NPASS Compound

Structure

CID232523 OpenBabel06191716032D 24 24 0 0 0 0 0 0 0 0999 V2000 9.5263 -6.5000 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 10.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 1.7321 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 19 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 21 2 0 0 0 0 19 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:	332.27
Volume:	387.546
LogP:	7.095
LogD:	4.798
LogS:	-2.966
# Rotatable Bonds:	13
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.307
Synthetic Accessibility Score:	2.374
Fsp3:	0.636
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:	-4.869
MDCK Permeability:	1.6676814993843436e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	100.0038833618164%
Volume Distribution (VD):	5.255
Pgp-substrate:	0.5223218202590942%

ADMET: Metabolism

CYP1A2-inhibitor:	0.479
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.703
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.217
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	5.655
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.188
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.396
Skin Sensitization:	0.966
Carcinogencity:	0.04
Eye Corrosion:	0.832
Eye Irritation:	0.977
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC232523

Natural Product ID:	NPC232523
*Common Name:**	2-Methyl-5-{8(Z)-Pentadecenyl}Resorcinol
IUPAC Name:	2-methyl-5-[(Z)-pentadec-8-enyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	LDBPJTXLCRXBIJ-HJWRWDBZSA-N
Standard InCHI:	InChI=1S/C22H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-17-21(23)19(2)22(24)18-20/h8-9,17-18,23-24H,3-7,10-16H2,1-2H3/b9-8-
SMILES:	CCCCCC/C=CCCCCCCCc1cc(c(C)c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470556
PubChem CID:	6452209
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
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12510	Aronia arbutifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13070	Clibadium mexiae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	24.0	%	PMID[481341]

☑ 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 NPC232523 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	288
0.1-0.2	1606
0.2-0.3	4685
0.3-0.4	14353
0.4-0.5	5136
0.5-0.6	8801
0.6-0.7	5986
0.7-0.8	1510
0.8-0.85	174
0.85-0.9	89
0.9-0.95	44
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC158253
1.0	High Similarity	NPC204901
0.9899	High Similarity	NPC12640
0.9899	High Similarity	NPC201662
0.9899	High Similarity	NPC99836
0.9798	High Similarity	NPC37802
0.9697	High Similarity	NPC244513
0.9697	High Similarity	NPC227458
0.9697	High Similarity	NPC218879
0.9608	High Similarity	NPC33728
0.9608	High Similarity	NPC19808
0.9596	High Similarity	NPC242342
0.9596	High Similarity	NPC146798
0.9596	High Similarity	NPC94351
0.9596	High Similarity	NPC85479
0.9596	High Similarity	NPC302219
0.9596	High Similarity	NPC106396
0.9596	High Similarity	NPC24404
0.9596	High Similarity	NPC313030
0.9596	High Similarity	NPC222522
0.9596	High Similarity	NPC249828
0.9596	High Similarity	NPC168303
0.9596	High Similarity	NPC71002
0.9596	High Similarity	NPC53051
0.9519	High Similarity	NPC166995
0.951	High Similarity	NPC174981
0.9495	High Similarity	NPC11280
0.9495	High Similarity	NPC294186
0.9495	High Similarity	NPC147310
0.9495	High Similarity	NPC166313
0.9495	High Similarity	NPC284011
0.9495	High Similarity	NPC192032
0.9495	High Similarity	NPC72947
0.9495	High Similarity	NPC24407
0.9495	High Similarity	NPC137415
0.9423	High Similarity	NPC224527
0.9417	High Similarity	NPC299568
0.9417	High Similarity	NPC186385
0.9394	High Similarity	NPC10588
0.9394	High Similarity	NPC166761
0.9245	High Similarity	NPC263753
0.9245	High Similarity	NPC23804
0.9245	High Similarity	NPC117846
0.9223	High Similarity	NPC61033
0.9223	High Similarity	NPC305603
0.9216	High Similarity	NPC134829
0.9126	High Similarity	NPC109691
0.9126	High Similarity	NPC302681
0.9126	High Similarity	NPC470700
0.9126	High Similarity	NPC39097
0.9126	High Similarity	NPC39664
0.9126	High Similarity	NPC118286
0.9118	High Similarity	NPC102216
0.9118	High Similarity	NPC241891
0.9074	High Similarity	NPC246760
0.9074	High Similarity	NPC84999
0.9065	High Similarity	NPC319803
0.9065	High Similarity	NPC261343
0.9057	High Similarity	NPC225679
0.9057	High Similarity	NPC4493
0.9057	High Similarity	NPC476632
0.9057	High Similarity	NPC165770
0.9038	High Similarity	NPC54844
0.9029	High Similarity	NPC246056
0.8972	High Similarity	NPC43525
0.8962	High Similarity	NPC224870
0.8922	High Similarity	NPC143659
0.8922	High Similarity	NPC477685
0.8922	High Similarity	NPC252105
0.8922	High Similarity	NPC100340
0.8911	High Similarity	NPC80027
0.8909	High Similarity	NPC470760
0.8846	High Similarity	NPC474839
0.8829	High Similarity	NPC206
0.8829	High Similarity	NPC144343
0.8829	High Similarity	NPC190514
0.8829	High Similarity	NPC9592
0.8829	High Similarity	NPC48781
0.8824	High Similarity	NPC72729
0.8824	High Similarity	NPC129373
0.8824	High Similarity	NPC248396
0.8824	High Similarity	NPC48730
0.8818	High Similarity	NPC115808
0.8812	High Similarity	NPC6597
0.8812	High Similarity	NPC79241
0.8807	High Similarity	NPC107240
0.8788	High Similarity	NPC94139
0.8788	High Similarity	NPC147284
0.8788	High Similarity	NPC3358
0.8788	High Similarity	NPC306884
0.8788	High Similarity	NPC210497
0.8788	High Similarity	NPC162314
0.8788	High Similarity	NPC295295
0.8774	High Similarity	NPC63698
0.8774	High Similarity	NPC61885
0.8761	High Similarity	NPC24125
0.875	High Similarity	NPC119860
0.875	High Similarity	NPC184302
0.875	High Similarity	NPC30506
0.8738	High Similarity	NPC80800
0.8725	High Similarity	NPC33675
0.8725	High Similarity	NPC260775
0.8725	High Similarity	NPC299762
0.8713	High Similarity	NPC312132
0.8713	High Similarity	NPC259512
0.8687	High Similarity	NPC231150
0.8679	High Similarity	NPC66834
0.8667	High Similarity	NPC47284
0.8667	High Similarity	NPC292452
0.8654	High Similarity	NPC471228
0.8654	High Similarity	NPC235762
0.8641	High Similarity	NPC130756
0.8641	High Similarity	NPC12931
0.8641	High Similarity	NPC174911
0.8641	High Similarity	NPC70677
0.8627	High Similarity	NPC152097
0.8627	High Similarity	NPC291789
0.8624	High Similarity	NPC473521
0.8598	High Similarity	NPC306295
0.8596	High Similarity	NPC218753
0.8586	High Similarity	NPC192
0.8585	High Similarity	NPC53740
0.8585	High Similarity	NPC248904
0.8585	High Similarity	NPC469913
0.8584	High Similarity	NPC191866
0.8571	High Similarity	NPC33270
0.8571	High Similarity	NPC69261
0.8571	High Similarity	NPC475225
0.8559	High Similarity	NPC808
0.8545	High Similarity	NPC162113
0.8545	High Similarity	NPC62546
0.8532	High Similarity	NPC469912
0.8522	High Similarity	NPC39029
0.8519	High Similarity	NPC202647
0.8509	High Similarity	NPC69006
0.8491	Intermediate Similarity	NPC471350
0.8482	Intermediate Similarity	NPC123559
0.8482	Intermediate Similarity	NPC150624
0.8476	Intermediate Similarity	NPC108497
0.8476	Intermediate Similarity	NPC315022
0.8468	Intermediate Similarity	NPC249270
0.8462	Intermediate Similarity	NPC248573
0.8462	Intermediate Similarity	NPC161571
0.8462	Intermediate Similarity	NPC275053
0.8455	Intermediate Similarity	NPC302371
0.8455	Intermediate Similarity	NPC228452
0.8448	Intermediate Similarity	NPC18128
0.8448	Intermediate Similarity	NPC77789
0.8448	Intermediate Similarity	NPC122175
0.8447	Intermediate Similarity	NPC475078
0.844	Intermediate Similarity	NPC168657
0.844	Intermediate Similarity	NPC475018
0.8431	Intermediate Similarity	NPC32714
0.8421	Intermediate Similarity	NPC137294
0.8421	Intermediate Similarity	NPC85895
0.8421	Intermediate Similarity	NPC217174
0.8411	Intermediate Similarity	NPC310456
0.8411	Intermediate Similarity	NPC155072
0.8407	Intermediate Similarity	NPC277588
0.8407	Intermediate Similarity	NPC15860
0.8407	Intermediate Similarity	NPC320864
0.8407	Intermediate Similarity	NPC219070
0.8407	Intermediate Similarity	NPC127894
0.8407	Intermediate Similarity	NPC470759
0.8396	Intermediate Similarity	NPC315936
0.8393	Intermediate Similarity	NPC53906
0.8393	Intermediate Similarity	NPC232165
0.8384	Intermediate Similarity	NPC27974
0.8364	Intermediate Similarity	NPC54373
0.8362	Intermediate Similarity	NPC237667
0.8348	Intermediate Similarity	NPC223451
0.8333	Intermediate Similarity	NPC474352
0.8333	Intermediate Similarity	NPC152415
0.8333	Intermediate Similarity	NPC76938
0.8333	Intermediate Similarity	NPC245187
0.8319	Intermediate Similarity	NPC114064
0.8318	Intermediate Similarity	NPC117115
0.8305	Intermediate Similarity	NPC174729
0.8305	Intermediate Similarity	NPC139774
0.8304	Intermediate Similarity	NPC22610
0.8304	Intermediate Similarity	NPC276737
0.8302	Intermediate Similarity	NPC168393
0.8286	Intermediate Similarity	NPC130103
0.8283	Intermediate Similarity	NPC407
0.8283	Intermediate Similarity	NPC307235
0.8269	Intermediate Similarity	NPC474073
0.8261	Intermediate Similarity	NPC121866
0.825	Intermediate Similarity	NPC473221
0.8246	Intermediate Similarity	NPC50521
0.8246	Intermediate Similarity	NPC221549
0.8246	Intermediate Similarity	NPC244816
0.8246	Intermediate Similarity	NPC474933
0.8235	Intermediate Similarity	NPC131397
0.8235	Intermediate Similarity	NPC55903
0.8235	Intermediate Similarity	NPC29373
0.8235	Intermediate Similarity	NPC476254
0.8235	Intermediate Similarity	NPC105031
0.8224	Intermediate Similarity	NPC272029
0.822	Intermediate Similarity	NPC53567
0.822	Intermediate Similarity	NPC96940

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 NPC232523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	1032
0.2-0.3	1566
0.3-0.4	3004
0.4-0.5	1763
0.5-0.6	1105
0.6-0.7	349
0.7-0.8	45
0.8-0.85	6
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9417	High Similarity	NPD4750	Phase 3
0.9109	High Similarity	NPD846	Approved
0.9109	High Similarity	NPD940	Approved
0.899	High Similarity	NPD844	Approved
0.8713	High Similarity	NPD288	Approved
0.8462	Intermediate Similarity	NPD1242	Phase 1
0.8286	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD4749	Approved
0.8125	Intermediate Similarity	NPD7635	Approved
0.8077	Intermediate Similarity	NPD2859	Approved
0.8077	Intermediate Similarity	NPD2860	Approved
0.8058	Intermediate Similarity	NPD845	Approved
0.8019	Intermediate Similarity	NPD3020	Approved
0.8017	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD2933	Approved
0.7981	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD2934	Approved
0.7967	Intermediate Similarity	NPD4625	Phase 3
0.7903	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2342	Discontinued
0.7759	Intermediate Similarity	NPD6671	Approved
0.7736	Intermediate Similarity	NPD1809	Phase 2
0.7699	Intermediate Similarity	NPD3022	Approved
0.7699	Intermediate Similarity	NPD3021	Approved
0.7677	Intermediate Similarity	NPD9089	Approved
0.7624	Intermediate Similarity	NPD111	Approved
0.7589	Intermediate Similarity	NPD1444	Approved
0.7589	Intermediate Similarity	NPD1445	Approved
0.7576	Intermediate Similarity	NPD9093	Approved
0.7481	Intermediate Similarity	NPD6100	Approved
0.7481	Intermediate Similarity	NPD6099	Approved
0.746	Intermediate Similarity	NPD4908	Phase 1
0.7459	Intermediate Similarity	NPD1610	Phase 2
0.7431	Intermediate Similarity	NPD9273	Approved
0.7419	Intermediate Similarity	NPD6696	Suspended
0.7417	Intermediate Similarity	NPD1548	Phase 1
0.7402	Intermediate Similarity	NPD3027	Phase 3
0.7391	Intermediate Similarity	NPD1792	Phase 2
0.7344	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD422	Phase 1
0.7295	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD3091	Approved
0.7265	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD9094	Approved
0.7177	Intermediate Similarity	NPD3092	Approved
0.7177	Intermediate Similarity	NPD1201	Approved
0.7168	Intermediate Similarity	NPD9500	Approved
0.7165	Intermediate Similarity	NPD859	Approved
0.7165	Intermediate Similarity	NPD858	Approved
0.7165	Intermediate Similarity	NPD599	Approved
0.7165	Intermediate Similarity	NPD602	Approved
0.7154	Intermediate Similarity	NPD3019	Approved
0.7154	Intermediate Similarity	NPD2932	Approved
0.7154	Intermediate Similarity	NPD4059	Approved
0.7143	Intermediate Similarity	NPD2229	Approved
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2228	Approved
0.7143	Intermediate Similarity	NPD2234	Approved
0.7131	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD228	Approved
0.7099	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD943	Approved
0.7099	Intermediate Similarity	NPD1613	Approved
0.7087	Intermediate Similarity	NPD3094	Phase 2
0.7083	Intermediate Similarity	NPD1791	Approved
0.7083	Intermediate Similarity	NPD1793	Approved
0.7083	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD497	Approved
0.7063	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1778	Approved
0.7016	Intermediate Similarity	NPD2286	Discontinued
0.7	Intermediate Similarity	NPD496	Approved
0.7	Intermediate Similarity	NPD495	Approved
0.7	Intermediate Similarity	NPD498	Approved
0.6992	Remote Similarity	NPD1607	Approved
0.6992	Remote Similarity	NPD2568	Approved
0.6991	Remote Similarity	NPD3028	Approved
0.6978	Remote Similarity	NPD7390	Discontinued
0.6977	Remote Similarity	NPD2861	Phase 2
0.6977	Remote Similarity	NPD3018	Phase 2
0.6967	Remote Similarity	NPD7340	Approved
0.696	Remote Similarity	NPD1983	Approved
0.696	Remote Similarity	NPD1981	Approved
0.696	Remote Similarity	NPD1980	Approved
0.6957	Remote Similarity	NPD9610	Approved
0.6957	Remote Similarity	NPD9608	Approved
0.6953	Remote Similarity	NPD1129	Approved
0.6953	Remote Similarity	NPD1133	Approved
0.6953	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1131	Approved
0.6953	Remote Similarity	NPD1470	Approved
0.6953	Remote Similarity	NPD1134	Approved
0.6953	Remote Similarity	NPD1135	Approved
0.6949	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9618	Approved
0.6942	Remote Similarity	NPD9614	Approved
0.6935	Remote Similarity	NPD5691	Approved
0.6935	Remote Similarity	NPD4093	Discontinued
0.6923	Remote Similarity	NPD290	Approved
0.6917	Remote Similarity	NPD9379	Approved
0.6917	Remote Similarity	NPD9377	Approved
0.6894	Remote Similarity	NPD6407	Approved
0.6894	Remote Similarity	NPD6405	Approved
0.6891	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1751	Approved
0.688	Remote Similarity	NPD3095	Discontinued
0.688	Remote Similarity	NPD4589	Approved
0.688	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD9087	Approved
0.6866	Remote Similarity	NPD4097	Suspended
0.6864	Remote Similarity	NPD9266	Approved
0.6864	Remote Similarity	NPD2684	Approved
0.6864	Remote Similarity	NPD74	Approved
0.686	Remote Similarity	NPD1398	Phase 1
0.6855	Remote Similarity	NPD1759	Phase 1
0.6855	Remote Similarity	NPD7330	Discontinued
0.6855	Remote Similarity	NPD5304	Approved
0.6855	Remote Similarity	NPD5303	Approved
0.685	Remote Similarity	NPD2230	Approved
0.685	Remote Similarity	NPD2233	Approved
0.685	Remote Similarity	NPD2232	Approved
0.6846	Remote Similarity	NPD5736	Approved
0.6842	Remote Similarity	NPD1240	Approved
0.6842	Remote Similarity	NPD2238	Phase 2
0.6838	Remote Similarity	NPD5405	Approved
0.6838	Remote Similarity	NPD5404	Approved
0.6838	Remote Similarity	NPD5406	Approved
0.6838	Remote Similarity	NPD5408	Approved
0.6829	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD9493	Approved
0.6825	Remote Similarity	NPD3496	Discontinued
0.6797	Remote Similarity	NPD2983	Phase 2
0.6797	Remote Similarity	NPD2982	Phase 2
0.678	Remote Similarity	NPD9264	Approved
0.678	Remote Similarity	NPD9263	Approved
0.678	Remote Similarity	NPD9267	Approved
0.6777	Remote Similarity	NPD7843	Approved
0.6774	Remote Similarity	NPD1758	Phase 1
0.6774	Remote Similarity	NPD16	Approved
0.6774	Remote Similarity	NPD9613	Approved
0.6774	Remote Similarity	NPD856	Approved
0.6774	Remote Similarity	NPD9616	Approved
0.6774	Remote Similarity	NPD9615	Approved
0.6765	Remote Similarity	NPD9088	Approved
0.6765	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD709	Approved
0.6748	Remote Similarity	NPD7157	Approved
0.6746	Remote Similarity	NPD9381	Approved
0.6746	Remote Similarity	NPD9384	Approved
0.6724	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5283	Phase 1
0.672	Remote Similarity	NPD316	Approved
0.6719	Remote Similarity	NPD9269	Phase 2
0.6719	Remote Similarity	NPD2981	Phase 2
0.6716	Remote Similarity	NPD1555	Discontinued
0.6695	Remote Similarity	NPD968	Approved
0.6694	Remote Similarity	NPD7636	Approved
0.6692	Remote Similarity	NPD2797	Approved
0.669	Remote Similarity	NPD7447	Phase 1
0.6667	Remote Similarity	NPD600	Approved
0.6667	Remote Similarity	NPD596	Approved
0.6667	Remote Similarity	NPD9268	Approved
0.6667	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4659	Approved
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD9294	Approved
0.6667	Remote Similarity	NPD1755	Approved
0.6643	Remote Similarity	NPD3892	Phase 2
0.6642	Remote Similarity	NPD1510	Phase 2
0.6642	Remote Similarity	NPD6663	Approved
0.6642	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2195	Approved
0.6641	Remote Similarity	NPD2194	Approved
0.6641	Remote Similarity	NPD1091	Approved
0.6641	Remote Similarity	NPD6584	Phase 3
0.664	Remote Similarity	NPD317	Approved
0.664	Remote Similarity	NPD318	Approved
0.6639	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5311	Approved
0.6615	Remote Similarity	NPD5310	Approved
0.6613	Remote Similarity	NPD255	Approved
0.6613	Remote Similarity	NPD256	Approved
0.6594	Remote Similarity	NPD2935	Discontinued
0.6594	Remote Similarity	NPD1551	Phase 2
0.6593	Remote Similarity	NPD468	Phase 1
0.6593	Remote Similarity	NPD4060	Phase 1
0.6591	Remote Similarity	NPD3635	Approved
0.6591	Remote Similarity	NPD3637	Approved
0.6591	Remote Similarity	NPD3636	Approved
0.6589	Remote Similarity	NPD1608	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