NPASS Compound

Structure

CID162653 OpenBabel06191715532D 26 31 0 0 1 0 0 0 0 0999 V2000 0.8659 -0.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 2.9262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 2.4391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5340 1.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3792 0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6897 2.9257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6897 0.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0350 1.9505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2243 -1.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 2.4381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 1.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 1.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3795 0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5343 2.4381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5343 1.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5351 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 -0.4876 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2246 -0.4870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4618 2.7395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4618 1.1615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3800 -1.9496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 23 1 0 0 0 0 9 26 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	349.1
Volume:	336.994
LogP:	3.627
LogD:	3.299
LogS:	-6.05
# Rotatable Bonds:	0
TPSA:	60.39
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	3.363
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	4.8600606533000246e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.902
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	96.1962661743164%
Volume Distribution (VD):	0.66
Pgp-substrate:	1.4966331720352173%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.701
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.987
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	12.326
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.922
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.757
Carcinogencity:	0.965
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC162653

Natural Product ID:	NPC162653
*Common Name:**	YZRQUTZNTDAYPJ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	8-Hydroxydihydrosanguinarine
Standard InCHIKey:	YZRQUTZNTDAYPJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H15NO5/c1-21-18-12(3-2-10-6-15-16(7-13(10)18)25-8-24-15)11-4-5-14-19(26-9-23-14)17(11)20(21)22/h2-7,20,22H,8-9H2,1H3
SMILES:	OC1c2c3OCOc3ccc2c2c(N1C)c1cc3OCOc3cc1cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1921809
PubChem CID:	14313843
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002665] Benzophenanthridine alkaloids [CHEMONTID:0002667] Dihydrobenzophenanthridine alkaloids

*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
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4500.0	nM	PMID[541891]

☑ 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 NPC162653 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	375
0.1-0.2	2023
0.2-0.3	8970
0.3-0.4	8728
0.4-0.5	7671
0.5-0.6	11986
0.6-0.7	2252
0.7-0.8	623
0.8-0.85	51
0.85-0.9	10
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC302001
0.931	High Similarity	NPC179704
0.9266	High Similarity	NPC474904
0.9138	High Similarity	NPC287588
0.904	High Similarity	NPC249405
0.884	High Similarity	NPC312531
0.871	High Similarity	NPC23080
0.871	High Similarity	NPC193906
0.8674	High Similarity	NPC276674
0.8674	High Similarity	NPC33902
0.8596	High Similarity	NPC285941
0.8579	High Similarity	NPC320088
0.8571	High Similarity	NPC295676
0.8495	Intermediate Similarity	NPC78284
0.8475	Intermediate Similarity	NPC298979
0.8466	Intermediate Similarity	NPC212163
0.8457	Intermediate Similarity	NPC24954
0.8453	Intermediate Similarity	NPC148693
0.8453	Intermediate Similarity	NPC190461
0.8453	Intermediate Similarity	NPC118633
0.8453	Intermediate Similarity	NPC294790
0.8438	Intermediate Similarity	NPC156728
0.8438	Intermediate Similarity	NPC244606
0.8415	Intermediate Similarity	NPC248642
0.8413	Intermediate Similarity	NPC17677
0.837	Intermediate Similarity	NPC156576
0.8352	Intermediate Similarity	NPC114364
0.8352	Intermediate Similarity	NPC320223
0.8306	Intermediate Similarity	NPC126284
0.8295	Intermediate Similarity	NPC160298
0.8295	Intermediate Similarity	NPC232924
0.8295	Intermediate Similarity	NPC266753
0.8295	Intermediate Similarity	NPC306902
0.8295	Intermediate Similarity	NPC477559
0.828	Intermediate Similarity	NPC214116
0.8268	Intermediate Similarity	NPC247389
0.8268	Intermediate Similarity	NPC210918
0.8242	Intermediate Similarity	NPC199465
0.8242	Intermediate Similarity	NPC128560
0.8242	Intermediate Similarity	NPC229166
0.8212	Intermediate Similarity	NPC24264
0.8212	Intermediate Similarity	NPC219341
0.8212	Intermediate Similarity	NPC476432
0.8187	Intermediate Similarity	NPC471489
0.8177	Intermediate Similarity	NPC152212
0.8156	Intermediate Similarity	NPC16805
0.8156	Intermediate Similarity	NPC302527
0.8156	Intermediate Similarity	NPC225774
0.8156	Intermediate Similarity	NPC167546
0.8138	Intermediate Similarity	NPC296742
0.8132	Intermediate Similarity	NPC19520
0.8132	Intermediate Similarity	NPC149090
0.8118	Intermediate Similarity	NPC275132
0.8101	Intermediate Similarity	NPC233650
0.8087	Intermediate Similarity	NPC2314
0.8085	Intermediate Similarity	NPC57036
0.8085	Intermediate Similarity	NPC224293
0.8079	Intermediate Similarity	NPC46451
0.8075	Intermediate Similarity	NPC135772
0.8068	Intermediate Similarity	NPC76079
0.8063	Intermediate Similarity	NPC29472
0.8056	Intermediate Similarity	NPC238530
0.8056	Intermediate Similarity	NPC276944
0.8056	Intermediate Similarity	NPC168409
0.8056	Intermediate Similarity	NPC134858
0.8056	Intermediate Similarity	NPC232514
0.8049	Intermediate Similarity	NPC118121
0.8043	Intermediate Similarity	NPC477558
0.8042	Intermediate Similarity	NPC112676
0.8034	Intermediate Similarity	NPC477080
0.8032	Intermediate Similarity	NPC69213
0.8023	Intermediate Similarity	NPC31311
0.8023	Intermediate Similarity	NPC234392
0.8022	Intermediate Similarity	NPC241055
0.8021	Intermediate Similarity	NPC476575
0.8021	Intermediate Similarity	NPC116284
0.8011	Intermediate Similarity	NPC86144
0.8011	Intermediate Similarity	NPC304659
0.801	Intermediate Similarity	NPC117717
0.801	Intermediate Similarity	NPC159101
0.8	Intermediate Similarity	NPC189470
0.8	Intermediate Similarity	NPC82763
0.7989	Intermediate Similarity	NPC166014
0.7989	Intermediate Similarity	NPC27410
0.7989	Intermediate Similarity	NPC477186
0.797	Intermediate Similarity	NPC235076
0.7968	Intermediate Similarity	NPC476574
0.7968	Intermediate Similarity	NPC155442
0.7968	Intermediate Similarity	NPC312918
0.7968	Intermediate Similarity	NPC477561
0.7968	Intermediate Similarity	NPC32413
0.7968	Intermediate Similarity	NPC474506
0.7967	Intermediate Similarity	NPC158376
0.7967	Intermediate Similarity	NPC474931
0.7967	Intermediate Similarity	NPC205421
0.7967	Intermediate Similarity	NPC306555
0.7967	Intermediate Similarity	NPC81218
0.7967	Intermediate Similarity	NPC117188
0.7967	Intermediate Similarity	NPC150879
0.7967	Intermediate Similarity	NPC210140
0.7967	Intermediate Similarity	NPC145832
0.7967	Intermediate Similarity	NPC12053
0.7966	Intermediate Similarity	NPC138487
0.7966	Intermediate Similarity	NPC41178
0.7966	Intermediate Similarity	NPC93593
0.7966	Intermediate Similarity	NPC216459
0.7947	Intermediate Similarity	NPC186546
0.7947	Intermediate Similarity	NPC476576
0.7944	Intermediate Similarity	NPC60186
0.7941	Intermediate Similarity	NPC204446
0.7941	Intermediate Similarity	NPC23614
0.7941	Intermediate Similarity	NPC100079
0.7921	Intermediate Similarity	NPC146288
0.7914	Intermediate Similarity	NPC470879
0.7914	Intermediate Similarity	NPC258695
0.7903	Intermediate Similarity	NPC283999
0.7901	Intermediate Similarity	NPC324144
0.7898	Intermediate Similarity	NPC81733
0.7898	Intermediate Similarity	NPC326316
0.7889	Intermediate Similarity	NPC97072
0.7889	Intermediate Similarity	NPC215829
0.7882	Intermediate Similarity	NPC55470
0.788	Intermediate Similarity	NPC6152
0.7877	Intermediate Similarity	NPC476572
0.7869	Intermediate Similarity	NPC181653
0.7869	Intermediate Similarity	NPC190332
0.7865	Intermediate Similarity	NPC475754
0.7861	Intermediate Similarity	NPC188420
0.7861	Intermediate Similarity	NPC23219
0.7857	Intermediate Similarity	NPC136508
0.7857	Intermediate Similarity	NPC96603
0.7857	Intermediate Similarity	NPC13504
0.7857	Intermediate Similarity	NPC212794
0.7857	Intermediate Similarity	NPC78222
0.7857	Intermediate Similarity	NPC477563
0.7857	Intermediate Similarity	NPC196447
0.7857	Intermediate Similarity	NPC306843
0.7857	Intermediate Similarity	NPC253043
0.7853	Intermediate Similarity	NPC210148
0.7853	Intermediate Similarity	NPC233029
0.7853	Intermediate Similarity	NPC26601
0.7849	Intermediate Similarity	NPC187678
0.7842	Intermediate Similarity	NPC9867
0.7838	Intermediate Similarity	NPC470739
0.7838	Intermediate Similarity	NPC225597
0.7838	Intermediate Similarity	NPC239775
0.7838	Intermediate Similarity	NPC477640
0.7833	Intermediate Similarity	NPC149471
0.7833	Intermediate Similarity	NPC111485
0.7833	Intermediate Similarity	NPC271215
0.7829	Intermediate Similarity	NPC475959
0.7821	Intermediate Similarity	NPC186063
0.7819	Intermediate Similarity	NPC244554
0.7807	Intermediate Similarity	NPC112575
0.7802	Intermediate Similarity	NPC320104
0.7802	Intermediate Similarity	NPC1229
0.7784	Intermediate Similarity	NPC311991
0.7784	Intermediate Similarity	NPC474475
0.7784	Intermediate Similarity	NPC219162
0.7784	Intermediate Similarity	NPC168753
0.7784	Intermediate Similarity	NPC118274
0.7772	Intermediate Similarity	NPC100566
0.7766	Intermediate Similarity	NPC260118
0.7765	Intermediate Similarity	NPC325871
0.7765	Intermediate Similarity	NPC244112
0.7765	Intermediate Similarity	NPC99659
0.7759	Intermediate Similarity	NPC145304
0.7749	Intermediate Similarity	NPC180253
0.7749	Intermediate Similarity	NPC219170
0.7747	Intermediate Similarity	NPC80759
0.7747	Intermediate Similarity	NPC79402
0.7737	Intermediate Similarity	NPC276060
0.7735	Intermediate Similarity	NPC221864
0.773	Intermediate Similarity	NPC475686
0.773	Intermediate Similarity	NPC158148
0.773	Intermediate Similarity	NPC266176
0.773	Intermediate Similarity	NPC82533
0.773	Intermediate Similarity	NPC58766
0.773	Intermediate Similarity	NPC290759
0.7727	Intermediate Similarity	NPC130941
0.7725	Intermediate Similarity	NPC267408
0.7725	Intermediate Similarity	NPC192939
0.7725	Intermediate Similarity	NPC215747
0.7717	Intermediate Similarity	NPC476002
0.7717	Intermediate Similarity	NPC81247
0.7717	Intermediate Similarity	NPC476573
0.7717	Intermediate Similarity	NPC35627
0.7717	Intermediate Similarity	NPC195392
0.7713	Intermediate Similarity	NPC237044
0.7713	Intermediate Similarity	NPC265383
0.7701	Intermediate Similarity	NPC477020
0.7701	Intermediate Similarity	NPC192135
0.7701	Intermediate Similarity	NPC66341
0.7692	Intermediate Similarity	NPC119649
0.7692	Intermediate Similarity	NPC271388
0.7692	Intermediate Similarity	NPC205255
0.7692	Intermediate Similarity	NPC235143
0.7692	Intermediate Similarity	NPC230956
0.7688	Intermediate Similarity	NPC75958
0.7684	Intermediate Similarity	NPC211296

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 NPC162653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	776
0.2-0.3	988
0.3-0.4	1793
0.4-0.5	2761
0.5-0.6	2036
0.6-0.7	532
0.7-0.8	51
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8079	Intermediate Similarity	NPD3763	Approved
0.785	Intermediate Similarity	NPD4859	Phase 1
0.7744	Intermediate Similarity	NPD5582	Discontinued
0.7571	Intermediate Similarity	NPD4584	Approved
0.7566	Intermediate Similarity	NPD7479	Phase 2
0.7551	Intermediate Similarity	NPD7262	Phase 1
0.75	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD3051	Approved
0.7429	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2969	Approved
0.7394	Intermediate Similarity	NPD2970	Approved
0.7385	Intermediate Similarity	NPD6723	Discontinued
0.7356	Intermediate Similarity	NPD3816	Phase 1
0.7356	Intermediate Similarity	NPD3815	Phase 1
0.7354	Intermediate Similarity	NPD2489	Approved
0.7354	Intermediate Similarity	NPD27	Approved
0.7326	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD2421	Approved
0.7318	Intermediate Similarity	NPD2420	Approved
0.7316	Intermediate Similarity	NPD5938	Phase 3
0.7282	Intermediate Similarity	NPD8053	Approved
0.7282	Intermediate Similarity	NPD8054	Approved
0.7273	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7906	Approved
0.7258	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8156	Discontinued
0.7234	Intermediate Similarity	NPD6037	Discontinued
0.7219	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7831	Phase 2
0.7219	Intermediate Similarity	NPD7833	Phase 2
0.7208	Intermediate Similarity	NPD4663	Approved
0.7207	Intermediate Similarity	NPD5241	Discontinued
0.7188	Intermediate Similarity	NPD8099	Discontinued
0.7188	Intermediate Similarity	NPD8252	Approved
0.7188	Intermediate Similarity	NPD8251	Approved
0.7173	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6071	Discontinued
0.7143	Intermediate Similarity	NPD7313	Approved
0.7143	Intermediate Similarity	NPD4577	Approved
0.7143	Intermediate Similarity	NPD4420	Approved
0.7143	Intermediate Similarity	NPD7311	Approved
0.7143	Intermediate Similarity	NPD7312	Approved
0.7143	Intermediate Similarity	NPD7310	Approved
0.7143	Intermediate Similarity	NPD4578	Approved
0.7135	Intermediate Similarity	NPD4773	Phase 2
0.7135	Intermediate Similarity	NPD4772	Phase 2
0.7135	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4083	Discontinued
0.7112	Intermediate Similarity	NPD2563	Approved
0.7112	Intermediate Similarity	NPD2560	Approved
0.7107	Intermediate Similarity	NPD7309	Approved
0.7105	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3983	Phase 3
0.7104	Intermediate Similarity	NPD6031	Approved
0.7104	Intermediate Similarity	NPD6030	Approved
0.7095	Intermediate Similarity	NPD5177	Phase 3
0.7094	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5005	Approved
0.7087	Intermediate Similarity	NPD5006	Approved
0.7083	Intermediate Similarity	NPD2898	Approved
0.7083	Intermediate Similarity	NPD4481	Phase 3
0.7083	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6788	Approved
0.7056	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3301	Approved
0.7015	Intermediate Similarity	NPD5641	Discontinued
0.6996	Remote Similarity	NPD6625	Approved
0.699	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6877	Discontinued
0.6974	Remote Similarity	NPD5600	Discontinued
0.697	Remote Similarity	NPD7280	Phase 3
0.697	Remote Similarity	NPD7281	Phase 3
0.6968	Remote Similarity	NPD2978	Approved
0.6968	Remote Similarity	NPD2977	Approved
0.6954	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3920	Phase 2
0.6939	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4017	Approved
0.6931	Remote Similarity	NPD6063	Approved
0.6915	Remote Similarity	NPD7298	Approved
0.6915	Remote Similarity	NPD3398	Discontinued
0.6912	Remote Similarity	NPD6493	Phase 3
0.6911	Remote Similarity	NPD4796	Discontinued
0.6905	Remote Similarity	NPD5530	Phase 1
0.69	Remote Similarity	NPD6339	Approved
0.69	Remote Similarity	NPD6340	Approved
0.6897	Remote Similarity	NPD3922	Approved
0.6897	Remote Similarity	NPD3924	Approved
0.6897	Remote Similarity	NPD3921	Approved
0.6897	Remote Similarity	NPD3923	Approved
0.6895	Remote Similarity	NPD1743	Approved
0.6895	Remote Similarity	NPD1742	Approved
0.6895	Remote Similarity	NPD19	Approved
0.6891	Remote Similarity	NPD4010	Discontinued
0.6888	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3845	Phase 1
0.6872	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4951	Discontinued
0.6865	Remote Similarity	NPD6090	Discontinued
0.6847	Remote Similarity	NPD2488	Approved
0.6847	Remote Similarity	NPD2490	Approved
0.6845	Remote Similarity	NPD2974	Approved
0.6845	Remote Similarity	NPD2973	Approved
0.6845	Remote Similarity	NPD2975	Approved
0.6845	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6494	Phase 2
0.6839	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6612	Phase 2
0.6825	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3450	Approved
0.6794	Remote Similarity	NPD2493	Approved
0.6794	Remote Similarity	NPD3452	Approved
0.6794	Remote Similarity	NPD2494	Approved
0.6792	Remote Similarity	NPD7222	Phase 2
0.6791	Remote Similarity	NPD7827	Phase 1
0.6779	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8149	Discontinued
0.6771	Remote Similarity	NPD5604	Discontinued
0.677	Remote Similarity	NPD7922	Phase 1
0.6763	Remote Similarity	NPD4604	Approved
0.6763	Remote Similarity	NPD4605	Approved
0.6762	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5658	Approved
0.6755	Remote Similarity	NPD6357	Discontinued
0.6753	Remote Similarity	NPD7802	Discontinued
0.6749	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD3349	Phase 2
0.6746	Remote Similarity	NPD4580	Approved
0.6738	Remote Similarity	NPD4727	Phase 1
0.6738	Remote Similarity	NPD3641	Approved
0.6738	Remote Similarity	NPD3640	Phase 3
0.6738	Remote Similarity	NPD3639	Approved
0.6736	Remote Similarity	NPD7400	Phase 3
0.6734	Remote Similarity	NPD6184	Discontinued
0.6726	Remote Similarity	NPD7223	Discontinued
0.6726	Remote Similarity	NPD7224	Discontinued
0.6726	Remote Similarity	NPD4885	Approved
0.672	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5617	Suspended
0.6717	Remote Similarity	NPD5810	Discontinued
0.6716	Remote Similarity	NPD2845	Phase 2
0.6716	Remote Similarity	NPD2971	Approved
0.6716	Remote Similarity	NPD2843	Phase 2
0.6716	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2968	Approved
0.6703	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5150	Phase 2
0.6698	Remote Similarity	NPD4582	Approved
0.6698	Remote Similarity	NPD4583	Approved
0.6697	Remote Similarity	NPD7047	Phase 3
0.6685	Remote Similarity	NPD4474	Approved
0.6685	Remote Similarity	NPD4475	Approved
0.6685	Remote Similarity	NPD4108	Discontinued
0.6684	Remote Similarity	NPD3975	Discontinued
0.6682	Remote Similarity	NPD2899	Discontinued
0.6682	Remote Similarity	NPD3515	Approved
0.6682	Remote Similarity	NPD3516	Approved
0.6681	Remote Similarity	NPD4846	Phase 2
0.6667	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6107	Approved
0.6667	Remote Similarity	NPD6997	Phase 2
0.6667	Remote Similarity	NPD7549	Discontinued
0.6651	Remote Similarity	NPD4004	Approved
0.6651	Remote Similarity	NPD4002	Approved
0.6651	Remote Similarity	NPD5071	Phase 2
0.665	Remote Similarity	NPD6297	Approved
0.665	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3109	Approved
0.6648	Remote Similarity	NPD3110	Approved
0.6648	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6747	Phase 1
0.6632	Remote Similarity	NPD3296	Phase 1
0.6631	Remote Similarity	NPD7019	Approved
0.6631	Remote Similarity	NPD7020	Approved
0.663	Remote Similarity	NPD6674	Discontinued
0.6629	Remote Similarity	NPD5718	Phase 2
0.6622	Remote Similarity	NPD7805	Phase 3
0.6619	Remote Similarity	NPD6874	Approved
0.6618	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7125	Discontinued
0.6606	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7034	Discontinued
0.6603	Remote Similarity	NPD6527	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