NPASS Compound

Structure

NPC120677 OpenBabel07101718302D 28 34 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -0.7070 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 -2.2971 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -0.2728 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 8 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 9 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 15 1 0 0 0 0 9 21 1 1 0 0 0 10 13 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 22 2 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 6 0 0 0 15 18 1 1 0 0 0 15 23 1 0 0 0 0 16 18 1 6 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 1 0 0 0 18 28 1 0 0 0 0 19 12 1 1 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.08
Volume:	349.084
LogP:	2.052
LogD:	2.005
LogS:	-4.193
# Rotatable Bonds:	0
TPSA:	121.28
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	5.478
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.774
MDCK Permeability:	3.7634596083080396e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.15
20% Bioavailability (F20%):	0.083
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.711
Plasma Protein Binding (PPB):	88.6322021484375%
Volume Distribution (VD):	0.454
Pgp-substrate:	3.689854145050049%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.719
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.422

ADMET: Excretion

Clearance (CL):	11.361
Half-life (T1/2):	0.65

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.993
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.932
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.86
Carcinogencity:	0.881
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC120677

Natural Product ID:	NPC120677
*Common Name:**	AEHDWPXNIOFWQB-RSLGSOOPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AEHDWPXNIOFWQB-RSLGSOOPSA-N
Standard InCHI:	InChI=1S/C20H16O8/c21-9-7-12(22)19-18(28-19,15(9)23)16(24)14-17(25-14)20(19)26-10-5-1-3-8-4-2-6-11(27-20)13(8)10/h1-6,9,14-17,21,23-24H,7H2/t9-,14+,15-,16-,17+,18-,19-/m0/s1
SMILES:	O[C@H]1CC(=O)[C@@]23[C@@]([C@H]1O)(O2)[C@@H](O)[C@@H]1[C@H](C23Oc3cccc4c3c(O2)ccc4)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342641
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33512	berkleasmium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25237727]

☑ 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	6
MIC	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[483049]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[483049]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[483049]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[483049]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[483049]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[483049]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[483049]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[483049]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[483049]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[483049]

☑ 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 NPC120677 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	453
0.1-0.2	1764
0.2-0.3	3836
0.3-0.4	9295
0.4-0.5	9071
0.5-0.6	5845
0.6-0.7	8105
0.7-0.8	4286
0.8-0.85	28
0.85-0.9	7
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC74371
0.9935	High Similarity	NPC75944
0.987	High Similarity	NPC472153
0.9497	High Similarity	NPC472150
0.9497	High Similarity	NPC175082
0.9487	High Similarity	NPC472156
0.9024	High Similarity	NPC137460
0.8909	High Similarity	NPC472152
0.8896	High Similarity	NPC173630
0.8848	High Similarity	NPC103633
0.8841	High Similarity	NPC297404
0.8841	High Similarity	NPC11608
0.8831	High Similarity	NPC472155
0.8718	High Similarity	NPC288531
0.8659	High Similarity	NPC73148
0.8654	High Similarity	NPC472154
0.8545	High Similarity	NPC316457
0.8537	High Similarity	NPC183402
0.8471	Intermediate Similarity	NPC151704
0.843	Intermediate Similarity	NPC272656
0.8424	Intermediate Similarity	NPC193749
0.8418	Intermediate Similarity	NPC271076
0.8418	Intermediate Similarity	NPC23807
0.8408	Intermediate Similarity	NPC197461
0.8365	Intermediate Similarity	NPC97662
0.8353	Intermediate Similarity	NPC67424
0.8314	Intermediate Similarity	NPC470438
0.8304	Intermediate Similarity	NPC265214
0.8266	Intermediate Similarity	NPC470667
0.8266	Intermediate Similarity	NPC186800
0.8246	Intermediate Similarity	NPC222455
0.8246	Intermediate Similarity	NPC217378
0.8235	Intermediate Similarity	NPC118284
0.8235	Intermediate Similarity	NPC88789
0.8235	Intermediate Similarity	NPC179950
0.8235	Intermediate Similarity	NPC253662
0.8235	Intermediate Similarity	NPC281131
0.8235	Intermediate Similarity	NPC274618
0.8235	Intermediate Similarity	NPC308404
0.8235	Intermediate Similarity	NPC56077
0.8235	Intermediate Similarity	NPC276222
0.8235	Intermediate Similarity	NPC145038
0.8229	Intermediate Similarity	NPC299149
0.8229	Intermediate Similarity	NPC114257
0.8229	Intermediate Similarity	NPC277710
0.8229	Intermediate Similarity	NPC153578
0.8218	Intermediate Similarity	NPC61904
0.8218	Intermediate Similarity	NPC470949
0.8218	Intermediate Similarity	NPC144097
0.8218	Intermediate Similarity	NPC8573
0.8218	Intermediate Similarity	NPC65563
0.8217	Intermediate Similarity	NPC193920
0.8214	Intermediate Similarity	NPC470125
0.8212	Intermediate Similarity	NPC314672
0.8208	Intermediate Similarity	NPC21666
0.8208	Intermediate Similarity	NPC169977
0.8208	Intermediate Similarity	NPC45522
0.8208	Intermediate Similarity	NPC85368
0.8208	Intermediate Similarity	NPC24043
0.8208	Intermediate Similarity	NPC101026
0.8208	Intermediate Similarity	NPC470336
0.8208	Intermediate Similarity	NPC470335
0.8208	Intermediate Similarity	NPC42773
0.8198	Intermediate Similarity	NPC254855
0.8198	Intermediate Similarity	NPC156869
0.8198	Intermediate Similarity	NPC20505
0.8198	Intermediate Similarity	NPC282987
0.8198	Intermediate Similarity	NPC29958
0.8198	Intermediate Similarity	NPC259896
0.8198	Intermediate Similarity	NPC95866
0.8198	Intermediate Similarity	NPC235260
0.8198	Intermediate Similarity	NPC136042
0.8198	Intermediate Similarity	NPC255157
0.8198	Intermediate Similarity	NPC8704
0.8198	Intermediate Similarity	NPC287884
0.8198	Intermediate Similarity	NPC245014
0.8198	Intermediate Similarity	NPC155763
0.8198	Intermediate Similarity	NPC67326
0.8198	Intermediate Similarity	NPC84265
0.8192	Intermediate Similarity	NPC231254
0.8187	Intermediate Similarity	NPC92565
0.8187	Intermediate Similarity	NPC52550
0.8187	Intermediate Similarity	NPC223424
0.8187	Intermediate Similarity	NPC160156
0.8187	Intermediate Similarity	NPC127546
0.8187	Intermediate Similarity	NPC317489
0.8187	Intermediate Similarity	NPC173637
0.8187	Intermediate Similarity	NPC84362
0.8182	Intermediate Similarity	NPC315221
0.8182	Intermediate Similarity	NPC208069
0.8176	Intermediate Similarity	NPC19388
0.8176	Intermediate Similarity	NPC240431
0.8176	Intermediate Similarity	NPC277205
0.8176	Intermediate Similarity	NPC472049
0.8176	Intermediate Similarity	NPC55786
0.8171	Intermediate Similarity	NPC470334
0.8171	Intermediate Similarity	NPC35167
0.8171	Intermediate Similarity	NPC253521
0.8171	Intermediate Similarity	NPC113836
0.8171	Intermediate Similarity	NPC37668
0.8166	Intermediate Similarity	NPC478229
0.8166	Intermediate Similarity	NPC326278
0.8161	Intermediate Similarity	NPC115760
0.8161	Intermediate Similarity	NPC253685
0.8161	Intermediate Similarity	NPC214621
0.8161	Intermediate Similarity	NPC49344
0.8161	Intermediate Similarity	NPC264735
0.8161	Intermediate Similarity	NPC223426
0.8161	Intermediate Similarity	NPC3718
0.8161	Intermediate Similarity	NPC81042
0.8161	Intermediate Similarity	NPC210094
0.8161	Intermediate Similarity	NPC135277
0.8161	Intermediate Similarity	NPC43211
0.8161	Intermediate Similarity	NPC101191
0.8161	Intermediate Similarity	NPC34267
0.8161	Intermediate Similarity	NPC237435
0.8155	Intermediate Similarity	NPC470405
0.8155	Intermediate Similarity	NPC304741
0.8155	Intermediate Similarity	NPC471079
0.815	Intermediate Similarity	NPC190003
0.815	Intermediate Similarity	NPC134532
0.815	Intermediate Similarity	NPC471748
0.815	Intermediate Similarity	NPC176740
0.815	Intermediate Similarity	NPC26230
0.815	Intermediate Similarity	NPC60735
0.815	Intermediate Similarity	NPC476405
0.815	Intermediate Similarity	NPC117260
0.815	Intermediate Similarity	NPC471725
0.815	Intermediate Similarity	NPC155877
0.815	Intermediate Similarity	NPC245452
0.815	Intermediate Similarity	NPC33054
0.815	Intermediate Similarity	NPC203259
0.815	Intermediate Similarity	NPC175107
0.8144	Intermediate Similarity	NPC135391
0.8144	Intermediate Similarity	NPC78263
0.8144	Intermediate Similarity	NPC77672
0.8144	Intermediate Similarity	NPC197304
0.8144	Intermediate Similarity	NPC477833
0.8144	Intermediate Similarity	NPC54802
0.8144	Intermediate Similarity	NPC133671
0.814	Intermediate Similarity	NPC225434
0.814	Intermediate Similarity	NPC270578
0.814	Intermediate Similarity	NPC120099
0.814	Intermediate Similarity	NPC52382
0.814	Intermediate Similarity	NPC223747
0.814	Intermediate Similarity	NPC203050
0.814	Intermediate Similarity	NPC219904
0.814	Intermediate Similarity	NPC138927
0.8136	Intermediate Similarity	NPC97119
0.8136	Intermediate Similarity	NPC135831
0.8136	Intermediate Similarity	NPC297503
0.8136	Intermediate Similarity	NPC36138
0.8136	Intermediate Similarity	NPC313452
0.8129	Intermediate Similarity	NPC113093
0.8129	Intermediate Similarity	NPC113968
0.8129	Intermediate Similarity	NPC73855
0.8129	Intermediate Similarity	NPC328940
0.8129	Intermediate Similarity	NPC21100
0.8129	Intermediate Similarity	NPC197285
0.8129	Intermediate Similarity	NPC135599
0.8129	Intermediate Similarity	NPC277174
0.8125	Intermediate Similarity	NPC241423
0.8125	Intermediate Similarity	NPC126784
0.8125	Intermediate Similarity	NPC473571
0.8125	Intermediate Similarity	NPC470444
0.8125	Intermediate Similarity	NPC473682
0.8125	Intermediate Similarity	NPC110941
0.8125	Intermediate Similarity	NPC244903
0.8125	Intermediate Similarity	NPC470443
0.8114	Intermediate Similarity	NPC475246
0.8114	Intermediate Similarity	NPC472384
0.8114	Intermediate Similarity	NPC268533
0.8114	Intermediate Similarity	NPC472382
0.8114	Intermediate Similarity	NPC472380
0.8114	Intermediate Similarity	NPC169733
0.8114	Intermediate Similarity	NPC472385
0.8114	Intermediate Similarity	NPC198324
0.8111	Intermediate Similarity	NPC201814
0.8107	Intermediate Similarity	NPC139320
0.8107	Intermediate Similarity	NPC116458
0.8107	Intermediate Similarity	NPC170052
0.8107	Intermediate Similarity	NPC265885
0.8107	Intermediate Similarity	NPC282169
0.8107	Intermediate Similarity	NPC181465
0.8107	Intermediate Similarity	NPC182045
0.8107	Intermediate Similarity	NPC476215
0.8107	Intermediate Similarity	NPC297987
0.8107	Intermediate Similarity	NPC135846
0.8107	Intermediate Similarity	NPC246943
0.8107	Intermediate Similarity	NPC276377
0.8107	Intermediate Similarity	NPC173582
0.8107	Intermediate Similarity	NPC215710
0.8107	Intermediate Similarity	NPC473438
0.8107	Intermediate Similarity	NPC64305
0.8107	Intermediate Similarity	NPC249281
0.8107	Intermediate Similarity	NPC253788
0.8107	Intermediate Similarity	NPC163242
0.8103	Intermediate Similarity	NPC4390
0.8101	Intermediate Similarity	NPC65489
0.8095	Intermediate Similarity	NPC320283

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 NPC120677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	924
0.2-0.3	2008
0.3-0.4	2751
0.4-0.5	1804
0.5-0.6	888
0.6-0.7	296
0.7-0.8	82
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9935	High Similarity	NPD3787	Discontinued
0.9437	High Similarity	NPD3751	Discontinued
0.8161	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6797	Phase 2
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.7965	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6166	Phase 2
0.7965	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7054	Approved
0.7931	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5402	Approved
0.7907	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7472	Approved
0.7886	Intermediate Similarity	NPD7074	Phase 3
0.7811	Intermediate Similarity	NPD3817	Phase 2
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD3818	Discontinued
0.7751	Intermediate Similarity	NPD8455	Phase 2
0.774	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6782	Approved
0.7701	Intermediate Similarity	NPD6778	Approved
0.7701	Intermediate Similarity	NPD6779	Approved
0.7701	Intermediate Similarity	NPD6777	Approved
0.7701	Intermediate Similarity	NPD6776	Approved
0.7701	Intermediate Similarity	NPD6781	Approved
0.7701	Intermediate Similarity	NPD6780	Approved
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7672	Intermediate Similarity	NPD7435	Discontinued
0.7661	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD7075	Discontinued
0.7611	Intermediate Similarity	NPD8313	Approved
0.7611	Intermediate Similarity	NPD8312	Approved
0.7605	Intermediate Similarity	NPD5403	Approved
0.759	Intermediate Similarity	NPD5401	Approved
0.7588	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD1934	Approved
0.7574	Intermediate Similarity	NPD4380	Phase 2
0.7571	Intermediate Similarity	NPD7228	Approved
0.7558	Intermediate Similarity	NPD4966	Approved
0.7558	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD4965	Approved
0.7558	Intermediate Similarity	NPD3882	Suspended
0.7544	Intermediate Similarity	NPD2801	Approved
0.7544	Intermediate Similarity	NPD7819	Suspended
0.7544	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6799	Approved
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6190	Approved
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7698	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7448	Intermediate Similarity	NPD7870	Phase 2
0.7448	Intermediate Similarity	NPD7871	Phase 2
0.744	Intermediate Similarity	NPD1512	Approved
0.7436	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7874	Approved
0.7433	Intermediate Similarity	NPD6534	Approved
0.7433	Intermediate Similarity	NPD6535	Approved
0.7429	Intermediate Similarity	NPD5494	Approved
0.7423	Intermediate Similarity	NPD7701	Phase 2
0.7405	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6559	Discontinued
0.7403	Intermediate Similarity	NPD7240	Approved
0.7375	Intermediate Similarity	NPD6233	Phase 2
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7345	Intermediate Similarity	NPD6232	Discontinued
0.7341	Intermediate Similarity	NPD1465	Phase 2
0.7321	Intermediate Similarity	NPD1511	Approved
0.7318	Intermediate Similarity	NPD7473	Discontinued
0.7316	Intermediate Similarity	NPD7699	Phase 2
0.7316	Intermediate Similarity	NPD7700	Phase 2
0.7314	Intermediate Similarity	NPD3749	Approved
0.7312	Intermediate Similarity	NPD6798	Discontinued
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7801	Approved
0.7299	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6823	Phase 2
0.7229	Intermediate Similarity	NPD1549	Phase 2
0.7225	Intermediate Similarity	NPD7411	Suspended
0.7222	Intermediate Similarity	NPD1613	Approved
0.7222	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7783	Phase 2
0.7212	Intermediate Similarity	NPD6099	Approved
0.7212	Intermediate Similarity	NPD6100	Approved
0.7208	Intermediate Similarity	NPD8151	Discontinued
0.7204	Intermediate Similarity	NPD8434	Phase 2
0.7195	Intermediate Similarity	NPD7097	Phase 1
0.7179	Intermediate Similarity	NPD8320	Phase 1
0.7179	Intermediate Similarity	NPD8319	Approved
0.7178	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD1653	Approved
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.7108	Intermediate Similarity	NPD2796	Approved
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7076	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1091	Approved
0.7056	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3750	Approved
0.7037	Intermediate Similarity	NPD7095	Approved
0.7017	Intermediate Similarity	NPD3926	Phase 2
0.7012	Intermediate Similarity	NPD4060	Phase 1
0.7011	Intermediate Similarity	NPD3226	Approved
0.7011	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1247	Approved
0.6994	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4908	Phase 1
0.6966	Remote Similarity	NPD7768	Phase 2
0.6964	Remote Similarity	NPD5762	Approved
0.6964	Remote Similarity	NPD5763	Approved
0.6946	Remote Similarity	NPD3748	Approved
0.6946	Remote Similarity	NPD1510	Phase 2
0.6941	Remote Similarity	NPD4628	Phase 3
0.6933	Remote Similarity	NPD4625	Phase 3
0.6927	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6213	Phase 3
0.6927	Remote Similarity	NPD6212	Phase 3
0.6923	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8285	Discontinued
0.6919	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2974	Approved
0.6907	Remote Similarity	NPD2973	Approved
0.6907	Remote Similarity	NPD2975	Approved
0.689	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD919	Approved
0.6888	Remote Similarity	NPD4580	Approved
0.6882	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4004	Approved
0.6869	Remote Similarity	NPD4002	Approved
0.6864	Remote Similarity	NPD2346	Discontinued
0.6853	Remote Similarity	NPD2493	Approved
0.6853	Remote Similarity	NPD3450	Approved
0.6853	Remote Similarity	NPD2494	Approved
0.6853	Remote Similarity	NPD3452	Approved
0.6848	Remote Similarity	NPD4062	Phase 3
0.6842	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4583	Approved
0.6834	Remote Similarity	NPD4582	Approved
0.6829	Remote Similarity	NPD3027	Phase 3
0.6824	Remote Similarity	NPD2897	Discontinued
0.6821	Remote Similarity	NPD7390	Discontinued
0.6818	Remote Similarity	NPD7458	Discontinued
0.6813	Remote Similarity	NPD1608	Approved
0.6813	Remote Similarity	NPD8127	Discontinued
0.681	Remote Similarity	NPD2861	Phase 2
0.6784	Remote Similarity	NPD7680	Approved
0.6784	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2532	Approved
0.6782	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2534	Approved
0.6782	Remote Similarity	NPD2533	Approved
0.6766	Remote Similarity	NPD1933	Approved
0.6765	Remote Similarity	NPD7266	Discontinued
0.675	Remote Similarity	NPD1610	Phase 2
0.6744	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD2424	Discontinued
0.6707	Remote Similarity	NPD1240	Approved
0.6706	Remote Similarity	NPD1551	Phase 2
0.6704	Remote Similarity	NPD6844	Discontinued
0.6687	Remote Similarity	NPD3268	Approved
0.6687	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1652	Phase 2
0.6683	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8059	Phase 3
0.6648	Remote Similarity	NPD6273	Approved
0.6647	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5647	Approved
0.6628	Remote Similarity	NPD4534	Discontinued
0.6628	Remote Similarity	NPD5958	Discontinued
0.6627	Remote Similarity	NPD1607	Approved
0.6626	Remote Similarity	NPD3225	Approved
0.6625	Remote Similarity	NPD17	Approved
0.6618	Remote Similarity	NPD7930	Approved
0.6613	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.661	Remote Similarity	NPD920	Approved
0.6609	Remote Similarity	NPD2677	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