NPASS Compound

Structure

CID40070 OpenBabel06191715372D 23 27 0 0 1 0 0 0 0 0999 V2000 0.9567 -1.1052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3538 0.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5655 1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5653 0.4931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7107 1.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7103 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5644 -1.8232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7105 1.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2102 -2.4369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5655 1.4820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7110 -0.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1471 -1.8234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 -0.7087 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2100 -1.2095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8552 1.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8551 1.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5013 -1.2097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8550 0.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7108 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8553 0.4938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5016 -2.4371 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5657 0.4942 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 18 2 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 21 2 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 19 2 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 1 1 6 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.16
Volume:	323.592
LogP:	4.411
LogD:	3.585
LogS:	-3.972
# Rotatable Bonds:	0
TPSA:	21.06
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	3.472
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.99
MDCK Permeability:	3.0005672670085914e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.362
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.793

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	94.9865493774414%
Volume Distribution (VD):	2.078
Pgp-substrate:	4.064437389373779%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.948
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.884
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	8.082
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.781
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.727
AMES Toxicity:	0.941
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.526
Carcinogencity:	0.458
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC40070

Natural Product ID:	NPC40070
*Common Name:**	Decussine
IUPAC Name:	n.a.
Synonyms:	Decussine
Standard InCHIKey:	CSRPMFCRBOSISJ-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C20H19N3/c1-13-17-12-21-9-7-14(17)11-19-20-16(8-10-22(19)2)15-5-3-4-6-18(15)23(13)20/h3-7,9,11-13H,8,10H2,1-2H3/t13-/m1/s1
SMILES:	CN1CCc2c3C1=Cc1ccncc1[C@H](n3c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454319
PubChem CID:	156336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[22784551]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[25068578]
NPO4719	Strychnos dale	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288442]
NPO40938	Strychnos elaecocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288442]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288442]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7400820]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28058	Seseli grandivittatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28058	Seseli grandivittatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4719	Strychnos dale	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28058	Seseli grandivittatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5656	Hymenoxys turneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4719	Strychnos dale	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26991	Hypericum choisyanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15394	Angelica decursiva	Species	Apiaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	50.0	%	PMID[548510]

☑ 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 NPC40070 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	1056
0.1-0.2	11901
0.2-0.3	19057
0.3-0.4	5008
0.4-0.5	2141
0.5-0.6	1962
0.6-0.7	1048
0.7-0.8	399
0.8-0.85	96
0.85-0.9	23
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8897	High Similarity	NPC20144
0.8811	High Similarity	NPC251722
0.8811	High Similarity	NPC314102
0.8681	High Similarity	NPC150259
0.8658	High Similarity	NPC470111
0.8609	High Similarity	NPC470233
0.8533	High Similarity	NPC179787
0.8533	High Similarity	NPC201380
0.8526	High Similarity	NPC478182
0.8497	Intermediate Similarity	NPC476219
0.8477	Intermediate Similarity	NPC321911
0.8467	Intermediate Similarity	NPC63545
0.8435	Intermediate Similarity	NPC88097
0.8431	Intermediate Similarity	NPC325903
0.8411	Intermediate Similarity	NPC469811
0.8333	Intermediate Similarity	NPC477591
0.8333	Intermediate Similarity	NPC293487
0.8333	Intermediate Similarity	NPC280852
0.8311	Intermediate Similarity	NPC110126
0.8311	Intermediate Similarity	NPC73767
0.8302	Intermediate Similarity	NPC56233
0.8291	Intermediate Similarity	NPC478184
0.8289	Intermediate Similarity	NPC21605
0.8286	Intermediate Similarity	NPC46358
0.8278	Intermediate Similarity	NPC86288
0.8258	Intermediate Similarity	NPC476297
0.8255	Intermediate Similarity	NPC469779
0.8255	Intermediate Similarity	NPC469784
0.8255	Intermediate Similarity	NPC469768
0.8255	Intermediate Similarity	NPC469783
0.8255	Intermediate Similarity	NPC469780
0.8255	Intermediate Similarity	NPC469767
0.8255	Intermediate Similarity	NPC469761
0.8217	Intermediate Similarity	NPC56765
0.82	Intermediate Similarity	NPC473868
0.82	Intermediate Similarity	NPC63157
0.82	Intermediate Similarity	NPC469766
0.8188	Intermediate Similarity	NPC104483
0.8187	Intermediate Similarity	NPC478183
0.8182	Intermediate Similarity	NPC53947
0.8176	Intermediate Similarity	NPC84911
0.8176	Intermediate Similarity	NPC105127
0.8176	Intermediate Similarity	NPC317105
0.8163	Intermediate Similarity	NPC198988
0.8153	Intermediate Similarity	NPC236711
0.8143	Intermediate Similarity	NPC265605
0.8143	Intermediate Similarity	NPC48564
0.8143	Intermediate Similarity	NPC182570
0.8138	Intermediate Similarity	NPC69914
0.8125	Intermediate Similarity	NPC2165
0.8125	Intermediate Similarity	NPC195507
0.8121	Intermediate Similarity	NPC169433
0.8113	Intermediate Similarity	NPC470203
0.8113	Intermediate Similarity	NPC478185
0.8108	Intermediate Similarity	NPC325252
0.8108	Intermediate Similarity	NPC96102
0.8108	Intermediate Similarity	NPC29886
0.8108	Intermediate Similarity	NPC261195
0.8105	Intermediate Similarity	NPC288838
0.8099	Intermediate Similarity	NPC476322
0.8089	Intermediate Similarity	NPC51054
0.8086	Intermediate Similarity	NPC91895
0.8069	Intermediate Similarity	NPC476131
0.805	Intermediate Similarity	NPC255229
0.805	Intermediate Similarity	NPC44773
0.805	Intermediate Similarity	NPC229173
0.805	Intermediate Similarity	NPC470204
0.805	Intermediate Similarity	NPC81229
0.805	Intermediate Similarity	NPC122141
0.805	Intermediate Similarity	NPC215584
0.8049	Intermediate Similarity	NPC471579
0.8038	Intermediate Similarity	NPC129721
0.8037	Intermediate Similarity	NPC82331
0.8013	Intermediate Similarity	NPC59084
0.8013	Intermediate Similarity	NPC115611
0.8	Intermediate Similarity	NPC225018
0.8	Intermediate Similarity	NPC474958
0.7987	Intermediate Similarity	NPC221786
0.7987	Intermediate Similarity	NPC475990
0.7987	Intermediate Similarity	NPC206819
0.7987	Intermediate Similarity	NPC474880
0.7987	Intermediate Similarity	NPC318065
0.7975	Intermediate Similarity	NPC32534
0.7962	Intermediate Similarity	NPC138842
0.7929	Intermediate Similarity	NPC91958
0.7925	Intermediate Similarity	NPC216643
0.7922	Intermediate Similarity	NPC285731
0.7922	Intermediate Similarity	NPC314372
0.7908	Intermediate Similarity	NPC190296
0.7895	Intermediate Similarity	NPC2949
0.7895	Intermediate Similarity	NPC279081
0.7888	Intermediate Similarity	NPC194881
0.7875	Intermediate Similarity	NPC41257
0.7857	Intermediate Similarity	NPC81561
0.7857	Intermediate Similarity	NPC297486
0.7857	Intermediate Similarity	NPC240136
0.7857	Intermediate Similarity	NPC471402
0.784	Intermediate Similarity	NPC90723
0.7838	Intermediate Similarity	NPC82295
0.7834	Intermediate Similarity	NPC105818
0.7834	Intermediate Similarity	NPC24678
0.7832	Intermediate Similarity	NPC329825
0.7829	Intermediate Similarity	NPC32002
0.7829	Intermediate Similarity	NPC316811
0.7829	Intermediate Similarity	NPC315348
0.7812	Intermediate Similarity	NPC286427
0.7806	Intermediate Similarity	NPC469525
0.7803	Intermediate Similarity	NPC231536
0.7801	Intermediate Similarity	NPC162689
0.7801	Intermediate Similarity	NPC54102
0.7798	Intermediate Similarity	NPC12649
0.7793	Intermediate Similarity	NPC146373
0.7793	Intermediate Similarity	NPC166424
0.7793	Intermediate Similarity	NPC245244
0.7791	Intermediate Similarity	NPC274229
0.7786	Intermediate Similarity	NPC148140
0.7778	Intermediate Similarity	NPC230002
0.7764	Intermediate Similarity	NPC135141
0.7764	Intermediate Similarity	NPC92796
0.7758	Intermediate Similarity	NPC474897
0.7756	Intermediate Similarity	NPC478186
0.7756	Intermediate Similarity	NPC143872
0.775	Intermediate Similarity	NPC476464
0.7748	Intermediate Similarity	NPC218268
0.7736	Intermediate Similarity	NPC259644
0.7736	Intermediate Similarity	NPC469760
0.7736	Intermediate Similarity	NPC200214
0.7736	Intermediate Similarity	NPC469765
0.7736	Intermediate Similarity	NPC469763
0.7736	Intermediate Similarity	NPC469786
0.7736	Intermediate Similarity	NPC25008
0.7736	Intermediate Similarity	NPC73952
0.773	Intermediate Similarity	NPC271797
0.773	Intermediate Similarity	NPC21174
0.7725	Intermediate Similarity	NPC297034
0.7724	Intermediate Similarity	NPC122718
0.7724	Intermediate Similarity	NPC27740
0.7722	Intermediate Similarity	NPC33421
0.7707	Intermediate Similarity	NPC471957
0.7692	Intermediate Similarity	NPC470440
0.7692	Intermediate Similarity	NPC204141
0.7692	Intermediate Similarity	NPC159856
0.7688	Intermediate Similarity	NPC211572
0.7688	Intermediate Similarity	NPC80597
0.7688	Intermediate Similarity	NPC75540
0.7688	Intermediate Similarity	NPC212376
0.7688	Intermediate Similarity	NPC70922
0.7676	Intermediate Similarity	NPC143603
0.7662	Intermediate Similarity	NPC284635
0.766	Intermediate Similarity	NPC476566
0.7651	Intermediate Similarity	NPC194411
0.7651	Intermediate Similarity	NPC97343
0.7651	Intermediate Similarity	NPC282398
0.7651	Intermediate Similarity	NPC22079
0.7647	Intermediate Similarity	NPC24864
0.7633	Intermediate Similarity	NPC326575
0.7619	Intermediate Similarity	NPC317054
0.7619	Intermediate Similarity	NPC469938
0.7605	Intermediate Similarity	NPC201634
0.76	Intermediate Similarity	NPC475450
0.759	Intermediate Similarity	NPC63751
0.7578	Intermediate Similarity	NPC34844
0.7574	Intermediate Similarity	NPC472122
0.7574	Intermediate Similarity	NPC24594
0.7569	Intermediate Similarity	NPC215519
0.7562	Intermediate Similarity	NPC470823
0.7534	Intermediate Similarity	NPC290094
0.7531	Intermediate Similarity	NPC469785
0.753	Intermediate Similarity	NPC474561
0.753	Intermediate Similarity	NPC49954
0.7529	Intermediate Similarity	NPC157583
0.7516	Intermediate Similarity	NPC141926
0.7516	Intermediate Similarity	NPC281094
0.7515	Intermediate Similarity	NPC37423
0.7515	Intermediate Similarity	NPC275305
0.75	Intermediate Similarity	NPC265576
0.75	Intermediate Similarity	NPC250361
0.75	Intermediate Similarity	NPC307191
0.7485	Intermediate Similarity	NPC317430
0.7485	Intermediate Similarity	NPC133261
0.7485	Intermediate Similarity	NPC469762
0.7483	Intermediate Similarity	NPC101165
0.7483	Intermediate Similarity	NPC256893
0.7471	Intermediate Similarity	NPC99939
0.7471	Intermediate Similarity	NPC203754
0.7471	Intermediate Similarity	NPC150048
0.7471	Intermediate Similarity	NPC15102
0.7471	Intermediate Similarity	NPC308931
0.7467	Intermediate Similarity	NPC473587
0.7456	Intermediate Similarity	NPC472123
0.7456	Intermediate Similarity	NPC477611
0.7456	Intermediate Similarity	NPC161861
0.7455	Intermediate Similarity	NPC282231
0.7453	Intermediate Similarity	NPC216713
0.7442	Intermediate Similarity	NPC15840
0.7442	Intermediate Similarity	NPC472105
0.7442	Intermediate Similarity	NPC314919
0.7442	Intermediate Similarity	NPC187827
0.7439	Intermediate Similarity	NPC6436
0.7434	Intermediate Similarity	NPC473930

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 NPC40070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	762
0.2-0.3	1039
0.3-0.4	1930
0.4-0.5	2084
0.5-0.6	1745
0.6-0.7	903
0.7-0.8	217
0.8-0.85	31
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9306	High Similarity	NPD4547	Phase 3
0.8865	High Similarity	NPD3385	Approved
0.88	High Similarity	NPD2837	Discontinued
0.8767	High Similarity	NPD4637	Clinical (unspecified phase)
0.8639	High Similarity	NPD2006	Phase 2
0.8601	High Similarity	NPD3942	Approved
0.8601	High Similarity	NPD3944	Approved
0.86	High Similarity	NPD2430	Phase 2
0.8521	High Similarity	NPD3475	Approved
0.8521	High Similarity	NPD3476	Approved
0.8451	Intermediate Similarity	NPD3654	Approved
0.844	Intermediate Similarity	NPD2119	Approved
0.844	Intermediate Similarity	NPD2118	Approved
0.8392	Intermediate Similarity	NPD715	Phase 3
0.8322	Intermediate Similarity	NPD1722	Approved
0.8311	Intermediate Similarity	NPD786	Approved
0.8299	Intermediate Similarity	NPD6554	Approved
0.8299	Intermediate Similarity	NPD45	Approved
0.8282	Intermediate Similarity	NPD7111	Discontinued
0.825	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD5315	Discontinued
0.8228	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1683	Approved
0.8224	Intermediate Similarity	NPD7469	Discontinued
0.8219	Intermediate Similarity	NPD4028	Approved
0.8219	Intermediate Similarity	NPD4030	Approved
0.8219	Intermediate Similarity	NPD4029	Approved
0.8176	Intermediate Similarity	NPD3323	Discontinued
0.8143	Intermediate Similarity	NPD268	Approved
0.8143	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD271	Approved
0.8137	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD3100	Discontinued
0.8108	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD991	Phase 2
0.8056	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4047	Discontinued
0.8012	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2580	Discontinued
0.7937	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4957	Phase 2
0.7925	Intermediate Similarity	NPD6497	Approved
0.7895	Intermediate Similarity	NPD7394	Phase 2
0.7885	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5418	Discontinued
0.7867	Intermediate Similarity	NPD1256	Approved
0.7867	Intermediate Similarity	NPD1253	Approved
0.7867	Intermediate Similarity	NPD1254	Approved
0.7867	Intermediate Similarity	NPD1255	Approved
0.7857	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD4181	Approved
0.7834	Intermediate Similarity	NPD2172	Phase 1
0.7834	Intermediate Similarity	NPD2466	Phase 3
0.7834	Intermediate Similarity	NPD2462	Phase 3
0.7834	Intermediate Similarity	NPD2465	Approved
0.7831	Intermediate Similarity	NPD5065	Approved
0.7829	Intermediate Similarity	NPD2075	Approved
0.7829	Intermediate Similarity	NPD2068	Approved
0.7829	Intermediate Similarity	NPD2072	Approved
0.7829	Intermediate Similarity	NPD2070	Approved
0.7829	Intermediate Similarity	NPD2074	Approved
0.7829	Intermediate Similarity	NPD2073	Approved
0.7829	Intermediate Similarity	NPD2069	Approved
0.7829	Intermediate Similarity	NPD2071	Approved
0.7818	Intermediate Similarity	NPD3609	Approved
0.7818	Intermediate Similarity	NPD3610	Approved
0.7812	Intermediate Similarity	NPD4326	Phase 2
0.7805	Intermediate Similarity	NPD4639	Approved
0.7805	Intermediate Similarity	NPD4638	Approved
0.7805	Intermediate Similarity	NPD4640	Approved
0.7792	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2720	Phase 1
0.7784	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6771	Discontinued
0.7771	Intermediate Similarity	NPD7217	Approved
0.7771	Intermediate Similarity	NPD7216	Approved
0.775	Intermediate Similarity	NPD3115	Approved
0.775	Intermediate Similarity	NPD3113	Approved
0.775	Intermediate Similarity	NPD3112	Approved
0.775	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3114	Approved
0.7733	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4128	Approved
0.7708	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1661	Suspended
0.7702	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2640	Approved
0.7697	Intermediate Similarity	NPD2641	Approved
0.7697	Intermediate Similarity	NPD2333	Discontinued
0.7688	Intermediate Similarity	NPD6285	Phase 2
0.7688	Intermediate Similarity	NPD975	Approved
0.7688	Intermediate Similarity	NPD976	Approved
0.7688	Intermediate Similarity	NPD2165	Phase 1
0.7688	Intermediate Similarity	NPD977	Approved
0.7679	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5436	Phase 1
0.764	Intermediate Similarity	NPD2150	Discontinued
0.7636	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5254	Discontinued
0.7628	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD9583	Approved
0.7616	Intermediate Similarity	NPD5892	Approved
0.7614	Intermediate Similarity	NPD4615	Phase 2
0.7595	Intermediate Similarity	NPD4702	Approved
0.7595	Intermediate Similarity	NPD4703	Approved
0.7576	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2915	Discontinued
0.7574	Intermediate Similarity	NPD4075	Phase 2
0.755	Intermediate Similarity	NPD1993	Approved
0.755	Intermediate Similarity	NPD1994	Approved
0.755	Intermediate Similarity	NPD1995	Approved
0.7547	Intermediate Similarity	NPD1183	Approved
0.7546	Intermediate Similarity	NPD5255	Approved
0.7529	Intermediate Similarity	NPD4902	Discontinued
0.7529	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3339	Approved
0.7516	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4509	Discontinued
0.7515	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7564	Discontinued
0.75	Intermediate Similarity	NPD1404	Approved
0.75	Intermediate Similarity	NPD1403	Approved
0.75	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6281	Approved
0.7485	Intermediate Similarity	NPD3409	Phase 1
0.7485	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9357	Approved
0.7483	Intermediate Similarity	NPD803	Phase 1
0.7471	Intermediate Similarity	NPD5555	Phase 1
0.7471	Intermediate Similarity	NPD5104	Approved
0.747	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD947	Approved
0.7455	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2882	Phase 1
0.7451	Intermediate Similarity	NPD2142	Approved
0.7451	Intermediate Similarity	NPD2140	Approved
0.7451	Intermediate Similarity	NPD2141	Approved
0.743	Intermediate Similarity	NPD7618	Phase 3
0.743	Intermediate Similarity	NPD7619	Phase 3
0.7429	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3505	Approved
0.7427	Intermediate Similarity	NPD3506	Approved
0.7425	Intermediate Similarity	NPD2639	Approved
0.7425	Intermediate Similarity	NPD2642	Approved
0.7405	Intermediate Similarity	NPD5671	Approved
0.7399	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD9598	Discontinued
0.7389	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3961	Discontinued
0.7384	Intermediate Similarity	NPD4079	Approved
0.7384	Intermediate Similarity	NPD4076	Approved
0.7384	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5862	Discovery
0.7376	Intermediate Similarity	NPD4823	Approved
0.7376	Intermediate Similarity	NPD4824	Approved
0.7371	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6044	Discontinued
0.7368	Intermediate Similarity	NPD2771	Approved
0.7368	Intermediate Similarity	NPD3348	Phase 2
0.7365	Intermediate Similarity	NPD1313	Approved
0.7358	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD200	Phase 2
0.7355	Intermediate Similarity	NPD201	Phase 2
0.7348	Intermediate Similarity	NPD3830	Phase 1
0.7345	Intermediate Similarity	NPD2728	Approved
0.7345	Intermediate Similarity	NPD2730	Approved
0.7345	Intermediate Similarity	NPD2729	Approved
0.7341	Intermediate Similarity	NPD6595	Phase 3
0.7341	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1598	Discontinued
0.733	Intermediate Similarity	NPD6721	Phase 1
0.733	Intermediate Similarity	NPD7026	Phase 2
0.733	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7665	Phase 2
0.7326	Intermediate Similarity	NPD7666	Phase 3
0.7321	Intermediate Similarity	NPD1248	Discontinued
0.7299	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3813	Approved
0.7294	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3116	Approved
0.7294	Intermediate Similarity	NPD6828	Phase 2
0.7294	Intermediate Similarity	NPD3117	Approved
0.7294	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5590	Clinical (unspecified phase)

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