NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	506.14
Volume:	487.925
LogP:	5.203
LogD:	3.232
LogS:	-4.862
# Rotatable Bonds:	5
TPSA:	117.07
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	5.125
Fsp3:	0.52
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.093
MDCK Permeability:	2.414407572359778e-05
Pgp-inhibitor:	0.628
Pgp-substrate:	0.198
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.5320816040039%
Volume Distribution (VD):	3.342
Pgp-substrate:	3.907670736312866%

ADMET: Metabolism

CYP1A2-inhibitor:	0.629
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.658
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.87
CYP2C9-substrate:	0.345
CYP2D6-inhibitor:	0.949
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.798

ADMET: Excretion

Clearance (CL):	1.164
Half-life (T1/2):	0.012

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.975
Rat Oral Acute Toxicity:	0.807
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.77
Carcinogencity:	0.897
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.994

Download Data

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

Natural Product: NPC477994

Natural Product ID:	NPC477994
*Common Name:**	2-[(3S,6S)-6-[(2R,5S)-5-[6-[(2Z,4Z,6Z)-cycloocta-2,4,6-trien-1-yl]hexyl]oxolan-2-yl]dioxan-3-yl]acetic acid
IUPAC Name:	2-[(3S,6S)-6-[(2R,5S)-5-[6-[(2Z,4Z,6Z)-cycloocta-2,4,6-trien-1-yl]hexyl]oxolan-2-yl]dioxan-3-yl]acetic acid
Synonyms:	stolonoxide F
Standard InCHIKey:	DIHXQPVNIPQBLK-YDFHIJSTSA-N
Standard InCHI:	InChI=1S/C24H36O5/c25-24(26)18-21-15-17-23(29-28-21)22-16-14-20(27-22)13-9-5-4-8-12-19-10-6-2-1-3-7-11-19/h1-3,6-7,10,19-23H,4-5,8-9,11-18H2,(H,25,26)/b2-1-,7-3-,10-6-/t19?,20-,21-,22+,23-/m0/s1
SMILES:	C1C[C@@H](O[C@H]1CCCCCCC/2C/C=C\C=C/C=C2)[C@@H]3CC[C@H](OO3)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44628015
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO26094	Stolonica socialis	Species	Styelidae	Eukaryota	n.a.	At a depth between 3 and 15 m in Las Lajas (Cdiz, Spain) (3606'11'' N, 525'47'' W)	2003-SEP	PMID[20014800]
NPO26094	Stolonica socialis	Species	Styelidae	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	3
Others	6

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	4700	nM	PMID[20014800]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	5440	nM	PMID[20014800]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	6180	nM	PMID[20014800]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	2720	nM	PMID[20014800]
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	3210	nM	PMID[20014800]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	3710	nM	PMID[20014800]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	5440	nM	PMID[20014800]
NPT81	Cell Line	A549	Homo sapiens	TGI	=	5930	nM	PMID[20014800]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	6670	nM	PMID[20014800]

☑ 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 NPC477994 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	172
0.1-0.2	880
0.2-0.3	4823
0.3-0.4	11620
0.4-0.5	12459
0.5-0.6	9096
0.6-0.7	3487
0.7-0.8	155
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477993
0.8889	High Similarity	NPC263574
0.8889	High Similarity	NPC469747
0.8554	High Similarity	NPC469920
0.8095	Intermediate Similarity	NPC11796
0.8095	Intermediate Similarity	NPC218817
0.8072	Intermediate Similarity	NPC469514
0.8072	Intermediate Similarity	NPC239127
0.8046	Intermediate Similarity	NPC69469
0.8043	Intermediate Similarity	NPC478036
0.8043	Intermediate Similarity	NPC478037
0.7976	Intermediate Similarity	NPC281296
0.7952	Intermediate Similarity	NPC255060
0.7927	Intermediate Similarity	NPC167145
0.7889	Intermediate Similarity	NPC86005
0.7882	Intermediate Similarity	NPC121200
0.7831	Intermediate Similarity	NPC330016
0.7826	Intermediate Similarity	NPC313670
0.7802	Intermediate Similarity	NPC201046
0.7765	Intermediate Similarity	NPC240170
0.7765	Intermediate Similarity	NPC120776
0.7765	Intermediate Similarity	NPC145898
0.7738	Intermediate Similarity	NPC217725
0.7732	Intermediate Similarity	NPC469870
0.7732	Intermediate Similarity	NPC469871
0.77	Intermediate Similarity	NPC478038
0.7692	Intermediate Similarity	NPC477959
0.7647	Intermediate Similarity	NPC474447
0.7586	Intermediate Similarity	NPC82488
0.7586	Intermediate Similarity	NPC209995
0.7586	Intermediate Similarity	NPC308545
0.7527	Intermediate Similarity	NPC256902
0.7527	Intermediate Similarity	NPC118193
0.7526	Intermediate Similarity	NPC40812
0.75	Intermediate Similarity	NPC200446
0.7473	Intermediate Similarity	NPC475206
0.7471	Intermediate Similarity	NPC469495
0.7449	Intermediate Similarity	NPC83895
0.7449	Intermediate Similarity	NPC308567
0.7449	Intermediate Similarity	NPC187761
0.7449	Intermediate Similarity	NPC255592
0.7449	Intermediate Similarity	NPC261377
0.7447	Intermediate Similarity	NPC478004
0.7447	Intermediate Similarity	NPC478003
0.7447	Intermediate Similarity	NPC158388
0.7442	Intermediate Similarity	NPC266119
0.7426	Intermediate Similarity	NPC470519
0.7426	Intermediate Similarity	NPC469869
0.7426	Intermediate Similarity	NPC231271
0.7416	Intermediate Similarity	NPC117960
0.7416	Intermediate Similarity	NPC14044
0.7416	Intermediate Similarity	NPC172309
0.7391	Intermediate Similarity	NPC469483
0.7391	Intermediate Similarity	NPC475753
0.7386	Intermediate Similarity	NPC113363
0.7368	Intermediate Similarity	NPC472199
0.7368	Intermediate Similarity	NPC184463
0.7363	Intermediate Similarity	NPC471343
0.7356	Intermediate Similarity	NPC476264
0.7356	Intermediate Similarity	NPC476325
0.7347	Intermediate Similarity	NPC476612
0.7347	Intermediate Similarity	NPC476613
0.734	Intermediate Similarity	NPC97577
0.734	Intermediate Similarity	NPC307411
0.7333	Intermediate Similarity	NPC474252
0.7327	Intermediate Similarity	NPC4620
0.7326	Intermediate Similarity	NPC60718
0.7326	Intermediate Similarity	NPC199445
0.732	Intermediate Similarity	NPC475659
0.7303	Intermediate Similarity	NPC472948
0.7303	Intermediate Similarity	NPC103634
0.7294	Intermediate Similarity	NPC326024
0.7292	Intermediate Similarity	NPC476300
0.7273	Intermediate Similarity	NPC161855
0.7263	Intermediate Similarity	NPC51004
0.7262	Intermediate Similarity	NPC476660
0.7255	Intermediate Similarity	NPC220964
0.7255	Intermediate Similarity	NPC475676
0.7253	Intermediate Similarity	NPC170286
0.7245	Intermediate Similarity	NPC473859
0.7245	Intermediate Similarity	NPC180722
0.7245	Intermediate Similarity	NPC54731
0.7245	Intermediate Similarity	NPC165332
0.7245	Intermediate Similarity	NPC195645
0.7245	Intermediate Similarity	NPC473291
0.7234	Intermediate Similarity	NPC476706
0.7234	Intermediate Similarity	NPC309656
0.7234	Intermediate Similarity	NPC476707
0.7229	Intermediate Similarity	NPC209327
0.7229	Intermediate Similarity	NPC273508
0.7228	Intermediate Similarity	NPC183571
0.7222	Intermediate Similarity	NPC475481
0.7222	Intermediate Similarity	NPC21693
0.7222	Intermediate Similarity	NPC236649
0.7222	Intermediate Similarity	NPC79277
0.7216	Intermediate Similarity	NPC472198
0.7209	Intermediate Similarity	NPC474551
0.7204	Intermediate Similarity	NPC476982
0.7204	Intermediate Similarity	NPC476104
0.7204	Intermediate Similarity	NPC278283
0.7204	Intermediate Similarity	NPC478112
0.7188	Intermediate Similarity	NPC472197
0.7188	Intermediate Similarity	NPC30515
0.7188	Intermediate Similarity	NPC36491
0.7184	Intermediate Similarity	NPC475802
0.7184	Intermediate Similarity	NPC9303
0.7184	Intermediate Similarity	NPC16313
0.7176	Intermediate Similarity	NPC320119
0.7172	Intermediate Similarity	NPC266842
0.7159	Intermediate Similarity	NPC122847
0.7158	Intermediate Similarity	NPC469866
0.7158	Intermediate Similarity	NPC471342
0.7157	Intermediate Similarity	NPC474165
0.7157	Intermediate Similarity	NPC69171
0.7143	Intermediate Similarity	NPC107476
0.7143	Intermediate Similarity	NPC36954
0.7143	Intermediate Similarity	NPC313668
0.7143	Intermediate Similarity	NPC315836
0.7143	Intermediate Similarity	NPC473772
0.7129	Intermediate Similarity	NPC476611
0.7129	Intermediate Similarity	NPC472753
0.7129	Intermediate Similarity	NPC47880
0.7126	Intermediate Similarity	NPC81052
0.7115	Intermediate Similarity	NPC324327
0.7115	Intermediate Similarity	NPC194620
0.7115	Intermediate Similarity	NPC72813
0.7115	Intermediate Similarity	NPC326994
0.7115	Intermediate Similarity	NPC474421
0.7113	Intermediate Similarity	NPC475912
0.7113	Intermediate Similarity	NPC212486
0.7113	Intermediate Similarity	NPC320089
0.7108	Intermediate Similarity	NPC22101
0.7108	Intermediate Similarity	NPC271921
0.7108	Intermediate Similarity	NPC148192
0.7108	Intermediate Similarity	NPC127091
0.7108	Intermediate Similarity	NPC104537
0.7108	Intermediate Similarity	NPC330426
0.71	Intermediate Similarity	NPC203627
0.7097	Intermediate Similarity	NPC471344
0.7093	Intermediate Similarity	NPC474543
0.7093	Intermediate Similarity	NPC238425
0.7093	Intermediate Similarity	NPC472018
0.7087	Intermediate Similarity	NPC239162
0.7083	Intermediate Similarity	NPC473448
0.7083	Intermediate Similarity	NPC51653
0.7083	Intermediate Similarity	NPC476004
0.7083	Intermediate Similarity	NPC316228
0.7083	Intermediate Similarity	NPC474761
0.7079	Intermediate Similarity	NPC127526
0.7079	Intermediate Similarity	NPC3852
0.7071	Intermediate Similarity	NPC476315
0.7071	Intermediate Similarity	NPC469369
0.7071	Intermediate Similarity	NPC469528
0.7065	Intermediate Similarity	NPC473500
0.7065	Intermediate Similarity	NPC38295
0.7065	Intermediate Similarity	NPC156089
0.7065	Intermediate Similarity	NPC470313
0.7065	Intermediate Similarity	NPC475947
0.7065	Intermediate Similarity	NPC476983
0.7059	Intermediate Similarity	NPC474747
0.7059	Intermediate Similarity	NPC149371
0.7059	Intermediate Similarity	NPC475091
0.7059	Intermediate Similarity	NPC473596
0.7059	Intermediate Similarity	NPC478156
0.7059	Intermediate Similarity	NPC42526
0.7059	Intermediate Similarity	NPC225353
0.7059	Intermediate Similarity	NPC472754
0.7053	Intermediate Similarity	NPC202672
0.7053	Intermediate Similarity	NPC476708
0.7048	Intermediate Similarity	NPC233379
0.7048	Intermediate Similarity	NPC473807
0.7048	Intermediate Similarity	NPC474664
0.7048	Intermediate Similarity	NPC193765
0.7048	Intermediate Similarity	NPC327286
0.7048	Intermediate Similarity	NPC55972
0.7048	Intermediate Similarity	NPC14862
0.7048	Intermediate Similarity	NPC169888
0.7045	Intermediate Similarity	NPC49392
0.7045	Intermediate Similarity	NPC190400
0.7041	Intermediate Similarity	NPC5418
0.7033	Intermediate Similarity	NPC191711
0.7033	Intermediate Similarity	NPC476988
0.703	Intermediate Similarity	NPC475053
0.703	Intermediate Similarity	NPC288876
0.7024	Intermediate Similarity	NPC48218
0.7024	Intermediate Similarity	NPC473559
0.7024	Intermediate Similarity	NPC324981
0.7024	Intermediate Similarity	NPC141481
0.7021	Intermediate Similarity	NPC164393
0.7021	Intermediate Similarity	NPC262085
0.7019	Intermediate Similarity	NPC476738
0.7019	Intermediate Similarity	NPC476740
0.7011	Intermediate Similarity	NPC474321
0.701	Intermediate Similarity	NPC470379
0.701	Intermediate Similarity	NPC208886
0.701	Intermediate Similarity	NPC12172
0.701	Intermediate Similarity	NPC470373
0.701	Intermediate Similarity	NPC476705
0.7	Intermediate Similarity	NPC17326
0.7	Intermediate Similarity	NPC475438

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 NPC477994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1302
0.2-0.3	4005
0.3-0.4	2453
0.4-0.5	749
0.5-0.6	408
0.6-0.7	79
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7935	Intermediate Similarity	NPD7983	Approved
0.7447	Intermediate Similarity	NPD6698	Approved
0.7447	Intermediate Similarity	NPD46	Approved
0.734	Intermediate Similarity	NPD6101	Approved
0.734	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD5778	Approved
0.7245	Intermediate Similarity	NPD7839	Suspended
0.7188	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD6435	Approved
0.7041	Intermediate Similarity	NPD5282	Discontinued
0.7033	Intermediate Similarity	NPD5369	Approved
0.6947	Remote Similarity	NPD4251	Approved
0.6947	Remote Similarity	NPD4250	Approved
0.6923	Remote Similarity	NPD5368	Approved
0.6907	Remote Similarity	NPD7838	Discovery
0.6882	Remote Similarity	NPD7154	Phase 3
0.6842	Remote Similarity	NPD4249	Approved
0.6837	Remote Similarity	NPD7637	Suspended
0.6792	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8515	Approved
0.6754	Remote Similarity	NPD8516	Approved
0.6754	Remote Similarity	NPD8517	Approved
0.6754	Remote Similarity	NPD8513	Phase 3
0.6739	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5786	Approved
0.6574	Remote Similarity	NPD6686	Approved
0.6562	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5363	Approved
0.6559	Remote Similarity	NPD4820	Approved
0.6559	Remote Similarity	NPD4252	Approved
0.6559	Remote Similarity	NPD4821	Approved
0.6559	Remote Similarity	NPD4822	Approved
0.6559	Remote Similarity	NPD4819	Approved
0.6526	Remote Similarity	NPD5362	Discontinued
0.6522	Remote Similarity	NPD4271	Approved
0.6522	Remote Similarity	NPD4268	Approved
0.6522	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8074	Phase 3
0.6471	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8444	Approved
0.6455	Remote Similarity	NPD6371	Approved
0.64	Remote Similarity	NPD5785	Approved
0.6374	Remote Similarity	NPD8039	Approved
0.6356	Remote Similarity	NPD7830	Approved
0.6356	Remote Similarity	NPD7829	Approved
0.6353	Remote Similarity	NPD3197	Phase 1
0.6348	Remote Similarity	NPD7641	Discontinued
0.633	Remote Similarity	NPD6412	Phase 2
0.6303	Remote Similarity	NPD8340	Approved
0.6303	Remote Similarity	NPD8342	Approved
0.6303	Remote Similarity	NPD8341	Approved
0.6303	Remote Similarity	NPD8299	Approved
0.6275	Remote Similarity	NPD6399	Phase 3
0.6273	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8451	Approved
0.625	Remote Similarity	NPD8273	Phase 1
0.6226	Remote Similarity	NPD6648	Approved
0.6198	Remote Similarity	NPD8448	Approved
0.6182	Remote Similarity	NPD6685	Approved
0.6176	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3732	Approved
0.6167	Remote Similarity	NPD7492	Approved
0.6162	Remote Similarity	NPD6422	Discontinued
0.6146	Remote Similarity	NPD4790	Discontinued
0.6139	Remote Similarity	NPD1695	Approved
0.6139	Remote Similarity	NPD5370	Suspended
0.6136	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4225	Approved
0.6116	Remote Similarity	NPD6616	Approved
0.6102	Remote Similarity	NPD6319	Approved
0.6102	Remote Similarity	NPD6054	Approved
0.6082	Remote Similarity	NPD5209	Approved
0.6066	Remote Similarity	NPD7078	Approved
0.6061	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5765	Approved
0.6049	Remote Similarity	NPD4266	Approved
0.6049	Remote Similarity	NPD3194	Approved
0.6049	Remote Similarity	NPD3195	Phase 2
0.6049	Remote Similarity	NPD3196	Approved
0.6048	Remote Similarity	NPD8392	Approved
0.6048	Remote Similarity	NPD8391	Approved
0.6048	Remote Similarity	NPD8390	Approved
0.602	Remote Similarity	NPD5332	Approved
0.602	Remote Similarity	NPD5331	Approved
0.6019	Remote Similarity	NPD5344	Discontinued
0.6018	Remote Similarity	NPD6421	Discontinued
0.6016	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6370	Approved
0.5983	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7500	Approved
0.5981	Remote Similarity	NPD7638	Approved
0.5966	Remote Similarity	NPD6059	Approved
0.596	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7642	Approved
0.595	Remote Similarity	NPD8328	Phase 3
0.5946	Remote Similarity	NPD5048	Discontinued
0.5941	Remote Similarity	NPD7524	Approved
0.5935	Remote Similarity	NPD8293	Discontinued
0.5929	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7640	Approved
0.5926	Remote Similarity	NPD3172	Approved
0.5926	Remote Similarity	NPD7639	Approved
0.5917	Remote Similarity	NPD6015	Approved
0.5917	Remote Similarity	NPD6016	Approved
0.5913	Remote Similarity	NPD8297	Approved
0.5913	Remote Similarity	NPD6053	Discontinued
0.5913	Remote Similarity	NPD6912	Phase 3
0.5905	Remote Similarity	NPD7748	Approved
0.5888	Remote Similarity	NPD6084	Phase 2
0.5888	Remote Similarity	NPD6083	Phase 2
0.5888	Remote Similarity	NPD7902	Approved
0.5868	Remote Similarity	NPD5988	Approved
0.5865	Remote Similarity	NPD5284	Approved
0.5865	Remote Similarity	NPD5281	Approved
0.5862	Remote Similarity	NPD4632	Approved
0.5859	Remote Similarity	NPD6695	Phase 3
0.5849	Remote Similarity	NPD5695	Phase 3
0.5847	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7115	Discovery
0.5843	Remote Similarity	NPD7331	Phase 2
0.5842	Remote Similarity	NPD7334	Approved
0.5842	Remote Similarity	NPD6684	Approved
0.5842	Remote Similarity	NPD5330	Approved
0.5842	Remote Similarity	NPD7521	Approved
0.5842	Remote Similarity	NPD6409	Approved
0.5842	Remote Similarity	NPD7146	Approved
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD6881	Approved
0.584	Remote Similarity	NPD7319	Approved
0.5827	Remote Similarity	NPD2613	Approved
0.5826	Remote Similarity	NPD1719	Phase 1
0.581	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6675	Approved
0.5804	Remote Similarity	NPD6402	Approved
0.5804	Remote Similarity	NPD7128	Approved
0.5804	Remote Similarity	NPD5739	Approved
0.5794	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7798	Approved
0.5765	Remote Similarity	NPD6109	Phase 1
0.5758	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5697	Approved
0.5748	Remote Similarity	NPD7260	Phase 2
0.5743	Remote Similarity	NPD1694	Approved
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7102	Approved
0.5738	Remote Similarity	NPD8080	Discontinued
0.5729	Remote Similarity	NPD6932	Approved
0.5729	Remote Similarity	NPD4756	Discovery
0.5728	Remote Similarity	NPD6672	Approved
0.5728	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5737	Approved
0.5728	Remote Similarity	NPD6903	Approved
0.5726	Remote Similarity	NPD8133	Approved
0.5726	Remote Similarity	NPD7507	Approved
0.5714	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD7515	Phase 2
0.5714	Remote Similarity	NPD8035	Phase 2
0.5714	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6009	Approved
0.5702	Remote Similarity	NPD7320	Approved
0.57	Remote Similarity	NPD6110	Phase 1
0.5692	Remote Similarity	NPD3616	Approved
0.5692	Remote Similarity	NPD2566	Approved
0.5692	Remote Similarity	NPD2570	Approved
0.5692	Remote Similarity	NPD4745	Approved
0.5692	Remote Similarity	NPD3087	Approved
0.5692	Remote Similarity	NPD2573	Approved
0.5692	Remote Similarity	NPD3089	Approved
0.5692	Remote Similarity	NPD2571	Approved
0.5692	Remote Similarity	NPD3090	Approved
0.5692	Remote Similarity	NPD2574	Discontinued
0.5692	Remote Similarity	NPD3615	Approved
0.5692	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD3088	Approved
0.5692	Remote Similarity	NPD3614	Approved
0.5692	Remote Similarity	NPD4746	Phase 3
0.5691	Remote Similarity	NPD7604	Phase 2
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD6617	Approved
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6649	Approved
0.569	Remote Similarity	NPD8130	Phase 1
0.5688	Remote Similarity	NPD5696	Approved
0.5686	Remote Similarity	NPD5279	Phase 3
0.5679	Remote Similarity	NPD29	Approved
0.5679	Remote Similarity	NPD28	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