NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	327.15
Volume:	333.293
LogP:	2.092
LogD:	2.76
LogS:	-1.999
# 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:	3.182
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:	-4.887
MDCK Permeability:	1.41E-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.484
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.927
Plasma Protein Binding (PPB):	75.91%
Volume Distribution (VD):	1.697
Pgp-substrate:	18.31%

ADMET: Metabolism

CYP1A2-inhibitor:	0.693
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.719
CYP2D6-inhibitor:	0.263
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.897

ADMET: Excretion

Clearance (CL):	15.254
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.492
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.534
AMES Toxicity:	0.516
Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.774
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC477563

Natural Product ID:	NPC477563
*Common Name:**	(6As)-Boldine
IUPAC Name:	(6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol;2,2,2-trifluoroacetic acid
Synonyms:	(6As)-Boldine
Standard InCHIKey:	XERQSBGIQXGHOA-ZOWNYOTGSA-N
Standard InCHI:	InChI=1S/C19H21NO4.C2HF3O2/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18;3-2(4,5)1(6)7/h7-9,13,21-22H,4-6H2,1-3H3;(H,6,7)/t13-;/m0./s1
SMILES:	CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)O.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16215785
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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 NPC477563 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	258
0.1-0.2	1408
0.2-0.3	6029
0.3-0.4	12154
0.4-0.5	5275
0.5-0.6	11668
0.6-0.7	4961
0.7-0.8	672
0.8-0.85	153
0.85-0.9	80
0.9-0.95	34
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC306843
1.0	High Similarity	NPC253043
1.0	High Similarity	NPC212794
1.0	High Similarity	NPC96603
1.0	High Similarity	NPC196447
1.0	High Similarity	NPC136508
1.0	High Similarity	NPC13504
1.0	High Similarity	NPC78222
0.9934	High Similarity	NPC324144
0.987	High Similarity	NPC306555
0.987	High Similarity	NPC12053
0.987	High Similarity	NPC81218
0.987	High Similarity	NPC474931
0.987	High Similarity	NPC158376
0.987	High Similarity	NPC145832
0.987	High Similarity	NPC117188
0.987	High Similarity	NPC205421
0.9682	High Similarity	NPC239775
0.9675	High Similarity	NPC1229
0.9673	High Similarity	NPC27410
0.9673	High Similarity	NPC166014
0.9618	High Similarity	NPC26240
0.9618	High Similarity	NPC69712
0.9618	High Similarity	NPC477562
0.956	High Similarity	NPC229166
0.956	High Similarity	NPC128560
0.956	High Similarity	NPC199465
0.9539	High Similarity	NPC325871
0.9539	High Similarity	NPC99659
0.9497	High Similarity	NPC477020
0.9497	High Similarity	NPC192135
0.9497	High Similarity	NPC66341
0.9494	High Similarity	NPC168753
0.9494	High Similarity	NPC118274
0.9441	High Similarity	NPC114364
0.9441	High Similarity	NPC320223
0.9416	High Similarity	NPC476572
0.9359	High Similarity	NPC60186
0.9304	High Similarity	NPC81247
0.9304	High Similarity	NPC35627
0.9304	High Similarity	NPC476573
0.9268	High Similarity	NPC116284
0.9264	High Similarity	NPC474507
0.9216	High Similarity	NPC326316
0.9216	High Similarity	NPC81733
0.9207	High Similarity	NPC477561
0.9207	High Similarity	NPC312918
0.9207	High Similarity	NPC155442
0.9207	High Similarity	NPC476574
0.9141	High Similarity	NPC476577
0.9141	High Similarity	NPC148709
0.9141	High Similarity	NPC173416
0.9125	High Similarity	NPC298979
0.9119	High Similarity	NPC302527
0.9119	High Similarity	NPC167546
0.9119	High Similarity	NPC16805
0.9096	High Similarity	NPC135772
0.9062	High Similarity	NPC24264
0.9062	High Similarity	NPC476432
0.9038	High Similarity	NPC276588
0.9038	High Similarity	NPC110416
0.9038	High Similarity	NPC207757
0.9038	High Similarity	NPC204828
0.9038	High Similarity	NPC295691
0.9038	High Similarity	NPC39701
0.9038	High Similarity	NPC172765
0.9038	High Similarity	NPC278799
0.9038	High Similarity	NPC189266
0.9038	High Similarity	NPC127674
0.9038	High Similarity	NPC54379
0.9038	High Similarity	NPC2413
0.9038	High Similarity	NPC184026
0.9038	High Similarity	NPC469817
0.9038	High Similarity	NPC5238
0.9038	High Similarity	NPC249797
0.9038	High Similarity	NPC193949
0.9026	High Similarity	NPC192768
0.9026	High Similarity	NPC88249
0.9026	High Similarity	NPC151895
0.9026	High Similarity	NPC97221
0.9026	High Similarity	NPC220858
0.902	High Similarity	NPC428
0.902	High Similarity	NPC246587
0.902	High Similarity	NPC135538
0.902	High Similarity	NPC24233
0.902	High Similarity	NPC476571
0.902	High Similarity	NPC147390
0.9006	High Similarity	NPC247389
0.9006	High Similarity	NPC210918
0.9	High Similarity	NPC225774
0.9	High Similarity	NPC24465
0.8994	High Similarity	NPC82763
0.8981	High Similarity	NPC186063
0.8961	High Similarity	NPC477565
0.8961	High Similarity	NPC103379
0.8954	High Similarity	NPC321505
0.8954	High Similarity	NPC191376
0.8954	High Similarity	NPC179825
0.8944	High Similarity	NPC13916
0.8944	High Similarity	NPC264850
0.8944	High Similarity	NPC219341
0.8935	High Similarity	NPC476576
0.8935	High Similarity	NPC186546
0.8922	High Similarity	NPC248642
0.8916	High Similarity	NPC126284
0.8889	High Similarity	NPC478093
0.8889	High Similarity	NPC204947
0.8876	High Similarity	NPC320088
0.8869	High Similarity	NPC156576
0.8861	High Similarity	NPC203784
0.8861	High Similarity	NPC170503
0.8861	High Similarity	NPC126519
0.8848	High Similarity	NPC477558
0.8841	High Similarity	NPC149090
0.8841	High Similarity	NPC19520
0.8837	High Similarity	NPC473589
0.8837	High Similarity	NPC478092
0.8837	High Similarity	NPC30182
0.8837	High Similarity	NPC478091
0.8831	High Similarity	NPC476151
0.8824	High Similarity	NPC185838
0.8812	High Similarity	NPC160298
0.8812	High Similarity	NPC232924
0.8812	High Similarity	NPC266753
0.8812	High Similarity	NPC477559
0.8812	High Similarity	NPC306902
0.8802	High Similarity	NPC32154
0.8797	High Similarity	NPC244112
0.878	High Similarity	NPC6152
0.8773	High Similarity	NPC150879
0.8773	High Similarity	NPC210140
0.8765	High Similarity	NPC57036
0.872	High Similarity	NPC83198
0.872	High Similarity	NPC204908
0.8712	High Similarity	NPC124657
0.8696	High Similarity	NPC235143
0.8696	High Similarity	NPC205167
0.8696	High Similarity	NPC205255
0.8696	High Similarity	NPC271388
0.8696	High Similarity	NPC230956
0.8696	High Similarity	NPC119649
0.8696	High Similarity	NPC249274
0.8683	High Similarity	NPC241704
0.8671	High Similarity	NPC26601
0.8667	High Similarity	NPC152212
0.8655	High Similarity	NPC214116
0.865	High Similarity	NPC276944
0.865	High Similarity	NPC232514
0.865	High Similarity	NPC238530
0.865	High Similarity	NPC169743
0.865	High Similarity	NPC134858
0.8647	High Similarity	NPC33902
0.8647	High Similarity	NPC276674
0.8642	High Similarity	NPC80759
0.8642	High Similarity	NPC79402
0.8634	High Similarity	NPC221864
0.8634	High Similarity	NPC111485
0.8631	High Similarity	NPC118633
0.8631	High Similarity	NPC148693
0.8631	High Similarity	NPC294790
0.8623	High Similarity	NPC329969
0.8616	High Similarity	NPC2295
0.8616	High Similarity	NPC477564
0.8614	High Similarity	NPC231371
0.8608	High Similarity	NPC277669
0.8608	High Similarity	NPC76213
0.8605	High Similarity	NPC275680
0.8605	High Similarity	NPC22115
0.859	High Similarity	NPC16107
0.859	High Similarity	NPC210437
0.859	High Similarity	NPC476144
0.859	High Similarity	NPC106295
0.859	High Similarity	NPC51957
0.8589	High Similarity	NPC233650
0.858	High Similarity	NPC220961
0.8571	High Similarity	NPC128019
0.8571	High Similarity	NPC476567
0.8571	High Similarity	NPC136860
0.8563	High Similarity	NPC78284
0.8563	High Similarity	NPC152680
0.8563	High Similarity	NPC190783
0.8563	High Similarity	NPC232386
0.8562	High Similarity	NPC213206
0.8562	High Similarity	NPC188163
0.8562	High Similarity	NPC470925
0.8562	High Similarity	NPC474915
0.8562	High Similarity	NPC328750
0.8535	High Similarity	NPC7467
0.8535	High Similarity	NPC130941
0.8529	High Similarity	NPC286119
0.8521	High Similarity	NPC190461
0.8506	High Similarity	NPC475754
0.8497	Intermediate Similarity	NPC314682
0.8494	Intermediate Similarity	NPC241055
0.8488	Intermediate Similarity	NPC16357
0.8488	Intermediate Similarity	NPC302245
0.8488	Intermediate Similarity	NPC95426
0.8485	Intermediate Similarity	NPC240841
0.8485	Intermediate Similarity	NPC42549
0.8485	Intermediate Similarity	NPC250846

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 NPC477563 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	713
0.2-0.3	1097
0.3-0.4	2063
0.4-0.5	2579
0.5-0.6	1767
0.6-0.7	616
0.7-0.8	126
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD2420	Approved
0.8889	High Similarity	NPD2421	Approved
0.8606	High Similarity	NPD27	Approved
0.8606	High Similarity	NPD2489	Approved
0.8598	High Similarity	NPD3051	Approved
0.859	High Similarity	NPD4584	Approved
0.8562	High Similarity	NPD4664	Clinical (unspecified phase)
0.8545	High Similarity	NPD2970	Approved
0.8545	High Similarity	NPD2969	Approved
0.848	Intermediate Similarity	NPD8053	Approved
0.848	Intermediate Similarity	NPD8054	Approved
0.8439	Intermediate Similarity	NPD7906	Approved
0.8314	Intermediate Similarity	NPD4577	Approved
0.8314	Intermediate Similarity	NPD7312	Approved
0.8314	Intermediate Similarity	NPD4578	Approved
0.8314	Intermediate Similarity	NPD7311	Approved
0.8314	Intermediate Similarity	NPD7313	Approved
0.8314	Intermediate Similarity	NPD7310	Approved
0.8276	Intermediate Similarity	NPD4663	Approved
0.8274	Intermediate Similarity	NPD2898	Approved
0.8266	Intermediate Similarity	NPD7309	Approved
0.8263	Intermediate Similarity	NPD4010	Discontinued
0.8171	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5241	Discontinued
0.8144	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD3845	Phase 1
0.8113	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD8252	Approved
0.807	Intermediate Similarity	NPD8251	Approved
0.807	Intermediate Similarity	NPD8099	Discontinued
0.8059	Intermediate Similarity	NPD4481	Phase 3
0.8034	Intermediate Similarity	NPD2490	Approved
0.8034	Intermediate Similarity	NPD2488	Approved
0.8024	Intermediate Similarity	NPD7831	Phase 2
0.8024	Intermediate Similarity	NPD7833	Phase 2
0.8024	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD8156	Discontinued
0.8	Intermediate Similarity	NPD7298	Approved
0.8	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6788	Approved
0.7939	Intermediate Similarity	NPD4773	Phase 2
0.7939	Intermediate Similarity	NPD4772	Phase 2
0.7927	Intermediate Similarity	NPD4017	Approved
0.7901	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD3450	Approved
0.7838	Intermediate Similarity	NPD2494	Approved
0.7838	Intermediate Similarity	NPD2493	Approved
0.7838	Intermediate Similarity	NPD3452	Approved
0.7836	Intermediate Similarity	NPD6071	Discontinued
0.7805	Intermediate Similarity	NPD3640	Phase 3
0.7805	Intermediate Similarity	NPD3639	Approved
0.7805	Intermediate Similarity	NPD3641	Approved
0.7798	Intermediate Similarity	NPD2560	Approved
0.7798	Intermediate Similarity	NPD2563	Approved
0.7756	Intermediate Similarity	NPD3110	Approved
0.7756	Intermediate Similarity	NPD3109	Approved
0.7751	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD4583	Approved
0.7713	Intermediate Similarity	NPD4582	Approved
0.7697	Intermediate Similarity	NPD2971	Approved
0.7697	Intermediate Similarity	NPD2968	Approved
0.7697	Intermediate Similarity	NPD6030	Approved
0.7697	Intermediate Similarity	NPD6031	Approved
0.7673	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4002	Approved
0.766	Intermediate Similarity	NPD4004	Approved
0.7625	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2973	Approved
0.7622	Intermediate Similarity	NPD2974	Approved
0.7622	Intermediate Similarity	NPD2975	Approved
0.7602	Intermediate Similarity	NPD4055	Discovery
0.7564	Intermediate Similarity	NPD5155	Approved
0.7564	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD5156	Approved
0.753	Intermediate Similarity	NPD6090	Discontinued
0.7516	Intermediate Similarity	NPD5718	Phase 2
0.75	Intermediate Similarity	NPD3594	Approved
0.75	Intermediate Similarity	NPD2605	Approved
0.75	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7047	Phase 3
0.75	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2606	Approved
0.75	Intermediate Similarity	NPD4580	Approved
0.75	Intermediate Similarity	NPD3595	Approved
0.75	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3060	Approved
0.7485	Intermediate Similarity	NPD5177	Phase 3
0.7471	Intermediate Similarity	NPD7802	Discontinued
0.7469	Intermediate Similarity	NPD4726	Approved
0.7469	Intermediate Similarity	NPD4725	Approved
0.7469	Intermediate Similarity	NPD4721	Approved
0.7468	Intermediate Similarity	NPD2674	Phase 3
0.7453	Intermediate Similarity	NPD1753	Discontinued
0.745	Intermediate Similarity	NPD6997	Phase 2
0.7436	Intermediate Similarity	NPD3637	Approved
0.7436	Intermediate Similarity	NPD3636	Approved
0.7436	Intermediate Similarity	NPD3635	Approved
0.7435	Intermediate Similarity	NPD4040	Phase 1
0.743	Intermediate Similarity	NPD6297	Approved
0.7427	Intermediate Similarity	NPD2978	Approved
0.7427	Intermediate Similarity	NPD2977	Approved
0.7416	Intermediate Similarity	NPD6042	Phase 2
0.7416	Intermediate Similarity	NPD42	Phase 2
0.7396	Intermediate Similarity	NPD4005	Discontinued
0.7394	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6107	Approved
0.7365	Intermediate Similarity	NPD1424	Approved
0.7362	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4474	Approved
0.7358	Intermediate Similarity	NPD4475	Approved
0.733	Intermediate Similarity	NPD3448	Approved
0.733	Intermediate Similarity	NPD2491	Approved
0.733	Intermediate Similarity	NPD3057	Approved
0.7314	Intermediate Similarity	NPD4666	Phase 3
0.7308	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3124	Discontinued
0.7296	Intermediate Similarity	NPD3145	Approved
0.7296	Intermediate Similarity	NPD3144	Approved
0.7284	Intermediate Similarity	NPD6896	Approved
0.7284	Intermediate Similarity	NPD6895	Approved
0.7278	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4236	Phase 3
0.7273	Intermediate Similarity	NPD4237	Approved
0.7268	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6851	Approved
0.7268	Intermediate Similarity	NPD6853	Approved
0.7263	Intermediate Similarity	NPD8095	Phase 1
0.7262	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4123	Phase 3
0.7257	Intermediate Similarity	NPD5709	Phase 3
0.7246	Intermediate Similarity	NPD6667	Approved
0.7246	Intermediate Similarity	NPD7124	Phase 2
0.7246	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6666	Approved
0.724	Intermediate Similarity	NPD2972	Approved
0.724	Intermediate Similarity	NPD3533	Approved
0.7232	Intermediate Similarity	NPD4166	Phase 2
0.7229	Intermediate Similarity	NPD5754	Discontinued
0.7219	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4257	Approved
0.7212	Intermediate Similarity	NPD4256	Phase 2
0.7209	Intermediate Similarity	NPD6072	Discontinued
0.7202	Intermediate Similarity	NPD7598	Phase 2
0.7193	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6688	Approved
0.7191	Intermediate Similarity	NPD6687	Approved
0.7186	Intermediate Similarity	NPD5160	Discontinued
0.7182	Intermediate Similarity	NPD7479	Phase 2
0.7178	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4727	Phase 1
0.7176	Intermediate Similarity	NPD5976	Discontinued
0.7172	Intermediate Similarity	NPD7827	Phase 1
0.716	Intermediate Similarity	NPD7447	Phase 1
0.7135	Intermediate Similarity	NPD6747	Phase 1
0.7135	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4873	Discontinued
0.7127	Intermediate Similarity	NPD5312	Approved
0.7127	Intermediate Similarity	NPD5313	Approved
0.7126	Intermediate Similarity	NPD6748	Discontinued
0.7126	Intermediate Similarity	NPD5772	Approved
0.7126	Intermediate Similarity	NPD5773	Approved
0.7124	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4420	Approved
0.7118	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7037	Approved
0.7102	Intermediate Similarity	NPD5604	Discontinued
0.7101	Intermediate Similarity	NPD7213	Phase 3
0.7101	Intermediate Similarity	NPD7212	Phase 2
0.7099	Intermediate Similarity	NPD2238	Phase 2
0.7089	Intermediate Similarity	NPD3053	Approved
0.7089	Intermediate Similarity	NPD3055	Approved
0.7086	Intermediate Similarity	NPD5977	Approved
0.7086	Intermediate Similarity	NPD5978	Approved
0.7083	Intermediate Similarity	NPD3692	Discontinued
0.7081	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4093	Discontinued
0.7076	Intermediate Similarity	NPD1914	Approved
0.7076	Intermediate Similarity	NPD2122	Discontinued
0.7074	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1669	Approved
0.7066	Intermediate Similarity	NPD4162	Approved
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7062	Intermediate Similarity	NPD7400	Phase 3
0.7059	Intermediate Similarity	NPD7907	Approved
0.7052	Intermediate Similarity	NPD4675	Approved
0.7052	Intermediate Similarity	NPD4678	Approved
0.7049	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6612	Phase 2
0.7047	Intermediate Similarity	NPD4107	Approved
0.7035	Intermediate Similarity	NPD5676	Approved
0.7029	Intermediate Similarity	NPD4585	Approved
0.7024	Intermediate Similarity	NPD6331	Phase 2
0.7022	Intermediate Similarity	NPD5677	Discontinued
0.7013	Intermediate Similarity	NPD5303	Approved
0.7013	Intermediate Similarity	NPD5304	Approved
0.7012	Intermediate Similarity	NPD823	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