NPASS Compound

Structure

CID134829 OpenBabel06191715492D 26 27 0 0 0 0 0 0 0 0999 V2000 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -1.7321 4.0000 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 0.8660 2.5000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.0000 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 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 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 21 1 0 0 0 0 15 21 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.26
Volume:	408.309
LogP:	7.733
LogD:	4.701
LogS:	-3.77
# Rotatable Bonds:	13
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	1.913
Fsp3:	0.5
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:	-5.087
MDCK Permeability:	1.1243632798141334e-05
Pgp-inhibitor:	0.208
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	99.48583984375%
Volume Distribution (VD):	2.579
Pgp-substrate:	0.2882504463195801%

ADMET: Metabolism

CYP1A2-inhibitor:	0.743
CYP1A2-substrate:	0.187
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.958
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	7.695
Half-life (T1/2):	0.581

ADMET: Toxicity

hERG Blockers:	0.56
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.78
Skin Sensitization:	0.971
Carcinogencity:	0.026
Eye Corrosion:	0.935
Eye Irritation:	0.979
Respiratory Toxicity:	0.686

Download Data

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

Natural Product: NPC134829

Natural Product ID:	NPC134829
*Common Name:**	5-(12'-Phenyldodecyl)-Resorcinol
IUPAC Name:	5-(12-phenyldodecyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	LBWBDHYIXVJYGM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H34O2/c25-23-18-22(19-24(26)20-23)17-11-8-6-4-2-1-3-5-7-10-14-21-15-12-9-13-16-21/h9,12-13,15-16,18-20,25-26H,1-8,10-11,14,17H2
SMILES:	C(CCCCCCc1cc(cc(c1)O)O)CCCCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516904
PubChem CID:	44575635
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]
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]
NPO561	Lindsaea chienii	Species	Lindsaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10974	Acarus immobilis	Species	Acaridae	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]
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]

☑ 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	=	3.26	ug ml-1	PMID[572873]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.84	ug ml-1	PMID[572873]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.87	ug ml-1	PMID[572873]
NPT140	Organism	Artemia	Artemia	LC50	=	0.33	ug.mL-1	PMID[572873]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	T/C	=	45.0	%	PMID[572873]

☑ 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 NPC134829 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
0.9898	High Similarity	NPC302681
0.9898	High Similarity	NPC39097
0.9898	High Similarity	NPC39664
0.9898	High Similarity	NPC109691
0.9898	High Similarity	NPC118286
0.9898	High Similarity	NPC470700
0.9897	High Similarity	NPC241891
0.9798	High Similarity	NPC54844
0.9796	High Similarity	NPC246056
0.9691	High Similarity	NPC100340
0.9691	High Similarity	NPC143659
0.9691	High Similarity	NPC284011
0.9691	High Similarity	NPC72947
0.9592	High Similarity	NPC146798
0.9592	High Similarity	NPC94351
0.9592	High Similarity	NPC85479
0.9592	High Similarity	NPC302219
0.9592	High Similarity	NPC106396
0.9592	High Similarity	NPC24404
0.9592	High Similarity	NPC313030
0.9592	High Similarity	NPC222522
0.9592	High Similarity	NPC249828
0.9592	High Similarity	NPC242342
0.9592	High Similarity	NPC53051
0.9592	High Similarity	NPC168303
0.9592	High Similarity	NPC71002
0.9588	High Similarity	NPC10588
0.9495	High Similarity	NPC30506
0.9495	High Similarity	NPC102216
0.949	High Similarity	NPC166313
0.949	High Similarity	NPC137415
0.949	High Similarity	NPC11280
0.949	High Similarity	NPC147310
0.949	High Similarity	NPC24407
0.949	High Similarity	NPC294186
0.949	High Similarity	NPC192032
0.9412	High Similarity	NPC19808
0.9412	High Similarity	NPC33728
0.9388	High Similarity	NPC166761
0.9381	High Similarity	NPC291789
0.9327	High Similarity	NPC166995
0.9314	High Similarity	NPC174981
0.9231	High Similarity	NPC225679
0.9231	High Similarity	NPC4493
0.9231	High Similarity	NPC476632
0.9231	High Similarity	NPC224527
0.9231	High Similarity	NPC165770
0.9216	High Similarity	NPC158253
0.9216	High Similarity	NPC305603
0.9216	High Similarity	NPC204901
0.9216	High Similarity	NPC61033
0.9216	High Similarity	NPC232523
0.9208	High Similarity	NPC474839
0.9192	High Similarity	NPC248573
0.9192	High Similarity	NPC275053
0.9192	High Similarity	NPC161571
0.9175	High Similarity	NPC32714
0.9143	High Similarity	NPC43525
0.9118	High Similarity	NPC201662
0.9118	High Similarity	NPC12640
0.9118	High Similarity	NPC99836
0.9109	High Similarity	NPC119860
0.9072	High Similarity	NPC76938
0.9057	High Similarity	NPC117846
0.9057	High Similarity	NPC23804
0.9057	High Similarity	NPC261343
0.902	High Similarity	NPC37802
0.902	High Similarity	NPC292452
0.8972	High Similarity	NPC107240
0.8942	High Similarity	NPC63698
0.8942	High Similarity	NPC61885
0.8932	High Similarity	NPC248904
0.8922	High Similarity	NPC227458
0.8922	High Similarity	NPC244513
0.8922	High Similarity	NPC218879
0.8899	High Similarity	NPC470760
0.8899	High Similarity	NPC127894
0.8899	High Similarity	NPC15860
0.8899	High Similarity	NPC219070
0.8899	High Similarity	NPC470759
0.8889	High Similarity	NPC53906
0.8889	High Similarity	NPC84999
0.8889	High Similarity	NPC246760
0.8868	High Similarity	NPC268032
0.8857	High Similarity	NPC186385
0.8857	High Similarity	NPC202647
0.8857	High Similarity	NPC299568
0.8812	High Similarity	NPC294741
0.8807	High Similarity	NPC114064
0.8807	High Similarity	NPC115808
0.8796	High Similarity	NPC22610
0.8796	High Similarity	NPC276737
0.8788	High Similarity	NPC274678
0.8776	High Similarity	NPC162314
0.8776	High Similarity	NPC210497
0.8776	High Similarity	NPC295295
0.8776	High Similarity	NPC147284
0.8776	High Similarity	NPC94139
0.8776	High Similarity	NPC3358
0.8776	High Similarity	NPC306884
0.8774	High Similarity	NPC475018
0.8763	High Similarity	NPC192
0.8727	High Similarity	NPC69261
0.8727	High Similarity	NPC33270
0.8727	High Similarity	NPC474933
0.8716	High Similarity	NPC808
0.8687	High Similarity	NPC151715
0.8667	High Similarity	NPC176527
0.8649	High Similarity	NPC144343
0.8649	High Similarity	NPC190514
0.8649	High Similarity	NPC48781
0.8649	High Similarity	NPC9592
0.8641	High Similarity	NPC168393
0.8636	High Similarity	NPC150624
0.8636	High Similarity	NPC141090
0.86	High Similarity	NPC26244
0.8585	High Similarity	NPC58427
0.8585	High Similarity	NPC114392
0.8585	High Similarity	NPC34864
0.8585	High Similarity	NPC105727
0.8584	High Similarity	NPC24125
0.8571	High Similarity	NPC184302
0.8571	High Similarity	NPC217174
0.8559	High Similarity	NPC277588
0.8558	High Similarity	NPC323810
0.8545	High Similarity	NPC167934
0.8532	High Similarity	NPC62546
0.8532	High Similarity	NPC263753
0.8532	High Similarity	NPC162113
0.8532	High Similarity	NPC319803
0.8529	High Similarity	NPC80027
0.8515	High Similarity	NPC82664
0.8515	High Similarity	NPC473388
0.8515	High Similarity	NPC216520
0.8515	High Similarity	NPC132271
0.8515	High Similarity	NPC292730
0.8509	High Similarity	NPC237667
0.8496	Intermediate Similarity	NPC223451
0.8496	Intermediate Similarity	NPC69006
0.8485	Intermediate Similarity	NPC45040
0.8482	Intermediate Similarity	NPC206
0.8468	Intermediate Similarity	NPC123559
0.8462	Intermediate Similarity	NPC315022
0.8455	Intermediate Similarity	NPC228287
0.8455	Intermediate Similarity	NPC180508
0.8447	Intermediate Similarity	NPC48730
0.8447	Intermediate Similarity	NPC213730
0.8447	Intermediate Similarity	NPC248396
0.8447	Intermediate Similarity	NPC129373
0.8426	Intermediate Similarity	NPC168657
0.8426	Intermediate Similarity	NPC2682
0.8426	Intermediate Similarity	NPC94045
0.8407	Intermediate Similarity	NPC191866
0.8396	Intermediate Similarity	NPC67250
0.8393	Intermediate Similarity	NPC244816
0.8393	Intermediate Similarity	NPC221549
0.8393	Intermediate Similarity	NPC50521
0.8393	Intermediate Similarity	NPC195466
0.8381	Intermediate Similarity	NPC315936
0.8378	Intermediate Similarity	NPC472893
0.8367	Intermediate Similarity	NPC27974
0.8365	Intermediate Similarity	NPC7686
0.8365	Intermediate Similarity	NPC12221
0.8365	Intermediate Similarity	NPC91461
0.8365	Intermediate Similarity	NPC40258
0.8362	Intermediate Similarity	NPC53567
0.835	Intermediate Similarity	NPC51333
0.835	Intermediate Similarity	NPC78119
0.835	Intermediate Similarity	NPC92730
0.835	Intermediate Similarity	NPC132078
0.835	Intermediate Similarity	NPC216468
0.835	Intermediate Similarity	NPC260775
0.8349	Intermediate Similarity	NPC296920
0.8349	Intermediate Similarity	NPC90520
0.8348	Intermediate Similarity	NPC39029
0.8348	Intermediate Similarity	NPC476633
0.8317	Intermediate Similarity	NPC128062
0.8304	Intermediate Similarity	NPC85292
0.8304	Intermediate Similarity	NPC54507
0.8304	Intermediate Similarity	NPC229147
0.8291	Intermediate Similarity	NPC140521
0.8288	Intermediate Similarity	NPC249270
0.8286	Intermediate Similarity	NPC168829
0.8276	Intermediate Similarity	NPC120172
0.8276	Intermediate Similarity	NPC122175
0.8276	Intermediate Similarity	NPC18128
0.8276	Intermediate Similarity	NPC77789
0.8273	Intermediate Similarity	NPC280606
0.8273	Intermediate Similarity	NPC473521
0.8269	Intermediate Similarity	NPC130756
0.8269	Intermediate Similarity	NPC12931
0.8269	Intermediate Similarity	NPC70677
0.8261	Intermediate Similarity	NPC102639
0.8257	Intermediate Similarity	NPC224870
0.8257	Intermediate Similarity	NPC242178
0.8252	Intermediate Similarity	NPC32674
0.8252	Intermediate Similarity	NPC156313
0.8252	Intermediate Similarity	NPC225464
0.8252	Intermediate Similarity	NPC152097
0.8252	Intermediate Similarity	NPC474073

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 NPC134829 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
0.9192	High Similarity	NPD1242	Phase 1
0.8857	High Similarity	NPD4750	Phase 3
0.8725	High Similarity	NPD940	Approved
0.8725	High Similarity	NPD846	Approved
0.86	High Similarity	NPD2859	Approved
0.86	High Similarity	NPD2860	Approved
0.8529	High Similarity	NPD3020	Approved
0.85	High Similarity	NPD2934	Approved
0.85	High Similarity	NPD2933	Approved
0.8235	Intermediate Similarity	NPD844	Approved
0.8165	Intermediate Similarity	NPD3022	Approved
0.8165	Intermediate Similarity	NPD3021	Approved
0.7981	Intermediate Similarity	NPD288	Approved
0.7961	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD7635	Approved
0.7925	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD9089	Approved
0.7818	Intermediate Similarity	NPD2342	Discontinued
0.7805	Intermediate Similarity	NPD3027	Phase 3
0.7805	Intermediate Similarity	NPD4625	Phase 3
0.775	Intermediate Similarity	NPD4749	Approved
0.7732	Intermediate Similarity	NPD9093	Approved
0.7731	Intermediate Similarity	NPD1610	Phase 2
0.7692	Intermediate Similarity	NPD1548	Phase 1
0.7692	Intermediate Similarity	NPD845	Approved
0.7679	Intermediate Similarity	NPD1792	Phase 2
0.76	Intermediate Similarity	NPD111	Approved
0.7586	Intermediate Similarity	NPD6671	Approved
0.7581	Intermediate Similarity	NPD4908	Phase 1
0.7581	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1445	Approved
0.7568	Intermediate Similarity	NPD1444	Approved
0.7561	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3028	Approved
0.7414	Intermediate Similarity	NPD2229	Approved
0.7414	Intermediate Similarity	NPD2228	Approved
0.7414	Intermediate Similarity	NPD2234	Approved
0.7395	Intermediate Similarity	NPD3091	Approved
0.7383	Intermediate Similarity	NPD1809	Phase 2
0.7379	Intermediate Similarity	NPD9094	Approved
0.7364	Intermediate Similarity	NPD2568	Approved
0.735	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1613	Approved
0.7344	Intermediate Similarity	NPD943	Approved
0.7344	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4093	Discontinued
0.7295	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1201	Approved
0.7295	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3092	Approved
0.7273	Intermediate Similarity	NPD3019	Approved
0.7273	Intermediate Similarity	NPD2286	Discontinued
0.7273	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2932	Approved
0.7273	Intermediate Similarity	NPD4059	Approved
0.7257	Intermediate Similarity	NPD968	Approved
0.7248	Intermediate Similarity	NPD9273	Approved
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.72	Intermediate Similarity	NPD3094	Phase 2
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD6099	Approved
0.7177	Intermediate Similarity	NPD2982	Phase 2
0.7177	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2983	Phase 2
0.7154	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD9500	Approved
0.7143	Intermediate Similarity	NPD602	Approved
0.7143	Intermediate Similarity	NPD858	Approved
0.7143	Intermediate Similarity	NPD859	Approved
0.7143	Intermediate Similarity	NPD599	Approved
0.7132	Intermediate Similarity	NPD6405	Approved
0.7132	Intermediate Similarity	NPD6407	Approved
0.712	Intermediate Similarity	NPD5311	Approved
0.712	Intermediate Similarity	NPD5310	Approved
0.7119	Intermediate Similarity	NPD5283	Phase 1
0.7107	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2981	Phase 2
0.7094	Intermediate Similarity	NPD228	Approved
0.7087	Intermediate Similarity	NPD3018	Phase 2
0.7083	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1470	Approved
0.7059	Intermediate Similarity	NPD1793	Approved
0.7059	Intermediate Similarity	NPD1791	Approved
0.7054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4659	Approved
0.7034	Intermediate Similarity	NPD9379	Approved
0.7034	Intermediate Similarity	NPD9377	Approved
0.701	Intermediate Similarity	NPD9087	Approved
0.7009	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6584	Phase 3
0.6992	Remote Similarity	NPD3095	Discontinued
0.6992	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1751	Approved
0.6992	Remote Similarity	NPD4589	Approved
0.6967	Remote Similarity	NPD5303	Approved
0.6967	Remote Similarity	NPD5304	Approved
0.6967	Remote Similarity	NPD7330	Discontinued
0.696	Remote Similarity	NPD2232	Approved
0.696	Remote Similarity	NPD2233	Approved
0.696	Remote Similarity	NPD2561	Approved
0.696	Remote Similarity	NPD2230	Approved
0.696	Remote Similarity	NPD2562	Approved
0.696	Remote Similarity	NPD1608	Approved
0.6953	Remote Similarity	NPD5736	Approved
0.6949	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2238	Phase 2
0.6947	Remote Similarity	NPD1240	Approved
0.6935	Remote Similarity	NPD1980	Approved
0.6935	Remote Similarity	NPD1983	Approved
0.6935	Remote Similarity	NPD1981	Approved
0.693	Remote Similarity	NPD9608	Approved
0.693	Remote Similarity	NPD9610	Approved
0.6929	Remote Similarity	NPD3055	Approved
0.6929	Remote Similarity	NPD4103	Phase 2
0.6929	Remote Similarity	NPD3053	Approved
0.6929	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5451	Approved
0.6917	Remote Similarity	NPD9618	Approved
0.6917	Remote Similarity	NPD497	Approved
0.6917	Remote Similarity	NPD9614	Approved
0.69	Remote Similarity	NPD9088	Approved
0.6866	Remote Similarity	NPD1510	Phase 2
0.6861	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3892	Phase 2
0.686	Remote Similarity	NPD709	Approved
0.6855	Remote Similarity	NPD9384	Approved
0.6855	Remote Similarity	NPD9381	Approved
0.685	Remote Similarity	NPD6696	Suspended
0.6842	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1607	Approved
0.6842	Remote Similarity	NPD5314	Approved
0.6838	Remote Similarity	NPD2684	Approved
0.6835	Remote Similarity	NPD7390	Discontinued
0.6833	Remote Similarity	NPD496	Approved
0.6833	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD495	Approved
0.6833	Remote Similarity	NPD498	Approved
0.6825	Remote Similarity	NPD9269	Phase 2
0.6825	Remote Similarity	NPD2235	Phase 2
0.6825	Remote Similarity	NPD2231	Phase 2
0.6818	Remote Similarity	NPD3061	Approved
0.6818	Remote Similarity	NPD6346	Approved
0.6818	Remote Similarity	NPD1555	Discontinued
0.6818	Remote Similarity	NPD3062	Approved
0.6818	Remote Similarity	NPD3059	Approved
0.6815	Remote Similarity	NPD5405	Approved
0.6815	Remote Similarity	NPD5404	Approved
0.6815	Remote Similarity	NPD5406	Approved
0.6815	Remote Similarity	NPD5408	Approved
0.6803	Remote Similarity	NPD405	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9294	Approved
0.6797	Remote Similarity	NPD2797	Approved
0.6797	Remote Similarity	NPD1164	Approved
0.6794	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7447	Phase 1
0.6774	Remote Similarity	NPD9268	Approved
0.6772	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6583	Phase 3
0.6772	Remote Similarity	NPD6582	Phase 2
0.6772	Remote Similarity	NPD1755	Approved
0.6765	Remote Similarity	NPD7266	Discontinued
0.6754	Remote Similarity	NPD4818	Approved
0.6754	Remote Similarity	NPD4817	Approved
0.6752	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5535	Approved
0.675	Remote Similarity	NPD7843	Approved
0.6748	Remote Similarity	NPD16	Approved
0.6748	Remote Similarity	NPD9613	Approved
0.6748	Remote Similarity	NPD9616	Approved
0.6748	Remote Similarity	NPD9615	Approved
0.6748	Remote Similarity	NPD856	Approved
0.6744	Remote Similarity	NPD2194	Approved
0.6744	Remote Similarity	NPD2195	Approved
0.6742	Remote Similarity	NPD6663	Approved
0.6739	Remote Similarity	NPD3750	Approved
0.6721	Remote Similarity	NPD7157	Approved
0.672	Remote Similarity	NPD17	Approved
0.672	Remote Similarity	NPD2667	Approved
0.672	Remote Similarity	NPD2668	Approved
0.672	Remote Similarity	NPD4626	Approved
0.6718	Remote Similarity	NPD5156	Approved
0.6718	Remote Similarity	NPD5155	Approved
0.6718	Remote Similarity	NPD7095	Approved
0.6696	Remote Similarity	NPD4656	Approved
0.6696	Remote Similarity	NPD4658	Approved
0.6695	Remote Similarity	NPD74	Approved
0.6695	Remote Similarity	NPD9266	Approved
0.6694	Remote Similarity	NPD7741	Discontinued
0.6694	Remote Similarity	NPD316	Approved
0.6694	Remote Similarity	NPD1759	Phase 1
0.6693	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD3636	Approved
0.6692	Remote Similarity	NPD3635	Approved
0.6692	Remote Similarity	NPD3637	Approved
0.6692	Remote Similarity	NPD4060	Phase 1

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