NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	438.17
Volume:	430.257
LogP:	4.121
LogD:	2.32
LogS:	-2.696
# Rotatable Bonds:	5
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	4.136
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056
MDCK Permeability:	1.1121907846245449e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.281
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	99.81182098388672%
Volume Distribution (VD):	0.399
Pgp-substrate:	0.6586052775382996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.454
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.452
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	6.128
Half-life (T1/2):	0.094

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.491
Carcinogencity:	0.316
Eye Corrosion:	0.196
Eye Irritation:	0.911
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC476532

Natural Product ID:	NPC476532
*Common Name:**	Siphonodyctial B2
IUPAC Name:	[6-[(E)-[(2S,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-ylidene]methyl]-2-formyl-3,4-dihydroxyphenyl] hydrogen sulfate
Synonyms:	Siphonodictyal B2
Standard InCHIKey:	MMPODADSKBDMPK-QGKRBUCPSA-N
Standard InCHI:	InChI=1S/C22H30O7S/c1-13-6-7-18-21(2,3)8-5-9-22(18,4)16(13)10-14-11-17(24)19(25)15(12-23)20(14)29-30(26,27)28/h10-13,18,24-25H,5-9H2,1-4H3,(H,26,27,28)/b16-10+/t13-,18?,22+/m0/s1
SMILES:	C[C@H]\1CCC2[C@@](/C1=C/C3=CC(=C(C(=C3OS(=O)(=O)O)C=O)O)O)(CCCC2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	22833273
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0004258] Arylsulfates [CHEMONTID:0002626] Phenylsulfates

*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
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	San Salvador in the Bahamas (12-26 m depth)	2001-MAR; 2003-JUL	PMID[17309298]
NPO9771	Aka coralliphagum	Species	Niphatidae	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	14

Activity Type	# Activity
Cell Line	1
Organism	11
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IZ	=	6	mm	PMID[17309298]
NPT2	Others	Unspecified		Activity	=	88.8	%	PMID[17309298]
NPT2	Others	Unspecified		Activity	=	25.3	%	PMID[17309298]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	0	mm	PMID[17309298]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	0	mm	PMID[17309298]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	0	mm	PMID[17309298]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	0	mm	PMID[17309298]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	IZ	=	0	mm	PMID[17309298]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	13	mm	PMID[17309298]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	0	mm	PMID[17309298]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	0	mm	PMID[17309298]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IZ	=	0	mm	PMID[17309298]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	IZ	=	15	mm	PMID[17309298]
NPT2701	Organism	Pythium debaryanum	Pythium debaryanum	IZ	=	0	mm	PMID[17309298]

☑ 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 NPC476532 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	393
0.1-0.2	1472
0.2-0.3	3293
0.3-0.4	8479
0.4-0.5	11186
0.5-0.6	5184
0.6-0.7	9073
0.7-0.8	3565
0.8-0.85	45
0.85-0.9	3
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC476533
0.9861	High Similarity	NPC474191
0.972	High Similarity	NPC476535
0.8904	High Similarity	NPC476534
0.8716	High Similarity	NPC92079
0.8693	High Similarity	NPC48949
0.8639	High Similarity	NPC141368
0.8639	High Similarity	NPC206207
0.8591	High Similarity	NPC187843
0.8487	Intermediate Similarity	NPC68441
0.8477	Intermediate Similarity	NPC199936
0.8477	Intermediate Similarity	NPC238629
0.84	Intermediate Similarity	NPC471853
0.8323	Intermediate Similarity	NPC478050
0.8312	Intermediate Similarity	NPC63918
0.8311	Intermediate Similarity	NPC475917
0.8301	Intermediate Similarity	NPC244691
0.8289	Intermediate Similarity	NPC474961
0.8278	Intermediate Similarity	NPC203063
0.8267	Intermediate Similarity	NPC123714
0.8261	Intermediate Similarity	NPC161947
0.8261	Intermediate Similarity	NPC155302
0.8255	Intermediate Similarity	NPC194764
0.8255	Intermediate Similarity	NPC264112
0.8255	Intermediate Similarity	NPC65005
0.8243	Intermediate Similarity	NPC474224
0.8243	Intermediate Similarity	NPC474117
0.8228	Intermediate Similarity	NPC161778
0.8221	Intermediate Similarity	NPC101769
0.8219	Intermediate Similarity	NPC244441
0.8217	Intermediate Similarity	NPC280295
0.8212	Intermediate Similarity	NPC143438
0.821	Intermediate Similarity	NPC32694
0.821	Intermediate Similarity	NPC472275
0.821	Intermediate Similarity	NPC87431
0.82	Intermediate Similarity	NPC290030
0.8182	Intermediate Similarity	NPC10764
0.8176	Intermediate Similarity	NPC273248
0.8171	Intermediate Similarity	NPC473286
0.817	Intermediate Similarity	NPC135524
0.817	Intermediate Similarity	NPC248068
0.8163	Intermediate Similarity	NPC85342
0.8163	Intermediate Similarity	NPC291001
0.816	Intermediate Similarity	NPC470694
0.8158	Intermediate Similarity	NPC181560
0.8158	Intermediate Similarity	NPC169452
0.8148	Intermediate Similarity	NPC45146
0.8148	Intermediate Similarity	NPC84571
0.8148	Intermediate Similarity	NPC235018
0.8148	Intermediate Similarity	NPC297212
0.8141	Intermediate Similarity	NPC10842
0.8138	Intermediate Similarity	NPC476536
0.8133	Intermediate Similarity	NPC191976
0.8129	Intermediate Similarity	NPC75295
0.8125	Intermediate Similarity	NPC130589
0.8125	Intermediate Similarity	NPC68727
0.8125	Intermediate Similarity	NPC134287
0.8113	Intermediate Similarity	NPC113608
0.8113	Intermediate Similarity	NPC268992
0.8113	Intermediate Similarity	NPC51824
0.8113	Intermediate Similarity	NPC470338
0.8113	Intermediate Similarity	NPC470337
0.811	Intermediate Similarity	NPC472278
0.811	Intermediate Similarity	NPC473313
0.811	Intermediate Similarity	NPC220313
0.811	Intermediate Similarity	NPC476295
0.811	Intermediate Similarity	NPC329669
0.8105	Intermediate Similarity	NPC204045
0.8105	Intermediate Similarity	NPC472904
0.8105	Intermediate Similarity	NPC305845
0.8101	Intermediate Similarity	NPC470037
0.8098	Intermediate Similarity	NPC311740
0.8095	Intermediate Similarity	NPC62219
0.8092	Intermediate Similarity	NPC472903
0.8092	Intermediate Similarity	NPC162939
0.8092	Intermediate Similarity	NPC138099
0.8092	Intermediate Similarity	NPC190457
0.8092	Intermediate Similarity	NPC242994
0.8089	Intermediate Similarity	NPC471907
0.8086	Intermediate Similarity	NPC46736
0.8086	Intermediate Similarity	NPC185258
0.8086	Intermediate Similarity	NPC172770
0.8079	Intermediate Similarity	NPC147418
0.8079	Intermediate Similarity	NPC471905
0.8075	Intermediate Similarity	NPC142339
0.8075	Intermediate Similarity	NPC470762
0.8075	Intermediate Similarity	NPC474167
0.8065	Intermediate Similarity	NPC471906
0.8063	Intermediate Similarity	NPC107109
0.8063	Intermediate Similarity	NPC477047
0.8063	Intermediate Similarity	NPC477048
0.8063	Intermediate Similarity	NPC93552
0.8054	Intermediate Similarity	NPC267205
0.8054	Intermediate Similarity	NPC111845
0.8052	Intermediate Similarity	NPC73061
0.8052	Intermediate Similarity	NPC193555
0.8052	Intermediate Similarity	NPC291078
0.805	Intermediate Similarity	NPC75377
0.805	Intermediate Similarity	NPC35
0.805	Intermediate Similarity	NPC221249
0.8037	Intermediate Similarity	NPC119224
0.8037	Intermediate Similarity	NPC476280
0.8037	Intermediate Similarity	NPC228785
0.8037	Intermediate Similarity	NPC14353
0.8037	Intermediate Similarity	NPC56085
0.8037	Intermediate Similarity	NPC80375
0.8036	Intermediate Similarity	NPC307286
0.8026	Intermediate Similarity	NPC230811
0.8026	Intermediate Similarity	NPC61398
0.8026	Intermediate Similarity	NPC416
0.8025	Intermediate Similarity	NPC78103
0.8025	Intermediate Similarity	NPC179732
0.8025	Intermediate Similarity	NPC236796
0.8025	Intermediate Similarity	NPC37543
0.8025	Intermediate Similarity	NPC469584
0.8025	Intermediate Similarity	NPC79053
0.8025	Intermediate Similarity	NPC199463
0.8013	Intermediate Similarity	NPC223836
0.8013	Intermediate Similarity	NPC258856
0.8013	Intermediate Similarity	NPC34482
0.8013	Intermediate Similarity	NPC471690
0.8013	Intermediate Similarity	NPC254847
0.8012	Intermediate Similarity	NPC113906
0.8012	Intermediate Similarity	NPC39184
0.8012	Intermediate Similarity	NPC472048
0.8	Intermediate Similarity	NPC180944
0.8	Intermediate Similarity	NPC270837
0.8	Intermediate Similarity	NPC474394
0.8	Intermediate Similarity	NPC3744
0.8	Intermediate Similarity	NPC282780
0.8	Intermediate Similarity	NPC166480
0.8	Intermediate Similarity	NPC236132
0.8	Intermediate Similarity	NPC293454
0.8	Intermediate Similarity	NPC474519
0.8	Intermediate Similarity	NPC12461
0.8	Intermediate Similarity	NPC131799
0.8	Intermediate Similarity	NPC7483
0.7988	Intermediate Similarity	NPC471969
0.7988	Intermediate Similarity	NPC40491
0.7988	Intermediate Similarity	NPC278052
0.7988	Intermediate Similarity	NPC266314
0.7988	Intermediate Similarity	NPC278427
0.7988	Intermediate Similarity	NPC61010
0.7987	Intermediate Similarity	NPC175738
0.7987	Intermediate Similarity	NPC10467
0.7987	Intermediate Similarity	NPC135801
0.7975	Intermediate Similarity	NPC85121
0.7975	Intermediate Similarity	NPC100123
0.7975	Intermediate Similarity	NPC197856
0.7975	Intermediate Similarity	NPC238279
0.7975	Intermediate Similarity	NPC203077
0.7975	Intermediate Similarity	NPC329091
0.7975	Intermediate Similarity	NPC166036
0.7973	Intermediate Similarity	NPC233056
0.7964	Intermediate Similarity	NPC471975
0.7964	Intermediate Similarity	NPC470374
0.7964	Intermediate Similarity	NPC478060
0.7964	Intermediate Similarity	NPC470377
0.7964	Intermediate Similarity	NPC107009
0.7964	Intermediate Similarity	NPC478059
0.7963	Intermediate Similarity	NPC77807
0.7963	Intermediate Similarity	NPC14561
0.7963	Intermediate Similarity	NPC5379
0.7962	Intermediate Similarity	NPC470570
0.7961	Intermediate Similarity	NPC49911
0.7961	Intermediate Similarity	NPC277559
0.7961	Intermediate Similarity	NPC53001
0.7961	Intermediate Similarity	NPC53414
0.7961	Intermediate Similarity	NPC53206
0.7961	Intermediate Similarity	NPC170742
0.7952	Intermediate Similarity	NPC25361
0.7952	Intermediate Similarity	NPC326520
0.795	Intermediate Similarity	NPC89474
0.795	Intermediate Similarity	NPC124714
0.795	Intermediate Similarity	NPC250557
0.7949	Intermediate Similarity	NPC21599
0.7949	Intermediate Similarity	NPC48762
0.7949	Intermediate Similarity	NPC193703
0.7947	Intermediate Similarity	NPC14377
0.7947	Intermediate Similarity	NPC290803
0.7947	Intermediate Similarity	NPC153088
0.7947	Intermediate Similarity	NPC129752
0.7947	Intermediate Similarity	NPC278375
0.7945	Intermediate Similarity	NPC49647
0.7945	Intermediate Similarity	NPC227741
0.7945	Intermediate Similarity	NPC295202
0.7945	Intermediate Similarity	NPC136342
0.7939	Intermediate Similarity	NPC206605
0.7939	Intermediate Similarity	NPC294965
0.7939	Intermediate Similarity	NPC215612
0.7937	Intermediate Similarity	NPC19980
0.7937	Intermediate Similarity	NPC70320
0.7937	Intermediate Similarity	NPC45291
0.7937	Intermediate Similarity	NPC227485
0.7935	Intermediate Similarity	NPC137649
0.7933	Intermediate Similarity	NPC314048
0.7933	Intermediate Similarity	NPC138472
0.7927	Intermediate Similarity	NPC474287
0.7927	Intermediate Similarity	NPC320359
0.7927	Intermediate Similarity	NPC475886

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 NPC476532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	904
0.2-0.3	1720
0.3-0.4	3015
0.4-0.5	1997
0.5-0.6	869
0.6-0.7	269
0.7-0.8	35
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8487	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD943	Approved
0.784	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2801	Approved
0.7725	Intermediate Similarity	NPD6232	Discontinued
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7561	Intermediate Similarity	NPD1934	Approved
0.7517	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7483	Intermediate Similarity	NPD1201	Approved
0.7396	Intermediate Similarity	NPD5494	Approved
0.7391	Intermediate Similarity	NPD1511	Approved
0.7389	Intermediate Similarity	NPD2935	Discontinued
0.7355	Intermediate Similarity	NPD230	Phase 1
0.7346	Intermediate Similarity	NPD2534	Approved
0.7346	Intermediate Similarity	NPD2532	Approved
0.7346	Intermediate Similarity	NPD2533	Approved
0.7326	Intermediate Similarity	NPD6166	Phase 2
0.7326	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3882	Suspended
0.7321	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD9269	Phase 2
0.7312	Intermediate Similarity	NPD8166	Discontinued
0.7301	Intermediate Similarity	NPD1512	Approved
0.7299	Intermediate Similarity	NPD5844	Phase 1
0.7251	Intermediate Similarity	NPD6959	Discontinued
0.7239	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6234	Discontinued
0.7229	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD3300	Phase 2
0.7188	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3026	Approved
0.7181	Intermediate Similarity	NPD3023	Approved
0.716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD37	Approved
0.7114	Intermediate Similarity	NPD3019	Approved
0.7107	Intermediate Similarity	NPD1510	Phase 2
0.7101	Intermediate Similarity	NPD7819	Suspended
0.7088	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6559	Discontinued
0.7062	Intermediate Similarity	NPD7074	Phase 3
0.7059	Intermediate Similarity	NPD3817	Phase 2
0.7047	Intermediate Similarity	NPD9268	Approved
0.7047	Intermediate Similarity	NPD3024	Approved
0.7047	Intermediate Similarity	NPD3025	Approved
0.7039	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2800	Approved
0.7018	Intermediate Similarity	NPD4966	Approved
0.7018	Intermediate Similarity	NPD4967	Phase 2
0.7018	Intermediate Similarity	NPD4965	Approved
0.7018	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD2932	Approved
0.6981	Remote Similarity	NPD6651	Approved
0.6981	Remote Similarity	NPD1607	Approved
0.6977	Remote Similarity	NPD7075	Discontinued
0.6966	Remote Similarity	NPD7472	Approved
0.6962	Remote Similarity	NPD1240	Approved
0.6954	Remote Similarity	NPD1247	Approved
0.6951	Remote Similarity	NPD6190	Approved
0.6949	Remote Similarity	NPD7228	Approved
0.6948	Remote Similarity	NPD1164	Approved
0.6948	Remote Similarity	NPD3094	Phase 2
0.6928	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD6599	Discontinued
0.6914	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1465	Phase 2
0.6901	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7251	Discontinued
0.6885	Remote Similarity	NPD8150	Discontinued
0.6882	Remote Similarity	NPD7411	Suspended
0.6871	Remote Similarity	NPD1549	Phase 2
0.686	Remote Similarity	NPD5402	Approved
0.6852	Remote Similarity	NPD1551	Phase 2
0.6852	Remote Similarity	NPD6099	Approved
0.6852	Remote Similarity	NPD6100	Approved
0.6846	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4750	Phase 3
0.6828	Remote Similarity	NPD3022	Approved
0.6828	Remote Similarity	NPD3021	Approved
0.6821	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5711	Approved
0.6818	Remote Similarity	NPD5710	Approved
0.6797	Remote Similarity	NPD3092	Approved
0.6792	Remote Similarity	NPD6663	Approved
0.679	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7003	Approved
0.6782	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3095	Discontinued
0.6772	Remote Similarity	NPD3027	Phase 3
0.6765	Remote Similarity	NPD3226	Approved
0.6758	Remote Similarity	NPD7808	Phase 3
0.6752	Remote Similarity	NPD5736	Approved
0.6752	Remote Similarity	NPD9494	Approved
0.6748	Remote Similarity	NPD2796	Approved
0.6744	Remote Similarity	NPD6801	Discontinued
0.6742	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2346	Discontinued
0.6703	Remote Similarity	NPD8434	Phase 2
0.6687	Remote Similarity	NPD3750	Approved
0.6687	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2799	Discontinued
0.6667	Remote Similarity	NPD5026	Approved
0.6667	Remote Similarity	NPD5028	Approved
0.6667	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD36	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD4955	Approved
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD5034	Approved
0.6667	Remote Similarity	NPD4954	Approved
0.6648	Remote Similarity	NPD919	Approved
0.6646	Remote Similarity	NPD3620	Phase 2
0.6646	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1613	Approved
0.6646	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3091	Approved
0.663	Remote Similarity	NPD8312	Approved
0.663	Remote Similarity	NPD8313	Approved
0.6629	Remote Similarity	NPD7229	Phase 3
0.6625	Remote Similarity	NPD3764	Approved
0.6625	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5038	Approved
0.6613	Remote Similarity	NPD5037	Approved
0.6612	Remote Similarity	NPD5030	Phase 2
0.6609	Remote Similarity	NPD5761	Phase 2
0.6609	Remote Similarity	NPD5760	Phase 2
0.6605	Remote Similarity	NPD447	Suspended
0.6604	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3749	Approved
0.6587	Remote Similarity	NPD4628	Phase 3
0.6582	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6778	Approved
0.658	Remote Similarity	NPD6781	Approved
0.658	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6776	Approved
0.658	Remote Similarity	NPD6780	Approved
0.658	Remote Similarity	NPD6779	Approved
0.658	Remote Similarity	NPD6782	Approved
0.658	Remote Similarity	NPD6777	Approved
0.6577	Remote Similarity	NPD7635	Approved
0.6573	Remote Similarity	NPD8127	Discontinued
0.6573	Remote Similarity	NPD7199	Phase 2
0.657	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7699	Phase 2
0.6562	Remote Similarity	NPD7700	Phase 2
0.6559	Remote Similarity	NPD5036	Approved
0.6557	Remote Similarity	NPD5953	Discontinued
0.655	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.655	Remote Similarity	NPD920	Approved
0.6541	Remote Similarity	NPD5035	Approved
0.6538	Remote Similarity	NPD6020	Phase 2
0.6527	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5031	Approved
0.6522	Remote Similarity	NPD7240	Approved
0.6522	Remote Similarity	NPD5027	Approved
0.6522	Remote Similarity	NPD5029	Approved
0.6513	Remote Similarity	NPD6823	Phase 2
0.6513	Remote Similarity	NPD9493	Approved
0.6505	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3926	Phase 2
0.65	Remote Similarity	NPD4908	Phase 1
0.65	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6273	Approved
0.649	Remote Similarity	NPD5951	Approved
0.6486	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8151	Discontinued
0.648	Remote Similarity	NPD7435	Discontinued
0.6478	Remote Similarity	NPD2798	Approved
0.6458	Remote Similarity	NPD940	Approved
0.6458	Remote Similarity	NPD846	Approved
0.6453	Remote Similarity	NPD5403	Approved
0.6448	Remote Similarity	NPD7286	Phase 2
0.644	Remote Similarity	NPD6212	Phase 3
0.644	Remote Similarity	NPD6213	Phase 3
0.644	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2313	Discontinued

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