NPASS Compound

Structure

CID132385 OpenBabel06191715492D 34 38 0 0 0 0 0 0 0 0999 V2000 1.7468 -5.8408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0564 2.0672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6857 -0.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1662 -1.9879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5581 -0.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0753 -1.6368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4672 -0.0621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4223 -3.8763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4160 -2.9056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4984 -1.7271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5400 0.5153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7398 -1.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3881 0.0371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7411 -3.8872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4076 -1.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2259 -0.6739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5849 -4.3671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5722 -2.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6909 0.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7347 -2.9166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7016 -0.9560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8585 -1.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5614 -1.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0107 -0.9745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8692 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8371 0.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 -0.9374 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8307 -1.4664 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1350 -0.3228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0325 -2.9472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5913 -5.3459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8249 1.4699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 0.4770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 34 1 0 0 0 0 4 6 1 0 0 0 0 4 15 2 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 29 1 0 0 0 0 13 28 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 16 30 1 0 0 0 0 17 32 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 28 2 0 0 0 0 24 27 1 0 0 0 0 24 29 1 0 0 0 0 25 31 2 0 0 0 0 26 27 2 0 0 0 0 26 33 1 0 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.17
Volume:	467.073
LogP:	4.869
LogD:	3.537
LogS:	-6.731
# Rotatable Bonds:	7
TPSA:	89.91
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	2.714
Fsp3:	0.185
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.956
MDCK Permeability:	1.1775247912737541e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.073
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	98.24166107177734%
Volume Distribution (VD):	0.356
Pgp-substrate:	2.575132131576538%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.142
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.89
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	7.419
Half-life (T1/2):	0.151

ADMET: Toxicity

hERG Blockers:	0.783
Human Hepatotoxicity (H-HT):	0.503
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.867
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.084
Carcinogencity:	0.651
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC132385

Natural Product ID:	NPC132385
*Common Name:**	Tyraminoporpine
IUPAC Name:	n.a.
Synonyms:	Tyraminoporpine
Standard InCHIKey:	IXBCBSBEBBIYDT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H24N2O5/c1-32-17-8-9-18-20(14-17)25(31)22-21-19(11-13-28-23(18)21)26(33-2)27(34-3)24(22)29-12-10-15-4-6-16(30)7-5-15/h4-9,11,13-14,29-30H,10,12H2,1-3H3
SMILES:	COc1ccc2-c3c4c(ccn3)c(c(c(c4C(=O)c2c1)NCCc1ccc(cc1)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651050
PubChem CID:	15489513
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003018] Isoaporphines [CHEMONTID:0004118] Oxoisoaporphines

*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
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473438]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8281582]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20526	Menispermum dauricum	Species	Menispermaceae	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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	2090.0	nM	PMID[504432]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC50	>	2090.0	nM	PMID[504432]
NPT1505	Cell Line	J82	Homo sapiens	IC50	>	2090.0	nM	PMID[504432]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	2090.0	nM	PMID[504432]

☑ 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 NPC132385 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	571
0.1-0.2	3464
0.2-0.3	12691
0.3-0.4	5044
0.4-0.5	12972
0.5-0.6	5813
0.6-0.7	1731
0.7-0.8	385
0.8-0.85	21
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC270515
0.9348	High Similarity	NPC208522
0.8913	High Similarity	NPC49547
0.8739	High Similarity	NPC74575
0.8534	High Similarity	NPC470018
0.8368	Intermediate Similarity	NPC470022
0.8347	Intermediate Similarity	NPC24019
0.8326	Intermediate Similarity	NPC210434
0.8299	Intermediate Similarity	NPC41501
0.8272	Intermediate Similarity	NPC15406
0.8189	Intermediate Similarity	NPC210296
0.8174	Intermediate Similarity	NPC470017
0.8167	Intermediate Similarity	NPC22481
0.8133	Intermediate Similarity	NPC90875
0.8087	Intermediate Similarity	NPC470020
0.8075	Intermediate Similarity	NPC246381
0.8072	Intermediate Similarity	NPC473188
0.8072	Intermediate Similarity	NPC183537
0.8066	Intermediate Similarity	NPC182907
0.8066	Intermediate Similarity	NPC189903
0.805	Intermediate Similarity	NPC233334
0.8042	Intermediate Similarity	NPC278525
0.8026	Intermediate Similarity	NPC146976
0.8025	Intermediate Similarity	NPC108342
0.8	Intermediate Similarity	NPC77878
0.7983	Intermediate Similarity	NPC236668
0.7976	Intermediate Similarity	NPC142385
0.7886	Intermediate Similarity	NPC166722
0.7871	Intermediate Similarity	NPC124313
0.7869	Intermediate Similarity	NPC473182
0.7863	Intermediate Similarity	NPC84164
0.7863	Intermediate Similarity	NPC207283
0.7857	Intermediate Similarity	NPC137353
0.7852	Intermediate Similarity	NPC89549
0.7846	Intermediate Similarity	NPC473183
0.7833	Intermediate Similarity	NPC322482
0.783	Intermediate Similarity	NPC162530
0.7792	Intermediate Similarity	NPC118121
0.7791	Intermediate Similarity	NPC72905
0.7764	Intermediate Similarity	NPC473184
0.7751	Intermediate Similarity	NPC475844
0.7747	Intermediate Similarity	NPC134637
0.7733	Intermediate Similarity	NPC473187
0.7724	Intermediate Similarity	NPC172222
0.7724	Intermediate Similarity	NPC329631
0.7712	Intermediate Similarity	NPC202605
0.7712	Intermediate Similarity	NPC112206
0.7699	Intermediate Similarity	NPC173080
0.7695	Intermediate Similarity	NPC200888
0.7671	Intermediate Similarity	NPC101350
0.7664	Intermediate Similarity	NPC473185
0.7647	Intermediate Similarity	NPC235076
0.7645	Intermediate Similarity	NPC216612
0.7645	Intermediate Similarity	NPC122463
0.7638	Intermediate Similarity	NPC63971
0.7638	Intermediate Similarity	NPC91868
0.7633	Intermediate Similarity	NPC274640
0.7631	Intermediate Similarity	NPC235685
0.7631	Intermediate Similarity	NPC472061
0.7625	Intermediate Similarity	NPC204446
0.7625	Intermediate Similarity	NPC23614
0.7625	Intermediate Similarity	NPC100079
0.7621	Intermediate Similarity	NPC253675
0.7582	Intermediate Similarity	NPC179287
0.7571	Intermediate Similarity	NPC474688
0.7571	Intermediate Similarity	NPC477112
0.7567	Intermediate Similarity	NPC227824
0.7564	Intermediate Similarity	NPC36229
0.7564	Intermediate Similarity	NPC476581
0.7564	Intermediate Similarity	NPC16452
0.755	Intermediate Similarity	NPC39370
0.7546	Intermediate Similarity	NPC45048
0.7541	Intermediate Similarity	NPC94842
0.754	Intermediate Similarity	NPC119134
0.7521	Intermediate Similarity	NPC46451
0.7521	Intermediate Similarity	NPC473179
0.7509	Intermediate Similarity	NPC279589
0.75	Intermediate Similarity	NPC474701
0.75	Intermediate Similarity	NPC298449
0.75	Intermediate Similarity	NPC144452
0.749	Intermediate Similarity	NPC225279
0.749	Intermediate Similarity	NPC478045
0.749	Intermediate Similarity	NPC251160
0.749	Intermediate Similarity	NPC6786
0.7479	Intermediate Similarity	NPC188420
0.747	Intermediate Similarity	NPC148889
0.747	Intermediate Similarity	NPC473186
0.7469	Intermediate Similarity	NPC122436
0.7469	Intermediate Similarity	NPC51388
0.7462	Intermediate Similarity	NPC53534
0.7458	Intermediate Similarity	NPC271215
0.7458	Intermediate Similarity	NPC149471
0.7458	Intermediate Similarity	NPC266931
0.7449	Intermediate Similarity	NPC208084
0.7447	Intermediate Similarity	NPC9482
0.7438	Intermediate Similarity	NPC473513
0.7436	Intermediate Similarity	NPC31930
0.743	Intermediate Similarity	NPC260434
0.743	Intermediate Similarity	NPC201508
0.7422	Intermediate Similarity	NPC107123
0.7418	Intermediate Similarity	NPC174049
0.7418	Intermediate Similarity	NPC150239
0.7418	Intermediate Similarity	NPC276657
0.7417	Intermediate Similarity	NPC316981
0.7409	Intermediate Similarity	NPC285254
0.7409	Intermediate Similarity	NPC202503
0.7402	Intermediate Similarity	NPC217554
0.7396	Intermediate Similarity	NPC100734
0.7396	Intermediate Similarity	NPC88923
0.7396	Intermediate Similarity	NPC315634
0.7395	Intermediate Similarity	NPC18348
0.7393	Intermediate Similarity	NPC218388
0.7391	Intermediate Similarity	NPC133140
0.7391	Intermediate Similarity	NPC195268
0.7386	Intermediate Similarity	NPC232225
0.7383	Intermediate Similarity	NPC284141
0.7381	Intermediate Similarity	NPC295228
0.7377	Intermediate Similarity	NPC74360
0.7375	Intermediate Similarity	NPC208284
0.7375	Intermediate Similarity	NPC302807
0.7375	Intermediate Similarity	NPC220337
0.7371	Intermediate Similarity	NPC255800
0.7371	Intermediate Similarity	NPC96584
0.7358	Intermediate Similarity	NPC152620
0.7356	Intermediate Similarity	NPC303374
0.7353	Intermediate Similarity	NPC193238
0.7353	Intermediate Similarity	NPC193777
0.7353	Intermediate Similarity	NPC222561
0.735	Intermediate Similarity	NPC476578
0.735	Intermediate Similarity	NPC476582
0.735	Intermediate Similarity	NPC4071
0.7349	Intermediate Similarity	NPC252251
0.7344	Intermediate Similarity	NPC296482
0.7344	Intermediate Similarity	NPC53069
0.7344	Intermediate Similarity	NPC202768
0.7336	Intermediate Similarity	NPC184408
0.7336	Intermediate Similarity	NPC247803
0.7333	Intermediate Similarity	NPC290689
0.7331	Intermediate Similarity	NPC207686
0.7328	Intermediate Similarity	NPC478083
0.7324	Intermediate Similarity	NPC315499
0.7323	Intermediate Similarity	NPC11408
0.7315	Intermediate Similarity	NPC78609
0.7308	Intermediate Similarity	NPC67401
0.7303	Intermediate Similarity	NPC87413
0.73	Intermediate Similarity	NPC258048
0.7295	Intermediate Similarity	NPC116701
0.7295	Intermediate Similarity	NPC293151
0.7291	Intermediate Similarity	NPC477531
0.7291	Intermediate Similarity	NPC475253
0.7287	Intermediate Similarity	NPC178858
0.7284	Intermediate Similarity	NPC237740
0.7283	Intermediate Similarity	NPC282346
0.728	Intermediate Similarity	NPC183777
0.7276	Intermediate Similarity	NPC174760
0.7273	Intermediate Similarity	NPC129897
0.7273	Intermediate Similarity	NPC219087
0.7265	Intermediate Similarity	NPC473822
0.7262	Intermediate Similarity	NPC472589
0.7261	Intermediate Similarity	NPC309845
0.7261	Intermediate Similarity	NPC11464
0.7259	Intermediate Similarity	NPC161801
0.7252	Intermediate Similarity	NPC244543
0.7252	Intermediate Similarity	NPC472588
0.7251	Intermediate Similarity	NPC209174
0.7247	Intermediate Similarity	NPC60621
0.7247	Intermediate Similarity	NPC7560
0.7245	Intermediate Similarity	NPC191489
0.7238	Intermediate Similarity	NPC304183
0.7236	Intermediate Similarity	NPC213530
0.7236	Intermediate Similarity	NPC193267
0.7234	Intermediate Similarity	NPC17677
0.7224	Intermediate Similarity	NPC27041
0.7222	Intermediate Similarity	NPC473639
0.7218	Intermediate Similarity	NPC280272
0.7216	Intermediate Similarity	NPC15801
0.7208	Intermediate Similarity	NPC284685
0.7208	Intermediate Similarity	NPC308943
0.7208	Intermediate Similarity	NPC216369
0.7206	Intermediate Similarity	NPC132642
0.7205	Intermediate Similarity	NPC182222
0.7202	Intermediate Similarity	NPC48353
0.7202	Intermediate Similarity	NPC96405
0.7202	Intermediate Similarity	NPC171409
0.7202	Intermediate Similarity	NPC473180
0.7197	Intermediate Similarity	NPC285558
0.7195	Intermediate Similarity	NPC46561
0.719	Intermediate Similarity	NPC199667
0.7183	Intermediate Similarity	NPC207620
0.7181	Intermediate Similarity	NPC160898
0.7178	Intermediate Similarity	NPC39679
0.7178	Intermediate Similarity	NPC207873
0.7178	Intermediate Similarity	NPC171787
0.7178	Intermediate Similarity	NPC100573
0.7177	Intermediate Similarity	NPC280799
0.7176	Intermediate Similarity	NPC477549
0.7173	Intermediate Similarity	NPC234197
0.7172	Intermediate Similarity	NPC39500
0.7171	Intermediate Similarity	NPC13249
0.7171	Intermediate Similarity	NPC478078

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 NPC132385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	681
0.2-0.3	1055
0.3-0.4	1730
0.4-0.5	2409
0.5-0.6	2065
0.6-0.7	798
0.7-0.8	113
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8802	High Similarity	NPD8091	Phase 3
0.7942	Intermediate Similarity	NPD6494	Phase 2
0.7866	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4429	Discontinued
0.7819	Intermediate Similarity	NPD5022	Discontinued
0.7747	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD7395	Discontinued
0.7698	Intermediate Similarity	NPD5488	Discontinued
0.768	Intermediate Similarity	NPD6790	Phase 1
0.7649	Intermediate Similarity	NPD6716	Phase 1
0.7647	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3763	Approved
0.751	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7509	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD7859	Phase 2
0.748	Intermediate Similarity	NPD6963	Approved
0.748	Intermediate Similarity	NPD6964	Approved
0.7472	Intermediate Similarity	NPD7925	Phase 2
0.7472	Intermediate Similarity	NPD7924	Phase 2
0.7443	Intermediate Similarity	NPD6530	Approved
0.7443	Intermediate Similarity	NPD6531	Approved
0.744	Intermediate Similarity	NPD7558	Phase 2
0.7418	Intermediate Similarity	NPD6242	Discontinued
0.7417	Intermediate Similarity	NPD7069	Discontinued
0.7409	Intermediate Similarity	NPD7426	Phase 1
0.7396	Intermediate Similarity	NPD7803	Approved
0.7391	Intermediate Similarity	NPD3922	Approved
0.7391	Intermediate Similarity	NPD3924	Approved
0.7391	Intermediate Similarity	NPD3923	Approved
0.7391	Intermediate Similarity	NPD3921	Approved
0.7383	Intermediate Similarity	NPD6230	Discontinued
0.7381	Intermediate Similarity	NPD3006	Discontinued
0.7375	Intermediate Similarity	NPD4502	Phase 2
0.7375	Intermediate Similarity	NPD5416	Discontinued
0.7371	Intermediate Similarity	NPD4373	Phase 2
0.7344	Intermediate Similarity	NPD3816	Phase 1
0.7344	Intermediate Similarity	NPD3815	Phase 1
0.7336	Intermediate Similarity	NPD5482	Discontinued
0.7333	Intermediate Similarity	NPD7417	Discontinued
0.7325	Intermediate Similarity	NPD8149	Discontinued
0.732	Intermediate Similarity	NPD4952	Phase 3
0.7305	Intermediate Similarity	NPD1483	Discontinued
0.7287	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5902	Approved
0.7284	Intermediate Similarity	NPD5903	Approved
0.7265	Intermediate Similarity	NPD5632	Approved
0.7262	Intermediate Similarity	NPD8244	Phase 2
0.7248	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7708	Approved
0.7244	Intermediate Similarity	NPD7853	Phase 2
0.7241	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7994	Phase 2
0.7233	Intermediate Similarity	NPD7922	Phase 1
0.7227	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6962	Phase 2
0.7208	Intermediate Similarity	NPD7955	Approved
0.7208	Intermediate Similarity	NPD7956	Approved
0.7208	Intermediate Similarity	NPD5429	Discontinued
0.7203	Intermediate Similarity	NPD3986	Discontinued
0.7185	Intermediate Similarity	NPD8363	Approved
0.7185	Intermediate Similarity	NPD8364	Approved
0.718	Intermediate Similarity	NPD6228	Discontinued
0.7178	Intermediate Similarity	NPD5658	Approved
0.7171	Intermediate Similarity	NPD3259	Approved
0.7171	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5530	Phase 1
0.716	Intermediate Similarity	NPD4561	Discontinued
0.716	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD3809	Discontinued
0.7137	Intermediate Similarity	NPD2951	Discontinued
0.7132	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4795	Phase 2
0.7123	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5612	Discontinued
0.7104	Intermediate Similarity	NPD6517	Phase 3
0.7103	Intermediate Similarity	NPD4845	Discontinued
0.7091	Intermediate Similarity	NPD8467	Approved
0.7091	Intermediate Similarity	NPD8466	Approved
0.7091	Intermediate Similarity	NPD8465	Approved
0.7082	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5930	Phase 3
0.7066	Intermediate Similarity	NPD7222	Phase 2
0.7056	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5891	Approved
0.7037	Intermediate Similarity	NPD2916	Discontinued
0.7033	Intermediate Similarity	NPD3794	Approved
0.7033	Intermediate Similarity	NPD3795	Approved
0.7029	Intermediate Similarity	NPD3217	Phase 2
0.7029	Intermediate Similarity	NPD1739	Approved
0.7029	Intermediate Similarity	NPD1740	Approved
0.7028	Intermediate Similarity	NPD2899	Discontinued
0.7027	Intermediate Similarity	NPD7886	Phase 2
0.7027	Intermediate Similarity	NPD7885	Phase 2
0.7025	Intermediate Similarity	NPD7010	Phase 3
0.7024	Intermediate Similarity	NPD3925	Approved
0.702	Intermediate Similarity	NPD4131	Phase 3
0.702	Intermediate Similarity	NPD5936	Approved
0.702	Intermediate Similarity	NPD5939	Approved
0.7012	Intermediate Similarity	NPD1954	Phase 1
0.7011	Intermediate Similarity	NPD5450	Discontinued
0.7	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7603	Discontinued
0.6996	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7675	Phase 3
0.6996	Remote Similarity	NPD7674	Phase 3
0.6989	Remote Similarity	NPD8459	Approved
0.6989	Remote Similarity	NPD8425	Approved
0.6989	Remote Similarity	NPD8460	Approved
0.6989	Remote Similarity	NPD8426	Approved
0.6985	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7278	Phase 2
0.6984	Remote Similarity	NPD7279	Phase 2
0.6978	Remote Similarity	NPD7169	Suspended
0.6974	Remote Similarity	NPD6456	Discontinued
0.6968	Remote Similarity	NPD8427	Approved
0.6968	Remote Similarity	NPD8429	Approved
0.6968	Remote Similarity	NPD8428	Approved
0.6967	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7404	Approved
0.6953	Remote Similarity	NPD1505	Phase 2
0.6949	Remote Similarity	NPD5937	Approved
0.6942	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3263	Phase 3
0.6926	Remote Similarity	NPD6290	Phase 2
0.6926	Remote Similarity	NPD4885	Approved
0.6926	Remote Similarity	NPD1392	Approved
0.692	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7181	Phase 3
0.6917	Remote Similarity	NPD2175	Phase 3
0.6917	Remote Similarity	NPD2176	Approved
0.6917	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2177	Approved
0.6914	Remote Similarity	NPD5479	Discontinued
0.6913	Remote Similarity	NPD3920	Phase 2
0.6911	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7467	Discontinued
0.6897	Remote Similarity	NPD8016	Phase 3
0.6897	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6709	Phase 3
0.6885	Remote Similarity	NPD3003	Approved
0.6883	Remote Similarity	NPD5475	Discontinued
0.688	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6569	Phase 2
0.6877	Remote Similarity	NPD6995	Phase 1
0.6877	Remote Similarity	NPD1856	Discontinued
0.6877	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD8358	Approved
0.6866	Remote Similarity	NPD8463	Approved
0.6866	Remote Similarity	NPD5532	Phase 2
0.6865	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5640	Discontinued
0.6862	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3746	Discontinued
0.6857	Remote Similarity	NPD7452	Approved
0.6857	Remote Similarity	NPD7453	Approved
0.6856	Remote Similarity	NPD4350	Approved
0.6856	Remote Similarity	NPD4349	Approved
0.6855	Remote Similarity	NPD7225	Discontinued
0.6855	Remote Similarity	NPD5866	Approved
0.6853	Remote Similarity	NPD6568	Discontinued
0.6849	Remote Similarity	NPD1038	Approved
0.6844	Remote Similarity	NPD5901	Discontinued
0.6844	Remote Similarity	NPD4875	Phase 3
0.6844	Remote Similarity	NPD4876	Phase 3
0.6842	Remote Similarity	NPD7013	Phase 3
0.6842	Remote Similarity	NPD7012	Phase 3
0.6833	Remote Similarity	NPD7948	Phase 1
0.6832	Remote Similarity	NPD5905	Phase 1
0.6827	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.682	Remote Similarity	NPD5805	Approved
0.682	Remote Similarity	NPD4368	Phase 2
0.6818	Remote Similarity	NPD7413	Phase 3
0.6818	Remote Similarity	NPD8349	Phase 1
0.6816	Remote Similarity	NPD8101	Phase 3
0.6809	Remote Similarity	NPD7555	Discontinued
0.68	Remote Similarity	NPD7673	Phase 3
0.6794	Remote Similarity	NPD6750	Phase 2
0.6788	Remote Similarity	NPD4894	Discontinued
0.6787	Remote Similarity	NPD8093	Discontinued
0.6784	Remote Similarity	NPD7548	Discontinued
0.6783	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5469	Phase 3
0.6777	Remote Similarity	NPD5999	Phase 2
0.6776	Remote Similarity	NPD4035	Approved
0.6776	Remote Similarity	NPD6987	Phase 1
0.6776	Remote Similarity	NPD4037	Approved
0.6776	Remote Similarity	NPD4039	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