NPASS Compound

Structure

NPC38964 OpenBabel07101718242D 45 51 0 0 1 0 0 0 0 0999 V2000 -0.8660 7.5000 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 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 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 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 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 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 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 6.0622 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 2.5981 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 38 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 7 2 0 0 0 0 5 21 1 0 0 0 0 6 8 2 0 0 0 0 6 20 1 0 0 0 0 7 28 1 0 0 0 0 8 29 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 37 1 0 0 0 0 12 38 1 0 0 0 0 13 20 2 0 0 0 0 13 26 1 0 0 0 0 14 21 2 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 16 30 1 0 0 0 0 17 23 2 0 0 0 0 17 32 1 0 0 0 0 18 24 2 0 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 39 2 0 0 0 0 22 24 1 0 0 0 0 23 33 1 0 0 0 0 24 36 1 0 0 0 0 25 26 1 0 0 0 0 25 28 2 0 0 0 0 26 29 2 0 0 0 0 27 15 1 1 0 0 0 27 33 1 0 0 0 0 27 37 1 0 0 0 0 28 40 1 0 0 0 0 29 42 1 0 0 0 0 30 31 2 0 0 0 0 30 44 1 0 0 0 0 31 45 1 0 0 0 0 32 34 2 0 0 0 0 32 43 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 34 44 1 0 0 0 0 35 45 1 0 0 0 0 36 38 1 0 0 0 0 36 41 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.24
Volume:	617.931
LogP:	6.115
LogD:	3.499
LogS:	-7.976
# Rotatable Bonds:	6
TPSA:	97.77
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	3.794
Fsp3:	0.278
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.267
MDCK Permeability:	2.8441987524274737e-05
Pgp-inhibitor:	0.782
Pgp-substrate:	0.792
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.709

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.207
Plasma Protein Binding (PPB):	85.69398498535156%
Volume Distribution (VD):	1.161
Pgp-substrate:	5.782697677612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.24
CYP2C19-substrate:	0.714
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.695
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.285
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	4.937
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.748
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.458
AMES Toxicity:	0.457
Rat Oral Acute Toxicity:	0.664
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.224
Carcinogencity:	0.306
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC38964

Natural Product ID:	NPC38964
*Common Name:**	Secolucidine
IUPAC Name:	n.a.
Synonyms:	Secolucidine
Standard InCHIKey:	IPZZJEUUDCPILE-MHZLTWQESA-N
Standard InCHI:	InChI=1S/C36H34N2O7/c1-37-11-10-23-17-32(43-4)34-35(45-31-18-24-22(16-30(31)44-34)9-12-38(2)36(24)41)33(23)27(37)15-20-6-8-29(42-3)26(13-20)25-14-21(19-39)5-7-28(25)40/h5-8,13-14,16-19,27,40H,9-12,15H2,1-4H3/t27-/m0/s1
SMILES:	O=Cc1ccc(c(c1)c1cc(ccc1OC)C[C@@H]1N(C)CCc2c1c1Oc3cc4c(cc3Oc1c(c2)OC)CCN(C4=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450834
PubChem CID:	44559884
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO33281	pseuhxandra sclerocarpa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8676127]

☑ 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	1
Others	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	>	100000.0	nM	PMID[570246]
NPT2	Others	Unspecified		Ratio IC50	<	0.8	n.a.	PMID[570246]

☑ 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 NPC38964 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	349
0.1-0.2	1630
0.2-0.3	5816
0.3-0.4	11776
0.4-0.5	4617
0.5-0.6	7344
0.6-0.7	9102
0.7-0.8	1962
0.8-0.85	92
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC82056
0.8743	High Similarity	NPC65312
0.8743	High Similarity	NPC139783
0.8691	High Similarity	NPC95426
0.8691	High Similarity	NPC302245
0.8691	High Similarity	NPC16357
0.8601	High Similarity	NPC275680
0.8601	High Similarity	NPC22115
0.852	High Similarity	NPC256124
0.8462	Intermediate Similarity	NPC206900
0.8446	Intermediate Similarity	NPC274716
0.8446	Intermediate Similarity	NPC167116
0.8446	Intermediate Similarity	NPC254441
0.841	Intermediate Similarity	NPC208890
0.84	Intermediate Similarity	NPC475654
0.8394	Intermediate Similarity	NPC223690
0.8394	Intermediate Similarity	NPC185639
0.8394	Intermediate Similarity	NPC54654
0.8394	Intermediate Similarity	NPC181796
0.8394	Intermediate Similarity	NPC239824
0.8394	Intermediate Similarity	NPC8836
0.8394	Intermediate Similarity	NPC271013
0.8394	Intermediate Similarity	NPC15414
0.8394	Intermediate Similarity	NPC42663
0.8394	Intermediate Similarity	NPC279228
0.8394	Intermediate Similarity	NPC222661
0.8394	Intermediate Similarity	NPC49075
0.8394	Intermediate Similarity	NPC90998
0.8394	Intermediate Similarity	NPC311973
0.8394	Intermediate Similarity	NPC229373
0.8394	Intermediate Similarity	NPC104196
0.8394	Intermediate Similarity	NPC290005
0.8394	Intermediate Similarity	NPC285931
0.8394	Intermediate Similarity	NPC328155
0.8394	Intermediate Similarity	NPC182052
0.8394	Intermediate Similarity	NPC258657
0.8394	Intermediate Similarity	NPC290582
0.8394	Intermediate Similarity	NPC7715
0.8394	Intermediate Similarity	NPC217748
0.8394	Intermediate Similarity	NPC251735
0.8359	Intermediate Similarity	NPC212237
0.8359	Intermediate Similarity	NPC116465
0.8342	Intermediate Similarity	NPC286119
0.8299	Intermediate Similarity	NPC30779
0.8283	Intermediate Similarity	NPC478093
0.8272	Intermediate Similarity	NPC12424
0.8272	Intermediate Similarity	NPC251580
0.8272	Intermediate Similarity	NPC129518
0.8272	Intermediate Similarity	NPC41376
0.8241	Intermediate Similarity	NPC30182
0.8241	Intermediate Similarity	NPC473589
0.8241	Intermediate Similarity	NPC478091
0.8241	Intermediate Similarity	NPC478092
0.8232	Intermediate Similarity	NPC191132
0.8232	Intermediate Similarity	NPC473716
0.8232	Intermediate Similarity	NPC60295
0.8232	Intermediate Similarity	NPC475597
0.822	Intermediate Similarity	NPC227060
0.822	Intermediate Similarity	NPC10908
0.822	Intermediate Similarity	NPC317145
0.822	Intermediate Similarity	NPC198498
0.822	Intermediate Similarity	NPC76682
0.822	Intermediate Similarity	NPC317439
0.822	Intermediate Similarity	NPC63646
0.822	Intermediate Similarity	NPC276890
0.822	Intermediate Similarity	NPC115284
0.8187	Intermediate Similarity	NPC293093
0.8186	Intermediate Similarity	NPC254581
0.8182	Intermediate Similarity	NPC274661
0.8182	Intermediate Similarity	NPC82457
0.8182	Intermediate Similarity	NPC175890
0.8182	Intermediate Similarity	NPC11296
0.8182	Intermediate Similarity	NPC48490
0.8111	Intermediate Similarity	NPC315914
0.81	Intermediate Similarity	NPC24260
0.8071	Intermediate Similarity	NPC302275
0.8061	Intermediate Similarity	NPC239584
0.801	Intermediate Similarity	NPC243454
0.801	Intermediate Similarity	NPC475479
0.8	Intermediate Similarity	NPC241704
0.8	Intermediate Similarity	NPC222524
0.799	Intermediate Similarity	NPC14507
0.799	Intermediate Similarity	NPC47077
0.7929	Intermediate Similarity	NPC73492
0.7929	Intermediate Similarity	NPC299990
0.7919	Intermediate Similarity	NPC32154
0.7919	Intermediate Similarity	NPC99723
0.7902	Intermediate Similarity	NPC267414
0.7892	Intermediate Similarity	NPC24228
0.7892	Intermediate Similarity	NPC234318
0.7882	Intermediate Similarity	NPC85381
0.7871	Intermediate Similarity	NPC41122
0.7871	Intermediate Similarity	NPC318805
0.7868	Intermediate Similarity	NPC327005
0.7854	Intermediate Similarity	NPC83019
0.7846	Intermediate Similarity	NPC227683
0.7824	Intermediate Similarity	NPC268503
0.7824	Intermediate Similarity	NPC42549
0.7824	Intermediate Similarity	NPC264850
0.7824	Intermediate Similarity	NPC317272
0.7824	Intermediate Similarity	NPC13916
0.7824	Intermediate Similarity	NPC250846
0.7824	Intermediate Similarity	NPC240841
0.7824	Intermediate Similarity	NPC256012
0.7805	Intermediate Similarity	NPC204580
0.7778	Intermediate Similarity	NPC471031
0.7778	Intermediate Similarity	NPC469689
0.7772	Intermediate Similarity	NPC24465
0.7761	Intermediate Similarity	NPC249996
0.7756	Intermediate Similarity	NPC477258
0.7744	Intermediate Similarity	NPC83198
0.7744	Intermediate Similarity	NPC204908
0.774	Intermediate Similarity	NPC316164
0.7736	Intermediate Similarity	NPC46990
0.7734	Intermediate Similarity	NPC281581
0.7723	Intermediate Similarity	NPC316292
0.7723	Intermediate Similarity	NPC169387
0.7723	Intermediate Similarity	NPC185031
0.7723	Intermediate Similarity	NPC477259
0.7716	Intermediate Similarity	NPC152680
0.7716	Intermediate Similarity	NPC190783
0.7716	Intermediate Similarity	NPC232386
0.7703	Intermediate Similarity	NPC244191
0.77	Intermediate Similarity	NPC195538
0.77	Intermediate Similarity	NPC257269
0.77	Intermediate Similarity	NPC230276
0.7668	Intermediate Similarity	NPC80759
0.7668	Intermediate Similarity	NPC79402
0.7665	Intermediate Similarity	NPC239775
0.7662	Intermediate Similarity	NPC476202
0.765	Intermediate Similarity	NPC119068
0.765	Intermediate Similarity	NPC40496
0.7644	Intermediate Similarity	NPC247639
0.7644	Intermediate Similarity	NPC25084
0.7633	Intermediate Similarity	NPC281629
0.7621	Intermediate Similarity	NPC471563
0.7619	Intermediate Similarity	NPC473660
0.7619	Intermediate Similarity	NPC119818
0.7619	Intermediate Similarity	NPC328700
0.7619	Intermediate Similarity	NPC202771
0.7619	Intermediate Similarity	NPC2173
0.7617	Intermediate Similarity	NPC205255
0.7617	Intermediate Similarity	NPC271388
0.7617	Intermediate Similarity	NPC135006
0.7617	Intermediate Similarity	NPC235143
0.7617	Intermediate Similarity	NPC230956
0.7617	Intermediate Similarity	NPC119649
0.7614	Intermediate Similarity	NPC168753
0.7614	Intermediate Similarity	NPC118274
0.7594	Intermediate Similarity	NPC314946
0.7576	Intermediate Similarity	NPC475215
0.7576	Intermediate Similarity	NPC108434
0.7565	Intermediate Similarity	NPC221864
0.7561	Intermediate Similarity	NPC82763
0.7559	Intermediate Similarity	NPC314596
0.7556	Intermediate Similarity	NPC211215
0.7549	Intermediate Similarity	NPC162694
0.7548	Intermediate Similarity	NPC279665
0.7537	Intermediate Similarity	NPC185275
0.7524	Intermediate Similarity	NPC226708
0.7513	Intermediate Similarity	NPC158376
0.7513	Intermediate Similarity	NPC145832
0.7513	Intermediate Similarity	NPC306555
0.7513	Intermediate Similarity	NPC117188
0.7513	Intermediate Similarity	NPC205421
0.7513	Intermediate Similarity	NPC12053
0.7513	Intermediate Similarity	NPC81218
0.7513	Intermediate Similarity	NPC474931
0.7512	Intermediate Similarity	NPC98583
0.7512	Intermediate Similarity	NPC315253
0.7512	Intermediate Similarity	NPC80472
0.7512	Intermediate Similarity	NPC469437
0.75	Intermediate Similarity	NPC470646
0.75	Intermediate Similarity	NPC125352
0.7488	Intermediate Similarity	NPC201055
0.7488	Intermediate Similarity	NPC64576
0.7488	Intermediate Similarity	NPC254045
0.7488	Intermediate Similarity	NPC151470
0.7488	Intermediate Similarity	NPC265380
0.7487	Intermediate Similarity	NPC60186
0.7487	Intermediate Similarity	NPC153631
0.7487	Intermediate Similarity	NPC10871
0.7475	Intermediate Similarity	NPC27887
0.7475	Intermediate Similarity	NPC474507
0.7464	Intermediate Similarity	NPC66909
0.7463	Intermediate Similarity	NPC129533
0.7463	Intermediate Similarity	NPC4200
0.7463	Intermediate Similarity	NPC150977
0.7463	Intermediate Similarity	NPC123259
0.7463	Intermediate Similarity	NPC100251
0.7453	Intermediate Similarity	NPC67346
0.7453	Intermediate Similarity	NPC97086
0.7453	Intermediate Similarity	NPC286135
0.7451	Intermediate Similarity	NPC324742
0.7449	Intermediate Similarity	NPC299436
0.7449	Intermediate Similarity	NPC475393
0.7437	Intermediate Similarity	NPC43065
0.7435	Intermediate Similarity	NPC119669
0.7432	Intermediate Similarity	NPC44040
0.7429	Intermediate Similarity	NPC14622

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 NPC38964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	712
0.2-0.3	1222
0.3-0.4	2097
0.4-0.5	2444
0.5-0.6	1672
0.6-0.7	631
0.7-0.8	140
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8394	Intermediate Similarity	NPD8054	Approved
0.8394	Intermediate Similarity	NPD8053	Approved
0.8308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD8156	Discontinued
0.822	Intermediate Similarity	NPD8251	Approved
0.822	Intermediate Similarity	NPD8252	Approved
0.822	Intermediate Similarity	NPD8099	Discontinued
0.788	Intermediate Similarity	NPD6997	Phase 2
0.7778	Intermediate Similarity	NPD7048	Phase 3
0.7767	Intermediate Similarity	NPD7047	Phase 3
0.7755	Intermediate Similarity	NPD7177	Discontinued
0.7671	Intermediate Similarity	NPD7907	Approved
0.765	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5006	Approved
0.7619	Intermediate Similarity	NPD5005	Approved
0.7598	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD7291	Discontinued
0.75	Intermediate Similarity	NPD5676	Approved
0.7488	Intermediate Similarity	NPD2494	Approved
0.7488	Intermediate Similarity	NPD3452	Approved
0.7488	Intermediate Similarity	NPD3450	Approved
0.7488	Intermediate Similarity	NPD2493	Approved
0.7487	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD8095	Phase 1
0.7476	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2974	Approved
0.7464	Intermediate Similarity	NPD2973	Approved
0.7464	Intermediate Similarity	NPD2975	Approved
0.7453	Intermediate Similarity	NPD3057	Approved
0.7429	Intermediate Similarity	NPD4420	Approved
0.7424	Intermediate Similarity	NPD5242	Approved
0.7421	Intermediate Similarity	NPD4665	Approved
0.7421	Intermediate Similarity	NPD4111	Phase 1
0.7402	Intermediate Similarity	NPD6618	Phase 2
0.74	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD7584	Approved
0.7391	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4582	Approved
0.7383	Intermediate Similarity	NPD4583	Approved
0.7373	Intermediate Similarity	NPD8152	Approved
0.7373	Intermediate Similarity	NPD8153	Approved
0.7371	Intermediate Similarity	NPD3448	Approved
0.7371	Intermediate Similarity	NPD2491	Approved
0.7371	Intermediate Similarity	NPD3533	Approved
0.7371	Intermediate Similarity	NPD2972	Approved
0.7363	Intermediate Similarity	NPD5312	Approved
0.7363	Intermediate Similarity	NPD5313	Approved
0.7363	Intermediate Similarity	NPD5844	Phase 1
0.7361	Intermediate Similarity	NPD7701	Phase 2
0.7358	Intermediate Similarity	NPD4580	Approved
0.7347	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD4004	Approved
0.7336	Intermediate Similarity	NPD4002	Approved
0.7315	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7811	Phase 3
0.7311	Intermediate Similarity	NPD7810	Phase 3
0.7308	Intermediate Similarity	NPD2490	Approved
0.7308	Intermediate Similarity	NPD2488	Approved
0.7304	Intermediate Similarity	NPD7549	Discontinued
0.7289	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD8149	Discontinued
0.7281	Intermediate Similarity	NPD7585	Approved
0.7277	Intermediate Similarity	NPD4107	Approved
0.7277	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6020	Phase 2
0.7268	Intermediate Similarity	NPD6385	Approved
0.7268	Intermediate Similarity	NPD6386	Approved
0.7261	Intermediate Similarity	NPD7942	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7783	Phase 2
0.7254	Intermediate Similarity	NPD824	Approved
0.725	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6181	Discontinued
0.7236	Intermediate Similarity	NPD6959	Discontinued
0.7235	Intermediate Similarity	NPD7583	Approved
0.7233	Intermediate Similarity	NPD6853	Approved
0.7233	Intermediate Similarity	NPD6851	Approved
0.7225	Intermediate Similarity	NPD4584	Approved
0.722	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5564	Approved
0.7212	Intermediate Similarity	NPD7906	Approved
0.7208	Intermediate Similarity	NPD6788	Approved
0.7193	Intermediate Similarity	NPD8059	Phase 3
0.7193	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2968	Approved
0.7184	Intermediate Similarity	NPD2971	Approved
0.7169	Intermediate Similarity	NPD8151	Discontinued
0.7163	Intermediate Similarity	NPD4482	Phase 3
0.7162	Intermediate Similarity	NPD7654	Discontinued
0.7157	Intermediate Similarity	NPD5978	Approved
0.7157	Intermediate Similarity	NPD5977	Approved
0.7157	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7693	Approved
0.7129	Intermediate Similarity	NPD6166	Phase 2
0.7129	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4363	Phase 3
0.7123	Intermediate Similarity	NPD4360	Phase 2
0.7122	Intermediate Similarity	NPD6297	Approved
0.7122	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6232	Discontinued
0.7112	Intermediate Similarity	NPD6625	Approved
0.7107	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7497	Discontinued
0.7094	Intermediate Similarity	NPD3446	Phase 1
0.7094	Intermediate Similarity	NPD7473	Discontinued
0.7092	Intermediate Similarity	NPD4773	Phase 2
0.7092	Intermediate Similarity	NPD7110	Phase 1
0.7092	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4772	Phase 2
0.7085	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7833	Phase 2
0.7085	Intermediate Similarity	NPD7831	Phase 2
0.7067	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD8320	Phase 1
0.7064	Intermediate Similarity	NPD8319	Approved
0.7062	Intermediate Similarity	NPD3641	Approved
0.7062	Intermediate Similarity	NPD3640	Phase 3
0.7062	Intermediate Similarity	NPD3639	Approved
0.7053	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6894	Phase 1
0.7044	Intermediate Similarity	NPD2898	Approved
0.7035	Intermediate Similarity	NPD2899	Discontinued
0.703	Intermediate Similarity	NPD6071	Discontinued
0.7024	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1465	Phase 2
0.7019	Intermediate Similarity	NPD7312	Approved
0.7019	Intermediate Similarity	NPD7313	Approved
0.7019	Intermediate Similarity	NPD7311	Approved
0.7019	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7310	Approved
0.7018	Intermediate Similarity	NPD7696	Phase 3
0.7018	Intermediate Similarity	NPD7697	Approved
0.7018	Intermediate Similarity	NPD7698	Approved
0.7015	Intermediate Similarity	NPD5494	Approved
0.7009	Intermediate Similarity	NPD4361	Phase 2
0.7009	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7039	Approved
0.7005	Intermediate Similarity	NPD7038	Approved
0.6991	Remote Similarity	NPD8285	Discontinued
0.6991	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7074	Phase 3
0.6986	Remote Similarity	NPD7309	Approved
0.6986	Remote Similarity	NPD4040	Phase 1
0.6986	Remote Similarity	NPD7870	Phase 2
0.6986	Remote Similarity	NPD7871	Phase 2
0.6985	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5353	Approved
0.6974	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1934	Approved
0.697	Remote Similarity	NPD7577	Discontinued
0.697	Remote Similarity	NPD7298	Approved
0.6967	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7922	Phase 1
0.6965	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8161	Suspended
0.695	Remote Similarity	NPD7768	Phase 2
0.6946	Remote Similarity	NPD3051	Approved
0.6944	Remote Similarity	NPD5071	Phase 2
0.6942	Remote Similarity	NPD42	Phase 2
0.6942	Remote Similarity	NPD6042	Phase 2
0.6938	Remote Similarity	NPD4577	Approved
0.6938	Remote Similarity	NPD4578	Approved
0.6935	Remote Similarity	NPD7819	Suspended
0.6931	Remote Similarity	NPD2904	Discontinued
0.6926	Remote Similarity	NPD7223	Discontinued
0.6926	Remote Similarity	NPD7224	Discontinued
0.6923	Remote Similarity	NPD7708	Approved
0.692	Remote Similarity	NPD7827	Phase 1
0.6919	Remote Similarity	NPD4663	Approved
0.6916	Remote Similarity	NPD4466	Phase 1
0.6912	Remote Similarity	NPD2969	Approved
0.6912	Remote Similarity	NPD2970	Approved
0.6911	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6107	Approved
0.6891	Remote Similarity	NPD7886	Phase 2
0.6891	Remote Similarity	NPD7885	Phase 2
0.6884	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6776	Approved
0.6881	Remote Similarity	NPD6777	Approved
0.6881	Remote Similarity	NPD5457	Discontinued
0.6881	Remote Similarity	NPD6781	Approved
0.6881	Remote Similarity	NPD6778	Approved
0.6881	Remote Similarity	NPD6779	Approved
0.6881	Remote Similarity	NPD6780	Approved
0.6881	Remote Similarity	NPD6782	Approved
0.688	Remote Similarity	NPD7803	Approved
0.6878	Remote Similarity	NPD2489	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