NPASS Compound

Structure

NPC476151 OpenBabel07101718282D 23 25 0 0 1 0 0 0 0 0999 V2000 3.3569 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8914 -2.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.4659 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3660 -4.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.4659 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 7.4282 -0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.4659 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1.3660 -5.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 23 1 0 0 0 0 4 7 1 0 0 0 0 4 13 2 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 14 18 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 19 22 1 0 0 0 0 M CHG 2 20 1 22 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.17
Volume:	333.059
LogP:	-0.237
LogD:	0.954
LogS:	0.632
# Rotatable Bonds:	3
TPSA:	52.52
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.885
Synthetic Accessibility Score:	3.551
Fsp3:	0.368
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:	-5.419
MDCK Permeability:	2.3533728381153196e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.943
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	31.587339401245117%
Volume Distribution (VD):	3.141
Pgp-substrate:	61.12305450439453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.732
CYP2D6-inhibitor:	0.174
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.788

ADMET: Excretion

Clearance (CL):	4.775
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.199
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.683
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.317
Carcinogencity:	0.145
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.495

Download Data

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

Natural Product: NPC476151

Natural Product ID:	NPC476151
*Common Name:**	(+/-)-Oblongine
IUPAC Name:	1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium-8-ol;chloride
Synonyms:	(+/-)-Oblongine
Standard InCHIKey:	UWPGKSRZKKLEFW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H23NO3.ClH/c1-20(2)11-10-14-6-9-17(23-3)19(22)18(14)16(20)12-13-4-7-15(21)8-5-13;/h4-9,16H,10-12H2,1-3H3,(H-,21,22);1H
SMILES:	C[N+]1(CCC2=C(C1CC3=CC=C(C=C3)O)C(=C(C=C2)OC)O)C.[Cl-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL540908
PubChem CID:	157128
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
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8254346]
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	>	10000.0	ng/ml	PMID[555693]

☑ 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 NPC476151 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	269
0.1-0.2	1651
0.2-0.3	8864
0.3-0.4	8990
0.4-0.5	5744
0.5-0.6	11432
0.6-0.7	4461
0.7-0.8	859
0.8-0.85	268
0.85-0.9	96
0.9-0.95	60
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC103379
0.9857	High Similarity	NPC477565
0.9712	High Similarity	NPC185838
0.9574	High Similarity	NPC179825
0.9574	High Similarity	NPC191376
0.9574	High Similarity	NPC321505
0.9517	High Similarity	NPC193949
0.9517	High Similarity	NPC184026
0.9517	High Similarity	NPC2413
0.9517	High Similarity	NPC5238
0.9517	High Similarity	NPC39701
0.9517	High Similarity	NPC295691
0.9517	High Similarity	NPC189266
0.9517	High Similarity	NPC110416
0.9517	High Similarity	NPC249797
0.9517	High Similarity	NPC54379
0.9517	High Similarity	NPC204828
0.9517	High Similarity	NPC278799
0.9517	High Similarity	NPC207757
0.9517	High Similarity	NPC276588
0.9517	High Similarity	NPC172765
0.9517	High Similarity	NPC469817
0.9517	High Similarity	NPC127674
0.9507	High Similarity	NPC428
0.9507	High Similarity	NPC135538
0.9507	High Similarity	NPC476571
0.9507	High Similarity	NPC147390
0.9507	High Similarity	NPC24233
0.9507	High Similarity	NPC246587
0.9448	High Similarity	NPC2295
0.9448	High Similarity	NPC477564
0.9353	High Similarity	NPC314682
0.9306	High Similarity	NPC60538
0.9306	High Similarity	NPC207824
0.9301	High Similarity	NPC16107
0.9301	High Similarity	NPC51957
0.9301	High Similarity	NPC106295
0.9301	High Similarity	NPC476144
0.9301	High Similarity	NPC210437
0.9286	High Similarity	NPC328750
0.9286	High Similarity	NPC474915
0.9286	High Similarity	NPC213206
0.9286	High Similarity	NPC188163
0.9241	High Similarity	NPC192768
0.9241	High Similarity	NPC97221
0.9241	High Similarity	NPC151895
0.9241	High Similarity	NPC220858
0.9241	High Similarity	NPC88249
0.9236	High Similarity	NPC7467
0.9178	High Similarity	NPC76213
0.9178	High Similarity	NPC277669
0.9133	High Similarity	NPC27410
0.9133	High Similarity	NPC166014
0.9079	High Similarity	NPC238530
0.9079	High Similarity	NPC232514
0.9079	High Similarity	NPC276944
0.9021	High Similarity	NPC136860
0.9021	High Similarity	NPC128019
0.9021	High Similarity	NPC476567
0.902	High Similarity	NPC264850
0.902	High Similarity	NPC13916
0.9	High Similarity	NPC131204
0.9	High Similarity	NPC301050
0.8986	High Similarity	NPC133011
0.8986	High Similarity	NPC82285
0.898	High Similarity	NPC274026
0.8954	High Similarity	NPC24465
0.8947	High Similarity	NPC60186
0.8933	High Similarity	NPC147091
0.8919	High Similarity	NPC326316
0.8919	High Similarity	NPC81733
0.8903	High Similarity	NPC204908
0.8903	High Similarity	NPC83198
0.8889	High Similarity	NPC324144
0.8867	High Similarity	NPC41178
0.8867	High Similarity	NPC138487
0.8867	High Similarity	NPC216459
0.8859	High Similarity	NPC26601
0.8844	High Similarity	NPC475959
0.8841	High Similarity	NPC160193
0.8839	High Similarity	NPC117188
0.8839	High Similarity	NPC205421
0.8839	High Similarity	NPC12053
0.8839	High Similarity	NPC474931
0.8839	High Similarity	NPC306555
0.8839	High Similarity	NPC298979
0.8839	High Similarity	NPC145832
0.8839	High Similarity	NPC81218
0.8839	High Similarity	NPC158376
0.8831	High Similarity	NPC477563
0.8831	High Similarity	NPC306843
0.8831	High Similarity	NPC96603
0.8831	High Similarity	NPC212794
0.8831	High Similarity	NPC13504
0.8831	High Similarity	NPC136508
0.8831	High Similarity	NPC253043
0.8831	High Similarity	NPC196447
0.8831	High Similarity	NPC78222
0.8816	High Similarity	NPC111485
0.8808	High Similarity	NPC146288
0.8774	High Similarity	NPC81247
0.8774	High Similarity	NPC35627
0.8774	High Similarity	NPC476573
0.8767	High Similarity	NPC130926
0.8766	High Similarity	NPC1229
0.8734	High Similarity	NPC190783
0.8734	High Similarity	NPC232386
0.8734	High Similarity	NPC152680
0.871	High Similarity	NPC134858
0.8699	High Similarity	NPC294249
0.8696	High Similarity	NPC172403
0.8684	High Similarity	NPC186063
0.8684	High Similarity	NPC31311
0.8684	High Similarity	NPC234392
0.8671	High Similarity	NPC193528
0.8658	High Similarity	NPC92541
0.8658	High Similarity	NPC219162
0.8654	High Similarity	NPC250846
0.8654	High Similarity	NPC256012
0.8654	High Similarity	NPC42549
0.8654	High Similarity	NPC268503
0.8654	High Similarity	NPC240841
0.8654	High Similarity	NPC317272
0.8645	High Similarity	NPC233650
0.8636	High Similarity	NPC249274
0.8636	High Similarity	NPC205167
0.8627	High Similarity	NPC476572
0.8625	High Similarity	NPC241704
0.8618	High Similarity	NPC325871
0.8618	High Similarity	NPC99659
0.8618	High Similarity	NPC93593
0.8616	High Similarity	NPC2314
0.8609	High Similarity	NPC37272
0.8608	High Similarity	NPC168753
0.8608	High Similarity	NPC118274
0.8599	High Similarity	NPC210140
0.859	High Similarity	NPC121275
0.859	High Similarity	NPC284183
0.859	High Similarity	NPC4138
0.8571	High Similarity	NPC92191
0.8571	High Similarity	NPC59028
0.8562	High Similarity	NPC170503
0.8562	High Similarity	NPC203784
0.8562	High Similarity	NPC126519
0.8553	High Similarity	NPC239775
0.8544	High Similarity	NPC470324
0.8543	High Similarity	NPC476568
0.8542	High Similarity	NPC253429
0.8523	High Similarity	NPC253883
0.8523	High Similarity	NPC95075
0.8523	High Similarity	NPC90844
0.8523	High Similarity	NPC144863
0.8519	High Similarity	NPC32154
0.8516	High Similarity	NPC215829
0.8516	High Similarity	NPC232924
0.8516	High Similarity	NPC266753
0.8516	High Similarity	NPC97072
0.8516	High Similarity	NPC477559
0.8516	High Similarity	NPC160298
0.8516	High Similarity	NPC306902
0.8506	High Similarity	NPC475326
0.85	High Similarity	NPC192135
0.85	High Similarity	NPC66341
0.85	High Similarity	NPC477020
0.8497	Intermediate Similarity	NPC244112
0.8491	Intermediate Similarity	NPC69712
0.8491	Intermediate Similarity	NPC477562
0.8491	Intermediate Similarity	NPC26240
0.8487	Intermediate Similarity	NPC233029
0.8487	Intermediate Similarity	NPC210148
0.8481	Intermediate Similarity	NPC150879
0.8467	Intermediate Similarity	NPC130941
0.8457	Intermediate Similarity	NPC114364
0.8457	Intermediate Similarity	NPC320223
0.8452	Intermediate Similarity	NPC221864
0.8447	Intermediate Similarity	NPC199465
0.8447	Intermediate Similarity	NPC229166
0.8447	Intermediate Similarity	NPC128560
0.8442	Intermediate Similarity	NPC247639
0.8442	Intermediate Similarity	NPC25084
0.8428	Intermediate Similarity	NPC66573
0.8418	Intermediate Similarity	NPC124657
0.8415	Intermediate Similarity	NPC8836
0.8415	Intermediate Similarity	NPC15414
0.8415	Intermediate Similarity	NPC42663
0.8415	Intermediate Similarity	NPC328155
0.8415	Intermediate Similarity	NPC271013
0.8415	Intermediate Similarity	NPC251735
0.8415	Intermediate Similarity	NPC279228
0.8415	Intermediate Similarity	NPC54654
0.8415	Intermediate Similarity	NPC222661
0.8415	Intermediate Similarity	NPC104196
0.8415	Intermediate Similarity	NPC7715
0.8415	Intermediate Similarity	NPC182052
0.8415	Intermediate Similarity	NPC239824
0.8415	Intermediate Similarity	NPC258657
0.8415	Intermediate Similarity	NPC290582
0.8415	Intermediate Similarity	NPC217748
0.8415	Intermediate Similarity	NPC229373
0.8415	Intermediate Similarity	NPC223690

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 NPC476151 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	746
0.2-0.3	1048
0.3-0.4	1669
0.4-0.5	2623
0.5-0.6	1821
0.6-0.7	786
0.7-0.8	237
0.8-0.85	30
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9301	High Similarity	NPD4584	Approved
0.9286	High Similarity	NPD4664	Clinical (unspecified phase)
0.8675	High Similarity	NPD4773	Phase 2
0.8675	High Similarity	NPD4772	Phase 2
0.8667	High Similarity	NPD4017	Approved
0.8571	High Similarity	NPD5241	Discontinued
0.8544	High Similarity	NPD2898	Approved
0.8535	High Similarity	NPD4010	Discontinued
0.8526	High Similarity	NPD7201	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD8054	Approved
0.8415	Intermediate Similarity	NPD8053	Approved
0.8414	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD3640	Phase 3
0.8411	Intermediate Similarity	NPD3641	Approved
0.8411	Intermediate Similarity	NPD3639	Approved
0.8411	Intermediate Similarity	NPD6031	Approved
0.8411	Intermediate Similarity	NPD6030	Approved
0.84	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7831	Phase 2
0.8397	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7833	Phase 2
0.838	Intermediate Similarity	NPD5718	Phase 2
0.8377	Intermediate Similarity	NPD7298	Approved
0.8333	Intermediate Similarity	NPD2421	Approved
0.8333	Intermediate Similarity	NPD6788	Approved
0.8333	Intermediate Similarity	NPD2420	Approved
0.8311	Intermediate Similarity	NPD5177	Phase 3
0.8302	Intermediate Similarity	NPD6071	Discontinued
0.8269	Intermediate Similarity	NPD2560	Approved
0.8269	Intermediate Similarity	NPD2563	Approved
0.8231	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD8252	Approved
0.821	Intermediate Similarity	NPD8099	Discontinued
0.821	Intermediate Similarity	NPD8251	Approved
0.8199	Intermediate Similarity	NPD2489	Approved
0.8199	Intermediate Similarity	NPD27	Approved
0.8182	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD8156	Discontinued
0.8137	Intermediate Similarity	NPD2969	Approved
0.8137	Intermediate Similarity	NPD2970	Approved
0.8112	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD3051	Approved
0.8069	Intermediate Similarity	NPD4474	Approved
0.8069	Intermediate Similarity	NPD4475	Approved
0.8069	Intermediate Similarity	NPD2674	Phase 3
0.8026	Intermediate Similarity	NPD3845	Phase 1
0.7973	Intermediate Similarity	NPD6895	Approved
0.7973	Intermediate Similarity	NPD6896	Approved
0.7952	Intermediate Similarity	NPD6297	Approved
0.7947	Intermediate Similarity	NPD3060	Approved
0.7943	Intermediate Similarity	NPD2232	Approved
0.7943	Intermediate Similarity	NPD2230	Approved
0.7943	Intermediate Similarity	NPD2233	Approved
0.7927	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1424	Approved
0.7919	Intermediate Similarity	NPD1753	Discontinued
0.7908	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6107	Approved
0.7901	Intermediate Similarity	NPD7802	Discontinued
0.7877	Intermediate Similarity	NPD3144	Approved
0.7877	Intermediate Similarity	NPD3145	Approved
0.7871	Intermediate Similarity	NPD6090	Discontinued
0.7857	Intermediate Similarity	NPD2667	Approved
0.7857	Intermediate Similarity	NPD2668	Approved
0.7857	Intermediate Similarity	NPD3124	Discontinued
0.7834	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5978	Approved
0.7812	Intermediate Similarity	NPD5977	Approved
0.7792	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6748	Discontinued
0.777	Intermediate Similarity	NPD3110	Approved
0.777	Intermediate Similarity	NPD2238	Phase 2
0.777	Intermediate Similarity	NPD3109	Approved
0.7765	Intermediate Similarity	NPD6851	Approved
0.7765	Intermediate Similarity	NPD6853	Approved
0.7764	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4166	Phase 2
0.7733	Intermediate Similarity	NPD7906	Approved
0.7727	Intermediate Similarity	NPD3692	Discontinued
0.7727	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD4055	Discovery
0.7714	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4237	Approved
0.7712	Intermediate Similarity	NPD4162	Approved
0.7712	Intermediate Similarity	NPD4236	Phase 3
0.7706	Intermediate Similarity	NPD7313	Approved
0.7706	Intermediate Similarity	NPD7312	Approved
0.7706	Intermediate Similarity	NPD4577	Approved
0.7706	Intermediate Similarity	NPD7310	Approved
0.7706	Intermediate Similarity	NPD4578	Approved
0.7706	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7311	Approved
0.7671	Intermediate Similarity	NPD3636	Approved
0.7671	Intermediate Similarity	NPD3635	Approved
0.7671	Intermediate Similarity	NPD3637	Approved
0.767	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7309	Approved
0.766	Intermediate Similarity	NPD4093	Discontinued
0.7655	Intermediate Similarity	NPD3053	Approved
0.7655	Intermediate Similarity	NPD3055	Approved
0.7651	Intermediate Similarity	NPD4481	Phase 3
0.7628	Intermediate Similarity	NPD7598	Phase 2
0.7625	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7110	Phase 1
0.7619	Intermediate Similarity	NPD5312	Approved
0.7619	Intermediate Similarity	NPD5313	Approved
0.7613	Intermediate Similarity	NPD5160	Discontinued
0.7589	Intermediate Similarity	NPD5303	Approved
0.7589	Intermediate Similarity	NPD5304	Approved
0.7582	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4123	Phase 3
0.7572	Intermediate Similarity	NPD4663	Approved
0.7568	Intermediate Similarity	NPD5155	Approved
0.7568	Intermediate Similarity	NPD5156	Approved
0.7564	Intermediate Similarity	NPD7124	Phase 2
0.755	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6331	Phase 2
0.7548	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD2488	Approved
0.7543	Intermediate Similarity	NPD2490	Approved
0.7534	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4103	Phase 2
0.7534	Intermediate Similarity	NPD4098	Discontinued
0.7532	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2977	Approved
0.7531	Intermediate Similarity	NPD2978	Approved
0.7517	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1669	Approved
0.75	Intermediate Similarity	NPD3594	Approved
0.75	Intermediate Similarity	NPD2605	Approved
0.75	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2606	Approved
0.75	Intermediate Similarity	NPD7281	Phase 3
0.75	Intermediate Similarity	NPD4005	Discontinued
0.75	Intermediate Similarity	NPD824	Approved
0.75	Intermediate Similarity	NPD7280	Phase 3
0.75	Intermediate Similarity	NPD5604	Discontinued
0.75	Intermediate Similarity	NPD3595	Approved
0.7485	Intermediate Similarity	NPD6687	Approved
0.7485	Intermediate Similarity	NPD6688	Approved
0.7484	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1914	Approved
0.7483	Intermediate Similarity	NPD6584	Phase 3
0.7483	Intermediate Similarity	NPD7905	Discontinued
0.7469	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6667	Approved
0.7452	Intermediate Similarity	NPD6666	Approved
0.7451	Intermediate Similarity	NPD2156	Approved
0.7451	Intermediate Similarity	NPD2155	Approved
0.7451	Intermediate Similarity	NPD2154	Approved
0.7443	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5773	Approved
0.7423	Intermediate Similarity	NPD5772	Approved
0.7419	Intermediate Similarity	NPD7037	Approved
0.7419	Intermediate Similarity	NPD7153	Discontinued
0.7412	Intermediate Similarity	NPD4873	Discontinued
0.7403	Intermediate Similarity	NPD2161	Phase 2
0.7399	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4659	Approved
0.7381	Intermediate Similarity	NPD4083	Discontinued
0.7379	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2122	Discontinued
0.7375	Intermediate Similarity	NPD5976	Discontinued
0.7372	Intermediate Similarity	NPD6364	Approved
0.7372	Intermediate Similarity	NPD44	Approved
0.7368	Intermediate Similarity	NPD7479	Phase 2
0.7362	Intermediate Similarity	NPD5720	Discontinued
0.7361	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2234	Approved
0.7357	Intermediate Similarity	NPD2229	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7357	Intermediate Similarity	NPD2228	Approved
0.7355	Intermediate Similarity	NPD3656	Approved
0.7351	Intermediate Similarity	NPD3532	Approved
0.7351	Intermediate Similarity	NPD7477	Discontinued
0.7351	Intermediate Similarity	NPD3530	Approved
0.7351	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3531	Approved
0.7349	Intermediate Similarity	NPD5709	Phase 3
0.7348	Intermediate Similarity	NPD8095	Phase 1
0.7347	Intermediate Similarity	NPD5311	Approved
0.7347	Intermediate Similarity	NPD5310	Approved
0.7346	Intermediate Similarity	NPD4678	Approved
0.7346	Intermediate Similarity	NPD6876	Approved
0.7346	Intermediate Similarity	NPD6875	Approved
0.7346	Intermediate Similarity	NPD4675	Approved
0.7345	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1024	Discontinued
0.733	Intermediate Similarity	NPD7291	Discontinued
0.7325	Intermediate Similarity	NPD5754	Discontinued
0.7308	Intermediate Similarity	NPD4257	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