NPASS Compound

Structure

NPC2295 OpenBabel07101719142D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 -2.5981 1.5000 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 1 21 1 0 0 0 0 2 5 1 0 0 0 0 2 11 2 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 12 16 2 0 0 0 0 13 19 1 0 0 0 0 14 10 1 6 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.14
Volume:	298.468
LogP:	1.221
LogD:	2.085
LogS:	-1.82
# Rotatable Bonds:	3
TPSA:	61.72
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	2.842
Fsp3:	0.294
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:	-5.012
MDCK Permeability:	1.4887655197526328e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.94
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	62.61174011230469%
Volume Distribution (VD):	2.341
Pgp-substrate:	28.795242309570312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.438
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.738
CYP2D6-inhibitor:	0.837
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.811

ADMET: Excretion

Clearance (CL):	13.168
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.503
Human Hepatotoxicity (H-HT):	0.434
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.807
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.924
Carcinogencity:	0.253
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC2295

Natural Product ID:	NPC2295
*Common Name:**	(1S)-Norjuziphine
IUPAC Name:	(1S)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-8-ol
Synonyms:	(1S)-Norjuziphine
Standard InCHIKey:	BXWMZVREXWPYKF-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C17H19NO3/c1-21-15-7-4-12-8-9-18-14(16(12)17(15)20)10-11-2-5-13(19)6-3-11/h2-7,14,18-20H,8-10H2,1H3/t14-/m0/s1
SMILES:	COc1ccc2c(c1O)[C@@H](NCC2)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462757
PubChem CID:	15690956
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
NPO32610	nectandra salicifolia	Species	Lauraceae	Eukaryota	trunk bark	lower montane rainforest in Costa Rica	n.a.	PMID[8786363]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.1	ug.mL-1	PMID[450354]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.1	ug.mL-1	PMID[450354]

☑ 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 NPC2295 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	268
0.1-0.2	1678
0.2-0.3	9643
0.3-0.4	8199
0.4-0.5	6292
0.5-0.6	11535
0.6-0.7	3938
0.7-0.8	798
0.8-0.85	186
0.85-0.9	111
0.9-0.95	40
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477564
0.9724	High Similarity	NPC277669
0.9724	High Similarity	NPC76213
0.9586	High Similarity	NPC207824
0.9586	High Similarity	NPC60538
0.9586	High Similarity	NPC103379
0.9586	High Similarity	NPC477565
0.9448	High Similarity	NPC476151
0.9315	High Similarity	NPC321505
0.9315	High Similarity	NPC191376
0.9315	High Similarity	NPC179825
0.9286	High Similarity	NPC35627
0.9286	High Similarity	NPC476573
0.9286	High Similarity	NPC81247
0.9267	High Similarity	NPC127674
0.9267	High Similarity	NPC276588
0.9267	High Similarity	NPC5238
0.9267	High Similarity	NPC39701
0.9267	High Similarity	NPC172765
0.9267	High Similarity	NPC54379
0.9267	High Similarity	NPC184026
0.9267	High Similarity	NPC295691
0.9267	High Similarity	NPC469817
0.9267	High Similarity	NPC189266
0.9267	High Similarity	NPC2413
0.9267	High Similarity	NPC204828
0.9267	High Similarity	NPC278799
0.9267	High Similarity	NPC207757
0.9267	High Similarity	NPC110416
0.9267	High Similarity	NPC249797
0.9267	High Similarity	NPC193949
0.9252	High Similarity	NPC147390
0.9252	High Similarity	NPC246587
0.9252	High Similarity	NPC135538
0.9252	High Similarity	NPC428
0.9252	High Similarity	NPC476571
0.9252	High Similarity	NPC24233
0.9241	High Similarity	NPC294249
0.9178	High Similarity	NPC185838
0.9	High Similarity	NPC220858
0.9	High Similarity	NPC88249
0.9	High Similarity	NPC192768
0.9	High Similarity	NPC97221
0.9	High Similarity	NPC151895
0.8994	High Similarity	NPC477020
0.8994	High Similarity	NPC192135
0.8994	High Similarity	NPC66341
0.8987	High Similarity	NPC477562
0.8987	High Similarity	NPC26240
0.8987	High Similarity	NPC69712
0.8974	High Similarity	NPC121275
0.8974	High Similarity	NPC4138
0.8974	High Similarity	NPC284183
0.8903	High Similarity	NPC27410
0.8903	High Similarity	NPC166014
0.8897	High Similarity	NPC211468
0.8897	High Similarity	NPC219233
0.8897	High Similarity	NPC170170
0.8854	High Similarity	NPC232514
0.8854	High Similarity	NPC276944
0.8854	High Similarity	NPC238530
0.8836	High Similarity	NPC314682
0.8836	High Similarity	NPC323123
0.8831	High Similarity	NPC170503
0.8831	High Similarity	NPC126519
0.8831	High Similarity	NPC203784
0.8828	High Similarity	NPC253429
0.8812	High Similarity	NPC475215
0.8812	High Similarity	NPC108434
0.88	High Similarity	NPC106295
0.88	High Similarity	NPC210437
0.88	High Similarity	NPC16107
0.88	High Similarity	NPC476144
0.88	High Similarity	NPC51957
0.8797	High Similarity	NPC13916
0.8797	High Similarity	NPC264850
0.8776	High Similarity	NPC328750
0.8776	High Similarity	NPC188163
0.8776	High Similarity	NPC474915
0.8776	High Similarity	NPC213206
0.8773	High Similarity	NPC474507
0.8765	High Similarity	NPC148709
0.8765	High Similarity	NPC476577
0.8765	High Similarity	NPC173416
0.8759	High Similarity	NPC131204
0.8759	High Similarity	NPC301050
0.8758	High Similarity	NPC133011
0.8758	High Similarity	NPC82285
0.875	High Similarity	NPC109925
0.8742	High Similarity	NPC7467
0.8734	High Similarity	NPC24465
0.8726	High Similarity	NPC60186
0.871	High Similarity	NPC147091
0.8688	High Similarity	NPC83198
0.8688	High Similarity	NPC204908
0.8681	High Similarity	NPC160692
0.8671	High Similarity	NPC324144
0.8654	High Similarity	NPC79328
0.8634	High Similarity	NPC152212
0.8625	High Similarity	NPC117188
0.8625	High Similarity	NPC205421
0.8625	High Similarity	NPC474931
0.8625	High Similarity	NPC158376
0.8625	High Similarity	NPC12053
0.8625	High Similarity	NPC81218
0.8625	High Similarity	NPC145832
0.8625	High Similarity	NPC306555
0.8616	High Similarity	NPC196447
0.8616	High Similarity	NPC306843
0.8616	High Similarity	NPC136508
0.8616	High Similarity	NPC253043
0.8616	High Similarity	NPC212794
0.8616	High Similarity	NPC13504
0.8616	High Similarity	NPC96603
0.8616	High Similarity	NPC78222
0.8616	High Similarity	NPC477563
0.8614	High Similarity	NPC135772
0.8606	High Similarity	NPC312918
0.8606	High Similarity	NPC477561
0.8606	High Similarity	NPC476574
0.8606	High Similarity	NPC155442
0.8599	High Similarity	NPC111485
0.8553	High Similarity	NPC1229
0.8533	High Similarity	NPC136860
0.8533	High Similarity	NPC128019
0.8533	High Similarity	NPC476567
0.8528	High Similarity	NPC232386
0.8528	High Similarity	NPC152680
0.8528	High Similarity	NPC190783
0.8526	High Similarity	NPC187022
0.8526	High Similarity	NPC80129
0.8521	High Similarity	NPC11296
0.8521	High Similarity	NPC175890
0.8521	High Similarity	NPC82457
0.8521	High Similarity	NPC274661
0.8521	High Similarity	NPC48490
0.8506	High Similarity	NPC274026
0.8483	Intermediate Similarity	NPC33338
0.8483	Intermediate Similarity	NPC302171
0.8483	Intermediate Similarity	NPC300020
0.8476	Intermediate Similarity	NPC477558
0.8476	Intermediate Similarity	NPC329969
0.8471	Intermediate Similarity	NPC29647
0.8471	Intermediate Similarity	NPC60295
0.8471	Intermediate Similarity	NPC186063
0.8471	Intermediate Similarity	NPC191132
0.8452	Intermediate Similarity	NPC81733
0.8452	Intermediate Similarity	NPC326316
0.8447	Intermediate Similarity	NPC240841
0.8447	Intermediate Similarity	NPC42549
0.8447	Intermediate Similarity	NPC304659
0.8447	Intermediate Similarity	NPC250846
0.8447	Intermediate Similarity	NPC317272
0.8447	Intermediate Similarity	NPC256012
0.8447	Intermediate Similarity	NPC86144
0.8447	Intermediate Similarity	NPC268503
0.8428	Intermediate Similarity	NPC205167
0.8428	Intermediate Similarity	NPC249274
0.8408	Intermediate Similarity	NPC216459
0.8408	Intermediate Similarity	NPC41178
0.8408	Intermediate Similarity	NPC138487
0.8405	Intermediate Similarity	NPC118274
0.8405	Intermediate Similarity	NPC168753
0.8397	Intermediate Similarity	NPC26601
0.8397	Intermediate Similarity	NPC37272
0.8395	Intermediate Similarity	NPC298979
0.8395	Intermediate Similarity	NPC210140
0.8385	Intermediate Similarity	NPC209377
0.8377	Intermediate Similarity	NPC475959
0.8354	Intermediate Similarity	NPC146288
0.8354	Intermediate Similarity	NPC239775
0.8354	Intermediate Similarity	NPC160931
0.8354	Intermediate Similarity	NPC37205
0.8353	Intermediate Similarity	NPC186546
0.8353	Intermediate Similarity	NPC476576
0.8345	Intermediate Similarity	NPC160193
0.8344	Intermediate Similarity	NPC470324
0.8333	Intermediate Similarity	NPC56887
0.8333	Intermediate Similarity	NPC195392
0.8333	Intermediate Similarity	NPC223077
0.8333	Intermediate Similarity	NPC193853
0.8323	Intermediate Similarity	NPC475393
0.8323	Intermediate Similarity	NPC32154
0.8323	Intermediate Similarity	NPC189470
0.8302	Intermediate Similarity	NPC475326
0.8301	Intermediate Similarity	NPC130926
0.8282	Intermediate Similarity	NPC204947
0.8272	Intermediate Similarity	NPC39103
0.8272	Intermediate Similarity	NPC134858
0.8272	Intermediate Similarity	NPC2770
0.8263	Intermediate Similarity	NPC320223
0.8263	Intermediate Similarity	NPC114364
0.8253	Intermediate Similarity	NPC128560
0.8253	Intermediate Similarity	NPC229166
0.8253	Intermediate Similarity	NPC199465
0.8239	Intermediate Similarity	NPC234392
0.8239	Intermediate Similarity	NPC31311
0.8232	Intermediate Similarity	NPC66573
0.8225	Intermediate Similarity	NPC42663
0.8225	Intermediate Similarity	NPC271013

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 NPC2295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	706
0.2-0.3	1097
0.3-0.4	1712
0.4-0.5	2701
0.5-0.6	1768
0.6-0.7	727
0.7-0.8	233
0.8-0.85	23
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD4584	Approved
0.8776	High Similarity	NPD4664	Clinical (unspecified phase)
0.8767	High Similarity	NPD1632	Clinical (unspecified phase)
0.8684	High Similarity	NPD6031	Approved
0.8684	High Similarity	NPD6030	Approved
0.8543	High Similarity	NPD3845	Phase 1
0.8526	High Similarity	NPD7298	Approved
0.8421	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2898	Approved
0.8333	Intermediate Similarity	NPD4010	Discontinued
0.8228	Intermediate Similarity	NPD4773	Phase 2
0.8228	Intermediate Similarity	NPD4772	Phase 2
0.8225	Intermediate Similarity	NPD8054	Approved
0.8225	Intermediate Similarity	NPD8053	Approved
0.8224	Intermediate Similarity	NPD3060	Approved
0.8217	Intermediate Similarity	NPD4017	Approved
0.8194	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3055	Approved
0.8194	Intermediate Similarity	NPD3053	Approved
0.8137	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2421	Approved
0.8129	Intermediate Similarity	NPD2420	Approved
0.8117	Intermediate Similarity	NPD5241	Discontinued
0.8105	Intermediate Similarity	NPD4162	Approved
0.8098	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6297	Approved
0.8077	Intermediate Similarity	NPD1424	Approved
0.8052	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2977	Approved
0.8012	Intermediate Similarity	NPD2489	Approved
0.8012	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD27	Approved
0.8012	Intermediate Similarity	NPD2978	Approved
0.8	Intermediate Similarity	NPD5160	Discontinued
0.7987	Intermediate Similarity	NPD2674	Phase 3
0.7975	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3640	Phase 3
0.7975	Intermediate Similarity	NPD3641	Approved
0.7975	Intermediate Similarity	NPD7831	Phase 2
0.7975	Intermediate Similarity	NPD3639	Approved
0.7975	Intermediate Similarity	NPD7833	Phase 2
0.7974	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6107	Approved
0.7919	Intermediate Similarity	NPD5718	Phase 2
0.7914	Intermediate Similarity	NPD6788	Approved
0.7907	Intermediate Similarity	NPD6851	Approved
0.7907	Intermediate Similarity	NPD6853	Approved
0.7892	Intermediate Similarity	NPD6071	Discontinued
0.7877	Intermediate Similarity	NPD5311	Approved
0.7877	Intermediate Similarity	NPD5310	Approved
0.7871	Intermediate Similarity	NPD5177	Phase 3
0.7853	Intermediate Similarity	NPD2560	Approved
0.7853	Intermediate Similarity	NPD2563	Approved
0.7844	Intermediate Similarity	NPD2969	Approved
0.7844	Intermediate Similarity	NPD2970	Approved
0.7843	Intermediate Similarity	NPD2155	Approved
0.7843	Intermediate Similarity	NPD2156	Approved
0.7843	Intermediate Similarity	NPD2154	Approved
0.7811	Intermediate Similarity	NPD8251	Approved
0.7811	Intermediate Similarity	NPD8252	Approved
0.7811	Intermediate Similarity	NPD8099	Discontinued
0.78	Intermediate Similarity	NPD3145	Approved
0.78	Intermediate Similarity	NPD3144	Approved
0.7799	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7598	Phase 2
0.7784	Intermediate Similarity	NPD3051	Approved
0.7784	Intermediate Similarity	NPD4166	Phase 2
0.7765	Intermediate Similarity	NPD4873	Discontinued
0.7765	Intermediate Similarity	NPD8156	Discontinued
0.7733	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD823	Approved
0.7712	Intermediate Similarity	NPD817	Approved
0.7692	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4666	Phase 3
0.7658	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2677	Approved
0.764	Intermediate Similarity	NPD5976	Discontinued
0.7633	Intermediate Similarity	NPD4083	Discontinued
0.7632	Intermediate Similarity	NPD4474	Approved
0.7632	Intermediate Similarity	NPD3530	Approved
0.7632	Intermediate Similarity	NPD4475	Approved
0.7632	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3531	Approved
0.7632	Intermediate Similarity	NPD3532	Approved
0.7605	Intermediate Similarity	NPD5709	Phase 3
0.7582	Intermediate Similarity	NPD3059	Approved
0.7582	Intermediate Similarity	NPD3062	Approved
0.7582	Intermediate Similarity	NPD3061	Approved
0.758	Intermediate Similarity	NPD7153	Discontinued
0.7571	Intermediate Similarity	NPD7906	Approved
0.7566	Intermediate Similarity	NPD598	Approved
0.7566	Intermediate Similarity	NPD597	Approved
0.7566	Intermediate Similarity	NPD601	Approved
0.7548	Intermediate Similarity	NPD6895	Approved
0.7548	Intermediate Similarity	NPD6896	Approved
0.7544	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7311	Approved
0.7543	Intermediate Similarity	NPD7313	Approved
0.7543	Intermediate Similarity	NPD4577	Approved
0.7543	Intermediate Similarity	NPD7312	Approved
0.7543	Intermediate Similarity	NPD7310	Approved
0.7543	Intermediate Similarity	NPD4578	Approved
0.7532	Intermediate Similarity	NPD2460	Phase 3
0.7532	Intermediate Similarity	NPD2459	Approved
0.7532	Intermediate Similarity	NPD2458	Approved
0.7516	Intermediate Similarity	NPD1130	Approved
0.7516	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1132	Approved
0.7516	Intermediate Similarity	NPD1136	Approved
0.7515	Intermediate Similarity	NPD5720	Discontinued
0.7515	Intermediate Similarity	NPD7802	Discontinued
0.7514	Intermediate Similarity	NPD7479	Phase 2
0.75	Intermediate Similarity	NPD2232	Approved
0.75	Intermediate Similarity	NPD1753	Discontinued
0.75	Intermediate Similarity	NPD2230	Approved
0.75	Intermediate Similarity	NPD2233	Approved
0.75	Intermediate Similarity	NPD7309	Approved
0.7484	Intermediate Similarity	NPD2989	Phase 2
0.7484	Intermediate Similarity	NPD2986	Phase 2
0.7484	Intermediate Similarity	NPD3054	Approved
0.7484	Intermediate Similarity	NPD5314	Approved
0.7484	Intermediate Similarity	NPD3052	Approved
0.7469	Intermediate Similarity	NPD6090	Discontinued
0.7468	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3124	Discontinued
0.744	Intermediate Similarity	NPD4055	Discovery
0.7439	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5977	Approved
0.7425	Intermediate Similarity	NPD5978	Approved
0.7421	Intermediate Similarity	NPD5062	Approved
0.7421	Intermediate Similarity	NPD5061	Approved
0.7416	Intermediate Similarity	NPD4663	Approved
0.7415	Intermediate Similarity	NPD2667	Approved
0.7415	Intermediate Similarity	NPD2668	Approved
0.7407	Intermediate Similarity	NPD2874	Phase 2
0.7407	Intermediate Similarity	NPD3645	Discontinued
0.7401	Intermediate Similarity	NPD6618	Phase 2
0.7399	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3122	Phase 3
0.7389	Intermediate Similarity	NPD2488	Approved
0.7389	Intermediate Similarity	NPD2490	Approved
0.7375	Intermediate Similarity	NPD6748	Discontinued
0.7372	Intermediate Similarity	NPD2653	Approved
0.7365	Intermediate Similarity	NPD4585	Approved
0.7365	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD593	Approved
0.7361	Intermediate Similarity	NPD595	Approved
0.736	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4256	Phase 2
0.7358	Intermediate Similarity	NPD4257	Approved
0.7356	Intermediate Similarity	NPD6042	Phase 2
0.7356	Intermediate Similarity	NPD42	Phase 2
0.7355	Intermediate Similarity	NPD3110	Approved
0.7355	Intermediate Similarity	NPD3109	Approved
0.7355	Intermediate Similarity	NPD2238	Phase 2
0.7346	Intermediate Similarity	NPD1774	Approved
0.7342	Intermediate Similarity	NPD3156	Discontinued
0.7338	Intermediate Similarity	NPD1336	Approved
0.7338	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD824	Approved
0.7329	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3692	Discontinued
0.7322	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4727	Phase 1
0.7312	Intermediate Similarity	NPD4236	Phase 3
0.7312	Intermediate Similarity	NPD4237	Approved
0.7303	Intermediate Similarity	NPD9619	Approved
0.7303	Intermediate Similarity	NPD9621	Approved
0.7303	Intermediate Similarity	NPD9620	Approved
0.7301	Intermediate Similarity	NPD3536	Discontinued
0.7301	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2120	Phase 2
0.7283	Intermediate Similarity	NPD4481	Phase 3
0.7279	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3687	Approved
0.7273	Intermediate Similarity	NPD3686	Approved
0.7267	Intermediate Similarity	NPD6331	Phase 2
0.7267	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5313	Approved
0.7257	Intermediate Similarity	NPD5312	Approved
0.7256	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD52	Approved
0.7256	Intermediate Similarity	NPD7526	Approved
0.7255	Intermediate Similarity	NPD3636	Approved
0.7255	Intermediate Similarity	NPD3637	Approved
0.7255	Intermediate Similarity	NPD3635	Approved
0.7246	Intermediate Similarity	NPD7110	Phase 1
0.7246	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6087	Phase 1

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