NPASS Compound

Structure

NPC32413 OpenBabel07101718312D 26 30 0 0 1 0 0 0 0 0999 V2000 -0.6578 -5.3240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3755 -3.1242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 -3.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1038 -4.0979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 -2.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4093 -3.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 -2.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3517 -2.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5831 -4.3268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4507 -2.5609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 9 25 1 0 0 0 0 9 26 1 0 0 0 0 10 14 2 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 8 1 6 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.14
Volume:	350.823
LogP:	1.856
LogD:	2.504
LogS:	-2.162
# Rotatable Bonds:	3
TPSA:	58.18
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.914
Synthetic Accessibility Score:	3.377
Fsp3:	0.4
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:	-4.93
MDCK Permeability:	2.080655212921556e-05
Pgp-inhibitor:	0.081
Pgp-substrate:	0.114
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.897
Plasma Protein Binding (PPB):	84.17993927001953%
Volume Distribution (VD):	1.722
Pgp-substrate:	10.110374450683594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.26
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.368
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.188
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	5.182
Half-life (T1/2):	0.178

ADMET: Toxicity

hERG Blockers:	0.391
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.217
AMES Toxicity:	0.222
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.16
Carcinogencity:	0.168
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC32413

Natural Product ID:	NPC32413
*Common Name:**	CHTZCWLHHIYAJY-LBPRGKRZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CHTZCWLHHIYAJY-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C20H21NO5/c1-22-13-5-4-10-8-12-15-11(6-7-21-12)17(23-2)20-19(25-9-26-20)16(15)14(10)18(13)24-3/h4-5,12,21H,6-9H2,1-3H3/t12-/m0/s1
SMILES:	COc1c(OC)ccc2c1c1c3[C@H](C2)NCCc3c(c2c1OCO2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254551
PubChem CID:	44448151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18217715]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	16500.0	nM	PMID[531579]

☑ 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 NPC32413 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	402
0.1-0.2	1859
0.2-0.3	9039
0.3-0.4	9143
0.4-0.5	6594
0.5-0.6	11429
0.6-0.7	3336
0.7-0.8	635
0.8-0.85	172
0.85-0.9	58
0.9-0.95	23
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474506
0.9939	High Similarity	NPC470879
0.9939	High Similarity	NPC258695
0.9877	High Similarity	NPC23219
0.9816	High Similarity	NPC112575
0.9643	High Similarity	NPC57036
0.9571	High Similarity	NPC6152
0.9512	High Similarity	NPC19520
0.9512	High Similarity	NPC149090
0.9471	High Similarity	NPC476576
0.9471	High Similarity	NPC186546
0.9448	High Similarity	NPC204947
0.9387	High Similarity	NPC304659
0.9387	High Similarity	NPC86144
0.9329	High Similarity	NPC247389
0.9306	High Similarity	NPC117717
0.9294	High Similarity	NPC135772
0.9268	High Similarity	NPC24264
0.9268	High Similarity	NPC219341
0.9268	High Similarity	NPC476432
0.9264	High Similarity	NPC189470
0.9231	High Similarity	NPC267408
0.9207	High Similarity	NPC225774
0.9207	High Similarity	NPC16805
0.9207	High Similarity	NPC167546
0.9207	High Similarity	NPC302527
0.9176	High Similarity	NPC155442
0.9176	High Similarity	NPC477561
0.9176	High Similarity	NPC312918
0.9176	High Similarity	NPC476574
0.9167	High Similarity	NPC477558
0.9118	High Similarity	NPC474507
0.9096	High Similarity	NPC210918
0.9024	High Similarity	NPC160298
0.9024	High Similarity	NPC306902
0.9024	High Similarity	NPC232924
0.9024	High Similarity	NPC477559
0.9024	High Similarity	NPC266753
0.9	High Similarity	NPC173416
0.9	High Similarity	NPC476577
0.9	High Similarity	NPC148709
0.8988	High Similarity	NPC152212
0.8966	High Similarity	NPC214116
0.8957	High Similarity	NPC203784
0.8957	High Similarity	NPC126519
0.8957	High Similarity	NPC170503
0.8947	High Similarity	NPC114364
0.8947	High Similarity	NPC320223
0.892	High Similarity	NPC475754
0.8902	High Similarity	NPC476572
0.8902	High Similarity	NPC476575
0.8882	High Similarity	NPC66341
0.8882	High Similarity	NPC477020
0.8882	High Similarity	NPC192135
0.8864	High Similarity	NPC82763
0.883	High Similarity	NPC128560
0.883	High Similarity	NPC199465
0.883	High Similarity	NPC229166
0.8793	High Similarity	NPC248642
0.8793	High Similarity	NPC275132
0.878	High Similarity	NPC99659
0.878	High Similarity	NPC325871
0.8765	High Similarity	NPC69712
0.8765	High Similarity	NPC477562
0.8765	High Similarity	NPC26240
0.8757	High Similarity	NPC281581
0.8757	High Similarity	NPC298979
0.8743	High Similarity	NPC156576
0.8735	High Similarity	NPC7393
0.8713	High Similarity	NPC239775
0.871	High Similarity	NPC46990
0.8706	High Similarity	NPC241055
0.8678	High Similarity	NPC126284
0.8655	High Similarity	NPC168753
0.8655	High Similarity	NPC118274
0.8639	High Similarity	NPC168409
0.8598	High Similarity	NPC326316
0.8598	High Similarity	NPC81733
0.8588	High Similarity	NPC81247
0.8588	High Similarity	NPC35627
0.8588	High Similarity	NPC476573
0.858	High Similarity	NPC116284
0.8545	High Similarity	NPC114124
0.8538	High Similarity	NPC205421
0.8538	High Similarity	NPC474931
0.8538	High Similarity	NPC306555
0.8538	High Similarity	NPC158376
0.8538	High Similarity	NPC81218
0.8538	High Similarity	NPC145832
0.8538	High Similarity	NPC12053
0.8538	High Similarity	NPC117188
0.8514	High Similarity	NPC118633
0.8514	High Similarity	NPC294790
0.8514	High Similarity	NPC148693
0.8492	Intermediate Similarity	NPC237579
0.848	Intermediate Similarity	NPC193853
0.848	Intermediate Similarity	NPC56887
0.848	Intermediate Similarity	NPC223077
0.8475	Intermediate Similarity	NPC299990
0.8475	Intermediate Similarity	NPC73492
0.8443	Intermediate Similarity	NPC216459
0.8443	Intermediate Similarity	NPC41178
0.8443	Intermediate Similarity	NPC244112
0.8443	Intermediate Similarity	NPC138487
0.8439	Intermediate Similarity	NPC75958
0.8427	Intermediate Similarity	NPC302275
0.8421	Intermediate Similarity	NPC253043
0.8421	Intermediate Similarity	NPC209377
0.8421	Intermediate Similarity	NPC306843
0.8421	Intermediate Similarity	NPC136508
0.8421	Intermediate Similarity	NPC212794
0.8421	Intermediate Similarity	NPC196447
0.8421	Intermediate Similarity	NPC96603
0.8421	Intermediate Similarity	NPC78222
0.8421	Intermediate Similarity	NPC477563
0.8421	Intermediate Similarity	NPC13504
0.8415	Intermediate Similarity	NPC475959
0.8393	Intermediate Similarity	NPC146288
0.8363	Intermediate Similarity	NPC1229
0.8363	Intermediate Similarity	NPC324144
0.8362	Intermediate Similarity	NPC475479
0.8362	Intermediate Similarity	NPC243454
0.8333	Intermediate Similarity	NPC47077
0.8333	Intermediate Similarity	NPC123323
0.8333	Intermediate Similarity	NPC14507
0.8315	Intermediate Similarity	NPC239584
0.8314	Intermediate Similarity	NPC180306
0.8306	Intermediate Similarity	NPC256124
0.8303	Intermediate Similarity	NPC37144
0.8303	Intermediate Similarity	NPC59907
0.8298	Intermediate Similarity	NPC156728
0.8298	Intermediate Similarity	NPC244606
0.8287	Intermediate Similarity	NPC312531
0.8284	Intermediate Similarity	NPC31311
0.8284	Intermediate Similarity	NPC234392
0.8266	Intermediate Similarity	NPC68328
0.8266	Intermediate Similarity	NPC195392
0.8253	Intermediate Similarity	NPC211296
0.8246	Intermediate Similarity	NPC166014
0.8246	Intermediate Similarity	NPC27410
0.8239	Intermediate Similarity	NPC2314
0.8226	Intermediate Similarity	NPC212163
0.8225	Intermediate Similarity	NPC76079
0.8214	Intermediate Similarity	NPC233029
0.8214	Intermediate Similarity	NPC210148
0.8212	Intermediate Similarity	NPC179704
0.8198	Intermediate Similarity	NPC80759
0.8198	Intermediate Similarity	NPC79402
0.8197	Intermediate Similarity	NPC473716
0.8197	Intermediate Similarity	NPC475597
0.8192	Intermediate Similarity	NPC329969
0.8187	Intermediate Similarity	NPC477080
0.8161	Intermediate Similarity	NPC264850
0.8161	Intermediate Similarity	NPC13916
0.8156	Intermediate Similarity	NPC244554
0.8156	Intermediate Similarity	NPC220961
0.8152	Intermediate Similarity	NPC478093
0.8152	Intermediate Similarity	NPC302001
0.8152	Intermediate Similarity	NPC24260
0.8146	Intermediate Similarity	NPC287588
0.8144	Intermediate Similarity	NPC219162
0.814	Intermediate Similarity	NPC119649
0.814	Intermediate Similarity	NPC235143
0.814	Intermediate Similarity	NPC230956
0.814	Intermediate Similarity	NPC271388
0.814	Intermediate Similarity	NPC205255
0.8138	Intermediate Similarity	NPC295676
0.8129	Intermediate Similarity	NPC79328
0.8118	Intermediate Similarity	NPC93593
0.8108	Intermediate Similarity	NPC478091
0.8108	Intermediate Similarity	NPC473589
0.8108	Intermediate Similarity	NPC30182
0.8108	Intermediate Similarity	NPC478092
0.8103	Intermediate Similarity	NPC24465
0.8103	Intermediate Similarity	NPC276944
0.8103	Intermediate Similarity	NPC238530
0.8103	Intermediate Similarity	NPC232514
0.8084	Intermediate Similarity	NPC130941
0.8081	Intermediate Similarity	NPC221864
0.8079	Intermediate Similarity	NPC76682
0.8079	Intermediate Similarity	NPC231371
0.8079	Intermediate Similarity	NPC198498
0.8079	Intermediate Similarity	NPC317145
0.8079	Intermediate Similarity	NPC276890
0.8079	Intermediate Similarity	NPC227060
0.8079	Intermediate Similarity	NPC115284
0.8079	Intermediate Similarity	NPC63646
0.8079	Intermediate Similarity	NPC10908
0.8079	Intermediate Similarity	NPC65403
0.8079	Intermediate Similarity	NPC317439
0.8077	Intermediate Similarity	NPC16357
0.8077	Intermediate Similarity	NPC9867
0.8077	Intermediate Similarity	NPC302245
0.8077	Intermediate Similarity	NPC95426
0.807	Intermediate Similarity	NPC29647
0.8066	Intermediate Similarity	NPC249405
0.8045	Intermediate Similarity	NPC293093
0.8043	Intermediate Similarity	NPC274661
0.8043	Intermediate Similarity	NPC175890
0.8043	Intermediate Similarity	NPC11296

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 NPC32413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	778
0.2-0.3	1127
0.3-0.4	2267
0.4-0.5	2688
0.5-0.6	1466
0.6-0.7	512
0.7-0.8	101
0.8-0.85	5
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	NPD8099	Discontinued
0.8079	Intermediate Similarity	NPD8252	Approved
0.8079	Intermediate Similarity	NPD8251	Approved
0.8034	Intermediate Similarity	NPD8156	Discontinued
0.8024	Intermediate Similarity	NPD4584	Approved
0.7988	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6788	Approved
0.7956	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1424	Approved
0.7907	Intermediate Similarity	NPD7298	Approved
0.7865	Intermediate Similarity	NPD4481	Phase 3
0.7853	Intermediate Similarity	NPD3051	Approved
0.7824	Intermediate Similarity	NPD6031	Approved
0.7824	Intermediate Similarity	NPD4727	Phase 1
0.7824	Intermediate Similarity	NPD6030	Approved
0.7772	Intermediate Similarity	NPD8054	Approved
0.7772	Intermediate Similarity	NPD8053	Approved
0.7742	Intermediate Similarity	NPD7906	Approved
0.7738	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD5005	Approved
0.772	Intermediate Similarity	NPD5006	Approved
0.7709	Intermediate Similarity	NPD2969	Approved
0.7709	Intermediate Similarity	NPD2970	Approved
0.7701	Intermediate Similarity	NPD3384	Approved
0.7701	Intermediate Similarity	NPD3383	Approved
0.7701	Intermediate Similarity	NPD3382	Approved
0.7657	Intermediate Similarity	NPD2977	Approved
0.7657	Intermediate Similarity	NPD2978	Approved
0.7638	Intermediate Similarity	NPD7827	Phase 1
0.7622	Intermediate Similarity	NPD4578	Approved
0.7622	Intermediate Similarity	NPD4577	Approved
0.7607	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4420	Approved
0.7594	Intermediate Similarity	NPD4663	Approved
0.7571	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD27	Approved
0.7569	Intermediate Similarity	NPD2489	Approved
0.7557	Intermediate Similarity	NPD4585	Approved
0.7544	Intermediate Similarity	NPD2421	Approved
0.7544	Intermediate Similarity	NPD2420	Approved
0.7529	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4055	Discovery
0.7527	Intermediate Similarity	NPD7311	Approved
0.7527	Intermediate Similarity	NPD7310	Approved
0.7527	Intermediate Similarity	NPD7312	Approved
0.7527	Intermediate Similarity	NPD7313	Approved
0.7514	Intermediate Similarity	NPD5976	Discontinued
0.7487	Intermediate Similarity	NPD7309	Approved
0.7485	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3845	Phase 1
0.7485	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD2968	Approved
0.7433	Intermediate Similarity	NPD2971	Approved
0.7429	Intermediate Similarity	NPD4017	Approved
0.7385	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2975	Approved
0.7371	Intermediate Similarity	NPD2974	Approved
0.7371	Intermediate Similarity	NPD2973	Approved
0.736	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD4859	Phase 1
0.7348	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6723	Discontinued
0.7308	Intermediate Similarity	NPD6107	Approved
0.7296	Intermediate Similarity	NPD8095	Phase 1
0.7283	Intermediate Similarity	NPD7124	Phase 2
0.7273	Intermediate Similarity	NPD6297	Approved
0.7268	Intermediate Similarity	NPD4166	Phase 2
0.7268	Intermediate Similarity	NPD6071	Discontinued
0.7259	Intermediate Similarity	NPD4580	Approved
0.7253	Intermediate Similarity	NPD5677	Discontinued
0.7246	Intermediate Similarity	NPD3109	Approved
0.7246	Intermediate Similarity	NPD3110	Approved
0.7241	Intermediate Similarity	NPD7598	Phase 2
0.7225	Intermediate Similarity	NPD5241	Discontinued
0.7222	Intermediate Similarity	NPD3450	Approved
0.7222	Intermediate Similarity	NPD2560	Approved
0.7222	Intermediate Similarity	NPD2494	Approved
0.7222	Intermediate Similarity	NPD2563	Approved
0.7222	Intermediate Similarity	NPD3452	Approved
0.7222	Intermediate Similarity	NPD2493	Approved
0.7216	Intermediate Similarity	NPD3641	Approved
0.7216	Intermediate Similarity	NPD3639	Approved
0.7216	Intermediate Similarity	NPD3640	Phase 3
0.7211	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD2898	Approved
0.7181	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7833	Phase 2
0.7143	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7831	Phase 2
0.7135	Intermediate Similarity	NPD4005	Discontinued
0.712	Intermediate Similarity	NPD6853	Approved
0.712	Intermediate Similarity	NPD6851	Approved
0.7114	Intermediate Similarity	NPD4582	Approved
0.7114	Intermediate Similarity	NPD4583	Approved
0.7113	Intermediate Similarity	NPD2488	Approved
0.7113	Intermediate Similarity	NPD2490	Approved
0.711	Intermediate Similarity	NPD3060	Approved
0.7074	Intermediate Similarity	NPD6042	Phase 2
0.7074	Intermediate Similarity	NPD42	Phase 2
0.7069	Intermediate Similarity	NPD5754	Discontinued
0.7066	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4004	Approved
0.7065	Intermediate Similarity	NPD4002	Approved
0.7056	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4772	Phase 2
0.7056	Intermediate Similarity	NPD4773	Phase 2
0.7054	Intermediate Similarity	NPD8152	Approved
0.7054	Intermediate Similarity	NPD8153	Approved
0.7049	Intermediate Similarity	NPD5604	Discontinued
0.7035	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5160	Discontinued
0.7027	Intermediate Similarity	NPD7802	Discontinued
0.7024	Intermediate Similarity	NPD5718	Phase 2
0.7015	Intermediate Similarity	NPD3515	Approved
0.7015	Intermediate Similarity	NPD3516	Approved
0.7011	Intermediate Similarity	NPD5709	Phase 3
0.701	Intermediate Similarity	NPD3349	Phase 2
0.7005	Intermediate Similarity	NPD6625	Approved
0.7	Intermediate Similarity	NPD5457	Discontinued
0.6989	Remote Similarity	NPD4010	Discontinued
0.6974	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4666	Phase 3
0.6954	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7047	Phase 3
0.6927	Remote Similarity	NPD7549	Discontinued
0.6923	Remote Similarity	NPD37	Approved
0.6919	Remote Similarity	NPD3763	Approved
0.6919	Remote Similarity	NPD7400	Phase 3
0.6915	Remote Similarity	NPD4107	Approved
0.6914	Remote Similarity	NPD4162	Approved
0.6914	Remote Similarity	NPD5177	Phase 3
0.6901	Remote Similarity	NPD6997	Phase 2
0.6891	Remote Similarity	NPD7280	Phase 3
0.6891	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7281	Phase 3
0.6888	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4474	Approved
0.6882	Remote Similarity	NPD4475	Approved
0.6882	Remote Similarity	NPD6037	Discontinued
0.6879	Remote Similarity	NPD4108	Discontinued
0.6878	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7466	Approved
0.6872	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5089	Approved
0.6868	Remote Similarity	NPD5090	Approved
0.6863	Remote Similarity	NPD4040	Phase 1
0.6862	Remote Similarity	NPD5242	Approved
0.6856	Remote Similarity	NPD6618	Phase 2
0.6854	Remote Similarity	NPD3124	Discontinued
0.6842	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3454	Phase 3
0.6837	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2677	Approved
0.6832	Remote Similarity	NPD6612	Phase 2
0.6831	Remote Similarity	NPD5720	Discontinued
0.6821	Remote Similarity	NPD6111	Discontinued
0.6821	Remote Similarity	NPD6895	Approved
0.6821	Remote Similarity	NPD2200	Suspended
0.6821	Remote Similarity	NPD6896	Approved
0.6813	Remote Similarity	NPD4678	Approved
0.6813	Remote Similarity	NPD4675	Approved
0.6811	Remote Similarity	NPD4966	Approved
0.6811	Remote Similarity	NPD4967	Phase 2
0.6811	Remote Similarity	NPD4965	Approved
0.6805	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5582	Discontinued
0.68	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4482	Phase 3
0.6788	Remote Similarity	NPD3705	Approved
0.6776	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7479	Phase 2
0.6763	Remote Similarity	NPD2492	Phase 1
0.6763	Remote Similarity	NPD2568	Approved
0.6763	Remote Similarity	NPD2653	Approved
0.6761	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5297	Approved
0.6758	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5977	Approved
0.6757	Remote Similarity	NPD5978	Approved
0.6757	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6841	Approved
0.6751	Remote Similarity	NPD6843	Phase 3
0.6751	Remote Similarity	NPD6842	Approved
0.6738	Remote Similarity	NPD6234	Discontinued
0.6723	Remote Similarity	NPD4237	Approved
0.6723	Remote Similarity	NPD6674	Discontinued
0.6723	Remote Similarity	NPD4236	Phase 3
0.6722	Remote Similarity	NPD7447	Phase 1
0.6722	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4606	Clinical (unspecified phase)

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