NPASS Compound

Structure

NPC471668 OpenBabel07101719252D 32 35 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 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 5.1962 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 -1.7321 -0.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 2.5981 -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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.8660 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 1.7321 1.0000 0.0000 C 0 0 2 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 0.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 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 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 21 2 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 30 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 16 27 1 0 0 0 0 17 23 1 0 0 0 0 17 24 2 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 23 1 0 0 0 0 20 30 1 0 0 0 0 22 15 1 1 0 0 0 22 24 1 0 0 0 0 23 26 2 0 0 0 0 24 25 1 0 0 0 0 25 29 1 0 0 0 0 26 31 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 6 0 0 0 29 7 1 6 0 0 0 30 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.35
Volume:	500.245
LogP:	7.689
LogD:	5.232
LogS:	-5.937
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	4.644
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.918
MDCK Permeability:	9.158390639640857e-06
Pgp-inhibitor:	0.984
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.574
Plasma Protein Binding (PPB):	97.32962036132812%
Volume Distribution (VD):	3.607
Pgp-substrate:	2.1891307830810547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.282
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.187
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.53
CYP2D6-substrate:	0.712
CYP3A4-inhibitor:	0.663
CYP3A4-substrate:	0.685

ADMET: Excretion

Clearance (CL):	12.074
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.272
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.278
Carcinogencity:	0.719
Eye Corrosion:	0.003
Eye Irritation:	0.481
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC471668

Natural Product ID:	NPC471668
*Common Name:**	7-(Menth-1-En-4-Ol)-Ferruginol
IUPAC Name:	(4bS,8aS,10S)-10-[(4-hydroxy-4-propan-2-ylcyclohexen-1-yl)methyl]-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol
Synonyms:
Standard InCHIKey:	IYKBYZQSSGTINJ-WPHAXYCQSA-N
Standard InCHI:	InChI=1S/C30H46O2/c1-19(2)23-17-24-22(15-21-9-13-30(32,14-10-21)20(3)4)16-27-28(5,6)11-8-12-29(27,7)25(24)18-26(23)31/h9,17-20,22,27,31-32H,8,10-16H2,1-7H3/t22-,27+,29-,30?/m1/s1
SMILES:	CC(C)C1=C(C=C2C(=C1)C(CC3C2(CCCC3(C)C)C)CC4=CCC(CC4)(C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3091480
PubChem CID:	72724973
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24210499]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	whole plants	east Texas, USA	2009-2011	PMID[24210499]
NPO18892	Salvinia molesta	Species	Salviniaceae	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
GI50	7

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	GI50	=	58410.0	nM	PMID[541324]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	75000.0	nM	PMID[541324]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	48050.0	nM	PMID[541324]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	54190.0	nM	PMID[541324]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	62910.0	nM	PMID[541324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	87280.0	nM	PMID[541324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	60440.0	nM	PMID[541324]

☑ 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 NPC471668 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	340
0.1-0.2	1728
0.2-0.3	3635
0.3-0.4	9397
0.4-0.5	10341
0.5-0.6	10869
0.6-0.7	5049
0.7-0.8	1112
0.8-0.85	141
0.85-0.9	60
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC93071
0.9554	High Similarity	NPC126002
0.9537	High Similarity	NPC260323
0.9537	High Similarity	NPC176279
0.945	High Similarity	NPC250323
0.9369	High Similarity	NPC35797
0.9369	High Similarity	NPC192948
0.9286	High Similarity	NPC308311
0.9286	High Similarity	NPC38893
0.9286	High Similarity	NPC477137
0.9279	High Similarity	NPC195922
0.9266	High Similarity	NPC141782
0.9266	High Similarity	NPC13482
0.9204	High Similarity	NPC477136
0.9204	High Similarity	NPC172219
0.9204	High Similarity	NPC304510
0.9167	High Similarity	NPC151477
0.9123	High Similarity	NPC471671
0.9115	High Similarity	NPC219112
0.9107	High Similarity	NPC268160
0.9099	High Similarity	NPC46940
0.9074	High Similarity	NPC21594
0.9043	High Similarity	NPC469644
0.9027	High Similarity	NPC147179
0.9027	High Similarity	NPC469719
0.9018	High Similarity	NPC715
0.9009	High Similarity	NPC95716
0.8981	High Similarity	NPC117115
0.8957	High Similarity	NPC154030
0.8957	High Similarity	NPC206
0.8947	High Similarity	NPC141001
0.8947	High Similarity	NPC308828
0.8947	High Similarity	NPC469663
0.8947	High Similarity	NPC92
0.8929	High Similarity	NPC62867
0.8929	High Similarity	NPC177962
0.8909	High Similarity	NPC11554
0.8889	High Similarity	NPC259703
0.8889	High Similarity	NPC32322
0.887	High Similarity	NPC16030
0.8839	High Similarity	NPC470770
0.8839	High Similarity	NPC151537
0.8839	High Similarity	NPC77772
0.8839	High Similarity	NPC322753
0.8839	High Similarity	NPC266937
0.8829	High Similarity	NPC58865
0.8814	High Similarity	NPC249340
0.8814	High Similarity	NPC154696
0.8814	High Similarity	NPC162935
0.8803	High Similarity	NPC135467
0.8803	High Similarity	NPC260832
0.8793	High Similarity	NPC469609
0.8772	High Similarity	NPC471534
0.8761	High Similarity	NPC228425
0.875	High Similarity	NPC132720
0.875	High Similarity	NPC296683
0.8739	High Similarity	NPC11250
0.8739	High Similarity	NPC478058
0.8718	High Similarity	NPC151197
0.8707	High Similarity	NPC299180
0.8689	High Similarity	NPC108164
0.8684	High Similarity	NPC322239
0.8684	High Similarity	NPC317869
0.8673	High Similarity	NPC469912
0.8667	High Similarity	NPC471187
0.8661	High Similarity	NPC314187
0.8611	High Similarity	NPC211885
0.8607	High Similarity	NPC43000
0.8607	High Similarity	NPC100414
0.8607	High Similarity	NPC325294
0.8607	High Similarity	NPC321822
0.8596	High Similarity	NPC471179
0.8595	High Similarity	NPC181334
0.8583	High Similarity	NPC71094
0.8583	High Similarity	NPC297057
0.8583	High Similarity	NPC176208
0.8571	High Similarity	NPC241001
0.8559	High Similarity	NPC271274
0.8537	High Similarity	NPC471077
0.8532	High Similarity	NPC252105
0.8525	High Similarity	NPC137750
0.8525	High Similarity	NPC124030
0.8522	High Similarity	NPC263753
0.85	High Similarity	NPC253627
0.8487	Intermediate Similarity	NPC99734
0.8482	Intermediate Similarity	NPC320439
0.8475	Intermediate Similarity	NPC48342
0.8475	Intermediate Similarity	NPC164649
0.8468	Intermediate Similarity	NPC219286
0.8468	Intermediate Similarity	NPC99557
0.8462	Intermediate Similarity	NPC154511
0.8462	Intermediate Similarity	NPC474358
0.8462	Intermediate Similarity	NPC247858
0.8462	Intermediate Similarity	NPC474387
0.8462	Intermediate Similarity	NPC137496
0.8462	Intermediate Similarity	NPC257540
0.844	Intermediate Similarity	NPC225506
0.844	Intermediate Similarity	NPC72729
0.843	Intermediate Similarity	NPC121168
0.843	Intermediate Similarity	NPC471794
0.843	Intermediate Similarity	NPC152946
0.8417	Intermediate Similarity	NPC328504
0.8403	Intermediate Similarity	NPC42657
0.8393	Intermediate Similarity	NPC53740
0.8393	Intermediate Similarity	NPC155072
0.8387	Intermediate Similarity	NPC84672
0.8387	Intermediate Similarity	NPC69424
0.8387	Intermediate Similarity	NPC72667
0.8387	Intermediate Similarity	NPC176130
0.8387	Intermediate Similarity	NPC78364
0.8378	Intermediate Similarity	NPC272029
0.8378	Intermediate Similarity	NPC238696
0.8376	Intermediate Similarity	NPC84999
0.8376	Intermediate Similarity	NPC246760
0.8374	Intermediate Similarity	NPC4286
0.8374	Intermediate Similarity	NPC76119
0.8362	Intermediate Similarity	NPC321589
0.8361	Intermediate Similarity	NPC198014
0.8349	Intermediate Similarity	NPC33675
0.8349	Intermediate Similarity	NPC299762
0.8349	Intermediate Similarity	NPC122005
0.8349	Intermediate Similarity	NPC252821
0.8347	Intermediate Similarity	NPC474115
0.8333	Intermediate Similarity	NPC108129
0.8333	Intermediate Similarity	NPC477037
0.8333	Intermediate Similarity	NPC318581
0.8333	Intermediate Similarity	NPC318552
0.8333	Intermediate Similarity	NPC190501
0.8333	Intermediate Similarity	NPC478121
0.8333	Intermediate Similarity	NPC325544
0.832	Intermediate Similarity	NPC201069
0.8319	Intermediate Similarity	NPC27252
0.8319	Intermediate Similarity	NPC472980
0.8319	Intermediate Similarity	NPC472979
0.8306	Intermediate Similarity	NPC254492
0.8305	Intermediate Similarity	NPC312105
0.8305	Intermediate Similarity	NPC261973
0.8304	Intermediate Similarity	NPC138942
0.8304	Intermediate Similarity	NPC47284
0.8293	Intermediate Similarity	NPC199273
0.8291	Intermediate Similarity	NPC107240
0.8291	Intermediate Similarity	NPC249270
0.8288	Intermediate Similarity	NPC168829
0.8288	Intermediate Similarity	NPC269212
0.8268	Intermediate Similarity	NPC243305
0.8261	Intermediate Similarity	NPC224870
0.8257	Intermediate Similarity	NPC79241
0.8257	Intermediate Similarity	NPC6597
0.8257	Intermediate Similarity	NPC77492
0.8254	Intermediate Similarity	NPC171460
0.8254	Intermediate Similarity	NPC303910
0.8254	Intermediate Similarity	NPC276238
0.825	Intermediate Similarity	NPC323074
0.825	Intermediate Similarity	NPC176893
0.8241	Intermediate Similarity	NPC144682
0.8241	Intermediate Similarity	NPC222146
0.824	Intermediate Similarity	NPC186889
0.824	Intermediate Similarity	NPC476536
0.823	Intermediate Similarity	NPC469913
0.823	Intermediate Similarity	NPC310456
0.8226	Intermediate Similarity	NPC87985
0.822	Intermediate Similarity	NPC474486
0.8214	Intermediate Similarity	NPC288411
0.8205	Intermediate Similarity	NPC117846
0.8203	Intermediate Similarity	NPC85595
0.8203	Intermediate Similarity	NPC321086
0.8198	Intermediate Similarity	NPC477685
0.8198	Intermediate Similarity	NPC51015
0.8197	Intermediate Similarity	NPC142198
0.8197	Intermediate Similarity	NPC77569
0.8182	Intermediate Similarity	NPC103916
0.8182	Intermediate Similarity	NPC68339
0.8182	Intermediate Similarity	NPC92730
0.8175	Intermediate Similarity	NPC47288
0.8174	Intermediate Similarity	NPC186385
0.8174	Intermediate Similarity	NPC299568
0.8165	Intermediate Similarity	NPC312132
0.8165	Intermediate Similarity	NPC259512
0.816	Intermediate Similarity	NPC71610
0.8151	Intermediate Similarity	NPC115808
0.8145	Intermediate Similarity	NPC224342
0.8145	Intermediate Similarity	NPC265413
0.8145	Intermediate Similarity	NPC248557
0.8145	Intermediate Similarity	NPC10154
0.8142	Intermediate Similarity	NPC243601
0.814	Intermediate Similarity	NPC49742
0.814	Intermediate Similarity	NPC476282
0.813	Intermediate Similarity	NPC321402
0.8125	Intermediate Similarity	NPC108497
0.8125	Intermediate Similarity	NPC312341
0.8125	Intermediate Similarity	NPC19856
0.8125	Intermediate Similarity	NPC471851
0.812	Intermediate Similarity	NPC166995
0.812	Intermediate Similarity	NPC302371
0.8115	Intermediate Similarity	NPC164852
0.8115	Intermediate Similarity	NPC129176
0.8099	Intermediate Similarity	NPC258366
0.8099	Intermediate Similarity	NPC31296
0.8099	Intermediate Similarity	NPC79933
0.8099	Intermediate Similarity	NPC473974

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 NPC471668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	989
0.2-0.3	1294
0.3-0.4	2931
0.4-0.5	2042
0.5-0.6	1157
0.6-0.7	307
0.7-0.8	83
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD7635	Approved
0.8487	Intermediate Similarity	NPD4059	Approved
0.8482	Intermediate Similarity	NPD2342	Discontinued
0.8475	Intermediate Similarity	NPD3091	Approved
0.8333	Intermediate Similarity	NPD2932	Approved
0.8333	Intermediate Similarity	NPD3019	Approved
0.8241	Intermediate Similarity	NPD1809	Phase 2
0.8197	Intermediate Similarity	NPD3092	Approved
0.8182	Intermediate Similarity	NPD3020	Approved
0.8174	Intermediate Similarity	NPD4750	Phase 3
0.8165	Intermediate Similarity	NPD288	Approved
0.8073	Intermediate Similarity	NPD844	Approved
0.8033	Intermediate Similarity	NPD3095	Discontinued
0.7982	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD5736	Approved
0.7946	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3094	Phase 2
0.7909	Intermediate Similarity	NPD2859	Approved
0.7909	Intermediate Similarity	NPD2860	Approved
0.789	Intermediate Similarity	NPD845	Approved
0.7886	Intermediate Similarity	NPD2286	Discontinued
0.7863	Intermediate Similarity	NPD3022	Approved
0.7863	Intermediate Similarity	NPD3021	Approved
0.7818	Intermediate Similarity	NPD2933	Approved
0.7818	Intermediate Similarity	NPD2934	Approved
0.7805	Intermediate Similarity	NPD4093	Discontinued
0.7803	Intermediate Similarity	NPD4097	Suspended
0.7778	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2605	Approved
0.7752	Intermediate Similarity	NPD2606	Approved
0.7742	Intermediate Similarity	NPD1751	Approved
0.7734	Intermediate Similarity	NPD4624	Approved
0.7731	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6696	Suspended
0.771	Intermediate Similarity	NPD6663	Approved
0.7705	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5156	Approved
0.7692	Intermediate Similarity	NPD5155	Approved
0.768	Intermediate Similarity	NPD3026	Approved
0.768	Intermediate Similarity	NPD3023	Approved
0.7661	Intermediate Similarity	NPD3024	Approved
0.7661	Intermediate Similarity	NPD3025	Approved
0.7634	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD3594	Approved
0.7615	Intermediate Similarity	NPD3595	Approved
0.7603	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4626	Approved
0.7597	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7340	Approved
0.7557	Intermediate Similarity	NPD4625	Phase 3
0.7538	Intermediate Similarity	NPD3636	Approved
0.7538	Intermediate Similarity	NPD3635	Approved
0.7538	Intermediate Similarity	NPD3637	Approved
0.7519	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD5327	Phase 3
0.7462	Intermediate Similarity	NPD2194	Approved
0.7462	Intermediate Similarity	NPD2195	Approved
0.746	Intermediate Similarity	NPD4589	Approved
0.7459	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2234	Approved
0.7459	Intermediate Similarity	NPD2229	Approved
0.7459	Intermediate Similarity	NPD2228	Approved
0.7445	Intermediate Similarity	NPD4725	Approved
0.7445	Intermediate Similarity	NPD4721	Approved
0.7445	Intermediate Similarity	NPD4726	Approved
0.7426	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7742	Approved
0.7426	Intermediate Similarity	NPD7743	Approved
0.7417	Intermediate Similarity	NPD1792	Phase 2
0.7414	Intermediate Similarity	NPD940	Approved
0.7414	Intermediate Similarity	NPD846	Approved
0.7407	Intermediate Similarity	NPD6353	Approved
0.7398	Intermediate Similarity	NPD497	Approved
0.7385	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1201	Approved
0.7344	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6671	Approved
0.7333	Intermediate Similarity	NPD5735	Approved
0.7317	Intermediate Similarity	NPD1398	Phase 1
0.7317	Intermediate Similarity	NPD496	Approved
0.7317	Intermediate Similarity	NPD495	Approved
0.7317	Intermediate Similarity	NPD498	Approved
0.7302	Intermediate Similarity	NPD7330	Discontinued
0.7302	Intermediate Similarity	NPD5303	Approved
0.7302	Intermediate Similarity	NPD5304	Approved
0.7286	Intermediate Similarity	NPD7003	Approved
0.7286	Intermediate Similarity	NPD8166	Discontinued
0.7259	Intermediate Similarity	NPD4140	Approved
0.7259	Intermediate Similarity	NPD4060	Phase 1
0.7246	Intermediate Similarity	NPD5404	Approved
0.7246	Intermediate Similarity	NPD5406	Approved
0.7246	Intermediate Similarity	NPD5408	Approved
0.7246	Intermediate Similarity	NPD6099	Approved
0.7246	Intermediate Similarity	NPD5405	Approved
0.7246	Intermediate Similarity	NPD6100	Approved
0.7244	Intermediate Similarity	NPD5691	Approved
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1242	Phase 1
0.7176	Intermediate Similarity	NPD1283	Approved
0.7174	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1444	Approved
0.7167	Intermediate Similarity	NPD1445	Approved
0.7165	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD111	Approved
0.7143	Intermediate Similarity	NPD7636	Approved
0.7133	Intermediate Similarity	NPD7390	Discontinued
0.7133	Intermediate Similarity	NPD7041	Phase 2
0.7133	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1470	Approved
0.7113	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1651	Approved
0.7092	Intermediate Similarity	NPD3638	Discontinued
0.709	Intermediate Similarity	NPD4908	Phase 1
0.7083	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8032	Phase 2
0.7042	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7095	Approved
0.7023	Intermediate Similarity	NPD2232	Approved
0.7023	Intermediate Similarity	NPD2233	Approved
0.7023	Intermediate Similarity	NPD2230	Approved
0.7015	Intermediate Similarity	NPD2861	Phase 2
0.7014	Intermediate Similarity	NPD2420	Approved
0.7014	Intermediate Similarity	NPD2421	Approved
0.7	Intermediate Similarity	NPD3143	Discontinued
0.6984	Remote Similarity	NPD5951	Approved
0.6972	Remote Similarity	NPD6674	Discontinued
0.6966	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9500	Approved
0.6917	Remote Similarity	NPD8651	Approved
0.6905	Remote Similarity	NPD5283	Phase 1
0.6901	Remote Similarity	NPD7037	Approved
0.6901	Remote Similarity	NPD4257	Approved
0.6901	Remote Similarity	NPD4256	Phase 2
0.6899	Remote Similarity	NPD7741	Discontinued
0.6894	Remote Similarity	NPD3070	Discontinued
0.6891	Remote Similarity	NPD3028	Approved
0.6884	Remote Similarity	NPD3109	Approved
0.6884	Remote Similarity	NPD3110	Approved
0.6875	Remote Similarity	NPD8131	Suspended
0.6875	Remote Similarity	NPD405	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7294	Phase 1
0.6853	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1793	Approved
0.685	Remote Similarity	NPD1791	Approved
0.6849	Remote Similarity	NPD3645	Discontinued
0.6842	Remote Similarity	NPD1669	Approved
0.6835	Remote Similarity	NPD3657	Discovery
0.6828	Remote Similarity	NPD3300	Phase 2
0.6822	Remote Similarity	NPD7644	Approved
0.6818	Remote Similarity	NPD1610	Phase 2
0.6818	Remote Similarity	NPD1611	Approved
0.6815	Remote Similarity	NPD6584	Phase 3
0.6797	Remote Similarity	NPD709	Approved
0.6797	Remote Similarity	NPD7157	Approved
0.6794	Remote Similarity	NPD7725	Approved
0.6794	Remote Similarity	NPD2668	Approved
0.6794	Remote Similarity	NPD2667	Approved
0.6794	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7458	Discontinued
0.6765	Remote Similarity	NPD4208	Discontinued
0.6763	Remote Similarity	NPD6346	Approved
0.6746	Remote Similarity	NPD228	Approved
0.6739	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2211	Approved
0.6736	Remote Similarity	NPD2209	Approved
0.672	Remote Similarity	NPD5451	Approved
0.6719	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6273	Approved
0.6689	Remote Similarity	NPD6090	Discontinued
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD2157	Approved
0.6643	Remote Similarity	NPD2979	Phase 3
0.6643	Remote Similarity	NPD2238	Phase 2
0.6642	Remote Similarity	NPD4212	Discontinued
0.6619	Remote Similarity	NPD3764	Approved
0.6618	Remote Similarity	NPD1164	Approved
0.6618	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4103	Phase 2
0.6617	Remote Similarity	NPD1980	Approved
0.6617	Remote Similarity	NPD1983	Approved
0.6617	Remote Similarity	NPD1981	Approved
0.661	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6049	Phase 2
0.6601	Remote Similarity	NPD5929	Approved
0.6599	Remote Similarity	NPD3845	Phase 1
0.6599	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5763	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