NPASS Compound

Structure

CID10588 OpenBabel06191715332D 23 23 0 0 0 0 0 0 0 0999 V2000 -0.8660 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 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 5.5000 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 0.0000 4.0000 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 -0.8660 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 -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 2 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 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 19 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.22
Volume:	364.977
LogP:	4.529
LogD:	4.22
LogS:	-3.095
# Rotatable Bonds:	12
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	2.736
Fsp3:	0.429
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:	-5.002
MDCK Permeability:	4.013640864286572e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	99.97745513916016%
Volume Distribution (VD):	1.74
Pgp-substrate:	0.5549153089523315%

ADMET: Metabolism

CYP1A2-inhibitor:	0.913
CYP1A2-substrate:	0.511
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.616
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.983
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.808
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	6.612
Half-life (T1/2):	0.958

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.332
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.97
Carcinogencity:	0.301
Eye Corrosion:	0.645
Eye Irritation:	0.962
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC10588

Natural Product ID:	NPC10588
*Common Name:**	Cardol 8'z,11'z,14'-Triene
IUPAC Name:	5-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzene-1,3-diol
Synonyms:	5-{8(Z),11(Z),14-Pentadecatrienyl}Resorcinol; Cardol 8'Z,11'Z,14'-Triene
Standard InCHIKey:	OOXBEOHCOCMKAC-UTOQUPLUSA-N
Standard InCHI:	InChI=1S/C21H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h2,4-5,7-8,16-18,22-23H,1,3,6,9-15H2/b5-4-,8-7-
SMILES:	C=CC/C=CC/C=CCCCCCCCc1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459603
PubChem CID:	13259919
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
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
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]
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.	n.a.	Database[HerDing]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
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]
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]
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]

☑ 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
IC50	1
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	88.0	%	PMID[509480]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	ID50	=	0.04	mM	PMID[509480]
NPT169	Cell Line	B16-F10	Mus musculus	Ratio	=	40.0	n.a.	PMID[509481]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	74.0	%	PMID[509481]
NPT89	Individual Protein	Seed lipoxygenase-1	Glycine max	IC50	=	60000.0	nM	PMID[509479]
NPT27	Others	Unspecified		Activity	=	102.0	%	PMID[509481]
NPT27	Others	Unspecified		Activity	=	98.0	%	PMID[509481]

☑ 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 NPC10588 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	285
0.1-0.2	1685
0.2-0.3	5579
0.3-0.4	13926
0.4-0.5	4968
0.5-0.6	8923
0.6-0.7	5565
0.7-0.8	1452
0.8-0.85	179
0.85-0.9	67
0.9-0.95	36
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC284011
0.9894	High Similarity	NPC72947
0.9789	High Similarity	NPC24404
0.9789	High Similarity	NPC146798
0.9789	High Similarity	NPC302219
0.9789	High Similarity	NPC106396
0.9789	High Similarity	NPC242342
0.9789	High Similarity	NPC85479
0.9789	High Similarity	NPC94351
0.9789	High Similarity	NPC168303
0.9789	High Similarity	NPC222522
0.9789	High Similarity	NPC71002
0.9789	High Similarity	NPC53051
0.9789	High Similarity	NPC249828
0.9789	High Similarity	NPC313030
0.9787	High Similarity	NPC166761
0.9688	High Similarity	NPC241891
0.9684	High Similarity	NPC147310
0.9684	High Similarity	NPC166313
0.9684	High Similarity	NPC137415
0.9684	High Similarity	NPC11280
0.9684	High Similarity	NPC294186
0.9684	High Similarity	NPC24407
0.9684	High Similarity	NPC192032
0.9588	High Similarity	NPC134829
0.949	High Similarity	NPC39664
0.949	High Similarity	NPC118286
0.949	High Similarity	NPC39097
0.949	High Similarity	NPC302681
0.949	High Similarity	NPC470700
0.949	High Similarity	NPC109691
0.9479	High Similarity	NPC143659
0.9479	High Similarity	NPC100340
0.9394	High Similarity	NPC158253
0.9394	High Similarity	NPC61033
0.9394	High Similarity	NPC305603
0.9394	High Similarity	NPC232523
0.9394	High Similarity	NPC204901
0.9394	High Similarity	NPC54844
0.9388	High Similarity	NPC37802
0.9388	High Similarity	NPC246056
0.9293	High Similarity	NPC201662
0.9293	High Similarity	NPC99836
0.9293	High Similarity	NPC12640
0.9286	High Similarity	NPC218879
0.9286	High Similarity	NPC244513
0.9286	High Similarity	NPC227458
0.9286	High Similarity	NPC102216
0.9286	High Similarity	NPC30506
0.9208	High Similarity	NPC33728
0.9208	High Similarity	NPC19808
0.9167	High Similarity	NPC291789
0.9149	High Similarity	NPC295295
0.914	High Similarity	NPC192
0.9109	High Similarity	NPC174981
0.9029	High Similarity	NPC476632
0.9029	High Similarity	NPC224527
0.9029	High Similarity	NPC4493
0.9029	High Similarity	NPC225679
0.9029	High Similarity	NPC165770
0.902	High Similarity	NPC186385
0.902	High Similarity	NPC299568
0.9	High Similarity	NPC474839
0.898	High Similarity	NPC275053
0.898	High Similarity	NPC161571
0.898	High Similarity	NPC248573
0.8947	High Similarity	NPC3358
0.8947	High Similarity	NPC162314
0.8947	High Similarity	NPC210497
0.8947	High Similarity	NPC94139
0.8947	High Similarity	NPC306884
0.8947	High Similarity	NPC147284
0.8942	High Similarity	NPC43525
0.8942	High Similarity	NPC166995
0.89	High Similarity	NPC119860
0.8878	High Similarity	NPC80027
0.8857	High Similarity	NPC261343
0.8857	High Similarity	NPC117846
0.8854	High Similarity	NPC76938
0.8812	High Similarity	NPC292452
0.8774	High Similarity	NPC107240
0.8763	High Similarity	NPC32714
0.875	High Similarity	NPC168657
0.8738	High Similarity	NPC63698
0.8738	High Similarity	NPC61885
0.8725	High Similarity	NPC248904
0.8723	High Similarity	NPC27974
0.8692	High Similarity	NPC84999
0.8692	High Similarity	NPC246760
0.8692	High Similarity	NPC53906
0.8679	High Similarity	NPC162113
0.8679	High Similarity	NPC319803
0.8679	High Similarity	NPC263753
0.8679	High Similarity	NPC62546
0.8679	High Similarity	NPC23804
0.8667	High Similarity	NPC268032
0.8654	High Similarity	NPC202647
0.8614	High Similarity	NPC315022
0.8611	High Similarity	NPC123559
0.86	High Similarity	NPC48730
0.86	High Similarity	NPC248396
0.86	High Similarity	NPC294741
0.86	High Similarity	NPC129373
0.8598	High Similarity	NPC276737
0.8598	High Similarity	NPC22610
0.8586	High Similarity	NPC474073
0.8586	High Similarity	NPC152097
0.8585	High Similarity	NPC473521
0.8571	High Similarity	NPC475018
0.8571	High Similarity	NPC274678
0.8571	High Similarity	NPC224870
0.8557	High Similarity	NPC55903
0.8532	High Similarity	NPC69261
0.8532	High Similarity	NPC33270
0.8532	High Similarity	NPC15860
0.8532	High Similarity	NPC470760
0.8532	High Similarity	NPC127894
0.8532	High Similarity	NPC470759
0.8532	High Similarity	NPC219070
0.8532	High Similarity	NPC474933
0.8529	High Similarity	NPC315936
0.8519	High Similarity	NPC808
0.85	High Similarity	NPC260775
0.8469	Intermediate Similarity	NPC151715
0.8462	Intermediate Similarity	NPC176527
0.8455	Intermediate Similarity	NPC190514
0.8455	Intermediate Similarity	NPC144343
0.8447	Intermediate Similarity	NPC471350
0.844	Intermediate Similarity	NPC141090
0.844	Intermediate Similarity	NPC150624
0.844	Intermediate Similarity	NPC114064
0.844	Intermediate Similarity	NPC115808
0.8438	Intermediate Similarity	NPC280347
0.8438	Intermediate Similarity	NPC242240
0.8438	Intermediate Similarity	NPC318325
0.8438	Intermediate Similarity	NPC123273
0.8438	Intermediate Similarity	NPC177420
0.8431	Intermediate Similarity	NPC168393
0.8431	Intermediate Similarity	NPC108497
0.8416	Intermediate Similarity	NPC130756
0.8416	Intermediate Similarity	NPC12931
0.8416	Intermediate Similarity	NPC130103
0.8416	Intermediate Similarity	NPC72729
0.8416	Intermediate Similarity	NPC70677
0.8404	Intermediate Similarity	NPC150837
0.84	Intermediate Similarity	NPC475078
0.84	Intermediate Similarity	NPC6597
0.84	Intermediate Similarity	NPC79241
0.8396	Intermediate Similarity	NPC242178
0.8384	Intermediate Similarity	NPC26244
0.8384	Intermediate Similarity	NPC222146
0.8381	Intermediate Similarity	NPC105727
0.8381	Intermediate Similarity	NPC34864
0.8381	Intermediate Similarity	NPC114392
0.8381	Intermediate Similarity	NPC58427
0.8378	Intermediate Similarity	NPC184302
0.8365	Intermediate Similarity	NPC164576
0.8365	Intermediate Similarity	NPC469913
0.8364	Intermediate Similarity	NPC277588
0.8351	Intermediate Similarity	NPC55561
0.8351	Intermediate Similarity	NPC312304
0.835	Intermediate Similarity	NPC323810
0.8349	Intermediate Similarity	NPC167934
0.8333	Intermediate Similarity	NPC113460
0.8333	Intermediate Similarity	NPC25493
0.8333	Intermediate Similarity	NPC19680
0.8333	Intermediate Similarity	NPC252105
0.8333	Intermediate Similarity	NPC477685
0.8317	Intermediate Similarity	NPC33675
0.8317	Intermediate Similarity	NPC299762
0.8316	Intermediate Similarity	NPC155393
0.8304	Intermediate Similarity	NPC223451
0.8304	Intermediate Similarity	NPC69006
0.83	Intermediate Similarity	NPC132271
0.83	Intermediate Similarity	NPC292730
0.83	Intermediate Similarity	NPC473388
0.83	Intermediate Similarity	NPC259512
0.83	Intermediate Similarity	NPC216520
0.83	Intermediate Similarity	NPC82664
0.83	Intermediate Similarity	NPC312132
0.8288	Intermediate Similarity	NPC9592
0.8288	Intermediate Similarity	NPC48781
0.8288	Intermediate Similarity	NPC206
0.8286	Intermediate Similarity	NPC66834
0.8283	Intermediate Similarity	NPC316301
0.8283	Intermediate Similarity	NPC152415
0.8283	Intermediate Similarity	NPC27323
0.8283	Intermediate Similarity	NPC245187
0.8269	Intermediate Similarity	NPC47284
0.8265	Intermediate Similarity	NPC231150
0.8265	Intermediate Similarity	NPC45040
0.8265	Intermediate Similarity	NPC304541
0.8257	Intermediate Similarity	NPC228287
0.8257	Intermediate Similarity	NPC180508
0.8252	Intermediate Similarity	NPC235762
0.8252	Intermediate Similarity	NPC471228
0.8252	Intermediate Similarity	NPC196479
0.8247	Intermediate Similarity	NPC258219
0.8235	Intermediate Similarity	NPC174911
0.8235	Intermediate Similarity	NPC213730

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 NPC10588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	1019
0.2-0.3	1559
0.3-0.4	2960
0.4-0.5	1817
0.5-0.6	1067
0.6-0.7	374
0.7-0.8	50
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9082	High Similarity	NPD940	Approved
0.9082	High Similarity	NPD846	Approved
0.902	High Similarity	NPD4750	Phase 3
0.898	High Similarity	NPD1242	Phase 1
0.8571	High Similarity	NPD844	Approved
0.8384	Intermediate Similarity	NPD2859	Approved
0.8384	Intermediate Similarity	NPD2860	Approved
0.8317	Intermediate Similarity	NPD3020	Approved
0.83	Intermediate Similarity	NPD288	Approved
0.8283	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD2933	Approved
0.8283	Intermediate Similarity	NPD2934	Approved
0.8235	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD9089	Approved
0.8065	Intermediate Similarity	NPD9093	Approved
0.8	Intermediate Similarity	NPD845	Approved
0.7963	Intermediate Similarity	NPD3022	Approved
0.7963	Intermediate Similarity	NPD3021	Approved
0.7917	Intermediate Similarity	NPD111	Approved
0.7863	Intermediate Similarity	NPD4749	Approved
0.785	Intermediate Similarity	NPD1445	Approved
0.785	Intermediate Similarity	NPD1444	Approved
0.7677	Intermediate Similarity	NPD9094	Approved
0.767	Intermediate Similarity	NPD1809	Phase 2
0.7636	Intermediate Similarity	NPD1792	Phase 2
0.7623	Intermediate Similarity	NPD4625	Phase 3
0.7623	Intermediate Similarity	NPD3027	Phase 3
0.7615	Intermediate Similarity	NPD2342	Discontinued
0.7589	Intermediate Similarity	NPD7635	Approved
0.7544	Intermediate Similarity	NPD6671	Approved
0.7542	Intermediate Similarity	NPD1610	Phase 2
0.7524	Intermediate Similarity	NPD9273	Approved
0.7521	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7419	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD9500	Approved
0.7398	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4908	Phase 1
0.7377	Intermediate Similarity	NPD599	Approved
0.7377	Intermediate Similarity	NPD859	Approved
0.7377	Intermediate Similarity	NPD858	Approved
0.7377	Intermediate Similarity	NPD602	Approved
0.7368	Intermediate Similarity	NPD2229	Approved
0.7368	Intermediate Similarity	NPD2234	Approved
0.7368	Intermediate Similarity	NPD2228	Approved
0.735	Intermediate Similarity	NPD3091	Approved
0.7345	Intermediate Similarity	NPD228	Approved
0.7321	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9087	Approved
0.7304	Intermediate Similarity	NPD1793	Approved
0.7304	Intermediate Similarity	NPD1791	Approved
0.7281	Intermediate Similarity	NPD9379	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.728	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3092	Approved
0.725	Intermediate Similarity	NPD422	Phase 1
0.7227	Intermediate Similarity	NPD3019	Approved
0.7227	Intermediate Similarity	NPD2932	Approved
0.7227	Intermediate Similarity	NPD4059	Approved
0.7222	Intermediate Similarity	NPD3028	Approved
0.7188	Intermediate Similarity	NPD2568	Approved
0.7188	Intermediate Similarity	NPD9088	Approved
0.7182	Intermediate Similarity	NPD9610	Approved
0.7182	Intermediate Similarity	NPD9608	Approved
0.7165	Intermediate Similarity	NPD1613	Approved
0.7165	Intermediate Similarity	NPD943	Approved
0.7165	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD9614	Approved
0.7155	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD9618	Approved
0.7154	Intermediate Similarity	NPD3094	Phase 2
0.7154	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7107	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1201	Approved
0.7083	Intermediate Similarity	NPD2286	Discontinued
0.7083	Intermediate Similarity	NPD9384	Approved
0.7083	Intermediate Similarity	NPD9294	Approved
0.7083	Intermediate Similarity	NPD9381	Approved
0.7083	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2684	Approved
0.7059	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD968	Approved
0.7049	Intermediate Similarity	NPD9269	Phase 2
0.7043	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2861	Phase 2
0.7023	Intermediate Similarity	NPD6099	Approved
0.7023	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD9268	Approved
0.6992	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2983	Phase 2
0.6992	Remote Similarity	NPD2982	Phase 2
0.6991	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9613	Approved
0.6975	Remote Similarity	NPD16	Approved
0.6975	Remote Similarity	NPD856	Approved
0.6975	Remote Similarity	NPD9615	Approved
0.6975	Remote Similarity	NPD9616	Approved
0.6942	Remote Similarity	NPD4626	Approved
0.6942	Remote Similarity	NPD3095	Discontinued
0.6942	Remote Similarity	NPD1751	Approved
0.6935	Remote Similarity	NPD6696	Suspended
0.693	Remote Similarity	NPD9266	Approved
0.693	Remote Similarity	NPD74	Approved
0.6923	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5283	Phase 1
0.6917	Remote Similarity	NPD316	Approved
0.6917	Remote Similarity	NPD1759	Phase 1
0.6911	Remote Similarity	NPD2230	Approved
0.6911	Remote Similarity	NPD2233	Approved
0.6911	Remote Similarity	NPD2981	Phase 2
0.6911	Remote Similarity	NPD2232	Approved
0.6905	Remote Similarity	NPD3018	Phase 2
0.6899	Remote Similarity	NPD2238	Phase 2
0.6891	Remote Similarity	NPD405	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1133	Approved
0.688	Remote Similarity	NPD1470	Approved
0.688	Remote Similarity	NPD1135	Approved
0.688	Remote Similarity	NPD1129	Approved
0.688	Remote Similarity	NPD1131	Approved
0.688	Remote Similarity	NPD1134	Approved
0.6855	Remote Similarity	NPD9622	Approved
0.6855	Remote Similarity	NPD4659	Approved
0.6855	Remote Similarity	NPD1755	Approved
0.6842	Remote Similarity	NPD9267	Approved
0.6842	Remote Similarity	NPD9263	Approved
0.6842	Remote Similarity	NPD9264	Approved
0.6842	Remote Similarity	NPD290	Approved
0.6838	Remote Similarity	NPD7843	Approved
0.6833	Remote Similarity	NPD317	Approved
0.6833	Remote Similarity	NPD318	Approved
0.6833	Remote Similarity	NPD1758	Phase 1
0.6825	Remote Similarity	NPD6584	Phase 3
0.6822	Remote Similarity	NPD6405	Approved
0.6822	Remote Similarity	NPD6407	Approved
0.6818	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD256	Approved
0.6807	Remote Similarity	NPD7157	Approved
0.6807	Remote Similarity	NPD255	Approved
0.6803	Remote Similarity	NPD4589	Approved
0.68	Remote Similarity	NPD5311	Approved
0.68	Remote Similarity	NPD5310	Approved
0.6777	Remote Similarity	NPD5303	Approved
0.6777	Remote Similarity	NPD5304	Approved
0.6774	Remote Similarity	NPD2562	Approved
0.6774	Remote Similarity	NPD2231	Phase 2
0.6774	Remote Similarity	NPD2561	Approved
0.6774	Remote Similarity	NPD2235	Phase 2
0.6774	Remote Similarity	NPD1608	Approved
0.6772	Remote Similarity	NPD5736	Approved
0.6769	Remote Similarity	NPD1240	Approved
0.675	Remote Similarity	NPD9493	Approved
0.675	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1981	Approved
0.6748	Remote Similarity	NPD3496	Discontinued
0.6748	Remote Similarity	NPD1983	Approved
0.6748	Remote Similarity	NPD1980	Approved
0.6746	Remote Similarity	NPD3055	Approved
0.6746	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4103	Phase 2
0.6746	Remote Similarity	NPD3053	Approved
0.6744	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5451	Approved
0.6723	Remote Similarity	NPD475	Phase 2
0.6723	Remote Similarity	NPD497	Approved
0.6718	Remote Similarity	NPD230	Phase 1
0.6695	Remote Similarity	NPD821	Approved
0.6694	Remote Similarity	NPD1091	Approved
0.6693	Remote Similarity	NPD2194	Approved
0.6693	Remote Similarity	NPD9620	Approved
0.6693	Remote Similarity	NPD9621	Approved
0.6693	Remote Similarity	NPD9619	Approved
0.6693	Remote Similarity	NPD2195	Approved
0.6692	Remote Similarity	NPD1510	Phase 2
0.6691	Remote Similarity	NPD3892	Phase 2
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD2667	Approved
0.6667	Remote Similarity	NPD2668	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD709	Approved
0.6642	Remote Similarity	NPD5404	Approved
0.6642	Remote Similarity	NPD5405	Approved
0.6642	Remote Similarity	NPD5406	Approved
0.6642	Remote Similarity	NPD5408	Approved
0.6641	Remote Similarity	NPD3636	Approved
0.6641	Remote Similarity	NPD3637	Approved
0.6641	Remote Similarity	NPD1555	Discontinued
0.6641	Remote Similarity	NPD3062	Approved
0.6641	Remote Similarity	NPD3635	Approved
0.6641	Remote Similarity	NPD3061	Approved
0.6641	Remote Similarity	NPD3059	Approved
0.6639	Remote Similarity	NPD7330	Discontinued
0.6639	Remote Similarity	NPD9545	Approved
0.6639	Remote Similarity	NPD498	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