NPASS Compound

Structure

CID110416 OpenBabel06191715462D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 0.0000 1.0000 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 3.4641 3.0000 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 0.8660 1.5000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 20 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	327.15
Volume:	333.293
LogP:	2.156
LogD:	2.826
LogS:	-1.724
# Rotatable Bonds:	2
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.888
Synthetic Accessibility Score:	3.053
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.062
MDCK Permeability:	1.978200816665776e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.146
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.096

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	92.62212371826172%
Volume Distribution (VD):	1.03
Pgp-substrate:	8.635332107543945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.763
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.601
CYP2D6-inhibitor:	0.785
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.878

ADMET: Excretion

Clearance (CL):	17.463
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.296
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.803
Carcinogencity:	0.156
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC110416

Natural Product ID:	NPC110416
*Common Name:**	3,9-Dimethoxy-5,8,13,13A-Tetrahydro-6H-Isoquino[3,2-A]Isoquinoline-2,10-Diol
IUPAC Name:	3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
Synonyms:
Standard InCHIKey:	JKPISQIIWUONPB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3
SMILES:	COc1cc2CCN3C(c2cc1O)Cc1c(C3)c(OC)c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL595489
PubChem CID:	5290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Ki	5
Others	4

Activity Type	# Activity
Individual Protein	4
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT296	Individual Protein	Sigma opioid receptor	Homo sapiens	Ki	=	269.0	nM	PMID[479866]
NPT244	Individual Protein	Dopamine D3 receptor	Homo sapiens	Ki	=	101.0	nM	PMID[479866]
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Ki	=	115.5	nM	PMID[479866]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Ki	=	5.6	nM	PMID[479866]
NPT2	Others	Unspecified		Ki	=	9.0	nM	PMID[479866]
NPT2	Others	Unspecified		Ratio Ki	=	20.6	n.a.	PMID[479866]
NPT2	Others	Unspecified		Ratio Ki	=	18.0	n.a.	PMID[479866]
NPT2	Others	Unspecified		Ratio Ki	=	1.1	n.a.	PMID[479866]
NPT2	Others	Unspecified		Ratio Ki	=	30.0	n.a.	PMID[479866]

☑ 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 NPC110416 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	284
0.1-0.2	1652
0.2-0.3	8684
0.3-0.4	9313
0.4-0.5	5749
0.5-0.6	11219
0.6-0.7	4445
0.7-0.8	892
0.8-0.85	234
0.85-0.9	141
0.9-0.95	58
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189266
1.0	High Similarity	NPC184026
1.0	High Similarity	NPC204828
1.0	High Similarity	NPC295691
1.0	High Similarity	NPC54379
1.0	High Similarity	NPC207757
1.0	High Similarity	NPC276588
1.0	High Similarity	NPC39701
1.0	High Similarity	NPC5238
1.0	High Similarity	NPC172765
1.0	High Similarity	NPC127674
1.0	High Similarity	NPC249797
1.0	High Similarity	NPC2413
1.0	High Similarity	NPC469817
1.0	High Similarity	NPC278799
1.0	High Similarity	NPC193949
0.9724	High Similarity	NPC220858
0.9724	High Similarity	NPC192768
0.9724	High Similarity	NPC151895
0.9724	High Similarity	NPC97221
0.9724	High Similarity	NPC88249
0.9655	High Similarity	NPC477565
0.9655	High Similarity	NPC103379
0.9586	High Similarity	NPC135538
0.9586	High Similarity	NPC476571
0.9586	High Similarity	NPC24233
0.9586	High Similarity	NPC147390
0.9586	High Similarity	NPC246587
0.9586	High Similarity	NPC428
0.9539	High Similarity	NPC238530
0.9539	High Similarity	NPC276944
0.9539	High Similarity	NPC232514
0.9517	High Similarity	NPC179825
0.9517	High Similarity	NPC476144
0.9517	High Similarity	NPC476151
0.9517	High Similarity	NPC106295
0.9517	High Similarity	NPC191376
0.9517	High Similarity	NPC210437
0.9517	High Similarity	NPC16107
0.9517	High Similarity	NPC51957
0.9517	High Similarity	NPC321505
0.9477	High Similarity	NPC264850
0.9477	High Similarity	NPC13916
0.9452	High Similarity	NPC7467
0.9412	High Similarity	NPC24465
0.9379	High Similarity	NPC185838
0.9276	High Similarity	NPC111485
0.9267	High Similarity	NPC2295
0.9267	High Similarity	NPC477564
0.9241	High Similarity	NPC136860
0.9241	High Similarity	NPC128019
0.9241	High Similarity	NPC476567
0.9216	High Similarity	NPC166014
0.9216	High Similarity	NPC27410
0.9133	High Similarity	NPC76213
0.9133	High Similarity	NPC277669
0.9103	High Similarity	NPC317272
0.9103	High Similarity	NPC42549
0.9103	High Similarity	NPC240841
0.9103	High Similarity	NPC256012
0.9103	High Similarity	NPC474915
0.9103	High Similarity	NPC250846
0.9103	High Similarity	NPC328750
0.9103	High Similarity	NPC268503
0.9103	High Similarity	NPC188163
0.9103	High Similarity	NPC213206
0.9097	High Similarity	NPC324144
0.9079	High Similarity	NPC216459
0.9079	High Similarity	NPC41178
0.9079	High Similarity	NPC138487
0.9073	High Similarity	NPC37272
0.9045	High Similarity	NPC145832
0.9045	High Similarity	NPC205421
0.9045	High Similarity	NPC474931
0.9045	High Similarity	NPC12053
0.9045	High Similarity	NPC81218
0.9045	High Similarity	NPC158376
0.9045	High Similarity	NPC306555
0.9045	High Similarity	NPC117188
0.9038	High Similarity	NPC96603
0.9038	High Similarity	NPC13504
0.9038	High Similarity	NPC284183
0.9038	High Similarity	NPC136508
0.9038	High Similarity	NPC477563
0.9038	High Similarity	NPC253043
0.9038	High Similarity	NPC306843
0.9038	High Similarity	NPC78222
0.9038	High Similarity	NPC121275
0.9038	High Similarity	NPC196447
0.9038	High Similarity	NPC4138
0.9038	High Similarity	NPC212794
0.9034	High Similarity	NPC314682
0.9032	High Similarity	NPC60186
0.902	High Similarity	NPC146288
0.9	High Similarity	NPC207824
0.9	High Similarity	NPC60538
0.8987	High Similarity	NPC204908
0.8987	High Similarity	NPC83198
0.8951	High Similarity	NPC32154
0.8947	High Similarity	NPC82285
0.8947	High Similarity	NPC133011
0.8896	High Similarity	NPC147091
0.8896	High Similarity	NPC31311
0.8896	High Similarity	NPC234392
0.8868	High Similarity	NPC66573
0.8861	High Similarity	NPC476573
0.8861	High Similarity	NPC35627
0.8861	High Similarity	NPC81247
0.8854	High Similarity	NPC1229
0.8841	High Similarity	NPC290005
0.8841	High Similarity	NPC8836
0.8841	High Similarity	NPC239824
0.8841	High Similarity	NPC217748
0.8841	High Similarity	NPC328155
0.8841	High Similarity	NPC42663
0.8841	High Similarity	NPC182052
0.8841	High Similarity	NPC104196
0.8841	High Similarity	NPC54654
0.8841	High Similarity	NPC222661
0.8841	High Similarity	NPC90998
0.8841	High Similarity	NPC290582
0.8841	High Similarity	NPC285931
0.8841	High Similarity	NPC271013
0.8841	High Similarity	NPC223690
0.8841	High Similarity	NPC251735
0.8841	High Similarity	NPC49075
0.8841	High Similarity	NPC15414
0.8841	High Similarity	NPC279228
0.8841	High Similarity	NPC258657
0.8841	High Similarity	NPC181796
0.8841	High Similarity	NPC311973
0.8841	High Similarity	NPC185639
0.8841	High Similarity	NPC229373
0.8841	High Similarity	NPC7715
0.8828	High Similarity	NPC301050
0.8828	High Similarity	NPC131204
0.8827	High Similarity	NPC241704
0.882	High Similarity	NPC190783
0.882	High Similarity	NPC232386
0.882	High Similarity	NPC2314
0.882	High Similarity	NPC152680
0.8812	High Similarity	NPC109925
0.8788	High Similarity	NPC274716
0.8788	High Similarity	NPC254441
0.8788	High Similarity	NPC167116
0.878	High Similarity	NPC286119
0.8774	High Similarity	NPC186063
0.8758	High Similarity	NPC81733
0.8758	High Similarity	NPC239775
0.8758	High Similarity	NPC326316
0.8758	High Similarity	NPC108434
0.8758	High Similarity	NPC475215
0.8727	High Similarity	NPC30779
0.8726	High Similarity	NPC205167
0.8704	High Similarity	NPC192135
0.8704	High Similarity	NPC66341
0.8704	High Similarity	NPC477020
0.8701	High Similarity	NPC233029
0.8701	High Similarity	NPC210148
0.8696	High Similarity	NPC69712
0.8696	High Similarity	NPC477562
0.8696	High Similarity	NPC26240
0.8696	High Similarity	NPC118274
0.8696	High Similarity	NPC168753
0.8693	High Similarity	NPC274026
0.8688	High Similarity	NPC210140
0.8688	High Similarity	NPC298979
0.8684	High Similarity	NPC475959
0.8683	High Similarity	NPC212237
0.8683	High Similarity	NPC116465
0.8667	High Similarity	NPC294249
0.8659	High Similarity	NPC320223
0.8659	High Similarity	NPC114364
0.8654	High Similarity	NPC247639
0.8654	High Similarity	NPC25084
0.865	High Similarity	NPC128560
0.865	High Similarity	NPC199465
0.865	High Similarity	NPC229166
0.8631	High Similarity	NPC22115
0.8631	High Similarity	NPC275680
0.8627	High Similarity	NPC92541
0.8608	High Similarity	NPC249274
0.8599	High Similarity	NPC475326
0.8599	High Similarity	NPC476572
0.859	High Similarity	NPC187022
0.859	High Similarity	NPC99659
0.859	High Similarity	NPC80129
0.859	High Similarity	NPC325871
0.8581	High Similarity	NPC26601
0.858	High Similarity	NPC274661
0.858	High Similarity	NPC48490
0.858	High Similarity	NPC175890
0.858	High Similarity	NPC206900
0.858	High Similarity	NPC11296
0.858	High Similarity	NPC82457
0.8562	High Similarity	NPC3375
0.8562	High Similarity	NPC255607
0.8562	High Similarity	NPC134858
0.8529	High Similarity	NPC191132
0.8529	High Similarity	NPC60295

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 NPC110416 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	761
0.2-0.3	1075
0.3-0.4	1769
0.4-0.5	2623
0.5-0.6	1772
0.6-0.7	745
0.7-0.8	186
0.8-0.85	29
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9517	High Similarity	NPD4584	Approved
0.9103	High Similarity	NPD4664	Clinical (unspecified phase)
0.8841	High Similarity	NPD8054	Approved
0.8841	High Similarity	NPD8053	Approved
0.8645	High Similarity	NPD4773	Phase 2
0.8645	High Similarity	NPD4772	Phase 2
0.8625	High Similarity	NPD4010	Discontinued
0.859	High Similarity	NPD7298	Approved
0.8519	High Similarity	NPD2898	Approved
0.8497	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD2420	Approved
0.8431	Intermediate Similarity	NPD2421	Approved
0.8415	Intermediate Similarity	NPD8252	Approved
0.8415	Intermediate Similarity	NPD8251	Approved
0.8415	Intermediate Similarity	NPD8099	Discontinued
0.8397	Intermediate Similarity	NPD4017	Approved
0.8387	Intermediate Similarity	NPD3641	Approved
0.8387	Intermediate Similarity	NPD3639	Approved
0.8387	Intermediate Similarity	NPD3640	Phase 3
0.8385	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD8156	Discontinued
0.8301	Intermediate Similarity	NPD5241	Discontinued
0.8293	Intermediate Similarity	NPD27	Approved
0.8293	Intermediate Similarity	NPD2489	Approved
0.8267	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6031	Approved
0.8153	Intermediate Similarity	NPD6030	Approved
0.8148	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7833	Phase 2
0.8148	Intermediate Similarity	NPD7831	Phase 2
0.8129	Intermediate Similarity	NPD3845	Phase 1
0.8121	Intermediate Similarity	NPD2969	Approved
0.8121	Intermediate Similarity	NPD2970	Approved
0.8086	Intermediate Similarity	NPD6788	Approved
0.8061	Intermediate Similarity	NPD3051	Approved
0.8013	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6107	Approved
0.7987	Intermediate Similarity	NPD5718	Phase 2
0.7962	Intermediate Similarity	NPD3124	Discontinued
0.7952	Intermediate Similarity	NPD6071	Discontinued
0.7935	Intermediate Similarity	NPD5177	Phase 3
0.7933	Intermediate Similarity	NPD2674	Phase 3
0.7931	Intermediate Similarity	NPD7906	Approved
0.7919	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2563	Approved
0.7914	Intermediate Similarity	NPD2560	Approved
0.7907	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7313	Approved
0.7907	Intermediate Similarity	NPD7312	Approved
0.7907	Intermediate Similarity	NPD7310	Approved
0.7907	Intermediate Similarity	NPD7311	Approved
0.7861	Intermediate Similarity	NPD7309	Approved
0.7836	Intermediate Similarity	NPD6297	Approved
0.7811	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4577	Approved
0.7803	Intermediate Similarity	NPD4578	Approved
0.7784	Intermediate Similarity	NPD7802	Discontinued
0.7771	Intermediate Similarity	NPD4663	Approved
0.7748	Intermediate Similarity	NPD3145	Approved
0.7748	Intermediate Similarity	NPD3144	Approved
0.7746	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4166	Phase 2
0.7733	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6896	Approved
0.7727	Intermediate Similarity	NPD6895	Approved
0.7722	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5313	Approved
0.7719	Intermediate Similarity	NPD5312	Approved
0.7707	Intermediate Similarity	NPD3060	Approved
0.7697	Intermediate Similarity	NPD4474	Approved
0.7697	Intermediate Similarity	NPD4475	Approved
0.7677	Intermediate Similarity	NPD1753	Discontinued
0.7667	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6853	Approved
0.7657	Intermediate Similarity	NPD6851	Approved
0.7651	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4481	Phase 3
0.764	Intermediate Similarity	NPD6090	Discontinued
0.764	Intermediate Similarity	NPD2488	Approved
0.764	Intermediate Similarity	NPD2490	Approved
0.7636	Intermediate Similarity	NPD2978	Approved
0.7636	Intermediate Similarity	NPD2977	Approved
0.7625	Intermediate Similarity	NPD7598	Phase 2
0.7605	Intermediate Similarity	NPD4055	Discovery
0.7595	Intermediate Similarity	NPD4162	Approved
0.7578	Intermediate Similarity	NPD1424	Approved
0.7568	Intermediate Similarity	NPD2232	Approved
0.7568	Intermediate Similarity	NPD2230	Approved
0.7568	Intermediate Similarity	NPD2233	Approved
0.7562	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6748	Discontinued
0.7541	Intermediate Similarity	NPD8095	Phase 1
0.7533	Intermediate Similarity	NPD3055	Approved
0.7533	Intermediate Similarity	NPD3053	Approved
0.7532	Intermediate Similarity	NPD3110	Approved
0.7532	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3109	Approved
0.75	Intermediate Similarity	NPD3692	Discontinued
0.75	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5978	Approved
0.7485	Intermediate Similarity	NPD5977	Approved
0.7484	Intermediate Similarity	NPD4237	Approved
0.7484	Intermediate Similarity	NPD4236	Phase 3
0.7483	Intermediate Similarity	NPD2668	Approved
0.7483	Intermediate Similarity	NPD2667	Approved
0.7468	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2238	Phase 2
0.741	Intermediate Similarity	NPD7110	Phase 1
0.741	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7280	Phase 3
0.7401	Intermediate Similarity	NPD7281	Phase 3
0.7394	Intermediate Similarity	NPD824	Approved
0.7394	Intermediate Similarity	NPD4005	Discontinued
0.7391	Intermediate Similarity	NPD5160	Discontinued
0.7378	Intermediate Similarity	NPD2122	Discontinued
0.7366	Intermediate Similarity	NPD3450	Approved
0.7366	Intermediate Similarity	NPD3452	Approved
0.7366	Intermediate Similarity	NPD2493	Approved
0.7366	Intermediate Similarity	NPD2494	Approved
0.7365	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4123	Phase 3
0.736	Intermediate Similarity	NPD6618	Phase 2
0.7347	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7124	Phase 2
0.7345	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5156	Approved
0.7338	Intermediate Similarity	NPD5155	Approved
0.7329	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5772	Approved
0.7321	Intermediate Similarity	NPD5773	Approved
0.732	Intermediate Similarity	NPD3635	Approved
0.732	Intermediate Similarity	NPD3636	Approved
0.732	Intermediate Similarity	NPD3637	Approved
0.7314	Intermediate Similarity	NPD4873	Discontinued
0.7297	Intermediate Similarity	NPD4093	Discontinued
0.7283	Intermediate Similarity	NPD6688	Approved
0.7283	Intermediate Similarity	NPD6687	Approved
0.7278	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2606	Approved
0.7273	Intermediate Similarity	NPD3595	Approved
0.7273	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3594	Approved
0.7273	Intermediate Similarity	NPD2605	Approved
0.7273	Intermediate Similarity	NPD7479	Phase 2
0.7253	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3656	Approved
0.7249	Intermediate Similarity	NPD4582	Approved
0.7249	Intermediate Similarity	NPD4583	Approved
0.7238	Intermediate Similarity	NPD7291	Discontinued
0.7237	Intermediate Similarity	NPD5310	Approved
0.7237	Intermediate Similarity	NPD5311	Approved
0.7237	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2156	Approved
0.7233	Intermediate Similarity	NPD2154	Approved
0.7233	Intermediate Similarity	NPD2155	Approved
0.723	Intermediate Similarity	NPD5303	Approved
0.723	Intermediate Similarity	NPD5304	Approved
0.7222	Intermediate Similarity	NPD6331	Phase 2
0.7215	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD823	Approved
0.7215	Intermediate Similarity	NPD817	Approved
0.7209	Intermediate Similarity	NPD2904	Discontinued
0.7209	Intermediate Similarity	NPD4666	Phase 3
0.7207	Intermediate Similarity	NPD2971	Approved
0.7207	Intermediate Similarity	NPD2968	Approved
0.7207	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7037	Approved
0.7204	Intermediate Similarity	NPD4420	Approved
0.72	Intermediate Similarity	NPD5938	Phase 3
0.7196	Intermediate Similarity	NPD4002	Approved
0.7196	Intermediate Similarity	NPD4004	Approved
0.7193	Intermediate Similarity	NPD5604	Discontinued
0.719	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4103	Phase 2
0.719	Intermediate Similarity	NPD4098	Discontinued
0.7184	Intermediate Similarity	NPD4083	Discontinued
0.7178	Intermediate Similarity	NPD2677	Approved
0.7171	Intermediate Similarity	NPD1669	Approved
0.7169	Intermediate Similarity	NPD1914	Approved
0.716	Intermediate Similarity	NPD5061	Approved
0.716	Intermediate Similarity	NPD5062	Approved
0.7158	Intermediate Similarity	NPD4040	Phase 1
0.7152	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7151	Intermediate Similarity	NPD2975	Approved
0.7151	Intermediate Similarity	NPD2974	Approved
0.7151	Intermediate Similarity	NPD2973	Approved
0.7151	Intermediate Similarity	NPD7549	Discontinued
0.7151	Intermediate Similarity	NPD5709	Phase 3
0.7143	Intermediate Similarity	NPD6875	Approved
0.7143	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD3296	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