NPASS Compound

Structure

CID314333 OpenBabel06191716122D 25 29 0 0 1 0 0 0 0 0999 V2000 1.4598 -1.6109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4909 -4.9924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5627 -1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5766 -1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5766 -2.1124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7420 -0.6670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7420 -2.5942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7347 0.0779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8486 0.4566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5902 -1.4724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3100 -1.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6805 -0.3662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -1.1265 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1907 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9075 -1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9910 -0.8510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9075 -2.1124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4246 -1.6306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1721 -0.9481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4581 -3.3237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4619 -1.6738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9910 -2.4102 0.0000 N 0 0 0 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 2.4216 -3.3048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9928 -4.1675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 25 1 0 0 0 0 3 14 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 2 0 0 0 0 7 17 2 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 6 0 0 0 19 23 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 21 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.18
Volume:	352.745
LogP:	3.569
LogD:	3.471
LogS:	-4.099
# Rotatable Bonds:	3
TPSA:	45.33
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	5.011
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983
MDCK Permeability:	2.4545923224650323e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	90.2657470703125%
Volume Distribution (VD):	1.834
Pgp-substrate:	6.524744510650635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.435
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.817
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.557
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	7.479
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.655
Human Hepatotoxicity (H-HT):	0.66
Drug-inuced Liver Injury (DILI):	0.648
AMES Toxicity:	0.638
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.076
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC314333

Natural Product ID:	NPC314333
*Common Name:**	CMKFQVZJOWHHDV-QYWJTTNJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CMKFQVZJOWHHDV-QYWJTTNJSA-N
Standard InCHI:	InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13?,19-,21+/m1/s1
SMILES:	CCC1=CC2CN3[C@H]1[C@@](C2)(C(=O)OC)c1[nH]c2c(c1CC3)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1418171
PubChem CID:	5315744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type 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
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
NPO9380	Catharanthus ovalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27273	Catharanthus longifolius	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27273	Catharanthus longifolius	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9380	Catharanthus ovalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5881	Catharanthus roseus	Species	Apocynaceae	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
Potency	5

Activity Type	# Activity
Individual Protein	2
Others	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	31622.8	nM	PMID[548589]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[548589]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	35481.3	nM	PMID[548589]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[548589]

☑ 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 NPC314333 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	314
0.1-0.2	1596
0.2-0.3	9744
0.3-0.4	21374
0.4-0.5	4794
0.5-0.6	2189
0.6-0.7	1982
0.7-0.8	602
0.8-0.85	68
0.85-0.9	28
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC329858
0.9066	High Similarity	NPC162730
0.8989	High Similarity	NPC55493
0.8962	High Similarity	NPC474116
0.8696	High Similarity	NPC241024
0.8601	High Similarity	NPC330009
0.8601	High Similarity	NPC469928
0.8541	High Similarity	NPC52557
0.8525	High Similarity	NPC269886
0.8525	High Similarity	NPC472295
0.8525	High Similarity	NPC472210
0.8525	High Similarity	NPC81802
0.8525	High Similarity	NPC247735
0.8513	High Similarity	NPC96321
0.8513	High Similarity	NPC473041
0.8474	Intermediate Similarity	NPC477065
0.8449	Intermediate Similarity	NPC214428
0.8427	Intermediate Similarity	NPC469896
0.8407	Intermediate Similarity	NPC111602
0.8407	Intermediate Similarity	NPC175474
0.8407	Intermediate Similarity	NPC63199
0.8407	Intermediate Similarity	NPC196251
0.8407	Intermediate Similarity	NPC102338
0.8385	Intermediate Similarity	NPC469743
0.8378	Intermediate Similarity	NPC19692
0.8378	Intermediate Similarity	NPC220151
0.837	Intermediate Similarity	NPC472292
0.8368	Intermediate Similarity	NPC475847
0.8368	Intermediate Similarity	NPC185742
0.8361	Intermediate Similarity	NPC472112
0.836	Intermediate Similarity	NPC137589
0.8351	Intermediate Similarity	NPC475778
0.8325	Intermediate Similarity	NPC277350
0.828	Intermediate Similarity	NPC474121
0.827	Intermediate Similarity	NPC472113
0.8247	Intermediate Similarity	NPC234999
0.8235	Intermediate Similarity	NPC472293
0.8202	Intermediate Similarity	NPC189812
0.8202	Intermediate Similarity	NPC329688
0.8167	Intermediate Similarity	NPC219336
0.8158	Intermediate Similarity	NPC313985
0.8158	Intermediate Similarity	NPC79129
0.8158	Intermediate Similarity	NPC195461
0.8158	Intermediate Similarity	NPC294909
0.8158	Intermediate Similarity	NPC254240
0.8158	Intermediate Similarity	NPC81654
0.8158	Intermediate Similarity	NPC199851
0.8158	Intermediate Similarity	NPC312870
0.8158	Intermediate Similarity	NPC128265
0.8158	Intermediate Similarity	NPC49196
0.8158	Intermediate Similarity	NPC249150
0.8137	Intermediate Similarity	NPC311906
0.8111	Intermediate Similarity	NPC15573
0.8111	Intermediate Similarity	NPC14113
0.8111	Intermediate Similarity	NPC145885
0.8111	Intermediate Similarity	NPC183662
0.8111	Intermediate Similarity	NPC84827
0.8111	Intermediate Similarity	NPC217372
0.8105	Intermediate Similarity	NPC472297
0.8105	Intermediate Similarity	NPC472296
0.8087	Intermediate Similarity	NPC472119
0.8066	Intermediate Similarity	NPC213468
0.8061	Intermediate Similarity	NPC471304
0.8053	Intermediate Similarity	NPC50503
0.8042	Intermediate Similarity	NPC245916
0.8035	Intermediate Similarity	NPC285469
0.8033	Intermediate Similarity	NPC19679
0.8019	Intermediate Similarity	NPC474192
0.8019	Intermediate Similarity	NPC475720
0.8011	Intermediate Similarity	NPC271797
0.8011	Intermediate Similarity	NPC234987
0.8011	Intermediate Similarity	NPC21174
0.7981	Intermediate Similarity	NPC473105
0.7956	Intermediate Similarity	NPC267885
0.7955	Intermediate Similarity	NPC16667
0.7935	Intermediate Similarity	NPC143533
0.7917	Intermediate Similarity	NPC63157
0.7917	Intermediate Similarity	NPC473868
0.7903	Intermediate Similarity	NPC235684
0.7901	Intermediate Similarity	NPC203468
0.7901	Intermediate Similarity	NPC110500
0.7901	Intermediate Similarity	NPC149155
0.7895	Intermediate Similarity	NPC21605
0.7892	Intermediate Similarity	NPC258480
0.7889	Intermediate Similarity	NPC6982
0.7877	Intermediate Similarity	NPC317430
0.7877	Intermediate Similarity	NPC78020
0.7874	Intermediate Similarity	NPC207726
0.7869	Intermediate Similarity	NPC248041
0.7869	Intermediate Similarity	NPC126709
0.7861	Intermediate Similarity	NPC472323
0.7845	Intermediate Similarity	NPC472123
0.7826	Intermediate Similarity	NPC15840
0.7826	Intermediate Similarity	NPC91179
0.7814	Intermediate Similarity	NPC111275
0.7807	Intermediate Similarity	NPC160381
0.7807	Intermediate Similarity	NPC66210
0.7793	Intermediate Similarity	NPC475816
0.7784	Intermediate Similarity	NPC113626
0.7772	Intermediate Similarity	NPC283219
0.7761	Intermediate Similarity	NPC472291
0.7754	Intermediate Similarity	NPC472107
0.7754	Intermediate Similarity	NPC79062
0.7747	Intermediate Similarity	NPC34508
0.7747	Intermediate Similarity	NPC161861
0.7742	Intermediate Similarity	NPC472108
0.7742	Intermediate Similarity	NPC139291
0.774	Intermediate Similarity	NPC469720
0.774	Intermediate Similarity	NPC67056
0.7737	Intermediate Similarity	NPC472097
0.7735	Intermediate Similarity	NPC280548
0.7725	Intermediate Similarity	NPC321708
0.7722	Intermediate Similarity	NPC474561
0.7722	Intermediate Similarity	NPC49954
0.7708	Intermediate Similarity	NPC276517
0.7692	Intermediate Similarity	NPC329747
0.7685	Intermediate Similarity	NPC152768
0.7685	Intermediate Similarity	NPC148183
0.768	Intermediate Similarity	NPC306376
0.7676	Intermediate Similarity	NPC55772
0.7668	Intermediate Similarity	NPC472116
0.7667	Intermediate Similarity	NPC470508
0.7656	Intermediate Similarity	NPC478078
0.7653	Intermediate Similarity	NPC471944
0.765	Intermediate Similarity	NPC81939
0.7639	Intermediate Similarity	NPC473540
0.7619	Intermediate Similarity	NPC62749
0.7619	Intermediate Similarity	NPC315555
0.7617	Intermediate Similarity	NPC289299
0.7617	Intermediate Similarity	NPC57994
0.7615	Intermediate Similarity	NPC475666
0.7614	Intermediate Similarity	NPC260900
0.7609	Intermediate Similarity	NPC472586
0.7606	Intermediate Similarity	NPC228835
0.7606	Intermediate Similarity	NPC472294
0.7602	Intermediate Similarity	NPC329793
0.76	Intermediate Similarity	NPC33421
0.7594	Intermediate Similarity	NPC71037
0.7592	Intermediate Similarity	NPC469470
0.7592	Intermediate Similarity	NPC469501
0.7592	Intermediate Similarity	NPC95783
0.7588	Intermediate Similarity	NPC471191
0.7586	Intermediate Similarity	NPC221100
0.7586	Intermediate Similarity	NPC234078
0.7582	Intermediate Similarity	NPC63751
0.7581	Intermediate Similarity	NPC270009
0.7581	Intermediate Similarity	NPC472443
0.758	Intermediate Similarity	NPC17437
0.7566	Intermediate Similarity	NPC133003
0.7565	Intermediate Similarity	NPC88315
0.756	Intermediate Similarity	NPC21638
0.7556	Intermediate Similarity	NPC282231
0.7553	Intermediate Similarity	NPC472104
0.7553	Intermediate Similarity	NPC472444
0.7552	Intermediate Similarity	NPC138370
0.7551	Intermediate Similarity	NPC74413
0.7544	Intermediate Similarity	NPC2949
0.7544	Intermediate Similarity	NPC59084
0.7543	Intermediate Similarity	NPC37548
0.7527	Intermediate Similarity	NPC28848
0.7527	Intermediate Similarity	NPC14325
0.7525	Intermediate Similarity	NPC476874
0.7525	Intermediate Similarity	NPC193761
0.7514	Intermediate Similarity	NPC194640
0.7513	Intermediate Similarity	NPC252338
0.7512	Intermediate Similarity	NPC477066
0.7512	Intermediate Similarity	NPC475910
0.75	Intermediate Similarity	NPC255229
0.75	Intermediate Similarity	NPC192270
0.75	Intermediate Similarity	NPC279918
0.75	Intermediate Similarity	NPC81229
0.75	Intermediate Similarity	NPC67288
0.7487	Intermediate Similarity	NPC476098
0.7487	Intermediate Similarity	NPC17059
0.7477	Intermediate Similarity	NPC478081
0.7477	Intermediate Similarity	NPC477067
0.7477	Intermediate Similarity	NPC478082
0.7473	Intermediate Similarity	NPC84347
0.7472	Intermediate Similarity	NPC38736
0.7472	Intermediate Similarity	NPC470507
0.7471	Intermediate Similarity	NPC470440
0.7463	Intermediate Similarity	NPC478157
0.7463	Intermediate Similarity	NPC474412
0.746	Intermediate Similarity	NPC472109
0.746	Intermediate Similarity	NPC472110
0.746	Intermediate Similarity	NPC159125
0.7459	Intermediate Similarity	NPC194881
0.7453	Intermediate Similarity	NPC33949
0.745	Intermediate Similarity	NPC132539
0.7449	Intermediate Similarity	NPC227582
0.7449	Intermediate Similarity	NPC262898
0.7449	Intermediate Similarity	NPC141454
0.7448	Intermediate Similarity	NPC46413
0.7443	Intermediate Similarity	NPC187951
0.7441	Intermediate Similarity	NPC472762
0.744	Intermediate Similarity	NPC82070
0.744	Intermediate Similarity	NPC281049
0.7436	Intermediate Similarity	NPC181502
0.7436	Intermediate Similarity	NPC85066
0.7433	Intermediate Similarity	NPC293472

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 NPC314333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	496
0.2-0.3	725
0.3-0.4	1546
0.4-0.5	2616
0.5-0.6	2551
0.6-0.7	892
0.7-0.8	136
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4499	Approved
0.8158	Intermediate Similarity	NPD4501	Approved
0.8158	Intermediate Similarity	NPD4601	Approved
0.8158	Intermediate Similarity	NPD4600	Approved
0.8158	Intermediate Similarity	NPD4500	Approved
0.8148	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD6176	Phase 1
0.7935	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD482	Approved
0.7857	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2094	Phase 2
0.7838	Intermediate Similarity	NPD2095	Phase 2
0.7838	Intermediate Similarity	NPD2092	Phase 2
0.7806	Intermediate Similarity	NPD5901	Discontinued
0.7796	Intermediate Similarity	NPD2091	Phase 2
0.7796	Intermediate Similarity	NPD2096	Phase 2
0.7778	Intermediate Similarity	NPD2844	Phase 3
0.7747	Intermediate Similarity	NPD750	Phase 2
0.7732	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2510	Approved
0.7688	Intermediate Similarity	NPD2509	Approved
0.7677	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD4948	Discontinued
0.767	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5473	Discontinued
0.7629	Intermediate Similarity	NPD5003	Discontinued
0.7626	Intermediate Similarity	NPD5426	Phase 3
0.7617	Intermediate Similarity	NPD4602	Approved
0.7614	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD3393	Approved
0.7598	Intermediate Similarity	NPD3394	Approved
0.7598	Intermediate Similarity	NPD3389	Approved
0.758	Intermediate Similarity	NPD8358	Approved
0.7577	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7470	Discontinued
0.7569	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4075	Phase 2
0.7463	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1534	Approved
0.7446	Intermediate Similarity	NPD1325	Approved
0.7446	Intermediate Similarity	NPD1326	Approved
0.7438	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7618	Phase 3
0.7436	Intermediate Similarity	NPD7619	Phase 3
0.7419	Intermediate Similarity	NPD5065	Approved
0.7411	Intermediate Similarity	NPD4397	Phase 1
0.7409	Intermediate Similarity	NPD2565	Phase 2
0.7409	Intermediate Similarity	NPD2564	Approved
0.7404	Intermediate Similarity	NPD6770	Approved
0.74	Intermediate Similarity	NPD8072	Approved
0.7394	Intermediate Similarity	NPD4076	Approved
0.7394	Intermediate Similarity	NPD4079	Approved
0.7389	Intermediate Similarity	NPD4506	Discontinued
0.7382	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD2915	Discontinued
0.7374	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6664	Approved
0.7358	Intermediate Similarity	NPD4334	Discontinued
0.7351	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3505	Approved
0.734	Intermediate Similarity	NPD3506	Approved
0.7327	Intermediate Similarity	NPD7957	Phase 1
0.7327	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5472	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5104	Approved
0.7286	Intermediate Similarity	NPD6249	Phase 2
0.7286	Intermediate Similarity	NPD6248	Phase 2
0.7282	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD3319	Phase 1
0.7277	Intermediate Similarity	NPD3318	Approved
0.7277	Intermediate Similarity	NPD3320	Approved
0.7268	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8073	Approved
0.7257	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD484	Approved
0.725	Intermediate Similarity	NPD6479	Discontinued
0.7249	Intermediate Similarity	NPD2144	Approved
0.724	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5475	Discontinued
0.7225	Intermediate Similarity	NPD3038	Discontinued
0.7225	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8386	Phase 2
0.7198	Intermediate Similarity	NPD7454	Approved
0.7198	Intermediate Similarity	NPD7455	Approved
0.7196	Intermediate Similarity	NPD5471	Phase 3
0.7192	Intermediate Similarity	NPD6987	Phase 1
0.7192	Intermediate Similarity	NPD8098	Approved
0.7188	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6595	Phase 3
0.7171	Intermediate Similarity	NPD2916	Discontinued
0.7165	Intermediate Similarity	NPD5444	Phase 1
0.7158	Intermediate Similarity	NPD1630	Approved
0.7157	Intermediate Similarity	NPD4315	Phase 2
0.7151	Intermediate Similarity	NPD3100	Discontinued
0.715	Intermediate Similarity	NPD7777	Approved
0.715	Intermediate Similarity	NPD53	Approved
0.715	Intermediate Similarity	NPD7778	Approved
0.7143	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4520	Approved
0.7129	Intermediate Similarity	NPD5293	Phase 2
0.7128	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6242	Discontinued
0.7119	Intermediate Similarity	NPD5254	Discontinued
0.7114	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6999	Discontinued
0.7111	Intermediate Similarity	NPD4462	Approved
0.7111	Intermediate Similarity	NPD4463	Approved
0.7108	Intermediate Similarity	NPD3947	Discontinued
0.7108	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5913	Phase 3
0.7107	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4326	Phase 2
0.7102	Intermediate Similarity	NPD1722	Approved
0.7098	Intermediate Similarity	NPD5596	Phase 2
0.7095	Intermediate Similarity	NPD4702	Approved
0.7095	Intermediate Similarity	NPD4703	Approved
0.7093	Intermediate Similarity	NPD3385	Approved
0.7092	Intermediate Similarity	NPD7233	Approved
0.7092	Intermediate Similarity	NPD7234	Approved
0.7087	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8094	Discontinued
0.7073	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2882	Phase 1
0.7068	Intermediate Similarity	NPD7865	Approved
0.7068	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2213	Approved
0.7065	Intermediate Similarity	NPD2214	Approved
0.7062	Intermediate Similarity	NPD6178	Phase 3
0.7059	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2920	Discontinued
0.7053	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5140	Approved
0.7043	Intermediate Similarity	NPD1631	Approved
0.7043	Intermediate Similarity	NPD5138	Approved
0.7043	Intermediate Similarity	NPD3323	Discontinued
0.7041	Intermediate Similarity	NPD3961	Discontinued
0.7041	Intermediate Similarity	NPD8431	Approved
0.7039	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1683	Approved
0.7037	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8093	Discontinued
0.7033	Intermediate Similarity	NPD2837	Discontinued
0.703	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7878	Phase 2
0.7026	Intermediate Similarity	NPD5075	Discontinued
0.7024	Intermediate Similarity	NPD8283	Approved
0.7024	Intermediate Similarity	NPD56	Approved
0.7024	Intermediate Similarity	NPD8282	Approved
0.7021	Intermediate Similarity	NPD4639	Approved
0.7021	Intermediate Similarity	NPD4638	Approved
0.7021	Intermediate Similarity	NPD4640	Approved
0.702	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2336	Approved
0.7019	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6376	Discontinued
0.7	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5898	Approved
0.6995	Remote Similarity	NPD5899	Approved
0.6995	Remote Similarity	NPD6452	Discontinued
0.6995	Remote Similarity	NPD5897	Approved
0.6995	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7010	Phase 3
0.699	Remote Similarity	NPD5809	Phase 3
0.6989	Remote Similarity	NPD786	Approved
0.6985	Remote Similarity	NPD5505	Discontinued
0.6984	Remote Similarity	NPD1575	Approved
0.6984	Remote Similarity	NPD1573	Approved
0.6981	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6158	Phase 2
0.6978	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5487	Phase 1
0.6974	Remote Similarity	NPD7564	Discontinued
0.6972	Remote Similarity	NPD7780	Approved
0.6972	Remote Similarity	NPD7781	Approved
0.697	Remote Similarity	NPD6281	Approved
0.6968	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD6226	Phase 3
0.6963	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD8364	Approved
0.6962	Remote Similarity	NPD8363	Approved
0.6961	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4885	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