NPASS Compound

Structure

NPC474470 OpenBabel07101718332D 24 28 0 0 1 0 0 0 0 0999 V2000 3.0558 -2.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6370 0.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7328 0.6211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1398 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0758 -1.2692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1398 -0.0854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3687 -0.7365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8033 -0.7771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7886 -2.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5408 -1.1230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8085 -0.6481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5408 -0.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7389 -1.1230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7389 -0.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 -0.9451 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9519 0.1289 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6744 -1.4003 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.6929 -2.5653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4071 0.9748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3967 -1.3367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3967 -0.2175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6171 -1.2961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 3 2 0 0 0 0 2 12 1 0 0 0 0 4 11 2 0 0 0 0 4 14 1 0 0 0 0 5 12 1 0 0 0 0 5 16 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 17 1 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 9 23 1 0 0 0 0 10 20 2 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 12 24 1 6 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 6 0 0 0 16 19 1 0 0 0 0 17 18 1 6 0 0 0 17 21 1 0 0 0 0 18 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.13
Volume:	318.867
LogP:	1.086
LogD:	0.887
LogS:	-3.146
# Rotatable Bonds:	2
TPSA:	68.23
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	5.163
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.012
MDCK Permeability:	4.3869800720131025e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.138
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	41.429813385009766%
Volume Distribution (VD):	1.303
Pgp-substrate:	55.573856353759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.289
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.249
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.672
CYP2D6-inhibitor:	0.921
CYP2D6-substrate:	0.627
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.665

ADMET: Excretion

Clearance (CL):	3.859
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.297
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.291
AMES Toxicity:	0.38
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.243
Carcinogencity:	0.781
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC474470

Natural Product ID:	NPC474470
*Common Name:**	Yemenine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NWAYYOQRSAEORM-GYIHYUDTSA-N
Standard InCHI:	InChI=1S/C18H19NO5/c1-10(20)24-12-2-3-18-13-6-15-14(22-9-23-15)4-11(13)7-19(8-17(18)21)16(18)5-12/h2-4,6,12,16-17,21H,5,7-9H2,1H3/t12-,16-,17-,18+/m0/s1
SMILES:	CC(=O)O[C@H]1C=C[C@@]23[C@H](C1)N(C[C@@H]2O)Cc1c3cc2OCOc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469438
PubChem CID:	44559492
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae 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
NPO23263	Crinum yemense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270564]
NPO23263	Crinum yemense	Species	Amaryllidaceae	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	1
Others	10

Activity Type	# Activity
Others	11

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	10.4	%	PMID[489206]
NPT27	Others	Unspecified	Activity	=	110.5	%	PMID[489206]
NPT2	Others	Unspecified	Inhibition	=	38.1	%	PMID[489206]
NPT27	Others	Unspecified	Activity	=	100.6	%	PMID[489206]
NPT2	Others	Unspecified	Inhibition	=	69.0	%	PMID[489206]
NPT27	Others	Unspecified	Activity	=	80.1	%	PMID[489206]
NPT2	Others	Unspecified	Inhibition	=	93.0	%	PMID[489206]
NPT27	Others	Unspecified	Activity	=	66.6	%	PMID[489206]
NPT2	Others	Unspecified	Inhibition	=	98.5	%	PMID[489206]
NPT27	Others	Unspecified	Activity	=	51.0	%	PMID[489206]
NPT2	Others	Unspecified	IC50	=	4900.0	nM	PMID[489206]

☑ 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 NPC474470 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	227
0.1-0.2	1124
0.2-0.3	3410
0.3-0.4	11109
0.4-0.5	8273
0.5-0.6	13708
0.6-0.7	3990
0.7-0.8	668
0.8-0.85	109
0.85-0.9	34
0.9-0.95	33
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC158148
0.9688	High Similarity	NPC266176
0.9688	High Similarity	NPC82533
0.9688	High Similarity	NPC290759
0.9568	High Similarity	NPC225597
0.9568	High Similarity	NPC477640
0.9568	High Similarity	NPC470739
0.9565	High Similarity	NPC58766
0.9565	High Similarity	NPC475686
0.9506	High Similarity	NPC474475
0.9451	High Similarity	NPC304675
0.9394	High Similarity	NPC237044
0.9337	High Similarity	NPC474325
0.9281	High Similarity	NPC244554
0.9281	High Similarity	NPC474745
0.9264	High Similarity	NPC57812
0.9264	High Similarity	NPC474324
0.9207	High Similarity	NPC475845
0.9198	High Similarity	NPC218614
0.9193	High Similarity	NPC215829
0.9193	High Similarity	NPC97072
0.9152	High Similarity	NPC474708
0.9146	High Similarity	NPC100566
0.9146	High Similarity	NPC252960
0.9141	High Similarity	NPC247972
0.9118	High Similarity	NPC475981
0.9118	High Similarity	NPC474746
0.908	High Similarity	NPC320104
0.9062	High Similarity	NPC78733
0.9036	High Similarity	NPC311991
0.903	High Similarity	NPC190332
0.903	High Similarity	NPC181653
0.9012	High Similarity	NPC230098
0.8922	High Similarity	NPC75958
0.8882	High Similarity	NPC15919
0.8817	High Similarity	NPC2314
0.8757	High Similarity	NPC65403
0.8743	High Similarity	NPC476002
0.8667	High Similarity	NPC59028
0.8667	High Similarity	NPC92191
0.8663	High Similarity	NPC118633
0.8663	High Similarity	NPC294790
0.8663	High Similarity	NPC148693
0.8659	High Similarity	NPC147091
0.8629	High Similarity	NPC9867
0.8614	High Similarity	NPC4304
0.8589	High Similarity	NPC148898
0.8589	High Similarity	NPC223124
0.8547	High Similarity	NPC187678
0.8547	High Similarity	NPC49353
0.8503	High Similarity	NPC205167
0.8503	High Similarity	NPC249274
0.8466	Intermediate Similarity	NPC223125
0.8462	Intermediate Similarity	NPC231198
0.8457	Intermediate Similarity	NPC475959
0.8427	Intermediate Similarity	NPC141440
0.8409	Intermediate Similarity	NPC102760
0.8409	Intermediate Similarity	NPC248642
0.84	Intermediate Similarity	NPC126284
0.8364	Intermediate Similarity	NPC233029
0.8364	Intermediate Similarity	NPC210148
0.8363	Intermediate Similarity	NPC150879
0.8362	Intermediate Similarity	NPC156576
0.8354	Intermediate Similarity	NPC274026
0.8324	Intermediate Similarity	NPC237579
0.8323	Intermediate Similarity	NPC31311
0.8323	Intermediate Similarity	NPC234392
0.8305	Intermediate Similarity	NPC275132
0.8297	Intermediate Similarity	NPC33256
0.8295	Intermediate Similarity	NPC99179
0.8294	Intermediate Similarity	NPC59567
0.8286	Intermediate Similarity	NPC241704
0.8263	Intermediate Similarity	NPC138487
0.8263	Intermediate Similarity	NPC41178
0.8263	Intermediate Similarity	NPC216459
0.8246	Intermediate Similarity	NPC238530
0.8246	Intermediate Similarity	NPC276944
0.8246	Intermediate Similarity	NPC232514
0.8225	Intermediate Similarity	NPC477080
0.8225	Intermediate Similarity	NPC111485
0.8214	Intermediate Similarity	NPC146288
0.8207	Intermediate Similarity	NPC215098
0.8207	Intermediate Similarity	NPC70290
0.8207	Intermediate Similarity	NPC124302
0.8207	Intermediate Similarity	NPC73020
0.8207	Intermediate Similarity	NPC14622
0.8207	Intermediate Similarity	NPC46744
0.8202	Intermediate Similarity	NPC233718
0.8192	Intermediate Similarity	NPC32154
0.8187	Intermediate Similarity	NPC233650
0.8167	Intermediate Similarity	NPC214116
0.8166	Intermediate Similarity	NPC78359
0.8166	Intermediate Similarity	NPC40389
0.8166	Intermediate Similarity	NPC148014
0.8166	Intermediate Similarity	NPC65490
0.8166	Intermediate Similarity	NPC315707
0.8161	Intermediate Similarity	NPC474953
0.816	Intermediate Similarity	NPC130926
0.815	Intermediate Similarity	NPC210918
0.8144	Intermediate Similarity	NPC82285
0.8144	Intermediate Similarity	NPC133011
0.814	Intermediate Similarity	NPC180306
0.814	Intermediate Similarity	NPC134858
0.8132	Intermediate Similarity	NPC63152
0.8128	Intermediate Similarity	NPC119818
0.8128	Intermediate Similarity	NPC202771
0.8128	Intermediate Similarity	NPC328700
0.8128	Intermediate Similarity	NPC2173
0.8118	Intermediate Similarity	NPC226652
0.8118	Intermediate Similarity	NPC72788
0.8118	Intermediate Similarity	NPC120671
0.8118	Intermediate Similarity	NPC314100
0.8118	Intermediate Similarity	NPC106786
0.8107	Intermediate Similarity	NPC180756
0.8107	Intermediate Similarity	NPC323443
0.8092	Intermediate Similarity	NPC24264
0.8092	Intermediate Similarity	NPC124657
0.8092	Intermediate Similarity	NPC476432
0.807	Intermediate Similarity	NPC165797
0.8059	Intermediate Similarity	NPC129603
0.8049	Intermediate Similarity	NPC185838
0.8046	Intermediate Similarity	NPC247389
0.8046	Intermediate Similarity	NPC210140
0.8035	Intermediate Similarity	NPC225774
0.8035	Intermediate Similarity	NPC16805
0.8035	Intermediate Similarity	NPC167546
0.8035	Intermediate Similarity	NPC302527
0.8034	Intermediate Similarity	NPC320223
0.8034	Intermediate Similarity	NPC114364
0.8025	Intermediate Similarity	NPC474915
0.8025	Intermediate Similarity	NPC328750
0.8025	Intermediate Similarity	NPC213206
0.8025	Intermediate Similarity	NPC188163
0.8023	Intermediate Similarity	NPC128560
0.8023	Intermediate Similarity	NPC199465
0.8023	Intermediate Similarity	NPC229166
0.8012	Intermediate Similarity	NPC428
0.8012	Intermediate Similarity	NPC24233
0.8012	Intermediate Similarity	NPC476571
0.8012	Intermediate Similarity	NPC147390
0.8012	Intermediate Similarity	NPC246587
0.8012	Intermediate Similarity	NPC135538
0.8011	Intermediate Similarity	NPC57272
0.8	Intermediate Similarity	NPC476575
0.8	Intermediate Similarity	NPC160570
0.8	Intermediate Similarity	NPC116284
0.8	Intermediate Similarity	NPC7018
0.7989	Intermediate Similarity	NPC94499
0.7989	Intermediate Similarity	NPC219341
0.7989	Intermediate Similarity	NPC220961
0.7965	Intermediate Similarity	NPC18402
0.7963	Intermediate Similarity	NPC314682
0.7952	Intermediate Similarity	NPC191376
0.7952	Intermediate Similarity	NPC179825
0.7952	Intermediate Similarity	NPC321505
0.7952	Intermediate Similarity	NPC476151
0.7943	Intermediate Similarity	NPC298186
0.7943	Intermediate Similarity	NPC301189
0.7943	Intermediate Similarity	NPC298979
0.7941	Intermediate Similarity	NPC76079
0.7941	Intermediate Similarity	NPC93593
0.7935	Intermediate Similarity	NPC226708
0.7931	Intermediate Similarity	NPC169743
0.7906	Intermediate Similarity	NPC80472
0.7904	Intermediate Similarity	NPC59907
0.7904	Intermediate Similarity	NPC37144
0.7895	Intermediate Similarity	NPC37205
0.7895	Intermediate Similarity	NPC160931
0.7892	Intermediate Similarity	NPC117717
0.7889	Intermediate Similarity	NPC267408
0.7877	Intermediate Similarity	NPC283999
0.7874	Intermediate Similarity	NPC293871
0.7874	Intermediate Similarity	NPC124433
0.7861	Intermediate Similarity	NPC266753
0.7861	Intermediate Similarity	NPC477559
0.7861	Intermediate Similarity	NPC232924
0.7861	Intermediate Similarity	NPC306902
0.7861	Intermediate Similarity	NPC160298
0.7857	Intermediate Similarity	NPC477565
0.7857	Intermediate Similarity	NPC103379
0.7853	Intermediate Similarity	NPC329911
0.7849	Intermediate Similarity	NPC475326
0.7844	Intermediate Similarity	NPC16107
0.7844	Intermediate Similarity	NPC51957
0.7844	Intermediate Similarity	NPC210437
0.7844	Intermediate Similarity	NPC106295
0.7844	Intermediate Similarity	NPC476144
0.7838	Intermediate Similarity	NPC319549
0.7836	Intermediate Similarity	NPC172765
0.7836	Intermediate Similarity	NPC278799
0.7836	Intermediate Similarity	NPC189266
0.7836	Intermediate Similarity	NPC276588
0.7836	Intermediate Similarity	NPC54379
0.7836	Intermediate Similarity	NPC204828
0.7836	Intermediate Similarity	NPC2413
0.7836	Intermediate Similarity	NPC184026
0.7836	Intermediate Similarity	NPC249797
0.7836	Intermediate Similarity	NPC39701
0.7836	Intermediate Similarity	NPC207757
0.7836	Intermediate Similarity	NPC5238

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 NPC474470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	548
0.2-0.3	947
0.3-0.4	2177
0.4-0.5	2667
0.5-0.6	1850
0.6-0.7	668
0.7-0.8	132
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8208	Intermediate Similarity	NPD4481	Phase 3
0.8207	Intermediate Similarity	NPD4420	Approved
0.8198	Intermediate Similarity	NPD6071	Discontinued
0.8166	Intermediate Similarity	NPD2563	Approved
0.8166	Intermediate Similarity	NPD2560	Approved
0.8128	Intermediate Similarity	NPD5006	Approved
0.8128	Intermediate Similarity	NPD5005	Approved
0.8095	Intermediate Similarity	NPD4772	Phase 2
0.8095	Intermediate Similarity	NPD4773	Phase 2
0.8046	Intermediate Similarity	NPD2970	Approved
0.8046	Intermediate Similarity	NPD2969	Approved
0.8035	Intermediate Similarity	NPD6107	Approved
0.8025	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3051	Approved
0.7975	Intermediate Similarity	NPD4236	Phase 3
0.7975	Intermediate Similarity	NPD4237	Approved
0.7944	Intermediate Similarity	NPD7280	Phase 3
0.7944	Intermediate Similarity	NPD7281	Phase 3
0.7903	Intermediate Similarity	NPD5582	Discontinued
0.7898	Intermediate Similarity	NPD27	Approved
0.7898	Intermediate Similarity	NPD2489	Approved
0.7895	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD4584	Approved
0.7838	Intermediate Similarity	NPD7296	Approved
0.7831	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4210	Discontinued
0.7797	Intermediate Similarity	NPD2898	Approved
0.7791	Intermediate Similarity	NPD2977	Approved
0.7791	Intermediate Similarity	NPD2978	Approved
0.7771	Intermediate Similarity	NPD5241	Discontinued
0.7713	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6851	Approved
0.7705	Intermediate Similarity	NPD6853	Approved
0.7688	Intermediate Similarity	NPD5773	Approved
0.7688	Intermediate Similarity	NPD5772	Approved
0.768	Intermediate Similarity	NPD6297	Approved
0.7676	Intermediate Similarity	NPD7906	Approved
0.7667	Intermediate Similarity	NPD5313	Approved
0.7667	Intermediate Similarity	NPD5312	Approved
0.7665	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3639	Approved
0.7647	Intermediate Similarity	NPD3641	Approved
0.7647	Intermediate Similarity	NPD3640	Phase 3
0.7622	Intermediate Similarity	NPD4663	Approved
0.7602	Intermediate Similarity	NPD3687	Approved
0.7602	Intermediate Similarity	NPD3686	Approved
0.7571	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7313	Approved
0.7554	Intermediate Similarity	NPD4577	Approved
0.7554	Intermediate Similarity	NPD7312	Approved
0.7554	Intermediate Similarity	NPD7311	Approved
0.7554	Intermediate Similarity	NPD7310	Approved
0.7554	Intermediate Similarity	NPD4578	Approved
0.7514	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7309	Approved
0.7487	Intermediate Similarity	NPD2975	Approved
0.7487	Intermediate Similarity	NPD2973	Approved
0.7487	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2974	Approved
0.7473	Intermediate Similarity	NPD8156	Discontinued
0.7458	Intermediate Similarity	NPD7831	Phase 2
0.7458	Intermediate Similarity	NPD7833	Phase 2
0.7458	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4017	Approved
0.7442	Intermediate Similarity	NPD6031	Approved
0.7442	Intermediate Similarity	NPD6030	Approved
0.7427	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8053	Approved
0.7419	Intermediate Similarity	NPD8054	Approved
0.7418	Intermediate Similarity	NPD8252	Approved
0.7418	Intermediate Similarity	NPD8099	Discontinued
0.7418	Intermediate Similarity	NPD8251	Approved
0.74	Intermediate Similarity	NPD7827	Phase 1
0.7389	Intermediate Similarity	NPD4166	Phase 2
0.7374	Intermediate Similarity	NPD5677	Discontinued
0.7371	Intermediate Similarity	NPD4580	Approved
0.7366	Intermediate Similarity	NPD2971	Approved
0.7366	Intermediate Similarity	NPD2968	Approved
0.7353	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3060	Approved
0.7333	Intermediate Similarity	NPD2494	Approved
0.7333	Intermediate Similarity	NPD3452	Approved
0.7333	Intermediate Similarity	NPD3450	Approved
0.7333	Intermediate Similarity	NPD2493	Approved
0.733	Intermediate Similarity	NPD7298	Approved
0.732	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD2490	Approved
0.7316	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD2488	Approved
0.7301	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4010	Discontinued
0.7263	Intermediate Similarity	NPD5604	Discontinued
0.7263	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4727	Phase 1
0.7235	Intermediate Similarity	NPD4162	Approved
0.7232	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4582	Approved
0.7222	Intermediate Similarity	NPD4583	Approved
0.7222	Intermediate Similarity	NPD5709	Phase 3
0.7219	Intermediate Similarity	NPD1375	Discontinued
0.7219	Intermediate Similarity	NPD3656	Approved
0.7212	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6788	Approved
0.7194	Intermediate Similarity	NPD4107	Approved
0.7186	Intermediate Similarity	NPD2492	Phase 1
0.7182	Intermediate Similarity	NPD4666	Phase 3
0.7172	Intermediate Similarity	NPD4002	Approved
0.7172	Intermediate Similarity	NPD4004	Approved
0.7163	Intermediate Similarity	NPD6997	Phase 2
0.7159	Intermediate Similarity	NPD4005	Discontinued
0.7158	Intermediate Similarity	NPD6688	Approved
0.7158	Intermediate Similarity	NPD6687	Approved
0.7158	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3885	Approved
0.7126	Intermediate Similarity	NPD4123	Phase 3
0.7122	Intermediate Similarity	NPD7047	Phase 3
0.7121	Intermediate Similarity	NPD3057	Approved
0.712	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6667	Approved
0.711	Intermediate Similarity	NPD6666	Approved
0.7101	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1753	Discontinued
0.71	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6385	Approved
0.7079	Intermediate Similarity	NPD6386	Approved
0.7074	Intermediate Similarity	NPD7039	Approved
0.7074	Intermediate Similarity	NPD7038	Approved
0.7074	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4482	Phase 3
0.7065	Intermediate Similarity	NPD5242	Approved
0.7052	Intermediate Similarity	NPD2677	Approved
0.7048	Intermediate Similarity	NPD5718	Phase 2
0.7048	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5976	Discontinued
0.7041	Intermediate Similarity	NPD6896	Approved
0.7041	Intermediate Similarity	NPD6895	Approved
0.7037	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2972	Approved
0.7035	Intermediate Similarity	NPD3533	Approved
0.7035	Intermediate Similarity	NPD5177	Phase 3
0.703	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3536	Discontinued
0.7029	Intermediate Similarity	NPD1424	Approved
0.7023	Intermediate Similarity	NPD6625	Approved
0.7019	Intermediate Similarity	NPD3705	Approved
0.7017	Intermediate Similarity	NPD4967	Phase 2
0.7017	Intermediate Similarity	NPD4966	Approved
0.7017	Intermediate Similarity	NPD4965	Approved
0.7017	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7124	Phase 2
0.701	Intermediate Similarity	NPD5676	Approved
0.7005	Intermediate Similarity	NPD5095	Phase 3
0.7005	Intermediate Similarity	NPD5096	Phase 3
0.7	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2904	Discontinued
0.6989	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD52	Approved
0.6989	Remote Similarity	NPD7526	Approved
0.6978	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3124	Discontinued
0.6966	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2238	Phase 2
0.6961	Remote Similarity	NPD5977	Approved
0.6961	Remote Similarity	NPD5978	Approved
0.6959	Remote Similarity	NPD2161	Phase 2
0.6954	Remote Similarity	NPD3692	Discontinued
0.695	Remote Similarity	NPD3448	Approved
0.695	Remote Similarity	NPD2491	Approved
0.6947	Remote Similarity	NPD7549	Discontinued
0.6943	Remote Similarity	NPD6842	Approved
0.6943	Remote Similarity	NPD6843	Phase 3
0.6943	Remote Similarity	NPD6841	Approved
0.694	Remote Similarity	NPD7400	Phase 3
0.6932	Remote Similarity	NPD4739	Approved
0.6931	Remote Similarity	NPD7999	Approved
0.6927	Remote Similarity	NPD4675	Approved
0.6927	Remote Similarity	NPD4678	Approved
0.6919	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7315	Approved
0.6915	Remote Similarity	NPD6042	Phase 2
0.6915	Remote Similarity	NPD3933	Discontinued
0.6915	Remote Similarity	NPD42	Phase 2
0.6905	Remote Similarity	NPD5745	Approved
0.6898	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4055	Discovery
0.6882	Remote Similarity	NPD823	Approved
0.6882	Remote Similarity	NPD817	Approved
0.6882	Remote Similarity	NPD2653	Approved
0.6881	Remote Similarity	NPD4040	Phase 1
0.6875	Remote Similarity	NPD1774	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