NPASS Compound

Structure

NPC469547 OpenBabel07101718222D 27 30 0 0 1 0 0 0 0 0999 V2000 0.3364 5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5657 -0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5383 2.3029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3304 3.2811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7951 1.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3793 3.5901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8441 1.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6851 3.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9420 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 4.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6362 2.9209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 3.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1009 1.2737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1499 1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 19 2 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 16 27 1 0 0 0 0 17 1 1 6 0 0 0 18 25 2 0 0 0 0 20 10 1 6 0 0 0 20 22 1 0 0 0 0 21 23 1 6 0 0 0 22 23 1 1 0 0 0 23 24 1 6 0 0 0 24 18 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.24
Volume:	402.623
LogP:	5.217
LogD:	4.559
LogS:	-5.45
# Rotatable Bonds:	5
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	4.505
Fsp3:	0.625
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:	-4.64
MDCK Permeability:	3.004975224030204e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.574
Plasma Protein Binding (PPB):	96.60868835449219%
Volume Distribution (VD):	1.256
Pgp-substrate:	1.74064040184021%

ADMET: Metabolism

CYP1A2-inhibitor:	0.447
CYP1A2-substrate:	0.677
CYP2C19-inhibitor:	0.873
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.829
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.703

ADMET: Excretion

Clearance (CL):	15.3
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.415
AMES Toxicity:	0.396
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.918
Carcinogencity:	0.317
Eye Corrosion:	0.054
Eye Irritation:	0.838
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC469547

Natural Product ID:	NPC469547
*Common Name:**	Oblongolide Z
IUPAC Name:	1-[(1S,3aS,5aR,7S,9aS,9bR)-7,9b-dimethyl-1-(2-phenylethoxy)-3,3a,5a,6,7,8,9,9a-octahydrobenzo[g][2]benzofuran-1-yl]ethanone
Synonyms:	Oblongolide Z
Standard InCHIKey:	WFMHAGOWQRBMPG-QECFBVRUSA-N
Standard InCHI:	InChI=1S/C24H32O3/c1-17-9-12-22-20(15-17)10-11-21-16-27-24(18(2)25,23(21,22)3)26-14-13-19-7-5-4-6-8-19/h4-8,10-11,17,20-22H,9,12-16H2,1-3H3/t17-,20-,21+,22-,23-,24+/m0/s1
SMILES:	C[C@H]1CC[C@H]2[C@H](C1)C=C[C@H]1[C@]2(C)[C@](OCCc2ccccc2)(OC1)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086914
PubChem CID:	44627609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO33230	Phomopsis sp. BCC 9789	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038128]

☑ 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	4
MIC	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	32000.0	nM	PMID[518868]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	37000.0	nM	PMID[518868]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	60000.0	nM	PMID[518868]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	=	14000.0	nM	PMID[518868]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	26000.0	nM	PMID[518868]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	136000.0	nM	PMID[518868]

☑ 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 NPC469547 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	238
0.1-0.2	1117
0.2-0.3	1987
0.3-0.4	6339
0.4-0.5	15051
0.5-0.6	15616
0.6-0.7	2167
0.7-0.8	178
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8049	Intermediate Similarity	NPC470818
0.8017	Intermediate Similarity	NPC326664
0.7946	Intermediate Similarity	NPC471186
0.7913	Intermediate Similarity	NPC137315
0.7903	Intermediate Similarity	NPC470816
0.7899	Intermediate Similarity	NPC61651
0.7886	Intermediate Similarity	NPC328107
0.7863	Intermediate Similarity	NPC241851
0.7845	Intermediate Similarity	NPC471189
0.7818	Intermediate Similarity	NPC221825
0.7798	Intermediate Similarity	NPC226041
0.776	Intermediate Similarity	NPC100402
0.776	Intermediate Similarity	NPC9180
0.7727	Intermediate Similarity	NPC145052
0.7719	Intermediate Similarity	NPC244933
0.7719	Intermediate Similarity	NPC94751
0.7719	Intermediate Similarity	NPC142326
0.7719	Intermediate Similarity	NPC85560
0.7674	Intermediate Similarity	NPC475493
0.7658	Intermediate Similarity	NPC476042
0.7652	Intermediate Similarity	NPC470007
0.7627	Intermediate Similarity	NPC143768
0.7627	Intermediate Similarity	NPC477475
0.7627	Intermediate Similarity	NPC477476
0.7623	Intermediate Similarity	NPC202015
0.7623	Intermediate Similarity	NPC470814
0.7623	Intermediate Similarity	NPC476645
0.7615	Intermediate Similarity	NPC476644
0.7603	Intermediate Similarity	NPC222968
0.7603	Intermediate Similarity	NPC323440
0.7603	Intermediate Similarity	NPC80605
0.7603	Intermediate Similarity	NPC45794
0.76	Intermediate Similarity	NPC318067
0.7589	Intermediate Similarity	NPC264728
0.7561	Intermediate Similarity	NPC473243
0.7561	Intermediate Similarity	NPC238861
0.7561	Intermediate Similarity	NPC77000
0.7542	Intermediate Similarity	NPC280789
0.7542	Intermediate Similarity	NPC471188
0.7538	Intermediate Similarity	NPC469499
0.7538	Intermediate Similarity	NPC471880
0.75	Intermediate Similarity	NPC470764
0.75	Intermediate Similarity	NPC478162
0.75	Intermediate Similarity	NPC473399
0.75	Intermediate Similarity	NPC203732
0.75	Intermediate Similarity	NPC469569
0.75	Intermediate Similarity	NPC21929
0.75	Intermediate Similarity	NPC7435
0.75	Intermediate Similarity	NPC478165
0.75	Intermediate Similarity	NPC473216
0.7481	Intermediate Similarity	NPC471862
0.748	Intermediate Similarity	NPC476599
0.748	Intermediate Similarity	NPC204784
0.7477	Intermediate Similarity	NPC103048
0.746	Intermediate Similarity	NPC469742
0.7459	Intermediate Similarity	NPC152812
0.7458	Intermediate Similarity	NPC265513
0.7438	Intermediate Similarity	NPC260886
0.7438	Intermediate Similarity	NPC9274
0.7436	Intermediate Similarity	NPC192577
0.7434	Intermediate Similarity	NPC128248
0.7434	Intermediate Similarity	NPC133809
0.7434	Intermediate Similarity	NPC136810
0.7434	Intermediate Similarity	NPC225079
0.7426	Intermediate Similarity	NPC471856
0.7422	Intermediate Similarity	NPC48992
0.7417	Intermediate Similarity	NPC67377
0.7417	Intermediate Similarity	NPC294458
0.7411	Intermediate Similarity	NPC120393
0.7407	Intermediate Similarity	NPC475400
0.7407	Intermediate Similarity	NPC84288
0.7402	Intermediate Similarity	NPC295664
0.7398	Intermediate Similarity	NPC318173
0.7395	Intermediate Similarity	NPC218855
0.7387	Intermediate Similarity	NPC12695
0.7385	Intermediate Similarity	NPC471832
0.7377	Intermediate Similarity	NPC242764
0.7377	Intermediate Similarity	NPC105141
0.7364	Intermediate Similarity	NPC115797
0.7364	Intermediate Similarity	NPC268607
0.7364	Intermediate Similarity	NPC51448
0.7355	Intermediate Similarity	NPC221275
0.7355	Intermediate Similarity	NPC474408
0.7344	Intermediate Similarity	NPC294050
0.7344	Intermediate Similarity	NPC328997
0.7339	Intermediate Similarity	NPC476484
0.7333	Intermediate Similarity	NPC470253
0.7328	Intermediate Similarity	NPC472682
0.7328	Intermediate Similarity	NPC474307
0.7328	Intermediate Similarity	NPC472692
0.7323	Intermediate Similarity	NPC51079
0.7323	Intermediate Similarity	NPC470815
0.7323	Intermediate Similarity	NPC325740
0.7323	Intermediate Similarity	NPC140118
0.7323	Intermediate Similarity	NPC12881
0.7321	Intermediate Similarity	NPC469891
0.7321	Intermediate Similarity	NPC469890
0.7321	Intermediate Similarity	NPC469892
0.7317	Intermediate Similarity	NPC268930
0.7317	Intermediate Similarity	NPC94425
0.7315	Intermediate Similarity	NPC9822
0.7315	Intermediate Similarity	NPC231591
0.7315	Intermediate Similarity	NPC298115
0.7311	Intermediate Similarity	NPC95126
0.7311	Intermediate Similarity	NPC475002
0.7299	Intermediate Similarity	NPC472236
0.7299	Intermediate Similarity	NPC472235
0.7295	Intermediate Similarity	NPC62138
0.7287	Intermediate Similarity	NPC146239
0.7287	Intermediate Similarity	NPC473423
0.7281	Intermediate Similarity	NPC112552
0.728	Intermediate Similarity	NPC988
0.728	Intermediate Similarity	NPC232958
0.728	Intermediate Similarity	NPC289432
0.7279	Intermediate Similarity	NPC476643
0.7273	Intermediate Similarity	NPC234637
0.7273	Intermediate Similarity	NPC130591
0.7273	Intermediate Similarity	NPC471721
0.7266	Intermediate Similarity	NPC472693
0.7266	Intermediate Similarity	NPC472694
0.7265	Intermediate Similarity	NPC474111
0.7265	Intermediate Similarity	NPC329705
0.7258	Intermediate Similarity	NPC254233
0.7252	Intermediate Similarity	NPC147561
0.725	Intermediate Similarity	NPC292834
0.7248	Intermediate Similarity	NPC67585
0.7248	Intermediate Similarity	NPC303967
0.7248	Intermediate Similarity	NPC110420
0.7236	Intermediate Similarity	NPC212891
0.7232	Intermediate Similarity	NPC469893
0.7231	Intermediate Similarity	NPC316553
0.7231	Intermediate Similarity	NPC195224
0.7222	Intermediate Similarity	NPC50872
0.7222	Intermediate Similarity	NPC144547
0.7218	Intermediate Similarity	NPC144257
0.7218	Intermediate Similarity	NPC159811
0.7213	Intermediate Similarity	NPC215419
0.7213	Intermediate Similarity	NPC474095
0.7213	Intermediate Similarity	NPC473869
0.7203	Intermediate Similarity	NPC470391
0.719	Intermediate Similarity	NPC471481
0.719	Intermediate Similarity	NPC93287
0.7188	Intermediate Similarity	NPC8990
0.7182	Intermediate Similarity	NPC125226
0.7177	Intermediate Similarity	NPC471553
0.7176	Intermediate Similarity	NPC225103
0.7168	Intermediate Similarity	NPC239185
0.7167	Intermediate Similarity	NPC291799
0.7164	Intermediate Similarity	NPC329913
0.7164	Intermediate Similarity	NPC126516
0.7155	Intermediate Similarity	NPC274443
0.7154	Intermediate Similarity	NPC135730
0.7143	Intermediate Similarity	NPC234337
0.7143	Intermediate Similarity	NPC474223
0.7143	Intermediate Similarity	NPC471107
0.7143	Intermediate Similarity	NPC475827
0.7143	Intermediate Similarity	NPC105709
0.7143	Intermediate Similarity	NPC472394
0.7143	Intermediate Similarity	NPC183339
0.7143	Intermediate Similarity	NPC471100
0.7143	Intermediate Similarity	NPC476225
0.7143	Intermediate Similarity	NPC133389
0.7132	Intermediate Similarity	NPC317163
0.7132	Intermediate Similarity	NPC477369
0.7132	Intermediate Similarity	NPC184109
0.7131	Intermediate Similarity	NPC196075
0.7121	Intermediate Similarity	NPC472388
0.7121	Intermediate Similarity	NPC473443
0.7121	Intermediate Similarity	NPC49272
0.7119	Intermediate Similarity	NPC100767
0.7111	Intermediate Similarity	NPC212207
0.7111	Intermediate Similarity	NPC23894
0.7109	Intermediate Similarity	NPC108286
0.7105	Intermediate Similarity	NPC134882
0.7103	Intermediate Similarity	NPC294134
0.7099	Intermediate Similarity	NPC230331
0.7099	Intermediate Similarity	NPC262936
0.7099	Intermediate Similarity	NPC30491
0.7097	Intermediate Similarity	NPC469843
0.7091	Intermediate Similarity	NPC108026
0.709	Intermediate Similarity	NPC15850
0.709	Intermediate Similarity	NPC472656
0.7087	Intermediate Similarity	NPC472981
0.7077	Intermediate Similarity	NPC470765
0.7077	Intermediate Similarity	NPC473082
0.7077	Intermediate Similarity	NPC275576
0.7075	Intermediate Similarity	NPC270507
0.7073	Intermediate Similarity	NPC93181
0.7073	Intermediate Similarity	NPC228936
0.7071	Intermediate Similarity	NPC470231
0.7071	Intermediate Similarity	NPC80895
0.7071	Intermediate Similarity	NPC471912
0.7069	Intermediate Similarity	NPC244427
0.7069	Intermediate Similarity	NPC222390
0.7069	Intermediate Similarity	NPC474112
0.7068	Intermediate Similarity	NPC470278
0.7068	Intermediate Similarity	NPC472418
0.7068	Intermediate Similarity	NPC472361
0.7059	Intermediate Similarity	NPC112903
0.7054	Intermediate Similarity	NPC85511

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 NPC469547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	802
0.2-0.3	1157
0.3-0.4	3200
0.4-0.5	2464
0.5-0.6	1051
0.6-0.7	249
0.7-0.8	14
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8087	Intermediate Similarity	NPD7094	Approved
0.8087	Intermediate Similarity	NPD6858	Approved
0.7642	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1989	Approved
0.7355	Intermediate Similarity	NPD2629	Approved
0.7273	Intermediate Similarity	NPD7961	Discontinued
0.7252	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3672	Approved
0.7248	Intermediate Similarity	NPD3673	Approved
0.7193	Intermediate Similarity	NPD2066	Phase 3
0.7177	Intermediate Similarity	NPD6065	Approved
0.7168	Intermediate Similarity	NPD3495	Discontinued
0.7143	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD1693	Approved
0.713	Intermediate Similarity	NPD1087	Approved
0.7117	Intermediate Similarity	NPD1088	Approved
0.7083	Intermediate Similarity	NPD2067	Discontinued
0.7073	Intermediate Similarity	NPD4766	Approved
0.7054	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7798	Approved
0.7016	Intermediate Similarity	NPD3317	Approved
0.7016	Intermediate Similarity	NPD4198	Discontinued
0.7009	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1929	Approved
0.7009	Intermediate Similarity	NPD1930	Approved
0.7008	Intermediate Similarity	NPD2932	Approved
0.6964	Remote Similarity	NPD7631	Approved
0.6942	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1090	Approved
0.6937	Remote Similarity	NPD1086	Approved
0.6937	Remote Similarity	NPD1089	Approved
0.6929	Remote Similarity	NPD3025	Approved
0.6929	Remote Similarity	NPD3024	Approved
0.6917	Remote Similarity	NPD7055	Discontinued
0.6905	Remote Similarity	NPD7610	Discontinued
0.6903	Remote Similarity	NPD1563	Approved
0.6897	Remote Similarity	NPD7239	Suspended
0.6889	Remote Similarity	NPD6663	Approved
0.6885	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7305	Phase 1
0.6875	Remote Similarity	NPD3019	Approved
0.6875	Remote Similarity	NPD7609	Phase 3
0.6855	Remote Similarity	NPD6010	Discontinued
0.685	Remote Similarity	NPD7009	Phase 2
0.6847	Remote Similarity	NPD800	Approved
0.6842	Remote Similarity	NPD5736	Approved
0.6842	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7084	Phase 3
0.6838	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6685	Approved
0.6822	Remote Similarity	NPD3023	Approved
0.6822	Remote Similarity	NPD3026	Approved
0.6807	Remote Similarity	NPD5909	Discontinued
0.6803	Remote Similarity	NPD4233	Approved
0.6803	Remote Similarity	NPD4234	Approved
0.68	Remote Similarity	NPD5951	Approved
0.6774	Remote Similarity	NPD2607	Approved
0.6765	Remote Similarity	NPD8032	Phase 2
0.6744	Remote Similarity	NPD5125	Phase 3
0.6744	Remote Similarity	NPD5126	Approved
0.6726	Remote Similarity	NPD1239	Approved
0.6724	Remote Similarity	NPD1565	Approved
0.6724	Remote Similarity	NPD1566	Phase 3
0.6724	Remote Similarity	NPD1564	Approved
0.6723	Remote Similarity	NPD6647	Phase 2
0.6721	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5347	Phase 2
0.6696	Remote Similarity	NPD5346	Phase 2
0.6694	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4576	Approved
0.6693	Remote Similarity	NPD4574	Approved
0.6692	Remote Similarity	NPD4879	Approved
0.6667	Remote Similarity	NPD1756	Approved
0.6667	Remote Similarity	NPD1752	Approved
0.6641	Remote Similarity	NPD5618	Discontinued
0.6641	Remote Similarity	NPD4807	Approved
0.6641	Remote Similarity	NPD4806	Approved
0.6624	Remote Similarity	NPD7799	Discontinued
0.6615	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5305	Approved
0.6615	Remote Similarity	NPD5306	Approved
0.6607	Remote Similarity	NPD6672	Approved
0.6607	Remote Similarity	NPD5737	Approved
0.6604	Remote Similarity	NPD225	Approved
0.6604	Remote Similarity	NPD227	Approved
0.6589	Remote Similarity	NPD4479	Discontinued
0.6587	Remote Similarity	NPD2650	Approved
0.6587	Remote Similarity	NPD2652	Approved
0.6585	Remote Similarity	NPD2182	Approved
0.6583	Remote Similarity	NPD5765	Approved
0.6557	Remote Similarity	NPD5706	Approved
0.6557	Remote Similarity	NPD5704	Approved
0.6557	Remote Similarity	NPD5705	Approved
0.6542	Remote Similarity	NPD9490	Approved
0.6529	Remote Similarity	NPD1237	Approved
0.6528	Remote Similarity	NPD8166	Discontinued
0.6518	Remote Similarity	NPD4793	Discontinued
0.6518	Remote Similarity	NPD650	Approved
0.6515	Remote Similarity	NPD7436	Approved
0.6515	Remote Similarity	NPD7437	Approved
0.6515	Remote Similarity	NPD6287	Discontinued
0.65	Remote Similarity	NPD1932	Approved
0.6496	Remote Similarity	NPD7008	Discontinued
0.6493	Remote Similarity	NPD5667	Approved
0.6486	Remote Similarity	NPD7606	Phase 3
0.6471	Remote Similarity	NPD7057	Phase 3
0.6471	Remote Similarity	NPD7058	Phase 2
0.6462	Remote Similarity	NPD7741	Discontinued
0.6455	Remote Similarity	NPD9491	Approved
0.6452	Remote Similarity	NPD2329	Discontinued
0.6446	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4106	Approved
0.6439	Remote Similarity	NPD4135	Approved
0.6439	Remote Similarity	NPD4136	Approved
0.6429	Remote Similarity	NPD6355	Discontinued
0.6429	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD6912	Phase 3
0.6422	Remote Similarity	NPD226	Approved
0.6414	Remote Similarity	NPD7487	Discontinued
0.6412	Remote Similarity	NPD5585	Approved
0.6412	Remote Similarity	NPD1651	Approved
0.6406	Remote Similarity	NPD1711	Phase 2
0.6406	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7478	Approved
0.6391	Remote Similarity	NPD2610	Approved
0.6391	Remote Similarity	NPD4218	Approved
0.6391	Remote Similarity	NPD4216	Approved
0.6391	Remote Similarity	NPD4217	Approved
0.6391	Remote Similarity	NPD4215	Approved
0.6391	Remote Similarity	NPD3131	Approved
0.6391	Remote Similarity	NPD2609	Approved
0.6391	Remote Similarity	NPD2611	Approved
0.6391	Remote Similarity	NPD3132	Approved
0.6391	Remote Similarity	NPD2608	Approved
0.6391	Remote Similarity	NPD2612	Approved
0.6387	Remote Similarity	NPD9495	Approved
0.6358	Remote Similarity	NPD7028	Phase 2
0.6357	Remote Similarity	NPD2979	Phase 3
0.635	Remote Similarity	NPD5204	Approved
0.6343	Remote Similarity	NPD6637	Approved
0.6343	Remote Similarity	NPD3972	Approved
0.6341	Remote Similarity	NPD5048	Discontinued
0.6341	Remote Similarity	NPD8407	Phase 2
0.6333	Remote Similarity	NPD1238	Approved
0.6316	Remote Similarity	NPD531	Approved
0.6311	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6882	Approved
0.6296	Remote Similarity	NPD5327	Phase 3
0.6293	Remote Similarity	NPD6050	Approved
0.6293	Remote Similarity	NPD5694	Approved
0.6291	Remote Similarity	NPD7458	Discontinued
0.6288	Remote Similarity	NPD4102	Approved
0.6288	Remote Similarity	NPD4105	Approved
0.6288	Remote Similarity	NPD5981	Approved
0.6286	Remote Similarity	NPD7714	Approved
0.6286	Remote Similarity	NPD7713	Phase 3
0.6286	Remote Similarity	NPD7715	Approved
0.6283	Remote Similarity	NPD7334	Approved
0.6283	Remote Similarity	NPD6684	Approved
0.6283	Remote Similarity	NPD5330	Approved
0.6283	Remote Similarity	NPD7146	Approved
0.6283	Remote Similarity	NPD7521	Approved
0.6283	Remote Similarity	NPD6409	Approved
0.6277	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6085	Phase 2
0.6277	Remote Similarity	NPD2798	Approved
0.6271	Remote Similarity	NPD4094	Approved
0.6271	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6049	Phase 2
0.6269	Remote Similarity	NPD1281	Approved
0.6261	Remote Similarity	NPD6673	Approved
0.6261	Remote Similarity	NPD6080	Approved
0.6261	Remote Similarity	NPD6904	Approved
0.626	Remote Similarity	NPD164	Approved
0.6258	Remote Similarity	NPD8368	Discontinued
0.625	Remote Similarity	NPD5926	Approved
0.625	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD4199	Phase 3
0.6239	Remote Similarity	NPD1508	Approved
0.6239	Remote Similarity	NPD6399	Phase 3
0.6232	Remote Similarity	NPD3662	Phase 3
0.6232	Remote Similarity	NPD3664	Approved
0.6232	Remote Similarity	NPD3661	Approved
0.6232	Remote Similarity	NPD3663	Approved
0.6222	Remote Similarity	NPD4878	Approved
0.622	Remote Similarity	NPD3644	Approved
0.622	Remote Similarity	NPD3643	Approved
0.622	Remote Similarity	NPD3642	Approved
0.6214	Remote Similarity	NPD4621	Approved
0.6214	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4619	Approved
0.6212	Remote Similarity	NPD3091	Approved
0.6207	Remote Similarity	NPD5692	Phase 3
0.6187	Remote Similarity	NPD4620	Approved
0.6187	Remote Similarity	NPD5201	Approved
0.6187	Remote Similarity	NPD4617	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