NPASS Compound

Structure

NPC474708 OpenBabel07101718292D 31 35 0 0 1 0 0 0 0 0999 V2000 -1.6257 -5.2726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2012 -2.2647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8629 -5.9192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0226 -3.2486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0785 -5.5819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0812 -3.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5232 -0.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9599 0.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0900 -2.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1327 0.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1327 -1.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7927 0.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0881 -0.7326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9115 -1.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4285 -0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4285 -1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8369 -0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8369 -1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3272 -2.9674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2571 -4.5979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3184 -2.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7927 -1.6462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0299 -0.9996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6142 -2.6301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.1985 -4.2606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4970 -1.9554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6102 -0.0748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6102 -1.3904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5058 -3.9513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3770 -3.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 25 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 13 29 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 17 18 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 24 1 0 0 0 0 19 30 1 1 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 22 16 1 6 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 1 0 0 0 24 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	427.2
Volume:	428.797
LogP:	4.205
LogD:	3.43
LogS:	-4.71
# Rotatable Bonds:	8
TPSA:	74.3
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.508
Synthetic Accessibility Score:	4.255
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	4.0203449316322803e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	85.26433563232422%
Volume Distribution (VD):	2.04
Pgp-substrate:	5.322120666503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.667
CYP1A2-substrate:	0.157
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.456
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.676
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	17.607
Half-life (T1/2):	0.292

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.676
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.055
Carcinogencity:	0.439
Eye Corrosion:	0.003
Eye Irritation:	0.02
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: NPC474708

Natural Product ID:	NPC474708
*Common Name:**	XFPKJBMPXIIKGU-ZMUKGBGYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XFPKJBMPXIIKGU-ZMUKGBGYSA-N
Standard InCHI:	InChI=1S/C24H29NO6/c1-3-5-20(26)30-19-9-14-7-8-25-12-15-10-17-18(29-13-28-17)11-16(15)22(23(14)25)24(19)31-21(27)6-4-2/h9-11,19,22-24H,3-8,12-13H2,1-2H3/t19-,22-,23+,24+/m0/s1
SMILES:	CCCC(=O)OC1C=C2CCN3C2C(C1OC(=O)CCC)C4=CC5=C(C=C4C3)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479819
PubChem CID:	44570429
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004120] Lycorine-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
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013823]
NPO25024	Lycoris traubii	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	2
Others	2

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.67	ug.mL-1	PMID[493617]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.53	ug.mL-1	PMID[493617]
NPT2	Others	Unspecified		Ratio IC50	=	21.7	n.a.	PMID[493617]
NPT2	Others	Unspecified		Ratio IC50	=	27.5	n.a.	PMID[493617]

☑ 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 NPC474708 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	242
0.1-0.2	1171
0.2-0.3	3607
0.3-0.4	11548
0.4-0.5	7789
0.5-0.6	14029
0.6-0.7	3358
0.7-0.8	778
0.8-0.85	106
0.85-0.9	42
0.9-0.95	21
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC475845
0.9872	High Similarity	NPC57812
0.9872	High Similarity	NPC474324
0.963	High Similarity	NPC474745
0.9568	High Similarity	NPC474325
0.9565	High Similarity	NPC304675
0.9506	High Similarity	NPC237044
0.9455	High Similarity	NPC475981
0.9455	High Similarity	NPC474746
0.9341	High Similarity	NPC230098
0.9187	High Similarity	NPC320104
0.9152	High Similarity	NPC474470
0.9136	High Similarity	NPC181653
0.9136	High Similarity	NPC190332
0.9018	High Similarity	NPC100566
0.8931	High Similarity	NPC78733
0.8855	High Similarity	NPC65403
0.8848	High Similarity	NPC266176
0.8848	High Similarity	NPC290759
0.8848	High Similarity	NPC82533
0.8848	High Similarity	NPC158148
0.8795	High Similarity	NPC75958
0.878	High Similarity	NPC247972
0.8743	High Similarity	NPC477640
0.8743	High Similarity	NPC470739
0.8743	High Similarity	NPC225597
0.8735	High Similarity	NPC58766
0.8735	High Similarity	NPC475686
0.8712	High Similarity	NPC4304
0.8688	High Similarity	NPC148898
0.8683	High Similarity	NPC311991
0.8683	High Similarity	NPC474475
0.8679	High Similarity	NPC223125
0.8667	High Similarity	NPC180306
0.8647	High Similarity	NPC148693
0.8647	High Similarity	NPC118633
0.8647	High Similarity	NPC294790
0.8614	High Similarity	NPC476002
0.8598	High Similarity	NPC97072
0.8598	High Similarity	NPC215829
0.8598	High Similarity	NPC249274
0.8598	High Similarity	NPC205167
0.8588	High Similarity	NPC33256
0.8571	High Similarity	NPC210148
0.8571	High Similarity	NPC223124
0.8571	High Similarity	NPC233029
0.8563	High Similarity	NPC210918
0.8554	High Similarity	NPC231198
0.8553	High Similarity	NPC475959
0.8538	High Similarity	NPC15919
0.8537	High Similarity	NPC477080
0.8529	High Similarity	NPC187678
0.8497	Intermediate Similarity	NPC102760
0.8494	Intermediate Similarity	NPC218614
0.8488	Intermediate Similarity	NPC244554
0.848	Intermediate Similarity	NPC35680
0.8443	Intermediate Similarity	NPC167546
0.8443	Intermediate Similarity	NPC16805
0.8443	Intermediate Similarity	NPC302527
0.8415	Intermediate Similarity	NPC234392
0.8415	Intermediate Similarity	NPC146288
0.8415	Intermediate Similarity	NPC31311
0.8409	Intermediate Similarity	NPC237579
0.8393	Intermediate Similarity	NPC476432
0.8393	Intermediate Similarity	NPC24264
0.8354	Intermediate Similarity	NPC138487
0.8354	Intermediate Similarity	NPC216459
0.8354	Intermediate Similarity	NPC41178
0.8343	Intermediate Similarity	NPC252960
0.8343	Intermediate Similarity	NPC247389
0.8333	Intermediate Similarity	NPC225774
0.8315	Intermediate Similarity	NPC63152
0.8305	Intermediate Similarity	NPC141440
0.8295	Intermediate Similarity	NPC9867
0.8287	Intermediate Similarity	NPC46744
0.8287	Intermediate Similarity	NPC70290
0.8287	Intermediate Similarity	NPC215098
0.8287	Intermediate Similarity	NPC73020
0.8287	Intermediate Similarity	NPC14622
0.8287	Intermediate Similarity	NPC124302
0.8286	Intermediate Similarity	NPC275132
0.8284	Intermediate Similarity	NPC219341
0.8256	Intermediate Similarity	NPC2314
0.825	Intermediate Similarity	NPC130926
0.8208	Intermediate Similarity	NPC49353
0.8207	Intermediate Similarity	NPC2173
0.8207	Intermediate Similarity	NPC202771
0.8207	Intermediate Similarity	NPC328700
0.8207	Intermediate Similarity	NPC119818
0.8205	Intermediate Similarity	NPC7018
0.8204	Intermediate Similarity	NPC106786
0.8202	Intermediate Similarity	NPC166979
0.8198	Intermediate Similarity	NPC149090
0.8198	Intermediate Similarity	NPC19520
0.8197	Intermediate Similarity	NPC72788
0.8197	Intermediate Similarity	NPC314100
0.8197	Intermediate Similarity	NPC120671
0.8197	Intermediate Similarity	NPC226652
0.8172	Intermediate Similarity	NPC80472
0.8166	Intermediate Similarity	NPC59567
0.8161	Intermediate Similarity	NPC241704
0.8155	Intermediate Similarity	NPC306902
0.8155	Intermediate Similarity	NPC232924
0.8155	Intermediate Similarity	NPC477559
0.8155	Intermediate Similarity	NPC160298
0.8155	Intermediate Similarity	NPC266753
0.8146	Intermediate Similarity	NPC162694
0.814	Intermediate Similarity	NPC6152
0.8133	Intermediate Similarity	NPC76079
0.8113	Intermediate Similarity	NPC328750
0.8113	Intermediate Similarity	NPC213206
0.8113	Intermediate Similarity	NPC474915
0.8113	Intermediate Similarity	NPC188163
0.8103	Intermediate Similarity	NPC128560
0.8103	Intermediate Similarity	NPC199465
0.8103	Intermediate Similarity	NPC229166
0.8098	Intermediate Similarity	NPC37144
0.8098	Intermediate Similarity	NPC59907
0.8095	Intermediate Similarity	NPC59028
0.8095	Intermediate Similarity	NPC111485
0.8095	Intermediate Similarity	NPC92191
0.8084	Intermediate Similarity	NPC180756
0.8084	Intermediate Similarity	NPC147091
0.8084	Intermediate Similarity	NPC323443
0.8081	Intermediate Similarity	NPC241055
0.8079	Intermediate Similarity	NPC248642
0.8079	Intermediate Similarity	NPC116284
0.8068	Intermediate Similarity	NPC126284
0.8068	Intermediate Similarity	NPC220961
0.8068	Intermediate Similarity	NPC32154
0.805	Intermediate Similarity	NPC314682
0.8035	Intermediate Similarity	NPC474953
0.8034	Intermediate Similarity	NPC156576
0.8024	Intermediate Similarity	NPC325871
0.8024	Intermediate Similarity	NPC93593
0.8024	Intermediate Similarity	NPC99659
0.8012	Intermediate Similarity	NPC238530
0.8012	Intermediate Similarity	NPC306669
0.8012	Intermediate Similarity	NPC136860
0.8012	Intermediate Similarity	NPC476567
0.8012	Intermediate Similarity	NPC276944
0.8012	Intermediate Similarity	NPC232514
0.8012	Intermediate Similarity	NPC128019
0.8011	Intermediate Similarity	NPC319549
0.8011	Intermediate Similarity	NPC114364
0.8011	Intermediate Similarity	NPC320223
0.8	Intermediate Similarity	NPC274026
0.7988	Intermediate Similarity	NPC7467
0.7967	Intermediate Similarity	NPC94499
0.7966	Intermediate Similarity	NPC27887
0.7966	Intermediate Similarity	NPC267408
0.7955	Intermediate Similarity	NPC283999
0.7929	Intermediate Similarity	NPC476572
0.7927	Intermediate Similarity	NPC210437
0.7927	Intermediate Similarity	NPC106295
0.7927	Intermediate Similarity	NPC51957
0.7927	Intermediate Similarity	NPC16107
0.7927	Intermediate Similarity	NPC476144
0.7919	Intermediate Similarity	NPC150879
0.7919	Intermediate Similarity	NPC298979
0.7917	Intermediate Similarity	NPC244112
0.7912	Intermediate Similarity	NPC226708
0.791	Intermediate Similarity	NPC477560
0.7907	Intermediate Similarity	NPC168409
0.7904	Intermediate Similarity	NPC82285
0.7904	Intermediate Similarity	NPC133011
0.7879	Intermediate Similarity	NPC130941
0.7877	Intermediate Similarity	NPC299990
0.7877	Intermediate Similarity	NPC233718
0.7877	Intermediate Similarity	NPC73492
0.7865	Intermediate Similarity	NPC258695
0.7865	Intermediate Similarity	NPC470879
0.7865	Intermediate Similarity	NPC99179
0.7861	Intermediate Similarity	NPC304659
0.7861	Intermediate Similarity	NPC86144
0.7857	Intermediate Similarity	NPC82763
0.7845	Intermediate Similarity	NPC214116
0.7844	Intermediate Similarity	NPC476579
0.7841	Intermediate Similarity	NPC4669
0.7836	Intermediate Similarity	NPC165797
0.7831	Intermediate Similarity	NPC219162
0.7821	Intermediate Similarity	NPC476574
0.7821	Intermediate Similarity	NPC32413
0.7821	Intermediate Similarity	NPC312918
0.7821	Intermediate Similarity	NPC155442
0.7821	Intermediate Similarity	NPC474506
0.7821	Intermediate Similarity	NPC477561
0.7821	Intermediate Similarity	NPC160193
0.7816	Intermediate Similarity	NPC298186
0.7816	Intermediate Similarity	NPC301189
0.7814	Intermediate Similarity	NPC473716
0.7814	Intermediate Similarity	NPC475597
0.7809	Intermediate Similarity	NPC23219
0.7805	Intermediate Similarity	NPC185838
0.7784	Intermediate Similarity	NPC477258
0.7778	Intermediate Similarity	NPC118804
0.7771	Intermediate Similarity	NPC476571
0.7771	Intermediate Similarity	NPC428
0.7771	Intermediate Similarity	NPC246587
0.7771	Intermediate Similarity	NPC24233

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 NPC474708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	579
0.2-0.3	951
0.3-0.4	2277
0.4-0.5	2677
0.5-0.6	1819
0.6-0.7	554
0.7-0.8	111
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8443	Intermediate Similarity	NPD6107	Approved
0.8402	Intermediate Similarity	NPD4481	Phase 3
0.8287	Intermediate Similarity	NPD4420	Approved
0.8207	Intermediate Similarity	NPD5006	Approved
0.8207	Intermediate Similarity	NPD5005	Approved
0.816	Intermediate Similarity	NPD3640	Phase 3
0.816	Intermediate Similarity	NPD3641	Approved
0.816	Intermediate Similarity	NPD3639	Approved
0.815	Intermediate Similarity	NPD5312	Approved
0.815	Intermediate Similarity	NPD5313	Approved
0.8113	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7280	Phase 3
0.8023	Intermediate Similarity	NPD7281	Phase 3
0.8011	Intermediate Similarity	NPD7296	Approved
0.7964	Intermediate Similarity	NPD4773	Phase 2
0.7964	Intermediate Similarity	NPD4772	Phase 2
0.7963	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4584	Approved
0.7861	Intermediate Similarity	NPD4166	Phase 2
0.7816	Intermediate Similarity	NPD2970	Approved
0.7816	Intermediate Similarity	NPD2969	Approved
0.7784	Intermediate Similarity	NPD4210	Discontinued
0.7778	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3051	Approved
0.7722	Intermediate Similarity	NPD2971	Approved
0.7722	Intermediate Similarity	NPD2968	Approved
0.7697	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2489	Approved
0.767	Intermediate Similarity	NPD27	Approved
0.7657	Intermediate Similarity	NPD6071	Discontinued
0.7616	Intermediate Similarity	NPD2560	Approved
0.7616	Intermediate Similarity	NPD2563	Approved
0.7602	Intermediate Similarity	NPD7298	Approved
0.7594	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7827	Phase 1
0.7542	Intermediate Similarity	NPD8156	Discontinued
0.7529	Intermediate Similarity	NPD4017	Approved
0.7526	Intermediate Similarity	NPD4107	Approved
0.7515	Intermediate Similarity	NPD6030	Approved
0.7515	Intermediate Similarity	NPD6031	Approved
0.75	Intermediate Similarity	NPD5582	Discontinued
0.7486	Intermediate Similarity	NPD6853	Approved
0.7486	Intermediate Similarity	NPD8251	Approved
0.7486	Intermediate Similarity	NPD8099	Discontinued
0.7486	Intermediate Similarity	NPD6851	Approved
0.7486	Intermediate Similarity	NPD8252	Approved
0.7484	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD2898	Approved
0.7459	Intermediate Similarity	NPD6297	Approved
0.7446	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7313	Approved
0.7432	Intermediate Similarity	NPD7310	Approved
0.7432	Intermediate Similarity	NPD7311	Approved
0.7432	Intermediate Similarity	NPD7312	Approved
0.7419	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4727	Phase 1
0.741	Intermediate Similarity	NPD4237	Approved
0.741	Intermediate Similarity	NPD4236	Phase 3
0.7396	Intermediate Similarity	NPD4482	Phase 3
0.7391	Intermediate Similarity	NPD7309	Approved
0.7382	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD2490	Approved
0.738	Intermediate Similarity	NPD2488	Approved
0.7356	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6385	Approved
0.7341	Intermediate Similarity	NPD6386	Approved
0.7314	Intermediate Similarity	NPD5978	Approved
0.7314	Intermediate Similarity	NPD5977	Approved
0.7287	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2974	Approved
0.7277	Intermediate Similarity	NPD2973	Approved
0.7277	Intermediate Similarity	NPD2975	Approved
0.7273	Intermediate Similarity	NPD6788	Approved
0.7273	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7906	Approved
0.7273	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4859	Phase 1
0.7257	Intermediate Similarity	NPD5772	Approved
0.7257	Intermediate Similarity	NPD2977	Approved
0.7257	Intermediate Similarity	NPD5773	Approved
0.7257	Intermediate Similarity	NPD2978	Approved
0.7256	Intermediate Similarity	NPD2492	Phase 1
0.7254	Intermediate Similarity	NPD4580	Approved
0.7247	Intermediate Similarity	NPD5677	Discontinued
0.7243	Intermediate Similarity	NPD4578	Approved
0.7243	Intermediate Similarity	NPD4577	Approved
0.7238	Intermediate Similarity	NPD6625	Approved
0.7232	Intermediate Similarity	NPD7831	Phase 2
0.7232	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7833	Phase 2
0.7219	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4663	Approved
0.7219	Intermediate Similarity	NPD5241	Discontinued
0.7204	Intermediate Similarity	NPD8053	Approved
0.7204	Intermediate Similarity	NPD8054	Approved
0.7197	Intermediate Similarity	NPD3705	Approved
0.7181	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4967	Phase 2
0.7175	Intermediate Similarity	NPD4966	Approved
0.7175	Intermediate Similarity	NPD4965	Approved
0.7167	Intermediate Similarity	NPD4010	Discontinued
0.716	Intermediate Similarity	NPD5754	Discontinued
0.7152	Intermediate Similarity	NPD2653	Approved
0.7151	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7110	Phase 1
0.7135	Intermediate Similarity	NPD5604	Discontinued
0.7135	Intermediate Similarity	NPD3124	Discontinued
0.7128	Intermediate Similarity	NPD3450	Approved
0.7128	Intermediate Similarity	NPD2494	Approved
0.7128	Intermediate Similarity	NPD3452	Approved
0.7128	Intermediate Similarity	NPD2493	Approved
0.7127	Intermediate Similarity	NPD5242	Approved
0.7127	Intermediate Similarity	NPD6687	Approved
0.7127	Intermediate Similarity	NPD6688	Approved
0.7126	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5718	Phase 2
0.7107	Intermediate Similarity	NPD4582	Approved
0.7107	Intermediate Similarity	NPD4583	Approved
0.7102	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6234	Discontinued
0.7093	Intermediate Similarity	NPD1424	Approved
0.7093	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3057	Approved
0.709	Intermediate Similarity	NPD7291	Discontinued
0.7083	Intermediate Similarity	NPD3656	Approved
0.7076	Intermediate Similarity	NPD6667	Approved
0.7076	Intermediate Similarity	NPD6666	Approved
0.7075	Intermediate Similarity	NPD6723	Discontinued
0.7069	Intermediate Similarity	NPD3687	Approved
0.7069	Intermediate Similarity	NPD3686	Approved
0.7059	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4004	Approved
0.7056	Intermediate Similarity	NPD4002	Approved
0.7053	Intermediate Similarity	NPD6997	Phase 2
0.703	Intermediate Similarity	NPD3110	Approved
0.703	Intermediate Similarity	NPD3109	Approved
0.7027	Intermediate Similarity	NPD3885	Approved
0.7022	Intermediate Similarity	NPD5353	Approved
0.7019	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5976	Discontinued
0.701	Intermediate Similarity	NPD5564	Approved
0.701	Intermediate Similarity	NPD7047	Phase 3
0.7006	Intermediate Similarity	NPD37	Approved
0.7006	Intermediate Similarity	NPD3384	Approved
0.7006	Intermediate Similarity	NPD6896	Approved
0.7006	Intermediate Similarity	NPD3383	Approved
0.7006	Intermediate Similarity	NPD6895	Approved
0.7006	Intermediate Similarity	NPD3382	Approved
0.7005	Intermediate Similarity	NPD2972	Approved
0.7005	Intermediate Similarity	NPD3533	Approved
0.7	Intermediate Similarity	NPD7400	Phase 3
0.6995	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6876	Approved
0.6989	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6875	Approved
0.6985	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1375	Discontinued
0.6977	Remote Similarity	NPD7124	Phase 2
0.6976	Remote Similarity	NPD5980	Discovery
0.6949	Remote Similarity	NPD6873	Phase 2
0.6946	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4040	Phase 1
0.6927	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7802	Discontinued
0.6919	Remote Similarity	NPD3448	Approved
0.6919	Remote Similarity	NPD2491	Approved
0.6919	Remote Similarity	NPD7228	Approved
0.6915	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7248	Discontinued
0.6884	Remote Similarity	NPD7497	Discontinued
0.6872	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4585	Approved
0.6868	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4475	Approved
0.6867	Remote Similarity	NPD4474	Approved
0.6865	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4108	Discontinued
0.686	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6618	Phase 2
0.6842	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5297	Approved
0.6839	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4005	Discontinued
0.6825	Remote Similarity	NPD7549	Discontinued
0.6824	Remote Similarity	NPD2161	Phase 2
0.6823	Remote Similarity	NPD3349	Phase 2
0.6818	Remote Similarity	NPD7427	Discontinued
0.6818	Remote Similarity	NPD5457	Discontinued
0.6814	Remote Similarity	NPD5676	Approved
0.6813	Remote Similarity	NPD5709	Phase 3
0.6805	Remote Similarity	NPD6111	Discontinued
0.6802	Remote Similarity	NPD3060	Approved
0.6802	Remote Similarity	NPD4162	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