NPASS Compound

Structure

NPC469719 OpenBabel07101718192D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.7591 2.2406 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 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -0.3955 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7700 2.0316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 18 2 0 0 0 0 14 17 2 0 0 0 0 15 19 1 1 0 0 0 15 21 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 21 4 1 6 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.22
Volume:	347.217
LogP:	4.518
LogD:	3.539
LogS:	-4.127
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	4.108
Fsp3:	0.714
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:	-4.737
MDCK Permeability:	2.785226024570875e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.326
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	96.55345916748047%
Volume Distribution (VD):	1.357
Pgp-substrate:	4.113337993621826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.763
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.749
CYP3A4-inhibitor:	0.612
CYP3A4-substrate:	0.65

ADMET: Excretion

Clearance (CL):	13.923
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.362
Skin Sensitization:	0.808
Carcinogencity:	0.034
Eye Corrosion:	0.018
Eye Irritation:	0.739
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC469719

Natural Product ID:	NPC469719
*Common Name:**	Dasyscyphin E
IUPAC Name:	(4S,4aR,6aS,11aR,11bR)-4,6a,8,11b-tetramethyl-1,2,3,4a,5,6,11,11a-octahydrobenzo[a]fluorene-4,7-diol
Synonyms:	Dasyscyphin E
Standard InCHIKey:	DHFXPJCRRFHREQ-QANQIFJLSA-N
Standard InCHI:	InChI=1S/C21H30O2/c1-13-6-7-14-12-16-19(2)9-5-10-21(4,23)15(19)8-11-20(16,3)17(14)18(13)22/h6-7,15-16,22-23H,5,8-12H2,1-4H3/t15-,16-,19+,20+,21+/m1/s1
SMILES:	CC1=C(C2=C(CC3C2(CCC4C3(CCCC4(C)O)C)C)C=C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163004
PubChem CID:	46905058
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO9819	Dasyscyphus niveus	Species	Hyaloscyphaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18771321]
NPO9819	Dasyscyphus niveus	Species	Hyaloscyphaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6401	Organism	Magnaporthe grisea 70-15	Magnaporthe oryzae 70-15	Inhibition	=	100.0	%	PMID[469879]

☑ 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 NPC469719 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	333
0.1-0.2	1740
0.2-0.3	3280
0.3-0.4	8981
0.4-0.5	11435
0.5-0.6	12200
0.6-0.7	3843
0.7-0.8	741
0.8-0.85	103
0.85-0.9	36
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC322753
0.9091	High Similarity	NPC260323
0.9091	High Similarity	NPC176279
0.9027	High Similarity	NPC92
0.9027	High Similarity	NPC469663
0.9027	High Similarity	NPC471668
0.9018	High Similarity	NPC195922
0.9009	High Similarity	NPC250323
0.9	High Similarity	NPC141782
0.8938	High Similarity	NPC35797
0.8938	High Similarity	NPC192948
0.8919	High Similarity	NPC77772
0.8889	High Similarity	NPC117115
0.8879	High Similarity	NPC99734
0.886	High Similarity	NPC308311
0.886	High Similarity	NPC38893
0.886	High Similarity	NPC477137
0.886	High Similarity	NPC219112
0.885	High Similarity	NPC471534
0.885	High Similarity	NPC268160
0.8839	High Similarity	NPC46940
0.8829	High Similarity	NPC13482
0.8818	High Similarity	NPC64586
0.8807	High Similarity	NPC310456
0.8793	High Similarity	NPC126002
0.8793	High Similarity	NPC93071
0.8783	High Similarity	NPC172219
0.8783	High Similarity	NPC304510
0.8783	High Similarity	NPC477136
0.8772	High Similarity	NPC147179
0.8761	High Similarity	NPC715
0.875	High Similarity	NPC95716
0.875	High Similarity	NPC470770
0.875	High Similarity	NPC266937
0.8727	High Similarity	NPC151477
0.8707	High Similarity	NPC471671
0.8707	High Similarity	NPC48342
0.8707	High Similarity	NPC164649
0.8696	High Similarity	NPC154511
0.8696	High Similarity	NPC247858
0.8696	High Similarity	NPC137496
0.8696	High Similarity	NPC308828
0.8696	High Similarity	NPC257540
0.8696	High Similarity	NPC141001
0.8696	High Similarity	NPC474387
0.8696	High Similarity	NPC474358
0.8673	High Similarity	NPC62867
0.8673	High Similarity	NPC177962
0.8661	High Similarity	NPC132720
0.8655	High Similarity	NPC297057
0.8649	High Similarity	NPC11554
0.8649	High Similarity	NPC306295
0.8644	High Similarity	NPC328504
0.8632	High Similarity	NPC469644
0.8624	High Similarity	NPC238696
0.8621	High Similarity	NPC16030
0.8571	High Similarity	NPC58865
0.8559	High Similarity	NPC190501
0.8559	High Similarity	NPC318552
0.8559	High Similarity	NPC320439
0.8547	High Similarity	NPC469609
0.8547	High Similarity	NPC206
0.8519	High Similarity	NPC72729
0.8487	Intermediate Similarity	NPC259703
0.8487	Intermediate Similarity	NPC32322
0.8468	Intermediate Similarity	NPC53740
0.8468	Intermediate Similarity	NPC21594
0.8448	Intermediate Similarity	NPC84999
0.8448	Intermediate Similarity	NPC246760
0.844	Intermediate Similarity	NPC51015
0.844	Intermediate Similarity	NPC252105
0.8435	Intermediate Similarity	NPC317869
0.8426	Intermediate Similarity	NPC299762
0.8426	Intermediate Similarity	NPC33675
0.8421	Intermediate Similarity	NPC151537
0.8421	Intermediate Similarity	NPC469912
0.8417	Intermediate Similarity	NPC77569
0.8417	Intermediate Similarity	NPC249340
0.8417	Intermediate Similarity	NPC162935
0.8417	Intermediate Similarity	NPC142198
0.8407	Intermediate Similarity	NPC314187
0.8403	Intermediate Similarity	NPC260832
0.8403	Intermediate Similarity	NPC68339
0.8403	Intermediate Similarity	NPC135467
0.8393	Intermediate Similarity	NPC27252
0.8393	Intermediate Similarity	NPC472979
0.839	Intermediate Similarity	NPC154030
0.8378	Intermediate Similarity	NPC47284
0.8364	Intermediate Similarity	NPC19856
0.8362	Intermediate Similarity	NPC249270
0.8348	Intermediate Similarity	NPC471179
0.8348	Intermediate Similarity	NPC228425
0.8347	Intermediate Similarity	NPC11250
0.8347	Intermediate Similarity	NPC176208
0.8333	Intermediate Similarity	NPC241001
0.8333	Intermediate Similarity	NPC79241
0.8333	Intermediate Similarity	NPC6597
0.8319	Intermediate Similarity	NPC79933
0.8319	Intermediate Similarity	NPC31296
0.8319	Intermediate Similarity	NPC258366
0.8319	Intermediate Similarity	NPC473974
0.8319	Intermediate Similarity	NPC151197
0.8305	Intermediate Similarity	NPC299180
0.8304	Intermediate Similarity	NPC271274
0.8293	Intermediate Similarity	NPC124030
0.8288	Intermediate Similarity	NPC272029
0.8279	Intermediate Similarity	NPC471187
0.8276	Intermediate Similarity	NPC322239
0.8268	Intermediate Similarity	NPC85595
0.8264	Intermediate Similarity	NPC253627
0.8264	Intermediate Similarity	NPC154696
0.8264	Intermediate Similarity	NPC475166
0.8241	Intermediate Similarity	NPC259512
0.8241	Intermediate Similarity	NPC312132
0.823	Intermediate Similarity	NPC472980
0.8224	Intermediate Similarity	NPC289769
0.822	Intermediate Similarity	NPC472862
0.8214	Intermediate Similarity	NPC243601
0.8211	Intermediate Similarity	NPC181334
0.8198	Intermediate Similarity	NPC269212
0.8198	Intermediate Similarity	NPC108497
0.8197	Intermediate Similarity	NPC321402
0.8197	Intermediate Similarity	NPC478058
0.8197	Intermediate Similarity	NPC471794
0.8197	Intermediate Similarity	NPC121168
0.819	Intermediate Similarity	NPC302371
0.8182	Intermediate Similarity	NPC211885
0.8182	Intermediate Similarity	NPC225506
0.8174	Intermediate Similarity	NPC296683
0.8167	Intermediate Similarity	NPC323074
0.8167	Intermediate Similarity	NPC42657
0.8158	Intermediate Similarity	NPC149455
0.8158	Intermediate Similarity	NPC64642
0.8158	Intermediate Similarity	NPC472982
0.8148	Intermediate Similarity	NPC222146
0.8145	Intermediate Similarity	NPC137750
0.8142	Intermediate Similarity	NPC155072
0.813	Intermediate Similarity	NPC198014
0.8125	Intermediate Similarity	NPC475225
0.8125	Intermediate Similarity	NPC254965
0.8125	Intermediate Similarity	NPC327811
0.8103	Intermediate Similarity	NPC224527
0.8099	Intermediate Similarity	NPC477037
0.8099	Intermediate Similarity	NPC325544
0.8099	Intermediate Similarity	NPC318581
0.8091	Intermediate Similarity	NPC122005
0.8091	Intermediate Similarity	NPC252821
0.808	Intermediate Similarity	NPC100414
0.808	Intermediate Similarity	NPC321822
0.808	Intermediate Similarity	NPC325294
0.808	Intermediate Similarity	NPC145659
0.808	Intermediate Similarity	NPC9292
0.808	Intermediate Similarity	NPC43000
0.807	Intermediate Similarity	NPC66834
0.8067	Intermediate Similarity	NPC33900
0.8065	Intermediate Similarity	NPC248557
0.8065	Intermediate Similarity	NPC15127
0.8056	Intermediate Similarity	NPC245187
0.8056	Intermediate Similarity	NPC152415
0.8053	Intermediate Similarity	NPC138942
0.8053	Intermediate Similarity	NPC99557
0.8053	Intermediate Similarity	NPC219286
0.8051	Intermediate Similarity	NPC107240
0.8049	Intermediate Similarity	NPC71094
0.8049	Intermediate Similarity	NPC120172
0.8049	Intermediate Similarity	NPC152946
0.8036	Intermediate Similarity	NPC471228
0.8036	Intermediate Similarity	NPC168829
0.8036	Intermediate Similarity	NPC235762
0.8031	Intermediate Similarity	NPC131684
0.8031	Intermediate Similarity	NPC276238
0.8017	Intermediate Similarity	NPC176893
0.8016	Intermediate Similarity	NPC108164
0.8016	Intermediate Similarity	NPC471077
0.8016	Intermediate Similarity	NPC78364
0.8016	Intermediate Similarity	NPC69424
0.8016	Intermediate Similarity	NPC176130
0.8016	Intermediate Similarity	NPC30491
0.8016	Intermediate Similarity	NPC262936
0.8016	Intermediate Similarity	NPC84672
0.8	Intermediate Similarity	NPC4286
0.8	Intermediate Similarity	NPC87985
0.8	Intermediate Similarity	NPC156313
0.8	Intermediate Similarity	NPC76119
0.8	Intermediate Similarity	NPC77492
0.7982	Intermediate Similarity	NPC469913
0.7982	Intermediate Similarity	NPC144682
0.7969	Intermediate Similarity	NPC108129
0.7967	Intermediate Similarity	NPC474115
0.7966	Intermediate Similarity	NPC321589
0.7966	Intermediate Similarity	NPC117846
0.7966	Intermediate Similarity	NPC263753
0.7965	Intermediate Similarity	NPC475580
0.7965	Intermediate Similarity	NPC56168
0.7965	Intermediate Similarity	NPC288411
0.7963	Intermediate Similarity	NPC55903
0.7953	Intermediate Similarity	NPC201069
0.7951	Intermediate Similarity	NPC103916
0.7951	Intermediate Similarity	NPC478121
0.7949	Intermediate Similarity	NPC54373

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 NPC469719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	973
0.2-0.3	1121
0.3-0.4	2939
0.4-0.5	2219
0.5-0.6	1254
0.6-0.7	255
0.7-0.8	64
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8879	High Similarity	NPD4059	Approved
0.8727	High Similarity	NPD2342	Discontinued
0.8707	High Similarity	NPD3091	Approved
0.8673	High Similarity	NPD7635	Approved
0.8559	High Similarity	NPD3019	Approved
0.8417	Intermediate Similarity	NPD3092	Approved
0.8403	Intermediate Similarity	NPD2932	Approved
0.825	Intermediate Similarity	NPD3095	Discontinued
0.8241	Intermediate Similarity	NPD288	Approved
0.8148	Intermediate Similarity	NPD844	Approved
0.8145	Intermediate Similarity	NPD3094	Phase 2
0.8131	Intermediate Similarity	NPD845	Approved
0.808	Intermediate Similarity	NPD4624	Approved
0.8018	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD5736	Approved
0.7982	Intermediate Similarity	NPD1809	Phase 2
0.7931	Intermediate Similarity	NPD4750	Phase 3
0.7928	Intermediate Similarity	NPD3020	Approved
0.7886	Intermediate Similarity	NPD3026	Approved
0.7886	Intermediate Similarity	NPD3023	Approved
0.7869	Intermediate Similarity	NPD3024	Approved
0.7869	Intermediate Similarity	NPD3025	Approved
0.7769	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD6663	Approved
0.7727	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4097	Suspended
0.7661	Intermediate Similarity	NPD2286	Discontinued
0.7658	Intermediate Similarity	NPD2859	Approved
0.7658	Intermediate Similarity	NPD2860	Approved
0.7638	Intermediate Similarity	NPD6696	Suspended
0.7627	Intermediate Similarity	NPD3021	Approved
0.7627	Intermediate Similarity	NPD3022	Approved
0.7615	Intermediate Similarity	NPD4625	Phase 3
0.7594	Intermediate Similarity	NPD6353	Approved
0.7581	Intermediate Similarity	NPD4093	Discontinued
0.7576	Intermediate Similarity	NPD3620	Phase 2
0.7576	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2934	Approved
0.7568	Intermediate Similarity	NPD2933	Approved
0.7559	Intermediate Similarity	NPD5327	Phase 3
0.7559	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD1751	Approved
0.75	Intermediate Similarity	NPD7741	Discontinued
0.7481	Intermediate Similarity	NPD7743	Approved
0.7481	Intermediate Similarity	NPD7742	Approved
0.748	Intermediate Similarity	NPD7340	Approved
0.7479	Intermediate Similarity	NPD1792	Phase 2
0.7459	Intermediate Similarity	NPD497	Approved
0.7444	Intermediate Similarity	NPD4140	Approved
0.7414	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2605	Approved
0.7405	Intermediate Similarity	NPD2606	Approved
0.7402	Intermediate Similarity	NPD1201	Approved
0.7388	Intermediate Similarity	NPD5735	Approved
0.7381	Intermediate Similarity	NPD4626	Approved
0.7377	Intermediate Similarity	NPD495	Approved
0.7377	Intermediate Similarity	NPD498	Approved
0.7377	Intermediate Similarity	NPD496	Approved
0.7377	Intermediate Similarity	NPD1398	Phase 1
0.7355	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5155	Approved
0.7348	Intermediate Similarity	NPD5156	Approved
0.7328	Intermediate Similarity	NPD3636	Approved
0.7328	Intermediate Similarity	NPD3635	Approved
0.7328	Intermediate Similarity	NPD3637	Approved
0.7308	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4749	Approved
0.7273	Intermediate Similarity	NPD3595	Approved
0.7273	Intermediate Similarity	NPD3594	Approved
0.7266	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3638	Discontinued
0.7266	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6671	Approved
0.7252	Intermediate Similarity	NPD2194	Approved
0.7252	Intermediate Similarity	NPD2195	Approved
0.7252	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4589	Approved
0.7236	Intermediate Similarity	NPD2234	Approved
0.7236	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD2228	Approved
0.7236	Intermediate Similarity	NPD2229	Approved
0.7236	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1445	Approved
0.7227	Intermediate Similarity	NPD1444	Approved
0.7222	Intermediate Similarity	NPD7330	Discontinued
0.7222	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7179	Intermediate Similarity	NPD940	Approved
0.7179	Intermediate Similarity	NPD846	Approved
0.7177	Intermediate Similarity	NPD5951	Approved
0.7176	Intermediate Similarity	NPD1470	Approved
0.7163	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4725	Approved
0.7122	Intermediate Similarity	NPD4721	Approved
0.7122	Intermediate Similarity	NPD4726	Approved
0.7111	Intermediate Similarity	NPD8032	Phase 2
0.7101	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5304	Approved
0.7087	Intermediate Similarity	NPD5303	Approved
0.7077	Intermediate Similarity	NPD2230	Approved
0.7077	Intermediate Similarity	NPD2233	Approved
0.7077	Intermediate Similarity	NPD2232	Approved
0.7059	Intermediate Similarity	NPD4060	Phase 1
0.705	Intermediate Similarity	NPD5405	Approved
0.705	Intermediate Similarity	NPD5404	Approved
0.705	Intermediate Similarity	NPD6100	Approved
0.705	Intermediate Similarity	NPD5406	Approved
0.705	Intermediate Similarity	NPD5408	Approved
0.705	Intermediate Similarity	NPD6099	Approved
0.7031	Intermediate Similarity	NPD5691	Approved
0.7031	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6972	Remote Similarity	NPD7003	Approved
0.697	Remote Similarity	NPD1283	Approved
0.6957	Remote Similarity	NPD2157	Approved
0.6949	Remote Similarity	NPD1242	Phase 1
0.6929	Remote Similarity	NPD7636	Approved
0.6923	Remote Similarity	NPD3143	Discontinued
0.6923	Remote Similarity	NPD8131	Suspended
0.6912	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD111	Approved
0.6905	Remote Similarity	NPD1793	Approved
0.6905	Remote Similarity	NPD1791	Approved
0.6899	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1651	Approved
0.6897	Remote Similarity	NPD3645	Discontinued
0.6884	Remote Similarity	NPD3657	Discovery
0.6875	Remote Similarity	NPD7610	Discontinued
0.687	Remote Similarity	NPD1611	Approved
0.6857	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.685	Remote Similarity	NPD709	Approved
0.6846	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD9500	Approved
0.6831	Remote Similarity	NPD4257	Approved
0.6831	Remote Similarity	NPD4256	Phase 2
0.6818	Remote Similarity	NPD3070	Discontinued
0.6797	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4908	Phase 1
0.6744	Remote Similarity	NPD7644	Approved
0.6742	Remote Similarity	NPD1281	Approved
0.6736	Remote Similarity	NPD8166	Discontinued
0.6736	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6273	Approved
0.6719	Remote Similarity	NPD6387	Discontinued
0.6719	Remote Similarity	NPD4198	Discontinued
0.6718	Remote Similarity	NPD7725	Approved
0.6715	Remote Similarity	NPD7095	Approved
0.6713	Remote Similarity	NPD7037	Approved
0.6712	Remote Similarity	NPD2420	Approved
0.6712	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7390	Discontinued
0.6712	Remote Similarity	NPD7041	Phase 2
0.6712	Remote Similarity	NPD2421	Approved
0.6694	Remote Similarity	NPD4720	Approved
0.6694	Remote Similarity	NPD4717	Approved
0.6694	Remote Similarity	NPD4718	Approved
0.6693	Remote Similarity	NPD5283	Phase 1
0.6691	Remote Similarity	NPD6346	Approved
0.6689	Remote Similarity	NPD5699	Approved
0.6667	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6049	Phase 2
0.6667	Remote Similarity	NPD2209	Approved
0.6667	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2211	Approved
0.6667	Remote Similarity	NPD1616	Discontinued
0.6667	Remote Similarity	NPD1981	Approved
0.6667	Remote Similarity	NPD1983	Approved
0.6667	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3028	Approved
0.6667	Remote Similarity	NPD1980	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3300	Phase 2
0.6643	Remote Similarity	NPD2346	Discontinued
0.6642	Remote Similarity	NPD1669	Approved
0.6642	Remote Similarity	NPD1755	Approved
0.6623	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7831	Phase 2
0.6623	Remote Similarity	NPD7833	Phase 2
0.6618	Remote Similarity	NPD6584	Phase 3
0.6617	Remote Similarity	NPD1610	Phase 2
0.6614	Remote Similarity	NPD1138	Approved
0.6612	Remote Similarity	NPD4818	Approved
0.6612	Remote Similarity	NPD4817	Approved
0.6596	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5125	Phase 3
0.6591	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1778	Approved
0.6591	Remote Similarity	NPD2667	Approved
0.6591	Remote Similarity	NPD5126	Approved
0.6591	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2668	Approved
0.6571	Remote Similarity	NPD3109	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