NPASS Compound

Structure

NPC474966 OpenBabel07101718292D 28 30 0 0 1 0 0 0 0 0999 V2000 -2.7591 3.2406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 0.8090 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 1 7 2 0 0 0 0 2 13 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 6 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 6 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 14 1 6 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 22 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.19
Volume:	400.321
LogP:	2.747
LogD:	2.814
LogS:	-3.506
# Rotatable Bonds:	7
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	4.249
Fsp3:	0.5
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:	-4.63
MDCK Permeability:	1.619767317606602e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.259

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.311
Plasma Protein Binding (PPB):	77.87911224365234%
Volume Distribution (VD):	0.879
Pgp-substrate:	15.162910461425781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.326
CYP3A4-inhibitor:	0.752
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	5.864
Half-life (T1/2):	0.43

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.464
Drug-inuced Liver Injury (DILI):	0.239
AMES Toxicity:	0.248
Rat Oral Acute Toxicity:	0.388
Maximum Recommended Daily Dose:	0.288
Skin Sensitization:	0.303
Carcinogencity:	0.884
Eye Corrosion:	0.005
Eye Irritation:	0.039
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC474966

Natural Product ID:	NPC474966
*Common Name:**	Dysodanthin B
IUPAC Name:	(2R,3S,3aS,5R)-5-methoxy-3-methyl-3a-prop-2-enyl-2-(3,4,5-trimethoxyphenyl)-2,3,4,5-tetrahydro-1-benzofuran-6-one
Synonyms:	dysodanthin B
Standard InCHIKey:	NUJJSWCDYDXRAO-FPZBQUANSA-N
Standard InCHI:	InChI=1S/C22H28O6/c1-7-8-22-12-18(26-5)15(23)11-19(22)28-20(13(22)2)14-9-16(24-3)21(27-6)17(10-14)25-4/h7,9-11,13,18,20H,1,8,12H2,2-6H3/t13-,18-,20-,22+/m1/s1
SMILES:	CC1C(OC2=CC(=O)C(CC12CC=C)OC)C3=CC(=C(C(=C3)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490365
PubChem CID:	44576118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO14069	Endlicheria dysodantha	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1665173]
NPO14069	Endlicheria dysodantha	Species	Lauraceae	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
ED50	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.68	ug ml-1	PMID[505590]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	4.09	ug ml-1	PMID[505590]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.76	ug ml-1	PMID[505590]
NPT140	Organism	Artemia	Artemia	LC50	=	334.2	ppm	PMID[505590]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	52.0	%	PMID[505590]

☑ 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 NPC474966 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	422
0.1-0.2	1374
0.2-0.3	3023
0.3-0.4	7653
0.4-0.5	11138
0.5-0.6	4587
0.6-0.7	9347
0.7-0.8	4997
0.8-0.85	129
0.85-0.9	21
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC475170
0.9296	High Similarity	NPC25496
0.9124	High Similarity	NPC145769
0.9078	High Similarity	NPC46180
0.8951	High Similarity	NPC50696
0.8849	High Similarity	NPC37065
0.8832	High Similarity	NPC339621
0.8832	High Similarity	NPC280399
0.8832	High Similarity	NPC233961
0.8759	High Similarity	NPC476841
0.8759	High Similarity	NPC476843
0.8759	High Similarity	NPC232883
0.8699	High Similarity	NPC476362
0.8671	High Similarity	NPC278076
0.8652	High Similarity	NPC211386
0.8621	High Similarity	NPC28326
0.8611	High Similarity	NPC51681
0.8591	High Similarity	NPC177830
0.8571	High Similarity	NPC472560
0.8552	High Similarity	NPC476840
0.8552	High Similarity	NPC476842
0.854	High Similarity	NPC112571
0.854	High Similarity	NPC285725
0.854	High Similarity	NPC50683
0.8533	High Similarity	NPC62354
0.8523	High Similarity	NPC472567
0.8521	High Similarity	NPC72796
0.8521	High Similarity	NPC44245
0.8514	High Similarity	NPC30720
0.8477	Intermediate Similarity	NPC151425
0.8477	Intermediate Similarity	NPC28724
0.8462	Intermediate Similarity	NPC209229
0.8456	Intermediate Similarity	NPC117463
0.8442	Intermediate Similarity	NPC476340
0.8435	Intermediate Similarity	NPC15743
0.8431	Intermediate Similarity	NPC476363
0.8421	Intermediate Similarity	NPC327225
0.8417	Intermediate Similarity	NPC222127
0.8417	Intermediate Similarity	NPC82862
0.8414	Intermediate Similarity	NPC322021
0.8411	Intermediate Similarity	NPC163002
0.8406	Intermediate Similarity	NPC186845
0.8406	Intermediate Similarity	NPC9891
0.8406	Intermediate Similarity	NPC88297
0.8403	Intermediate Similarity	NPC166184
0.8366	Intermediate Similarity	NPC25127
0.8365	Intermediate Similarity	NPC42230
0.8365	Intermediate Similarity	NPC474948
0.8345	Intermediate Similarity	NPC473093
0.8345	Intermediate Similarity	NPC473092
0.8345	Intermediate Similarity	NPC470962
0.8345	Intermediate Similarity	NPC8050
0.8333	Intermediate Similarity	NPC294972
0.8322	Intermediate Similarity	NPC30890
0.8322	Intermediate Similarity	NPC213482
0.8322	Intermediate Similarity	NPC212697
0.8312	Intermediate Similarity	NPC117154
0.8299	Intermediate Similarity	NPC210354
0.8299	Intermediate Similarity	NPC176586
0.8298	Intermediate Similarity	NPC470624
0.8298	Intermediate Similarity	NPC237169
0.8286	Intermediate Similarity	NPC328682
0.8286	Intermediate Similarity	NPC54321
0.8286	Intermediate Similarity	NPC281864
0.8272	Intermediate Similarity	NPC474568
0.8267	Intermediate Similarity	NPC310259
0.8255	Intermediate Similarity	NPC474982
0.8247	Intermediate Similarity	NPC287504
0.8243	Intermediate Similarity	NPC273657
0.8243	Intermediate Similarity	NPC106920
0.8239	Intermediate Similarity	NPC475953
0.8239	Intermediate Similarity	NPC474647
0.8235	Intermediate Similarity	NPC476434
0.8235	Intermediate Similarity	NPC476335
0.8227	Intermediate Similarity	NPC150809
0.8224	Intermediate Similarity	NPC238366
0.8224	Intermediate Similarity	NPC69752
0.8217	Intermediate Similarity	NPC298093
0.8212	Intermediate Similarity	NPC470511
0.8212	Intermediate Similarity	NPC262804
0.8212	Intermediate Similarity	NPC474999
0.8212	Intermediate Similarity	NPC40654
0.8212	Intermediate Similarity	NPC299923
0.8207	Intermediate Similarity	NPC471182
0.82	Intermediate Similarity	NPC474799
0.82	Intermediate Similarity	NPC474446
0.8194	Intermediate Similarity	NPC188962
0.8194	Intermediate Similarity	NPC202249
0.8194	Intermediate Similarity	NPC474478
0.8194	Intermediate Similarity	NPC42871
0.8194	Intermediate Similarity	NPC471746
0.8188	Intermediate Similarity	NPC475000
0.8188	Intermediate Similarity	NPC177644
0.8188	Intermediate Similarity	NPC191158
0.8188	Intermediate Similarity	NPC18211
0.8187	Intermediate Similarity	NPC476277
0.8182	Intermediate Similarity	NPC280476
0.8182	Intermediate Similarity	NPC119985
0.8182	Intermediate Similarity	NPC153453
0.8182	Intermediate Similarity	NPC239302
0.8176	Intermediate Similarity	NPC151423
0.8176	Intermediate Similarity	NPC476822
0.8176	Intermediate Similarity	NPC40237
0.8175	Intermediate Similarity	NPC312713
0.8175	Intermediate Similarity	NPC172676
0.8175	Intermediate Similarity	NPC57268
0.8175	Intermediate Similarity	NPC65933
0.8175	Intermediate Similarity	NPC216929
0.8175	Intermediate Similarity	NPC126935
0.817	Intermediate Similarity	NPC201547
0.817	Intermediate Similarity	NPC259058
0.817	Intermediate Similarity	NPC216917
0.817	Intermediate Similarity	NPC178048
0.8163	Intermediate Similarity	NPC147379
0.8163	Intermediate Similarity	NPC470855
0.8158	Intermediate Similarity	NPC476342
0.8153	Intermediate Similarity	NPC250076
0.8146	Intermediate Similarity	NPC195919
0.8146	Intermediate Similarity	NPC216314
0.8146	Intermediate Similarity	NPC120924
0.8141	Intermediate Similarity	NPC477380
0.8133	Intermediate Similarity	NPC27106
0.8133	Intermediate Similarity	NPC474158
0.8129	Intermediate Similarity	NPC121783
0.8129	Intermediate Similarity	NPC18449
0.8129	Intermediate Similarity	NPC34902
0.8125	Intermediate Similarity	NPC288743
0.8125	Intermediate Similarity	NPC266848
0.8125	Intermediate Similarity	NPC158331
0.8125	Intermediate Similarity	NPC136750
0.8121	Intermediate Similarity	NPC477696
0.8121	Intermediate Similarity	NPC477697
0.8121	Intermediate Similarity	NPC470811
0.8121	Intermediate Similarity	NPC185607
0.8121	Intermediate Similarity	NPC474288
0.8117	Intermediate Similarity	NPC473732
0.8117	Intermediate Similarity	NPC95498
0.8117	Intermediate Similarity	NPC474414
0.8117	Intermediate Similarity	NPC246566
0.8113	Intermediate Similarity	NPC476244
0.8105	Intermediate Similarity	NPC181250
0.8105	Intermediate Similarity	NPC12854
0.8099	Intermediate Similarity	NPC153547
0.8095	Intermediate Similarity	NPC44573
0.8095	Intermediate Similarity	NPC178290
0.8089	Intermediate Similarity	NPC471479
0.8089	Intermediate Similarity	NPC471515
0.8089	Intermediate Similarity	NPC19097
0.8089	Intermediate Similarity	NPC477885
0.8089	Intermediate Similarity	NPC258644
0.8089	Intermediate Similarity	NPC220462
0.8086	Intermediate Similarity	NPC165456
0.8085	Intermediate Similarity	NPC223807
0.8082	Intermediate Similarity	NPC143895
0.8079	Intermediate Similarity	NPC193779
0.8079	Intermediate Similarity	NPC471590
0.8077	Intermediate Similarity	NPC284353
0.8069	Intermediate Similarity	NPC287745
0.8067	Intermediate Similarity	NPC27159
0.8067	Intermediate Similarity	NPC92693
0.8067	Intermediate Similarity	NPC143092
0.8067	Intermediate Similarity	NPC9966
0.8067	Intermediate Similarity	NPC70853
0.8067	Intermediate Similarity	NPC16353
0.8067	Intermediate Similarity	NPC218841
0.8065	Intermediate Similarity	NPC475116
0.8056	Intermediate Similarity	NPC475856
0.8056	Intermediate Similarity	NPC72046
0.8056	Intermediate Similarity	NPC175067
0.8056	Intermediate Similarity	NPC65183
0.8056	Intermediate Similarity	NPC261812
0.8056	Intermediate Similarity	NPC204215
0.8054	Intermediate Similarity	NPC31751
0.8054	Intermediate Similarity	NPC253481
0.8054	Intermediate Similarity	NPC472335
0.8054	Intermediate Similarity	NPC58229
0.8054	Intermediate Similarity	NPC472332
0.8054	Intermediate Similarity	NPC253722
0.805	Intermediate Similarity	NPC187354
0.8043	Intermediate Similarity	NPC477886
0.8042	Intermediate Similarity	NPC172673
0.8039	Intermediate Similarity	NPC261548
0.8039	Intermediate Similarity	NPC10304
0.8039	Intermediate Similarity	NPC63256
0.8039	Intermediate Similarity	NPC125570
0.8039	Intermediate Similarity	NPC474903
0.8039	Intermediate Similarity	NPC476058
0.8038	Intermediate Similarity	NPC257914
0.8038	Intermediate Similarity	NPC104459
0.8038	Intermediate Similarity	NPC325122
0.8038	Intermediate Similarity	NPC475095
0.8038	Intermediate Similarity	NPC238405
0.8038	Intermediate Similarity	NPC195832
0.8038	Intermediate Similarity	NPC472565
0.8028	Intermediate Similarity	NPC210674
0.8026	Intermediate Similarity	NPC153620
0.8026	Intermediate Similarity	NPC24257
0.8026	Intermediate Similarity	NPC472333
0.8026	Intermediate Similarity	NPC40818
0.8026	Intermediate Similarity	NPC208507

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 NPC474966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	855
0.2-0.3	1702
0.3-0.4	2693
0.4-0.5	1948
0.5-0.6	1087
0.6-0.7	443
0.7-0.8	74
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
0.8217	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD3882	Suspended
0.7974	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7937	Intermediate Similarity	NPD1247	Approved
0.7834	Intermediate Similarity	NPD1934	Approved
0.7812	Intermediate Similarity	NPD919	Approved
0.773	Intermediate Similarity	NPD3926	Phase 2
0.773	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3027	Phase 3
0.7722	Intermediate Similarity	NPD37	Approved
0.7707	Intermediate Similarity	NPD6599	Discontinued
0.7688	Intermediate Similarity	NPD4965	Approved
0.7688	Intermediate Similarity	NPD4967	Phase 2
0.7688	Intermediate Similarity	NPD4966	Approved
0.7683	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6166	Phase 2
0.7683	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2801	Approved
0.7673	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6234	Discontinued
0.7582	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4110	Phase 3
0.7554	Intermediate Similarity	NPD5536	Phase 2
0.755	Intermediate Similarity	NPD2796	Approved
0.7548	Intermediate Similarity	NPD6799	Approved
0.7548	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3705	Approved
0.7518	Intermediate Similarity	NPD5283	Phase 1
0.7516	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7453	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1512	Approved
0.7442	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5844	Phase 1
0.7419	Intermediate Similarity	NPD6190	Approved
0.741	Intermediate Similarity	NPD5242	Approved
0.74	Intermediate Similarity	NPD6355	Discontinued
0.7389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7028	Phase 2
0.7368	Intermediate Similarity	NPD7808	Phase 3
0.7368	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2403	Approved
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2981	Phase 2
0.7355	Intermediate Similarity	NPD4628	Phase 3
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6797	Phase 2
0.7325	Intermediate Similarity	NPD1511	Approved
0.7321	Intermediate Similarity	NPD7473	Discontinued
0.732	Intermediate Similarity	NPD6099	Approved
0.732	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD7075	Discontinued
0.7315	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2982	Phase 2
0.731	Intermediate Similarity	NPD7251	Discontinued
0.731	Intermediate Similarity	NPD2983	Phase 2
0.7301	Intermediate Similarity	NPD5402	Approved
0.7294	Intermediate Similarity	NPD7074	Phase 3
0.729	Intermediate Similarity	NPD2800	Approved
0.7289	Intermediate Similarity	NPD8127	Discontinued
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD6801	Discontinued
0.7278	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD3146	Approved
0.7278	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD4380	Phase 2
0.7266	Intermediate Similarity	NPD1241	Discontinued
0.7255	Intermediate Similarity	NPD3748	Approved
0.7246	Intermediate Similarity	NPD6232	Discontinued
0.7241	Intermediate Similarity	NPD3972	Approved
0.7235	Intermediate Similarity	NPD7054	Approved
0.723	Intermediate Similarity	NPD3018	Phase 2
0.7226	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1613	Approved
0.7219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7472	Approved
0.7192	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6111	Discontinued
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.717	Intermediate Similarity	NPD2533	Approved
0.717	Intermediate Similarity	NPD2534	Approved
0.717	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD17	Approved
0.7152	Intermediate Similarity	NPD7124	Phase 2
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7134	Intermediate Similarity	NPD7819	Suspended
0.7133	Intermediate Similarity	NPD7095	Approved
0.7126	Intermediate Similarity	NPD2968	Approved
0.7126	Intermediate Similarity	NPD2971	Approved
0.7117	Intermediate Similarity	NPD6385	Approved
0.7117	Intermediate Similarity	NPD5090	Approved
0.7117	Intermediate Similarity	NPD6386	Approved
0.7117	Intermediate Similarity	NPD5089	Approved
0.7115	Intermediate Similarity	NPD1549	Phase 2
0.711	Intermediate Similarity	NPD7240	Approved
0.7107	Intermediate Similarity	NPD4357	Discontinued
0.7105	Intermediate Similarity	NPD1240	Approved
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7097	Intermediate Similarity	NPD2438	Suspended
0.7091	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD1651	Approved
0.7083	Intermediate Similarity	NPD5585	Approved
0.7081	Intermediate Similarity	NPD5403	Approved
0.7081	Intermediate Similarity	NPD920	Approved
0.7067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5401	Approved
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8032	Phase 2
0.7037	Intermediate Similarity	NPD1653	Approved
0.7035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4585	Approved
0.7027	Intermediate Similarity	NPD1876	Approved
0.7025	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD8166	Discontinued
0.7019	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1607	Approved
0.7013	Intermediate Similarity	NPD6651	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4534	Discontinued
0.7	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5297	Approved
0.6994	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2979	Phase 3
0.6981	Remote Similarity	NPD3887	Approved
0.698	Remote Similarity	NPD3266	Approved
0.698	Remote Similarity	NPD3267	Approved
0.6978	Remote Similarity	NPD2974	Approved
0.6978	Remote Similarity	NPD2975	Approved
0.6978	Remote Similarity	NPD2973	Approved
0.6974	Remote Similarity	NPD1296	Phase 2
0.6974	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1357	Approved
0.6964	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1243	Approved
0.6962	Remote Similarity	NPD2654	Approved
0.6957	Remote Similarity	NPD4580	Approved
0.6957	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4908	Phase 1
0.6948	Remote Similarity	NPD3657	Discovery
0.6941	Remote Similarity	NPD7229	Phase 3
0.6937	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1465	Phase 2
0.6928	Remote Similarity	NPD4062	Phase 3
0.6923	Remote Similarity	NPD7157	Approved
0.6914	Remote Similarity	NPD6559	Discontinued
0.6914	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6873	Phase 2
0.6899	Remote Similarity	NPD2424	Discontinued
0.6899	Remote Similarity	NPD5958	Discontinued
0.6887	Remote Similarity	NPD2861	Phase 2
0.6883	Remote Similarity	NPD4060	Phase 1
0.6883	Remote Similarity	NPD3620	Phase 2
0.6883	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6959	Discontinued
0.6879	Remote Similarity	NPD2163	Approved
0.6879	Remote Similarity	NPD2935	Discontinued
0.6865	Remote Similarity	NPD4107	Approved
0.6863	Remote Similarity	NPD3268	Approved
0.6863	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2067	Discontinued
0.6849	Remote Similarity	NPD5691	Approved
0.6846	Remote Similarity	NPD4749	Approved
0.6846	Remote Similarity	NPD5327	Phase 3
0.6846	Remote Similarity	NPD4359	Approved
0.6839	Remote Similarity	NPD447	Suspended
0.6835	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6004	Phase 3
0.6835	Remote Similarity	NPD1358	Approved
0.6835	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6005	Phase 3
0.6835	Remote Similarity	NPD5763	Approved
0.6835	Remote Similarity	NPD6002	Phase 3
0.6828	Remote Similarity	NPD2494	Approved
0.6828	Remote Similarity	NPD2493	Approved
0.6824	Remote Similarity	NPD1281	Approved
0.6824	Remote Similarity	NPD1610	Phase 2
0.6818	Remote Similarity	NPD7685	Pre-registration
0.6815	Remote Similarity	NPD651	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6273	Approved
0.6809	Remote Similarity	NPD4582	Approved
0.6809	Remote Similarity	NPD4583	Approved
0.6807	Remote Similarity	NPD7411	Suspended
0.6803	Remote Similarity	NPD1778	Approved
0.68	Remote Similarity	NPD8651	Approved
0.6798	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2490	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