NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	299.15
Volume:	315.764
LogP:	2.263
LogD:	2.428
LogS:	-2.173
# Rotatable Bonds:	3
TPSA:	52.93
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.915
Synthetic Accessibility Score:	2.775
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	1.72E-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.893
30% Bioavailability (F30%):	0.177

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	70.21%
Volume Distribution (VD):	2.369
Pgp-substrate:	20.99%

ADMET: Metabolism

CYP1A2-inhibitor:	0.234
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.726
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.9

ADMET: Excretion

Clearance (CL):	18.028
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.391
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.83
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.915
Carcinogencity:	0.367
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC477565

Natural Product ID:	NPC477565
*Common Name:**	(1S)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-8-ol;2,2,2-trifluoroacetic acid
IUPAC Name:	(1S)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-8-ol;2,2,2-trifluoroacetic acid
Synonyms:	(1S)-Juziphine
Standard InCHIKey:	KBUDZZRXWSJABG-RSAXXLAASA-N
Standard InCHI:	InChI=1S/C18H21NO3.C2HF3O2/c1-19-10-9-13-5-8-16(22-2)18(21)17(13)15(19)11-12-3-6-14(20)7-4-12;3-2(4,5)1(6)7/h3-8,15,20-21H,9-11H2,1-2H3;(H,6,7)/t15-;/m0./s1
SMILES:	CN1CCC2=C([C@@H]1CC3=CC=C(C=C3)O)C(=C(C=C2)OC)O.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	54579939
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
NPO11152	Neolitsea dealbata	Species	Lauraceae	Eukaryota	Barks	Thomas Road, 1.5km West of Yungaburra, Australia	1998-MAY	PMID[20732809]
NPO11152	Neolitsea dealbata	Species	Lauraceae	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	7

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT1523	Cell Line	NFF	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT27	Others	Unspecified		IC50	>	100000	nM	PMID[20732809]

☑ 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 NPC477565 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	229
0.1-0.2	1285
0.2-0.3	5877
0.3-0.4	12239
0.4-0.5	5050
0.5-0.6	11739
0.6-0.7	5208
0.7-0.8	801
0.8-0.85	158
0.85-0.9	81
0.9-0.95	27
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103379
0.9857	High Similarity	NPC476151
0.9716	High Similarity	NPC191376
0.9716	High Similarity	NPC179825
0.9716	High Similarity	NPC321505
0.9655	High Similarity	NPC54379
0.9655	High Similarity	NPC204828
0.9655	High Similarity	NPC172765
0.9655	High Similarity	NPC193949
0.9655	High Similarity	NPC207757
0.9655	High Similarity	NPC5238
0.9655	High Similarity	NPC189266
0.9655	High Similarity	NPC110416
0.9655	High Similarity	NPC469817
0.9655	High Similarity	NPC276588
0.9655	High Similarity	NPC295691
0.9655	High Similarity	NPC39701
0.9655	High Similarity	NPC2413
0.9655	High Similarity	NPC127674
0.9655	High Similarity	NPC278799
0.9655	High Similarity	NPC249797
0.9655	High Similarity	NPC184026
0.9648	High Similarity	NPC476571
0.9648	High Similarity	NPC147390
0.9648	High Similarity	NPC246587
0.9648	High Similarity	NPC135538
0.9648	High Similarity	NPC428
0.9648	High Similarity	NPC24233
0.9586	High Similarity	NPC477564
0.9586	High Similarity	NPC2295
0.9574	High Similarity	NPC185838
0.9379	High Similarity	NPC220858
0.9379	High Similarity	NPC88249
0.9379	High Similarity	NPC97221
0.9379	High Similarity	NPC192768
0.9379	High Similarity	NPC151895
0.9315	High Similarity	NPC277669
0.9315	High Similarity	NPC76213
0.9267	High Similarity	NPC166014
0.9267	High Similarity	NPC27410
0.922	High Similarity	NPC314682
0.9211	High Similarity	NPC238530
0.9211	High Similarity	NPC276944
0.9211	High Similarity	NPC232514
0.9178	High Similarity	NPC207824
0.9178	High Similarity	NPC60538
0.9172	High Similarity	NPC210437
0.9172	High Similarity	NPC16107
0.9172	High Similarity	NPC51957
0.9172	High Similarity	NPC106295
0.9172	High Similarity	NPC476144
0.9155	High Similarity	NPC188163
0.9155	High Similarity	NPC213206
0.9155	High Similarity	NPC328750
0.9155	High Similarity	NPC474915
0.915	High Similarity	NPC264850
0.915	High Similarity	NPC13916
0.9143	High Similarity	NPC131204
0.9143	High Similarity	NPC301050
0.9122	High Similarity	NPC82285
0.9122	High Similarity	NPC133011
0.911	High Similarity	NPC7467
0.9085	High Similarity	NPC24465
0.9079	High Similarity	NPC60186
0.9067	High Similarity	NPC147091
0.9032	High Similarity	NPC83198
0.9032	High Similarity	NPC204908
0.902	High Similarity	NPC324144
0.8968	High Similarity	NPC81218
0.8968	High Similarity	NPC306555
0.8968	High Similarity	NPC158376
0.8968	High Similarity	NPC117188
0.8968	High Similarity	NPC145832
0.8968	High Similarity	NPC205421
0.8968	High Similarity	NPC474931
0.8968	High Similarity	NPC12053
0.8961	High Similarity	NPC136508
0.8961	High Similarity	NPC306843
0.8961	High Similarity	NPC196447
0.8961	High Similarity	NPC477563
0.8961	High Similarity	NPC96603
0.8961	High Similarity	NPC212794
0.8961	High Similarity	NPC78222
0.8961	High Similarity	NPC13504
0.8961	High Similarity	NPC253043
0.8947	High Similarity	NPC111485
0.8903	High Similarity	NPC476573
0.8903	High Similarity	NPC81247
0.8903	High Similarity	NPC35627
0.8897	High Similarity	NPC476567
0.8897	High Similarity	NPC136860
0.8897	High Similarity	NPC128019
0.8896	High Similarity	NPC1229
0.8861	High Similarity	NPC152680
0.8861	High Similarity	NPC232386
0.8861	High Similarity	NPC190783
0.8859	High Similarity	NPC274026
0.8836	High Similarity	NPC294249
0.8816	High Similarity	NPC186063
0.88	High Similarity	NPC326316
0.88	High Similarity	NPC81733
0.8782	High Similarity	NPC250846
0.8782	High Similarity	NPC268503
0.8782	High Similarity	NPC240841
0.8782	High Similarity	NPC317272
0.8782	High Similarity	NPC42549
0.8782	High Similarity	NPC256012
0.8766	High Similarity	NPC249274
0.8766	High Similarity	NPC205167
0.875	High Similarity	NPC216459
0.875	High Similarity	NPC138487
0.875	High Similarity	NPC41178
0.8742	High Similarity	NPC37272
0.8742	High Similarity	NPC26601
0.8734	High Similarity	NPC118274
0.8734	High Similarity	NPC168753
0.8726	High Similarity	NPC210140
0.8726	High Similarity	NPC298979
0.8725	High Similarity	NPC475959
0.8718	High Similarity	NPC284183
0.8718	High Similarity	NPC4138
0.8718	High Similarity	NPC121275
0.8714	High Similarity	NPC160193
0.8693	High Similarity	NPC146288
0.8679	High Similarity	NPC239775
0.8671	High Similarity	NPC470324
0.8649	High Similarity	NPC130926
0.8642	High Similarity	NPC32154
0.8636	High Similarity	NPC475326
0.8625	High Similarity	NPC477020
0.8625	High Similarity	NPC66341
0.8625	High Similarity	NPC192135
0.8616	High Similarity	NPC69712
0.8616	High Similarity	NPC477562
0.8616	High Similarity	NPC26240
0.8599	High Similarity	NPC134858
0.858	High Similarity	NPC320223
0.858	High Similarity	NPC114364
0.8571	High Similarity	NPC172403
0.8571	High Similarity	NPC128560
0.8571	High Similarity	NPC199465
0.8571	High Similarity	NPC229166
0.8571	High Similarity	NPC234392
0.8571	High Similarity	NPC31311
0.8553	High Similarity	NPC66573
0.8552	High Similarity	NPC193528
0.8544	High Similarity	NPC124657
0.8543	High Similarity	NPC219162
0.8543	High Similarity	NPC92541
0.8537	High Similarity	NPC181796
0.8537	High Similarity	NPC279228
0.8537	High Similarity	NPC7715
0.8537	High Similarity	NPC15414
0.8537	High Similarity	NPC54654
0.8537	High Similarity	NPC285931
0.8537	High Similarity	NPC223690
0.8537	High Similarity	NPC8836
0.8537	High Similarity	NPC182052
0.8537	High Similarity	NPC311973
0.8537	High Similarity	NPC239824
0.8537	High Similarity	NPC42663
0.8537	High Similarity	NPC229373
0.8537	High Similarity	NPC290582
0.8537	High Similarity	NPC251735
0.8537	High Similarity	NPC290005
0.8537	High Similarity	NPC104196
0.8537	High Similarity	NPC217748
0.8537	High Similarity	NPC222661
0.8537	High Similarity	NPC258657
0.8537	High Similarity	NPC185639
0.8537	High Similarity	NPC49075
0.8537	High Similarity	NPC271013
0.8537	High Similarity	NPC90998
0.8537	High Similarity	NPC328155
0.8535	High Similarity	NPC233650
0.8519	High Similarity	NPC241704
0.8516	High Similarity	NPC476572
0.8509	High Similarity	NPC2314
0.8506	High Similarity	NPC93593
0.8506	High Similarity	NPC325871
0.8506	High Similarity	NPC99659
0.85	High Similarity	NPC109925
0.8493	Intermediate Similarity	NPC170170
0.8493	Intermediate Similarity	NPC211468
0.8493	Intermediate Similarity	NPC219233
0.8485	Intermediate Similarity	NPC254441
0.8485	Intermediate Similarity	NPC274716
0.8485	Intermediate Similarity	NPC167116
0.8481	Intermediate Similarity	NPC3375
0.8481	Intermediate Similarity	NPC255607
0.8476	Intermediate Similarity	NPC286119
0.8462	Intermediate Similarity	NPC59028
0.8462	Intermediate Similarity	NPC92191
0.8452	Intermediate Similarity	NPC203784
0.8452	Intermediate Similarity	NPC170503
0.8452	Intermediate Similarity	NPC126519
0.8447	Intermediate Similarity	NPC475215
0.8447	Intermediate Similarity	NPC476331
0.8447	Intermediate Similarity	NPC108434
0.8435	Intermediate Similarity	NPC323123

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 NPC477565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	658
0.2-0.3	1014
0.3-0.4	1866
0.4-0.5	2553
0.5-0.6	1915
0.6-0.7	797
0.7-0.8	178
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9172	High Similarity	NPD4584	Approved
0.9155	High Similarity	NPD4664	Clinical (unspecified phase)
0.8671	High Similarity	NPD2898	Approved
0.8662	High Similarity	NPD4010	Discontinued
0.8562	High Similarity	NPD4772	Phase 2
0.8562	High Similarity	NPD4773	Phase 2
0.8553	High Similarity	NPD4017	Approved
0.8537	High Similarity	NPD8053	Approved
0.8537	High Similarity	NPD8054	Approved
0.8533	High Similarity	NPD1754	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD2421	Approved
0.8467	Intermediate Similarity	NPD2420	Approved
0.8456	Intermediate Similarity	NPD5241	Discontinued
0.8418	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD2489	Approved
0.8323	Intermediate Similarity	NPD27	Approved
0.8301	Intermediate Similarity	NPD3640	Phase 3
0.8301	Intermediate Similarity	NPD3641	Approved
0.8301	Intermediate Similarity	NPD3639	Approved
0.8301	Intermediate Similarity	NPD6031	Approved
0.8301	Intermediate Similarity	NPD6030	Approved
0.8299	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7831	Phase 2
0.8291	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7833	Phase 2
0.8269	Intermediate Similarity	NPD7298	Approved
0.8264	Intermediate Similarity	NPD5718	Phase 2
0.8228	Intermediate Similarity	NPD6788	Approved
0.8207	Intermediate Similarity	NPD2674	Phase 3
0.82	Intermediate Similarity	NPD5177	Phase 3
0.8199	Intermediate Similarity	NPD6071	Discontinued
0.8165	Intermediate Similarity	NPD2563	Approved
0.8165	Intermediate Similarity	NPD2560	Approved
0.8158	Intermediate Similarity	NPD3845	Phase 1
0.8148	Intermediate Similarity	NPD2969	Approved
0.8148	Intermediate Similarity	NPD2970	Approved
0.811	Intermediate Similarity	NPD8252	Approved
0.811	Intermediate Similarity	NPD8251	Approved
0.811	Intermediate Similarity	NPD8099	Discontinued
0.8086	Intermediate Similarity	NPD3051	Approved
0.8069	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD8156	Discontinued
0.8039	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3145	Approved
0.8014	Intermediate Similarity	NPD3144	Approved
0.8	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4475	Approved
0.7959	Intermediate Similarity	NPD4474	Approved
0.7867	Intermediate Similarity	NPD6895	Approved
0.7867	Intermediate Similarity	NPD6896	Approved
0.7857	Intermediate Similarity	NPD6297	Approved
0.7849	Intermediate Similarity	NPD7906	Approved
0.7843	Intermediate Similarity	NPD3060	Approved
0.7832	Intermediate Similarity	NPD2230	Approved
0.7832	Intermediate Similarity	NPD2233	Approved
0.7832	Intermediate Similarity	NPD2232	Approved
0.7831	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7311	Approved
0.7824	Intermediate Similarity	NPD4577	Approved
0.7824	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7312	Approved
0.7824	Intermediate Similarity	NPD7313	Approved
0.7824	Intermediate Similarity	NPD4578	Approved
0.7824	Intermediate Similarity	NPD7310	Approved
0.7821	Intermediate Similarity	NPD1424	Approved
0.7815	Intermediate Similarity	NPD1753	Discontinued
0.7805	Intermediate Similarity	NPD7802	Discontinued
0.7805	Intermediate Similarity	NPD6107	Approved
0.7793	Intermediate Similarity	NPD3055	Approved
0.7793	Intermediate Similarity	NPD3053	Approved
0.7778	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7309	Approved
0.7771	Intermediate Similarity	NPD6090	Discontinued
0.7756	Intermediate Similarity	NPD3124	Discontinued
0.7746	Intermediate Similarity	NPD2668	Approved
0.7746	Intermediate Similarity	NPD2667	Approved
0.7736	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4162	Approved
0.7716	Intermediate Similarity	NPD5978	Approved
0.7716	Intermediate Similarity	NPD5977	Approved
0.7712	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4663	Approved
0.7677	Intermediate Similarity	NPD6748	Discontinued
0.7677	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6853	Approved
0.7674	Intermediate Similarity	NPD6851	Approved
0.7667	Intermediate Similarity	NPD2238	Phase 2
0.7667	Intermediate Similarity	NPD3109	Approved
0.7667	Intermediate Similarity	NPD3110	Approved
0.7657	Intermediate Similarity	NPD2488	Approved
0.7657	Intermediate Similarity	NPD2490	Approved
0.7654	Intermediate Similarity	NPD2977	Approved
0.7654	Intermediate Similarity	NPD2978	Approved
0.7651	Intermediate Similarity	NPD4166	Phase 2
0.7651	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3692	Discontinued
0.7628	Intermediate Similarity	NPD5160	Discontinued
0.7625	Intermediate Similarity	NPD824	Approved
0.7622	Intermediate Similarity	NPD4055	Discovery
0.7613	Intermediate Similarity	NPD4236	Phase 3
0.7613	Intermediate Similarity	NPD4237	Approved
0.7606	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3635	Approved
0.7568	Intermediate Similarity	NPD3636	Approved
0.7568	Intermediate Similarity	NPD3637	Approved
0.756	Intermediate Similarity	NPD4481	Phase 3
0.7552	Intermediate Similarity	NPD4093	Discontinued
0.7532	Intermediate Similarity	NPD7598	Phase 2
0.7531	Intermediate Similarity	NPD7110	Phase 1
0.7531	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4873	Discontinued
0.7529	Intermediate Similarity	NPD5312	Approved
0.7529	Intermediate Similarity	NPD5313	Approved
0.7484	Intermediate Similarity	NPD4123	Phase 3
0.7483	Intermediate Similarity	NPD5310	Approved
0.7483	Intermediate Similarity	NPD5304	Approved
0.7483	Intermediate Similarity	NPD5303	Approved
0.7483	Intermediate Similarity	NPD5311	Approved
0.7468	Intermediate Similarity	NPD2155	Approved
0.7468	Intermediate Similarity	NPD7124	Phase 2
0.7468	Intermediate Similarity	NPD2156	Approved
0.7468	Intermediate Similarity	NPD2154	Approved
0.7467	Intermediate Similarity	NPD5155	Approved
0.7467	Intermediate Similarity	NPD5156	Approved
0.7457	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6331	Phase 2
0.7452	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4098	Discontinued
0.7432	Intermediate Similarity	NPD4103	Phase 2
0.7432	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1669	Approved
0.7414	Intermediate Similarity	NPD7280	Phase 3
0.7414	Intermediate Similarity	NPD7281	Phase 3
0.741	Intermediate Similarity	NPD5604	Discontinued
0.7407	Intermediate Similarity	NPD4005	Discontinued
0.7403	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3594	Approved
0.74	Intermediate Similarity	NPD2605	Approved
0.74	Intermediate Similarity	NPD2606	Approved
0.74	Intermediate Similarity	NPD3595	Approved
0.7396	Intermediate Similarity	NPD6687	Approved
0.7396	Intermediate Similarity	NPD6688	Approved
0.7391	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1914	Approved
0.7383	Intermediate Similarity	NPD6584	Phase 3
0.7383	Intermediate Similarity	NPD7905	Discontinued
0.7378	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3656	Approved
0.7365	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6667	Approved
0.7358	Intermediate Similarity	NPD6666	Approved
0.7357	Intermediate Similarity	NPD228	Approved
0.7338	Intermediate Similarity	NPD823	Approved
0.7338	Intermediate Similarity	NPD817	Approved
0.7333	Intermediate Similarity	NPD5772	Approved
0.7333	Intermediate Similarity	NPD5773	Approved
0.7325	Intermediate Similarity	NPD7037	Approved
0.7325	Intermediate Similarity	NPD7153	Discontinued
0.7321	Intermediate Similarity	NPD4666	Phase 3
0.7321	Intermediate Similarity	NPD2904	Discontinued
0.7314	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5938	Phase 3
0.7308	Intermediate Similarity	NPD2161	Phase 2
0.7297	Intermediate Similarity	NPD4659	Approved
0.7296	Intermediate Similarity	NPD2677	Approved
0.7294	Intermediate Similarity	NPD4083	Discontinued
0.7284	Intermediate Similarity	NPD5976	Discontinued
0.7284	Intermediate Similarity	NPD2122	Discontinued
0.7283	Intermediate Similarity	NPD3452	Approved
0.7283	Intermediate Similarity	NPD2494	Approved
0.7283	Intermediate Similarity	NPD3450	Approved
0.7283	Intermediate Similarity	NPD2493	Approved
0.7283	Intermediate Similarity	NPD7479	Phase 2
0.7279	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD44	Approved
0.7278	Intermediate Similarity	NPD6364	Approved
0.7273	Intermediate Similarity	NPD5720	Discontinued
0.7268	Intermediate Similarity	NPD8095	Phase 1
0.7267	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5709	Phase 3
0.726	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6876	Approved
0.7256	Intermediate Similarity	NPD4678	Approved
0.7256	Intermediate Similarity	NPD6875	Approved
0.7256	Intermediate Similarity	NPD4675	Approved
0.7255	Intermediate Similarity	NPD3532	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