NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	257.14
Volume:	269.098
LogP:	2.343
LogD:	1.962
LogS:	-3.37
# Rotatable Bonds:	0
TPSA:	29.54
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	3.533
Fsp3:	0.562
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:	-4.642
MDCK Permeability:	4.170263127889484e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.158
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.791
Plasma Protein Binding (PPB):	56.570228576660156%
Volume Distribution (VD):	2.589
Pgp-substrate:	45.83580780029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.979
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	10.911
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.596
Human Hepatotoxicity (H-HT):	0.629
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.298
Carcinogencity:	0.606
Eye Corrosion:	0.013
Eye Irritation:	0.115
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC133817

Natural Product ID:	NPC133817
*Common Name:**	Isoelaeocarpine
IUPAC Name:	(6aS,12aR,12bR)-11-methyl-1,2,3,5,6,6a,12a,12b-octahydrochromeno[2,3-g]indolizin-12-one
Synonyms:	Isoelaeocarpine
Standard InCHIKey:	DXTYYNIKCKARPP-OSAQELSMSA-N
Standard InCHI:	InChI=1S/C16H19NO2/c1-10-4-2-6-12-14(10)16(18)15-11-5-3-8-17(11)9-7-13(15)19-12/h2,4,6,11,13,15H,3,5,7-9H2,1H3/t11-,13+,15-/m1/s1
SMILES:	Cc1cccc2c1C(=O)[C@H]1[C@@H](O2)CCN2[C@@H]1CCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL608812
PubChem CID:	44423026
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17451272]
NPO40114	Elaeocarpus angustifolius	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31736307]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	IC50	=	13600.0	nM	PMID[560195]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	50000.0	nM	PMID[560197]

☑ 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 NPC133817 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	259
0.1-0.2	1171
0.2-0.3	3638
0.3-0.4	11476
0.4-0.5	6366
0.5-0.6	10898
0.6-0.7	8664
0.7-0.8	208
0.8-0.85	3
0.85-0.9	1
0.9-0.95	4
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476443
0.8636	High Similarity	NPC68967
0.8065	Intermediate Similarity	NPC297322
0.7908	Intermediate Similarity	NPC281104
0.7907	Intermediate Similarity	NPC27887
0.7895	Intermediate Similarity	NPC222524
0.7821	Intermediate Similarity	NPC477258
0.7799	Intermediate Similarity	NPC476444
0.7791	Intermediate Similarity	NPC35680
0.7784	Intermediate Similarity	NPC477259
0.7784	Intermediate Similarity	NPC169387
0.774	Intermediate Similarity	NPC166979
0.7727	Intermediate Similarity	NPC214629
0.7657	Intermediate Similarity	NPC115906
0.7647	Intermediate Similarity	NPC284842
0.7616	Intermediate Similarity	NPC129578
0.7542	Intermediate Similarity	NPC208890
0.7541	Intermediate Similarity	NPC215098
0.7541	Intermediate Similarity	NPC46744
0.7541	Intermediate Similarity	NPC124302
0.7541	Intermediate Similarity	NPC70290
0.7541	Intermediate Similarity	NPC14622
0.7541	Intermediate Similarity	NPC73020
0.7532	Intermediate Similarity	NPC477412
0.7527	Intermediate Similarity	NPC174783
0.7486	Intermediate Similarity	NPC162694
0.7486	Intermediate Similarity	NPC24228
0.7485	Intermediate Similarity	NPC214239
0.7473	Intermediate Similarity	NPC119818
0.7473	Intermediate Similarity	NPC2173
0.7473	Intermediate Similarity	NPC328700
0.7473	Intermediate Similarity	NPC202771
0.7459	Intermediate Similarity	NPC314100
0.7459	Intermediate Similarity	NPC72788
0.7459	Intermediate Similarity	NPC226708
0.7459	Intermediate Similarity	NPC120671
0.7459	Intermediate Similarity	NPC226652
0.745	Intermediate Similarity	NPC314329
0.7444	Intermediate Similarity	NPC141440
0.7443	Intermediate Similarity	NPC327005
0.7443	Intermediate Similarity	NPC309692
0.7438	Intermediate Similarity	NPC477537
0.7438	Intermediate Similarity	NPC477535
0.7436	Intermediate Similarity	NPC477536
0.7414	Intermediate Similarity	NPC227683
0.7412	Intermediate Similarity	NPC153631
0.7381	Intermediate Similarity	NPC180756
0.7381	Intermediate Similarity	NPC323443
0.738	Intermediate Similarity	NPC67346
0.738	Intermediate Similarity	NPC97086
0.7374	Intermediate Similarity	NPC116007
0.7368	Intermediate Similarity	NPC224657
0.7354	Intermediate Similarity	NPC80472
0.7353	Intermediate Similarity	NPC475780
0.7348	Intermediate Similarity	NPC469437
0.7342	Intermediate Similarity	NPC217914
0.7333	Intermediate Similarity	NPC469540
0.7333	Intermediate Similarity	NPC26285
0.7333	Intermediate Similarity	NPC469539
0.7326	Intermediate Similarity	NPC311781
0.7314	Intermediate Similarity	NPC67978
0.7314	Intermediate Similarity	NPC303581
0.7308	Intermediate Similarity	NPC279596
0.7303	Intermediate Similarity	NPC470162
0.7303	Intermediate Similarity	NPC470163
0.7301	Intermediate Similarity	NPC469978
0.7296	Intermediate Similarity	NPC216149
0.7296	Intermediate Similarity	NPC208170
0.7296	Intermediate Similarity	NPC232996
0.7287	Intermediate Similarity	NPC140577
0.7287	Intermediate Similarity	NPC232533
0.7287	Intermediate Similarity	NPC43069
0.7283	Intermediate Similarity	NPC469816
0.7283	Intermediate Similarity	NPC469815
0.7273	Intermediate Similarity	NPC298884
0.7273	Intermediate Similarity	NPC470841
0.7273	Intermediate Similarity	NPC7467
0.7268	Intermediate Similarity	NPC63152
0.7267	Intermediate Similarity	NPC476569
0.7255	Intermediate Similarity	NPC470858
0.7251	Intermediate Similarity	NPC26353
0.725	Intermediate Similarity	NPC477534
0.7248	Intermediate Similarity	NPC35744
0.7246	Intermediate Similarity	NPC228906
0.7246	Intermediate Similarity	NPC469416
0.7246	Intermediate Similarity	NPC471348
0.7244	Intermediate Similarity	NPC473271
0.7244	Intermediate Similarity	NPC228184
0.7243	Intermediate Similarity	NPC33256
0.7239	Intermediate Similarity	NPC329493
0.7237	Intermediate Similarity	NPC182646
0.7234	Intermediate Similarity	NPC316164
0.7233	Intermediate Similarity	NPC298900
0.7232	Intermediate Similarity	NPC308267
0.7229	Intermediate Similarity	NPC470088
0.7225	Intermediate Similarity	NPC35345
0.7225	Intermediate Similarity	NPC471651
0.7222	Intermediate Similarity	NPC473007
0.7219	Intermediate Similarity	NPC207239
0.7212	Intermediate Similarity	NPC51957
0.7212	Intermediate Similarity	NPC210437
0.7212	Intermediate Similarity	NPC16107
0.7212	Intermediate Similarity	NPC476144
0.7212	Intermediate Similarity	NPC223873
0.7212	Intermediate Similarity	NPC106295
0.7208	Intermediate Similarity	NPC474264
0.7198	Intermediate Similarity	NPC329790
0.7197	Intermediate Similarity	NPC301717
0.7196	Intermediate Similarity	NPC286135
0.7196	Intermediate Similarity	NPC243483
0.7195	Intermediate Similarity	NPC471639
0.7195	Intermediate Similarity	NPC130926
0.7195	Intermediate Similarity	NPC471643
0.7193	Intermediate Similarity	NPC118804
0.719	Intermediate Similarity	NPC56332
0.7186	Intermediate Similarity	NPC219560
0.7184	Intermediate Similarity	NPC474858
0.7182	Intermediate Similarity	NPC83511
0.7181	Intermediate Similarity	NPC171023
0.7179	Intermediate Similarity	NPC57552
0.7176	Intermediate Similarity	NPC146288
0.717	Intermediate Similarity	NPC209858
0.7167	Intermediate Similarity	NPC298339
0.7166	Intermediate Similarity	NPC83019
0.7159	Intermediate Similarity	NPC474708
0.7152	Intermediate Similarity	NPC470160
0.7152	Intermediate Similarity	NPC290404
0.7151	Intermediate Similarity	NPC125924
0.7143	Intermediate Similarity	NPC301341
0.7143	Intermediate Similarity	NPC476579
0.7143	Intermediate Similarity	NPC471542
0.7143	Intermediate Similarity	NPC119669
0.7133	Intermediate Similarity	NPC201284
0.7133	Intermediate Similarity	NPC54243
0.7125	Intermediate Similarity	NPC470844
0.7125	Intermediate Similarity	NPC106606
0.7124	Intermediate Similarity	NPC141252
0.7124	Intermediate Similarity	NPC11799
0.7118	Intermediate Similarity	NPC78733
0.7118	Intermediate Similarity	NPC41178
0.7118	Intermediate Similarity	NPC138487
0.7118	Intermediate Similarity	NPC216459
0.7112	Intermediate Similarity	NPC66909
0.7112	Intermediate Similarity	NPC204580
0.711	Intermediate Similarity	NPC469479
0.7102	Intermediate Similarity	NPC475845
0.7099	Intermediate Similarity	NPC233707
0.7099	Intermediate Similarity	NPC314682
0.7097	Intermediate Similarity	NPC264938
0.7089	Intermediate Similarity	NPC470977
0.7089	Intermediate Similarity	NPC470976
0.7089	Intermediate Similarity	NPC7012
0.7089	Intermediate Similarity	NPC196979
0.7086	Intermediate Similarity	NPC124657
0.7083	Intermediate Similarity	NPC106328
0.7083	Intermediate Similarity	NPC314946
0.7083	Intermediate Similarity	NPC223125
0.7083	Intermediate Similarity	NPC35150
0.7081	Intermediate Similarity	NPC99854
0.7079	Intermediate Similarity	NPC329992
0.7076	Intermediate Similarity	NPC147091
0.7067	Intermediate Similarity	NPC32298
0.7066	Intermediate Similarity	NPC471346
0.7066	Intermediate Similarity	NPC470019
0.7065	Intermediate Similarity	NPC473008
0.7063	Intermediate Similarity	NPC324117
0.7063	Intermediate Similarity	NPC1249
0.7059	Intermediate Similarity	NPC471649
0.7056	Intermediate Similarity	NPC121400
0.7055	Intermediate Similarity	NPC26589
0.7055	Intermediate Similarity	NPC328750
0.7055	Intermediate Similarity	NPC477408
0.7055	Intermediate Similarity	NPC474915
0.7055	Intermediate Similarity	NPC473444
0.7055	Intermediate Similarity	NPC188163
0.7055	Intermediate Similarity	NPC213206
0.7051	Intermediate Similarity	NPC45537
0.7048	Intermediate Similarity	NPC469385
0.7048	Intermediate Similarity	NPC184702
0.7048	Intermediate Similarity	NPC470932
0.7048	Intermediate Similarity	NPC290038
0.7047	Intermediate Similarity	NPC157958
0.7047	Intermediate Similarity	NPC314596
0.7047	Intermediate Similarity	NPC478075
0.7045	Intermediate Similarity	NPC474324
0.7045	Intermediate Similarity	NPC57812
0.7044	Intermediate Similarity	NPC183103
0.7044	Intermediate Similarity	NPC474340
0.7044	Intermediate Similarity	NPC477406
0.7044	Intermediate Similarity	NPC118253
0.7044	Intermediate Similarity	NPC325568
0.7043	Intermediate Similarity	NPC94499
0.7041	Intermediate Similarity	NPC472298
0.7041	Intermediate Similarity	NPC8337
0.7041	Intermediate Similarity	NPC85747
0.7037	Intermediate Similarity	NPC284184
0.7033	Intermediate Similarity	NPC102760
0.7032	Intermediate Similarity	NPC2771
0.703	Intermediate Similarity	NPC96692
0.703	Intermediate Similarity	NPC471644

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 NPC133817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	633
0.2-0.3	940
0.3-0.4	1942
0.4-0.5	2543
0.5-0.6	1849
0.6-0.7	940
0.7-0.8	109
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6844	Discontinued
0.7988	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3142	Approved
0.7947	Intermediate Similarity	NPD3140	Approved
0.7908	Intermediate Similarity	NPD2569	Approved
0.7908	Intermediate Similarity	NPD2567	Approved
0.7764	Intermediate Similarity	NPD3639	Approved
0.7764	Intermediate Similarity	NPD3640	Phase 3
0.7764	Intermediate Similarity	NPD3641	Approved
0.7701	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4424	Discontinued
0.7669	Intermediate Similarity	NPD2651	Approved
0.7669	Intermediate Similarity	NPD2649	Approved
0.7657	Intermediate Similarity	NPD2968	Approved
0.7657	Intermediate Similarity	NPD2971	Approved
0.7584	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5890	Approved
0.7576	Intermediate Similarity	NPD5889	Approved
0.7572	Intermediate Similarity	NPD5313	Approved
0.7572	Intermediate Similarity	NPD5312	Approved
0.7564	Intermediate Similarity	NPD5689	Approved
0.7564	Intermediate Similarity	NPD5688	Approved
0.7541	Intermediate Similarity	NPD4420	Approved
0.7531	Intermediate Similarity	NPD4662	Approved
0.7531	Intermediate Similarity	NPD4661	Approved
0.7516	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4098	Discontinued
0.7473	Intermediate Similarity	NPD5006	Approved
0.7473	Intermediate Similarity	NPD5005	Approved
0.7459	Intermediate Similarity	NPD4107	Approved
0.7457	Intermediate Similarity	NPD3446	Phase 1
0.7453	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5977	Approved
0.744	Intermediate Similarity	NPD5978	Approved
0.7439	Intermediate Similarity	NPD7427	Discontinued
0.7438	Intermediate Similarity	NPD2654	Approved
0.7436	Intermediate Similarity	NPD4618	Approved
0.7436	Intermediate Similarity	NPD4622	Approved
0.7425	Intermediate Similarity	NPD7577	Discontinued
0.7425	Intermediate Similarity	NPD6280	Approved
0.7425	Intermediate Similarity	NPD6279	Approved
0.741	Intermediate Similarity	NPD6585	Discontinued
0.7403	Intermediate Similarity	NPD2490	Approved
0.7403	Intermediate Similarity	NPD2488	Approved
0.7403	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5754	Discontinued
0.738	Intermediate Similarity	NPD3057	Approved
0.7375	Intermediate Similarity	NPD2897	Discontinued
0.736	Intermediate Similarity	NPD4078	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1307	Phase 2
0.7353	Intermediate Similarity	NPD1309	Phase 2
0.7326	Intermediate Similarity	NPD4482	Phase 3
0.7321	Intermediate Similarity	NPD7248	Discontinued
0.7317	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4474	Approved
0.7308	Intermediate Similarity	NPD4475	Approved
0.7299	Intermediate Similarity	NPD4481	Phase 3
0.7293	Intermediate Similarity	NPD7291	Discontinued
0.7287	Intermediate Similarity	NPD3533	Approved
0.7287	Intermediate Similarity	NPD2972	Approved
0.7287	Intermediate Similarity	NPD2491	Approved
0.7262	Intermediate Similarity	NPD4773	Phase 2
0.7262	Intermediate Similarity	NPD4772	Phase 2
0.725	Intermediate Similarity	NPD4476	Approved
0.725	Intermediate Similarity	NPD4477	Approved
0.7243	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4361	Phase 2
0.7239	Intermediate Similarity	NPD3692	Discontinued
0.7233	Intermediate Similarity	NPD2200	Suspended
0.7219	Intermediate Similarity	NPD7317	Phase 3
0.7213	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4584	Approved
0.7209	Intermediate Similarity	NPD6862	Phase 2
0.7202	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3448	Approved
0.7193	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3051	Approved
0.7184	Intermediate Similarity	NPD6808	Phase 2
0.7181	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD8161	Suspended
0.7167	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2970	Approved
0.7143	Intermediate Similarity	NPD2969	Approved
0.7135	Intermediate Similarity	NPD7318	Phase 3
0.7135	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1336	Approved
0.7133	Intermediate Similarity	NPD3444	Approved
0.7133	Intermediate Similarity	NPD3445	Approved
0.7133	Intermediate Similarity	NPD3443	Approved
0.7128	Intermediate Similarity	NPD8285	Discontinued
0.7126	Intermediate Similarity	NPD6107	Approved
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7112	Intermediate Similarity	NPD2975	Approved
0.7112	Intermediate Similarity	NPD2974	Approved
0.7112	Intermediate Similarity	NPD5564	Approved
0.7112	Intermediate Similarity	NPD2973	Approved
0.7111	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD27	Approved
0.7102	Intermediate Similarity	NPD2489	Approved
0.7099	Intermediate Similarity	NPD2346	Discontinued
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD2798	Approved
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.7091	Intermediate Similarity	NPD6666	Approved
0.7091	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6667	Approved
0.709	Intermediate Similarity	NPD4580	Approved
0.7077	Intermediate Similarity	NPD5676	Approved
0.7076	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6039	Approved
0.7059	Intermediate Similarity	NPD2230	Approved
0.7059	Intermediate Similarity	NPD7110	Phase 1
0.7059	Intermediate Similarity	NPD2232	Approved
0.7059	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2233	Approved
0.7055	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1712	Approved
0.7048	Intermediate Similarity	NPD3124	Discontinued
0.7044	Intermediate Similarity	NPD3110	Approved
0.7044	Intermediate Similarity	NPD2238	Phase 2
0.7044	Intermediate Similarity	NPD3109	Approved
0.7037	Intermediate Similarity	NPD2796	Approved
0.7025	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5159	Phase 2
0.7013	Intermediate Similarity	NPD5157	Phase 1
0.7013	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6315	Phase 2
0.6989	Remote Similarity	NPD5710	Approved
0.6989	Remote Similarity	NPD4166	Phase 2
0.6989	Remote Similarity	NPD7315	Approved
0.6989	Remote Similarity	NPD5711	Approved
0.6981	Remote Similarity	NPD7713	Phase 3
0.6975	Remote Similarity	NPD2156	Approved
0.6975	Remote Similarity	NPD1753	Discontinued
0.6975	Remote Similarity	NPD2155	Approved
0.6975	Remote Similarity	NPD2154	Approved
0.6971	Remote Similarity	NPD5494	Approved
0.6971	Remote Similarity	NPD2904	Discontinued
0.697	Remote Similarity	NPD6748	Discontinued
0.6968	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2493	Approved
0.6963	Remote Similarity	NPD2494	Approved
0.6962	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6386	Approved
0.6959	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7037	Approved
0.6949	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4583	Approved
0.6943	Remote Similarity	NPD4040	Phase 1
0.6943	Remote Similarity	NPD4582	Approved
0.694	Remote Similarity	NPD6618	Phase 2
0.6933	Remote Similarity	NPD6032	Approved
0.6928	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2163	Approved
0.6927	Remote Similarity	NPD6620	Discovery
0.6915	Remote Similarity	NPD4111	Phase 1
0.6915	Remote Similarity	NPD4665	Approved
0.6914	Remote Similarity	NPD743	Approved
0.6911	Remote Similarity	NPD5457	Discontinued
0.691	Remote Similarity	NPD2898	Approved
0.691	Remote Similarity	NPD2246	Approved
0.691	Remote Similarity	NPD2248	Approved
0.6908	Remote Similarity	NPD6382	Discontinued
0.69	Remote Similarity	NPD5980	Discovery
0.6899	Remote Similarity	NPD6832	Phase 2
0.6899	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1341	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4002	Approved
0.6891	Remote Similarity	NPD4004	Approved
0.6883	Remote Similarity	NPD4217	Approved
0.6883	Remote Similarity	NPD3132	Approved
0.6883	Remote Similarity	NPD3131	Approved
0.6883	Remote Similarity	NPD2612	Approved
0.6883	Remote Similarity	NPD4216	Approved
0.6883	Remote Similarity	NPD2609	Approved
0.6883	Remote Similarity	NPD2608	Approved
0.6883	Remote Similarity	NPD2611	Approved
0.6883	Remote Similarity	NPD2610	Approved
0.6883	Remote Similarity	NPD4215	Approved
0.6883	Remote Similarity	NPD4218	Approved
0.6882	Remote Similarity	NPD4210	Discontinued
0.6879	Remote Similarity	NPD7819	Suspended
0.6878	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2245	Discovery
0.6875	Remote Similarity	NPD6321	Discontinued
0.6875	Remote Similarity	NPD3452	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