NPASS Compound

Structure

NPC77772 OpenBabel07101719142D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 -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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 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 2.5981 -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 -2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 15 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 18 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 1 0 0 0 16 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 1 0 0 0 19 21 1 0 0 0 0 20 3 1 6 0 0 0 21 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.22
Volume:	353.137
LogP:	4.425
LogD:	4.195
LogS:	-4.286
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	4.006
Fsp3:	0.619
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:	-4.671
MDCK Permeability:	1.5264562534866855e-05
Pgp-inhibitor:	0.786
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.481
Plasma Protein Binding (PPB):	94.06824493408203%
Volume Distribution (VD):	1.936
Pgp-substrate:	7.452930450439453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.614
CYP1A2-substrate:	0.523
CYP2C19-inhibitor:	0.591
CYP2C19-substrate:	0.587
CYP2C9-inhibitor:	0.399
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.853
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	10.335
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.957
Carcinogencity:	0.114
Eye Corrosion:	0.764
Eye Irritation:	0.95
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC77772

Natural Product ID:	NPC77772
*Common Name:**	Arenarol
IUPAC Name:	2-[[(1R,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol
Synonyms:	Arenarol
Standard InCHIKey:	FBMAHDGTCDISLJ-PSMQTCRGSA-N
Standard InCHI:	InChI=1S/C21H30O2/c1-14-6-5-7-19-20(14,3)11-10-15(2)21(19,4)13-16-12-17(22)8-9-18(16)23/h8-9,12,15,19,22-23H,1,5-7,10-11,13H2,2-4H3/t15-,19+,20-,21+/m0/s1
SMILES:	Oc1ccc(c(c1)C[C@]1(C)[C@@H](C)CC[C@@]2([C@H]1CCCC2=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096605
PubChem CID:	10470916
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000136] Hydroquinones

*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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]

☑ 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	5
MIC	10

Activity Type	# Activity
Cell Line	2
Individual Protein	1
NON-MOLECULAR	1
Organism	9
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	3400.0	nM	PMID[502935]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3700.0	nM	PMID[502935]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	128.0	ug.mL-1	PMID[502935]
NPT1	Others	Radical scavenging activity		IC50	=	19000.0	nM	PMID[502934]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[502935]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[502935]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	4.0	ug.mL-1	PMID[502935]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	4.0	ug.mL-1	PMID[502935]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	2.0	ug.mL-1	PMID[502935]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[502935]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	4.0	ug.mL-1	PMID[502935]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	4.0	ug.mL-1	PMID[502935]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	8.0	ug.mL-1	PMID[502935]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	128.0	ug.mL-1	PMID[502935]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	3.6	ug.mL-1	PMID[502935]

☑ 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 NPC77772 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	321
0.1-0.2	1650
0.2-0.3	3383
0.3-0.4	9304
0.4-0.5	10328
0.5-0.6	11903
0.6-0.7	4709
0.7-0.8	896
0.8-0.85	137
0.85-0.9	50
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC266937
0.9808	High Similarity	NPC470770
0.9714	High Similarity	NPC177962
0.9714	High Similarity	NPC62867
0.9612	High Similarity	NPC320439
0.9537	High Similarity	NPC141001
0.9533	High Similarity	NPC471534
0.9231	High Similarity	NPC47284
0.9159	High Similarity	NPC141782
0.9143	High Similarity	NPC155072
0.9143	High Similarity	NPC53740
0.9107	High Similarity	NPC323074
0.9074	High Similarity	NPC260323
0.9074	High Similarity	NPC176279
0.9038	High Similarity	NPC269212
0.9027	High Similarity	NPC477037
0.9027	High Similarity	NPC318581
0.9027	High Similarity	NPC325544
0.9009	High Similarity	NPC92
0.9009	High Similarity	NPC469663
0.9009	High Similarity	NPC308828
0.9	High Similarity	NPC195922
0.9	High Similarity	NPC268160
0.8991	High Similarity	NPC250323
0.8981	High Similarity	NPC13482
0.8972	High Similarity	NPC11554
0.8942	High Similarity	NPC12221
0.8919	High Similarity	NPC469719
0.8919	High Similarity	NPC192948
0.8919	High Similarity	NPC35797
0.8919	High Similarity	NPC147179
0.8899	High Similarity	NPC95716
0.8899	High Similarity	NPC322753
0.8868	High Similarity	NPC117115
0.8857	High Similarity	NPC108497
0.885	High Similarity	NPC469609
0.8846	High Similarity	NPC129373
0.8846	High Similarity	NPC248396
0.8846	High Similarity	NPC48730
0.8839	High Similarity	NPC219112
0.8839	High Similarity	NPC477137
0.8839	High Similarity	NPC38893
0.8839	High Similarity	NPC471668
0.8839	High Similarity	NPC308311
0.8835	High Similarity	NPC152097
0.8818	High Similarity	NPC46940
0.8807	High Similarity	NPC132720
0.8803	High Similarity	NPC248557
0.8774	High Similarity	NPC475580
0.8774	High Similarity	NPC272029
0.8772	High Similarity	NPC469644
0.8762	High Similarity	NPC252105
0.8762	High Similarity	NPC477685
0.8761	High Similarity	NPC16030
0.8761	High Similarity	NPC304510
0.8761	High Similarity	NPC477136
0.8761	High Similarity	NPC172219
0.875	High Similarity	NPC260775
0.875	High Similarity	NPC84999
0.875	High Similarity	NPC246760
0.875	High Similarity	NPC299762
0.875	High Similarity	NPC33675
0.8739	High Similarity	NPC715
0.8727	High Similarity	NPC54373
0.8727	High Similarity	NPC469912
0.8704	High Similarity	NPC151477
0.8696	High Similarity	NPC260832
0.8696	High Similarity	NPC135467
0.8684	High Similarity	NPC471671
0.8684	High Similarity	NPC206
0.8679	High Similarity	NPC233827
0.8667	High Similarity	NPC130756
0.8667	High Similarity	NPC12931
0.8667	High Similarity	NPC70677
0.8667	High Similarity	NPC72729
0.8654	High Similarity	NPC79241
0.8654	High Similarity	NPC6597
0.8654	High Similarity	NPC475078
0.8649	High Similarity	NPC302371
0.8649	High Similarity	NPC228425
0.8636	High Similarity	NPC296683
0.8611	High Similarity	NPC469913
0.8611	High Similarity	NPC54765
0.8611	High Similarity	NPC271274
0.8609	High Similarity	NPC93071
0.8609	High Similarity	NPC126002
0.8598	High Similarity	NPC475225
0.8585	High Similarity	NPC51015
0.8585	High Similarity	NPC80800
0.8558	High Similarity	NPC312132
0.8558	High Similarity	NPC259512
0.8545	High Similarity	NPC58865
0.8544	High Similarity	NPC152415
0.8522	High Similarity	NPC164649
0.8522	High Similarity	NPC48342
0.8519	High Similarity	NPC138942
0.8512	High Similarity	NPC47288
0.8512	High Similarity	NPC176590
0.8505	High Similarity	NPC235762
0.8505	High Similarity	NPC471228
0.8491	Intermediate Similarity	NPC225506
0.8475	Intermediate Similarity	NPC478058
0.8462	Intermediate Similarity	NPC222146
0.8462	Intermediate Similarity	NPC259703
0.8462	Intermediate Similarity	NPC328504
0.8462	Intermediate Similarity	NPC32322
0.8455	Intermediate Similarity	NPC64586
0.8455	Intermediate Similarity	NPC95344
0.8448	Intermediate Similarity	NPC42657
0.8447	Intermediate Similarity	NPC55903
0.8447	Intermediate Similarity	NPC29373
0.844	Intermediate Similarity	NPC310456
0.844	Intermediate Similarity	NPC67250
0.844	Intermediate Similarity	NPC21594
0.8435	Intermediate Similarity	NPC299180
0.8426	Intermediate Similarity	NPC238696
0.8426	Intermediate Similarity	NPC323810
0.8426	Intermediate Similarity	NPC288411
0.8403	Intermediate Similarity	NPC471187
0.8396	Intermediate Similarity	NPC122005
0.8396	Intermediate Similarity	NPC252821
0.8396	Intermediate Similarity	NPC92730
0.8393	Intermediate Similarity	NPC224527
0.8393	Intermediate Similarity	NPC151537
0.8393	Intermediate Similarity	NPC275627
0.839	Intermediate Similarity	NPC253627
0.839	Intermediate Similarity	NPC162935
0.839	Intermediate Similarity	NPC249340
0.8378	Intermediate Similarity	NPC314187
0.8376	Intermediate Similarity	NPC190501
0.8376	Intermediate Similarity	NPC99734
0.8376	Intermediate Similarity	NPC318552
0.8374	Intermediate Similarity	NPC472793
0.8365	Intermediate Similarity	NPC76938
0.8365	Intermediate Similarity	NPC245187
0.8365	Intermediate Similarity	NPC289769
0.8364	Intermediate Similarity	NPC66834
0.8362	Intermediate Similarity	NPC154030
0.835	Intermediate Similarity	NPC306074
0.8348	Intermediate Similarity	NPC247858
0.8348	Intermediate Similarity	NPC154511
0.8348	Intermediate Similarity	NPC474387
0.8348	Intermediate Similarity	NPC257540
0.8348	Intermediate Similarity	NPC137496
0.8348	Intermediate Similarity	NPC474358
0.8333	Intermediate Similarity	NPC249270
0.8333	Intermediate Similarity	NPC168829
0.8319	Intermediate Similarity	NPC471794
0.8319	Intermediate Similarity	NPC176208
0.8319	Intermediate Similarity	NPC11250
0.8319	Intermediate Similarity	NPC98372
0.8318	Intermediate Similarity	NPC174911
0.8318	Intermediate Similarity	NPC211885
0.8306	Intermediate Similarity	NPC153019
0.8306	Intermediate Similarity	NPC473047
0.8305	Intermediate Similarity	NPC241001
0.8305	Intermediate Similarity	NPC129176
0.8302	Intermediate Similarity	NPC225464
0.8302	Intermediate Similarity	NPC77492
0.8302	Intermediate Similarity	NPC156313
0.8293	Intermediate Similarity	NPC206028
0.8291	Intermediate Similarity	NPC471449
0.8291	Intermediate Similarity	NPC151197
0.8291	Intermediate Similarity	NPC121866
0.8291	Intermediate Similarity	NPC51341
0.8288	Intermediate Similarity	NPC279887
0.8288	Intermediate Similarity	NPC306295
0.8288	Intermediate Similarity	NPC68260
0.8286	Intermediate Similarity	NPC32714
0.8276	Intermediate Similarity	NPC320864
0.8269	Intermediate Similarity	NPC147284
0.8269	Intermediate Similarity	NPC210497
0.8269	Intermediate Similarity	NPC3358
0.8269	Intermediate Similarity	NPC306884
0.8269	Intermediate Similarity	NPC94139
0.8269	Intermediate Similarity	NPC162314
0.8252	Intermediate Similarity	NPC192
0.825	Intermediate Similarity	NPC198014
0.8246	Intermediate Similarity	NPC317869
0.8246	Intermediate Similarity	NPC322239
0.8235	Intermediate Similarity	NPC154696
0.8235	Intermediate Similarity	NPC142198
0.8235	Intermediate Similarity	NPC77569
0.8235	Intermediate Similarity	NPC475839
0.8214	Intermediate Similarity	NPC186385
0.8214	Intermediate Similarity	NPC33728
0.8214	Intermediate Similarity	NPC26013
0.8214	Intermediate Similarity	NPC299568
0.8214	Intermediate Similarity	NPC19808
0.8214	Intermediate Similarity	NPC282855
0.8208	Intermediate Similarity	NPC82664
0.8208	Intermediate Similarity	NPC216520
0.8208	Intermediate Similarity	NPC473388
0.8208	Intermediate Similarity	NPC132271
0.8208	Intermediate Similarity	NPC292730
0.8198	Intermediate Similarity	NPC474352
0.819	Intermediate Similarity	NPC316301
0.819	Intermediate Similarity	NPC27323
0.8182	Intermediate Similarity	NPC219286
0.8182	Intermediate Similarity	NPC61685

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 NPC77772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	953
0.2-0.3	1134
0.3-0.4	2918
0.4-0.5	2154
0.5-0.6	1278
0.6-0.7	316
0.7-0.8	76
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9029	High Similarity	NPD289	Clinical (unspecified phase)
0.8991	High Similarity	NPD7635	Approved
0.8558	High Similarity	NPD288	Approved
0.8532	High Similarity	NPD2342	Discontinued
0.8522	High Similarity	NPD3091	Approved
0.8462	Intermediate Similarity	NPD844	Approved
0.8396	Intermediate Similarity	NPD3020	Approved
0.8376	Intermediate Similarity	NPD4059	Approved
0.8376	Intermediate Similarity	NPD3019	Approved
0.8269	Intermediate Similarity	NPD845	Approved
0.8235	Intermediate Similarity	NPD3092	Approved
0.822	Intermediate Similarity	NPD2932	Approved
0.8214	Intermediate Similarity	NPD4750	Phase 3
0.819	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD3094	Phase 2
0.8113	Intermediate Similarity	NPD2859	Approved
0.8113	Intermediate Similarity	NPD2860	Approved
0.8113	Intermediate Similarity	NPD1809	Phase 2
0.8067	Intermediate Similarity	NPD3095	Discontinued
0.8053	Intermediate Similarity	NPD3021	Approved
0.8053	Intermediate Similarity	NPD3022	Approved
0.8019	Intermediate Similarity	NPD2934	Approved
0.8019	Intermediate Similarity	NPD2933	Approved
0.7949	Intermediate Similarity	NPD6671	Approved
0.7895	Intermediate Similarity	NPD1792	Phase 2
0.7863	Intermediate Similarity	NPD497	Approved
0.784	Intermediate Similarity	NPD5736	Approved
0.7833	Intermediate Similarity	NPD4093	Discontinued
0.7778	Intermediate Similarity	NPD498	Approved
0.7778	Intermediate Similarity	NPD495	Approved
0.7778	Intermediate Similarity	NPD496	Approved
0.7769	Intermediate Similarity	NPD1751	Approved
0.7742	Intermediate Similarity	NPD6696	Suspended
0.7705	Intermediate Similarity	NPD3026	Approved
0.7705	Intermediate Similarity	NPD3023	Approved
0.7686	Intermediate Similarity	NPD3024	Approved
0.7686	Intermediate Similarity	NPD3025	Approved
0.7661	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD1201	Approved
0.7642	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2605	Approved
0.7638	Intermediate Similarity	NPD2606	Approved
0.7632	Intermediate Similarity	NPD1445	Approved
0.7632	Intermediate Similarity	NPD1444	Approved
0.7623	Intermediate Similarity	NPD2286	Discontinued
0.7619	Intermediate Similarity	NPD4624	Approved
0.7597	Intermediate Similarity	NPD6663	Approved
0.7589	Intermediate Similarity	NPD846	Approved
0.7589	Intermediate Similarity	NPD940	Approved
0.7583	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD7340	Approved
0.7578	Intermediate Similarity	NPD5156	Approved
0.7578	Intermediate Similarity	NPD5155	Approved
0.7559	Intermediate Similarity	NPD2861	Phase 2
0.7559	Intermediate Similarity	NPD3635	Approved
0.7559	Intermediate Similarity	NPD3637	Approved
0.7559	Intermediate Similarity	NPD3636	Approved
0.7557	Intermediate Similarity	NPD4097	Suspended
0.75	Intermediate Similarity	NPD3594	Approved
0.75	Intermediate Similarity	NPD3595	Approved
0.748	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD2195	Approved
0.748	Intermediate Similarity	NPD4589	Approved
0.748	Intermediate Similarity	NPD2194	Approved
0.7479	Intermediate Similarity	NPD2229	Approved
0.7479	Intermediate Similarity	NPD2234	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD1398	Phase 1
0.7459	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4625	Phase 3
0.744	Intermediate Similarity	NPD2230	Approved
0.744	Intermediate Similarity	NPD2232	Approved
0.744	Intermediate Similarity	NPD2233	Approved
0.7405	Intermediate Similarity	NPD3620	Phase 2
0.7405	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1470	Approved
0.7385	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4749	Approved
0.7381	Intermediate Similarity	NPD5327	Phase 3
0.7345	Intermediate Similarity	NPD1242	Phase 1
0.7339	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD111	Approved
0.7333	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7330	Discontinued
0.7317	Intermediate Similarity	NPD5304	Approved
0.7317	Intermediate Similarity	NPD5303	Approved
0.7313	Intermediate Similarity	NPD7743	Approved
0.7313	Intermediate Similarity	NPD7742	Approved
0.7273	Intermediate Similarity	NPD1793	Approved
0.7273	Intermediate Similarity	NPD4140	Approved
0.7273	Intermediate Similarity	NPD1791	Approved
0.7266	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1611	Approved
0.7218	Intermediate Similarity	NPD5735	Approved
0.7217	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4726	Approved
0.7206	Intermediate Similarity	NPD4725	Approved
0.7206	Intermediate Similarity	NPD4721	Approved
0.7185	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD968	Approved
0.7164	Intermediate Similarity	NPD6353	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7132	Intermediate Similarity	NPD6099	Approved
0.7132	Intermediate Similarity	NPD6100	Approved
0.7131	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3638	Discontinued
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7073	Intermediate Similarity	NPD709	Approved
0.7069	Intermediate Similarity	NPD9500	Approved
0.705	Intermediate Similarity	NPD8166	Discontinued
0.7049	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5283	Phase 1
0.7043	Intermediate Similarity	NPD3028	Approved
0.7029	Intermediate Similarity	NPD4257	Approved
0.7029	Intermediate Similarity	NPD4256	Phase 2
0.7016	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7636	Approved
0.7015	Intermediate Similarity	NPD6346	Approved
0.7	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5951	Approved
0.699	Remote Similarity	NPD9088	Approved
0.6985	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5691	Approved
0.6984	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1755	Approved
0.6972	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1610	Phase 2
0.695	Remote Similarity	NPD3300	Phase 2
0.6947	Remote Similarity	NPD6584	Phase 3
0.694	Remote Similarity	NPD8032	Phase 2
0.6929	Remote Similarity	NPD7003	Approved
0.6929	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1283	Approved
0.6917	Remote Similarity	NPD7095	Approved
0.6905	Remote Similarity	NPD7741	Discontinued
0.6889	Remote Similarity	NPD2238	Phase 2
0.6885	Remote Similarity	NPD228	Approved
0.6884	Remote Similarity	NPD5405	Approved
0.6884	Remote Similarity	NPD2935	Discontinued
0.6884	Remote Similarity	NPD5406	Approved
0.6884	Remote Similarity	NPD5408	Approved
0.6884	Remote Similarity	NPD5404	Approved
0.6875	Remote Similarity	NPD1980	Approved
0.6875	Remote Similarity	NPD1981	Approved
0.6875	Remote Similarity	NPD1983	Approved
0.6875	Remote Similarity	NPD3143	Discontinued
0.687	Remote Similarity	NPD2797	Approved
0.687	Remote Similarity	NPD9273	Approved
0.686	Remote Similarity	NPD5451	Approved
0.6855	Remote Similarity	NPD9618	Approved
0.6855	Remote Similarity	NPD9614	Approved
0.685	Remote Similarity	NPD1651	Approved
0.685	Remote Similarity	NPD5585	Approved
0.6825	Remote Similarity	NPD7644	Approved
0.6812	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6090	Discontinued
0.68	Remote Similarity	NPD7157	Approved
0.68	Remote Similarity	NPD6387	Discontinued
0.6797	Remote Similarity	NPD1778	Approved
0.6797	Remote Similarity	NPD2667	Approved
0.6797	Remote Similarity	NPD2668	Approved
0.6788	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7037	Approved
0.6783	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2420	Approved
0.6783	Remote Similarity	NPD7390	Discontinued
0.6783	Remote Similarity	NPD7041	Phase 2
0.6783	Remote Similarity	NPD2421	Approved
0.6769	Remote Similarity	NPD2231	Phase 2
0.6769	Remote Similarity	NPD2235	Phase 2
0.6769	Remote Similarity	NPD3070	Discontinued
0.6765	Remote Similarity	NPD3109	Approved
0.6765	Remote Similarity	NPD3110	Approved
0.6761	Remote Similarity	NPD8131	Suspended
0.6744	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3645	Discontinued
0.6723	Remote Similarity	NPD9610	Approved
0.6723	Remote Similarity	NPD9608	Approved
0.672	Remote Similarity	NPD2629	Approved
0.6718	Remote Similarity	NPD6582	Phase 2
0.6718	Remote Similarity	NPD4659	Approved
0.6718	Remote Similarity	NPD1669	Approved
0.6718	Remote Similarity	NPD6583	Phase 3
0.6716	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3657	Discovery
0.6714	Remote Similarity	NPD5763	Approved
0.6714	Remote Similarity	NPD5762	Approved
0.6714	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4818	Approved
0.6695	Remote Similarity	NPD4817	Approved
0.6694	Remote Similarity	NPD9377	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