NPASS Compound

Structure

CID258480 OpenBabel06191716062D 25 29 0 0 1 0 0 0 0 0999 V2000 -2.9820 1.6310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5535 -0.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2371 0.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5943 -2.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1200 -1.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5948 -2.4941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6462 -0.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 0.2262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6768 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -0.2544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 -1.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 1.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1209 -1.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1804 -0.2544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8506 -1.3764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 0.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1804 -1.0253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6466 -0.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 -1.5059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8263 0.0547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9253 -0.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6525 -0.5087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7140 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -1.0253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 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 13 2 0 0 0 0 7 18 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 25 1 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 24 2 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 8 1 6 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 2 0 0 0 0 17 11 1 6 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 9 1 1 0 0 0 19 22 1 0 0 0 0 20 8 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.18
Volume:	352.745
LogP:	2.226
LogD:	2.618
LogS:	-2.844
# Rotatable Bonds:	1
TPSA:	34.47
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	4.976
Fsp3:	0.476
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:	-4.781
MDCK Permeability:	2.1751209715148434e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.139
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.349

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	66.18150329589844%
Volume Distribution (VD):	1.482
Pgp-substrate:	35.065738677978516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.803
CYP1A2-substrate:	0.583
CYP2C19-inhibitor:	0.488
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.45
CYP2D6-inhibitor:	0.93
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	7.216
Half-life (T1/2):	0.455

ADMET: Toxicity

hERG Blockers:	0.218
Human Hepatotoxicity (H-HT):	0.677
Drug-inuced Liver Injury (DILI):	0.669
AMES Toxicity:	0.913
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.075
Carcinogencity:	0.959
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC258480

Natural Product ID:	NPC258480
*Common Name:**	Alstonerine
IUPAC Name:	n.a.
Synonyms:	Alstonerine
Standard InCHIKey:	PMIRJPWEIZTLEG-KTGNWYGMSA-N
Standard InCHI:	InChI=1S/C21H24N2O2/c1-12(24)16-10-25-11-17-14(16)8-20-21-15(9-19(17)22(20)2)13-6-4-5-7-18(13)23(21)3/h4-7,10,14,17,19-20H,8-9,11H2,1-3H3/t14-,17+,19-,20-/m0/s1
SMILES:	CC(=O)C1=COC[C@@H]2[C@H]1C[C@@H]1N([C@H]2Cc2c1n(C)c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL606749
PubChem CID:	10382386
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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19678	Alstonia macrophylla	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	3
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	20.7	%	PMID[490230]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	27.7	%	PMID[490230]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[490231]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[490231]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10000.0	nM	PMID[490231]

☑ 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 NPC258480 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	307
0.1-0.2	1505
0.2-0.3	9330
0.3-0.4	20640
0.4-0.5	5756
0.5-0.6	2329
0.6-0.7	2306
0.7-0.8	433
0.8-0.85	61
0.85-0.9	22
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9641	High Similarity	NPC66210
0.9471	High Similarity	NPC472112
0.9341	High Similarity	NPC15840
0.9235	High Similarity	NPC79062
0.9235	High Similarity	NPC472107
0.9138	High Similarity	NPC472113
0.9017	High Similarity	NPC472323
0.8994	High Similarity	NPC234987
0.8953	High Similarity	NPC472119
0.8876	High Similarity	NPC245916
0.8786	High Similarity	NPC143533
0.8785	High Similarity	NPC254240
0.8785	High Similarity	NPC312870
0.8785	High Similarity	NPC199851
0.8785	High Similarity	NPC128265
0.8785	High Similarity	NPC294909
0.875	High Similarity	NPC102338
0.875	High Similarity	NPC196251
0.875	High Similarity	NPC63199
0.875	High Similarity	NPC111602
0.8728	High Similarity	NPC113626
0.8652	High Similarity	NPC472097
0.8649	High Similarity	NPC238457
0.8564	High Similarity	NPC472116
0.8531	High Similarity	NPC478077
0.8497	Intermediate Similarity	NPC472122
0.8497	Intermediate Similarity	NPC24594
0.8474	Intermediate Similarity	NPC264176
0.8466	Intermediate Similarity	NPC472104
0.8452	Intermediate Similarity	NPC81229
0.8452	Intermediate Similarity	NPC255229
0.8448	Intermediate Similarity	NPC326575
0.8352	Intermediate Similarity	NPC187827
0.8352	Intermediate Similarity	NPC472105
0.8333	Intermediate Similarity	NPC175474
0.8333	Intermediate Similarity	NPC234078
0.8333	Intermediate Similarity	NPC221100
0.8306	Intermediate Similarity	NPC220151
0.8306	Intermediate Similarity	NPC19692
0.827	Intermediate Similarity	NPC52557
0.8258	Intermediate Similarity	NPC472109
0.8258	Intermediate Similarity	NPC472110
0.8246	Intermediate Similarity	NPC271797
0.8246	Intermediate Similarity	NPC21174
0.8207	Intermediate Similarity	NPC289299
0.8207	Intermediate Similarity	NPC57994
0.8192	Intermediate Similarity	NPC133261
0.8187	Intermediate Similarity	NPC194881
0.8182	Intermediate Similarity	NPC249150
0.8182	Intermediate Similarity	NPC195461
0.8182	Intermediate Similarity	NPC313985
0.8182	Intermediate Similarity	NPC81654
0.8182	Intermediate Similarity	NPC79129
0.8182	Intermediate Similarity	NPC49196
0.8173	Intermediate Similarity	NPC472099
0.8115	Intermediate Similarity	NPC53344
0.8093	Intermediate Similarity	NPC472098
0.8075	Intermediate Similarity	NPC50503
0.8068	Intermediate Similarity	NPC472123
0.8056	Intermediate Similarity	NPC139291
0.8056	Intermediate Similarity	NPC159125
0.8056	Intermediate Similarity	NPC472108
0.8054	Intermediate Similarity	NPC81802
0.8054	Intermediate Similarity	NPC472210
0.8054	Intermediate Similarity	NPC247735
0.8054	Intermediate Similarity	NPC269886
0.8054	Intermediate Similarity	NPC472295
0.8045	Intermediate Similarity	NPC469896
0.7931	Intermediate Similarity	NPC469541
0.7921	Intermediate Similarity	NPC21638
0.7892	Intermediate Similarity	NPC314333
0.7889	Intermediate Similarity	NPC174788
0.7879	Intermediate Similarity	NPC152768
0.7879	Intermediate Similarity	NPC148183
0.7849	Intermediate Similarity	NPC117244
0.7849	Intermediate Similarity	NPC473763
0.7807	Intermediate Similarity	NPC472292
0.78	Intermediate Similarity	NPC82070
0.7797	Intermediate Similarity	NPC317430
0.7796	Intermediate Similarity	NPC329858
0.779	Intermediate Similarity	NPC248462
0.779	Intermediate Similarity	NPC219336
0.7789	Intermediate Similarity	NPC476114
0.7784	Intermediate Similarity	NPC20144
0.7778	Intermediate Similarity	NPC472293
0.7765	Intermediate Similarity	NPC161861
0.7761	Intermediate Similarity	NPC52254
0.7749	Intermediate Similarity	NPC81535
0.7749	Intermediate Similarity	NPC472297
0.7749	Intermediate Similarity	NPC472296
0.7735	Intermediate Similarity	NPC183662
0.7735	Intermediate Similarity	NPC217372
0.7735	Intermediate Similarity	NPC15573
0.7701	Intermediate Similarity	NPC469501
0.7701	Intermediate Similarity	NPC469470
0.7696	Intermediate Similarity	NPC475271
0.7654	Intermediate Similarity	NPC65080
0.7644	Intermediate Similarity	NPC469736
0.764	Intermediate Similarity	NPC56233
0.7637	Intermediate Similarity	NPC14325
0.7637	Intermediate Similarity	NPC28848
0.7629	Intermediate Similarity	NPC162730
0.7619	Intermediate Similarity	NPC55493
0.7604	Intermediate Similarity	NPC149708
0.7602	Intermediate Similarity	NPC472111
0.7602	Intermediate Similarity	NPC472064
0.7574	Intermediate Similarity	NPC305984
0.7565	Intermediate Similarity	NPC74413
0.7554	Intermediate Similarity	NPC91179
0.7548	Intermediate Similarity	NPC33949
0.7538	Intermediate Similarity	NPC260900
0.7538	Intermediate Similarity	NPC474116
0.7538	Intermediate Similarity	NPC472069
0.7538	Intermediate Similarity	NPC472063
0.7538	Intermediate Similarity	NPC472062
0.7529	Intermediate Similarity	NPC281094
0.7527	Intermediate Similarity	NPC189812
0.7527	Intermediate Similarity	NPC329688
0.7513	Intermediate Similarity	NPC472065
0.7512	Intermediate Similarity	NPC472291
0.75	Intermediate Similarity	NPC104483
0.7486	Intermediate Similarity	NPC121903
0.7475	Intermediate Similarity	NPC477065
0.7462	Intermediate Similarity	NPC327592
0.7461	Intermediate Similarity	NPC106824
0.7449	Intermediate Similarity	NPC328318
0.7449	Intermediate Similarity	NPC328596
0.7447	Intermediate Similarity	NPC118084
0.7446	Intermediate Similarity	NPC84827
0.7446	Intermediate Similarity	NPC14113
0.7446	Intermediate Similarity	NPC145885
0.7436	Intermediate Similarity	NPC249040
0.7433	Intermediate Similarity	NPC46895
0.7432	Intermediate Similarity	NPC469938
0.743	Intermediate Similarity	NPC478182
0.7424	Intermediate Similarity	NPC317373
0.7418	Intermediate Similarity	NPC158129
0.7406	Intermediate Similarity	NPC329631
0.7405	Intermediate Similarity	NPC12649
0.7401	Intermediate Similarity	NPC129721
0.7396	Intermediate Similarity	NPC198673
0.7391	Intermediate Similarity	NPC134586
0.7391	Intermediate Similarity	NPC84347
0.7385	Intermediate Similarity	NPC284338
0.738	Intermediate Similarity	NPC19679
0.7374	Intermediate Similarity	NPC472121
0.7371	Intermediate Similarity	NPC227582
0.7366	Intermediate Similarity	NPC73994
0.7366	Intermediate Similarity	NPC61011
0.7363	Intermediate Similarity	NPC471304
0.736	Intermediate Similarity	NPC57398
0.736	Intermediate Similarity	NPC295898
0.7354	Intermediate Similarity	NPC311858
0.7354	Intermediate Similarity	NPC235684
0.7354	Intermediate Similarity	NPC62749
0.7351	Intermediate Similarity	NPC211997
0.7351	Intermediate Similarity	NPC64436
0.7348	Intermediate Similarity	NPC214960
0.7348	Intermediate Similarity	NPC279527
0.7347	Intermediate Similarity	NPC214428
0.7347	Intermediate Similarity	NPC121327
0.7345	Intermediate Similarity	NPC285469
0.7341	Intermediate Similarity	NPC478186
0.734	Intermediate Similarity	NPC228835
0.7333	Intermediate Similarity	NPC478078
0.7333	Intermediate Similarity	NPC102008
0.7333	Intermediate Similarity	NPC168911
0.733	Intermediate Similarity	NPC478076
0.733	Intermediate Similarity	NPC200743
0.7314	Intermediate Similarity	NPC40070
0.7313	Intermediate Similarity	NPC472070
0.7313	Intermediate Similarity	NPC469589
0.7303	Intermediate Similarity	NPC113946
0.7302	Intermediate Similarity	NPC133003
0.7297	Intermediate Similarity	NPC267885
0.7296	Intermediate Similarity	NPC241024
0.7294	Intermediate Similarity	NPC88097
0.7282	Intermediate Similarity	NPC281049
0.7273	Intermediate Similarity	NPC143977
0.7263	Intermediate Similarity	NPC141612
0.7263	Intermediate Similarity	NPC135601
0.7263	Intermediate Similarity	NPC17273
0.7263	Intermediate Similarity	NPC293487
0.7259	Intermediate Similarity	NPC252338
0.7258	Intermediate Similarity	NPC83774
0.7254	Intermediate Similarity	NPC471386
0.7253	Intermediate Similarity	NPC49954
0.7253	Intermediate Similarity	NPC474561
0.7251	Intermediate Similarity	NPC238499
0.725	Intermediate Similarity	NPC475841
0.725	Intermediate Similarity	NPC474145
0.725	Intermediate Similarity	NPC277350
0.7249	Intermediate Similarity	NPC470003
0.7249	Intermediate Similarity	NPC472294
0.7245	Intermediate Similarity	NPC212213
0.7245	Intermediate Similarity	NPC239954
0.7243	Intermediate Similarity	NPC149155
0.7243	Intermediate Similarity	NPC203468
0.7243	Intermediate Similarity	NPC110500
0.7243	Intermediate Similarity	NPC469529

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 NPC258480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	523
0.2-0.3	658
0.3-0.4	1528
0.4-0.5	2552
0.5-0.6	2509
0.6-0.7	1076
0.7-0.8	104
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8785	High Similarity	NPD4501	Approved
0.8785	High Similarity	NPD4500	Approved
0.8207	Intermediate Similarity	NPD4602	Approved
0.8182	Intermediate Similarity	NPD4601	Approved
0.8182	Intermediate Similarity	NPD4600	Approved
0.8128	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4499	Approved
0.7789	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5104	Approved
0.7684	Intermediate Similarity	NPD2915	Discontinued
0.7665	Intermediate Similarity	NPD4520	Approved
0.7632	Intermediate Similarity	NPD7944	Discontinued
0.7624	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7665	Phase 2
0.7614	Intermediate Similarity	NPD7666	Phase 3
0.7604	Intermediate Similarity	NPD4397	Phase 1
0.7582	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD750	Phase 2
0.75	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD5075	Discontinued
0.7474	Intermediate Similarity	NPD6999	Discontinued
0.7474	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7568	Phase 1
0.741	Intermediate Similarity	NPD3385	Approved
0.7406	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8114	Approved
0.7374	Intermediate Similarity	NPD8115	Approved
0.7368	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4334	Discontinued
0.7366	Intermediate Similarity	NPD5899	Approved
0.7366	Intermediate Similarity	NPD5897	Approved
0.7366	Intermediate Similarity	NPD5473	Discontinued
0.7366	Intermediate Similarity	NPD5898	Approved
0.7363	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD1630	Approved
0.7354	Intermediate Similarity	NPD5444	Phase 1
0.7353	Intermediate Similarity	NPD3393	Approved
0.7353	Intermediate Similarity	NPD3394	Approved
0.7353	Intermediate Similarity	NPD3389	Approved
0.735	Intermediate Similarity	NPD2916	Discontinued
0.7348	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7482	Phase 2
0.734	Intermediate Similarity	NPD7483	Phase 2
0.7337	Intermediate Similarity	NPD7001	Phase 3
0.7333	Intermediate Similarity	NPD53	Approved
0.7333	Intermediate Similarity	NPD7778	Approved
0.7333	Intermediate Similarity	NPD7777	Approved
0.732	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2336	Approved
0.7291	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2095	Phase 2
0.7287	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2092	Phase 2
0.7287	Intermediate Similarity	NPD2094	Phase 2
0.7277	Intermediate Similarity	NPD7234	Approved
0.7277	Intermediate Similarity	NPD7233	Approved
0.725	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD2091	Phase 2
0.7249	Intermediate Similarity	NPD2096	Phase 2
0.7243	Intermediate Similarity	NPD482	Approved
0.7238	Intermediate Similarity	NPD1631	Approved
0.7228	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4948	Discontinued
0.7222	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5293	Phase 2
0.7213	Intermediate Similarity	NPD4640	Approved
0.7213	Intermediate Similarity	NPD4638	Approved
0.7213	Intermediate Similarity	NPD4639	Approved
0.7207	Intermediate Similarity	NPD4326	Phase 2
0.7204	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5426	Phase 3
0.72	Intermediate Similarity	NPD6987	Phase 1
0.7198	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2882	Phase 1
0.7174	Intermediate Similarity	NPD1575	Approved
0.7174	Intermediate Similarity	NPD1573	Approved
0.7172	Intermediate Similarity	NPD6479	Discontinued
0.7169	Intermediate Similarity	NPD3654	Approved
0.7165	Intermediate Similarity	NPD5505	Discontinued
0.7165	Intermediate Similarity	NPD4315	Phase 2
0.7158	Intermediate Similarity	NPD6178	Phase 3
0.7158	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1683	Approved
0.7143	Intermediate Similarity	NPD2307	Discontinued
0.7143	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6249	Phase 2
0.7121	Intermediate Similarity	NPD6248	Phase 2
0.712	Intermediate Similarity	NPD6227	Discontinued
0.712	Intermediate Similarity	NPD5555	Phase 1
0.7116	Intermediate Similarity	NPD4885	Approved
0.7114	Intermediate Similarity	NPD5901	Discontinued
0.7113	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6206	Phase 1
0.7102	Intermediate Similarity	NPD4547	Phase 3
0.7094	Intermediate Similarity	NPD2509	Approved
0.7094	Intermediate Similarity	NPD2510	Approved
0.7083	Intermediate Similarity	NPD5809	Phase 3
0.7079	Intermediate Similarity	NPD6158	Phase 2
0.7079	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6261	Phase 3
0.7069	Intermediate Similarity	NPD4047	Discontinued
0.7068	Intermediate Similarity	NPD7564	Discontinued
0.7062	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6281	Approved
0.7059	Intermediate Similarity	NPD1586	Approved
0.7056	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4204	Approved
0.7053	Intermediate Similarity	NPD4203	Approved
0.705	Intermediate Similarity	NPD7817	Phase 1
0.7047	Intermediate Similarity	NPD2383	Phase 1
0.7044	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7455	Approved
0.7039	Intermediate Similarity	NPD7454	Approved
0.7033	Intermediate Similarity	NPD2511	Approved
0.7031	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3947	Discontinued
0.7027	Intermediate Similarity	NPD2844	Phase 3
0.7027	Intermediate Similarity	NPD5862	Discovery
0.702	Intermediate Similarity	NPD5003	Discontinued
0.7018	Intermediate Similarity	NPD5891	Approved
0.7011	Intermediate Similarity	NPD5020	Approved
0.7011	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4524	Discontinued
0.7	Intermediate Similarity	NPD6770	Approved
0.7	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7957	Phase 1
0.6995	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6995	Phase 1
0.698	Remote Similarity	NPD6176	Phase 1
0.698	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6554	Approved
0.6977	Remote Similarity	NPD45	Approved
0.6976	Remote Similarity	NPD4506	Discontinued
0.6973	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4897	Phase 2
0.697	Remote Similarity	NPD4848	Phase 1
0.6968	Remote Similarity	NPD6790	Phase 1
0.6967	Remote Similarity	NPD6242	Discontinued
0.6965	Remote Similarity	NPD7727	Phase 2
0.6963	Remote Similarity	NPD7426	Phase 1
0.6963	Remote Similarity	NPD8408	Discontinued
0.6961	Remote Similarity	NPD7222	Phase 2
0.6954	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1587	Approved
0.6946	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4952	Phase 3
0.6943	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7730	Approved
0.693	Remote Similarity	NPD7731	Approved
0.6927	Remote Similarity	NPD7952	Approved
0.6927	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7953	Approved
0.6927	Remote Similarity	NPD7791	Approved
0.6927	Remote Similarity	NPD7789	Approved
0.6927	Remote Similarity	NPD7951	Approved
0.6927	Remote Similarity	NPD7790	Approved
0.6927	Remote Similarity	NPD7950	Approved
0.6919	Remote Similarity	NPD4418	Discontinued
0.6919	Remote Similarity	NPD7619	Phase 3
0.6919	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4427	Phase 2
0.6919	Remote Similarity	NPD7618	Phase 3
0.6916	Remote Similarity	NPD7271	Approved
0.6915	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD43	Approved
0.6915	Remote Similarity	NPD6182	Approved
0.6915	Remote Similarity	NPD5427	Suspended
0.6912	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6452	Discontinued
0.6908	Remote Similarity	NPD7470	Discontinued
0.6905	Remote Similarity	NPD8325	Phase 3
0.6905	Remote Similarity	NPD8326	Phase 3
0.6905	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5487	Phase 1
0.6891	Remote Similarity	NPD4957	Phase 2
0.6886	Remote Similarity	NPD8463	Approved
0.6884	Remote Similarity	NPD7935	Phase 2
0.6881	Remote Similarity	NPD5017	Discontinued
0.6878	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3905	Phase 3
0.6878	Remote Similarity	NPD6492	Phase 2

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