarity	NPD1129	Approved
0.6719	Remote Similarity	NPD1133	Approved
0.6719	Remote Similarity	NPD1135	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