NPASS Compound

Structure

NPC472105 OpenBabel07101718242D 25 30 0 0 1 0 0 0 0 0999 V2000 1.3044 0.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8730 1.2099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6017 0.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9218 -2.2345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4862 -1.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9669 -2.1341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0957 -0.5805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1243 0.6983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8316 -1.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7723 -0.4666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7893 -0.0686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5763 -1.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4873 0.2813 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6631 -0.9602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5426 -0.4568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1407 -0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8316 0.4801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5596 -0.0588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6631 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2584 -0.2327 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5763 0.2967 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 3 3 0 0 0 0 0 0 0 0 0 0.0577 -2.1426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8957 -0.2725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 23 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 12 2 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 1 1 1 0 0 0 11 19 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 8 1 1 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 1 0 0 0 18 20 1 0 0 0 0 18 23 1 1 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 M CHG 1 23 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.21
Volume:	350.78
LogP:	0.505
LogD:	1.127
LogS:	-0.828
# Rotatable Bonds:	0
TPSA:	34.39
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	6.278
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.805
MDCK Permeability:	4.08271916967351e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.251
Plasma Protein Binding (PPB):	50.77269744873047%
Volume Distribution (VD):	2.527
Pgp-substrate:	60.39193344116211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.354
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.379
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	1.964
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.785
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.037
Carcinogencity:	0.81
Eye Corrosion:	0.004
Eye Irritation:	0.034
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC472105

Natural Product ID:	NPC472105
*Common Name:**	LMYDARNIDZIMKO-ZCFHXPGJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LMYDARNIDZIMKO-ZCFHXPGJSA-N
Standard InCHI:	InChI=1S/C21H27N2O2/c1-11-19-13-8-18-20-14(12-6-4-5-7-16(12)22(20)2)9-17(15(13)10-25-11)23(18,3)21(19)24/h4-7,11,13,15,17-19,21,24H,8-10H2,1-3H3/q+1/t11-,13-,15-,17+,18+,19+,21-,23?/m1/s1
SMILES:	C[C@H]1OC[C@@H]2[C@@H]3[C@H]1[C@@H](O)[N+]1([C@H]2Cc2c([C@@H]1C3)n(C)c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338228
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline 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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[558607]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[558607]

☑ 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 NPC472105 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	319
0.1-0.2	1488
0.2-0.3	8073
0.3-0.4	22761
0.4-0.5	5386
0.5-0.6	2580
0.6-0.7	1751
0.7-0.8	302
0.8-0.85	20
0.85-0.9	8
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC187827
0.9812	High Similarity	NPC24594
0.9812	High Similarity	NPC472122
0.9515	High Similarity	NPC472109
0.9515	High Similarity	NPC472110
0.9398	High Similarity	NPC472104
0.9281	High Similarity	NPC472108
0.9281	High Similarity	NPC139291
0.9157	High Similarity	NPC326575
0.9102	High Similarity	NPC133261
0.896	High Similarity	NPC469470
0.896	High Similarity	NPC469501
0.8862	High Similarity	NPC472123
0.8834	High Similarity	NPC255229
0.8834	High Similarity	NPC81229
0.8713	High Similarity	NPC15840
0.8621	High Similarity	NPC79062
0.8621	High Similarity	NPC472107
0.8486	Intermediate Similarity	NPC472111
0.8483	Intermediate Similarity	NPC472097
0.8418	Intermediate Similarity	NPC472323
0.8362	Intermediate Similarity	NPC66210
0.8353	Intermediate Similarity	NPC317430
0.8352	Intermediate Similarity	NPC258480
0.8249	Intermediate Similarity	NPC472119
0.8207	Intermediate Similarity	NPC52557
0.8192	Intermediate Similarity	NPC143533
0.8161	Intermediate Similarity	NPC329688
0.8161	Intermediate Similarity	NPC189812
0.8156	Intermediate Similarity	NPC478077
0.8101	Intermediate Similarity	NPC62510
0.8066	Intermediate Similarity	NPC175474
0.8034	Intermediate Similarity	NPC113626
0.8021	Intermediate Similarity	NPC81654
0.8021	Intermediate Similarity	NPC79129
0.8021	Intermediate Similarity	NPC49196
0.8021	Intermediate Similarity	NPC249040
0.8021	Intermediate Similarity	NPC313985
0.8021	Intermediate Similarity	NPC195461
0.8021	Intermediate Similarity	NPC249150
0.8011	Intermediate Similarity	NPC150048
0.8011	Intermediate Similarity	NPC121903
0.8011	Intermediate Similarity	NPC203754
0.8	Intermediate Similarity	NPC245916
0.7989	Intermediate Similarity	NPC19679
0.7965	Intermediate Similarity	NPC469541
0.7946	Intermediate Similarity	NPC57994
0.7946	Intermediate Similarity	NPC289299
0.7943	Intermediate Similarity	NPC158129
0.7935	Intermediate Similarity	NPC472113
0.7923	Intermediate Similarity	NPC472112
0.7914	Intermediate Similarity	NPC50503
0.7865	Intermediate Similarity	NPC234987
0.7865	Intermediate Similarity	NPC211997
0.7836	Intermediate Similarity	NPC129721
0.7835	Intermediate Similarity	NPC475422
0.7826	Intermediate Similarity	NPC95783
0.7824	Intermediate Similarity	NPC87755
0.7818	Intermediate Similarity	NPC20144
0.7812	Intermediate Similarity	NPC474145
0.7812	Intermediate Similarity	NPC475841
0.7809	Intermediate Similarity	NPC134586
0.7807	Intermediate Similarity	NPC472116
0.7737	Intermediate Similarity	NPC312870
0.7737	Intermediate Similarity	NPC294909
0.7737	Intermediate Similarity	NPC254240
0.7737	Intermediate Similarity	NPC128265
0.7737	Intermediate Similarity	NPC199851
0.7696	Intermediate Similarity	NPC476492
0.7692	Intermediate Similarity	NPC469589
0.7674	Intermediate Similarity	NPC285469
0.765	Intermediate Similarity	NPC174788
0.765	Intermediate Similarity	NPC472294
0.7636	Intermediate Similarity	NPC104483
0.7629	Intermediate Similarity	NPC238457
0.7614	Intermediate Similarity	NPC470508
0.7612	Intermediate Similarity	NPC52254
0.76	Intermediate Similarity	NPC194881
0.7581	Intermediate Similarity	NPC63199
0.7581	Intermediate Similarity	NPC196251
0.7581	Intermediate Similarity	NPC111602
0.7581	Intermediate Similarity	NPC102338
0.7571	Intermediate Similarity	NPC49954
0.7571	Intermediate Similarity	NPC474561
0.7571	Intermediate Similarity	NPC54988
0.7563	Intermediate Similarity	NPC126066
0.7557	Intermediate Similarity	NPC476446
0.7557	Intermediate Similarity	NPC78375
0.7557	Intermediate Similarity	NPC311276
0.7557	Intermediate Similarity	NPC469813
0.7539	Intermediate Similarity	NPC149708
0.7514	Intermediate Similarity	NPC207726
0.75	Intermediate Similarity	NPC473763
0.75	Intermediate Similarity	NPC117244
0.75	Intermediate Similarity	NPC16667
0.7487	Intermediate Similarity	NPC118832
0.7487	Intermediate Similarity	NPC274291
0.7487	Intermediate Similarity	NPC264166
0.7487	Intermediate Similarity	NPC329708
0.7487	Intermediate Similarity	NPC47059
0.7487	Intermediate Similarity	NPC165349
0.7486	Intermediate Similarity	NPC474880
0.7486	Intermediate Similarity	NPC221786
0.7472	Intermediate Similarity	NPC160105
0.7459	Intermediate Similarity	NPC472586
0.7446	Intermediate Similarity	NPC233936
0.7443	Intermediate Similarity	NPC229173
0.7442	Intermediate Similarity	NPC40070
0.7432	Intermediate Similarity	NPC472443
0.743	Intermediate Similarity	NPC63751
0.7429	Intermediate Similarity	NPC469762
0.7425	Intermediate Similarity	NPC88097
0.7412	Intermediate Similarity	NPC472100
0.7407	Intermediate Similarity	NPC243716
0.7405	Intermediate Similarity	NPC472444
0.7405	Intermediate Similarity	NPC159125
0.7404	Intermediate Similarity	NPC33949
0.7404	Intermediate Similarity	NPC253580
0.7403	Intermediate Similarity	NPC314603
0.7403	Intermediate Similarity	NPC34508
0.7401	Intermediate Similarity	NPC282231
0.74	Intermediate Similarity	NPC264176
0.7389	Intermediate Similarity	NPC82070
0.7386	Intermediate Similarity	NPC84508
0.7386	Intermediate Similarity	NPC67056
0.7377	Intermediate Similarity	NPC151939
0.7376	Intermediate Similarity	NPC476114
0.7374	Intermediate Similarity	NPC475910
0.7371	Intermediate Similarity	NPC469785
0.7366	Intermediate Similarity	NPC471506
0.7363	Intermediate Similarity	NPC469938
0.7363	Intermediate Similarity	NPC221100
0.7363	Intermediate Similarity	NPC469592
0.7363	Intermediate Similarity	NPC234078
0.7363	Intermediate Similarity	NPC471080
0.736	Intermediate Similarity	NPC40779
0.736	Intermediate Similarity	NPC194640
0.736	Intermediate Similarity	NPC21174
0.736	Intermediate Similarity	NPC271797
0.7358	Intermediate Similarity	NPC102008
0.7356	Intermediate Similarity	NPC470126
0.7351	Intermediate Similarity	NPC314394
0.7345	Intermediate Similarity	NPC279918
0.7344	Intermediate Similarity	NPC231342
0.7337	Intermediate Similarity	NPC477548
0.7337	Intermediate Similarity	NPC219336
0.7337	Intermediate Similarity	NPC248462
0.7333	Intermediate Similarity	NPC201700
0.7333	Intermediate Similarity	NPC154293
0.7323	Intermediate Similarity	NPC53344
0.7314	Intermediate Similarity	NPC470507
0.7313	Intermediate Similarity	NPC472098
0.7312	Intermediate Similarity	NPC163055
0.7304	Intermediate Similarity	NPC281049
0.7304	Intermediate Similarity	NPC469594
0.7297	Intermediate Similarity	NPC300688
0.7297	Intermediate Similarity	NPC469896
0.7296	Intermediate Similarity	NPC476874
0.7295	Intermediate Similarity	NPC475271
0.7293	Intermediate Similarity	NPC280548
0.7293	Intermediate Similarity	NPC474897
0.7288	Intermediate Similarity	NPC230869
0.7288	Intermediate Similarity	NPC475990
0.7287	Intermediate Similarity	NPC474707
0.7283	Intermediate Similarity	NPC15573
0.7283	Intermediate Similarity	NPC183662
0.7283	Intermediate Similarity	NPC28848
0.7283	Intermediate Similarity	NPC14325
0.7283	Intermediate Similarity	NPC217372
0.7277	Intermediate Similarity	NPC475602
0.7273	Intermediate Similarity	NPC477156
0.7273	Intermediate Similarity	NPC477157
0.7258	Intermediate Similarity	NPC71037
0.7257	Intermediate Similarity	NPC469760
0.7257	Intermediate Similarity	NPC73952
0.7257	Intermediate Similarity	NPC469786
0.7257	Intermediate Similarity	NPC25008
0.7257	Intermediate Similarity	NPC259644
0.7257	Intermediate Similarity	NPC469765
0.7257	Intermediate Similarity	NPC469763
0.7253	Intermediate Similarity	NPC126492
0.7249	Intermediate Similarity	NPC119700
0.7249	Intermediate Similarity	NPC204565
0.7247	Intermediate Similarity	NPC477158
0.7245	Intermediate Similarity	NPC475506
0.7243	Intermediate Similarity	NPC270009
0.724	Intermediate Similarity	NPC473178
0.724	Intermediate Similarity	NPC474177
0.7238	Intermediate Similarity	NPC469462
0.7234	Intermediate Similarity	NPC163421
0.7234	Intermediate Similarity	NPC188387
0.7233	Intermediate Similarity	NPC472099
0.7225	Intermediate Similarity	NPC21605
0.7222	Intermediate Similarity	NPC472106
0.7216	Intermediate Similarity	NPC211572
0.7216	Intermediate Similarity	NPC80597
0.7216	Intermediate Similarity	NPC75540
0.7216	Intermediate Similarity	NPC476219
0.7216	Intermediate Similarity	NPC212376
0.7216	Intermediate Similarity	NPC70922

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 NPC472105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	541
0.2-0.3	651
0.3-0.4	1723
0.4-0.5	2882
0.5-0.6	2329
0.6-0.7	741
0.7-0.8	103
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8021	Intermediate Similarity	NPD4601	Approved
0.8021	Intermediate Similarity	NPD4600	Approved
0.8011	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD4602	Approved
0.7749	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4500	Approved
0.7737	Intermediate Similarity	NPD4501	Approved
0.766	Intermediate Similarity	NPD7944	Discontinued
0.764	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4638	Approved
0.7627	Intermediate Similarity	NPD4640	Approved
0.7627	Intermediate Similarity	NPD4639	Approved
0.7614	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6227	Discontinued
0.7602	Intermediate Similarity	NPD2882	Phase 1
0.7592	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3385	Approved
0.7541	Intermediate Similarity	NPD8408	Discontinued
0.7529	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5862	Discovery
0.7527	Intermediate Similarity	NPD2383	Phase 1
0.7514	Intermediate Similarity	NPD5104	Approved
0.75	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6158	Phase 2
0.7487	Intermediate Similarity	NPD4039	Approved
0.7487	Intermediate Similarity	NPD4033	Approved
0.7487	Intermediate Similarity	NPD31	Approved
0.7487	Intermediate Similarity	NPD4035	Approved
0.7487	Intermediate Similarity	NPD4037	Approved
0.7487	Intermediate Similarity	NPD4038	Approved
0.7487	Intermediate Similarity	NPD32	Approved
0.7487	Intermediate Similarity	NPD4034	Approved
0.7487	Intermediate Similarity	NPD4122	Approved
0.7487	Intermediate Similarity	NPD4036	Approved
0.7486	Intermediate Similarity	NPD5899	Approved
0.7486	Intermediate Similarity	NPD5897	Approved
0.7486	Intermediate Similarity	NPD5898	Approved
0.7457	Intermediate Similarity	NPD4120	Approved
0.7457	Intermediate Similarity	NPD4121	Phase 3
0.7433	Intermediate Similarity	NPD8021	Approved
0.7433	Intermediate Similarity	NPD8020	Approved
0.7432	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4520	Approved
0.7418	Intermediate Similarity	NPD2380	Approved
0.7418	Intermediate Similarity	NPD2382	Approved
0.7418	Intermediate Similarity	NPD2381	Approved
0.7416	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5743	Approved
0.7414	Intermediate Similarity	NPD5741	Approved
0.7414	Intermediate Similarity	NPD5742	Approved
0.7394	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD53	Approved
0.7358	Intermediate Similarity	NPD7777	Approved
0.7358	Intermediate Similarity	NPD7778	Approved
0.7354	Intermediate Similarity	NPD6281	Approved
0.7351	Intermediate Similarity	NPD4204	Approved
0.7351	Intermediate Similarity	NPD4203	Approved
0.7344	Intermediate Similarity	NPD7935	Phase 2
0.7333	Intermediate Similarity	NPD5021	Discontinued
0.733	Intermediate Similarity	NPD4326	Phase 2
0.7318	Intermediate Similarity	NPD2915	Discontinued
0.7302	Intermediate Similarity	NPD4334	Discontinued
0.7301	Intermediate Similarity	NPD3654	Approved
0.7297	Intermediate Similarity	NPD6595	Phase 3
0.7273	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4957	Phase 2
0.7268	Intermediate Similarity	NPD6492	Phase 2
0.7267	Intermediate Similarity	NPD1683	Approved
0.7263	Intermediate Similarity	NPD8063	Discontinued
0.7253	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4079	Approved
0.7243	Intermediate Similarity	NPD4076	Approved
0.7236	Intermediate Similarity	NPD7222	Phase 2
0.7234	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5075	Discontinued
0.7234	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5555	Phase 1
0.7225	Intermediate Similarity	NPD4702	Approved
0.7225	Intermediate Similarity	NPD4703	Approved
0.7225	Intermediate Similarity	NPD4547	Phase 3
0.7222	Intermediate Similarity	NPD8115	Approved
0.7222	Intermediate Similarity	NPD8114	Approved
0.7219	Intermediate Similarity	NPD5596	Phase 2
0.7219	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD750	Phase 2
0.7202	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD1325	Approved
0.7198	Intermediate Similarity	NPD1326	Approved
0.7191	Intermediate Similarity	NPD5255	Approved
0.7189	Intermediate Similarity	NPD8122	Approved
0.7189	Intermediate Similarity	NPD3506	Approved
0.7189	Intermediate Similarity	NPD3505	Approved
0.7189	Intermediate Similarity	NPD8123	Approved
0.7186	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7957	Phase 1
0.7179	Intermediate Similarity	NPD4397	Phase 1
0.7174	Intermediate Similarity	NPD5065	Approved
0.7173	Intermediate Similarity	NPD4499	Approved
0.7168	Intermediate Similarity	NPD7469	Discontinued
0.7157	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5100	Phase 3
0.7129	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7112	Discontinued
0.712	Intermediate Similarity	NPD7234	Approved
0.712	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7233	Approved
0.7119	Intermediate Similarity	NPD6285	Phase 2
0.7114	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7666	Phase 3
0.7114	Intermediate Similarity	NPD7665	Phase 2
0.7112	Intermediate Similarity	NPD6452	Discontinued
0.7112	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD45	Approved
0.7101	Intermediate Similarity	NPD6554	Approved
0.7098	Intermediate Similarity	NPD4315	Phase 2
0.7097	Intermediate Similarity	NPD6159	Phase 2
0.7097	Intermediate Similarity	NPD2144	Approved
0.7093	Intermediate Similarity	NPD4047	Discontinued
0.7092	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7482	Phase 2
0.709	Intermediate Similarity	NPD7483	Phase 2
0.7079	Intermediate Similarity	NPD6026	Approved
0.7077	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD3038	Discontinued
0.7068	Intermediate Similarity	NPD8431	Approved
0.7059	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6248	Phase 2
0.7056	Intermediate Similarity	NPD6249	Phase 2
0.7049	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5913	Phase 3
0.7041	Intermediate Similarity	NPD6206	Phase 1
0.7037	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1661	Suspended
0.7028	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6978	Phase 2
0.7027	Intermediate Similarity	NPD7418	Discontinued
0.7027	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD43	Approved
0.7027	Intermediate Similarity	NPD6182	Approved
0.7019	Intermediate Similarity	NPD6455	Phase 3
0.7016	Intermediate Similarity	NPD5444	Phase 1
0.7015	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7001	Phase 3
0.7014	Intermediate Similarity	NPD7271	Approved
0.7014	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7474	Suspended
0.7005	Intermediate Similarity	NPD7111	Discontinued
0.7005	Intermediate Similarity	NPD6261	Phase 3
0.6989	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7452	Approved
0.698	Remote Similarity	NPD7453	Approved
0.6978	Remote Similarity	NPD5138	Approved
0.6978	Remote Similarity	NPD5140	Approved
0.697	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6999	Discontinued
0.6968	Remote Similarity	NPD8386	Phase 2
0.6965	Remote Similarity	NPD8272	Phase 2
0.6963	Remote Similarity	NPD3082	Discontinued
0.6957	Remote Similarity	NPD3393	Approved
0.6957	Remote Similarity	NPD3389	Approved
0.6957	Remote Similarity	NPD3394	Approved
0.6954	Remote Similarity	NPD5003	Discontinued
0.6952	Remote Similarity	NPD5501	Discontinued
0.6949	Remote Similarity	NPD4462	Approved
0.6949	Remote Similarity	NPD4463	Approved
0.6948	Remote Similarity	NPD7730	Approved
0.6948	Remote Similarity	NPD7731	Approved
0.6947	Remote Similarity	NPD2092	Phase 2
0.6947	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2094	Phase 2
0.6947	Remote Similarity	NPD2095	Phase 2
0.6944	Remote Similarity	NPD2581	Approved
0.6944	Remote Similarity	NPD2582	Approved
0.6939	Remote Similarity	NPD4427	Phase 2
0.6936	Remote Similarity	NPD5020	Approved
0.6931	Remote Similarity	NPD5530	Phase 1
0.6923	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6569	Phase 2
0.6923	Remote Similarity	NPD8326	Phase 3
0.6923	Remote Similarity	NPD6619	Phase 3
0.6923	Remote Similarity	NPD8325	Phase 3
0.6915	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4181	Approved
0.6915	Remote Similarity	NPD4886	Phase 2
0.6911	Remote Similarity	NPD2091	Phase 2
0.6911	Remote Similarity	NPD2096	Phase 2
0.6911	Remote Similarity	NPD6178	Phase 3
0.6908	Remote Similarity	NPD8112	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