NPASS Compound

Structure

CID57812 OpenBabel06191715392D 23 27 0 0 1 0 0 0 0 0999 V2000 -0.7670 -3.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7673 -2.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -2.6580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5345 -0.8858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7671 0.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3022 0.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3018 -1.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7676 0.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4328 -0.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5343 -3.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7674 -1.3288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5347 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5345 -0.8862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7672 -2.2150 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0694 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0692 -0.8865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7674 -1.3289 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0002 -0.8859 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 -2.3016 -3.9872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9121 0.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9118 -1.1605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5344 -2.6581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 3 1 0 0 0 0 2 11 2 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 19 1 0 0 0 0 6 12 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 12 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 20 2 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 1 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 13 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.13
Volume:	310.077
LogP:	2.589
LogD:	2.449
LogS:	-2.994
# Rotatable Bonds:	2
TPSA:	48.0
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	3.956
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:	-4.681
MDCK Permeability:	5.030382817494683e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	79.16187286376953%
Volume Distribution (VD):	2.076
Pgp-substrate:	16.31121063232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.65
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.38
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.372
CYP2D6-inhibitor:	0.975
CYP2D6-substrate:	0.621
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.466

ADMET: Excretion

Clearance (CL):	14.351
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.573
AMES Toxicity:	0.266
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.042
Carcinogencity:	0.94
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC57812

Natural Product ID:	NPC57812
*Common Name:**	Acetylcaranine
IUPAC Name:	n.a.
Synonyms:	Acetylcaranine
Standard InCHIKey:	SEWQEQSXDGJDGG-ZTFGCOKTSA-N
Standard InCHI:	InChI=1S/C18H19NO4/c1-10(20)23-14-3-2-11-4-5-19-8-12-6-15-16(22-9-21-15)7-13(12)17(14)18(11)19/h2,6-7,14,17-18H,3-5,8-9H2,1H3/p+1/t14-,17-,18-/m1/s1
SMILES:	CC(=O)O[C@@H]1CC=C2CC[NH+]3Cc4cc5c(cc4[C@H]1[C@@H]23)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522145
PubChem CID:	258956
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
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ja01076a047]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10846753]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6512532]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5324	Crinum macrantherum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5324	Crinum macrantherum	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
ED50	1
IC50	5

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.23	ug ml-1	PMID[503706]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	56000.0	nM	PMID[503707]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3500.0	nM	PMID[503707]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	1.97	ug.mL-1	PMID[503708]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	100.0	ug.mL-1	PMID[503708]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	35.9	ug.mL-1	PMID[503708]

☑ 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 NPC57812 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	248
0.1-0.2	1264
0.2-0.3	4142
0.3-0.4	12258
0.4-0.5	7214
0.5-0.6	13359
0.6-0.7	3225
0.7-0.8	784
0.8-0.85	113
0.85-0.9	55
0.9-0.95	23
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474324
0.9935	High Similarity	NPC475845
0.9872	High Similarity	NPC474708
0.9686	High Similarity	NPC304675
0.9625	High Similarity	NPC237044
0.9565	High Similarity	NPC474325
0.9506	High Similarity	NPC474745
0.9333	High Similarity	NPC475981
0.9333	High Similarity	NPC474746
0.9304	High Similarity	NPC320104
0.9264	High Similarity	NPC474470
0.925	High Similarity	NPC190332
0.925	High Similarity	NPC181653
0.9222	High Similarity	NPC230098
0.913	High Similarity	NPC100566
0.9045	High Similarity	NPC78733
0.8963	High Similarity	NPC65403
0.8957	High Similarity	NPC158148
0.8957	High Similarity	NPC290759
0.8957	High Similarity	NPC266176
0.8957	High Similarity	NPC82533
0.8902	High Similarity	NPC75958
0.8889	High Similarity	NPC247972
0.8848	High Similarity	NPC470739
0.8848	High Similarity	NPC225597
0.8848	High Similarity	NPC477640
0.8841	High Similarity	NPC475686
0.8841	High Similarity	NPC58766
0.882	High Similarity	NPC4304
0.8797	High Similarity	NPC148898
0.879	High Similarity	NPC223125
0.8788	High Similarity	NPC474475
0.8788	High Similarity	NPC311991
0.8773	High Similarity	NPC180306
0.875	High Similarity	NPC294790
0.875	High Similarity	NPC148693
0.875	High Similarity	NPC118633
0.872	High Similarity	NPC476002
0.8704	High Similarity	NPC205167
0.8704	High Similarity	NPC97072
0.8704	High Similarity	NPC249274
0.8704	High Similarity	NPC215829
0.8679	High Similarity	NPC210148
0.8679	High Similarity	NPC233029
0.8679	High Similarity	NPC223124
0.8667	High Similarity	NPC210918
0.8662	High Similarity	NPC475959
0.8659	High Similarity	NPC231198
0.8642	High Similarity	NPC477080
0.8639	High Similarity	NPC15919
0.8631	High Similarity	NPC187678
0.8598	High Similarity	NPC218614
0.8588	High Similarity	NPC244554
0.8545	High Similarity	NPC16805
0.8545	High Similarity	NPC302527
0.8545	High Similarity	NPC167546
0.8519	High Similarity	NPC234392
0.8519	High Similarity	NPC31311
0.8519	High Similarity	NPC146288
0.8506	High Similarity	NPC237579
0.8494	Intermediate Similarity	NPC476432
0.8494	Intermediate Similarity	NPC24264
0.8475	Intermediate Similarity	NPC33256
0.8457	Intermediate Similarity	NPC41178
0.8457	Intermediate Similarity	NPC138487
0.8457	Intermediate Similarity	NPC216459
0.8443	Intermediate Similarity	NPC247389
0.8443	Intermediate Similarity	NPC252960
0.8434	Intermediate Similarity	NPC225774
0.8391	Intermediate Similarity	NPC9867
0.8383	Intermediate Similarity	NPC219341
0.8382	Intermediate Similarity	NPC102760
0.8382	Intermediate Similarity	NPC275132
0.8363	Intermediate Similarity	NPC35680
0.8354	Intermediate Similarity	NPC130926
0.8353	Intermediate Similarity	NPC2314
0.8312	Intermediate Similarity	NPC7018
0.8304	Intermediate Similarity	NPC49353
0.8303	Intermediate Similarity	NPC106786
0.8294	Intermediate Similarity	NPC149090
0.8294	Intermediate Similarity	NPC19520
0.8263	Intermediate Similarity	NPC59567
0.8256	Intermediate Similarity	NPC241704
0.8253	Intermediate Similarity	NPC306902
0.8253	Intermediate Similarity	NPC232924
0.8253	Intermediate Similarity	NPC266753
0.8253	Intermediate Similarity	NPC160298
0.8253	Intermediate Similarity	NPC477559
0.8235	Intermediate Similarity	NPC6152
0.8232	Intermediate Similarity	NPC76079
0.8217	Intermediate Similarity	NPC474915
0.8217	Intermediate Similarity	NPC328750
0.8217	Intermediate Similarity	NPC213206
0.8217	Intermediate Similarity	NPC188163
0.8202	Intermediate Similarity	NPC63152
0.8199	Intermediate Similarity	NPC59907
0.8199	Intermediate Similarity	NPC37144
0.8198	Intermediate Similarity	NPC229166
0.8198	Intermediate Similarity	NPC128560
0.8198	Intermediate Similarity	NPC199465
0.8193	Intermediate Similarity	NPC59028
0.8193	Intermediate Similarity	NPC92191
0.8193	Intermediate Similarity	NPC111485
0.8192	Intermediate Similarity	NPC141440
0.8182	Intermediate Similarity	NPC147091
0.8182	Intermediate Similarity	NPC180756
0.8182	Intermediate Similarity	NPC323443
0.8177	Intermediate Similarity	NPC46744
0.8177	Intermediate Similarity	NPC70290
0.8177	Intermediate Similarity	NPC73020
0.8177	Intermediate Similarity	NPC124302
0.8177	Intermediate Similarity	NPC215098
0.8177	Intermediate Similarity	NPC14622
0.8176	Intermediate Similarity	NPC241055
0.8171	Intermediate Similarity	NPC248642
0.8171	Intermediate Similarity	NPC116284
0.8161	Intermediate Similarity	NPC220961
0.8161	Intermediate Similarity	NPC126284
0.8161	Intermediate Similarity	NPC32154
0.8153	Intermediate Similarity	NPC314682
0.8129	Intermediate Similarity	NPC474953
0.8125	Intermediate Similarity	NPC156576
0.8121	Intermediate Similarity	NPC325871
0.8121	Intermediate Similarity	NPC99659
0.8121	Intermediate Similarity	NPC93593
0.8113	Intermediate Similarity	NPC128019
0.8113	Intermediate Similarity	NPC136860
0.8113	Intermediate Similarity	NPC476567
0.8107	Intermediate Similarity	NPC276944
0.8107	Intermediate Similarity	NPC238530
0.8107	Intermediate Similarity	NPC232514
0.8103	Intermediate Similarity	NPC114364
0.8103	Intermediate Similarity	NPC320223
0.8098	Intermediate Similarity	NPC328700
0.8098	Intermediate Similarity	NPC274026
0.8098	Intermediate Similarity	NPC202771
0.8098	Intermediate Similarity	NPC2173
0.8098	Intermediate Similarity	NPC119818
0.809	Intermediate Similarity	NPC166979
0.8087	Intermediate Similarity	NPC226652
0.8087	Intermediate Similarity	NPC314100
0.8087	Intermediate Similarity	NPC120671
0.8087	Intermediate Similarity	NPC72788
0.8086	Intermediate Similarity	NPC7467
0.8065	Intermediate Similarity	NPC80472
0.8057	Intermediate Similarity	NPC267408
0.8046	Intermediate Similarity	NPC283999
0.8034	Intermediate Similarity	NPC162694
0.8025	Intermediate Similarity	NPC16107
0.8025	Intermediate Similarity	NPC210437
0.8025	Intermediate Similarity	NPC106295
0.8025	Intermediate Similarity	NPC476144
0.8025	Intermediate Similarity	NPC51957
0.8024	Intermediate Similarity	NPC476572
0.8012	Intermediate Similarity	NPC150879
0.8012	Intermediate Similarity	NPC244112
0.8012	Intermediate Similarity	NPC298979
0.8	Intermediate Similarity	NPC477560
0.8	Intermediate Similarity	NPC133011
0.8	Intermediate Similarity	NPC82285
0.8	Intermediate Similarity	NPC168409
0.7975	Intermediate Similarity	NPC130941
0.7966	Intermediate Similarity	NPC299990
0.7966	Intermediate Similarity	NPC73492
0.7966	Intermediate Similarity	NPC233718
0.7955	Intermediate Similarity	NPC99179
0.7955	Intermediate Similarity	NPC258695
0.7955	Intermediate Similarity	NPC470879
0.7953	Intermediate Similarity	NPC304659
0.7953	Intermediate Similarity	NPC86144
0.7944	Intermediate Similarity	NPC82763
0.7939	Intermediate Similarity	NPC476579
0.7933	Intermediate Similarity	NPC214116
0.7929	Intermediate Similarity	NPC165797
0.7927	Intermediate Similarity	NPC219162
0.7922	Intermediate Similarity	NPC160193
0.791	Intermediate Similarity	NPC476574
0.791	Intermediate Similarity	NPC32413
0.791	Intermediate Similarity	NPC312918
0.791	Intermediate Similarity	NPC474506
0.791	Intermediate Similarity	NPC155442
0.791	Intermediate Similarity	NPC477561
0.7907	Intermediate Similarity	NPC301189
0.7907	Intermediate Similarity	NPC298186
0.7901	Intermediate Similarity	NPC185838
0.7901	Intermediate Similarity	NPC475597
0.7901	Intermediate Similarity	NPC473716
0.7901	Intermediate Similarity	NPC319549
0.7898	Intermediate Similarity	NPC23219
0.7895	Intermediate Similarity	NPC306669
0.787	Intermediate Similarity	NPC118804
0.7866	Intermediate Similarity	NPC246587
0.7866	Intermediate Similarity	NPC476571
0.7866	Intermediate Similarity	NPC24233
0.7866	Intermediate Similarity	NPC135538
0.7866	Intermediate Similarity	NPC147390
0.7866	Intermediate Similarity	NPC428
0.7857	Intermediate Similarity	NPC94499
0.7853	Intermediate Similarity	NPC27887
0.7849	Intermediate Similarity	NPC124657

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 NPC57812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	613
0.2-0.3	956
0.3-0.4	2304
0.4-0.5	2678
0.5-0.6	1760
0.6-0.7	547
0.7-0.8	110
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
0.8503	High Similarity	NPD4481	Phase 3
0.8323	Intermediate Similarity	NPD6107	Approved
0.8217	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8177	Intermediate Similarity	NPD4420	Approved
0.8098	Intermediate Similarity	NPD5005	Approved
0.8098	Intermediate Similarity	NPD5006	Approved
0.8063	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4773	Phase 2
0.8061	Intermediate Similarity	NPD4772	Phase 2
0.8037	Intermediate Similarity	NPD3639	Approved
0.8037	Intermediate Similarity	NPD3641	Approved
0.8037	Intermediate Similarity	NPD3640	Phase 3
0.8035	Intermediate Similarity	NPD5312	Approved
0.8035	Intermediate Similarity	NPD5313	Approved
0.8025	Intermediate Similarity	NPD4584	Approved
0.791	Intermediate Similarity	NPD7280	Phase 3
0.791	Intermediate Similarity	NPD7281	Phase 3
0.7907	Intermediate Similarity	NPD2969	Approved
0.7907	Intermediate Similarity	NPD2970	Approved
0.7901	Intermediate Similarity	NPD7296	Approved
0.7879	Intermediate Similarity	NPD4210	Discontinued
0.7849	Intermediate Similarity	NPD3051	Approved
0.7791	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2489	Approved
0.7759	Intermediate Similarity	NPD27	Approved
0.7746	Intermediate Similarity	NPD6071	Discontinued
0.7746	Intermediate Similarity	NPD4166	Phase 2
0.7706	Intermediate Similarity	NPD2563	Approved
0.7706	Intermediate Similarity	NPD2560	Approved
0.7692	Intermediate Similarity	NPD7298	Approved
0.7667	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8156	Discontinued
0.7619	Intermediate Similarity	NPD4017	Approved
0.7611	Intermediate Similarity	NPD2968	Approved
0.7611	Intermediate Similarity	NPD2971	Approved
0.7605	Intermediate Similarity	NPD6031	Approved
0.7605	Intermediate Similarity	NPD6030	Approved
0.7581	Intermediate Similarity	NPD5582	Discontinued
0.758	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8252	Approved
0.7571	Intermediate Similarity	NPD8099	Discontinued
0.7571	Intermediate Similarity	NPD8251	Approved
0.7557	Intermediate Similarity	NPD2898	Approved
0.7527	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7312	Approved
0.7514	Intermediate Similarity	NPD7311	Approved
0.7514	Intermediate Similarity	NPD7310	Approved
0.7514	Intermediate Similarity	NPD7313	Approved
0.75	Intermediate Similarity	NPD4727	Phase 1
0.75	Intermediate Similarity	NPD4237	Approved
0.75	Intermediate Similarity	NPD4236	Phase 3
0.7487	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7309	Approved
0.7449	Intermediate Similarity	NPD7827	Phase 1
0.7442	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4107	Approved
0.7377	Intermediate Similarity	NPD6853	Approved
0.7377	Intermediate Similarity	NPD6851	Approved
0.7375	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6788	Approved
0.7351	Intermediate Similarity	NPD7906	Approved
0.7348	Intermediate Similarity	NPD6297	Approved
0.7346	Intermediate Similarity	NPD2492	Phase 1
0.7341	Intermediate Similarity	NPD2977	Approved
0.7341	Intermediate Similarity	NPD2978	Approved
0.7341	Intermediate Similarity	NPD5773	Approved
0.7341	Intermediate Similarity	NPD5772	Approved
0.7337	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5677	Discontinued
0.7322	Intermediate Similarity	NPD4577	Approved
0.7322	Intermediate Similarity	NPD4578	Approved
0.7314	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7833	Phase 2
0.7314	Intermediate Similarity	NPD7831	Phase 2
0.7312	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5241	Discontinued
0.7297	Intermediate Similarity	NPD4663	Approved
0.7292	Intermediate Similarity	NPD4482	Phase 3
0.729	Intermediate Similarity	NPD3705	Approved
0.7283	Intermediate Similarity	NPD8053	Approved
0.7283	Intermediate Similarity	NPD8054	Approved
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2490	Approved
0.7273	Intermediate Similarity	NPD2488	Approved
0.7258	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4010	Discontinued
0.7246	Intermediate Similarity	NPD5754	Discontinued
0.7232	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6386	Approved
0.7225	Intermediate Similarity	NPD6385	Approved
0.7219	Intermediate Similarity	NPD3124	Discontinued
0.7216	Intermediate Similarity	NPD5604	Discontinued
0.7209	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6687	Approved
0.7207	Intermediate Similarity	NPD6688	Approved
0.7205	Intermediate Similarity	NPD5718	Phase 2
0.72	Intermediate Similarity	NPD5977	Approved
0.72	Intermediate Similarity	NPD5978	Approved
0.7188	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1424	Approved
0.7176	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD2973	Approved
0.7173	Intermediate Similarity	NPD2975	Approved
0.7173	Intermediate Similarity	NPD2974	Approved
0.7169	Intermediate Similarity	NPD3656	Approved
0.7157	Intermediate Similarity	NPD4859	Phase 1
0.715	Intermediate Similarity	NPD4580	Approved
0.7143	Intermediate Similarity	NPD6625	Approved
0.7134	Intermediate Similarity	NPD2653	Approved
0.7117	Intermediate Similarity	NPD3110	Approved
0.7117	Intermediate Similarity	NPD3109	Approved
0.7104	Intermediate Similarity	NPD3885	Approved
0.7093	Intermediate Similarity	NPD5976	Discontinued
0.7091	Intermediate Similarity	NPD6895	Approved
0.7091	Intermediate Similarity	NPD6896	Approved
0.7086	Intermediate Similarity	NPD3384	Approved
0.7086	Intermediate Similarity	NPD3382	Approved
0.7086	Intermediate Similarity	NPD3383	Approved
0.7079	Intermediate Similarity	NPD7400	Phase 3
0.7072	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1375	Discontinued
0.7062	Intermediate Similarity	NPD4965	Approved
0.7062	Intermediate Similarity	NPD4967	Phase 2
0.7062	Intermediate Similarity	NPD4966	Approved
0.7059	Intermediate Similarity	NPD7124	Phase 2
0.7059	Intermediate Similarity	NPD6667	Approved
0.7059	Intermediate Similarity	NPD6666	Approved
0.7052	Intermediate Similarity	NPD3686	Approved
0.7052	Intermediate Similarity	NPD3687	Approved
0.703	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7110	Phase 1
0.7026	Intermediate Similarity	NPD3452	Approved
0.7026	Intermediate Similarity	NPD2494	Approved
0.7026	Intermediate Similarity	NPD3450	Approved
0.7026	Intermediate Similarity	NPD2493	Approved
0.7017	Intermediate Similarity	NPD5242	Approved
0.7005	Intermediate Similarity	NPD4582	Approved
0.7005	Intermediate Similarity	NPD4583	Approved
0.7	Intermediate Similarity	NPD7802	Discontinued
0.699	Remote Similarity	NPD3057	Approved
0.6984	Remote Similarity	NPD7291	Discontinued
0.6983	Remote Similarity	NPD6234	Discontinued
0.6981	Remote Similarity	NPD6723	Discontinued
0.6957	Remote Similarity	NPD6997	Phase 2
0.6954	Remote Similarity	NPD4002	Approved
0.6954	Remote Similarity	NPD4004	Approved
0.6952	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4475	Approved
0.6951	Remote Similarity	NPD4474	Approved
0.6949	Remote Similarity	NPD4585	Approved
0.6946	Remote Similarity	NPD4108	Discontinued
0.6941	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5297	Approved
0.6914	Remote Similarity	NPD4005	Discontinued
0.6912	Remote Similarity	NPD7047	Phase 3
0.691	Remote Similarity	NPD5353	Approved
0.6907	Remote Similarity	NPD5564	Approved
0.6905	Remote Similarity	NPD2161	Phase 2
0.6904	Remote Similarity	NPD2972	Approved
0.6904	Remote Similarity	NPD3533	Approved
0.6898	Remote Similarity	NPD7549	Discontinued
0.6895	Remote Similarity	NPD3349	Phase 2
0.6893	Remote Similarity	NPD37	Approved
0.6889	Remote Similarity	NPD5709	Phase 3
0.6886	Remote Similarity	NPD6111	Discontinued
0.6884	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5177	Phase 3
0.6882	Remote Similarity	NPD4162	Approved
0.6882	Remote Similarity	NPD3060	Approved
0.6878	Remote Similarity	NPD5980	Discovery
0.6875	Remote Similarity	NPD6876	Approved
0.6875	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6875	Approved
0.6862	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4666	Phase 3
0.6842	Remote Similarity	NPD6331	Phase 2
0.6837	Remote Similarity	NPD8095	Phase 1
0.6836	Remote Similarity	NPD6873	Phase 2
0.6834	Remote Similarity	NPD4040	Phase 1
0.6833	Remote Similarity	NPD4055	Discovery
0.6832	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2420	Approved
0.6821	Remote Similarity	NPD2421	Approved
0.6818	Remote Similarity	NPD3448	Approved
0.6818	Remote Similarity	NPD2491	Approved
0.6811	Remote Similarity	NPD7228	Approved
0.6809	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2238	Phase 2
0.6806	Remote Similarity	NPD6843	Phase 3

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