NPASS Compound

Structure

CID287504 OpenBabel06191716092D 31 33 0 0 1 0 0 0 0 0999 V2000 2.5173 5.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6819 3.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2916 2.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8739 1.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8794 1.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6984 3.3988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2807 2.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6929 3.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2738 3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0605 -0.0464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0996 4.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1106 4.2078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2752 2.7988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 3.9945 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 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 11 1 0 0 0 0 6 16 2 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 18 2 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 10 31 1 0 0 0 0 11 19 1 0 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 6 0 0 0 15 20 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 21 2 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 30 1 0 0 0 0 19 24 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 12 1 6 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.16
Volume:	424.056
LogP:	1.455
LogD:	1.763
LogS:	-4.381
# Rotatable Bonds:	8
TPSA:	123.91
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	3.631
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.018
MDCK Permeability:	1.639770925976336e-05
Pgp-inhibitor:	0.511
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	75.42459869384766%
Volume Distribution (VD):	0.477
Pgp-substrate:	29.56243133544922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.475
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.446
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.7

ADMET: Excretion

Clearance (CL):	10.689
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.3
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.273
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.87
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.058
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC287504

Natural Product ID:	NPC287504
*Common Name:**	(-)-(7's,8S,8'r)-4,4'-Dihydroxy-3,3',5,5'-Tetramethoxy-7',9-Epoxylignan-9'-Ol-7-One
IUPAC Name:	(4-hydroxy-3,5-dimethoxyphenyl)-[(3S,4R,5S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methanone
Synonyms:
Standard InCHIKey:	ANCVHDRNDJRUOT-DJEJFTSGSA-N
Standard InCHI:	InChI=1S/C22H26O9/c1-27-15-5-11(6-16(28-2)20(15)25)19(24)14-10-31-22(13(14)9-23)12-7-17(29-3)21(26)18(8-12)30-4/h5-8,13-14,22-23,25-26H,9-10H2,1-4H3/t13-,14+,22+/m0/s1
SMILES:	OC[C@@H]1[C@H](OC[C@H]1C(=O)c1cc(OC)c(c(c1)OC)O)c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797772
PubChem CID:	53356211
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795843]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27668963]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9871.1	Ficus benghalensis var. krishnae	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6514	Desmotrichum fimbriatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12736	Galleria mellonella	Species	Pyralidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10825	Nerine sarniensis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9577	Triclisia dictyophylla	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6012	Dumoria heckelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO35	Zanthoxylum dinklagei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10298	Symbiodinium microadriaticum	Species	Symbiodiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1743	Neurospora terricola	Species	Sordariaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	<	30.0	%	PMID[549643]

☑ 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 NPC287504 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	374
0.1-0.2	1310
0.2-0.3	3125
0.3-0.4	7687
0.4-0.5	10540
0.5-0.6	4420
0.6-0.7	5066
0.7-0.8	7268
0.8-0.85	2403
0.85-0.9	486
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC25127
0.9728	High Similarity	NPC151425
0.966	High Similarity	NPC62354
0.9524	High Similarity	NPC474903
0.9419	High Similarity	NPC475738
0.932	High Similarity	NPC30890
0.9184	High Similarity	NPC46161
0.9184	High Similarity	NPC239608
0.9167	High Similarity	NPC76687
0.9161	High Similarity	NPC472962
0.9161	High Similarity	NPC472961
0.9156	High Similarity	NPC129684
0.9156	High Similarity	NPC299520
0.9108	High Similarity	NPC18100
0.9108	High Similarity	NPC124038
0.9091	High Similarity	NPC469474
0.9085	High Similarity	NPC250557
0.9079	High Similarity	NPC75695
0.906	High Similarity	NPC213482
0.9051	High Similarity	NPC472277
0.9045	High Similarity	NPC81679
0.9045	High Similarity	NPC472635
0.9041	High Similarity	NPC4796
0.9032	High Similarity	NPC190020
0.9032	High Similarity	NPC77679
0.9032	High Similarity	NPC84935
0.9032	High Similarity	NPC469584
0.9032	High Similarity	NPC78103
0.9026	High Similarity	NPC79998
0.9026	High Similarity	NPC31018
0.9026	High Similarity	NPC255807
0.9013	High Similarity	NPC472279
0.9007	High Similarity	NPC125570
0.8994	High Similarity	NPC119589
0.8994	High Similarity	NPC43065
0.8994	High Similarity	NPC235610
0.8993	High Similarity	NPC207732
0.8987	High Similarity	NPC205265
0.8987	High Similarity	NPC469475
0.8987	High Similarity	NPC472281
0.8987	High Similarity	NPC469518
0.8987	High Similarity	NPC475985
0.8968	High Similarity	NPC150227
0.8968	High Similarity	NPC250922
0.8961	High Similarity	NPC469550
0.8961	High Similarity	NPC18727
0.8961	High Similarity	NPC124714
0.8954	High Similarity	NPC272566
0.8954	High Similarity	NPC267091
0.8954	High Similarity	NPC19980
0.8954	High Similarity	NPC45291
0.8954	High Similarity	NPC476434
0.8947	High Similarity	NPC139293
0.8947	High Similarity	NPC40290
0.8947	High Similarity	NPC264289
0.8947	High Similarity	NPC264550
0.8947	High Similarity	NPC473091
0.8947	High Similarity	NPC195763
0.8947	High Similarity	NPC142876
0.8947	High Similarity	NPC102003
0.8947	High Similarity	NPC333691
0.8947	High Similarity	NPC92722
0.8947	High Similarity	NPC69430
0.8947	High Similarity	NPC200060
0.8944	High Similarity	NPC102277
0.8944	High Similarity	NPC212748
0.8944	High Similarity	NPC279209
0.8938	High Similarity	NPC247973
0.8931	High Similarity	NPC300053
0.8931	High Similarity	NPC108433
0.8931	High Similarity	NPC326520
0.8924	High Similarity	NPC312056
0.8924	High Similarity	NPC472964
0.8924	High Similarity	NPC84515
0.8917	High Similarity	NPC472624
0.8917	High Similarity	NPC472630
0.8917	High Similarity	NPC472902
0.8917	High Similarity	NPC470326
0.8917	High Similarity	NPC472631
0.8917	High Similarity	NPC24627
0.8917	High Similarity	NPC328102
0.891	High Similarity	NPC474208
0.891	High Similarity	NPC474055
0.891	High Similarity	NPC470402
0.891	High Similarity	NPC156057
0.891	High Similarity	NPC210084
0.891	High Similarity	NPC474836
0.891	High Similarity	NPC472598
0.891	High Similarity	NPC472910
0.891	High Similarity	NPC472914
0.891	High Similarity	NPC52530
0.891	High Similarity	NPC475267
0.891	High Similarity	NPC96167
0.891	High Similarity	NPC472911
0.891	High Similarity	NPC222814
0.891	High Similarity	NPC181960
0.891	High Similarity	NPC162869
0.891	High Similarity	NPC472913
0.891	High Similarity	NPC291508
0.891	High Similarity	NPC245758
0.891	High Similarity	NPC48208
0.891	High Similarity	NPC99597
0.8903	High Similarity	NPC16082
0.8903	High Similarity	NPC300757
0.8903	High Similarity	NPC45849
0.8903	High Similarity	NPC200761
0.8903	High Similarity	NPC130589
0.8903	High Similarity	NPC82592
0.8903	High Similarity	NPC477503
0.8903	High Similarity	NPC180901
0.8903	High Similarity	NPC199926
0.8903	High Similarity	NPC134287
0.8903	High Similarity	NPC208197
0.8903	High Similarity	NPC470327
0.8896	High Similarity	NPC121522
0.8896	High Similarity	NPC236637
0.8896	High Similarity	NPC477231
0.8896	High Similarity	NPC209487
0.8896	High Similarity	NPC473236
0.8896	High Similarity	NPC291802
0.8896	High Similarity	NPC100263
0.8896	High Similarity	NPC39732
0.8896	High Similarity	NPC131266
0.8896	High Similarity	NPC472912
0.8896	High Similarity	NPC260979
0.8896	High Similarity	NPC323626
0.8896	High Similarity	NPC269451
0.8896	High Similarity	NPC35763
0.8896	High Similarity	NPC181209
0.8896	High Similarity	NPC257648
0.8896	High Similarity	NPC60972
0.8896	High Similarity	NPC100971
0.8896	High Similarity	NPC219582
0.8896	High Similarity	NPC216769
0.8896	High Similarity	NPC324233
0.8896	High Similarity	NPC245382
0.8896	High Similarity	NPC302950
0.8889	High Similarity	NPC469506
0.8889	High Similarity	NPC338131
0.8889	High Similarity	NPC239363
0.8889	High Similarity	NPC243891
0.8882	High Similarity	NPC194653
0.8882	High Similarity	NPC203747
0.8882	High Similarity	NPC15329
0.8882	High Similarity	NPC80710
0.8882	High Similarity	NPC131451
0.8882	High Similarity	NPC288813
0.8882	High Similarity	NPC287395
0.8882	High Similarity	NPC139364
0.8882	High Similarity	NPC254702
0.8882	High Similarity	NPC183655
0.8875	High Similarity	NPC128293
0.8875	High Similarity	NPC207575
0.8875	High Similarity	NPC13481
0.8875	High Similarity	NPC170245
0.8874	High Similarity	NPC165389
0.8868	High Similarity	NPC329669
0.8868	High Similarity	NPC472278
0.8868	High Similarity	NPC473313
0.8868	High Similarity	NPC273959
0.8868	High Similarity	NPC133065
0.8867	High Similarity	NPC142165
0.8861	High Similarity	NPC472634
0.8861	High Similarity	NPC158188
0.8861	High Similarity	NPC26326
0.8861	High Similarity	NPC471499
0.8861	High Similarity	NPC308992
0.8861	High Similarity	NPC134783
0.8861	High Similarity	NPC87431
0.8861	High Similarity	NPC188486
0.8861	High Similarity	NPC266314
0.8859	High Similarity	NPC477697
0.8859	High Similarity	NPC312256
0.8859	High Similarity	NPC477696
0.8859	High Similarity	NPC470811
0.8854	High Similarity	NPC55738
0.8854	High Similarity	NPC329091
0.8854	High Similarity	NPC172202
0.8854	High Similarity	NPC284127
0.8854	High Similarity	NPC196879
0.8854	High Similarity	NPC476410
0.8854	High Similarity	NPC195832
0.8846	High Similarity	NPC320825
0.8846	High Similarity	NPC235165
0.8846	High Similarity	NPC470328
0.8846	High Similarity	NPC255106
0.8846	High Similarity	NPC278778
0.8846	High Similarity	NPC472916
0.8846	High Similarity	NPC472626
0.8846	High Similarity	NPC317383
0.8846	High Similarity	NPC209614
0.8846	High Similarity	NPC13858
0.8846	High Similarity	NPC291878
0.8846	High Similarity	NPC326037
0.8846	High Similarity	NPC35038
0.8846	High Similarity	NPC195796
0.8839	High Similarity	NPC250822
0.8839	High Similarity	NPC276409
0.8839	High Similarity	NPC280937
0.8839	High Similarity	NPC75279

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 NPC287504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	817
0.2-0.3	1752
0.3-0.4	2581
0.4-0.5	2028
0.5-0.6	1041
0.6-0.7	451
0.7-0.8	133
0.8-0.85	21
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8968	High Similarity	NPD3882	Suspended
0.8938	High Similarity	NPD3818	Discontinued
0.8896	High Similarity	NPD1934	Approved
0.8718	High Similarity	NPD2801	Approved
0.8718	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD6167	Clinical (unspecified phase)
0.8696	High Similarity	NPD6168	Clinical (unspecified phase)
0.8696	High Similarity	NPD6166	Phase 2
0.8608	High Similarity	NPD4868	Clinical (unspecified phase)
0.8562	High Similarity	NPD5494	Approved
0.8526	High Similarity	NPD4380	Phase 2
0.8485	Intermediate Similarity	NPD7074	Phase 3
0.8424	Intermediate Similarity	NPD7054	Approved
0.8377	Intermediate Similarity	NPD1511	Approved
0.8373	Intermediate Similarity	NPD7472	Approved
0.8313	Intermediate Similarity	NPD3817	Phase 2
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8272	Intermediate Similarity	NPD6234	Discontinued
0.8269	Intermediate Similarity	NPD1512	Approved
0.8255	Intermediate Similarity	NPD230	Phase 1
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.8231	Intermediate Similarity	NPD3027	Phase 3
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6797	Phase 2
0.8214	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD37	Approved
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.8148	Intermediate Similarity	NPD4967	Phase 2
0.8148	Intermediate Similarity	NPD4966	Approved
0.8148	Intermediate Similarity	NPD4965	Approved
0.8137	Intermediate Similarity	NPD1465	Phase 2
0.8118	Intermediate Similarity	NPD7808	Phase 3
0.8098	Intermediate Similarity	NPD7075	Discontinued
0.8092	Intermediate Similarity	NPD1510	Phase 2
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8067	Intermediate Similarity	NPD943	Approved
0.8067	Intermediate Similarity	NPD1240	Approved
0.8052	Intermediate Similarity	NPD1549	Phase 2
0.8036	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6801	Discontinued
0.7961	Intermediate Similarity	NPD1607	Approved
0.7953	Intermediate Similarity	NPD7685	Pre-registration
0.7953	Intermediate Similarity	NPD6559	Discontinued
0.7949	Intermediate Similarity	NPD4628	Phase 3
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2796	Approved
0.7914	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7819	Suspended
0.7911	Intermediate Similarity	NPD6799	Approved
0.7898	Intermediate Similarity	NPD6190	Approved
0.7866	Intermediate Similarity	NPD5402	Approved
0.7852	Intermediate Similarity	NPD9494	Approved
0.7844	Intermediate Similarity	NPD1247	Approved
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7844	Intermediate Similarity	NPD6959	Discontinued
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7799	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2800	Approved
0.775	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD919	Approved
0.7712	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1613	Approved
0.7703	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7411	Suspended
0.7654	Intermediate Similarity	NPD5403	Approved
0.7651	Intermediate Similarity	NPD5353	Approved
0.7647	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5242	Approved
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8434	Phase 2
0.758	Intermediate Similarity	NPD2935	Discontinued
0.756	Intermediate Similarity	NPD3749	Approved
0.7543	Intermediate Similarity	NPD7240	Approved
0.7532	Intermediate Similarity	NPD2344	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD920	Approved
0.7436	Intermediate Similarity	NPD447	Suspended
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7768	Phase 2
0.7394	Intermediate Similarity	NPD1653	Approved
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7366	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6385	Approved
0.7365	Intermediate Similarity	NPD6386	Approved
0.7362	Intermediate Similarity	NPD4357	Discontinued
0.7358	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD1551	Phase 2
0.7358	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2309	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1243	Approved
0.7318	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7266	Discontinued
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7288	Intermediate Similarity	NPD5953	Discontinued
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7256	Intermediate Similarity	NPD7390	Discontinued
0.7248	Intermediate Similarity	NPD9268	Approved
0.7246	Intermediate Similarity	NPD3226	Approved
0.7244	Intermediate Similarity	NPD3764	Approved
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7225	Intermediate Similarity	NPD8127	Discontinued
0.7219	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.7195	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3748	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7178	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4110	Phase 3
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5760	Phase 2
0.7176	Intermediate Similarity	NPD5761	Phase 2
0.7175	Intermediate Similarity	NPD7286	Phase 2
0.7171	Intermediate Similarity	NPD3972	Approved
0.7171	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7117	Intermediate Similarity	NPD2654	Approved
0.7115	Intermediate Similarity	NPD4908	Phase 1
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7097	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7229	Phase 3
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7078	Intermediate Similarity	NPD1876	Approved
0.7075	Intermediate Similarity	NPD5283	Phase 1
0.7073	Intermediate Similarity	NPD8166	Discontinued
0.7068	Intermediate Similarity	NPD7680	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7067	Intermediate Similarity	NPD9545	Approved
0.7066	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7051	Intermediate Similarity	NPD3018	Phase 2
0.7041	Intermediate Similarity	NPD3455	Phase 2
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7035	Intermediate Similarity	NPD5978	Approved
0.7035	Intermediate Similarity	NPD5977	Approved
0.7025	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2163	Approved
0.7021	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6832	Phase 2
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.7	Intermediate Similarity	NPD1933	Approved
0.6994	Remote Similarity	NPD2346	Discontinued
0.6994	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1610	Phase 2
0.6993	Remote Similarity	NPD3705	Approved
0.6987	Remote Similarity	NPD5647	Approved
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	Phase 3
0.6979	Remote Similarity	NPD7698	Approved
0.6974	Remote Similarity	NPD17	Approved
0.6968	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4361	Phase 2
0.6961	Remote Similarity	NPD7038	Approved
0.6961	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7039	Approved
0.6951	Remote Similarity	NPD2424	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